High School Archives — Page 567 of 805 — NSFW story

My first blowjob

A hot past confession.

When I was a very young girl I had a gay friend. I met him in high school. I was young and totally virgin. But with a huge desire to suck dick. After thinking about it for a few months I asked him to let me suck his cock.

At first he flatly refused. I begged him for days. After a few days he barely accepted. We agreed on the day. We went to my house (I only lived with my mother and always worked in the afternoons).

He was very nervous. We went to my room. We laughed nervously and he turned on the TV and tried to distract me (we had limited time since my mother always arrived at 5pm and we left school at 2pm) I tried to hug him, kiss him and touch his cock. He retired nervously laughing. I got on my knees “kidding” in front of him, he was sitting. I opened my mouth and told him to put his cock in my mouth. Read more »

The Company Christmas Party [MF]

As I am sitting at my desk at work, looking at a picture of my wife and I, I am reminded of one of my favorite excursions with her.

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The plane touched down in NOLA as several members of my company exited the plane. We’re here for the company Christmas party where we sometimes do it big by flying out all the employees and their partners for a weekend away somewhere to celebrate. One of the nicest perks we have.

My wife, a 5′ 1″ cutie with a booty, dark brown hair down to her mid back, brown eyes, 34B breasts, 115 lbs, gorgeous smile, and curvy in all the places that makes men stop and stare. She grips my hand, calming me. I’m honestly a pretty anxious flyer. Hate heights. Myself, 5′ 8″, black hair and brown eyes, 160 lbs, somewhat slim and building towards the dad bod and actively trying to fend it off. Pretty average in the department downstairs with a straight upward curve. It’s weird but I make it work. Read more »

Sex with my childhood friend who is now a married woman [MF]

**Like I’ve said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I’m generally considered a good-looking guy (6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give.**

Brooke and her family moved into my neighborhood when I was nearing the end of elementary school. They were two houses down to the left if you were facing my house. Our neighborhood was fairly quiet. Brooke was the same age as me. She had one sister who was three years older than us. I don’t think any of us spoke for the first year or so. We would see each other from across the way, but always fell victim to the awkward feelings of youth and retreated back into ourselves. All of that changed the following year. Read more »

First Time Without a Condom [MF]

I definitely had a huge change of heart about condoms a few years ago and never went back. I was about 19, and a Freshman in college. The year had been hard on me being away from my very beautiful Israeli girlfriend who had been accepted to another school. We had been dating for all of our senior year of high school and were doing our best to make it work long distance. She was a virgin when we started dating and was hesitant to lose her virginity. After months of dating and doing everything else except actual penetration, she was ready. The condoms we used were very basic, but I knew them to be very sturdy (so as to put her mind at ease.) It was a beautiful experience, and one I will never forget. She was shaking as I penetrated her for the first time, gently shushing her and kissing her softly until I was deep inside of her. We went slowly and after maybe 20 minutes, we both orgasmed and collapsed. Now, though this is a fond memory, it’s not one I like to look back on too often. Of course, halfway through the second half of the semester, she dumped me…. Read more »

The Student Teacher [MF] [Repost] [Long]

This is a repost. Apparently people didn’t read the note I put at the bottom, and flagged my story as fake, so I’ll post it here at the top now: ***Yes, of course the text screen shots are not the actual conversation. I made it using a stupid website. It is how I remember the conversation. I did it because I wanted to switch it up and it was a tribute to the awesome saga of the guy with the big dick with the hot cousin. I wish he would come out of hiding and tell some more stories.***

I’m a 39-year-old teacher in a high school in Appalachia. Several years ago I was married and we were lucky enough to have a son we named Sam. Then I became single (not going into why). After a few months of crawling inside a bottle I decided to get my shit together and focus all of my efforts on being a decent human being and spend all of my time and effort to do the best job I can to raise my son. He’s now in 8th grade (7th grade during this story). I’m six feet tall about 175 pounds. I’m in good shape. Read more »

The Student Teacher [MF]

I’m a 39-year-old teacher in a high school in Appalachia. Several years ago I was married and we were lucky enough to have a son we named Sam. Then I became single (not going into why). After a few months of crawling inside a bottle I decided to get my shit together and focus all of my efforts on being a decent human being and spend all of my time and effort to do the best job I can to raise my son. He’s now in 8th grade (7th grade during this story). I’m six feet tall about 175 pounds. I’m in good shape.

