High School Archives — Page 23 of 805 — NSFW story

Cuddles and Sex with My Stepsister Part 1

The sound of lightning snapped outside of my window. It was raining hard outside and had been all day. It was now 10 pm and I was laying in my bed with the lights off and watching television. A horror movie was on as it felt like the perfect movie for a rainy night. It was a B-movie featuring a monster that seemed to target only high school teenagers, especially girls. Many of the girls were half-naked or completely nude when the monster attacked. It was a silly movie but entertaining.

There was a knock at my door. “Hey, can I come in?” My stepsister Darlene said.

“Sure.”

Darlene opened the door and stepped into my room. My stepsister was wearing very short shorts and a t-shirt. Her curly blond hair fell to her shoulders and strands of it hung in front of her face. She closed the door behind her and walked over to my bed.

“What are you watching?” Darlene asked me as she looked at the television. The monster was inside a girl’s house and was silently climbing the stairs. There was a shot of the girl in the shower. The camera zoomed in on her tits. Read more »

[MF] She (F18) wanted to give me (M18) the college experience

I’d had the biggest crush on Emily for a couple years now. The idea that an “older” woman would even give me the time of day, much less show any interest in me, was so captivating I found her near impossible to resist. In truth, she was only about 3.5 months older, but that put her a year ahead of me and when you’re in high school, it seems to make a difference.

Emily and I rarely had classes together over the years. I never had the courage to make a move on (aka talk to) her until we were assigned as lab partners my junior year of high school. Our conversations went from minimal to light conversation to flirting fairly quickly, with her tousling my hair every chance she could get (“it’s always so soft,” she’d marvel). I’d stammer through a response, enjoying the physical contact but still fairly insecure. To add to the complexion, she was dating a kid on my basketball team who I wouldn’t consider a friend, but when you’re in the moment, chemistry on your varsity team is important and I didn’t want to jeopardize that. All that said, it didn’t stop us from texting fairly often. One night towards the end of the school year, she texted me late. Read more »

Caught my son jerking off into my panties, and then…

A few years back, I started to find several pairs of my panties in my son’s hamper when I was going to do laundry. They were obviously used and very messy and I honestly didn’t know how to react.

This was before we were intimate with each other the way we are now, if you’re at all familiar with my post history.

Anyway.

In the end I did nothing and hoped that he wouldn’t do it again, that it was just sort of a one-time thing, something he did out of curiosity and that I wouldn’t need to talk to his father about it.

His father was a very abusive man who I have since left, but I was heavily under his control back in those days, which meant I always reported everything that went on in our house back to him.

Unfortunately, that was a foolish hope and of course my panties kept popping up in his hamper, all sticky and wet. And the longer I didn’t say anything to him or my ex-husband about it, the harder it became to say anything at all. Read more »

I was an adorable redhead’s (26F) first after her divorce [MF]

A few years ago I met with a gorgeous redhead from whisper. I had seen a post of hers when I was on the east coast for business, we started chatting and flirting, hit it off, and decided to meet for a date at the beach boardwalk. Turned out she was very recently divorced at 26, and I was her first “real” date ever, since she started seeing her ex when they were sophomores in high school. They had never really been on a proper date before, which meant I ended up being her first date she’d ever been on.

When I saw her walking toward me in a cute little red dress, she was actually cuter than the pictures she had sent me, which is rarely the case. She was clearly nervous, but a good conversationalist and obviously also quite smart, which I appreciated. We got some sort of board walk snack and sat on a bench and talked, with the conversation quickly moving to BDSM since she hadn’t been able to do any of that with her ex husband and she was curious about it. Between the conversation and how good she looked, I started to get pretty hard under my pants. I was wearing jeans and evidently my cock was pressing hard against the fabric along of the upper part of my pant leg, because she kept glancing down and I could tell she was getting a little flustered. I noticed and asked if she wanted to go find somewhere to park that was more secluded. She asked “and what?” sort of teasingly, and I just responded “I’m sure we’ll figure something out.” Read more »

Surprise fuck with a friend on the bathroom floor [MF]

Ever have a friend you just need to fuck and get it over with?

Annie was that girl for me.We went to high school together and she dated a few of my friends, so she was always part of the group. She also happened to be good friends with [R](https://www.reddit.com/r/gonewildstories/comments/x0tq33/dorm_room_sleepover_goes_exactly_how_youd_expect/?utm_source=share&utm_medium=web2x&context=3) and [Elle](https://www.reddit.com/r/gonewildstories/comments/y4zzm4/fucking_in_the_closet_with_her_mom_right_outside/?utm_source=share&utm_medium=web2x&context=3), both of whom you can [read](https://www.reddit.com/r/gonewildstories/comments/y0wlcb/fucking_our_way_around_the_apartment_to_my_exs/?utm_source=share&utm_medium=web2x&context=3) [more](https://www.reddit.com/r/gonewildstories/comments/x5zn42/not_quite_cheating_but_still_not_quite_allowed_mf/?utm_source=share&utm_medium=web2x&context=3) [about](https://www.reddit.com/r/gonewildstories/comments/zr3umc/fucking_her_like_a_slut_in_her_dads_car_mf/?utm_source=share&utm_medium=web2x&context=3) [on my](https://www.reddit.com/r/gonewildstories/comments/101p9xi/changing_room_quickie_mf/?utm_source=share&utm_medium=web2x&context=3) [profile](https://www.reddit.com/r/gonewildstories/comments/10nub9h/double_orgasm_while_driving_mf/?utm_source=share&utm_medium=web2x&context=3). We even had a brief fling in high school that involved making out in her basement, but that was it. College came, we went out separate ways, saw one another during breaks and were perfectly friendly, but nothing more.

