“Bro can I try them on?”
Sam froze. Was his roommate Dave asking to wear the white Calvin Klein boxer briefs that Sam is wearing right now? The underwear that’s not even his own underwear, but that belong to his (secret) boyfriend Tyler?
It’s late Friday night and Sam and Dave are about to go bed. Both sleep in just their underwear, and both are already stripped down. Sam usually wears black Nike boxer briefs but he wore this pair because they belong to Tyler, and Sam and Tyler had fucked for the first time that morning in this dorm room.
Dave had noticed the last time Sam had worn these too, when he wore them home from Tyler’s dorm room after a hike where they got really sweaty and so Sam showered at Tyler’s dorm and Tyler loaned these to Sam in the first place.
“Bro last time I wore these you said it was weird that I was wearing these because his dick and balls had been all over it. Fuck dude at least then they had been washed, but now you want to wear them even though my dick is literally right on it?” Sam lectured Dave.
“Yeah but whatever bro. We’ve used each other’s towels enough that I don’t care, your ball cooties have been on me plenty already.”
A few weeks into the semester Sam’s dorm floor got into a series of pranks in the shower room of stealing the towels of guys leaving them hanging on their room door, leaving the guy in the shower either very wet or very bold to walk back naked to his room. (Freshmen boys have quite the sense of humor.) It had happened to Sam and to Dave a few times, but usually only one at a time so they just used the same towel. The only time both of their towels had been swiped they got lucky and Drew1 came into the shower room with them, since he saw them hanging on their door.
“Um, you sure bro?” Sam said.
“Yeah I’ve been wearing these basic Hanes forever bro, like my Mom bought these for me. I want to see what I’ve been missing, maybe it’s time to upgrade, impress the ladies”
“Bro you gotta get a lady to take your pants off first before she can be impressed with your fancy big boy underwear"
“Fuck you dude, I’m talking with a few, more GIRLS than you”
Sam wondered what Dave meant by that, the delivery was a little…specific.
“You can wear mine so you don’t have to make any extra laundry” Dave said.
“Fine whatever” Sam said, and took off the underwear and tossed them to Dave. Dave stood up and took off his Hanes and tossed them to Sam, both of them standing naked holding the other’s underwear.
Dave felt the cotton fabric. “These seem nice bro, very smooth.”
“Whatever bro, just don’t go smelling them” Sam said, actually being very serious. Sam had gotten hard multiple times the rest of the day after he and Tyler fucked each other and there was a fair amount of precum in those CKs, though thankfully all dry by now.
Sam put on Dave’s underwear. “These are, um, I guess OK. They’re what, a large? I would probably be better in a medium. I think I like the Nikes better but hey, good to know if I need some underwear I can take yours.”
Dave was stepping into Sam/Tyler’s CKs. “Oh dude these are really nice. This fabric is so much better than Hanes. Yeah I gotta get some of these so I’m ready”
Dave was admiring himself in the CKs, which were probably a touch too small for him. But they did make his ass look better and showed off his dick much nicer than the Hanes he normally wore, and yeah, if he ever does get anywhere with a girl he really should get a few pairs.
“OK bro give ‘em back now” Sam said.
“No bro I meant let me try them on and sleep in ‘em, why do you think I gave you mine?” Dave said.
“Bro”
“You got to wear these all day and you slept in them the the last time, let me see what sleeping in these is like”
Sam briefly considered outing himself to Dave right then and there and telling him that those were his boyfriend’s underwear that he just lost his anal virginity to that morning and he really wanted to wear them tonight, but decided not to. In fact, Sam decided that if he pressed too hard about getting them back right now it might be weird. Sam was really worried that Dave suspected something and he did NOT want to deal with that right now.
“Fine dude, sleep in ‘em, I just get them back tomorrow.”
“Deal bro, good night” Dave said, and climbed into bed.
Sam was a little grumpy and it took him a bit to fall asleep. No so for Dave, who was asleep practically right away.
* * * * * * * * * *
The autumn sun had already been up for almost two hours when Sam woke up. He lifted up the covers to check, yeah, it wasn’t a dream he was wearing Dave’s underwear. His morning wood was at full attention, but Dave’s underwear was roomy enough that it had plenty of room to flop around. There were some advantages to these Hanes.
