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The time I [M26] played truth or dare with my high school crush [F25] and hooked up with her [MF]
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CrimsonKnight46 is a male/female couple
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So this story takes place back when I was 20 and she was 19. Me and my friend Lex (not real name) met when we were a junior a sophomore in high school. We hit it off pretty quickly and became really good friends. We had so many things in common and were so inseparable that half our highschool always assume we were dating. However this was not the case since we always had our own things going on. We almost never single when the other was, but when we were we would constantly flirt and banter back and forth or just lay on the couch cuddled up. We even made out a few times for fun but nothing even expanded out of that and I didn't want to push it since I didn't want to screw up what we had. I was young, sue me.

For context Lex was tall, had pale skin, bright blonde hair that went down to the middle of her back, a slender body with a nice perky b cup chest and some how a nice round butt with thicc thighs. That woman never lifted a weight but game my quads a run for their money. Not to mention she would always wear these tight fitting dresses that cling on to her in the best of ways.

I was still living at home at the time and my parents were away for the weekend so I invited her over to hang out and we could get drinks and watch movies. Ah the days when I had to illegally aquire alcohol, what a rush. So on that cold winter day she came over, she brought a few beers and I had bought a bottle of absolute and some orange juice to makes screw drivers. We broke out the horror movies and started drinking the beers first to Nightmare on Elm Street. By the end of the movie we had crushed the 6 pack and were feeling a little tipsy.

She asked me to grab the vodka so I made us screw drivers and we made it a quarter way through child's play before I paused and went to my kitchen (why I can't remember) while there she followed me in and we started having a conversation so we sat at the table and I pulled 2 shot glasses from the case and asked her if she wanted to drink the vodka straight. She agreed and we kept talking. After a few minutes she asked if I wanted to play truth or dare. I genuinely didn't think much of it but it sound fun so sure. The first couple of times we picked truth, nothing over the top just general embarrassing shit. Till one point where I picked dare. "I dare you to strip down as far as you are comfortable with me."

I had to take a minute, asked her maybe twice if she was serious and she said she was so being that I was super comfortable with her I stripped down completely naked and sat back down. She laughed but she didn't try to hide that every chance she got she would stare at my cock which was now pretty hard. So next up she picked dare and I asked her to do the same. She stood up and did a little side to side movement with her hips and she slowly slipped her dress off to reveal the matching red lace bra and panty set she had on. "And that's all you get, gonna have to work harder for the rest" as she winked at me. I just laughed it off and we kept drinking.

We would up killing the bottle and we were pretty drunk. We both stood up and she admitted she was feeling a little woozy so I walked her over to my living room. I had 2 couches on opposite sides of my living room. I carried her over to one and laid her down and cover her up with a blanket and I was way too drunk to get dressed and crashed on the other and fell asleep. After what seemed like maybe 20 ish mins I woke up to her bringing the blanket over to my couch and saying she wanted to cuddle up and she just hopped facing me still in just her underwear. It was impossible not be hard at this point. She pulled in closer to me and felt my cock poke her stomach.

Before I had a chance to apologize she placed her hand on it. I thought maybe she did that by accident and didn't notice till she said "you know I gotta admit you have a really nice dick, I've been wanting to play with it since you took your pants off" as she starts stroking me. Every now and again she would rub her thumb on the head and I'd lose my mind. I couldn't take it anymore and I slipped my hand into her panties and started rubbing her clit. She let out a gasp and said "please don't stop rubbing". I continue massaging her clit and only stop to slip her panties off. She at one point puts her leg over my side and move her hips close and starts grinding her pussy on my dick. She was so wet.

After a little while of that she asks to go upstairs and she leads me to my own room. She undoes her bra and shows me her nice perky that I take a sec to kiss and suck on before she pushes me backwards into my own bed. Lex climbs on top of me and grabs my cock "I've been wanting to do this for a while now" as she lowers herself onto it. She grinds her hips into mine and rides me for what feels like an eternity. I even held her down and took turns just thrusting into her which made her eyes roll back. I turn her over and start fucking her missionary but we are going HARD. Slamming the headboard so hard that things around my room are falling over. She has come several times during a of this but I'm close and she says "cum on tits". I pull out and cum all over over and she starts jerking me off. I'm so sensitive at this point that I flop back on bed.

We stay cuddled up in bed for a while but unfortunately she had to leave later on during the day. This wound up being the one and only time we hooked up but it was memorable. We still talk and bring it up from time to time and just laugh about it. Oh what could have been.

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Posted
3 years ago