How I had anal sex for the first time. [F/M] [anal] [true story]

I’ve had fingers in my ass, I’ve worn a butt plug, I’ve enjoyed the rare occasion of an enthusiastic ass-eater, but I’ve never actually had anal sex in the penis-in-butthole sense.

Well. Until now.

I recently reconnected with someone I’ve previously been sexually acquainted with (it was a very brief time period a couple of years ago). Nowadays we are giving a friends-with-benefits style relationship a go together and so far it’s been extremely rewarding as far as both the friendship and the benefits.

Something you should know about my FWB is that he is a deep-in-the-booty ass man. A true connoisseur. He delights in all things derriere. He is a rear-end reveler. An asshole afficionado.

He wants those buns, hun.

He and I talked about this in text conversations a few times before we ever did anything. Why? Well, I wanted to know the details of what all he enjoyed doing with booties (almost everything) and how we could incorporate his love of butts into our time together. Because, honestly? I’ve never spent much time developing my enjoyment of butt stuff. It’s mostly been an off-chance side note in my sex life, not a main event. To be completely transparent, I was worried that I wasn’t going to deliver to his level of assjoyment (ass+enjoyment, obviously).

Finally, we had a date night together. Now, here’s the thing, I was all ready to jump on his face and ride myself to an orgasm, enjoy some good old fashioned fucking, and, if ass stuff happened, it happened. But then, that day, three hours before our date, my period started. I knew it was coming. All the signs were there. The calendar was correct, I was draggy, and my back was stiff, and I had dropped four things while emptying the dishwasher that day (I get oddly clumsy when my period is near, no joke). So it was no surprise when I went to the bathroom and saw the writing on the wall (no, not *literally*, yeesh).

I broke the news to FWB. I was mopey about it. He, being the really excellent human that he is, assured me that he expected nothing that evening except my company. And cuddles. And nerdy TV (currently watching Vox Machina). All perfectly delightful things that I was prepared to participate in with enthusiasm.

The thing is, though, that I’m atrociously attracted to this fine fellow and I wanted to jump his bones in any way that I could that evening because, well, fuck, he makes me feel *things* and they’re very *strong* and cause a lot of *squirming* and *wet panty situations*.
So, with my period well under way but my heart set on getting some hot, sexy, naked time with this guy, I was already imagining, as I drove over there, that butt stuff was gonna be on the menu.

I’m going to fast forward you to the main course:
Arrived. Kissed. Dinner. Tv. Cuddling. Making out. Grinding on his lap. Politely demanding that he take me to his bed.

And there we were, having enjoyed stripping off our clothing (me down to my panties and him naked) and driving each other to the edge of sanity with moany, sweaty, sexy, foreplay, until I was kneeling between his legs and giving what I have been told (repeatedly) was the “best blowjob” (thankyouverymuch).

Several minutes into making him feel so good that he was talking affectionate nonsense, I asked if he wanted to cum on my ass, thinking that he’d either jerk off or rub himself over my ass however he liked so that he could finish. He was definitely eager to change positions and mount up behind me (at this point I had discarded of the panties). He slid his slick cock between my cheeks over and over while I savored that delicious feeling of being pinned to the mattress, pressed close together and in a very vulnerable pose.

I was liking the feeling so much, in fact, that I started to get a sense of excited anticipation every time the tip of his cock pressed against my asshole as he thrust forward.
So much, in fact, that I told him — a little breathlessly — that I was game if he was to try butt sex that night. He knew I had never successfully done it before, and I was very confident in both his prior experience and his wonderful, conscientious him-ness.

So he got out the lube and a towel and got to work on using his fingers around my asshole, then over, then slowly and steadily inside. There were some involuntary shivers and gasps on my part as I tried to regulate my body’s response to the very foreign feeling of a whole finger up one’s butt. But it wasn’t *only* overstimulating. It was also thrilling and extreeeemely exposed.
It made me want to be filled up by him. It made me want to feel the full thrust of his hips push his cock into me. It made me want to make every inch of me accessible to him.

He got up from the bed and pulled me with comical ease down to the foot of the bed so that my feet were on the floor and my torso remained splayed across his comforter. And with not too much effort — though very, very slowly — he fit the tip of his cock into my ass while I tried to measure my breathing and relax for him (no easy feat, I’m highly reactive to all sorts of touch).

I can’t do the feeling justice with words, but it was a mixture of my body’s natural defenses shouting “EXCUSE ME, THAT DOESN’T GO THERE” and my mind saying “Oooohhhh myyyyy” as I felt him press himself further and further into me.

And then he pulled back a little. And, let me tell you, that is a WHOLE SENSATION.
One that my body reacts to *strongly*. I know I audibly gasped and probably jumped a little. But then he was right back to pushing in and I could concentrate on relaxing again. This happened a few more times, and each time I could relax a little, tiny bit easier. All the while, my hands gripped the sheets and I writhed on his mattress with excitement and pleasure and reckless abandon. There were expletives. There was whimpering and moaning and panting. And there was a lot of very raw need to be fucked into oblivion.

He worked up to a rhythm. I was on the verge of losing my mind to the overload of information that my body was trying to process all while overflowing with the desire to give over every bit of me and completely surrender to the moment. Fuck, it was so good…

I reached down between my legs to trace circles over my clit with my fingers, coaxing an orgasm to build up while he leaned into me, his movements powerful and his breathing punctuated with grunts and groans of the spine tingling sort.
My fingers and his cock and the excitement of the entire evening pushed me over the edge and into the overwhelming embrace of a fucking *great* orgasm.

Soon after, he was asking me if he should cum in my ass.

I answered with a resounding yes.

And he did.

And it was glorious.

And that is how I ended up having anal sex for the first time.

Source: reddit.com/r/eroticliterature/comments/t99b60/how_i_had_anal_sex_for_the_first_time_fm_anal