Tag: High School

How I ended up having anal sex with a girl before PIV (Interracial, Virgins, Long) [m18/f18]

So some disclaimers: this is long and will take a while to get to the sexual stuff. I have changed some superficial details and names to protect identities but otherwise this is a completely true story of my first sexual experiences and how I ended up having anal sex with a girl before I’d had PIV sex. I am not a writer of any description and this is my first attempt at a story so be gentle. Also, be assured that there is no Loch Ness Monster. Look for the break if you want to skip to where things get sexual.

I left high school a virgin. Not just a virgin, but a never been kissed virgin. Girls wouldn’t just turn me down, they seemed to be a bit insulted that I thought I had a chance. I was short, pale, and geeky. I had acne, braces and was painfully shy. I went off to University aged 18 with my acne gone and braces removed. Regardless, I had built up a lot of insecurities about my attractiveness. Girls didn’t seem to be horrified by me anymore but I was still no girl’s fantasy. A solid 5 out of 10. But that was ok, I had long since made peace with the fact that I was no model. My confidence slowly grew from nothing to still almost non-existent but something. I went on a few casual dates and even kissed a couple of girls, but never got any further than that. Read more »

Morning Sex of the Future [Mf][Oral]

*Sometime in the future…*

The sun was rising, on what promised to be another hot South California day, when Alex awoke in his cozy bed with the usual morning hard-on. His wife, Genia, was still sleeping soundly, rather she was still unconscious from her nightly habit of pills and wine. He gently eased out of bed and put on a pair of sweat pants before leaving the room and making his way down stairs, through the kitchen and out the sliding glass door into the backyard and a gray early morning mist. He quickly walked to the far end of the pool heading for the Man Cave located in the converted pool house. Alex put a lot of work into the Man Cave installing a couch, a sixty inch screen, small kitchen and bathroom. It’s the place where Genia makes him stash all his ‘tasteless man junk’; a bean bag, antique movie posters, and the PacMan arcade game he restored himself. And best of all, it was home to Shelby. Read more »

A naughty, slutty fantasy fuck with my neighbor that was two years in the making (f/m)

This story happened years ago when I was at the peak of being a bratty slut.

 

My parents are both executives and we live in an affluent neighborhood in a southeastern state. We live next door to Mike and Lilly, who are in their late 30s and own their own business. I’m Kenzie.and I was a 19 year old college student when this affair happened. I’m 5’8″ 140 lbs, brunette with 32B tits and I’m told I have a nice waist to ass ratio. I was home from college for the summer and got to act on a fantasy I’ve had since I was 17. I still feel bad because I seduced a married man and I’m nervous his wife will somehow find out one day.

 

The Backstory:

 

When I was a junior in high school, my parents had a backyard, spring bbq with friends and neighbors. This was the first time I felt sexual energy between myself and our next door neighbor Mike. I had only recently started fantasizing about older men and found I was attracted to handsome men with power. I think it started with feelings for my physics teacher. Read more »

My [F]irst [M]onster Cock

Hi, my name is Ashleigh and I’m a size queen. Now, that doesn’t mean I’m an elitist. If I only fucked huge dicks, I would barely ever get laid. I just prefer a penis size that most women would find to be uncomfortable or outright painful. But some of the best sex I’ve ever had was from average sized guys. Being a “size queen”, to me, means the bigger you are, the more likely I am to fuck you for the sake of fucking you. This story is how I learned that I really do love monsters.

By the end of high school, I had sex with 29 different guys. It was a lot, but it was spread out over time and over social groups (theater, stoners, tennis). Some were just once, some were quite a few times. Now I was 5’5”, tan with short dark blonde hair, 105lb and athletic, with a 32D bra, so if I wanted to get with a willing guy, I could get him. I was (and am) a very sexual person, so I took advantage of this: I had 3 or 4 FWB who I could fool around with at any time, and if someone new caught my eye, I would fuck him too. I kept track of it all in a little book, and realized that I liked the bigger dicks. I felt fuller and more satisfied. Read more »

Revenge Is A (Naked Cumsoaked) B*tch [Mf] [blkmail] [huml] [reluc]

Summer was that girl in high school. The almighty popular one – tall, fit, perfectly blonde, perfectly tanned. She was always dripping in Tiffany, drove a white BMW and threw all the best parties. Whenever Spring Break came around, people waited anxiously for her to post bikini pictures. The second those albums came out on Facebook, word spread across town like wildfire. By evening, every male classmate and teacher would have jacked off to Summer’s tits at least once. And, of course, they would have saved the rest of the album to a private folder for future use.

