There's a Second Ring?!

I was fresh out of college and living on my own in Brooklyn. I was still deep in the closet, deeper in denial, and started working 60 hours per week at a job I hated to pay the bills and the student loans more importantly. So I was experiencing adulthood for real and the stress was getting to me.

I was horny and it had been a while since I had sex with a girl and even longer since I hooked up with a guy. I remember having gone out for karaoke with friends after work on Friday and getting home pretty wasted and horny. I was looking at porn, and eventually, it lead me to the Craigslist personals. Started with the ads posted in the Women Seeking Men, and responded to like two because they were all nasty women that I would never even let suck my dick. Then out of curiosity looked at some of the Men Seeking Men, the ones that had pictures were mostly hot guys, faceless of course (not much has changed in the online world). A lot of the posts were vague in what they wanted, but some of these guys were looking to get pounded or looking to "destroy" someone else's hole which really didn’t appeal to me.

I posted my own ad in the Men Seeking Women, then basically copy-pasted it into the Men Seeking Men section...you know, just to know. A few minutes later I passed out.

I woke up around 11:00 am Saturday, hungover. After a long shit, even longer shower I found myself drinking water and eating crackers checking the dozens of email responses I had from CL. I had forgotten all about it, but it was fun to read the responses. Few women responded, most of them desperate housewives looking to either be “my mommy” or looking to fulfill some sort of fantasy that I wasn't interested in. The guys that responded mostly just wanted more info, or were beyond the age I had posted I was interested in. A few seemed nice and I responded. Most of those filtered themselves out by either not responding or coming back with things like, "can't send pics" or "I only bareback" (which I was not trying to do).

One guy, who was 23, 5'8", black, 145lbs, sent a face pic along with a dick pic. His dick looked huge. At this point, I had only been with guys in the 5"-6" range, and not many of them either. He had said that he was a total top, into “everything mild to wild.” I told him I wasn't sure what I was looking for, but that I was certain his dick was going to be too big for me.

He responded by telling me we didn't have to do anything I didn't want to do, he'd be fine with “just kissing and mutual j/o, if anything else happens that's great, but no pressure.” The thought of playing with his dick made mine diamond-hard. So I agreed, and sent him my address, but not my phone number and real name because that would be too intimate.

When he arrived we went straight to my bedroom and with just a “hey” and a handshake of name exchanges we were on the bed and he started kissing me. I had only recently gotten over my lack of comfort with kissing other guys at this point so I was trying to be more into it and he made it easy, he was very sexy and wasn’t aggressive with his kissing.

Clothes came off quickly, shirts, his pants, my shorts. I was only in some grey Old Navy briefs and he was in some Hanes boxer briefs, both of us tenting hard...his obviously way bigger and it had my heart pounding. He could tell I was nervous so he kept the momentum moving forward, breaking our kiss and hooking his fingers in the waistband of my underwear, pulling them down as I lifted my ass off the bed to let him. He tossed them onto the floor and slid his underwear off even quicker, his dick made an audible thwack against his abs as he did.

Even more nervous now, seeing it in person was incredibly intimidating, he just smiled at me and got back between my legs. Spreading them wide so his dick could rest on mine and his balls on mine as we continued to kiss and explore each other's bodies. He smelled so good and every touch felt amazing, his skin was so smooth, very little hair anywhere, even his hard meaty dick was soft to the touch and dripping with precum which was now leaking onto my balls and that space between my balls and ass as his dick slipped down from time to time as we continued to frot and makeout.

It didn't take long before he started to move south, softly sucking a nipple as his fingers rubbed my hole eliciting a soft moan from me. It had just been too long, it wasn't that I wanted any butt action...just had been so long that my body just reacted that way. He kept moving down and engulfed my cock, took me all the way down without hesitation, and was quickly sucking like a pro. I was massaging his head as he did so, fuck it felt so good.

