My first foursome

Despite knowing Mallory, Sam and Julia for a whole school semester, and fucking them throughout, we actually would not have a foursome until the beginning of summer. After getting intimate with them it was something I wanted to do, but we never really got the chance to, until that day.

So it began during dinner on the day school ended…which Sam and Julia paid for (read “Competitive Fucking” Story). And we were just talking about normal things, and then Julia told us that her family was gonna be out of state next weekend and she asked if the four of us wanted to spend the weekend with her at her place (with her family not knowing I was there). Julia was an only child and because she struggled to make friends (before we came in), she would get pretty lonely, and this was quite often with her parents. Mallory and Sam both said they’d love to, and because I lived alone, I would have no problems. And the plan was set, we would spend 2 nights at Julia’s place.

My Friends and their competitive fucking

To So this story happened at the end of my junior school year. school would end at the beginning of June. So on the last Friday of April, the 4 of us went to have lunch after school. At the restaurant, Sam would come up with an idea, she would say that since school would end in a month, she declared that she, Mallory and Julia play a game throughout the month of May. Now… because our group treats sex as a normal activity the 4 of us would do, it ended up making Mallory and Sam quite competitive. They would do things either with themselves, or with me to one up the other. Like this one time, they wore buttplugs the entire day to see who took it off first (Mallory lost that one) and another time they would play a game of Uno, and the winner of the game would get dicked down 2 out of 3 (Sam lost that 2-1).

Good God I’m in a Hentai Now!

I have told you about my two fuck buddies, Mallory and Samantha. But they aren’t my only friends in the school, there’s a third. This story began the same week I met Mallory, but the steamy parts happened after I started fucking Sam, so its another long story.

So around the same week where I would meet my first Friend with Benefits, Mallory, I decided to join the school’s anime club. I enjoy anime so obviously I would go there to spend my Fridays. The first two weeks it was pretty normal, people watched anime, talked about it etc. The Thursday after however, I noticed there was a girl sitting reading a manga while everyone was watching a show. I saw it was Miss Kobayashi’s Dragon Maid, so I sat beside her to spark a conversation. She was a cute Asian girl, and she engaged in the conversation well. She would introduce herself (Lets call her Julia), and we would have a pretty lively conversation. She was wearing pretty baggy clothing, track pants and a loose hoodie. We ended up becoming friends that day, and I would also find out that we were in the same AP English Class. This was around the time Mallory and I were hanging out normally, such as going to the gym together.

(M)y School’s Cheerleader Squad hid a Gem. Part 2

Another week after that, another Pep Rally was announced on Friday of that week where the school would give the 8th Graders a tour of the school, and then welcome them into the school for next year. I wanted to hangout with Mallory and Sam after because we were gonna have a three day weekend, so I decided to wait at the cafeteria for them. Mallory said she needed to do some after school work so she went to do that. After about 20 minutes of waiting, I was approached by Sam, she was wearing her cheerleader outfit, and seeing it up close, I could tell her fat white tits were spilling out of her bra. She asked me what I was doing, I told her I was waiting for her and Mallory, but that Mallory is busy. She then told me that she wasn’t feeling well so she asked to not attend the Pep Rally, so she asked if I wanted to hangout with her, and of course, I said yes. We walked around the school, and with her beside me, I could smell the perfume she was wearing, but all that was in my mind were the constant jiggling of her massive milkers within that tight cheerleader outfit. She then told me excitedly, “I found something really cool in the gymnasium building, I wanna show you”. Walking around the gymnasium building I noticed it was definitely older than the rest of the school. She took me to this old bathroom that’s not used, and then took me into a stall. She then told me that Mallory kept talking about mine and her sexual experiences together after the day she told her we were fuck buddies… and then the words that shocked me, “I want in” said Samantha. And to be honest, I could not take it anymore, I said yes please without hesitation because I’ve wanted to fuck this fat assed white girl since the day I met her. And as soon as I agreed, she took off her cheerleader uniform top, where I finally got to see her small bra trying its best to hold her heavy honkers trying to spill out, my cock could not stop throbbing, as it just wanted her more than anything. Sam then pulled my jeans down and slowly started stroking my cock. I leaked so much on her hands she stopped to lick it off then started sucking while caressing my balls. I hope Mallory doesn’t see this but at the time I thought Sam sucked better (They used to compete a lot). What made me glad at that time is that Mallory didn’t come to school the day before and she didn’t have the time to suck me off in the morning that day either, so my fat balls were absolutely full and blue, and with Sam’s sucking and ball squeezing, I could definitely feel I was on the verge of really cumming.

(M)y Highschool Cheerleader Squad hid a Gem. Part 1

This story happened after about 2 months into my FWB relationship with Mallory, we would become regular fuck buddies, getting it on whenever we had the chance since we only had 1 class together. Sometimes she would begin my school morning with a blowjob in the bathroom before class, I would say Mallory became my best friend in school along with FWB as we didn’t just fuck and nothing else, we would do all sorts of things.

Going back to the story, we were told that today the school was having a Pep Rally. Usually I skip Pep Rallies, but today Mallory and I were gonna go see a movie so we decided to attend the Pep Rally to pass the time until the movie starts. As we went to the gymnasium, we passed by the cheerleader squad on their way to the backdoor of the gymnasium. They all walked in a line, until my eyes caught one of the cheerleaders around the middle of the line. A blonde girl with thick legs, a large ass (yes a PAWG) and large jiggling tits (she was a 36DDD) which really caught my eye. [Bit of Backstory: Because of my Big Breast fetish, I can really only get hard to women with “abnormally” large breasts, DD is the smallest I’d go] So I was staring as she walked by, she didn’t notice, but Mallory sure did, and jabbed me softly, giggling as once again a Busty girl captured my Size Queen ass.

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(M)y first Sexual Experience back in Highschool

This ones a bit long and the sex comes pretty late so i apologise.

During the second half of my Junior year in highschool (that’s Grade 11 for people living outside the US) I transferred to a new school. Obviously being an introvert, I wouldn’t really approach and talk to people, so for the first few days I wouldn’t make that many friends. I just went on with classes normally and went on my way.

However, around my 2nd week in school, during our history class, we were given a group project, and we would be in teams of two. And I got grouped with this Latina girl (Let’s call her Mallory). She was definitely pretty, and we didn’t talk much on our first day but we did our introductions and she seemed like a nice girl. But on the second day we met, I saw that Mallory was wearing a tight shirt and I noticed that her tits were absolutely massive (She said she was a 34F). I had no idea that she was hiding all of that because she was wearing a pretty loose top the first day we met. Throughout the day I couldn’t stop staring at them, and it was hard to sit near her due to my hard-on. And because the group project was a two week long ordeal (and this was an AP class so a lot of work) I could not wear jeans, and decided to wear loose track pants to give my dick more room.