All characters are over 18
Sam woke up to the sound of the dorm room door opening, and he caught a brief glimpse of his roommate Dave, maybe heading to the shower?
Sam closed his eyes again but started his wakeup process. His brain started to engage and tell him basic facts.
What day is it…Monday, I think.
That means class at 11, if Dave is just getting up, it’s probably about 8:30. I could open my eyes and see but nah.
What’s going on this week? Umm, no midterms yet, first one isn’t until after Valentines. That’s Friday, did I remember to tell Tyler I don’t give a shit about Valentine’s day? Yeah I think so.
Tyler, is he here? My dick is hard, I hope he is…No, he slept at his dorm last night, but he blew me while Dave and Maddie were out for a walk last night. Oh, right, I think Maddie slept here last night, I wonder if she’s still here. I should roll over and see.
Sam rubbed his eyes and then rolled over to look at Dave’s bed. He stretched a bit and then opened his eyes.
Maddie, Dave’s girlfriend, was there, sitting up in bed but still partially covered in a blanket, scrolling on her phone.
She wasn’t wearing a shirt, or a bra, her tits were just out and exposed.
“Good morning Sammy” she said to him, smiling and looking at him briefly before going back to her phone.
“Umm, good morning to you too. Um, you know you’re topless right?”
“Yeah, I sleep better when they’re free, I just haven’t gotten to put my shirt back on yet, I will before I go shower silly”
“Yeah but like I’m here”
“They’re just boobs Sam, it’s no big deal’
“I mean, it kinda is, like they’re not something you show just anyone”
“I’ve been sleeping in here a couple times a week for a few months now, I figured you’ve gotten used to me. Besides you’re shirtless too, just in your underwear, like me”
With that she threw back the blanket to show that she still had a pair of panties on.
“Yeah but like, not um, that’s different, me shirtless isn’t showing you anything.”
“Oh Samuel, my sweet book smart but oh so dumb boy. Every morning you get out of bed when I’m here and you’re wearing those black underwear you think they’re hiding your morning boner. I hate to tell you this, but they don’t hide it, you’ve shown me plenty I don’t think you show just anyone”
Sam blushed. Oh shit, he hadn’t realized that Maddie could tell.
“It’s OK, I don’t mind. I know it happens to boys in the morning. Dave wakes up with a boner every morning too. I’m guessing you’ve got one now, don’t you? Come on, throw back the covers, let’s see you in your underwear”
Sam wasn’t sure why he did it but he pulled his blanket down to his knees so Maddie could see him in just his underwear. His morning wood hadn’t died down at all.
“Yeah, see Sam, I have a pretty good idea of what your penis is like when it’s hard. And you’ve got nothing to be ashamed of, by the way, it looks like Tyler has something fun to play with.”
“Umm, thanks Maddie”
Maddie laughed. “Oh Sam, you’re fun to tease. Anyway if I can’t have the girls out in front of my boyfriend’s gay roommate, then the universe just isn’t fair”
“Bi roommate, his bi roommate” Sam countered.
“Touché, Sam. Fine, get a good look at them then, if you want to have a memory to jack off to later.”
Maddie giggled as she turned her upper torso towards Sam and pressed her breasts together, and she bounced a little bit in the bed to make them jiggle.
Sam laughed. “To be honest I probably haven’t jerked off to boobs in a long time, but thanks”
“What do you jack off to?” Maddie asked, her voice getting a little softer.
“Umm, depends. I guess gay porn on my phone, like some threesomes or something maybe, just what catches my eye”
“What about at night? Dave says you guys jack off at night but you’re supposed to pretend you’re asleep and not notice the other guy doing it, do you watch then?”
“Nah, on those nights I just try to imagine something, like me and Tyler having sex”
“Do you ever think about Dave? I know you’ve jacked off with him, he told me about the time with you and Max, and about what happened the day that he and I had sex for the first time and how you helped him out before our date. Thanks, by the way, I’m glad he lasted longer our first time together”
Holy fuck, Sam thought, he didn’t think Dave would ever have told Maddie about that.
“Umm you’re welcome again. I was glad to help him out”
“Yeah I knew he was a virgin going in but he was a lot better than I expected, and he’s actually really good now”
“Good to know, I bet he is”
“You know, you can jack off at night when I’m here, I know about the rules you set with Dave, and I know you and Tyler do it on nights when it’s just Dave, so like if you want to do it you should go ahead, I don’t mind”
“Yeah, I don’t know, it feels less weird for me and Tyler because like it’s guys and stuff, I’m not sure how I’d feel about it with you. Besides, Dave never does anything with you while I’m here, even though he could.”
