That ti[m]e I [f]ucked my high school crush in the ass

(I wrote this up approximately ten years ago, right after the event. Just found it recently. Everything described here took place after we graduated, and thus the participants are over 18–don’t get too excited, ya perv.)

I had a huge crush on Meghan in high school. She haunted me like a ghost, always in my dreams and daydreams, but things never quite got started between us. I never got the timing right, I suppose. She’s incredibly gorgeous, in a way that’s more cute than seductive (most of the time). She’s tiny–I doubt she’s ever weighed more than a hundred pounds in her life–with a moon shaped face, freckles, and lips that are always sticking out slightly in a little pout. Even though she’s small, she’s well built for her size–her tits are big for her frame, about the size of large oranges, and her ass is firm. I always imagined it to be perfectly ripe for a good fucking…

Anyway, one of Meghan’s best friends goes to school with me now, and we actually live in the same dorm. She lives several floors above me, and one day, she let me know via facebook that Meghan was visiting. Her friend confided in me that she (Meghan, that is) had just gone through a bad breakup with one of her foreign boyfriends. She always managed to get boys from Spain, England, Portugal–anywhere but the US–and that she’d decided to take a week off school to visit friends to cheer herself up. I hadn’t seen her in over six months by this point, and my crush was almost gone, but I was still excited to see an old friend, so I went upstairs and found them sitting together, chatting about high school, and I joined in. Then, her friend had to go to class, but she invited me to hang out in her room and keep Meghan company.

“Thanks for staying,” Meghan said. We were both sitting on her friend’s bed. She was under some blankets while I was on top of them. “Do you know what happened?” she asked, and cocked her head to one side.

“About your break up? Yeah, I heard.”

Meghan sighed. “I don’t want to make a big deal about it but I feel so miserable. I just want to forget him and the past six months…”

I comforted her as best I could–trying to make her laugh, telling her stories, anything I could think of–but she remained melancholy.

“It’s just hard,” Meghan sighed.

“That’s what she said,” I said before thinking. She smiled but did not laugh.

“Thanks for trying to cheer me up, though. I really appreciate it…” She trailed off and we were silent for several moments. The way she was sitting in bed, she looked like an invalid, in blankets up to her belly.

“You know what he did?” Meghan said all of a sudden. “He fucked every single girl on his floor! Every girl!”

Before I could catch myself, I blurted out: “At once?!”

I thought I was in trouble because Meghan was silent, stunned, but then she started laughing. “No… I don’t think so at least…” She leaned forward and hugged me.

“Thank you,” she whispered, resting her head on my shoulder. I hugged her back, enjoying her soft, flowery scent.

“I just wish,” she went on. “That he hadn’t been my first… I loved him so much and he was my first… my only…”

This surprised me a little. She’d had so many foreign boyfriends, I just naturally assumed she preferred European cock to American cock.

“I just wish my first time had been with a nice, sweet guy…” She blushed now. “Don’t take this the wrong way, but I wish my first time had been with a guy like you. That’d make this all easier.”

“You know,” I said, almost choking over my words. “I had a huge crush on you in high school.”

She looked up at me, her eyes a little glassy. “Really? I wish I had known.”

In my mind, I was kicking my adolescent self, but in the real world, I just stroked Meghan’s back. She seemed to like this–she hmmmed with contentment and when I ran my fingers up her spine, feeling each individual vertebra through her shirt, she shivered a little.

“I just want to forget him,” she continued. “Do you think… Well, no, it’s not fair to you.”

“What? I just want to help.”

“Well, could you help me forget him?”

I knew damned well what she meant but I wanted to hear her say it. My cock started getting hard.

“What do you mean?”

“Well, I don’t want a relationship right now… I don’t want you getting the wrong idea… But maybe you could, you know… take my mind off him?” Her freckled cheeks were glowing red now and she had trouble looking me in the eye. I took her chin in my hand and turned her head up to look at me.

“What do you want me to do?”

