Back when my friends and I hit the same bar every weekend, there was a regular we called Gap-Tooth Sally.
(None of us knew her real name.) Sally was young and pretty attractive from the neck down, but she had a witchy face and a prominent gap between her front teeth that you could easily fit a finger through.
We all joked about Sally because when the hour got late and the bar thinned out, Sally would start pawing one of us, hoping to find someone willing to fuck her. Being young and cruel, we would mock each other and say, “You’re going home with Gap-Tooth Sally!” “No, you’re going home with Gap-Tooth Sally!” and then go back to someone’s place to get even more wasted and pass out in front of the TV.
But a man has physical needs and if too much time passes without having these needs met, things can get…very ugly. So one Saturday night after too many beers, the bar was closing, my friends were gone, and there was Sally telling me I was cute and rubbing my thigh. Fuck it, I thought to myself. I’m gonna fuck Gap-Tooth Sally.
Sally lived in an apartment building down the block. She had a roommate, so we crept quietly down a dark hallway into her bedroom. Immediately upon closing her door, Sally pressed me against the wall and started sucking my face and rubbing her crotch against me. Meanwhile, I was already having regrets and contemplating escape — but it was too late. So I gave in, peeling off my clothes and taking off my glasses. Luckily, I’m very nearsighted so without my glasses every face becomes a blur. Now I could be fucking anyone!
She pushed me down on the bed and hopped on my cock like it was a ride at the carnival.
“Suck my dick,” I ordered, and Sally obediently dropped to her knees and sucked my cock till it was rock-hard and raging to fuck anything.
“I wanna fuck you from behind,” I said, and Sally got on the bed on all fours and wiggled her ass at me. This is what doggie-style was made for! She had a big round ass that was perfect for squeezing and I pounded her pussy from behind while she groaned at the top of her lungs. I’m not sure if she actually had an orgasm that night, but every second my dick was in her she howled and writhed like this was the best fucking known to mankind.
I was too drunk to come, and after a while my dick started to droop. But as soon as it fell out between her ass cheeks, Sally was there to suck it back to life. Then she pushed me down on the bed and hopped on my cock like it was a ride at the carnival. She fucked me so hard it felt like my dick might break off, while I pulled her full tits out of her red bra and kneaded them. I tried hard not to smile as I thought of my friends and how they were all going to lose their shit when I told them who I’d gone home with.
Once again I lost my hard-on, so I stopped fucking and squinted in the direction of my clothes, thinking I should just get dressed and get the hell out of there. But Sally refused to let me leave without coming.
She put my sleepy whiskey dick back in her mouth and sucked and tugged and jerked, tickling my balls and groaning as if my cock was the most delicious thing she’d ever tasted.
When I finally told her I didn’t think I could come, she said, “I love a challenge,” and pushed me back down. This time, she started slowly, running her tongue hard and wide from the base to the head. As I grew, she increased her speed, stopping every few seconds to let a giant trail of spit dangle from her mouth to my cock as she jerked it with perfect pressure. I got into it, grabbing her head and pushing my cock deep down her throat.
Sally moaned and worked harder, faster, while her hand followed her mouth all over my cock. Suddenly, I shot a massive load down her throat that shook my whole body and left me paralyzed. Sally gobbled it all to the last drop. She was still blurry, but I could vaguely make out her gap-tooth smile.