Sam

I lost my virginity as a grand conclusion to entire series of events that involved two of my friends, who I’ll call Brian and Mike. He wanted me, I was too afraid to want him; mainly because I was fifteen when he started pursuing me. I just didn’t want to lose it to him; it didn’t seem like it would have been “special” in my naive eyes. While he was pursuing me, I fell in love with Mike. I was far too afraid to approach Mike, however, during our (and I hate admit this) initial period of friendship over facebook. I started having strong feelings for him, and eventually wound up pretty much falling for him, even though I hadn’t met him in person. I was depressed for a month or two when he didn’t show any real interest and stopped messaging me over facebook, and then wound up with a boyfriend. I think it’s pathetic too. Afterwards, I started having a spark of feeling for Brian and forgot about Mike for a while.
Brian and I flirted menacingly over the next few months, and, finally, Brian asked me out, but I turned him down, again thinking that it wouldn’t be special enough. We stopped talking to eachother afterwards for a while, but we both ended up at the same birthday party. We generally ignored eachother for the majority of the party, but then Brian went up to the platform of the club we were in and started dancing and making out with some kid I’ll call Justin. I instantly felt something I had never felt before. It was like my stomach had fallen into my thighs and I couldn’t remember where I was, so I took a second look, and immediately climbed the stairs into the lounge, away from Brian, Justin, and the dance floor.
Brian ad Justin started dating after a week or so, finalizing the fact that I had lost Brian. I had figured out too late that I was helplessly in love with him. I had played with him just as I had played with so many other guys, but this time I had lost the game, and won the most valuable lesson I will ever learn about love; it doesn’t last forever. For the summer afterwards I pined over Brian, always depressed, and occasionally near tears. I was finally able to get over Brian after three months of severe depression (the kind I’m good at hiding) and moved on by blowing up with some slutty kid and telling myself I’d never date again. That’s how I started talking to Mike again.
Mike sent out a notice over facebook that said something about free HIV testing, and naturally, being a melodramatic gay boy, I decided that after one pathetic hookup that I had the deadly virus, and started asking about it. We struck up a rather long conversation, and I eventually admitted to having had a crush on him and to still being a virgin. He said that I was really cute, or something like that, and we started joking about a contract where I signed my virginity away to him. We both took it seriously.
I finally met Mike some time later (while Brian and Justin were still dating) at his house, and we had what I would call a great time together. No sexual activity or anything, despite the fact that we wrestled on his bed and he got a boner, and then I kissed his neck on my way out.
Brian and I had started talking to eachother again because I had become friends with his brother, and he claimed that he owned my viriginity. I still had a few feelings for him, and wanted to have sex with him, but he said he wouldn’t fuck me if I had sex with Mike. This made things difficult, as I had started falling for Mike again.
Within two weeks, Brian and Justin broke up, leaving Brian distraught, and me feeling bad for him. I agreed to have sex with him over Thanksgiving break, and immediately became frustrated with my decision to do so. I cared a lot about Mike, but Brian seemed to need some condolence from me, i.e. taking my virginity. I visited Mike again before Thanksgiving, and again we had fun doing what was basically nothing but pure, boyish fun. We ended up lying on his couch together, in eachothers arms. It was the best I have ever felt in my life.
The next week, Brian came to my school and picked up me twice. The first time, we went to the Library and made out in the elevator. I could barely move because I was so scared and ashamed; I felt as though I were betraying Mike. The second day, Brian brought me back to his house, and I was as giddy as a school boy on the first day of school, having always wanted to see his house/ his room. We went into his room, and I saw a book that I had been meaning to collect from the library because I need a piece of information out of it, so I picked it up and sat down on his bed. After a minute or so, Brian took the book out of my hands. I suddenly knew that I wasn’t going to be able to turn back if I let another second go by. I reacted to late. Brian pushed me back on his bed so that my head was against the wall, not the head board, and I started shaking violently, petrified of what was about to happen. We kissed for a decent amout of time, and finally he pulled of my shirt and pants, but left my t shirt on. He then took off the majority of his clothes, save his wife beater and underwear. He made a crack at my underwear, as it was very heterosexually juvenial looking, before he laid me down length wise on his bed, and propped my legs up and my arms above my head. He got between my legs and we started kissing again. I was still shaking quite bit. He put his hand on the elastic strap of my underwear, saying “Moment of truth, kid?” I don’t remember if I responded to his sarcastic remark or not. He took off his shorts. I could feel his penis pressing against my ass. He put on a condom, and picked up some lube, which was the scariest part for me, although I cannot say truly why. He started jacking me off a bit with the lubricant, but I made it clear to him that I didn’t wanted to cum before he did, if at all, without saying a word. He put the lubricant on his penis, and on the opening of my ass. Then he put my legs up on his shoulders, and I stopped shaking. He prodded my ass a few times to make me loosen up, and then he pushed in.
I gasped and cringed and started breathing really hard. I asked him if it hurt like this everytime, and he said that it burned, but it didn’t necesarily hurt, everytime. After a while, I told him to try and make me scream. He pushed in almost all the way and I let out a completely uninhibitied cry that would have woken up people for a mile. He finally started pumping into me toward the end (although he was kind enough not to go all the way in) and it hurt so bad that I almost started crying. When he came al over the shirt my friend had imprinted for me, I suddenly got my mind back; I had just betrayed Mike.
So Mike, if you are reading this, and I’m sure you’ve figured out who you are by now, I just want to tell you I’m sorry. I wanted my first time to be with you, because those strong feelings I have (although I may be mistaken) well, I think they may be love.
But then again, they’re probably nothing, just like always. I should really be apologizing to Brian here; he’s the one who still cares about me. So I’m sorry to you too, Brian. I’m really not worth you.
*All names have been changed.* (Except for mine)

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