Didn't crossdress until my late teens/early twenties. And then only once, tried it for a sexual experience.
From what I can remember, whilst being extremely erotic, making love to a woman whilst dressed as a woman, but it was also strangely comfortable. Didn't think that much about it, and buried it, denied just how I felt whilst I was dressed that way. In part that was down to my own insecurities, and generational stigma/views surrounding transvestism (as it was known back in the day).
I have body dismorphia about my ankles (as a male they're way to thin), and quite recently over a scar from a biopsy I had on a cancerous growth just outside of my lung, where they had to put a drain in my chest to catch any blood that may have been leaking. (Cancer is currently in remission after receiving radiotherapy last year).
Fast forward 30yrs, a misinterpreted comment from my gf (her exact words were "I could **** your arse right now") now me being a dirty minded fucker, immediately thought about being pegged by the woman I love, being used in that way by her, it was an immediate turn on.
It quickly became an obsession, I fantasised about it constantly. Even going as far as buying a strap on and a strapless dildo for her to use on me. At first she thought I was bisexual or even homosexual, took me a while to explain to her that,whilst I was almost desperate for her to peg me, in no way shape or form do I find the male body to be sexually attractive, and that I was only sexually interested in women (especially her).
Only to find that she wasn't comfortable doing it.
So I became frustrated, and as frustrated men do, I turned to porn, to **** myself off watching women **** their man in the arse. Whilst scrolling through a porn site, one day I came across (literally as well as figuratively), a video, and there was this male dressed as a woman, wearing a short black skirt, a blouse, and suspenders bent over a table whilst a woman was fucking him with a strap on. He didn't look uncomfortable or ashamed by the way he was dressed (or by the fact that he was getting fucked). My mind made connections that I thought were long forgotten, stirred up strong feelings and emotions that I couldn't explain, why was I feeling this way?
The more I thought about it, the more confused I felt. A week or so went by, and I tried talking to my gf about how I was feeling, and that I wanted to try being feminised. However she refused to listen or even talk about it. So I brutally ripped the proverbial plaster off, one morning after a Nightshift. I bought some lace panties, and a pair of suspenders, and wore them as well as a lace teddie negligè, belonging to my gf, under my PJs, and after I had a couple of JD's and coke, we went to bed, and I laid next to her.
OMG, it was the single most erotic experience of my life, my whole body was tingling, and felt like it was on fire, we started to kiss and caress each other, until she felt what I was wearing through my PJs, although she didn't know what it was. She jumped out of bed, in shock, and asked me what I was wearing. So I showed her, the look of disgust on her face hurt so bad. I was expecting to feel guilty and ashamed. But I didn't feel that way at all, I felt complete, like I had found a missing part of me, that I didn't even know was missing. I felt so comfortable and relaxed, so unashamed. And so fucking horny, (I won't tell me how many times I wanked off that day), she left the room, but I didn't take them off as I felt so comfortable, so confident in myself. Next thing I know I'm trying some of her clothes on (we're more or less the same size), it just felt right, and familiar.
Sadly my gf and I are no longer a couple, although she is very supportive of my female persona (Dion). She just can't/doesn't want to see me in heels, skirts & dresses.
From what I can remember, whilst being extremely erotic, making love to a woman whilst dressed as a woman, but it was also strangely comfortable. Didn't think that much about it, and buried it, denied just how I felt whilst I was dressed that way. In part that was down to my own insecurities, and generational stigma/views surrounding transvestism (as it was known back in the day).
I have body dismorphia about my ankles (as a male they're way to thin), and quite recently over a scar from a biopsy I had on a cancerous growth just outside of my lung, where they had to put a drain in my chest to catch any blood that may have been leaking. (Cancer is currently in remission after receiving radiotherapy last year).
Fast forward 30yrs, a misinterpreted comment from my gf (her exact words were "I could **** your arse right now") now me being a dirty minded fucker, immediately thought about being pegged by the woman I love, being used in that way by her, it was an immediate turn on.
It quickly became an obsession, I fantasised about it constantly. Even going as far as buying a strap on and a strapless dildo for her to use on me. At first she thought I was bisexual or even homosexual, took me a while to explain to her that,whilst I was almost desperate for her to peg me, in no way shape or form do I find the male body to be sexually attractive, and that I was only sexually interested in women (especially her).
Only to find that she wasn't comfortable doing it.
So I became frustrated, and as frustrated men do, I turned to porn, to **** myself off watching women **** their man in the arse. Whilst scrolling through a porn site, one day I came across (literally as well as figuratively), a video, and there was this male dressed as a woman, wearing a short black skirt, a blouse, and suspenders bent over a table whilst a woman was fucking him with a strap on. He didn't look uncomfortable or ashamed by the way he was dressed (or by the fact that he was getting fucked). My mind made connections that I thought were long forgotten, stirred up strong feelings and emotions that I couldn't explain, why was I feeling this way?
