I gathered the web for the best shemale sex stories for your reading pleasure. If you like sensual and sexual transsexual sex stories, look no further. Enjoy
I was done with my so-call girlfriend named Tammy she kept going like a yo-yo constantly breaking up and saying she wanted me again. She was a knockout at 5'5" blonde hair and weighing about 105 but she was flaky to say the least. After she said she wanted to breakup again a 3d time in 6 months I told her to lose my number and not call me again. I went to the gym to work out my frustation when this guy who worked there came up to me. He said," Are you John?" I said," Yeah I will be done here in a few minutes if somebody is waiting." He said," No, it isn't that well, this lady who was on the stationary bike told me to give you this." I took the piece of paper in his hand and looked at it and saw it was somebody's number. He said," It is a lady and I think her name is Terri and she is about 5'6" brunette and really a looker." I said," Really, well I just broke up again." He said," Well, I would call her up I don't think she will stay available for long." I got done working out and went to take my shower and change clothes in the locker room. I usually don't work out in a gym but tonight I was particularly frustrated. I was about 5'7" to 5'8" and weighed a pretty muscular 160 lbs. I got to my pickup and started it up and drove the 10 minutes back to my place. After going inside the house I was renting I went to the wall where my cordless phone was at and dialed the number. I sat down in my recliner and I heard a very sexy voice answer with a hello. I asked," Is this Terri? The guy at the gym handed me your number and my name is John." She said," Yes, I don't usually do this but I noticed how handsome you were and you were so focused on your workout." I laughed and said," I call that my Breakup Workout." She laughed and said," Did you break up enough to get that body that sexy?" I laughed and said," Well, that is what happens when a man was so obsessed with a flaky blonde. That and I work with a residential and commercial paving crew." She said," I am not usually this forward but I was wondering if you were free to go out Friday night?" I said," Sure, when do you want me to pick you up?" She said," How about 7 and here are my directions to my house." I had a pad and a pen I wrote it down and repeated it back to her. She said," I will see you there and I am so looking forward to it." I hung up the phone and just thought I couldn't believe it I broke up with my ex-girlfriend and now had a date for Friday night. Friday night got here and I had just stepped out of the shower and was towel drying my hair. I went to my bedroom and put on a pair of boxers and got out my new pair of Wranglers I had just bought. Than I got out a real nice snapped down western shirt and my polished boots and got dressed and saw I still had 45 minutes before I was to pick up Terri. I got dressed and put on my belt and my boots and than I got out my hat and put it on. Within 20 minutes I found Terri's house and saw I still had about 10 minutes to spare but I walked up to her door and rang the doorbell. Terri said," Come on in I have something to tell you." I said," Oh, come on please don't tell me you are married." She said," No it isn't anything like that but before we go out you have to accept all of me." I said," How could I not, you are so beautiful." She said," Keep that in mind because I am not genetic female. Let me give you a little background. I was born male genetically but everything about me was female. I knew I was not really male even though biologically I was. My voice never changed during puberty I never grew really any body hair to speak of and my hips are more feminine. I was called sissy in school until at 13 1/2 my parents without surgery allowed a change in gender. Ever since than I have lived my life as a pre-op transsexual woman." I looked at her and said," I can't believe I am going to say this but you are still a beautiful lady to me. I still consider myself lucky to be going out on a date with you and I am more than happy to pick up the tab." She said," Ok then I am glad you still look at me like that. You know at the gym I wear a fake vagina down there? I do that so other ladies don't feel ill at ease when I am taking a shower and luckily there aren't any gay women in there." I took here by the arm and we walked out to the truck. Our first date went better than I can imagine we went out to eat and than we went out and danced until the wee hours of the morning. Yes, we do move onto a beautiful relationship which I will tell you about in coming chapters.
Credit: https://www.nifty.org/nifty/transgender/she-male/shemale-surprise Wolf
This story is a work of fiction and contains descriptions of explicit sexual acts of boys and men discovering their sexuality. It contains graphic scenes of sex between consenting underage boy and adult males... If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission. Copyright 2017 Wolf, All rights reserved. You may contact me at firstname.lastname@example.org if you like. All flames will be ignored. Shemale Surprise By Wolf I was a shy boy, named Jacob, as a result I did have sex until I was eighteen-years-old. Growing up as an only child of strict southern fundamentalist parents meant that I was severely punished when they caught me masturbating. Shame stayed with me all of the time because I couldn't stop playing with myself. I felt like there was something wrong with me. We lived in a rural area, so there were no children my age to play with. At school I was too embarrassed to talk to girls. Even if there was a girl that was interested in me I didn't recognize the signals. Hiking allowed me to get away from my parents so that I could masturbate in the woods. Lifting dead weights developed my upper body. I developed a 48-inch chest, 20- inch bisects, 34-inch waist, 44-inch ass, 26-thighs, on a five- foot 11-inch frame. Upon graduating from high school I convinced my parents that I wanted to go to college in another State because I wanted to get away from my parents. I was told that if I wanted to go to college I had to do it on my own. They were not going to play for my college. I applied to a University 2,000 miles from home and was accepted. I worked hard all summer to save up as much as possible. I had to live as cheaply as possible. I lived in a cheap apartment in a rough neighborhood, commute by public transportation. I found a job that would allow me to take time off for classes. It was a warehouse job that required stacking 52 pound empty steel barrels after they were painting. My build was the reason I was hired. There was another guy working with me in the barrel house. He was an intimidating guy when I first met him. His name was Donald. He had a build every bit as strong as mine, but his arms, chest and back was covered with tattoos. His head was shaved and he sported a dark mustache with a goatee and always looked like he had a three day beard. But working with him I found that he was a nice guy. We developed a pretty good friendship. He encouraged me to stay in school. During lunch-brakes we found that we shared the interest in weight lifting and the outdoors. . He seemed to be as shy as me, because we never allowed the other to see us use the bathroom facilities. That would change after the first academic year. The university was on a quarter-system so after the spring quarter there was a week break before the summer quarter. Don invited me to go backpacking in the mountains with him. Getting away for a few days was just what I needed, so I accepted. I was an experienced hiker, so I packed my backpack for a three day outing. The weather was balmy, so tents wouldn't be needed. I simply packed a plastic tarp to sleep to use as a ground cloth, or make a shelter if it rained. I pack as lightly as possible. My down sleeping bag weighs only 1.5 pounds. Don picked me up at my apartment in an old Ford pickup and I tossed my pack in the back with his. He was wearing shorts, so I saw the tattoos on his legs for the first time. It was a four hour drive to the parking lot at the head of the trail. We locked up the truck and saddled up for the hike up the trail. We were in no rush, so we took our time hiking up the trail, stopping to drink water and enjoy the sound of birds and the sound of woodpeckers hammering holes in trees. It is unbelievable how loud the sound of a woodpecker carries in the woods. It sounds like someone is chopping down a tree with an ax. The air is desiccated and my nostrils were dry and filled with the smell of cider and pine trees. The trail made a lot of switched backs and came close to a stream with cold running water, so refilling our water bottles was no problem. When we met other hikers coming down the trail we exchanged pleasantries. Don knew the trail, so when he chose to take a fork in the trail that led to another peak I simply followed. This trail was rougher and we didn't meet any hikers. When we reached a small valley with a small lake he told me that we would camp there tonight after we reach the peak. It took another couple of hours to reach the peak. We were well above the tree line and had a 360 view of the forest below. There was a 50 caliber ammunition can chained to the peak with lined book and pencil in it. We signed the book and dated it. We sat on the rocks ate our lunch and enjoyed the view. At that altitude it got uncomfortable cold as soon as our bodies cooled off. We pulled out windbreakers to keep warm. Eventually we started back down the trail. When we reached the small lake we went around the lake to get as far away from the trail as possible. We simply laid our ground clothes on a relatively flat area, and unrolled our sleeping bags to air out and allow the down fathers to fluff up. We stuffed our puffy jackets into our sleeping bag stuff sacks to use as pillows. We broke out our backpacking stoves. I went to the stream feeding the lake to fill collapsible bottles with water. Don and I worked well as a team. We had dehydrated food packages and some items to make the food go farther and add taste. We made backrests out of sticks like American Indians made. Three legged tripod with sticks bound together and hung over the tripod. We ate our fill because the hike had worked up a good apatite. When nature called we went off into the rocks far enough to do our business so that our waist would not leach into the lake. We were enjoying each other's company, but Don finally said, "Jacob I have something to confess to you, and I hope we can remain friends after I tell you." I wondered what he could tell me that might affect our friendship. Don said, "I am a hermorphadite!" I was so niece I didn't know what he was talking about. For all I knew he was talking about an ethnic group. He knew that I didn't understand what he was talking about. "When I was born they listed my sex as female because I had a vagina, and my parents named me Donna. When I reach puberty everything changed. I changed into a boy. I was picked on by bullies until I got into weightlifting and martial-arts. Now everything about me in male except for my sex organ, I don't have a penis. I have a vagina and clitoris like a woman!" I still didn't completely understand what he was talking about. Don asked, "Do you want to see?" I was puzzled, but curious, "Sure." Don leaned forward to pull his T-shirt over his head. I had seen is arms and before, but now I saw the designs on his chest and lower abdomen. There were swirling line circling his man tits and there was something like a crest or coat-of-arms on his ripped belly disappearing into his hiking shorts. His back was covered in a colorful dragon with wings spread from shoulder to shoulder. I was mesmerized by the tattoos on his body. The next thing he removed his boots and sock before standing up to remove his hiking shorts and underwear. As the underwear came down I saw the bottom of that coat-of- arms just above his pubic hair. When he stepped out of shorts and underwear he spread his muscular legs so that I could see what his crotch looked like. I was speechless there was no penis or scrotum. I couldn't believe that he had been born that way. They must have been cut off. Don placed his first two fingers on either side of the mound and pressed when it opened I saw the ridge ending in a clitoris like a little dick, and there were another set of flabby lips and I saw the pink opening of my first vagina along with the opening of his urethra. He used his index finger to stimulate the clit kind 'a like I do when I masturbate. He told me that I could touch it if I wanted to. I had seen pictures of naked women before, so I knew what a pussy looked like, and his pussy looked just like the ones in pictures. I reached out and touched the warm slimy flesh. That ridge leading to the clit felt like stiff rubber covered with a layer of moist slippery skin. His clit seemed to get harder and even larger. It actually stuck out like a penis. Don said, "Would you like to fuck me?" "I have never fucked anyone before." Don's face light up "You're a virgin, I have never taken someone's cherry before!" The idea of getting to fuck someone gave me a hard-on right away. Don saw the bulge in my hiking shorts, and he smiled as he reached out and stroked the front of my shorts. I was immobile, so Dom started removing my shorts. At least I managed to pull my own T-shirt off while Don pulled my shorts and underwear down. I stepped out of them with my boots and socks still on. Other than that we were both naked. We lay on his sleeping bag. I had no idea how to go about this, so Don started hugging and kissing me. It was strange kissing a guy with a mustache and goatee, particularly when he started sticking his tongue into my mouth. While we were kissing he ran his hand down my body and started masturbating me like I had always done. It was so much more exciting having someone else masturbating me. It was the same thing that my parents had punished me for doing was so wickedly sexy and wrong at the same time. I had a ragging boner. It felt like it was hard enough that someone could hang from it. It felt so much better than it did when I masturbated myself. Don moved down my body and took my cock into his mouth and sucked on me. If anything my cock got even harder. The strange thing was that as much as I was enjoying the blowjob I couldn't cum. After Don had sucked me long enough to make his throat raw he lifted his head and announced, "I'm going to fuck myself on your cock the first time Jacob!" He stood up and straddled my hips facing me. When he squatted down he reached between his legs to take hold of my dick and guide it to his cunt. He settled down on me until his flesh was pressing against my pubic bone. Then he started lifting his body up and down. He was actually fucking himself on my dick. I still couldn't cum, until Don pinched my nipples and twisted them in opposite directions. At that moment I felt like my cock exploded. I was no longer a virgin. Don managed to maneuver his body around without my cock pulling out of his cunt so that he was lying on top of me, and started kissing me again. When he realized that my cock was not going soft he rolled us over so that I was on top. I didn't have to be told how to pump my hips up and down. I fucked him for what seemed like a long time. By the time I had my second orgasm we were watching each other by moonlight. We didn't want it to end so we put his bag on top of mine and we got into his bag together after I removed my boots and socks. We had the lake to ourselves all weekend. We took full advantage of it. Don sucked me off several times, and I sucked his pussy and tongued my cum out of his cunt. He even rolled me over and licked and stuck his tongue into my asshole. That even made my cock hard right after cumming in his mouth. That evening Don had me fuck him in the asshole as well as his pussy. I even tongue fucked his asshole after I shot my load in his ass. We spent so much time fucking that we had a ravenous appetite. When we weren't fucking we were eating. It was a good thing we brought more food than me needed because we ate a week's ration of food in two days. When we packed up to come out, I was so tired that I felt like my knees were going to buckle at any moment. Don invited me to move into his apartment. I was one happy boy. I was getting sucked nightly and had my chose of pussy or ass to fuck as well. Anyone seeing Donald would never suspect that he was anything more than one hell of a good looking man with the body as good as any Mr. Universe. To prevent anyone noticing the lack of a bulge in his pants he wore a jock strap filled with a rolled of a pair of socks. We did get teased about being gay, but I didn't care. After school I eventually moved on, but never found another guy like Donald. If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to email@example.com
I saw an ad in the local personals and wow was this woman beautiful. She stood at 5'11" shoulder length brunette hair brown eyes 30 B cup breasts and weighed at 140 lbs. The ad said seeking man for possible LTR but said he had to be man enough to take her whims. I decided to respond to the ad and left my cell number. A week later I got a call and I heard a sexy sultry voice on the other side. She said," My name is Alexandria and it seems you are interested in dating and a possible Long Term Relationship?" I said," Yes, I am your ad said I had to be man enough to take your whims." She said," Yes, it would be easier for me to show and tell you. There will be no sex this evening." I said," Sure, show me what?" She said," Can I come over to your house or apartment?'" I said," Sure," I gave her my address and she read it back to me. She said," I have a feeling I know where you are at give me about 20 minutes. Well, I did a little picking up and 20 minutes later I heard the doorbell rang. I opened the door and there she was standing i 5" heels and a long dress that split on the side and she smiled hugged and kissed me passionately for a few seconds and came in and sat down on the couch. She looked at me gave me and smiled the most intoxicating smile. She said," I am all lady but I am what you would call a shemale. Some women like me have gender reassignment surgery but not me. I enjoy my dick and I enjoy what I can do with it. If we have the relationship you would be able to make love to me but I do want to e able to own your ass." I said," I can't believe it you can't be." She got up and unzipped her skirt and let slip down to the floor and then took off her panties and untaped her cock. It was starting to get hard and I could see it was getting hard. She smiled and said," This sexy thing is 8" long ad 2" thick and you better be ready to be topped by me. Another thing I will share you with my friends I have shemale friends. First, we will just date and get to know each other before the night I take your cherry. The one thing I want you to remember is I am a class lady." I thought about for a few minutes and I said," You know what I love the idea of going out with you." She said," Wonderful, how about we go out Saturday.?" I said," Yes, we can go to the Olive Garden." She smiled and said," Great, 7 will be ideal for me." I said," 7 sounds good for me." She went to the door and we kissed goodbye and she walked to her sports car. I shook my head as I closed the door thinking about Alexandra. Well, as I was going to sleep I didn't really appreciate what changes was about to happen in my life.
