Author: ayoungamerican01

Married co-worker [F] and the young man [M]: an affair (LONG)

Everything I’ve written previously has been about my collegiate experiences–my first time with an older woman ([1](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/), [2](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/)) and about [an experience with an ex girlfriend, where I gave her an orgasm in front of her dad without him realizing](https://www.reddit.com/r/gonewildstories/comments/5aykbh/orgasm_in_front_of_girlfriends_unknowing_dadmf/) (most of the commenters believe he knew–but I still naively don’t think so!). I have to confess the following experience does come with a little bit of guilt because she was married (it’s so weird how the married also makes it exponentially sexier, which she did specifically mentioned quite a few times). Our first interaction was last March and we decided to chill out recently.

As a reminder, 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 »

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 »

Late 40’s [F] and the college boy [M]: A first for both of us Pt. 2

Thanks for all the positive notes on my first post–really glad everyone liked it. I’ll definitely get to the PMs soon. That post is [here](gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both).

I actually was about halfway through writing about getting my a previous gf off under the covers with her dad in the room (and how she paid me back w/ a quickie just as he walked out), but really do appreciate the asks for me to finish telling about my first night with Kim–so I’m sharing that instead.

As a refresher, 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 »

Late 40’s [F] and the college boy [M]: A first for both of us

Just discovered this subreddit recently and I’m a total nube to writing about my experiences–so hopefully these won’t be a waste of your time. Please be gentle!

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler 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.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs. Read more »