“Something like this–” She leaned forward and kissed me. It was a soft kiss, virginal, no tongue, but I was raging hard now, and all of my crushed dreams of high school came back to me. I held her while she kissed me, letting her set the pace. I felt her soft tongue licking my lips and I responded in kind, licking her smooth, pink lips without haste. I felt her clutch at me, and in one swift movement, she tossed the covers around me. I was on top of her now, and she smiled at me.

“Is this okay?”

“I’ve been wanting to do this since I was sixteen,” I told her and this delighted her. I realized she hadn’t been wearing pants–only underwear–which explained why she’d stayed in bed. She wrapped her smooth, pale legs around me.

“Now you can’t get away,” she said, like a playful little girl. I kissed her again, a little harder this time, pressing my mouth around hers. I felt her gasp a little.

“I don’t want to get away,” I said when we broke the kiss. That brought on another barrage of kisses from her: hot quick ones, wet, and ephemeral, peppering my face and neck. I returned fire by latching onto her neck, suckling her hot flesh and running my tongue up and down her throat. She reached her hands under my shirt, running them over my back, gripping and clutching at my shoulders. Then, she turned her attention to my chest, running her hands over me, teasing my nipples, and even scratching at me with her nails. All the while, I was kissing her, tasting her lips, her tongue, her mouth, and her flesh.

“Is this helping?” I asked in between.

“Yes,” she said, almost panting. “But I need more.” With that, she forced my shirt over my head. She latched her lips onto one of my nipples and started suckling, biting me a little, and running her tongue all around it. I ran my fingers through her hair–the soft, smooth, fragrant hair that I had watched every day for two years in high school–and cupped one of her breasts through her shirt. I felt her own nipple pressing against the fabric, so I reached down into her shirt, worked my hand into her bra cup, and took her tit in my hand, massaging it, and letting my fingers tease her nip.

I wanted to see her tits, I decided, so I tore her shirt over her head and as fast as I could, I unsnapped her bra, leaving her only wearing a tight little Victoria’s secret thong. She beamed up at me, thrusting her chest forward, offering herself to me and I took her up on it. I took one breast into my mouth, suckling her flesh, and she whimpered softly. I tried to busy my other hand with her other breast, but she brought it up to her mouth and began to suck and lick at my fingers. I was surprised at how erotic this was–feeling her hot little tongue run up and down my fingers, and then imagining it on my cock…

I kept suckling her breast, though, and used my tongue to flick her pink, swollen little nipple back and forth. I bit her once, and she gasped, and I felt her teeth on my fingers. I began to expand outward from her nipple, biting and licking and sucking at the rest of her tit, and she loved this. Then, I switched to her other breast, and started all over again.

All the while, I had ignored her crotch, saving the best for last. She took my unused hand and pressed it down against her thong while I sucked her breast, whispering in my ear: “See what you’re doing to me?”

I hummed into her breast. “Just fuck me all ready,” she said, almost like a porn star–so unlike the sweet, innocent, cute girl from high school yet just as desirable. Still, I wasn’t going to give it to her so soon. I had other plans. I began to lick and suck my way down her soft, firm belly, dipping my tongue into her belly button, and down, down, down to her crotch. I felt her tremble in anticipation but I wasn’t going to give into her right away. Instead, I started licking and sucking and nibbling my way down her leg, over her thigh. She whined in disappointment but she seemed to like this too, especially when I started, inch by inch, to make my way up her smooth, pale inner thigh. This drove her wild–I was barely touching her but she was moaning like I was fucking her. I got closer and closer to her crotch, until I could smell her pussy and I skipped over it entirely, moving to her other thigh, and nibbling all the way down to her knee. She groaned, and trying without luck to grind her hips against my face. Then, I started to make my way up again, a little fast this time, and she was getting really into it now. I got up to her crotch, and slowly pulled her thong to the side, revealing the cunt I had lusted after for so long. It was perfectly hairless, shaved cleaned, and glistened pink with her arousal. Her clit peeking out, winking at me, so I gave it a slight lick. Meghan gasped and tried to press her pussy into my face but I held her down. I blew a deep, warm breath on it and she whimpered. Finally, I ran my tongue from top to bottom and then bottom to top before burying my face in her hot, wet hole.

