Ty - "Maybe we should try it"

The words, "maybe we should just try it," are six words that bounce around in my head the way song lyrics do for other people.

In the fall of 1990, I was fresh out of high school going to GW studying political science among other things. My roommate was a bit of a jock, he was on the football team back in high school. Not good enough for a scholarship, but it still looked good on his applications and frankly shows in his physique.

I suffer from a bit of Ugly Duckling Syndrome. I had a terribly long awkward phase that lasted from 6th grade through senior year of high school. It was one thing to the next. My nose grew faster than the rest of my head, my teeth needed braces throughout all of high school, acne, I was way too skinny for my growth spurt in 10th grade, I must have grown a foot that summer and put on no muscle.

Last summer however, the braces came off, I took a summer job working as a lifeguard and that lifestyle of sun and exercise helped my skin clear up and I managed to put on just enough muscle to not be "beanpole" anymore. My hair grew out a bit and my head grew in to fit my nose, my jaw filled out to match my dad instead of my mom.

Unfortunately my self confidence was in the basement. I was always the "funny" friend, never the hot friend. So my virginity was firmly intact. I had never even kissed a girl.

My roommate Jason was a quiet guy, very shy for a football bro. So it took a couple weeks for us to get to know each other. The real ice breaker was when he came back to the dorm room after a canceled class, I wasn't expecting him and on these mornings I would take time to jerk off because my first class wasn't until 11 am. I was laying on top of my blankets, completely naked because I had just come back from taking a shower and was going to town on my dick. Jason walked in and got an eyeful of me trying desperately to cover myself but I had made the bed and it was like the blankets were nailed down.

He just stared at me, "oh shit," he laughed and then tossed his backpack on his bed. "Sorry, Ty, my class was canceled," his grin was not helping as I jumped off the bed trying to hide my dick behind my hands but it was rock hard and 7 inches long.

I pulled a clean pair of underwear out of a drawer and pulled them on. My briefs did nothing to hide the fact that I was hard, but at least I wasn't on full display. "Sorry Jay, I...uh...," I turned seven shades of red.

He chuckled, "it's cool man, I do it all the time when you're out."

I slipped on a pair of sorts and a clean t-shirt. I tried not to make eye contact.

It's really not a big deal man, don't be embarrassed. If you want I can leave and let you finish, or we could do it together if you want.

This is a thought that never crossed my mind, and he tossed it out so casually.  I laughed, "what?" My eyes must have been huge.

"What? You've never jerked it with your friends? Never had a circle jerk?" He chuckled. His eyes seemed to drift up and down my body.

I lay on my bed and pulled out a textbook, quickly adjusting my still-hard dick to tuck it into the waistband of my underwear. "No, I can't say that I have." I opened the book. Not having been reading the book, I just thumbed through the pages trying to will my horniness to go away.

“Well…if you want, I could certainly use some relief,” he said softly.

I looked over at him out of the corner of my eye. He was sitting on his bed, staring right over at me, waiting for an answer. His knees were washing back and forth, every time they went wide I could see his underwear-clad package held firmly in place and it looked like it might be growing. I turned my head to look directly at him, “are you serious right now?”

“Yeah, dude, we both have needs, I don’t know about you but back home I would jerk off multiple times per day and since moving in here I’ve been lucky to do it two or three times per week. It’s fucking frustrating,” he shrugged. “And I really hate trying to do it in the showers, it's really uncomfortable…I much prefer to do it in here.”

I huffed, closing my book and sitting up to match his body language. “Well…yeah, it’s frustrating, I would do it every night before bed back home, it would help me sleep, and now I’m sharing a room and have trouble sleeping as it is from your snoring,” we both laughed, “but yeah, being sexually frustrated doesn’t help.”

He rubbed his crotch, “So what are we saying? Do you want to jerk off together or were you thinking some sort of sock on the door kinda signal when choking it solo and wanting privacy?”

I swallowed hard, “well,” I started to say.

“We should definitely have a signal for if we’re having sex in here,” he interrupted.

I swallowed hard again, “oh,” my head bobbed like a clueless fool for a second, “yeah.”

“Ty,” he narrowed his eyes, “you’ve had sex before right?” He slowly tipped his head to one side.

I felt my skin flush, “um…not exactly,” I mumbled.

His eyebrow raised, “no way, a good-looking guy like you…a virgin?”

“I wouldn’t say that,” I stopped him.

He scoffed, “are you for real, have you seen yourself?”

I started to feel really uncomfortable, “I don’t know…” I shrugged, looking away.

“Ty, I just saw you naked, you’ve got a great physique and a big dick, you’re basically a model,” he said with seriousness in his tone. “For real, I’ve seen most of my friends naked and they don’t look half as good as you, you just need some confidence and you'll be beating them off with a stick,” he said.

I chuckled, “I don’t know, I’m not even a little experienced,” I shrugged, looking down at the ground.

“Well,” he raised an eyebrow and a corner of his smile came up on the other side, “if we become jerk-off buddies, you can get some experience that way. The hardest thing for me was the not knowing, it can be scary, I mean, what if I shot my spunk at the first touch from excitement,” he laughed, “that would be embarrassing, and then what if she told all the women I know that I have some kind of premature ejaculation problem,” we both laughed at this one.

“I don’t know man, wouldn’t it be weird?” I asked nervousness in my voice, my dick getting hard again at the idea of someone else touching it.

“Only if you make it weird, it’s not like you’re a homo right?” He shrugged.

“No, I’m not, I swear,” this never crossed my mind, it was never an option either.

“Good, me neither, it’s one thing to have fun and get some relief with your buddy, but it’s totally another thing to be a fudge-packer,” he chuckled.

I huffed, “yeah,” I shook my head at the thought.

Growing up in a Southern Baptist family, homosexuality was not talked about except to let you know those people were going straight to you know where. So I never let myself give it a first thought.

“So, you want to do it?” He broke my concentration.

“Huh?”

“You want to jerk off, finish what you started, I’ll help you out,” he offered.

“Oh, umm,” that rush of nervousness and embarrassment returned.

“Come on man, you know you need to finish what you started or you'll get blue balls, and I really want to rub one out before my next class,” he said, adjusting himself in his shorts.

“Uh…ok, I guess I could try it,” I stammered. “How do we…”

He got off his bed and came over to mine. Sitting next to me. I physically started shaking from nerves and excitement.

