High School Archives — Page 680 of 805 — NSFW story

[MF] Fingered a recently turned 18 yo in my car last night. No sex but left me pent up.

Picture of girl in this real story: https://imgur.com/a/AIKEl

Don’t care if you believe me or not, this happened:

I went on a date for the second time with this girl “C” last night. She just graduated from high school in socal this year and moved to the bay area last month to start college for the fall. I have a couple mutual friends with her and was surprised to find her on tinder. Anyways, long story short we went on a date last month that was pretty boring and then another one last night. Here’s where it gets good. Read more »

She wants to be filled. [MF] +F Cheating

So I’ve been reading the stories here for a while, and now I have something I have to post.

I’m 21 and just started my senior year of college. I go to a really small school for art. It’s been a lot of fun. Being an art school everyone is fairly open minded about things, especially nudity and sex.

My very first day of freshman year, in my very first class I sit next to a super cute redhead. Amanda. Tall and skinny. Small breasts, but a nice ass. Her curly red hair framed a round face. Pale skin, nice lips, and tons of freckles. And the greenest eyes I have ever seen.

We were both bored, so she and I ignored the teacher and quietly chatted. We are both photography majors, so of course we talked about that. After we went and got coffee. We had to back for different classes after, so I asked her if she wanted to get dinner after. Read more »

My Little Brother’s Girlfriend [MF] [Oral] [Anal]

I leave my room and head to the bathroom, wrapped in a towel. As I hurry through the den I see my little brother on the couch, his girlfriend is next to him, her legs draped over his lap. I had come home from college to watch the house while our parents were out of town, and being the cool older brother I am, had agreed to let Dan have Jenna stay over night. They are seniors in high school after all, and I remember how hard it was to get in some good alone time. I duck quickly into the bathroom and get into the shower.

As I bathe, my thoughts turn to Jenna, admittedly not for the first time. I recall the young latina lounging on the couch. Her dark, smooth legs were quite visible in the shorts she’s wearing. Her breasts, a respectable b cup if I had to guess, had been complimented well by her tight shirt.

I grin and touch my stiffening cock absentmindedly. I had passed through the room fast, but had I not seen her eyes move behind her glasses, passing over my bare chest? Wishful thinking perhaps, which speaking of… Read more »

[MF] Testing Out Tinder Pt. 1 – Back Story

I was traveling abroad after a recent breakup and figured it was the perfect opportunity to try out Tinder – a service not available the last time I was single. I put together my profile with the help of some close female friends and turned it on a few days after I landed. I had no concept of Tinder in the US, but where I was, very few profiles had info, and many of the photos were pretty bad. On top of that, I was dodging descriptions that included pricing. After some mindless swiping, I was matched with a cute woman a year older than me (30s). We started exchanging simple messages back and forth and I suggested drinks on a Tuesday night. She asked if I spoke Spanish – not really. I asked if she spoke English – very little. I suggested that we could use Google Translate (GT) on my phone to communicate and she thought it sounded like fun. Read more »

The first time we [m]ade love, the second time we [f]ucked.

It was 12:30am and the bar was fucking lit. A seemingly endless stream of young, overly inebriated humans continued to flow into one of the most popular bars on campus. We had just finished another round of $60 dollar shots, and I was in the fucking zone. I was riding a wave of endorphins, the source of which was directly under my arm, regaining her composure from the straight patron shot. I kissed her cheek, while I removed my arm and asked the bartender to close out my tab. I wanted to ensure a quick exit… I knew what the future held. She grabbed my hand and we pushed our way through the sea of sweaty half naked woman, none of which required a second glance. Everything I needed was holding my hand. I would have followed her off of a fucking cliff. Read more »

[MF] [Oral] Finally home alone

So, a quick background here. My wife and I have been married 5 years. Second marriages for both of us, although we dated senior year of high school. We are both 45 years old. Before anyone asks, we are both average build, Think Kevin James 2011and model Candice Huffine, you can google them both.
My Step-Daughter lives with us she is 22, and I have been involved in some way her entire life.

It’s difficult at times for my wife and I to be alone in our house. Our daughter is home with her boyfriend most nights watching TV in her room or just hanging out with us. When we were dating after our divorces, we only saw each other on weekends once or twice a month based on schedules and not living in the same state. When we saw each other during those weekends, … well we fucked like rabbits, in every room, position and rarely got dressed. I’ll go into more of that if this works out. Since we’ve been married and life is happening, it’s harder to get time alone, and be ‘in the mood’ as they say. So sometimes you take that opportunity when it presents itself, whether one or the other isn’t expecting it. Read more »

I was young and immoral. She was young, insecure, and not very bright. “The Big Head” by me. [M/F, M+/F, kinky, cheating]

The Big Head
by me
***
[M/F, M+/F, kinky, cheating]
***

It was my first time in a position of “power”. That is, it was my first time working anywhere where they put me in charge of somebody.

I was, technically speaking, the Assistant Manager of the chain-restuarant I’d been a line-cook at for two whole years since graduating high school. And boy did it go to my head.

