No Regrets

by Wander Wonder

3 Jun 2011 4595 readers Score 8.7 (54 votes) PDF Mobi ePub Txt


'Hey, Clayton, are your parents here yet?' Jimmy asked.

I looked up from my computer. 'Naw, they're coming tomorrow. Yours?'

'Same.'

I nodded. Jimmy looked around, one hand holding the cardboard box closed.

'Here.' I handed him the packing tape. 'My momma's going to help me after graduation.'

'Thanks.'

I watched his back for a moment. Jimmy and I had been good roommates. He was going to work for his dad's marketing firm in June. I was going to start my job teaching P.E. at an epically backwoods junior high school in Lickin, Missouri. We had nothing in common. I'd given him the predictable nickname 'Jimmy Dean' and he had come up with the system for sharing and replacing food. That was pretty much the whole of our relationship. We didn't talk much and we hung out in completely different circles. Still, things like knowing what he had been looking for without him saying anything - that made me feel like it hadn't been such a bad thing to room with Jimmy for four years instead of moving in with a friend.

'Aw, fuck it,' Jimmy exclaimed suddenly. 'It's at the bottom of the damn box.'

I didn't turn around. 'Just use my toothpaste, man.'

'Cool. Thanks.'

I yawned and shut off my computer. Jimmy had some honors frat thing before the ceremony tomorrow, and I was meeting my parents for breakfast in the morning. We both had to be up early, which maybe was why we were both in our room the night before graduation. I should have been out getting stoned and wasted. Instead I had helped Jimmy pack some of his stuff, watched Boyz n the Hood, and was going to bed at 10:30 p.m.

I was under the covers before Jimmy came back from the shower and turned out the light. We had tried bunking our beds to save space freshman year, but Jimmy tossed all the time, so we've slept across the room from each other ever since. We both stared into the darkness and let our eyes adjust. The moon lit what it could from behind the blinds, highlighting the bare walls, the boxes piled on top of each other in the corner, and Jimmy's empty desk.

'This is weird,' I said, breaking the stillness.

'The room is so empty,' Jimmy commented.

'Yeah, it's like when we first moved in,' I replied.

'Except this time, like, it's more permanent. Our shit will never be in here again.'

We both lay in silence for a moment. Jimmy was right. We'd moved out of three other dorm rooms. We'd had this moment before, when our stuff was being packed away, when the halls were quiet; this was a heavier feeling. Jimmy and I had made no promises to keep in touch. We weren't friends, really, but we had been awesome roommates. This was the end of an era.

'I'll miss you, man,' I said suddenly. I had never said anything with more sincerity in my life.

Slowly Jimmy sat up, blanket spilling down his shoulders. 'Come here, Clayton.'

I heard it in his tone then. Maybe I had missed it before, or maybe it hadn't been there before. I got out of bed and padded over to his. There was a weird kind of calmness covering the room. We weren't breathing hard or anything and I didn't have butterflies. My skin tingled, though, when Jimmy reached his arm around my shoulders and pulled me in. I don't know know if he kept his eyes open, but I closed mine.

Jimmy kissed me. Jimmy kissed me after four years of living side by side, dating girls, only yelling at each other to clean shit up, hating each other's music, never having a real conversation, and deciding our life plans independent from each other. Jimmy kissed me and I opened my mouth. I pressed his lips open with mine and ran my tongue over his. Jimmy kissed me, and I kissed him back.

No, that wasn't exactly it. Jimmy wasn't just kissing me. We were making out. I was climbing into his bed and he was scooting over for me. Jimmy was tangling his pale legs with mine and I had my hand on the back of his neck. He was wrapping an arm around my waist. I was pressing my groin to his, tangling my fingers in his auburn hair, and stroking his tongue with mine. Suddenly we pulled apart and gasped for air.

'This is so stupid,' Jimmy breathed, laughing a little.

I settled my head on the pillow, just far away enough from his to be able to focus my eyes. 'Yeah, this is a fucking waste.'

Jimmy trailed his fingertips down my side. 'Are we really going to do this anyway?'

'Yeah.' I didn't have to think about it.

'Like all the way? Like fucking?'

'Do you want me to, like, actually fuck you? In the butt?'

The brown eyes staring into mine blinked slowly. 'Kind of.'

'Then I will.'

Jimmy smiled a little. ''Kay.'

I pulled Jimmy's boxers off, wondering if we'd always been so comfortable around each other because there had been some sort of underlying attraction between us. Jimmy stroked my back as I kissed his flat stomach and gently massaged his balls.

'Do you remember our freshman year,' he said, 'when you knew it was my birthday even though I didn't tell anyone? I thought you were psychic.'

