Casey - The Regular

Tim is my backup hookup. We met at a bar about a year ago, closing time, and I was drunk, needing to have sex. He's not my usual type. He's decent-looking, but he's ten years older than me. I'm 23, so I usually stay on this side of 30 when it comes to sex. At closing time, you have to make the choice to go home with a Tim or go home and jerk off, and I went home with Tim. 

Sex with Tim was ok. I topped him, we both got off, and that’s really all I wanted. He gave me his number and told me to call him the next time I was horny. I told him I would. Of course, I fully intended to throw his number away as soon as I got back to my apartment.

A few days later, when I went to do laundry, I found the number in my jeans and decided to keep it, just in case. I didn’t have to call, and it’s good to have a backup.

I ended up calling him a month or so later when I was home alone, drinking, and he invited me over for round two. This became a semi-regular thing, me calling him every six weeks or so if I was in the mood and looking for something quick and easy.

It's usually decent sex. Decent enough, anyway. I'll go over, we kiss, strip, fuck, we both cum, then I'll dress and go home. He sometimes asks to fuck me after and I tell him maybe next time, but I only bottom when I’m in a very specific mood and he doesn’t get me in that mood. He’s turned on by my body enough that I don’t think he cares that we don’t have any connection other than sex. I make a point of keeping my body lean and cut, burning out my abs every morning. During sex he's always enjoying the lines of my muscles and rubbing his hands up and down my abs while I fuck him or he rides on top of me. He's in decent shape, but softer than I usually look for. I do like the body hair, though. It's just enough to make him look masculine but not ape-like. I barely have a dusting of hair between my pubes and my naval, which is probably the reason I try to stay as cut as possible; otherwise, I’d look prepubescent.

In June of 1996, my roommate celebrated his 24th birthday at a bar not far from Tim’s place, which is nice because I went without jerking off for a few days, hoping I’d get laid tonight and knowing I had Tim as a backup if I didn’t. For a good portion of the night, I was chatting with this sexy friend of my roommate, from his office, only to find out after about two hours into the conversation and two Long Island Iced Teas that he’s married…to a woman. 

I he didn’t give off the impression that he was straight, although I did get the feeling he was a strict top, and I was so turned on by him I was willing to bottom. Over the course of two hours I had built it up in my head that we would be going back to his place and he’d be fucking my brains out, but that ship has sailed.

Around closing time, after I finished my third Long Island, I was pretty wasted, but still had full balls and needed to get laid, so I picked up the payphone and called Tim.

“Hello?” Tim answered after a few rings.

“Tim? It’s Casey,” I tried my best not to slur my words, plugging one ear to hear him over the music.

“Oh, hey, what’s going on?” He asked in a sultry tone, knowing exactly why I was calling so late.

“I’m out celebrating my roommate's birthday. What are you up to?” I had to shout over the jukebox.

“I just got in, had a going away party for a coworker, you know how it is,” he knew I didn’t care for the details. “You want to come over?”

“Yeah, I was thinking about it. The bar I’m at is not far from your place, and I thought…why not give you a call?”

He laughed, “Why not come over then?”

“If you’re up for it, I can be there in twenty minutes,” I told him.

“Yeah, that’ll give me time to shower,” he said, a little more excited than when he answered.

“Alright, I’ll be over soon, then,” I told him.

“Ok, see you soon, sexy,” he hung up before I could respond.

I paid my tab, told my roommate I would be out late, and headed out.

I walked the dozen blocks to Tim’s place. I thought it would sober me up a little, but it just pushed the Long Islands more into my blood stream and the dirty thoughts about getting fucked into my head, making me even more horny.

Tim buzzed me in as soon as I hit the buzzer, and I stumbled into his building. He lives on the third floor of a walk-up, and I struggled to get up the stairs without tripping, which I found hilarious.

“I need to pee,” was the first thing I said to him.

He chuckled, eyes glazed over from partying with his friends, pointing towards the half-open bathroom door, “Go for it.” His face was all red, clearly he had just as much to drink as I had, but he was still happy to see me, his white Calvin Klein briefs didn’t hide his bulge well. He’s at least seven inches, circumcised, and on the thick side, another one of the reasons I’ve always topped him.

He wasn't in the living room when I came out of the bathroom, so I went to the bedroom. He was naked, on the bed, stroking his hard dick. I grinned and quickly stripped my clothes off, climbing into the bed, straddling him. I starting the sloppy makeout session, sitting on his dick and rocking back and forth on it, teasing him but more focused on how good it feels on my hole. He leaks a lot of precum so I love rubbing the head of his cock on my hole, but I never let him push in. I usually tease him and let him think he’s going to fuck me, then I get off his lap and fuck him. While dry humping tonight, he kept trying to push into me raw, but even drunk I have my wits about me and ride up with his hips, barely keeping his head from popping into my very horny hole. It does feel good, though, the tip just kissing my tight pucker.

I wasn’t planning to let him fuck me, but something came over me as I kissed him again. “You have a condom?” I broke our kiss.

