Tag: High School

[F/F/M/M] “Why don’t you join us?” Part 1

To preface this story I first want to say that I am not the best storyteller. But I’ve been asked to share this story, and it is an entertaining story, so here it goes.

I was a naïve little junior in high school. My life revolved around dance class and schoolwork. I had a couple good friends whose lives were similar and other than that didn’t talk much to other people. I was known to be quiet, innocent, and hardworking. People were always surprised when I mentioned smoking or drinking. They weren’t activities that I did regularly, but I did occasionally partake in them. So while I certainly wasn’t innocent, I wasn’t a wild child either, that would come later.

The one area where I was beginning to be a bit devious was with sex. I was the first of my group of friends to have a boyfriend and have sex. However, I quickly realized that I wasn’t interested in him and broke up with him. Shortly after I came out as bi (a whole other great story) and slept with a girl for the first time too. Second semester sophomore year, I began hooking up with one guy who I would continue to see throughout high school. Read more »

Fucked in the Hard Rock Cafe

This was a while ago so I'll see how well I can describe this.

My girlfriend and I met up in Denver (I was a freshman at CU and she was still in high school [18+ don't worry] at the time so we had to get together on the weekends) and decided to go to 16th street mall for dinner. Didn't have any specific plans but we decided that we would go to the Hard Rock Cafe to get a burger and I love looking at the music memorabilia. Not the classiest joint but whatever, the story moves on.

Since we don't get to see each other very frequently, especially now that she goes to Michigan (this was 1 week before she left), I always like to see her in a nice dress. In particular my favorite is a nice black one that frames her boobs nicely and has thin straps. In all honesty I think the dress just looks really pretty but those are some bonus features. Side story this is the 2nd version of this dress because we broke the strap from me fucking her a little too hard and her boobs bounced too much to keep it together. Read more »

A young, 18 year-old (m)an and his 51 year old, pot-growing, hippy ex-girl(f)fiend

Central Coast, California, Sept. 2012

I had just graduated high school that May at 17 years-old. I was city boy based in Chicago, and was suffering a broken heart. I was in search of something, a cognitive shift, perhaps. So that June I bought a one way ticket to NorCal where I fell in love with the state. The traveling itself was an amazing experience; I saw my first weed farm, I was offered to do porn in San Francisco, I dropped LSD in Las Vegas, and enjoyed the fresh Colorado air. I came back to Chicago, had my 18th birthday and decided I would move back.

I did what any 18-year old would do – get a job. My friend offered me a job at a burger joint his old man owned, and gladly accepted. They were greeks, and I, being an American born to pure-bred Russians, we shared one and only one thing in common: fucking women, and talking about fucking women. Within the first few minutes of my first shift, my friends father, Cris, asked me:

"You ever fuck a chick in the ass?"

To which I responded, Read more »

I’m back. College Story: Mind Blowing Sex With the Girl From Work Who Wasn’t my Type [m/f]

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones. I will post new stories as well when I have a chance. Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. Not to be arrogant, but I am generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give. Read more »

What it’s like to hide from your best friend’s roommate while giving him head [M/F]

It’s 12 noon right now and I’m writing this while it’s still fresh in my memory. I have no idea what time this is going to be posted, but might as well write down what I remember.

Some of you probably know Mark by now. For those who don't, Mark's my best friend here in college. We aren't friends with benefits, but we have had some fun together a couple of times. Fucking aside, Mark's one of the nicest people I know, and one of the best people to be around. You know that BuzzFeed video of the six types of guy friends you have? He'd probably be the third one.

Anyway, onto the story: I couldn't stop thinking about sex this week. The only time I wasn't thinking about fucking someone was while I was dissecting some animals. Listening to lectures? Screw that, all I can imagine is giving head. Taking a shower? Nope, I start thinking about is an older guy grabbing my ass. Eating lunch? Nuh-uh, what's going on in my mind is having a teacher eat me out. I had no escape. Read more »

Fucking around with (m)y girl(f)riend while her housemates slept

While I was in college I briefly got back together with my high school girlfriend, Erica. The first time we were together we would give each other head, but we never had sex. She gave the best blowjobs though – she always let me cum in her mouth, something that no one else that I've been with would do. We broke up when we went to school, but during our sophomore years got back together at Thanksgiving break.

Erica had shortish black hair, brown eyes, and the palest white skin. I loved the contrast between her hair and her skin, sometimes she would wear black knee-highs and bracelets to bed, which really turned me on. She had perky nice-sized breasts with beautiful pink nipples. She would hover between a b-cup and a c, depending on her weight. The second (and last) time we dated, she was on the skinnier end of her weight range, about 120 pounds. She didn't shave her pussy, but she naturally had very little hair down there. She had the best-tasting, wettest cunt it has ever been my pleasure to lick. Read more »

Sex with [m]y best [f]riend thanks to the world’s greatest wingman, the hot tub. Also featuring [m][f][f][f] non-participants.

I'm a details person, which I think is rather the point of these stories. Nevertheless, I'll let you know where the naked time begins if you want to skip ahead.

In the early fall before my senior year at college, my best friend and I made plans to meet up with another one of our closest friends the evening before move in day on campus. My best friend (Rachel) and I (Rob) each lived a few hundred miles away from school in opposite directions and our other friend (Kate) lived just a few towns over from school. The plan was to get there mid-afternoon, spend the day/night partying, then drag our hungover asses over to school and help each other move in as we were sharing a house that year. Let's be honest though, it was really all just an excuse to have an extra day to party together before the semester started. Read more »

My friend and I hooked up a few times after failed set ups with others

This happened a long time ago in college. I had just broken up with my gf of three months, because a friend told me she likely fucked another guy at a party. It wasn't a big loss and I could write stories just about her and how slutty she was…

I had a sorta friend named Angela from high school that I got to know better in college, because we both had astronomy our first year and a few weeks in, we noticed each other and started sitting next to each other in class. Angela heard I broke up with my gf and said she knew someone that liked me. So long story short, I went on two dates with Angela's friend and I wasn't really into her. She was pretty quiet and shy, and the second time we went out together was a party where I got wasted. So, we didn't hook up or anything and I think Angela told her friend that I wasn't really interested, and I would probably just hit it and quit it, which wasn't what she was looking for…Angela also knew I was pursuing a volleyball player that lived in my building.

  Read more »

The story of how I traded my virginity for a Play Station 3. [MFF]

I made the mistake of sharing this story with a friend who turned out to not be much of a friend at all. I can look back on it now and laugh, but at the time I was a much different person, and as you may have guessed, the story got out. It was incredibly humiliating, however, I know now its really not that big of a deal for a horny teenager. I am M.

15 pounds over weight, shy, kinky as hell, masturbating twice a day just would not cut it any longer, so to craigslist I turned. I was honest, "eager, young, shy, high school kid looking to loose his virginity." I was about as bold and honest with the title as I could be. The thought of being turned away at the door was unbearable, so I wanted to be sure everything was out on the table. 2 million selfies or so later I found one or two that were acceptable and the ad went live. I was positive someone would recognise me, but to be honest, I was so desperate I didn't think twice about it. Read more »