My Boyfriend Bill We met when his older brother was dating my younger sister. Our parents had decided that the families needed to meet so my father had agreed to grill dinner for both extended families. That meant that we had about thirty people around the pool most of whom weren't wearing more than the most basic swim suits. Since my sister and I had grown up with a pool we thought of swim fashion as much as we did school wear. Even at twenty six I would go over to my parents to swim when the weather was nice enough and I had more than an extra hour. Pat hadn't been there as much the last year, which made the days in the sun more about swimming laps and getting a tan than gossip like we always shared. Pat is a big boobed gal. She had told me she was a 38 EE when she graduated from college. That had helped her find the job she wanted but had been causing her grief with the other employees at the stock brokerage. She had met Brad when she was out to lunch with a college friend that was in the city visiting and closing some of her parent's accounts. The friend had taken Brad along with her to met Pat, he is her cousin and lives near our parents. Pat hadn't been dating much since she had moved back to the city because she was working too much and somewhat disgusted with men because of the harassment she had to put up with at work. Sometimes she even took it out on me. To Pat's delight she instantly liked Brad and he her. They had their first date two night later. He treated her with more respect than I would have thought she deserved, but then he didn't know that she had been the high school 'go to' bang. While in college she had continued that until she had an unwanted pregnancy. She lost the fetus in the first three or four months, it was enough to change her. She moved to a different college for her last two years where no one knew her and changed her ways. She would often bitch at me when she was home that no sex was not the way to live a happy life. That was preaching to the choir. I hadn't had sex since my freshman year at Penn State when the guy I was with got freaked out that I had a cunt hidden under my balls. I'd had a few freaks in his fraternity try to get me to show them what I was like but I hadn't shown any one; I was home after I graduated before I dared going to a gay bar. I played with a few guys but didn't let my secret out, its easy if all you do is suck a few dicks or fuck an ass or mouth in a dark room. At least I was getting my balls drained and my parents noticed that I was happier than I had been in years, Mom thought I had a girl friend. My father knew I preferred boys but had made me promise not to tell her until I found the one I planned on living with for the rest of my life, that seemed unlikely to me so she was left in ignorance. She is oblivious about so much. All I can think is that she must have thought that Pat had periods twice a month from the number of tampons we went through. I don't quite understand the biology of it, but I didn't show any external signs of female sexuality until I was around eleven or twelve. I was playing with myself, I loved doing that, what boy doesn't? I had lifted my balls to play with them and one finger felt something odd and sensitive underneath them. I knew where my asshole was and that wasn't my asshole. I tried looking in the mirror to help me understand what I was feeling but I couldn't make sense of what I was seeing. I thought about asking my mother and father but they had never answered any questions about sex so I doubted they would help me. I thought about asking Pat but I was embarrassed, she was younger and better informed. I was supposed to have a physical for junior high wrestling. It was going to be the first one I'd had since I was a baby. I convinced my father that it had to be him that took me. My mother was always the one that took us to the dentist and doctor but he finally agreed that he would pick me up at school during his lunch hour and take me to see his doctor. If I remember right that was the first time I went to a doctor other than a pediatrician. The doctor was younger than my father but my father said he was the best one that had ever been in the neighborhood. Because of the timing there wasn't anyone ahead of us when we arrived so I was taken to an exam room and told to undress. I was nervous and thought about backing out of wrestling so I didn't have to go through this but part of me wanted to know what was happening to me. I was 5'3", 102 pounds and when the nurse turned me over to the doctor dressed in only a pair of tiny whiteys. The exam room was warm so I wasn't bothered by sitting there like that waiting for the doctor. I thought the wrong person had walked into the room when the door opened, there was a Tyson Beckford clone grinning at me. I could have melted on the exam table he exuded so much sex. He shook my hand introduced himself and picked up the forms the nurse had left in a plastic holder on the back of the door. I hadn't had any sex at that point, but I knew what I wanted as the Dr. tapped my knees, listened to my lungs and heart. The time had arrived. He told me to drop my underwear so he could check for a hernia. Could I ask him? I had to didn't I? I didn't want anyone seeing what it was in the showers after practice and not know what I should tell them. He had me turn and cough and said to pull my underwear up. I couldn't wait any longer. "Doc? Will you look at something?" "Jimmy your penis is fine, your testicles are growing just fine." "That's not what I want you to look at." He sounded a little impatient as he asked what he was to look at. "Can you tell me what this is under my testicles?" I had to use the same word he used although I had been calling them balls since the fourth grade when the girl in front of me in handwriting class told everyone she could see my balls up the leg of my shorts. I laid back on the table and lifted them up. "Do your parents know about this?" He had gotten close enough that I could feel his breath on my balls and the slit that had been growing under them for about six months. "No, do you have to tell them?" "You are going to need them to know. You are going to need their support, Jimmy." "Can you tell me first? I want to know what it is before you bring my father in here." I knew there was a good reason to have him bring me instead of my mother. He and I often would keep things from her and I hoped this was one of those things. "I am going to have to do a more detailed exam, but from what I can see I think you have a girl's opening." When I didn't respond he said, "a vagina." "Doc, I'm serious. What is growing under there?" "Jimmy, I am serious, too. We will need to have an MRI to see what is going on inside of you but from what I see I think you are inter-sexed." My father was as surprised as me, maybe more since I'd had six month to think about what was happening to me. For a few minutes he couldn't say anything or didn't know what to say. The Doctor had covered me with the gown I had worn to be weighed and now took it off so my father was able to see what he was talking about. He stuttered out a few syllables but nothing comprehensible. The hot doc left us alone and said he would be back after he saw the next patient. My father stared, making me uncomfortable. "Can I put the gown over me again?" "Sure, son. Am I still supposed to call you son? Or are you my daughter now?" "I think I'm still your son. Although I have this under my balls I haven't grown tits." He had seldom touched me in the last few years unless we were in the swimming pool but laying there he did feel my chest, I supposed to see if I was developing but it was odd. "You may still be too young for that. We need to tell your mother what is going on." "We can't. She will tell the whole street and the boys will treat me like a girl. I don't want this THING to stop me from being a boy and wrestling against other boys." "Jimmy, I don't know enough about the girl things to help you if you have a period." "That Mr. Kennedy is why I need to do a more thorough exam, possibly with a gynecologist and a urologist. You will want to know if you son is capable of having a normal sex life and maybe even if it is possible for him to get pregnant." "No one is going to fuck me!" I knew enough about how girls got pregnant to say that proudly. What did the doctor think I am? "Is he going to grow tits?" I wanted to know that, too." If I did there wasn't going to be any way I could continue passing as a boy. My thinking was already changing, I was talking about passing as a boy instead of being a boy. Life is going to get difficult isn't it? "We should be able to find out with a hormone test, but this is an area of anatomy that isn't taught in med school, I am going to need help if you want me to be Jimmy's doctor. It might be better to find a doctor at the university that has more experience with inter-sexed children." "And if he wants to stay a boy?" Dad had wanted a boy when mom was pregnant and wasn't ready to give up the one he has. Thank you, Dad. "If necessary he could be given hormone shots that will maintain that appearance. I don't know what can be done about the vagina. Most likely something, transsexuals are having that kind of surgery every day somewhere in the country." "So doc, am I supposed to have a boyfriend or girlfriend?" "Yes. You can have either. Your dick works? I didn't ask while I was giving you the physical." If he had moved my balls much more when doing the hernia check he wouldn't have had to ask. "What do you mean? I can piss out of it and it gets hard 10 times a day." I had to back that down, I didn't want my dad thinking I was a fiend. "Does anything shoot out of it yet? Sperm?" He looked uncomfortable asking that, like the next question was asking me to prove it. "His mother says he has had a few wet dreams." That was news to me, what did it even mean? "When you agree to having the other doctors exam him, we will have to take a sample from you, Jimmy. I think we should do this as soon as convenient, Mr. Kennedy. I don't think there is any reason to be worried, but I want both of you to know exactly what Jimmy needs to do and if there is anything that you or his mother need to be concerned with. "You haven't found blood in your underwear have you, Jimmy?" "No. Will that happen to me?" The idea scared me. "We need to find out. Can I speak to a gynecologist and a urologist or at least find you someone at the university more familiar with inter-sexed children?" "Jimmy, this is going to be your life. What do you think you want to do? Are you ready to learn more about what is going to happen, or do you want to wait ?" "Mr. Kennedy, I wouldn't wait. If he has fully functioning ovaries and is producing estrogen he is going to have to make a choice whether he is going to live as a boy or a girl before he starts developing a beard or tits." The rest of that year my mother questioned my father about why he would take me to this Dr. or that one when I appeared to be as healthy as ever. I didn't get to wrestle that year since I was taking regular testosterone shots. They were on the prohibited list for Junior High School students. If I still wanted to wrestle when I made it to High School it wouldn't matter since they are not on that list. I didn't notice many changes that year although both my cock and my vagina seemed to get larger and I started to see regular explosions of sperm before I even started jacking off multiple times every day. One of the changes I did notice was that I started liking boys more than girls and noticed their butts whether in singlets, football shorts, tight blue jeans or naked in the shower after gym. The only thing I needed to be careful about in gym or the shower was how I bent over. Mostly I didn't but if I needed to I was careful that my butt was faced away from anyone. It was after gym class when I was in ninth grade that I first fucked a boy. I was ecstatic, I knew why I had been noticing all the buts and would have tried to fuck everyone but the boy wanted to turn me around and fuck me. No way I was going to let him see that I had a vagina. Through high school I fucked a few more boys but I always kept my pants on and when it came time for them to get off I sucked their dicks. I even started enjoying that and would do a few boys without getting to fuck them. Now you know about me. Bill came to the backyard BBQ with his family. He is a year older than Brad so that makes him two years younger than me, twenty-four. I could see that he didn't want to be there but sitting around in his preppy shorts and no shirt I wanted to make him comfort. I had Pat introduce me, she warned me that although Brad had told her that Bill was bi-sexual she had only ever seen him with his girlfriend, Cheri. It was only then that I remembered that she had told me about her boyfriend complaining that his brother was as happy being with a man as he was with a woman and some times he even seemed happier. "Why haven't you been swimming?" "My suit is a bit small for our relatives, if some of the more conservative leave I'll get in the water." "So, I'm scandalizing them in this Speedo? Perhaps I should just streak over to the grill and get you a steak and some corn. How would they feel seeing you served by a naked man?" I didn't much care and my parents didn't either. As long as I didn't slip in the grass and fall with my legs open no one would know anything. The pair of Speedos I was wearing weren't really that much more than going naked anyway, they covered my asshole, cunt, balls but showed everyone that I had a long thick cock. "Don't do that, I'll get in the pool with you." Bill stood,I saw he was about two inches taller than me and about thirty pounds heavier and should have been a swimsuit model for the male Sports Illustrated that had started coming out in answer to the female version that had been out for years. I had instantaneously gotten stiff when Bill bent over to remove his shorts. I am a butt pirate and proud of it, when he turned back around his eyes lingered on my hard dick pushing my suit away from my body. I caught that he was staring and didn't move or say a word until he fought his impulse and brought his eyes up to mine. "Something you might like?" He didn't wait to answer, he jumped into the deep end of the pool. I followed him. If there weren't so many of