So the next 5 years are a bit fuzzy. I remember lots of masterbation, which was usually revolved around me dressing up, or putting high school photos of my head on women in catalogs (before photoshop), or somewhat successful sketches drawing myself female. Sometimes just downloading a photo of a shemale was enough to get me off. I wasn't really thinking about why something like that turned me on, I was just thinking "Hey, that's a woman with a cock, that's sort of like a really good crossdresser".
Eventually I started dating, and about a month or two after we met in person I shyly asked if she knew what a crossdresser was. She said yes, and I said sometimes I like to do that. It was as if I just told her I like chocolate because it didn't phase her in the least.
We eventually moved in together, and later got married (still married to her). I crossdressed on and off. Sometimes in front of her, sometimes when she wasn't around. Ironically I got more flak when I did it alone, because she didn't want to feel like I had to hide it from her. For some reason, the desire became stronger when she wasn't around. I don't know if it was because it felt awkward to get aroused by it, or if it just felt weird to be dressed as a girl in front of her. Over the years, there's been moments where she's helped me brush my wig, do my makeup, paint my nails, on one occasion to get my aroused she described in detail about how she was going to crossdress me.
Fast forward about 10 years, I decide to dress up one night with the intention of making love to her while dressed. She felt awkward as I approached her, even asking "what are you doing?". I said I wanted to make love to her. She went along with it, but I could tell she felt weird about it (even though she had a few lesbian experiments). Maybe a real girl is different than a guy dressed as a girl to her. We both orgasmed, but I could tell she didn't enjoy it as much as I did.
I should also add at this point that we tried swinging for a very short period. We had oral sex with only one other couple, but we attended this thing called a "BBW dance". Basically someone rents a hotel hall, rents a DJ, a bartender, orders some pizza, and a bunch of plus sized women attend. Most of the guys are either overweight themselves, or have a fat fetish. Anyway, me and my wife both attended, but me not being an outgoing person didn't have much luck (even though I could have probably said hi to any of these ladies and they'd say yes). She would play with other guys, and quite frankly I was ok with this. I felt like I wasn't sexually satisfying her, so why not some other guy? It was almost as if I was playing the part of the cuckhold husband without realizing it. That sort of faded off when my wife contracted herpes from someone, and not the mouth kind. At one point, I tried meeting with another crossdresser, and I not only gave a HJ, I also gave him a BJ. He wasn't feeling well that night, so we had to cut it short before either of us came, but I got a taste for men.
Now fast forward to about 6 months ago. I decide to try my luck again, dress up and get aroused. I wrap my arms around the back of her from behind the couch, and kiss her. I tell her that I'm horny, and she sort of just shrugs it off. I could tell that this was a revisit from a few years ago. I felt so shot down. Here we're supposed to be a couple to fulfill each other's sexual needs, and she isn't able to fulfill mine. The next 6 months are dry in bed. I blame the dogs interrupting us, I blame being tired, I blame just not being in the mood, anything that will excuse my lack of trying. Eventually when it hits a month of no sex, I'll usually try my best on a weekend morning to satisfy her (any woman pent up with sexual frustration is eventually going to get moody). Well this last session was possibly the most depressing one of my life. After very easily making her cum (I usually have to slow down so she doesn't go too fast), she decides to return the favor. She gets me aroused fairly quickly, mostly due to the fact that in my head my fantasy is nursing my cock along. My fantasy is that once I cum, I'm going to be transformed into a woman, and I'm going to have to get dressed up all pretty and stay that way for the rest of the day. We might even go out shopping together as girlfriends, perhaps she'll invite her old fuck buddy over and we'll both suck his cock together. This fantasy is a win-win because not only is the fantasy itself arousing, but the fantasy is about cumming so that I can become what is arousing me in the first place (becoming a woman), so that's like motivation for my cock.
Now because I'm feeling aroused and hard, I tell her to get on top. Most of the time, our sex life is oral simply because I have issues with keeping it up. I know she really likes "SEX", not just oral, so I figure I better take this opportunity. As soon as she climbs on top of me, all I can think about is staying hard, finding the hole and getting my cock in that hole so I can stay aroused. Of course I psych myself out, and I quickly go limp. I think that in the back of my head, I'm also thinking "Sex as a man, this doesn't turn me on"
So she scoots down, and tries to get me aroused again. Time to kick in the fantasy because I know if I simply rely on the feeling of my cock getting sucked, I won't get hard, and then after 5 minutes it'll get overly sensitive, and then I REALLY won't get hard. Oh look, I'm getting hard. My cock wants to be a pussy, and the rest of me wants to put on a pretty dress and heels and makeup, and oh lord I'm about to cum, there's she blows.
That was yesterday, and I couldn't be more depressed. At what point do I reveal how I really feel? I mean I hardly understand any of this, and somehow I'm supposed to explain this to her? I almost feel like I need couples therapy because if it's just me against her, I know I'll lose, or made to feel like I've been hiding something when the truth is I don't even know who the hell I am or what I'm supposed to feel. I mean seriously, how do you explain to a normal person what it's like to have the gender of one brain, and the sexuality of another gender. Most people know one gender, either you want to be a woman and have sex as a woman, or you want to be a man having sex as a man. Who in their right mind thinks like a dude 99% of the time, but thinks like a woman in bed? Crossdreamers like me, and probably thousands of other mis-understood people like me, that's who.
