My favorite sexual memory isn't so much a single act - more of a bunch of intertwined ones.
I've always been pretty monogamous and never felt comfortable cheating. I was dating a girl for several months at this point. She was really the first freaky girl I'd ever been with and the first girl I ever had that loved ROUGH sex.
She lived about an hour away from me and I usually only saw her once a week.
Meanwhile, in the college town I was living in, I became friends with a group of student (guys and girls), and they adopted me on their intramural soccer team. I also hung out with them quite a bit. One of the girls -- a cute, petite little 20 year old, had a massive crush on me. I knew it all along, but never acted on it. I didn't even tell her or the others that I had a girlfriend, because I enjoyed innocently flirting with the girls - especially the one who had a crush on me.
A few months had passed since I was in the group of friends, when things started getting sour with my girlfriend. We began having breakup conversations.
At the same time, things started getting extra flirty with the college girl.
After a fight with my girlfriend over our status, I decided I wasn't going to visit her that night, and would instead go out with my friends, including the cutie crushing on me.
The night was increasingly alchohal infused and by 1 am, I was dancing dirty with the girl in a dark club. On a whim, I decided to put my hand down her skirt and gently touch her vagina. She reached down, grabbed my cock, and whispered, "I want your cock."
We bolted out of the club and into her friend's house. I tore off her clothes, ignored the condom in my pocket, and fucked her incredibly tight pussy. A few hours after we had sex, as she laid naked in bed, she told me she'd only been with one man before me. Her high school boyfriend. She also told me that she wasn't sure how to give a blowjob, and never thought she was good at it.
I told her "the key is letting the guy take control, if you're comfortable with it."
She said, "I am."
Within seconds, she was on her knees.
I slowly began fucking her throat.
She gagged a few times, looked up at me and apologized. "Sorry, she said. That's gross."
I kissed her forehead and said "no, no...I love that."
That's all she needed. She looked up at me, and began furiously gagging on my cock. She was desperate to pleasure me. I pinned her to the bed and fucked her face like it was her pussy. We started 69'ing and her pussy was soaking wet.
Finally, I told her to get on her knees, and I absolutely blasted her face with my load. She was shocked...as jizz dripped off her eyes, nose, and chin.
I cleaned her off, told her she was beautiful, and that I needed to head home. She stood in front of me naked, hugged me, and asked me when we'd see each other again. Tonight? I said. She smiled.
On the way home, I called my "technically still" girlfriend on the phone. She asked if I wanted to come over for lunch and talk.
I skipped the shower, and got on the highway.
I was so at peace from the previous night, that when we sat down to talk, all the anger had gone away. We both agreed that we should spend some time apart, just to see how it goes.
On the way back to her house I thought to myself..."you know what man...you're not cheating on anyone at this point...just go for it."
I pulled her into her bedroom and said "friends with benefits?" She laughed and I stripped her naked.
It had only been two hours since I came all over the other girl's face, and said goodbye as she stood naked - as if waiting for me to return. Now, as I looked at my recently-named ex, I compared their bodies. My ex had bigger and better tits and a thin runway strip over her pussy. She was thin-ish, but only in moderately good shape. The 20 year had an incredibly tight body, little tits, and was totally shaved.
She pulled me onto the bed and spread her legs.
But I had another idea.
I knew I was certainly a funky from the prior night of condom-less sex and no shower. So I thought to myself...hmm, let's see if she can tell what she's tasting.
I sat her up on the bed and put my cock in her mouth.
She sucked it for 10 seconds, then coughed and said, "hey! think you could shower before you put your dick in my mouth!" I said, "haha sorry, sorry. Long night of dancing."
I fucked her bareback, made her cum, pulled her up by the ponytail, and blasted on her face too.
On the way home, my dick was hard the whole time, thinking about how I just made my now ex gf taste the dried pussy juice of a girl who had a massive crush on me.
I went home, showered, slept for 5 hours, and showered again. Then I took the 20 year old out for a beer, and fucked her again.
As we made out in the shower afterwards, and she told me I was incredible.
I layed her down on the bed, took whipped cream out of my bag, and completely shocked her by licking her everywhere. Including her asshole. She never experienced anything like that.
It was an insane 36 or so hours!
Sadly, I ended up breaking the cutie's heart after a couple months of amazing sex. A few years later, I reconnected with my ex and he hooked up a few times --- totally emotion-free. Just for fun. I admitted to her what happened that night, and admitted that I wanted her to taste the college girl's pussy. She was pissed in a joking way, but called me a sick bastard and actually thought it was pretty hot.
She asked me to see the girl. I pulled up some of her hottest (clothed) pictures. Didn't want to let on that I safely protected naked shots of both of them
