Anal Archives — Page 785 of 957 — NSFW story

[MFF] My first girlfriend constantly tested me.

I’m going to preface this by saying that this was one of the more strange sexual encounters I’ve had in my life.

I lost my virginity to a girl that I have known practically my entire life. We went to the same school from first to eighth grade, and then went to the same high school together. Despite the fact, I was never really close with her until my senior year. In all honesty, I had always thought she was kind of annoying. She was the artsy type, not that there’s necessarily a problem with that, but she was always very pompous about it. She acted very snobbish and cultured, and constantly critiqued and attacked people for their taste in music, movies, and books.

I first got to know her on a personal level when there were only two or three months left in my senior year of high school. I was paired with her and some other people to work on a project. I really wasn’t looking forward to it, namely because I was paired with her, and the other people I was paired with were burnouts who didn’t do shit. We quickly came to this realization, and agreed to work on it together. Read more »

The Hole [MM] [anal] [blowjob] [used]

The belt started to irritate my wrist, but I couldn’t care less. I’ve been tied here for forty minutes already, and not even one caressing hand have found me. It was my first time in a dungeon like this. Tied up to a desk, with your lower half sticking out into the publicly accessible place. Decent pay. Not that I cared. The thrill of being used was enough. I never had a boyfriend, but my fantasies were getting out of control, and even though I was red as the Soviet flag when I arrived here, I quickly realized that the customers will not see my face.
But it’s been forty minutes. At least. Is my butt too ugly? I waxed the important areas. It’s not that there are no customers; five minutes after opening the first arrived and there has been constant moans since. There were twelve of us in service. A couple of my colleagues were in the same position in me; some were on the other side of a gloryhole. The “luckiest” were also on another side of two gloryholes, but not as receivers. Read more »

Confession – fmff, bondage, spanking, dub/con, queening, oral, anal, etc etc

Click, Click, Click, Click, the sound of her heels echoing through the empty church, the noise felt like thunder to her as she walked down the aisle towards the alter. Stopping momentarily she knelt, bowing her head slightly before crossing herself and turning towards the confessional. She walked in and pulled the curtain closed behind her before seating herself on the wooden bench and crossing her stocking clad leg. After a moment of waiting she heard the shutter slide open and became aware of the silhouette of the priests face through the screen.

It had been a while since she had attended the confession and she had to search for the words. “Forgive me father it has been some time since my last confession. “ she started out. As far as the church was concerned her list of sins was considerable, and she thought for a moment where to begin. A wicked grin crossed her face then as she formed the words and began to outline her sins. As she started listing them she could imagine the priest slowly getting outraged as her “indecency”. She put a sultry lilt into her voice trying to tease him “oral sex, anal sex, lesbian sex” she was goading him, trying to get a reaction. She could hear him breathing deeply as she listed them. Read more »

The Milking [Milking][Femdom][Bondage][Forced Orgasm][Anal Play][Nipple Play][Edging]

Your balls ache. It has been so so long since you have seen her and you shift uncomfortably in your seat. The sounds in the boardroom echos past your ears, nothing sinks in and you just can’t concentrate. Your cock twitches and your mind races as you imagine her beautiful face. That black, thick eyeliner, the long lashes, the dark lips smirking at you. You shift again in your chair and feel the eyes of the other board members on you as sweat starts to bead on your forehead.

Your mind wanders and before you know it the other board members are filing out of the room while you sit, pained and desperate in your leather arm chair. You tap your papers on the desk and place them gingerly in your briefcase, trying to stall until your inappropriately timed erection calms down. When all the other men are gone you eagerly pull your phone out of the pocket of your blazer. You know her number off by heart now, obsessed with her and what she does to you. You tap rapidly at your screen, hoping and praying that she will respond quickly. Read more »

The Milking [Milking][Femdom][Bondage][Forced Orgasm][Anal Play][Nipple Play][Edging]

Your balls ache. It has been so so long since you have seen her and you shift uncomfortably in your seat. The sounds in the boardroom echos past your ears, nothing sinks in and you just can’t concentrate. Your cock twitches and your mind races as you imagine her beautiful face. That black, thick eyeliner, the long lashes, the dark lips smirking at you. You shift again in your chair and feel the eyes of the other board members on you as sweat starts to bead on your forehead.