'Whatever,' I responded between licks and kisses. 'I didn't label that beer or anything. It was a shitty gift, anyways.'

'Not for a freshman it wasn't. Still,' Jimmy laughed. 'I didn't ever think you'd be sucking my dick.'

I shrugged, not wanting to remove my lips from the first cock I'd ever had in my mouth. It was fucking good. It felt so raw, so primal to be doing something like this. A man's dick is one of the most precious parts of his body, and I was trying to fit Jimmy's down my throat. There were a few girls out there who actually seemed to enjoy sucking cock, and I could understand why. I had the power. Jimmy was at my mercy.

'Oh god, Clayton,' he moaned when I pulled back, sucking hard. 'Oh, fuck, that's so good.' His fists clenched. 'Fuck yes. Oh, god.'

I tugged his pink balls and bobbed my head up and down. Jimmy stroked my head and shoulders, breathing heavily. I was careful at first, trying not to touch him with my teeth, but when Jimmy started rolling his hips I got bold. Lipping at his nuts, sucking one into my mouth while jacking him, stroking at his taint, then his asshole - I could manipulate my roommate like a marionette. It surprised us both a little when I got bold enough to go for Jimmy's ass with my tongue. He held on to his knees to give me access and panted, occasionally heaving an 'oh, fuck' into the air. It was almost embarrassing how loud we were, and even through the lust that had my face buried in another dude's ass, a white boy nonetheless, I was grateful that we'd waited until everyone was gone for the summer.

I had barely figured out how to get half of Jimmy's dick down my throat when he tugged at my hair. 'Stop, stop, I'm gonna come,' he said.

'Naw, it's cool, man,' I replied. I figured it wouldn't be all that bad as long as I didn't try to inhale at the same time.

'Thanks, but we've still got to get up in the morning.' Jimmy let go of his legs and scooted back, preventing me from diving back down on him. 'I'm good with just coming once tonight. Besides, you have stubble. I don't want to be all raw down there.'

'Got it. Make it a big one, and then shuteye.' I nodded in agreement, then burst out laughing. 'What the fuck is going on?'

'I know, it's totally weird that we're doing this,' Jimmy said, grinning.

'I was about to ask if you had packed your condoms,' I snorted.

'Fuck no!' Jimmy retorted. 'You think I want my mom opening up that box? Like, she knows I've had sex, probably, but we don't fucking talk about it. I was leaving them for you to deal with.'

I reached over to the dresser between our beds and opened the second drawer, dragging my erection over my roommate's stomach on the process. Sure enough, there were a couple left. Plus there was the unopened bottle of lube that Jimmy's polo buddies had given him as a gag gift for his birthday.

'Gimme the condom,' Jimmy said. He got on his hands and knees to roll it onto my cock with his mouth, which felt fucking amazing. He compressed his lips as tightly as he could on the way up, tugging my nuts a little while he did. My hips bucked before I could think to not choke him.

'Where the hell did you learn that?' I panted.

Jimmy grinned, jacking me slowly. 'I saw it on porn, dude. Where do you think?' He turned round and grabbed a pillow. 'Now you be gentle, you hear? Don't try to shove that monster in me all at once.'

'Aye aye.' I opened the bottle of lube and poured a generous amount on my fingers. When I used my left hand spread the cheeks apart, Jimmy's small hole winked at me. 'Chill, bro. Just tell me if anything hurts.'

'Okay.'

Jimmy put his head into the pillow. I stroked his asshole once, twice, then dipped my finger inside. I could feel the muscles tense, so I rubbed the small of his back. Jimmy relaxed. It was completely surreal; working one, then two fingers inside of him. The third finger was the tipping point. I listened to his pained moans changed to lusty 'uhn's' and 'mm's' in the dark room, especially when I curled my fingers down and massaged the bump of his prostate gland. Jimmy trembled, gripping the sheets while he leaned into my touch.

'Fuck.' Jimmy dragged the word out. 'Fuck me.'

'Are you sure?' I asked as I kneaded his white buttocks with my free hand. I hoped to god he didn't say no - I was hard as iron, aching to get off and turned on to the point of torture.

Jimmy nodded and spread his knees even farther apart. 'Yeah, I want it.'

'Thank god,' I replied, getting a laugh from my roommate. 'Breathe, okay, bro? I'll go slow.'

I spread his butt cheeks, noticing that Jimmy's asshole didn't look like such an impenetrable fortress anymore. The flesh beneath my hands was firm, but damn was there a lot of it.

