Gender bending

Discussion in 'General fetish discussions' started by Obedient Little Puppy, Jun 15, 2009.

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  1. 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' :D) 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 :D
     
  2. EZRA

    EZRA Member

    As a product of the 80's I spent a lot of time bending gender rolls, mostly just looking for androgyny than trying to female.
    I liked skirts alot but mostly due to the comfort aspect of them.
    I would like to occasionally go" Drag" but with my large frame and general pumpkin headiness
    I could never pull it off. and if it's not convincing it wouldn't be fun for me.
    Boys don't hold any charm for me so I don't think I would be into GOTU dressing up
    But I would enjoy pretending to be a girl( for a little while) being seduced by an older woman.
     
  3. pyroaquatic

    pyroaquatic Member

    I have crossdressed before. Damn I look sexy and feel sexy. I have a skinny hourglass figure
    and the long slender legs.

    The only thing that stands out is my huge adam's apple... and nose.

    and something else.


    I was convincing enough so that a random guy whipped out his tiny cock and thought it would be a good idea to ask if i wanted to play with it.

    He was quite shocked when I told him mine was bigger. >:eek:

    Ah... Rocky Horror Picture Show. Those were the days. I miss the black and white stockings and dressing up all goth Lolita like.
     
  4. Post pics? ;)
     
  5. nix

    nix Guest

    Occasionally I dress up as a woman, but so far the only clothes I have that fit me are panties and a skirt. My partner wants to dress me up tastefully in full girl outfit but we just haven't had the time to buy the required stuff (plus we don't want to spend money on something we're not going to use much. We're cheapskates I guess :D).
     
  6. pyroaquatic

    pyroaquatic Member

    perhaps if i can ever get in contact with my former Mistress. i mostly did it for her... although there was some me in there that wanted it to. I feel pretty, oh so pretty!
     
  7. allen

    allen New Member

    I've actually never considered doing this, but I would try it out if it came to that
     
  8. EZRA

    EZRA Member

    Evrybody needs to feel pretty once and a while.

    pretty and witty!
     
  9. pyroaquatic

    pyroaquatic Member

    my Former mistress does not have the pictures anymore. :c

    oh well.
     
  10. sweetkink

    sweetkink New Member

    i havent done it but i would love to play out a scene like this with absolute conviciton! if i could stay "in character" i think it would be very hot. thanks for the idea!
     
  11. priya

    priya New Member

    Master and i have talked about me dressing up as a boy a few of times, but have never really got around to doing it. We just discussed it a couple of days ago, and we might try it over the weekend. Will keep you posted on how it goes. :)
     
  12. Design

    Design New Member

    my friend who is a girl wants to dress me up like a girl should i let her.
     
  13. master jey

    master jey Moderator

    let her dude it's fun i have tried womens clothing looks nice on me
     
  14. Little_M

    Little_M Member

    My ex would enjoy it when I'd dress up like a boy, and I liked it too, especially in a military roleplay-context... Usually, it'd end with my crossdressing exposed, etc. He never crossdressed... And he probably wouldn't have made a very pretty girl xD
     
  15. A couple of weeks ago, I did some more cross dressing as part of a switch session...well, I was a cat burglar, dressed all in black and wearing a ski mask. I managed to overpower my master, and he said afterward that it was deply humiliating, and yet such an unbelievable turn on, to be overpowered and controlled by someone so little ;) And we're doing the same thing again this weekend too... :D
     
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