Sam heard Dave stir a bit and watched his eyes open up and turn to look at him.
“Morning dude” Dave said, somewhat mumbling.
“Good morning, how’d you sleep?” Sam asked
“Not bad, pretty good actually. I was out quick, I barely had a chance to really see how these felt. Maybe they’re good for me and help me sleep”
“Yeah I was tired and slept OK last night, it was a long week, gonna be lazy today, finished my homework yesterday” Sam answered.
“Nice dude. Um, I’m gonna go shower like right away bro, you staying here for a while?”
“Yeah dude. Leave those CKs here and put them in my laundry”
Dave hesitated. “Bro don’t worry about them, I’m gonna wear them to the shower and then I’ll wash them, I’ll give them back to you clean”
“No bro, they’re not mine so I don’t want to have to worry about them and explain why I lost them, leave them here, I’ll wash them"
Dave seemed more hesitant. “No bro I insist, I’m gonna wash them”
Sam was starting to get pissed now. He really fucking wanted Tyler’s underwear back and was pissed at himself for letting Dave even wear them much less sleep in them, and now Dave wanted to keep them for longer. Fuck that.
“Dude I want them back”
“Sam it’s cool, I’ll take care of them."
Sam really wasn’t thinking straight he was so pissed. He stood up and took off Dave’s Hanes and tossed them back to him. “Bro give me Tyler’s underwear” he demanded
Sam still had his morning wood but he didn’t fucking care, so he was standing naked and hard in front of Dave, his 7 inch cock sticking straight out.
“Bro, please, let me take care of it.”
“What the fuck dude, why won’t you give them to me” the naked Sam said stepping closer. “Take them off now"
“Sam, I can’t dude”
“Why, did you fucking jizz in them dude?”
Dave turned bright red and didn’t say anything.
“BRO. Are you fucking serious right now?” Sam yelled. “Take them off"
Dave got out of bed and stood up. Yeah there was a damp spot in the CKs, and Dave’s cock was hard in them. Dave reluctantly pulled down the boxer briefs and let them fall to the floor.
Sam was still pissed, but he realized this was the first time he had ever seen Dave’s cock hard. It turned out that Dave was a grower, and his cock was a good 6.5 inches and thick when it was hard, which Sam would never have guessed from whenever he and Dave were naked in the showers.
“Fuck bro, you shot a load in my bud’s underwear? I mean“
“I obviously didn’t fucking mean to bro, it’s not like I jerked off in them last night. Fuck it just happens to guys some times, don’t be such an asshole about it. I’ll wash them, whatever. You know how it is, fuck look at your morning wood bro, you’re just as hard as me“
Sam had to admit to himself that Dave had a point.
“But fuck dude I didn’t even want you to wear them but I was a good friend and let you and then you jizzed in underwear that wasn’t even mine, yeah I’m fucking pissed, why didn’t you control yourself?”
“Fuck you Sam. What the fuck is your problem? I’ve seen you get up in the morning, you think I don't notice but you have a fucking cum spot in your underwear all the fucking time, what the fuck is wrong with you, why don’t you fucking control yourself?” Dave shot back, starting to lose his temper too.
“My problem is you dude. You’re always fucking here. Yeah, I have a lot of fucking wet dreams because I never get any fucking time to myself dude. When the fuck am I supposed to jack off if you’re always here watching anime or whatever the fuck you’re doing. I never get any time in this room to myself and the rare times I do I never know if you’re coming right back because you never fucking tell me anything. You ever notice that I always tell you how long I’m gonna be gone for when I leave? Do you think it’s because I think you’re my fucking mom bro? No it’s so you know that you have some privacy for a while, so if you want to jack off or bring a girl back or whatever you want, you know. I can’t jack off at night because you wake up if a fucking leaf falls off a tree across the street, trust me I’ve tried and gave that shit up the first week. Fuck it’s been like 2 and half, almost 3 months and I’m fucking going crazy dude. Fuck.”