“Let’s just pull our junk out and start stroking, on the count of three,” he said, looking down at my crotch and pulling his shirt up so it was over his head but still on his shoulders.

I couldn’t speak, I just nodded up and down.

“Ok, one, two, three,” he counted and then yanked his shorts and briefs down to his ankles. I hesitated but did the same with far less finesse, my hard dick sprang up and hit my abs, precum already oozing from the tip from all the previous excitement and now this.

I didn’t look over at his dick and just started stroking mine. His hairy leg touching my leg, the heat radiating off his body was about to set me off. I started stroking quickly, until he put his left arm around my waist, grabbed my hip, and pulled me closer until our bare hips touched. He reached his right hand over, grabbing my hand, pulling it off my dick so he could grab it.

“Oh shit,” I took a sharp breath, the feeling of someone touching my dick was fucking amazing. He slowly started stroking me, I just kept my eyes laser-focused on his hand pumping up and down my cock, my balls tingling from the start. “Oh man,” my breath hitched. I could feel his hot breath on my shoulder. I was not going to last long, my balls were already tightening and all of this was just too much, “Oh God,” I groaned, feeling my balls spasm, my cock twitch, and the most intense orgasm I’d ever had rushed through my body as cum exploded all over my shirt in several huge spurts as he pumped harder and squeezed harder, “Oh man,” I felt my body twitch under his control. I opened my eyes and saw his fist slow down, covered in my thick white cum as he smeared it over my now extremely sensitive head. “Fuck man,” I twitched and he chuckled.

“Wasn’t that better?” His hand released my cock and I watched as he went straight to his dick, which I hadn’t looked at until now. It was a little shorter than mine but definitely thicker and angrier, with many more visible veins with an upward curve. I didn’t know what to do so I just watched as he jerked himself, something was so hot about him stroking off while staring at my softening cum-coverd dick. It was not lost on me that that hand had some of my cum on it and he was making his dick slick with it as he pumped himself.

He flexed his muscles, his thick thighs stretched wide and then contracted as he gently rocked his hips on the edge of my bed, he grunted, and without warning I watched a massive rope of cum shoot out of his cock and it landed on his shirt. He pointed his dick away and the next rope hit my upper thigh, the next getting the side of my leg and on his leg, until the ropes stopped shooting and just dribbled out and coated his hand and cock as his chest heaved and his abs clenched, “fuck,” he groaned giving his dick a few last strokes.

I was in shock, did this just happen? I felt the wetness of my cum soaking through my shirt, it was definitely happening. Jay’s cum was on my leg and getting watery, steaking its way down and I could feel it wetting my crotch and dripping between my balls and inner thigh. It was gross, I felt so disgusted with myself.

Jay hopped off the bed and grabbed a small towel from under his bed, wiping his cum off his abs, pubes, cock, and hand, then offering it to me to wipe myself off. I grabbed it and even though I tried to only use the dry parts of the towel I felt dry parts of my skin get cum from the towel on them and I couldn’t help but cringe. I handed it back to him quickly. Then ripped my t-shirt off and tossed it in my clothes bin, pulling my briefs up quickly along with my shorts. I felt the wetness that was between my balls and thigh now smearing from the elastic leg hole of my underwear. I can’t believe I just did that.

“You ok?” he asked, tossing the cum covered towel in his dirty clothes bin.

“Yeah, I just have to go to class,” I stood and got a clean t-shirt, pulling it on.

“OK, well, don’t be weird about this. We don’t have to do it again, but it’ll be a much more fun year if we do,” he said, pulling his shirt back down.

I nodded, “Totally,” and awkwardly threw my backpack over my shoulder and headed out as quickly as possible.

I had three classes back to back and then did dinner with some friends in the cafeteria. The entire day all I could think about was jerking off with Jay, well letting him jerk me off and then cum on me. At first, it nearly made me sick to my stomach, but as I mulled it over and rationalized it through the day I came around. It was definitely weird, but man oh man did it feel good to have someone else touch me. As I finished dinner I saw Jay come in with a couple of his friends, I gave him a casual nod and a Boy Scout salute and he did the same with a knowing smile.

I couldn’t help but smile, knowing we had shared an orgasm together earlier just kinda sent a rush through me. The mental images of his big dick shooting cum were burned into my memory and replaying on a loop in my head.

When I got back to the dorm Jay wasn’t there. I had it in my head that when I got back he’d be there, we would exchange pleasantries and then he would jerk me off again. That didn’t happen.

I did my homework and read some chapters of my assigned reading. Somewhere around 9 pm, I couldn’t handle it anymore. I took off my shirt and shorts, slid my hand into my briefs, and started to stroke my dick. It was hot in the dorm, I slid my briefs down a little more and saw there was a slight discoloration on the right leg hole from Jay’s cum this morning. It made me stroke harder, I pulled my underwear off completely and examined the cum stain, continuing to jerk myself. Concentrating on the details from this morning, about how good it felt to have Jay touch me, how hot his cum was on my skin. I was getting close to blowing my load again.

The sound of keys in the door distracted me, I tried to put the underwear back on before Jay walked in but I got tangled and he got a similar full show to what he saw this morning.

“Well, well, well,” He geared.

The sound of my waistband snapping on my tight skin echoed through the room as he locked the door. The room wasn’t big so it was only a few steps from the door to my bed and he was about 6’2” so he closed the gap between us in two steps. I sat up quickly, feet on the floor. He stood in front of me, his crotch at my eye level. I could see he was already hard in his short blue shorts with white piping all around the seams. I looked up at him.

“Are we going to rub one out before bed?” He asked, his hand slipping into his shorts and groping himself.

I nodded, “uh…ok.”

My heart skipped a beat as he pulled his cock and balls over the waistband, it looked bigger than it had this morning, his balls looked huge. He slowly stroked himself, watching me. I reached into my underwear and pulled my dick and balls out just like he had done, my dick was so hard it hurt. I just went into full-speed stroking, not to enjoy this but to cum as quickly as possible.

He took a half step closer to me, his dick went right in my face, I instinctively leaned away from it, not wanting it to touch me and fell on my back. I didn’t lose my grip or slow down as I jerked myself. I kept glancing up to see him stroking himself. He pulled his shirt up over his head again which put his abs and chest on display, his muscles tightening and contracting with every breath as he got closer to cumming. He quietly grunted and groaned, rocking on his toes as he flexed, I jerked faster, keeping speed with him. He stepped forward again, now between my legs with my feet still on the floor, but his hairy legs brushed my inner calves and knees.

