This is about the first time I broke a girl's cherry. My first high school girlfriend was a year older than me and wasn't a virgin when she took my virginity. She showed me how to fuck over a period of three months. Almost every day after school, we'd go to her house....both her parents worked....and fuck our brains out. The guy at the pharmacy once asked me how in the world I was buying rubbers 2-3 times a week. I'd just grin and say nothing. Anyway, we broke up and I moved on. What I moved onto was the new girl in school.
Her name was Allie and she came to our school early in junior year. She was a year younger than the rest of us as she skipped a grade early on in her life. Allie was an athlete and had the body to prove it. She was as tall as me....6'...and had long legs, an incredibly tight ass and small boobs that were impossibly perky. She was the perfect specimen of teen beauty. Even if her tits were bigger, it wouldn't have made her more attractive because the rest of her was so perfect.
We began dating almost immediately. I was a popular jock and she made friends fast with the group. We went to basketball games and parties and the typical things teens do....which included making out and me trying to fuck her. As she rebuffed each attempt I made, it got more and more frustrating. Finally, she confided that she was a virgin and had been afraid to give her cherry to a guy as she and her family moved a lot...her dad was some corporate exec and got transferred often. This was her 4th high school in 3 years and she didn't want to give it up to a guy and be told they're moving the next day.
At a party one night, we had some beers and found a room to ourselves. She may have been a virgin, but she did give some good head. She rationalized it by telling herself as long as a guy rubs her clit and gets her off, she could return the favor. She told me she also liked the taste of cum and how it felt when a cock erupted in her mouth. We got on the bed and I slid my hand down her unzipped jeans. Her clit sprang to attention under my finger as I rubbed her love button hard. She ground her hips hard against me and threw her head back. Her cunt was steamy-hot and I rubbed even harder.
She grabbed my hand and pressed me into her harder as she came. She panted and groaned and bit my shoulder as she finished. By this time, my cock was ready to rip out of my jeans. I stood up and undid the zipper and pulled them down to my knees. She must have been really turned on because she never sucked my cock so well before. Normally, she had one speed with her hand and didn't use her tongue enough, but that night she was like a porn starlet.
I got really weak in the knees and grabbed the back of her head for balance. She took this as a sign to suck and stroke harder and she responded like a pro. I was making these gutteral grunts and sounds while she sucked away on me. I wasn't sure how long I was going to last...usually it took her a while to bring me off....but it quickly became apparent this was going to be much faster. She looked up at me and said "You like it like this?" As she got the words out of her mouth, my cock erupted. The first squirt landed right on her chin. She quickly put my cock back in her mouth and sucked me dry. After I was empty, she wiped the cum off her chin and licked it off her hand. I figured we were done for the night and pulled my pants up.
She then surprised me by what she said. "I want you to be my first. Tonight. I'm ready and can't wait anymore. My pussy aches and I want to feel sex. Nobody is home at my house...we could go there. I don't want my first time to be at a party on a strange bed. Ok?" I almost asked her to repeat what she said, but didn't want her to change her mind. I nodded, grabbed her hand and we left the party. We drove to her house and got out of the car. I pulled a couple rubbers out of my glove box, but she surprised me again.
"You don't need those if you don't want. I've been on the pill since I was 14. My periods get all screwed up if I don't regulate them. Is that ok?"
Fuck yeah it was!! I had never fucked without a rubber before and eagerly looked forward to feeling what pussy actually felt like. We scrambled inside and went right to her bedroom. She got an old towel from the linen closet to spread under us in case she bled. We stripped each other quickly and I got my first look at her naked....she was perfect. Her bush was naturally sparse and her pussy lips were already swelling up a bit. I had seen her tits before, but the whole package was breathtaking. I guess I was staring too long because she asked if there was something wrong.
"No, Allie....you are incredible. I just can't believe I'm the lucky guy who gets to be your first." I said. She had never seen me naked either and took me in for a minute. I was rock hard again, obviously, and ready to pop her right there, but didn't want to frighten her. I told her to lay down and spread her legs.
"Are you going to lick my pussy? I hope you want to because I want you too before I get messy down there. I was afraid to ask." I lowered my face down to her perfect virgin pussy and just stared at it for a second. Her light brown pubes were soft as a feather and framed those lips perfectly. Her lips were fully engorged and her pussy was wide open for me. I was afraid to finger her too deeply since she still was cherry, so I just used my tongue. As I licked her hard and fast....I didn't know much about going slow at first back then....she ground her pussy into my face. I nibbled and sucked on her clit until she was moaning and trembling. I knew she was close to coming and was curious what would happen if I put a finger in her tight butthole.
I licked my index finger and slid it in slowly. She gasped and rotated her hips and seemed to like it. I was only in to the middle knuckle and started making the "come here" motion with it. That did it....she immediately began to scream and buck her hips and her cunt went into serious spasms. She was having an orgasm that was 10X as hard as any my fingers had ever given her. She wasn't prepared for the intensity and began to cry as she released. I licked her until she pushed my head away.
"Oh GOD, that was amazing. You need to stop for a second so I can catch my breath!!"
