[MM] That time I tried a cock ring

This happened a bit over a year ago.

First, some important background: I’m relatively inexperienced when it comes to bottoming. I’m also probably 80/20 bi leaning toward women, but sometimes I just crave the D. When with guys, I’m always a total bottom—can’t even get hard if I (try to) top, but staying hard as a bottom feels natural. I’m also circumcised (this is important because I imagine it’d be more difficult to keep a cock ring on the head if uncircumcised). As with many bottoms, I’m always in search of that elusive prostate/anal orgasm(s). I got really close one time, but the guy unfortunately didn’t last long enough.

I bought an Aneros a while back and it happened to come with a vibrating cock ring as a free gift. I didn’t think anything of it first as I had never been a fan of cock rings. Oh boy, was I wrong to ignore them. It’s even funnier because the Aneros never actually did much for me other than slightly enhancing my regular orgasms while adding a bunch more cleanup/prep work.

I got a bright idea: Why not try it on the head of my cock? I put it where the vibrating part was on the top first and it was pretty… meh. Turned it over so the vibrating part was on the bottom and … unnngggggg. Yeah. Queue trying it in various ways for a while. So first, picture this: Me, watching porn like normal at my computer, the cock ring resting on the edge of the desk so it is sort of pushing up into the bottom of my cock. Oh yeah. That was amazing, no hands needed.

Then I got another idea. Why not use my bed and fantasize about getting pounded while kind of grinding into it? That worked too, although with a little bit extra effort (only when flat on my stomach which, coincidentally enough, also just so happens to be the same position that one guy got me really close to an anal orgasm in). Another huge perk I quickly found was that, where I would normally have to wait at least 10-15 minutes after jerking off before I could have another orgasm, in this way I stayed hard and could orgasm again within several couple of minutes. I think you all know where this is going, so I’ll skip ahead a bit. Sorry if the following isn’t the best written; I was trying to relay an experience moreso than a story so the dialogue and such is pretty light, plus this happened over a year ago.

Using only the best apps and having sublime standards, I selected a lucky gentleman to come over one fine evening for a few drinks. Let’s call him Joey. He turned out to be my best top compared to any before him or since (so far). We had already talked about what we were into, favorite positions, safety, etc. We were of similar age (early 20s), both in decent shape (slightly above average; not muscular, not overweight), went to the same college, and he was a total top. I also told him about my idea with the cock ring and that I was the type that if I came, I wanted it to be either from him making me cum or otherwise as long as it wasn’t me jerking myself off. I don’t like to touch my cock while getting fucked, unless the top is about to finish, since that makes the sensation focus a lot more on it rather than my ass. He also wasn’t overly hung which was perfect since I’m more tight than I wish I was, so anything more than slightly above average is a no-go. I’d guess about 7”, circumcised, and of similar girth (average/slightly above average) to myself without a curve. I did the full works—cleaned myself up, took care of my body hair (it feels so much more sensitive everywhere when shaved or, even better, epilated), etc. I also let him know that it had been like a week since I had last came, so if he got me going I’d likely turn into a complete slut quite quickly.

Come the night of reckoning. Joey came over. He was a bit of a reverse catfish, being quite a bit more toned than I expected. I’m about 5’9 and 145lbs. He was probably about 6’ and maybe 170lbs. A bit taller than me which was exactly what I liked. I always prefer to hang out a bit beforehand to help lower nerves and build a (very) basic connection, so we had a few drinks. We were hanging out on my futon with Lord of the Rings Extended Edition on and he pulled me closer. I looked at him and could see the same need in his eyes that I had, so I went for it. We started making out a bit, and I eventually pulled him over so he was on top of me, laying between my legs and grinding onto me as we kissed. My hands explored his back as well as his ass, pulling him tighter against me in anticipation of what was to come. I was already rock hard, and I’m sure he could feel it rubbing on his stomach even through our clothing. Especially seeing as I was only wearing thin, silky shorts that I usually wear while working out; there wasn’t any hiding through those.

