Tag: High School

How the Spontaneous Friend-cation Turned into the Fuck I Never Expected [FM]

This sex-venture took place about three years ago. I recently traveled (not ideal during a pandemic, I know) to the same general location it happened. It provided some welcomed memories for a lonely night lol

I’m a wordy motherfucker, so skip to the *** if ya know… you need to get things going quickly.

It’s also very long and potentially includes some typos. Bear with me.

So, about three years ago I was roped into one of those impulsive friend-cations. One of my best friends from high school and I remained good friends through college and still are quite close. For our purposes, we’ll call him “Joe.” After high school, our friend group evolved to include Joe’s older sister. She had only been a year ahead of us and they are quite close as siblings. It also helped she had very attractive friends. One of which, let’s call her “Jenn”, Joe was downright infatuated with.

I can’t really blame him. Jenn was (and is) a smoke show. Back then her hair was long and very blonde, and all kinds of curly. She is beautiful and thick, with big tits, big thighs, and a little extra everywhere. She has this “cannot be bothered” attitude and is just effortlessly hot. Read more »

[MFM] First time ever sharing my girlfriend with the best friend.

Hi there, new here( had to create another account so it could be secret lol). A little context. I’ve been with my gf since high school almost 10 years now. Time is flying. We love sex when we have it, although it’s not as often because we both work all the time. My girlfriend let’s call her A, she loves attention though, it’s been hot out in NJ and on the weekends we go over to my dads pool. With the heat wave the water would be HOT, and the weather humid and perfect outside. The weekends are for drinking, my girlfriend has 34DD titties and they are amazing. To play with, touch, look at you name it. My best friend let’s call him, C. Comes over to hangout also. We’ve been weekend chillin all summer but this happened probably end of July. He’s always looking at her as she gets in and out of the pool. He also has had bad luck with girls, getting strung along for months on months by this one girl. So he is deprived. None of this was planned it sort of just happened. ~~~~ Thanks alcohol. Lol. Okay the good stuff. A was wearing a very revealing top. He could not stop commenting on it. The entire night we are downing glasses of alcohol. So we are all drunk by this time and it’s 3am I think by this time. My girlfriend complained about being hot so I said just take your bathing suit off. Which she replied “okay” and she got right out of her bikini and there was just a naked goddess swimming around in front of us. She would swim around and do flips in the water and then just pop up and lay on a raft stomach down so her booty was in the air. C just kept saying “your so lucky dude” over and over again. You could tell he was getting worked up. Then my girlfriend sits on the ladder with her boobs out and he’s just jaw dropped by this time. I started feeling them, and asked him “do you want to feel?” He asked A “can I?” I said sure, and he felt one and then the other. While we’re also talking about random sex stuff that night. I was also a little nervous because I never let anyone do that before, but there was some sort of rush… after a few minutes I said something along the lines of “ A get out of the pool and go on the grass, I want that booty on the ground “ “ she replied “are you sure?” Of course I said. My friend was a little confused. I said she’s going to give us both a handjob. (That’s what I was comfy with) so A got out and we followed her naked self to the side of the house. C said he was rock hard so I said take it out. A took my hard cock in her mouth and started sucking me off and jerking C off. You could tell she was liking it. She turned more to focus on C and he was playing with her boobs at the same time. I was standing there jerking off so I decided to get down behind her. She was dripping wet, i took some of her wetness and spread it between her boobs. I said to titty fuck her. C started pumping away between her boobs while I slid right into her, he was moaning in pleasure a little( fun fact any girl he’s been with had small boobs.) A was also moaning in pleasure from being used from both sides. I ended up shooting my load all over her ass after 5 minutes from it being so hot to actually share my girlfriend. Once I finished my girlfriend laid down and let him on top to finish titty fucking her . He blasted all over her boobs and face. It was dark so I didn’t really get to see that sight haha. Once we were done she got a towel and cleaned off. C headed home all satisfied. I’d say I’m a good friend:p
Drove home and fucked my girlfriend again. The next day we had to have fucked at least 5 times, the most we ever have in one day. A few weeks later we were all hanging out again In the pool, that’s a story for another time. Have any of you ever had an encounter like that? Let me know what you thought! I think it awakened something in me lol

[FF] I ate my college frenemy’s pussy like my life depended on it.