Evan was no exception. He remembered the days when he received texts from friends to alert him of the “Summer Blockbuster.” He’d drop everything he was doing to rush to his computer, pick his favorite shots and then whip out his dick. He remembered a particularly depraved year when he printed out a photo just to cum all over it. The shot was a beautiful one of Summer laughing, her blue eyes crinkling, her perfect teeth glistening. Evan remembered firing his thick load all over her wide-open mouth.

He’d picked the picture because it was such a lie. Read more »

[m/f] Matching with my middle school best friend on Tinder

I’ve had this sitting on my laptop for a week. Not really debating on posting it; I just haven’t gotten around to it until now. It’s pretty long too because I felt like you needed to hear all the backstory to appreciate it.

I was browsing Tinder like any other night, sitting on the toilet while swiping left and right. Then I saw an old friend that I haven’t seen since like 10th grade because she moved away with her dad while her mom stayed here. She would come back for Christmas and summer break, but I would always be gone with family.

I decided not to go with my family this summer. I’m 22 now, a real man. So I liked her, got off the toilet, and went to watch Bob’s Burgers. I was just waiting for one of my friends to text me to do something. Then I got a message on Tinder from the girl, Heather. “Hey handsome :)”

A little bit about me: My name is Chris, I’m 6’5, and I’m 195 lbs. I have brown hair that’s bleached, short on the sides, longer on top it goes past my eyes if I pull it down my face, but that’s usually loosely styled on top. Read more »

UPDATE: Fucked the work experience girl again last weekend [M35/F18]

[PREVIOUS POST](https://www.reddit.com/r/gonewildstories/comments/4q9m5z/fucked_the_work_experience_girl_last_weekend/)

*tldr: After striking up a friendship with the work experience girl (Laura), I gave her my number (at great risk) during her last day at the office. Turns out that she also had a crush on me and incidentally was a horny sex freak. Last weekend we had sex all night in a budget hotel room.*

———–

 

After the events of last weekend, to say I’ve had a bit of a spring in my step all week would be a massive understatement. Not only did I get to have sex for the first time in literally years, but knowing that I still had the ability to attract younger girls at my age was a massive confidence booster. I consciously had to tone down my borderline obnoxious cheer after one of my co-workers, correctly assuming that I had gotten laid, starting pressing me for details. After realizing that revealing the truth would most likely have consequences – or at least be highly scandalous – I played coy, resolving to keep the affair to myself for the time being.

  Read more »

The Ten Year-Itch (M/F)

**NAUGHTY BITS AFTER THE JUMP**

Carrie (27) and I (28) have been friends since high school. We went to a pretty preppy boarding school together and she was in the year below me. Both being tennis enthusiasts, she managed the Varsity boys team while I gave up my spot to help coach JV since they didn’t have a coach and I could basically hang out with her all day. Just the two of us. She was new to the school that year but we got along well and my JV players seemed wowed by the fact that I got along with the tall, gorgeous, statuesque blonde who had a charming smile that seemed to hide a naughty side as well.

Nothing had ever happened between us. Years later, we’re still friends, we went to the same college, we hang out in the same social circles, we talk all the time. She’s retained her marvelous figure, her sharp features and blonde tresses haven’t aged a day, and if anything, the years have added a sense of security to her that says “I know what the fuck I’m doing.” I’ve dated a few girls she’s introduced to me, and she’s hooked up with a few of my friends. Nothing serious. We’re close but there was always a barrier on talking about a few things. Sex, relationships, that sort of thing. Read more »

[F]un ti[M]es with an old friend at his beach house.

So this happened this past weekend and since I love reading through this sub I figured I would contribute a little as well. I’m 21, recently graduated from college and recently dumped by my long time boyfriend :( 5’7, slim figure, blonde hair and and 34B breasts for those that want to know. You can skip to the dashed line if you want to get to the hot stuff.

This story begins when I got a snap from Greg, who had just moved out to a tiny town after graduating for work. we’ve been good friends since high school but never hooked up even though we’re both attracted to each other. I could definitely feel him staring at my ass whenever I would walk away in yoga pants, and had I not been dating my ex at the time maybe something would have happened, who knows. He’s six feet, athletic build, brown hair and a light beard.

The snap he sent showed him on a beach in his new town with the tagline ‘come visit me before I tan myself into a leather couch’. I figured he’d sent it to a few people but given my recent breakup and our mutual attraction I decided it wouldn’t hurt to flirt back a bit. Read more »

Off the Courts • Part 1 [MF]

I love my job. Not many women work seriously in my field but I love it. I started coaching tennis when I was in high school. I actually hated playing tennis as a junior player but I need to make some money for myself, since my family was hit pretty hard during the recession. When I first started coaching most of my students were in elementary school and I honestly didn’t know anything. I’ve moved around quite a bit and I’ve learned have a greater respect for the sport. Read more »