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It was still dark when I awoke, lying on my side in the bed. I had a morning hard-on, and there was an arm over me from behind, with a hand gently resting on my titty. Eyes still shut, I rolled back over and reached down. A dick. A really big one. Colin. I heard him murmur softly, “Michaela.”
My head started to clear, and the events of the night before came into focus. After a long round of four-way snuggling, Colin and I had wanted to sleep, and his wife, Allison, and my husband, Bobby, wanted to fuck, so they went off to the guest room. I pressed my face into Colin’s hairy chest and he held me, pushing his big erection against my smaller one, and that’s the last thing I remembered until morning.
Stroking Colin’s penis brought him around, and he bent down to suckle on my nipples. “I’m so horny, Kayla,” he murmured. “I want you. I dreamed of fucking you all night long. In my dreams, you had a vagina.”
Rubbing his cock a bit harder now, I whispered, “You know I don’t have a pussy, Colin. But whatever I have is yours to take.” He reached down between my legs, gave my nuts a gentle squeeze and began sliding my uncut foreskin up and down over the head of my very hard penis. Eventually, he pulled the covers down, moved down between my legs, and started sucking my organ like the lover that he is.
I should probably mention a few things.
I was born biologically male, but as far back as I can remember, I always felt like a girl. As a child, I gravitated more toward the girls, their toys and their games, than to the boys. It wasn’t always easy, and I caught a lot of flack from the other boys. Having gone away to college at eighteen, I would occasionally encounter gay boys in the dorms here and there, and we would discreetly find ways to go off in private, hold hands, kiss a bit, and eventually pull down our pants and explore. In between, I masturbated. A lot. Virtually every day, sometimes more than once. I knew this wasn’t normal. I must, I thought, be some kind of a pervert. Surely all the other guys weren’t jacking off this much. They spoke of it in such insulting terms. But, I found, at a minimum, I needed to do it every night just to fall asleep, and besides, it felt so good.
Even to this day, I play with myself often. Typically when waking up in the morning, with my usual erection, but not so much to make myself come as just to clear my head and come around. I especially love it lying next to Bobby or Colin, or both of them, with them pulling their penis at the same time. In particular, Colin playing with that huge cock is something to see. He can hold it with both fists at once, like a baseball bat, and still have plenty of head sticking out. This routine usually ends with my dick in a mouth, and someone’s dick in mine, but again, less to have orgasms then and there as to leave us filled for the day with dirty thoughts so that the nights can be memorable.
For a long time, I thought I was gay, but the idea of femininity kept intruding on my persona. The other gay college boys were still, well, boys, just boys who liked cock instead of pussy. Some of them were quite masculine in appearance and behavior, although others were more femme. But I fantasized, imagined, dreamed of myself becoming a woman, wearing women’s clothes, openly dating straight men, doing all the things that women do, in bed as well as out.
When I finally learned about transsexuality, and the things that could be done, medically and surgically, to transition from a man to a woman, I was enthralled. This is what I wanted. What I had been drawn toward my entire life. My parents were sympathetic, but they insisted I not take any irrevocable steps until I was through with school. I got through college and a master’s program in M.E as a male, albeit an effeminate one with androgynous clothing and longish, wavy, styled hair.
After graduation, I was ready for the transition. My parents were on board. I told everyone else that I was taking a year off to travel, and I started meeting with psychologists, doctors and surgeons. After all the evaluations and consultations, I decided on my plan. I would begin the courses of hormones needed to alter my body and my mind, and I would have surgery to build real breasts with larger nipples. I would not, however, have the gender reassignment surgery. I was not going to give up my penis in order to acquire an artificial vagina and clitoris. As they say, it will never be as good as God made it, and the truth is, I liked my uncircumcised penis. I liked it becoming hard. I liked playing with my foreskin, something that I knew a lot of the guys didn’t have, pulling it up and down over my cockhead. I loved the way it felt when I would come, spurting semen all over myself. And I definitely loved rubbing it against another man’s body and hard dick, having it sucked by him and sliding it into his bottom, unloading my come into his hot openings. I didn’t need a vagina. I was well able to satisfy the men with my own gerze escort mouth and bottom, and I had been around long enough to know that there were, in fact, men out there, available men, who loved women and yet were attracted sexually to a phallus. I would just have to find them.
