• Mistress Windy Whispers

Sissy Sissy GangBang

Updated: Feb 20

Oct 2019

Dominatrix Diaries by Mistress Windy Whispers


One of my favorite sissy clients, “Marsha”, booked a session with me. ‘She’ asked me for “something special”; she said she was feeling dirty. It was her lucky day because I was feeling extra devious. I had some new helpers at my dungeon, a couple female apprentices that I like who were asking to learn the trade of Domination. In order to deliver Marsha the session of her dreams, it was going to be a group effort.


Before Marsha arrived, 4 of us Dommes were at the dungeon preparing for her session. We were all looking fierce, as usual. My newest and youngest addition, The Empress, was wearing black lacy bra, high waisted strappy panties, and high heels. Queen Kat, my BBW Domme, was in a leather corset, high-waisted panties, and knee high boots. Goddess Athena, my transgender Sissy Queen, was wearing latex bralette, latex bikini bottoms, and high heel stilletos. I am wearing latex top, PVC vinyl waist cincher, high waisted latex bottoms, and high heels. We get out a couple sissy options to dress Marsha in, makeup, wig, and shoes. All of us put on our leather strap-on harness and picked out the dildo we wanted to use.


Marsha arrives to the dungeon, slightly trembling, looking very nervous. She was apprehensive about her request for something special and did not know anything about my plans. We collected her tribute and had her strip down to her panties and stockings. Goddess Athena rode Marsha into the sissy room of the dungeon on her back, like a pony ride. We bound Marsha’s hands upright to a suspension rig and her feet to a spreader bar. We placed a gag in Marsha’s mouth and a blindfold over her eyes so her final transformation result would be a surprise.

For Marsha’s sissification, we started at the ground and worked out way up. We selected a black pair of high-heel stilettos. Then we put her useless clitty in a chastity device cockcage. Goddess Athena held onto the key on a chain around her neck. We added a garter for Marsh’a outfit to keep her stockings up and then found the right corset, added fake boobs, and then cinched her up. For her face, we selected a black hair long wig. For makeup, we applied foundation, powder, lipstick, mascara, and eye shadow. Her slut look was complete.

Sissy training was next. We had to make sure her slut skills were up to all of our liking. We had Marsha walk for us. We each watched and laughed at her unsteady gait, giving her different pointers how to look more feminine and sassy. We had her answer us respectfully using only her high-pitched Marsha sissy voice. We put on some stripper music and instructed Marsha to give us a little tease dance shaking her booty, while we all giggled and pointed. Then we made Marsha get on her knees while we gathered in a circle around her with our strap-ons ready to teach cock sucking. We each took our turn face-fucking Marsha with our dildos. She was gagging, spitting, and eyes watering with the first girl but we continued with her cocksucking training until it was my turn at the end. I used the squirting dildo that I had filled up with a purchased ‘Jizz’ solution. When I was satisfied with her BJ, I released my load onto all over her slutty face and into her mouth until she was gagging again. We kept in this position for awhile after we were done with her- kneeling, panting, cum-covered face with a pool of fluids underneath her.


Marsha’a sissy training was complete and we were ready to move onto her punishment. Marsha is very slutty. She craves my femme cock. She has dirty thoughts all day and then is a cocktease at night. Sometimes I make her wear panties to work under her man clothes; her inner slut really comes out then! We had Marsha bend over the table and then bound her hands to her feet using a spreader bar. We each took turns spanking Marsha, repeatedly telling her things like: what a naughty girl she is, how slutty she looked in that outfit, how useless her clitty is and that’s why it deserves to be locked up, and how we are going to make her our Barbie slut fucktoy to use how we want. Marsha took the spankings like a good gurl, although she was whining and wiggling. We had her use her Marsha voice and Thank Us for each spanking and ask for another. Her ass was brilliantly red by the time the 4 of us were done with her!


We were ready to ‘have our way’ with Marsha since she was conveniently already in a compromising position bent over. We took turns one-by-one, using our strap on’s to ‘own’ Marsha’s pussy. Marsha was no size queen, she was tight and we had to work it in. It seemed like each girl had to work harder than the next, until it was MY turn. I let Marsha drop to her knees to a doggystyle position. One of the girls teased Marsha’s caged clitty as I began using my 8-inch long cock. It was a respectful size and although Marsha was whining and wiggling, she took it for me, each and every stroke.


When we were all finished with Marsha, we wanted entertainment. We unlocked her clitty from the chastity cockcage. There were cage imprints on her clitty for trying to get hard while she was being pegged. Immediately her clitty started dripping with pre-cum excitement. We wanted Marsha to stroke her clitty and do a slut dance for us. We smiled, laughed, and talked amoungst ourselves as Marsha tried desperately to impress us with her stroking and dancing skills. Her attempts, however, were fruitless and we all agreed that she could do better. We decided that it would be best for Marsha to go home with her clitty caged at least for the night, that we would consider unlocking it tomorrow. Marsha would have to convince us tomorrow that she should be released from the cage by begging to our satisfaction and confessing to us what a dirty gurl she is.

It was time for Marsha’s aftercare from such an intense, invigorating session being our playtoy. We let Marsha get cleaned up. We took off her sexy sissy clothes and replaced them with her boring man clothes. However, Marsha had to keep on the panties and cockcage chastity device. We all took turns hugging her and telling her how much fun we had and then Marsha went home….



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