• Category Archives Erotica
  • Hot Crossdressing story from Reddit

    /u//Ishouldstopbutdont posted this hot crossdressing story from Reddit in /r/confession/

    “[No Regrets]
    I’m a woman in my 20s and I guess I’m attractive enough. For whatever reason, I find it entertaining/cute/funny/fun when guys cross dress.

    I discovered a while ago that it’s really easy to get them to do it. I’ll flirt with guys anywhere once I trust them enough not to be crazy (coworkers, classmates, friends/acquaintances etc.). Then I’ll tell them how I like guys cross dressing.

    Once that’s done, I usually get them to go to the mall together where I pick out clothes for them to buy to wear (including underwear, of course). Back at my place, I get them to wear it, do they’re makeup etc. they’re usually kinda nervous but willing (I tune up the flirting). I usually just hang out with them, leaving them wanting more. I’ll invite them back on later days, dress them up again and keep it going on multiple days (sometimes getting new outfits) and continually teasing them.

    After a few times, I start getting them to do chores around the house like cleaning and making dinner. It’s amazing how many will just do it and I love watching it. If a guy’s really easy to control and keeps coming back hoping for more, I’ll turn it up a notch and get him silly outfits like a French maid outfit to work around the house in.

    I’ll keep this going until the guy just gives up.

    Basically, it gives me entertainment and gets chores done. I never promise anything and never lie to them; so, it is technically all their own free will.

    I guess it’s kinda wrong, but I don’t really feel bad.”

    Her followup post says:

    “I guess some people like this and some are fascinated.
    Like I said, I never make false promises. I just ask them to dress up and do the chores. If they wanna go out, I usually just ask them to come over instead and they always oblige. After a number of times they’re usually competent enough to pick out outfits (which they keep at my place) and do their own makeup (which I get them to buy for themselves, of course). I think they’re extra careful doing the laundry cuz that’s their clothes in there, too. In terms of the french maid outfits, the first few times I bought it for the guys as a gift, but later realized that they’re more than happy to pay. So, I just tell them I think they’d look awesome in one and just tell them which one to order.

    I have boxes full of clothes and makeup and stuff (even wigs) from guys. Once they stop coming I ask them if they’d at least like to pick up their stuff but they never do, so I ask if I can have it and they just let me.

    So, I guess it’s kinda bad, but they’re all willing participants and I never make any promises that I break. Plus, it entertains me to no end.”

    How many of you would go for that fantasy in a heart beat?