Tag: Anal

First Anal [f/m]

This one is by request ;)

This memory is a little fuzzy (it's been a long while) but as a milestone in my sexual history most of the important snapshots are still there.

It was the summer between sophomore and junior year. (NOTE – seriously, all my BEST stories seem to take place during summer, I should wear a chastity bathing suit). I was 16 and newly single. My ex-boyfriend and I had a typical, tumultuous teenage relationship (that would go on/off again for the next 7 years or so, far too long). My friend and I went to a summer festival concert and ran into one of my ex's best friends, Benji (not his real name). Ben had just graduated and was headed off to an Ivy League school for college. He was already a cocky motherfucker but the Ivy League prestige definitely put a new spring in his step. As did his newly pierced tongue. Read more »

Staying Out [MM][Anal]

Click on my name for the previous stories in this series Feeling His Way Through and Mark Figures It Out

"Hey, Tad, you gotta minute?" Paige asked before the first bell rang.

"Sure, Paige, what's up?" Tad absently touched his bruised lip as he stopped. Their schoolmates routed around the two of them to create an oasis in the crowded hallway.

Paige's impromptu baby shower on Friday during lunch in the school cafeteria indirectly led to her ex-boyfriend and reluctant baby-daddy to give Tad a fat lip. It wasn't swollen anymore after three days, but the mottled skin still bore the clear imprint of Charlie Johnson's knuckles.

"I wanted to apologize for what happened Friday," she said, not quite meeting his eyes.

"That's not on you," Tad said with a dismissive wave. "You only went out with him. You didn't make him hit me."

"No, but I spun him up on purpose and knew he was unstable. If I hadn't done that he might not have hurt you." She gave him the kind of stern look that implied how seriously she took her apology. Read more »

My fuck buddy and I (21F/30M) just had the best sex we’ve ever had: oral, anal, and crazy squirting

I (21F) have been seeing my fuck buddy (30M) off and on for a couple of years now. We are pretty adventurous, enthusiastic about fucking each other, and insanely sexually compatible. Tonight we had some of the best sex we've ever had, which is saying something, and I wanted to share it.

It started with me coming over to his place just as it was getting dark. We'd been looking forward to meeting for a week, and had already discussed some dirty things we wanted to try. He had pot this time which is wonderful because we are both extra horny when we're high.

We took off our clothes and I watched a porn he already had on in his living room while I smoked a bowl and he ate my pussy and asshole eagerly. For probably 15 minutes I let him eat me and get me soaking wet. In between bowls we changed positions a few times. I sucked his cock and made him moan in a way I didn't even know I was capable of. I rode him for a while, cowgirl and reverse cowgirl, getting us so worked up I drenched his cock in my juices alone. Read more »

Fro[m] hook-up to personal [f]uck toy

Not a native English speaker but this isn't Shakespeare so what the hell. Also, I suck at formatting.

A few weeks ago I met this girl on OKC. She was married but looking for a side gig since her hubby was regularly seeing other women, too and it seemed like she wanted to do some catching up. We hit it off pretty well and while we kept most of our privates lifes to ourselves, we quickly seemed to click on a sexual level and talked/sexted in explicit detail about how our first encounter should look. We met shortly thereafter and had hours of amazing, very rewarding sex but at that point I had no idea how much better things were going to get. Read more »

Worst prostitute ever! [m/f]

He didn't actually use that phrase but he strongly implied it.

Let's call him Kevin. Kevin had been a regular of the escort agency I worked for, long before I arrived and years after I left both the agency and the glamorous world of prostitution, I'm guessing he still is.

The woman that ran the agency loved him. It wasn't just because he was a frequent customer and the amount of money he pumped into the agency, I think it was because he fulfilled her expectation on every level of what her ideal customer would be like.

He was fat (pudgy rather than obese) balding and his 50’s, every woman’s dream, and he just wanted to be our friend. He also wanted to fuck us in the arse and urinate on us, though he was still a good bloke apparently!.

