Anal Archives — Page 938 of 957 — NSFW story

First Time [anal] [mf]

Background:

I have been obsessed with anal for as long as I can remember. The first porn I ever watched with anal was a VHS copy of "Debbie does dallas" that I snuck from my dad's stash when I was about 14, I was blown away (pun intended). I'd say about 90% of the porn I watch is anal related and although I do enjoy vaginal sex I fucking love anal! It's so hot and dirty that I just can't help myself.

Here is my story:

My girlfriend and I were teenagers when we lost our virginity to each other after being together for about 5 months. With the milestone of our virginity gone I was eager to take things to the next step and finally try anal. Problem was I really didn't know how to approach it. We really never spoke about it except in passing one day but really discussing other people, regardless of who we were talking about the sheer thought about discussing it was a massive turn on. I didn't even speak openly about it with my close friends and it felt a bit like too taboo and a hidden desire. Read more »

[F/18] – Family Vacation: How I hooked up with my step-brother in the hotel room

We just came back from a weeks vacation in California, and I'm still shaking every time I think of what transpired. Let me give you all a few visuals and background. I'm 18, my step-brother 19, and my dad has been married to his mom for 7 years. Basically, I've known him a good chunk of my life. He's very attractive. A little over 6 feet tall, lean but a little muscular, dirty blonde hair, and perfect blue eyes. If you're wondering about me… I'm 5"4, brown hair, brown eyes, kind of pale, skinny, and most guys would call me either average or a little above average probably. Nothing super crazy. Also, nothing at all has ever happened sexually between us up until this vacation. Not even flirting or hints. Read more »

Mark Figures It Out [MM][Anal]

The throbbing beat of the subwoofers made the gin and tonic in Toby's glass quiver in time with the music. He sipped again as his eyes scanned the room for fresh meat. The new semester always brought in guys looking to find out if that twitch they got glancing around the communal showers in high school meant something. And Toby considered himself the best person to answer all their questions.

One guy caught his eye because of the timid way he approached the bar. He was in good shape judging from the way his tight jeans and UCF soccer jersey outlined his muscles. Toby stepped closer before anyone else could and leaned against the bar next to him without getting too close. He drained his gin and tonic and put the glass down hard.

"Boris! Can I get another gin and tonic?" Boris the bartender was only wearing a bow tie and tight leather pants. Despite his cut, muscular body he was currently off the market dating the owner. Such a pity.

"Can I get a bud?" The soccer jersey guy asked.

"You have to ask louder than than," Toby said as he leaned closer, then turned to face the bartender again. "Hey Boris! Add a bud to my tab." Read more »

Introducing the innocent girl to anal [m/f]

Over the last week or so I've had a great time writing about my time dating this sexually repressed woman and how insanely hot it was to break down her sexual barriers one by one. I'm sad to say I'm just about out of stories about her… but this final (or maybe penultimate) installment might be my favorite one yet. If you want to read the rest of the stories for some background, here they are:

Making her beg / Making her squirt / Eating her out

We'd been dating for ballpark five months, and the sex continued to be phenomenal. I kept pushing the boundaries, she kept resisting and eventually caving in. I came to realize that she loved the process of being corrupted as much as I loved being the corrupter– she was a sub to her core and came the hardest when she was being "forced" to do something that she felt was degrading or wrong. The hottest part was how she'd always end up begging for it– watching this nice Catholic girl implore me to choke her, to call her a whore, to make her squirt– those times remain some of the hottest memories of my life. Read more »

My unexpected threesome

If you've read my first post, you'll know that last summer I experimented with my sexuality. About a month after my first hookup with a guy, I was back on grindr and looking for more.

After about a half hour of pointless conversations, I wound up talking to two separate profiles who later told me that they were partners and both wanted me to come over. I talked to one of them a bit longer (just made it easier to discuss instead of going back and forth) and he told me that one of them was more a top and one more a bottom. I had been wanting to try bottoming ever since I began to play with my own prostate.

