(F)ingered (m)y ex girlfriend's virgin butthole while another ex girlfriend slept next to use | 2016

This story took place when I was a freshman in high school. I had been dating this girl named Samantha for about six months. Both of us were virgins, but had experimented sexually with each other. We used touch each other’s naughty parts while watching movies and go down on each other occasionally too.

Anyway flash forward to one night freshman year. Samantha and I had broken up a week before, but we had the same friend group so we still saw quite a bit of each other. On this night a group of us were spending the night our friend Katie’s house. This group included Samantha, another ex-girlfriend of mine named Cindy, and myself.

Now at this point in time Samantha absolutely hated my guts, yet somehow, when it came time for all of us to go to sleep, I ended up sleeping between Samantha and Cindy in a bed in the basement.

I was pretty skinny back then, tan skin, dark hair and eyes. Samantha was blonde with grey-green eyes. She was very flat-chested, but had nice puffy little pink nipples and an amazing ass. Cindy had brown hair and blue eyes. She was a little pudgy, but had quite a nice pair of breasts.

So here we are, all three of us laying in a bed together, with me in the middle. Samantha and I got in a stupid argument, typical of a recently broken up couple, and fell asleep extremely angry with each other.

I woke up in the middle of the night and felt Samantha stirring next to me. I felt bad, so I leaned over and whispered in her ear,

“I’m sorry I’m such an asshole”.

She didn’t say anything. All she did was roll over into a position so that we were spooning and place my hand on one of her little breasts. She wasn’t wearing a bra and I could feel her excited nipple poking up through the thin fabric of her tank top. All the while Cindy was asleep not two feet away from us.

We laid like this for a few minutes, neither of us saying anything. Just me rubbing her little nipple and her starting to grind her barely covered bottom on my now extremely hard cock. Finally, she rolled over and whispered to me, “I’m horny” as she reached down into my boxers and found my very excited dick. She slowly stroked me up and down while staring at me with big, eager, puppy dog eyes. We started furiously making out and she continued to work my cock while I groped her ass in a way that only an inexperienced teenager is capable of.

I began playing with her little pussy and she had to stifle her moans in order to not wake Cindy. She broke off our kiss in order to say the most magical words that can come from a girl’s mouth:

“You can do anything you want to me”.

I immediately took my finger that was still slick with her juices and found her brown little bumhole. I started teasing it by circling my finger around it, feeling all the lines of her balloon knot. Slowly I slid a finger into her asshole as she softly whimpered into my ear. She continued to work my throbbing cock as I slid two fingers into her ass and another back into her pussy.

We kept this up for a while until I was furiously pumping my fingers in and out of her little virgin pussy and butthole. She kept jerking me off until I came underneath the covers and then slid my fingers out of her with a wet little pop.

We kissed for a little while longer before she looked at me and said, “Promise you won’t think I’m weird for liking that”.

I whispered “Of course not”, and then we both fell asleep while listening to Cindy’s soft breathing next to us.