Fast forward to a few years out of college. Annie had joined one of my best friends in visiting my city and they brought along a third friend. For your visual accompaniment, I’m just under 6-feet tall, athletic build, but not overly muscular. Dark hair, dark eyes, short beard.

Annie is tall. A few inches taller than me actually, she was a volleyball player with strong legs, a fit ass and wonderfully proportionate tits. Read more »

Hooking up with the hot punk high school girl from the grocery store (M22/F18) (Age gap) (slow build)

It was the mid 1990s and I was living with some friends from college after we graduated. We lived right outside a major city, but our close in suburb had the feel of the city and you could walk to everything you needed, including a small grocery store. I ended up walking into that grocery store almost every day and I noticed a very attractive girl working one of the cash registers. My housemates and I all thought she was hot and would always try to go to her checkout lane.

She was a thin, long-legged, punk/goth girl with her hair died bright red and cool makeup on her very pretty face. She had a lip ring and a tiny stud in her nose. She sometimes would small talk, but usually in a very bored tone. One day, I walked up to the register with one of my housemates and she smiled broadly and said, “I love that band.” I was wearing a black concert tshirt from a punk band that I really liked. There was a long line, so we only chatted briefly.

As we walked back to my house, my housemate said, “The hot chick liked your shirt.” Read more »

A Snapshot (College Story) [19m, 19f]

Some years before college, before the youth homes, the psych ward, the bad behaviors and addictions, and his eventual bottoming out, Dennis looked in his father’s Sports Illustrated Swimsuit Edition and gawked. The woman sitting on the beach, smiling at him casually as if asking what he was doing there and liking that was there all at once, had perfect legs. They stretched across the sand into the pictures foreground. Dennis then understood that he had a thing for legs. He tried to find the Sports Illustrated Swimsuit Edition again, several weeks later, and was disappointed to find that his father had apparently taken it with him to prison. So, he sat on the edge of the bed and closed his eyes and remembered the legs…

Seven years later it was October of 2018 and Dennis sat on a porch outside a house party in Carbondale, Illinois. He had turned nineteen a few days before. He sat there with his friend Kurt, whom he’d known since high school. They sipped their beer and watched the partygoers stumbling out of the front door at one in the morning.

“Where did you get this beer, man?” Dennis said. Read more »

[MF] My shy, nerdy girlfriend deep throats me for the first time… and something unexpected happens!

*Note: This is a true story about a girl I’m calling Becca, who I dated for about a year. I wrote one story about her, which you can find in my history, and I’ve been asked to write more! If you like the story, please reach out, I’d love to chat!*

…

Becca and I had been seeing each other for a few weeks. We lived about an hour apart, so we really only saw each other on weekends. But during the week we would flirt and sext online, usually cumming once or twice a night together.

When we were together, Becca was extremely shy. She’d warmed up to me, but around anyone else, even my roommates, she clammed up and blushed whenever she was asked questions. She was cute, though! Becca was short, with a curvy body and thick, curly brown hair. She wore big glasses on her heart-shaped face. She was extremely my type, and even now I find myself gravitating towards women who look like her.

Becca was also very nerdy. She worked in the sciences, played Dungeons & Dragons, and in high school had a series of crushes on men and women in her favorite anime. When she was interested in something, she went into serious research mode, and would text me for hours about what she’d learned. Read more »

[FM] I got caught naked at the mall

I don’t know why of all the dares this is the one I wanted to do. But I found myself walking back into the mall by myself.

After my dressing room adventures I wanted to try something else and thanks to Reddit, I was given an idea.

I stood outside the mens bathroom of the busy mall, trying to wait for it to be completely empty but it just wasn’t happening with all the traffic.

The handicap stall would be at the far end so I had to go deep.

Finally, I put my head down and charged in…running right into a guy coming out.

“Oops, my bad.” He said, and kept walking. I stepped into the men’s bathroom. A line of 10 urinals were on the wall with dividers between each one. Five guys were spaced out on them. The other wall was all stalls.

None of the guys noticed me, eyes on the wall in front of them so I quickly walked down to the end, trying not to look over at the guy’s peeing (ok I peeked) and with my heart beating out of my chest, got into the last stall. Read more »