Tag: High School

The Book of Jennifer – Chapter 1

PROLOGUE

My name is Tyler Kane. I’m a writer. And have been for a very long time. Since I was a kid, I’ve been obsessed with writing. Making stories out of everything from real life events to deep fantasies and often a combination of the two.

I write mostly horror or thriller novels now, but my love for writing started in high school. Senior year. When I started writing erotica. But not just run of the mill fantasies. I decided that I would keep a book for every relationship I have and, in it, detail the events of said relationship. Happy to say after all these years, I have had some truly euphoric relationships. Ones that I look fondly back on. And so I decided that writing them and keeping them to myself wasn’t enough.

I will publish my writings for free for the people of the internet. So you too can live life through my eyes. (At least the good parts.) But to keep it orderly I will release one book at a time. One for each relationship. Because I have to type out all these based on my notebook writings, I will not release them in order of occurrence. Rather the order in which I type them. The following chapters depict my relationship with Jennifer. Enjoy. Read more »

[M]y night of [F]irsts

So, I was a late bloomer, sort of.

I did fine talking to girls and all, but as a somewhat overweight kid from pretty much birth up through, well, now, I had a MAJOR confidence problem when it came to actually thinking girls were into me. All through high school and college, up until I was probably 27 or 28, I just defaulted to thinking girls weren’t into me.

When high school ended, I was still a virgin. I’d made out, had a girl topless a few times, fingered a girl. But I’d never had my pants off, and I had certainly never gone down on a girl. I made it through my first semester of college with little more than that, not even getting what I’d managed once every six or so months back in high school.

Then came second semester, January weather, and a gift from god in the form of a six foot redhead with a tendency to decide she wanted someone at random and then Take. Fucking. Charge.

I ran into her as I was walking into my dorm building at something like eight o’clock one random Wednesday evening. She was hanging with a couple of friends, having a cigarette outside. I’d seen her around at a couple of parties, knew her name, she knew mine. Read more »

The Hotel [MF]

“That’ll be 12.50 Sir”

I see the hotel in front of me.  

“Sir! That’ll be 12.50?!”

“Oh! Sorry I was districted”
I say digging into my pocket for the fare. 
Handing him a 10 and a 5 dollar bill. 
“That’s good, keep the change”

He gets out of the  cab and helps me bring my luggage to the door. 

I get the counter and give my name. The gentleman takes my credit card and taps on keys in rhythmic tune on the keyboard. 
He hands me my card back along with the key card for my room, I gather my luggage and make my way to the elevator. 

I fall. . . 
Falling freely with my arms wide open. 
Hitting the soft surface of the blankets then the firmness of the mattress. 
I let out a long groan of satisfaction that I’m done traveling for the day. 

I turn onto my back folding my hands on my chest. 
Feels so good to get away, even for just a night. 
There’s a vibration on the bed. 
I reach my arm out and begin sliding my hand around and find my cell. 

“Hello?” Read more »

[MF] stranded with the babysitter (very long)

ok guys, this happened a few weeks ago and i just absolutely NEED to tell someone. This story is absolutely full of bad decisions so if you can get past that then read on. Also prepare for horrible grammar and past tense present tense flip flops

Some backstory, im a 25 year old busy (married) professional with children. I hired a nanny (the title says babysitter because come on, thats way hotter. She is in fact a nanny which is basically a babysitter that i pay a lot more.) About 8 months ago. Her name is alyssa. Shes 19 yo petite, long brunette hair that almost touches her bubbly ass, with a perky pair of c cup breasts. Long legs and a very cute face with full pouty lips. Shes very mature and smart as fuck, and insanely professional which helps because it forces me to behave and not say anything too inapropriate around her, and she is absolutely steller at her job. Basically our relationship up to this point has been very professionally platonic though i definitely have jerked off thinking about her often. Read more »

Double Feature Picture Show [MF] [Exhibition] [Rough] [Long]

“See it’s like he’s dead or something.” Jenny said, having pulled the sides of her backless dress forward, pushing the fabric between her now bare breasts. She gave her shoulders a shake to jiggle them a little. I certainly looked, it wasn’t an unpleasant sight, but she didn’t break my concentration like most of the other guys in the parking lot. I continued to mix her drink and hand it over.

Those who have been to Rocky Horror are aware the culture there is much more relaxed than most places. People dressed in skimpy lingerie, both men and women, business suits, and sometimes just night shirts all together tend to learn and be accepting of each other’s quirks.

I had mentioned before in stories here that for one reason or another I just don’t have the same drive as most people. I wouldn’t quite classify myself as asexual, as I still enjoy sex. It’s not a chore for me, but I just lack the same amount of interest in it as others except for certain… cases. Read more »

His Name was Richard [f] [M] [oral] [anal] [squirt] [cum]

You’re asking me: How do you know his name was Richard? And I’ll tell you: I went to the mail room and looked at his mail box. I got his last name, got on Google and searched. Bam. Richard. 47.

He was a silver fox. He had short but stylish silver hair and a beard to match, muscles — so many muscles! And a few old tattoos on his forearms. I wanted to fuck him. I wanted him to fuck me. But I was too shy.

My parents bought me the apartment when I enrolled in college. They rented it out for two years and then, this year when I became a junior, I moved into it. My very own place!

I saw Richard on my first night in the studio apartment. He was on his balcony smoking a pipe. A pipe of all things. I thought, this guy is probably an author. Didn’t hurt my fantasy when he sat down and pulled out a thick book.