I couldn’t help it, I let out an involuntary moan feeling his leg muscles flexing against mine as he stroked himself off. My eyes trailed up his body to meet his eyes. He was staring right back at me and smiling a devilish smile. He spread his legs a little which forced mine wider. It added to my pleasure somehow, I wasn’t going to last long. I watched him stroke and flex, then he suddenly contracted his abs and rocked up on his toes and let out a soft, “Oh fuck,” and a shot of cum flew out and landed on my chest and abs, a second on my cock, another a little higher up onto my chest, the heat and the smell of his cum sent me over the edge and I pressed my knees into his legs, my balls tightened and my body spasmed as an orgasm tore through me. My cum started flying out and pooling on my torso to mix with Jay’s cum. I stroked and stroked every last drop as my balls contorted and drained.

“Shit,” I groaned as the last of it dribbled out onto my pubes and my muscles relaxed as I breathed and relaxed into the mattress.

“Damn dude, sorry, I didn’t mean to coat you,” he chuckled. “Let me get you a rag.” he waddled over to his trunk and pulled out a tube sock, wiping the cum off his dick and his hand, and then waddled back over to me, “here,” he handed me the cum covered sock.

I gently used it to get as much of the cum off me as possible. His cum smeared with mine, but it was so hot, the smell was intoxicating, I never noticed the smell of cum before this moment. I was still breathing heavily, but I handed him the wadded up cum soaked sock and he tossed it into his clothes bin, then tucked his dick back into his underwear and shorts. I pulled my briefs back up and tucked my still-leaking dick back in.

“Fuck dude, I’m so glad you’re cool with this,” he grabbed a Gatorade and chugged it.

Am I cool with it? I asked myself, not feeling so cool now that I wasn’t horny, but I smiled at him, “Well, like you said, it’s just easier this way, not hiding it, and it’s not like either of us is gay right?”

“Fuck no,” he stopped chugging his drink to make clear, hitting the “F” really hard.

I nodded, “I’m going to go take a shower, no offense but I don’t want to sleep with your cum on me,” I laughed.

He chuckled and gave me a thumbs-up.

Over the next couple of days, we jerked off together almost every night. Mostly on separate beds, just watching each other from across the room. On Friday night he was out late and I was asleep before he got in.

On Saturday night I went down the hall where a friend and his roommate were hosting a Tetris Party in their dorm. They were the only guys who had a TV and Nintendo on our floor. It was great but went pretty late and I had a few too many Bud Lights.

After I won, I went back down the hall to my room. Jay was in already, he was at the desk working on a paper he should’ve started weeks ago.

“You’re doing homework on a Saturday night?” I teased.

“Yeah, this is due Monday, I’m gonna be working on it pretty late,” he kept writing, one finger on a line in his book so he didn’t lose it.

“That sucks for you, I don’t have anything but laundry and jerking off to do,” I laughed.

He snickered, “Well don’t let me stop you.” He turned his head to look at me, then down to my crotch and back up to meet my eyes.

I was wearing sweatpants since the Tetris Party was just down the hall with a couple of the guys who were wearing pajama pants or shorts, it was very casual.

I sat on my bed, “I guess I could do laundry,” I stretched and then lay flat on my back, my legs over the side of the bed waving open and then closed several times suggestively.

He shook his head, then turned to me, “I could take a quick break if you want to jerk me off.”

Up to this point, he had jerked me off twice but we mostly jerked ourselves off from our separate beds. I had been wondering what it would feel like to touch him and with the help of my friend Bud Light, I was feeling bold.

“Yeah, I’ll help you out,” I shrugged trying to seem indifferent, but it came out way too eager.

He put his pen down and was on his feet in seconds. He took the two steps over to me and was standing with his shins against my bed, his legs between mine. I used my abs to pull me up which put me at eye level with his crotch, which was already growing. I hooked my fingers in my waistband and lifted my ass a little to pull my underwear and sweats down enough to free my cock. Stroking right away, leaning back on my left elbow as my right hand went to work.

I watched as he reached his hand into his shorts, pulled his cock and balls over the waistband, and started stroking himself.

He only gave it a few tugs before he let it dangle in the air, “Well?”

My eyes moved from his dick to his eyes, “huh?”

“You gonna help me out or not?” He grinned.

My heart started beating fast, it was now or never. I sat back up, his dick inches from my face, I reached out for it, and for the first time in my life, I took another guy's dick in my hand. It is such a weird feeling, it’s hot, and soft to the touch but rigid at the same time, like the velvety skin moves independently over a hard rod. I’m sure it’s the same when I touch my dick but I get all the other pleasure when I touch myself so I don’t notice these sensations. He let out a soft moan when I squeezed his dick. It was noticeably thicker than when I held my own, my fingers didn’t connect around his like they do around mine.

I forgot about my dick and just focused on his, stroking him slowly, it was fun getting the instant reactions from touching him to hearing him react with sounds of pleasure. It’s also interesting how quickly your arm gets tired when you’re not getting the pleasure from the effort. I switched hands a few times, looking up at his face and seeing how much he was enjoying it was what kept me going.

“Play with my balls,” he whispered.

With my free hand, I cupped his balls, rolling the heavy sack between my fingers, he let out a moan. I jerked him faster. He rocked his hips like he was gently fucking the air as I beat him off as fast as I could, squeezing gently on his balls I felt them tighten, his dick swelled in my fist and then it jerked at the same time he let out a gasp of air and it happened. Almost in slow motion, I saw the head of his cock swell, then a massive rope of molten hot cum rocketed out and hit me in the face, I kept jerking him and squeezed tighter on his balls instinctively, closing my eyes to not get any cum in them and the next rope hit me dead on my lips, the next landing on my now soft cock and the next on my sweatpants as the last of it dribbled out onto my fist. I tried to breathe in but my nose almost sucked in the cum on my lips so I was forced to open my mouth to breathe, some of his cum running into my now-open mouth. I tried to blow it out with my breathing but it was too late, I could taste his cum mixing with my saliva.

