We usually think of sex as having only two options. In fact, at least in my case, there have been three. The first case is sex as a man. That assumes I ever was a man, but that’s another topic for another story. I’m going to set this story’s beginning as sex when I was equipped as a man and perceived by my partner as a man.
The first time I had sex under this description I was seventeen. I was in my new girlfriend’s childhood bedroom. Her mother was at work and she had invited me over. She was much more sexually experienced than I was. She was known in school as exotic and wise beyond her years. She normally dated much older guys, so I was constantly trying to understand why she had chosen me, a spindly blonde surfer boy who sat next to her in Art class. She was every young man’s fantasy. Long sun-kissed brown hair to the middle of her back. Dark, large, almond-shaped eyes, olive skin, a stunning smile, and a figure that was all beautiful feminine curves. She could literally have any guy in school and for some unknown reason, she chose me. She asked me if I was going to a certain party on Saturday and I said, “yes.” She asked me for a ride, and the rest was what led me to this point sitting on her bed in her bedroom. I still couldn’t quite believe it.
She gently guided me that afternoon and I was all nerves. I already knew that I was “different,” and wasn’t sure I would be able to perform with a woman. My entire sexual experience to that point had been primarily with myself and always involved fantasizing about being female. Often wearing something feminine like panties, bra, or slip I’d stolen from my mother or sister. Always by myself and always when I was alone. It was a secret world I hadn’t shared with anyone. Now I was confronted with a beautiful 17-year-old woman with the most gorgeous feminine body I could imagine. She was everything I wanted to be. However, that wasn’t what my body had learned to react to, and very little happened. She seemed to understand, and gently stroked me and kissed me until I began to respond. I managed to complete the act, but only barely. Over the following two years we dated, I found more immediate excitement in our encounters and discovered the pleasures of “being male.” I eventually shared shared my feminine side with her, and then everything changed. My sharing allowed her to share also. Her secret was that she didn’t care for sex at all. We tried to live like two platonic girlfriends. We went shopping for clothes and played with makeup did our nails and hair but eventually I had to admit that I liked sex and missed it. We parted with lots of tears but lots of love and understanding that we both needed something different.
I was still young and managed to get accepted to Art School. I can’t say I was ever a promiscuous person, but lovers found me. I was an attractive young man, and women could see I was shy. As a result, I usually found myself with a more assertive woman. Some wanted me to be more aggressive while others were good with being the assertive one. Eventually I thought I found my “one” and married. She held joy athleticism and laughter for me and our love making was like another playful sport. Unfortunately my female side wouldn’t stay buried and as it emerged my wife responded with disgust. She didn’t want a woman as a partner so she began an affair with a wealthy older man and we had an explosive and psychologically devastating end. I felt like a piece of land that had just been fire bombed. Everything burned to the ground, left black and smoking. I also found myself single again and back in the sexual arena. I resolved to make changes so this could never happen again. I had been left and thoroughly shamed for who I was. I had to at least attempt to explore this feminine side that was causing so much damage to myself and my partners.
This is when I began to experiment with men, but only when dressed as a woman. I knew deep down I wanted to transition, but at this point in my life that goal was impossible. There was no internet yet and the only information about transitioning was from other girls I met at Trans clubs found through word of mouth. The men who chose me during this time came to these clubs specifically to meet girls that weren’t “all” woman.
I’m not sure how to categorize these relationships except that it was again a time of learning. Learning to enjoy a man’s strong hands on me. His rough face and his assertiveness. I found I enjoyed it. I used to love planning my outings during this time. Shopping for just the right dress and heels, jewelry and makeup. I would bathe and shave and put on some sensual music at home as I got ready. This took some effort, because I had a pretty significant beard and body hair during this time. But it was all part of my mental and physical transformation. I felt some kinship with biological women I had dated in this process of “getting ready” and began to understand that this could be foreplay. Feeling sexy was as important as sex itself. Perhaps more so. I always made sure I wore exotic lingerie and tall heels. I wasn’t going to waste these evenings on half measures. By the time I was finally ready to step outside the house I was usually feeling pretty hot. I was lean, tanned and youthful, with long sexy legs. I hoped someone would notice me at the Trans bar which was my destination. And they did. I would sit at the bar or take a spin or two on the dance floor, but eventually a man would approach me and ask if he could buy me a drink. I learned the bar courtship dance and my female role in it. I found it interesting that as a man I had never approached a woman the way these men approached me. I really enjoyed the new power I seemed to have.
I learned to know the signs of my new power. I could see a man circle in as I sat enjoying a drink or chat with a girlfriend next to me at the bar. If they were brave enough they would ask to sit down at the seat I had made sure to reserve by placing my purse there. These might be men who were confident and had visited a place like this before, or it might be a timid man who battled his inner desires to be with someone like me. Both found their way here as I had. Through some inner need that drove them to be themselves. “How are you tonight?” Or, “you look nice.” A number of the same phrases any woman hears at any bar were directed at me to initiate conversation. They bought me drinks and promised me things if only I would give them want they wanted. But I knew better. Only once did a man get past my guard.
He was so handsome. All my girlfriends saw him walk in even as I did. Hunky, dark, tall, well dressed with a rakish smile. He never asked to sit next to me but sat down with confidence as if he knew I couldn’t say no. I could smell him and feel his physical presence as if he had already touched me. I was no longer in charge. My power already gone. Although I briefly felt like a princess, our encounter was short lived and only once. I learned that I wasn’t so much special as new and unknown to him. Afterwards, I noticed knowing smirks among some of the other women at the club. I was literally nothing more than the flavor of the night. A tough lesson but one well learned. I was more careful about such men afterwards.
