Final Sissy story I wrote. Again very erotic and bondage oriented. 18+
From Date to Slave
When I met Jenny on the dating site I never imagined how beautiful she would be in person. It seemed like we hit it off right away at our first meeting at the coffee shop. After we were done having a few cups of coffee I got into her car and she said we'd be going to a party, if I had only asked what kind of party it was.
Upon our arrival I could tell instantly it was a fetish party of some sort based off of how the few people I saw was dressed. After we were inside I was asked to put these wrist and ankle cuffs on, Since everyone around seemed to be wearing them I didn't see anything wrong with putting them on. Jenny had to help me with the wrist cuffs and I was able to put the ankle cuffs on without a problem.
I met a few new people that and some people I think I recognize. We walked into a big room with a bunch of what looked to be medical tables. Most were empty but a couple had people on them. Jenny asked me to get up onto one of the tables
I hopped up onto the table and Jenny slowly attached my right wrist to the table and directed me to get up onto the table on my hands and knees. After I complied she hooked up my left wrist to the table. Not even a moment later the ankle cuffs were attached as well.
While in my secured state Jenny cut all my clothes off. I was then repositioned so I'd have to stick my butt into the air. Jenny and someone else proceeded to insert a butt plug into my ass that had a hose attached to it. The plug was inflated and it was now secured and was not being pulled out anytime soon.
They proceeded to give me an enema and was told I needed to be cleaned out for the rest of the night. A cleaning out I thought, what the hell did I get myself into?
The entire time the enema was settling inside of me, Jenny rubbed my stomach and calmed me a little bit and said she knows this is what I wanted and will get a great bondage experience of my life. She said she'd be in control with a master as well as whoever else they care to help train me to be the best sex slave I could be.
After my enema cleansing was over with they put another thing up my ass, it was much smaller than the enema butt plug that was just inside of me. Jenny told me that they were gonna milk me dry so i could have the endurance for the later festivities. My mind went black and I now knew what it was up my ass, a prostate massaging device.
It was moved around and they lightly stroked my dic-k and I felt like I was peeing slowly but it turned out to be all my milky c-um built up inside leaking and oozing out into a small glass. This went on for what seemed like an hour or so, but was probably more like 20-30 minutes. After they had me emptied out of all my milky c-um I was allowed to sit up regular again.
A pen-is gag was pulled out from a drawer from the table and I watched as it was covered with all of my milky c-um. After the pen-is gag was covered entirely I was told to open wide and it was shoved into my mouth and the gag was then locked onto me without any hope of removing it. I was told to clean it up and enjoy the flavor as it was a taste I would have again later on in the evening.
A chastity device was locked onto my dic-k and a pair of metallic like pants were put on me as well that left a rear hole for access to my butt or for me to use the bathroom. Since they just flushed out my bowels with that enema earlier, I could only assume it was for the access and not a bathroom break.
A large flesh toned body unitard was pulled out for me to wear. I reluctantly put it on and I was helped out for the last part as I couldn't zip it up back since the hands were more like mittens since the fingers were sewed together.
After the unitard was on, I was taken to another room. I saw five other guys that were dressed similar to me sitting on a hanging bench and all of them I could hear whimpering a little bit. As I got closer to the hanging bench I figured out why they were whimpering, there was a big dil-do on the bench where I'd would be sitting. The crotch zipper on my unitard was unzipped and some gel was rubbed onto my butt and some was also rubbed onto the dil-do that was starring at me in the face. I was then lifted up and lowered onto the dil-do. It was excruciating to feel it go into my ass opening me up. It felt like I was being ripped apart starting at my ass.
My wrists were attached to the chains holding the bench in the air. My ankles were attached to each other effectively securing me onto the bench. My feet dangled from the bench and there was no way I could lift myself off of the dil-do and the more I moved it made me more aware of the dil-do inside of me. My new bondage home suc-king on a pen-is gag still covered in my own milk-c-um. After I myself started to whimper with the other boy slaves I felt a little shock in my ass which made me yelp and all the other slaves must have been shocked too since we all yelped in unison.
The shocking of the dil-do is all of our asses effectively made us fuc-k the dil-do on our own. I just sat there and suc-ked on the pen-is gag almost like it was a pacifier trying to calm me down for all that was happening so fast around me. I even started to move my tongue around instinctively licking every inch of the pen-is gag locked inside my mouth.
I saw one of the guys being removed from his bondage pen-is bench and they started to add leather straps all over his body. Now he was effectively in a full body harness with hooks n rings all over it. They even put wrist cuffs and leg cuffs on him along with thigh cuffs, I am sure it was for putting him in any position they wanted. I saw a horse bench with wheels being brought out and they were fast to hook him up to it and I watched as he struggled against his bonds as if he knew what was coming and he didn't want anything to do with it.
He was wheeled through a door and vanished into the dark and I could only imagine what was going to happen to him.
I think I am next as I watch a small bench of sorts wheeled in front of me. I see a few hooks and straps on it. Jenny walks in and asks if I am ready, I just looked all lost and then the shock came again from the dil-do I was plugged onto and I looked like I nodded yes and she replied great!
Jenny hooked my hands from the chains and someone else helped her pull me off of the dil-do so they could strap me into the bench below me. I am made to kneel on the bench and my ankles were locked down to the bench. There were two straps per leg that were pulled down to keep me in the kneeling position. I was ordered to lay my chest onto the bench so they could finish. Another strap was pulled around my back and kept me from getting up. My hands were finally attached to the bench.
