I was at a houseparty with 13 people I consider regulars (people whom I invite and that invite me to parties). These parties are great because everyone knows eachother and everyone likes eachother. About one hour in we decided to play a drinking game for the first time (we were high school seniors who haven’t really gotten the chance to try it yet) called King’s Cup. Kings’ Cup is, for the ignorant (you can skip to the next paragraph if you know what King’s Cup is, but we included some different rules that are important to the plot), a game where a deck of cards (we used two to extend the game) is equally distributed among the players. The smaller decks are then made into a ring from where we pick one card in a clockwise fashion. In the middle there’s a cup (not important to this story). Each card is given a action that has to be preformed (we played without the ‘last person to do this has to drink’ actions and replaced them with truth and dare instead). The card that is really relevant to this story is of course the king. The king allows the one who picks it to make a rule. Usually when a new king is picked, we discard the old rule, but because we wanted to get drunk and have fun, we decided to allow three rules to be in play at once, which worked out amazingly for everyone.
Tag: High School
The First First [MF] [oral]
I lost my virginity in college, freshman year, to an exchange student from England . . .
Jessa.
She wasn’t the fittest girl I’d ever met. She was only slightly shorter than me, and had a fair bit of ‘padding’ – I tend to consider her as the founder of my enjoyment for both fit and thicker women. Her breasts, while it was a few more days before I got to see them in all their glory, were large and welcoming. Her size allowed her to have a fantastic ass: fantastic for grabbing, slapping, squeezing, biting . . . she kept her blonde hair cut to the middle of her back, just the right length to hold onto during particularly fast-pacing fucking in doggy-style.
For whatever reason someone wouldn’t want to go to bed with her, her British accent and oh-so-nasty vocabulary swept the board and replaced any hesitation with anticipation.
After years, I get a booty call from my first gf, and it turns out she’s quite freaky :) (dp, face fucking, gentle femdom)
So, I did not mean for this to be so lengthy, but I was kind of reliving this as I was typing. It takes a couple of unexpected turns, to say the least. If you read this to the end, you’ll probably at least get a boner or a sploosh out of it, maybe even cum?
This story happened in my mid 20’s…
I dated this girl, “Jess”, in late middle school and early high school. We were each others’ first, in every way. We experimented sexually more than many adult couples do. We were head over heels for each other. Our parents found out we were fucking, and we were banned from seeing each other. We were ripped apart, and we attended different schools and virtually never saw each other. For a few years after that, we’d meet up a few times and fuck like rabbits in the park or out in the country. Having never had any closure from our relationship ending, it was always very passionate. We eventually started dating other people, and I took off to college after graduation, and she remained in our small little southern town.
Wrapping Up the Night [MMf] [DP/anal] [group] [voy]
**Continued** from *Dancing in the Basement*, *Emily in the Shower*, and *The Private Party* – links in comments
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The main floor is nearly empty, at least in the halls. I head to the bathroom to see if Emily was still in there.
The room is dark, but her shirt is still on the floor. I grab it and head to the kitchen to look for her. I wasn’t sure what I would do if she’d gotten in trouble, but I felt responsible to find her. There are only a few people in the kitchen, and they deny seeing her even come through to go outside. I go back to the main hallway, and decide to check the bedroom.
First I knock softly on Ashley’s door, and crack it open. It’s dark, and there are a few people sleeping on the bed. I flip the lights on and head over to see if any of them are Emily, or Ashley. None are, and one of the sleepers who woke up to the light suggests I check the guest bedroom. Apparently, the guy says, that bedroom has been the place to be all night, even with its door closed.
I Got Fucked by My [(T)MtF] Teen Bully [M] At a Reunion
I grew up in a pretty small town where everyone knew everything going on. If you’ve read my previous posts, you probably have a good idea of my life and personality up to now lol. But just to recap, I always knew I was different from an early age. I was a shy petite boy and had trouble fitting in with other boys in school. I didn’t like getting dirty playing in fields like other boys my age and so I was bullied. It wasn’t anything too bad but there was this one boy in Junior High School named Matt who was especially rough on me. He was like the Alpha in his little group of overly masculine boys and it seemed like he would go out of his way to belittle me. I was definitely not as confident (for sure in the closet) about my sexuality at the time, but anyone with eyes could tell that I was different. My hair was longer than most 12-13 year old boys, and I liked to roll up my shorts just a little bit to make myself feel like I was wearing the girl’s uniform set. Of course the girls had skirts but we’ll get into that later.