In college, I had a bit of a mean girl streak. To be fair, I still do, and now that I’m approaching my late twenties I’m trying to act more mature and be more empathetic / give more people the benefit of the doubt, but when I was 19 years old I’ll admit I was kind of the worst. I was stuck up about basically everything, from my looks to my body to my SAT scores (which btw if any teens are reading this, nobody gives a shit about your test scores the **second** you step foot on campus so don’t talk about them).

I still cringe remembering how much I bragged about myself at that age.My friend group at the time only made me even more of a brat. We were all in the same semi-academic sorority (closer to a secret society tbh), most of us graduated from the same prep schools and had scored summer internships at the same banks/tech companies, and all of us were thin and good-looking. We thought we were both the hottest and smartest girls on campus, and we were often rude to girls that we thought were “beneath” us. Read more »

An old friend confessed that he had a crush on me back in high school so I showed him what I look like with a cum covered face [FM]

Okay so with this whole pandemic going on, my high school 10 year reunion has been called off until further notice. I was looking forward to it though because there are some people that I really regret drifting apart from. So me and a few of my friends who I still hang out with (who btw have no idea about my lifestyle as a swinger) decided to host our own small one, only with a handful of people who we really cared about seeing. (Irresponsible I know, but we told everyone to show up with masks and we were just only going to sit in the backyard and hangout in the afternoon with some drinks.) Anyways, the small little reunion was pretty chill and it was great seeing some people again and finding out what everyone is up to.

I went back to the kitchen to grab myself another glass of wine and started chatting up with a guy friend that I haven’t seen in forever. We started reminiscing about all the teachers we had together etc. and he showed me pictures of his wife and kids. I commented on how pretty his wife was and he said thanks and told me that in high school he actually had the biggest crush on me. I was genuinely surprised and asked him why he never told me! Read more »

The Sleepover (Part 1) [MFFFFMm] [Group] [Long]

A few weeks ago, a Reddit user asked for a story, gave me the basics, was specific about some things (names and relationships) but let me run wild with the rest. I wanted to give him credit, but he’s gone quiet, so I’ve changed the names to avoid any offence. Oh, and he wanted it long, so I have to split over 2 parts.

To the guy who requested, you know who you are, hope you like it mate.

I was dating this girl called Hannah, we weren’t too serious but had gotten physical a few times, enough to be booty call to each other, etc. One time she tells me her friend Becky is having a bit of a party, private thing, her parents are out of town and she has the house to herself, so had invited a few of her close friends over. No Project-X deal, just a quiet-ish night, except the girls were to bring their boyfriends for company – I didn’t fit that category but I had nothing else planned so Hannah wanted me to come. There were enough bedrooms for us all so wasn’t like we’d have to be on top of each other or anything, and it’d be nice to have a night where we didn’t have to worry about our roommates or parents interrupting our night-time fun. Read more »

How I found out I have a big cock (M F 20s). The second girl he ever fucked opens his eyes to a world of possibilities.

I went off to college a virgin for some reason girls seemed only interested in friendship with me. I have a cute youthful looking face but as a young man it was a disadvantaged because I looked like I was 12 when I was 19, slim and athletic I had a nice body 5‘9“ and 155 pounds.

as for my package I love the way it looks so much if I could I wouldn’t change a thing. For starters i’m a thick 9 inches when I’m hard but I’m a grower not a shower which used to bother me a lot when I was a young man worried about locker room showers and stuff like that. But that was before I knew I had a really big cock.

