Tag: High School

A friend’s fix-up leads [M]e to hook up with three [F]’s.

Because this story involves not one but three women (all of whom know each other), and is very detailed, to protect their anonymity I am going to use initials instead of first names.

This journey starts off in late 1995, a friend who came from the same hometown as me set me up with her younger sister who I will call “K.” K was still in high school but 18. K had very pretty, cat-like eyes and large breasts. During winter break back in our hometown, we went to a movie and back to her (and my friend/her sister’s) house. We go into K’s room, shut the door, and talk on her bed for a while. Finally, I make a move. It is well-received. We mainly kiss but eventually K’s top and bra come off and I am treated to feeling and sucking some awesome, pendulous 18 y o breasts.

I am really into K. She visits my friend/her sister at our college a month or two later. I make time to visit with her but am crestfallen to learn that she is dating someone her own age in high school. No big deal – we behave like adults, awkwardness is avoided, and we remain friends. Read more »

[MF] The Wild Weekend That Kicked Off An 8 Month Stretch of Wild Fucking. Part 1 – Blowjobs and Big Asses

Almost exactly 10 years ago this week started a 8 month run of the most wild and promiscuous sex streaks of my life. I was recently out of college (22m) and I had a job that paid me enough to pay my bills and then party my ass off. In the year leading up to this 8 month run, I had lost my virginity in May and with the help of working out I finally felt confident to shoot my shot with women. This 8 month period shot my number of partners from 4 or 5 to well over 25. The streak ended that fall when I met my now wife, but it was the perfect example of someone “sewing their wild oats.”

I had a good mix of partners that were FWB, one night stands, friends, acquaintances, and complete strangers. When I lost about 20-25 lbs, started working out, and just lost my baby face I noticed I got a lot more attention from women that I was interested in but they were not interested in me until now. I had come into my own. So girls I knew that were previously not interested in hooking up, were some of the ones now interested. This particular story that kicked off everything has a bit of both. Read more »

Ambushed and deflowered by my best friends [FFF]

I’ll start by telling a little bit about myself. My name is Anna, I’m 19 years old and just finished my first year of college. I still live with my parents because it’s cheaper than living on my own, their house is relatively close to my college and I frankly enjoy the comfort of not having to worry about stuff like bills, cooking and laundry. In highschool I used to play soccer, but when I went to college I stopped because half the team stopped and I didn’t want to start in a new team. I tried to substitute this loss of activity by going to the gym, but as we all know it can sometimes be hard to drag yourself to the gym so my goal of three times a week has not been met as much as I wanted for the past year. Luckily the ‘freshman ten’ doesn’t apply to me so my athletic build hasn’t yet left me. Before this story took place I was still a virgin: I’d kissed with some guys and some girls, but no one but me had even touched my nether region, or vice versa. I don’t have a conclusive sexual orientation. Before college I’d considered myself mostly straight. I had the classic short-lived high school boyfriends with whom I never did more than kiss. But in college I also drunkenly kissed with a few girls and surprisingly enjoyed it just as much. So at the least I’ll describe myself as bi-curious, who cares anyway nowadays? Read more »

23(M)y first blowjob from a BBW

We were in high school. Really good friend and we would always hang out with somewhat the same group of friends after school to go smoke of chill at her house. Her mom didn’t mind us smoking and hanging out there, that’s why I loved coming over so much. Honestly she was such a great person and I never saw her more than a friend since I wasn’t really attracted to girls with a little more cushion for the pushing in(BBW), like I do now. We always just chilled and since we were so comfortable and close with each other we would talked about our sexual experiences and how we were both really good at doing what we do; the eating pussy, her sucking really good dick, not having a gag reflex you know the usually stuff when you’re tryna fuck the person directly next to you. Lol. Looking back at it now i missed so many signs i could of capitalize on because I only saw her as a friend. Read more »

Solving a lifetime problem [FF]

You guys think you got a problem, well picture this, a small round balloon glued to a much larger round balloon with four of those long balloons that clowns blow up to make balloon sculptures at children’s parties hanging off the big balloon. On the front two large balloons, same size as the top balloon, glued on. That’s me. I’m five foot ten inches, pale white, black hair and 250lbs. Obese is a word. No one wants to spend any time with someone so fat, which leads to anxiety and depression, which causes my eating disorder which causes me to be so fat.

It’s not like I got any control over it, it’s just a condition I’ve had and I’ve been to counselors and psychologists, joined weight loss organizations and a lot of other shit and it just doesn’t take. Who wants to be near a fat woman? All I’ve had from all of these is “it’s your fault you’re so fucking fat.” They don’t say it like that, but they all say it. Then one day it changed for me. Read more »

A Friendly Visit [MFM][OC]

“Hi Love, just wanted to remind you that Joe will be staying with us for a couple nights this weekend,” read the text that I sent to my wife, Amber.  Her reply, “Oh yes, I remembered and I know you’re looking forward to it.”  I was indeed looking forward to it, but I suspected Amber was also looking forward to it more than she was letting on.

