How I lost my virginity in the weirdest, but hottest way. [18/19 MFMFMFM] Long, buildup

All this happened at a party when I was much younger.

We were at an older friends house, she celebrated her 19th birthday. She always had a rich and extravagant family, so it was a sleepover party. We were three girls [Sally, birthday girl. Italian, dark hair. Annie, tiny blonde with short hair and a radiant smile. Nadia, chubby shy girl] and four boys [me, scrawny funny guy with glasses. Luke, tall shy dude. Nick, popular handsome kid. Danny, the class clown] – boys were intended to sleep in the guest room and the girls in Sallys super king size bed. Her parents cleared the area after the main party actions were over, probably to have some alone time themselves. We all retreated to Sallys room, where she had a computer with flat rate internet – a miracle back then. We did typical kids stuff like pretend to be someone else in chat rooms and everyone chimed in what to type for maximum fun. It got us in a really lighthearted mood, and someone suggested we'd play a card game. After a few rounds, someone said "let's make it interesting" and suggested we'd play a raunchier version of the game – the first one to drop out of a round would have to do whatever the winner of the round dared them to do. Basically a slower but fun "truth or dare".

It started out really slow and timid, with dares like "do a headstand" or "take a shot" (we didn't have much, but some alcohol). After a couple of these, Sally won a round after I had screwed up first. She knew I always liked Annie, and she was the giggly-motherly type of girl, so she suggested me to give Annie a shoulder massage. She was gymnast so she had some muscle on her back, plenty to give her a nice massage, which I was confident doing. I sat behind her and started rubbing her back and shoulders, and she definitely appreciated it. I got really nervous, but tried to play my cards right so I just stayed close behind her after i was done, to continue the game from there. The next loser was Sally, and she was dared to go do "7 minutes in heaven" with Nick. We all laughed like it was a shameful or bad thing to be doing, but when they came back I felt like they definitely enjoyed it, even though they didn't tell anyone what happened. We continued, and the first clearly raunchy dare came on. Danny was dared by Luke to give Nadia a quick kiss, maybe in a mean spirit cause Nadia was "the fat girl" and you weren't supposed to want to kiss her or something. But Danny wasn't so shallow, and just went with it and said he actually liked it – I figured he was just being nice, but I would be proven wrong just a while later. When Sally won the round she was able to dare Nick to take off his t-shirt. She clearly had planned that before, and didn't hide that she enjoyed what she saw when he stripped it off. She clearly was more than in the mood, and decided to take it up a notch. She had gotten "sex dice" as a fun gift, and proposed we'd have to use these to decide what to do when winner and loser were a girl and a boy. We very shyly agreed, as no one wanted to be the buzzkill. If you don't know what sex dice are, it's two dice with one having body parts on them (like feet, butt, pussy, ..) and the other one an action (touch, massage, kiss..). So .. the game quickly got off the rails.

When we had the first boy-girl combo it was Luke and Nadia. Luke won and was allowed to roll the dice, and got "Caress" and "Free Choice". He scooped over to Nadia and first looked like he wanted to touch her boobs, but shied out and told her to turn around and rubbed her ass for a couple of seconds. Both got back to their spots with hot red faces, but didn't look unhappy. We had a couple of "normal" dare rounds, where some of us had to take off pieces of clothing, and some of us were quickly in underwear. This was clearly the most sexual situation I had ever been in. It was clear that nobody would object to anything that was dared or the dice would show, and it was just a matter of time until something really explicit was bound to happen. And it did. Sally again lost a round (I think on purpose) and Danny won. The dice were rolled, and showed "kiss" and "penis". We all stopped breathing for a moment, as we knew it was a possibility but didn't really know what would happen when it happened. "I won't do it in front of you guys" – "But how do we know you really did it?" – "She should just do it in here, but in the corner turned away from us. So we kind of know they're going at it!" We all agreed that this was going to be the policy from here on out. They got in the corner, we could all only see Dannys back. He fiddled around the front of his pants, Sally started to giggle, it took her a while after getting closer to his crotch, and then we heard a smooch. They actually did it, now there was no way back. We teased them and asked stupid questions like "oouh how did you like it?" because nobody really knew how to deal with this – but we just continued to play. Two girls were the candidates this time, and I leaned into Annie (who won) and whispered a suggestion for a dare – Nadia should take off her bra. She shook her head, but we encouraged her as she still had a (tight) top on, and she could just wiggle her bra off. She obliged, and her big boobs looked amazing inside the bit of cloth that the top provided. I knew now we would gradually get more and more naked and had to do whatever the dice commanded.

