A crossdressing sissy fantasy

Last week  on Erotic Humiliation Calls, I asked my crossdressing readers to send me a fantasy or story to post. Here is one such fantasy from sissy Megan S.


My crossdressing fantasy would be going to a party with my lingerie under my male clothes. It would be pink panties, pink bra, garter belt and black stockings. One of the women at the party would notice my panty lines in my slacks and the bra outline in my shirt. She tells some of her male friends who gang up on me when I go to the john.

Three guys burst through the door and wrestle me to the floor. They pull my shoes and slacks off and then my shirt to expose my crossdressing. I am escorted to the living room and paraded around for all the guests some of whom are my friends who knew nothing of my fetish.

A woman shouts, “This sissy slut is dressed to be fucked!” My panties are removed and stuffed in my mouth. My hands are tied behind my back and I am placed face down in chair with my ass in the air. My co-worker Amy, who invited me to the party, lubes up my asshole and the male guests take turns fucking my ass. Amy is holding my butt cheeks open and encouraging the males to fuck my “mangina” hard!

I take 8-10 loads of cum in my ass and then it is the women’s turn who start fucking my ass with strap-ons. For the end I am put on my back and the women ride my cock to multiple orgasms. When I cum I am told to eat it. Needless to say that lingerie set is ruined, but it was definitely worth it :) Coerced cock/dildo/pussy sucking and anal sex to the extreme!

Coerced cock/dildo/pussy sucking and anal sex to the extreme is exactly right, Megan! Thank you for such an exciting fantasy!

I am still taking other submissions if any of you crossdressers would like to send me a fantasy or a real life experience. Just email me on sylvia@enchantrixempire.com and I will try to post it for you.


2 comments to A crossdressing sissy fantasy

  • Megan S.

    Ms. Sylvia,

    Thank you for posting my fantasy on your blog. It is one of many with most being caught and punished for crossdressing by a dominant woman like yourself. Maybe you could introduce my tight “mangina” to your strap-on cock? Or better yet some of your male friends:)

  • Sylvia

    I would love to have all my studs come over and make you their slut, Megan! Of course I’d have to break you in with my dildo first while my girlfriends watched and giggled. :)

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