Tag: High School

The Cheerleader – Part 1

This is my first time attempting to write a story. I didn’t want to just write something short; I like to “world build” when I create things, so I know part 1 doesn’t have much action, but I intend this to be probably 3 or 4 parts. Suggestions are welcome.

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I inwardly groan as my alarm clock starts buzzing. My favorite thing about college so far has been that I don’t have a single class before ten in the morning. I lay there for a couple of minutes before rolling over and turning my alarm off. I like my room to be cold at night, and as I climbed out of my bad, I felt the cool air on my bare legs and my midriff. I could feel goosebumps rising on my arms and glancing in the mirror I could see my nipples hardening under my thin nightshirt. I’m about 5’8”, with green eyes, and light brown brown hair that comes down just below my shoulders. I’m fairly petite at only 130 pounds; I wish my boobs were a little bigger, but I am not unhappy with their B-cup size. I’ve always been told that I’m pretty, but in my mind I’m just average. I try not to think about the upcoming cheerleader tryouts as visions of making a fool of myself start to flash through my mind. Read more »

my greatest sexual experience of college….my first squirter [MF]

this is my first attempt at this so please bear with me…

(backstory) prior to college i’d only ever been with one girl, who i dated through all of high school. when we broke up not long after starting college, a whole new world of girls was opened up to me. one of the girls that really caught my attention was a beautiful asian. we’ll call her susan. susan and i had some classes together but never really hung out socially. after sophomore year when we had gotten to know each other a little better, i worked up the courage to ask her out. it’s important to note that if you saw us together walking down the street your first thought would be “how the hell did he get that girl.” we started dating, but i didn’t really see it progressing in to something serious, so i wasn’t really as invested as she was. eventually about 6 months in to our relationship she broke up with me, which i was not at all surprised about. we had amazing sex throughout our relationship, which didn’t stop after we broke up…. Read more »

Discovery of a Cuckquean – Part 1 – [MFf] – Female Cuckolding

This is a story about me being an asshole to a young woman. She was a an asshole to me first, but still, fair warning. It is not always a nice story and I don’t think any of us come out looking unstained. It is a story about my being an asshole and her discovering that she loved it and that she was a cuckqueen.

To understand how this came about, you have to understand my past with Mel. Mel was my first love. My stupid, ridiculous, teenage love. We were off and on all through high school with a very serious senior year. We decided to be LTR going into college and spoke on the phone almost every day with regular phone and cam-sex sessions.

Winter break was to be our first face-to-face since we had left for college. I had saved my pennies to buy her plane tickets to come stay with me over the break and then, the night before her flight, she dropped the hammer. She had been dating someone seriously for months and at that point considered ME to be the other man and was breaking it off with me. Read more »

We Went All Out For Our First Swinging Vacation. (PART 1)

PART 1

We drove up to the resort in mostly silence, but it wasn’t uncomfortable. The playlist my wife and I had been listening to had run out and we hadn’t bothered to put anything else on. My mind was racing, because I could barely believe that we were actually going through with this. I know her mind must have been a mess of thoughts as well. She just looked out the window, watching the growing thickness in the tree line along the highway. There were times that the silence freaked me out, made me think this was a bad idea. However, I’d then catch a glimpse of her slowing running her fingers along her bare thigh, while wearing her pink shorts and then a slight, barely audible, moan.

“You scared me there for a second babe,” I said to Jess. “You’re not getting cold feet are you?”

Jessica looked over at me with a slight fire in her eyes. “I’d be lying if I said I’m not nervous as hell. What if everyone thinks I’m the boring, ugly one?” Read more »

Best Friend Backup Plan [mf] [teasing, oral]

Descriptions:

I’m 5’10”, 175lbs., in pretty solid shape at the time of this story. I had short, dark, “styled” hair and was generally considered a pretty good looking guy.

Stacy was about 5’2″, 95lbs, absolutely tiny frame that somehow had perky b-cups, very cute face, and shoulder length “blonde” hair.

Background:

I had grown up with Stacy from when we were in elementary school. Our mom’s worked together, were great friends, etc. I’m almost exactly 1 year older than her a grade ahead, so we didn’t really hang out much but we knew each other well from seeing each other in school and when our moms would get together.