“Samuel, again, for such a smart boy you can be very dumb. Dave and I fuck all the time while you’re here, you just sleep through it. I mean, we did it last night. Here, look”
Maddie took her left breast and held it up, wanting Sam to look at it.
“He shot his cum on me last night, some of it’s still there, dried on”
Sam felt his hard dick stirring, precum flowing. “Is that something you’re into?”
“Getting cummed on? Yeah, I love it when Dave squirts on my tits.”
“Well cheers sister, I like getting a load on my chest too, I love it when Tyler blows on me. His cumshots are huge, big ropes hitting me.” This was maybe a bit more information than he meant to share with Maddie but Sam was having fun talking about boyfriend sex with Maddie.
“Yeah it’s just the best, isn’t it? It’s like, really warm right when it hits you but there’s this cool edge to it. Mmm, I fucking love it” Maddie said.
Sam noticed that she had lowered a hand down to her crotch and was subtly feeling herself.
“How do Tyler’s loads compare to Dave’s?”
Sam adjusted his cock through his underwear, and Maddie definitely noticed that he did.
“Tyler shoots more than Dave, but Dave has pretty good-sized cums, they just don’t like go that far.”
“Yeah I don’t mind, it means less surprises, I don’t have to worry about where he’s going to get his mess if I’m doing stuff with him” Maddie said.
Both Maddie and Sam were conspicuously feeling themselves through their underwear and each of them knew.
“How about you, what are your cumshots like?”
“Um, I shoot a lot, but not like the big ropes or big busts that Tyler or Dave have, mine are more like small shots but lots of them.” Sam answered, his voice getting a little nervous, sensing where this was going.
“Do you want to show me?” Maddie asked. “I’m pretty sure you want to jack off before class now, right? I know I can’t go to class feeling like this, I need some relief”
“What about Dave?” Sam asked.
“I assure you Dave is not going to mind” Maddie said. Had she and Dave talked about this, Sam wondered?
Sam didn’t verbalize his answer, but instead lifted his ass off the bed and pulled down his boxerbriefs. His 7 inch twink cock instantly sprang out and upwards. Sam gripped it and started to stroke.
Maddie did the same, pulling off her panties. Her pubic hair was mostly trimmed away except for a landing strip above her pussy.
“Exactly like I expected. You have a pretty penis Sam. Do you need any lube? Dave has some”
“Nah, I am usually OK without it. I have used Dave’s lube before though, it’s good, but I am fine without it today”
“Are you going to watch some porn?”
“No, just my imagination is fine for today.”
Maddie was petting herself, rubbing her clit while watching Sam stroke his dick.
“What are you thinking about?” Maddie asked Sam.
“The blowjob Tyler gave me last night. While you and Dave were out on your walk, he sucked me off and swallowed my load while we were on the futon.”
“You didn’t suck him off too?”
“No we weren’t sure when you’d be back, and besides Tyler is way more into sucking dick than I am. I like it but he loves it, and he’s amazing at it”
“Mmm that sounds hot Sam” Maddie said, starting to slide her finger around her pussy lips.
Sam and Maddie continued to masturbate, moaning every now and then, watching the other.
“You know, if you and Dave wanted to do more stuff, you can, you don’t have to limit it to just jacking off.”
“I’m not sure Dave is really into that, he wasn’t all into our jerk off with Max, like I think he was OK by himself.”
“Yeah, not everything. Like I don’t think he’d want to suck your dick, but I think he’d be down with it if you or I guess Tyler sucked him off sometime. Speaking of Tyler, he’s a bottom right, so you’re the top?”
“Mmmmhhmmm” Sam moaned as he jerked his dick faster before he could answer Maddie. “Tyler is a bottom, but I’m actually a bottom too”
“Oh, how does that work? Damn I really hoped you’d be a top”
“We can fuck each other if need be, but sometimes we find other guys to top us”
“I don’t think Dave would top you guys sorry, but I think he’d enjoy getting fucked by you, he’s definitely got a thing for some ass play. I made him cum with a finger up his ass last night, and I’ve used my vibrator on him, he loves it. He wouldn’t let himself get fucked by just any guy, but I think he trusts you enough to do it, and I bet he’d love getting the real thing sometime instead of my toys.”
“Yeah, maybe… oh shit… hang on… oh fuck I’m going to cum Maddie”
Sam tossed his head back and jerked even faster, and Maddie watched as Sam’s body tensed up and then released, Sam’s dick shooting his load all over his chest.
“Oh very nice Sammy, that’s really hot” Maddie said, watching intently.