I was a real prick. I wrote employees up for anything and didn’t give a shit that they hated me for it. The GM was this middle-aged guy who loved using me as the scapegoat for any of the anger the waitstaff (especially the waitstaff! kitchen, front house, bar– no other department was nearly as bad at complaining and being all around dumbasses as the fucking waitstaff) had to direct somewhere. They played pranks on me, they talked about me behind my back, and I knew all about it because one of the linecooks was a friend of mine. He was trying to get me to chill.

When he told me that I literally said, “Are you kidding? Why would I ‘chill’? I love this fucking job!” Read more »

First group try. [Group] [MF]

Through high school I had done what most of us do, take what I could get. Oral sex seemed to be a one-way street where I gave it, they tried it, and then told me to just fuck them. The fucking was missionary, them on top, or doggy style as the big finishing move. I was much more open than anyone I was ever with. Me and Ann had sex on the couch once. It was as you would expect, missionary.
This was college. I was lucky enough to live in a large house, with fairly liberal roommates. There was a hot tub in a Gazebo. We lit it with Christmas lights, just the white ones. It was nice enough. The house was out of the way, fairly private, and the usual for parties.
I met Rose on Yahoo Chat. I miss the local section of that chat room. I could chat anonymously with locals. I could private chat, and talk dirty. I met some really fun people in person from the rooms. Rose was the high bar of those.
She was two years older than I was, and had a lot more sexual experience. Things like trying anal, or watching porn and having sex at the same time seemed like bucket list items to me. They were fun to her. She was comfortable. She knew what she was doing. She had done a lot of it before.
Rose was 5’10”. Brown hair. B cup breasts with perfect nipples, but her ass was the star of the show. It formed a heart when she bent over. Her pussy would swell, and she was usually very wet. Speaking of her pussy, it was delicious. She was the first one to ever just sit on my face, something I enjoy to this day.
One day she and I were having the “compatibility talk.” Seeing what each other wanted sexually. We were too young to know the other stuff. Monogamous, open, what we wanted to try. This is a conversation I have always repeated. You learn a lot. I know that I need a certain type to keep me entertained.
Her stuff was easy. Toys. Blindfolds. Handcuffs. Her big thing was that she wanted me to learn to make her squirt. She could do it herself, but no guy had. Easy enough. I always fear the conversation from my side. How do you tell someone that their being spit roasted would be OK. If they wanted to fuck your best friend it is a plus? That you enjoy fucking women in serious relationships.
I started easy, told her that I would love any number of group scenarios. Also, would love to try anal. She chuckled, and asked if that was it. I told her it was. She chuckled, and dropped her pants. “Anal is easy, we need friends for the rest…” Dick instantly hard, throbbing.
I remember getting it in to this day. She puta condom on me, then pulled it off. Lightly coating me in it. She took the condom over her finger, rubbed her ass, then slowly put it in, and pulled it out. “ready, I will lead. You don’t need to just ram that in there…”
My dick is just above normal. Nice head, decent length. I always thought of myself as small. My best friend has a huge dick, and that is really all I had to compare mine to. I knew he was big, but I had no idea being thinner and two inches shorter was good for most women. He is actually just glad when one can take him.
She got on all fours, and guided me in. My favorite feeling is entering for the first time. This time is seared into my mind. A little pressure. I wondered if it would happen as I felt the tiniest pinhole of an opening start. She exhaled, and took me in a little at a time. Just the tip. Pause. Breath. Sliding in another inch. Out a bit, pause, breath, in a little more until it was all the way. I slowly pumped until I was done.
A few weeks later we had some friends over. Brandon was my best friend, Jenn was his eventual wife, and someone I always wanted. She was actually like one of the guys. Cool. We liked her. She could wing man, or talk, hang out, whatever. I was very close with her. Them dating made us all closer.
The night went as usual. Dinner. Hanging out. Movie. Drinking. Hot tub. Brandon forgot their suits. What a dumb fuck.
After a quick debate, we all decided skinny was what was happening. We grabbed full drinks, and departed for the Gazebo. I always had to go first. Take off the top cover keeping the heat in, and all that. This worked to my advantage. Brandon always just stepped over the side. Any girls always used the steps. I always grabbed the lay down spot near the steps. Most jets, best view of them getting in, and jet control.
Tonight, that view was naked. Rose got in, and told me to take a look as Jenn got in. Jen leaned way over making eye contact. Her large breasts hung nicely. She put one leg in, then stood up looking down at me. She said, “what have I done” as she turned around, bent over, and gave me the rear end view of my life. She then just fell forward into her somewhat usual seat in the corner. Brandon got in from the side with minimal incident. He was very drunk.
Rose told me she wanted me to sit on the side. I was a little warm, so I did. She started playing with my dick. Jenn bit her lip. Brandon said OK, and pulled Jenn close. Same room was a fantasy. This was happening.
Rose took me down her throat. Rose gave amazing head. One of the few people I enjoyed it from was her. She slowly raised her hips from the water facing Brandon. Jenn was very sexy, but Rose won the ass department. After a few minutes, I reached back to feel her gorged pussy. This thing was super wet. Dripping.
Jenn had mounted Brandon’s giant cock. I remember watching her position herself high in the water, move a hand down, and slowly sink down. It took about a minute. Once it was in she looked like it was OK, but painful. He looked like he didn’t want to hurt her. I remember Brandon being fixated on Rose’s ass and pussy. She was showing him what I had. I knew it. I loved it.
Rose looked up and asked if I was ready to put on a show. Of fucking course I was. This was my moment. I stood positioning myself behind her swollen, throbbing wet pussy, and guided myself in. She was so wet. It felt like we were using lube. There was no easing in, no slow going. I inserted until I was fully in, and started fucking.
Brandon was just watching at this point. I remember him asking Jenn if he could blow inside her, and her saying no. There was a small, hushed discussion I couldn’t hear, then “Ah, OK…UNNGGGHHH!!!” from him. At this point, He was watching. So was she.
Rose came hard. Her pussy tightened around my cock, and she asked if she was to wet. I learned always say yes to this, because it always leads to anal. She told me to fuck her ass. I had never heard it like that before. She was putting on a show. I remember her saying “for the record, a dick his size will never get my ass” as she pointed at Brandon.
For the first time in my life I was sexually superior to Brandon. I had lasted longer. Not only that, but he was watching me, and Jenn was looking like She was ready for a turn. My smaller dick got anal, his didn’t. His girl wouldn’t even take his cum.
I aligned my head with her asshole. It was pretty well lubed from how wet she was. I rubbed my hand from her pussy to her asshole, it was more than wet enough to spare the necessary lube. As I applied pressure I remember Rose shifting her hips right. I remember wondering what just happened. Did I hurt her? I pulled back a bit.
She leveled her hips. Moved a hand back to her ass cheek, pulling at it. Pushing back on me, and shifting her hips left. I felt her ass open. Left, right, left, right, lef6t, right, then I found myself fully hilted in her ass. “I said fuck my ass” she said. I knew only to start pounding as hard as I could.
I came soon after that. Sitting in the tub she looked pleased. Brandon got out, saying to “carry on” and that he had the spins. Jenn sat for a minute. Rose got out to check on Dan. I remember sitting there with Jenn. I wanted her next. I wanted to cum in every last crevice she could offer, just to come back and use my cum as lube for a second time. I wanted to fuck her like he couldn’t.
She slid over, adjusting the jets to off. Her breast hit my hard cock. She asked what we should do about it…but then I heard Rose. He is sick, where are the blankets…Fuck.
She insisted I get out first. I stood. There was this moment where my hard cock was inches from her face. She smiled, and looked at it, then me. She said she had an idea of how to start with that. Her face said feed me your cock…my conscious said get blankets and a trash can for Brandon.
It later turned out a group sex night had been planned by Rose. Brandon liked fucking drunk, and wanted to be too drunk. Brandon later told me he wished I fucked her, because she kind of held it against him that I hadn’t.
More will follow in later stories.

