Surprise! How a trusted, yet devious friend [M] fulfilled my [F23] stranger [M] fantasy

I always find it incredibly arousing to read and hear stories about other’s slutty adventures – the more promiscuous, spontaneous and somewhat irresponsible the better. No shocker… I’m a big fan of this sub. One question I always love to ask, and love when others ask me, is “What’s the fastest you’ve gone from meeting someone, to having them inside you?” This is the story of my answer.

If you’ve read [my previous stories](https://www.reddit.com/r/gonewildstories/comments/fppy8e/six_close_friends_in_a_dark_closet_group/), you may know that I’ve developed a knack for going after that incredible rush you feel when a cock enters you (or is shoved in your mouth), and you don’t know to whom it belongs. I’ve been lucky enough to have had a few adventures with a group of friends where either darkness or blindfolds helped to facilitate that type of situation. Still, I always knew it had to be someone in the group. I knew I wanted to take it to the next level, to actually have sex with a true stranger. The only question was how to do it safely, while still keeping up the fun and intrigue.

***

One small dare for me, one giant leap for Aaron’s Virginity [FM]

*You’ll really want to make sure you’ve read Part I of this story before continuing:* [*I love a good challenge: Tricking my way into Aaron’s bed [FM]*](https://www.reddit.com/r/gonewildstories/comments/hsq6q3/i_love_a_good_challenge_tricking_my_way_into/)

As I left Aaron’s car and headed into class, a drop of cum still in my mouth, I could not stop thinking about the previous few hours with him and how unique it was compared to so many of my other sexual experiences. Given how headstrong and determined he was to avoid doing anything with me throughout, I knew we had made quite a bit of progress considering he had just masterbated to orgasm in front of me, while staring lustfully into my eyes throughout. You always want what you can’t have, and at this point, my desire to actually fuck Aaron had taken over and was idling in my brain all day, making staying attentive in class nearly impossible.

I sensed that Aaron would eventually come around, but it might require moving more slowly than I’m used to, which could be a fun little game for me. I wanted to meet up again, so I texted him a few hours later: “Well, that was surprisingly fun. If you’ve got cum on other parts of your body that need licking off, I’m sure I can misplace my keys again ;-)”. I saw the typing indicator pop up and disappear on and off for what seemed like 20 minutes, until it just stopped entirely. Silence.

Nothing like a good challenge [FM]

*Really appreciated the amazing reaction to my first story:* [*Six Close Friends in a Dark Closet*](https://www.reddit.com/r/gonewildstories/comments/fppy8e/six_close_friends_in_a_dark_closet_group/)*. At over 3.5K upvotes, I’m absolutely floored by the response, and everyone’s PMs of support and thanks. This one’s a bit different, but I hope you’ll still enjoy it!*

This story takes place during my freshman year of college. I wanted to try and meet some new friends outside of my little bubble and joined a study group for a large gen ed course. It was there that I met Aaron, an older tall nerdy kid who was overly friendly and easy to talk to. I’ve always had a thing for guys with glasses, and slowly realized I had a bit of a crush. We hung out quite a bit over the first couple weeks and my advances weren’t quite working the way they usually do. It was strange – I could tell he liked me, or at least was attracted to me, but he seemed to always be stopping himself from making any moves.

Six Close Friends in a Dark Closet [Group]

*This is my first post about a true story that happened a few years ago. Would love any feedback (or just let me know if this was the post that got you off!)*

I’ve had a small group of friends for a while – we’ve all known each other since high school. We’re all very chill, open, and have had a lot of fun “experiences” with each other over the years, both one on one and all together as a group. Our group adventures are my favorite, and they all started one night when we were all back home for winter break or something during our sophomore year of college. One of my friend’s families are very wealthy and they had a nice house near the water that we’d all go out to sometimes. We all met up there for a weekend. While at this point we had been friends for a while, and a couple of us had dated, we were just very comfortable around each other. We’d gone skinny dipping together, been naked in hot tubs, that kind of thing – though nothing overtly sexual yet.