This girl Stacey was in my algebra class freshman year of college. I sat right beside her and used to try to flirt with her and get her to give me answers. She always acted kind of shy about it, but seemed kind of into it. It made it feel like a challenge to me, so I kept on throughout the semester. I would always ask her at the end of class when she was going to let me take her out to dinner. She would just laugh and say, “Not sure. I’ll think about it” while she smiled and blushed. Finally one day towards the end of the semester when I asked her she said, “okay, you can take me out on Friday.” I was so used to her saying no that I did a double take when she said yes.
Tag: Anal
21F two nights ago
long story short, ive had a lot of questions about it since i posted on dirtypenpals so im assuming people would like to hear the full story, so i found this subreddit! :)
I had my very first threesome on thursday night and it actually came about because of a pretty poor joke aha basically i was out with my boyfriend (student nights here are on wednesday and thursday) and he told me that he wanted to fuck me when we got in, then cum in my mouth. I responded with the amazing line "the only way youre gonna put it in my mouth after sex tonight is if it's because someone else is still fucking me" now believe me, this was not meant as an invitation but he just looked at me and said completely straight-faced, "okay, lets get someone."
it was actually pretty hot in a weird way, dancing with my boyfriend but being actively encouraged to look at other guys and find one for us to talk to aha
Feelin’ His Way Through 3 [MM][anal]
Click on my username to see the first two parts of this story.
Tad bounced into the kitchen to find his Mom sitting at the breakfast table with her cup of coffee and a dreamy look on her face. He was wearing his sweats and running shoes, ready to leave the house as soon as he could without making her suspicious.
Mark had been gone by the time he'd cleaned the puke out of the trashcan at the side of the house. The stench of bourbon and pizza would have raised too many questions with his mom and he didn't want to talk about what happened. Not yet, anyway. He'd taken a long shower after cleaning up and resolved to stop dreaming about being with Mark. It had been a mistake, but he had learned something from the experience; he wanted more. And that meant coming out about who he was.
"Looks like you had a good date," Tad asked with a wide, forced smile.
"He was very nice," Mom said. "Where's Mark? I figured you two would be sleeping off a pizza and video game hangover."
Cynthia’s beginning part 2 – M/f – d/s
I want to inventory each step along the path. But, to be fair, it was a slow one at first. Each day seemed to add a new small step of perversion and sexual discovery for Cynthia. It would take too long to detail it all.
We moved very slowly. Tieing her legs and her hands. Having her beg to cum. Having her call me sir. For the most part it was all the same though. I’d tie her up on the bed and fuck her. We added layers each time. This time I spanked her as we fucked. This time she begged to cum. This time I threatened to fuck her ass. This time I tied her kneeling and that time laying. Hands up, hands down, etc. Then we started to incorporate pain. A bit of spanking. Nipple biting. Some smacks to the face.
The first night I spanked her, we were both taken back by how much she loved it. We were naked. Her across my knee. I demanded she count each spank and by 20 she was begging me to fuck her. Begging to have my cock inside her. I made her wait to 50. She came so hard I thought she would pass out.
My Affair: The First Broken Rule [M/F]
This is the third in a series. You can read the first two parts here and here.
My wife and I had been at the club for a little over 30 minutes. It was still relatively early on a Saturday night and there were just a few people there with us. More friends would be arriving soon, but only one was truly on my mind. Rachel would be here any moment and my heart was pounding.
It would be the first time we’d seen each other in public with our significant others since we began our affair. She was nervous, too, and had been texting me all day. On one hand, we were both aroused at the thought of having to pretend there was nothing going on; that we hadn’t been intimate; that we hadn’t already broken our first rule. On the other, we both knew the danger if anyone found out.
Over the last five weeks, we had settled into something of a routine. Everything seemed to be going as planned, but looking back now I can see that escalations in our behavior started almost immediately. We weren’t breaking rules, but we were pushing the boundaries almost from the start.
