Filthy professors [f/m]: Adventures in ass play | 2016

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Short prequel: About 15 years ago, I tried anal with my high school boyfriend….once. I swore never again, and until Dylan, I had never so much as reconsidered that decision. Dylan’s an ass man. For a skinny white girl, I like to think mine’s pretty decent…not big, but it’s round, perky, and firm.
Long before we ever crossed that line, Dylan and I had talked about sex and our preferences quite a bit. I was adamantly anti-anything in my ass. Eventually I’ll learn to never say never, because Dylan has rocked my world and turned everything I thought I knew about sex and what I liked upside down.
One afternoon, we were in my office with the door locked and lights out. I was riding on top of him…slow and deep to make it last. He had his hands on my cheeks and gradually ran his finger closer to my asshole. He just grazed it at first, probably to see how I’d react, and then started moving his finger in small circles, down towards my pussy (where his cock was still buried balls deep) and then back up to my ass again. The sensation was amazing. That feeling, which I couldn’t even really describe, made me curious about other ass play. I couldn't believe that I was even considering it. The next day, we were naked in my office again (it’s shocking that we get anything productive done), and I was laying on my stomach. We really hadn’t discussed it, but I couldn’t stop thinking about that sensation from the day before. After fucking me doggy style for a couple minutes, I told him I wanted to try just the tip in my ass. He was shocked that I was asking, I was shocked that I was asking, but I wanted to feel it. He said that if his dick got anywhere near my asshole, he would probably cum immediately. My V gets so excessively wet when we fuck that no additional lube was needed on his cock. He only put in about an inch at first and made sure I was ok. I told him to go a little deeper. That first time, I could only take about half of his cock (to my credit, he’s big….really big), but as soon as he pulled out, he jacked himself until he came all over my back and ass. It was so much and so warm. We both admitted later that we were worried that attempting anal could go really badly, but we were both intrigued and wanted to try more. Being an academic, I read…a lot…and about everything. Ass play was no exception. I read tips and stories and googled positions. I talked to my gay best friend (who, after seeing Dylan, said he’d like to take it in the ass too). The position that intrigued me most was straddling like in cowgirl but inserting PI-ass rather than PIV. I liked the idea of having control over depth and speed….and I really liked that there’d be full access to my clit for rubbing and teasing.
Dylan was pretty stoked to try it. When we finally got the chance, I told him to lay down and let me take charge. He was already rock hard, but I kept massaging him with lube and then slowly rubbed the tip of his cock on my ass. Slowly, very slowly, it slid in. First, just a couple of inches, then a few more, and finally I sat all the way back and had his entire cock in my ass. It didn’t hurt as much as it just felt so full. I started grinding slowly. I bent down to kiss him and realized that at that angle, I had the fullness of his cock in my ass, and I could grind both my V and clit against his pelvis. It was earth shaking, like sensory overload. I had to take it slow that first time, so the build-up was gradual, but when all of that tension finally exploded, it was the most intense orgasm of my life. Waves of complete ecstasy were flowing from my clit, all the way back through my ass, down my thighs. I couldn't walk for the est of the day without my legs shaking, and just like that, I was hooked. There’s no other O quite like it. He had made me feel so good that as soon as I was done cumming, I told Dylan to fuck me any way he wanted. He bent me over, and in doggy style, he fucked me hard in the ass until he came inside of me. We both just collapsed on the floor and stared at each other, simultaneously shocked and amazed by what had just happened.
This was only the beginning of our adventures in ass play. There’s not much I won’t do for a man who can make me cum so hard that I forget where I am. Sometimes, he has to hold his hand over my mouth because I can’t stop myself from moaning his name when I cum. There’s been so much licking, teasing, biting, and fucking, but my personal favorite are the pictures Dylan’s taken of his cock as it enters my ass. This man makes me lose all my inhibitions and self-control….in the best and most orgasmic ways.