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.

I got a bit brazen with it after some time, brushing my hands through his hair, touching his chest, slyly grabbing his junk as I walked by. He’d always smile or laugh, but then for some reason stop himself and get embarrassed. At the time I was super confused by the reaction, or rather the lack of one. I should mention that I was seeing someone else at the time — not seriously. He was much older, lived far away, and we only saw each other when I’d have a chance to fly out. But, I know I called him my boyfriend once in front of Aaron and he had a pretty strict moral code about that kind of thing. With me, there’s always room for interpretation, and I haven’t exactly ever had a straightforward monogamous relationship before, but Aaron didn’t know any of that and I didn’t think enough to explain it. He thought I was taken, and had enough self control to keep our relationship platonic while still seemingly enjoying the occasional crotch-grab from me. Getting him to cross the line with me became a fun challenge. This story is about my somewhat crazy attempt at completing that challenge.

One night in the middle of the week, I purposely locked myself out of my apartment (for real, I did it so I couldn’t get back in without calling campus services, which would not be a new experience for me, but this time I did it on purpose – no backing out!). I texted Aaron and told him I had locked myself out, that my roommate wasn’t around, and that I had already used up all my free key replacements for the year. I asked if I could come stay at his place for the night until my roommate got back the following morning. I didn’t have a car, so I also asked him to pick me up. He said of course and came by to get me a few minutes later.

Aaron lived off-campus in a house with 3 other women he was friends with and knew from the dorms when he was a freshman, but he had his own room and bathroom. We arrived back at his house, and we hung out a bit, ate some leftover pizza, and watched some TV. When it got to be around midnight, he suggested we head to sleep and then went and got some extra sheets and started laying them out on the couch for me. Damn. He was not getting the hint and this was going to be harder than I thought.

I ignored the couch and walked back with him to his room and tried to get him to play a game. He was up to hang out more and asked me what I wanted to play. I said “Something fun? Maybe a strip game?”. He smiled. “Sure”. He took out a deck of cards and suggested poker, but I responded by saying I didn’t know how to play (true). He kept listing off card games and I honestly didn’t know how to play any of them. Finally, he suggested “war”, which however boring, I did know how to play ;-). I know war is the most basic, boring, least exciting card game that exists, but is there anything stripping won’t make more exhilarating?

We started to play, with the basic rules that whoever won each round could either ask the other to remove a piece of clothing, or put back on a piece of their own clothing. I lost the first couple of rounds, and took off my sweater and shoes. I won a round and he took off his shirt. We went back and forth a bit; I was excited, he seemed nervous. He ended up taking back a couple of clothing items once I got down to just my bra and underwear. I don’t know if he was trying to save himself, or save me. Once I lost the extra items again, and he was down to just his boxers, we finally hit a do-or-die moment. I lost the round, and he looked at me and said “Are you sure you’re comfortable with this?” I took off my bra, revealing my perky 34Cs, and his jaw dropped. He literally stared at them for minutes. I’m a somewhat decent looking woman, but I’m super proud of my breasts and he gave a look that said “I couldn’t have imagined they could be this good.”

I asked if we should keep playing, and he said yes, as I started to see a tent form in his boxers. I lost again, and removed my pink cheeky underwear. His tent was now fully pitched.

We played one last round, he lost, and gladly took off his boxers. He had a nice dick – what seemed to be a respectable 5-6 inches, cut, with trimmed pubes. We stared at each other for a bit, and he kind of marveled at me telling me I was “incredibly hot”. I waited for him to make a move, which I knew he wanted, but he never did. I was about to reach towards him when he got up and said we should get to bed because he had an early class, helped pick up my clothes, and then HE WALKED ME OUT BACK TO THE COUCH and said goodnight!

He went to bed and shut his door. I didn’t know what to do — I don’t think I’d ever felt rejected like that before, even though I knew he really wanted me. If he had ever told me to stop, I would have – I’m big on consent and everyone being on the same page, but my interpretation of the situation was that he wanted to, and didn’t want to put me in a position of cheating on my “boyfriend”. I decided I had to keep trying, but I’d respect his wishes and not do anything unless he started it. I waited a few minutes, and then walked back towards his room, still naked, and opened the door. It was dark, and he was in bed. I got in the bed, got under the covers with him, and said “The couch isn’t really comfortable”. He smiled.

I turned away from him so he could spoon me, and sure enough I felt his dick press up against my back as he got closer. He shifted around slowly, his cock sliding down my ass. All this build up and anxiety had made me incredibly horny and wet; all I wanted was for him to make a real move. He took his penis and started to rub it against my butt, inching closer to my pussy, but never quite getting close enough. Not facing him, I had no idea what he was feeling or thinking. Finally, he brushed his dick against my lips and I moaned. He immediately backed off – not the reaction you’re hoping for! He said “I think we should go to sleep”, closed his eyes, and turned and faced away from me. Frustrated and at the same time impressed with his willpower, I called it a night and we fell asleep.

The next morning, I woke up first, somehow even hornier than I was the night before. As Aaron started to stir awake, I sat up, exposing my chest for him to see. He woke up and smiled at me, and without really thinking about it, I found my hands on my pussy as I started to rub myself slowly. I continued and began to be a bit more audible, commanding his attention as he started to realize what I was doing. I went for it and began to purposefully masterbate for him, looking into his eyes as I touched myself and moaned. He stared intently as I started moving faster and approached orgasm. I grasped his hand with my free palm and came right in front of him. After the moment subsided, he started to speak – “Did you just—” “Yes”, I cut him off.

He lost it and made a face like he was giving up, throwing off the covers revealing his hard, almost bursting cock. His hand immediately moved towards it, and he began to stroke himself, while keeping eye contact with me. It was incredibly hot. I’ve been with my share of guys, but I don’t think I had ever had anyone masterbate *for* me like this before. He continued for a few minutes, the pent up frustration of holding it all in the night before visibly shedding from his emotions, as his hand moved up and down with increasing speed. Part of me just wanted to jump him right there, but mostly, I just wanted to watch. Here we were, each having these very individual intimate moments… together. Technically, he could say I didn’t cheat.

After a few minutes, I could tell he was getting closer and I got up and moved to the edge of the bed and sat directly in front of him, showing off a bit as I stared at both him and his cock, my legs lightly touching his on the bed. I had one hand on my breast lightly pinching my nipple, the other on my pussy. He gazed back at me with needy eyes, began to moan, and softly yelled “I’m coming!” as what must have been at least 5 streams of cum shot out of his dick all over his chest, neck and face. He’d definitely been working on that one a while. We continued to stare at each other and smile as cum dripped down his balls and I realized my finger was now fully inside my pussy. I took it out and licked it, and he smiled and got up to clean himself off.

It was about 20 minutes to 9 now and he had to get to class, so we got dressed and Aaron dropped me back off on campus. As I was about to leave the car and looked back at him, I realized I was pretty sure he knew I made up the whole story about locking myself out from the moment I first texted. I also noticed he had some cum on his ear that he had missed when cleaning up, and it had just started to drip a bit. As soon as I saw it, he noticed it too in the rearview mirror and blushed.

I leaned in, licked it off his ear, smacked my lips together and smiled, then left the car. I had a pretty good feeling I’d be getting more soon….

Source: reddit.com/r/gonewildstories/comments/hsg1c0/nothing_like_a_good_challenge_fm