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lost bet = lost cherry

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Age when it happend: 17
Where it happened: My Bedroom
Langauge: English
Sex: Female
Rating: 9
Category: Straight

Well, my 1st time kind of sucked. I was a junior in high school, and a cheerleader. I went all of 100lbs (soaking wet, haha) and was a “flyer” on the team. Anyway I was the typical cheerleader. Always flirting with guys, dating/breaking up every week, ext. With all the guys I dated, I doubt anyone would have even believed that I was still a virgin in my junior year, but I really was.
Well, one night I was at a pool party, and it was the “bad” time of the month, if you know what I mean. A bunch of my friends kept asking me to go into the pool with them, and I subtitle hinted that I was at the peak of my cycle. Well, my friend Angie is like..”well, duh, just put in a tampon”. Well, after this conversation went on much more then I wanted it to, and I finally had to tell my little secret. that being that not only was I a virgin, but I could not put in a tampon, because I had a microperforate hymen. That being a real thick hymen (aka “cherry”) with just a very small opening. It made my periods really bad…lot of cramps, and the flow was real erratic. The time I tried using a tampon, it was like hitting a brick wall when putting it in. My doctor told me I would likely need a minor surgery for it, but I was way to embarassed to have it done any time soon.
So; in the process of explaining all this, one of the guys (Scott) at the party hears this whole conversation. Well, the next day at school in history class all he did was tease me over it. Saying stuff like, such a cute perky cheerleader, you’d never guess her cherry is still intact, blah blah… I was so embarrassed, but he brought it up and joked about it almost every single day. Near the end of the semester we had a big test coming up, and in the midst of one of our arguments ( I think i was telling him how stupid he was) he said he’d get a better score on the test then me. So I said fine; we’ll make a bet then. If I win you will shut up for the rest of the school year, and next, about everything, and you will all the busy work assignments for me for the rest of the year. He was like “OK, and if I win?” and i was like: YOU WON’T, and he said; “if I win I get your cherry”. I was like “yeah right, you wish” and he was like ok fine; no bet then. So after we kept berating one another, I finally said FINE, and we made the bet! I really thought I would win, but figured if i lost nothing was really going to happen anyway, and even if it did, he would not get to far with the way my hymen was.
Well, when the test scores came out, I’ll never forget..I scored a 84. He gets his, and I glimpse over and my throat dropped when i saw he got a 92. Did not take long and he was like “moment of truth; what did you score Amy?”. I reluctantly showed him, and he was like “OHHHHH, how unfortunate. You know what that means?” I was like yeah, whatever. He’s like your just going to renig on the bet now? Finally I said, FINE, you won, what now? he said, come over to my place tonight. I was like TONIGHT, FUCK NO. He was like yeas, TONIGHT, YOU LOST; SO DEAL WITH IT! So after lots of arguing; I finally said if you want your bet YOU come and get it. I’ll be at MY place after 5 night, and everyone will be gone till 10.
We left it at that, and I did not expect him to even come over, and even if he did, i would get a good laugh at him trying to pop my cherry and not being able to. Well, long story made short, he came over at about 8 PM. I was surprised, but not not really nervous, or anything like that. i really did not think he would do it. He was like “This won’t take long, take me to your bedroom”. So up to my room we went, and he ordered me to remove my clothes. So off came my clothes down to my bra and panties. Then i started to get real red in the face, and embarrassed about it. he then said something like “TODAY” and i finally took off my bra and then panties, and he ordered me to lay on my bed, while he began to remove his clothes. When he got down to his under pants, and took them off, his cock was as hard as a rock, and it was WAY bigger then i would have ever pictured. I was kind of scared, but trying not to laugh to, because I knew he would not be able to penetrate me. I could not even get a little tampon inside me.
In no time he got on the bed, spread my legs apart, and then he began to lick my pussy. I never expected that to feel like it did. i mean it really was like pure bliss. It made me tingle head to toes, and I felt my pussy become very very wet from the pleasure of it. Well, the feeling was pretty short lived as he moved right to fuck me. I laid on my back, legs spread wide, and he moved in with his cock that looked like a freaking cucumber. He used his fingers to kind of spead me open, and just started to jam it in my opening. My pussy kind of looked like a walnut with a paper cut in it. I was kind of nervous but also still trying to hold back laughter; as i knew there was no way he’d be able to get it into me! Well as he began to shove it in, he was quickly met by my unique cherry, and it was like hitting a brick wall! I was trying not to laugh my ass off, but the small penetration he had was hurting like hell!
He pulled out of me, and I was like HAHAH…thinking it was over! But he quickly grabbed both my legs with his hands, spread them real wide, and tilted my whole body way back. He then then got in a position like right over the top of me, and once again directed his cock into me. This time when he hit my cherry, he just started to thrust down into me real hard. OMG; it felt like I was being split in half. I mean it hurt like a bitch. I grabbed onto my bed post, like holding a doctors hand when pain comes. He just kept thrusting harder and harder, and literally just jammed his way in. It felt like a jack hammer. It burnt like hell, and the pain was throbbing. Finally he broke through and was completely into me. It felt like a knife stabbed me, and was twisting. Once he was fully in me, he began to thrust in and out, faster and faster. It was like a hot knife stabbing me. It hurt like a bitch, and there was literally nothing i could do. He was in a position that I could not get him out of me if I tried.
I totally sucked. i did not think he would ever be able to penetrate me. Not only did he, he banged me a good 15 minutes, and when he pulled out, he came all over my face that was all ready covered in tears from the pain of the whole thing. I just laid there in pain as he got back dressed. He got dressed, thanked me for honoring the bet, and we did not say much more, and he left.
When it was over; I got to get a glimpse of my devirginization. My pussy looked like a paper cut before, and now it looked like a deep heavy scar from the gorge. there was blood EVERYWHERE from it, and i was kind of freaked. it was all over my pussy, between my legs, and all over the bed. As i got up to go to the bathroom to get something to clean it all up, I was still throbbing with so much pain between my legs, that i could barely walk. It was no fun at all, but I guess that’s what you get for making a stupid bet, and loosing.

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