his relatives and a few of mine I might have molested him right then and there. There was no doubt in my mind that I wanted to go to bed with him, yes go to bed. Strip naked and throw back the sheets and fuck that ass. There was also no doubt I would go down on him. "I was told you are bi-sexual." "Not so loud, please." He swam the few strokes to the other side of the pool where there was nobody sitting around. "You heard right, does bi-sexuality interest you?" "Very much. You have a very nice butt. Your face and chest are pretty good too." My interest in bi-sexuality was in finding a bi-sexual man that might want to enjoy my cunt. "Do you always compliment butts before anything else?" "Whenever I see one that I want to fuck? I do." I had moved close enough to him that I could whisper that and rub a hand over the suit coating his butt a little tighter than paint. "And this one is very nice." "Thank you. What if I want to fuck you?" "You need to get in bed with me and ask that question." I had managed to keep my cunt virgin but if Bill is truly bi-sexual I was more than ready to lose that. I was willing to give him all three of my openings, something I had never felt I would be willing to do. But, he was going to have to get into bed with me to find that out. He was cute and looked strong, but what was it that was attracting me? His butt? His cock? Or the Bi-sexuality? "Do you live here with your parents?" "No, I'm living at 1100 Market St. on the twenty third floor." "Not the penthouse?" "When I bought my apartment the penthouse wasn't for sale and I needed a place to lay my head within the week." I laughed at that, I couldn't have afforded the penthouse even if it had been up for sale. Anyway I was only down one floor. "I've been swimming in the pool on the roof of that building. Last year on Labor Day I was invited to a skinny dipping party hosted by a couple on the tenth floor. There were about ninety people there, men and women. Both sexes were swinging both ways, it was one of the wilder parties I have ever attended. Is that pool clothing optional all the time?" "No, during the day there are too many children, around nine PM they are chased off the roof and for two hours it is clothing optional, adult only. I have never seen much that interested me up there. If I had seen you we would have already become good friends." "You think fucking is going to make us friends?" "No but sex is going to make us want to know more about each other. When I find out more about you I am going to want to have you as a friend. At least." "What do you know about me?" "Not enough. I do know you are out of college and working for a bank. That you are family oriented. You are very good looking and interested in sex." "I could say those last two things about you too." "Thank you." We were far enough away from every one that I was feeling brave, I pushed up closer to Bill and pulled his hand down so that it slid into my Speedo and grasped my cock. "Are you ready to go find out more about me?" "I promised my parents that I wouldn't leave until after we ate and our brother and sister made their announcement." He held up a finger and wiggled it. I hadn't known this was to be an engagement party, I wondered if my parents knew. I would have expected them to do it more formally. If I went to bed with my sister's brother-in-law would that be incest? I had never had a brother but the idea of having sex with a brother had always been exciting and now I might actually be doing the next best thing? I could wait until after we ate. "Do you have a car here or did you come with your brother or parents?" "I rode. Why?" "I only have one parking spot at the condo, but I will be happy to take you with me and then to work on Monday." "What about tomorrow?" "You and I are going to spend it in bed." We both laughed at my arrogance but I was hoping that I was serious. I hadn't ever met anyone that I wanted to spend that much time with, I just had to hope he felt the same way. Bill hadn't taken his hand away from where I put it before that but when he heard me propose a day in bed he pushed his hand further into my suit. I started to freeze, he was centimeters away from finding my secret. I wanted him to know but I wanted him to find out by seeing what I was hiding. "No further, you can go there when we are in my bed." I could have kissed him but I did a back dive that exposed my package to him before I went under the water and away. I needed to get away to get my cock to soften so that I wasn't displaying an erection to the entire gathering, my sister would never have forgiven me if Brad's family got upset. A couple minutes later Bill swam to the opposite side of the pool and talked to his mother and my sister, about two minutes later he walked out of the poll not displaying anything but a nice tight butt. I stayed at the shallow end of the pool tossing a ball back and forth with my five year old twin cousins. We stayed there until we heard my father ring a dinner bell Pat and I had given him the year he bought the over-sized grill. I ate dinner with the twins' parents and only when desert was put out did I join Bill. We played footsies under the table which I think some of the kids saw and laughed at. The announcement Pat and Brad made was not what I had been expecting when Bill had wiggled his finger. Instead Brad announced that he had been hired by the only international company in the city. The party slowly broke up, I helped clean up some of the mess. The immediate families were sitting at two tables getting to know each other better. I let my mother know I was leaving and Bill told Brad that he was going with me. We got the look from my sister and Brad, we waved bye and ran to my car. I would have bee arrested for running red lights if he hadn't been a harsh navigator. I still made it home in less time than any other time, there was no doubt I was feeling the need and desire to get Bill in bed. We hadn't touched since we'd been in the pool, but after I parked we kissed so passionately that I was leaking precum in my Speedos. We continued the kiss in the elevator until we arrived on my floor and I had to dig out my pass card and work it into the door, it was almost worn out so it took some time. While I did that Bill played with my butt. I hoped that meant I had picked the right man to be the one to deflower me. One step into the apartment nerves took over. "I need a drink to calm down. Can I get you something?" I had thrown my shirt on a chair I had been given from my grandparents' summer cottage, the only thing in the living room that was really out of place. I opened the pulled out bar, I haven't fully stocked it since I don't drink that often. "I have scotch, gin, vodka, tequila or bourbon. I have sodas for mixers and a few bottles of Miller light and Corona light." I poured myself a triple shot of scotch, I knew I was going to need it to let Bill see that I am inter-sexed, actually I shouldn't say that. I am a true hermaphrodite, I have working testes and ovaries. I have managed not to grown tits only because of the hormone shots but the doctors have warned that the shots are not strong enough to act as birth control. I haven't had to worry about that up until then. If Bill is truly bi-sexual he may want what no one else has taken, I'm afraid that it is going to hurt, I've had a dick in my ass that hurt the first time, but there was no hymen. "I will take a Miller's. Why have you gotten so nervous. You've been with other guys right?" "I have done some things with guys, but you will be the first man I have ever allowed to see me naked." As soon as I said that I knew how foolish I was being and dropped my shorts, leaving me in the Speedo he had seen me in at my parent's. Bill had followed my lead and was standing by the floor to ceiling window in his Speedos holding a beer looking out on the city. The view is uninterrupted by anything, standing there you can be completely undressed and nobody can tell, the windows are treated to see out but not back in and there is nothing to that side which would put anyone up high enough to see anyway. "You never took a shower in all the gym classes you must have taken or after the wrestling matches your sister said you won up to state?" "The guys saw me from the front or saw my butt, but they never saw between my legs." I wasn't trying to be coy but I was having trouble coming out with it. "Believe me I have seen enough assholes that one more won't be shocking. I don't mean they're all the same but I won't be shocked at one more. "You probably have seen lots of cocks and cunts too?" The scotch was doing its job, I was feeling a little braver. "More than most guys I guess. I would like to stay with one person but I have been going back and forth between sucking dick and fucking pussy since high school. I don't know if I can settle for just one, so unless I fall completely head over heels in love I guess I will be playing both sides of the fence for a while." He had come back to the bar and gotten a second bottle of beer. "And you?" I poured myself some more of the liquid courage and reached over to pull down the back of his swim suit. "Yeah, I noticed you liked ass while we were 'swimming', do you like being fucked too?" "Every time I've had a man in my ass I've loved it." I was backing away again. "Then let's go find a bed, I want to find out if you're all talk or a great fuck." If not now when? "Bill, if I was a girl would you want to fuck me?" "Where did that come from? If you were a girl? If you looked like your sister I guess I would." He had turned around so that I was pulling his suit down from the front freeing his cock and balls. They were lovely, about seven inches long and heavy, full balls that I wanted to suck. I knew I could take that much cock in my ass if he wasn't going to fuck my cunt but I held his cock for a moment hoping that he would. "Follow me." I turned to go to the bedroom, his hand slipped into my suit and a finger rubbed at my asshole. Bill, be my savior. "Before you get carried away going for my ass I want you to know that I have never been just a bottom, if you fuck me I'm going to fuck you too." "Such sweet promises." I think he meant it. I stood by the side of my bed not sure how to do what I had to do. Bill didn't wait for me to undress, he untied the suit and started the Speedos sliding down my legs. I took a huge swallow of scotch and let the Speedo fall to the floor. I couldn't just let him discover the truth on his own, it felt dishonest. "Bill, lift my balls." It wasn't what I meant and I know he thought I was being weird. "Wait. Let me lay down beside you. Bill, I want you to get between my legs and then lift my balls." "Just lift them, I can't suck on them?" He hadn't moved where I asked, he was just groping my dick and licking at my left nipple. That felt nice, I had never had anyone touch me there, I wanted him to never stop but I knew if we were to get past my nerves he was going to have to accept what I have between my legs and without seeing it he would never do that. I took the hand that was stroking my cock and slowly moved in under my balls until a finger was touching the opening no man is supposed to have. I don't quite know what was in his head at the moment, I had moved his hand from the most male part of me to the least male part and he hadn't reacted other than to caress it like it was something he expected to find. I guess it was three minutes later that he sat up, looked at my face and then moved where I had told him to at first. I think he was unbelieving when he finally lifted my balls, I tried to decipher the look on his face but it was a look I had never seen before. With his other hand he touch what he had just been feeling a moment before. I was glad I had the scotch running through my system, if I hadn't I would probably gotten out of the bed and hidden. "Are you going through the transition?" He had completely misunderstood. "No. Bill I am a natural hermaphrodite. Both my dick and my cunt are real. That is the reason nobody ever saw all of me in the showers after working out. I had hoped that one day I would find a man that liked both that I might want to have take my virginity. I had my eyes closed as I talked to him. The next thing I felt was wet. It took me a moment to know what he was doing was what he might have done with any girl he bedded but was the greatest feeling I had experienced since the first time I'd had my cock sucked. Then he was moving from my balls to the opening. It surprised me and almost drove me to an orgasm when he went all the way down on my cock, moved to licking my balls and onto my cunt. And finally to my asshole. He couldn't know what he was doing to me but I was begging to be fucked by the time his tongue was on my cunt again. With my feet over his ears the tip of his cock entered me a little then hit the flower that I had kept intact too long. "Fuck me." I was afraid he was going to stop. I think he had taken some virgins before and knew what to do. The pain passed quickly and he was in me. I was the happiest man in the city! I had told him we would be staying in bed the entire next day and we did. Turns out that his ass is as talented as his tongue so I was buried in him fucking as often as he fucked me whether my cunt or my asshole. When Monday morning arrived I didn't want to get dressed for work or to take him home. He texted me at noon, inviting me to dinner that night. We were both exhausted and struggled to make it through the day but seeing the other got a second breath. There are weeks I wish he was more oriented to my cock and other weeks when he ignores my cunt but I wouldn't trade him for two men. I asked him to move into the condo with me four months after we started fucking. Pat was upset that I got one of the brothers, Brad had run off to explore Asia. He didn't tell her but Bill told me that he was looking to find a child bride, the younger the better. Bill says he can't imagine leaving me but he has been asking some strange sexual questions that are arousing me in ways I have never thought possible. How would a three some actually work? His mother asked last night if we have talked about having children. Little did she know that I have been cutting my testosterone shots back in the hope that I do become pregnant. Bill says he wants to be a father. A cock sucking father? Why not?
