Losing my [M18] virginity to my crush [F18], the quiet artsy girl at school

Let’s call her Anna.

This happened the Friday night after our high school graduation, in her bedroom at 1AM, while her parents were sound asleep upstairs (her bedroom was on the lower level).

Anna was an artist type, quiet, often spending her lunches alone in the high school library reading a book.

I’d had a crush on her for years, both because I tend to find myself attracted to quiet type girls (I’m a quiet, introspective type myself), but also because her breasts were very large (34H cup, I later learned). Ever since I became interested in girls, I’d always had a (probably unhealthy) fixation/weakness for extremely large breasts.

It’s obvious to me now Anna was insecure about her body, but I loved watching her walk through the hallways at school. Even though she always worse loose fitting sweatshirts/hoodies in a hopeless attempt to conceal her figure, they merely hung like a drape over her incredible, massive bust. I lamented never having a gym class with her where I might’ve seen her with a little less clothing on. She had a cute face, young and girlish with freckles. She wore glasses and no makeup, and I really liked that too – There was something very natural about her.

It was obvious she didn’t like attention, but I was very fortunate to have a class with her during the final quarter of our senior year. We all had to pick partners for a class project; I took the opportunity to ask to work with her, playing it “I guess we’re the only ones left”.

We got along really well and found we had lots in common for high schoolers – feeling like outsiders, the way we think about certain things, etc. We became fast friends and enjoyed each others company. I felt silly for not getting to know her sooner.

She invited me over to her house for the final leg of the project – a presentation board with stuff on it – and we sat at her desk going over graphic layouts. When I turned to her to as I was speaking, she leaned in very suddenly and kissed me. I cannot begin to describe how exhilarating and unreal this moment was. Although I’d had dreams about this kind of moment, I was completely unprepared for it happening in reality. She was very enthusiastic and pushed her tongue into my mouth quite awkwardly, leaning in and wrapping her arms around my shoulders. I put my arms down around the small of her back, quite surprised at how small her waist turned out to be as I held her through the baggy cotton of the sweatshirt.

Anna and I became better kissers through the rest of the spring. Spending more and more late nights in her bedroom. Usually I’d drive over on a friday night after both of our respective households had gone to bed. She would wait for my car at her bedroom window, greet me on her front porch, silently lead me down the half flight of stairs (split level ranch house) to the basement and into her bedroom, and we’d immediately begin kissing all over again.

The first time we kissed, I’d been a little too nervous to become completely turned on, but by the second time and every time thereafter, I had to deal with the rock-hard erection which grew in my pants. After a few minutes into kissing, I’d have to pull my hands away from her back and adjust my cock, pointing it to one side and slightly up toward the waistline of my pants, where it didn’t hurt as much to be constricted.

I should mention that my cock is larger-than-average (to the point of causing problems in bed). She took notice of it very quickly, and although she was a virgin, she knew it wasn’t normal. When we awkwardly began to discuss the possibility of having sex, she made it very clear that she was intimidated by my cock and nervous about being in pain. But she was also mesmerized by it – after a few weekends, she began to rub my erection through my pants while we kissed, taking a break from kissing to look down at the outline of it in my jeans, sometimes whispering “wow” or “it’s so fucking big”.

Mind you, up until later, these makeout sessions never ended with clothes coming off or any kind of orgasm for me. I’d started to finger her with my hand down her pants and underwear, totally mesmerized by the look on her face while I did it. Later on 3 or 4AM, I’d drive home and make myself cum, but I slept badly those nights, dreaming only of the intimacy, oversleeping until noon or 1PM the next afternoon.

Anna didn’t want me putting my hands on her breasts at first. Although they always pressed against my chest while we kissed, she wasn’t quite ready for me to give them attention. Despite my fixation with her chest I was totally fine with this, as I was completely overwhelmed already.

The Friday night after our high school graduation, I went over to visit her as usual. We began in her room, she kept me pinned against the door kissing me. After a few minutes, she took her hands away from my back and started gently massaging my trapped erect cock with both hands. I moaned at the sensation and she early started to rub it more aggressively in response, hopelessly trying to grab it / wrap her hands around it through the denim of my jeans.