After several minutes of him tonguefucking my mouth and grinding into me, he sits up and starts taking off his clothes. Naturally, I can’t let him just be naked alone, so I do the same. He finishes taking everything off first, and by the time I’m done he has his cock—now magnificently hard—in one hand while watching me. I could see the precum glistening in the small amount of light from the TV and city lights coming in through the windows. I don’t even ask before kneeling in front of him, each of my hands on his thighs. I needed to have it in my mouth. I needed to taste it and feel it. So I did, starting with a teasing lick up each side and then the bottom, stalling a little at the frenulum (bonus points if you know this) before doing a quick lick at the tip to taste his precum.

After sampling the deliciousness, I took as much of his cock into my mouth as I could. I don’t have deepthroating skills—I wish I did since it’s a bit of a dream of mine—but I took at least 4-5” in before I felt my gag reflex starting to act up and pulled back a bit, giving the bottom a nice long lick as I pulled off. To make up for this lack of skill, one thing I like is to avoid using my hands on his cock. Only my mouth. My hands held onto his thighs, sometimes drifting up to his belly as I took as much of him as I could. This continued for a while, and he eventually placed his hand on my head as he rested his head back and let out a slight groan, guiding me up and down his cock. During this, I was also fingering myself, starting with one before moving up to two to get myself ready and loosen up a bit.

It was 5-10 minutes of that. Maybe probably longer. I’m not sure because I was too into sucking his cock; I loved it too much and it tasted way too good. Did I mention that sucking a nice cock is one of the best things ever? He had a lot of precum and it was incredibly sweet. One of the benefits of living in a smallish studio apartment is that the bed is never far. After those dozen or so minutes of being on my knees in front of him, he pulled me up and whispered, *I’m going to fuck you so hard*, before kissing me. Say no more. We got up and made the five steps toward the bed, but before I got onto it he grabbed me and turned me around, pushing me to my knees next to the bed. At this point, I was rock hard and really needed his cock inside of me, but at the same time I still had the craving of sucking him.

Conflict management of that sort is never easy for me. Thankfully, he was more on the dominant side, in contrast to my more submissive side, and he knew how to direct. I knelt as he stood in front of me, once again taking him into my mouth as he guided me with a firm hand on the back of my head. Quite a bit more precum had already accumulated since we moved from the futon. I savored the taste, unable to help myself from letting out a small *mmmm*. My hands grabbed his thighs, wanting to pull more and more of him into my mouth. As I did this, he grabbed a condom I had tactically placed on the nightstand beside the bed. He pulled me up and pushed me onto the side of the bed, still half standing with my top half lying flat against it. He put the condom on and lubed both his cock as well as my ass, using his fingers to tease me a bit. Now, as I said previously, I’m tighter than I wish I was. I usually prefer to start in cowgirl since that helps me to go at my own pace at first, but at this point I was too into it to complain.

He grabbed one of my hips as he aligned and inched his cock forward, ever so slowly pushing into me. Being so tight, I had already told him we would have to go slow and ease into it at first. His head entered, stretching me and making me feel a little pain but nothing too bad. I felt his cock inching in, filling me up. I let out a small, involuntary *mmmm* as if tasting my favorite ice cream for the first time in a year which, well, that wasn’t far off since it had been a very long time. I felt his body against my ass as he was all the way in. He stayed there for about twenty seconds, completely filling me up and letting me adjust to his size. I did a few kegels to tease him. They must have worked, because he let out a small groan of pleasure.