Credit: https://www.nifty.org/nifty/transgender/she-male/perks by
Legal stuff. This story is fiction and is intended for mature readers only. If it is not legal to read this story in your jurisdiction, or if you are not over the age of 18, or 21, depending on where you are, please close this page now. Warning - there may be references to the smoking fetish in this story. If you enjoy accessing erotic literature on nifty, please donate to nifty at http://donate.nifty.org/donate.html. Nifty is run for us all by volunteer(s) whose dedication is admirable and should be supported by all our community. If you have any feedback, please feel free to email me at Ronald DOT Shearing AT yahoo DOT com. I'd been Information Security Officer at a major financial institution for 3 years now. We were located to the east of New York City in a state of the art office campus. Fifteen hundred employees all told. The work was challenging. Cybersecurity was an ever-changing art, and I was kept busy. One Friday night I was last out of the office when an email virus alert popped up in our Group inbox. It pointed to a user who worked in the executive suite, a personal assistant whose name was Amy Smith. She sounded familiar. As I checked Amy's profile I saw from her staff picture she was what would be termed a MILF. Yes, I remembered her vaguely, office party, sexy but aloof. A secretary to some managers in the senior Back Office management team, I'd say mid 40s to 50 years old, it was hard to tell these days. There was no mistaking from her profile picture Amy was hot. Light brown hair with blonde highlights, deep blue eyes, striking cheekbones, full lips, her chin perhaps a little square. From her file, I could also see she was single, and lived about a 15-minute drive North from the office complex. Rather than delegating to offline support I decided to take a look myself. I was 37, divorced, and hadn't had a girlfriend for a while, and I wasn't going to be doing much that night anyway. Maybe she'd be thankful for some personal IT support. As I checked the alert in more detail, I was surprised at what I saw. In this digital age where everyone has a smartphone, a PDA, a tablet, a laptop, no-one really downloads porn at work these days. Some idiots might do on the guest Wi-Fi, but the information I was scrolling through indicated that Amy Smith's desktop PC and her work laptop had been used to access a large number of adult-oriented websites. I immediately remoted to Amy's desktop PC and logged on as an Administrator. As I checked her browsing history, this appeared to be a regular thing for Amy. Amy (or someone using Amy's PC, possibly a senior manager, I had to consider that option) had been browsing hard-core porn sites, pay sites even, and dating sites, a few of them aimed at the transgendered market. I knew some people weren't that computer literate these days, but on a scale of one to stupid, this was STUPID. I next checked Amy's email client and found the quarantined email. She'd been getting notifications from dating sites to her work email address. Unreal. I still couldn't be 100% sure it wasn't one of Amy's bosses with an uncontrollable lust for kink, so I mentally marked this one down as "sensitive". I could see from checking the online Org Chart attached to her profile that Amy looked after a couple of very senior managers. What if one of them was the "freak"? Dialing up my security management console intranet page, I then noticed that Amy's laptop was currently actively connected to the company network remotely. I instant messaged Amy immediately. "Security alert, please call Mr. Bell ..." and then without really considering it much I entered my cellphone number rather than the helpline 800 number. About 60 seconds later, my cell rang. It was an unknown caller. I picked up. "Hi, Information Security Officer Rob Bell speaking, how may I help?" There was a nervous pause. Then a slightly husky female voice started talking. The voice was slightly deep, albeit in a sexy kind of way. "Ah, ehm, Mr. Bell, this is Miss Smith. Miss Amy Smith from Back Office executive on the 26th floor. I'm at home, ehm, working late, and I got a message on my laptop to call" "Yes, Miss Smith ..." "Please, Mr. Bell, call me Amy" "Yes, Amy. Amy there's a security issue with your laptop" "Oh!?" Amy exclaimed. "Yes, Amy. We need to get your laptop cleaned. I can talk you through the procedure, or ..." I know now I was being a little less than truthful, and I guess my baser instincts had kicked in subconsciously. Maybe a trip to Amy's place (and as I looked at her profile pic again, Amy was definitely a hot MILF), was what made me fail to mention I could have cleaned the laptop remotely from my desk in the office. Plus, if a senior manager was the guilty party I tried to convince myself this might be better dealt with off-site. Amy interrupted, "I don't know how to do that Mr. Bell. I'm not good with computers!" "Rob, call me Rob. I'm still at the office Amy. I can see you live a little North on the Parkway, that's on my way home. If you don't have guests or anything arranged, I could call at your place and we could look at the problem together?" Amy hesitated for a few seconds. "Well, yes, ah, I was just checking emails. I guess that would work. I don't have any definite plans for tonight. Yet" Yet. Interesting. "OK, I'll be there in 20 minutes. Amy, can you do me a favor and shut the lid on your laptop until I get there. Security issues like this are serious and I don't want either of us to make the problem worse than it already is" "Sure, Mr. Bell, I mean Rob." I wrote down directions to Amy's place then ended the call. Worst case scenario I thought I'd get to spend an hour or two in the company of a hot MILF doing the necessary housekeeping on her laptop, maybe getting to know her better. If this was an issue caused by one of Amy's bosses we'd also need to discuss how to handle it sensitively (being honest, top dogs got away with a lot of shit in our company, I'd seen this before). In actuality, the security breach was minor, after all our systems had the virus file quarantined. The situation we were looking at here had been exacerbated by the breach of company policy on online behavior, and porn usage to the extent I'd just seen by any ordinary Joe in the company was likely a firing offense. Best case formal warning. In truth, I should already have been escalating to my management. Let's see what the hot Amy had to say about the situation. I didn't necessarily want to get Amy into trouble, but I had a job to do. I grabbed my coat and car keys and headed to the parking garage. After a wrong turn, it took me slightly longer than 30 minutes to get to Amy's building. She had a duplex in a newish condo development. I parked in a guest parking slot, readied myself and walked up to Amy's front door. I pushed the doorbell. About 30 seconds later I saw a shape through the frosted glass, then the door opened. A nervous Amy looked at me. Wow. She was even hotter in the flesh. Tall and thin, with a very decent rack partially covered by a deep green silk blouse open to show some cleavage (I guessed boob-job, and a good one at that). Long sensual legs descending from a short black tight pencil skirt to feet in red high heels. Expertly applied make-up with light brown and blond highlighted hair tucked up. The look finished with brown rimmed eyeglasses. This was a red-blooded male's secretary sexual fantasy look if ever there was one. "Ah, hi, eh, Mr. Bell. I mean, Rob! Come in please", Amy smiled, a little nervously it seemed to me. I walked in behind Amy, not missing the chance to look at her tight ass swaying through her skirt as she led me to a couch in the open living area the front door had given immediate access to. "The laptop's over here" There was a low oval glass table by the couch. There I could see the dark gray work laptop, lid closed shut, next to what looked like a glass of white wine and an ashtray with 2 cigarette butts smeared with dark red lipstick. The shade Amy was wearing now. An open pack of Marlboro Reds lay nearby along with a silver cigarette lighter. Amy pointed to the couch and I sat down. "I'm going for a top up, Rob. Would you like a glass of wine? A beer? I have some beer in the fridge" "A beer would be great, Amy. Then we'll get to the bottom of this laptop issue" Amy squinted at me nervously. "One minute, Rob". As Amy stepped through to the kitchen area I couldn't take my eyes off her taut ass, the shape accentuated beautifully by her tight skirt. I also noticed black lines up the back of Amy's tights. Fuck, Amy was a hot one. In under a minute Amy returned and handed me a Coors. She had filled her wine glass nearly to the top and took a nervous gulp as she sat down beside me. "Mr. Bell, sorry, Rob, is it ok if I have a cigarette?" Amy asked nervously. "Of course, it's your house, and it's Friday night, anything you like. Hopefully this won't take too long". I smiled then continued, "Before we get to the laptop, do other people use it?" Amy clicked her silver lighter on and took a deep pull on her Marlboro as she lit it. She exhaled a thick plume of smoke towards the ceiling. "No. I never share passwords." "OK, Amy. The thing is, on your desktop at work, and I'm pretty sure also this laptop, there's been a lot of unauthorized access to some websites of a, I guess you'd say, 'mature' nature" Amy's eyes widened. She looked at her cigarette, flicked some ash into the ashtray in front of her, then took another deep drag. "Rob, I'm sorry, I, well, ..." I interrupted. "Amy, don't get upset right now. In some ways, you've highlighted an issue with our web-blocking software. You could argue it's my department's fault that you can access these sites. They should be prohibited. I'll be working with my team on that first thing Monday. OK. Before we look at the laptop, you're sure no-one else could have accessed your machines?" Taking a quick nervous drag of her Marlboro, Amy shook her head. "OK, shall we?", I nodded to the laptop. "Please log on and we'll check a few things and clean things up if necessary" Amy crushed her cigarette out. "Rob, do we have to do this? I know I'm in trouble. But can't you just wipe the laptop, give me a fresh one, I don't know, however you do this stuff?" Amy nervously reached for another Marlboro, lit up. I noticed that Amy had a very sensual way of smoking a cigarette. To be honest, this close to Amy, with the way she looked, I was starting to feel my cock stiffen in my suit pants. "Maybe we just say it's broken? I could drop it on the kitchen floor?" Amy seemed to be a little desperate. "I'm sorry Amy. If we don't do this together now, I'll have to take the laptop, it's company property after all, and it will be much worse if we have to do this with Human Resources in the room" Amy took a deep pull on her cigarette. "OK, but, there are personal things on there that you mustn't tell anyone at work about. Please?" Amy put the hand without the cigarette on my knee. "Let's look and work out what we do, OK?" I was trying to put Amy at ease, but I was also quickly realizing this could go even better than I'd anticipated. I left Amy's hand on my knee, then opened the laptop. Amy lifted her hand from my knee, dangled her cigarette between her lips and logged on. Fuck, she really was bad with computers. In front of me was an almost full screen webpage for a site for "TV Chicks" to hook up on. I could see a personal profile. "AmyTV" Wait! I was confused. I could see Amy in a black Basque and stockings staring at the camera. It was Amy Smith, the hot mature sitting next to me on the screen. I gulped. Fuck, this was unexpected! Amy broke me out of my stunned silence. "Rob, you can't tell anyone about this". I quickly flicked to another screen, a photo roll. I almost fainted. Amy in a pink pvc bra and open crotch pvc panties, black patent leather thigh length boots, her thin stiff 7-inch long cock pointing at the camera. I automatically started scrolling through the photos. After a few shots of Amy in various erotic poses, I got an even bigger surprise when the picture on the screen showed Amy with a younger female assistant from the HR team in our office, Suzy Seeger. Both were posing on the couch, dark-haired dark-eyed Suzy, who most of the guys in the office felt had the best tits in the company, was naked except for a pair of hold- up stockings. Amy was wearing the black Basque I'd seen in the hook-up site profile photo I'd looked at initially, a garter belt and stockings. Amy had a hand under one of Suzy's huge floppy breasts. Both were smoking. My hard- on went up a notch. I scrolled forward as if in a dream. I forgot Amy was next to me. I was now scrolling through pictures from the same session. Beautiful, big-titted Suzy sucking an older guy's cock, only his body visible, gray pubic hair. TV MILF Amy sucking the same older guy's cock it looked like, the guy's face wasn't visible in this shot either. Suzy sucking Amy's she-cock. Wow! Amy's cock wedged an inch or so into Suzy's gaping pussy. Then the shocker. Amy's she-cock in the older guy's mouth. Fuck. I recognized the older guy. Lawrence Bodicker, head of Accounting. I took a deep breath. I turned to Amy. "Amy, you shouldn't have this shit on a work laptop" The photos had got me fully turned on. I was stiff in my pants, my cock was almost bursting to get out. I clicked through the rest of the pictures. The last two shots. Massive tits Suzy facing the camera, a reverse cow-girl DP; Amy's she-cock poking into Suzy's tight butthole from underneath, Lawrence Bodicker's short fat cock slipped into Suzy's cunt. As I turned back to Amy, she placed her hand on my crotch. "Rob, I don't want to lose my job. I also don't want Mr. Bodicker to get in trouble. Or young Suzy. Mr. Bodicker has a wife. Kids. Suzy's a great girl. How about we work this out? I can feel how you feel about me? I take it you've never been with a