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Sissy Slut Finally Gets a Release

Sissy Slut Finally Gets a Release

by Sissybottomboy
10 min read
4.69 (16400 views)
sissychastitycum from analtraininghandsfree
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After two trips to the glory hole and having multiple guys cum inside both my ass and my mouth, I was still never able to cum. I've been caged for over 7 months but I haven't had an orgasm in 3 or 4. He thinks I haven't had one in 7. My horniness was so high that I could not focus on things through out the day. I had a little hole in the end of the pink plastic cage I had on, and rubbing myself through it certainly felt good, but I was still unable to cum.

My boyfriend Mark recently got mad at me for going behind his back and trying to orgasm as he wants me to stay denied full time. We have a pretty good sex life all things considered. I am basically his free use sex slave and while I do enjoy the lifestyle a lot, I feel so pent up and horny and desperate to get a release.

He fucks me almost ever day, and sometimes for long periods of time. I get so turned on feeling his thick cock slide in and out of my ass, but every time I feel the pleasure building closer and closer to an orgasm, he finishes. It's been like this for months, he basically has me trained to get close but never finish.

Mark has the keys to my cage and he keeps them in a safe which has a passcode. I have tried to get into it when he isn't around but it's too secure and I cannot get into it without him knowing I did. I have a few dildos but he expressly forbids me from having any vibrators. I had a vibrating toothbrush I snuck in but when he found me with it, he through it out.

One day I had finally had enough. I was sitting on the couch wearing nothing but my cage and a tshirt when he came home from work, stood infront of me and started to undo his belt. Typically, when he did this, I would open my mouth and allow him to slide his cock into me, but today I refused. He kept trying to get me to suck him but I wouldn't and eventually, he gave up.

He put his pants back on and sat beside me and asked me what was wrong. I told him straight up that I wasn't enjoying the chastity anymore, it was a lot of fun to wear but it's gone too far and I need to have an orgasm. He told me he was still training me to cum from anal but I told him that wasn't good enough. Why does everyone I have sex with get to orgasm, but I never do?

I laid down the law and told him that I needed an actual orgasm, no more of this constant brain melting edging that I've been subjected to for months. After a bit of pushback he finally agreed. He said it wouldn't be happening tonight though and told me I still had to blow him. I just laughed and told him to get himself off.

He sat on the couch beside me and pulled his cock out and started stroking. I was watching him and he was getting harder and harder. He stroked and stroked for a couple of minutes before he finally stood up and walked over to me and shot his cum all over my cage. The warm sticky cum landed in the slit at the end and it actually felt really good, but I couldn't even do anything to get off.

"oh fuck yeah that felt so good" mark started to say while I sat there with his cum all over my legs and cage. "I'll get you off tomorrow, don't worry" he said as he put his cock away again. I went to bed the most frustrated I had been since the chastity journey started. I had no idea what was in store for me and Mark always liked to surprise me. I laid awake until late before finally dozing off.

When I woke up, Mark wasn't home. I made myself a coffee and sat around anxiously waiting for what he had in store. I was sitting around the corner when I heard the door open. I could hear mark talking with someone else, but I couldn't see who. "wait here, i'll go get him" mark said before walking into the room.

He acted startled when he saw me "Oh you're already awake?" he said as he saw me on the couch. "I promise you that you would orgasm today and I mean it" he said as he stood blocking the door way. He reached into his pocket and pulled out a blindfold and told me I had to wear it. I let him put it on me and after it was on, he told the other man it was safe to come into the room.

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"This must be the bitch in heat" said the other man. He had a very deep voice and I recognized it as one of the men who fucked me at the glory hole. "Don't worry I'll get her to cum" he said to mark as they slowly started to guide me toward the bedroom.

I entered the bedroom and the man instructed me to get on my knees arch my back and show him my ass. I complied with orders. He reached down and started to gently squeeze my balls. He asked mark when the last time I came was and mark said over 6 months. "wow she must be extra full then" said the man as he slapped my ass.

I stood there in this position and I could feel him start to play around with my cage. I was excited and thinking it was getting taken off, but it wasn't. I reached down to feel what he did and he put a condom over the end of my cage. "Don't want you to make a mess everywhere, do we now" he said as he once again slapped my ass.

Before I could even react, I could feel cold lube being dumped onto my ass. Before I even knew what was going on, I could feel his cock rubbing up and down my hole. "I hope you're ready to cum bitch" he said as he slowly started to push his cock into me.