Sam continued to jerk his cock, slower now, and squeezing the remaining bits of cum out of his cock.
“Whew” Sam said. “That was a good start to the day. How are you doing over there, did you finish”
Maddie laughed. “Not yet but I’m well on my way and I have no doubt I’m going to cum this morning, thanks for letting me watch that Sam.”
Sam got out of bed, his cock still half-hard, and he wiped his chest clean with his underwear, and put on some gym shorts. Maddie was still naked in Dave’s bed.
“So, um, maybe you can go shower now? Can you tell Dave to hurry up and get back here too? Oh, and you should probably take a longer shower than normal, unless you want to come back and watch us have sex.” Maddie said with a grin.
“Um, yeah, I think I’ll take that longer shower. But you and Dave have fun”
Sam got his shower stuff together and was about to leave.
“Thanks Sam, oh, and two more things. First, tell Dave that he’s probably going to be late for his 9:30 class. And second, tell him “Maddie got the answers to the questions she was wondering about, and the answers were ‘Yes’”
Sam paused before leaving. “Maddie, did you and Dave plan any of this out, on how this morning started?”
Maddie laughed. “Have a good shower Sam”
= = = = = = = = = = =
Sam couldn’t wait for Valentine’s day, but not because he had anything romantic planned with Tyler. No, it was Dave. He driving Sam crazy worrying about how he was going to make the day perfect for Maddie and all week he would not fucking shut up about it.
It was noon on Valentine's day, and Sam was counting down the hours until the next morning. Dave was coming back up from the dorm front desk to pick up a package. Dave had ordered a necklace as a Valentine’s day gift for Maddie and was supposed to have arrived Tuesday but it got delayed and Dave had not shut up about it since.
“Finally, it’s fucking here” Dave said as he came back in the room. He set the box on the desk, carefully sliced the tape, and took out the other box, the inner box, and finally opened the jewelry box and took the necklace out.
Sam looked at it. “Oh, that’s pretty” he said, being honest. Dave had picked out a nice necklace.
“Yeah, I think she’s really going to like it. Hrm, I think you open it like this, just unclapse this thing”
Dave struggled with it and couldn’t get it.
“Sam can you try it”
Sam took a look and tried to open it but couldn’t either.
“Maybe just leave it for her, she’s probably done this with other necklaces before and knows the trick”
“No, I need to make sure it’s perfect for her” Dave said. “I think I’ve got it, I just need to…”
Sam heard the faint but distinct sound of the metal snapping.
“FUCK” Dave said as the necklace fell apart, parts of it flying in different directions.
“Oh no bro”
Sam helped Dave find as many parts of the necklace as he could, but it was hopeless, the necklace was ruined.
“Fuck me, it’s too late to get another one. Motherfucking god damn”
“Bro it’ll be OK. You got her flowers and you’ve got dinner reservations at the nice Italian place it’ll be fine”
Dave nodded but was still on edge.
An hour later Maddie knocked on the door and came in. Dave jumped up and went right to meet her.
“Happy Valentine’s day my love”
“Happy V-day to you too Dave” she said, and then turned away to sneeze a couple of times.
“Bless you” Sam said reflexively.
“Did the flowers arrive yet?” Dave asked.
“Um, yes, they did. And I love you, and the card was sweet, and they’re beautiful, but um, I think you forgot part of the conversation we had about them.”
“Wait, I got you lilies, you said you loved them? Did they deliver the wrong kind?”
“Nope, you got me lilies” she said, sneezing again. “I yeah, I said I loved the way they looked, but you missed the part where I said I can’t get close to them because I’m allergic”
“Oh fuck me. I’m so so sorry. Is it bad?”
“Nothing a Zyrtec and 4 hours of open windows won’t fix. But they’re beautiful and I love that you tried” she said as she kissed Dave goodbye before going to her afternoon classes. “But, I had to give them Zoe - who’s way down the hall”
A few hours later Maddie knocked at their door again and came in. Tyler was there now too, sitting on Sam’s bed scrolling his phone.
“Hi Sam, hi Tyler. Where’s Dave?” Maddie asked. Maddie was dressed up - not formal wear, but something nicer than college students normally wear.
“He’s in the shower, he’ll be back soon.” Sam answered. “You all ready for the big date? Dave won’t shut up about it”
“Oh trust me I know. I mean, I’m looking forward to it, it’s nice to spend time with him and the food at that place is really good, but I’m not the sort of girl who gives a shit about Valentine’s day, you know?”
“Yeah, me and Tyler are the same way.” Sam said.
“But it means a lot to him, so I’ll play along.” Maddie replied. “What are you and Tyler doing?”