Sally had to make out with Luke, Nick had to massage Annies ass (which made me furious, but I had to stay calm), and then I finally was one of the win/losers, together with Nadia. I rolled the dice and held my breath. The dice were on "Sex" and "Free Choice". Holy fucking shit. This side of the action-die surely wasn't intended for party games. Everyone freaked out. I felt a lot of pressure, but knew that Nadia must have felt the same, so I wanted to be fair and asked "can i just choose any bodypart?" -"yes" -"well, then it's her hand." Phew. I was still really really nervous, but at least I didn't have to have my first "real" time with Nadia because of a game. We hesitantly got into the corner, I reached into my boxers and asked her if she was ready. She nodded, so I slowly pulled out my half mast of a dick. She slowly reached towards it and wrapped her hand around it. It was the first time anybody else touched it, and I instantly got hard. She started rubbing and jerking it, first looking away, but then being curious as it grew in her hand. It felt amazing. I turned my head around – everyone was frozen and staring intently – and I asked "does sex mean .. finish?" and after a very short discussion they said yes. She continued jerking me off and i felt an orgasm build up – three strokes later, I came all over her right hand, both of us breathing heavily. I put my dick back in my boxers (still showing a bulge, as I didn't really need to recover after this hotness), and we returned. Nadia wanted to get a tissue to clean her hands off, but someone said "stop – keep it. how about we dare the next girl to lick it off?" You could hear a couple of "yees" and "nooos", but as the boys were in bigger numbers the yes vote won. The girls agreed to this under the condition that they were allowed to make a rule for the next boy to lose as well, and we obviously agreed. He would have to get completely naked. So we agreed, and continued playing. I was nervous, and when I saw who lost my heard pounded. Annie had very bad cards. She would have to lick my cum off of Nadias hand. She looked scared and had a red face, and hesitated. She looked me in the eyes, and then put her lips on Nadias hand which was stretched out in front of her face. She put her tongue out and ran it all over Nadias hand, who had my cum on it and had jerked me off just moments before. She licked it all clean, and swallowed my cum.

When it was over I looked up again, and noticed that things had gone out of control. Sally and Nick were very close to each other and I was sure to see Nicks hand vanish somewhere behind her ass. Luke and Danny definitely both had huge boners inside their boxer shorts, which they didn't try to hide anymore. Annie scooped back to her spot in front of me, and I decided to get up closer to her and we kind of continued playing. I put my free hand on the side of Annies back during the round, and she leaned into me a little. I was freaking out. I noticed Annie was about to lose again, and I gave it my all to be the winner in this round. I didn't want anybody else to be the one to do something with her. But it didn't work. Luke trumped me in the last round, and I felt like in hell. I didn't look when he threw the dice, but the group loudly proclaimed the outcome anyways. Lick and Ass. They got in the corner again, this time Annie facing towards us. She slowly slid down her pants on her backside, but it wasn't enough for Luke. He pushed her on all fours and dropped her pants. I was boiling – he could clearly see her pussy that way. He lowered his head between her ass cheeks and started licking and kissing her, and I wanted to look away but Annie looked right at me with a sad look on her face and mouthed a "sorry" – I doubt anyone else could see it. After a couple of terrible moments, they stopped and came back to the bed.

The next round I had a bad one, and got close to losing but didn't give a fuck, I'd be happy to participate in some dice action – but when I threw my last card away and said "I'm out" I remembered that we still had an open losers' bet. The girls went crazy and all yelled "naked naked naked!". There was no way out. I had a raging boner anyways and wasn't ashamed of my size (jsut a bit of the rest of my skinny body), and i knew i had to do it. So I slowly took off all my clothes, sliding down my boxers revealing my boner in front of everyone felt awesome. When the girls finished cheering, I got back to my spot, this time even closer behind Annie so my nudity wouldn't be too visible to everyone. My dick was just inches away from her elbow.

Annie was in bra and the tight sweatpants she wore for the sleepover. As we continued with the game, the next two rounds were Nadia/Sally (Sally had to get topless – great mid sized tits full on display now) and Me/Danny (I told him to get blindfolded and be of free use to Nadia, who took his hand and used it to first rub Sallys then her crotch, asking him to tell which one was hers just from feeling. he got it right, so as a reward she reached into his boxers, pulled his dick out and kissed his red, thick tip. in front of all of us. the rules of the game had changed yet again.

When Annie saw the action, she reclined towards me, so that her backside rested on my raging boner. I pushed it into her, and she could definitely feel my hardon just below her bra strap. We just stayed like that for the next round of the game. I lost it because I couldn't focus at all. I really really hoped Annie would win or that we just stopped the game and went wild anyways, but that didn't happen. Sally won the round. I cursed my luck, but Annies hand softly reaching over my thigh had my hopes up for the rest of the night. I would just endure whatever I had to do. Sally rolled. She didn't look too happy either, pretty much everyone in the room knew she wanted Nick. The dice landed on "Sex" and "Pussy". If nothing or nobody intervened, I would have my first time with Sally. I didn't really know how to proceed, but I slowly robbed towards Sally uttering things like "well then … i guess.." As I passed Annie, I looked at her and she looked a bit sad, so I decided to kiss her. She kissed me back, and after a couple of seconds the group got loud (everyone but Sal) saying things like "ey! stop guys! You have to follow the game here! Go to Sally!". She was in the corner of the bed, looking a bit upset, but she slowly nodded as I looked at her. I got in front of her, she spread her legs and I reached for her panties (I was already butt naked). I asked "off or to the side?" and she answered it by getting rid of them. Her tiny italian pussy with a pitch black landing strip was in full display for me, and probably for the rest of the group as well – but I didn't notice anything else happening around me. I was afraid to mess up, so I said "you guide me at your speed". Literally nobody had condoms there, as we were pretty inexperienced and most of us virgins (I think only Nick had had a girlfriend before that point), so I negotiated that I didn't need to cum this time for the "Sex" to count. Sally took my Cock, put it onto her vagina and softly pressed it into her. Having this view in front of me, I forgot everything else. I thrusted towards her and slid into her pussy. There were we, two butt naked friends losing their virginity to each other in front of their buddies. It felt incredible, and Sally soon seemed into it so I thrusted and fucked her for what felt like a couple of minutes to me, but it's impossible to tell. We didn't kiss or look at each other at all, and when I felt an orgasm build I stopped as I remembered that I shouldn't come, and that Annie was behind me watching us. I pulled out and said "that is enough." But I was the horniest I have ever been in my life, and what I saw when I turned around didn't help. Nick was already naked and robbing towards Sally as I backed off of her, Nadia was in between Luke and Danny who both had their dicks out and she jerked both of them – and Annie just sat there, with gloomy eyes, looking at my throbbing dick that was pointing at her.