Barely a moment later, she reach up for the bottom of my shirt and began to lift it off. I was delirious and overwhelmed, my heart pounding, but I could’ve been more eager to help her. She fumbled with the shirt and I took it off for her. She pulled herself against me to kiss me again, feeling the cotton of her sweatshirt against my naked torso.

She stopped, stepped away and gave me a little bit of a nervous look, and began to pull the sweatshirt up over her head. She struggled as she quickly but awkwardly worked it around her breasts, but my heart practically stopped when she tossed it aside. She was topless except for a gigantic, flesh colored bra which shaped her breasts into giant twin globes – somewhere between the size of a cantaloupe and a kickball. She had her hands up at first (lifting the sweater up to take it off), but as she lowered her hands again, I was astounded watching the way her breasts moved. They looked like they were almost trapped in the bra cups (in retrospect, I think her sizing was off) and bulged out slightly where they met in the middle. To this day (10 years later) I have never seen such deep cleavage.

She was looking at my face, nervously gauging my reaction, but I could not have been happier. I told her she was incredibly beautiful, pulled her close and kissed again, and this seemed to break her spell. I felt her mouth curl into a big smile as she pressed her lips to mine; she exhaled and laughed with relief, kissing me ever harder in earnest. With my hands on the small of her back again (and indeed it was small. hourglass being an understatement), I finally explored its bare skin.

She stopped, led me toward her little twin bed, and asked me to lie back. I didn’t know what was going to happen, but I very eagerly sat back, atop the comforter, propping myself up on the pillow. Standing beside the bed, she very quickly pulled down her pants and underwear. Her hips were quite wide and I remember being entranced by how dark and hairy her bush was (I’d only felt it up to this point).

She climbed into bed and straddled me, wearing nothing but the bra. She smiled down at me with a mix of affection and nervous excitement. My heart began to pound as she then reached behind her back and began to unhook her bra.

As she pulled the bra straps down from her shoulders, her breasts began to change shape dramatically, transforming into gigantic teardrops as they fell across her torso, covering her belly button. This same motion of pulling down the straps also turned her previous deep high cleavage into an extremely long and low cleavage, pocked with deep stretch marks. Her areolae were small but her nipples were stiff and quite large, each one as big as the tip of my little finger.

I couldn’t have been more turned on in my life. I fell in love with her naked breasts instantly, and although I was eager to touch them, she instructed me not to. Instead, she reached for my waistband and early began to pull my pants down.

Once she pulled down my boxer shorts, my cock sprang up against my torso in full force. She stared down at it with a wild intensity that almost caught me off guard. She stared at it for a good while, saying nothing, before I finally realized that she was rubbing her clit with one hand.

Seeing that she’d opened the door to masturbation, I began to reach down to grab my cock, but she stopped to pull my hand away, catching me off guard again. She then told me in an unexpectedly authoritative tone: “No. don’t you touch it. This cock is *mine*.”

Overwhelmed as I’d been up to this point, I didn’t even know what to think now. Instead, I finally resolved to submit myself to whatever was about to happen, not knowing what it might be. But I was loving it.

She shifted herself back a bit, leaning down to examine my cock more closely as her tits sat themselves on my thighs. She stared at it wildly, probing it up and down with her fingers, and I could feel her breath against it. Without looking up at me, she licked her lips and very suddenly and clumsily attempted to open her mouth around the head. It felt awkward as she tried to open her mouth around it, lightly grazing her teeth against it, going about two or three inches before she stopped to catch her breath. That’s when she finally looked up at me and said (something like) “I’ve wanted to fuck you for a long time, but I can’t even get your cock in my mouth”.

Nevertheless, she sat up again, pulling herself forward and straddling me, positioning her vagina against my shaft (sitting up against my torso). I could feel the labia against my cock for the first time, and her eyes never left mine. She still had that delirious, intense look on her face.

