The Life and Fantasies of a Sissy!

The following story is partly true and partly fiction. The names have been changed to protect the guilty. I hope you enjoy the story as much as i did living parts of it and wishing i had lived the rest of what is here.

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A number of years ago i saw an ad from Mistress Kay and was fascinated by what i saw and read. After thinking about it for a while i sent Her an introductory email and waited for a reply. The reply came the next day and after exchanging a number of emails and a few phone calls a first visit to Mistress Kay's dungeon was arranged. Following Her instructions i arrived wearing lingerie under my regular clothes. After exchanging greetings She instructed me to remove my male clothes and follow Her into the dungeon. After nearly two hours of sensuous torture i found myself tied on my back with my feet higher than my head. Mistress Kay was inserting larger and larger sounds in clit my while She stroked my hardening clit. Finally without warning I erupted in orgasm shooting the current sound over my head to both our surprise!

The next visit a few months later having followed Mistress Kay's instructions i painted my toe nails and finger nails a bright red. i was wearing white stockings with pink garter belt, panties and bra under khaki slacks and a light colored dress shirt with open toed low pumps. Mistress took me into Her dungeon where a remote controlled vibrator was inserted in my ass and bright red lipstick is applied to my lips. Mistress then instructed me to get my pants back on so we could go out for dinner, embarrassment and excitement started to set-in. We went to a small restaurant where we sat side by side at a table. The rules were to keep my hands visible on the table, speak to the waitress, but let Mistress order. Whenever the waitress was around the plug in my ass would start to vibrate. After a nice stimulating dinner we returned to Mistress's dungeon for a great session of sensuous teasing and painful suffering.

The next time i saw Mistress Kay she instructed me to buy as feminine shorts and top pajama set of stretchy soft material. i was to wear this with stockings, high heels and bright red lipstick to Mistress' new dungeon. When i arrived at the dungeon there was a work crew working next door and i had to walk by them on my way in, to some whistles and cat calls. When I got to the door Mistress let me in. After exchanging greetings Mistress tied me to a spanking bench and put a mask on my face. She then started to probe my anus and play with my clit. Then there was a knock at the door which Mistress answered. i could not see the door so I did not know what was going on. Shortly Mistress Kay covered my eyes with her hands. When she removed them i was looking at three hard cocks. Mistress said, "Open your mouth slut and service these real men!" And the first of the cock slide into my mouth. Sometime later with a sore mouth and a face covered with cum, the three cocks left. Mistress then tied me on my back covered in cum as i was and proceed to torture my clit with needles and sounds. After amusing Herself with my sore little clit Mistress decided to wash off my face with Her sweet delicious pee. While enjoying this treat my little clit squirted which i was forced to eat and wash down with some more golden nectar. And another rewarding session with Mistress Kay ended.

Sometime after this session Mistress Kay contacted me and asked if i could be available for a surprise and fun on one of three different dates. She said that She had a surprise for me and that i would have an interesting time. A few days before the agreed upon date Mistress sent an email with some final instructions. i arrived at the designated time bring the requested items with me. Mistress Kay took me to the bathroom off the dungeon and said to call Her when i was ready. i quickly stripped off my male clothes and started douching my sissy pussy. After four douches it was clean and I took a quick shower. After drying off i put on a bra to hold my tits and followed this with hose, garter belt and heels, before topping it off with my maids outfit. Following this i applied red lipstick and let my Mistress know i was ready.

A few minutes later a beautiful brunette in a revealing nurse outfit came into the bathroom and introduced herself as Lady Nancy. She took me out into the dungeon and said that Mistress Kay had asked her to prepare me for what was ahead. She stated that they wanted to control all of my orifices and activities. She bent me over the spanking bench and lubed up my sissy pussy before inserting an anal plug. Lady Nancy then had me sit on the bench driving the plug further into me as she put ankle cuffs on me, joined by a short hobble chain. Lady Nancy then laid me back on the bench and inserted a Foley catheter and clamped the end off so that i could not urinate. Then a ball stretched was attached that had a strap with a ring going below and between my balls. Lady Nancy then sat me up and had wrist cuffs, a collar and an O-ring gag, forcing my mouth open. She threaded a chain through a ring in the collar and attached each end to the wrist cuffs; i had use of my hands but could not touch or protect my clit. Lady Nancy clipped a leash to the collar and led me into Mistress Kay's living room. She then attached a short chain between the ring on the ball stretcher and the center of the hobble chain, now every step I would take would pull on my balls. Mistress Kay came in to inspect Lady Nancy's handy work. This was met with approval and Mistress Kay showed me where the wine and snacks for lunch were. i was then taken to the center of the living room facing the sofa and chairs where Mistress Kay put a blind fold over my eyes and told me to stand there.

