High School Archives — Page 253 of 805 — NSFW story

Life as a 19y/o [F] Sugar Baby – Part I

I sit in the half-full cafe as the jingle of cups and saucers surround me. The cute barista that offhandedly flirts with me when I get a coffee here is looking over at my empty table. I try not to let her know I notice her. I’m waiting for my date. Well, actually my client. My Sugar Daddy.

The newest one. The others are a story for another day but this is the Daddy I want to write about today. He’s very average. I know that doesn’t sound sexy but if you want the truth? Most Sugar Daddies are not Christan Grey. They are Michael Scott but less attractive (I dunno what that says about my Steve Carrel fetish) They are emotionally stunted civil engineers. The newly divorced middle-aged high school teacher or in Daniel’s case, just a well-off businesses owner with very mundane looks and awkward social skills. Read more »

I 20 [F] had wild sex with an old flame 23[M] in a parking garage and we almost got caught. (long)

I had my first kiss when I was in high school, with a guy who was 2 years older than me. We weren’t dating, and weren’t even friends, but we’d be forced to hang out once a week or so at dinners because our parents were close. I had had a bit of a crush on him, he was shy and dorky and a very talented pianist. I thought my feelings were unrequited, but one day, when we were in his room and our parents were having drinks, he locked his door and went “Wanna make out?”. I straddled him very un-sexily, we kissed with our tongues swatting about, it was painfully awkward and it never happened again. Later that year, he moved abroad for college and his family moved with him.

Fast-forward 5 years, I’m a 20 year old college student with enough experience to make me pretty sexually confident. And he’s gone from boring, awkward dork to sexy, business school graduate with a jawline that could cut steel. I know this only through Instagram posts and stories though; we haven’t been in touch at all for the last 5 years. It was his birthday a few days ago, as told to me via Facebook notification, and I don’t know what came over me, but I decided to message him a birthday wish and ask how his family’s doing. I didn’t expect a very enthusiastic response, and I didn’t get one. He sent a laconic few words. “Thank you! We’re fine, hope you and your family are well too :)”. Read more »

How I messed up the ending of my first threesome (in high school) [MFF]

This is a story about how I fucked up my first threesome. It was the high school senior class play wrap party (all participants were 18). My family owned a hunting cabin deep in the Poconos woods, about two miles back behind our home off a single lane road, that we rented to New Yorkers during hunting season, so the party (like many others in high school) was in the empty cabin.

This takes place in 1975. I’d been in all four class plays during my high school career. I don’t know if it was like this elsewhere, but with all four there was always a lot of random making out during rehearsal breaks. Girls with steady boyfriends not in the play would just start pawing and kissing me, or someone else. There was no intercourse or oral, but a LOT of petting and under clothes grouping, finger blasting, and the like. This could happen four or five times a night, with different pairings.

It was always confusing for me. Five or ten minutes of lust and then, when rehearsal ended, it’s like it never happened. Read more »

Candid Camera

Faith was still hungover when she woke up. She out on one of Liv’s bathrobes and made her way to the kitchen. She couldn’t believe that Liv’s house looked so clean. The party was small but it was wild and before the part of the night where Faith couldn’t remember anymore Liv’s house looked like a hurricane had blown through it. But this morning she woke up in a house that was clean, but not suspiciously so. There were a couple blankets and an empty popcorn bowl in the living room like Liv and Faith had just stayed up late watching movies, which is what Liv’s parents had been told was the agenda for the night. When she woke up Faith had been naked and so was Liv. She didn’t think anything had happened… this time. Faith had come a long way from the good Christian girl she had been at the start of senior year. (Behind closed doors, that is. To the town she was still the Reverend’s perfect little angel.) She knew that all the boys she had been with were forgivable, but if her father ever knew she had lain with girls she would be out on her ass disowned. Her father had been so disappointed when she broke up with Jesse Singer. He sang in the church choir and was a star of the wrestling team and above all a good Christian boy. But senior year when Liv became a sexually adventurous free spirit, Faith decided she wanted to dip her tow into the waters of sin herself. Jesse had kept her secret but refused to take the plunge with her, so they broke up. Faith had actually lost her virginity to Liv. All the boys she slept with were boys Liv had already slept with. Read more »

(M/F) A costly mistake leads to a painful lesson.

I was running late for a lecture when it happened. The Porche in front of me hit the brakes suddenly and I was just slightly too close. I skidded agonisingly then with a delicate “crunch” came to a stop.

“Shit!” I said and got out to inspect the damage.

Surely it couldn’t be too bad.

An attractive blonde, maybe mid-30s emerged from the Porche, looking not surprisingly quite unhappy.
“Are you okay?” I asked anxiously.

She adjusted the jacket of her charcoal business suit, which truth be told, fitted her extremely well.
“Yes, I’m fine, you hardly touched me. Let’s hope there’s not too much damage.”

“Sorry, I was too close, I’m running late.”

Ironically, the bumper of my clunker was barely dented, but the back of her car was going to need some serious work. My heart sank.

“Well that’s not going to be cheap. I hope you’re insured.” She said.

I wasn’t, and as a university student there was no way I as going to be able to pay for the repairs.

“Right,” she sighed. “I live just around the corner. Follow me there and we’ll work something out.” Read more »

How Diane uses her vibrator [F18][College][Masturbation]

“For the seniors… this is the last dance… You may never compete again. You’ll have your whole lives to remember what you did during your career as an athlete… so make it count… don’t hold back… when you cross that line, I want your tank to read empty… I’m so proud of all of you… when you put in the kind of work that you all did over these last few months… Hell, over these last few years… your whole young athletic careers have been leading up to this race. So, honor yourself by taking every moment of agony… every sacrifice… every time you didn’t take the easy way out… all of your love… all of your strength… all of your grit… empty that tank!”

Half the girls standing in a circle around the coach had tears in their eyes while the rest were steely focused. Diane bounced in the cold air to keep warm. Like many of the girls, she wasn’t wearing the university logo shorts of her uniform, only jet-black leggings. It seemed all the girls had arrived at the same conclusion after trying on the dainty shorts on top of their slick tights and noticing how the billowing material of the shorts created a diaper effect and the look was anything but flattering. After some trial and error, Diane was had settled on her favorite brand, Rabbit, High and Mighty, which she wore over her Marmot thong that looked completely seamless. There was no need to use ones imagination in order to speculate what Diane looked like naked from the waist down in those jet black tights. Read more »

The time my best friend sucked the cum out of me

Well, I received pretty positive feedback on how I filled my girlfriend’s sister with a huge load of warm cum, so I figured I would tell another story. And yes, I am still trying to fuck the sister again.

I met my best friend, Sam, in High School. She and I had a great friendship throughout the years. We were able to become close with each other, vulnerable even, without actually dating or fooling around. I will admit, though, I have stroked myself thinking about her on more than one occasion.

As we grew older, we would flirt and tease more and more, but again, never acted on anything. Then, one night, I’m alone in my apartment and I’m talking to her while watching Netflix. It’s absolutely freezing outside, it had just snowed, and I’m bundled up. For whatever reason, I was absolutely worked up. My cock was hard, aching even, and every time I moved, my cock would rub against my shorts, my blanket, my leg, whatever, and it was begging me to stuff it into a warm, tight pussy. Which is hard to do when you’re alone. Read more »