Sam turned around and crashed his hands on the wall and leaned up against it, ass hanging out to Dave. Roommates argue all the time, though usually not when both are naked and hard.
“Bro. I’m sorry” Dave said quietly. “I guess I didn’t realize…” he trailed off.
Sam sighed and turned around. “No, I’m sorry too. I should have figured out how to tell you this without waiting months and blowing up about it. You’re a good roommate and a good friend, I didn’t mean it when I said my problem was you, I know I got lucky with roommates.”
“But yeah we gotta figure out some alone time setup” Sam added.
“OK, new rule. We’re just honest with each other, or at least we tell each other when we need something. If you need some alone time, because you need to jerk it or just want some time away from me, just ask dude. I’ll go see the Drews or go to the comic book store or some shit. You don’t even have to say what you’re gonna do, just ‘hey can I have the room for a while’ and I’ll go, no questions asked.” Dave said.
“Yeah, OK, that’ll help.” Sam said. “And you’ll give me some timeframes for how long you’re gone so I can plan?”
“Sure dude, easy enough.” Dave replied.
“And fuck dude, if it’s night and you need to get off, just go for it dude.” Dave continued, “If I wake up I’ll just roll over. But same goes for you too bro, if I’m jacking it and you see, you roll over too. No free shows.“
“Yeah, I can do that” Sam said.
“Bro you’re one of the best friends I’ve ever had.” Dave said. “And we’re arguing over cum in underwear that doesn’t belong to either of us, I think we’re pretty close. No more secrets between us, OK bro?”
“Yeah, no more secrets” Sam lied. There was a secret Sam was not ready to tell Dave, but he thought when the time comes, Dave will be OK with it.
“I know I got lucky to get you as a roommate Sam, and I’m glad. I mean fuck I could have gotten Drew2 as a roommate, that would have been shit.”
Sam laughed, “Yeah, I mean I like Drew2 but fuck it must be tough for Drew1 to room with him and get kicked out all the time for whatever girl Drew2 is fucking that night. Someday maybe you’ll get a girl too bro”
Dave laughed too, “Fuck you just watch bro. Someday every weekend night you and Drew1 will be stuck sleeping together in the lounge.“
Dave looked at Sam. “So, we good?”
“Yeah, we’re good, sorry I was an ass” Sam replied.
“So, um, like a really spaced-out bro hug then? I mean, I’d come in for a real hug, but fuck you’re gonna put an eye out with that thing” pointing to Sam’s still fully hard cock.
Sam laughed and reached out and got his arm partially on Dave’s arm, both of them being sure not to get their erections anywhere near each other.
“I’m gonna go get that shower now bro, you coming?” Dave said.
“Nah, i’m lazy today, I’m gonna go back to bed I think, you go” Sam replied.
“OK. Well, how about this, as the first use of the new ‘timeline’ rule. I’m gonna take an extra long shower. You won’t see me for at least 30 minutes. You do with that information whatever you want, Sam.”
“Roger Lt. Dave” Sam said, saluting Dave in the process, and his hard cock waving as he snapped to attention.
Dave rolled his eyes. “OK PRIVATE Sam”
Dave bent down and picked up the CKs. “I’ll put these in your laundry basket. I’ll get you some rubber gloves or some shit so you can deal with them when you go wash next time.”
Sam got back into his bed and pulled the blanket over him, and Dave put on some shorts and got his clean clothes together, and headed down to the shower.
When Dave was gone, Sam tossed the blanket back and grabbed his cock and started to jerk off. He missed Tyler and wished that he was here with him. It had been almost exactly 24 hours before when Tyler had been in this bed with him, fucking his ass and blowing cum all over him. Sam closed his eyes and remembered what Tyler’s dick felt like when Tyler was inside Sam.
Sam got an idea and got up and went to his closet and grabbed his laundry basket and took out the CK boxerbriefs, and took them back to his bed. Sam laid back, and started to jerk his cock while wrapping the CKs around his shaft.
