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
"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
"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
"Can I put the gown over me again?"
"Sure, son. Am I still supposed to call you son? Or are you my
"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
"Does anything shoot out of it yet? Sperm?" He looked
uncomfortable asking that, like the next question was asking me to prove
"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
"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
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
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
"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.
"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
"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
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
"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
"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
"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
"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
"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
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
"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
"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
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?