Credit: https://www.nifty.org/nifty/transgender/she-male/i-cant-believe-it/i-cant-believe-it-1

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/house-of-shemales

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.

Credit: https://www.nifty.org/nifty/transgender/she-male/my-boyfriend-bill

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
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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.