[F/M] my first weekend at college, experimenting with anal
It was my first weekend of college, and my new roommates and I had gone to frat row to experience our first real college party. Almost as soon as we walked in one of my friends started flirting with some guy, who introduced me to his brother, Jordan. Jordan was about 6 feet tall, stocky, with a little bit of scrufflong, dirty blonde hair and an extremely sexy accent. I guess I should mention what I look like as well, I'm about 5'6, 140 lbs, with D cup boobs that are just big enough to make up for the extra weight I'm carrying around my waist. I've got short red hair, and the pale skin and freckles to match.
Good Christian girls wait until marriage…but I’ll take it in the bu[m] [f]or you
I was really good friends with Laura all throughout middle school and high school. We ended up going to the same college together across the country and became even closer. She was a pretty religious girl and hung out with pretty religious friends who I ended up getting decently close with.
Her room mate sophomore year was this gorgeous blonde named Melanie. Mel was about 5'4" C cup breasts and a thin yet remarkably curvy figure. She was rather flirty and whenever I would come by their apartment she would flirt heavily with me. I had always thought she was joking because she was dating one of the biggest guys on the football team. So, naturally I assumed it was with everyone. One more thing about Mel…She was kind of bitchy. She looked down on a lot of people and had a certain air about her. The kind of "I'm a hot Christian girl that will tease you until you beg…then do nothing because I'm saving myself" air about her.
[MF] My anal birthday present
I'm going to be describing one of the hottest experiences of my life. But first, let me give a little backstory.
I met Sarah towards the beginning of the school year while orientation was still going on. The attraction between us was instant. Sarah was super adventurous as well as gorgeous. She was tall, had gorgeous tan skin with faint tanlines where her bathing suit had been, dirty blonde hair, and had an ass to kill for. It was that perfect athletic shape (closest example I can think of is Jessica Biel) and I worshipped that ass. As a rower for our school, she was probably one of the strongest girls I've ever met, but damn was she hot.
Since we were both adventurous we always did fun things like camping on the beach on school nights, driving down the coast with her chilling out of the sunroof, blaring Paul Simon. It was definitely a playful kind of love. Additionally, the sexual tension between us was insanely high. While sitting on the beach and looking at the sunset, she would sit on my lap and I'd feel myself getting hard as she would shift and slide around on my lap. When she would notice the bulge down there, resting between her cheeks, her face would get flushed and she would crack a little embarrassed smile. She hadn't been with any guys yet, and since she was brought up in a relatively religious household, she had to suppress her sexual desires most of her life. I was ecstatic to be the release valve for those desires.
A walk in the park [F/M]
This is from last summer. There was this girl, with whom we had a kind of a BDSM relationship thing going (Dominant/submissive).
So one night, at quite a late time, we went to the park. It was really quiet, but still the thought of getting caught was exciting. I stripped her naked and tied her on a tree, her back facing me at first. I had the whip I usually used with me, but I thought it would be better to just spank her using a branch. We were both overachievers and it seemed a good idea haha. So, I started spanking (or whipping?) her with a branch, while she counted every blow, thanking me after each one. If she would make a mistake, I would start all over. She did make some mistakes so the total count was a lot! After I was done, her ass and back were red and stinging in the most pleasurable way. Pain was never an issue with her
After that, I untied her, got her on her knees and tied her hands on the tree, above her head. I also tied her torso, so that she could not move. Which led to oral play. Of course, during all that verbal humiliation was happening.
My Affair: The Beginning
I’ve known Rachel for quite some time. We met via a group of social media enthusiasts back in 2007 when Tweet-Ups were still a thing. She and my wife hit it off pretty well and soon we were hanging out with Rachel and her husband quite a bit. They’re about our age, a little younger. Rachel is a grad student. Her husband works in IT. She’s very cute, in fact she looks a bit like my ex-girlfriend Laura (see my previous stories for some info on her).
Rachel has smaller breasts, but they’re perkier than Laura’s. Her skin is pale, her hair a lighter brown and her eyes a wistful blue. She’s not as curvy through the hips, but her legs are longer.
She’s one of those people who has very little in the way of a filter on her brain. No subject is taboo. She talks openly about just about everything from her bathroom habits to how many times she’s been caught masturbating by her parents, her brothers, her college roommates and a neighbor. I find it refreshing. My wife, on the other hand, isn’t quite so open. She thinks Rachel is a little weird. She likes her, but sometimes the conversations make her blush.