I actually lost my virginity to two boys at once when I was young, and I initiated it! It’s a super kinky story, but there’s back-story that you need to know. If you like to read kinky shit, keep going. If not, hit me up in chat!
There was a neighbor boy I fooled around with when I was too young to talk about (forum rules). Nothing crazy. He’d sneak over, through my window, at night and we’d basically dry-hump and make out. I was a horny kid. Like really horny. I had older brothers and would sneak into their rooms and swipe their VHS porn. I’d sit in my room alone at night and watch actresses like Jenna Jamison. And OMG I had the biggest crush on Peter North! All that to say, I knew what was up.
So this neighbor boy and I would sneak around. He’d climb in my window and we’d make out all hot and heavy. We never took our clothes off, and I never even let him put his hand up my shirt or down my shorts (or pants), but he was all over my goodies over my clothes. He’d get crazy hard too! One day, I decided that I was going to go down on him. That’s another story tho…
About 3-4 months after I basically started sucking him off any time he snuck over, I was hanging out with him and another neighbor boy. We always hung out on Sundays. Our families would go to church, the three of us would walk home after, and our parent’s would stay for various groups, events and meetings. So the three of us would hang out and watch all the football games.
I love football, and we’d be alone pretty much until the late game, when we’d all go home for dinner. The room we’d watch the games in was over the garage in my neighbor’s house. He had a crush on me, but had no idea I was sneaking around with the other boy. And I flirted with them both, shamelessly. I never wanted a “boyfriend”, but I didn’t need one. I had their full attention all the time.
I knew already they had both had sex before. They were both 2-years ahead of me in school, and I knew the girl(s) they had slept with. So that was always in the back of my mind. One Sunday, we were walking home to do our usual ritual and I decided that today was the day. I was going to try and proposition them.
Immediately, I had all these ideas in my head of how to initiate it. Like a porn movie. We were almost through the first quarter of the first game and I got up and went into the bathroom. I had been sitting on the floor with Jim (names changed for privacy), it was his parent’s house. We were leaning up against the couch on the floor and Tom, the boy I had been sneaking around with for almost 3-years now, was sitting on the couch behind us.
As I stared into the bathroom mirror I got so nervous. What if they got all weird? I knew Tom would be down, but I had way kinkier things in mind. With butterflies in my stomach, and my heart racing, I took off all my clothes and walked out totally naked.
At first neither of them noticed. Tom was still on the couch, and Jim on the floor. I just kinda announced out loud: “I want to have sex, and I really want it to be with the two of you.” Tom got up and walked toward me. As much as we’ve fooled around, he’d never seen me naked. I extended my hands out to Jim, on the floor, and helped him up. His eyes were huge, and because he jumped up so awkwardly, when he got to his feet we were pressing against each other. So I kissed him.
I looked at him and said to him, I really want this. He kissed me again, and then we really started making out heavy. As his hands are all over me, Tom got behind me and started kissing my neck. So I’m standing there between these two older boys, totally naked, and they’re kissing and touching me all over. I can’t even verbalize how horny that made me.
I got Jim to sit on the couch, and as I helped him get undressed and prepared to suck his dick on my knees on the floor in front of him, Tom took his clothes off. I leaned forward and with Jim’s penis in my hand, put my mouth on it and started going down on him, and as he leaned back, I felt Tom pull up behind me, his fingers rub my pussy, and then his penis press inside me.
I should add at this point that I get really wet. So wet that I used to get embarrassed about it, that is until I realized that guys think that’s hot. Anyway, his penis slid inside me and just like that, I was having sex with the two of them.
I orgasmed straight away. It was really good too, and that only make me more horny. I wasn’t about to do anal or anything like that—the thought didn’t even cross my mind—so we didn’t do any DP shit or anything like that. We pretty much just spent the next 35-40 minutes, with me letting them take turns with me. One fucking my pussy while I blew the other one.
Finally, we were all on the floor. I was on my hands and knees getting fucked from behind by Tom, doggy style, and Jim was sitting in front of me with his legs out straight, and I was sucking his dick. He warned me he was about to cum, but I didn’t slow. I kept sucking his dick as he ejaculated in my mouth.
Still getting fucked from behind while a guy is cumming in my mouth ruined me, in hindsight. I fucking loved it! WAY too much. When he was done, I laid there with my head in his lap, clinging to his penis, at Tom continued from behind. I orgasmed really hard, and before I was even done, Tom came in me from behind.
I was so out of breath, laying there panting, clinging to one penis with Tom holding his inside me. Then, he slowly pulled it out and I could instantly feel the semen spill out. I reached back quickly, knowing I would be so embarrassed if it had left a spot on the floor. I turned onto my back and looked up at Tom, who was still on his knees with his penis dangling there. Laying against Jim’s chest, as Tom got up he helped me up and I scurried to the bathroom with my hand over my crotch.
I had no idea what to do. This was all new. I’d always swallowed it. Now it’s spilling out of me. I sat on the toiled and as I took some toilet paper and wiped my hand, all this cum just poured out from inside me into the water. It sounded like I was peeing! It just kept coming, and when it finally stopped I wiped, got dressed, and came out.
Both of them were dressed and back to watching football. We finished watching whatever game was on as I snuggled between them on the couch. We talked a little about it, mostly in kinky ways. I told them how much I liked it, and how good it was. Hyped them up. And it was good. I had 7 orgasms!
After the game I went home, ate, did some homework, then went to bed. Later that night Tom snuck over and he and I had sex again. First time we were naked together in my bed. We did it in missionary. It was so sexy having him on top of me. I felt so close to him. He got me off 4 times and then came inside me again. I hadn’t showered or anything, so in less than just a few hours that boy had cum inside me twice. Sure, I knew wat could happen, I just didn’t care. I fucking loved it. To me, that was the kinky part!