Kylie’s first double vaginal penetration with me and my roommate. [MFM]

Near the end of my 2011 spring semester of college, I engaged in what I believe is one of the most pleasurable sex act I have ever had. Bear with me, as this story is long, but so sexy it will be worth it. It took place in June after me, my best friend Jay and our friend-with-benefits Kylie were all done with finals the last week of school. From my previous stories, you would remember that Kylie was this amazingly cute and sexy girl of which Jay and I had a threesome with, after a college party early that year. In fact, I lost my virginity that amazing and passionate night. Anyway, both Jay and I shared our dorm room, and became friends. Once we met Kylie, we pretty much became blood brothers. That entire semester was filled with a ridiculous amount of sex with her, and we were thrilled. Though we never pursued romantic relationships with her to keep things casual; we were quite the trio, and still keep in touch (non-sexually) today. Jay and I are definitely straight, but were super okay with our situation, and actually found it super arousing to both sexually please a girl together. We definitely have a different type of connection, given that we have seen each other at some of the most intimate and vulnerable times.

Anyway, I remember it was a Thursday afternoon, and I had a final that morning. Kylie and Jay were finished with all of their exams on Wednesday. Everyone knows finals are stressful, and the last few weeks we did not see much of each other, as we were concentrating on final projects and studying. I literally only saw Jay when he came to the dorm to sleep. But it was over, finally! However it was kind of busy still since move-out day for summer break was Saturday. Once I was done with my last exam, I went straight to my room to do some more packing. Jay was doing the same when I got there. He asked me how I did on the test, and I responded that it was touch and go, but I was confident in my answers. We then started talking about how we were already through our first year. Time indeed flies. The packing continued, and we got to the subject of Kylie and how we ought to have a last hurrah with her before summer, if she was up for it. What better way to celebrate the end of finals week that with on of our “sessions.” It sunk in that we would not see each other for a few months, which was also kind of a bummer. So Jay gave her a call and put her on speaker.

She answered and said, “I was wondering when you two would finally call me!” We laughed and asked her what she wanted to do tonight. All of us needed to make a little more progress on packing up, and she said she could come over around 4 o’clock and we would head somewhere for food off campus. Kyle ended the call with, “We are really gonna celebrate later,” in a suggestive voice, “so don’t wear yourselves out too much packing up.” God we loved it when she teased us about what sexual escapades were in store. Just the thought about it gave us both a semi-boner. At about 3 o’clock we were pretty much done getting our shit together for the day and I went to shower. The stress of the week made me put my normal hygiene habits on hiatus. So I scrubbed myself down to almost surgical standards, making myself squeaky clean for the night’s events. When I got out to dry, Jay was by the sink naked, intently manscaping his pubes with his electric beard trimmer. I said, “Sprucing up, eh?” He responded, “Hell yeah, it’s been too long since we last got our dicks wet, my friend.” I then threw on some khakis and a polo, crashing on my bed to be on my phone for a bit while Jay showered.

It was approaching four, so Jay and I headed down and were hanging outside waiting for Kylie to show up. “Well hello!” we heard her voice from behind us, and there she was, wearing a pink casual sundress and her hair tied up. She looked absolutely beautiful and beaming with her gorgeous brown eyes. I asked if she was ready to go, and Jay asked her what kind of food she wanted. Kylie replied that it was a good day for sushi, and not anything heavy. That seemed like a good plan, especially since we were gonna have a naughty naked workout later. With that, we all headed to my car, and went to the really awesome sushi place in town. The meal was good, and we split edamame and like five sushi rolls. We got on the topic of summer plans and how we were gonna miss each other a lot until next year. Trying to be as adult as possible, we discussed some sexual ground rules for the summer. We agreed that we would try hard to keep in touch, and to not sleep with anyone else if we could help it. If any of us did want to hook up with someone over the break, we would let our trio know, and make sure to use condoms. Don’t worry, we were in a quiet part of the restaurant and no one heard us! But yeah, there was no way we were not gonna keep this arrangement another semester. A way to relieve stress, stave off horniness, with few strings attached? Hell yeah!

