True Confessions: Beginnings
The first real flesh penis which ever penetrated my ass belong to a M2F Crossdresser. A simple statement, but as with all such things there is a fairly complicated story which led up to the event.
I was such a straight guy up until my mid/late thirties that it hurts to talk about it now. I was a high school and college jock, lost my virginity to a bleached blond in a whorehouse at at 17, served in an elite military unit which involved jumping out of airplanes, married and divorced to former homecoming queens twice, and worked in a high pressure business job which required a relatively high level of aggressive behavior. Doesn't sound liked a guy who uses the Xhamster handle of StarrSluttCD, does it?
My second wife and I were having difficult times, and headed eventually into divorce. She was staying out with her girlfriends three or four times a month, and although she insisted adamantly that there wasn't anything going on with other men, I was still angry and suspicious. I really didn't feel much like going out with "the guys" because I really don't like drinking beer, telling stale dirty jokes, drooling over barmaids, watching sports in a group, making sarcastic comments, playing golf for skins, or most other aspects of the good old boy culture. So, I started playing around on the internet while I was watching TV when my wife was out, shifting back and forth between sitcoms and ball games on cable, and news, social and porn sites on the computer. This was back in the late 90's when Amazon was still a joke to Sears and Penney's, Ebay still involved mostly the sale of used items by private individuals, and pornography was mostly still pictures of Playboy type models spreading their legs, or elaborately posed insertions of John Holmes-sized penises into impossibly flawless vaginas. Even then, Photoshop was an amazing tool!
One evening, however, I chanced across an early transgender website, it wasn't even heavy on pornography, it was simply nude photos of an androgynous male person, slightly rounded and completely smooth body, smallish breasts, a wig, makeup and high heels. I was transfixed by the content, however, and spent most of that evening exploring that site and searching for more like it. Over the period of several weeks, I became more and more focused on the transgender internet, and actually started looking forward to the nights when my wife would go out with her girlfriends. There was a huge sexual component to my interest at that time, I admit that I was masturbating furiously and frequently, and I began to develop an overwhelming curiosity about what it would be like to have sex with a transgender woman. Since I was already suspicious that my wife was having extramarital sex, it was easy for me to convince myself that I was justified in seeking sexual release for myself, and I signed up for several dating sites.
It took at least six-seven-eight months after my interest was first piqued until I finally began hooking-up with local transgender girls, and I wound up having sexual intercourse with three of them. At the time, I viewed myself as strictly an Admirer, and always met these girls when I was presenting as a male in Drab. We had good sex together, but at that point in time I didn't do anything except kiss them, caress them all over with my hands, and penetrate them with my penis. Although I was tempted on several occasions in the heat of the moment, I never sucked on any of them, partly because they were all fairly much committed to the idea that they were women, and didn't want men who were interested in their male genitalia, and partly because I was wasn't sure that I really wanted to have a penis in my mouth. This pattern continued for a while, another several months at least, and I must have had intercourse 12-15 times in that time span.
One of the things which was surprising to me was that although the girls were not getting any substantial, direct penile contact from me, they were having a great time, and enjoying the sex at least as much as I was. That made me curious, and the phenomenon known as The Drift first started to appear in my psyche. At first, I think I was just curious to see what my body would look like if I was presenting as a woman, but whatever the true reason was, I began shaving my body all over, and began to do a much different exercise regime at the gym in order to shape and tone my body rather than maintain and develop muscle bulk. As I became more slender and free of body hair, I liked what I saw in the mirror, and (just out of curiosity I told myself) I bought a decent wig, a makeup kit, some thong panties, and a few pairs of thigh-high stockings. I think that when I began to admit that I was hooked, and was a crossdresser myself was when I bought silicon breast forms and started taking photos of myself while wearing the wig, the makeup, and the lingerie. Skirts, blouses, girl jeans, heels, and girl sandals all of a sudden began to be what I was searching for at the stores, and I quickly learned the best times to visit the local Thrift stores which sell used women's clothing for cheap.
