Winner's Choice - Sex Stories

Winner's Choice

“I choose . . ,” Jake paused. “. . . a blowjob!” It was really pretty stupid on my part when you think about it. I was wearing nothing but a pair of panties and I decided to raise the bet by saying ‘If you win, you get to choose. Anything, anything you want’. I knew the moment that those words left my mouth what Jake wanted to put in my mouth. Trevor and Liv had both folded and were just watching the hand play out. I think they knew what was going to happen but I was just too stubborn to fold and gracefully give my panties up. Instead, I being ‘Little Miss Confident’ with a full house hand of Jacks over 9s offered up my ‘Anything you want’ bid. When Jake called my bid and laid down four 3s I cried foul. Not at anyone in particular but I was just in disbelief that I could have lost so many hands that when I finally had a nice hand I was beat. So when Jake said ‘a blowjob’ it wasn’t really a surprise. In the five months that Jake and I had been dating I had successfully avoided, dodged, evaded and in general hid every time he wanted a blowjob. We had been fucking pretty much from the first date. We hit it off right away and well he “hit it right away”. Within three hours of our meeting his hands were on my tits and his cock was buried deep between my legs. By three hours and three minutes of our first date his cum was seeping out of my pussy and down his cock. Ever since then it’s been non-stop sexual gymnastics with the one exception, blowjobs. Up until today I have given a ...

... grand total of zero blowjobs. Yeah, I’m something of a blowjob virgin. I’ve seen the videos and heck, I’ve even seen girls at college intentionally letting some guy impale their throat with a hard cock. But I just haven’t been able to bring myself to let a guy put his dick in my mouth. I’ve been close. Billy Flynn was two inches away from the sexual promise land of every high school boy when I puked in his lap. Numerous guys have tried the ‘let me straddle your chest technique’ or let me ‘tittie fuck you’ with no intention of stopping there. Billy had so generously bestowed upon me my ‘cock crazy’ monikier the night I almost gave him head. You see Billy had convinced me that he was going to show me all the things I had been missing as a virgin and led me behind a wood pile when everyone was coupling up at a party. Once we were concealed from everyone's view he proceeded to teach me the finer points of French Kissing. Five seconds later Billy awkwardly shove his hand up my blouse. He pushed my bra up just far enough so the underwire was pressing into the middle of my boob causing me to wince in pain. Not satisfied with my boob he navigated his hand under my miniskirt. He started pawing at my pussy and finally grabbed my panties and pulled them down do my knees. With all the tact of a gorilla trying to drink tea, Billy then attempted to shove his finger in my pussy but did nothing more than spear the inside of my upper thigh. Bill was not going to be discouraged by how ‘tight’ I ...