My First Time: Anal [MF]

*Context: Based on the the DMs and questions I’ve been getting – which I fucking love by the way – I started thinking about writing a series of posts about my first times. E.g. my first blowjob, first time having sex, first threesome, etc. I can’t post things here that happened when I was under 18, so I’ll probably write those up and post them elsewhere, maybe on my Patreon.*

*(I’ve previously written about my first time with a girl, which was in college, and my first time touching a boy, which was in high school so I posted to Patreon.)*

*You know me… my name is Riley. I’m 26 years old, and a bit of a girl-next-door type. Specifically, I’m a 5’4” brunette with brown eyes, I wear my hair long, a bit past shoulder length, and I stay pretty toned with cycling classes. I’m no supermodel, but I’ve never had trouble attracting a guy (or even a girl).*

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In between my senior year of high school and college, I was dating a guy named Taran. He was tall, like 6’4”, lean, and played on the basketball team. White guy, smarter than your typical athlete, but just into having a good time.

Basically he was the perfect summer fling, and we both knew there was no chance it would continue into the college.

He ultimately went to BC and played college ball there briefly before some injury. But that’s a completely irrelevant detail.

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We were having sex throughout the summer, basically every time we could get away from our parents and families. Since I was on birth control and we were exclusive, we could skip condoms, basically skip everything except fucking like rabbits.

And we fucked a lot.

In his car, in my bedroom, in the bathroom, etc.

We were both super attracted to each other, and both horny virtually all the time.

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In the middle of July, we went to a friend’s beach house on the shore. Eight of us were staying there, and although we weren’t all coupled, everyone there was hooking up with someone else there.

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I honestly don’t remember how it came up, but as we were hanging out one night, near a bonfire on the beach, one of the girls sat with her boy and said something about sticking “it up her butt”.

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I don’t remember all of the conversation, but then Taran (my boyfriend) teased her in response, “I bet you like that don’t you?” We were all very close, so it didn’t seem weird, although looking back it definitely strikes me as a bit aggressive.

I raised an eyebrow when she said, “yeah, I do actually,” and then she rather coyly took a drink from the beer bottle she was holding.

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Now, I know this doesn’t exactly seem crazy, but we had just graduated high school, and most of us didn’t have any experience with anal.

Vaginal sex had been more than enough to keep us all, um, stimulated.

But she went on to explain that her and her boyfriend had tried to preserve her virginity for a while, and so had stuck to anal sex, you know the story.

She wasn’t Catholic, but I guess she had her reasons.

​

Taran looked up at me and seemed impressed, and we went on drinking, occasionally making references to anal and other “crazy” sex stuff.

We had been going to bed around maybe 2am, and as we started walking back from the beach to the house that night, I leaned against Taran and he put his arm around me.

We were both wearing our swim suits and t-shirts. So, he basically had trunks on and a t-shirt, and I had my bikini and top, with a t-shirt mostly for a bit of warmth.

Although we had our own room, we wound up falling on the couch in the living room, and everyone else went off to various guest rooms and other places in the house.

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Soon we were all alone, and started making out.

Making out was huge at that age, remember?

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We kissed for a long time, Taran eventually started to feel up my breasts, and grab my ass.

I straddled him, kissing him deeply and letting him grope all of my butt, letting him feel everything he wanted under my bikini bottom.

I don’t remember thinking it at the time, but given that I was literally eighteen, my ass was incredible – I was probably at “peak ass” in terms of smoothness, roundness, general juiciness.

It still is pretty damn, but it was on a whole different level then.

And based on his bulging cock, which was just centimeters and two layers of clothing from my pussy, Taran definitely appreciated my “peak ass”.

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I pulled off his shirt, exposing his lean but toned, and mostly hairless, chest. Then I pulled off my own shirt as well.

He pulled the strings at my bikini top, and in short order our bare chests were rubbing against each other.

I wanted his cock out, and moved out of his lap to get in a position so I could pull down his trunks. He lifted himself off the couch, and when I got them down, he kicked them across the floor.

We were still in the living room, but we didn’t care about anyone seeing.

Then I stood next to the couch, turning away from him to give him a full view of my ass as I pushed my bikini bottom to the floor.

