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.

Femdom for Sissy

40 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.

    1. Then we start living as a real girl slut who made money for our love by becoming online whore. Thenmade us a pornstar, everysexsession must be upload. Become top most wanted sissy slut and worldwide know.

  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.

  15. my sissy fantasy actually happened before. I was taking the red line from the valley to to Hollywood. I got off the station and saw a panty shop. I new I started a fascinating attraction to them a few years back. Well I met 3 Latina transgenders there. They started talking to me. They asked if the panties were for a girl. I said no they are for me. They invited me over to their motel room. We smoked and talked. Then I saw the bulges peaking out from underneath their tight mini skirts. They instruct me to get naked. Then they gently pull the panties over my lol cutest clitty. She dawned a blonde wig on me. Then came the Lycra pink skirt. She pulled a cami out next. (All sz small, except for skirt xs) then she pulled out matching white stripper heals. Make up, and gave me a name. Arianna. Then they initiated me by making me take all of them in each hole. As I finished they said it’s my turn to pay for the room, get down SantaMonica and make some money bitch💄

  16. My sissy fantasy is this. I would be dressed up in my mothers naughty teddy lingerie. I would be wearing stockings, and her pink heels. She doesn’t know I wear her stuff. Then I would go to the bathroom where the bathtub would be filled with nothing but cum. I would then get in the tub wearing my mothers lingerie. I would bathe in the cum. Then I would get hard and add my cum to it. After I had my fun I would start to drink it all. It would take me a while to finish it but I would love to do that.

  17. being forced to stand for hours in the heels im wearing in the photo i uploaded to make Mistress happy

  18. I paid a black cock $200 to assfuck me in panties,bra w fake tits and pantyhose mask. It was stank BBC which now turns me on. it will make you a faggot. Now I have BBC’S BEGGING TO BUTTFUCK ME. stank black cock fucks best

  19. To be caught in my offsprings bra and panties and busted by then and then humiliated as they plainly see I’m hard for them and have been since my lesbo ex gf who’s sexually listed over them caused me to do the same.

  20. to be caught by a female only with her panties and bra on. have her teach e a lesson/taking photo s. she makes me go with here out in the back yard. locks the door so I can t go escape with out going out on busy street in my panties and bra. mean while she has sent photo s to her friends and my guy friends. telling them to hurry over. my male boss even gets a invite. im spanked and teased and made suck off all 15 guys. my friends and my boss. they all told me I will b sucking them off every week from now on. I can t wait for this

  21. My room mate discovers my crossdressing and tells his girlfriend. She is a cocktail waitress at a local lounge. Her and a couple other of the waitresses blackmail me. I am completely feminized by them. Then I must work at the lounge as a cocktail waitress so the girls can take vacation time. I must wear the same little uniform. Leotard, tights, short skirt and high heel sandals. My hair done toenails, fingernails painted and full make up. I work out very well and begin to enjoy my work in heels. After about a month my girlfriend and the others love my predicament so much it is made permanent. I end up as one of my ex girlfriends room mate. Working full time as a cute cocktail waitress.

  22. I’m put on a full feminization’s schedule but to pay for my training my owner requires i work as a sissy hooker turning in all the cash. She advertises me cheap but with extreme benefits to hire, keeping me working long hours to fit the bill. I’m listed as a cock sucking magician and offers free rim jobs for every blow a which are only a dollar with extended rim time, guaranteed cum in my mouth orgasm, then after an 8 to 10 hour day i must go work in the glory hole for about 4 to 5 more hours. low pay! long hours and loads all day and night down my throat and it’s da after day and it only gets busier


  24. My sissy fantasy came true, when my now ex told all of her friends about me wearing panties 24/7 and how she pegged me with a double-end dildo, just so she could feel something in her pussy, once in a while, because even when I could get hard, she couldn’t feel me hardly, at all.
    Even now, a year since she told me that she was getting so much cock that she wanted me gone, I still get off on the shame of being known by all her friends as a faggot bitch who prefers being fucked, rather than fucking.

  25. SharonTart
    My fantasy…
    To be a chastity locked feminized maid to my wife and the men she cuckolds me with, and forced to perform clean up duties after they have sex. She always turns the pillow talk to get them to suggest new ways to feminize me further and humiliate me more. One of her lovers is a policeman and says she should make me walk the red light distract all night dressed like a whore whenever he sleeps over. He said eventually I would get arrested for prostitution, held in jail overnight and released the next day to walk home past all the neighbours. My wife becomes obsessed with making this my reality.

  26. To be completely exposed locked in a cage and forced to dress up and be a girly girl all the time. Become a viral sissy and do sissy porn.

  27. my fantasy, dream is to be made sissy famous online as a diaper sissy and knowing that strangers who may have seen the post know im a diapered sissy. Maybe asked to Publically to prove im wearing , unable to refuse any diaper
    checks . unable to refuse any requests to please any or many mens cocks, as the will expose me publically unless i make them cum n satisfy their horny needs. maybe women might befreind/ dominate/humiliate me, who like diaper sissys like me..I would love to have a dominant woman/mommy/carer to support and encourage my
    diaper life and behaviour. i love the idea of public diaper checks without permission and being asked anywere if im diapered/wet my diaper etc

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