trans-girl? Let me show you how good this can be" I let out a pant as Amy squeezed my cock through my pants, hard. As I opened my mouth to speak Amy leaned in and kissed me hard. I gave my answer by responding to Amy's kiss wildly, forcefully pushing my tongue back into Amy's mouth. Amy gave my cock a tighter squeeze through my pants, then lifted both her hands and started to unbutton my shirt. We continued our French kissing until Amy got to the last shirt button above my pants waistband. Amy stood up and slowly unbuttoned her silky green blouse. She slipped the blouse off as I disentangled my own suit coat and work shirt and threw them to the side of the couch. Amy's tits looked magnificent, they were tightly squeezed into a low cut lacy black brassiere. Not as big as Suzy's natural jugs, but still sexy as fuck. Amy smiled at me staring at her breasts. "Like them, Rob? They cost a lot of money" I gulped a "yes" by way of response as Amy unfastened her bra from behind and her firm round silicon boobs popped out. Amy then unzipped her skirt which slid down her thighs revealing striped top hold up stockings. Black lacy panties covered what now appeared to be a not insignificant bulge. Fuck, this was exciting me. Much more than I expected. Amy pushed me back slightly onto the couch and unbuckled my belt. Quickly undoing the button on my pants waistband, she expertly unzipped my pants. I arched my back against the couch carefully, allowing Amy to pull my pants down. She threw these to my right and then squeezed my aching hard-on through my boxers. As Amy loosened her hair which flopped down over her shoulders in front of me, she leaned closely into my groin and started nibbling on my cock through the cotton of my boxer shorts, her sensitive bites driving me crazy with desire. Fuck, I was loving this. Amy raised herself up onto the couch beside me, and we started to kiss passionately once more. I could feel Amy's hard thin rod rubbing against my leg. Instead of revulsion I was surprised to find it was turning me on. Then all of a sudden, the doorbell went. FUCK! As we paused, Amy looked at me and smiled. "Rob, trust me on this one. Stay just as you are on the couch" I looked back at Amy aghast. What the fuck! I was suddenly terrified. Amy wasn't seriously going to let someone in? With me with a stiff cock busting out of my boxer shorts and my work clothes scattered around the floor? "Amy, you must be fucking kidding, you ..." and then to my horror the door to the room clicked open and in walked Suzy Seeger. She of the best tits in the office fame. FUCK. ING. HELL. Suzy just smiled at me from across the room, took a deep pull on the last remnants of a cigarette she was holding, walked towards Amy and me, stubbed the cigarette out in the ashtray on the oval coffee table and immediately pulled Amy to her and gave her a slow lingering tongue kiss. I was speechless. Amy, her cock still fully erect, sat down to my right, and Suzy, discarding a beige short rain coat to reveal a short powder blue colored lycra dress which her massive tits seemed to be stretching to get out of, sat down to my left. Amy spoke first. "Rob, when you called me to tell me you were stopping by, I knew we, I mean Suzy and me, were in trouble. I called Suzy. I mean, I was prepared to take the chance of seducing you myself, I can be very persuasive with a man's dick in my mouth, but if you hadn't been so open to me being trans, well Suzy here was back-up." Suzy had picked up the pack of Marlboros, first lighting one and passing it across me to Amy, then lighting one for herself. She still hadn't said anything. But as she exhaled a flume of blue gray smoke, she pressed her massive tits against my left arm. Amy continued. "Rob, do what you need to do to my laptop and work PC. But first, let's me, Suzy and you have a little fun. Suzy thinks you're cute, anyway, don't you Suzy?" Suzy exhaled another plume of smoke. "Had my eye on this one for a while," Suzy smiled, "Much cuter than the managers we usually fuck." I noted Suzy had said 'managers', plural. Suzy put her hand to my face, tilted my mouth to hers, and kissed me hard, her gorgeous wet lips and tongue forcing my own mouth open. I felt Amy, grip my boxers and free my cock, then shuddered as she locked her lips around the bulbous head of my shaft. I tensed like I'd received an electric shock. Christ, she, he, she, I was confused, was GOOD. Amy started sucking my cock with a slow up-and-down motion, as Suzy broke off our kiss and peeled her lycra dress off from the top. My eyes widened as Suzy's massive natural melons flopped free. Fuck, they were amazing. As she removed a thin black thong she was wearing, Suzy urged me on. "Suck them Rob, go on, suck my massive titties!" I didn't need to be asked twice, greedily wrapping my lips around the giant areola of one of Suzy's huge boobs, before hungrily switching to the other. Amy removed her mouth from my cock, took a last deep draw of her cigarette, and stubbed it out in the ashtray. Suzy also leaned back and discarded her cigarette in the ashtray. As I leaned back, this time it was Suzy who grabbed the base of my shaft and swallowed my cock. I convulsed. Amy smiled at me, then tapped Suzy on the shoulder. "Suzy, let's share" This was like living a wet dream. Amy and Suzy both ran their tongues up the length of my shaft, then took turns teasing my glans with their tight lips. Amy then took control of my cock head as Suzy started to flick her tongue over my tight ball sack. I started to moan loudly. This seemed to focus the 'girls'. Freeing my cock from her mouth Amy leaned back allowing Suzy to straddle me. With the minimum of fuss Suzy gently directed the tip of my cock to the entrance to her by now dripping wet pussy, then lowered herself down firmly, spearing her cunt with my, by now, throbbing hard cock. We simultaneously let out a gasp, then Suzy started a steady rhythmic motion as she started to milk me with her tight cunt hole. I felt Amy give a tight squeeze of my balls, then stand up. I was losing myself in Suzy, this was the best sex I'd had in years. Hell, ever, if I was being honest. I noticed Amy position herself on the back of the couch, the upper part, then carefully slide her she-cock into Suzy's mouth, only inches from my own mouth. Suzy growled as she upped the pace on my rod, and Amy also started to let out breathless high pitched moans as Suzy's succulent lips milked her cock. Then it happened. Suzy slid Amy's cock out from between her lips and leaned her mouth towards mine, directing Amy's shiny purple cock head towards my own lips with her tongue. My breath stopped for a second. Then without really thinking I wrapped my lips around Amy's she-cock. And started to suck. Suck a cock, for the first time in my life. Suzy almost squealed in delight as Amy started to pump my mouth with her thin stiff delicate rod. Fuck! I was sucking a cock. I didn't care, it felt amazing, I genuinely surprised myself by how much I was enjoying this, my first time sucking tranny cock. Suzy suddenly stopped pumping, and issued a guttural moan. "FUCK, I'm cuummmmiiinnnggg!" Amy reacted by pulling back slightly withdrawing her cock from my mouth. Sliding down so her face was close to Suzy's, Amy locked her lips onto Suzy's as Suzy's orgasm rippled through her body, her fleshy tits quivering in time to the contractions I could feel emanating from Suzy's soaking wet vagina, still tightly clamped around my erect member. As Suzy's orgasm subsided, Amy turned to face me. "Don't come yet, Rob, it's my turn. Fuck my tight asshole, please, fuck me" Suzy pulled herself off of my still rigid cock, then sat down alongside me on the couch. Amy grabbed my hand. "Rob, behind me on the floor. Fuck me from behind while I lick Suzy's cunt" Amy got down on all fours as Suzy lit a cigarette. Suzy held the cigarette so that Amy could take a puff, then directed Amy to her glistening wet cunt. Amy tongued Suzy's clitoris, then started licking. I knelt behind Amy's ass. Pinching my soaking wet shaft at the base, I positioned the tip of my cock at the entrance to Amy's poop tube, then slowly pushed my groin forward. Fuck. The intense feelings that filled me as I slid my full length into Amy's shemale butthole were like nothing I'd felt before. Amy stopped tonguing Suzy's cunt for a second. Then I started pumping. Amy started squealing in ecstasy as I rode her. Suzy started to feverishly rub her clit. I knew I couldn't last long. As I felt the pressure build, I let myself go. With each spurt of my come into Amy's tight asshole I let out a loud yell. While I'd shot my load into Amy's rectum, my eyes had been closed. I opened my eyes to see Suzy smile at me. "You're good, Rob. I hope you can re-charge your batteries. I really want to feel your stiff cock in my asshole" Amy slipped my spent cock out of her asshole. "Rob, do what you need to do with the laptop. Then after, Suzy and me will fuck your brains out again. OK?" I nodded. This was going to turn into a very good Friday night. Part Two to follow.
Credit: https://www.nifty.org/nifty/transgender/she-male/my-new-life by
I had a pretty normal life until I met Sherie and then my life changed dramatically, You see Sherie is a big cock transgender woman or as she is known in some circles a shemale, Not only that she has 4 brothers and 8 men friends who you can say have big cocks and big sexual appetites. Yes, I serve them all and I can't believe it. How did this begin very innocently I met a beautiful lady at the lake close to m house first I was fishing had no luck and the weather got hot. I was swimming and came out and went to the cooler and I saw this tall curvacious woman when I went to get a water out of my cooler. She said," My name is Sherie and I am so thirsty and don't want to go all the way to my car." I said," I understand, I have a lot of water in the cooler if you want." She said," That would be great thank you." She sat down next to me and I handed her a bottled water. I said," My name is John and it is my pleasure to meet you." She said," It is so nice to meet you. I know I am being forward first asking for water and now asking are you married?" I said," No, I am not married." She said," I am glad." Sherie is about 5'9" and weighs about 160 lbs and has breasts that are about 28 dd breasts and a washboard stomach. she has well-defined biceps and thighs and calves and she has shoulder length brunette hair and green eyes a very beautiful lady. She said," I had the misfortune and poor choices of falling for married men." I said," I am very single so you don't have to worry there." As for me, I am of average height and weight may be a bit shorter than average height. I stand 5'8" weigh about 175 lbs and have brown hair blue eyes and my cock I have been told well endowed at about 7," I think. She said," I see you have a rod and reel and your tackle box." I said," Ya, I came here to go fishing first but no luck so I decided to go fishing." She said," Understandable .:" She is curvasious and I think pretty athletic, and beautiful and I couldn't take my eyes off of her. I said," I would love to go out with you if you would like that." She smiled and said," I am glad you will find I am a very one man woman though you can say I run in interesting social circles which in time you will find out." I thought about it for a moment and said," That is alright with me." After that we swam and talked and all of a sudden I saw it was getting close to 5:30 and Sherie was smiling. She asked," Why don't you come to my house? I have something to show and tell you. I can cook you a good dinner." I said," Sure," We both walked hand in hand until we got to the parking area and she got in a Mazda RX-7 and I got in my pickup and we both backed out and I followed her car. After about 20 minutes we arrived to a split-level brick house and I walked up behind her as she opened the door. She unlocked the door and smiled and kissed me and walked inside. She cooked chicken breasts with brussel spouts corn on the cob and brought out cantelope slices within 30 minutes we were at her beautiful table eating dinner. After cleaning up we got to the living room and we sat down on the couch. She said," First, I have to say I am not a conventional woman but I am all lady. So what do you see when you look at me?" I said," A beautiful lady." She said," Once I show and tell you I want you to remember that." She took off her shorts and pulled down her panties and removed the medical tape and I couldn't believe what I saw. It was flaccid what looked like about 41/2" cock. I shook my head in disbelief as she sat on the couch. She said," I was born biologically a male but really feminine and one thing I do have this beautiful cock. My breasts are real and very much mine. This cock when I am aroused is 8 1/2" and yes I do love banging a tight hole. You will treat me as the lady I am. Yes, I will be dominant here and you can say I will own that ass of yours." I asked," Tonight? You are a beautiful lady." She said," Not tonight but will you accept me as your lady and will you take me out on dates as your lady?" I said," Yes." All of a sudden we kissed for a couple of minutes then she said." Well, we are now dating." She got up and retucked her cock and put up her panties and she had shorts up and rezipped. She said," I am not embarrassed about my cock but it can be a bit distracting. What do you do?" I said," I do sheetrock and handyman." She said," That is a young man's job I hope you can do something else when you get older." I said," I think I will be able to." We talked until about 10 and I said," I have to go home but let's do go out next week." She came up and handed me a card and it was her name and number and we kissed for a couple of minutes. I left her place and arrived home about 20 minutes later and undressed and crawled into bed and wondering what my life will hold with Sheriee before slowly falling asleep.
