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Most Memorable Sex and Greatest Regret  

Ushawu 50M
16 posts
4/14/2019 1:12 am
Most Memorable Sex and Greatest Regret

I will tell you about the time I was giving an ex-girlfriend and her girlfriend a ride on my way to work so she could borrow my car.

Her friend convinced my ex to take my cock out so she could see it (because my ex-girlfriend liked to brag about how big it is and how well I use it) and once it was out my ex's friend said "Nice cock" and grabbed it which quickly hardened me. This must have made my ex jealous because she immediately bent over and took my cock into her mouth ...and straight down her throat, balls-deep!

I'm pretty sure that was an accident from going down on me so quickly, but to her credit she didn't choke, she just backed off and started sucking my cock like a fiend, clearly intent on draining me while her friend watched.

Whether it was from jealousy or because she got herself too turned on from so wantonly sucking my cock, when her friend suggested she fuck me right then and there, my ex didn't hesitate to pull her jeans off, yank mine down, and mount my now very-ready cock without saying a word.

I managed to pull over before she made us crash while she got into position -- her chest pressed up tight against mine, knees up on either side of me in a sort-of crouching position, with her chin on my right shoulder. Once we were back on the road, my ex pumping her pussy furiously on my cock, her friend reached around and slid her hand along my leg then squeezed my ex's ass then cupped my balls, making out with my ex over my shoulder at the same time.

My ex was dripping wet and her friend was lubing her fingers with my ex's cum already dripping down my shaft and balls, trying (unsuccessfully) to get her fingers up into my ex's pussy alongside my cock. I could tell she was trying to do else down there but I didn't know what it was until I felt her fingers against my cock on the other side of the membrane between my cock and my ex's ass!

The sensation of her friend's fingers rammed up her ass made my ex orgasm hard immediately. Her hips were gyrating like she was having a seizure, and she must have squirted because she completely soaked me (and the seat, which still has the stain to this day) which surprised me enough to make me lose my concentration and shoot my load too, deep inside her.

We finished cumming in/on each other just as I was pulling into the parking lot at work. Unfortunately my work ethic prevented me from just taking the night off and bringing the three of us back to my ex's place to enjoy a proper threesome, but I wasn't exactly thinking straight after that. Honestly, our only concern at that point was getting disentangled without anyone seeing us.

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