Sam was mostly turned on by the idea of having a bit of Tyler with him while he jerked off, and he imagined Tyler fucking him with each stroke he took on his dick with the CKs. At the same time, Sam could feel the now cold and damp spot in the CKs on his cock as he stroked from the cum Dave left in them. Dave’s cock was pretty thick, and if Dave does jack off some night, Sam might not turn over and he might watch instead. Sam kept jerking as he mostly thought about Tyler’s cock, but sometimes about Dave’s cock too.
As Sam jacked off, his fantasy changed. It was still Tyler pounding his ass, but he imagined different guys sitting on the futon jerking off and watching as he did. It was a whole group of them. First it was Dave, who was jerking off and then got up and came over and dropped his load all over Sam’s chest. Then it was Nick, the guy on Tyler’s floor with the massive 9 inch cock who Sam and Tyler had jerked off with last weekend. In Sam’s fantasy, Max from down the hall was soon sitting next to Nick and they were both jerking off, and then they came over and shot their loads on Sam’s chest and Tyler kept fucking Sam. After they finished cumming, Sam closed his eyes and imagined Mike was sitting on the futon and jerking off. Sam hadn’t seen Mike, his friend from high school, since way back in the summer when their friend Stacey sucked them both off at the end of party and they both shot their loads on her bed. Soon Sam was imagining Mike standing over him and then shooting his jizz on Sam’s chest.
Finally Sam kept his fantasy on Tyler and his 7 inch cock ramming up his ass. Sam stroked the CKs faster, imagining Tyler fucking him harder and harder until finally Sam shot his cum all over the CKs, mixing his hot semen with the damp mess that Dave had dropped in them earlier. Sam leaned back and quietly said “Oh, fuck” and waited for a bit as his dick deflated, and he kept dabbing up the cum as the last bits oozed out of the head of his cock.
Sam got up and put the CKs in his laundry basket, and put on some shorts and a t-shirt. Sam looked around and saw a pullover that he had been wearing some that week and put them in his laundry basket, as well as his pants from yesterday, so the CKs were covered up some in the basket. Sam didn’t think that Dave was going go looking in his closet, but just in case, Sam figured that he didn’t want to explain to Dave why there was more cum in them.
Dave still wasn’t back from the shower, but Sam felt like getting up and going, so he gathered up his shower things and went down to shower. Sam got in and Dave was out of the shower but was shaving at a sink.
Sam said “Hey I’ll be quick if you want to go get breakfast with me soon”
Dave nodded yes and so Sam went to get a shower, and got through his shower quick and was back in the room before long.
As he entered, Dave was all set to go to breakfast. “You um, get enough time to yourself?” Dave asked.
Sam laughed “Yeah bro, I’m good. You can be in here all day with me if you want”
“Sounds good bro” Dave said. “Though I might ask you to give me the room for a while, not sure I got everything out last night.”
“On that note, let’s go get breakfast.” Sam laughed again. “Fuck this new setup is going to be weird, isn’t it? Good, but weird”
Dave opened the door and the two of them left for breakfast.
* * * * * * * * * *
Sam and Dave hung out in the room after breakfast, they left the door open and hung out. Dave played some Baulder’s Gate on their PS5, Sam played Zelda on his Switch. Max stopped by and hung out for a bit but then disappeared to go watch some football at the student union. They microwaved some Easy Mac for lunch and kept just being lazy. Sam texted Tyler to see what was up, Tyler was out with his Dad trying to find a good birthday gift his Dad can give his Mom. “I have no idea what the fuck she wants. Probably some more bottles of Rosé” Sam texted back and said you can’t go wrong with some diamond earrings.
At some point Sam got up to go use the bathroom, and on his way back, just before he got to his room, Sam looked down the hall and he saw a big guy stepping out of a room. Sam looked a bit more carefully, and fuck, it was Nick. Sam quickly counted doors past the fire extinguisher on the wall, and holy fuck, Nick was coming out of the Drews’ room, which meant he was there to see Drew1 since Drew2 was at home this weekend. Sam stood there as Nick came down the hall. Nick didn’t slow down as he passed Sam except to say ‘sup bro?’ as he went passed. Sam watched him as he went past, and just before he turned the corner, Nick paused and gave Sam a wink.