I got closer, hugged her and went in for a kiss. This time we deeply made out, until I had managed to open her bra behind her back (it took some fiddling). I took it off and just looked at her tits for a while, they were tiny but really firm and cute. I couldn't believe that I finally kissed that girl I had a crush on for so long, and was going to see her naked. I grabbed her tits and nipples and leaned in to make out with her again. The times of giving a fuck were over, and everyone was getting crazy on the one bed. I pushed Annie down on her back and took off her sweatpants, and was surprised to see she didn't wear any panties. Her pussy wasn't shaven, but her pubic hair was really thin and almost blonde. I pushed my head down to taste her, but as I felt that she was grooling like crazy already I couldn't wait. I realigned her hips and bent myself down on top of her, this time being more confident to find the entrance to the vagina myself. When I had found her hole, I went in for another kiss as I shoved myself inside her. She was much tighter than Sally, and I instantly came. I tried not to panic and act like it didn't happen, but I'm pretty sure she knew, as my second load was still big enough and my dick was pumping. I had to stay still and struggled so my penis didn't slip out. After a while of kissing, massaging her ass and boobs, and her telling me "she had always wanted this" (I couldn't believe it), I got fully hard again. Finally, I slowly started to fuck her. At first I was still very sensitive, but as time went on I could go faster and harder. She started to moan – I was secretly in love with this girl for a long time and now I made her moan. My dick slipped in and out of her tight pussy, and I grinded myself all over her body. When it got tiring (I wasn't about to come for a long time…), I pushed myself back and asked her to switch position. I told her to get on her knees when she nodded, and turned her around so we would face the rest of the group. And man, it had evolved to a full blown teenage orgy. Sally and Nick were fucking in the back corner like madmen, and Nadia was in the middle of the bed, lying on her back, getting railed by Danny while sucking and licking Lukes insanely large cock. After I could turn away from all of that, I stood up and got behind Annie who was on her knees on the edge of the bed. Her ass and pussy stretched out towards me, I felt all of my dreams fulfilled – I always had a fetish for that view, shoutout to /r/rearpussy! I quickly entered her again, and started to fuck her while looking at the carnage on the bed. This was truly unbelievable. We all just did our thing, after a while Luke and Danny switched positions – Luke barely fit his dick into Nadia. Every boy probably came two or three times in the next couple of minutes. When I finally felt it creep up again I thrusted as hard and deep into Annie as I could and blew my last load, balls deep into her pussy. She moaned very loudly, but I never knew or asked if she had come as well.

We just laid down and kissed and cuddled after that, and for a while the others just continued fucking around us. I was in heaven, seeing Annie smile at me like this. Nick and Sally collapsed and stayed closely together in their corner, and after a while the devils threesome slowed down as well. The two dudes were spent. But Nadia, apparently the stereotypically slutty fat girl, had other plans. She proclaimed "now I fucked two, but I won't leave until I had all of you!", sitting in the middle of the bed on her lower legs with her crotch pushed forward. I saw Nick twitch, give a kiss to Sally and rob over to Nadia. He was rock hard and they just instantly got at it in front of five horny pairs of eyes. After a few minutes, he slid out and fell back, and Nadia motioned towards me. I embraced Annie and whispered "I guess I have to do Nadia if that's okay", and she said nothing – but young and dumb me just went for it. I got on my back and let Nadia, who was much bigger than me, ride me. Sally didn't really want in on any of this, and after Nadia seemed satisfied (or just tired), we all stopped and split into the two rooms – the threesome went to the guest room and the two couples stayed on Sallys bed, and we all slept really quickly.

In the morning, everyone acted much more reserved and not sure how to deal with the situation. Annie and I had a fling for a couple of months after that, just like Nick and Sally. I'm not too sure, but I think Nadia started to casually sleep around with any horny boy who was willing to.

Source: reddit.com/r/gonewildstories/comments/41tv7j/how_i_lost_my_virginity_in_the_weirdest_but