Tag: High School

A few stories that were dug up during chats this past weekend (tM, tMF, TMM).

(sigh, I guess my account has once again been locked out. Whatever so I made a new one. I'll post pics again later but here are some things I was planning on posting on my /u/gurlypussy account.

A few chats this weekend led to me retelling a few stories that I thought I would compile here. I'm not trying to write a book but a few people asked some cool questions, I told some stories and copy and pasted most of it here.

  • My first time with a guy
  • My first threesome
  • The first time I was really slutty.

My first time with a guy.

My first time with a guy was when I was in college. I'd had girlfriends in high school but I was just starting to explore crossdressing and was really interested in following through with it so one weekend I did just that. I met a few guys in a chatroom online, exchanged a few photos and picked out one guy in particular. He was nearby and could host which was good because I had roommates at the time and was still pretty secretive about my sexlife. So we agreed on a time for later in the day for me to go to his place with no pretenses other than I wanted to see what it was like to be fucked. Read more »

My Last Summer at Home (FFM, mild domination)

During high school I lived in a small town in the mid-west where nothing ever happens. We had a drive-in movie that had just reopened, a bowling alley, a pizza joint, a supermarket, and two gas stations. The summer before I left for Iowa State University, I worked in our town's supermarket so I had some spending money in the fall. When I wasn't working, I just read books or surfed the web. On the cool summer nights, I cruised the quiet streets our little town with my best friend Jill. She was always there for me through good times or bad, and we sure had fun that summer before going off to the big world.

Jill and I operated the checkouts at the supermarket and we would always tease our boss Rickey, just to make the days more interesting. Rickey was a year younger than us, but he was the owners son, so he was our manager. He was cute and easy to embarrass, so we cut him a break and followed his rules most of the time. Rickey was shorter than us and probably 120 lbs. soaking wet, so he wasn't hard to intimidate. We liked to think we were so worldly, particularly in our little short blue uniforms. Rickey's dad had let us pick them out from a uniform catalog, and we chose the shortest ones they sold just to tease Rickey. Read more »

Losing my virginity as a christian camp counselor [F/m]

I’ve been a long time lurker here and have always considered this sub one of my favorite guilty pleasures—a pleasure that neither my family or fiancé would find appropriate or appreciate. I’m too embarrassed and fearful of judgment to buy and own books, and watching rather than reading tends to be a bit much for me so the internet and sites like literotica help to quench my thirsty imagination though I do have to sift through a lot.

I don’t really have many stories of my own to add to the archive, let alone anything remotely like most things on here, but I’m getting married in less than a month and the closer it gets to the date the more I look back and dwell on what little experience I do have.

I’ve only been with two men, my fiancé and the man I lost my virginity to. Recently, every time we discuss the upcoming nuptials and especially the honeymoon, it seems like the knowledge of my one previous experience has somehow become a point of contention. And honestly, the fact that it’s being discussed so much has me thinking about it more than I think is healthy. Read more »

Isabella: A Fantasy [fM]

“Blood, sex, and death.” The holy trinity of every Gothic horror novel, according to Mr. Fitzgerald. He was the high school literature teacher I hopelessly crushed on, and I couldn’t help but notice his eyes lingering on me when he said that second word.

I was a senior back then, about to graduate. The spring when my classmates were perpetually tuned out during class, with only the summer ahead and college on their minds. But I still had unfinished business here, and this day in May he wore a light blue button-up and chinos just snug enough to drive my imagination wild. When he perched on the edge of his desk reading from The Strange Case of Dr. Jekyll and Mr. Hyde, I let my eyes wander up and down his body, picturing his skin on mine. By then I’d dreamt up this sultry side to him, one he hid away at work, but which made him all the more irresistible . . .

He was the new cute teacher this year, fresh out of college, the one the girls whispered about between classes. For a while, I tried to pretend I wasn’t one of them – after all, how cliched is it to have the same crush as everyone else? Yet his charm was undeniable. Intimidating, even. And by God, who else could make the classics so sexy? Read more »

My [F]avorite and [F]irst Ho[m]ecoming Dance

I posted earlier with a different story about Polly and I (under a different username…don't ask)…But this story is a couple months later with two different girls. Be warned this is going to be long.

I was a junior in high school and had never attended a school dance. Not that I thought I was too cool or any of that, I just didn't really have all that much of an interest the first two years. I was always working or hanging with friends. One year I was invited by this girl I had been flirting with for a while, Jennifer.

Jennifer was rather tall, tan, light brown hair down to her middle back, South African with a slight accent and stunningly gorgeous set of blue/green eyes. She had long shapely legs that caused me to almost turn to putty when she was around and lastly her boobs. Eeeh Gods they were perfect!