Eventually I started dating, and about a month or two after we met in person I shyly asked if she knew what a crossdresser was. She said yes, and I said sometimes I like to do that. It was as if I just told her I like chocolate because it didn't phase her in the least.
We eventually moved in together, and later got married (still married to her). I crossdressed on and off. Sometimes in front of her, sometimes when she wasn't around. Ironically I got more flak when I did it alone, because she didn't want to feel like I had to hide it from her. For some reason, the desire became stronger when she wasn't around. I don't know if it was because it felt awkward to get aroused by it, or if it just felt weird to be dressed as a girl in front of her. Over the years, there's been moments where she's helped me brush my wig, do my makeup, paint my nails, on one occasion to get my aroused she described in detail about how she was going to crossdress me.
Fast forward about 10 years, I decide to dress up one night with the intention of making love to her while dressed. She felt awkward as I approached her, even asking "what are you doing?". I said I wanted to make love to her. She went along with it, but I could tell she felt weird about it (even though she had a few lesbian experiments). Maybe a real girl is different than a guy dressed as a girl to her. We both orgasmed, but I could tell she didn't enjoy it as much as I did.
I should also add at this point that we tried swinging for a very short period. We had oral sex with only one other couple, but we attended this thing called a "BBW dance". Basically someone rents a hotel hall, rents a DJ, a bartender, orders some pizza, and a bunch of plus sized women attend. Most of the guys are either overweight themselves, or have a fat fetish. Anyway, me and my wife both attended, but me not being an outgoing person didn't have much luck (even though I could have probably said hi to any of these ladies and they'd say yes). She would play with other guys, and quite frankly I was ok with this. I felt like I wasn't sexually satisfying her, so why not some other guy? It was almost as if I was playing the part of the cuckhold husband without realizing it. That sort of faded off when my wife contracted herpes from someone, and not the mouth kind. At one point, I tried meeting with another crossdresser, and I not only gave a HJ, I also gave him a BJ. He wasn't feeling well that night, so we had to cut it short before either of us came, but I got a taste for men.
Now fast forward to about 6 months ago. I decide to try my luck again, dress up and get aroused. I wrap my arms around the back of her from behind the couch, and kiss her. I tell her that I'm horny, and she sort of just shrugs it off. I could tell that this was a revisit from a few years ago. I felt so shot down. Here we're supposed to be a couple to fulfill each other's sexual needs, and she isn't able to fulfill mine. The next 6 months are dry in bed. I blame the dogs interrupting us, I blame being tired, I blame just not being in the mood, anything that will excuse my lack of trying. Eventually when it hits a month of no sex, I'll usually try my best on a weekend morning to satisfy her (any woman pent up with sexual frustration is eventually going to get moody). Well this last session was possibly the most depressing one of my life. After very easily making her cum (I usually have to slow down so she doesn't go too fast), she decides to return the favor. She gets me aroused fairly quickly, mostly due to the fact that in my head my fantasy is nursing my cock along. My fantasy is that once I cum, I'm going to be transformed into a woman, and I'm going to have to get dressed up all pretty and stay that way for the rest of the day. We might even go out shopping together as girlfriends, perhaps she'll invite her old fuck buddy over and we'll both suck his cock together. This fantasy is a win-win because not only is the fantasy itself arousing, but the fantasy is about cumming so that I can become what is arousing me in the first place (becoming a woman), so that's like motivation for my cock.
Now because I'm feeling aroused and hard, I tell her to get on top. Most of the time, our sex life is oral simply because I have issues with keeping it up. I know she really likes "SEX", not just oral, so I figure I better take this opportunity. As soon as she climbs on top of me, all I can think about is staying hard, finding the hole and getting my cock in that hole so I can stay aroused. Of course I psych myself out, and I quickly go limp. I think that in the back of my head, I'm also thinking "Sex as a man, this doesn't turn me on"
So she scoots down, and tries to get me aroused again. Time to kick in the fantasy because I know if I simply rely on the feeling of my cock getting sucked, I won't get hard, and then after 5 minutes it'll get overly sensitive, and then I REALLY won't get hard. Oh look, I'm getting hard. My cock wants to be a pussy, and the rest of me wants to put on a pretty dress and heels and makeup, and oh lord I'm about to cum, there's she blows.
That was yesterday, and I couldn't be more depressed. At what point do I reveal how I really feel? I mean I hardly understand any of this, and somehow I'm supposed to explain this to her? I almost feel like I need couples therapy because if it's just me against her, I know I'll lose, or made to feel like I've been hiding something when the truth is I don't even know who the hell I am or what I'm supposed to feel. I mean seriously, how do you explain to a normal person what it's like to have the gender of one brain, and the sexuality of another gender. Most people know one gender, either you want to be a woman and have sex as a woman, or you want to be a man having sex as a man. Who in their right mind thinks like a dude 99% of the time, but thinks like a woman in bed? Crossdreamers like me, and probably thousands of other mis-understood people like me, that's who.
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