After we finished our meal, we got in the car and I came up with a plan. I said, “We should rent a motel room tonight, our room is a mess.” Jay agreed, and Kylie said that sounded good, but that she wanted to bring an overnight bag. Thus, we went back to campus to grab some stuff. Kylie went up to her dorm and Jay ran up to ours. I just asked him to grab me a t-shirt, boxers, deodorant, and a toothbrush. After fantasizing about the night in my car for a few minutes, Jay got back with a backpack and we went over to pick up Kylie, who was waiting for us with a tote bag of her stuff. We were off to the Quality Inn nearby, and we could not contain our excitement, My heart was beating fast in anticipation. Kylie said, “You guys are so gonna fuck my brains out, I hope you know!” I responded from the back seat, “You have no idea, I’ve been pent up for weeks.” Jay, driving, started to playfully grope her side, tickling her, and she started squealing and giggling: “Oh my god, stop it Jay, ten and two asshole!” Just to get to speed this along a little, we finally got to our room and it went down.

The door closed and I locked it. As soon as I turned around Kylie had pulled her dress off, leaving just a white lace bra and matching thong. Frantically, I got naked along with Jay. He went up to her and they kissed passionately, as I pulled down the covers of the bed. Grabbing her around the waste, I playfully pulled her onto the bed with me, her screaming slightly and laughing. Jay hopped on the bed to continue kissing her, while I gently pulled off her panties. There was her pussy, as amazing as ever, her outer labia curved like two crescent moons, with darker, slightly protruding. inner labia. This time around, she shaved herself completely smooth. I could not help but put a finger inside as she gasped. Jay got her bra off and was sucking on her now hard, darker brown nipples, on her perfectly firm B-cup breasts. Kylie proceeded to order both me and Jay to lay down on our backs, side-by-side. Kneeling between us, she moistened her hand with saliva, and stroked my shaft gently which was heavenly. Then, while pleasuring me with her hand, she began to bend over and take Jay in her mouth and give him a very wet blowjob. God I really needed this, and just closed my eyes and took in the sensation. Hearing the blowjob get more intense with slurping and sucking sounds, Jay began to moan a little. Abruptly, she stopped with him and gave her oral attention to me.

Jay was like “Hey, why did you stop, I was close to coming!” Kylie responded, releasing me, “I don’t want you to come yet! I want to see who can last the longest. Whoever comes first is the loser!” Kind of frustrated, Jay said, “Fine, I’m gonna win, though,” and stroked himself while Kylie worked on me. God, she was making it hard not to explode, the way fluttered her tongue against the tip and under the head of my penis. It took a lot of concentration, but I held off a little, and after hearing my breathing increase, she stopped and went back to orally stimulate an increasing impatient Jay. That was close, any longer and I would not be able to hold it back anymore. I was too sensitive to stroke myself, so I just caught my breath as she worked Jay up. He was grunting and moaning again, and it kept me rock hard. I knew he would not be able to resist blowing a load this time. As he got close (knowing from his vocalizations), I pleasured my member again. Jay said, “Goddamit I’m gonna come, fuck! Ahh!” Kylie released him from her giving mouth and started jerking him off. A few seconds later, Jay began to grunt, and Kylie aimed him towards her chest and he came powerfully. In fact, his first spurt went over her shoulder and into the air! The rest splashed into her neck and boobs.

“I win!” I announced breathlessly, while Jay laughed. Stroking myself vigorously, I was getting really horny up by what I just saw. Kylie immediately came over to me to finish me off. Jay’s load was all over her and I could smell its distinct scent. Literally within like thirty seconds of her mouth expertly teasing my dick, it was go time. I said, “Jesus, I’m coming!” And I just let go, spraying at least four strong blasts of sperm straight into her mouth and throat, as she swallowed. It was quite a bit and she started coughing and laughing at the same time. She said, “Shit,” coughing in between, “down the wrong pipe!” We all laughed. Clearly she was a little too enthusiastic. That’s what happens when we were pent up, not being together for a while. Jay got up off the bed while Kylie collapsed on her back next to me, both of us exhausted. Then she grabbed my hand and interlaced her fingers with mine and we just lay there catching our breath. We looked into each other’s eyes and just laughed then kissed gently and sweetly. Jay came over with a wet washcloth and cleaned his sticky splatter off Kylie’s neck and breasts, she then leaned over to give him a brief kiss in gratitude. We all laid on the bed on our backs side by side, as Jay and I recovered for about twenty minutes, joking around and talking.