“Oh God, ugh,” I groaned, releasing his dick, using my hand that was on his balls to wipe as much cum off my mouth as I could, now both my hands had his cum on them and the more I tried to wipe off the worse I made the situation, smearing it on my face, my lips, more got into my mouth as I tried to spit and wipe away the cum that was already in there. I just couldn’t win. I was coated. I heard him chuckle.

“Hold on, I’ll get you a rag,” he kept giggling.

My eyes still closed, I heard him rustling around across the room, then a few seconds passed and he was putting a piece of cloth in my hands, “Here, use this.” I wiped off my hands, then like an idiot wiped off my face, smearing the cum covered cloth on my face, just making this worse instead of better. He kept laughing at me, but I was eventually able to open my eyes and see what I was doing.

“Dude, how can you make such a mess?” I groaned, trying to clean myself off.

He laughed, “Sorry, it felt so good, I think I unloaded my entire nut sack.”

I looked up at him as he wiped his dick off with his hand and then tucked his dick back into his shorts. He took the small amount of cum that he got on his hand and wiped it on my arm.

“Ahh, man, come on,” I groaned.

He chuckled, “you’re already coated,” he shrugged.

I threw the cum rag at him, “yeah, I’m not happy about that,” I shook my head, my smile betraying me.

“Looked like you enjoyed it,” he tossed the rag in his clothes bin.

I purposefully stopped smiling, “It’s gross man.”

“Alright, alright, I owe you one,” he smiled, sitting back in his chair.

“Yeah, a really good one,” I chuckled.

I grabbed my shower stuff and went down the hall to shower, thankfully it was empty so I was able to finish myself off instead of bothering him while Jay’s trying to get his homework done.

Over the next couple of weeks, we both were pretty busy with classes and other social activities, so we were only able to jerk off together about once each week. We made the most of it though.

To my surprise, I really enjoyed how it felt to make him cum, but I refused to let myself read too much into it. I decided it would feel just as good when I someday (hopefully soon) make a girl cum.

He was really enjoying finding new ways to cum on me, I couldn’t be sure but it seemed that no matter how we were getting off he always managed to get some if not all of his load on me. With him standing in front of me it was pretty easy for him to blow all over and he always aimed for my face. When laying next to each other he would roll slightly onto his side at the last second and unload right onto my crotch, forcing me to finish with his cum on me, likely as a sort of lube depending on how accurate he was with his aim. Impressively, when I was standing in front of him, with his legs spread around mine, and him seated on the edge of the bed, he still managed to aim himself so that his load shot out and hit my balls and coated my grundle. I don’t know how he does it. At first, I was grossed out by it, but by the time we were closing in on the Thanksgiving break, I was more impressed by it and a small part of me looked forward to it, like it was a gold star sticker I got to wear after doing a good job as a friend and helping him get off.

I went home for Thanksgiving and didn’t see Jay for a week, jerking off at home by myself just wasn’t as much fun as doing it with Jay. I confessed as much on our first night back in the dorm.

“Yeah, every time I jerked it at home, I pictured you watching me and it helped me get off,” he chuckled.

“I’m glad you said that, I was starting to think I might be weird or something,” I felt a bit of relief.

“Nah, it’s just more fun and feels way better when we do it together,” he admitted.

The conversation alone had me turned on, but after confessing how much I was enjoying our bonding time, I didn’t want to make it seem like it was something I needed by suggesting in this moment that we do it.

After we ate and went back to the dorm, he mentioned that he hung out with his ex-girlfriend while he was back home.

“We didn’t do anything, but it really made me miss…sex,” he laughed.

I smiled, “Yeah, I guess I’m lucky that way, can’t miss something I never had.”

He chuckled, “I guess. I was thinking though, if you’re up for it, I used to do this thing with my best friend Cal back in high school,” He paused.

“Yeah?” I looked at him from across the room.

“Well, when we would jerk off together, he wasn’t any bigger than you so we would do this thing where he would sit on my lap and jerk our dicks together, it kinda felt like we were fucking in a way…because of the motions and touching and stuff,” he got twitchy in his movements and gestures.

“You want me to sit on your lap and jerk you off?” I tried to clarify.

“Not exactly, but kinda,” his face got red.

“I mean, we could try it, if you say it feels good…I believe you,” I shrugged.

He walked over to my bed, pulled off his shirt, and tossed it back on his bed. “It does.” His pants and underwear were on the floor and he quickly got into my bed. “Take off your clothes,” he said in a more hushed tone.

I quickly stripped off my shirt, he yanked my pants and briefs down, tossing them onto the floor. I went to lay back down next to him but he grabbed my waist and pulled me on top of him.

“Here, like this,” he said, as I straddled his upper thighs and he grabbed my ass pulling me forward until my balls were dangling on his and our hard dicks were lined up with each other. Then he grabbed both our cocks in one hand and started stroking us together, I let out a soft moan. “Feels good right?”

“Yeah,” I said in a breathy voice. It really did feel good, and his body under mine was adding a new pleasure factor that I couldn’t wrap my head around, but the hair of his legs tickling my ass, his hairy balls tickling my balls, the heat of his body radiating up into my body, I let out a soft moan again.

He smiled at me, “You try,” he let go of our dicks.

I grabbed both of us and slowly started stroking like it was one big cock. The control was intense, the heat of his cock on mine felt so good, we both let out soft moans. He started gently rocking his hips up which forced me up with him, like riding the waves at the beach, he was really getting into it and I just kept stroking us both. He held my hips in his big hands, rocking my hips in time with his gyrating hips, all the parts of my body rocking with his, him looking up at me and smiling, it all was too much and felt so good. Without warning my balls instantly tightened and I felt my cum rocket out onto his chest as my body contracted and relaxed shooting rope after rope of cum all over him, a staggered, “Oh, fuck,” hitching on my breath as I rode out the newest most intense orgasm of my life.

“Dang Ty, that was awesome,” he smiled. I felt a little post-nut clarity of embarrassment as I watched him scoop up my cum and then use it as lube on his dick. A part of me recoiled at the sight, but a small part of me was really flattered that he was using my jizz as a lubricant.

I tried to get off his lap but he pulled me back down with his other hand, “hold on, I’m almost there,” he said in a gravelly voice. He rocked his hips, squeezing my upper thigh with his free hand and I watched as he fists his dick harder and faster, my cum smearing all over his shaft then he pointed it at me, and a massive rope of cum shot out onto my lower abs, the next onto my trimmed pubes and then my balls, “shit…ahhh,” he groaned finishing off his orgasm as the last of his load drained onto his fist, mixing his cum with mine. “Fuck,” he huffed, “That felt good,” he huffed again, releasing his grip on my thigh.

