Teen
2007-01-11

We hadn't talked in months but I was feeling desperate and I knew she could cure what was aching me. Sasha and I had joined a youth group together almost two years ago. From the get-go I knew she liked me but I just ignored her. She was the kind of girl that would be there for me whenever I felt like having her. You know, that girl you knew as a kid who isn't the best looking but there's something about her that you're really attracted to -- that was Sasha. Sasha had long dirty blonde hair and her eyes were a bright green. At about 5'4 and 120lbs, this 19 year old was a small package just waiting for me to unwrap her. I saw her sign on to MSN and, having that "I want some soon" feeling in my pants, decided to start a conversation with Sasha. Twenty minutes of flirting later I had dinner plans -- my place, I would cook and she'd bring dessert. Friday evening. It wasn't a date, it was just dinner between two friends. She didn't know what I was cooking up but she was definitely happy to be invited. At six she rang my bell. After a big hug I let her in; we sat on the sofa catching up a little. I wasn't interested in what she had to say but she liked the sound of her own voice and I knew keeping her happy was my passport to pleasure. When Sasha started to slow up on that small talk I volunteered to start dinner.

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    In tight jeans and a cute green T-shirt that accented her eyes, Sasha wanted to help. I've got a small kitchen but I made some room for her and let her saddle up beside me. As I passed behind her to get food out of the fridge I was sure to casually touch my hand to the small of her back, just to get her accustomed to my touch. By the time dinner was ready I had my hands on her butt, back, sides and legs. It was all going to plan. Sasha enjoyed her dinner and the wine I served with it. She was not the drinking type so the wine had the desired effect: not drunk but just enough to take her inhibitions away. This was a girl with so little experience with a guy. A virgin, Sasha had only taken her top off for one guy, the kid she dated in high school for a year. After dinner we had a little more small talk. As that faded I turned to my game plan -- it called for a game of truth or dare. She was young enough and inexperienced enough that this sounded like a fun game to her. We started with the stupid stuff. Go yell out the window. Take three shots of tequila.

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   Who was your first crush? It was all clean fun. Then I went to work. I asked her how far she'd gone with a guy. Turns out she had only made out with her top off. Never had an orgasm. Didn't know what it was like to get head or give it. Then she picked a dare. As I had planned out in the days leading up to our dinner, I'd just dare her to kiss me. That would get the ball rolling for sure. "Sasha, I dare you to kiss me. "Sasha gave me that 'I'm going to pretend I'm not liking this but gawd I like it' look. She gave me her best kiss on the lips. For a girl with so little experience it was a surprisingly good kiss. But I knew Sasha's weakness was her competitive streak. "What? That's all you've got? You can kiss better than that, can't you?" I quipped.

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  Then she put one leg over me, straddling my lap. Sasha leaned in and gave me a deep, passionate kiss with all the tongue she had. From that point on she was mine. Forget Truth or Dare, we just made out for the next 20 minutes. Wanting to push her as far as she'd go, I started to feel Sasha up. Her 36C breasts were full and I wanted badly to free them from her bra. But as I put my hands up her shirt, Sasha became visibly uncomfortable. I pulled away and went around back. Unsnapping Sasha's bra, she pretended to get upset, giggled a bit and then let me have my way. Soon her breasts were in full view. I played with her nipples to my heart's content. They were a little larger than a quarter in diameters, dark pink in color and, until fully erect, her nipples pointed inwards. Just like her, her breasts weren't the nicest I'd ever seen but something about them drew me in. After a few minutes of massaging, licking and rubbing, her nipples were like bullets. As we continued to make out, I made sure to hide the clock.

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   Unfortunately Sasha didn't realize she had missed her train home. No trains would come until 9AM so she had to stay the night. Wanting to get her into bed I offered a night shirt and boxers of mine that were at least three sizes too big. I thought they fit perfectly -- so loose they were easy to remove. With a little hesitation we went to the bedroom. But Sasha wanted to set some ground rules: "Don't touch between my legs -- everything else is okay. "I agreed to her condition but I knew she would change her mind after some careful teasing.