I knew he could see it all – my slender thighs, the back of my pussy, my tight asshole.

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As I stood back up, and turned to face him, I again straddled him, grabbing his cock impatiently and positioning it under my pussy.

And I should mention again, Taran was tall, and his dick reflected that. He was easily 8 inches long, and thin, and at that point by far the longest I had ever had. Also circumcised and perfectly straight. Just a really beautiful, clean, white cock.

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I only hesitated a moment before sliding down on his long, straight dick, smiling broadly as I felt it fill my pussy and watched him throw his head back in pleasure.

I grinded down hard on his cock for a bit, then started riding it up and down, feeling it slide out, then rock deep back inside of me, over and over again.

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Taran was also grabbing my ass. First my hips, but then fully my ass, and I was conscious of the fingers on his right hand edging closer and closer to my asshole.

He had expressed interest in my ass before, but obviously the reference earlier in the night to anal had us both thinking the same thing.

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Soon his middle finger was right over my asshole, not pushing in, but grazing it as I rode up and down on him.

Breaking our rhythm slightly, I sat all the way down on him, feeling him deep inside me, and looked into his eyes.

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“You can do it. Try it.”

He looked at me, “Yeah? I can play with your ass a bit?”

I nodded, smiling, biting my lower lip a little bit.

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His finger pressed a bit harder against my asshole, and then he pulled his hand away, licking his finger and putting it back against my asshole, slightly better lubricated now.

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I felt the pressure, and, although it was really exciting because it was clearly something new for us, it wasn’t particularly unique, in the sense that it was basically just part of my ass.

It wasn’t like touching my clit or something, which was just electrifying the first time.

Granted, my ass was rather sensitive, but generally it was just ticklish, like when Taran touched it lightly, or it was tingly sometimes if I was building towards an orgasm.

I nodded, and I subconsciously clenched up as I felt him push his finger into my ass.

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Realizing that it would go better if I relaxed, I tried to sit back a little, and closed my eyes as I almost thought about trying to fuck his finger with my ass.

I remember this being tough, and it probably was harder both due to the lack of lube and the tightness of my virgin ass.

I took hold of his hand, raising it to my mouth, and sucked on his middle finger while I looked into his eyes.

Then I placed his hand back against my ass, and pushed down on it while trying to pull his hand into my ass at the same time. I just could tell I was going to have to be firm to make it go in. But mostly we were just awkward, and didn’t really know what we were doing.

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Still straddling him on the couch, I let go of his hand, and sat down fully on his lap, inching towards him so our bodies were against each other, and he had plenty of room to reach around and play with my ass.

I wrapped my arms around his neck, leaned against him so I was laying against his body, and put my head on his shoulder. I started kissing his neck softly.

​

He had free reign to do whatever he wanted to it.

He touched my pussy, getting some of my wetness on his finger, and then started circling my asshole with it.

I relaxed against his body, soon able to concentrate on the sensation of his finger and becoming open to it at the same time.

I also started lightly pushing out with my ass. It’s hard to explain, but I knew he could feel my asshole pulsating in and out, and that it was both a turn-on, and made it more inviting to finger.

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After a few more moments, he slid his middle finger in about an inch.

I instantly felt myself clench up around him, and focused on relaxing again.

Then I whispered, “more.”

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I could feel his heart pounding against his chest, and he started moving his finger in and out slightly, and pushing in a bit further each time.

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The rest of this might seem weird, so move on if you’re not familiar with the sensations of anal (or even if you’re just not turned on by them).

It really felt like I had to poop.

Which was kinda scary.

Looking back through “anal sex” tips, you’re supposed to practice on yourself, and with a dildo, and all the other things.

Mostly so you could get used to the feelings.

I hadn’t done any of that.

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I wasn’t really ready for this.

But I didn’t let that stop me then, and I’ve never stayed in my comfort zone since.

Plus, Taran was being surprisingly good…

Forceful but gentle, insistent but tender.

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Soon he told me that he had gone as far as he could go, and I felt the palm of his hand flat against my ass.

Interestingly, after he got in, it wasn’t too overwhelming to feel him push in deeper.