Ever so slowly, he started small movements, moving his cock about half an inch out, then back in. It still hurt slightly, but less than when he first entered me. He did this slowly for about a minute, slowly working up how much he’d move. Half an inch, then all the way back in. Then an inch. Then an inch and a half. He worked up to the full length and, by that point, it didn’t hurt anymore at all. It was pure pleasure now, feeling him hold my hips as he slowly thrust into me. I was ready. I looked back at him and told him, *Fuck me however you want.*

That must have opened the floodgates in his mind because he didn’t hold back anymore. His grip on my hips became even more firm to pull me backward to meet him as he thrust forward. He sped up, fucking me harder with his full 7” nearly coming out before going all the way back in. The slapping sound each time he bottomed out in me turned me on even more, making me think, *Fuuuck he’s fucking me so hard*. It felt incredible, and a minute later he still wasn’t slowing down at all. My mind had already reached a state of ecstasy, not able to think of basically anything other than the feeling of his cock in me as he pounded me hard. He grabbed my wrists and held them in the middle of my back. He took his right hand and gave me a fairly hard spank, making me immediately let out a slight *oh* in blissful surprise. I had quite a bit of precum leaking down my leg by then, but I didn’t know that he was barely even getting started.

A couple of minutes (maybe? Time became irrelevant to me and I had no idea how long it was) of that continued with him bending me over the side of my bed, and by then I was bit of a mess, unable to get enough of his cock. Eventually, he pulled out and I felt empty. Thankfully, not for long. He told me to get up onto the bed on my back, so I did so. He took a little time to re-lube before he climbed on top of me between my legs and started kissing me. I could feel his cock sliding against my ass as we made out and he slowly ground against me, teasing without entering.

This only lasted a short time before he whispered to me, *Do you want it?* Of course, I immediately answered, *Yesss*. That must not have been enough for him, because he told me to beg for it. *Please… fuck me, have your way with me*. I was not one to avoid dirty talk; I loved it. He reached down and pushed his cock in, once again filling me up and making me let out a small moan at the surprise of how full I felt. We didn’t have to start out slow this time since I was already used to it, so he immediately started thrusting balls deep into me at a nice pace. My own cock was rock hard rubbing between us since he was laying against me. His mouth was against my ear, and I could hear his breathing and small grunts as he pounded into me. He wasn’t alone in that; even when I tried, I couldn’t stop myself from letting out heavy breaths and small moans each time he thrust into me. The fact that I couldn’t hold them in turned me on even more somehow, and my hands explored his back looking for anything to grab and hold, wanting him to fuck me deeper and harder. I grabbed his ass, trying to pull him deeper into me. His hands explored me as well. First with his left hand on the top of my head and his right hand cradling the back of my neck, at times turning my head so he could kiss me as he fucked me. We also had a bit of a laugh because even when his tongue was in my mouth, I couldn’t help moaning into his mouth. Then both of his hands grabbing my ass to pull me deeper onto his cock.

After a few minutes of this, he pushed himself up and grabbed my legs, putting them over his shoulders. *Unng*. This is one of my favorite positions because it lets him get deep. Not slowing down at all, he pounded into me as my own, still adamant, cock bounced around between us. This one really got me going, and my moans were getting a bit louder. My hands gripped his arms, desperate for something to hold onto. He must have noticed because he grabbed them, holding them down on either side of me. I was going crazy; I couldn’t do anything other than take his cock as he pounded away. This might have lasted five minutes or even ten or more. I had no idea because each thrust destroyed any thought I might have been processing. He told me, *Yeah, take that cock. You like it?* I somehow verbalized *yes* a couple times, but that was about the limit of my speech ability. He told me afterward my eyes kept rolling back which, well, I don’t exactly remember but have no reason to doubt it. There seemed to be a continuous stream of precum coming out of my cock at this point, making a mess all over my belly. My legs also started quivering. He noticed the huge puddle on my belly and slightly paused, asking if I came, but I said no and to not stop unless I said to, even if I did cum. He grinned. Little did I know what I was getting myself into with that.

He grabbed my legs and pulled them together, flat against his front. One arm held around about my knees, the other held a bit lower over my thighs. My cock was also trapped on the underside of my legs, so I could feel it sometimes bouncing against him as he thrust in. I thought he was deep when my legs were over his shoulders, but this surprised me even more. His strength also surprised me as he pulled me upward, my ass several inches off the bed as he pounded me. His hands switched to my hips, his arms still tight enough together to force my legs together as he held me off the bed and thrust in and out. I could see sweat glistening on his shoulders from the low light. He was already far beyond any of the (few) other guys I had been with whether it was amount of pleasure, how long he lasted, or anything else. By then I was like jelly in his arms, ready to do anything he said.

