the-story-of-me
FIRST TIME SEX STORIES

The Story Of Me

The Story Of Me

by quimby1_7
14 min read
4.33 (11400 views)
adultfiction

I was a very late bloomer. I was barely 130lbs until my senior year and could not put on weight to save my life. I was under 5'10 for most of my high school life and didn't hit that height until my senior year. In fact I went from 5'7 to 5'10 basically during the spring of my junior year of high school.

This reality kind of kept me shy. I mean, what would a girl want with a 5'7 120lb kid, when there were so many "men" at the school?

I had finally stumbled into a girlfriend my senior year. Really, she pursued me. Like most of the women in my life now that I think about it. But Kay is a story for another day. This is a story about my first time.

It was 1999 and the internet was new, and fresh, and full or horny, lonely people. It felt safe to put out personal ads, trying to find someone. Expanding your world of opportunity in one simple step.

I got lucky. Well, not that kind of getting lucky, at least not yet. After only a couple of days of having a personal ad up there, I got hit. Her name was Samantha and she was attending university about 4 hours away from me. We started having daily chats, which eventually turned into daily phone calls, and finally a reveal of ourselves. Well not like nude pics, but our senior photos from high school. We chatted all year, phone, IM, e-mail. I was slowly building feelings for her and her for me.

We met during winter break. She came by my place with her friend, and seeing her, in person, my heart never felt so high. It was immediate attraction. She was only 5'2, but her eyes, were pools of blue. Her hair, this beautiful mess of blonde highlighted curls. Samantha was a dream, a cute adorable dream. I took her and her friend out to eat, and seeing her remove her winter coat, showing off a fully stuffed sweater. The way here breasts lifted and heaved as she talked. To this day I have not seen a better chest on a woman. By the end of dinner, I knew I was in love with her.

As we walked back to the car, I knew I had to make a move. I reached out for her hand, holding it gently in mine. I spun her toward me just as we got to the car. Planting a simple sweet kiss on her lips. Her sweetness was apparent. My peck fell into a full on lover's kiss. Our tongues touching, electricity flowed through my body. Honestly, married to a different woman today, I have never felt that same energy and excitement in a kiss.

The rest of the night was a blur. Driving and picking up my friend, going to a local university bar to dance, every time we drove anywhere Samantha and I were holding hands.

At the bar, as Samantha and I danced, I had an opportunity to fully view everything that Samantha had to offer. My eyes watched as she turned and shook her hips, grinding her round booty into me. Her waist and hips belied a perfectly flat stomach that ended in the massive mountains of her chest. We would hold each other close as slow songs came on and I would get swept up in the sweet berry scent of Samantha's hair.

The evening came to a close and her friend dropped me off. Samantha walked me to my door and I invited here inside. There we decided to say goodnight to each other.

My lips pressed into hers, our tongues swirled together. Electricity and heat flowing between us, I found my hand sliding up her sweater to feel her full firm breasts, each more than two handfuls big. I felt her hand on my crotch as I told her how beautiful she was.

Soon I had her sweater up over her beautiful bra, pulling down the cup to expose her nipple and sucking on her massive breast. Her hands in my hair, moaning, saying yes and calling me cutie. My right hand found its way into her tight jeans, feeling her mound through her lacey underwear. Her wetness had soaked through completely. I found a way to slide my fingers into her damp lacey panties and began to rub her. Her mouth ground into my mine, moaning into me as my fingers worked her full pussy lips, finding her clit and strumming her closer and closer to a climax.

Her body tensed as she came on my fingers. Our lips never leaving each other. I kneeled and pulled her panties down as far as I could. Her jeans tight, and her round ass planted firmly against my car. My tongue snaked its way between her perfect lips, her light pubes tickling my nose, as I found a way to lap her wetness and soon her clit. Samantha pulled me to my feet "I want you to keep going, but my friend is probably wondering what happened to me" she said. I helped her compose herself, and kissed her lips again, walking her to the door. Hugging her tightly and kissing her again, I finally said goodnight.

As I watched her perfect ass walk its way to her friend's car, I couldn't help but think about how much I was in love with this pretty little girl.

I closed the door, sighed and sniffed my fingers. Her beautiful scent still on my hand.

But this was not my first time. I, like the lonely virgin that I was, went to my room and stroked myself to completion. Taking time to enjoy Samantha scent on my hand. Dreaming of the day that I would finally get to be a man.

