(Long, but totally worth it!)
In my first two years of college, my roommate Jay and I both would both have sex with our friend with benefits, Kylie. Regularly, almost weekly, we would have a threesome with her. In fact, I lost my virginity to Kylie when we first did the deed. Though it sounds crazy, I could have not have first had sex in a better environment, as Jay is one of my best friends. My nerves were calmed in a very supportive environment. They both kind of guided me through it, every step of the way. It was incredibly hot to basically take turns with her and communicate with her on such an intimate level. In hindsight, it was fairly reckless to not wear condoms, but she was on very good birth control (an insert in her arm) and we were very upfront with our sexual history. During all of our erotic activities with her, we never used condoms and it really upped the pleasure level. Anyway, because of this, we made an agreement to be exclusive sexual partners with only her. This only changed a few times, when we brought more people we trusted into the mix.
Yes, we had a few occasions where it was more than the three of us. The first time, Kylie surprised Jay and I by organizing it. One of her good girl friends, who was also quite sexually open, brought her exclusive boyfriend to join us in a small orgy over fall break our sophomore year. Unbeknownst to Jay and I, Kylie was talking her her friend Becca about spicing things up with her boyfriend Hunter. She told Becca about what we had going on with me and Jay, though keeping it quiet. We did not really tell anyone about our relationship, since it was unconventional. Basically, Kylie explained to Becca how hot threesomes were, and exciting it would be to have a group sex encounter. As I said, Kylie chose to ask Becca about this because as a friend of hers, she was sexually open. Hunter must’ve been similar to Becca in openness, because he immediately accepted the offer along with his girlfriend. Of course, Hunter was also very interested in having sex with Kylie for some variety. And Becca was all about experiencing three guys in one session.
All us guys are straight, but Kylie made out with, and masturbated together with Becca a few times in high school. Jay and I did not really know much about her bi-curious tendencies. When Kylie brought all this up, we were surprised and quite turned on! So basically it would be three guys only interacting with the girls in our proposed little orgy. There would be some play between the girls though, or at least we were told. Hunter and Becca had a lot of trust in their relationship, and were also exclusive with each other. We all knew each other to be clean (with the girls on good birth control), so we decided to go raw. Plus, an event like this would be that much more pleasurable with sensitivity unhindered. We planned to all meet up over fall break, which lined up the same week for all of us, after mid-terms. Hunter and Becca would take a road trip from their college in Wisconsin to our college in Vermont. We all told our families we were gonna spend break “visiting” friends. There was going to be a whole lot more than visiting over this break. We were super excited about this.
On Sunday after break started, Becca and Hunter got into town and we all helped pitch for a hotel room with two queen beds for them to stay in for a couple nights during their visit. Given that there were not many people in the dorms, we were not gonna risk trying all this in a cramped space with only two twin beds. And trying to sneak five people in our dorm room (especially males and females) was out of the question. Jay and I were barely able to sneak Kylie in our room without drawing attention or getting into trouble. Our college was pretty strict about limiting the potential for crazy things to occur in or building. There was a lot of supervision. With a hotel room, we would have plenty of space to spread out, and be able to be a little louder. Unhindered vocalization adds a lot to the experience of group sex. Communicating pleasure with a lot of people is super erotic, and allows us to work each other up and synchronize orgasms. Not to mention clean up was a lot easier in a hotel room. There were going to be quite a bit of sexy bodily fluids involved in our shindig.
It was early Sunday night when they finally got into our college town after a day of driving. Needless to say, they were tired and we went to go out to dinner at a fairly nice restaurant after they got settled in their hotel room. Becca was wearing a black dress that complimented her black hair nicely. Kylie was wearing a strapless blue dress. All us guys were wearing our nicer clothes too, and it was a lot of fun to go out like the adults we finally were. I know we were still college students, but we felt classy as hell. Knowing what we were going to do together in the next few days, made us feel more mature too. There was a lot of personal growth that occurred these last two semesters, that’s for sure! Conversing with Hunter and Becca came as naturally as talking to friends, like nothing was different among us. Folks who think that there is something fundamentally wrong with those who indulge in group sex are mistaken. We are just like everyone else socially, but just go further to know each other on a extremely intimate level. I was really looking forward to being naked and vulnerable with all these people.