While the transition was going on, I grew my hair long, experimented with makeup until I was happy with the results, and learned to shop for women’s clothes. Mom was a great help, and took me on many out of town shopping trips and visits to salons for hair styling and beauty education. I legally changed my name from Michael to Michaela. I had to learn body shaving, not just leg and armpit hair, but also the hair that still grew on my butt despite the hormones. Facial and chest hair, what little I had, all seemed to go away with the meds. I also decided to shave my scrotum smooth, but to leave my thick pubic hair intact except for some feminine trimming and shaping. I loved the look, but it was a cumbersome routine every day, and when winter came and I was covered up with warm clothes all the time, I stopped and just let the hair grow in everywhere. It made me feel like a natural girl, and I loved it, but with spring, warmer weather and skimpier clothes returning, I resumed my shaving regimen once again.
After nearly a year, with the surgery behind me and the lessons in beauty and fashion well-learned, I was, I felt, completely a woman, and a darned attractive one at that. I got stares from men on the street, they’d ask for my number and hit me up with crazy pickup lines. I was ready to dive into the deep end.
I started looking for an engineering position, and found one a few hundred miles away from home. Excellent, I thought. I could make a fresh start, where nobody knew me or was likely to learn of my history. I rented an apartment in an old building in a hip neighborhood, moved in and went to work.
Over the next few years, I took jobs at a couple of different places. I liked the companies well enough, but I quickly learned that you often have to move out to move up, and five years out of school, I took a new job with a consumer products company.
Working at the company was fine. I was doing product design for a wide range of items, working with a team of engineers and marketing types. One of the girls in marketing, Wendy, was just about my age, and very friendly. Wendy was gorgeous, blonde, curvy, outgoing and exuberant, and we quickly became close girlfriends. We’d hang out on Sundays and talk about our dates and our sex lives. Well, Wendy did, anyway. I wasn’t dating much and my sex life was pretty thin, but I made it seem like I was just going through a dry spell. I never told Wendy about my trans background. I just wanted to be another regular girl; it’s why I had moved away from home after my transition.
After we’d been hanging out for a few weeks, Wendy told me about a guy friend of hers who wasn’t seeing anybody, and asked if I was interested in meeting him. She said she’d known him a long time, he was in marketing as well, and he was handsome and nice. I agreed to meet him. I wasn’t expecting much, he might be really nice, but as soon as intimacy became an issue, he would probably run for the hills upon discovering my true nature. Most of the men I met did, and of the ones who didn’t, most of them were just novelty seekers or filling out their bucket lists. Nevertheless, early on a Saturday evening, I accompanied Wendy to a local bar, where she introduced me to Robert.
I don’t remember a lot of the details, but from the moment I saw him, Robert looked perfect. He said the right things, he did the right things, and I found myself wanting to know more. Robert asked about my work, my interests. We talked about movies. We found we both loved real cinema, not the comic book action flicks so much, or the endless stream of remakes and sequels coming out of Hollywood. We talked about music, about books, about where our lives were heading. After an hour or so, it was clear we were both fascinated. Wendy excused herself and left us alone, offering some pretext or other for having to run out. Robert asked if I would like to join him for dinner, and to continue our conversation, and after he paid the tab, we walked down the street to a casual steakhouse.
Dinner was terrific, and we continued talking for hours, working through a couple of bottles of wine. At no time did I feel pressured, or that Robert was trying to hustle me into the sack. I think we could have sat there, drinking wine and talking all night long. But eventually it got late, and Robert offered to walk me back to my car, parked a couple of blocks away. Arriving there, we said goodnight and he gave me a sweet kiss, not too long and not too quick, and I drove off. In the car, I made up my mind that, before he could ever ask me out, I would reveal myself entirely to him. This all just seemed too good, and I wasn’t going to blow it by getting giresun escort him into bed and then springing a penis on him by surprise. If I came clean up front, it might scare him off, but at least I’d know right away that we weren’t meant to be. If he didn’t scare, then there was a chance that we might be real, and I wouldn’t have my secret hanging over my head as we began dating.