Sam thought about it for a second, and was absolutely reeling as he realized what it might mean as he went back into the room. He sat down on his bed as he watched Dave play for a few minutes, and took out his phone to text Tyler.
“bro just saw Nick on the floor in my dorm, he was leaving a friends room, didn’t say anything to me”
Tyler texted back a few minutes later. “you gonna scooby doo that mystery bro?”
“yeah. either its a boring class project situation or else things are about to get interesting here”
“have fun bro. Dad found some nice earrings, thanks for the idea”
It had been about 30 minutes since Sam saw Nick, and Sam stood up. “Hey I was gonna go wander the floor for a bit. Did you um, want that alone time?”
Dave paused his game and thought about it. “Yeah, now might be good. Maybe an hour bro?”
“Damn dude, OK, you got it.” Sam put on his shoes and left, closing the door behind him, and locking it just to be safe for Dave.
Sam headed down the hall to the Drews’ room and knocked on the door. Drew1 answered it, wearing jeans and a hoodie.
“Hey Sam, come in”. Drew looked a little disheveled and distracted.
Sam walked in. Drew was playing Fortnite on his PC. “You wanna play?” Drew asked.
“Nah, I’m good just hanging out. You can play, I’ll watch.”
Sam pulled Drew2’s chair over and sat next to Drew1 and watched for a while. Eventually he started to strike up a conversation. “You having a good weekend alone?
“Yeah, it was nice getting to sleep early on a Friday night and sleeping in my own bed the entire night” Drew said slowly.
For a guy who claimed to be doing good, Drew1 was not fitting the part. His inflection was down and he wasn’t making eye contact at all with Sam.
Sam hesitated. Something was off and maybe the last thing in the universe Drew wanted to talk about was Nick and why he might have been here. But at the same time, maybe that’s what’s got Drew upset. Sam let Drew play for a few more minutes while he mulled it over.
Sam decided it was worth trying to find out. “So how is Nick?” Sam asked.
“Uh, Nick who?” Drew said, suddenly very tense.
“Nick, the guy who was here like 30 minutes ago.”
“Oh, he’s uh, he’s fine.”
“That’s good, he lives over in Davis, right.”
“Yeah, not sure”
“Oh, OK. How do you know him?” Sam asked.
“I um, I know him from, um, I know him from a thing” Drew stammered.
“Really bro?”
“Yeah, I know him, from, um, I know him from a, um, a class.”
Sam took in a deep breath. “Drew, it’s OK.” Drew looked dejected.
“I’m going to tell you something that only two other people know.” Sam continued. “You have to promise me you tell know one else. Not Drew2, not Dave, no one”
Drew1 looked away and Sam could see Drew fidgeting. “You’ll be the third person I tell. You can keep this a secret?”
Drew nodded, not making eye contact with Sam.
“Drew, I think you know basically what I’m going to say. I’m bisexual. Nick is one of the other people who knows that, and I know Nick is bi as well. Nick wasn’t here for class, was he?”
Drew sighed, looked at Sam and then looked away, and hook his head no.
“Are you gay or bi, Drew?”
Drew didn’t answer, and just sat there.
Sam stood up, and stood Drew up too, and pulled him in close for a hug. Drew sighed deeply, and melted into Sam. Sam felt his dick stir a little bit, and hoped that Drew didn’t feel it.
“It’s OK Drew. I’m not going to tell anyone, this all between us.”
Drew had buried his face into Sam’s neck and shoulder. “I um, I don’t know what I am” Sam heard him say, muffled by Sam’s body.
“Everything’s fine Drew, it’s OK not to know and to explore.” Drew pulled his head out from Sam’s body, and Sam released him from the hug.
“I did stuff with girls in high school, but since this summer all my sex dreams have been mostly about guys” Drew said. “I’ve been talking to some girls, and even fooled around with some girls at parties that Drew2 has dragged me too, like he went home with some girl and I followed along with them and that girl’s roommate. Drew2 fucked that girl in their dorm room and me and her roommate went to sleep in the other bed. As they were fucking she got horny and she reached in and started to jerk me off and I played with her tits, and then she told me to fuck her so I did, she was loud and so Drew2 knew I was fucking her while he fucked the other girl. it was good, but, um yeah. Drew2 thought it was awesome though and still tells me that he’s gonna make that happen again for me, but I dunno. I don’t think that’s all I want.”
