Free Use Glory Hole Sissy

I recently started dating a guy, we'll call him Mark, and he was very kinky. He loved to dominate me in and out of the bed room. Things started out slow, but after a month of dating he had me very well trained.

I was locked in a chastity cage full time, and whenever he commanded me to do so, I would service him. He would fuck me in the ass whenever he wanted, and he loved to finish in my mouth, forcing me to swallow his cum every time. He would also randomly pull down his pants and shove his ass in my face, telling me to be a good sissy bitch and eat it. I loved doing all of this as it made me feel so submissive to him.

I would never get an orgasm myself, I could get close while caged and being fucked but I just could never get over the hump. There was several occasions where I would feel like I was about to cum and he would pull out, spin me around and empty out his balls into my mouth.

He would always tell me about his previous sexual escapades, how he would go to a glory hole nearby and have his cock serviced by guys. I heard lots of stories about that glory hole. I heard about guys being tied up and then used all night, and I honestly found that to be quite hot. I playfully went along with it, saying I'd love to go there and try it sometime.

A few days later he told me he had a surprise for me. I had a hunch on what it was, but I went along because I was super horny, intrigued and frustrated from being denied for over a month. He told me to put my plug in and make sure my ass was ready, before he reached into a drawer and pulled out a blindfold and a leather collar that had a chain attached to it. He put the blindfold on me and then attached the collar and begin to direct me where to go. I went outside and got into his car and he started it up and began driving

About 15 minutes later he parked the car and got out. He walked around and opened the door and grabbed the leash. "come with me" Mark said, as he guided me where to go. We walked for about a minute before I heard a door open, it sounded like we were walking in to a convenience store. "watch your step" he said as I walked in and nearly tripped "we're almost there".

I heard another door open, this one was much creakier. I walked through the door way and I heard him rustling around with the chain. "wait here" he said as he left the room. I heard the door next to this stall open up immediately and figured he was going to make me suck his dick through the glory hole. Instead, though, I felt the chain pull me toward the wall. I was completely blindfolded this whole time and playing along, waiting for whatever was next.

I felt his hand on the back of my head as I got close to the wall. "watch your head" he said as he guided my head through a big hole in the wall. This wasn't your standard glory hole, it was big enough to fit my entire head through. As soon as my entire head was through the hole, I felt the chain around my neck get tighter, like it was being tied to something. I tried to pull my head back through the hole, but I couldn't. I was stuck.

Mark pulled up the blind fold and I saw that he had a massive smile on his face. He left the room and I heard him say 'we got one back here boys' before coming back into the room my head was in. I asked him who he was talking to and he told me not to worry about it. I started to talk some more, but he pulled his pants down and put his cock right up to my lips and my instincts kicked in and I started sucking. He was already rock hard when I took him into my mouth, which was a little unusual because usually I had to make him hard.

There was porn on a tv in the room, and it was some video compilation about cumming from anal. I was too distracted with his cock in my mouth and the porn that was on, because while this was going on I suddenly felt someone pulling my pants down, and then pulling the buttplug out of me. First the plug came out, then some icy cold, lube covered finger rubbed against it. It made me jump a little because it was freezing, but I couldn't move anywhere, I was bound and immobilized. Mark took a step back and was staring me right in the face, gauging my reaction to what as going on in the other room.

Whoever was in the room with my ass was squeezing my balls really hard and it was quite painful, but I couldn't do anything. Next thing I feel is a cock slap against my ass and then rub against my hole, a second later I felt a slap on my ass and whoever was there, had pushed their cock into me. I could feel his hands on my hips as he slid in and out, fucking me roughly. He kept reaching down and squeezing my balls while fucking me. I didn't enjoy that part at all but there was nothing I could do to stop it.

I was watching the cum from anal instructions on the tv and each thrust began to feel better and better. I could feel myself getting closer and closer to an orgasm. Whoever was fucking me was doing a good job, it felt really good. I could hear my ass cheeks slapping with each thrust. Mark just stood there watching my face still, he looked completely fascinated by what he was seeing.

Thrust after thrust, I could hear the man fucking me grunting louder and louder. I could also feel my cock leaking precum everywhere. The video was saying to relax and let your instincts take over to cum from anal, and I felt like I was finally getting close when all of a sudden the guy started moaning really loud. He pushed all the way in and stopped thrusting right as I felt like I was on the edge, dumping his load deep inside of me. He pulled out and gave my ass one final spanking before sliding the butt plug in.

I was so horny and frustrated, I felt like I was so close and yet, so far away. Mark, sensing my frustration, stood there laughing at me. We talked a little, and a couple of minutes later I heard the door open again. I felt the plug get pulled out again, and this time the man said "wow that is a well used hole". Before I could even react he was inside of me. I could feel his hips up against my ass, and I don't know if my hole was loose or if his dick was smaller, but there was not nearly as much resistance this time.

