High School Archives — Page 698 of 805 — NSFW story

That Killer Blue Dress [MF]

My [last story](https://www.reddit.com/r/gonewildstories/comments/3kzo56/the_one_that_broke_my_heart_mf/) got a lot of positive, supportive responses and though it’s been over a year I’ve decided to share a few more stories. These are all real, though I may have misremembered details and added a little dramatic effect. Memory is a funny thing like that. It can make you hate someone you loved, or love someone you hated. It can convince you with absolute surety of an experience even if it never happened. In that way I am only human and nothing more. As usual this is a long read and I’m sorry if not especially interesting. I’ll leave you a bookmark to skip to the parts you want to read.
Not quite a year had passed since she had broken my heart, maybe only a few months. A wounded heart makes you forget time and space, makes you unreal in your own mind. Things blend together and I cannot even remember how much time passed between “Katy” and I’s one tryst and when I could again feel like I was real.

At this time I was working in a cubicle of a small office on the second floor of a financial building. I won’t bore you with details but we worked on the retail sales side of the financial industry and my team was small but hard working. Read more »

[MF] My second high school crush/large breasted experience

Hello again! Thanks for all the responses and PMs from my last post. I encourage you all to reach out via PM. If you haven’t read my first story see it [here](https://www.reddit.com/r/gonewildstories/comments/6cnbw4/my_first_largebreasted_high_school_crush/).

If you want to ignore the setup and just get to the sexy part, scroll down, I have it labeled.

Some more context on this, in my last story I brought up two girls in my high school that I had huge crushes on. We’re calling them Kristin and Aly on here. My last post was about my first experience with Kristin, this one is about Aly.

So some context about Aly. She was much different from Kristin. She was athletic(ran cross country and played basketball, had to wear 3 sports bras to keep her 34DDDs from hitting her face when she ran, now that’s dedication), popular and super cute. She had boyfriends in high school and did not really have a bad reputation. The only people who talked badly about her were girls that were just jealous of the attention she got from her tits. I totally would have been ok dating her if we were both available/if I had more confidence. I don’t know if I can explain how breathtaking her body was, she had huge natural tits but she had a tight and athletic body. Most girls with my ideal hugeness of tits have some fat on her. She also had a gorgeous smile. Not gonna lie, I totally pumped off a few times to her Facebook summer album throughout HS. Read more »

[M]y [F]irst large-breasted/ high school crush experience

Sorry there’s a lot of exposition here scroll down if you just want the sexy part

Okay so some context here: Deep down I have always been a boob guy. I have also been more concerned with what people thought of me so I only dated a certain type of girl (typically goody good who isn’t too gifted in the boob category). So this all starts at the end of high school where my HS GF and I had just broken up.

There were two girls at my HS that I had a huge crush on, really admiring both of their large tits. Lets just call them Kristin and Aly. This story is about Kristin… See another post for Aly.

Kristin was not only super cute with giant boobs but she also had a bit of a reputation. She had been with or was rumored to have been with a lot of guys and she was kind of a loner. She didn’t care what people thought of her, I admired that. I was obsessed with how I was perceived by my peers so, even though I was always into her especially with the stories I heard, I never made a move. Read more »

[MF] Let’s all laugh about the time I got a boner during a school physical from an old ass nurse

DISCLAIMER: this story did not end in any sexual activities. It is just a funny/embarrassing story that happened to me years ago. I’m sure some of you will be able to fantasize it and take it wherever you want (I do), but most will probably not get off from reading it. Skip to the line to avoid background info.

You know how you can just suppress embarrassing shit that happens to you to the point where you forget it even happened? Well, this is one of those times. I recently remembered this while high as beans and figured I’d share it with you strangers.

This happened about 7 years ago while I was in high school (freshman or sophomore), so some of the details are hazy. I’ll try to retell it with as much accuracy as possible. Read more »

“The Best Fuck” My “Friend” Ever Had..[MF][Cheating] (Part One)

This story goes back a long ways..

When I was in high school one of my best friends started dating this girl called, “Cindy”. She was.. fucking stunning. She was probably 5’6 or so, she had darker hair with big tits (probably Cs), and a round ass.

She was popular, but had a little more brooding to her than a cheerleader vibe. So a lot of guys didn’t know what to make or do with her. She played varsity tennis and was good, very good. All I remember from watching her was, I was watching perfection. Longer legs that were lost in an amazing ass. Her tits were full, welcoming. Her skin was tanned and her smile was blinding. She was gorgeous.

One evening, she called me. The call was made under the pretense that her and my friend, “Brad”, had just gotten into this big fight and she was calling me as his friend to try to understand him better. I knew this wasn’t her true intent. I had never knew her before she started dating my friend. But we had talked briefly here and there and she always left the conversation with a questionable smile. Read more »

In case of an emergency break a cock [MF]

It was the second half of freshman year. I met Anna in the first week of class. I made a joke about Shakespeare being just the Elizabethean era’s version of the pro wrestling. That made her laugh. I had broken up with my high school girlfriend and was not looking for anyone at the time and she was seeing someone else. So we just started to hang out and enjoy each other’s company

We had become close with the odd uncertainty of mutual attraction that we could speak of dispassionately and do nothing about. By the time registration for the second semester had rolled around, we decided to take a core class together, and we chose Astronomy as both needed to knock off a science class. We thought it would be easy enough, but whoops, it was not. It was a brain breaker calculus based class.