We parted ways after dinner, and Becca and Hunter went back to their hotel room to sleep. On the other hand, Jay and I went back to our dorm room, sneaking in Kylie. It was late and we were tired. However, we were super horny in anticipation for tomorrow’s events, especially after hanging out with our guests to be joining us. Before the three of us went to sleep, we had a quickie to calm down. We both had a turn with her in missionary position, finishing inside her once each. She had two orgasms, climaxing immediately after each of us guys blew our load. Talk about being on the same wavelength! It was absolutely delightful, and we cuddled with Kylie (her between us) until we fell asleep, enjoying the warmth of her soft skin against ours. In the early morning, we three went on a run to start the day off with some good runner’s high. It was quite a chilly morning, and we all warmed up together in the shower, once we returned. We took extra care to wash and groom thoroughly, in preparation of the sexy encounter with Becca and Hunter that afternoon in their hotel room.
The plan was to all meet in the central business district of our college town at noon to walk around. For a Monday at noon, it was pretty lively downtown. The local high school kids must’ve been on fall break as well. Though a cold morning, it turned out to be a super nice day, warm enough to not wear jackets or sweatshirts. After an hour of walking around and shooting the shit, we were all getting hungry. It would be a good idea not to eat anything heavy to weigh us down later. One of the best foods to eat before going at it is sushi, the perfect mix of simple carbs for energy, veggies and protein, without feeling too full afterwards. So sushi it was. This meal was definitely more flirty than last night’s, and the vibe was full of excitement. Lots of joking, laughing and enthusiasm, getting to really know each other’s personalities. Becca was really a hoot to be around, very bubbly and enthusiastic. Hunter was definitely more of a reserved person, but with a dry sense of humor. I could tell we would all be compatible in the bedroom. It was time to find out.
We were full of butterflies when Jay, Kylie and I were driving to the hotel. I don’t know why we were nervous, but I guess it was because we were about to do something so new. My heart was racing, sitting in the back seat. Kylie was in the passenger seat and I gently grabbed her hand. She looked at me and saw I was a little tense. She said, “Hey, this is gonna be super awesome.” I smiled at her and immediately relaxed. She was great at making things so comfortable. When I lost my virginity to her, she made all my first time nerves disappear. This was another first for me, experiencing two girls in the presence of two other guys. Maybe it was because I felt like I did no know Becca very well, and that she was Hunter’s actual girlfriend. Honestly, I was now getting thrilled at that fact. It was gonna be a blast to see Becca naked and please her sexually. Jay then added his hand to ours, saying “Let’s do this thing.”
Time seemed to go in slow motion, and we finally pulled up to the hotel and parked. Becca and Hunter were waiting for us in the lobby. We walked together to the room, and Kylie whispered into my ear “Relax, I’m here. We will figure it out as we go. This is new to me too.” She put her hand on my back and gave me a rub of encouragement. All of us were pretty silent going to the room, excited and aroused. We all had a smirk on our faces. Before we knew it, we were in the room and the door closed. Becca said, “Oh right, lets put out the “Do Not Disturb” sign. That would probably be good!” We all laughed a little as she went to place it on the handle. Jay and I sat on one bed and Kylie sat between us. Becca sat on the other, kicking off her shoes. Hunter went of over to the fridge and got out a small bottle of vodka and a few shot glasses. He said, “Anybody up for a shot of liquid courage? We also have water and some energy drinks.” All of us said sure at the same time and laughed to break the ice a little. We all took a shot. For a little we just talked and joked around a little bit until we loosened up, getting barefoot and comfortable. Kylie made the first move by taking off her tank top.
One after the other, we removed our shirts. We were all wearing casual clothes. The girls both had yoga pants, and Becca was wearing a flannel shirt. Us guys were wearing t-shirts and khakis/jeans. Kylie and Becca were now in their bras, pink and white respectively. Me, Jay and Hunter were very fit and muscular, looking quite good without our shirts on and the ladies commented on it. Both Kylie and Becca had amazingly flat stomachs, and Becca sported a cute little belly button piercing. I’ve described the appearance of me, Jay and Kylie is previous stories. But I will focus on describing the appearances of Becca and Hunter in this encounter. Becca was fairly taller than Kylie, and had black hair. Her eyes were a beautiful shade of green and had beautiful, faint freckles on her face. She had thinner, but naturally reddish lips. Becca’s eyebrows were full and jet black, accentuating her eyes nicely. Playing volleyball, she had a muscular and round butt, a bit larger and rounder than Kylie’s. Her legs were long and toned. I had not seen her undressed yet, but I could tell she had breasts that were quite small. Her bra was definitely an A-cup and Kylie was at least a size larger. Hunter was actually a little shorter than Becca, broad-shouldered, deep-chested with brown hair. He had quite a lot of chest hair compared to Jay and I, which was definitely a change of scenery.
