The [f]irst ti[m]e she let me put it in her ass. | 2016

We were dating in college. She was a dusty blonde with 36C tits, 30 inch waist, muscular ass, and covered in freckles head to toe. When she took her clothes off it always made me horny as hell - I couldn't resist her. We were young at the time, and still experimenting - she had fingered herself for me while I watched, I had jerked off into her mouth, we had fucked in every position we could think of, and I'd already cummed into her mouth, into her pussy, and onto her tits multiple times.

One night, after we had already had a speedy, but delightful, fuck - her on her back, arms stretched out above her head, tits heaving, gasping for breath as I came into her pussy - we decided to sleep in the nude in my dorm room. She turned on her side, with her back to me, my right arm under her head, and my left arm draped over her side. While falling asleep, I started to idly toy with her nipples with my right hand, and out of pure instinct, my left hand reached down to her pussy. She became wet, and her nipples, which had been soft, rapidly became hard.

She turned her head to me and asked "Have you ever wanted to fuck me in the ass?"

I could barely use words at this point - I think my response was "uhuh."

Her reply "then do it. Don't hold back."

I proceeded to press the head of my cock against her asshole and slowly press in. She pressed back, and hard. Suddenly, I was in her ass almost to the hilt. At this point she was holding the hand I had against her pussy and pushing it in movements against her clit.

She then reached her hand toward my balls, and pulled them up against her clit, forcing my cock all the way into her ass. At this point she let out a little yelp, then said, in a calm tone "good... good boy. Keep fucking my ass."

Despite her request not to hold back, I did a bit. I slowly, very slowly, pulled in and out, while she held onto my balls with one hand and now rubbed her clit with the other. At this point, we were still one our sides, and I had both my arms wrapped around her, squeezing her breasts as hard as I dared.

About two or three minutes later, she started to breath very heavily, and started gasping. She then said, very loudly "oh god.. I'm cumming.. please... please cum in my ass.. I'm cummmiiiiiiing" and I felt her entire body convulse. She shook from head to toe, I could feel her pulse in her nipples, and she writhed as her ass clenched my cock. I couldn't hold on - I came again, though this time, because most of my cum had been spent on her pussy, it was not a huge load. Just a few short squirts, but she gasped each time.

A few minutes later, after I pulled out, she turned around and put her arms around me. She kissed my neck, nuzzled her forehead against my chin, pressed her breasts against my chest, threw her leg over mine, then fell asleep. I followed shortly thereafter.

On waking, she asked me "so did you fuck me in the ass last night, or was that just a dream?"

"I did, and you cummed really, really hard."

"Good - I just wanted to check, because my ass is sore. My pussy isn't though."

More good times ensued.