Joe was in the process of moving from Ohio to Florida and I had offered him the guest room in our North Carolina home as a layover point. Joe and I were lifelong friends that met in High School and continued our friendship to the present; we’re in our 40’s now. 

Amber had met Joe several times and always enjoyed his company and engaging in conversation with him.  The two of them were in the same profession and were never short of topics to discuss.  Of course that also afforded them time to enjoy stealing longer gazes of each other; fueling the naughtier thoughts I suspected both of them were having.    Read more »

A Drinking Game [F] [rape]

The red solo cup made a sharp crackling sound as Chloe crushed it in her hands. She took the balled-up mess of plastic and tossed it through the air. It sailed with a perfect arc and swished into the trash can.

“Yes!”, she exclaimed. Everything was going her way. She had just turned 18, had taken first place at the high school swim meet earlier, and was now at one the biggest parties of the year. She still had her hot pink swim uniform on under her clothing.

Chloe normally didn’t drink much, but tonight was a special occasion. She was a little bit of a celebrity. Maybe it was just her inflated imagination, but it seemed like everyone at the party knew her name.

With her finished drink successfully disposed of, she found a nearby empty couch and sat down heavily.

She was normally very coordinated and light on her feet, but she was exhausted from the long day and the small amount of alcohol in her system was wearing her down.

She laid her head back and focused on her breathing, willing the room to stop spinning. She’d only had a few drinks, but her small body didn’t even break 130 pounds, even when her long blonde hair was soaked from the pool. Read more »

[29F] I’m going to ask you to imagine something

Imagine this.

Imagine that you’re part of a friend group, a very close friend group, of two guys and three girls. Now imagine you’ve been close friends for maybe 15 years, since early high school, and imagine that this is just an incredibly normal, though somewhat nerdy and academically successful, group of friends.

Imagine that you’re the shyest, nerdiest guy in the group, and naturally, you’ve grown up maybe fantasizing about any – or all – of the three girls in the group on and off over a long period of friendship. That would be natural, right?

Now imagine there’s a fourth girl, who isn’t a part of the main group, but is very close friends with a few of you from the group, and very familiar with it. She occasionally joins you and hangs out as well.

Now imagine you’ve come to be in your late 20s, and you still haven’t had any sexual experience in your life. Every week, you still hang out with your close group of friends, get together and chat, maybe watch something, pretty consistently, every week. Read more »

46[F] Girls Trip to Fort Lauderdale

Picture this! Trying to survive a very long cold winter, you take a trip with your five best girlfriends to a beach house in Fort Lauderdale. Most are married, including yours truly. We hit the town with a vengeance and end up at a beachside bar. I am wearing a cotton crochet dress with heels…. hair down and just so happy to be away from all of my obligations.

He approaches me. “Do you want to dance?”

I oblige.

The night is a whirlwind.

I am trying to hide from my friends so we can make out like two teenagers.

He is a great dancer with beautiful curly locks and tanned skin. Turns out he had previously been in the Coast Guard and was working on a private boat for a family that had just returned from several months at sea/land in the Caribbean. He admits that he is 31 and has not had sex since he left because he had so many obligations for this rich family.

First bad idea, we head to the beach. It is windy. My dress is now around my waist, tits out the top and my panties around my ankles. Bodies contorted…. a few too many drinks. We see police coming at us from down the beach. Panties up. Dress down. Read more »

Nudie magazines in the woods leads to first blow job (Part 2) (mm) (sub)

I was standing in the woods pants down, stiff cock and nudie mag in my hand. Jim, a jock from my high school had followed me. “Let me see one of those, Kenny” he demanded and sat down on a nearby log. Mmmm he said and pulled down his pants and boxers revealing a thick cock with mushroom head. He started moving his hand up and down his cock. I had never jerked and just stared standing with pants down and a hard cock.

“How come you’re not jerking” he said. “Come over here. I’ll show you. Grab my cock. Remember I saw you take those mags. That’s right Kenny boy! Now move your hand slowly up and down my cock…pull on my knob…mmm…now stroke my shaft, up and down… faster boy! Mmmm. Keep stroking…” I was getting harder stroking his cock and then he moaned and spurted cum everywhere. My hand was covered in milky cum.

“Now you’re turn! Take all your clothes off and jerk yourself!” I barely touched my cock before cum shot out all over the ground spurting almost four feet. Good one Kenny he said. Come back tomorrow same time for more. That night I stoked and stroked thinking about breasts pussies and cocks.