I learned it was a beautiful heart that I sought and that was hard to find in these bars. Most men’s motivation for going into a Trans friendly club weren’t to connect so deeply. I met married men lying to their wives and “straight” men acting out fantasies, but very few who cared more for my heart than for the exotic difference between my legs. I began to care less for the empty flattery and more for what a saw in someone’s eyes. That’s how I fell in love with my second wife.
She was a butch lesbian or an unacknowledged Trans man. She was a powerful force. Her heart was vast and fathomless. Her emerald eyes called to me like a cool forest stream after walking on a hot dusty road. Our connection was immediate and knocked me backwards. There was no guile or deceit in her but a strength and persistent desire that seemed like a slow but relentlessly moving tectonic plate. I fell backwards and she caught me and stood firmly by my side as I socially transitioned.
As a transbian my parts still fit together with hers like puzzle pieces, but our dynamic was still Yin and Yang. She was completely dominant but gentle at the same time. She was an exquisite lover, and had a touch and physical awareness I found almost hyper natural. Our love making like a perfect shining dew drop sliding on an impossibly thin silvery thread of spider silk towards a center that finally snapped exploding with a rain of countless sparkling beads. My orgasms had changed noticeably due to hormone therapy. Finely woven and delicate rather than so roughly hewn as they had been prior. The waves were larger and longer but not so steep and abrupt. Deep but perfectly defined ocean swells rather than messy stormy rough waves jumping up and crashing hard on a rocky beach. I wished I could stay there forever rolling across that magical sea, but my partner could not. Her intensity was her undoing and substance abuse slowly took away my greatest joy day by day. She drifted further and further away from me until she disappeared beyond the horizon altogether. I finally found myself simply trying to stay afloat.
I felt alone and homeless as a vulnerable Trans woman in a world that seemed suddenly more hostile. My physical difference felt like a gun held to my temple. Men and women wanted me, but not when they knew I held a different surprise for them. Society and the government seemed to be turning against me too. I decided to align my genitals with my exterior appearance. I was hoping to physically transition and “shoot the moon” by collecting all the unwanted cards in one place. I was going to make myself an attractive woman with a vagina and date a successful cis man. I would do what every attractive middle-aged woman attempts. To make my next lover one who could support me. If a woman has that choice, why wouldn’t she? My first ex had done it. Maybe I could now too. I scheduled my surgery and rolled the dice again.
I won’t get into the challenge of arriving at my surgical date or the months of recovery, but suffice to say each was it’s own very significant journey. But I did eventually arrive at my planned destination where the parts between my legs matched what the rest of me felt like. A woman. To be clear, there’s a major difference between what I possess and what a Cis-woman has. Superficially they are quite similar, but the parts are in no way identical. My vagina was constructed from my penis and scrotum with a clitoris, labia and vaginal canal formed in the same space as a woman’s from those parts.
Imagine having “ghost-limb” syndrome between your legs and that will give you some idea of what happened to the nerve signals that now traveled to my brain from between my legs. I could swear I had an itch in a place that no longer existed in the same way. “Healing” involved me and my brain trying to make sense out of these rerouted connections. To be sure, it took months for me to feel them at all, but eventually I began to experience sexual stimulation again. The litmus test would be penetration by a man. At least that was my standard.
I had volunteers. Nearly every close male friend who knew of my surgery volunteered, bless their hearts. They were so thoughtful! All humor aside, I could have allowed someone familiar to “test-drive” my new equipment, but I just didn’t like the idea. I still imagined it somehow being a little more meaningful than that. I did fool around with a couple of guys who put their hands down my pants and seemed ok with what they found there, but I didn’t have sex for almost a year after my surgery.
And it was with someone special. A man who at first thought he met a cisgender woman. A man who saw my heart and was successful. In short, he was everything I had hoped for. I shared about myself after our second date. He was surprised and we had a couple of challenging days, but he decided to stay and remained very interested and attracted. Our intimacy was sweet and tender. He was an extremely giving lover and I experienced my first clitoral orgasms when he went down on me. I was shocked at how quickly I came. My orgasms again different. Not the thin strand of spider silk they had been before, but a trip up a long ladder rung by rung. My excitement rising step by step. Upward and upward, occasionally missing a rung or slipping backwards. Sometimes going any further seeming impossible, but my lover’s sensitive touch seemed to know how to get me moving again. The first few times I doubted I could get there at all, but soon my confidence grew and my guardedness fell away allowing me to truly surrender to his touch.
Penetration didn’t happen for months. I was a little scared of him entering me and he was careful not to go too quickly. I still dilate daily and his penis, when engorged was larger than any of my dilators. But finally the moment was right and he gently guided himself in. The moment was profound and my eyes welled up and tears ran down my cheeks as he rhythmically began to thrust himself inside me. I found the feeling of having him inside me unbelievably fulfilling as a woman and confirming. I felt like I had arrived at the end of an incredibly long epic journey. Like Odysseus arriving home after his 20 year odyssey, the end of my wandering was here in this man’s bed with him inside me.
No more changes to make and hopefully no more unexpected change in partners ahead for me now. I’m content and my intimacy close and meaningful. Orgasms have differed along the way in duration or intensity, but through it all it was my heart that longed for connection, joy and a sense of togetherness. For me, that is available now without reservation. They say that the largest sex organ is between your ears, but it certainly helps if what’s between your legs matches what your brain imagines being there.
