When I was in high school I had an on/off relationship with a girl named Jessica. She was a very pretty, athletic girl from a wealthy family. Think college soccer player; slim with an ass you could bounce a quarter off of. For visual I was 5’9″, 160 lbs, around 9% bf, shaggy brown hair, and 7″ for those that care. Her family loved and trusted me and we still talk occasionally to this day. The problem was Jessica was absolutely crazy. She strung me along, fought about everything and overall was a drain on me life. When I was 19 she had broken up with me in a particular fit of crazy and burned all the belongings she had of mine. About a month after that her family offered me a good bit of money plus access to their sweet house and liquor cabinet for a week while they were on vacation to housesit.
In the month we were broken up I started talking to another girl on AIM (yeah a long time ago) named Sasha. Sasha was around 5’6″, tan brunette with blonde highlights just past her shoulders, large B cups with a thick ass. She played softball at the same high school my ex went to and it turns out they were best friends turned mortal enemies. Through our late night chats I could tell that Sasha was also crazy, but in the best way. I look back now and it’s obvious she had some issues that she planned to work out on every hard dick she could find.
I’m a few crowns in one Friday night while house sitting and decide I could use some company and know just who to call. 30 minutes later I’m in a hot tub in my boxer briefs with a beautiful 18 yr old girl, listening to some shitty emo, and getting harder by the second.
Sasha started asking me about Jessica and if we had ever been in this hot tub together giving me not so subtle hints. I told her “Yeah, actually she gave me a blowjob while I sat on the edge right here.” She grinned like the damn Cheshire cat, took her top off and said “I bet I’m better.” I’m now rock hard and my head is poking out the bottom of my underwear but decide I want to push this rivalry a little further. “Well, I don’t know. Jessica doesn’t have a gag reflex.” She lit up and I knew the challenge was accepted.
I sat up on to the edge of the hot tub and let her pull down my underwear while my hard cock sprung out and slapped against my stomach. Sasha proceeded to suck my dick like she was trying to suck the chrome off a trailer hitch. She looked in my eyes while trying to get deep like she was looking directly in my soul. In all reality she could only get about halfway down and the skill was sub par but the enthusiasm was top notch.
“You know, Jessica never lets me have sex with her out here.” I told her while she was stroking me with a mouthful of my balls. In my head it wasn’t like I was doing this in her room. It wasn’t that fucked up.
It was a warm summer night so we both hopped out of the hot tub, did one wipe with a towel then laid them down on to the soft rug they had on their pool deck. I quickly untied her bottoms and threw them aside. Her shaved pussy looking me square in the face and I dove in face first. Circling her clit with my tongue while working 1, then 2 fingers inside. She was dripping wet already and moaning for me to finger her harder. Message received. I kissed my way up her smooth stomach to her perky tits and started gently sucking on her nipples while I continued my digital assault on her pussy. I used 2 fingers and the bowling grip and started to hammer at her g spot. She loved this rough play and let out an orgasm with a high pitch scream I’ll never forget when I bit down on her nipple.
We both caught our breath and without another word she got on all fours. “Please fuck me hard daddy…” She trailed off. Ok, didn’t know I liked that power dynamic but the twitch in my dick affirmed I sure did. I was still young and not used to rough sex of any kind. Previous girls always wanted something gentle, loving. Sasha wanted me to try to split her in half and I was willing to try.
I kneeled behind her, lined up and with one long, strong thrust was balls deep in heaven. I stayed all the way in, dick twitching trying to adjust to it’s new surroundings, while I ran my hands all over her thick ass. I began to piston in and out of her shaved snatch, picking up the pace with every stroke. I had the greenlight to experiment so I did. For the first time that night I grabbed a fistful of a girls hair and she squeeled with delight. I licked my other thumb and let it trace circles around her tight little asshole. She only panted “Yes!” I pushed a little and went in to the first knuckle and Sasha shook like I had just turned her to a vibrate setting. This was amazing and it’s only been 5 minutes.
I could already feel the end was in sight so I released my grip from her hair and her ass and slowed down my pace. I slowly pulled out so I was almost all the way out then hammered back in. The visual of my slick cock filling her up will never leave my mind. But I was going to pound her again before I came. I grabbed both her elbows, pulling her back to me, hooked my left arm between them behind her back, and used my right to pinch and twist her nipples while biting on her neck. I couldn’t take another second and told her I was going to blow.
She said she wanted to see it so she rolled over and I straddled her stomach while stroking my cock. I grabbed her head from the back and made her watch as a shot my load all over her perky tanned tits.
We both laid on the towels for a few minutes before she smiled, got up, and hopped in the pool to wash my cum off of her.
She eventually left and I called Jessica later that night and let her and the family know everything was fine at the house. I felt a little guilty but through college they both used me as fuck buddies periodically. She never found out but as far as I know they still hate each other.
Source: reddit.com/r/gonewildstories/comments/a2re3a/the_worst_thing_i_m_ever_did_f
Well played, my man!!!
how is this the worst thing…sounds like a great night.