My school works with a (somewhat) local university. Each semester they send us a few student teachers. For those who don’t know, whenever you finish up an education degree, you don’t spend much time as a student the last semester. The school sets you up in a teaching position in the area you will be certified in to practice actual teaching. If you are worth anything at all, it’s highly stressful and extremely time consuming because it’s really a semester long job interview that can make or break you. Read more »

[MF] Like A Virgin

I’ll lead in with some backstory that definitely contributes to the plot, but I’ll mark where the fun part starts for those of you that prefer!

We’d been seeing each other off-and-on for a couple months; while I’m unsure of the exact date this transpired, mid-January seems a safe bet. He was a relatively good Christian boy, only recently second-guessing his ties to his faith. At maybe 5’10” and 20 years old, he was a bit shorter than my other flings, and a bit huskier too. A combination of good eating and weightlifting had created a man who was, in my eyes, the perfect human teddy bear. Cuddly, but able to pick me up and toss me around when the situation called for such. I was barely 19, a solid 5’1″ in combat boots, and I’ve had my physique described as “porn star”-esqe in the past. A truly ideal hourglass body, breasts that, in relation to my rib cage, I cannot find a bra to contain, and an ass I take pride in for good reason – for all intents and purposes, rather hot. I dye my hair fairly often, but if memory serves me correctly, I was sporting ginger hair at the time. We were polar opposites in a lot of ways: his religion, morals, and law-abiding demeanor countered how I’d spent my high school years, but we clicked emotionally and intellectually, in a way I still don’t quite understand. Read more »

Ode to Craigslist: My First Milf [MF]

As I’ve mentioned in previous posts, I discovered the Lifestyle after getting dumped by my high school sweetheart. Well, this is Genesis, the very beginning. Also, in light of recent events with the loss of Casual Encounters, I thought I’d share my very first CL success story. In those days AFF, Craigslist and SLS were the only real means of finding a hookup online.

I realized that posting was really the best was to find someone to play with. Single ladies, I don’t envy you. May your inbox RIP. I posted my ad and within a few hours, I was chatting with Joyce. She said she was older but played coy about her age for a while. She said she loved younger studs with stamina. We flirted by IM and exchanged some pics. Before I knew it, she was inviting me over. Nervous as fuck, I agreed and gave her my cell number. Read more »

[FM] An Affair with a Married Man; The Best Sex of my Life (20f,42m)

About myself: I’m a 20 year old college athlete who makes top grades and spends a ton of time on Reddit. I started dating a guy over last summer my parents set me up with through church. (my family is very religious , I’m not but I hate to disappoint them so I go) He is good looking, nice and caring but something is missing. I said yes to dating him because my parents loved him. The hardest thing about dating him was he wanted to wait for marriage to have sex . Over that period of time I had become very good at putting on a mask and pretending to be happy while pushing down what I want.

This all took place during the past holiday break a few months ago now. My family consists of my mom , dad and older brother. A week into me being home we went out to eat with my Mom’s best friend and her Husband. They wanted to see me since I was back in town because they are like 2nd parents to me. I had banged up my knee earlier in the fall training so they asked me how it was feeling. I shared with them it had been hard because I haven’t been able to run since the injury. The husband (I will call him Mr.Thompson) felt bad for me and invited me to use their pool at anytime over the break to train. They have a lap pool they keep heated in the winter I used it in high school for workouts. I decided to take him up on his offer. Read more »