My dick fell out of his mouth and he started to jerk it, then licking and sucking my balls, more moans came out of my mouth, then his tongue went across my tight pucker and he got a barely audible, "mmm fuck" from me.

He kept at it, the perfect combination of jerking me and eating my hole, the pleasure was too much I was going to cum quickly...real quick. He could tell from the way I was breathing and my toes were starting to curl, so he backed off, coming back up for a kiss, his huge cock now rubbing against my hole as we sucked each other's tongues. He broke the kiss, "You like that?"

"Mmmhmmm" was all I could moan with his tongue back down my throat. He shifted his weight and I felt the tip of his dick pressing against my hole, my eyes shot open when I realized he wasn't asking about the rim job but asking about his dick rubbing at my hole. I broke the kiss this time, "wait, wait, wait," I mustered, breathing heavily, "I'm not ready, I don't think I can handle it, man." He just smiled at me, "No problem, we'll go slow," he grinned.

My brain was doing that math meme of confusion, the fog of pleasure had me confused if what I said equaled what he said as he spits on his dick and tried to push the tip in, it hurt like hell, I winced and put a hand on his hip, "wait, wait, wait," I inhaled sharp. "We need a condom and lube and...and...I don't know man, I've never taken anything that big," I tried to shut it down, my heart beating fast. I was so nervous, like a virgin about to experiment for the first time.

"I got you," he reached over to his pants and pulled out a condom and a packet of lube and something else. He started to stroke himself with a small amount of the lube, then rolled the condom on his massive dick and he locked eyes with me to smile. I don't know how I ended up here, this I'm fairly certain is specifically what I told him I wasn't down for, and yet here we are, his huge cock head now rubbing around my hole expecting to get in.

He leaned over and grabbed a small brown bottle, shaking it like it was spray paint, he opened it and brought it to my face, I didn't know what it was but there was no way I was going to drink something from an unlabeled little bottle like that so I turned my head and shifted out of the way. "What is that?"

He laughed, "It's poppers, gives you a quick rush, you want some?" He asked and then I watched him plug one of his nostrils and inhale deep, then he did it again on the other side. "It will make it easier," he told me while his dick nudged my hole again. "Ok," I took a long pause, "How do I..." I started to ask and he quickly put the bottle under my nose, closing one side, and told me to inhale deep. I did, and it was the quickest high I ever had, not that I had much if any experience at that point, but wow. My head started spinning, my heart racing more than it was, everything got blurry for a second as my head relaxed into the pillow and the rush took over my body. I was honestly concerned I had just made a huge mistake and that I was about to pass out and be taken advantage of. But it quickly leveled out and I just felt relaxed and horny, he told me to go again from the other side, and I did and took an even deeper inhale this time. Again the rush took me, even harder this time.

"Oh man," I said, my hands went from pushing his hips from entering me to running through my hair as I enjoyed the sensation. I felt him start to enter me, and it…it didn’t hurt, suddenly felt so good, not easy, but all the good feelings felt better and the sting was a much more subtle almost dull feeling. He took his time and just entered slowly until he was most of the way in. We started to kiss again, I felt so full, more so than I had ever felt with other guys. He started to pull out and push back in, small, gentle thrusts, just enough to help me loosen up a little more. Which was easier now that he was inside and my brain stopped panicking that he would rip me open.

"I knew you could take it," he smiled at me, this time he thrust a little harder and to my surprise deeper, hitting something inside me that I didn't know existed, this felt weird. Like he had hit the bottom of how deep someone can go inside me. He thrust again and again, he hit the cap and it stung but also felt good, like when someone pushes on your belly button.

"You're really tight," he said almost out of breath, working hard to thrust into me. I just nodded, my face probably showing the slight discomfort every time he bottomed out. "You want some more poppers?" he asked, thrusting and hitting that new spot deep inside a little harder this time. I just nodded.

