Tag: Group

[T]he roommate situation. One trans girl living with two straight males, a story about a group of friends who cave into cheap sexual urges and keep shameful secrets from everybody else they know.

Soooo, I’m a 23-year-old trans girl, completely passable, often told I’m cute, am often hit on by guys who are surprised when I tell them what’s up. If you want to know more about me including some pics I’ve posted, check out my post history! I’ve only been sexually active with guys for about a year now, but it’s been a hell of a year. (A story about my first time is also in my post history).

Recently, I moved in with a couple of straight male roommates. One of my roomies I’ve known for years and consider a good friend (we’ll call him Adam), the other is a friend of his who I didn’t know all that well until more recently (we’ll call him Jeromy).

To preface this, I knew for sure Adam wasn’t into me sexually and after hanging out with Jeromy a few times, I didn’t get that vibe from him either (or I never would have moved in, I don’t need that kind of drama in my life.) So when they offered me a chance to move into a new vacancy at their really nice house for really cheap, I jumped on it! Read more »

Babysitter loses her virginity [mast] [str8 fM] [throat fuck] [virgin] [multiple orgasm]

I was nearing the end of high school and had just turned 18. I was still a virgin, mostly by choice. None of the guys in my year group ever interested me. Maybe it was because I had grown up with them and they all still seemed to be quite immature. I would never openly admit it, but I knew that I was pretty. I was 5ft 4 and 120 lbs, had long wavy brown hair to match my light brown eyes, I was slim with a perky butt and perfect C cup boobs. Boys were always chasing after me, trying to be the first to enter my pussy. I liked the attention, but my gaze was always directed towards older men… like the man that I babysat for.

Mr Pearce was a single father in his 40’s but looked much younger than his age. He had dark hair cut short around the back and sides, but he liked to leave it a little messy on the top. His skin was a dark tan which outlined his muscles perfectly. He liked to keep himself in shape, I knew this because of the indoor gym at his house. His eyes were blue like the deep sea… easy to get lost in. His face was very chiselled with high cheekbones and a strong brow, he always kept a five o’clock shadow. He was a very handsome man and I always struggled to keep my eyes off of him. Read more »

[MF] I learned a lot about wife on New Year’s Eve.

Never knew this had happened until almost exactly a month ago. You’ll have to learn what I learned about my own wife by reading further. Even though I’m passing along the story second hand (with permission), there is enough detail that you won’t regret it.

We’re playing games at the house of a sorority sister of my wife. I don’t remember the name, but it is a sort of truth-or-dare type knockoff of Cards Against Humanity. During one round, I “guess” wrong on how my wife would answer a question on one of the cards. Much to my surprise, she answer “yes” to “Have you ever had sex in public?”

I was stunned. Honestly, even a little hurt. I’d actually asked her that question once or twice over the years. I think I’d always asked something more like, “Have you had sex in front of other people?” But, the answer was always no.

She was a sex craved lunatic in college, and I knew that. I just figured that was something that just hadn’t happened, despite some other stories that I’ve been told (and even a few things I witnessed myself before we started dating) that sometimes make me wonder why that slut doesn’t make more appearances these days. Read more »

Math grad student is surprisingly experienced [FM]

(set in the early 2000s, before hooking up apps existed, and chat rooms were all the rage)

Ashley really didn’t like this conversation. She was sitting in a local college bar with the other math grad and doctoral students from the university. Even though there was a much bigger city nearby that most of the students from her school would go to so they could revel with the students from the much larger university located there, the bar was packed. They were towards the back of the bar; the noise was loud but not deafening.

Ashley wouldn’t normally come out drinking, but midterms had just finished, and she had a particularly hard one in Partial Differential Equations. God that class was hard, like rethink getting a PhD in mathematics hard. She agreed to join them and had ordered a girly drink, but now she regretted coming.

“Seven” said Miranda with a chuckle, her large breasts shook to join her large tummy. “Another prime number!” responded Ethan, he had said five. They were all past tipsy, but not quite drunk. “Wooo” said Mark, high fiving Ethan. Mark had been the only broken double digits with eleven, another prime. That made sense, Mark was really hot, especially for someone involved in math. Ashley had answered “x” when asked and when probed confessed “x is greater than 0”. She really didn’t want to say it was actually one. Read more »

The events when the girl lost my card to ropes me into 4 girls [group]

So I’m 23. I invited the girl I lost my v-card during teenage mutant ninja turtles in 2014 on a family vacation. From there have worked extremely hard in college and landed an amazing tech job. A certain city shooting occurs and we reconnect. I invite the girl to my holiday party in San Francisco. Have an amazing time. Completely forgetting about Santacon being the next day. Luckily have my hometown/college friends throwing party/pregame. God damn college friends visiting the city. See my frat half amazing catch up with and the ladder wack. Mostly 30 people I know from dorms are dropping in from battle ubers. Its 1p.m. Some people are operating at the brain capacity of a toaster.

Booze go down hard, fucked up comments come up.