Jay has a shorter refractory period than I do, and was developing another erection, apparently ready for round two. Kylie was definitely ready to get her pussy filled as soon as possible. She said to Jay, “Let’s do it facing each other, sitting up. I really want to look at you while you fuck me.” They got into position on the bed, joining their groins together and started to hug and kiss hotly, with their legs straddling each other’s waist. Slowly, Jay inserted inside her, and begun arch himself in and out of her. They held onto each other so neither of them would fall backwards. Kylie started to moan softly, and said, “You are really hitting my clit! This feels amazing.” They looked so intimate and close, and my boner was back now, too. I went behind Kylie, and knelt behind her, supporting her against Jay, kissing her neck and shoulder, and nibbling on her ear. She tucked her now damp hair behind her ear and turned towards me a little, and we shared a really passionate kiss, stifling her squeals and moans. Then she leaned back into me and I put my hands on her bouncing tits. At this point, Jay was thrusting into Kylie hard while she played with her clit, and I could feel the reverberations. Both Jay and Kylie started getting pretty loud, and he announced he was about to come again. Kylie said, “Okay baby, come inside me!” He grunted, and gave about five more pronounced thrusts with each ejaculation.

Jay was still inside her, after coming, while they caught their breaths. Not wanting to make a mess on the sheets, Kylie had me run into the bathroom for a hand towel. I quickly handed one to them, and she folded it in half, and Jay lifted them both off the bed to put the towel underneath them. Jay’s cock flopped out of her, followed by a creamy torrent of his genetic information onto the towel. That was so freaking hot, and I was now uncomfortably stiff. The last remnants of Jay’s come dribbled out of her, and she wiped herself dry. I was ready for my turn. Both of them were quite sweaty, and she lay on her back, legs splayed, giving me full access to her wet, rosy and engorged vulva. I got on top of her, belly to belly and made out with her for a little. Then I sat back up and knelt down between her legs and slid my hard-as-steel dick inside a little too fast, making Kylie wince a little, her letting out a surprised squeal. As always, it felt so good; perfectly warm, slick and textured, thanks to Jay’s previous labor. Kylie had her fingers in her mouth and her eyes closed, moaning softly as I pumped in and out slowly and deeply. This was so comforting and relaxing, feeling like I was home. I needed this very much and savored it, wanting it never to end. Leaning forward, I put one hand on her boob and gently pinched her nipple, and used my other hand to rub her girl pearl with my thumb. She orgasmed and I was about to shoot.

Kylie was so wet, and each of my plunges produced an enticing squishy sound. Her fluids were running down my scrotum and dripping off. I said, in a breathy voice, “I’m getting close to coming.” She replied, “Okay, I want you to hold me when you do.” Cradling her head with one hand, and my other around her writhing torso, I pulled her to me tightly. Kylie rested her head on my shoulder, and put her arms around my shoulders. The closeness put me over the edge, and I began to unload my balls deep inside of her, making unintelligible grunts and moans. I held onto her as I rolled on my back, and she layed on top of me as we made out, my softening penis still inside her. Jay pushed a towel by my butt and balls, to absorb the backflow as Kylie lifted herself off of me. Running down my ballbag and crack was a warm mixture our combined sex fluids. We were a hot mess, spent and we collapsed on our sides facing each other, looking into each other’s eyes. Laughing and breathing heavily, we calmed down a little and relaxed. Kylie said, “Oh man that was good. Holy crap, dude!” I sat up and dried my junk and butt with the towel and passed it to Kylie, and she did the same. Jay was sitting in the chair just watching what went down. He said, “God, that was hot as shit! Could you guys have made more of a mess though?” I flipped him the bird. The aroma of freshly had sex was abound, and it was intoxicating!

In the bathroom, Kylie and I peed, freshened up, and drank some water. All of us really needed a break, so Jay and I cuddled with her in the bed under the covers, completely naked, and watched some TV. Thinking in advance, Kylie brought a bottle of Gatorade and some chocolate in her bag, so we replenished our calories and electrolytes. After chilling out in bed for about an hour, we were getting horny again. Kylie was playing footsie with us guys, and we were fondling her boobs and butt in return. I will always remember this, how upfront Kylie was and how she knew what she wanted, and being super chill at the same time. She said, “It would be super hot if you guys both fucked me at the same time. Like both of your cocks in my pussy, at the same time.” I busted out laughing and said, “There is no way in hell that we would both fit!” Jay responded, “I was gonna say, that’s would be kind of hard. No pun intended.” Kylie then went on to say that she was sure we could, because she has been working on herself with a large dildo she bought. We were both surprised, she never told us about this. It was a surprise for us she was saving before the break. At this point, I was super aroused by the idea, and so was Jay. She literally planned it all out and we immediately proceeded to give this thing a try.