'You know, Jimmy,' I commented, jiggling the pale mounds, 'you have a certifiable bubblelicious ass.'

Jimmy laughed. 'Quit fucking around.'

'No seriously,' I insist, pushing my cock head against the tight ring of muscle, watching it slowly yield to me. 'I never said anything because - ' I had to pause or explode. It was so hot inside Jimmy's ass. I only had the tip in, but it was the best fucking thing I had ever felt in my life, ' - it would have been totally gay, but you really do have like a Jennifer Lopez ass.'

'This is as close as you'll ever get to fucking her,' Jimmy gritted out. His hands were clenched and his toes were curled.

'Jimmy, does this hurt?' I asked, concerned. If he started bleeding or something I really would stop.

Jimmy laughed, a burst of sound tinged with pain. 'Holy fuck, yes, but keep going.'

'Really?'

'I have a dick in my ass, Clayton,' he snapped. 'I need time to get used to it.'

I blessed all the lucky stars for not making me test my self control. I slid in, slowly, making sure that Jimmy was as relaxed as possible by running my hands over his back and sides. He braced himself on one arm so that he could pull on his dick, which told me it didn't hurt so badly anymore.

'I feel like Wesley Snipes,' I told my roommate. 'Or Sidney Poitier, except I've already met your parents.'

Jimmy laughed, more easily this time, and the sudden release of his internal muscles is enough to let me slide me cock all the way into him. We groaned in sync.

'Does this mean that I've gone black, and can never go back?' he huffed. 'Or does getting fucked not count?'

'Shut up, white boy,' I commanded with a small thrust. 'You dated Teja Ann for like a year, and she's the ghetto-est girl I know.'

'So I know who to blame for this,' he replied, jiggling his ass. It was like an earthquake around my dick, sending aftershocks through my body.

'Holy shit,' I breathed.

'You like?' Jimmy asked, pushing himself up to do it again.

Was he kidding? It felt like his ass was trying to pull the cum from my balls. 'Hell yeah, I like.'

'How about this?' Jimmy watched me over his shoulder as he ground his ass in circles.

'Shit yes.' I had to clench my ass to keep from shooting off then. I didn't know from where Jimmy got his dirty dancing skills, but he could move those hips of his. 'How are you doing on that end?'

'Good, good,' he chuckled. 'Doesn't really hurt anymore. Actually, it feels pretty good if - '

I grabbed him by the hips, angled my dick downward, and thrust. Jimmy's arms gave out.

'That, yes, oh fuck yeah,' he gasped into his pillow. His voice was shaky. 'Holy shit, I think you hit my prostate.'

I pulled out slowly, until just the head of my cock was left in his tight ring, and thrust my pelvis again. Our bodies met with a smack. Jimmy moaned wordlessly and I did it again. It was a million degrees inside his ass. Every time I pulled back Jimmy tightened up as though he was trying to keep me buried in him. The pressure on my cock was unbelievable - so much tighter than pussy.

I was sweating like crazy, so much that it was rolling down my chest. Jimmy was humping back at me, trying to stuff himself full of my cock, and jacking himself like crazy. Any second I was going to blow.

'Clayton, I'm gonna come!' Jimmy exclaimed suddenly. 'Don't stop fucking me; fuck me hard.'

I hammered him with every ounce of my strength, our balls slapping together loudly. With one hand on his buttocks for balance I leaned over and wrapped my hand around the tip of Jimmy's dick. His long, low groan was punctuated by my forceful thrusts, and he started shooting into my fist, thick and slimy cum running over my fingers and dripping onto the sheets. As soon as Jimmy started coming his ass clenched around my cock, gripping me so fucking tightly that I felt it up the back of my neck. I exploded, shaking and digging my fingers into his hips as I spurted shot after shot of hot jizz into his ass.

'Wow,' Jimmy chuckled, flopping bonelessly onto his stomach. 'Just, wow.'

With trembling fingers I pulled the condom off and tossed in the general direction of the trash can. I lay down beside him. 'Yeah,' I agreed. I held up the hand that I had used to make him come. 'You shot like crazy.'

Jimmy held my hand up for inspection. 'I'm lying on the other half of that shit.' He sucked my index finger into his mouth, pulling the cum off of it with his tongue and teeth. If I hadn't just climaxed I would have been immediately hard. 'That doesn't taste like I thought.'

It didn't seem to bother him, though, because he completely cleaned my hand of his spooge before he let go. Jimmy pulled me onto his chest and wrapped his arms around my upper torso.

'What time is the alarm set for?' Jimmy asked sleepily, stroking my scalp.