“What do you want, Drew?” Sam asked.
“Well, I think lately I want to get fucked by a dude” Drew said.
Sam laughed. “Bro, have you ever been fucked by a dude? Nick does not have, um, like a starter dick”
“Yeah fuck dude, I found that out the hard way” Drew said, “I figured this weekend was my chance to explore since Drew2 was gone, so I downloaded Grindr and chatted with some dudes. That guy messaged me and we chatted, he said he wanted to top someone, I said I was alone and would be down, so he came over. Fuck he’s hot man”
“I had some condoms and lube I got right after Drew2 left, so I thought I was ready. We made out with me for a bit and then told me to get naked and get on all fours, and it sounded really hot and I was into it. He put a finger in me and it was awesome dude, but then he tried to put his dick in me and I just couldn’t take it, I fucking cried bro. I told him he had to stop before he even got all of his dick into me.”
Drew reached over and grabbed a kleenex and blew his nose, and then continued. “He pulled his dick out of me and fuck it was such a relief. I said I was sorry I just couldn’t do it, but that I’d try to suck him or jerk him off and he could do whatever he wanted to with my cock. But he said that the whole reason he came here was to fuck and if I couldn’t do that then he wasn’t that interested. He said he was sorry but that he just didn’t think it was gonna work out, and so he put his clothes on and left.”
Sam nodded and said “Sorry, that sucks”
“Yeah, I was so humiliated” Drew said. “I was hoping for a good time and it went awful. I mean it could have been worse, he stopped right when I told him to and he was cool about it, but I mean I thought it was really going to happen for me and it was over in 10 seconds, I didn’t cum, he didn’t cum, I just had a sore ass covered in lube”
They sat there in silence for a moment.
“Have you ever been fucked?” Drew asked.
“Yeah, actually for the first time yesterday.”
“Oh nice bro, was it good?”
“Yeah, the guy was perfect, he was gentle and slow and we both had a good time. I fucked him for the first time and he fucked me for the first time, it was really nice.”
“Sweet dude. He could take you?”
“Yeah. I had to go really slow but he eventually took it.”
“How big is your dick bro?”
“7 inches”
“Nice bro, you got me beat. I’m only maybe 6”
“That’s plenty bro” Sam assured Drew.
Drew hesitated, and then asked. “Can I see it bro?”
Sam paused, and decided that he was comfortable with Drew for this. “Only if I get to see yours”
Drew stood up and pulled down his shorts, and his cock bounced up, fully hard. Close to 6, Sam wasn’t really sure, but it was fine.
“Now you” Drew said.
Sam stood up and dropped his shorts first, showing Drew his underwear, the usual black Nike boxerbriefs. Then Sam pulled those down and freed his dick, all 7 inches sticking straight out.
“That’s a nice cock Sam. Can I touch it?”
“If we’re gonna do this, why don’t we go to the bed?” Sam suggested.
Drew walked over to his bed, kicking away his shorts and pulling off his shirt to get fully naked. Sam did the same. Sam admired Drew’s ass as he bent over and cleared a space on the bed off for Sam.
“Fuck dude you’re really hot” Drew said.
“You look good yourself Drew.”
They sat down next to each other, and Drew reached over and touched Sam’s cock, just along the shaft at first but then he grabbed a good grip on it and stroked it some.
“Mmm, there you go Drew, that’s it”
Sam reached over and took Drew’s cock into his hand. Drew gasped as he did it.
“Fuck, Sam, um, that feels good bro”
The two of them stroked each other’s cocks for a bit.
“What do you want me to do Sam? Do you want me to suck you or…” Drew asked.
“Um, I’m OK just to chill and let you do what you want, I like to be cummed on, so if you want to do something for me, when you shoot, you should cover my chest with your load.”
Drew nodded. “I can do that”
Drew kept stroking Sam’s cock.