From before we joined the agency we were told we had to provide all the services the agency offered. So while a woman at another agency might not want to offer say, anal sex and her agency might work around it, our agency wouldn’t. In fairness when they were always up front about it. In practice how it worked was that your first time with a new client, if he asked for something like anal, you’d say not now, but once we’ve had a few bookings we’ll do it then. Read more »

Licking and pegging my adorable partner [MF][peg][anal][Fdom][Msub]

(Okay, so this is my first pervy post of any kind. Please be gentle, I just get these drawn-out fantasies and writing them down is the only way for me to get them out of my head. Might as well share them here.)

 

The view from our balcony at night is one I never truly tire of; the sight of the moonlight on the calm, blue sheet below is so very calming. Out here, the distant noises of cars and gulls are audible over the quiet sound of the shower running in the bathroom. The cool breeze blows the long, dark hair back from my face and flows over my bare legs. I stand still and enjoy the smell of the sea until the spray of cascading water in the background suddenly stops and I hear the shower curtain sliding open.

  Read more »

I Bully and Humiliate My Obnoxious and Hot Roommate via an Unwanted Spanking While Everyone Laughs. [spanking] [mmf] [huml] [nc] [Mdom]

[This is a work of fiction but may bring to mind what actually happens sometimes all around the world e.g. in India (often in far more extreme form) so girl-tourists should use caution in India. Nobody herein described is meant to resemble any real person alive or dead. This text is not to be construed as a guide to appropriate behavior and condemns gender-violence of any kind. It's possible that the reader will get off to this. If he does not, he may get off pondering its moral message. Trigger Warning: hipsters, contempt, ACAB.]

Two policemen rode together in a police-car to what they thought was a crackhouse but was in fact your law-abiding, sovereign home. Due to a minor error in transcription, they'd been given the wrong address. As they drove, one policeman ranted the following to his partner shortly before bursting through your front door and killing you and your whole family. Read more »

Lodge Adventures: Part 3 [Ff/mmm]

This is the last installment of my series about a pretty debauched spring break I had my senior year of college. This is my last story from this week, but I'll probably be sharing some more from the rest of my life soon!

Part 1

Part 2

The final night before we leaving the cabin was kind of a bacchanal, everything was packed except only what we needed for the night and a mountain of booze. We had rationed out our alcohol pretty well (even though we’d brought an incredible amount to begin with) and we were trying to finish off everything so we wouldn’t have to haul it back into town with us. This resulted in what I’m pretty sure was one of the craziest nights in the lives of most of the people there. The night started out in an incredibly liberated atmosphere where half the people there had fucked the other half before that moment, and it was amazing the whole thing didn’t actually just turn into a massive orgy, instead of only bordering on one. Read more »

Repost (previously Lost): Becoming a Bit of a Whore By u/engineeringgirl

In high school no boys ever noticed me. I was too busy to have a boyfriend. Always studying. Going to after school activities. Anything to get into a good college. The boys only wanted the pretty girls. The cheerleaders. When I got to college everything changed. In one class, my engineering class, I was one of only 5 girls. Soon 3 dropped out. Suddenly I was the center of attention. Everyone wanted me to join their study groups. These 3 cute guys always sat next to me. From the beginning. I also had Math and Physics with them. So we always sat together. Two of them were roommates. The third was next door. My room was one floor up. We hung out a lot together.

Their names were James, Tom and Ken. I had a lot of firsts with them. It was fun hanging out with guys. I barely had any guy friends in high school. One night while drinking (also a first), the topic of sex came up. I told them I wasn’t interested in a boyfriend. I was focused on school. Tom, who is also asian, agreed. Ken and James did not. We talked about sex. I admitted I was a virgin. So were Tom and James. Ken had a girlfriend in high school. They asked if I was interested in losing my virginity. I said of course. I jokingly asked if they were volunteering. They quickly said yes. I brushed it off as the alcohol talking. There was an awkward pause after that. Someone quickly changed the subject. Read more »