Losing my virginity in a threesome (M/F/M) *Long* | 2016

Most of this is back-story but, if it’s well received, I’ll definitely post more of our sessions!

My senior year of high school, I had become good friends with a guy (We'll call him Chris) in one of my classes. I never really checked out guys or anything, but Chris was a decent looking guy. He was also on one of the sports teams at school, so he was in good physical shape. I'd be lying if I said I didn't want to see him naked.

His girlfriend, however (we'll call her Stacey), was easily one of the hottest girls in our school. She was slim, beautiful tan skin and dark hair. Granted, she knew she was hot, and sometimes could be a little bitchy and conceited because of it. She wasn pretty shy most of the time, but also was a total selfie whore and loved the attention.

Chris and I had started hanging out after school, sometimes at my house, sometimes at his. Once when we were at his house, Stacey had come over as well and I had finally got to meet her officially. Chris and I just played video games or watched TV while she would stare at her phone or laptop. We still all talked and joked around and got comfortable with each other. Eventually, one day, Stacey brings up the question, “Sooooo, when did you lose your virginity?”

I hadn’t told them I was still a virgin, and was a little hesitant to do so for fear of being judged. Regardless, I spoke up and said, “I actually haven’t had sex yet.”

They both look at me a bit bewildered. “Really?!” they said almost in unison. “I know, it’s tragic,” I replied, just trying to ease things over. They laughed and said it was totally cool. I admitted that I had done just about everything else but actual penetration, so I wasn’t completely inexperienced. I even asked if they’ve had sex, to which they replied they have. I didn’t think much of it after that.

The next day at school (a Friday), Chris and I were chatting it up as usual about whatever we could think of. Eventually, he looks at me like he wants to say something but it hesitant at the same time. I ask if everything is ok and, after contemplating something he looks at me and says, “Are you wanting to lose your virginity?” I look at him a little puzzled and said “Yea, I guess so. Why?” He looked at me and said, “Promise you’re not gonna judge and we’ll still be cool?” I was pretty confused at this point and said “Yea, sure!” He replied, “Well, Stacey and I talked about it and, if you want, she’ll take your virginity.” I looked at him amazed, like he didn’t actually say that. “What Really?!” I asked. He laughed and said “Yea, man. We’re both cool with it. But we have some conditions.” I asked what they were; expecting just using a condom, but he also added that he wanted to watch and join in, aka a threesome. I was a little taken back, having never thought of that before, but ultimately I agreed, as it meant I’d get to be inside Stacey.

Once he got my approval, he messaged her and told her. She had replied and asked since it was the weekend if we wanted to do it after school. I said sure, and of course that became my obsession for the rest of the day. When school was finally over, we met up outside the building and told each other we’d go home and get ready and come over later. After an hour or so of “personal grooming,” I told him I’d come over. He replied it was cool and that he had condoms I could borrow. I arrived and was greeted at the door by Stacey. She wasn’t wearing any lingerie or anything, just jeans and a tank top, which she still looked hot in.

We went to his room and all talked for a bit just to ease into things. Then, at one point, he says “Oh by the way, my parents get home in about an hour, so yea,” he trailed off. Stacey and I just laughed and looked at each other with a devilish grin. I asked if it was cool it we start, to which they both said sure. She was acting very giggly and said “Idk how to start!” Chris motioned for me to approach her, which I did, and began kissing her.

As we made out, he started touching her boobs and she felt his dick bulging in his pants, getting hard. She then started feeling my dick getting hard and whispered, “This is fucking hot!” After a few more minutes, she got up off the bed where we all were, stood before us and removed her tank top. She was wearing a very cute polka dot bra that complimented her slim physique. She then looked at us and said, “Jeans or bra next. What would y’all like?” We looked at each other, both smiling and shrugging. Eventually, Chris said “Tits, babe,” and she proceeded to undo her bra. She had small B cups, which looked amazing. I told her so, and she smiled and thanked me, giggling.

She then asked us both to come to her, which we did. We stood around her, both fondling her boobs as she moaned with pleasure and started undoing our pants. They came off almost in unison, and my curious side finally got to see Chris’ dick. He was slightly bigger than me, but I didn’t want to say anything to freak him out or anything. However, he had looked over at me and, after seeing it exclaimed “Dang, man. Nice!” I laughed and said thanks, and ended up complementing his as well. Stacey even said, “Hey, I’m the lucky girl who gets two cocks!” We laughed again as she got on her knees and began to suck.

After a while of her going back and forth between his dick and mine (balls included), she asked what time it was. He looked at his phone and said we had less than 30 minutes. “Oh shit,” Stacey replied, looked at us and said simply asked, “So, are we doing this?” Chris and I looked at each other, both still hard, and said sure! He had wanted to go first, and I was fine with it, since it was his girlfriend after all. He lied down and she proceeded to take off her jeans and black thong and got on top of him and slid his bare dick into her. I watched them for a few minutes from the foot of the bed, watching his balls smack against her tight ass, as he trusted up into her pussy. He then wanted to change positions, with him fucking her from behind while she sucked me. After a few more minutes, she asked if I was ready, to which I eagerly said yes. She helped me put a condom on and laid on her back, while her and Chris made out a little. She then helped slide me inside her and let out a moan of happiness. “Feels good, huh?” asked Chris. I told him yea and took my time getting used to the feeling. After a couple of minutes of getting a rhythm going, he put his dick next to her mouth and she proceeded to suck him. The combination of my friend getting blown while I fucked his girlfriend made me build up pretty quick and cum soon afterwards.

Once I finished, we all high fived (I know, it’s lame) and Chris continued fucking her until he cam all over her stomach. Seeing his hard dick all wet from her pussy got me pretty hard once again, but almost right after he finished, we could hear a car pulling up the driveway. He threw on a pair of shorts and said he’d stall whoever would walk through the door while we got cleaned up. We shared a towel and afterwards, Stacey asked, “I hope it was ok.” “It was great!”, I replied, and leaned in to kiss her again, which she liked.

This was just the first of several sessions we all had together. If there’s any interest, I’ll post some more!