He slowed and pulled out, telling me to turn over onto all fours. I also put on the cock ring at this point. After turning over onto my hands and knees, he immediately pushed all the way into me and grabbed my hips, quickly picking the pace back up. I couldn’t stop myself from letting out a small *oh* or *mmm* on almost every thrust it felt so good, especially when he would spank me. I remember afterward I looked back and thought it made a lot more sense why women moan so much more than men. It wasn’t that I was trying to turn him on even more or anything like that. It was that I just could. not. stop. myself from moaning each time he went all the way in. And he went all the way in fast, pounding me hard with my moans almost continuous, melting across thrusts. The combination of his pounding and the vibrations on the head of my cock were nearly unbearable in sensation. He left one hand on my hip and grabbed my shoulder, pulling me up slightly and even harder onto his cock. He pulled my hair which was just barely long enough for a good grip; it’s fairly thick and I keep it long enough to style and such, but in previous encounters it was always a bit shorter so I had never been able to experience hair pulling. Turns out, it’s now one of my favorite things. I don’t know how long he pounded me from behind. It felt even longer than when he had bent me over the side of the bed.

He paused and grabbed my arms, holding onto them fully extended behind me so my chest was still held up off the bed. He only fucked me like this for a short time before going forward a bit, my face going straight into the soft bed. He let go and pushed me down so I was flat on my stomach, my cock pointing downward on the back of my thighs as my legs were tight together with the cock ring continuing to buzz along. Laying flat on top of me with his chest against my back and his mouth next to my ear, he thrust in and out. One arm was placed under my neck while the other was on my hip.

I could hear his fast breathing and feel the warm air as he exhaled. *Oh*. In this position, every single thrust was hitting my spot. I couldn’t help wiggling around a bit, trying to somehow get his cock even deeper inside of me by thrusting backwards onto him. I could also feel that something had fundamentally changed inside of me. A pressure was building, but not like a regular orgasm when jerking off. My whole pelvic area turned warm, then hot as the feeling spread out. My fingers tingled and were desperately searching for something to squeeze, finding only the sheets on the bed. I was acutely aware of how hard his cock felt inside of me and how full it made me feel. I never imagined myself going full porn star dirty talk, but I specifically remember involuntarily exclaiming quite loudly stuff like, *oh, oh, oh fuck, I’m going to cum, fuck me, fuck me* or similar. Somehow, he responded to this by going even faster and whispered into my ear, *Yeah, cum for me. Cum on that dick* as he grunted in effort. That was more than enough to send me over the edge as I announced, *Fuuuuuckkkkkk, I’m coming, I’m coming* and continuously let out loud moans, completely unable to control my verbalizations or my body as I quivered beneath him. He would later tell me that I moaned more than a lot of the girls he had been with, which I found kind of funny. The fact that he was entirely on top of me and in control, and that all I could do was keep taking it as he pounded into me through my orgasm, made it all the hotter.

I’m not entirely sure how long the orgasm lasted as it was basically just a sanctuary of pure bliss. Then came the surprise. I became somewhat more cognizant after I started to come slightly down from the orgasm-high, except… unlike when I had orgasmed while getting fucked before, it still felt amazing. I like to define it as the difference between cumming *while* getting fucked versus cumming *from* getting fucked. There was no comparison, as when I had orgasmed while getting fucked by guys before, I would tighten up and have to stop almost immediately after because it started hurting. This… this was entirely different. My orgasm had subsided, but my whole body still felt warm and every time he thrust fully into me was still ecstasy with none of the expected pain. The best part was that he hadn’t slowed down a bit, still pounding into me just as fast as he was leading up to my orgasm. I barely whimpered out, *Fuck… it still feels good*.