He slid in and out and I was trying to focus on orgasming, but it didn't feel nearly good enough. I could hear a clapping sound each thrust and he was fucking me hard, but I didn't feel like I was getting any closer to cumming. After about 2 minutes, I could hear his breathing become more laboured and I felt him start to squeeze my hips. One loud moan later and he was all the way in, dumping the second load of the day into me. A few seconds later, he pulled out and slid the plug back in. I could feel my hole trying to push it out but I was trying to squeeze and hold it in.

Immediately after this guy left, the door opened again and someone else walked in. I felt a spanking on my ass and the buttplug I was trying to hold in instantly fell out. As soon as it fell out, I could feel a cock slide in to replace it. He kept spanking me while penetrating me, and it was starting to feel really good. i could feel strings of precum dripping down all over my legs while he was using my hole. He fucked me like this for a couple of minutes before telling me to push my thighs together and I did that, and it made it feel even better. I felt like I was finally going to be able to cum.

I could feel the pleasure building and building as he slid in and out of me. I was finally going to cum and get my release. Right as I felt like I was going to go over the edge though, he grabbed my hips and slid all the way in. He was already cumming inside of me, right as I was so close to getting a release. He pulled out and then put the plug in me again, but it just fell right out. He put it in again and it fell right out, again.

"This plug doesn't fit anymore" he said and mark walked out and went into the other room. He picked it up and slid it in and it slid out again. "Well thats no good" he said as he left the room again. About a minute later he came back and put another, much larger plug into me. This one didn't fall out.

He walked out and then back into the room my head was in and started calling me a good boy. It was super hot. We talked a little but it was cut short when I heard the door open and shut. "oh damn a locked slut" he said, "Can I unlock this slut?". Mark looked me in the eyes with a smirk and then told the man back "absolutely not, I want this slut to cum from anal".

"Ah well" the man said in a deep, manly voice. He sounded super hot, and it sounded like he was a black guy. I felt the plug get pulled and it came out super slow. After another spanking, he said "You ready for this BBC bitch?" and before I could respond, he had already slid inside of me. This cock felt way bigger than any of the others, and it was actually a little painful to start. He spread my ass with his hands and slid in as deep as he possibly could and then stopped for a couple of seconds.

"Mmm I'm gonna stretch you out real good" he said as he slowly began to pull out again. The pain started to subside and it was quickly replaced with pleasure. I looked at mark and he was just standing there silently, smiling at me. The first 3 guys were kind of gentle, but this guy was just slamming me super hard. I could heard my ass cheeks getting clapped super loud with each thrust. It was super hot. I could feel the pleasure beginning to grow and grow, it felt like I was finally going to be able to cum. He kept jackhammering away and the pleasure just kept growing and growing.

"I'm gonna make you cum like a girl, slut" he said as he continued to pound me. It felt so good. He kept spanking me and squeezing my ass super rough and it was such a massive turn on. I felt myself getting really close to cumming, but, just like earlier, he was also getting really close. I could hear his breathes and moans and grunts and he was not going to last much longer. I tried to focus all of my energy on cumming and watching the cum from anal hypno on the tv, but right before I got there, he slid all the way in and stopped.

I could feel his cock spasming inside of me as he emptied out his balls deep inside of me. I was not able to cum from anal, and my frustration and denial levels had peaked. 4 guys got to use my ass to cum and I didn't even get to cum once. I could feel the larger plug get inserted into my ass again, and when it was in, he gave me one final spanking and left the room.

Mark left the room and I heard him say "anyone else?". After that, he came back in and put the blindfold back on me, and untied the chain. I pulled my head back out of the gloryhole and pulled up my pant, which had been around my ankles the whole time. He came around and grabbed the leash before guiding me out of the place again

While walking through the building, I heard someone tell mark "bring him back some time" and mark just laughed and said "we'll see what he wants". We got to the front of the place and I heard the big door open again. We went outside and a minute later we were back in his car and driving home.

15 minutes later, we arrive back home and I get out of the car and we go into the house. We're chatting about the experience and he reminds me that I still have an ass full of cum. I go to the bathroom and remove the plug, I look at it and its at least 3x the size of my old one. Mark is standing at the door and he laughs "you really got stretched out didn't you".

I sit down and the four loads come out of me into the toilet. My cock was still locked and leaky from the whole experience, but I was not able to cum again. I was so frustrated. I asked mark if I could use a vibrator to cum and he said "no, I want you to cum from anal only, slut"

He told me he would take me there again if I wanted and I just smiled and said "we'll see".