A Night With A Craigslist Transsexual

Credit https://www.gaydemon.com/ markerss

I had always fantasized about being with a transsexual, but never had the guts to pursue it. I had responded to several Craigslist ads to meet trannys, but after only few messages, I usually became overly nervous and I never went through with it. However, there was one Craigslist ad that simply said, “Satisfaction Guaranteed.” The photos she posted were great and she even had her own web site. She looked to have a pretty face, a nice body, and great boobs, and so, I decided to try to contact her. Just like all the other, I became nervous after hitting the send button, but when she finally responded back, she seemed to be personable in her message back.

In my email back, I tried to start with small talk but she was not into any small talk, but instead she referred me to her website where she had contact information. I was attracted to her and when I went to her website, she had a photo gallery, a bio page, and even a page with reviews.

Her name was Victoria, she was listed as 5’6″ tall and it said she weighed about 130 pounds. She looked to be Latina, with long wavy brown hair, and a great shape. Her website also listed her rates and she ensured that there would be no time constraints, because she wanted to make sure customers where fully satisfied. I continued to want to meet her, fantasizing about being with her, and looking at her photos often.

I tried to contact her again through email to find out where she lived and what her schedule was like and in her reply, she told me where she live, it happened to be very close to where I worked, and she gave me a phone number to call when I was ready to meet. I was nervous about meeting her, but I wanted to do it and I felt if I was ever going to do it, now would be the time. I finally got up the nerve one afternoon to telephone her, but I did not know what to expect. The phone rang and rang and finally her answering machine picked up and I had to leave a message. I was somewhat disappointed, but in a way relieved. However, soon my phone was ringing; she had called me back and when I answered she introduced herself and we talk for a short while. I explained that I had never done this before and she tried to reassure me that she would be patient and she guaranteed I would enjoy it. She finished by again suggesting that I call when I am ready to meet and I said, ‘ Okay,” and she immediately told me, “Hope to see you soon.”

When we hung up, I was ready to meet her and I considered what would be a good day and a time to get together. I decided to try to schedule something

