Obedient Little Puppy
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My master has dressed up as a woman for me on a couple of occasions now. And let me tell you, when he does, he looks absolutely gorgeous 
However, I recently tried dressing up as a boy for him. I tend to dress kinda scruffy/casual most of the time anyway, jeans or combats, and very rarely wear skirts or dresses. Luckily for me (what with being lazy) I didn't have to put as much effort into this as my master had to put into 'becoming' a woman; T-shirt, jeans, no makeup, hair completely hidden inside a beanie hat. Oh, and I took a pair of rolled up ankle socks and stuffed this down the front of my underwear (tight little 'girlie' boxers, funnily enough bearing the slogan 'Boys Stink') in order to look just that little bit more authentic
Anyway, for this scenario it was only me who changed gender, I became a nervous young man questioning his sexuality, while he became the older and wiser one with plenty of experience with men.
The game progressed smoothly enough, it felt a bit strange but I soon relaxed into it. By this point he was rubbing my 'cock' and I kinda had to fake sounds of pleasure to begin with, but then suddenly I felt the rolled up socks nudging between my lips and rubbing against my clit and so it wasn't faked any more
I don't yet feel confident for us to indulge in full on anal sex, so he just teased around the outside of my rear hole and continued rubbing my 'cock' but then I kind of spoiled things by, in character, admitting to actually being female. This revelation made him very angry and he punished me with a good hard spanking, before locking me up in my bathroom cupboard for a while to think about what I'd done. I did enjoy this, but kind of wish I'd just kept the game going as it had been, but when we talked after he said it didn't matter either way as we'd had fun, and that until I was ready for anal sex we wouldn't be able to progress much further with that, so I'm looking forward to overcoming that
Oh, he does have another plan; to take me into the blokes' toilets dressed as a boy and make me give him a blowjob. I asked if he wanted my appearance to fool anyone we saw, or if he wanted them to know that I was in fact a girl, and his response was 'it depends what sort of people they are'
Has anyone else ever dressed up as the opposite sex for kinky fun? I'm particularly interested about hearing any stories of (straight) girls dressing as boys, as men dressing as women seems to be more popular?
Sorry this went on a bit, I got a bit carried away I think
However, I recently tried dressing up as a boy for him. I tend to dress kinda scruffy/casual most of the time anyway, jeans or combats, and very rarely wear skirts or dresses. Luckily for me (what with being lazy) I didn't have to put as much effort into this as my master had to put into 'becoming' a woman; T-shirt, jeans, no makeup, hair completely hidden inside a beanie hat. Oh, and I took a pair of rolled up ankle socks and stuffed this down the front of my underwear (tight little 'girlie' boxers, funnily enough bearing the slogan 'Boys Stink'
) in order to look just that little bit more authentic Anyway, for this scenario it was only me who changed gender, I became a nervous young man questioning his sexuality, while he became the older and wiser one with plenty of experience with men.
The game progressed smoothly enough, it felt a bit strange but I soon relaxed into it. By this point he was rubbing my 'cock' and I kinda had to fake sounds of pleasure to begin with, but then suddenly I felt the rolled up socks nudging between my lips and rubbing against my clit and so it wasn't faked any more
I don't yet feel confident for us to indulge in full on anal sex, so he just teased around the outside of my rear hole and continued rubbing my 'cock' but then I kind of spoiled things by, in character, admitting to actually being female. This revelation made him very angry and he punished me with a good hard spanking, before locking me up in my bathroom cupboard for a while to think about what I'd done. I did enjoy this, but kind of wish I'd just kept the game going as it had been, but when we talked after he said it didn't matter either way as we'd had fun, and that until I was ready for anal sex we wouldn't be able to progress much further with that, so I'm looking forward to overcoming that
Oh, he does have another plan; to take me into the blokes' toilets dressed as a boy and make me give him a blowjob. I asked if he wanted my appearance to fool anyone we saw, or if he wanted them to know that I was in fact a girl, and his response was 'it depends what sort of people they are'
Has anyone else ever dressed up as the opposite sex for kinky fun? I'm particularly interested about hearing any stories of (straight) girls dressing as boys, as men dressing as women seems to be more popular?
Sorry this went on a bit, I got a bit carried away I think
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