Things started to really get going when Becca started kissing Kylie and getting playful with her. Before we knew it, they peeled off their yoga pants and were in their bras and underwear and cuddling together and laughing. All us guys could do was watch them get affectionate, in stunned silence. Kylie said, “Come on you guys! Take your pants off!” In unison, we got down to only boxers/briefs, with noticeable bulges underneath. All that was left among all of us was underwear. Becca, with a sly look on her face, whispered something into Kylie’s ear. Kylie replied, “You want to? That sounds hot!” Without any warning, both the girls got completely naked. Again, most of you know what Kylie looks like naked from previous stories. We’ve never interacted with Becca sexually before, so this was new. She clearly prepared for this and was completely hairless down there. Kylie had let hair grow in a little, but kept groomed nicely. Becca has a super pink vulva, and looked quite unique. She had two paper-thin inner folds along her slit, and a less pronounced outer labia. It was like beautiful wings of a butterfly or petals of a flower. She did not have nearly as pronounced of nipples as Kylie, and were quite pink in color.
Back to the story: the girls were now completely naked on the bed together. All us guys were sitting on the other bed just watching them and getting hard. Kylie and Becca were laying backward, propped up on pillows side by side. Their legs were up and splayed, giving us a fully view of their girly parts. Then, they started to finger themselves gently, looking at us in pleasure, smiling. Apparently, they wanted to compete on who would come first from masturbating, to get us guys aroused. Indeed we were, and Jay said, “Screw it.” He proceeded to take his boxers off, his dick springing up at attention and balls dangling. He started to slowly stroke himself. Becca said “There’s one!” I was uncomfortably hard and needed to free myself of my boxer briefs. Both Hunter and I followed suit and took the plunge to get completely naked too. Kylie said, “It took them long enough!” We all laughed a little. Not only did the girls mastubate themselves, they traded off and fingered each other, moaning and kissing in between. It was so hot and still, us guys were transfixed looking at them, soothing our raging boners with our hands. All of a sudden, Becca has an orgasm, saying “Oh god!” She squirted a little. I almost came then and there but resisted by stopping stroking. We did not know Becca could squirt!
The girls both had an orgasm each and could tell us guys were really worked up and horny. Imagine three guys, sitting side by side, at full mast, breathing heavily, and trying not to overstimulate themselves. I said, “My dick really needs some attention.” Kylie said, “I’ll be right there! You guys stay where you are.” Both girls said something to each other and got up, grabbed some pillows and walked to bed we were on. Becca said, “Scoot closer together!” We did as we were told. They knelt on pillows and Kylie took me in her mouth, and started stroking Jay (sitting between me and Hunter) with her other hand. Becca starting giving Hunter a blowjob too, and she gently handled Jays scrotum, while Kylie was stroking him. The three guys started to all groan in pleasure. My god, did Kylie’s mouth feel good, especially her tongue rubbing against the tip. There were two girls and three penises, so they switched off. Jay got the best of both worlds, and got a blowjob and handjob by both girls, being in the middle. Our noises signaled that we were gonna come soon. I was certainly getting very close.
Hunter said, “I think I’m gonna come!” Becca opened her mouth, aiming her boyfriend. Kylie, Jay and I watched as he spurted sizable ropes of jizz into her mouth. This was so hot, watching Becca show his emission in her mouth to all of us, then swallowing it. She stood up for a second and they kissed passionately. This visual threw Jay over the edge, and he announced his impending ejaculation. Kylie quickly took him into her mouth, deep enough for him to come down her throat. I see and hear her swallowing, bringing me seconds to release. There was no time for me to warn Kylie (who was kissing Jay intensely) so I sat up a little and blasted all over her neck, surprising her. She said, “Holy shit!,” as I doused her with my hot fluids. Immediately, it started to run down her boobs and belly. Jay and I both were notorious for our large and runny ejaculates. Basically, Kylie has has come to expect a bit of cleanup from both me and Jay. Laughing, Kylie asked for a towel to wipe off. Becca said, “Just a second.” She licked some of my come off Kylie’s neck and gave her a nice wet kiss. It was so freaking sexy. I went to the bathroom, brought back a towel and dried her off. Becca said, “Awww! You are quite the gentleman!” We laughed.