“Video games and fucking” Tyler said, not looking up from his phone.
“Sounds nice. No stress” Maddie laughed. “Here or back in Tyler’s room”
“Here. Ryan and Hannah are going to watch some concert livestream so my room is busy tonight” Tyler said.
“So, Dave knows this, but make sure he texts when you guys leave the restaurant, unless you want to see me and Tyler naked”
Maddie laughed. “Honestly, I wouldn’t mind, but we’ll text”
Maddie sat down to wait for Dave to get back from the shower, and she didn’t have to wait long. Dave bounded back into the room in his shorts, kissed Maddie, and started to get dressed to go to dinner.
“So I’ve fucked the flowers and your gift, but this dinner is going to perfect, the food at Sal’s is supposed to be amazing.” Dave said.
“Wait, you’re going to Sal’s Trattoria tonight?” Tyler asked.
“Yeah, best Italian in town”
“Sorry bro, I hate to tell you this but you’re not eating there tonight.”
Tyler rapidly scrolled through his phone and then showed Dave a post on the university’s subreddit.
“Sal’s is on fire!” the post read, with a photo of flames shooting out of the building.
“FUCK” Dave said as he sat down in his desk chair and put his head in his hands.
“Bro, don’t worry, Tyler and I got you. Get dressed, and you and Maddie go for a walk. Be back here at 7 sharp.”
Sam got Dave and Maddie bundled off, and looked at Tyler. “OK, here’s the plan” he said as he was texting someone. “We’re going to make a romantic dinner for them. You go to the store over on 3rd, get some salad, some bread, and like a frozen lasagna or something. I’m going to go find some candles and stuff. Wyatt’s got an airfryer in his room, we can use that and the microwave to put this together, it won’t be as good as Sal’s but they’ll just have to roll with it.”
Sam’s phone dinged. “Wyatt says he’s cool to help. OK, meet back here in 25 minutes”
Sam knocked on a couple of different girl’s dorm rooms but eventually he found some nice candles and actually some fancier plates than they had, and even something that could pass as a table cloth. Tyler got back with the groceries, and they microwaved up some lasagna and made some cheesy garlic bread in Wyatt’s airfryer. Sam knew that Dave had a few bottles of wine and he pulled out a red. Sam “borrowed” a study table from the floor lounge and two chairs, and got the tablecloth on and lit the candles right at 6:58, right before Dave and Maddie returned.
Sam welcomed them back to the dorm room and seated them at their impromptu restaurant, and poured them each a glass of wine.
“So the food isn’t going to be quite as good as Sal’s, but I hope you two can have a romantic dinner anyway”
Sam pressed send on his phone to text Tyler, and Tyler and Wyatt brought the food down and set it before Dave and Maddie.
“Bro, this is awesome, thank you for doing this.” Dave told Sam.
“Yes, this is very sweet Sammy, thank you” Maddie said, pulling Sam in to give him a kiss on the cheek.
“OK, we’ll leave you two alone, enjoy your dinner” Sam said, and he, Tyler, and Wyatt all left and went back to Wyatt’s room.
“Bro that was a really nice thing you did for your roommate” Wyatt said once they were back in his room.
“This day meant so much to him I didn’t want to see it all go to shit” Sam said. “But what about you, you’re not taking a nice boy out for dinner?”
“Nah, I don’t have anything serious going on now” Wyatt said, with a bit of dejection in his voice “Closest I got is this guy, kinda a friends-with-benefits. He’s hot as fuck, 6’3, athletic, bi, 7 and a half inch dick. We fuck every so often but I dunno that I want a boyfriend yet, and his roommate situation has been fucked up, but he just got some new ones so I dunno, maybe”
“What about you guys, you weren’t going to have a nice romantic date tonight?”
Sam laughed. “No, I was just going to kick Tyler’s ass at Mario Kart and then Tyler was going to fuck my ass while Dave and Maddie were at dinner”
“No for real, I was going to kick his ass in Mario and then he was going to fuck me” Tyler objected.
Wyatt laughed too. “I see, loser has to top? Well boys, how about this, you can play Mario Kart on Max’s switch and then you guys can fuck here, but since it’s my room and I let you use my air fryer, I get to watch you guys fuck”
Tyler reached over and grabbed Sam by the crotch. “We can skip the Mario Kart, Sam, I’ll fuck you babe, happy Valentine’s”
“Hell yeah boys” Wyatt said. In one move he pulled his shorts and underwear down and kicked them off, and grabbed a chair as he pulled off his shirt. Wyatt’s 8 inch cock was already hard.
