Tag: High School

The blackmail (FM) PART 1

Hello reader, this will be quite a long one. In order for me to explain how the blackmail happened, I would first like to tell you how it all started.

It started a few months ago. I was bored out of my mind, scrolling on my phone, when I first saw his post. He was promising a good time but he wanted someone who would completely give him control.

I read the post twice, found myself typing a reply, but quickly erased it. I closed the app and threw my phone on the bed, next to me. I was a good girl, what was I thinking! This was definitely not for me! I tried to keep myself busy, but my mind kept cycling back to that post. I was too curious, so I caved in. I messaged the author, asking what he meant exactly. He replied instantly. Telling me he wanted to find a slut willing to do absolutely anything he wanted. Something about the way he said it really turned me on. I told him I was willing to give it a try, but this would be my first time. So he agreed to start slow. Read more »

My friend’s girlfriend [F] gave [M]e a handjob

I was driving around after my high school graduation and saw my friend’s
girlfriend at the roller rink. She had blonde feathered hair, huge juicy tits that defied gravity, and well proportioned curves in Calvin Klein jeans. I loved watching her shake her ass when she skated.

She asked me for a ride and we drove around looking for our friends at all the local spots. That got boring real quickly, so she suggested we park. She slid over to my side of the front seat and
started to kiss me while she stuck her hand down my pants.

I pulled down her pants and underwear. She had wispy blonde pubic hair. I unclasped her bra and felt her warm chest. We continued to kiss while our hands roamed each other’s body. I found her wet pussy and began fingering her. She was moaning in my ear while I kissed her neck. I was rock hard in her tiny hand. She guided my hand to her clit. The attention I was giving her clit caused her to dig her nails into my arm as she came. Read more »

Gave a 28 Year Old Woman Her First Orgasm (from sex) and Other Firsts [MF]

My first real job had me working in a cubicle in an office when I was just out of school and in my early 20’s. I’m a pretty average guy, 6 feet tall, sandy brown hair. Natalie worked in the cube next to mine and we hit it off right from the start. She was in her late 20s at the time, about 5 feet tall, curly black hair, curvy with big tits. She was friendly, but also sarcastic as hell. The age difference was not that significant, but she had been working for years, was married, owned a house, etc. so had had a lot more life experiences than me. Or so it seemed.

I learned that she actually lived out-of-state and her actual work assignment was at our company’s office near her home. She was only filling in at our office on a temporary basis and would be returning to her permanent office once the company had hired and trained some people to fill the role here. So, she typically stayed in a hotel near the office (paid for by the company) M-F and drove home to spend the weekend with her husband. Read more »

Justin and Sandy [MFM]

Justin’s cock was shorter than mine but a lot thicker, and uncut. 

Sandy was on her knees in between us, stroking our boners hesitantly but with a glint in her eye. ‘What in the fuck is going on?’ She laughed. ‘I don’t know but I’m not mad at it’ I said, almost gasping with pleasure…

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I met up with Sandy and Justin the summer after our junior year of college. We were in the same physics lab in high school and were good friends then but hadn’t really kept in touch. 

Justin was handsome, tall, and athletic – a basketball player. More attractive and generally more popular than Sandy and I. 

Sandy was a D-1 soccer player. Cute, mousy face, very short with a thick athletic ass.

I’m basically a nerd, but funny and charming – my personality making up for my less than average looks. 

I had always had a crush on Sandy. I think Justin did too, but he was mainly interested in more traditionally attractive girls. 

So that summer Justin invited us over to swim at his parents’ place while they were in North Carolina. We were going to have some beers and try to stay cool in that sweltering August heat. Read more »

I took the virginity of a Christian (teens, virginity)

Kelly is a very religious girl, being raised in a strong Christian home filled with rules and restrictions that most kids our age are pretty used to ( 17-18 year olds). I knew from the beginning that I loved her, from the moment I became best friends with her in my junior year of high school. She’s got the cutest face, and the sexiest body that I could not stop staring at when I first saw her. Big c-cup tits that always showed cleavage no matter how much she tried to hide them. Even on cold days while wearing a sweater they were still visible- and being a virgin at the time, all it takes is a little imaging to stir up some sexy visions of how amazing they looked under that sweater. She also has the best hips I’ve ever seen, with an amazingly big and firm ass thats to die for, especially when she wore tight skinny jeans that would bring out its round and sexy shape.

