What’s your naughtiest sissy fantasy?

Out of all of your kinky thoughts, what’s your naughtiest sissy fantasy? Princess wants to hear your sissy secrets! Leave your responses below or over on twitter.

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17 thoughts on “What’s your naughtiest sissy fantasy?

  1. My naughtiest sissy fantasy is to be locked up in chastity, dressed up as a frilly sissy and plugged. My wife would have a bull coming over and then i have to make him hard for my wife with my mouth. When he is hard i have to stay in the corner forced to watch how the bull and my wife have a great time. After the bull shooted hios load in my wife i have to clean both with my tongue.

  2. My naughtiest sissy fantasy would be to get completely dressed up and look as feminine as possible, with my sissy clitty locked in chastity. Full make up, lingerie, fishnets, high heels, wig and and collar locked on my neck reading, “cum dumpster.”
    Then I would want to take an Uber downtown to an area where there are some popular clubs. I would leave my chastity key at home and the key to my collar. I will then suck any man’s cock that wanted me to. Then I would beg him to organize a bukkake party for me right away. Maybe they could talk the bar owner into letting us use one of the rooms in the back. I would want the bukkake party to be free to anyone who wanted to cum in my mouth. Hopefully there would be 100 men or more!

  3. Another hot fantasy of mine is to get all dressed up as sissy as possible. Full make up, wig, stockings and garter, fake boobs, bra, and a cute little black party dress. Of course I would also be locked in chastity. I would leave the key at home and go for a drive. I would find a secluded public bathroom and put on a little sissy photo shoot there. I would then post pictures and a screen shot of my location and post it on every website i could. I would then take off my party dress and set it on fire flushing the remains down the toilet. I would then take a sharpie and write degrading things on my sissy body. Things like fucktoy on my chest, sissy clitty with an arrow pointing down, cum dumpster on my forehead, and whore and slut in the insides of my legs. I would then stay there in fear and anxiousness for hopefully dozens of men to show up and gangbang me. I would be their helpless little sissy gangbang cum dumpster…..

  4. If you can seriously, safely, organize a bukkake party in the north Texas area, please message me with details. I am a sissy crossdresser willing to be the cum dumpster……

    1. Being in a school gurl outfit led into a room of multiple men with big hard cocks ready to fuck me like the slutsissy bitch i am.

  5. I would love to be dressed up like a complete sissy, in chastity, and watch one or more girls do a blowbang. Then when it was time for the guys to start cumming, the girls would gather around me. The men would jack off on my sissy slut face while the girl took videos and pictures with their phones. They would also make sure all semen was properly scooped into my mouth from my face so that I would have to swallow all of it.

  6. Dreaming to become a full time gay SUCKretary at Nigerian Embassy.
    Fluent french correspondence and heavy DICKtation from A to O in the morning. Stress relief duting lunch time. Creampie service in the afternoon. And overnight care for visitors.
    And after working overtime walking home legs apart.

  7. My naughtiest sissy fantasy Is:
    Hot hooked by a female stranger online, Who convince me to give her all my info and details (ID also).
    Then After some Easy task Like, take a pic while wearing panties or take a video while fucking yourself in the ass then She would convince me to travel to her (wherever She Is) USA, Russia, Thailand anywhere in order to “meet her and do some sessions”.
    But once i got there i Will slowly get in trouble because She start drug me, then She rape me and make me sign contracts in order to give to her all my belonging, She then takes me to the hospital and After a long surgery she Will monetize my new body by selling me as a hooker for her.
    I Will ofc get beaten by her man if i dont Obey, get starved, abused ecc.
    Ofc I LOVE THIS and i Hope It Will happen to me.

  8. To be hogtied Blindfolded and gagged up and stored away in a drag queens super feminine closet (my bed being put away in a giant princess treasure/box, wearing chastity and vibrating panties and buttplug both on highest setting) only reprieves to be let out is 1. to perform at gay bars (lipsynch or oral services in the bathrooms) my reward either to be tickled for hours or milked till i cum (the drag queens choice). 2. Or be her Rubber doll where after shes done i do maidwork around the house and then have to eat food in a doggybowl while the drag queen uses me as her legstool and then ties me up on her bed and lies on top of me and smothers and grinds on me causing me to either moan in pain or moan in pleasure depending on if the chastity is still on or off.

  9. It’s a rather long one but to make it short it would be;

    I have on panties. Bra , and hose wit pants and a blouse with a ball cap and wig. I set up a meet, or go to a glory hole and meet a black man and suck him. He likes it takes me to his house strips me bonds me up and has me suck his cock as he calls a dozen friends over and they use me for 3 days then tells me they are keeping me and they turn me into a real dedicated sissy slut slave bimbo for bbc.

  10. I want to be used and abused. Multiple men sling whatever they want to me. Fuck my sissy pussy, fist me, Fuck my throat, fill me from both ends while jerking another 2. Cum in me, on me, around me, make me crawl around and lick it up, piss on me, in me, doesn’t matter. Use and abuse me.

  11. My naughtiest sissy fantasy is;
    Having my neck and wrists locked in a pillory while wearing my sissy pink turtleneck sweater dress and stretchy leggings in front of a large group. While standing on display I would be pelted in the face with used condoms and eggs, and bare bottom paddle spanked. A large cucumber would be shoved all the way up inside my butt and left there to be cooked inside of me by my body heat while everyone takes turns fucking my face. After swallowing everyone’s load I would made to push out my warm cucumber and have it force fed to me bite by bite. After my meal is have a dildo shoved down my throat and gagged in place.. Everyone would then line up behind me and take turns fucking me bareback. After everyone was out of cum I would be pelted in the face some more.

  12. my fantasy is being dressed in bra and panties and having my face slapped with multiple cocks and sucking them all and being drenched in lovely cum

  13. I wish men new my secret. I wear panties and bras. I’d suck any cock that’s taking it out. No need of asking just pull it out and push it into my mouth. Any place/any time/any cock. That’s what sissies are for.

  14. Having strangers know im a diaper sissy. Publically encouraged to prove im wearing , unable to refuse any requests to please cocks, especially black cock and women who like diaper sissys like me to support and encourage such behaviour and do diaper checks or questions in various places.

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