How I Slowly Began to Change
Before long a rhythm had established itself between me and Stefan. He would regularly ask me if I had new pictures of me crossdressing, and I’d send him a few now and again to keep him happy. Occasionally he would buy me clothes, which would always come in the mail from some online shop or other. And frequently, at least once a week (and every time after he had sent me a ‘gift’ of clothes) her would demand I come over to his place so he could "show his appreciation of me”.
But as much as this felt like they had established themselves, I was also aware of slow changes. My crossdressing wardrobe, which up to now had been orientated to being more ‘cute’ and ‘pretty’ started to look more sexy as my own choices were replaced by Stefan’s gifts. The pretty dresses got replaced by much tighter ones and by slutty miniskirts. Cute girly panties by lacy, erotic lingerie. Fishnet and patterned tights were added alongside my plain nylons. Shoes got higher and more provocative. I wore high-heeled boots for the first time because of Stefan. Denim started to play a bigger role in my wardrobe: cut-offs and short shorts, denim mini-skirts and tight skinny jeans. He got me four long luxurious new wigs: two blonde ones, a brunette one and a new black-haired one.
And our sexual contact and behaviour changed over time. The second time he fucked my ass it was almost as uncomfortable and painful as the first, but after that it got easier. Similarly I got used to giving him blowjobs, and though the first time he came in my mouth and made me swallow his sperm I found it really disgusting and degrading, and it made me nauseous for the rest of the day, in time I came to accept that too. It was the same for the times he would give me a facial. I stopped thinking of the humiliation of having another man’s cum covering my face. I knew I had to put up with all of these things - he was protecting my privacy and he did buy me all those gifts of clothes after all - so I made myself learn to not make a big deal out of it and get used to it instead. I had to admit that I kind of enjoyed sucking his thick, hard cock when he let me control the rhythm, and I convinced myself that I kind like the full feeling in my ass when he restrained himself to just gently anally fucking me in a more gentle and slow way.
Was I becoming less straight because I was leaning to be more accepting of being fucked by a man, and even starting to enjoy little parts of it? Surely these were just defensive mechanism I had developed to deal with the experience? My mind was getting a bit cloudy on the topic. I was finding it a bit harder every week to think clearer. Soon I wasn’t even protesting anymore if he didn’t just let me suck his cock in my way, but instead face fucked me aggressively, or if anal sex with me wasn’t always gentle but often involved him plunging his cock forcefully into my asshole (what he always referred to as some variant of ‘pussy’: my ‘boi-pussy’ or ‘sissy-pussy’ or ‘ass-pussy’). I let him spank my ass, both lightly in appreciation or repeatedly and severely in punishment. And I stopped arguing with him when he called me a ‘faggot’ or a ’sissy-faggot’. I was hardly in a position to argue when dressed in a bimbo blonde wig, a slutty mini-dress and strappy stiletto heels, a cock deep in my ass and having already had more foreign sperm in me by that point then I probably had blood.
Some psychological dynamic was at play, as I had started to associate his sperm as a reward for succeeding with crossdressing. As soon as i started to get dresses, and my hands touched the clothes and the wig I was selecting for that evening, I began to get images of his cock hardening, to yearn a for the success of having dressed sexy enough to cause him to cum, to feel a little bit of hunger for the appreciative shot of sperm in my mouth or my asshole, or over my face or ass. Sure getting fucked by a man was a sign of having excelled at crossdressing, of being almost woman-like? The reward of sperm was the greatest possible masculine commentary on my success at posing as a woman, what I’d been doing alone since I was fifteen?
These were all very confusing thoughts for this straight guy!
But as much as this felt like they had established themselves, I was also aware of slow changes. My crossdressing wardrobe, which up to now had been orientated to being more ‘cute’ and ‘pretty’ started to look more sexy as my own choices were replaced by Stefan’s gifts. The pretty dresses got replaced by much tighter ones and by slutty miniskirts. Cute girly panties by lacy, erotic lingerie. Fishnet and patterned tights were added alongside my plain nylons. Shoes got higher and more provocative. I wore high-heeled boots for the first time because of Stefan. Denim started to play a bigger role in my wardrobe: cut-offs and short shorts, denim mini-skirts and tight skinny jeans. He got me four long luxurious new wigs: two blonde ones, a brunette one and a new black-haired one.
And our sexual contact and behaviour changed over time. The second time he fucked my ass it was almost as uncomfortable and painful as the first, but after that it got easier. Similarly I got used to giving him blowjobs, and though the first time he came in my mouth and made me swallow his sperm I found it really disgusting and degrading, and it made me nauseous for the rest of the day, in time I came to accept that too. It was the same for the times he would give me a facial. I stopped thinking of the humiliation of having another man’s cum covering my face. I knew I had to put up with all of these things - he was protecting my privacy and he did buy me all those gifts of clothes after all - so I made myself learn to not make a big deal out of it and get used to it instead. I had to admit that I kind of enjoyed sucking his thick, hard cock when he let me control the rhythm, and I convinced myself that I kind like the full feeling in my ass when he restrained himself to just gently anally fucking me in a more gentle and slow way.
Was I becoming less straight because I was leaning to be more accepting of being fucked by a man, and even starting to enjoy little parts of it? Surely these were just defensive mechanism I had developed to deal with the experience? My mind was getting a bit cloudy on the topic. I was finding it a bit harder every week to think clearer. Soon I wasn’t even protesting anymore if he didn’t just let me suck his cock in my way, but instead face fucked me aggressively, or if anal sex with me wasn’t always gentle but often involved him plunging his cock forcefully into my asshole (what he always referred to as some variant of ‘pussy’: my ‘boi-pussy’ or ‘sissy-pussy’ or ‘ass-pussy’). I let him spank my ass, both lightly in appreciation or repeatedly and severely in punishment. And I stopped arguing with him when he called me a ‘faggot’ or a ’sissy-faggot’. I was hardly in a position to argue when dressed in a bimbo blonde wig, a slutty mini-dress and strappy stiletto heels, a cock deep in my ass and having already had more foreign sperm in me by that point then I probably had blood.
Some psychological dynamic was at play, as I had started to associate his sperm as a reward for succeeding with crossdressing. As soon as i started to get dresses, and my hands touched the clothes and the wig I was selecting for that evening, I began to get images of his cock hardening, to yearn a for the success of having dressed sexy enough to cause him to cum, to feel a little bit of hunger for the appreciative shot of sperm in my mouth or my asshole, or over my face or ass. Sure getting fucked by a man was a sign of having excelled at crossdressing, of being almost woman-like? The reward of sperm was the greatest possible masculine commentary on my success at posing as a woman, what I’d been doing alone since I was fifteen?
These were all very confusing thoughts for this straight guy!
8 years ago
Jay
It happens to all of us
Jay