As a teenager we didn’t have the Internet and the only porn and I had was my dad’s stack of old playboys that hardly ever showed a cock there was one picture that did a hairy 70s Burt Reynolds looking motherfucker laying naked on the bed with a hot busty blonde his cock was completely soft but huge and looking at that I thought I might be seriously lacking. Read more »

How I [M19] became a cuckold son about mom mixed with near-future fantasy

Hello everyone. I am Davis and I am 19. Here I am gonna tell you people how I got into the cuckold thing about my mother. So, let’s get to it-
My mom has always been a bit more beautiful both in face and physically then most of the women of her age. Being the son of such a attractive lady is not that easy. During my high school days I used to hear a lot of things about her from the guys back there. They sometimes back talked and sometimes mock me. I have always been a bit introvert type so they used those words pretty easily. Sometimes they would say sexual things too. Talk about “Davis’s mom is so hot” type of stuff. I always feel utterly disgusted about all these. My mom is 37 now. She had me when she was 18. My mom and dad got divorced about a year ago. After that I got to stay with my mom and her life with me as a single mom started. She works at a fashion designing store as a sales-woman. After the divorced she took a little break and started dating a few people and tried to get into a relationship. But things didn’t work out well. So she gave up seeking for relationships and started doing one-night-stands. It was like this- she usually went to the bar at weekends after a long hard week to relax a bit and meet random strangers and bring them home. I didn’t realize it for quite some time. One night I woke up in thirst at 2am in the morning and went to the hall to get some water when I heard some noise coming from my mom’s bedroom. I got curious that what could be the noises so late at night. Besides I was also confused since I just woke up and couldn’t get my head clear. I started walking slowly towards her room. The closer I was getting, more clear the sounds were heard. I stopped at the door of her bedroom and discovered it was locked from inside and I could hear clearly. I could hear two voices from inside. At this point I still remember how fast my heart was beating and my adrenaline rush was so intense. This was because one voice I could recognize of my mother’s but the other one was a guy I didn’t know at all. It didn’t take me much to realize what was happening inside. I wanted to run away as fast as I could but my legs felt like as if they were made of stone. I completely forgot about thirst of water at that time. All I was thinking was who it could be with my beautiful sweet mother inside our own home! I suddenly realized that I was getting a real hard one down my pants. You could clearly relate those few times when you get so hard and blood rushing towards the organ so fast that it itself beats up and down in a rhythm like a heartbeat. That was happening with me. I was standstill. I don’t know why I put my hand inside my pants but soon as my fingers touched my penis, I ejaculated and blew a huge load off. It was one of the best and memorable orgasm I ever had. Suddenly I was a bit ashamed of what I have done and ran towards my room and locked the door from inside. I cleaned myself up and sat on my bed. I couldn’t wait till morning so I could see who that was with my mother. I could still hear very few almost vanishing distant sounds of them having sex. Everything went quiet after a while. It was almost 7 am when I heard the front door opening. The front door was a bit cranky so opening it made some noise. Luckily I could see the front of our house including the door from my room’s window. I rushed to my window curiously. I could see a guy about 25/30 of age opening the door and putting one step outside. My mom was behind him at the doorstep. I was very shocked to see that as he was about to walk forward, my mom pulled him from behind with a laugh and he put his arms around my mom’s hip hugging her. Then he bend my mom over a bit backwards and have her a deep french kiss and said good bye. I was hard again. I quickly went to my bed and took my load off. After that I though all day about it. It felt so good just thinking about him having sex with my mom. As days went by I realize my mom was doing this every weekend. So it became a routine for me to listen to them and jerk off. Even I also enjoyed the dirty talks guys said about mom at school after that time. It has been going like this ever since. The guys my mom brought never lasted. It was almost every weekend when she brought in a new guy. Sometimes there was exception that a same guy came over for several weekends. I always wait for the weekend to come so that I can listen to them and have some fun. Even some weekends if I am lucky they come home so drunk that they forget to lock the door. At that time I could easily get a sneak peek from the door. The most asked question from people I get is – “Have you never talked about it with your mom?” The answer is – I think my mom realizes very well that I know. Because some weekends my mom comes home early with the guy and make him introduced with me as her friend. I take it easily. Even we have dinner together and do a little talk. Then I go to my bed saying goodnight to them and they head towards her bedroom. I get most excitement when the guy also has breakfast with us before leaving. They indirectly talk about how good my mom is in bed while we three are having breakfast. My mom giggles and softly pokes them with her elbow and we all three laugh a bit. It excites me so much. This has been going ever since. I don’t mind because I realize everyone has needs. I just want my mom to be happy. Also I get some fun as well. I have been focused into it so deeply that I never thought of getting a girl for me. I can give up that if it takes for my mom to keep her happy forever. This has become a lifestyle for me and I enjoy it.
However my ultimate fantasy is maybe someday my mom falls in love with one of the guys and decide to marry again. Afterall, our household needs a strong dad figure. I would be very happy to see my sweet mom having all the satisfaction she needs from her new husband. I would be okay if my new step dad likes to tease me and humiliate me. I will do all the household works for them. As a token of gratitude I hope they will sometimes let me watch when they get along. Just having sex is kinda boring. I like how a guy would OWN my mom. Make her completely forget to care about his son and shift all the love and focus on her new man. It would be hot if my mom loves seeing me humiliated and teased and team up with my step dad in tormenting me as much as they want. I will always be their good cuck son.
All I want from you guys to support me in this fully and it would be so nice if you people would explain my psychology behind it. All kinds of opinion both positive and negative are welcome. You can also hit me up for a talk if you want. But please do not come up with desparate messages or just simple “hey/hi”s. I am looking for a nice discussion so please make that approach not just roleplaying. It would be easier if you have any questions you need answers about this so you can explain better. I am open for chat and voice chat too. Hoping to hear from you guys soon. Thanks for reading this long post.