I headed over to their house – a pretty nice place. It creeped me out that they had some sort of security cam set up with monitors, but I thought nothing of it. Their bedroom was tiny and barely fit a bed and a tv inside, but on that tv was some really hot gay porn. Read more »

A Plasticised Doll’s Story [MF] [sci-fi][anal][drugs][nc][prost]

I guess my story started out like so many other girls who disappeared on the streets. After being kicked out by my parents I started selling my body for drug money on the street corner down-town. That was when I met up with Steve. He took me off the streets and gave me a drugs, lots of drugs, so much I didn't realize what he was doing. As I learned later he bombed my system with growth hormones and estrogen, my already ample breasts exploded in size, my pussy became engorged. He also starved me at the same time, feeding me laxatives and emptying out my stomach.

Why was I chosen? Apparently a rich mobster had taken a liking to fucking me and wanted me 'done up' for him. I remembered him, he loved doggy style and liked ramming my ass then my cunt in that order…. not healthy for me but for drug money I would do anything.

Anyways, drugged out of my mind I remember them strapping me to some weird table with me on my hands and knees, with my legs spread apart and my ass pointing up. I thought I was just going to be fucked like in some kinky scene.. how wrong I was. Read more »

Nympho Cu[m]slut Girl[F]riend RETURNS!

I've written about my ex-girlfriend Kerry before, but now I have a fresh story to tell! I haven't spoken to her in about 10 years. We dated on and off (mostly on. . .) for about 7 years starting in HS and through college, and then had a FWB/booty call relationship while being best friends for years after college. However, at that point, I had missed my chance to marry her and knew we were never really going to get back together as a couple, so when I met my now wife and started dating her, I had to break things off with Kerry. It was too hard to be so close but not together and it worked out better for both of us to get some space, so we could find our spouse or even be open to a long-term relationship. So I said my peace to her and cut off communication and haven't looked back (other than remembering/fantasizing about some of the crazy things we did to/with each other).

The other day, I went on Facebook to check out my feed and noticed that there was a message in my inbox. I clicked over to the inbox and a message from Kerry was waiting. Her message was short and quick: Read more »

Sins, Shadows, and Soju Bombs [Threesome][MMF][DP][Interracial][Superheroes][Creampie][Post-orgasm torture][power play]

A short story I wrote using original characters created by Silenced Nocturne, a friend of mine, and one of her friends. She also did a lot of heavy editing in the story, keeping things in character, adding details I'd forgotten, and generally improving the story. She's awesome, check out her works at the link above!

As always, comments and constructive criticism are not only appreciated, but welcomed.

Sin sighed and pinched the bridge of his nose. “So, that went well.”

Ji chuckled. “As well it could have, anyway. I didn’t think they’d kill you, you’re doing too well in London for that. But in the event they decided that you’d screwed up, well…You know what they’d do to you. Getting demoted wouldn’t be so bad compared to that, Sin Ji-Hoon.” The short gangster strode to the refrigerator, opened it, and cracked open a bottle of hangover cure. He downed the entire glass in seconds.

Sin grimaced. “That stuff is disgusting.”

Ji choked, then grinned cheekily. “And that’s why you have hangovers. I’ll take Morning Care over a migraine any day.” He flung the bottle at the trash can, knocking it over. He knelt to pick it up, nodding to himself. Read more »

Double Headed Dildo Drama (Follow-up to the Alyssa story) [m/f]

So after that one night with Alyssa things pretty much went back to normal. Neither of us mentioned what happened, and if she seemed to ignore me a little more than before in social settings no one really noticed. I just figured that in the clear, sober light of day she realized what happened and thought it was a mistake. And while I felt a bit dejected, I couldn't really blame her. I guess when you've been facialized by a friend you've never really had feelings for, you can feel a bit awkward about social interactions with them.

But did she have feelings for me? Besides drunk and horny? Was there a reason she called me, or was I just available? Was it interest or luck?

I spent about a week with these thought churning through my head. It felt like high school awkwardness all over again. But after a little while, and no signs from Alyssa whatsoever, I was able to just chalk it up as a fun experience and a small boost to my ridiculously small self confidence.

Then a few months later, she called me again. Read more »