I lost my virginity to two boys at once, and I initiated it. I wrote in another post here, about the first time a boy came in my mouth. He was one of the boys. They were both neighbors in fact, but I had been sneaking around with the one for over two years before this. Finally, on a Sunday after church, I decided I wanted to do it!
We always hung out after church on Sundays. Our families would all go together, and then our parents would stay for various events and things, awhile we’d all go (the two boys and me) the one boy’s house and hang out in his parent’s bonus room and watch all the NFL football games.
I loved football more than they did! We’d hang out, undisturbed, pretty much until the start of the late game. We’d all head home for dinner when our parents got home. It was the same routine every Sunday. On this particular Sunday, I decided I was going to proposition them for sex.
Like I wrote in my other post, I was a very horny teen. I had been watching porn for a long time before this, so I knew what was up! I also fucking LOVED sucking off the one boy. He had been sneaking around with me for so long, and the second boy had no idea. He had a total crush on me and was totally unaware that I was pretty much sucking off his best friend 3-4 times a week!
Anyway, we made it through the first quarter of the early game. I knew if I was going to get away with this I couldn’t wait too much longer. No one would be home for hours, but this was all uncharted territory for me. I didn’t want to get caught or look obvious when anyone returned later.
I was so nervous too! I always flirted like crazy with both of them. It was all very much in fun. And there was always a lot of inuendo between them and me. As we sit there watching, my heart raced. I was on the floor next to the boy’s house we were at, we’ll call him Jim. He and I were sitting on the floor leaning against the couch. The other boy was sitting on the couch behind us. We’ll call him Tom. Tom was the one I was already fooling around with.
Truth be told, I liked Jim more. If I was ever going to “date” one of them like BF and GF, it would have been him, but Tom and I were freaky. Lol But I digress. Lol I finally got up during a TV time out and went into the bathroom.
The bonus room we hung out in was over Jim’s parent’s garage. It was a finished room they turned into a theatre room. It had its own bathroom, and a bar that his parents kept loaded. Of course we would take drinks from time to time. Most importantly though, it was pretty cut off from the rest of the house, and if anyone came home we’d hear the garage door open.
As I went into the bathroom and closed the door behind me, I spent what felt like forever staring in the mirror. How was I going to do this? What if they said no? What if one agreed and the other didn’t? I had a solution for that, but I was hell-bend on doing it with both of them, and yet another Jenna Jameson movie was stuck in my head, totally obscuring my expectations of how this was going to play out.
I peed, and then washed my hands and fixed my hair, then I took off all of my clothes and walked out of the bathroom totally naked.
At first, neither of them noticed. They both sat there watching the game. Then Tom looked over and I watched his jaw drop. Jim looked too, and quickly hopped up off the floor. I stepped toward them and reached my hands out to Jim, as he extended them and held mine. Tom asked, “what is this?!?”
I told them, “I want to have sex, and I want my first time to be with the two of you.” Neither of them said anything, but they also didn’t visibly or inaudibly disagree with wanting it too. I pressed my body up against Jim’s and kissed him and then took his shirt off, pulling it up over his head. When it was off I pressed my tits against his chest and we kissed more.
My heart was racing 700 mph. Neither of them were virgins. I was worried I would not be as good. As he and I continued to kiss, his hands grasped my ass cheeks. Tom got up off the couch and got behind me. He put his hands around my waist from behind so I turned and as he took me in his arms next, I leaned in and kissed him. We made out for a second or two, and then I told them both to get undressed.
I stood there watching as both boys took off all their clothes. I was drenched. Like really drenched! I get really wet. Like embarrassingly wet. I used to be self-conscious about it, that is until I realized guys think it’s hot. I made Jim sit down on the couch and I got on my knees on the floor in front of him. I put my hair back with a hair tie I had on my wrist and then leaned in, took his penis in his hand, he laid back, and I started sucking his dick.
As I was doing that, I felt Tom get behind me. I felt his outside of mine on the floor, and I spread mine a little. I knew it was about to happen. He must have licked his hand because when he put it on my pussy it was already wet, but I know I soaked his fingers too, as they slid through me, and then just like that, I felt his penis push up inside me.
I lost it. I mean my legs went weak. For like a second. I dipped, before getting it back and refocusing on the penis in my mouth. Tom maybe thrust himself in and out of me 10-12 times and I orgasmed so fucking hard I think I stated squealing. My thighs quivered like I was violently cold. I had Jim’s dick in my mouth and I was moaning on it as drool spilled out of my mouth down his shaft.
Tom kept thrusting. It was so hot. He was pushing places inside me that I don’t think I’ve ever touched by myself. And his dick felt so fucking hot. I could tell I was a total mess down there too. And I could also tell he fucking loved it! I orgasmed again and then he pulled out of me, almost giggling in amazement.
I orgasm really easy. It’s not at all uncommon for me to get myself off 8-9 times masturbating in just a few minutes. Having sex was proving even easier at getting me off! When Tom pulled out he and Jim switched places. Tom sat on the couch and I got on my hands and knees on top of it, perpendicular to Tom. As I started going down on him, Jim got behind me on the couch and started fucking me from behind.