Samantha and I met again the next night. We went bowling, and laughed and had fun. Our goodnight was just as passionate as the previous night. Dipping my fingers into her tight little honeypot. Her hand stroking me through my pants. I wanted nothing more than to be with her, for this cute, sexy girl to take my virginity. But it was not to be that evening.

It was never to be any evening, actually. I helped her babysit on New Year's Eve. Another wonderful night with this 19 year old beauty. However, Mother Nature was not on our side that evening. I did spend that New Year's Eve fighting the urge to cum. We played, and we played hard. I explored her massive breasts, as she played with my cock. But, if I could not get her off, I wasn't going to let myself get off. It only seemed fair.

After that night, nothing physical happened again for us. Oh, I loved Samantha. But time just was not on our side nor distance for that matter.

πŸ“– Related First Time Sex Stories Magazines

Explore premium magazines in this category

View All β†’

Samantha went back to her university and I went back to my work then school routine. Samantha and I still talked every day through IM or phone. Occasionally even having a little fun on the phone. Overall though, I was sad, and missing my love. Those feelings, that sadness often showed up on my face at work, or in conversations.

Anne, a friend from work tried to cheer me up as best she could. Taking me to lunch, trying to get me to do other things, go to movies, shopping etc. I would confide in her what was going on, or how cool Samantha was. We would talk about it at lunch or while Anne was on a smoke break.

Whether it was my lack of any game or just being dense, I never realized what Anne was really trying to get me to do.

One night in late January, Anne and I had hung out all day. Spending time at the mall and eventually ending up at a movie. It was a late showing, and we didn't get out until 10pm. We headed back to my place and continued hanging out, talking with the TV on in the background. Anne asked me a few questions about Samantha. What did I like about her, what it was like when I kissed her? I willingly shared. Almost excitedly shared.

That's when it happened.

"If Samantha was here right now, what would you do?" Anne asked me.

"I would definitely kiss her" I said.

"Like this?" Anne leaned in and kissed me on my lips. I was full of shock, but then comfort. Her taste was smoky and sweet. A mixture of tobacco and cherry cola. Something that I have never tasted again. The kiss lingered, and evolved into a more passionate kiss.

I was in my own head as I kissed Anne. How had I not seen this coming? How could I not have known? It wasn't until years later that I realized that I had not noticed because I had been blinded by my love of Samantha to not notice any other women.

Anne was built different from Samantha. She was 5'8, a natural blonde, her hips were more narrow than Samantha, but with a subtle curve. Her face was not as cute, and greatly helped by makeup. But that is one of the issues with being of Scandinavian descent. Blotchiness in pale skin is far more prevalent. Anne had the right curves, but I had been blind to it.

The midnight talk shows came and went on the TV and I realized it was awfully late to send this poor girl home. I asked if she would like to stay the night and we turned off the TV and headed to my room.

I let Anne pick one of my shirts to wear to bed and left to change into my sleeping clothes. A simple white t-shirt and black shorts. When I came back Anne was in my futon wearing my senior football camp shirt. The shirt barely passed the bottom of her hips and I finally saw the length of her legs, and truly noticed the heft and perkiness of her D-cup breasts.

I slid in next to her and we pulled the blankets up. Immediately we went back to kissing. My hands exploring her body, sliding up the t-shirt and feeling her naked breast. It surprised me, she had made that decision on what to wear under her shirt. Her full firm breast felt nice, and I noticed much smaller nipples then what Samantha had. Pert D-cups with almost pin prick nipples, I had to see them for myself. I slid the shirt up and began kissing and sucking her breasts.

As my tongue flicked at her tight firm nipples my hand found itself between those long smooth legs, feeling the heat and moistness of Anne's crotch. My fingers pressed into her firmly as she let out her moans. Her wetness surrounded my fingers as she passionately kissed me. My fingers rocked her supple pussy lips. Over and over, using what knowledge I had to massage her to climax. She kissed me hard as her body trembled in my arms, and at that point Anne took over.

Anne pushed me onto my back and kissed down my body. She teased and sucked my nipples, and licked down my abs as she slowly pushed her fingers under the waistband of my shorts. Pushing my shorts down, Anne let out a brief gasp as my hardened dick sprung forth.