Sam and Tyler started to undress each other as Wyatt went to his drawer and got a bottle of lube, and then sat in the chair and slicked up his dick. Sam was naked first, and then got on his knees and pulled Tyler’s underwear down to suck his cock. Tyler let Sam stroke and suck him for a few minutes, then pulled him up and pushed him onto the bed.
Sam laid on the edge of the bed on his back, sideways across the bed. Tyler got down on his knees on the floor, kneeling in front of Sam and the bed, and Sam put his legs up over Tyler’s shoulders. Tyler lined his dick up with Sam’s hole and pushed himself into Sam.
Wyatt got up and off the chair, and came and sat next to Sam, his legs touching the floor, with a perfect view of watching Tyler fuck Sam. Wyatt continued to jack himself off, and leaned over and kissed Sam as Tyler fucked him.
Sam shot his load first, covering his twink chest with his jizz.
“Cum on me this time babe, I want to feel your load hit my chest too” Sam said as he felt Tyler getting closer to cumming.
Tyler pulled his penis out of Sam and stood up. “Fuck Sam here it is” he said as he hit his release, ropes of cum landing on Sam’s chest.
“Yeah babe give me that cum” Sam said. He smiled and wiggled his body as the semen kept landing on him. When Tyler finally finished, he sat down next to Sam on the other side from Wyatt, and started to make out with Sam.
Wyatt got off the bed and stood in front of Sam, stroking his dick. “Jesus fuck bros that was so hot shit I’m going to cum too. Fuck Sam here’s my cum too, oh fuuuuhhhuucck”. Wyatt’s cum fell out of the end of his cock, landing in large blobs on Sam’s chest, mixing with the load from Sam and Tyler.
Wyatt sat down on the bed next to Sam, and rested his head on Sam’s shoulder as Sam and Tyler went back to making out. The three naked boys rested together, Sam felt the cum oozing down his chest.
“So, how long til Dave and Maddie are done?” Wyatt asked.
“Um, I’d guess another hour and a half, two hours maybe?” Sam said.
“You guys want to play some Mario Kart then?” Wyatt wondered.
“So long as we stay naked” Sam laughed.
Sam, Tyler, and Wyatt played Mario Kart for a while, and it turned out Tyler easily dominated. As the winner, Tyler got to choose what he wanted, and he picked sucking a load out of Sam and Wyatt.
Two hours later Dave texted the all clear, and Sam and Tyler went to clean up the room and take care of the dishes while Dave took Maddie to go look at the stars. Everyone got what they wanted out of Valentine’s Day.
= = = = = = = = = = =
“So, should we watch a movie, or play video games, or what do you want to do?” Dave asked, opening another bottle of wine. It was Sunday night and Dave and Sam were in their dorm room, along with Maddie and Tyler.
Sam shook his head. “No movie, I’ve had too much to drink and couldn’t follow it.”
“I’d play video games if you want” Tyler said, hopefully.
“Works for me” Dave said. “Maddie do you want in?”
“I was thinking something different. How about some cards?” she said.
Sam tilted his head. “Um, yeah, I guess we could do that. What game do you want to play?”
“Poker. Actually, let’s make it strip poker.” Maddie giggled.
Sam and Tyler both looked at Dave.
“Hey I do what she tells me” Dave said.
Tyler shrugged. “Up to you Sam”
“If you want to get naked for us I guess that’s fine Maddie, you should watch out me and Tyler are good at this game” Sam blustered.
Dave found his cards and some chips, and they set the rules. Texas Hold ‘em, if you go to the showdown and don’t win you have to take off an item of clothing. The guys could count each sock as an item of clothing, Maddie had to take both socks off at once to make up for her bra. Dave and Tyler sat on the futon, Sam on his bed, and Maddie in a chair, and they got underway.
The first few hands were a slow start, with a lot of folding, after the first 5 hands there had only been a few socks lost. But Dave opened another bottle of wine, which was now the 5th bottle the group was working on, and things started to pick up.
Dave lost his shirt, then Sam lost his on the next hand.
As Dave was dealing, Maddie looked at Sam. “So Sam, you had a girlfriend before college, right? Did you have sex with her?”
“Yup” Sam said, taking a big swallow of his wine. “We did”
“Like sex sex or just blowjobs?”
“Oh, I fucked her” Sam said. “I mean I probably wasn’t great at it but I did.”
“And how about you Tyler?” Maddie asked.
“Um, no, no girlfriends or boyfriends for me before college. Sam was first for sex and dating” he answered, also taking a big drink of his wine.