Hunter suggested us dudes return the favor and take turns eating the girls out. Kylie and Becca got comfortable splaying out next to each other, leaning against pillows and the headboard. I needed to explore Becca’s distinctively delicate pussy lips with my tongue. Hunter gave me a nod of permission and I climbed on the bed and asked Becca if I could go down on her first. She warmly agreed and she leaned up to give me a tender kiss signifying her approval. It was absolutely electric, and she put my hand on her boob as our lips met. I drowned out who was doing what, and I focused on her vulva. I lay on my stomach before her, and ran my tongue from her clitoris to her vaginal opening, feeling the texture of her dainty pussy lips. I spread her open and put the tip of my tongue as far as possible inside her opening. She tasted a little different from Kylie, but still awesome. As I was licking, she began to squeal and moan, getting super wet. All of a sudden, she gushed warm pussy juiced into my mouth, her saying, “Don’t stop!” I didn’t and she squirted a little bit more.
I could hear Kylie squeal and giggle in delight as Hunter buried his face into her vulva. She said, “Oh my god, Hunter. That feels amazing!” Jay was making out with Becca as I went down on her, only taking breaks for her to moan. My tongue, lips and mouth were getting tired and asked Jay if he wanted go down on her. So he had his turn and I went to go check on Kylie. She was coming down from a freshly had orgasm and reached her hand out to me. I held her hand and I went in to kiss her deeply, our tongues fluttering together. We then put our arms around each other and held each other tight as she orgasmed again from Hunter’s oral. My head was resting on her shoulder and I felt her warm breath on my ear as she vocalized. I felt so close to her in that moment. Hunter sat up and we both traded off kissing Kylie and Becca. Jay got Becca to orgasm and gush one more time with his oral skills. The girls cuddled, fingered and kissed for a while as we watched, penises sticking straight up once again, desperate to penetrate and inseminate.
Becca and Kylie stopped messing around and laid back to rest for a second. Becca called over to Hunter, saying, “Babe, let’s do it sideways.” She rolled on her side and Hunter got on the bed and his side, facing her. They kissed a little, and Becca lifted up her leg, letting Hunter arch forward and enter her. They writhed and gyrated together, making some of the hottest sex sounds I ever heard. Before I knew it, Jay was setting up with Kylie in doggie-style. Damn, I wanted to get in her right now but I would have to wait my turn. I had space to interact with Kylie as Jay was working her from the rear. She let me scoot in under her on my back, and lay on top of me, stomach to stomach and breast to chest. We interlaced our fingers and kissed each other’s lips, ears and necks. When she took a second to orgasm, and moan/squeal at Jay’s thrusts, she put her head on my shoulder with the side of my face against hers. We rocked together in rhythm with Jays hips, and I could feel her perspiration from her temples and hairline drip on me. We were all one organism.
Kylie was whining, telling Jay to go faster. She giggled and gasped in another orgasm. Every time Jay went in and out, I could hear squishy sounds. This meant that she gushed a little around his dick, as the same sound always happened with me inside her. Drops of her juices landed on my leg and testicles. Jay said, “Awwww. Shit. I’m about to come.” Kylie said, “Come inside me, don’t hold back.” These were the magic words, and Jay started grunting and gasping for breath as he made his last pronounced and slow thrusts, injecting his seed. When he pulled out, I could feel the warm and runny mixture of fluids flow onto my dick and balls and down my butt. Yes, I know it sound gross, but it felt amazing. Primal and animalistic is the best way to describe it, knowing they just finished one of the most important biological function of mating. Jay just fulfilled his natural urge to combine his very self with Kylie in the form of offspring. Something about that is hot to me, and the evidence of the act was spilling over on me. What can I say? I have my kinks.