She tasted better than most girls–I had no problem with licking her indefinitely, sucking on her pussy lips and clit, digging my tongue inside of her, and swirling it around her little nub. She rocked her hips against me in a steady rhythm, moaning a little louder each time. I don’t know how much time had passed, but I was suckling her clit hard, when she started shaking more than before. She grabbed my head, pressing it straight into her pussy, and came. My face was covered in her juices and she lay there panting, her breasts rising and falling.

“That was amazing,” she said, opening her arms and gesturing for me to lie on top of her. She began to lick her fluids off my face. I loved the feeling of her tongue running over my skin.

“Now will you fuck me?” she said, still a little dazed from her orgasm. I undid my pants, and tore them off along with my underwear. I guided my cock slowly inside of her.

“Wait,” I said. “Should I–”

“No, it’ll be fine. Just fuck me now,” she ordered. “I want to feel you.”

I didn’t need anything more. I pushed into her, and immediately, I was overcome by her cunt, hot, wet, sopping all ready. She moaned, arching her back. I had dreamed of this for so long, thought I’d never get it, and now, here I was, balls deep inside of her.

I began to thrust, not very fast at first, but she whispered that she wanted it faster. I figured she was all ready slippery enough to take it hard, so I began to pound her cunt as hard as I could, pulling all the way out and slamming in deep each time.

Meghan was loving this and each time, she raised her hips up to meet my cock. She wrapped her legs around me, giving me more room to plunge deep into her. And God, she was tight. It was good I had eaten her out before, or else she might not have been wet enough for me. Even now, she was whimpering from the feeling of being stretched.

“I feel so full,” she gasped again, as I pushed into her. I loved the feeling of her cunt sliding over me. I was getting close, so I picked up speed, pressing into her faster and faster. She was almost screaming now, and just clutched at me as I began to cum. She arched herself once against, and her pussy tightened around my cock, as if milking me.

I pulled out of Meghan and lay next to her. She was panting a little bit but pounced on top of me, kissing me and grasping at my cock.

“That was so good,” she whispered in my ear. She bit at my earlobe, and tugged at me. “But I still want more.” She slid down my body and took my cock into her mouth. She sucked at it, drinking down the combined juices that covered it. I was hard again immediately in her hot little mouth and she seemed to take great pride in showing me how deep she could take me, because she would glance up at me, to make sure I was watching, and then slide my cock down her throat.

She pulled off my dick and squatted over it. She lowered herself onto it slowly, letting her pussy get accustomed once again. She was so small–barely five feet, I should mention–that my cock was driven deep into her. She began to rock her hips slowly, holding onto my hands for support. She closed her eyes, and had this blissful look on her face. She began to bounce up and down now, and I thrust up to me her when she came down, driving my crotch against hers, and grinding against her clit. This she loved, and she went faster and faster, and drove against me harder and longer, wiggling her hips and making herself yelp from the pleasure. Myself, I loved the feeling of being driven deep into that sopping wet pussy I had long for, over and over. We kept that up for almost twenty minutes, when I started getting close. Meghan seemed to be on the verge too, and she came down herd on me, grinding her hips against at a frantic pace. She started to shake again and I could tell she would cum in a second. I wanted to cum with her, so in a single, rather acrobatic move that I didn’t know I was capable of, I flipped both of us over so I was on top, and pounded into her harder and faster than I ever had before. She screamed and started to cum, and so did I. We gripped one another as her pussy shook and my cock filled it once again with my seed.

After that, we lay there, enjoying the afterglow. Two times, I thought to myself. Pretty good. I figured we were done.

“That was so nice,” Meghan said, stroking my hair. “I really need that.”

“Always here to help.”

“I wish I could give you something… Don’t get me wrong, I don’t want a relationship now, but I still want to give you something…”

I had no idea what she meant. Was this the start of my career as a gigolo?

She saw the where I was staring at her and quickly explained herself. “No, not like that. I mean, I gave him my virginity but really, I wish I’d given it to you. I just wish I could do something like that for you…” She paused for a long time. “Actually, there is something I could give you…”

Again, I knew what she meant, and I was excited, but I still wanted to hear her say it. “What do you mean?”

