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Kinky Newbie
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Aug 29, 2015

I go on line to a Femdom Escort site and set up a date with a beautiful women. When she arrives at my apartment she looks at me and she tells me I am dressed wrong for our date and to strip naked. She proceeds to dress me as follows. First she lubes me up and inserts a 10 function prostate massager but doesn’t turn it on Then she locks me in a chastity cage she brought just for me and puts they key in her purse. She slips a sexy shear neon pink thong on me. Then she dresses me in my silky black pants, a silky white dress shirt and black slip on dress shoes with no socks.

We get in her car and she drives us to this adult store. I figure she is getting some toys. Once inside she takes my hand and pulls me into the gloryhole booth section and we find two adjoining booths. She ask me if I have ever been to one and I answer truthfully that I haven’t. Once in the booth she takes out wrist restraints and cuffs my wrist behind my back. Then she takes out and puts on my neck a leather collar with “SISSY” on it with a leash attached to the collar, She then takes off my pants, pulls down my thong around my ankles, pushes me to my knees in front of the gloryhole and turns on the prostate vibrator.

She tells me if I ever want to get out of that chastity cage I have to suck a cock. I tell her I won’t suck a man’s cock. “You’re not”, she replies and she pulls up her skirt, pulls down her thong and out drops a perfect thick limp 6 inch cock. “You’re going to suck mine if you ever want out of that cage.” Then she goes to the adjoining booth, grabs the leash through the gloryhole, pulls my face and mouth tight against the gloryhole and says, “Suck it until I say stop”. After I choke and finally swallow her huge load I try to pull away and she says. “Where do you think you’re going? Did you hear me say stop. I think I am good for two more loads. Now suck me hard my sissy boi.” Thirty minutes later after I have sucked and swallowed her third load she pulls away and let’s go of the leash. I rub my aching jaw from all that sucking waiting for her to return with my pants. She doesn’t and I am left with my hands cuffed behind my back, a Sissy collar and leash around my neck, a thong around my ankles wearing nothing else but my shoes, a silky white dress shirt and oh yeah a vibrating prostate massager in my ass and a chastity cage locked on my cock and balls. Then I realize my phone and wallet were in my pants too. I sneak and shuffle with the thong around my ankles out to the girl at the sales counter covering myself as best I can by crouching over and the clerk says she left you this note and your phone. Then she un-cuffs my wrist and I quickly pull up my thong. The note says “I will leave your pants, wallet and keys in front of your apartment door. I took out my fee plus a generous tip from your wallet for showing you such a good time. Use your phone to call a friend for a ride home.”

P.S. “Oh, and I am mailing the key to that chastity cage to the address on your driver’s license you should get it in about a week.”

P.P.S.S. “I took a bunch of pics of you with my I Phone when you were on your knees, locked in a chastity cage, with a prostate massager in your ass, with a pink thong around your ankles and in a Sissy collar and leash in front of a gloryhole. I also took pics from my side of the gloryhole booth showing you sucking my big hard cock. If you don’t want them showing up on the internet they are for sale too for the bargain price of $500. You have my phone number obviously and I do take Pay Pal.”


Senior Kink Talk Member
  • Straight
  • Male
  • Switch
Jun 3, 2012
Crossdressed hotel sissy prostitute made to "sell" myself in the car park to a pre-arranged "client", let him walk me in heels, miniskirt, stockings and lingerie to the room and give him a blowjob...

Maybe have to dress up as a slutty hotel maid and tidy the room afterwards

Filmed doing a sissy striptease at a clothing donation bin


  • Straight
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May 15, 2022
My Favourite te fantasy , is that i am kidnapped by a shemale very cruel mistress , where i am treated like a fucking animal slut , i am whipped , caned , enema , needles play , gag i am eating her poop , drinking her piss and lots more punishment.


<:: Verified ::>
  • Straight
  • Male
  • Submissive
Jan 9, 2008
I recently discovered CBT is nice. I need to find ideas to make it painful.


Kinky Newbie
  • Straight
  • Male
  • Submissive
Jun 7, 2022
Oakville Ontario Canada
I get in to the car with a girl for a date and she has a gf in the back that gasses me until we get to her dungeon and then they undress me while I’m knocked out and tape my hands up and basically make me look like a rubber female maid with fake tits in ballet boots. After that they begin to strap me in to a chair and force me to watch and listen to femdom and sissy hypno while that’s happening they shove a butt plug up my ass and shock my cock and whip my ass after all that they gag me with a open mouth gag and spit roast me and they keep going for a while and finally they milk me repeatadly until I can no more while smothering and face sitting me and forcing me to suc and lick thei feet after wards thrown in a cage told they would continue tomorrow
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