Credit: https://www.nifty.org/nifty/transgender/she-male/the-suprize by Charles Cox
Stephanie stood there and watch her roomates Kevin and Robbie highfive eachother and whoop and holler. They had been watching a football game and apparently, their team scores. She didnt watch sports. "I'll be back in awhile guys". They grunted a reply without looking up. She was headed to the local market to get stuff to make the boys, her boys dinner. They had been living together as roomates for about a month now and Stephanie thought it was time she told them her "secret." She sighed as she rode the elevator down to the lobby. Outwardly, she looked like a woman in every way. Long curly blond hair, beautiful blue eyes, full breasts and a lean waist. Her secret was thatc Stephanie had been born Steven. Her two guys, whom she had grown to love more than anything were living with a trans girl. She still had her male parts but she shaved and waxed her face and legs and chest. She had taken estrogen which made her voice higher and her appearance more womanly. She didnt know how Kevin and Robbie would take the news. She feared they would pack up and leave. Tears filled her eyes and rolled down her cheeks as she began crossing the street. She didnt see the oncomming car until it was too late. When she came to, Stephanie heard voices. "No! Im not fucking staying here man! Im getting my shit and getting the hell out!" She knew that was Kevin. They must have been told what and what and who she was. "Robbie" she whispered. Her mouth was dry. "Hey! Your awake!" Robbie exclaimed. She felt his hand on her shoulder. Tell Kevin I'll refund his half of our rent." She felt tears well up in her eyes and roll down her cheeks. Robbie sighed. "You dont worry about that now. Just rest." She heard him sit. Slowly she opened her eyes. Robbie was sitting there looking like he hadnt showered in awhile. "How bad is it?" she asked. He shrugged. "The driver said if he hadnt slammed on his breaks, youd have been toast. Apart from a broken arm and some bumps and bruises, doc says you can probably go home tomarrow". Stephanie nodded. "Why dont you go home and get some sleep. When Im feeling better I'll start looking for a place to live." She and Kevin were renters. Robbie owned the apartment. Robbie was so handsome. Kind of like a Latino Jesus. Long curly black hair parted down the middle, intense brown eyes, trimmed stash and goatee and a lean, toned build. He laughed. "Why would you need to do that?" Stephanie stared at him. "Because now, everytime you look at me you'll feel uncomfortable". Robbie laughed. "Did I say I was uncomfortable?" She shook her head. "Wanna know a secret?" she nodded. He leaned in closer. "I already knew!" Stephanie gasped. "Since when?" He smirked at her obvious suprize. "Since I first met you. My last girlfreind was a shemale." Stephanie was glad she was laying down. His revelation would have made her faint. His dark eyes sparkled as he looked at her. "I was kinda hoping you'd want to be my girl!" Stephanie couldnt believe her ears. Tears welled up in her eyes and she blinked. "Are you serious?" he leaned down and kissed her gently. "Oh yeah!" He stayed with her and when she was well enough, took her back to the apartment. When they walked in the door Kevin was waiting. Stephanie feared the worst. He just stood there looking down at his sneakers. "Can I talk with you?" he asked. Robbie looked at her. "Who me?" he asked. Kevin shook his head. "I'll be in the next room if you need me baby!" he said giving her a peck on the cheek. "Baby?" Kevin asked with a slight smirk. Stephanie frowned. "He accepts me as I am." Kevin looked ashamed. "When I found out the truth, I didnt know what to think!" Stephanie nodded. "I wanted to be pissed at you but the more I thought about it, and you I.." he stopped, his bottom lip quivered. Stephanie moved to him. "Sweetheart, you can tell me anything. Im still me!" Kevin looked up at her with tears in his beautiful blue eyes and before he knew what he was doing, his lips were pressed against hers. When they parted Stephanie was smiling. "What was that for?" she asked smiling. Kevin smiled and he blushed. "I realized I love you. You and Robbie both." Robbie came out of his bedroom. "You do?" Kevin nodded. "Ive known I was in love with you two for awhile. I just didnt know it till Steph got hurt". Robbie moved in to hug him and then did something that made Stephanies heart race and her cock twitch. They kissed passionately. Kevin place his hand on Robbies ass and squeezed, causing him to moan softly. Seeing Robbies slight, leab build pressed up against Kevins muscular, bulky frame made her hot! "If we dont stop now, all three of us are gonna end up in the bedroom" Stephanie exclaimed. Robbie and Kevin both smirked. "Like that would be a bad thing?" Robbie exclaimed before taking her hand and leading her into her room as Kevin followed right behind. To be continued.... Hope you guys liked part 1 of my first Shemale series. Send me an e-mail at firstname.lastname@example.org and let me know what you think and as always please support Nifty. Without them, we wouldnt be able to express ourselves through our stories!
Credit: https://www.nifty.org/nifty/transgender/she-male/pans-servant/pans-servant-4 by Samathia
It was Kyle's birthday party and he had invited all his friends, including two very important women in his life. He was sandwiched between them at the second bar they visited. Simona was to the right of him and Leena to the left. Surrounding the semicircle of the table were other friends from school, work or people he had met around the city. At one point Simona told the table she was a Pansexual, Leena then interrupted her and said, "That's not a real thing." "I'm right here. Right in front of you. I'm a real thing." Leena started to go on about mental illness and Kyle sat back and watch the shit show erupt between them. Leena was already way too many drinks in for it only being 6pm in the evening, and could barely hold herself together. She kept asking the server for the same things over and over. As they left that bar to depart for another venue, one of Kyle's friends from work took Simona aside and said to her, "Try not to strangle Leena." If Kyle's co-worker only knew the half of it. The group jumped to a few more bars, but gradually dwindled in size. Eventually the last two of his coworkers departed for the night, and it with just Simona, Kyla and Leena, on an elevator to his apartment. Leena had mentioned something about wanting a cab home, but she was so drunk it was easy to convince her otherwise. Once they were all back to Kyle's place, they wasted on a little time, making more mixed drinks for themselves. Leena didn't need any more, but they fed them to her anyway, to make it easier as the night went on. Leena's complaints about Simona grew more vocal yet disjointed as her childlike intoxicated state grew. She was slapping Kyle and shoving Simona, but eventually two of them had her in Kyle's bed. They were stripping off her clothing. Leena tried to protest, but Kyle slapped her face yelling, "Shut up you disrespectful bitch." The slap was hard, harder than either Leena or Simon was expecting. Leena's head jerked drunkenly from side to side. Simona started to see a small tear form in Leena's eye and she immediately felt her cock starting to become hard. Kyle had his ropes out and it wasn't long before Leena was not only out of her dress, but had her hands tied to the posts of the bed. Her legs were still free, with Kyle and Simona between them making out. Leena began to protest and Simona pulled off her own shorts and her panties, and stuffed her panties in the bitch's mouth. They continued to make out between Leena's thighs, ignoring Leena's ever increasing protests through the gag. Leena's eyes sprung wide open as she saw Kyle hold Simona's growing cock in her hands. It was larger that Kyle's, only about an inch in length but much more around in girth. Kyle stroked the two massive members with one hand as they continued to kiss. His other hand was gently walking its way sensually up Leena's legs. Her own head was awash in emotion. She loved when Kyle did that too her; even grew to enjoy when he took his pleasure from here against her protest. But now he was making out with the a girl she despised; a girl who wasn't even a real woman. Leena would have yelled the words, "Tranny" and "Stupid bitch" if she hadn't been gagged by Simona's wet panties. She probably said those words anyway, but neither Kyle or Simona could discern them. They just noticed her muffled protests escalating as Simona lines up her cock to Leena's pussy. Tears were in Leena's eyes by now, even as Kyle grabbed her legs to steady her struggle. The ropes held very well, and Simona grew harder as the tip of her eight inch wonder slapped Leena's wet pussy. Leena looked away as a mischievous smile drew across Leena's countenance. The head of Simona's cock began to penetrate her, and the rest of her member felt harder as Leena stiffened and cried out. Slowly the cock eased its way in deep into Leena's wet and wanton pussy. Simona pushed it in half way at first, then slowly drew it out, and back in again. In that easy rhythm, she felt Kyle kissing her neck. Simona's breasts were very firm and round, although not as large as Leena's, nor did they look as big with Simoan's thicker body. She had tried to tell Kyle it was all muscle, but he could tell it was fat from her frivolous relationship with food, health and eating. Still Simona's breasts were big and she did not like gentle touches. She told Kyle she could only enjoy it when men and women pulled and squeezed hard at her breasts. Kyle was firmly squeezing one in his left hand as his other hand reached down between Simona's ass to cup her very nice balls. He squeezed and prodded with both hands as he kissed her neck. Leena continued to scream through the panties as Simona began to move faster. The weight of her plump body began to slam the massive cock into Leena. Before long Kyle could no longer hold onto her balls and let them slap freely against Leena's pussy. Kyle grew more erect as their thighs and skins collided. He began to pour lube on his cock, getting it nice and slick. Simona slowed momentarily as Kyla lined up his cock to Simona's ass. She was ready to take him and Kyla began to slide right in. Simona rocked back and fourth, fucking Leena while backing up further and further onto Kyle's hard dick. Eventually they began to fall into a good steady rhythm. Kyle and Simona's thrusts were almost synchronized. Leena could feel it now through her tears. When Leena turned to look at Simona, her eyes were locked straight into her own with a fiery lust deep within them. She couldn't look and turned away, focusing on the dresser next to the bed. She saw Kyle, the man she had let take her, resisting on that very first night, but now her reluctant lover. She watched his thin but tight ass thrust in rhythm and it was as if he were fucking her; fucking her with Simon as a condom between the two. Leena tried to focus on the mirror; focus on Kyle who was really fucking her. At first there was some relief when Simona's cock pulled out from her pussy, but it immediately was replaced with shock and screams and pain as Simona pushed it into her ass. Covered with her dripping pussy juices, Simona pushed it in with a steady, but slow force as Leena cried out. The panties in her mouth were soaked with spit and tears ran down Leena's face. Simona pulled out to the head, then slammed the cock back in. She did this several more times, thrusting very hard and vigorously, deep into Leena's ass. Eventually she paused, allowing Kyle to line back up with her asshole, and then they again began to fuck her together. They rode her together with Kyle biting Simona's neck, squeezing her tits and occasionally slapping her thick ass. They continued to fuck Leena through her cries until Simona and Kyle both began to cum. Simona started first, squirting her jizz straight into Leena's asshole, and Kyle followed only a few seconds after. They continued to trust as they cocks squirted out their creamy loads into the tight waiting assholes in front of them. Eventually the two of them collapsed forward right onto Leena. They kissed in front of her, both of them fondling Leena's massive tits with their hands. They then began to kiss Leena's breasts and bite at them gently. Simona lightly slapped at Leena's face saying, "How do you like being fucked by a Tranny you stupid cunt? Am I a real thing now? Did you like my real cock filling your asshole with my cum?" Leena only whimpered, "Answer me bitch!" Leena tried to say something, but it was unintelligible. Simona removed her panties, "What did you say?" Tears welled up in Leena's eyes as she said the words, "I want Kyle." The two of them laughed as she began to cry. Kyle cupped his hands around Leena's head, "It's okay baby. You were good tonight. You took Simona's cock so well. We know you really love her she cock. We know you love it. Tell me you love it." "I--," Leena began to stammer. "I---I---," Leena's voice was caught in her mouth for several more moments before she finally said, "I liked it." "Are you my little slut," asked Kyle. "Yes. Yes I'm your slut Kyle. I like it." "Good. We've got more for you." Before long, Kyle and Simona were hard again. They began to untie Leena and she didn't struggle. She was broken in now, like a horse knowing her place. They turned her on her fours and Kyle and Simona both took turns fucking her doggy. Simona got Leena to suck her cock while Kyle fucked her asshole again. They came several times, once on Leena's tits. The next time Simona came on her face and she started to cringe and close her eyes. Simona slapped her hard across her face, "Don't make faces! Don't dodge you stupid cunt. Take our loads!" The next load came from Kyle and she opened her mouth as he squired into her. Simoan pushed Leena's mouth on to Kyle's throbbing cock chocking her, and yelled at Leena to swallow. Leena gagged a bit but eventually took it down. The two of them continued to have their way with their little love slut, and eventually collapsed together. Kyle was in the middle, his arms wrapped around Simona, as Leena had hers wrapped around Kyle. The next morning Leena would awake to the sounds of Simona and Kyle fucking in the kitchen. It was right next to the bedroom in that small apartment. Her clothing was still on the couch, so there was no sneaking by them. They ordered her to get on all fours, and they spit roasted her. Simona skull fucked her while Kyle fucked her pussy from behind. Simona came first, cumming down Leena's throat. Kyle then came in her pussy. As they stepped away from her, Leena said, "Can I leave now?" "Yes," Simona answered. She was expecting the words to come from Kyle, but didn't wait. She ran to the couch and began to put on her clothing. "Leave your panties and bra," Simona said. Leena hesitated for a moment, then did as she was told. She put on her dress, took her purse and walked out of the apartment with her shoes in her hand. She didn't look back as she open and closed the door. As she walked away, she heard moans as the two of them began fucking again.
