My first time with another girl [FF]

I met Kyra at a club meeting for our honors program in college. She was the coolest girl in the room – and I was dying to impress her. She had short dark hair, tall with a fit figure. She had an engaging personality – made everyone want to be her friend.

I have always been shy and was never very popular in high school. I had a few close girl friends and dated a couple guys, but still pretty inexperienced. So when Kyra started taking to me, it never even occurred to me that she might have been flirting. I was glad to have made a connection with someone and thrilled when she asked me to chill in her dorm room after the meeting.

We spent about an hour gossiping, laughing, and getting to know each other. I told her about my family, life in the small town I grew up in, my favorite novel. She told me about the Econ TA she was having sex with. I didn’t know what to say, although secretly it turned me on to imagine her fucking anyone.

After Swim Class- (MMFF) [NSFW]

Pool Time
It was a sunny afternoon at the community college campus pool; when the topic of discussion came to oral sex, the three fresh out of high school kids looked to me for the answers to their misconceptions, because I was older, a whole 5 years older. Kimi, Mika, and Toshi had all gone to school together, and are now taking a summer class, and getting credits at the college campus pool, where they met me.

Kimi asked me what guys liked to have done to them down there, Mika gave me a funny bashful look and Toshi tried not to pay attention to Kimi’s question; it came out later he has had a crush on her throughout high school. Seeing Toshi’s discomfort I replied by asking if she had ever gone down on Toshi, or any guy for that matter. Now Toshi blushed. Kimi confessed to never seeing a penis in the flesh, let alone going down on a guy; Mika nodded with a sympathetic response. Toshi tried to brag by saying a girl has gone down on him before, but after a few minutes of badgering by the girls Toshi admitted to never have received a blowjob. I suggested for my young friends, after swim class, go back to my place to answer Kimi’s question. 

The Cabo Maid [mf]

My freshman year in college my family took a vacation to Cabo. The resort we stayed at was really nice, it had villas at one end and a separate hotel at the other. Being a family of 5, we were in one of the villas which didn’t have maid service, which who knows why my mom would be a fan of cleaning for everyone even while on vacation.

So the hotel was a couple minute walk down the boardwalk. There they had the big pool with the swim up bar, the slide, and the rest of the fun stuff. So for the week we were there, we spent most of our time at that pool or down at the beach.

Sleeping on a sofa bed in a two bedroom room with 4 of your family members leaves you absolutely no privacy, so a couple days in I was getting really horny, and spending days at the pool watching women walk by makes it no easier. Nor does having only a few girls my age either.

That Killer Blue Dress [MF]

My [last story](https://www.reddit.com/r/gonewildstories/comments/3kzo56/the_one_that_broke_my_heart_mf/) got a lot of positive, supportive responses and though it’s been over a year I’ve decided to share a few more stories. These are all real, though I may have misremembered details and added a little dramatic effect. Memory is a funny thing like that. It can make you hate someone you loved, or love someone you hated. It can convince you with absolute surety of an experience even if it never happened. In that way I am only human and nothing more. As usual this is a long read and I’m sorry if not especially interesting. I’ll leave you a bookmark to skip to the parts you want to read.
Not quite a year had passed since she had broken my heart, maybe only a few months. A wounded heart makes you forget time and space, makes you unreal in your own mind. Things blend together and I cannot even remember how much time passed between “Katy” and I’s one tryst and when I could again feel like I was real.

At this time I was working in a cubicle of a small office on the second floor of a financial building. I won’t bore you with details but we worked on the retail sales side of the financial industry and my team was small but hard working.

[MF] My second high school crush/large breasted experience

Hello again! Thanks for all the responses and PMs from my last post. I encourage you all to reach out via PM. If you haven’t read my first story see it [here](https://www.reddit.com/r/gonewildstories/comments/6cnbw4/my_first_largebreasted_high_school_crush/).

If you want to ignore the setup and just get to the sexy part, scroll down, I have it labeled.

Some more context on this, in my last story I brought up two girls in my high school that I had huge crushes on. We’re calling them Kristin and Aly on here. My last post was about my first experience with Kristin, this one is about Aly.

So some context about Aly. She was much different from Kristin. She was athletic(ran cross country and played basketball, had to wear 3 sports bras to keep her 34DDDs from hitting her face when she ran, now that’s dedication), popular and super cute. She had boyfriends in high school and did not really have a bad reputation. The only people who talked badly about her were girls that were just jealous of the attention she got from her tits. I totally would have been ok dating her if we were both available/if I had more confidence. I don’t know if I can explain how breathtaking her body was, she had huge natural tits but she had a tight and athletic body. Most girls with my ideal hugeness of tits have some fat on her. She also had a gorgeous smile. Not gonna lie, I totally pumped off a few times to her Facebook summer album throughout HS.

