Tag: High School

21 [F] I used to make money by sleeping with guys

I used to make money by sleeping with guys I knew through an online platform in exchange for money. After I graduated from high school, I did it for a few more years.

Then, one guy told me to stop doing it and offered me a place to stay and money to pay for school. He told me to go back to school and try to get my degree certificate in three years.

He is now the most important person in my life, both mentally and financially. Since he lives with his girlfriend, we don’t see each other very often, maybe once or twice a week at most. Most of the time, we spend one or two hours having sex at the place I rent.

He pays for my rent, bills, and other daily expenses, but he also has a lot of control over how I spend my time. He keeps track of where I am every hour, and he also calls me a lot. If I don’t answer the phone after two rings or tell him I’m going somewhere else, he might think I’m meeting up with other guys for money. Read more »

My former high school teacher made me cum real hard [F]

This happened when I was 21. I was at this event with a couple of friends when I saw Mr. S (50 something), my former math teacher from high school. When I was in high school, I didn’t have a crush for any of my teachers, and Mr. S wasn’t exactly hot, he was handsome but an average guy none the less. I remembered that he was married and really really wasn’t interested in anything else than say hi and maybe have some small talk. He smiled at me, but admitted that he didn’t remember me at all. We started to talk and agreed that the event was pretty boring. Actually, he had a good conversation and I was feeling entertained. I learned that he and his wife were separated, not divorced (ok, I took a risk there because he could be lying) and that’s why I accepted his invitation to go somewhere else and have dinner. Read more »

My first same-sex experience [MM]

So I identify as bisexual now, but there was a time that I didn’t. Went through high school being sure I was 100% straight, despite one occasion where I masturbated under the covers with a friend at a sleepover.

Fast forward to when I was 21 (I’m 27 now, so 2016), and my best friend from high school wanted to sleep over to catch up as we hadn’t hung out in ages. We slept on separate air beds next to each other, and got talking about sex during the night. This made us both horny and we were clearly touching ourselves under the covers, so eventually we both ended up totally naked with the covers off, masturbating next to each other. This time, however, we switched hands and started stroking each other. Feeling another guy hard in my hands for the first time was an awesome experience! After that he offered to go down on me and sucked me off until I came in his mouth. I was too nervous and confused to return the favour, so I stroked him a little more and then he took over and made himself cum. Read more »

[F]ucked my ex best friend’s ex [M]

When I was 16, still in high school, I had a best friend called Mary Anne. She was the definition of boy crazy.

When Mary Anne got a boyfriend, you’d never hear the end of it. Everything she said had to include him somehow. He’d hang out with us after school, go with us to every party. It was never ending.

His name was Marshall. He was our age, but way taller than both of us (we’re both pretty short, around 5’4), medium build, short brown hair. Just your average guy, but apparently a savage in bed. I got to know him pretty well from all the time we spent together, which was something Mary Anne wasn’t thrilled about, but oh well.

Fast forward a few months, Mary Anne cheated on him while he was on vacation with his parents. I was there when it happened, told her not to do it, but she wouldn’t listen. She did, however, beg me not to tell Marshall, and… I told him anyway, and he promptly broke up with her. Read more »

[Cuckold] I Love Thinking About How Other Men Fucked My Wife Better Than I Could

People are always asking what my ex-wife looked like. I’ll tell you this, she was beautiful. Far out of my league. She was always the prettiest girl in the room. She turned heads. I saw the way the partners in the law firm looked at her. She was half-American and half-Indonesian (think Tia Carrere. Think of her Playboy shoot. That’s kind of what my ex-wife looked like. A vague resemblance, mostly in the face.) She had a dark complexion. Sexy, dark eyes. Long, dark hair that I loved. She was 5’ 5” and skinny. I could put my hands around her waist if I squeezed. She had a really nice ass, but I’m not an ass man.

I’m a breast man, and my ex-wife had large breasts. Beautiful D cups that overflowed every bra she wore. Full. Round. Firm. I loved to feel them pressed up against me when we had sex. I loved to watch them bounce when she was on top of me. Her nipples were fantastic! Dark. Pointy. Medium size areola. They were the perfect size for sucking. Rolling my tounge around. Because her breasts were heavy, they hung, which made her areola look long. They were probably two inched long and an inch wide. When her nipples were hard, you could see them through her shirt. (Don’t waste my time asking for pictures, because you’re not going to get them. And it pisses me off.) Read more »

I fucked my FWB while her friend watched [M23]

This was years ago, but I clearly still think about it a lot. A bunch of friends and I were together drinking/smoking at a friends house while I was visiting from out of town during the holidays. Me and this girl who I was FWB with whenever I was in town were going to crash/hookup on a futon in his basement that night. Her friend ended up drinking too much and slept on the couch in the same room as our futon.