Credit: https://www.nifty.org/nifty/transgender/she-male/pans-servant/pans-servant-3 by Samathia
Kyle's had a whirlpool bathtub in his luxurious apartment's bathroom, and Simona loved to take long hot baths with him. They'd lay in a tub large enough easily accommodate his height her her plump body. The two would talk, kiss, massage each other, and play in the water. Candles were lit around the tub and the two of them had just finished smoking a joint. They had to put it out before it was done, as they couldn't keep the base from getting wet from their fingers. The roach lay in a tray next to a candle, Simona having Kyle wrapped on her arms with her back on an inflatable bath pillow. Simona was telling Kyle about high school. "So you were always a girl growing up," Kyle asked Simona, his head cradled against her neck and boobs. "Yes. My mother raised me as a girl," she answered. "But you had sex in high school?" "Yes, once. He was, a bit surprised," she said smiling in her cute manor. "What did he do?" "Well. I knew it would probably be alright. We had watched porn before and he had felt up my breasts. I knew from the porn he downloaded that he was into trannys. I had even asked him once if he'd suck a tranny cock and he said 'Yes.' "We first had sex in a storeroom out by the baseball field at our high school. His mom use to work the concession stands and had a key to the lock on that room. There was an old, torn leather couch in there and we had been going there for a while to make out. "We would play with each other pretty hard, and one day this boy started unclasping my bra and I took off his shirt. Our clothes started to form a pile next to the couch. I had undone his jeans first, his cock was already hard in my hands. When he undid my tight shorts, I couldn't hide it any longer. My cock was hard and pushing through my panties. "I could tell he was in shock. He dick was still hard though. He was excited, but unsure. We were horny but afraid. I kept kissing him, and we kept making out. I stroked him and felt him get harder. Then I started to suck his cock." Simona's hands were between Kyle's legs in the water. She felt it start to grow and push gently at her hand. She was glad this story was exciting him. "Eventually I was on top of him. He told me, 'wait, so how do we ... I mean...' "I put my hand against his lips and shushed him. Then put my cock right up to his mouth. He couldn't resist. He began sucking. He did what he knew from porn. He had a cock, so he knew more what to do than a teenage boy would know how to treat a pussy. I put my head in his hair and guided him. My own hand reaching behind me and keeping his cock hard with my hands. Eventually I slid him to the floor in front of the couch, told him to use more spit as he sucked and licked my cock. I added my own spit to help get my cock super wet and slobbery. "He looked up at me and asked if we were going to have sex. I told him, one of us would. I made him get back on the couch under me, but to have his face down. He looked a little scared, but he trusted me. I had grabbed one of the towels they kept around for running the concession stands. It was one of the clean ones in a bright blue bag. I could feel his body begin to tense up, with him down on the couch and me behind him; my cock slapping on his ass. "'Simona,' he started to ask; maybe plead. I couldn't quite tell. I shushed him again, said 'Here, put this in your mouth' shoving the towel in his teeth' before grabbing his hips, lifting him up to doggy and pushing my cock against his asshole" Simona could feel Kyle getting harder as she told the story. His was breathing heavily, his body began to sweat. She was glad; she was afraid of telling Kyle this story. She had a feeling it would be alright, but wasn't sure. Now she knew she had found the right man to share this with, and so she continued. "I'm so glad my cock was still covered in our spit. He was so tense when I put the head of my dick against his asshole. I could hear him start to yell with the towel in his mouth. It was something like, 'no' or 'I can't' but I pulled the towel tighter with both hands, not letting it go. My cock kept pushing up against his ass, his body squirming. Eventually I had to let go of the towel, to reach back and probe for his hole with my erection. "The head of my cock started to find its way in and I could hear him wimpier. I eased it in a bit, and once I knew I was in there, I didn't hold back and just thrust it in. He cried out and screamed, but that only made me harder. I was so hard Kyle, and I just started fucking and fucking him. Eventually I grabbed the towel and pulled tighter on the gag in case someone heard us. He kept screaming through the towel and I pulled back on them like reins on a horse. I kept riding him and riding him. Eventually he bit down on the towel on his own and I started slapping his ass as I fucked him. "I had never been so hard as I had been right then, fucking his tight virgin ass." Kyle was rock hard now and Simona started to gently run her fingernails up and down his member in the water, teasing him. "What happened after that? Were you afraid he'd tell someone," Kyle asked? "I came in his ass. I came so hard I was dripping cum all over that couch. He looked afraid at first. I told him that he couldn't tell anyone, and that if he did no one would believe him; that he'd be a little bitch if he said he got fucked by a girl. "He seemed to understand .. and you know we still dated. We kept having sex too. Eventually we started using Vaseline which made things easier. I let him fuck me a few times. We'd cum in each other's mouths. Even though I had forced myself into him that first time, I knew he liked it. I made him like it." By now Simona's hand was gripping Kyle's hard cock, her own thick member poking into Kyle's ass. He couldn't take it any more. Kyle lifted himself up, turned to look at Simon and said, "turn around bitch!" Simon complied and she immediately felt Kyle's cock on her ass. He grabbed some lube from the side of the tub, quickly covered his cock, and plunged it very fast and very hard into Simona. She was a little surprised, and yelled out a loud sharp mix of a scream and a moan. She knew she should have been expecting it though, and Kyle didn't wait for her to be ready for it. He started thrusting hard and fast. He fucked her and made small waves collect on the side of the hot tub. Water splashed as the quick slapping sound of his fit thigh muscles against her plump ass echoed in the bathroom. Their shadows flickered against the wall. His hands clenched at her curly hair and pulled back her skull as he continued to fuck. Simona's cock was also hard and waved through the water. She moaned as Kyle eventually let go of hear hair and wrapped his hands around her body and reached around to stroke her long hard cock. She pulled away from Kyle and told him to turn around. He faced the far window and heard the bottle of lube squirt. He are more ready than Simona, and she wasted no time, slamming the entire length of her member deep into Kyle's ass in one hard thrust. He groaned deep and hard and it made Simona grow harder. They were use to each other's cocks from the frequent fucking. The quick entry when they were both horny made for an incredibly tight sensation. On future nights when they were violently horny after a mad night out in a bar, they would continue to fuck each other like this; with just a little lube and no warm up. It made for some incredibly intense fucking. Simona put the thrusts of her thick and plump body against Kyle in long strokes that gradually got faster and harder. The slapping of their bodies was loud, Kyle's cock was thick in Simona's hands as she reached around. She fucked and grew harder when Kyle moaned out, "rape me Simona. Rape me like you raped your boyfriend in high school!" This threw Simona into a hormone infused frenzy. She thrust faster and faster, grabbing Kyle by his bony hips, and threw the full weight of her cock into him. Her thrusts slowed but were much more forceful, each one like a sledgehammer whaling down one one of those "test your strength" machines at the country fair; each trust so hard it would rip the bell of the scale. Eventually Simona came hard in Kyle's ass. He could feel the cum enter his ass, and he quickly pulled away from her, turned around, and began to vigorously stroke her cock. He stroked insanely fast as she continued to squirt her thick load into the hot tub. Squirt after squirt of hot creamy cum made its way onto Kyle's face and eventually into his mouth. He refused to stop even as the cum began to slow and then sucked her cock vigorously and relentlessly. He milked every last drop of cum into his mouth while squeezing and fondling her balls with his hands. She eventually pushed him away, and he tried to suck her cock again, but she slapped him yelling, "Stop it you fucking bitch. God damn you faggot!" Kyle just sat back and smiled. His cock was still hard and he started to stroke it. Simona reached forward and started stroking his member. He stood and she sucked hard and stroked fast. She worked his shaft and balls with her hands while sucking deeply. He was so hard he could barely contain himself and was shooting his load into her throat before he knew it. Simona put his cock in her mouth as he began to cum, sucking him deep. His cock was so sensitive until he could no long stand and plunged ass first back into the tub. They laughed and Simona enjoyed the taste of his cum deep at the back of her mouth.