'Seven-thirty,' I answered with a yawn. God and damn, but fucking like that sure took a lot out of me. 'Are you going to be okay sitting down all day tomorrow?'

'Hmph. I'll survive.'

I heard the smile in his voice.

Jimmy didn't toss at all that night. I awoke in the same way that I had fallen asleep, with my head pillowed on his chest and his arm wrapped around my shoulders. The alarm trilled aggressively, forcing us both to open our eyes and face the morning.

'My ass is sore,' was the first thing out of Jimmy's mouth.

'Shit,' I said, levering myself up to look at him. 'I didn't even think about, you know, what to do after, or anything.'

'Calm down, Clayton,' he replied casually, rubbing the sleep from his eyes. 'It's not a big deal. You just can't fuck me again today.'

I looked down to where our respective morning wood tented the blankets. We only had until about nine o'clock when our parents came before we had to face reality. 'Come shower with me,' I suggested. Our dorm had one bathroom for every two rooms, which allowed the university to advertise them as 'suites'. Thank god our suitemates were juniors and long gone by then.

True to the nature of our entire relationship, Jimmy didn't need me to tell him anything. We got in the shower, turned on the hot water, and Jimmy's hand were at my ass, kneading and probing to get me ready for him. He fucked me slowly, gently, steadily, as though there was no deadline or need to hurry. It calmed me down to let him take his time, to figure out where to touch me that made my knees buckle, to angle his thrusts so that I had no choice but to come for him. Sure, it hurt some, but Jimmy made it worth it.

I washed Jimmy's hair and he laughed as he shampooed my pubes since my scalp was bare. We got soap in our mouths when we made out; our hands slipped over each other's body in a kind of gentle caress. Jimmy squeezed my ass and I gave him a titty twister. It wasn't until we got out of the shower that we realized that we both had whisker burn on our faces and necks.

'Don't shave,' Jimmy laughed, kissing my cheek. 'Your parents won't be surprised to see you all scruffy. You'll look like a darker version of Common.'

'What about your folks?' I asked, taking the razor from his hand. Jimmy sat on the counter and while I shaved the stubble from his face. 'Going to tell them that we made out?'

'I'll tell them we wrestled,' he replied through still lips. 'And that I won.'

I rinsed out the razor, thinking that I should be weirded out by this incredible overnight intimacy. I was treating Jimmy like I would...I didn't know what. It was more than any sort of friendship. Not like a girlfriend - god help me if I ever had to shave my girlfriend's face. Jimmy and I, what were we now?

'I think we've always been like this,' Jimmy said, answering my unspoken thoughts. 'You and me, we just fit together.'

I followed his round naked ass back into our room. 'I should be more sad that my one and only lover will live so far away,' I said jokingly. 'Jimmy Dean, the other half of my two-person jigsaw puzzle.'

Jimmy laughed and rolled his eyes. 'As long as we have dicks, I think we'll find something to fit over our - damn it, what's the bulb-y part of a puzzle piece called? Prong?'

'Joke ruined.'

He shook his head. 'I know. Fuck my life.'

We didn't speak of the previous night or the shower any more. We didn't need to. I tied Jimmy's tie for him and he held my suit jacket for me to shrug into. Jimmy pretended to waddle bowlegged down the hall, which struck me as the funniest thing in the entire world. When we reached the front doors we went our separate ways with only a 'Later, man,' to indicate that we knew each other at all.

It wasn't until after the graduation ceremony was over in the afternoon that we saw each other again. There was a special reception for summa cum laude graduates, so there wasn't as large of a crowd. I was taking a picture with my advisor when I heard my roommate's voice.

'Clayton,' Jimmy called. 'Hey, Clayton, c'mere for a sec.'

I apologized to my parents and the professor and jogged over to my roommate. He pulled me into a fierce hug, and I wrapped my arms around him.

'You've been a fucking awesome roommate,' I said with a grin.

Jimmy pulled back a little, and for a second I thought he was going to kiss me right there, in front of our families and everyone. 'I'm glad we did it.'

'Yup. Me, too.' I knew what he meant. It was an elementary innuendo, but it was all we could manage in public.

My mom came over and gave Jimmy a hug when I released him. 'If you're ever in Springfield, sugar, you give us a call.'

'I will, ma'am. Thanks,' he replied with a smile. 'Keep this guy in line.'

I watched Jimmy disappear into the crowds with his parents. He turned once to throw me a wave and a smile, and I waved back. He'd be gone by the time I got back to the room.

'No regrets, sport?' my dad asked, clapping me on the shoulder. Maybe I had looked wistful.

'No regrets, Dad,' I answered truthfully. 'Not a one.'

by Wander Wonder

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