I swung my legs off him and grabbed a dark t-shirt from my dirty clothes, cleaning his cum off my balls and as much as I could off my abs but my pubes were too sticky to really get clean. He got off my bed and grabbed the t-shirt, quickly cleaning the rest of my cum off his chest and hand, then tossing the shirt at my face he laughed.

“Ugh, gross man,” I groaned out a laugh, tossing the shirt into the bin.

The next couple of weeks were about studying for finals. We didn’t share but one class so we didn’t study together and barely saw each other. Usually one of us would get back after the other was asleep. So we didn’t get to repeat this until we returned from winter break.

This time we were on his bed, me straddling his lap, him rocking us both to orgasm. He was squeezing my ass cheeks as he rocked our hips up and down and I stroked our cocks. The feeling of him massaging my ass was too much though and I quickly blew my load all over him.

“Damn Ty, you really liked that huh?” He smiled.

I felt embarrassed, but smiled, “it..was new,” I let out a half-hearted chuckle. I was going to get off him but he held my hips with one hand and started to stroke his dick with the other. Staring into my eyes, his chest heaving as his muscles contracted from the stroking, “sit up,” he said.

I quickly raised my ass off his legs, slightly on my knees and I felt him slide his dick below my balls and it slipped up my crack. He continued jerking himself off, watching my face as I enjoyed this weird feeling of my ass being played with, then he grunted, sliding his dick up and down my crack and I felt his wet hot cum shoot all up in my crack. He smeared it around with his cock head as he jerked out the last few drops and then let me sit back down.

He huffed out of breath, “shit man,” he smiled.

I scrunched up my face, “Dude, you shot on my ass?”

“Yeah,” he grinned, “I used to do that with Cal back in school, he said he loved how it felt.”

I thought about it for a second, it did kinda feel good in a weird way, I guess it was no real difference from him cumming on my face, chest, cock, or really any of the other parts of my body he’s unloaded on. I shook my head, “I guess, it’s weird though.”

He squeezed my thighs, getting some of his cum from his right hand on my one thigh, “good weird though?”

I shrugged, and chuckled, “I guess.”

“Good, I want to do it again after class tomorrow,” he smiled and rubbed my thighs some more.

“If you want, it’s cool I guess,” I slowly got off of him, my legs sore from straddling him.

After class let out I found myself almost rushing to get back to the dorm, where I waited and waited for Jay to get back so we could help each other get off again. Eventually, I went to dinner, didn’t see him in the dining hall and when I got back to the dorm he wasn’t back yet.

I eventually finished my homework and was ready to call it a night, so I stripped down to my underwear and got in bed. I clicked off the lamp and tried to go to sleep. I was sexually frustrated though, so I gave it a few more minutes and then jerked myself off quickly and it was just satisfying enough that I was able to fall asleep shortly after.

I woke up in the middle of the night to Jay stumbling in, pretty drunk, trying to be quiet. It wasn’t the first time, but this was the first time it happened when I had been waiting all evening for him to get back, so I was a bit pissy.

“What the fuck man, it’s,” I looked at the alarm clock, “1:30 in the morning.”

“Sorry man, I got caught up with something,” he slurred his words.

“Whatever man, just…go to sleep,” I huffed, rolling on my side toward the wall.

“Aww, don’t be mad, I was thinking about you while I was out,” he sat on the bed next to me, kicking his shoes off, then pulling his shirt over his head.

“I don’t care, I’m just trying to sleep,” I said.

“Ok, but I got something I think you’ll like,” he stood, shucking his pants. I heard his belt hit the floor with a clank.

I tried to ignore him, but I was awake now. I rolled back over and looked at him in the dim light, standing in his white briefs, his dick clearly hard, it was hard to be mad at him like this, especially since his being hard was making me get hard again. “What?”

He dug into his backpack and pulled out a small plastic bottle, “lube,” he whispered like it was a curse word in church.

I chuckled, “What?”

“Lube, you know, for when we,” he started to say.

I cut him off, “I know what lube is for, but do we need it?”

He walked over to my bed, “I was thinking maybe…we try something else?”

“What?” I didn’t see where he was going with this.

He stroked his dick from outside his underwear, “Well, you know how I was saying I liked to cum on my friend's ass and how he liked when I did it?”

“Yeah?” I rolled onto my back, looking up at him.

“Well, we would do this thing, where we would use lotion on his ass and he would let me rub my dick on hit…kinda like…faking the motions I do when I fucked my girlfriend, but with him,” he word vomited.

I was struggling to follow what he was saying, “What?”

“Look, if you like what we did yesterday…I really think you’ll like this too,” he said with a hopeful tone in his voice.

I thought about it for a second, “I mean, I guess we can try it…if you want.”

“I do,” he slid his hand into his underwear and grabbed his hard dick, “I really really do,” he chuckled.

“Right now?” I felt my dick getting hard.

“Yeah,” he pulled his underwear down and let them fall to his ankles, stepping out of them he got into my bed next to me.

I huffed, shaking my head, “I guess,” I lifted my ass and slipped my underwear off. “What do we do?”

“Just get on my lap like you did yesterday,” he instructed.

I tossed the covers off and hoisted my naked, tired body onto his lap. My eyes had adjusted to the moonlight so I could see his naked body as he looked up at me. He grabbed my ass and pulled me forward, sliding me up and over his dick so his cock was rock hard behind my ass. “Like this,” he said, gripping my ass tightly, he gently rocked his hips up and down, sending shivers of excitement up my spine as his cock slid up and down my crack.

He grabbed the bottle of lube, squirted some on his hand, and then reached behind me to smear it on his dick. I slowly stroked myself as I watched him prepare himself. His hand came back to the front and another massive glob of lube was squirt into his hand. He reached around and I expected him to rub it on his cock but he quickly smeared it all the way from my balls up my crack and across my hole.

“Woh,” I was surprised by both the tingling sensation of having my hole touched but also the entire action. “What are you doing?”

