High School Archives — Page 311 of 805 — NSFW story

Mutual Masturbation with a Cousin [MF]

This story is from when I was 18 years old, and I met Sarah, a cousin (2nd or 3rd) for the first time. She also 18 at the time, and we met at a wedding. It was very strange because I was introduced to her as a cousin, but my mind was processing her like a gorgeous, out-of-my-league girl. Sarah was very model-like, about 5’9″, slender with big, brown eyes and straight, light brown hair. She didn’t have big breasts or a big ass, but every part of her body was tone and define. She was one of those girls who looked 18 when she was 14 and at 18, when I met her, could have passed for 24.

Her and her family had just moved to our area and she was attending a new high school for senior year. She wasn’t friends with any of her peers, as she wasn’t interested in high school boys and high school girls were too intimidated by her. She kept to herself, spent her time painting, and occasionally dated some older men she would meet online. Read more »

Sisters (continuation) Swingers Party [FFM [Plus]

In order to follow this story you must read Sisters. I as I mentioned before, I kept a journal of projects I worked on, locations and people I met as a reference. After being in Grants Pass, OR for six months, I was required by contract to meet face to face with company officials to give them a progress status including cost and any projected milestones. Their headquarters was in my home town of Atlanta, so I call my relatives to let them know I was coming to town. As soon as I settled in at my brother’s place I had a note from my ex wife, she wanted to meet as soon as possible. Two days later we meet at a local restaurant, she never asked how I have been. She starts in about she is 3 months behind on payments for OUR house. In our divorce, she could stay in the house as long as she made the house payments, I paid the property taxes and insurance. She gave all kinds of reasons why she was late with the payments, I didn’t want to hear it, I was pissed. I told her I was selling the house immediately and she needed to move. I told her I would contact the mortgage company in order to make the payments current. When I left the restaurant, I contacted my lawyer, told him what was going on, he immediately started drawing up paper work for her to sign with a clause in the document that it was her fault for the delinquency. This was done so I could go back to mortgage company to clear my name for any bad debt associated with the house. Read more »

My First Threesome [FMF]

I was 18 at the time. Fresh out of high school working at a private investigators office which had some shady after-hours jobs. I answered the phones and did clerical work. All the major businessmen in the area would meet with my boss.

On Saturday nights, he would host poker games at the office, and I would waitress at them for some extra cash. Most of the men who would attend were downright crass. They would try groping me or try convincing me to sleep with them for money, but I would always politely decline. None of them were remotely attractive to me at all except Arthur.

Artie was an older man who was in his early 60’s but was extremely attractive. He was kind and had a contagious smile but more than that he had this energy about him, this calm dominant energy, that would instantly make my pulse increase. When he came to the office, he would come talk to me and actually ask me about my life all the while gazing deep into my eyes. While speaking to him I would be transfixed in his gaze like a deer in headlights. That first time he touched my face I felt electricity course through my veins running straight to my most sensitive parts. I honestly think he felt it too. Read more »

[FMF] Summer of 2001

The turn of the millennium was marked by the continuation of the underground clubs of the nineties, a whole new swathe of recreational drugs hitting the streets and the ladette attitude becoming the dominant force of British lady’s culture. Free women were bending over a car in a random car park at 3AM for a stranger to let her feel like a whore in a momentary escape of the crushing societal expectations placed upon her by the generations before.

It was at this time I met my husband-to-be on the dance floor in a nightclub with flickering strobe lights and lasers heightening the effects of the ecstasy coursing through my veins, ours eyes met, and I immediately begun to grind my ass against his crotch in rhythm to the loud music. Deep base pumped out of the speakers that surrounded us and our first five minutes together can be summed up with my leatherette mini skirt pulled up to just below my navel, a Victoria’s Secret black thong slid to the side, and three fingers deeply gouging out my wet pussy whilst surrounded by intoxicated revellers packed tightly on the arena floor. Read more »

My Best Friend’s Sister Gives Me a Blowjob [MF]

Anthony’s sister was very hot. She was two years younger than us and I never paid any attention to her until I came back home from college. I moved back home with the parents and spent all of my time hanging out with Anthony while I looked for a job.

We drank and chatted about the girls in town. I found out that Anthony had been hooking up with Tiffany Parker who had been the most popular girl in our high school. Everyone wanted her. She was drop-dead gorgeous with big breasts and ass. I had spent many nights jerking off to her while in high school. Anthony tried to play it off as if it wasn’t anything but I know he was proud that he was seeing her. He told me that things were getting kinda serious and he was thinking about proposing.

I was stunned by this. Anthony had always stated that he was never going to get married. He wanted to remain single forever due to his parent’s unhappy marriage. It was shocking to hear him say it but I also thought that we had both grown so much over the past four years. Read more »

Buddy and I catch my g[f] naked. (Mild / no sex)

Back in high school the neighbors next door had a few kids that I hung out with on the regular. Their youngest was about 7 years younger than me. We weren’t all that close back then, but started talking pretty regularly for awhile when he started college and I moved out of town. I actually came back in and helped them with admissions and a few things like that. Going forward we managed to keep in touch while his siblings drifted off. A good many years later I’m living not terribly far from where we grew up.

Last week he started a conversation with me. Generic stuff. ‘How’s things? Still work at [insert job]? What have I been up to?’

Turns out he was coming into town to visit his parents for the weekend and was curious about what I was up to. I told him I had plans to figure out the wiring in my girlfriend’s kitchen and he offered to help for an evening to break up the monotony of hanging out with his parents. Read more »

I (21F) finally had sex with my married (44M) teacher from high school.

It should be clear that there was never EVER any sexual activity of any kind during my time as his student.

I did always have a crush on him in high school; but he was the kind of teacher almost every female had a crush on too. I’ve always seen him as an older male version of myself. We’ve always gotten along and had a very close yet appropriate student-teacher relationship. I am fully aware of what grooming is and I fully understand that this was not it. I graduated at 18. We kept in touch since graduation and would periodically hang out as friends (go to art museums, smoke, get tacos, etc.). It’s important to note that I have babysat for the two children he has with his wife. I am quite close to him and his wife and his kids. We are both in open relationships/marriages.

My birthday was about a month ago, and we haven’t seen each other since I babysat for him i’m November. He invited me over to have a drink with him at the makeshift bar he set up for me since I can’t go out at 21 due to the pandemic. Read more »