I could hear movement in the room but couldn't see anything. If seemed like people were walking around me, but i couldn't be sure. Then i felt hands touching me all over, face, ass, clit, etc. Then whoever it was started spitting in my open mouth. After sometime this stopped and the room grew quite. i was told to remove my mask and there seated before me were several of the most beautiful dominate women i had ever seen. There was also another beautiful women setting at the feet of one of the women. Mistress Kay told me to serve the drinks and snacks to the group which I started to do. As i did he plug in my pussy started to vibrate and then it shocked me. Mistress Kay said "Hurry up and get your chores done or you will much worse." So I started serving the refreshments. i served the group snacks and drinks for the next twenty minutes or so. All the time they were touching me, talking about me, while the plug in my in my pussy was alternating between pleasure and sharp jabs of pain. Mistress Kay asked me if i was thirsty to which i replied "Yes." She instructed me to get a wine glass from the kitchen. When i returned and handed it to her she spit in it and then passed the glass to all the other dominates to do the same. When the glass arrived back to Mistress Kay she unplugged my catheter and filled the glass with my own piss. She then handed it to me to drink while the group laughed and humiliated me.

One of the Mistresses, whom i later learned was Mistress Snow, asked if she could use me for a minute. Permission was granted and she took me into the bathroom. She had me stand in a corner facing away from the toilet while she sat to pee. When She finished i was instructed to turn around and clean her pussy after which i thanked Her for being allowed this privilege. We then returned to the living where i was instructed to stand in the middle of the floor facing the group.

The lady who had been sitting on the floor stood and walked over and stood beside me. She was introduced as Mistress Dawn's slave Sandy. The group was told that Sandy would remove the chains from my wrists, ankles and ball. She would also remove the catheter and O-ring gag. Once this was done Sandy and i were to start dancing and making out. Sandy was to try to keep from coming and i was to try to make her come in 15 minutes. Music was turned on and shortly we were dancing and kissing. Tongues were out; necks were pleasured as hands roamed each body. Sandy's dress was the next thing to go, exposing her small breasts and very sexy body. i licked her breasts and armpits and teased her nipples as I sank to my knees. i reached up and started to pull down Sandy's panties and what should pop out in front of my face except eight inches of semi-hard clit, Sandy was a transsexual and sexy. As time was running out i started kissing, licking and sucking Sandy's sex big clit. After lubricating my finger i gently inserted it into Sandy's pussy ass and started to massage her prostate. Just as Sandy started to respond and fuck my face the shocks started coming in my pussy ass distracting me from the task at hand, or should i say in mouth. Needless to say Sandy did not cum and won the challenge. i never did find out what she won, but in the long run i think i won as well.

Mistress K and Lady Nancy went to the dungeon to prepare for my punishment. After resting for a few minutes i was lead up to the dungeon where i was instructed to take everything off except my garter belt and hose. Mistress Kay's torture table had been moved to the center of the room, with steps placed at one end. The table was covered in plastic, incontinence pads and a sheet. Mistress Kay instructed me to lie on the table with my head towards the steps. My arms and legs were bound to the four corners of the table as all of the guests arrived around the table. Everyone started to tease and torture me; nipples clamped and pierced, brought to the edge numerous times without relief, hands, hands vibrators, tens units, sounds and clamps on my clit and balls. While all of this was going on different members of the group were sitting on my face to receive oral pleasure, anal kissing or giving me golden nectar to drink. So much was going on that i could not keep up with everything that was being done with and to me. After sometime Mistress Kay announced that it was time for me to receive some relief. She climbed up and settled her beautiful pussy over my mouth and starts to stroke my cock. As i exploded into an orgasm Mistress Kay released her piss into my mouth and continued to stork the post come super sensitive clit until I was withering in pain and pleasure.

i can't wait to see what my next visit will bring...