“Really?” Maddie asked. “Like, nothing at all with girls”
“Nope” Tyler said. “Never even kissing”
Maddie laughed and leaned across the table, grabbed Tyler by the shirt and pulled him in for a kiss. “Well, we’ve fixed that”
That was the last time Maddie could have grabbed Tyler by his shirt, because he lost his shirt and then his pants on the next two hands. Dave was in his underwear soon after. Maddie was doing well, having just lost her socks.
On the next hand, Maddie’s full house beat Dave’s straight, and Dave stood up and dropped his CK briefs and sat down. His dick was soft, but Dave didn’t try to cover it.
“There we go babe, that’s what I was looking for. We’ll get some more boys naked with you soon.” Maddie laughed.
Maddie’s full house on the next hand beat Tyler’s flush, and so he stood and dropped his underwear. Tyler’s dick was also soft, and he sat down next to Dave.
“Oh, he is pretty when he’s naked Sam, lucky you!”
Sam and Maddie continued the game while Tyler and Dave watched, nude on the futon.
After that it seemed the game was not moving very fast, mostly it was one of Sam or Maddie folding before the hand was even played, but slowly the game moved on. Eventually Maddie lost her shirt, then Sam lost his pants, then Maddie lost her pants too.
Maddie, now in her bra and underwear, looked at the naked Dave and Tyler, and then at Sam who was also only in his underwear. “Do you think we should let them buy back in?”
“With what?” Sam asked.
“Well, I was thinking if Dave and Tyler made out for um, I dunno, 30 seconds? No, a minute, they could have their underwear back and rejoin”
“That sounds worth it” Sam said with a huge grin.
Tyler threw Sam a look of ‘are you sure about this’ and got a nod yes, so he put his hand behind Dave’s head and pulled him in.
“That’s it stud, kiss Tyler” Maddie said to Dave.
Sam watched as his roommate made out with his boyfriend. Sam felt his dick getting hard, even though neither Tyler nor Dave’s cock looked like it they were stirring yet.
It was about 30 seconds into the makeout session and they were just lightly kissing, but Tyler opened his mouth wider and started to probe into Dave with his tongue, who let Tyler into his mouth and the kissing got more sensual.
“And that’s……..time” Maddie said. Tyler released Dave and pulled back, but then leaned in and gave Dave a much smaller, brief kiss.
“OK, everyone back into their underwear” Sam said, and Dave and Tyler put theirs back on.
It really didn’t matter, gamewise. Two hands later, both Tyler and Dave were naked again. Maddie had also lost her bra, so it was just Sam in his underwear and Maddie in hers.
On the next hand, Sam looked at his cards - a jack and a five. There was also a jack and a five in the flop, so Sam could make two pairs - not great, but not awful. Sam decided to go for it.
“Two pairs” Sam announced as he put his cards down. “What do you have?”
Maddie laughed. “Two pairs” she said as she put down another jack and a five. “Tie”
“OK, your deal” Sam said to Maddie.
“No no no” Dave interjected. “If you don’t win, you take off a piece of clothing. Neither of you won”
Maddie and Sam looked at each other, and then their boyfriends as they stood up.
“Ready when you are” Maddie said.
Sam pulled down his black Nike boxerbriefs, and his hard 7 inches bounced up and stood straight out. Maddie took off her underwear and revealed that she was totally shaved. Both of them stood there for a moment.
Maddie walked over and stood in front of Sam, and then looked at Dave.
“I mean, I made out with his boyfriend, you can if you want” Dave said.
Maddie pushed Sam down so he was sitting on the bed, and then bent down and kissed him. Sam opened his mouth and let Maddie’s tongue come into his mouth, and he put his arms behind him to support himself as Maddie made out with him.
Maddie took a hand and placed it on Sam’s chest, and slowly ran it along him in a circular motion, going down from one nipple, down and across his stomach and then back up to his other nipple. She pushed him back on the bed and leaned over him, and took one of his hands and put it on one of her tits. Sam felt and cupped Maddie’s breast and they kept making out.
Maddie broke off the kiss and turned to Tyler and Dave. “Come sit on the end of the bed”
Sam watched as Tyler climbed onto the bed and then Dave sat next to him. Sam was on his back, sort of directly in front of them cutting across the bed, his dick still hard. Maddie reached down and took Sam’s cock into her hand and stroked him a few times.
Sam was very surprised at what came next.
Maddie pushed Sam all the way down so he was on his back, and then put her leg over one side of him while keeping a hand on his dick, and then lowered herself down on Sam and guided his penis into her.