Anyway, all of this Drift was taking place while I was having sex with the trans-girls, and not happening in a vacuum, although I still thought that even if I was a crossdresser, I was a Top. But, I was still curious about what the girls felt, so I began experimenting with anal toys, and eventually bought a seven inch dildo. Thanks to the wealth of information on the internet, I was able to stretch my internal anal ring with as little pain as could be done (still hurt like blue blazes!), learned to how to douche myself so I wasn't getting feces on the end of the dildo, and a bunch of other little tricks, like also practicing how to suck cock from instructional videos. And, all the time I was still telling myself that, "Oh, no, I'm not becoming a sissy bitch, not me! I'm still fucking those other girls who love my cock inside them!" I hadn't at this time, been together with any other person, male or female, while presenting as a girl, which also buttressed that self-lie.
One of the semi-truisms about gender identity is that it shouldn't be confused with sexual orientation. You can identify as a trans-woman and still be disinterested in having sex with a man, and vice-versa, and of course you can identify as a man and disinterested in having sex with a woman. So, while I was still thinking of my sexual identity as semi-straight (but kinky!) I was also becoming more and more femme. My wife, had gotten some limited idea of what was going on with my crossdressing, and had moved out to her own apartment, and I had freedom at home to dress whenever I wanted to, and I was becoming more proficient at makeup, walking in heels, choosing appropriate clothing and accessories, and just generally becoming more feminine in my appearance and mannerisms. I started thinking that maybe I could blend, if not pass, and began to enjoy the time that I was in feminine presentation as the "real me."
The Drift only goes one direction, they say, and eventually when you reach a certain point you realize that you feel like a woman, and that you need a man to validate that feeling. And, exactly how does a man validate that you are a woman? Well, we all know there's only one real answer to that question, right?
Again, because I felt uncomfortable at the idea of being a 'Sissy Bitch for a Real Man' as the Porno Trainer videos exhort us to be, I wanted my first experience to be with another crossdresser. Note, how I had progressed to the point where it was "another" not simply "a" crossdresser. None of the girls with whom I had been having sex were in the least interested. To one I didn't even mention the idea because she was totally and utterly opposed to even having her penis touched by me, one other simply got disgusted with me, and ended our relationship and we haven't spoken for years even tho' we see each other occasionally at local alt-life style bars and event, and the third just shook her head and laughed. She said that the joke is that the difference between an Admirer and a Transgender is two years, and I didn't even make it that long. She did, however, introduce me to a crossdreser whom she said occasionally Topped other trans-girls. For the sake of the story thread I'm going to call her Maxine although that's not even close to her real name.
I met with Maxine for coffee and a Danish when I was presenting in Drag, but she was still in Drab at the time. We hit it off pretty well, although we have completely different presentations. I am always trying to be more Fem in my voice, walk, mannerisms, makeup, clothes, whereas Maxine comes across as being more like one of the actors in the Bud Light commercials which featured guys who dress-up to get free beer at Ladies Night. It was kind of weird, because I'm fairly tall and slender, about five-eleven and a biscuit or two over a hundred fifty pounds, and smooth all-over, whereas Maxine is about five-eight and weighs about two-twenty, and doesn't shave her arms or legs. But, under the exterior she is one of the trans sorority, and she agreed to undertake the task of relieving me of my transgender virginity.
We hooked-up a few days later, she came over to my place in Drab, and changed into a wig and some femme lingerie, and we drank some wine and chated while I tried to get over my case of nerves. After a while, Maxine made her move, and pretty soon we were kissing and fooling around, and we did some mutual oral, and when she asked me if I was ready I bent over the arm of the couch on which we were sitting, arched my back, and spread my knees and presented her with my ass, naked and vulnerable (and pre-lubed!) for her pleasure. I wish I could say how wonderful it felt when I felt my first cock penetrate into my body, but truthfully I was so hung-up on the idea of being a good fuck that I don't remember. However, after she got her cock set in my ass and began fucking me in earnest I began to really get into the moment. It must have taken Maxine about seven or eight minutes to get to the point where she came, and in that time she totally cock-dominated me, to the point where all that I could think about was the cock which was pounding me into submission, and how good it felt. Maxine came inside me, wearing a condom, and said that I was a great fuck, and officially a cock-loving crossdressing slut. I discovered that I am one of the girls whose cock shrinks and becomes tiny when I am being fucked, and she also said that I whimpered and moaned beautifully.
After she left, I felt no shame, no embarrassment, nor degradation, no feeling of regret. I felt like the line on Star Trek, where no man had gone before, I was starting on a path where I had never been on before, and where it lead I knew not, but I knew that it was towards something that fulfilled something deep inside me.