In my head I was nervous. Nervous of Anne seeing my cock. I'm not small, but I am un-circumcised. Being an American, it is highly unusual to not be clipped so I was self-conscious of what her reaction would be. Anne's gasp at the sight of my dick sent chills through me, that she was disgusted or scared of it.

That fear quickly disappeared as I felt Anne's hot tongue slide up the underside of my fully engorged penis. Her tongue was all over it. I had forgotten how great it felt to feel the moist heat on my dick. It had been 4 years since I had a woman's (girl's) lips on my dick. I was in heaven as Anne happily, almost hungrily, licked my cock.

Anne engulfed me, working the head of my cock with her lips and tongue. Soon she was trying to get me all the way in her mouth. Moaning and tensing, I must have given her some indication that I was closer then I was. Anne looked up from my well sucked dick and asked "How far did you want to take this?" without even thinking of what she meant I responded.

"As far as you want to take this" I said.

πŸ›οΈ Featured Products

Premium apparel and accessories

Shop All β†’

With that, Anne slid up my body. Straddled my hips. Gripped my shaft, and guided my throbbing member into her well soaked hole.

The hot, velvety sensation of entering Anne coupled with her moan of pleasure as I stretched her. It was amazing, I pulled her to me, kissing her lips as she ground her tight little box on my cock. Her ample breasts and rock hard nipples pushed into my bare chest as she moaned and rode me faster, and faster. My futon squeaking loudly as she worked herself up and down my shaft.

She looked at me, and said "Your bed is so loud, come with me". Leading me to the floor by my hand, opening her long sexy legs in the moonlit dark, guiding me toward her entrance again.

I was on top. I was on top, and had never been on top before. I had never fucked any one, never even pretended to hump a pillow. But here I was being guided by a lustful woman, expecting me to make her cum. With my dick.

I entered here again and her legs hugged my hips. I did what I thought I should, grinding my cock into her, kissing her, sucking her neck and breasts.

I found a rhythm that kept making her moan and stuck with it. Soon her legs were squeezing me tightly and soon she was doing more than just moaning. "Oh god, yes, fuck me, yes, just like that" Anne was whispering hoarsely into my ear.

After what seemed like a long time later, I could feel myself building toward release. I pulled out, and Anne deeply as my cock shot its load all over Anne's thin layer of golden pubes.

Panting and moaning on top of this woman that I had never thought about sexually. The woman that just took my virginity. I was excited and surprised.

We got back into bed after I wiped my cum off of Anne. Holding her in my arms. Kissing her goodnight. Trying to fall asleep.

I must have nodded off at some point, only to awaken to a sexy woman in my arms. I kissed her neck gently. "Oh you can't sleep either" Anne whispered to me. "How can I with something so perfect lying next to me" I said back.

The next thing I know I have kissed my way down between her legs and I am licking Anne deeply. She is grinding on my mouth as she closes in on another orgasm. Anne cums on my tongue and I roll her hips so that she is on her stomach. I bite her cute round butt cheek as she lifts it into the air. Wiggling her hips and ass just a bit. Anne looks over her shoulder "Take me again" she coos.

I honestly fumble a bit trying to guide myself into her pussy from behind, but eventually work it out. Well in, as the case may be.

Holding her hips, I thrust smoothly in and out. Letting Anne's excitement guide my speed.

As she moans louder, I move faster. Doing everything I can to keep her happy. Soon my thighs are slapping into her, my full length driving into her perfect wet pussy.

Anne has to bury her face in the pillow as I fuck her from behind. Cumming hard on my cock. I can feel the grip of muscles around my dick, unable to pull out or push in with how tight she is gripping my member. Anne stays motionless, shivering as her contractions continue. Looking over her shoulder again, lust in her eyes, a huge smile on her face, she starts pushing herself back onto me.

Fucking me, slamming back onto my cock. Anne impales her pussy on my throbbing dick. I moan uncontrollably as she builds up speed. I can feel what is about to occur and guide her cute ass forward just a bit so I can get myself out of her pussy before I explode.

As she slams back into my thighs again, my cock rests along the length of her ass crack and fires its load. Spraying Anne's back with my thick white load.

"Holy, wow, that was amazing" Anne says to me.

I begin to rub the cum into her skin as I lay next to her, kissing her gently.

"I've never done it more than once, how were you able to?" Anne asks me.

"You just excite me so much" I say. Continuing to keep the secret that Anne took my virginity for another day.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like