He asked and I said yes [F23/M23]

This is a story of hooking up with a guy I had known for about 7 years as a platonic friend. His name was Brian, and we first met in high school, although we didn’t really run in the same circles until college where we became close. High school he was like an acquaintance, someone that you might say hi to or not depending on the day and whether you were already talking to someone else. When we found out we were going to the same college we became closer, and by about midway through freshman year we were good friends. At first there had been a decent sized group of us that came from the same high school, but as people acclimated to their new lives and new identities, it dwindled to just a handful. Brian and I were hanging out a lot at that point, and he was one of my best friends. I must admit, on a couple of occasions I even said that he was like a brother to me.

The other reason that nothing ever happened between us for all those years is that I didn’t really embrace my sexuality until college was almost over. I followed a somewhat typical pattern… when I first started having sex I only did it with boyfriends, then it became guys who I was hoping would become boyfriends. After a few times of having situations like that and having nothing come of it, I realized that it wasn’t the end of the world if sex was just sex, not part of a bigger story like I initially wanted it to be. I realized I liked sex, and I even liked the thrill of casual, naughty sex with people I don’t even know very well. This brings me basically to where I am today, a proud self declared slut. Brian was there for every step of this process, hearing my stories and meeting my boyfriends or dates, just as I would become friendly with his girlfriends.

So about a year after college, we were spending a weekend together. We had gotten together to watch football and for him to show me around the new city he had moved to, a beautiful metropolitan city that I had never visited before. The night before we had gone out drinking with friends of his, and I had slept in his guest room. Now we were just hanging around his apartment waiting for more people to come over for the game, but we had both woken up about five hours before kickoff, so we had a lot of time to kill. He was wearing old torn up jeans and a grey t-shirt. He’s average height and average build, with fluffy brown hair and had recently grown a real, professional looking beard that was much more becoming than the stubbly look he had rocked since high school. I planned to get all dressed up in school colors for the game, but I didn’t want to make him wait before I came out to say good morning, so I was wearing my pajamas, a t-shirt and short shorts. I didn’t think about it, but I must have been looking pretty cute because he said something like “well hello” when I came out of the guest room. I’m blonde and bronzed, 5’6 with a pretty decent figure. I have small boobs and a nice big butt, but everything else is tight.

He made bloody marys and we started chatting about the night before, and how I had been flirting with everyone including him. I’m actually much sluttier when I’m sober, when I drink I start to worry that I’m coming off as sloppy or desperate, so I don’t let anything really happen, but I do flirt a lot. So I told him honestly that I might be hoping to hook up with someone at some point while I was in town, but nothing was gonna happen last night. “So how dirty have you gotten?” he asked me playfully, “Did you really bang someone within an hour of meeting them?” This was referring to something I had said to him a few days earlier, without really telling him the story. I explained that, yes, I had been feeling really horny, so I went to a meat market club, sat down at the bar by myself and hoped someone acceptable would come along. And when I got lucky and was approached by a gorgeous male, I didn’t waste any time. “Wow,” he said with a chuckle, seeming impressed but not really knowing what else to think about the story. There was a pause while he picked up the glasses and took them into the kitchen, then came back with a couple of beers and handed me one that he had opened for me. I took a sip and looked at him, and from the way he was looking at me I could tell he was trying to decide whether or not to ask me something. Finally he blurted out, “Brook… do you think I could be one of the guys you hooked up with?”

At first I just laughed, because of the awkward way he had phrased it. But I had to think about it. I had really never thought of him that way before. On the other hand, he was far from unattractive. I liked the way he was looking at me, and the way he had looked at me earlier when he saw me in my pajamas and said “well hello”. We had been really close in a platonic way for years. But I like sex, and I didn’t see any reason to deny either of us all the pleasure we could find. “I’d be up for it,” I said with a smile, after what hopefully wasn’t too long of a pause. He smiled back, but I could tell he didn’t know what to say next. I hadn’t been clear whether I meant hypothetically up for it, or *up for it*, so I decided I’d better take the next step. “Your room, my room, or right here?” I asked.

“Definitely right here,” he said, moving toward me. There was this sudden hunger for me in his eyes that was a huge turn on. He took my face in his hands and kissed me, and it was just amazing. I found myself returning the kiss, hungering for him just as badly. It was strange, because we had never kissed before, but it didn’t have that feeling of unfamiliarity like most first kisses do. I already knew him, it was as if I already knew what he would be like. He pulled my body against him and started kissing me faster. I think I moaned his name at this point, and he started taking my clothes off. I realized he had been looking at my body all morning, and last night when we were out drinking as well, and now he was eagerly exploring it with his hands. The next thing I knew I was naked, and my hand was in his pants trying to get him hard. He took his cock out, and it was really nice, and then I was blowing one of my best friends on his couch. I knew things would never be the same between us again, but it didn’t bother me, mostly I was wondering what had taken us so long.

He was doing a good job of fingering me while I sucked his cock, and I was dripping wet. I looked up at him. “Please.” He didn’t reply, he just stood up and disappeared for a moment, coming back with a condom. He put it on and the gestured for me to get in his lap, so I straddled him and slowly guided his excellent dick inside me. Finally I took him all the way inside, my lips wrapping around the base of his shaft and we just looked at each other. It was this surreal moment where I realized I was actually fucking *Brian*. “Oh baby, you feel really good,” he said, and I thought it was funny that he said I felt good, when I was the one being filled up so perfectly. I started moving my hips and rode him until I came hard, while his hands ran over my hips and ass, squeezing and exploring me.

He flipped me over onto the couch and got down on the floor in front of it, spreading my pussy with his fingers and quickly finding my clit with his tongue. It was extremely sensitive from just cumming, so it felt really intense, but I didn’t want him to stop. Apparently it was an uncomfortable angle for him, because he stopped after a minute, grabbed my hand and led me into his room, where he threw me on the bed and continued going down on me. The moment’s rest had been all I needed to get past that uncomfortably intense feeling, and from there on it was pure bliss. I was so turned on it didn’t take long for me to cum again, and then I heard myself begging for his cock.

He pushed my knees back and buried his cock inside me, so deep that my knees were about even with my shoulders and my feet were on his shoulders. I remember crying out his name over and over as he just pounded away inside me, and hearing my name grunted in return, until, both of us struggling for breath, he came inside me.

We cuddled for a while afterwards. He confessed that he had had a crush on me for a long time. I told him honestly that I had had no idea. It took me completely by surprise, having known him as just a friend I had no idea he would be such a good lover. He said he hoped it wouldn’t be weird for me to stay with him now that this had happened. I said it was fine, but I wouldn’t be sleeping in the guest room anymore.

His friends came over as planned, we watched football and then went out as a group. We had sex again that night, and the next day before I left. Since then I’ve seen him twice, and we’ve had sex every time. We made the transition from friends to friends with benefits pretty smoothly, and it hasn’t messed things up at all. I still feel that I can talk to him, and we even still share everything about our love lives. But now I end up thoroughly fucked every time we have a reunion, and it’s a great bonus. So yeah, that’s my story, hopefully the first of many. I’d love to chat about it, so feel free to PM. Also, if it happens to make you cum, please let me know!

Source: reddit.com/r/gonewildstories/comments/45n2mz/he_asked_and_i_said_yes_f23m23