Tag: High School

[F] That time my slutty coworker was driving me out of my mind with desire…

With her blouse torn open, Linda looked so good it almost made me nauseous.

Not that there was ever a time when she didn’t look good.

I’d noticed her from the moment I’d hired on for the crappy summer job as an assistant manager.

On the surface, we didn’t have much in common. She was up front at the desk in a customer service role. She was outgoing and trendy and carefree in a way I’d never been–at least not in my professional life. She was just out of high school. And even though I was in college it seemed like she was from a completely different generation.

I was always conservative and shy and professional. And my personal style was more vintage and grown up. I was never cool or contemporary. Perhaps all of that was just a side-effect of years spent in boarding school. In any case, I was focused on getting valuable “real world” business experience. Or at least some strong recommendation letters and resume fodder that would help me in the years to come. Read more »

Surprise Midnight Cock Special Delivery

My wife and I have high libidos and we are open about discussing our sexual past. In high school, she lost her virginity to her boyfriend who would clandestinely sneak into her bedroom through the second floor window and fuck her with his curved cock. She never came, but he would always leave a condom overflowing with a heavy load of teenage cum before slipping out.

We replay this event several nights a week. She goes to bed first, and falls asleep. Sometimes she sleeps through the night, undisturbed. Other nights, I climb in through the bedroom window as a modern day Casanova, sporting my fat hard cock, swollen with anticipation. With her high libido, she always goes to bed horny, but never knows if tonight’s the night she will get a cock full of cum.

Last night was no exception. She was asleep on the bed as I entered through the window, slipping in silently. She was face down, wearing a pajama top, but with her bare, creamy, full ass exposed. I removed my tee shirt and shorts, and my manhammer immediately popped up, engorged and ready for action. Read more »

A summer party, a cock-hungry friend, and the shy new girl she abandoned [MF]

The summer after high school graduation. Everyone remembers that, right? Or doesn’t, because they ingested far too much alcohol. Such was the case for my group of friends. Except for one night..

It was a party like any other. My bud Eric had his parent’s house to himself all summer. It was a home halfway up a mountain, backed by an endless forest. Our parties there always included a bonfire, liquor pong, a customized box of party Jenga, and laptops with Warcraft 3 and Brood War.

15-20 people was the average number of attendees, and tonight was no exception. There were a few new faces, and a good split of guys and girls. We started with a bonfire and some Fireball pong outdoors. One of the new people was a beautiful brunette with long, dark hair, a curved hourglass shape that accented her perky ample tits and wide hips, and a half-moon ass so round and firm that it defied gravity. She had on large black glasses which really brought out her almost-Asian almond eyes, and a floral summer dress which showed off the most tantalizing glimpses of her pale breasts squished in it. The dress clung loosely to her body, accenting her curves, and it often road up to expose the bottom of her ass cheeks whenever she moved. Read more »

Poolside fun [FM] while my friend also gets hers [FM]

This one goes back a while ago towards the end of the summer before my senior year of college. We’re talking about 15 years ago, so some of the details aren’t tack sharp and I’ve filled them in. It’s long because I like to write, so feel free to skip to the good stuff at ******

My high school friend Liz and I were hanging out at her house just lounging around in her parents pool. Liz’s family had some serious money and she lived in a house out in the country with no neighbors that close.

“I’m bored,” Liz said after an hour or so. I shrugged. I was enjoying just relaxing with my last few days before I returned to school. She jumped up and ran into the house. Five minutes later she came back outside. She looked me up and down shook her head. “You’ve got to change,” she finally said. I looked down at myself. I was dressed for comfort in an old one piece from my time on the swim team. Liz grabbed my hand and pulled me inside and into her room. She rummaged through her drawers and tossed me a dark purple string bikini. “It’ll have to do,” she said, pulling off her own suit and reaching for something skimpy. “Your ass and tits won’t fit in anything else I own.” Read more »

The Ride Home from the Water Park [MF]{Cheating}

This happened almost 25 years ago, when I was only 18.