He reached for one on his nightstand. I grabbed the lube. Quickly applying it to my hole, adding some to his cock and teasing my hole a little more with the head of his hard dick before he reached around me and stretched the condom over his cock. I added more lube to his sheethed dick and started stroking him back to full erection. I lift up on my knees, pointing his dick at my hole, one hand on his chest to hold me steady and tried to ease him into me. I’m not an experienced bottom but I know how to breathe and get a dick in my hole. It stung a little, but I slipped it in a few inches at a time until I was fully impaled, sitting on his bush.

I leaned forward and kissed him, our tongues dancing between our mouths as I let my hole relax and get used to his girth before I sat up and started riding him. My left hand on his chest, my right hand on my dick, I started rocking my hips, grinding on his lap. Slow at first, trying to find the right angle to get the most pleasure out of that big dick. “Mmmm,” I hummed as my cock reacted to the angle of his dick inside me, pleasure creeping into my body as he gently thrust up to meet my ass. 

He was a little too focused on my pleasure and after a minute or two of riding him I noticed he was loosing his erection and my tight ass was pushing him out. So I reached back and started stroking him off to get him hard while I continued stroking myself off.

“Sometimes the condom makes me go soft,” he mumbled.

I waggled my eyebrows at him, “I’ll get you hard,” and continued to stroke us both. I could feel his dick reacting to my stroking, but not quite as hard as he was before the condom went on. He kept rubbing his hands up and down my abs. I gave his cock a hard squeeze as I stroked him, he felt a little harder so I sat up and put him against my ass, pushing him in he got past my outer ring and I dropped down on him. I was able to ride him for only a few seconds before my tight ass pushed him back out because he wasn’t hard enough. I quickly started stroking him again, getting frustrated in my drunken horniness.

“Do you just want to fuck me?” He offered, reading my frustration.

I smiled, “It was feeling really good,” I told him.

He smiled, reaching back behind me, pulling the condom off and stroking his dick back to life. It got pretty hard pretty fast and he started thumping it on my ass.

“Do you want to put it back in?” I asked, still stroking myself.

He nodded, stretched the condom back over his dick and held it for me to sit on. At full strength, his cock was a little more rigid and I struggled to get in and adjust to, but, “Mmm, yeah,” I moaned as I felt him stretch my insides and his stronger erection pushed deeper inside me. This time, he started rocking his hips up into me. It started feeling really good and I rocked back to meet his thrusts, “Oh fuck,” I mumbled stroking my dick faster as I adjusted my knees on the sides of his ribs so I could get more of his dick with each thrust. I felt my orgasm drawing closer, but only for a fleeting moment. With each additional thrust, I could feel his girth and length decreasing, getting softer until it was pushed out by my tight sphincter. 

I was desperate to cum from getting fucked and I huffed, reaching back and started stroking him again. The room was spinning a bit from the Long Islands and my horniness had me so close to an incredible orgasm but I was getting frustrated with his ability to maintain an erection and he could tell.

“You could fuck me, if you want,” he offered again.

I was too turned on and too blinded by how close I was to having a prostate orgasm. I hadn’t bottomed in almost a year, and I haven’t cum while getting fucked in at least two years; I needed this. Before I could think, the words flew out of my mouth, “What if we take the condom off and put it in bare?” I continued to stroke us both.

He grinned, “Well…I was tested recently and came back negative, so…we could, if you want.”

I ripped the condom off his dick and started stroking him furiously. Leaning over to kiss him until I could feel the rigidity of his dick thrusting into my hand in no time, begging to be put back into my hole. “You ready?” I broke our kiss.

“Uh-huh,” he nodded, his hard dick twitching in my fist.

I aimed his raw cock at my hole and slid my ass down on him. “Ungh,” I groaned. It was so thick now, and could’ve used more lube, but his head was pulsing in my guts and his girth teasing my prostate, and that’s all I needed to start riding him again.

“Oh fuck that feels good,” he moaned, gently thrusting up into my ass.

I started rocking my ass on his dick, holding myself up with my left hand on his chest as my right hand flew up and down on my own six inches of cut meat. “Fuck that feels good,” I moaned, feeling his flared head pegging my prostate with each new thrust.

“Yeah, you like that?” He moaned, trying to rock his hips in time with mine to give me more pleasure.

“Uh-huh,” I whimpered, feeling so good with his raw cock inside me, his precum leaking into my chute and adding that little bit of lube with each thrust. My heart was pounding; I could feel my orgasm building as we both picked up the speed. “I’m about to cum,” I warned him and he started thrusting harder into me. 

“Yeah, baby,” he moaned, his hips hitting harder against my ass.

I felt my prostate swelling against his thrusting shaft as my tight hole clenched down around his girth, thicker in the middle, so each thrust in and out felt a rhythmic pressing against my button. One from his head pounding into my guts, and the other from the thickness of his shaft. I rocked back and forth on him, spreading my knees wider around his ribs to get him even deeper into me. Rocking my ass on his shaft again, deeper, and deeper, tickling my insides with thrusts of pleasure. Then I felt it, my toes curled as my muscles flexed, “Oh fuck, I’m cumming,” I warned in a quiet breath as my balls drew up and splattered cum all over his furry torso, dumping pump after pump of my spunk all over him as he continued thrusting up into me. My body trembled from pleasure, “Ungh…mmm,” I huffed and moaned, finally sitting on his cock and catching my breath and groaning as he tried to continue thrusting into me.