He shook the bottle and just like before he did all the work, under one side, then the other, and then he took some quick hits and capped it off. As the rush took over me he started to thrust again, harder now and I felt it hit that cap deep inside, but then…he pushed through, all the way through, oh my god this was a new amazing feeling, my eyes rolled into the back of my head and I moaned. "Yeah, open up for me," he whispered, thrusting harder and deeper, pushing through that deep ring with every thrust, holy shit it was intense.

I didn't know what it was at the time, but he had popped the cherry on my second ring, it felt amazing and weird all at the same time. I started to jerk myself off, taking advantage of this moment of sexual bliss as he enjoyed my tight hole with each sensual thrust.

It didn't take me long, I felt that I was about to boil over, "I'm gonna cum," I said. He thrust deeper and with more determination, "Do it." He fucked me, not hard, but with deeper faster thrusts, focusing on my pleasure, fucking the cum right out of me, my toes curling my head back deep into the pillow and eyes closed as the orgasm rushed through my body like the poppers. Cum exploded everywhere, all over me, definitely some landing on the pillow next to me, I gasped and wreathed through the last of my orgasm.

I was out of breath, but he kept fucking me. Very quickly it went from the most amazing feeling in the world to feeling like my first time getting fucked even though the only thing that had changed was my own orgasm. I didn't want to blue ball him, I had been with girls in the past who would not let you finish and I certainly didn't want to be that guy, but man it was like my ass was on fire and he couldn't even reach my second ring because my ass was clamping down on the intrusion of his massive cock. "Are you close?" I asked while wincing, clenching my teeth.

"Kinda," he said out of breath.

"I don't know how much more I can take man," I warned. "Are you…can you cum quick?"

"I can if I take this condom off?" he said and kissed my neck while thrusting hard into me.

"Yeah, fine," I said just wanting it to stop and not be the bad guy.

"Yeah?" he looked me in the eyes.

"Yeah, just cum quick," I told him.

He pulled out all the way and relief washed over my body, I heard the condom snap off and I saw it tossed to the floor. He added some spit and started feeling for my hole again, which had now mostly sealed shut like a blast door on the Death Star. He reached quickly for the poppers, giving me more, the rush was amazing again, then the other nostril, and I let my legs fall to his sides so he had better access. "Another, deeper, and hold it as long as you can this time," he said and I listened taking an even deeper hit, nearly passing out but the rush was amazing!

I felt him spit again and start to push in, not nearly as easy as the previous time when I was still horny, but he got in, then after a few thrusts he hit that second ring and it stung like a bitch this time. Like hitting yourself on a bruise. After a few of those deep thrusts, I winced, "shit, are you close?"

"Getting there," he said, thrusting and kissing my neck. Holding on to my shoulders, pulling me into his thrusts. "Can I cum in you?"

The sirens went off in my head, **he's not wearing a condom**, thrust, thrust harder, thrusting deeper into that second ring. "You don't have anything do you?" I asked with naivety.

"No," he breathed into my ear, thrusting faster and deeper.

The poppers were wearing off with every thrust, I just wanted it to be done, so I shook my head from side to side, "if you want to, just cum quick," was all I could think to say.

It didn't take long, he thrust a few more long deep sensual thrusts, "I'm about to bust," he warned one last time, hitting deeper than before, his dick swelling to an impressive girth, "Oh fuck," he whispered as he pulled me tight and slammed into me, his cock pulsing as he nut deep inside me. "Mmm, ungh…mmmmm....mmmm," he moaned and collapsed onto me, smearing my cum between us as he caught his breath.

"Fuck," I whispered, catching my breath and taking it all in. Feeling his dick slowly soften inside me, leaving the second ring and then quickly out of my hole altogether.

"That felt so good," he mumbled, as he pushed himself off me and the bed. He went to my bathroom and cleaned himself up quickly, then he was getting dressed before I had even caught my breath or sorted a thought. "We should do this again," he smiled at me, pulling his shirt on. "I have to run," he smiled, and then walked out and I heard him pull the outside door behind him.

I had no intention of letting that happen again. At least that was what I told myself as I went to shower and gather my thoughts.