So with that we got into bed. It's a queen-size bed but for our purposes a single would have done the trick. Sasha was in my arms immediately and within seconds my tongue was in her mouth. After a few minutes of making out I went to work. I don't use any secret "moves" but my strategy succeeds more than 90% of the time -- especially with the girls who have little experience, want sex but don't want to come off as a slut. All I do is start by massaging their lower back and go from there. With my hand rubbing the small of Sasha's back, I lifted the back of her shirt just enough so my hand was on the flesh of her back. As we continued to kiss my hand crawled up her back and down her sides.

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   She cooed as I hit sensual spots on her neck and back. She was turning to putty. As Sasha relaxed more, her back and sides became her fleshy breasts and erect nipples. Feeling her body become a little bit tense, I spent another 18 minutes just playing with Sasha's breasts. As her apprehension turned back to pleasure I removed the over-sized t-shirt. With Sasha's top on my floor I began my journey south. While continuing to kiss, I moved my hand down around her knees. Very innocently, I began to run my fingers around her legs. Forceful enough not to tickle but not too hard either. I slowly made my way up to Sasha's thighs, the whole time firmly and sensually massaging her. As I started to feel more warmth, I knew I was getting close. When I got to her boxers I made sure to make it obvious that I was respecting her boundaries. That meant I moved my hand to the outside of her thigh and up on to her stomach, just above the waist band of the boxers I'd lent her for the night. From there I began to run my fingers on top of her nightwear, around the hip line. Sasha seemed okay with this so I slid my hand down until I could feel her partially shaven pubic hair.

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   Knowing that Sasha's clit was just a couple inches away, I began to lightly tease her by circling my fingers around the forbidden area. As she began to give into my teasing, I slipped my hand underneath her boxers, running my fingers around her very short bush and on to her inner thighs. That made Sasha breath a little heavier and even elicited a barely audible moan. Seeing the pleasure on her face I began to brush my hand lightly over the fat lips of Sasha's vagina. Every time a moved over her pussy I let my hand stay a little bit longer. When I knew she wouldn't object, I began massaging the outside of Sasha's vagina. With my pinky on one side and my thumb on the other, I started to massage from the crease of her legs inwards. Clearly she liked this because the heat emanating from Sasha's cunt was making my hand sweaty. When I reached the center of Sasha's pussy I used my middle and index fingers to push her lips apart. To no surprise, this girl was drenched. My fingers were lubricated completely within seconds. The only thing holding me back was the tightness of Sasha's vagina. Only one finger could fit but after two inches Sasha whimpered so I retreated and moved up an inch or two to finger her clit. Although I think I'm pretty smooth, I'm not the biggest playboy in town and don't exactly get into bed with a different girl every weekend. So finding Sasha's clit proved to be a little more difficult than I thought.

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   And since she hadn't ever had an orgasm I wanted to be sure to give her her first. Plus, I like the taste of pussy. So I moved down to the foot of the bed and spread Sasha's legs wide. I don't think she quite understood what I was doing until my tongue touched her cunt and she gasped excitedly. It still took me a couple minutes of tonguing her pussy to find her clit but when I did Sasha almost ripped my hair out. Once I had her clit on my tongue I didn't relent. I sucked it, nibbled it and fingered it trying not to get pushed away as Sasha's hips bucked with absolute pleasure. Then she yelled "STOP!" I quickly moved away. "Do you have a condom?"Sasha was a dog in heat. She was a virgin that needed cock badly. "Of course," I replied enthusiastically. (C'mon an hour ago she told me I couldn't touch her between the legs and now she's begging for sex. I was definitely feeling good. )So I jumped off the bed, ripped open my dresser drawer where I had a stash of rubbers and quickly ripped away the packaging. As I rolled the condom on my penis I realized that, though I'm not the longest in the world, I've got enough width to cause the exceedingly tight virgin a great deal of pain.

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   I suggested she go on top so she could control the pace. Sasha straddled me as she began to descend on my cock. I got my head in and then she lifted up as she moaned in pain. It wasn't me, it was her. I'd never inflicted the kind of pain Sasha was experiencing with my penis on another girl. She tried again but this time when her hymen met my penis Sasha almost went to tears.