Run into my great snowboard sender bro. Introduce my girl to his and from there she meets this girl… Read more »

Teacher Teacher[FM][oral][cheating]

Ray stood in the corner of the room, a beer in his hand and a smile on his face. The party was going great, and everyone seemed to be a lot of fun. Ray’s roommate, Bobby, had invited him, and though he was nervous about not knowing anybody, he was glad that he had decided to come. There were a lot of men at the house party, but a few women were hanging out on the patio as well. The people seemed friendly and talkative, and Bobby introduced him to a few people so that he could get in on the conversations and mingle a bit.

Bobby had moved in to Ray’s apartment a few months earlier, and was a perfectly considerate roommate. They got along well, and after about a month, Bobby had revealed to Ray that he was gay. Ray didn’t have any problem with this, of course, though he considered himself completely straight. He was comfortable enough after this amount of time that going to a private house party with him felt like it could be fun. When they arrived, he noticed there was dancing in the middle of the living room. There seemed to be a lot of men dancing, and only a few girls sort of in the middle of the group. He wondered if all of the men were trying to get close to the women, and though he enjoyed dancing, he didn’t want to crowd the ladies and make them more uncomfortable. Read more »

Into The Miasma

Afternoon. It was somehow afternoon already, and Helena had been out here since morning, nervously pacing around the front of the shop. It’s not that she was timid or anxious, on the contrary, she was eager to get what she wanted from inside. She just knew there might be certain complications. She shook her head. What was she so worried about? She was a paying customer, after all. She’d simply walk in, head held high, pay for her items and leave. No unnecessary drama. With a deep breath in, she pulled the hood of her cloak over her hair and walked through the front door.

She paused for a moment when she walked in – not intentionally, though. She was awed at the sight; She’d never been into a proper armory before. Her eyes traced the walls, mounted with too many weapons to count. Mannequins spread across the floor wore stunning suits of armor. There were even odd weapon types she didn’t even recognize. It was all so much to take in, and Edwin, the burly owner sat behind the counter, clearly noticed Helena’s confusion. He rolled his eyes. Read more »

The Christian Girlfriend Part 2 [MF]

[Part 1](https://www.reddit.com/r/sexstories/comments/etbs9a/the_christian_girlfriend_mf/)

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I was early, I waited in my car outside Mary’s house for more people to show up. House is an understatement it was a three story mansion with a giant swimming pool and a large open air balcony for parties. The weather was pleasant tonight, it was warm with a slight cool breeze.

Mary’s family was attending the Kentucky derby and a wedding. Her sisters were leaving for vacations with their friends the following day too. This meant she would be alone at home for the rest of the week. After the family left her, the eldest sister, Teresa had organised a party at their place. Everyone from their church group was invited. I was probably the only non church group person there. Our plan was once everyone leaves the party I sneak into her room and we hangout there.

People started arriving and I joined a group walking in. I was excited to see Mary, we weren’t getting to spend a lot of time recently due to other obligations. We did have many more sexual adventures since the first one at the parking lot. No intercourse yet but she did start reciprocating. Her blow jobs were terrible in the beginning, but she got better as I started sending her porn and guided her each time she worked on me. Within no time she was a pro and knew exactly what worked best on me. Read more »

The further adventures of Frank and Karen Part 6 [MF] [MM] [BDSM]

“OK Frank when we were in that adult shop I spotted something I wanted.
So later I went back and bought it for you.
Close your eyes and don’t look.” Karen told me.
Touching my cock she took my balls in hand and began to slide them through what felt like a ring.
Seconds later something encased my cock.
It had the feel of cold metal, smooth yet resilient.
It was then that I heard a “click”.
Looking down only to find my mommy daddy bits locked in a chastity cage.
Think of a miniature bird cage that has a bend in it pointing downwards.
My cock completely encased inside.
There was an opening at the tip that would allow me to pee and that’s about all.
If I were to have an erection I think I would be in a bit of pain as it attempted to push its way through the device. Read more »

Our Changing Relationship [MF] [MMF]

This may be just part one because it is an ongoing relationship and requires a little backstory. Names are changed for privacy. It’s been a lot of changing for both me and my gf and I needed to get this off my chest!

Also this is a new account just for this so please excuse the newness. If the mods need me to, I can verify that this is all true although dialogue is not exactly word for word obviously.

I(22) We’ll call me James and my gf, we’ll call her Sarah (20 turning 21 this month) have been dating since just after high school graduation(both 18). We had a great summer together before going long distance for the first year of college in the same state. It was hard and we took a month long break but managed to survive the year. Sarah transferred to my college for our sophomore year which we were both really excited about.

A bit about us, Sarah is 5’4 with hazel eyes, brown hair and in good skinny, even though she is shy about her stomach because it’s not “perfect”. She is on the smaller side at 32b but has a very nice ass. It’s big especially for her size but not so big that it doesn’t fit her. She knows she has a great butt and it’s something I have always complemented her on. Read more »