It was hot to have him deeper, but I remember being surprised that there was much sensation deep inside my ass, like there was deep inside my pussy.

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I told him to pull out – slowly! – and soon I felt my asshole close up around his exiting finger.

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I pushed off him, going from straddling him to laying down on the couch, on my stomach.

I looked back at him, “do you want to try it baby?”

Now, if you’re thinking, “But… lube!”

I hear you.

Totally.

We were young.

We did our best, and it was still hot. Even if lube is totally a necessity under normal conditions.

It worked out fine this time.

​

Taran leaned over me, rubbing his cock against my pussy, and then thrusting himself into my pussy with a moan.

He pulled his cock out of my pussy, dripping, and I didn’t really know what to do next, so I reached back behind me, grabbing both of my ass cheeks with either hand, and spreading them open, not really wide like a bad porno, but definitely enough to expose my ass and invite Taran inside.

He positioned his head against my asshole, wet with my own pussy juices, and awkwardly started to press in, holding himself above me with one arm.

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I’m not going to lie, it definitely hurt.

But not a lot. It was more just the kind of pain that brings tears to your eyes, and wakes you up.

I could definitely handle it.

And I did.

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I could feel my ass close around the head of his cock, and I could tell the thickest part was in.

It really felt very full, and the sense of him sliding further in was almost relaxing.

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When his hips met my ass, and the weight of his body was on top of me, I realized he was fully inside me and I was almost surprised.

I turned my head to the side so I could see him, and he could see me. I was no longer simply looking away trying to hide a pained facial expressions.

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He was able to kiss me, and he stayed still, deep in my ass, as our mouths opened to each other, tongues touching as we felt the deepest sense of physical intimacy.

It felt taboo, yes, and exciting.

But it also felt deeply sensual, like Taran was taking me in the most intimate way imaginable.

I still can’t imagine anything more carnal.

Anything more intense.

Anything closer.

​

He started rocking his hips slightly, clearly aware that fast movements could hurt.

At first it was just a rocking motion, not even sliding, just pulling my ass up slightly, then pushing it down.

Then he was fucking me, sliding more in and out, as I reached for his arms to grip them through the slight pain.

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There was nothing fancy. He didn’t reach underneath me and rub my clit. He didn’t choke me or slap me or anything.

It was the first time we had anal sex.

We needed nothing else.

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He warned me, “I’m getting close.”

“Okay baby. Okay.”

​

He grunted, clearly trying to control himself, but pushing his cock deep inside my ass.

Almost involuntarily, he pulled his cock out a bit, then pushed hard inside of me, pressing my body into the couch, and grunting hard while gripping my hands.

I couldn’t feel it at all. I remember that. The feeling of a man coming in my mouth or pussy is so explosive – the cum shooting into me is an almost violent, completely glorious experience. But in my ass, I’m mostly aware of the man himself.

I can’t feel the cum filling me, I can just feel the man pushing deep inside of me.

It’s hot on a different level.

Like my body has become its own vessel, that I gave to him.

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He collapsed on top of me, careful not to pull out quickly.

We lay quietly, thinking about what we had just experienced.

After a few moments, his softening penis pushed out of my ass, and I felt cum running down my thigh and leg. He went to the bathroom to clean up, and I continued laying there, feeling a swirling mix of emotions.

Euphoria. Empowerment. Excitement. And yes, continuing horniness.

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We didn’t do anal again that summer, but continued having great sex until we both left our separate ways for college.

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**The full list of my first experiences:**

[My First Time: Touching a Boy (only on Patreon due to Reddit content restrictions)](https://www.patreon.com/posts/my-first-time-23132832?utm_medium=social&utm_source=twitter&utm_campaign=postshare)

[My First Time: With a Girl (Reddit)](https://www.reddit.com/r/gonewildstories/comments/a35d00/my_first_time_with_a_girl_ff/)

[My First Time: Anal](https://www.reddit.com/user/RileyBryson/comments/a3rrqo/my_first_time_anal_mf/) (this story)

Source: reddit.com/r/gonewildstories/comments/a3s6tx/my_first_time_anal_mf