She sat up slightly and reached for my cock, positioning the tip against her bare vagina for the first time. The outside of it was wet, warm, wonderful.

Then she began to lower herself onto me, slowly. The inside of her vagina felt practically hot in temperature, velvety and soft, but quite tight. She clenched her eyes shut and opened her mouth wide as she worked the head into her vagina. It was so tight at first that it almost hurt, but my cock couldn’t have been more stiff. She looked like she was in pain but she didn’t stop, inching herself up and down until the head of my cock was finally inside. After a brief pause, she began to ride just the head by itself, moving herself up and down by the inch, seemingly getting used to it, drenched in sweat and breathing heavily. It was almost too tight at first, although it began to loosen slightly after a few minutes.

Over the next 10 minutes, she rode me slowly and sweated all over me as she slowly worked the first few inches of cock into her, totally committed. She began to moan softly in a higher pitch than her normal voice, which I wasn’t expecting either.

In retrospect, I don’t know how I lasted as long as I did. What amazed me more than anything else in this moment was how she’d transformed into something I’d never seen before. She’d become sort of like a different kind of animal, as though this moment of sex awakened something in her which I didn’t see before. Looking back, she was quite dominant and selfish when we had sex together, as though she was using me and my cock to pleasure herself. But the fact is – I loved it. I loved submitting to her and watching her float away on a cloud as she fucked me, completely consumed by her own gratification. It was an unbelievably hot turn-on for me.

Anyways: Once she’d decided she could go no deeper, she settled into a rhythm and began to ride. Her tits swung back and forth under their own heavy weight.

I was delirious with the sight in front of my eyes which would soon become a regular thing: Anna’s beautiful face above mine, her mouth hanging half open and her forehead drenched in sweat, her tiny shoulders and her wild dark hair that bounced around, all sitting atop two fabulously gigantic breasts which covered the bottom half of my vision, wobbling and hanging between us and slapping her little stomach (or my chest) as she rode me (depending on how high she was sitting up)

After a moment, she took that bossy tone again, ordering me to suck her nipple. I could not have been more excited to submit to her; I took the big rubbery thing between my lips and tried as best as I could to make love to it with my mouth. It took a short while while she instructed me how she wanted her nipple sucked, which was quite a bit harder than I’d expected – my mouth wasn’t quite strong enough to continuously suck it hard the way she liked it, and I had to take breaks to relax my mouth muscles, but I got better over time. Unlike smaller breasted girls I’d dated later on, Anna’s tits were so big that I could keep her nipple firmly in one place even as she bounced up and down on me. In this moment during our first time having sex, I’d never heard her speak this way before as she told me, almost grunting, “yeah, that’s it, suck on it, suck on it, etc” between ever louder moans.

I loved watching the faces she made when I sucked her nipples. She liked me to be aggressive in playing with her tits in a way I haven’t quite experienced since.

Anyway: I’d miraculously staved off approaching an orgasm up to this point, in part because she’d become extremely wet and also keeping her riding relatively slow, but what happened next caused me to lose all control.

Up to this point, Anna had kept her hands resting against the bed at either side of me. Without stopping her riding, she lifted one hand to her breast and pulled it away from my mouth. In that moment I figured all the stimulation might’ve been too much for her, but I couldn’t have been more wrong. With the heavy breast still spilling out around her little hand, she began to lift it up towards her face, angling the fat nipple toward her lips before she took it into her own mouth.

I was able to watch her do this for about one second before my orgasm hit. She sucked her nipple and pressed the surrounding tit flesh against her face, making a loud but muffled moan.

I seized up and cried out, spending the next ten seconds lost in space while I emptied buckets of cum deep into her tight vagina. I couldn’t tell whether she’d stopped moving or not, my awareness was completely gone.

Eventually I collapsed, completely spent and suddenly struck by an unexpected wave of complete exhaustion. I had never had an orgasm this intense, before or since.

Source: reddit.com/r/gonewildstories/comments/4nooko/losing_my_m18_virginity_to_my_crush_f18_the_quiet