Helping me stop smoking (MF)

So i’ve been a smoker since high school. It started at 16, my parents had sent me to an all girls catholic school. I became friends with a group of girls that smoke, drink and soon emulated their behaviour.

Its been 10 years now and i can’t stop smoking. My bf does not like it. A few days ago, I finally decided it was time to quit and my bf offered to help me. We agreed that if I smoked again, I would be punished. We had not agreed on any punishments yet, it would be up to him. In my mind I though the punishment would involve maybe doing his chores or paying a fine. I was wrong.

One afternoon, I got home from work, and had the place to myself. I did not expect him for another half an hour. The urge to smoke was very strong but I tried my best to resist. Went to take a long shower, trying to clear my mind, but the more I tried to fight it, the stronger the urge got, to the point that I finally caved in. I had a secret stash of cigarettes, I went to get one and went straight to the balcony. Read more »

Piece by Piece: Chapter One [MF] [Straight Sex] [Busty] [Huge Boobs] [Cheating]

“Both hands on the wheel stan,” I said as I looked over at my husband.

“Relax,” Stan said as he put down his phone. “Just Maxwell telling me about the meeting tomorrow,” he said with a smile.

“Well, he can wait,” I said, looking at the icy road ahead. I hated this stretch of road. It had claimed many lives, especially this time of night. “You guys have your seat belts on?” I asked our kids in the back seat.

“Yes,” they all chimed at once with slight annoyance.

“I have gotten us to your mum’s place and back home every year since we got married, not once have we had an accident,” Stan said as he shook his head. “Relax.”

It was easy for Stan to relax. He had never lost someone to this godforsaken road. Back in high school, I lost four of my friends. I was supposed to be with them, but at the last moment, I chickened out. We were all going to go to a motel out of town to have a substantial makeout session with the boys. Chuck Tidell was the guy my friend had picked out for me. He was tall and muscular, and he played on the basketball team. Read more »

PAWG college girl submitting complete to her new lover’s amazing cock. And becomes his exhibitionist play thing

In College I lost my virginity, I did it with a friend. A chubby plain looking read head that I really wasn’t that sexually attracted to. Her and I had lame sex, five or six times.

She was very shy and old fashion and I was very inexperienced. I had no confidence with her to try anything fun. Even though I’ve been watching porn and imagining great sex for years.

I have a high sex drive and a wild imagination. So I had a huge bucket list of sexual things I would like to try.

One day I nicely told her we’d be better off friends.

Over the next few weeks she got kind of obsessed with me. Even after I tried to break things off nicely, a couple more times.

At the time, I had a black-out drinking problem, and she used to wait until I was very drunk and find me. I kept waking up with her.

I could never remember the sex we were having but I started seeing and feeling signs that we were fucking like crazy. Some mornings my room reeked like pussy and my dick would be sore. I would see four or five used condoms all over the messed up room. Read more »