[m] Finally made her mines after 3 years of standby – GOT CAUGHT [fsub] [oral] [Str8] PART 1

So I liked this girl ever since Freshmen year of high school. Back in the old days she just had this little thing with “sibling friends” which i never understood but somehow i became her “daddy” LOL. I felt lucky asf but also she would always talk to me about her guys and such and eventually i just told her “if you’re gonna be talking bout this all the time, let’s just not talk”… and eventually we faded for about a year until sophomore year. We had french together and i was a fucking class clown LOL, we just made small talks and laughs at time but it was pretty rare. But even though she had a boyfriend i still liked her but was trying to move in and eventually got distracted and found a new girl lols. After a month or 2, they broke up and i was like “ight then”. Last week she hit me up again cause i posted something in facebook and she made small talks about it and it eventually got us ribbons once again. I eventually came out and told her that i’ve been liking her for 3 years and she just asked me to come over to her house. I obliged and went over extremely nervous and excited. She asked me to just talk it through from the beginning to the end with my heart and I did… after that she told me she never saw me that was but that she always wanted me, it’s just that she wouldn’t know how to put it out. After i heard that, i pulled her head and started kissing her and eventually got her on the bed. I then started to take off her shirt BUT THEN she stopped me and told me she was a virgin… i told her “so am i” and proceeded. Once i finally got to take it off, i saw her amazing TITS THAT SHE ALWAYS HID. omg her tits were so amazing but she always hid it :( I then started to suck on it while rubbing my cock against her clit at the same time then took off her bra and her leggings. I turned her around and she was wearing the thing i had a fetish with most… THONGS. I was harder than i ever was my whole life. Her amazing small but perfect ass.. THE GIRL OF MY DREAM WEARING WHAT I HAVE A FETISH WITH :O. I told her that she was fucking amazing and turned her back around and told her to suck my dick. By this time i already had pre cum flowing like crazy. She told me she never sucked dick before and i told her to suck it and play with the head of my dick at the same time because i’m super sensitive down there. She sucked it and hit all the right spots with her tongue! It’s like she was born to do this. She hit all the spots i didn’t even know i was sensitive at. She then started to flick her tongue against my pee hole and i just shot abbot of precum in her mouth. She kept doing this for another 20 minutes. Until we heard….