He adjusted his position so he was kind of on his knees straddling me, one hand still on my hip and the other on my shoulder as he continued to fuck me. Now, coming down from that orgasm had brought me slightly back to reality, but I was still cock-drunk and not in the best state to control myself. This shift in position seemed to restart the process, and needless to say I was quickly back to being a bit sloppy in the sound department. He moved his hands again, putting both of them onto my upper back and pushing me hard into the bed while continuing to pound me into it. Eventually, he dropped flat against my back again while still thrusting into me at a slower pace before whispering into my ear, *Where do you want me to cum?* Naturally, I answered back—with a few heavy breaths and soft moans interrupting my words as he kept thrusting into me—*Anywhere you want*. I could feel him smile against my ear and neck as whispered back, *Turn over.*

I obediently did so, and he immediately grabbed my legs and tossed them over his shoulders before pushing his cock all the way back into me. I gasped in surprise, not expected it so quickly yet also loving that he was just doing as he wanted. He tilted forward with his hands on either side of me and my cock still hard between us, but now with the cock ring off. Looking back, I probably should have left it on to see if I could have another orgasm, but that’s something to try again in the future. My own hands held onto his arms as he fucked me. I could tell that he knew it was his turn now, and the thought that I would be getting his cum and feeling his orgasm soon sent a mental wave of pleasure through me. I barely whispered out between heavy breaths and moans, *I want your cum*. He answered back, *You want me to cum in your mouth?* I had never sucked after getting fucked or otherwise had cum in my mouth as a result of a good fuck before, but it had been something I wanted to try for a long time. I wasn’t worried about cleanliness since he had worn a condom and I couldn’t fully deepthroat to the base anyway. The thought of it when he asked that pretty well sent my mind over the edge into full cockslut territory, so I excitedly responded with something along the lines of, *Yes, please cum in my mouth*.

He immediately picked up his pace, pounding me harder and harder. I could tell he was starting to get close, and in tandem my cock was also, once again, basically streaming a continuous river of precum over my belly. My legs were shaking uncontrollably—a lot more than the first time we were in this position—and even my hands had to hold onto his arms tightly to stop from quivering. My whole body felt like it was vibrating. I couldn’t stop myself from licking my lips and letting out an unbroken flow of moans as he kept going and going. He told me, *I’m getting close. Are you ready for it?* I enthusiastically exclaimed between all the, now quite loud, moans and heavy breathing, *Cum, please cum. Oh fuck I’m going to get cum in my mouth.*

All I could think about was his cock exploding in me as he continued to pound me while letting out small grunts on each thrust. A moment later, he exclaimed, *I’m going to cum*, and pulled out before ripping the condom off and standing up. At the same time, I jumped up as fast as I could to a sort of half-sitting/half-kneeling position and grabbed his cock, one hand on the base of it and the other gripping his thigh as I took as much of him into my mouth as I could. He put his hands on the back of my head, throwing his head back in pleasure as he grunted. I greedily sucked it as fast as I could while making sure to use my tongue for extra focus on the frenulum, wanting to taste it and feel it explode in my mouth. I didn’t have to wait long. After just two or three times moving my mouth up and down, I felt his cock tense up and the first spurt hit my tongue. I felt his hands tremble on the back of my head as they grabbed my hair and somewhat guided me. I let out a soft moan on his cock, feeling it rapidly throb as it unloaded stream after stream of hot cum. His cum was incredibly sweet and delicious. I kept sucking and sucking to work it out of him, unable to get enough as he grunted and groaned loudly. As his orgasm subsided and his cock started to throb less, I slowed down while continuing to use my tongue along the underside of his cock, still trying to work out as much of his cum as I could. I looked up at him and he was watching me, so I quickly pulled off and showed him my mouth before swallowing all of it. I quickly got back to work, taking as much of him into my mouth as I could which made him let out a bit of a laugh-moan and said, *Fuuuck, that feels so good*. I continued for another five or ten seconds, licking up and down each side to make sure I got any remaining cum off before kissing the tip.

Source: reddit.com/r/gonewildstories/comments/ugaspa/mm_that_time_i_tried_a_cock_ring