Arriving home, I crawled into bed and masturbated, thinking about the things Robert and I might do together. Afterward, I lay awake still, planning the way I could tell him the truth about me. At last, I realized that telling would not be enough. I would have to show him.
A couple of days later, I screwed up my courage and dialed Robert’s number. I asked him to come over and I gave him my address. I was committed now, there was nothing else to do but go through with it. I took a quick shot of whiskey, and when Robert arrived, I gave him a drink and sat him down in my easy chair, as, with no explanation, I started to take my clothes off. He stared, not knowing what was going on, as I bared my breasts, then I turned and slipped off my slacks and panties, giving him a full view of my naked bottom. Finally, I flashed him a big smile and turned to him, revealing my penis all at once, soft and hanging down. Predictably, Robert was shocked. But he didn’t run. I spoke to him, telling him about who I was, what I was, and how I was beginning to feel about him. He looked at me, all over. My body, my face and, yes, my cock, as well. He devoured me in that look. He smiled a warm smile, took my penis in his hand and told me how he was feeling about me, too. He wasn’t lecherous, he wasn’t slimy. He might have been talking to any girl who had captured his attention. He kissed me gently, and a huge wave of relief passed through me. Eventually, I put my clothes back on and we planned a real date for the weekend.
Dating quickly led to intimacy. We were both eager for it. We used our hands, learning about each other’s body, and our mouths, too, making love to each other’s hard member, receiving the love and swallowing it. We fell deeply for each other, and Robert came to realize that it was the love that mattered, not what kind of genitalia I had between my legs. After a long time, I offered my bottom to him, which he took tenderly and lovingly and, after a longer time still, he offered his to me. We were now as complete as a couple could be.
Then I got sloppy.
Relaxing at Wendy’s place one Sunday, I became careless and she discovered my secret, feeling my hard cock inside my baggy sweatpants. Wendy freaked out, called me names, and I got up and left. She ran over to Robert’s apartment and started jabbering to him about how I was a man, how I had a dick, and how she didn’t know when she introduced us, wouldn’t have introduced us had she known, and demanded to know if Robert was sleeping with a man. Robert calmed her down, told her all about me, about us. He made it very clear to Wendy that I was a woman, a real woman, not a make-believe woman, not an artificial woman, and certainly not a man. When I arrived at Robert’s a bit later, Wendy asked me questions and I did my best to answer them. We got past the harsh words, and along the way, she got it into her head that, because I had a penis, I should somehow still be attracted to women, should still want to have sex with them. After a lot of probing, I finally admitted to some wondering, something I had never even acknowledged to myself, and Wendy offered herself to help me satisfy my curiosity. Robert acquiesced after some discussion, and I proceeded to fuck Wendy, my first time ever with a woman. She sucked my dick, then had me lick her pussy, giving me directions about what felt good and what didn’t.
Wendy’s pussy was incredible. It was shaved totally smooth, and amazingly wet. She squirted in my face as I licked her, and then told me to climb up and stick it in. I loved the feeling as my cock slid into Wendy’s slippery, hot vagina. I’d fucked men’s asses many times, and this was similar, but much more, well, feminine. I lost myself in the feelings as we humped and kissed and moaned together, until eventually we came in an explosive simultaneous orgasm.
It was amazing. It blew my mind. It wasn’t better than sex with Robert – nothing was better than that – but the feelings and emotions were overwhelming nevertheless. With Robert watching the whole thing, I suggested afterward that maybe he and Wendy should take a turn. Wendy agreed, and as I got up, Robert climbed on top of her and crazily fucked her to about four or five orgasms in quick succession, after which she passed out. I was stunned. I’d heard of multiple orgasms in women, but of course had never seen them, and, physiologically, I am unable to experience them myself. When Wendy came back around, we all talked about what had happened and what it meant, and then Wendy suggested that maybe we should try an ongoing girne escort three way arrangement, with pussy for both Robert and me to fuck, two penises for Wendy’s pleasure, and the love we apparently felt for each other all the way around.
