gonewildstories Archives — Page 5286 of 5640 — NSFW story

CL meetup for a girl [F] to let me [M] cum on her panties

This happened about eight years ago but remains my greatest CL success story. I was in my late 20s. I’m not sure how old she was but I would guess mid-to-late 20s. Here’s the quick setup before I get to the good stuff… I’ve always had a panty fetish and I put a post on CL for a girl to let me cum on her panties. To my surprise, one of the responses seemed to be from a real, attractive girl who was into my fetish. Not for pay or anything like that. Just for fun. We exchanged several details and eventually decided for me to come to her apartment on a Saturday morning. The plan was for her to let me peruse her panty collection and pick out several different pairs for her to model for me while I took pictures with her camera. After the photoshoot, she would leave my favorite panties on and let me jerk off and cum on them. Read more »

[19m/26f] An explosive first impression.

*I’ve posted one story about S before [here](https://www.reddit.com/r/gonewildstories/comments/4hc8zn/19m26f_a_very_happy_ending/). I was very tempted to call this “S: Origins”, because it’s the story of how we first met. This one runs quite long, I’m afraid. Settle down and grab a hot beverage.*

*****

Getting an OKCupid account was an *awful* idea, or at least it felt like one at the time. If anyone ever asks, I tell them my ex made me do it, which is only half true – she made me do the personality test because she was keen to see what I registered as (turns out my highest trait is “kinky” and my lowest is “wholesome”, go figure). Actually having a go at using it, a few months out of a very messy breakup and feeling a little lonely in a circle of friends where most people had two or three partners, was entirely my call, and, in hindsight, it was a much better one than I thought. Read more »

Surprise window sex with my wife in a hotel

This past weekend my wife Allison and I traveled a few states over for a family reunion. Her moms side of the family is quite large so it always turns into a circus trying to coordinate with so many people. She knows my disdain for events like this, but I put on a happy face and go because she enjoys them. The first day there was just as expected, tons of probing questions from the aunts and uncles, when we will have kids etc. That evening since we were tired from traveling we decided to skip out on the various groups of people going to different places to eat and head to the hotel. We went up to the room for a little bit to get settled in, and then I left to go grab us some food from down the street. Read more »

Bookworm hooks up with the jock [F/M]

So first off my name is Avery and all this happened like a year and a half ago. I’m 5 foot, half Mexican, but really tiny and petite, long dark hair that’s usually curly, glasses. I’ve always been called cute and adorable, but not really “sexy.” I was an ugly duckling until about junior year of highschool but really didn’t come into my own fully until college. I’ve always been the shy type and kind of a bookworm with a side of tomboy thanks to three older brothers.

Anyways so this all happened freshman year of college but I need to set the background first! So through high school I just kind of blended in with the crowd. I wasnt super popular and a pretty reserved person. I had my few close friends and had a boyfriend for awhile but in general just kind of blended in. I definitely WASNT on any of the popular guys radars or anything. Read more »

A quickie ’bout a quickie (22F/18M)

I’m trying to get over some writer’s block… I miss y’all! So I thought it’d help to write up something quick and dirty.

We matched on Tinder. He had just gotten back into town for spring break. He’s way younger than I usually go for — which is to say he was younger than me. 18. A Freshman. I’m not even sure I fucked freshman when I was a freshman. But he was good in chat, tall and fit — a soccer player clearly putting his college athletic center to work. His hair was short and neat. His face was shadowed by uniform stubble. I’d say he was approaching dark and handsome, like he was preparing to say good-bye to his awkward teen years. I say “preparing to” because in person, it was clear that he still had a little growing up to do. He said he was of Persian-descent and had strict parents; growing up, he didn’t talk to girls that much. So it wasn’t a surprise when well into our first date the Friday he got into town, he put his v-card on the table.

And I happily took it. Read more »

[M]y [F]riend Holly in the Hot Tub

As promised, this is the story of how my friend Holly became my one night stand Holly. She then became my FWB Holly, but those are other tales. In my previous story, I noted that Holly was my ex’s younger sister. Five years younger than my ex, and 7 years younger than me. I became something of a mentor to her – got her a job, helped her apply for college, etc. And she had also grown into a really beautiful young woman. Holly was thin and waify with few curves, prominent hip bones, and boobs a little bigger than you’d expect on a frame like that. A brunette with long straight hair and huge blue eyes; I’ve always been a big fan of that combination.

I’d visit Holly when I was back in town to see my parents. Or, she’d visit me at my parents house, which had a really sweet hot tub. I didn’t know then just how far a hot tub goes to setting the scene with a girl. It’s actually crazy. Read more »

How I accidentally became my stepsister’s eskimo sister (F, if that wasn’t obvious)

So, a little bit of back story about me. I’m half Italian and half-Japanese. After she broke up with my father, my mother married a guy who was Japanese, and had a daughter from another marriage. My step-sister is only a few year’s younger than me, but she can be kind of a FOB sometimes, so I have always looked after her.

We ended up attending the same university when I was an undergraduate. We were only there for the last half of my Junior through my graduation. It was hard for my step-sister to establish her own identity, but she managed to avoid any classes I may have taken, and to cultivate her own circle of friends (she joined Greek life and all sorts of groups I’d have nothing to do with, I basically stuck to cultural orgs and RHA).

Anyway, one night I was swiping through tinder and I matched with a guy who was pretty cute, who told me he wanted to take things slow. We met up at a bar. My first impression was that he was taller than I expected, the second impression was that he was a really fly dresser. We chatted for a while and danced. I don’t remember us going back toward my apartment, but we ended up making out on the front stoop. I invited him up and he told me “remember, I said I wanted to take things slow.” Read more »

How I lost my virginity [M/F]

This is an old story and my memory isn’t great but I think I got the story, for the most part.

The summer before my freshman year of high school my father had invested in his dreams and went into business for himself by buying a restaurant. The building was an apartment on top and the restaurant was below. It was beat to shit by the people who had it before hand (top and bottom) so there was a lot of work to be done. With me being helpful and my father never being shy with exploring child labor out of me, we got started.

It is important to note that my parents separated well before this and my father and I were together while my two older sisters and mother lived in Ohio. Over the summer, one sister, Danielle, had a falling out with my mother and was spending a few weeks with my father and me in our shitty upstairs apartment. My other sister, Ariana, drove her to New York to my father’s apartment. Read more »