Needless to say, I had a rather large crush on her. She went to our rival high school and was a swimmer there. We met when we were young through our parents and were never really all that close until we ran into each other a few weeks before homecoming season when her family came over to mine for dinner and we reconnected. Read more »

Allie: Or, the Sleep-Over (MF) (Age gap)

Allie

The girls made their way down the crowded hallways at Thomas Paine High School. The two girls weaved through the throng of callous high schoolers, quiet amongst the hysteria of a Friday afternoon. The girls walked next to each other, books pressed to their chests, and straining to hold the line through the rough crowd. It was their 4rd period, which was the last for seniors, and it was Art.

Maddie turned to her friend, Allie, and said “I wanna skip. I’m too excited to hang out this weekend.” She jumped in front of her friend, ponytail bouncing, and begged: “please Allie. It’s just art. You’re a good artist anyway. Allie smiled and shook her head.

“My mom would be so mad if she found out!”

“Please Allie! We can watch Dr. Who!” She pleaded, shaking her shoulders from side to side.

“I can’t miss!”

“I’ll do anything!”

“Like what”

“I’ll…”

“Fine, but we’re watching Matt Smith!” Read more »

“An unceasing desire” Installment 1 of possibly many to come (hah)

So writing is fun, but takes a lot of time. If you guys like this story so far I'll add more later. It's going to be about man and his increasingly persistent libido, which leads to many interesting encounters but eventually disrupts his psychology and mental health and leads him to disaster and depression… until he encounters a mysterious girl named Lihua, who helps him to overcome this affliction.
 

Dear Lihua, Where to begin? After reading my note, you may not believe me. You may think that I am a deviant pervert, a delusional eromaniac or simply a stalker. But I must tell you, and I must thank you Lihua, for saving me from the torture that I had lived for thirty five years of my sad life.
 

Lihua, if that is your real name. We met only once nearly seven years ago. To you, that night was probably only a fleeting bit of fun or rebellion; you were so young and without a care in the world. You told me you were twenty three, but I didn't believe it even then. I could tell from your honest eyes and your smooth, tender skin… and from the way you giggled and your high voice. I only hope that you were of age… I imagine that since then you have changed quite a lot. I only hope that the world was not overly cruel in taking away your youth. I hope that I did not contribute to that inevitability…
  Read more »

Smart Boys are Dumb: A “Mostly True” Erotic Adventure (MF)

http://www.harlottesometimes.com/2015/03/smart-boys-are-dumb-mostly-true-erotic.html

Thank you so much reddit! You have ALWAYS been good to me. In appreciation, please enjoy my latest Flash Fiction. I've copied the entire story here.

If you enjoy my dirty little stories and want some more, feel free to ask! I get so HOT when you message me!

Smart Boys are Dumb

by Harlotte Sometimes

He and I just met. We’re sitting on the floor of someone’s dirty dorm room. Lots of people — we’re all Freshmen — crowd. They’re here to smoke. I’m here to get laid.

My “Friend” from high school told me I “simply must” come visit her fancy college. “Rich, smart boys are so gorgeous,” T said.

So here I am, “visiting.” I eye the kids in this room as they pass a joint. I wonder when the smart, rich boys will arrive.

T makes googly eyes and giggles for a tall, weird California kid. He brought the pot. T says he can get coke and E, but so far California has not delivered. Fancy College boys seem pretty square and inhibited. Most cough and choke on inhale. Read more »

Kerina’s College Humiliation, Ch.1: Kerina [f][Fsub][huml]

Kerina was from the country. She had done very well in High School, was skipped ahead a year and ended up in College at age 17. Kerina's parent were farmers and weren't very well off financially. The College that Kerina got into was in the city and so the best they could do for her was a shared dorm room.

Kerina was quite a beauty. She was 5'3 with long blonde wavy hair. Slim and pretty with a flat tummy and striking blue-green eyes. She didn't have large breasts, but they were by no means small either. She had had a few boyfriends whilst she was growing up but had never done more than kissing. Usually her relationships had broken up as the guy had wanted more but she wouldn't do it. She attended her local church and was generally well behaved and quiet.

So Kerina moved to the city. She was sharing her small dorm room with an older girl named Lisa. Kerina soon got used to her routine and spent most of her time in class, studying in her room or in the library, swimming laps in the pool occasionally going to the College's girl's church group and sleeping. Kerina really felt the pressure to do well, since she was younger than everyone else there. Read more »

The New Neighbor

1

Cheryl walked outside her door to a bright and sunny day.

"Lovely," she said out loud as she made her way to her car. Hitting the button to unlock the doors she noticed a moving van in the neighboring driveway. Had someone finally bought the house? She was still a bit early to meet her girlfriend Sharron at the mall so she decided it might be a good idea to meet these new neighbors. She walked around the white fence that separated the driveways.

There was movement inside the van. "Hello?" she said. "Is someone in there?"

The movement stopped. A moment later a young man hopped from the back. He was roughly six foot with blond hair in an almost crew-cut style. His build wasn't particularly impressive, but he could have been military. "Ugh," thought Cheryl. Military men had never been her thing, even less so when she was cheated on by her ex-husband who had been a military man himself. She ultimately chalked it up to her going for something outside of her normal preferences. It never would have worked out. Read more »