I think that's enough for now. More later. Thanks for reading this.
I was such a straight guy up until my mid/late thirties that it hurts to talk about it now. I was a high school and college jock, lost my virginity to a bleached blond in a whorehouse at at 17, served in an elite military unit which involved jumping out of airplanes, married and divorced to former homecoming queens twice, and worked in a high pressure business job which required a relatively high level of aggressive behavior. Doesn't sound liked a guy who uses the Xhamster handle of StarrSluttCD, does it?
My second wife and I were having difficult times, and headed eventually into divorce. She was staying out with her girlfriends three or four times a month, and although she insisted adamantly that there wasn't anything going on with other men, I was still angry and suspicious. I really didn't feel much like going out with "the guys" because I really don't like drinking beer, telling stale dirty jokes, drooling over barmaids, watching sports in a group, making sarcastic comments, playing golf for skins, or most other aspects of the good old boy culture. So, I started playing around on the internet while I was watching TV when my wife was out, shifting back and forth between sitcoms and ball games on cable, and news, social and porn sites on the computer. This was back in the late 90's when Amazon was still a joke to Sears and Penney's, Ebay still involved mostly the sale of used items by private individuals, and pornography was mostly still pictures of Playboy type models spreading their legs, or elaborately posed insertions of John Holmes-sized penises into impossibly flawless vaginas. Even then, Photoshop was an amazing tool!
One evening, however, I chanced across an early transgender website, it wasn't even heavy on pornography, it was simply nude photos of an androgynous male person, slightly rounded and completely smooth body, smallish breasts, a wig, makeup and high heels. I was transfixed by the content, however, and spent most of that evening exploring that site and searching for more like it. Over the period of several weeks, I became more and more focused on the transgender internet, and actually started looking forward to the nights when my wife would go out with her girlfriends. There was a huge sexual component to my interest at that time, I admit that I was masturbating furiously and frequently, and I began to develop an overwhelming curiosity about what it would be like to have sex with a transgender woman. Since I was already suspicious that my wife was having extramarital sex, it was easy for me to convince myself that I was justified in seeking sexual release for myself, and I signed up for several dating sites.
It took at least six-seven-eight months after my interest was first piqued until I finally began hooking-up with local transgender girls, and I wound up having sexual intercourse with three of them. At the time, I viewed myself as strictly an Admirer, and always met these girls when I was presenting as a male in Drab. We had good sex together, but at that point in time I didn't do anything except kiss them, caress them all over with my hands, and penetrate them with my penis. Although I was tempted on several occasions in the heat of the moment, I never sucked on any of them, partly because they were all fairly much committed to the idea that they were women, and didn't want men who were interested in their male genitalia, and partly because I was wasn't sure that I really wanted to have a penis in my mouth. This pattern continued for a while, another several months at least, and I must have had intercourse 12-15 times in that time span.
One of the things which was surprising to me was that although the girls were not getting any substantial, direct penile contact from me, they were having a great time, and enjoying the sex at least as much as I was. That made me curious, and the phenomenon known as The Drift first started to appear in my psyche. At first, I think I was just curious to see what my body would look like if I was presenting as a woman, but whatever the true reason was, I began shaving my body all over, and began to do a much different exercise regime at the gym in order to shape and tone my body rather than maintain and develop muscle bulk. As I became more slender and free of body hair, I liked what I saw in the mirror, and (just out of curiosity I told myself) I bought a decent wig, a makeup kit, some thong panties, and a few pairs of thigh-high stockings. I think that when I began to admit that I was hooked, and was a crossdresser myself was when I bought silicon breast forms and started taking photos of myself while wearing the wig, the makeup, and the lingerie. Skirts, blouses, girl jeans, heels, and girl sandals all of a sudden began to be what I was searching for at the stores, and I quickly learned the best times to visit the local Thrift stores which sell used women's clothing for cheap.
Anyway, all of this Drift was taking place while I was having sex with the trans-girls, and not happening in a vacuum, although I still thought that even if I was a crossdresser, I was a Top. But, I was still curious about what the girls felt, so I began experimenting with anal toys, and eventually bought a seven inch dildo. Thanks to the wealth of information on the internet, I was able to stretch my internal anal ring with as little pain as could be done (still hurt like blue blazes!), learned to how to douche myself so I wasn't getting feces on the end of the dildo, and a bunch of other little tricks, like also practicing how to suck cock from instructional videos. And, all the time I was still telling myself that, "Oh, no, I'm not becoming a sissy bitch, not me! I'm still fucking those other girls who love my cock inside them!" I hadn't at this time, been together with any other person, male or female, while presenting as a girl, which also buttressed that self-lie.