“Oh fuck Sam” Maddie moaned. “Mmm your dick feels great in my pussy”
For the first few thrusts Maddie was doing all of the work riding Sam’s cock, but after getting over the surprise Sam started to get into it, thrusting into Maddie as she bounced on his dick.
Sam caught a glimpse of Tyler and Dave - both of them were now rock hard and were jacking themselves off while they watched. Sam turned and looked up at Maddie as they fucked.
Sam wasn’t about to cum just yet but he started to wonder if he should nut in Maddie or pull out and maybe shoot his load on her tits? He put that thought out of his head for a moment and went back to enjoying the fuck.
Maddie had other ideas, though. She pushed Sam down and slowed down her thrusts, and Sam got the hint to hold up for a moment and see what was next.
“Dave, I want you to try this, and Tyler, it’s time for you to lose your girl virginity too.”
Maddie took herself off of Sam’s dick and pulled him up by the arm from off the bed, and then laid down on the bed.
“Dave, come here, lay down next to me.”
Dave and Maddie were both on their backs next to each other on the bed as Sam moved down towards the foot of the bed to join Tyler.
“We want you guys to fuck us both” Maddie said to them.
“Gently” Dave said, with some trepidation in his voice. “I know I can trust you to not hurt me Sam but still, fuck your dick is big. And bro, don’t cum in me, pull out first OK?”
“Tyler your dick looks big too, come here and let me show you how to use it” Maddie said to him.
Tyler crawled down the bed to get on top of Maddie and she kissed him as he pulled up. Sam got off the bed briefly to go grab some lube and a towel, and came back to the bed.
“Here, put the towel and this pillow under you” Sam said to Dave. “I’m going to lube you up first.”
Dave nodded, and then turned over to look at Maddie.
Maddie was making out with Tyler, her hands on his ass as he laid on top of her and one hand on her left boob. Tyler was gently grinding into Maddie’s stomach, his cock sliding between their bellies and leaving a trail of precum.
Sam spread a generous amount of lube on Dave’s ass and on his own cock, and slipped a finger into Dave to start to prep him. “Mmmm fuck Sam.”
Tyler and Maddie continued to make out as Sam slowly worked on Dave’s hole, adding another finger and letting Dave stretch. Finally he felt like Dave was ready.
“I’m going to fuck you now Dave, I’ll go slow, just tell me how it feels and if you want to me stop.”
“Hang on hang on” Maddie said, breaking off from kissing Tyler. “I want you boys to fuck us at the same time” she said.
Tyler pushed himself up off Maddie and grinned at Sam, and then leaned over to kiss him. Maddie took Dave’s hand and turned her head to kiss him as well.
Sam let go of Tyler’s mouth, and said to the straight couple “OK, we’re going in.”
Both Sam and Tyler lined their cocks up with places they were not expecting to go just an hour ago. Tyler put the head of his cock on Maddie’s pussy, and Sam pressed his cock against Dave’s hole, and looked at Tyler and nodded.
Dave and Maddie were kissing and holding each other’s hands, and Sam saw Dave squeeze Maddie’s hand harder and felt his body tense as Sam pushed his penis into Dave. At the same time he saw Tyler’s dick start to disappear into Maddie, and saw that she took a huge breath in as he slid into her.
Tyler had already gotten a few thrusts into and out of Maddie before Sam got his cock all the way into Dave, but Dave was taking it like a natural. Dave and Maddie released their kiss and both exclaimed in pleasure.
“Oh holy fuck Sam, damn this is good”
“Fuck me Tyler, give me that gay boy cock”
For never having fucked a girl before Tyler was actually pretty good at it. He got ahold of Maddie’s waist and used it for balance as he started to thrust deep into her, and she yelped each time his balls slapped into her.
Sam was taking it slow with Dave, moving with some hesitation because damn, he was fucking his straight roommate and he wanted to be gentle. But Dave had other ideas.
“Harder Sam, fuck me harder”
Sam leaned in and kissed Dave, and whispered to him. “OK bro, you asked for it”
Sam pushed himself all the way into Dave, right to the base of his cock and Dave cried out.
“OH FUCK.”
Sam pulled himself almost all the way out, so just the head of his dick was still in Dave, and then went deep again.
“FUUHHHUUUCK” Dave cried. “Damn yes fuck me Sam”
Sam reached with one hand and felt for Tyler’s hand, and found it and they squeezed together, an unspoken affirmation of “I’m balls deep in this other person but you’re the one I love” and they continued to fuck their friends.
Dave got close first. “Oh shit, I’m getting close, oh fuck Maddie this is so good”
“Keep fucking my boyfriend Sam make him cum, Oh shit your boyfriend’s cock is so good in me”
Sam got another couple of thrusts in before Dave reached the edge.