He only gave me a few seconds to recover before he started rocking his hips into me again. The pleasure quickly faded and the sting of having a cock thrust into my tight hole was returning. “Ow…ungh,” I groaned. “You didn’t cum?” I asked, knowing from how hard he was, that he hadn’t.

“Not yet,” he started thrusting hard into me.

I was glad he didn’t shoot in me, but fuck this was too much. “Are you close?” I groaned.

“Getting close,” he thrust deeper into my guts, that pang shooting deep into my stomach.

“Oh fuck, how close?” I asked, not wanting to give him blue balls like guys have done to me after they cum, but fuck this stings. I’ve never been on the receiving end of cumming before the the guy fucking you cums, I swear his dick is getting bigger with each thrust.

“Get on your back and I’ll cum real quick,” he suggested, pausing his thrusting into me.

I huffed, “Ok,” and nearly launched off his dick. I flopped down next to him on my back. He took the opportunity to relube, then pushed his stiff cock between my legs and the head popped into my hole and it stung worse than the first pump.

“Ahh, fuck,” I groaned.

“Sorry,” he pushed my legs back, my knees at his elbows as he quickly sank the rest of his inches into me with a bit of carelessness and way to fast.

“Ahhh... shit, that hurt,” I groaned, feeling that sting of reentry burning my hole and shooting into my guts.

He chuckled, “Sorry, it wouldn't go in. ” He leaned over me and started kissing me, and immediately went to full speed with his thrusting. The pain didn’t go away, but there was a hint of pleasure; his girth was still pushing on my prostate, and that felt really good, but the rest of it was too much.

“Ahh, shit, it really hurts,” I groaned. He thrust a few more times. “ungh... can we take a break?”

He thrust a few more times, even harder, and deeper, “I’m getting close,” he said.

“Ungh, how close?” I was digging my hands into his thighs, trying to lessen the thrusting, but he was on a mission. Each thrust digging deeper than the last, my ass clenching tighter and tighter.

“Real close,” He huffed, thrusting harder, leaning over me even more and kissed me reasuringly as he dug his dick deeper into my guts. I felt it pegging my prostate which did feel really good, but oh man, my ass was burning from stretching to accomodate his size increase as he continued to get harder and thicker since the condom came off.

I spread my legs wider in the air as he adjusted his knees around my hips and fucked me in small but deep thrusts. I moaned, being stretched to my limits. “Ungh…Are you close?” My voice begged for relief.

“Real close,” he held me tighter, fucking me harder.

“Ow,” I cried out, as my toes curled from the pain and pleasure mixture of his dick digging deeper into my guts and stretching my hole with a grind and thrust with each quick rock of his hips. I was about to shove him off, "Ow," I groaned, I couldn’t take another minute.

“I’m cumming,” he whispered in my ear, his voice pleading for me to let him finish. He laid his chest flat against mine, kissing me slopily and breathing heavily as he continued fucking me for another dozen thrusts. Each deeper than the last, rearranging my insides with his swelling head as he grunted and I felt the last thrust stretch me a little more forcing a moan out of me as his cock swelled to what felt like twice his natural size and twitched inside me as I felt his hot release coating my insides like a fire hose, putting out the burning of my raw skin against his. His next thrust slamming into me felt so good I couldn’t help but moan as his cock was coated with his slick cum and it shot even more into my guts with a heavy breath into my ear.

“Oh, mmmm,” I moaned as I felt my insides tremble from the sudden release of pleasure from his cock, that pain instantly gone and my body absorbed his orgasm to make it my own. “Ungh,” I groaned in satisfaction as his hips finally stopped thrusting and he stayed deep inside me, his cock still dumping the last of his load inside me with small pulses.

He rested for only a few seconds before he pulled out of me, his cock almost instantly soft, slick with the juice from his balls. “Damn that was good, baby,” he chuckled, sitting up.

I quickly wiped the wetness from my eyes from the intensity of his fucking. “That was intense,” I forced a smile, looking at my cum dripping down his chest through blury eyes.

“And don’t worry, I’m completely negative,” he added.

I know it was supposed to be reassuring, but the fog of sex was quickly clearing from my head, and it just sounded like a weird thing to say. I groaned, quickly rolling off the bed, struggling to stand. A combination of the Long Islands and the most extreme fucking I’ve ever had. “I have to… use the bathroom,” I told him, clenching my asshole as I wobbled to the bathroom.

I flushed his juice down the toilet and checked to make sure I wasn’t bleeding; thankfully, I wasn’t. I washed my face in the sink, shaking my head at my reflection for doing something so stupid, and with Tim of all people.

I went back to the bedroom and started getting dressed for my walk of shame home.

“You really don’t have to worry, I can show you my test results if you want,” he said.

I shook my head. “It’s okay; I trust you,” I lied. I just wanted to go home and try to erase his number and tonight from my brain.

The next morning, I promised myself, “never again.” The problem with going bareback with a guy is once you let him fuck you raw once…he’s going to want to do it every time.