“The Best Fuck” My “Friend” Ever Had.. [MF] [Cheating] (Part Two)

Before I continue with the story, a few more details.

First, more about Brad. Brad was the typical high school guy. He was reasonably athletic and played football. He was no stand out or all star but never the less had that fragile, jock ego about him. I wouldn’t say he was dumb, but the guy wasn’t [Will Hunting](https://media.giphy.com/media/3otOKtnGppPi5Q4hOw/giphy.gif) either.

I think it’s relevant so I’ll give you an example. One night a large group of friends were playing poker. With no obviously segue, Brad looks at me and says,” Have you ever read So Crates?” I said, “What?”, without flinching he said, “So Crates…?” I was at a loss for a beat but then understood, “Yeah, why do you ask?” He said, “Oh, I just wondered, it’s interesting stuff.” One of our other friends looks at me, “What the fuck are you guys talking about?”, “He’s talking about [Socrates](https://68.media.tumblr.com/4f38bdc5c634134f635599a36d1b8b39/tumblr_o2gvbrjYiy1qa32meo1_540.gif)” I replied.

I’ll continue from where I left off.

We were all together at someone’s house in a college town. It was just a smaller gathering but it kinda evolved into this instantaneous party. People were coming and going, watching a game on TV. A lot of drinking and smoking.. People I knew and a lot that I didn’t know, came and went.

[M]y [F]irst large-breasted/ high school crush experience

Sorry there’s a lot of exposition here scroll down if you just want the sexy part

Okay so some context here: Deep down I have always been a boob guy. I have also been more concerned with what people thought of me so I only dated a certain type of girl (typically goody good who isn’t too gifted in the boob category). So this all starts at the end of high school where my HS GF and I had just broken up.

There were two girls at my HS that I had a huge crush on, really admiring both of their large tits. Lets just call them Kristin and Aly. This story is about Kristin… See another post for Aly.

Kristin was not only super cute with giant boobs but she also had a bit of a reputation. She had been with or was rumored to have been with a lot of guys and she was kind of a loner. She didn’t care what people thought of her, I admired that. I was obsessed with how I was perceived by my peers so, even though I was always into her especially with the stories I heard, I never made a move.

[MF] Let’s all laugh about the time I got a boner during a school physical from an old ass nurse

DISCLAIMER: this story did not end in any sexual activities. It is just a funny/embarrassing story that happened to me years ago. I’m sure some of you will be able to fantasize it and take it wherever you want (I do), but most will probably not get off from reading it. Skip to the line to avoid background info.

You know how you can just suppress embarrassing shit that happens to you to the point where you forget it even happened? Well, this is one of those times. I recently remembered this while high as beans and figured I’d share it with you strangers.

This happened about 7 years ago while I was in high school (freshman or sophomore), so some of the details are hazy. I’ll try to retell it with as much accuracy as possible.

“The Best Fuck” My “Friend” Ever Had..[MF][Cheating] (Part One)

This story goes back a long ways..

When I was in high school one of my best friends started dating this girl called, “Cindy”. She was.. fucking stunning. She was probably 5’6 or so, she had darker hair with big tits (probably Cs), and a round ass.

She was popular, but had a little more brooding to her than a cheerleader vibe. So a lot of guys didn’t know what to make or do with her. She played varsity tennis and was good, very good. All I remember from watching her was, I was watching perfection. Longer legs that were lost in an amazing ass. Her tits were full, welcoming. Her skin was tanned and her smile was blinding. She was gorgeous.

One evening, she called me. The call was made under the pretense that her and my friend, “Brad”, had just gotten into this big fight and she was calling me as his friend to try to understand him better. I knew this wasn’t her true intent. I had never knew her before she started dating my friend. But we had talked briefly here and there and she always left the conversation with a questionable smile.

In case of an emergency break a cock [MF]

It was the second half of freshman year. I met Anna in the first week of class. I made a joke about Shakespeare being just the Elizabethean era’s version of the pro wrestling. That made her laugh. I had broken up with my high school girlfriend and was not looking for anyone at the time and she was seeing someone else. So we just started to hang out and enjoy each other’s company

We had become close with the odd uncertainty of mutual attraction that we could speak of dispassionately and do nothing about. By the time registration for the second semester had rolled around, we decided to take a core class together, and we chose Astronomy as both needed to knock off a science class. We thought it would be easy enough, but whoops, it was not. It was a brain breaker calculus based class.

So we started to spend every Thursday night in her dorm room together working on the homework we got on Wednesday that was due on Monday. We would work hard for a while, talk for a bit, work hard for a bit, and then have a couple of drinks.