This is my first time posting, so please forgive me if I make any mistakes.
This all started during my freshman year of college. My friend, we’ll call her Jill, and I both decided to go to a university that was about an hour away from our home town. Jill and I had never been exceptionally close until our senior year of high school when we got paired up for mixed doubles on our school’s tennis team. Upon learning we were going to the same university we made sure to find dorms that would be close to each other, so we could make sure to see each other often.
Jill is built like an amazon woman. She has big greyish blue eyes, long wavy light brown hair, lightly tanned skin, and she stands right at six foot tall. She’s always been extremely competitive which was greatly appreciated when we played doubles together, but this also caused her to be a bit of a gambler. She was constantly asking me if I wanted to make a bet on something or other with the punishments usually being something stupid like take a shot of soy sauce or yell something embarrassing in public.
One night after we got done playing some tennis the subject of Mario kart came up and Jill quickly said she bet she could kick my ass if we ever raced. I shrugged it off and told her there was no way that would ever happen and if we had a way to play I’d definitely take that bet. Jill shot me a sly smile and told me her roommate would be going out of town for the weekend, and that she still had her old Nintendo 64 at her parent’s house. She explained that she’d leave the next morning after class to go get it and come back so we could play that evening. I told her that I accepted her challenge and that all we had to do was figure out what the bet would be. She said not to worry about it and just to make sure I was at her place at 6 the next evening.
So the next day I took a quick shower after class, threw on a t-shirt and pair of shorts, and made my way towards Jill’s dorm. As I walked towards Jill’s I got a text from her that said to just walk on in when I got there, so a few minutes later when I found myself outside her door I didn’t hesitate to walk in. As I walked into her dorm I saw Jill sitting on her bed in a big white and black robe with her wavy hair tie up in a ponytail, something she always did when she was being serious. Looking at the TV she had everything set up and ready to go.
It wasn’t long before we started racing and yelling playful insults at each other as we played track after track. An hour or so later, Jill turned to me and said that the next cup was for all the marbles. The first two races went by fairly quickly with her winning one and me winning the other. Halfway through the third race I had a huge lead, thanks to some well placed bananas, but suddenly I caught something out of the corner of my eye. Jill, who had been sitting straight back and straight legged against her wall was now leaning forward and had moved her legs into a more spread sitting style. As I looked over to gloat I noticed that both of her tits had broken free of her robe and were hanging out completely visible. My fingers went numb and my attention on the game was completely non-existent.
Suddenly I was jolted back by Jill shouting with joy that she had beat me and we’d have to play the fourth race after all to break the tie. I told her she was on as I tried my best to get my focus back on the game as the next race started. While we raced I couldn’t help but take a few quick glances over at Jill’s big beautiful tits with her perfect pink nipples that stood erect in the cool room. Somehow even though I was significantly distracted I was in first place.
As I was halfway through the third lap with my victory all but guaranteed, Jill threw one of her long legs over my lap completely exposing her shaved pussy to me. This time I lost it and openly stared at her perfect bald lips that glistened with her arousal. The fanfare sounded as Jill crossed the finish line but in that moment I couldn’t have cared less.
It wasn’t until I heard Jill say my name that my concentration was finally broken. I looked up to her face and she had a sexy gleam in her eye as she said that she’d won and it was time for my punishment. She leaned towards me and grabbed me roughly by my hair and guided me down towards her soaking wet pussy. I quickly went to work passionately sucking and flicking her clit with my tongue. It wasn’t long before her body began to tremble from the force of her orgasm.
I shoved a finger into her tight soaking pussy and curled it up to stroke her G spot. She let out a high pitched moan as she was racked by another orgasm. I slowly pushed myself up onto my knees and began to lower my shorts when she put her hand over mine stopping me. She shook her head with a wicked smile and told me that I hadn’t won that privilege yet and maybe if I won the next bet I’d get to fuck her.
Frustrated by realizing I wasn’t going to get to fill her tight pussy with my painfully hard cock I swiftly lifted her legs up to where her pussy and asshole were both perfectly visible and began to take long passes with my tongue over her tight hole, dripping pussy, and finally her clit. Jill gripped my arms painfully hard as she was taken aback by my tongue gliding across her ass and pussy. Suddenly she exclaimed that she was cumming and she squirted all over my face and her now soaked bed.
We both laid there panting while she came down from her third orgasm. I removed my shirt and began drying my face when I heard Jill asking in a mocking voice if I wanted to make a bet. I looked at her with a smile on my face. She looked into my eyes with a hunger that’d I’d never seen in her before as she said, “I bet you can’t make me squirt like that again.”
I lowered my head looking into her eyes with the same hunger, “You’re on!”
Source: reddit.com/r/sexystories/comments/r54zn2/mf_high_school_teammate_turned_fwb_in_college
This is a great story! Well done!