And so, we began our triad. It was amazingly sensual, and added a dimension to Robert’s and my sex life that none of us had anticipated. Wendy, of course, was also dating men, and eventually met Colin. As best I understand, they knew immediately that they were made for each other, much like Robert and I had. Shortly after meeting Colin, Wendy put the triad on hold, feeling it wasn’t fair to him to be sleeping with us at the same time. When it became clear that they were serious, and obviously together for the long haul, we started talking about bringing Colin into the group, changing our threesome to a foursome. Of course, we had all already met as friends, and when Wendy told Colin about the group, he was all for it. Of course, it still fell to me to tell him about my special circumstance.
I invited him over one Saturday afternoon, and basically went through the same strip routine I had with Robert. In some ways, it was easier. I wasn’t risking getting my heart broken, as I had been with Robert. And Colin understood going in that penis play was expected to be part of the arrangement, although I don’t think he had admitted to himself yet that he would likely wind up offering his bottom to be penetrated. In any event, he was anticipating me having a vagina, not a penis, and was visibly shaken when I revealed the truth. We talked, as I had done with Robert, and Colin came to realize that making love with me would be less of an adjustment than having sex with Robert. In fact, he adapted to me fairly quickly, as we sucked each other’s cock and fucked each other’s bottom, but he and Robert took some time before thoroughly learning to enjoy each other’s bodies.
We all became the closest of friends, as well as lovers and family. Weddings happened, first Robert’s and mine, and then Wendy’s and Colin’s. Wendy became pregnant with a son (by Colin, of course, we were all careful) and a year later with a daughter. We were all thrilled with the babies, and with watching them grow. We became Aunt Kayla and Uncle Bobby, and even I began calling Robert “Bobby,” as everyone else already did.
The kids grew and, with family pressures on Wendy and Colin mounting, our foursome activity retreated to an occasional romp or out-of-town long weekend, but we all remained family. Bobby and I discussed adopting kids, but finally decided against it. Wendy and Colin’s kids, Jared and Joanna, became teenagers, with everything that implies, and eventually went off to college in different towns. Finding themselves essentially empty nesters, Wendy and Colin unexpectedly began spending more time with us, in and out of bed. The sex was warmer and more intimate than it had ever been before, reflecting years and years of a loving relationship going beyond eroticism.
And then tragedy struck.
I got a phone call one afternoon. Joanna was frantic. “Aunt Kayla, you and Uncle Bobby have to come to the hospital, right away! Mom and Dad have been in an accident!”
When we got there, Jared and Joanna were in a state. There had been a car crash, a bad one. Both their parents had been taken back in the ER, and nobody was telling them anything. We waited for hours, trying to get information out of the nurses, with little success. Eventually, a doctor came out to talk to the kids. They insisted that we be included in the conversation. It was bad. Wendy had been crushed in the car, and had lost a lot of blood. Despite their efforts, the trauma team had been unable to save her. Colin was better off, having suffered a broken leg and a head injury, but was still unconscious.
We waited around until Colin woke up, and crowded around, holding him as we broke the bad news. He took it hard, crying for his kids, who were in tears also. After a while, we got everyone calmed down, and helped Jared and Joanna make calls to grandparents, aunts and uncles. The next day, more lucid, Colin started thinking about burial arrangements, and we helped him call a funeral home. After a couple of days, the hospital released him, and everyone came back to our house, where we took care of Colin and the kids with meals, beds and assistance until everything calmed down. There would be family coming into town, and there was a lot to do.
The next few weeks were a blur. There was a funeral, with lots of relatives around, keeping the family from being alone. We stayed late at Colin’s house in the evenings, after everyone had gone back to their hotel rooms, being there for Colin and the kids. Colin, in particular, was off the rails. He kept saying how he wished he had passed with Wendy, and asking how was he going to live without her? Jared and Joanna kept telling him how they needed him, too, now that their mother was gone. Eventually, we’d get the kids to retire to their rooms for the night, and we’d sit with Colin, snuggling and telling him how everything would be all right, until, in the late hours and after a few stiff drinks, we’d help him to bed and drive ourselves home, only to start all over again the next day.
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