I kissed her and held her until she relaxed again, I said we'd try again in a little while and removed the condom. But now I needed to get off. I was straight forward about it:"Sasha, can you give me some head, I really need to cum. "Hesitantly Sasha agreed. "Yeah, I guess. But if I'm not good then don't get mad," she said. "I've never done this before. "I reassured her that if she just relaxed then she'd do great. Then I handed her a pillow and told her to get on her knees as I moved to sit at the end of the bed.

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  As she knelt before me she gave me a nervous, "are you really going to make me do this" kind of look. I ignored it, reassuring her that she'd be great. "Thanks," Sasha replied. "But could you just not look at me while I do this, I feel so dirty. "Without responding to her request, I put my hand at the back of Sasha's head and guided her towards my, hard, pulsing penis. Not really knowing what to do first, Sasha licked my head a little. When got the first taste of pre-cum in her mouth and adjusted to it, she took my cock into her mouth. She was doing well and I was enjoying it, though every minute or two she would scrape her teeth against my shaft. After about five minutes Sasha was feeling a little more comfortable and started to play with my balls. I was feeling great but I Sasha was only taking in about three inches of my dick. So I gave her some help. Putting both hands on the back of Sasha's head I started to push her head a little further. After three strokes she couldn't take it and had to gag. She spat on my floor to get the excess saliva out of her mouth and then as soon as she was ready again, I had my cock at her lips. Now I was ready to cum so I pushed her head further down my shaft.

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   Eventually my pubes were touching her nose and my dick was scraping the back of her throat with every thrust. Sasha was having trouble breathing but I ignored it as I fucked her mouth. As my balls tightened I moaned loudly as the first of four spurts of cum coated the back of Sasha's throat. Keeping my penis in her mouth, I was able to force her to swallow most of my load. But after swallowing hard a couple of times she started to gag uncontrollably and spat repeatedly on the floor. "Was I okay," were the first words out of Sasha's mouth once she had finished spitting. "It was everything I was hoping for," I said, trying to butter her up so she would keep putting out. "Thank you. "With that, I motioned her back into bed and, naked, we spooned for about an hour. As I regained my energy I began to kiss Sasha's neck and grind my penis into her ass. As the grinding became more intense, I pushed about her legs so I could rub my dick right against her, again, sopping wet pussy. I slid freely in between her legs, giving us both great pleasure. I was ready to try to fuck her again -- so determined that Sasha's hymen didn't stand a chance. Just like before, I moved my head between Sasha's legs. This time making a bee-line for her bulging clit.

 

   Within two minutes Sasha was promising me that she could take the pain if I would give her another chance with sex. So I went for the condom again. But this time I was on top. As I lined up my penis to enter her, I got distracted by the glassly look in Sasha's eyes. If I loved this girl I would have stopped. But since she kept saying yes and all I wanted from her was sex, I shoved my conscience aside and pushed myself inside her. Since I was looking her in the eyes I thought I might have entered the wrong hole. But when I looked down my head was an inch inside her vagina -- she was just that tight. So I loaded my hips and, with one swift motion, pushed myself as deep as I could go inside Sasha's virgin cunt. She screamed. Tears swelled in her eyes. Then came the sniffeling. "Why are you stopping?"I didn't need to be told again. Using short, quick strokes I pounded Sasha's tight pussy while using my finger to stimulate her clit and push it down into contact with my shaft. That got her hips moving.

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   She was like a bucking bronco. All I had to do was stay on for the ride. Ten minutes later and the orgasm that was building inside Sasha during her 19 year life began to errupt. As the walls of her vagina constricted I felt like my penis was in a vice. Then like a tropical storm my dick was pushed out of her pussy as Sasha sprayed her juices all over me. With her hips still convulsing, Sasha passed out. It was too much for her to handle. I had her over a few more times because she didn't mind having her throat fucked and turned out to be a great lay. But that's the only purpose she served so as soon as I found a girl I liked, I made up an excuse not to see Sasha anymore. Just in case I find myself desperate again, I made sure the door stayed open enough that I could call her. .