One of the semi-truisms about gender identity is that it shouldn't be confused with sexual orientation. You can identify as a trans-woman and still be disinterested in having sex with a man, and vice-versa, and of course you can identify as a man and disinterested in having sex with a woman. So, while I was still thinking of my sexual identity as semi-straight (but kinky!) I was also becoming more and more femme. My wife, had gotten some limited idea of what was going on with my crossdressing, and had moved out to her own apartment, and I had freedom at home to dress whenever I wanted to, and I was becoming more proficient at makeup, walking in heels, choosing appropriate clothing and accessories, and just generally becoming more feminine in my appearance and mannerisms. I started thinking that maybe I could blend, if not pass, and began to enjoy the time that I was in feminine presentation as the "real me."
The Drift only goes one direction, they say, and eventually when you reach a certain point you realize that you feel like a woman, and that you need a man to validate that feeling. And, exactly how does a man validate that you are a woman? Well, we all know there's only one real answer to that question, right?
Again, because I felt uncomfortable at the idea of being a 'Sissy Bitch for a Real Man' as the Porno Trainer videos exhort us to be, I wanted my first experience to be with another crossdresser. Note, how I had progressed to the point where it was "another" not simply "a" crossdresser. None of the girls with whom I had been having sex were in the least interested. To one I didn't even mention the idea because she was totally and utterly opposed to even having her penis touched by me, one other simply got disgusted with me, and ended our relationship and we haven't spoken for years even tho' we see each other occasionally at local alt-life style bars and event, and the third just shook her head and laughed. She said that the joke is that the difference between an Admirer and a Transgender is two years, and I didn't even make it that long. She did, however, introduce me to a crossdreser whom she said occasionally Topped other trans-girls. For the sake of the story thread I'm going to call her Maxine although that's not even close to her real name.
I met with Maxine for coffee and a Danish when I was presenting in Drag, but she was still in Drab at the time. We hit it off pretty well, although we have completely different presentations. I am always trying to be more Fem in my voice, walk, mannerisms, makeup, clothes, whereas Maxine comes across as being more like one of the actors in the Bud Light commercials which featured guys who dress-up to get free beer at Ladies Night. It was kind of weird, because I'm fairly tall and slender, about five-eleven and a biscuit or two over a hundred fifty pounds, and smooth all-over, whereas Maxine is about five-eight and weighs about two-twenty, and doesn't shave her arms or legs. But, under the exterior she is one of the trans sorority, and she agreed to undertake the task of relieving me of my transgender virginity.
We hooked-up a few days later, she came over to my place in Drab, and changed into a wig and some femme lingerie, and we drank some wine and chated while I tried to get over my case of nerves. After a while, Maxine made her move, and pretty soon we were kissing and fooling around, and we did some mutual oral, and when she asked me if I was ready I bent over the arm of the couch on which we were sitting, arched my back, and spread my knees and presented her with my ass, naked and vulnerable (and pre-lubed!) for her pleasure. I wish I could say how wonderful it felt when I felt my first cock penetrate into my body, but truthfully I was so hung-up on the idea of being a good fuck that I don't remember. However, after she got her cock set in my ass and began fucking me in earnest I began to really get into the moment. It must have taken Maxine about seven or eight minutes to get to the point where she came, and in that time she totally cock-dominated me, to the point where all that I could think about was the cock which was pounding me into submission, and how good it felt. Maxine came inside me, wearing a condom, and said that I was a great fuck, and officially a cock-loving crossdressing slut. I discovered that I am one of the girls whose cock shrinks and becomes tiny when I am being fucked, and she also said that I whimpered and moaned beautifully.
After she left, I felt no shame, no embarrassment, nor degradation, no feeling of regret. I felt like the line on Star Trek, where no man had gone before, I was starting on a path where I had never been on before, and where it lead I knew not, but I knew that it was towards something that fulfilled something deep inside me.
I think that's enough for now. More later. Thanks for reading this.
7 years ago