The last time this man fucked me, it was after I had already taken 3 cocks, this time was different though. My hole was not as worked in and his big cock felt like it was tearing me apart as he slowly worked his way in. I finally could feel his thighs pressed up against my ass. He was all the way inside me, but he wasn't moving, he was just standing there.

I relaxed my hole and he added more lube and finally, he started to thrust in and out. He told me to push my thighs together and I did, and it made his cock feel even bigger inside of me. I couldn't see what was going on but his cock felt really, really good. Mark is good at fucking, but this guy is great. He keeps a rhythm, has good size, and knows how to come off as dominant but caring.

I was on the bed, face down, ass up, getting my hole pounded super hard by this stud. I could feel little streams of precum dripping out of me and into the condom around my cage with each thrust. It felt so good. I felt like I was finally going to be able to orgasm.

As I was thinking that however, he grabbed me and told me to roll over onto my back. I complied with orders but the building sensation in my ass was gone after he pulled out to reposition. I laid on my back and all of the precum that dripped out of me dripped back onto and into my cage. He grabbed my legs and put my thighs together, then put my legs onto his shoulders and he climbed onto the bed.

He slid his cock into me in this position and began to fuck me really hard. I could hear the sound of his thighs pounding against my ass and the feeling of pleasure began to build again. I was finally going to cum. 4 months of pent up horniness was about to be unloaded.

He kept saying to relax and just let it happen, that my hole was my main source of pleasure and I need to learn to get a release from it. I began to focus really hard on the sensations and I felt like I was gonna cum anytime. I reached down and tried to touch myself and he just laughed.

He kept his cock all the way inside of me and began to slowly rotate my legs so that I was laying on my side. "keep your legs together bitch" he said as he began to fuck me in this new position. I was just sitting with my eyes closed as he thrusted in and out, basking in the warm tingly feeling I was experiencing.

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This guy was keeping up a constant rhythm and I was beginning to feel like it was only a matter of time. He fucked me while I was on my side for a bit, and eventually I somehow ended up flat on my stomach with him mounting me from behind.

He told me to keep my thighs together again and I did, and it made his already big cock feel massive inside me once again. The pleasure just kept building and building, I could feel the precum seeping out of me now. Thrust after thrust after thrust it began to become too much.

He whispered in my ear to relax and just let it happen and when he did, It happened. I could feel my still semi soft, caged cock start to twitch and unload. I began to moan in pleasure as my months of frustration had been undone. While I was face down, blindfolded and cumming in chastity, the man fucking me began to cum too. My ass began to tighten up with each rope I shot and it sent him over the edge. I could hear him moaning at the same time I was.

I don't know exactly how many ropes I shot, but it felt like 20. It didn't feel the same level of pleasure as the orgasms I used to have but it still felt really good. It felt good to finally cum, but I still had this feeling like I didn't cum properly.

I laid there face down and I could feel the cum inside of the condom that was on my cage. I don't know how full it was but I hadn't cum in 4 months. "Are you ready for your little treat now girl?" the man said as he began to fiddle around with my cage. "roll over and open your mouth slut" he commanded. I complied with orders and did it.

I could feel the rim of the condom touch my lips "swallow your frustration now sissy girl" he said, as the load I shot out less than a minute ago was deposited into my mouth. It was really thick, like I could feel long strings of thick cum in it. I've had a lot of loads in my mouth but never one like this. I just got hit with my post nut clarity as the load was swishing in my mouth and it made me cough and gag a little.

"swallow it bitch" he said as he put his hands on my shoulders and held me down. I tried to swallow it but it kept making me gag. After multiple attempts though, I finally got it down without coughing it up. 4 months of built up cum down my throat.

After this I just kind of laid there blindfolded while mark and the man talked. I didn't even think to undo my blindfold, I was just in pure bliss, sitting there like a slut who just got fucked into an orgasm. "Now this slut knows how to cum properly" said the man "you shouldn't hear anymore complaints from her".

I could hear them talking more in the other room when I got up and went into the bathroom. I cleaned myself up a bit and I heard the front door shut. Mark and the man both took off.

I looked down at my cage and realized that I still felt the same insatiable horniness I did before. I was finally able to cum, but I still felt so pent up. Like I hadn't cum at all. The cumming wasn't even the part that felt good, it was being fucked, and I was horny and needing to be fucked again already.

I thought orgasming would make me calm down, but it did the opposite. It didn't feel nearly as good as the old orgasms I would get from stroking and only made me miss them. I wasn't going to be getting any of those soon though, so I was going to have to settle for what I could.

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