Jenny said just a few final touches before we go out there. She pulled out a quite large butt plug and put it into my ass and it sure did hurt. Tears came down and I know soaked the mask's eyes. Finally she put a nose hook on me and hooked it onto the unitard effectively forcing me to lift my head forward.
I was wheeled into another room and was put into the center of the room. I could barely see all the people sitting in a circle. Jenny walked in front of me and asked if I would be good or would I need extra training. I did my best to say I'll be good while suc-king on the pen-is gag that is finally cleaned of my own c-um.
Jenny says good and removed the pen-is gag. Jenny rubbed my head and says that I'll really love this. Someone walked up to me and my head and mouth were near perfect level for his coc-k to be right in front of my mouth. I reluctantly opened my mouth know there was nothing I could do. He was shaved and seemed to be very sweaty. He was somewhat soft when he stuck it in my mouth. It however quickly grew and nearly filled my entire mouth.
This guy started to fuc-k my mouth and he went down my throat a little with ease because of the way my head was pulled up by the nose hook. He fuc-ked my mouth at different speeds, he'd fuc-k fast then slow. When he did it slow he made sure to get as far into my throat as he could. I licked his coc-k as best I could like I had done to the gag earlier. A few minutes later he came into my mouth, he shoved his coc-k as far as he could and I could feel his c-um shooting down my throat. He pulled out a little and told me to suc-k the rest out and clean him well. It didn't seem like the c-um would stop oozing out and officially made me a c-um eater.
After this guy was cleaned another stepped up in his place and didn't even wait to start fuc-king my mouth hard and fast without relent. He fuc-ked my throat fast and hard, he was gagging me pretty bad. Within minutes he too came and it shot down my throat. He too made me clean him off and suc-k out all the remaining c-um that his pulsating coc-k was shooting out. I must have done something right because he started to c-um again filling my mouth up and it was all I could do to make sure it didn't leak.
Three more guys fuc-ked my mouth, each of them fuc-ked it more gently than the first two guys. Hell I don't know they may have fuc-ked my face hard as the first two guys but I may have been used to it already or my mind was floating in subspace.
There was a gag pulled out that had a funnel on it and another pen-is gag. This was strapped onto my head and another rubber coc-k was now inside of my mouth strapped on not going anywhere. After the gag was locked into place the butt plug that was inside of me was pulled out and the gag muffled my cry of pain as it was ripped out.
I couldn't see anything behind me and god only knows how many guys were ready to fuc-k my ass now.
I felt one hand grab my right ass cheek and squeezed hard and it made me yelp and then he slapped my left ass cheek and I could feel him poking at my asshole. This would be my first time someone one has taken my hole and I could not do anything about it strapped down to this bondage rape rack. He was in and was slowly pushing his coc-k into my ass, he soon enough completely filled my ass with his coc-k. I could feel it pulsating or maybe that was just my nerves. All I know is I am being fuc-ked and I can feel my own dic-k trying to get hard in the chastity device. This guy started to fuc-k me ferociously ramming into my ass without remorse. He started to slow down and I think he was about to c-um. I could feel him shooting load after load into my ass.
He almost collapsed on top of me and then patted me on the head and told me I was the best in a long time and I should be proud. He then pulled out of me and another guy took his place. He took no time at all shoving his coc-k into my throbbing asshole. He held onto my shoulders and fuc-ked me but good. He let go of my shoulders and I could feel myself backing my ass up as much as I could like I wanted this. He fuc-ked me for another 5 minutes or so and unleashed his load into my bowels as well. After he pulled out another guy hopped right into place.
After 8 guys or so, I lost count, fuc-ked me in the ass I could feel the c-um dribbling out of my butt hole. I could feel them doing something as if they were catching and cleaning the c-um coming out. I thought this was weird. Not a moment later I knew what their plan was, all the c-um that went into my ass and dribbled out I was now going to drink down though the funnel pen-is gag.
Six younger looking guys came in front of me and started to beat off fast as they could. One guy already started to c-um and shot most of his load into the funnel filling it up more with my new protein treat. He also made sure he made a few squirts on my head and rubbed the c-um into my hair like it was a hair gel. Not a moment later the other five guys all started to c-um at the same time and all of them did their best to shoot their load as well into the funnel. These guys also made sure some c-um went on my face or in my hair. There was a lot of c-um in the funnel and I suppose I am glad that they clean out my ass with the enema earlier or I'd be scarfing down c-um and shit.
I suc-ked down the c-um as fast as I could for them, definantly something I don't think I want to do again.
I was wheeled back to the room with the bench with the dil-do sticking up as my old seat from earlier, I thought they were going to put me back on it, however I was wrong. I was wheeled into the room with all the tables and I was released form the restraining thing I was on and put onto the table I was at earlier. A few restraints were placed on my arms and then locked forcing my arms into a bent position. With my arms this way and the mittens on there was no way I could do anything.
The funnel pen-is gag was removed and replaced with a pony bit gag. This gag was also locked on without any chance of removal without the keys. After the gag was locked on I was then taken to another room. All I saw were several cages with what appeared to be other guys like myself. I was placed inside one of the cages and was told that I will make a great new addition if I do as well as I did tonight. They locked the cage and they left the room.
I glanced around and I saw the other sex slaves and wondered if this new life would be permanent or was this some game Jenny was playing. I could still taste the c-um in my mouth, my ass felt like it was on fire and my throat was sore. Will I be a free man once again or am I now a sex slave for the rest of my life?
Betty Pearl's Sissy Stories 20.1
Topic: From Date to Slave (Read 13784 times)