“Trust me,” he said, running his hand back up and down my crack, again across my hole, and then he grabbed my hips and started to rock his hips, sliding his dick up and down my crack and circling my ass hole to smear the lube. He again grabbed my hips and started rocking his hips under me, his lubed dick slid up and down my crack and at first I thought it was weird, but then he adjusted his hips a little and the angle of his dick sliding changed so the head was more like a big magic marker tracing the line from my balls until my ass turns into my back and I'll be honest it felt good, really good.

“Mmm,” I involuntarily moaned.

“Feels good right?” He gripped my hips tighter.

I put one hand on his abs to balance myself and started stroking my diamond-hard dick. Every time his head glides across my hole it does something to me, like stroking my dick from the inside out or something but the added pleasure is intense. I find myself rocking my hips with his, squeezing my ass muscles when his tip slides across my hole just makes it feel that much better. We rocked like this for a few minutes before he changed his rhythm and started bridging harder and faster.

“Oh fuck,” he whispered, slamming his hips up, his dick slid hard across my hole, the head caught on my tailbone and bent before sliding the tray of the way up my crack and I felt a hot steam of cum shoot up my back. He rocked his hips again and the second shot hit right across my hole, the next got the back of my balls as I rocked my hips to increase my pleasure from this new sensation. The heat of his cum, the intensity of pleasure from his cock rubbing on my hole, I grind my hips hard on him and my orgasm hit me like a truck. “Ungh,” I moaned a guttural sound, rocking my hips one more time as a tingle started at my ass hole and I clenched my ass cheeks around his slimy softening cock and the tingle hit me somewhere inside, my balls pulled so tight it all felt so good I shot a wad of cum right up over his shoulder hitting my pillow, “ahhh,” I groaned fisting my dick and shooting one rope after the next onto his abs as I instinctively rocked my hips on his cum covered lap. I threw my head back and groaned, slowing my stroking as the last of my cum oozed out of the tip and dripped down my fist.

“Fuck,” he huffed.

“Oh man,” I put my hand on his abs, in a pool of my cum to steady myself from falling down on him, I huffed out of breath, feeling weak from the intensity of my orgasm, the only thing I could do was smile and try to catch my breath.

He massaged my legs, from the thigh to my ass cheeks, not moving under me, just basking in his own post-orgasmic bliss.

I took one last deep breath, smelling the cum that filled the air, then I slowly raised my ass off his lap, feeling his cock stuck to my crack for a brief second and then separating with a trail of his cum. I didn’t know what to do at this point so I got off the bed, feeling his cum smearing between my ass cheeks and dripping down my balls as well as my leg, I couldn’t help but chuckle at the idea of how hot that was but also how gross this moment is. I felt cloth under my foot so I picked it up with my toes, it was his underwear, I used them to wipe up the mess, it was his cum after all, then handed the wet briefs to him to clean himself off.

I huffed out some air, then opened the bottle of water sitting on my desk, chugging it as I watched him wiping my cum off his body. He got up, tossed the underwear in his clothes bin, and then spanked my ass cheek.

“Ow,” I chuckled.

“Good game,” he laughed, crawling into his bed nude.

I shook my head, finished my water, and then climbed into my bed. I heard him start to snore after a couple of minutes and then I rolled over to go to sleep, my face rolling right into a splotch of my cum that shot over his shoulder. I wiped it off with my hand, not really caring at this point because I have his and my cum drying on my body at this point anyway…and I’m too tired to go shower.

I was caught up with stupid social stuff during the week and was only able to jerk off solo twice, and not at all the rest of the time. I was starting to realize why guys would complain after not having sex with their girlfriends for extended periods of time. Jerking off solo when I could be jerking off with Jason was just disappointing. Sure, and orgasm is nice, but it felt more like a clinical act, like a forced jerk. I’m certain a wise man once said, “A forced jerk is no jerk at all.”

I didn’t see Jay over the weekend because he had to go out of town for a family obligation. Monday night though, he was back at a decent hour and I didn’t have any homework, so we repeated the experiment almost exactly as we had the week before. This time I was far less hesitant because I knew it would feel good and was chasing that orgasm like a drug addict. Just like last time the orgasm was amazing.

The problem was I got a little too excited and blew my load pretty early in our session and after I came down from my state of bliss, it was really weird. I didn’t know how to act. Here I was, sitting on my roommate's lap while he rubbed his hard penis up and down my ass to get himself off. Then when he finally shot his load I tried to not get coated this time and slid myself forward on his body and landed in the pool of my cum that was on his abs. It was not great.

We cleaned up and for the next couple of days, we didn’t even jerk off across the room from each other. When I jerked off on my own, I wasn’t really interested in reviving our mutual jerk-off sessions, I just kinda wanted things to go back to the way they were.

As you can imagine, that didn’t last long. It only took a few days of solo jerking, then a couple of days of no time and energy to even do that for me to be so horny that after a night of Mario Party and Bud Light, I found myself stumbling back to the dorm wanting that good orgasm. Thankfully Jay had just gotten back to the dorm a few minutes before I had, so when I stumbled in he had just stripped down to his underwear because he was a bit tipsy and wanting to jerk off and go to sleep.

“Well, well, well,” I smirked, looking at him standing there in his white briefs.

He grinned, and threw his hands up like he had just been caught by the police, “you got me.”

“I want to help,” I said, trying not to sound drunk.

“I want a blow job,” he chuckled, then pulled his underwear down, his hard dick sprang free and waved in the air.

I chuckled, “nah, that’s gross,” I scrunched up my face, grabbing his dick in my hand and stroking it.

“Come on man, I won’t cum in your mouth,” he grinned.

I chuckled, “I’ve already had your cum in my mouth.”

“See, and you’re still alive,” he cocked his head to the side.

I thought about it as my hand slipped into my pants and I grabbed my dick. I looked at his dick, it was clean, and familiar, and if I’m honest the thought had crossed my mind years ago about what it might feel like if I tried it. My heart was beating fast, “is that something you and your friend used to do?”

His eyes met mine, and he swallowed hard, “umm, yeah, I mean, we tried it before.”

I nodded my head, taking a minute to respond, “and you liked it?”

He nodded his head.

“And you did it to him too?” I asked, my voice cracking from nerves.

He smiled and whispered, “yeah.”

“You won’t cum in my mouth?” I bit my lower lip, honestly tempted to do it.

He shook his head, “Not if you don’t want me to.”

“I don’t want you to,” I steeled my face.