Your mind wanders and before you know it the other board members are filing out of the room while you sit, pained and desperate in your leather arm chair. You tap your papers on the desk and place them gingerly in your briefcase, trying to stall until your inappropriately timed erection calms down. When all the other men are gone you eagerly pull your phone out of the pocket of your blazer. You know her number off by heart now, obsessed with her and what she does to you. You tap rapidly at your screen, hoping and praying that she will respond quickly. Read more »

It happened again, even [M]ore [F]ilthy talk during anal sex

[First story here](https://www.reddit.com/r/gonewildstories/comments/8i3e5y/i_am_a_big_fan_of_anal_sex_and_dirty_talk_and_my/)

Well, turns out she’s into it for my sake. I’ll cut right too it.

We were getting down, I was massaging her back and resting my bulge against her butt. It feels so good to have her squirm underneath me while she’s moaning as I rub out her tension.

Eventually we work into missionary from there. I’m kissing her neck, and slowly playing with her clit. She’s terrible with foreplay, and demands I put my cock in her. I place the head against her opening and it slips right into her warmth. A soft moan, a head tilt and eyes clenched in that beautiful agony.

We fuck like this for 10 minutes, but again, she tightens too much and with every thrust she begins to push me out. I move her towards the end of our bed, and she bends over. Sometimes doing it doggy will work!

I place my cock inside her again, but after what feels like just 30 seconds I hear and feel that pop of my cock as it’s pushed out of her. Defeated, I’m prepared to settle for shooting it on her ass, when she surprises me Read more »

My first prostate orgasm [MM]

I’m bi and specifically a total bottom but I wasn’t always this way. In high school I was always curious, or maybe always horny. It wasn’t until my freshman year in college that I started messing with guys. My first couple of times were awkward to say the least. I thought since I enjoyed fucking girls so much that I’d enjoy fucking guys too. Boy was I wrong, not only was I disgusted with topping a guy but I a lot of these guys were total stiffs (pun intended) in bed. I decided I try to bottom, at first I couldn’t fit anything past the tip because it hurt like hell. I finally read up on how to properly prepare and relax for anal sex. In no time I was seeking out the biggest dicks I could find (poppers helped with this) after a year or two of taking dick regularly I had never experienced the elusive prostate orgasm. Read more »

[MF] Blackmail fantasy becomes reality

This happened a few months ago. One day I got a text from an unexpected person, Jon. A little background, Jon is our neighbor’s son who is a senior in highschool. He is also a soccer hot shot we’ve heard. He is 6’1 and has the typical soccer body. He has blonde hair and green-ish eyes. Before this incident, his parents gave his number to me to check in on him as his parents went on a two week vacation. Also I kind of knew he had a crush on me and told Kyle to which Kyle responded and said “Who doesn’t have a crush on you?!”

So, I was surprised he texted out of the blue. I thought he needed something so I quickly opened the message and saw a video then looked further down and saw ‘;), stop by after 5’. I then played the video and saw what looked like a girl, whose hands were tied above her head. She was fully exposed and was being fucked, then I realized that girl was me. I was completely shocked! I sat there on my couch and weighed my options. I could tell his parents, tell Kyle, talk Jon out of what he probably wanted but then something inside me tingled. I always had a blackmail fantasy and this would be easy to explain to Kyle. It sounded like a really stupid reason. I decided to wear a regular shirt but put on low cut short-jeans. I also thought hard about wearing a bra but decided against it. Read more »

Fist of Legend [MF][ANAL][LIGHT WS][FIST]

For our birthdays, which are two days apart, my wife and I decided to have a sort of sex fest. We were staying with a friend for a week at the time because our house was getting the hardwood flooring re-done. Cassie was a bartender in the city and usually didn’t get home till about 3 in the morning.

The plan was, a freezing bottle of vodka with a couple of shot glasses, lots of candles, a couple dildos and a bottle of J-lube. If you’ve never used this stuff before you have to try it. It comes as a powder in a big bottle. You mix a couple teaspoons with half a cup of water and voila. This stuff was invented to assist in the birth of horses.

We anticipated a big mess so we decided to restrict our activities to the confines of our friend’s master bath, which was basically tile everywhere and a large walk-in shower. Read more »