Kylie rolled off me and came back with a towel, and we three cleaned up. One dry, I turned toward Becca and Hunter. I could hear their pleasure, but kind of tuned it out while Kylie and I were having a sensual moment. They were at an amazing angle of penetration, not quite missionary and not quite side-to-side facing each other. Her leg was sticking straight up as he thrust his cock deep inside her. A substantial wet spot under her butt had materialized. She must have been squirting like crazy. I could tell they were getting close to him finishing, moaning like crazy. She was also wet as all hell, making sloshing sounds. Hunter’s penis popped out of Becca by mistake, followed by one of her squirts, making her gasp. The laughed and kept going. It was so hot! Me, Jay and Kylie watched as he came inside her. The were kissing and just sitting there in recovery, his dick softening in her hole. As not to make the wet spot worse, Kyle grabbed another towel and tucked it under Becca’s butt a bit, to catch his seminal flowback and he withdrew.
A decent amount of Hunter’s jizz oozed out of Becca slowly, and dribbled onto the towel Kylie placed. Becca then squatted over it until the rest drizzled out. At this point, Hunter and Jay had come twice. I had yet to have vaginal sex that evening, and damn I was desperate. The girls knew this and they had an idea. To make things extra sexy, Becca and Kylie would let me have access to both of them until I can came. Becca lay on her back, and Kylie climbed on top of her, them facing each other. Their boobs and bellies were touching, and they started making out and playing with each other’s hair. I knelt behind them with my choice of pussy. Jay and Hunter were taking a break and recovering from coming. I penetrated Becca first to see how she felt. My god it was so moist and warm, still slippery with the remnants of Hunters load. My dick glided in and out of her like silk. At that moment I just realized that Becca was the second girl I’ve ever had sex with. That fact almost made me explode right then.
Becca was moaning as I pumped away. He pussy felt refreshingly different to Kylie’s, and it was hard to explain why. The rigidity was slightly different, as well as the slipperiness and feel of the head against the inner wall. It was amazing to finally feel her, and and connect with here in the most intimate way. Unfortunately I could not kiss her or look her in the eyes because of our positioning. She started to tense up a little around my shaft and the pleasure increased. All of a sudden I felt a rush of liquid against my shaft, I pulled all the way out and Becca squirted all over my balls. If I did not pull out I would have come way too soon. She was moaning in orgasm and her legs spasmed a little. Kylie gasped briefly as I slipped into her, not expecting it. She was still quite slippery from Jay’s contribution, and a little more came out when I pumped a few times. Knowing I was scooping out Jay’s competing sperm made me so rigid. My dick was being coated in semen that only a few minutes ago, was inside my good male friend’s prostate, and sprayed inside my good female friend’s vagina, which I was now penetrating. Fluid-bonding is an amazingly sexy thing. I felt so connected to Kylie and Jay.
I pumped in and out of Kylie a little bit more, and felt myself getting close. Wanting to savor the moment, I withdrew from Kylie to not overstimulate myself. Using both hands, I gently rubbed each of their clits, and the both let out a squeal and giggled. My dick needed get inside again, so I switched back to Becca and inserted. She moaned loudly as I began to thrust confidently. Her vagina was a little more dry now, as Hunter’s sperm was pretty much gone. This gave me more sensation and I was getting really worked up. I was gonna blow any minute now. Becca was approaching orgasm too, I could tell since she was making more noise and tightened around my dick a little bit more. As before, a rush of fluid came in contact with my member. Becca screamed a little and that was enough for me. I let out some loud moans and grunts as I shot three or four strong streams of fresh semen as far as I could inside of her. She squirted once more as I pulled out, followed by a torrent of my runny, milky-white mating liquid. Thank god Kylie, who thinks ahead, laid down a folded towel before we got started!
We had to take a little breather. All of us were now spent. Becca raided the mini-fridge and passed out some bottled water they bought. Everyone drank thirstily, especially Becca. It made sense, given she was a squirter, and needed to replenish her fluids. We all made sure to pee and rinse come residue off our genitals with the shower wand. The towel situation (we used half of them already) was organized and we started a “dirty” pile. Relaxing in the beds, all of us still comfortably naked, we turned on the TV and watched a few reruns of some sitcom. We did not pay much attention to it and mainly just talked and joked around. Down time in between sex sessions is where a lot of the bonding takes place. You get to really get to know people during this time. Funny enough, it is the same type conversation as a group of friends would have playing pool or something. The only difference was that we were having sex as a fun group activity instead. Society tends to have weird biases toward recreational sexual activity and always has to make it about romantic love. It’s just is never that simple. Humans are complex.