He nodded his head that he understood. I swallowed hard and got down on my knees, eye level with his cock head. A drop of glistening precum was forming at the tip. I stood back up, “I can’t do it,” I chuckled.

“Ow, come on man, don’t be a tease,” he grinned at me.

I sat on my bed and he walked over to me, standing so his dick was inches from my face. I could smell his scent like a perfume. He boldly closed the gap between us and his dick gently slid across my cheek. “Come on Ty, just give it a little attention.”

I grabbed it, gave it a few strokes, and then licked the head, tasting his precum on my tongue.

“Mmm, that’s it, do it again,” he moaned.

I licked the head again, it really didn’t taste anything like I thought it would. His precum was more sweet than salty like I heard cum tasted. I licked the head again, and again, then put my lips around the head like a lollipop and pulled it out of my mouth with a pop smack of my lips.

“See, not so bad is it?” He ran his fingers through my hair.

“I don’t know,” I licked it again. “I guess not.”

“Try to put more in your mouth,” he suggested.

I tried to do it, but his dick was just a little too big and I was only able to get the head in my mouth before my teeth were scraping his dick and he pulled it out quickly.

“Woah, careful,” he said, then tapped the head on my saliva-slicked lips.

“Sorry,” I said, putting my hands on his hips and pulling him back into my mouth.

I put in the best effort I could. Having never received a blow job, I really didn’t know what I was doing, but it was kinda fun to try. After a few minutes though he got a little overexcited and tried to push deeper into my mouth and my gag reflex kicked in nearly making me spew Bud Light all over him.

“Shit, sorry,” He said, pulling his cock from my mouth as I coughed and gagged a bit.

He quickly lay on his bed before I recovered and then gestured for me to climb on top as I had before. I gladly got on his lap and started stroking our dicks together. He pulled me forward and reached into the desk drawer near his bed to pull out his half-empty bottle of lube. He squirted it into his hand and was fast lubing us both up, tapping his cock on my crack. Then when I rocked up a little the head tapped on my hole and I let out an “mmm.”

We started to rock together, me stroking my dick to the rhythm of his hips, his dick sliding across my hole driving me wild.

He stopped rocking his hips and I found myself just grinding on his hard dick for my own pleasure.

“Want to try something else?” He asked.

I was so turned on and needed to cum, “yeah, what else?”

“Sometimes, when we were really horny, my buddy would let me push in,” he grinned.

I thought he was going to say he wanted to suck me off, this was a curveball, “what do you mean?”

“You know,” he reached around me, grabbing his cock and thumping it on my hole, “push in…” he let it hang out there for me to understand.

My heart started to race, “I don’t know about that,” I stopped stroking myself.

“Come on, just a little bit, if you don’t like it we don’t have to do it,” he pleaded, his hand leaving his cock and his finger started to gently circle my ring, that felt good. My brain was telling me don’t do it, but my dick was telling me to try it out.

I cocked my head to the side, “He would let you push inside, like in his ass?”

Jay grinned up at me, still circling my hole with his finger, letting the tip go around and then across, “Yeah, only when we were both single and really horny,” he said.

I huffed, “I am really horny,” then chuckled.

“Yeah?” He asked with a grin.

“I mean…I guess, maybe we should try it, just to see,” I shrugged, trying to play it cool but I was so nervous and excited I might cum if I touched my dick.

“Don’t toy with me Ty,” he cocked an eyebrow up.

“I’m not, I mean, it seems a little gay though,” I shrugged.

“It’s not, I’m not, you’re not, my buddy just got engaged to his girlfriend so he’s definitely not,” Jay chuckled. “It’s just fun and feels good, you like when I touch your hole with my dick right?”

I thought about it, “Yeah, it does feel good.”

“My buddy told me it’s like a million times better once you get it inside, and it definitely feels amazing for me when it’s inside,” he grinned, still rubbing my hole with his finger, he popped the tip in just a little and it did feel good, weird but good.

I took a deep breath, and shrugged my shoulders, “I guess, yeah, ok, just this one time.”

His smile got huge, “Oh man Ty, you’re going to love it.”

“So how does it work, you just push the head in?” I asked, genuinely unsure of the mechanics.

“Yeah,” he grabbed the lube and poured some onto his hand, then started to rub it on his dick and then my hole, getting us both real slick. “It might sting at first, for like a minute because you’re not used to it, but I promise that will go away once I’m in you.”

“In, like all the way? I thought you said just a little bit?” I started to get concerned.

“Well, I mean, however deep you want it to go, I’ll let you sit on it so you can control how much is in you,” he said, slipping his finger into my hole a little deeper and wiggling it around.

His finger did feel good inside me, not great, but if he’s done this with his friend before it can’t be that bad.

“Ok, should we like…get a condom?” I asked seriously, feeling his finger re-enter my hole with more lube on it, slipping in almost to the knuckle.

“No, we don’t need one, you can’t get pregnant if I cum in you so what’s the point?” He asked.

“I guess, but you’re not right?” I slowly started stroking my dick again.

“What?” He pushed a second finger into my hole, this stung a little but still slid in pretty easily.

“Unmmm, you’re not going to cum in me right?” I asked.

“Not if you don’t want me to,” he said, getting his two fingers in as deep as he could go.

His fingers felt uncomfortable inside me, “I don’t know about this man, this kinda feels weird.”

“That’s just my fingers, trust me, my dick will feel much better,” he smiled at me. “Just let me get in you and if you don’t like it we can stop.

My heart was beating in my throat, “Ok, let's just try it,” I shrugged.

He pulled his fingers out, adding a little more lube to his dick then I felt his dick slide between my cheeks and line up with my hole. He wiggled it there for a second, which felt great.

“Now just relax, take a deep breath, and let your ass muscles relax and my dick will pop in,” he said in a soothing tone.

I took a deep breath, and with the head of his dick pressed against my hole I tried to let it slide in, but the pressure was too intense and it didn’t go.

“You can do it, Ty, just enjoy it and remember to breathe,” he encouraged me.

I didn’t want to disappoint him so I adjusted how I was hovering above him and let the weight of my body and gravity do the work. Sure enough, the head popped in and holy fuck did that sting, like a holy-nope type of pain. I tried to catch myself as I started to fall backward, landing on my hands.

“Mmm, fuck Ty, that’s it, relax, breath, I promise that sting will go away,” he moaned and I swear he rocked his hips up so more than just the head popped into me.

