My best friend Samuel and I have been friends sense 4th grade and even are in the same college together, we also share a dorm room. For some people this might sound like a bad idea but for me, it was perfect. We always got along and knew each others boundaries. Samuels mom has always been there for me but I never thought of her as more than just my friends mom. Once I got to my senior year of high school I did start to notice her more for her body though. For a woman in her mid 40’s she looked good. She had Samuel a bit young so she was one of the younger parents in our friend group. She was short, about 5’5 with beautiful full lips, long Lucious brown hair and a chest that would satisfy any man. She had a slim waist and an ass that I dreamed about bouncing on my cock, but after we went off to college I never saw her until she came to visit
Tag: High School
[MF] [M]y ex-girlfriend [F] tried to win me back with wild public fuck
My ex and I had dated for a few years, starting at the end of high school. She was an absolute bombshell Latina who knew how to fuck, kind of a freak, and was much more experienced, she was my first.
After doing long distance for a while in college, I broke up with her over Christmas break for a number of different reasons (distance, curiosity/interest in other women, etc.). Although the sex was incredible, I knew I wanted to experience it with other people, not just her. When I broke the news, she was devastated.
We stayed in touch for the next few months before we both came back to our hometown for summer break. She texted me one morning asking me to meet her at a nearby park. I agreed, assuming she just wanted to talk and catch up and perhaps get some more closure on our relationship.
I drove to the park, jumped out of my car and saw she was waiting for me on a bench wearing the tightest booty shorts that barely covered half her ass and a light blue tank top that showed off her perfect tits.
I Never Thought Caddying Wood Be So Much Fun. (M) 18 (F)36,DDD
Like any other kid, all throughout High School I was always out of money and completely undersexed. When finally during the spring of my senior year my father helped me land a caddying gig at the posh Country Club near where we lived. My first weekend there I didn’t even get out on the course and made no money. I told the caddy master prior to leaving on Sunday “I know the game well”. But he told me “Kid, you’ve got to pay your dues, maybe next weekend”.
The next weekend was cold and blustery and I figured that meant some of the regular caddies would stay home. Unfortunately that also meant a lot the golfers stayed home. I decided to wait it out (what else was I doing to do, go home and jerk off). I played some cards with the other caddies but there was enough play where soon enough I was the only caddy left. I was contemplating going home when the caddy master came inside the caddy shack. He looked around for one of his more experienced caddies and said “Shit are you the only one left?” “Seriously, I’ll do a good job” I said. He thought for a second and then said “I guess I have no other choice. Here grab the bags for Mr. and Ms. Clark and kid, don’t fuck this up. Mr. Clark is the president of the club and Ms. Clark, well…you’ll see. And try not to stare at her tits okay”. He added “And the way she looks today, it’s gonna be tough. Hurry up I gotta go jerk off in my office.” “Okay” I thought, my dad said the caddy master was a little off. But at least it was a chance to make some money.
Meeting my best friend from high school (part 2)
After making me cum, it was my turn to make her orgasm. She led me up the stairs by my hand and I watched her ass move as we briskly moved up the two flights of stairs into her dorm room. She opened the door and led me inside, She closed the door and without a word took my shirt off. I grabbed her by her waist and pulled her into me and kissed her. I pushed her against the wall and put my hand gently around her throat, gently squeezing. “Harder” she moaned. I smirked and picked her up, her legs wrapping around her waist, still kissing me. I carried her to her bedroom and laid her down in her bed.
Daddy fucks the babysitter (true story)
During highschool I babysat on Friday and Saturday nights all the time. It was not unusual for innocent, young me to be driven home late at night by an older father who had a few too many drinks on his breath. Occasionally I’d catch a slow look or a subtle ‘growl’ but nothing ever really happened . . . other than the roots of a little fantasy beginning to grow in my young mind.
Then, shortly after college I had a brief stint as a nanny for a family during their winter ski vacation in Aspen, Colorado. It was long days of schlepping bratty children to ski school but the setting was gorgeous and the money was good so it wasn’t terrible. Plus, I played the part so well. Wearing little skirts and braids like these pics (which were taken recently for some role play . . . smartphones and selfies weren’t really a thing back then).
As the vacation went on – the mom and dad were grating on eachother, bad. They didn’t seem to like each other very much and would constantly argue. A few times I’d catch dad looking at me curiously. And, when they’d fight I’d get a clear look of “fuck this” from him. I thought it was pretty funny.