So we started to spend every Thursday night in her dorm room together working on the homework we got on Wednesday that was due on Monday. We would work hard for a while, talk for a bit, work hard for a bit, and then have a couple of drinks. Read more »

[FF] I cheated on my HS boyfriend w/ my virgin best friend

Hey, this is my first reddit submission. Talking about my first (and only) experience with a girl.

We were 15 and I’d already been with my high school boyfriend for a year. I’d been sexually active for a few months, but my best friend, Nina was still a virgin. We were both young with dark hair and tan skin. I was a little tinier than her, with small tits and a cute butt. She was a more voluptuous, with full, developed boobs that I was jealous of. She’d always been kind of a homophobe, so I was surprised as to what happened that night.

As per usual, I spent Saturday night sleeping at her house, and after a night of popcorn and movies, we crashed out in her bed… I had a really hot dream that night; I woke up feeling super horny. I was laying on my side with my back to Nina. Read more »

[MF] Graduation

It was a very special day my sister was graduating high school. It was an exciting day but wasn’t expecting for this day to be even more exciting. My sister was getting ready when I heard knocking on the door. It was two of her friends. One of them was my ex. We ended up staying friends after the break up. I greeted them in & walked them to my sisters room. I walked back to my room to watch a movie. Before starting it up I heard a knocking at my door. I told them to come in. It was my ex looking so beautiful & sexy with her tight short dress. She had my complete attention. “Can you help me zip my dress?” She asked. “Sure” I responded. We started talking about how we’ve grown since we first met each other. While zipping her dress I noticed that she wasn’t wearing a bra. “You better be careful” I said. “Why?” She said looking confused. “You don’t want your boobs popping out of your dress” I answered. “It’s not like you haven’t seen them before, ” she joked. “I know them very well, but they’re mine & I don’t want other people looking at them” I joked. We begin talking about the first time we had sex. How nervous she was loosing her virginity. “I’m really nervous about today, ” she said. I grabbed her & held her in my arms. “Don’t be nervous. You look very beautiful. Even though you dress might be a little too short.” I joked. I turned her around to see the back & it barely covered her ass. “Try to bend over to see if you can see under it” I asked. She leaned forward & the dress lifted up. You could see that big ass popping out little by little. When she stopped I couldn’t tell if was wearing panties. She normally wears thongs. “Are you wearing panties on?” I asked nervously. “No, ” she blushed. “Are you lying?” I asked. “Check if you don’t believe me, ” she answered. I wanted to check so bad, but I had a GF. She was at her mom’s getting ready with our daughter for the graduation. Temptation got to me & I lifted her dress up to her stomach. No panties! I was hard & ready to go. I rubbed her ass gently as I turned her around to see the front. Her pussy was clean shaved soft & smooth. “I’ve missed your hands on my body, ” she whispered. “Remember how we use to have sex before I’d go play soccer” she asked while I rubbed her ass. “What if we finish it with my graduation?” she asked blushing. She got on top of my lap. Sitting on top of my hard cock. “Looks like someone likes the idea, ” she joked. My mind was running wild. Especially now that she had her big ass on my cock. She began to move her ass around getting me more excited. I snapped & picked her up. I threw her on the bed. Spreading her legs open. Kissing her from her feet up her leg. Stopping at her inner thigh. Teasing her wet pussy. I began eating her out. Sticking my tongue deep inside her. Watching her moan with each lick. Her pussy was soaking wet. Dripping down to her ass. I flipped her around & slid my tongue between her ass. Eating her ass wets too. The good thing was that the movie was loud. “Wait! I don’t want my dress to get stained like the other one” she moaned. The other dress stained is another story for later. I unzipped her dress & gently took it off. Exposing her sexy body. Wide hips, big ass, tiny waist, & medium size breast. She threw me on the bed. She pulled my shorts & briefs off. Grabbing my cock & began licking it wet. I could tell she’s got way better from before. My cock was throbbing from how hard it was. She slides her body up & on top of me. Grabbing my cock & putting the tip on her pussy. She slowly went down on it. Moaning instantly as she went down. Starting out slow & picking up the pace. She wasn’t moaning anymore. She was screaming with a pillow on her face so they wouldn’t hear us. We were getting all sweaty & sticky. I was about to pull out when she pulled me closer. “Don’t pull out baby. Please cum inside me, ” she moaned. At that point I was so out of my mind. I was only thinking about that moment. So I pushed deep inside her & let it all out. She laid on top of me. Kissing each other knowing there’s a possibility she could be pregnant after this.

I Said You Can Call Me Becky [MF] [age gap] [teen] [milf] [oral] [anal] [cheating wife]

*(This is a bit longer than my last one, but that’s because it’s inspired by two audios that are related. There are flashbacks in this story which are separated and italicized for your convenience. Thanks for reading.)*

It was just shy of two in the afternoon, an hour before her son would get out of school, when there was a knock at the door. Having been completely spaced out, mindlessly folding laundry, Becky almost jumped at the sound. The just past forty year old answered the door, surprised, yet somehow expecting the boy, or man really, who stood on her doorstep. He stood, easily a foot taller than her, making no attempt to disguise the fact that he loved the sight of her voluptuous form in that snug little sundress. Maybe he had been a bit for discreet before, but now, he was brimming with confidence. Becky hated to admit that she loved that cocky hint of a grin on his face.

“Hey there, Mrs. C. Mind if I come in?” He spoke as if he had no idea what kind of effect he had on her, but he wasn’t fooling anyone. Read more »