Credit: https://www.nifty.org/nifty/transgender/she-male/pans-servant/pans-servant-2 by Samathia
Kyla first met Leena at a philosophy meetup. She was the type of girl who's essence would flow out immediately into an entire conversation. She was very tall, standing just over six feet even in flats. Her hair was thick and black, her skin surprisingly pale since her family was from northern Africa. She loved to berate people for socialist views, and when she'd have one to many to drink, she'd start complaining about the Jews. She was the life of the party and would gather everyone for late night bar hoping; most weekends drinking to excess. Kyle once invited her out with a small group of his friends, and she tried to bring in random strangers she met while smoking in front of the bars along with their group. Some of Kyle's other friends were having nothing to do with that. They eventually left, with a drunken Leena wanting to go dancing, but too exhausted to walk up a very shallow hill; demanding a cab. It was going to be one of those nights. They were kicked out of the first bar, the bouncer coming to up Kyle saying, "I'm sorry, you and your girlfriend have to leave. I shouldn't have let her in. She's too drunk." "She's not my girlfriend." "Don't care, when she gets out of the bathroom, she's got to go." Kyle had to hold Leen up and drag her with him forcing her out with him. She started talking to a stranger handing her a water bottle. Before the bouncer even reached him Kyle had it out of her hand. It could have been just water, but you never know in those shady places. They ended up sitting on a bench in a park across the street from the strip. Kyle told her he was into her. Leena responded that he didn't even know her. "The last guy I dated, we didn't have sex for the first year," Leena said. "I mean, I've had sex. I like sex .. but," she trailed off. Kyle took Leena's hand in his own and looked into her eyes. "You're right," he started. "I don't know you, but I want to." Gazing into each others eyes, Leena leaned in toward him and the two of them kissed. Their months met, hands slowly wrapping around each others backs in that dimly lit bench next to a city park. Their kisses were light, gentle, teasing the tops of each other's lips. Leena slowly pulled away from Kyle and said, "I want to go dancing." "I probably can't get you in anywhere. Unless you can pretend to be sober." "I'm sober," Leena said, standing up and lumbering awkwardly. Kyle rose up quickly and grasped her around her waste, holding her steady as she repeated the words, "Sober. I'm Sober." "Well .. okay. Let's give this a shot." The two of them were able to get into the next club. Pushed together on a crowded dance floor, Leena stood up on a couch with some other women until a bouncer told everyone to get down. She took Kyle's hand at one point and placed it on her breast as they danced together. Her head was cradled down against his neck, as Kyle's hand reached down to fondle her ass. It was past two in the morning when they left the club. Leena kept saying she wanted pancakes with nachos and tacos. Kyle kept her babbling long enough to walk her back to his place. She insisted on taking a cab home, but after a few "I want to show you something first" and "I have tacos at my place," Kyla got her back to his apartment. He insisted Leena drink a entire glass of water as she was continuing to babble about food. Pizza rolls were put in a toaster and he told her they'd be out soon, as he guided her to his couch, put on some soft music and began to kiss her. Their bodies embraced, Kyle's hands reaching around her dress and finding their ways into her thick back hair. Leena's hands grasped his face. She'd mention wanting to go home, he'd tell her he'd call her a cab after they ate pizza rolls and her hands would slap his face and push him away. Complains were silenced with kisses and Kyle's firm hands and words of, "Just stay here tonight," and "nothing will happen" and "I will sleep on the couch." Leena continued to babble about wanting tacos, on pancakes in a cab, but she seemed to be pacified by pizza rolls, and a vodka tonic. They sat on the couch and ate. Kyle had no coffee table so their drinks sat on the floor, and of course Leena inevitably kicked hers over. Kyle didn't care, because by that moment he was already pushing Leena down against the couch, kissing her neck softly. His hand cupped her amazingly round breasts and Leena began kiss deeper and more passionately. Leena struggled a bit, and attempted to slap him on his face and push Kyle away, but eventually he was undoing her bra clasp with just one hand, the other still fondling her breasts. Leena was a mess between trying to push him away and also grabbing his hand and helping Kyle play with her tits the way she liked. Eventually Kyle was pulling her dress up and over her head. There were murmurs of "no," but Leena was really too drunk to put up an effective fight. Under it she wore black lace panties and a bra covering very large and perfectly round double D cup breasts. Her body was beautiful, under that cute stripped dress she had been wearing all night. She was a little thick, but mostly curvy, with wonderfully large and ample breasts below her cute face and thick black hair. She squirmed a bit as Kyle reached his hand under her panties, but began to settle and moan as he started to play with her pussy. It was already wet against his touch. One of Leena's hands reached up to run through Kyle's short blond hair while her other attempted to undo Kyle's belt. Kyle of course had to help, Leena's hands slapping at his as he unbuckled. Leena reached down into his pants. His cock was already hard as she began to grip it firmly through his boxers with her long slender fingers. The two of them continued to kiss, and fight and play-fight. Leena couldn't tell what she wanted, both pushing Kyle away yet accepting the way his nimble fingers pleasured her moist and wanton snatch. Kyle continued to work off his jeans and boxers, and eventually Leena even helped him removed his skin tight t-shirt. Her hands pressed up against this chest, with its solid and firm muscles. Kyle pressed his hard penis against Leena's panties, the last piece of clothing either of them was wearing. She struggled a bit once again, but Kyle pulled them off and down past her long legs. She kicked a bit but Kyle was able to take control and hold her down; moving back up to her upper body. "No, no, I can't," Leena was spurting out in drunken words. But those words only made Kyle harder. And even as one hand pushed against his chest, in a terribly week attempt to push Kyle away, the other was still stroking his cock and firmly grasping his balls. Leena shrieked a bit as Kyle penetrated her. His hard cock pushed into her pussy as he plunged his shaft almost half way in at once. Leena was wet, yet still tight. She could feel Kyle's girth. He was a solid seven inches long, but a little thin; only moderately girthy. His cock pushed deeper into Leena's wetness, each slow thrust taking him deeper as Leena's protests turned to whimpering moans. Her eyes started to tear up a bit as she started to gasp. Moans of tortured pleasured arose from her as Kyle started fucking her faster. Eventually Leena gave in, her legs rose up and wrapped around his back. Her hands began to play with Kyle's nipples, pinching and teasing at them, as Kyle fucking her harder. Her moans were short, terse, and gasping at first, but grew into full, long moans of pleasure. She could hear the slapping of their two bodies, his thick balls clapping against her pussy, and his firm hands grasping her thighs and using them to drill deeper into her body. Leena's hands spread out from him, her arms began to flail a bit as the fucking continued to intensify. Her body jolted as Kyle began to rub her clit with on of his hands, the other firmly on her ankle. Sweat beaded up on their bodies and eventually Leena began to convulse in orgasm between the movements of Kyle's hand and thrusting member. Her body shook and shuttered, but Kyle did not slow down. He began to thrust harder as her body convulsed and her moans screamed out in a way that would surely wake the neighbors. Leena was awash in pleasure, and she uttered the words, "too much" but was too drunk to make it stop. She kept squirming, her body twisting from side to side until Kyle had finally got his fill. "Turn around," he said to her, more as an indication of what he was going to do to her rather than an order he knew she wouldn't be able to follow. He grasped her legs and waist and flipped her tall and thick body over on the couch, pulling up on her hips to get her on her knees. The fight was mostly gone from Leena, but she still had trouble staying on her knees. Kyle helped by grasping her hips firmly as he quickly plunged his cock deep in her pussy. Her elbows on the couch pillow, Leena belted out a moan that was mixed with a cry. Tears even began to form in her eyes and her cries made Kyle even harder as he fucked Leena. Kyle firmly grabbed her thick black hair in his fist and pulled her head back as he fucked her. Her cries continued to ring out as he continued to pound her harder, until each thrust of his cock was fully buried in her pussy. His hands let go of her hair and grabbed onto her massive tits that had been bouncing freely under her body. He gripped them firmly, pulling and squeezing them between his hands as he bent over her body. Eventually Kyle couldn't take it any more. His cock was ready to explode, so he pushed Leena off, grabbed her wrists and forced her to a position on her knees on the floor. His grabbed her face firmly in one hand as he was stroking his cock vigorously with the other. Leena closed her eyes, winced, as tried to look away, but Kyle wouldn't have it. He grabbed her head by her hair, forced her face to point at his cock and said, "Open your mouth bitch! Open it! Open it!" Tears were running down Leena's face, but eventually her mouth opened, and Kyle thrust his cock into her mouth. He began to fuck her face and she squirmed. Her eyes opened to look at him and he kept skull fucking her, feeling the cum build up inside of him. His orgasm was strong, cum squiring back into Leena's throat. Leena gagged, but Kyle's hand against the back of her head wouldn't allow her to pull away. She chocked on each squirt as it throttle the back of her throat. Her eyes watered as she chocked on the loads of cum, much of it forcing its way down her throat, out the sides of her mouth and even up her nose. She gagged and choked and eventually Kyle started fucking her mouth again towards the end of his orgasm. His cum continued to squirt for what felt like nearly a minute, to the point where Leena would suffocate on his cock and drown in his cum. But eventually his orgasm subsided and he pulled away from Leena's now dripping mouth. He sat back down at the couch and gazed at the drunk naked girl on his floor with his semen dripping in a mix of spit from her mouth. Leena sat there on the floor, gazed down for a bit with exhaustion in her downtrodden eyes. Eventually she climbed up onto the couch, not looking at Kyle, until she was curled up next to him. He took Leena in his arms, began to kiss her gently on her forehead and face. Leena's face cringed, her brows wrinkled and she began to cry even as she cuddled up next to Kyle's body. He grabbed her thick ass and moved her legs over his lap and cuddled her firmly. They sat like that on the couch for a few minutes. For the first time all night, Leena had nothing to say. Kyle's hand gently made their way through her hair and softly down her face. Her tears subsidized. Her sniffles began to cease. Kyle began to become hard again in only a few minutes. Leena could feel his thick member pushing up against her legs. Kyle's gaze met hers with a sly smile as Leena began to shake her head from side to side. He gently shushed her as he moved her body to straddle him on the couch. She struggled a little, but eventually was on top of him. She could feel Kyle's hands firmly on her hips and gently lowering her onto his cock. She grabbed it and guided it to her pussy, and was glad he was gentle as he slowly lowered her onto him. She began to rise up and down on his cock and Kyle played gently with her clit. Her mascara was smeared on her face from the tears as her eyes met Kyle's. They began to kiss, hesitantly, gently, even a little awkwardly. Then she felt Kyle began to thrust. She was no longer moving slowly on his cock, but was receiving thick hard thrusts that got faster and faster. Leena's fingernails began running to Kyle's hair, his mouth was sucking on her large tits. She began to moan with pleasure, and her body began to shutter as she once again came to orgasm. She shook and trembled as Kyle continued to thrust deep and hard into her pussy. Wave after wave of intense orgasm filled Leena's body like she had never experience before, and she began to fuck back again Kyle. She slammed hard onto his cock, rising all the way to the top and pushing back down. Kyle lay back on the couch, his hands moving to her breasts to squeezing and play with them. Leena kept riding him hard through the end of her orgasm, and kept fucking him with long hard stroked. Their bodies continued to slap together until Kyle finally erupted into Leena. She continued to buck and ride him as he came in her pussy. She could feel all his cum, so much cum from a second orgasm. She pulled off of Kyla and went to the floor, blowing his cock as he continued to cum, taking it deep into her mouth. His body convulsed as she wouldn't let up with her deep and passionate blowjob, milking his balls dry. Eventually Kyle couldn't take it anymore and pulled away. As Leena's hands tried to reach for his cock, he yelled, "oh god, you fucking bitch" and he saw her smile as he slapped her hands away. She laughed when he slapped her hard against her face. She lay on the ground, looking at Kyle sitting on the couch. His body was rock hard, and cum still glistened on his cock as it slowly softened. Kyle would help her off the floor and take her to his bed where he wrapped around her and held her as she slept. Twice in the night he would wake up and begin to fuck her, having his way with her and treating her has his sex toy. The second time was earlier in the morning, and she was sobering up a bit and struggling a bit; which only made Kyle harder and the fucking more intense. They awoke to the sun coming over through the window shades. Leena's eyes felt dry. "Did you enjoy last night?" Kyle asked her as she got up. Leena didn't turn to look at him. Her face betrayed a mix of sorrow and being hung over. She gently said, "Yes," and softly added moments later, "I did." She reached down to his cock, now rock hard again, without looking at him. She pulled and yanked at it and could hear Kyle moan. She continued to jerk and stroke it, faster and faster, not easing up, and within only two minutes it was throbbing in her hand as Kyle climaxed. She kept jerking him until his body stopped shuttering. Then she wiped the cum on her hand on his bed sheet. As she rose he grabbed her wrist saying, "Where are you going?" "I have to work today. I need to get home and shower," Leena said and pulled away. She went to the next room and quickly put on all her clothing that lay next to the couch. She made her way back past the bed room and Kyle asked, "Will I see you again?" Leena stopped walking towards the apartment door. She hesitated, but then turned to look at him. Her face was totally disheveled, her heeled shoes in her hand. Holding back the tears, she softly said the words, "Yes" and then turned back to the door she added gently, "Yes, I'd like that." Leena then walked to the door, opened it and left the apartment. She held her shoes in her hand, wiped as much of the makeup as she could off of her face using napkins she had in her purse. She was glad there was no one in the elevator as she carried her shoes in her hand. Outside his building, she was glad she was able to quickly call a taxi. She entered the cab and asked the driver to take her home. In her own bathroom in her apartment, she looked deep into the mirror. At first she started to cry, but then she fell to the floor and sobbed. Eventually she reached under the sink and found her vibrator. She turned it on and put it against her pussy. She began to insert it and push it in and out, harder and faster than she normally did when playing with herself, thinking about Kyle's cock and the way he made her gag on it in her mouth, bringing herself to orgasm once again, before passing out on the bathroom floor.