I held her in may arms until she calmed down a bit. We began to kiss softly and touch lightly. I was still hard as a rock and she grasped my cock with her hand and stroked me a bit. I knew if she kept at that, I was going to lose my load too quickly, so I got the towel and shoved it under her ass. I was ready to deflower this beauty.
"Are you ready? I am." I told her. She responded by opening her legs wide for me. I knelt between those perfect thighs and readied myself. She looked at me with total trust in her eyes.
"Promise me you'll go slow. I love you." I told her I loved her too and I meant it. I was no virgin and felt something new inside me. Now she was going to feel something new inside her.
We were both shaking a bit as I got my cock close to her pussy....that dripping, virgin pussy. A big glob of pre-cum oozed out of my cock, which I rubbed onto her wetness. She was grinding her hips and I could feel the heat off her pussy radiate onto my dick. I couldn't wait anymore and entered her.
She arched her back in surprise and locked eyes with me. She was expecting pain right away, but didn't feel anything but my cock head in her opening. I hadn't hit her hymen yet but eased myself up against it. She figured out that this was the moment she had been waiting for. I saw her grit her teeth and steel herself for the pain. I could feel the blood pulsing in my cock as I made the final push and tore thru her virginity.
She let out a yelp and shut her eyes tight. I slowly went balls-deep into her and she responded by squeezing my cock with her cunt muscles. I withdrew and re-entered her, going slowly to ease her into it. She opened her eyes, which were wet with tears of pain this time. I asked her if she wanted me to stop, but she said no, keep going. I gently fucked that tight little hole and glanced down between her legs. There was quite a bit of blood oozing from her, but the towel was doing it's job.
I began to suck and lick her tight little breasts that were tipped with hard little pebbles for nipples. She began whimpering and moaning a bit. I increased the speed of my thrusts, but was still going very slowly. I wasn't sure. but I thought I felt her pussy begin to tremble a bit as I slid in and out of her. I knew I was feeling her pussy grab my cock with every thrust inward.
I didn't realize it, but she had grabbed my ass by this time and was pushing me into her. Her nails were digging into me and it hurt. I laughed and told her not to be so rough with me and she laughed back. I knew she was getting into it because by this time there was no question that her little cunt was trembling with a future orgasm. She began to move her hips and arch her back and started to pant hard, her breaths coming short and quick now. Even at that age, I knew what that meant....she was getting close to coming. I kept the same rhythm going and started to kiss and suck her nips again.
She started squeezing me with her thighs and her ass started bucking as her first cock-inside-her orgasm ripped thru her. Her eyes opened wide, but I saw nothing but whites. Her mouth dropped open in a soundless scream and her cunt felt like a vise-grip on me. Her scream started in earnest as she nearly ruptured my eardrums. At that moment, I would have been happy to die immediately after I came. Allie's eyes rolled back into the front and she locked eyes with me again. I could tell she was shocked again by her orgasm's ferocity and intensity. She fell limp after it was over, trembling and shaking and quaking. She was covered in a fine sheen of sweat that I wanted to bathe in. She smelled incredible, even with the blood between her legs. The smell of fresh sex, sweat and musk from between our legs was the stuff of legends.
I was close to my own orgasm and began to thrust again. Allie was really charged up after losing her cherry and having an incredibly powerful orgasm. I was going to go nice and slow the rest of the way until I came, but she surprised me again.
"Fuck me hard. Pound me. I'm ready!!" she exclaimed. I gave her a hard kiss and threw her legs over my shoulders. She let out a surprised "WHOOP" and readied herself. I slammed into her as hard as I could and could tell she was still a bit tender, but could also tell she wanted me to fuck her hard until I came inside her. She reached under me and started stroking my balls that felt like they were about to burst. I was up on my toes for leverage, just hammering away on her, feeling her use her newfound pussy muscles on me. She had figured that out really quick and was using it to her pleasurable advantage.
I knew my time was short and told her I was going to come inside her if that was what she wanted. She assured me she did and I cleared my mind and focused on how good her incredibly tight cunt felt. I was absorbed in my own feelings when I felt her start to shake all over again. As I went into my last few strokes inside her, she grabbed my ass again and screamed, "OH MY GOD I'M GOING TO FUCKING COME AGAIN!!!!" and let loose with a gush of cum that splashed all over the both of us. It was like someone turned on a fountain or something. I couldn't hold back anymore and let loose inside her, scalding her insides with my white-hot sperm.
She squeezed me hard with her thighs, cunt and hands, trying to drain every drop out of me. She succeeded. We both collapsed and didn't move for what seemed like forever. I know that I was drained. After a bit, I got up and grabbed the bloody towel and cleaned her with it. We staggered to the shower and took a nice hot shower and got back into bed. For the rest of the night, we explored each other. I licked her cunt forever it seemed and introduced her to a rim job, which she loved. I fucked her doggy-style and let her get on top. We even did it standing up, with her bent over and her hands and feet on the floor. I lost count of her orgasms and know I came at least 6 times. Her insides must have been white for weeks.
We were glued to each other for the next two years, fucking like rabbits and doing everything we could think of. She got into anal and loved having me pound her little butthole. She could come just as easy with my dick up her ass as she could with it in her pussy. We ended the relationship when we went away to different colleges. There was just no way we could stay together on different coasts, but we'd get together from time to time and fuck for old times sake.