Kelly was aware of her amazing body, and always told me she hated it because her mom would verbally abuse her and insult her for not ever looking decent- which she can’t really be blamed for with that smoking hot body- it can’t be hidden. Read more »

[MF] Girlfriend watched me fuck her best friend

This summer my girlfriend and I drove up to Colorado to get a break from the heat and visit her best friend from high school. Ashley has always been a wild card. She has full sleeve of plant tattoos on her right arm, she shaves the side of her head and never wears a bra. I’ve met her a couple times before she she’s always been really nice but flirty.

We spent three days with her in the small mountain town. The first day we did a hike and explored the area. On the second day we went out to a brewery to see some live music and enjoy the IPAs and bourbon aged stouts the hipsters enjoy up there. We had several beers and made our way back home.

We sat on the couch about ready to head to bed. Ashley and my girlfriend look to each other, then Ashley walks over to me, leans over to put her hands on my knees, watches my eyes go right to her bra-less tits and says “Yeah, I don’t think he’ll mind.” Somewhat confused, I look over to my girlfriend to see her biting her lip and nodding. My dick instantly gets hard, I’ve been trying to sneak glances of Ashley’s nipples poking through her shirt all night. Read more »

Bachelorette party [MFF] [Long]

I used to work as a prep cook at a ski resort when I was 18. I lived in a small apartment with several friends about a kilometre from the restaurant, and would walk across the village to get to work. It was summer and there were plenty of people around for downhill mountain biking, hiking and some other activities, but it was also a spot for bachelor and bachelorette parties. 

I knew a lot of the people who lived up there full-time and we would hang out at each other’s establishments. It was a small community and a lot of the staff were foreigners with limited supports. There was a surprisingly good number of bosses that kept us fed and full of a few beers. The bad bosses lost all their best staff to the good ones, so there was some self interest, but we knew who had the big hearts. It was Friday, and every Friday I finished my early shift and hung out at my friend’s work while he finished up his day shift. I was always fed lunch and a beer because if the dinner prep team was running late I would help out. Most of our friends worked Friday nights so we would chill after work until everyone else clocked out.  Read more »

[MF] I (22F) am paying my way through college as a prom-date-for-hire, AMA

Answers to a few obvious questions:

– My clientele are rich families who want their son to have an attractive, presentable prom date.

– My dates must be 18 or older, no exceptions. rentals)

– I pass easily for high school age, and the backstory I give to my dates is that I go to school in a neighboring state and we met online. (If you google my “working” name you’ll find an IG account full of vaguely high-school-ish pics.)

– Obviously I can’t have a date at the same school twice but I live in a large metropolitan area and there are plenty of wealthy enclaves.

– I can generally only do 5-6 proms per season because they cluster around the same dates but they pay well enough (~5K USD per prom plus expenses—did I mention my clientele are rich?) to set me up for the year.

– Surprisingly, I was fully booked last year and this year, as many wealthy private schools held outdoor proms or small group “pod” proms with testing beforehand

– Do they get action? That’s entirely up to me, and it depends. If a guy is baseline courteous and polite he will at least get to make out a little. Read more »

Who’s the boss

How I came into money is insignificant. Sure I’d love to tell that story as well but in the interest of what this audience is interested in we’ll just skip that part.

I retired at the age of forty. I lived modestly considering the bankroll I’d managed to amass. I dated many beautiful young women who always turned out to be gold diggers.
By the age of forty five I had given up on dating all together. I still had respect for the opposite sex but I knew I wouldn’t find love.
I decided to give these women what they wanted. I liked women in their early to mid twenties.
They had the energy to keep up with my insatiable sex drive. I had simply learned to be up front and offer to pay them for a weekend of debauchery instead of having a woman pretend to love a man twenty years older than her in lieu of a more comfortable lifestyle. Read more »

Chloe the Roommate [TF/M]

This is my first time doing one of these. I dont see alot of these types of stories on here so I dont know if it will be popular but feedback is appreciated. I tired to go through and find spelling mistakes and grammer but I typed this on my hpone so it was hard. Anyways without further ado…

Chloe the Roommate

After coming back to school for my sophomore year at college I elected to stay in the dorms again. The dorms were split up by major so it was nice being around like minded people. While I made a lot of friends last year, they were more just classmates I came to realize as none of them “had the time” to chill over summer break. I decided to just focus on my Art major and hopefully get a new job as something close to that. Instead of befriending my new dormmate, I just decided to do the whole head nod thing when ever I see him. What I didnt plan on was that Him was a Her. Read more »