“Sam, I really trust you, I always did even before I knew this about you. I shouldn’t have gone to that Nick guy who was random and I barely knew. Would you, um, would you fuck me? I think it’d be good with you”
Sam was torn. Tyler and Sam had given each other permission to explore with other guys, but they had also decided to be boyfriends just the day before, and exploring up til now had meant jerking off with other guys. Did they really mean for fucking too?
At the same time, Drew was a good friend, and this was clearly sex that would be, somehow, different sex. It wasn’t some random hookup for Sam that was just about making his dick squirt, and it wasn’t the deep romantic sex that he and Tyler had shared on Friday. No, this was Sam helping his friend Drew. It was lust, yeah, but Drew was vulnerable and needed to do this with someone he trusted, this was sharing something inside a friendship. Tyler knew that Sam had some close friends on his dorm floor, and Sam knew that Tyler was going to understand that this was the right thing to share with Drew.
“Yeah, I’ll fuck you Drew. I’ll help you have good experience getting fucked by a dude.”
“Thanks Sam, this means a lot that I can do it with you.”
“How do you want it?”
Drew got up and went to his drawer and found his lube and condoms. “Um, Nick told me to get on my hands and knees and that sounded really hot. I think I’d like to do that.”
“OK, assume the position then” Sam laughed.
Drew got on is bed and got on all fours, leaving plenty of space for Sam to get behind him. Sam took a condom and rolled it down his cock, and then took the lube. He got behind Drew, and poured some of the lube on Drews now very exposed hole. Drew’s ass was pretty hairy, a fairly thick covering of black hair on his ass cheeks and getting thicker in his crack. Sam could still see some of the lube around Drew’s hole from Nick’s previous attempt. Sam put some lube on his finger and slipped it into Drew’s ass.
“Oh fuck” Drew exclaimed as Sam’s first finger went in. Sam left it there for a second, letting Drew relax. Sam decided he was going to follow the same playbook he used when fucking Tyler, since Drew’s hole felt as tight as Tyler’s did when he fucked him. Sam rolled his finger around to try to relax Drew’s hole and stretch him out a bit, and soon added a second and then a third finger. As Drew’s hole got less constricted around his fingers, Sam pulled them out. Drew moaned the entire time.
“I’m gonna put my dick in now, are you ready?” Sam asked. Drew turned his head back to look and said “Yeah Sam, I’m ready, please, fuck me”
Sam inserted the head of his cock into Drew’s hole, paused, and then pushed in a bit. “Oh fuck” he heard Drew say.
“I can go as slow or as fast as you want Drew. And if you need me to stop, I will. There’s nothing to be ashamed about. This will feel awkward at first but it shouldn’t hurt, and if you’re not ready for it we can do it again another day, you’re not ruining anything for me, I’m here for you”
Drew was breathing deep, and said “just hold there for a second, I think I can do this.”
Sam was happy to pause. He didn’t need to fuck Drew to be happy today.
“OK” Drew said. “I’m ready. Push in some more”
Sam pushed in a few more inches, and was about 4 inches into Drew now. He paused again,
“Fuck this was about as far as Nick got” Drew said. “Damn damn damn, this is a lot.”
“I can pull out, just tell me”
“No, give me time” Drew said, and waited “OK, give me some more”
Sam continued to push until his penis was almost entirely inside Drew.
“That’s it Drew, I’m all the way in, good job bro. I”m gonna slide out now”
Sam pulled back, slowly, until it was just his cockhead inside Drew.
Sam kept up just fucking Drew like he fucked Tyler. He slowly pushed back into Drew, paused, then slowly pulled back out, and paused again, and then repeated. He did that 3 times, and then stopped pausing when he was all the way in, and then stopped pausing when he was nearly out, and then he started to pick up the pace.
Drew switched from moaning as Sam pushed in and out to more grunting as Sam pushed all the way in.
“That’s it Drew, you’re taking my cock like a champ bro”
Sam kept fucking Drew, not quite at at full force porn pounding, but at a good thrusting speed now, Drew grunting with each thrust.
“Oh fuck Sam, this is better than I imagined, oh fuck it’s so good”
Sam was enjoying the fuck. Sam really was sure he was more of a bottom, but topping Drew felt good. Drew was jerking his dick while Sam fucked him.