Kylie got a tube of KY jelly from her bag, saying “I was reading that lube makes this a lot easier.” Man, she literally was reading up about this. Damn! Kylie then told Jay that he would come in from behind since he had the longer (but more narrow) penis. This worked out for me because I would be facing her, and therefore I could look at her. Taking charge, Kylie had Jay lay on his back with his legs dangling over the side of the bed, and began to give him a blowjob until he was super hard. I was stroking myself, pretty much already erect. Kylie squirted some lube on Jay’s member and started spreading it around with her hand. She then got up on the bed and squatted on Jay’s erection, as if she was going reverse cowgirl. She leaned back a little and supported herself with her elbows and splayed her legs outward. I now had easy access to Kylie’s filled hole. Somehow I had to squeeze my dick in there too. People might wonder if I was weirded out by penis-penis sliding contact, but not really. I only do it only in group sex scenarios when being sexual with a female, so I would no say I’m bisexual per se. Plus, I did it previously when Kylie took Jay and I in her mouth at the same time.

I took the lube and added a little squirt on Kylie’s slit, and put some on my uncomfortably inflated cock. Then, after I rubbed the underside of my shaft against her clit I said, “Alright, I’m going in!” Right before I was gonna push it in, right above Jay’s insertion, he accidentally flopped out with a faint popping sound. He laughed and said, “Oh shit, my bad! Fuck, I can’t reach it.” Kylie was leaning back on top of him, making it impossible to guide himself back in. I replied, “I got you, man.” In the heat of the moment, I gently and briefly grabbed his penis, and helped him re-insert. This was the first time I actually handled another dude’s junk, but I didn’t mind it, given the situation. Jay started thrusting in and out slightly to keep himself stiff, and Kylie moaned slightly, saying “Okay, now you.” I was super turned on, and proceeded to push inside, sliding against Jay. It was super tight and by inserting, Jay’s penis flopped out again. We all laughed. I pulled out and helped Jay back in her pussy. This time I held Jay in place so he would not fall out, and thrust myself inside. Kay let out an excited little yelp, and finally we were both inside her at the same time!

The sensation was like nothing else. Quite tight, but in a very pleasurable way. I could feel the underside of Jay’s shaft along mine, adding some amazing firmness. Funny enough, I could feel Jay’s heartbeat throbbing through him. The walls of Kylie’s pussy pushed back in such a way, that it felt like we would be pushed out if we did not thrust hard enough. What was awesome was that I could really feel the texture of Kylie’s vaginal walls because of the tight squeeze. Facial expressions on Kylie were hilarious, her eyes wide and her mouth gaping open, dealing with being stuffed to capacity. She was breathing heavily and letting out some squeaks, but completely non-verbal. After maybe a minute of experimentation, Jay and I figured out that alternating plunges made it easier to stay inside without popping out. The lubricated sliding feeling against each other’s member was absolutely terrific, not to mention our testicles bumping and rubbing. It was sensory overload, but I just concentrated and paced myself. The most sensitive part was the underside of my penis head, the frenulum, as it met Jay’s. Jesus it felt so good, better than anything else previous to this. Kylie started wimper, squeak and cry out a little as she had an orgasm.

I felt a deluge of wetness flood into Kylie, adding even more lubrication. Everytime we thrust inside, I could hear sloshing sounds, and feel fluid drip down my balls. Jay and I started to pick up the pace instinctually, absolutely loving the sliding friction and only wanting more. The only sound us guys were making were grunts and groans. I was sweating profusely, and my heart was racing. It took everything I had not to shoot my load, wanting the pleasure never to end. The end was near, the pressure in by prostate and urethra building, about to boil over. It was eruption time. Looking into Kylie’s scrunched face, I communicated with my eyes that I was coming soon. I leaned toward her and she put her arms around my neck, and looked into my eyes hungrily. Not being able to take it anymore, I let out a primordial growl as I spilled what felt like everything I had inside her, slowing my thrusts. If I were to guess, I think I have maybe five total spurts, which were very strong. Inside Kylie, it got super slippery, and there was less friction sliding past Jay. While I was passionately kissing Ky, Jay was making some noises and was so close to finishing. I was thrusting more slowly, but Jay was thrusting at top speed. Getting sensitive again, it was almost too much to handle as he sped up. It was a painfully good feeling.