A best bud and I [mm] got curious one night and dicks were touched
I have this friend from high school. He’s always been the best friend I’ve ever had. Like brothers. We’ve done just about everything together. We had a mmf threesome in high school but never touched each other. One time we jerked off in the same room and illuminated it all with a flashlight. He was pretty impressed with my size compared to his own and he said so. I’m uncut and he isn’t and he found that to be of particular interest to him. I showed him how it works with a foreskin and he was pretty facsinated, but again…no touching. That’s when we started the handjob joke. We said it in texts, in chat, in person. Just always in fun but never stopped this joke. It became funnier as time went on. Years pass and we both lived in different cities, and one summer evening we decided to get together for PlayStation games and weed. We played games for hours at his place, ordered pizza, and basically just trash talked all night. After several fat joints were shared we stopped playing games and just chatted about stuff from our past. Parties, girls, guy stuff…Eventually the threesome came up and we talked about why we didn’t do more with the cute girl we did it with in the tent that night. We talked about the jerking off night and how weird it was. He brought up the handjob joke again as we passed another joint back and forth. I laughed and asked him how he’d do it. He described what he’d do and did a gesture with his hand. So I told him he seemed to know what to do, and I just asked him if he wanted to try it. He laughed and then said yes. I didn’t take him seriously at all because we have had this joke at this point for literally 7 or 8 years. Half an hour passes, we’ve showered and we’re laughing and still smoking weed and now in just t-shirts and boxers basically ready for sleep but still wired. We roll more joints and put in a new game. We turn the lights out and just play PlayStation and chat for a bit, until my buddy just out of the blue asks me if I want that handjob..and he wasn’t joking this time. At this point the game is paused and the only light in the room is coming from the tv. I didn’t think he would really do anything so I said “Sure I’ve been waiting all this time!” He then confirmed with me that it’s okay and he rested his hand directly on the front of my boxers. He confirmed again and I nodded and he started moving his hand in circles. This is where it started getting tingly down there for me. I lit a joint and we share it while he continued circles over my boxers with an open palm. So at this point it had gotten hella real and I was nervous af because I wasn’t really expecting this for real and it was my best friend but we were high and horny and I wanted to see how far he would let it go. He unbuttoned the fly on my flannel boxers and he reached in while his fingers found what they were searching for. He pulled my dick out and it hardened the rest of the way. He then pulled out my balls and basically just stared at my junk for a while. After another confirmation that it was okay to proceed he wrapped his hand around my hard dick. I guess I didn’t expect his hand to be warm and it was actually kind of nice. He commented on how big I am a few times and he played with my dick very slowly for what seemed like over an hour. It was a mix of being extremely weirded out and loving it. His head made it to my stomach so he could lie down and see what he was doing. I just laid there letting him do it. He was definitely intrigued by my foreskin and by my size. At some point I said to him “Fuck this is weird!” We laughed. He hesitated while he was still jerking me and he said, “Do you want it to get weirder?” At the time I was thinking what could be weirder than my best dude jerking me off? He asked one more time if he was good to go and I said okay. Next thing I know, and it took a minute to start, he had put my dick in his mouth. Everything was so slow and exploring and Jesus it was amazing. I’ve never had a handjob or a blowjob with so much enthusiasm and interest. I think the blowjob lasted 15 minutes at least. He finished me like that and I warned him but he didn’t back off so I came in his throat…no spitting. He let me try on him and he said i was no good at it and that he enjoyed doing it, and I had obviously enjoyed it also. The weirdness of it was the best part I think.
Reunion with my best friend from high school
Before I went off to college I had a small but tightly knit group of friends. Out of all of us me and Brittany were definitely the closest, we would even hangout alone from time to time. I never thought of her as more than a friend or even a romantic partner. It’s not that she wasn’t attractive, it’s that I thought of her as my sister. We both applied for the same college but she ended up being rejected and had to find another school. That was fine with me because I wanted a fresh start with new friends anyway.
Fast forward a couple of years and I hear my phone ding from the other side of the room. I get up from laying in bed and see it’s a text from Brittany. “Why is she texting me at 3 AM?” I thought to myself as I unlocked my phone to read the message. It read “hey, it’s Brittany, I was wondering if you wanted to meet up and catch up a little”. I thought a little and decided that I would in fact meet with her “sure” I typed, “where do you want to meet?”. We continued talking and decided that I would pick her up from her dorm room and we would go do dinner and catch up. I put my phone back down on the counter and went back to bed.
[MF] [fucked a girl I wanted fuck in high school ]
Lil back story let’s call her Kenzie. When I was in high school around junior year me and Kenzie had a class next door to each other. Me and my friend would always be like damnn when we would see her. She was a small 5”3 tight girl with caramel skin, small tits and fat ass. I would tell my friend imagine if I hit that one day. I never spoke to her in high school or anything and I never fucked.
Until years later around March 2020. One of My friends (not guy from junior year) and his girlfriend, well his girlfriend was trying to set me up with someone and that girl ended up being Kenzie…
So we all decided to go hangout together one night at a fair. And the nights going good my friend and his girl do there own thing and I’m with Kenzie enjoying the fair. We are just casually talking not much flirting. It starts getting late so we decide to start driving back home. They drop me and Kenzie off at my house (cause me and Kenzie planned to hangout a little more and I’d take her home later) and they go home.
[MF] I (18M) had unexpected sex on the first date with a (18F)
After finishing high school I was well and truly bored browsing tinder during my Christmas holidays, I matched with an incredibly attractive eurasian girl, we got to talking for a couple days before she asked if she could come over, told me I was different from other guys on tinder. I accepted of course and when she arrived I put on one of my favorite comedy mockumentaries at the time.
I don’t want to mince words but to put it bluntly she did not find it funny whatsoever. This was quite funny to me at the time but after the movie had finished she turned to me and said stonefaced “You wanna have sex?”.
To clarify sex had not been brought up into conversation even once on tinder (I know, unusual).
I, completely flabbergasted at this proposition considering what she had thought of the movie we watched accepted rather giddily.
I remembered this recently after seeing this subreddit in r/all and just wanted to share a more lighthearted story where the mood pointed almost anywhere but sex.
That time I, a 22 [f] got turned out by my masseuse
I know guys always joke about it..but one time, I got one. I was working on my undergrad at the time, and studying a LOT. I had used this place for years and decided a massage would take the edge off.
Well, it did. And while I ALWAYS love a good massage, this one was…idk, different. I became really turned on, even before it started. While he was working my hamstrings/butt, I felt myself involuntarily hunching the air. Really pathetic. I was a lady, 4.0.student, and this guy had me, or could have had me, any way he wanted.
I was so wet, my thighs were dripping. His hands got really really close, and I kept trying to squirm until his hands touched me. Every time he would just move his hands and LAUGH! He started asking me if there was something I needed, if everything was okay. And me..
I just kept hunching the air. He was finally a bit more direct
Maam, if there’s something you need, use your words.