for that Friday afternoon, right after work. It would be easy to head over there after work and it would be the weekend. The next day when I called to set up something, I again had to leave a message, in which she returned my call almost immediately. I told her who I was and Victoria said, “Oh yea, I remember, you’re the one that had never done this, right.” I told her, yea and I express when I wanted to come by. She paused and then said, “I think that’ll work, sure.” She then asked if I knew how much the donation was and I replied, “Oh yea,” and she followed by telling me the address, and explained it was an apartment building and she told me where I should park, gave me the apartment number, and told me she would have to buzz me in. Victoria also asked me to call when I was on my way. I told her okay and expressed my excitement to meet her. She paused briefly and replied, “Me too, see you Friday, be sure to call me.” I said, “Okay,” and we hung up. When Friday came around, I was nervous but excited too, and when my day was over, I called her as I headed out. I again had to leave a message, but she called right back, and when I answered, I told her I was on my way. She said, “Okay, I’ll be here.” It did not take long before I was at her apartment building, parking my car. As she buzzed me into the building, I took a deep breath and headed up to her apartment. I knocked on the door and Victoria answered. She was dressed in a low cut, lace negligee and said hi about the same time as I did. We smiled at one another and she asked me in. Victoria closed the door behind and told me to go ahead and have a seat. I went over to the couch, sat down and waited for her. It was hard to believe but she was more attractive than her photos. She sat next to me and asked if I had the donation. I replied yes, and as I started to take out the envelope with the cash, she started to stand up. Victoria told me to go ahead and leave it on the coffee table and told me to follow her into the bedroom. I quickly threw the envelope on the table and followed her. She held the door waiting for me and then closed the door behind us. She was so hot; sexy in her negligee and as she approached me, she asked if I liked her and told me not to be nervous. She kissed me on the cheek a couple of times and then moved my head kissing me on the lips, eventually French kissing and feeling on each other. Victoria now started to take off my shirt and gradually moved us over to the bed. After taking off my shirt, she gently pinched and sucked my nipples. Victoria then had me sit down on the edge of the bed and she backed away slightly and did a strip tease, taking off her negligee and feeling on her boobs. She had great boobs and they looked so firm with nice little nipples. Her body was tight and she did have a great ass too. She kept her panties on but her cock was bulging, wanting to get out. Victoria now moved closer to me and pushing me back onto the bed, she told me to lie back. She started to rub my cock through my jeans and then proceed to undo my jeans, pulling them off. As she did, my boxer slid down and before I could grab them, Victoria grabbed them too, pulling them both off and casting my pants and boxers aside. My cock was not hard, so she quickly started by fondling it and eventually she put a condom on me and tried sucking it. It felt good as she sucked my cock, and I slowly got hard in her mouth. Victoria then stopped and climbed up on the bed so she was right next to my face. She pulled her panties to the side letting her cock hang right in my face. As she inched closer, she took hold of it trying to entice me to suck it and eventually asking me if I wanted to suck it. I did, but I was nervous to try it, but I paused and she continued to put her cock in my face, even touching it to my lips. She soon realized it was too soon, and stopped, moving down to suck my cock again. It felt great, but after only a little bit, she stopped again and looking up at me, she asked what I wanted to do. I again paused to think and as I did, she moved back up, straddling my chest, wanting me to suck her cock. Victoria’s cock was big and as she put a condom on her cock, she again pushed her cock in my face. I finally took it in my mouth and Victoria gradually leaned forward moving her cock in and out of my mouth. I could feel it growing harder and harder in my mouth, and I wanted to taste her cum and I think she wanted to cum too. She had me stop, and taking her cock out of my mouth, she told how good it felt. I nodded my head and she climbed off me. She then said she wanted to feel me in her. I again nodded my head and told her I wanted her to fuck me too. Victoria smiled and had me stand up. As I did, she climbed on the bed, got on all fours in the middle of the bed, and said, “Come on.” As I positioned myself behind her, I wanted to be in her. Her butt hole looked so nice and she reached around, handing me some KY, and told me to put some on my cock and on her ass too. As I applied some to her ass, she spread her ass cheeks and fingered her own ass. Victoria moaned and said, “Oh yea, put it in me.” I inched closer and she spread her legs apart allowing me to get closer. Her ass was so nice and as I started to push my cock in her ass, she pushed back letting my cock slowly slip in. I was all the way in her and as I started to fuck her, she said, “Oh yea, that feels so good. I want you to cum in me.” We moved back and forth and my cock pumped her ass. I was soon slapping against her ass, wanting to cum in her. I was close to cumming and trying to hold her close, I told her to stop. My cock started to throb inside her and she could feel it too. Victoria then tried to move back and forth again. We were both out of breath, and as I leaned forward, I kissed her on the back and reached around feeling on her boobs. I then gradually took my cock out of her ass, and as I did, she took hold of my cock and took off the condom, letting it drop to the floor. She rolled onto her back and pulled me down to kiss me. As we kissed, she remarked how nice it felt and asked what I thought. I told her it was great, but before I could finish she climbed off the bed and motioning, told me to get on all fours, and told me that she wanted to be in me now. I did not know what to do, but I could see her pushing her condom on her better and then helped to position me in the middle of the bed. She told me to put my head down on the pillow as she move around behind me, and got on the bed right between my legs. I did want to feel her in me and as she inched closer, she told me to relax. I nodded and I could feel her smear KY on my hole, and she slowly pushed her finger me. She gradually moved her finger in and out, to help me relax and even tried to get two fingers in me. It felt good and as she withdrew her fingers. She repositioned herself behind me and tried to put her cock in me. As she tried to push her cock in me, she remarked, “You are so tight.” She moved even closer, and I could feel her starting to push her cock in me. It hurt and when I tried to pull away. she asked what was wrong. I told her it hurt. She replied, ok and told me to try to relax. I nodded my head and she tried again, but this time as she pushed her cock in me, she simply started to wiggle her cock as she slowly pushed her cock in me. It still hurt but I wanted her in me, so I tried to relax. As Victoria continued to move her cock in and out of me the hurting subsided and soon she was deep inside me. She now started to fuck me, it continued to hurt a little, but I wanted to feel her cum in me. Her cock felt so big in me, especially when she pushed deep in me. When she did thrust deep in, it hurt causing me to rise up from time to time. She continued to have me relax and eventually I could her she was breathing hard. Suddenly, she pushed deep in me and as I rose up again she said, “I’m cumming.” She held me tight and I could feel her cock jerking inside me as she slowly started to fuck me again. I knew she had cum in me. She then leaned forward, forcing me flat on my stomach. Out of breath Victoria whispered, “That was great.” She then slowly withdrew her cock from my ass and I watched her take the condom off. She showed me how much cum there was and kissed me. She dropped it on the floor and gently rubbed my ass. It did feel good, and I wanted to do it again, but we eventually got out of bed, and got dressed. As I got dressed, she put on a shear robe, waiting for me to leave. As I left, we kissed at the door and Victoria said, “Anytime you want to play, let me know.” We kissed again and I felt on her tits one last time. It was all I had hoped for but at the same time, I have not had the opportunity to be with her again. I have thought about trying it again, but again have not had the chance.

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