The High School Reunion and The Hot Cheerleader [M/F] (long)
Hey all, it’s Jonathan again. I’m here to excite you with another sumptuous story of my wonderful sexual encounters. Hold on to your junk tightly, this is a good one. (skip to ****** for the good stuff)
It all started when I attended my 10 year high school reunion. I went to a small high school in a small town, only about 100 per graduating class, so I knew most of the people in my class pretty well. Small towns are great for a couple things, you know everyone’s business and it’s boring as hell. Thus, you know who’s fucking who and that’s all you have to do. Let’s just say the small town women know how to keep you warm at night. (and some of the guys too, not my thing though)
Most of my classmates and friends had moved away to bigger cities for better jobs, but the class got along really well so the reunions were highly attended. I arrived at the 10 year reunion still single, after being divorced some years earlier. Not my ideal situation, but a bunch of my guy friends were single too so I figured we would have a good party. I had no expectations for a hookup, as the small town didn’t offer many good options that weren’t taken.
Being denied sex by my ex helped me perfect fingering myself!
To start, I may be self-conscious, or not the most confident girl. However, there is no shortage of men (and some women) that have chased after me. Although I can’t particularly see why that is, it must mean I’m at least somewhat attractive, right?
I’m 20, 5’5″, dirty blonde hair, 115 lbs, 32C, was told I had the best ass in my high school days before I had a boyfriend. I’ve been compared to Christie Brinkley in her younger years, even told that it’s creepy how much we look alike (although I can’t see it).
Anyway, my last relationship lasted about 2 years. In the beginning, the sex was crazy. He was my second (and last, so far) sexual partner and he showed me what I thought “good sex” would be. However, after our first year, his interest in me seemed to slowly decline.
He wanted to spend more time with a particular male friend of his, who he openly thought was gay but was apparently too afraid to ask him.
I noticed that on the nights he would hang out with this friend, his phone would miraculously die and he wouldn’t want to have sex for several days after. I thought I could be paranoid, but the signs got worse and worse.
The best sex
Tired and hungry after work one day, I plan to go somewhere with some friends to grab a bite to eat before heading home. We all roll out the parking lot and go eat at a little burger place down the street. I had my two friends Charlie and Kenny, then a bunch of other people I work with. All of a sudden I hear someone call my name, it’s Anne. Anne is the one woman every guy wants to fuck, her curvaceous body, perky breasts, long dark hair, and her round juicy ass. The only down side was that she had a boyfriend who’d she been with for some time and I had a girlfriend who I have been with for a year.
In the corner, losing part of my virginity [mf]
“Stop flirting with me or kiss me.” So I did.
The summer after high school, my older brother’s friend got me a job barbacking at a small club – normal, relatively quiet, bar five nights a week, packed hip-hop club on the weekends. It was a great gig – cash under the table, minimal hours for enough money to have fun, a sharp increase in alcohol tolerance…
I was young and enjoyed the job, so I worked hard and quickly became the owner’s personal barback in the DJ room on weekends. She could count on me to keep everything stocked and glassware clean, which earned me a number of free shots and lessons in bartending.
We had a rapport but I didn’t think much of it – Alyssa was in her mid 30s, married, a couple of kids, not smoking hot but very cute. I had dated but nothing serious and I was pretty self-conscious about being a virgin. As a young, six-foot tall white guy with red hair to my shoulders I got a lot of attention from the mostly black female clientele but I had no game and never could figure out how to proceed. All summer the best I could do was an occasional makeout session.
Hiking + Tent + Thunderstorm = best night of sex ever [m/f] (long)
This is my first story, so let me set the background. (skip to ****** for the good stuff) This was the single greatest night of sex in my life, so the detail will be lengthy.
Let me introduce myself, my name is Jonathan and I have some stories to tell. Hopefully, these stories will charm you, make you laugh, turn you on, and give you a sense of the good sex life I’ve lived. I’ve had a wild ride over the years and thought I should share them.
About me, I’m a pretty average looking guy, 5’11”, dark brown medium length hair; I am not a skinny guy, about 230 lbs, but I work out often and am pretty athletic, an ex-football player. Lots of education and pretty successful in business, so I’m the type of guy that gets brought home to meet the parents a lot.