It was the end of summer vacation, and my friend group decided to do a little miniature caravan out to the water park a few hours away. It was one of those places with a tide pool and slides and a few non-water rides, but all in all a fun time and a good way to spend a random Wednesday when it wasn’t over-crowded. About fifteen of us went, but I was in the car with my friend Jason, his friend Steve (who I didn’t know well), and Steve’s girlfriend, Betsy (who I didn’t know at all).

I went to a private high school, so my friends were from all over the county. It was hard to get us together in a large group because some of us were over an hour away from the rest. Seeing everyone was great, and a lot of fun was had. Read more »

Caught my boss and coworker in the act [MF]

I just finished my summer internship at a consulting firm. When I started there at the beginning of summer, I instantly noticed this girl that I will call Summer. She was a year out of school making her 2 years old than me (23 and 21). She was the hottest girl in the office. She was an easy 8 in office clothes and based on her Instagram, a 10 when she cleaned up. She was a lean 5’8” redhead with D’s at least and a perky ass.

We hit it off right away. The firm had lots of social events and happy hours. I would hit on her at most of them and she seemed to reciprocate. A couple weeks in, the firm took us to a baseball game with free beer and food. She and I were really hitting it off and I thought I might close the deal that night. She was going easy on the beer because her team had a big client meeting the next morning. Around the 7th inning, her director came over and pulled her away so they and the others on the team could have a conversation about their meeting. Me and a few of the other interns went to load up on beers before they closed sales at the end of the inning. Read more »

[FM] Had sex with my old guidance counselor

I am 22 years old. I am half Dominican / half Irish. I am 5’8”, size 4, C-cup. I live a big city about 45 minutes from where I grew up.

I am an escort. I work for an agency. On days I work, I go to our incall location and the agency sends over men. They don’t tell me much more than their name and what they want to do.

Last week, they sent over a guy with a very common name who wanted to do some race play. A pretty normal sounding appointment. I think nothing of it until I open the door and there is my old high school guidance counselor.

I recognized him instantly. He gave me to standard body scan most men give me. It wasn’t until a minute later that he was looking at my face. He probably noticed my expression. He asked if we had met before. I said a long time ago. He face went pale and he asked if I went to a certain high school. I said yes. Read more »

[MF] Seducing my big sister’s married friend

Pooja is married, almost ten years elder to me and has been my playmate for almost a year. If you don’t like cheating stories, you should stop reading now.

Pooja has known me since I was twelve or thirteen; I am twenty-six now. During my adolescent years I never thought of her in a sexual manner. She is a friend of my eldest step sister. The last time I met Pooja was for my sister’s wedding when I was in high school. I have lusted and checked out every single friend of my elder sister. My sister is very good looking and had over half dozen good looking friends. Although I didn’t particularly single out any of them, everyone was an object of my dirty fantasies one time or the other. I have seen Pooja hang out in our pool with my sister many times when I was in school. She always treated me like a little brother.

Pooja is average in height, in her mid-thirties with an interesting attractive face. Her breasts are astonishingly upright, her ass is not small, but tight and very inviting. Her thighs are firm, round and even. With her professional, moderate style of dressing she is a mature, sensuous dish, always perfumed and well groomed. Read more »

First time exploring my bi side [MMF] [GROUP]

“Do you wanna come watch us fuck?”

Jason was a fit Australian man in his mid-40s, tan with a short-cropped, salt-n-pepper beard and black frame glasses. He resembled Santa Claus if he hit the gym five times a week and consumed protein shakes instead of milk and cookies. He and I had spoken of my desire to explore bi play and much of our talk revolved around this topic of conservation. His girlfriend, Raye, was in her mid-20s, a petite, toned body decorated with a shoulder and upper thigh tattoo. In her profile photos, her hair seemed to change colors more than a mood ring, each more vibrant than the last.

I stared at the text for what seemed like hours before deciding on a course of action. It was just past 1 AM, and I hadn’t anticipated an invitation given that we’d never met in person. I’d spoken to each of the couple separately about kinks and potential play, but our schedules hadn’t yet aligned to make it happen. Before I could say no, my dick took control of my phone and accepted. Read more »