The more I thought about it, the more confused I felt. A week or so went by, and I tried talking to my gf about how I was feeling, and that I wanted to try being feminised. However she refused to listen or even talk about it. So I brutally ripped the proverbial plaster off, one morning after a Nightshift. I bought some lace panties, and a pair of suspenders, and wore them as well as a lace teddie negligè, belonging to my gf, under my PJs, and after I had a couple of JD's and coke, we went to bed, and I laid next to her.
OMG, it was the single most erotic experience of my life, my whole body was tingling, and felt like it was on fire, we started to kiss and caress each other, until she felt what I was wearing through my PJs, although she didn't know what it was. She jumped out of bed, in shock, and asked me what I was wearing. So I showed her, the look of disgust on her face hurt so bad. I was expecting to feel guilty and ashamed. But I didn't feel that way at all, I felt complete, like I had found a missing part of me, that I didn't even know was missing. I felt so comfortable and relaxed, so unashamed. And so fucking horny, (I won't tell me how many times I wanked off that day), she left the room, but I didn't take them off as I felt so comfortable, so confident in myself. Next thing I know I'm trying some of her clothes on (we're more or less the same size), it just felt right, and familiar.
Sadly my gf and I are no longer a couple, although she is very supportive of my female persona (Dion). She just can't/doesn't want to see me in heels, skirts & dresses.
Didn't crossdress until my late teens/early twenties. And then only once, tried it for a sexual experience.
From what I can remember, whilst being extremely erotic, making love to a woman whilst dressed as a woman, but it was also strangely comfortable. Didn't think that much about it, and buried it, denied just how I felt whilst I was dressed that way. In part that was down to my own insecurities, and generational stigma/views surrounding transvestism (as it was known back in the day).
I have body dismorphia about my ankles (as a male they're way to thin), and quite recently over a scar from a biopsy I had on a cancerous growth just outside of my lung, where they had to put a drain in my chest to catch any blood that may have been leaking. (Cancer is currently in remission after receiving radiotherapy last year).
Fast forward 30yrs, a misinterpreted comment from my gf (her exact words were "I could fuck your arse right now") now me being a dirty minded fucker, immediately thought about being pegged by the woman I love, being used in that way by her, it was an immediate turn on.
It quickly became an obsession, I fantasised about it constantly. Even going as far as buying a strap on and a strapless dildo for her to use on me. At first she thought I was bisexual or even homosexual, took me a while to explain to her that,whilst I was almost desperate for her to peg me, in no way shape or form do I find the male body to be sexually attractive, and that I was only sexually interested in women (especially her).
Only to find that she wasn't comfortable doing it.
So I became frustrated, and as frustrated men do, I turned to porn, to wank myself off watching women fuck their man in the arse. Whilst scrolling through a porn site, one day I came across (literally as well as figuratively), a video, and there was this male dressed as a woman, wearing a short black skirt, a blouse, and suspenders bent over a table whilst a woman was fucking him with a strap on. He didn't look uncomfortable or ashamed by the way he was dressed (or by the fact that he was getting fucked). My mind made connections that I thought were long forgotten, stirred up strong feelings and emotions that I couldn't explain, why was I feeling this way?
The more I thought about it, the more confused I felt. A week or so went by, and I tried talking to my gf about how I was feeling, and that I wanted to try being feminised. However she refused to listen or even talk about it. So I brutally ripped the proverbial plaster off, one morning after a Nightshift. I bought some lace panties, and a pair of suspenders, and wore them as well as a lace teddie negligè, belonging to my gf, under my PJs, and after I had a couple of JD's and coke, we went to bed, and I laid next to her.
OMG, it was the single most erotic experience of my life, my whole body was tingling, and felt like it was on fire, we started to kiss and caress each other, until she felt what I was wearing through my PJs, although she didn't know what it was. She jumped out of bed, in shock, and asked me what I was wearing. So I showed her, the look of disgust on her face hurt so bad. I was expecting to feel guilty and ashamed. But I didn't feel that way at all, I felt complete, like I had found a missing part of me, that I didn't even know was missing. I felt so comfortable and relaxed, so unashamed. And so fucking horny, (I won't tell me how many times I wanked off that day), she left the room, but I didn't take them off as I felt so comfortable, so confident in myself. Next thing I know I'm trying some of her clothes on (we're more or less the same size), it just felt right, and familiar.
Sadly my gf and I are no longer a couple, although she is very supportive of my female persona (Dion). She just can't/doesn't want to see me in heels, skirts & dresses.
Arabic
French
Spanish
Portuguese
Deutsch
Turkish
Dutch
Italiano
Russian
Romaian
Portuguese (Brazil)
Greek