“Fuck I’m cumming don’t stop fucking me Sam” he yelled as he was jerking his dick.
Maddie was locked in kissing Dave when Sam felt Dave’s orgasm hit. He watched as Dave’s load launched out of his dick and landed in a puddle in the middle of his chest and felt his ass squeeze tight onto Sam’s cock. Sam slowed down his thrusts but still kept going.
Tyler was kissing Maddie’s neck as she kissed Dave and he rammed his dick into her pussy.
“Oh shit Maddie I’m going to shoot too” he half growled into her ear.
“Nut in me Tyler don’t pull out, I want to feel your cock finish in me”
“Oh fuck oh fuck oh fuck Maddie I’m cumming” Tyler exclaimed. Sam saw Tyler’s ass clench and he knew that Tyler was shooting a big load, he could read the different little motions of Tyler’s body and knew what each of them meant.
Sam was still fucking Dave, but he had slowed down quite a bit and so he decided he was going to finish as well. Remembering that Dave had asked him not to breed him, Sam pulled his cock out of Dave’s ass and crawled over to get between Maddie and Dave. Resting on his knees, Sam kept jerking his cock.
“Fuck Maddie I’m going to cum too, bring those tits over here”
Maddie laughed. “Yeah give me your cum Sammy, you know I love it” she said as she angled her chest to better face Sam. “Right here on the girls”
Tyler pulled his penis out from Maddie and got on his knees to kiss Sam, and Dave pulled himself around to kiss Maddie’s neck.
“Oh shit I’m there” Sam got out as his dick started to squirt his seed all over Maddie’s tits. Sam kept cumming and cumming, raining jizz down onto Maddie, before eventually subsiding and just squeezing the last few drops of cum out.
The four of them all collapsed. Sam fell backwards into Tyler, and Maddie rolled over onto Dave, Sam’s cum on her tits smearing into Dave’s chest. Both couples made out for a few moments, and then Tyler and Sam crawled close to Maddie and Dave, and the four of them laid together. There were a few kisses here and there, and hands kept exploring, Dave idly cupped Sam’s balls, Maddie took Sam’s hand and guided it to her clit, Tyler and Dave stroked each other’s semi-hard cocks, but no one seemed anxious to start fucking again. The four of them took some downtime to recover.
It didn’t take too long before things started to stir again. Sam noticed that Dave’s cock was hard again, and Tyler’s dick felt like it was starting to get hard again too.
“So, are we going to go for round two?” Sam asked the group.
Maddie crawled over the naked boys, getting a good feel of Sam’s cock as she did.
“Oh I need more dick tonight, but I want Dave to fuck me and put a second load in me”
Tyler kissed Sam’s neck. “And your pussy was great and all Maddie, but I want to breed a twink now”
Maddie took Dave by the hand and pulled him off Sam’s bed and back to Dave’s bed, kissing him as they collapsed onto the bed.
Sam got on his hands and knees and Tyler lube him up, and Maddie laid on her back as Dave mounted her and both couples started to fuck.
“God damn Tyler you filled her up, she’s so slick” Dave said to Tyler as both of them were fucking their partners.
“One night I’ll fuck you too Dave and you can feel what it’s like when I breed you. Ask Sam in a few minutes” Tyler answered. Dave laughed a little and then went back to fucking and kissing Maddie.
= = = = = = = = = =
Two hours later both Maddie and Tyler had gone back to their own dorm rooms for the night, and it was just Dave and Sam in the room. They were both in their underwear on their beds, about to call it a night.
“So, um, I mean everything is now different between us, but it’s still also the same, right?” Dave asked.
“Yeah, I think so. I mean, I’m a bottom so it’d be nice if you fucked me some time, and Tyler loves sucking dick so expect him to want to blow you now. But yeah, I’m glad that we could all do that together.”
“I’m glad too Sam.”
“So, was that her idea or your idea?”
“More hers. She keeps telling me that real dick is better than a toy, and that she wanted it to be from you. And she’s always thought Tyler was kind of cute and she wanted to see his dick too, she wasn’t sure she was going to fuck him but I guess she liked what she saw”
Sam laughed. “Yeah, real dick is good, but some toys are fun. Since hey you’re a bottom too, I’ll have Tyler bring over our favorite toy, it’s got two ends. Me and Maddie will watch the two of you use it.”
“Oh fuck, what I have I gotten myself into?”
Sam laughed. “Just wait, you’ll love it. Goodnight bro”
Sam turned off his light and rolled over. That was a pretty good Valentine’s season.
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