The girl I was with was a little hippie chick. 22, half-Asian, tattoos, straight brown hair with a few dreads, petite and fit. I’ll call her Kathleen here. Her friend was 23, BBW, pale, big blue eyes, massive tits bigger than her head, and a big round ass that she always squeezed into tight jeans. I’ll call her Marie here. I knew Marie wasn’t drunk enough to go right to sleep, just too much to drive. I got the feeling she wanted to join us but Kathleen would not have been down with that, even though she was very free spirited. Read more »

I Fucked a Girl (18) On Her Front Porch [MF]

This happened way back in high school, but it’s one of my favorite memories. I was dating this chick and after dinner with her parents, they went to bed and we watched a movie. She had a curfew of midnight and normally kicked me out at that time.

This time, though, as she was seeing me off, I started French kissing her right outside their front door. She reciprocated and I decided to take it as far as I could. I grabbed her waist firmly and started running my hands all over her body. When she started moaning in my mouth I knew I had her.

I turned her around and pressed her against her front door. Then I pulled down her tight ass yoga pants just enough to expose her pussy. She was wet for me, so I didn’t waste any time. I unzipped my pants, got my hard dick out and tried to fuck her. It took a couple of tries, but finally I got inside her. She gasped and I started fucking her against the door, telling her to be quiet or else her parents would find out. Read more »

After the [F]irst time I sucked dick, I became an addict.

This month marks 8 years of sucking dick for me.

I was pretty shy and inexperienced in high school. I got to college and started working at a job on campus as a freshman. One of the managers at my job was a senior, we’ll call him Ethan.

We became good friends over the year I worked alongside him. He ended up staying in our college town after he graduated so we continued hanging out occasionally. My sophomore year after a party I went back to his place planning to spend the night on his couch, but ended up with his cock in my mouth.

We got back and continued chatting on his couch. At some point we started to kiss. I took my shirt and bra off and climbed on top of him. We had never done anything remotely romantic or sexual before this point so you can imagine my surprise when he started to take off his pants as well. Read more »

31 [M] painting her in more ways than one

So this happened a few years ago. I was maybe 26-27? Anyways. I dabble in artwork and drawing. I specialize in anime but I’m kind of into drawing anything female. So one of my high school friends noticed my art page that I had and followed it. At first she would just comment and like and leave small comments. After a few months of this thought she DM’d me asking if I would draw her. I of course said sure, cause she was cute and had a great body so I’m terms of what I enjoyed doing it would be easy.

She sent me a picture of her and it was mild. So I drew something up just like a quick sketch and sent it back to her and she loved it. She didn’t request anything else for a few weeks, when all of a sudden she messaged again.

“Hey so this is awkward but I really want to ask you something “

“Sure, what’s up? Promise I don’t judge”

“Can you draw me again? But this time naked…” Read more »

We Met in the Dorm Shower [M/M]

All people depicted are over the age of 18.

*****

Sometimes I wonder what life would be like if I hadn’t met Chris, or if we’d met later. Not in a pining way that makes me wish for different. Just in a simple way. Would I be as happy? I probably would have had a bit more of a ho phase, but I got a lot of that out in high school, and it wasn’t like we didn’t have some fun times getting a third.

We met our freshman year of college. We kept seeing each other in passing. He was gorgeous, his dark red hair very attractive to me. He clearly lived somewhere in the building, or frequently visited someone who did, because we saw each other in the hallway all the time.

The frequency of our sightings progressed to nods of hello, eventually to greetings of “hey” and other short, monosyllabic acknowledgements. Our first actual conversation took place at the end of October. I walked into the dorm bathroom, headed for the shower. It was fairly early on a Saturday morning, which was when I tended to come to the usually empty showers to jerk off. On this morning though, he was in there. He had clearly just finished showering, the red hair that attracted me to him almost brown in its dampness. He only wore shorts, his pale chest exposed. He was incredibly lean and slightly muscular, a physique crafted from the years of swimming I would later learn about. Read more »