Inevitably, we all got horny again. All this sexual activity had everyone in a particularly high state of libido and sexual appetite. Group sex tends to have this effect, as it is much more exciting and stimulating than one-on-one encounters. This time around, we took our time and did not go so hard. We really wanted to savor the feelings and pleasure. To mix things up, we decided to have a little “game.” Both girls wore sleeping masks as not to be able to see. They lay side-by-side, legs apart, pelvises scooted close to the edge of the bed. Each of us guys, sporting decent erections, took turns to briefly penetrate and thrust in and out of one of the girls. The object was the girls to guess who’s penis it was based on feel. We also did it in reverse, where us guys were blindfolded and either girl would ride our boners in a squatting position as not to give themselves away. It was a lot of fun, and after a short bit, we could all tell the other gender apart based genital feel alone. This really turned us all on, and allowed us to have sex, but not long enough to come right away.
I need to wrap this story up, so I will be brief. As I said, this round was a lot more slow and sensual, and not as vigorous. After the blindfolded game, is was mostly missionary position and cowgirl. Here, we could really experience the person. Thrusts were slow and steady, kisses were gentle and passionate, deep eye contact was the norm. One of the best parts was watching facial expressions of pleasure. Us guys edged toward orgasm but stopped before we would go too far and ejaculate. Instead of just making sex noises, we would talk, joke, flirt and laugh. Honestly, I forget how many times I switched between Kylie and Becca. It was almost a blur, as I was just in the bone zone, dialed in. This was definitely the amazing orgy part of our get together. Working hard to not come to soon, we kept up like this for what seemed like hours.
Jay was the first to come a third time, inside Becca as they were having sex in standing position, semen dripping onto the carpet. I came my third time shortly after that, inside of Kylie as we went at it in missionary position. My seed spilled onto a towel underneath us. Hunter was last to come his third time. He came on Becca’s stomach, her sitting at the edge of the bed, and Hunter standing up. Jay was done for the night, and could not come again. Hunter and I were able to come a fourth time. He came inside Kylie and I came inside Becca. We were both laying next to each other on our backs, and both girls was riding us cowgirl-style. My final ejaculatuon was quite small in volume (like two spurts and one dry spasm) and quite a bit less satisfying than my others. It was still hot anyway. Now that we were all done with sex and busting nuts, we guys had a kissing and and cuddle fest with the girls to finish up. That was the cherry on top of such an incredible night. It was already nine o’clock. We had been in the hotel room for like six hours! Like they always say, time flies when you are having fun!
We snoozed for a little and then cleaned up, showered and got in our sleepwear. Becca, who was getting a little cold, wore warm, soft, pink pajama pants with a matching button-up pajama shirt. She wore no underwear or bra underneath and looked cute as shit. The guys just wore their underwear and t-shirts. Kylie just put on a big ass t-shirt and her panties. As always, you could see Kylie’s perky tits and hard nipples through her shirt. That was one of my favorite things! Small things like that add so much to our little casual triad between Kylie, me and Jay. Famished, we decided to order a late-night pizza to our room. We ate and watched TV. Now we were really worn out, as if we were working out all day (which we kind of were, LOL). It was like ten when we all passed out. Kylie, Jay and I slept in of the beds. Hunter and Becca took the other. I don’t think I have ever slept so soundly. We woke up in the morning and all went out for breakfast as if nothing was different. What an awesome, fulfilling experience! Hopefully we could do this again with Becca and Hunter. Time would tell.
My other stories:
How I lost my virginity to a college threesome. [MFM] from gonewildstories
The best oral sex I ever had: a “double-barrel” blowjob [MFM]. from gonewildstories
First-time shower threesome with Kylie. [MFM] from gonewildstories
Kylie’s first double vaginal penetration with me and my roommate. [MFM] from gonewildstories
Hot and quick sex with Kylie in the back of my car. [MF] from gonewildstories
Source: reddit.com/r/gonewildstories/comments/bf45gb/amazing_miniature_college_orgy_over_fall_break