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?