Years pass with us knowing each other, being friendly, but never really being friends until we start working at a local casual dining restaurant together. Within a few weeks, all that time and knowing each other exploded into full-on best friend status. All the background knowledge we had, the shared experiences, the inside jokes, all came together to make this incredible, platonic relationship. We hung out all the time outside work. We were both in high school when we started working there, so we’d hang out between classes, with overlapping circles of friends. We would approve or disapprove of each other’s dates. I mean, pure, platonic friendship at its finest. Read more »

Cubs Win! And so did I! [MF] [oral]

Hello friends. It is a good day for anyone born north of the Mason-Dixon line of Chicago baseball fandom. Even though I wouldn’t consider myself a die-hard fan, it was pretty awesome watching the Cubs win the World Series last night. But that wasn’t the only enjoyable thing that happened last night!

DC is the most transient town in America, so it’s easy to find a ton of other folks from your hometown. And since this town is tight as hell when it comes to socializing (politician, lobbyist, government worker or journalist, we all love booze, food and sex in some order). So when I decided to host a get together for Game 7 with other Cubs loyalists, it didn’t take long to fill my small apartment. Most of the people were guys and gals I’d met working here, but there was one old friend I reached out to. Read more »

And she was made to watch, suffer and be used – [MFF] – BDSM – Female Cuckolding – Humiliation

It was the week of my birthday and Leslie called to invite me over for a birthday dinner.

Now, Leslie and I have a complex history. We started off dating with a bit of BDSM with her as the sub, involved other women, experimentation and eventually, she discovered that she was a power-dominant and a lesbian. Fortunately, our relationship had always been more of a FWB thing and as she drifted from me as a dating partner, we stayed great friends and occasional lovers. We shared women on occasion when we were both single and Leslie had a real fetish for humiliating her submissives by bringing me into the bedroom. A lesbian cuckoldress.

Why me? Am I an incredible lover or some god of sex? (Well I like to think so) but no, its really just came down to three things. The first was that Leslie trusted me deep as I did her. The second was that she knew my tastes and that I could be a lot of fun in the bedroom. Finally, as a lesbian, she didn’t want to have to say that the number of men she had fucked was rising. She said I didn’t count, which I chose to take as a compliment. Read more »

Orgasm in front of girlfriend’s unknowing dad[MF]

Some people asked me to tell about the relationship I had with a married woman, and I’m sure I will at some point, but I do still have some guilt over being an adulterer (we just decided to try to chill out two months ago). Plus, to be perfectly honest, it’s a very, very long story for me to describe correctly. Hope you don’t mind me instead describing a quickie I had with a girl my age (I do sleep with “age appropriate” girls, too!).

If you do want to read about my first time with an older woman though, you can check it out [here (pt 1)](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/):

To just start with a little background, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence. Read more »

Devotee erotica – first try at this kind of thing

Hillary Davenport was running late. This was not unusual for the plain girl with golden hair. She always kept a full schedule. She believed that the busier she was the better her life would be. Idle hands, or so she told herself. Today she was increasingly flustered as she found herself dashing from one meeting to another all over the city. Perhaps she should have listened when her mother said accepting a job at Goldman Sachs while finishing her last year at Harvard was not the best idea. She dreaded becoming like the vapid heiresses in class who simply went to graduate school to find a husband.

Hillary was flying down the highway at 90 mph so that she would be on time for her appointment. She was coming from the registrar’s office, confirming she had completed all degree requirements to receive her MBA diploma later that Spring. She knew she had, of course, she was in the top 5% of her class.

She rummaged through her purse searching for her phone. In her rush to get on the road she had forgotten where she was going.

“Orthodontist – 5:30 p.m.” she said reading the screen while ignoring the road before her. Read more »

Fucking my Gf and her younger sister [MFF]

A little context before the story, this took place about a year ago and me and the older sister are no longer dating but still are decent acquaintances. So the story happened like this, we were at my girlfriends house alone watching this crime drama about a cereal rapist, now we’re both asian but she was this petite 5’6 fair girl with an amazing ass(she had a flat chest though about a couple B’s) while I was about 6 ft 165 lb and kinda muscular(went to the gym 5 times a week). She was always really prude about sex and we only ever did it twice within our second year of dating so it was kinda sparing. But for some reason the cereal rapist show turned her on and I noticed that so I took the opportune moment to kinda play with her and tease her a bit. Read more »