I liked this way more. I was totally in love with Tom’s penis. I had been going down on that boy for so long. It was what I knew. I knew exactly what he liked, except this time he tasted like me, and that turned me on so fucking much! The two of them did me like that for a bit. Jim got me off once, and then the boys had me sit on the couch and lay back and they took turns fucking me while kneeling on the floor in front of me.
Since this is a tell-all, I liked this the most. I liked watching Tom stand there with his penis in his hand, watching as Jim fucked me. And I liked looking down and watching both boy’s penis’s sliding in and out of me. They both made me orgasm a couple times. Then we moved to the floor.
Jim sat on the floor, leaning back with his legs spread out in front, holding himself up with his arms behind him. I got on my hands and knees in between his legs and started sucking his dick. With my ass up in the air, Tom got on his knees behind me and started fucking me doggy style.
I orgasmed pretty hard. He was fucking me pretty hard too. Slapping into me. My head would jerk as I held onto Jim’s penis, sucking it. My tits were swinging. Then, Jim told me he was going to cum. I looked up at him, still jerking while getting fucked from behind, and told him to cum in my mouth. I put my lips around his head of his penis, I felt it start to twitch, and at the same time, I tasted his cum start to ejaculate in my mouth.
I kept sucking and swallowing as he moaned with pleasure. He came a lot! Like a lot, a lot! Some spilled out of my mouth, and when he was done ejaculating, I looked him in the eye and licked it. I continued to hold onto his penis while Tom fucked me from behind. I’d occasionally kiss or lick it, or even put it back in my mouth, but for the most part I just hung on, with my head in Jim’s lap, while Tom fucked me.
I was moaning so hard. He felt so good inside me. I was concentrating on orgasming again when I heard him mumble that he was going to cum. Panting like crazy I’m pretty sure I moaned, “yes! Yes! Yes!” like 100 times, and then I felt his penis start throbbing.
It was so intense! At first he kept thrusting, but it must have become too much for him because he stopped and held very still, only grinding his penis around a little at a time inside me. I can feel it throbbing too. It’s so hot! My eyes roll back in my head and I cling on to Jim, picturing Tom’s penis pumping me full of his cum. And he’s so deep inside me too!
When he’s finally done cumming, I practically collapse in Jim’s lap. Top pulls out of me and it almost makes me sad. I didn’t want it to end. I laid on my tummy and then rolled over onto my back between Jim’s legs, scooting up against him, sitting with him as Tom stood over me, his dick swinging.
I could already feel his cum starting to leak out of me. It was so hot. I didn’t know what to do though. I got up off the floor with one hand over my pussy so none dripped. As I hurried to the bathroom, his cum pooled in my hand as it spilled out. I closed the door and then quickly sat on the toilet and it all came spilling out of me!
Obviously neither of them had used a condom. I didn’t even know what a condom was at that point. I also wasn’t stupid, I totally knew what could happen, having sex like that, but I didn’t care! Like I said, I was a total horn-ball. Still am! Once all his semen stopped spilling out of me, which took way longer than I thought it would, I cleaned myself up a bit and then got dressed.
When I came out they were both dressed, sitting on the couch in the dark, watching whatever game was on now. I was between them. Jim was on my right, I put my leg over his. Tom was on my left, and I leaned against him.
I told them both, “thank you for being such good sports. I really liked that.” I had on a plaid skirt, and given what we had just done, I was not at all self-conscious about them seeing my underwear when I spread my legs and put one over Jim’s. In fact, my cooch was right out in the open.
As we sat together kind of cuddling like that, one of them would touch one of my breasts or kiss me, or hold my hand. At one point, looking down at the crotch of my panties all soaked, I lifted my skirt and commented about how wet they were: “All your cum is leaking out of me Tom.” That really turned me on, and Jim was quick to clap back that he thought that was so hot. He asked me if I liked that he came in my mouth. I looked at him, with Tom holding my tit, hugging me, and said to him, “you tasted so good. I’d love to do that all again.”
Sadly, I needed to get home and change well before any of the adults (or my brothers) returned home. I got up and scurried off home. I ate with my parents that night. I remember sitting there in my pajamas, daydreaming about having sex. My mom even asked me what was wrong at one point because I was so distant.
Later that night, Tom snuck over and he and I had sex again. This time it was just the two of us, in my little twin bed. He took off all my clothes, whispering about how amazing I was earlier as he did. I was so fucking turned on! Then, he got on top of me, and we fucked in missionary. He got me off 4 times before cumming inside me again. I’m not gonna lie, I really wanted him to pull out and cum in my mouth like in the movies, but this was far sexier!
I hadn’t even showered, and here he was back inside me, pumping my little body full of his cum again. He’d cum inside me twice in less than a few hours. It was an absolute miracle he didn’t get me pregnant! The fact that he didn’t only emboldened me too! After that, we fucked any time he snuck over. And then once or twice a week I’d have sex with both of them at the same time! Boy do I have some stories for you!
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