Sam knew he was going to cum soon. “I’m about to cum Drew” he said.
“Cum in me bro” Drew replied
Sam picked up the pace and Drew started to thrust back into him, enjoying the pounding.
Sam felt his climax hit and his dick let out his load while he was shoved deep into Drew’s ass. “Oh fuck, yeah Drew” he yelled as he unloaded.
Sam pulled his cock out of Drew’s ass and flopped down on the bed. Drew straddled over Sam and jerked his cock until he shot his load.
“All my cum on your chest just like you wanted bro” he said as sprayed his jizz onto Sam. Drew cums a lot like Sam does, lots of little blasts that travel far, and probably more cum than Sam shoots. Drew left him pretty well covered.
Drew collapsed on the bed next to Sam, and took his hand.
“Thanks Sam. That was what I wanted today”
Sam leaned over and gave him a small kiss, nothing deep like he did with Tyler, but just want some close friends might if male affection wasn’t so taboo.
Sam looked at the clock. It had been about an hour since he left Dave alone, and so he could head back. Sam asked Drew for a towel and pulled off the condom, and wiped Drew’s load off of him. Sam found his clothes and got dressed again, and Drew put his shorts and shirt back on.
“So where does this leave you?” Sam asked.
“Lots to think about, honestly. It was fun, I would do it again, and you’re great. I think I might be bisexual too. I don’t know, maybe I’m gay, but girls aren’t awful. We’ll see. I might try to explore with some other guys, but it was good to have this first time be with a good friend.“
“I’m glad you trusted me for this Drew. We’re keeping this a secret, though. If you want to come out, go for it, but I’m not ready to yet, so you’re cool with that?”
Drew laughed. “Oh yeah, no, this whole thing is staying secret for a while, you included. Fuck if we tell Drew2 he’s going to draft us into being his gay wingmen and try to use us to help him pick up chicks."
“OK bro, I’m gonna get going. I’m guessing Dave wants to hang out and play video games and drink again tonight, you coming?”
“Yeah, I’ll see you guys later tonight.”
Sam left and went back to his dorm room. He used his key and was sure to fumble around a bit with it so Dave had plenty of warning, and only slowly opened the door. Dave was on the couch, same clothes as before but no shoes or socks now.
“You good bro?” Sam asked Dave.
“Yeah bro. You’re safe in here for the rest of the day”
The rest of the day was uneventful. Sam texted with Tyler some, and told him that yeah, there’s another bottom on the floor. Tyler texted back “good job in solving that one. Tell me all about it when I get back tomorrow night, let’s do dinner”
Max joined Dave and Sam for dinner, and Drew came down around 8 with a bottle of vodka and a big jug of orange juice so the four of them had screwdrivers while they played Mario Kart til 2am, and then Max and then Drew1 left for the night.
Dave and Sam stripped to their underwear and went to bed, Dave falling asleep quickly. Sam had cum twice that day, but he was still horny. He really wished he had gotten fucked today but that was more than he wanted to ask Drew1 to do. He wished Tyler was here to fuck him again. Sam’s cock was hard in his underwear, and he thought about it and he remembered what Dave said, so he took out his dick and started to jerk off under his sheet.
The noise woke Dave up. “Really bro, the first night?”
“Bro you said we could"
“Yeah, OK bro” Dave said and he rolled over to the other side, like he had agreed. Sam kept jerking under the sheets until he got close to cumming, when he pulled the sheet back and shot all over his chest. Sam laid there for a minute.
Suddenly something landed next to Sam. Startled, Sam picked it up to see what it was, and it was Dave’s underwear.
“Figured you needed a cumrag and I owed you one” Dave laughed.
Dave heard some commotion from Sam’s bed, and then Sam’s black Nike boxer briefs landed on Dave’s head.
“Goodnight bro” Sam said. He tossed Dave’s underwear on the floor and Dave tossed Sam’s underwear there too. Sam reached over and grabbed some tissues and wiped up his cum, and pulled his covers back up. He heard that Dave was already snoring.
Sam thought about how he’d see Tyler tomorrow night at dinner, and drifted off to sleep.
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