Tag: High School

Dorm room sleepover goes exactly how you’d expect [MF]

Freshman year of college. My girlfriend was a year younger and a senior in high school. Different things work for different people, but I would not recommend going to college with a long distance relationship. Not an excuse by any means, just a piece of advice with the benefit of hindsight.

I lived in the dorms and a friend of mine from high school, R, lived a few floors up in a triple room. If dorm life with one roommate makes it tough to get some privacy, a triple makes it impossible.

On this particular Saturday night, R’s roommates both had their boyfriends in town while my roommate was back home for the weekend. Being the gentleman that I am, I said she could sleep on our futon rather than fifth-wheeling it.

A bit of back story: Me, 5’11”, dark hair, dark eyes, 170 lbs, athletic, but skinny at this point. R was 5’6″ , light brown hair and cute, if not a little nerdy. She had an athletic build with average size tits and wide hips with a decent ass. We’d always been a little flirty, but she was friends with my girlfriend and she had just recently taken a break with one of my good friends, who she’d dated for several years. Read more »

How My Mom (51F) and I (25M) Became a Couple

Apologies for rambling with the backstory but figured it was helpful context:

Never talked about this with anyone but needed to get this off my chest. My dad wasn’t around growing up so it was just my mom and I. We weren’t some poor family abandoned by dad. My grandfather has a couple successful businesses that my mom worked for so we were fine growing up.

I was a pretty normal kid, played sports, did well in school, etc. Dated a little bit in high school but I really saw how possessive my mom could be at this age because she always found negative things to say about the girls I went out on dates with. I never told her about them but she found out thru the grapevine. She’s like the damn CIA smh lol

My mom is def a milf. A classic Italian mom with nice boobs, good ass, and smooth, soft skin with the jet black hair. I stroked my cock to her all the time growing up. She always dressed in yoga pants and a tank top around the house so nothing too sexy but enough to let my imagination run wild. She was overly affectionate. Always gave long lasting hugs while telling me she loved me. I never let go, always loved feeling her boobs nice and close. She always gave me kisses on the lips. When I was little they were pecks but as I got older, I held the kisses a little longer. She enjoyed it too. Read more »

[M32/f19] “You Rape What You Sow.” [trigger warning: Rape, Drugs, Degrading]

My name is Mason and I am 32 years old. I was born in Mexico but lived for almost ¾ of my life in the United States. A brief backstory without going much into detail, I, unfortunately got deported and was sent back to Mexico all of a sudden. I still had extended family in my place of birth but not my immediate family who were still back in the states. I didn’t know Mexico at all and was used to the US seeing as I haven’t been there since I was 5 or 6 years old. I couldn’t go back to the United States until I applied and got approved for a Permanent Resident Visa. I did apply and I got approved by some miracle. This is one of the fun and kinky things that happened to me after I was deported back to Mexico for those lonely but exciting years. Read more »

19 [M] I fucked my friends mom at a grad party [Cheating]

This was last summer . I had just turned 18 and was going to a grad party for a classmate who had graduated high school with me. I was particularly excited because this friends parents were known as the “cool “ parents who always let us drink / party.

This was a bigger party , lots of friends and friends parents . We started playing some beer pong and this one mom had came up to me and said she wanted to play . This mom was probably about age 40 but very attractive. She was petite but had nice big tits with a plump ass and you could tell she frequented the gym . Nice big lips , well dressed, knew how to look good.

A little about myself . I’m 6ft 1 .. very athletically built and consider myself decently handsome for sure . More importantly , very confident with women . At this point I was also very experienced
. ( had been with about 15 women ) definitely had a reputation for making the rounds. Read more »

Winter break fun with my ex gf, Josie. [MF 21] Part 6

Josie had just finished giving me a very long, edging blowjob/handjob. She was laying naked on the couch next to me with her head in my lap.

Josie said, “Alright, I guess I should head home before your parents get home from work. Your mom is nice but I can tell underneath, she cannot stand me.”

I said, “Josie, it’s not so much you, she just cannot stand any girl she thinks I am having sex with. Also, she probably hates your style.”

My mom was very old fashioned.

Josie said, “Oh, she hated other girls you brought home?”

I said, “Oh, man, I brought home this girl when I was 19 to spend almost a week. They tried to keep us separated, but we were so horny and they left us alone one afternoon. We took a shower together, which led to pretty much anything you might imagine. In fact, that was the first time a girl peed on me in the shower.”