I started thinking about his cock and I wondered if it was as thick as the book he was reading. I just needed an in. I’m shy, okay? Too shy. I’m not like the girls in my school who send guys a pic of their tits and say “come over.” Read more »

[MF] teacher student hookup

First time poster, long time reader!
There was this super fucking hot teacher in my high school, but i didn’t have the hots for him until the lad semester of senior year. I also caught him checking me out once in the parking lot. And at graduation we kept making eye contact, wild.
Anyways, nothing happened until that July. We started talking on Facebook and then he asked me on a date to meet up. So I drove over to his house (which was pretty far) and went up to his apartment. He was wearing a wife beater and shorts so obviously he didn’t want to go out (disappointing) but whatever. We sat there and talked for 3 hours before I guess he was tired of it and just pulled me into his lap and started making out with me. He un did my buttons and tried to finger me but the angle was too awkward so he pulled me up and took me to his bedroom. He laid me down, took my pants off and started fingering me there. I hadn’t really had anything big or had sex for a while actually so I was super tight. It hurt. He didn’t really know what he was doing either lmao. So he gets on top of me, puts a condom on and after sucking on my clit (that he did right, felt amazing) he put his dick in me. He was thick and he was like 9 inches so it really hurt. I’d never been that stretched out before. He did a few thrusts and I clearly remember him saying “give me that ass” hahahaha. So he flipped me over and we did prone bone. He lasted maybe 2 minutes and I was nowhere near getting off. I was disappointed because I thought he was a 2 pump chump. (I later found out it’d also been a while for him) after that he threw the condom away and we laid there with his dick a few inches from my face just out in the open and flabby. This was only my second person to have sex with so I was still very much not experienced. And he also didn’t really know what he was doing. But I went back for more and we ended up having a weird relationship for a few months.

[FWB] [MF] Asians FWB?

FWB?

So last weekend I was at my friends house because she needed some help moving into her new apartment.

I get to her old house and we spend about 30 minutes drinking coffee and catching up. We talked about our weekend plans and how work is going. Simple stuff like that. We have been friends since high school. We had a thing for each other during our freshmen year in high school but she wasn’t single for very long. I believe her and her boyfriend are still together but he now works out of state for an internship. She accepted a new job and is moving out to live closer to it.

But anyway, we finish catching up and start packing. She has already packed some boxes and I start loading those into my truck first. After a while, I finished loading all of the boxes and asked her if there’s anything else I could do. She said yes and I followed her to her room. There was a bunch of stuff scattered everywhere such as clothes, makeup, shoes, heels, random books, etc etc. Read more »

Letting it all hang out: [M]y future wi[F]e and her [F]reshman roommate

… some good times in college from a long time back!

The first glimpse:

This all starts at the beginning of freshman year. I’d just got to college and about a week in, I’d met everyone on my dorm floor but was still getting to know people. Naturally, I was especially interested in getting to know the freshman girls. This one particular night, after some or other social event, I and an upperclassman guy were chatting with Kate and Monica, two seemingly pleasant and attractive first-year soccer players who shared a room. It was late and they’d already changed into pyjamas — Monica in shorts and t-shirt and Kate in a short-legged onsie-type thing. They were sitting on a couple of bean bag chairs on the far side of their room and me and the other guy were standing in the doorway, and we were just chatting about random stuff — classes, home, people we knew. Turned out Kate and I were from the same state and Kate vaguely knew a couple of my friends from back home. Kate was a little restless and was shifting around on the chair. We were getting on to talk about some of Monica’s classes when I noticed in the corner of my eye that Kate’s legs were a little apart and the onesie had shifted itself to one side. A cute splash of golden curls with a little slit below were plainly visible. It was quite clear Kate had no idea she was doing this and there was a moment where I could have interrupted to alert her, but I couldn’t think of a tactful way to describe the situation, and then it seemed too late to do so. If the other guy had noticed anything, he made no sign, so I attempted to just ignore it and follow the conversation, while the sight of Kate’s pretty pussy continued to decorate my peripheral vision until she shifted again a few minutes later. After half an hour or so, with a few more glimpses as Kate got tired and slouched low in the chair, we all called in a night. Read more »

Sexy high school reunion led to sexy meta storytime – let [m]e know i[f] you want more! [meta]

So I’d just walked into my 10th High School reunion party when I saw her. Jenny Jones (not her real name, because her real name is Sarah Smith and she’d probably be annoyed about it being used in a dirty story online), my all-time HS crush. She was an unidentifyable mix of French and Asian and Black and Canadian and Jewish, she stood between 5’0” and 6’1”, with long thick slender legs and impossibly-perky antigravity-enabled tits that my cyborg-vision instantly identified as being perfect natural DD’s. Her flawless skin was pale like moonlight while also sporting a perfectly-smooth tan that definitely came from working outdoors rather than a tanning bed, and her makeup was bold and tastefully understated.

Jenny had been the captain of our schools volleyball team and soccer team and cheer squad and chess club, and had the ass and brains to match. I’d been madly in love with her when we were teens, but back then I was totally invisible to girls like her. We’d kept in loose contact on Facebook, and I’d come to really respect and admire her for her inspiring work to save orphans while also competing at the national level in woman’s synchronized diving, but it was clear she’d never forgotten her small-town roots, because her dirty pickup truck had a novelty license-plate holder that read “I’VE NEVER FORGOTTEN MY SMALL-TOWN ROOTS” and it was in her Instagram profile pic. Read more »