“Ahh, fuck…Jay, this fucking hurts, I can’t…”

“Yes you can, just breathe, relax, and breathe, the worst is already over,” he cooed.

The sting went all the way up my body, but I was at such an awkward angle there was no way I could just hop off without hurting myself or worse hurting Jay. I just tried to breathe like that was fucking helping, and I don’t know how to relax but I did my best to not panic because this did not feel good.

“Fuck man, I don’t know, it’s too big,” I said through clenched teeth.

“Just give it a minute, mmm,” he groaned, holding my hips so I didn’t jump off.

I felt my upper body strength giving out and my ass started to slide deeper onto his pole. Every millimeter stretched my hole in a way I had never felt before, the pain was excruciating but the heat coming off his dick filled me with something that could feel good if the stretching didn’t make me feel like I was being torn in half, and then his pubes were brushing against my ass, my ass had landed in his lap.

“Mmm, that’s it Ty, now just relax,” he moaned, still holding my hips but also massaging my ass at the same time.

I used all the strength I had left to pull myself back up so I was sitting on him cowboy. It still stung but as long as he didn’t move or breath it didn’t get worse. I made eye contact with him, he had a glint of euphoria I had never seen before, and his smile was so big, I just grinned and shook my head. I was still trying to catch my breath as I held my hands on his abs and felt him contracting his muscles, I felt his dick ever so slightly move inside me, pulsing with his heartbeat, this was by far the strangest thing I’d ever done for a friend.

He gently rocked his hips up into me, “oh shit, that’s weird,” I said.

“Feels good though, right?” He said with a near pleading in his voice.

“It’s ok, it doesn’t hurt as much as it did,” I confessed.

“See, and it will get better,” he promised.

He rocked his hips up into me again, “Oh man, this is too weird, I don’t know man.” The feeling was not anything I had ever wanted or expected. Having Jay’s dick inside me was way beyond “helping each other get off,” Jay was…was fucking me.

I tried to pull off but he held my waist and thrust gently up into me again, “no, wait, you said you’d give it a try,” Jay pleaded.

“Ungh…” I huffed out some air when he thrust up, opening me even deeper inside. “Mmph, this is what you and your friend do together?”

He thrust again, smooth but firm, “yeah, but he doesn’t feel as good as you do,” Jay whispered.

This made me feel a little tingly inside, “And you what, thrust a little, ungh, and then cum on his back like you did mine the last time?” I groaned, trying to let him get the maximum pleasure out of this.

He thrust a few more times, deeper with each thrust, building up a slow rhythm that was starting to feel good, “yeah,” he moaned, “sometimes he just lets me finish like this,” he kept thrusting, rocking his hips up into me, and I instinctively rocked with his hips like we had done before but with his dick inside me instead of going up my crack like before.

“Mmm, fuck,” I groaned, feeling him hit something inside me that shot lightning bolts of pleasure up into my body, a million times better than when it felt like he was jerking me off from the inside, this felt like he was systematically unraveling my body and building me up for a really intense orgasm. “But you still pull out right?” He thrust a little harder up and it made me raise my ass a little more which gave him more room to pull most of the way out and thrust deep into me. “Ungh, fuck, like…you do this and then cum on the outside?”

He grabbed my dick and started to stroke it while thrusting up into me, “sometimes he would let me finish inside, mmmm, it would always feel so good when he let me finish inside,” he moaned, his speed and intensity increasing.

Fuck, this felt so good, he was right, the pain had gone and the feeling of his slick cock pummeling my hole was driving me insane. I had no idea my ass could feel like this, that having a dick in you could feel so good, “mmm fuck that feels good,” I groaned.

“Yeah it does, I’m not going to last long,” he warned, thrusting harder as I started to grind my ass down.

I started stroking my dick, something inside me felt so good and every thrust was making me leak more precum, I wanted to cum so badly. Jay was holding my hips and thrusting up into me, moaning, “Jesus Ty, you’re going to make me cum.”

He kept thrusting harder into me, “Me too Jay, fuck I’m about to cum,” I warned him. I felt my ass clamping down on his dick, my balls tightening.

“Fuck I’m gonna cum,” he warned, “please let me cum in you,” he begged.

I felt his dick swell inside me, pushing against my walls even harder with every thrust, my ass clamping down tight, it sent me over the edge, “ungh, yeah,” I groaned and felt my balls pull in tight and my cock went rigid, his cock swelled inside me and I felt it twitch. We both moaned and groaned and I blew my load, hitting him on his neck, then chest.

“I’m cumming,” he held my hips and thrust hard into me, I felt a wet and warm sensation as he unloaded inside my ass, “mmmm fuck, ungh,” he groaned.

“Mmmm,” I threw my head back, my hand still jerking my cock, the last of my cum spewing onto his abs.

He was twitching under me, thrusting his cum slicked cock deep inside me as his head curled up and then flew back down onto the bed several times as he shot his massive load inside me, “oh fuck, ungh…” he gasped before finally he stopped thrusting and his body relaxed under me.

I let my ass slide down his shaft and just relaxed on him, catching my breath. “Holy shit,” I breathed deep.

He chuckled, “Yeah, I told you,” he grinned and then twitched as I rocked forward, letting is overstimulated cock slide out of my ass.

I slowly lift myself off him, wobbly walking to get a rag to clean the cum off his chest and handing it to him. I watched as he slowly cleaned himself up, then tried to hand it to me to clean myself up.

“I think yours is all inside me,” I chuckled.

He laughed, “Oh yeah, fuck…that was hot.”

I shrugged, “it was definitely different.”

There was a pregnant pause, “but…we’ll do it again right?” He asked, folding his arms behind his head, his naked body glistening in the dim light.

I shrugged, “I mean…it wasn’t terrible, so as your friend, if you need help getting off…I guess you can do that if you want.”

He grinned at me as I pulled on my briefs. Nodding his head, “Yeah, I’m definitely going to want to do that again.”

I climbed into my bed, “will I get to do that to you?”

He clicked off the light, “Nah, I tried it once, I didn’t like it the way you liked it.”

I thought about that for a while, I really did like it. I heard him start to snore. I rubbed my belly for a bit, wondering what to do now, his cum is inside me. I guess it just is what it is and if I want to do it again…I probably need to get used to having his cum inside me.