Josie laughed and said, “Certainly not the last…”

Josie was laughing as she was getting dressed. She said, “That is why I need to leave now. Your mom seems nice, but I can tell she doesn’t like me.” Read more »

I 32[M] Had a Pool Party with a Married 31[F]riend

This happened last month. I have known my friend, let’s call her Sarah for this story, since elementary school. We have lost most contact since high school aside from sending snaps back and forth from time to time. We both went on to God careers and are both married. Well, after all these years I ended up living across the street from Sarah’s sister and brother in law who I have become good friends with. One night they invited me down to their parents house for some drinks. I get there and the party they had was winding down but Sarah and her sister were still going strong. We sat on the back patio drinking, catching up, as well as discussing the woes of our marriages. Eventually Sarah’s sister decided to go to bed leaving us alone. We had a couple more drinks and I got to to head home, when I went to say goodbye and give her a hug something felt right and I went in for a kiss. Read more »

Ricky or Rikki? [MF][Trans][Rom]

We grew up together, Rob, Keri, Ricky and me, close neighbors so we gravitated together, easily. Ricky and Keri were – are twins, so wherever Ricky went, Keri was always there. We were the Four Musketeers. Rob was Athos, analytical, a planner, always behind our mischief. Ricky was Aramis, really good looking guy, but always seemed at odds with himself, in a perpetual dilemma. Keri was D’Artangnan. Being a girl, she was the outsider always proving herself, not that she needed to, to us, but to others, they underestimated her all the time and she wasn’t prepared to put up with any of their bullshit. And me, Greg, I was Porthos, loyal to a fault sometimes, and like the original, didn’t always get conversations, mainly because I had a hearing problem which I didn’t know about until I was in my teens. Read more »

[FM] I lost my virginity to a DILF

Sex is something that has always made me a little uneasy to talk about. So this is a little bit therapy for me, as much as I want you all to also enjoy what I write.

I guess by way of introduction, my name is Taylor. I’m 22-years-old. Im 5’5, blonde, and have DD implants. I was blessed with itty bitties, and while I know that might be what some guys go for, it was a point of insecurity for me growing up and in college. So when I had saved enough money, I got myself some boobies and my body confidence shot up.

I went through all of high school without much of a dating life. I had crushes, of course, but I was definitely what most would call a late bloomer in the looks department. I had braces and big thick glasses, and I was on the thicker side. I’m pretty much opposite now: a gym membership, Invasalign, and contacts will do that for you. It helps that I also learned how to apply makeup and style my hair so it was less, well, poofy. Read more »

The Time I Fucked My Friend’s Best Friend [M21/F22]

If anyone has read about the time I fucked Carly, this story is about the time I fucked her best friend.

I’m still in college, now a junior with much more experience than when I lost my virginity to Carly as a freshman. Carly and I had remained friends after our sexual encounters. We had begun dating for a bit as freshman but it never really worked out, so we decided staying friends and FWB was a better option for us.

Anyway, as with any friendships, you begin to make friends with other friend groups until you eventually know a lot of people through mutual relationships. That’s how I met Natalie.

Natalie was Carly’s best friend and had been all through elementary school and high school until she finally transferred to the college that we both went to her sophomore year. I found her extremely attractive although she didn’t necessarily fall into what I would consider my type. She was a little more alternative with her hair cut pretty short (occasionally spiked), nose ring, multiple other piercings (I’ll get into that later) and all of the other stuff you’d usually expect. Regardless, I still thought she was really attractive. She stood about 5’3” tall, probably weighed somewhere between 125-135 but thick in the thighs and a tight stomach. Read more »

[FM] Asking my best friend to help me try out bondage [Slow Burn][CNC/Dubcon][Bondage]

Me (female, 26) and Anthony (also 26) had always had a pretty special friendship. We had met on the first week of highschool, and my first impression of him was that he was kinda weird. I had always been a calmer person who observed other people a lot, and didn’t have a lot of buddies. Instead, I only really hung out with a handful of people, but these were really good, close friends.

As a shy, tomboyish girl I didn’t dare to speak to anyone at the beginning. I finally mustered up the courage to talk to Anthony, after I noticed that he seemed to really have taken a liking to another girl in the class. He was ashamed that I had noticed, but I instantly assured him that he should talk to her, and in the end he was lucky enough and she ended up being his first girlfriend. From that day on, we had been super close friends who shared most, if not everything from our personal lives. Read more »