“Well,” and she was blushing redder than she ever had before. “I mean, I’ve never had a guy back there…” I didn’t show any comprehension on my face so she continued. “…in my ass. Do you want to be my first there? Do you think that’s gross?”

I kissed her. “No, I’d be honored. Give me a minute, all right?”

I tossed my clothes on and ran down the hall. In my dorm, someone on each floor is elected a “condom czar”–that is, he or she is responsible for handing out condoms, and to a lesser extent, lubricant and other safe sex products. I found the condom czar’s room for our friend’s floor, and outside, there was a little basket with exactly what I wanted–individual packs of lube. I grabbed a few, and went back to the room.

Meghan was out of bed, still naked, and looking at herself in a full length mirror. She really was stunning naked.

“I was worried you weren’t coming back,” she said, smiling when she saw me. She had been cupping her tits when I came in. “Do you think they’re too small?”

“No, they’re perfect,” I told her with a kiss. She started undressing me, and when I was naked again, I showed her what I had. She blushed, and bit her lip nodding.

“How should we do this?” I had her get on the bed, on her hands and knees. She spread her ass cheeks, showing off her well fucked cunt, with my cum still inside, and her puckered, virgin asshole. I spread lube around her hole and then pushed a few fingers inside. God, she was tight. She moaned as I lubed her up, and fingered her.

“Are you sure you want to do this?” I asked, not sure if my cock would fit.

“Yes,” she said, sounding determined. “You’re nicer to me than any guy has ever been… I want something special with you.” I kissed her on the back of the head.

I covered my cock with all the lube I could and positioned myself. “Just try and relax,” I told her. I began to press in against her. She grunted, and pushed back against me. I kept her butt spread as I pushed.

“I don’t think it’ll–” I started to say but she groaned suddenly and the head of my cock went inside.

“Oh, God…” she whimpered, shaking.

“Does it hurt?”

“A little but… it feels good!”

I wasn’t sure if she was telling the truth, so I stayed still, letting her get used to the feeling. After a minute, she began to wiggle and press herself against me, forcing a little bit more of my cock inside. I pushed forward, and slowly, her ass consumed my dick. She was panting by the time I was all the way inside.

“How is it?”

“It hurts,” she whispered. “But, oh my God, I love it. I feel so close to you… I don’t care about him anymore… Thank you so much.”

I leaned forward, inadvertently causing my dick to move inside of her, and she gave a delighted moan. She craned her neck around so I could kiss her, and we shared one hot, wet kiss before I began to pump into her.

It was the tightest, most deliciously erotic thing I’d ever experienced. The feeling of erasing her pain by claiming her ass as mine was amazing. With each thrust, I felt like I might cum. Meghan was getting into it too. She met each of my thrust with one of her own.

“Oh, Gaaaaawd,” she moaned. “Fuck me just like that. Harder!”

I picked up the pace, driving my length into her deeper and faster, pounding her as hard as I dared to without hurting her, but she still wanted more. I gripped her hips and pulled out all the way before slamming back into her. She screamed and begged for more, so I did it again, and faster each time, plunging all the way through her each time. Soon, I was about to cum, so I gave her one more, good thrust, gripped her tits, and sprayed my cum deep into her asshole.

We lay there, our energy spent. I felt her pulse through her ass, and I’m sure she felt mine. I pulled out, finally, with a pop and she whimpered a little disappointed, and snuggled next to me, burying her head in my naked chest. We kissed for a while before we both got dressed.

“I’m leaving tomorrow,” she told me when we were clothed again.

“I figured,” I said, and kissed her again.

“This summer,” she said. “You’ll be around, right?”

“Of course.”

“Then, if I’m over him by then…”

I smiled, and we kissed once more. I left, knowing that her friend could come back any second and Meghan would have to cover up the evidence of our fucking. We still keep in touch and I’m looking forward to this summer…

Source: reddit.com/r/gonewildstories/comments/8rzkux/that_time_i_fucked_my_high_school_crush_in_the_ass