Sperm was trickling down my balls from my emission. Jay began to moan and grunt, until he almost yelled in pleasure. He began to inject his load, and I could feel it spraying against my softening dick. I felt the warmth of his jizz fill the cavity, making it slick again. The sensation turned me on and I was getting another erection! As Jay began to slow down his thrusts from coming, I began to speed up again. With each of my strokes, Jay’s seed began to leak out, making it less slippery, giving me friction to work with. At this point, Jay was going soft, still inside Kylie, thrusting very slowly. Here I was, still going, about to come again! I have never blown a wad back to back before, but I know it is possible. Kylie was reclined back, over a recovering Jay, and just looked at be in disbelief that I was still going. Nevertheless she was loving the sensation and getting super worked up, about to have one more orgasm. I knew this second load was not gonna be nearly as strong, but I was getting close. Then, Kylie began to climax, squealing and giggling, introducing more wetness in her still filled vagina.

This was all I needed. I leaned onto Kylie, laying my head on her boobs, as she lay all the way back on Jay; she was now sandwiched between us. I moaned as I delivered the smaller spurts of come, scraping the bottom of the barrel, followed by two dry spasms. Exhausted and a little light headed, I got off Kylie to relieve Jay underneath her, and collapsed face down on the bed next to them. My balls ached and my prostate was cramped up, as everything was emptied. Literally, I could not move, and calmed down and worked on catching my breath. I could not believe I came a total of four times that night, a new record. Kylie said, “Holy shit, that was the sexiest thing you guys have ever done with me.” She hopped off Jay and both of them began to cuddle in spoon position. Jay said, “Fuck that was crazy. A can’t believe we did that. I feel dirty now.” We all busted out laughing. And lay there for a good ten minutes, saying absolutely nothing, completely spent. I then got up to go to pee again, clean up with a washcloth, and get a big drink of water.

When I returned, I saw that side of the bed was quite damp, and a wet spot on on the carpet, and the area smelled strongly of musty, alkaline seminal fluid. Jay and Kylie got up to look, and were shocked at the mess we made. In our haste, we forgot to lay down a towel. Kylie said, “God I now feel really bad for housekeeping.” We all laughed about it, and definitely were gonna try our best to clean as much as we could. All of a sudden, Kylie cursed, and she pointed to her thigh, giving us a playfully exasperated look. A small trickle of jizz slowly made its way down her leg from her slit. She then said, “Last one to the shower is a rotten egg!” Kylie started running but Jay was too quick and playfully grabbed her and put her over his shoulder, like a naked sack of potatoes. She squealed in delight, started giggling, trying to get free. He carried her all the way to the bathroom. I got the shower ready, while Kylie and Jay both took a piss and drank some water. We crowded in the shower and cleaned off, getting a little handsy. After being naked forever, we all put on underwear and t-shirts, respectable again. It was was almost ten and we were exhausted. After we cleaned up the room a little bit, we passed out in the bed, cuddling with Kyle.

When morning came, we just hung out and talked in bed, excited about summer. However, we were bummed that we would of course not see each other for a while. We had quite the friendship mixed with intimacy, and got so close over the last semester. I know it is corny, but we were attached to each other and were going to struggle being apart. Perhaps a break was to do us good, as we all very much wanted to keep the casual, friends with benefits situation going. Being too dependent on each other was probably not a good thing. She was flying home late that night, and we decided to have one more small romp. It was more nice and intimate than anything, both of us had a turn with her missionary, injecting her with a last bit of us for the road. Very simple and sweet, kind of sexual bon voyage. We left just in the nick of time for checkout, and drove back to campus to finish getting ready to leave. A perfect end to my first year at college.

Source: reddit.com/r/gonewildstories/comments/9oup7k/kylies_first_double_vaginal_penetration_with_me