Benefits: [M]y first time with my best [f]riend | 2016

I've loved this subreddit ever since I first stumbled across it, so I thought I'd finally share some of my stories. This is the story of how I went from best friend to Mr. Benefits.

It was senior year of high school (junior for her) and I had just gotten out of a very long, not very physical relationship. I was skinny, kinda short, and a bit of a nerd: far from a total loser, but not exactly the kind of guy who picks up chicks at the drop of a hat. My best friend at the time was this girl Jamie (real name withheld). She was an asian brunette, a tad shorter than me with tanned skinn, average tits, and a nice ass. She was pretty cute, but I had never really seen her as more than a friend, especially not sexually.

In general I'm a pretty reserved person: the kind of guy who would groan at my soon-to-be-fratboy classmates' immaturity. Sure I thought about sex, no teen doesn't, but I kept my sexuality between me, the locked bathroom door, and an incognito window. Jamie, on the other hand, was an overtly sexual person. She would talk and make jokes about sex all the time, and constantly start conversations about watching porn and masturbating. She often fooled around with some of her other guy friends over skype, and occasionally in real life too (although it never got too far, a fact I confirmed later on). She and I would even joke about being friends with benefits sometimes, but I never thought anything of it.

That is until one night, during one of our usual playful text conversations, she said she wasn't joking anymore. I honestly thought she had lost her virginity a while ago, but she said she wanted to wait for me. She had a thing for nerdy guys (as evidenced by her choice of friends), but I was the only one she trusted to go all the way with (let's just say the other guys were less-than-chivalrous individuals). I was pretty shocked. I had never done anything like this before; I hadn't even fooled around with her like some of the other guys. Nevertheless, I made a plan for when my house would be empty and invited her over.

We sat there on the couch for a while, sheepishly waiting for something to happen. For a girl who's favorite subject was sex, I hadn't expected Jamie to be so timid. Finally I asked one last time if she really wanted to go through with this. I'm sure most guys out there would have slapped me in the face for risking such a golden opportunity, but I'm just not that kind of guy; I wasn't going to take advantage of my best friend. Thankfully, she said yes, but that she was too shy to make the first move (she's a bit of a sub, but I'll get to that another time). With one last breath, I awkwardly pounced.

I'd had plenty of kisses, and a few make outs, but there's nothing quite like two-horny-teens-alone-on-the-couch making out. You have to understand, my previous girlfriend was, to put it bluntly, a bit of a prude. In all our time we barely passed first base, not that I minded much. This was a whole new level of intimacy for me. Lips locking, tongues twisting, hands wandering. There's something special about the first time your fingers breach the forbidden zone of a girl's chest, or you feel the warm moisture of a pussy through panties. She pulled me in tighter, pressing her tits against me. Her body told the story of how long she had waiting for this and how much she wanted it.

Those ten minutes of erotic intensity were followed by thirty minutes of the most awkward oral sex in history. Sex is easy; once you're in it's hard to go wrong. But oral? Man did I have a lot to learn (another story for another day). It didn't help that our combined inexperience and her submissive nature led to me blurting out instructions in the most uncomfortable way imaginable. "Let's try 69 now, ok?" cringe

Finally, the time had come to do the deed. We re-hydrated (surprisingly important) before moving things to the bedroom, trying to ignore the nerd paraphernalia scattered on the floor. I suited up (safety first!) and prepared to slip in. Jamie, spread on her back, smiled at me. We were ready. I thrust forward and she stifled a yelp. There was already some blood from a vigorous fingering earlier, but I hadn't expected so much. "Well, at least you know I wasn't lying now," she joked. I'll skip the gory details (let's just say a couple of towels were retired that day), but it didn't matter; nothing was going to stop us now. Slowly but surely, we eased into a steady tempo.

When it comes to sex noises, there are two types of women: the kind that sound like they're being tickled, and the kind that sound like they're being tortured. Jamie was the latter, and for the over protective, extra cautious guy I am, that was worrisome. But every time I stopped to make sure she was ok, she told me to keep going. The more it hurt the more she wanted. I was beginning to see what kind of lover Jamie was. I wasn't sure if I liked it, but with my dick inside of her it sure did turn me on. We went like that for a while, and she rode me for a bit. Finally she stopped, out of breath, and panted "Can we do doggy style?" I don't know if she brought out some deep inner part of me, or if I was just eager to play into her fantasy, but I told her to ask nicely. She kissed me up my chest, staring at me with big puppy dog eyes, and asked again, "Please fuck me from behind." I knew she she wanted to be, and in that moment I decided that I liked it. Somehow, I managed to say, "Call me Daddy."

She's been daddy's little girl ever since.

Now, I'll never know what was going on with me at that point. Maybe the shock of finally having real sex just hadn't reached my penis, maybe I came early on and just never noticed, or maybe by some miracle I gained the endurance of seasoned professional. Whatever it was, that doggy style lasted for nearly an hour: a record I have yet to break again. It's still some of the best sex I've ever had. I thought Jamie had been enjoying herself before, but this took it to another level. Slow, powerful thrusts followed by rapid pounding. Ass bouncing as she flung her hair back, letting out moans too carnal to contain. She asked for a spanking, and while I was a newly christened Daddy, I wasn't really into the whole "hitting women" thing, even in this context. I gave her a slap from behind and her back arched in pleasure. "Harder," she pleaded, and I tried my best to let loose. Let me tell you, the only thing more satisfying than smacking a perfect ass as hard as you can is hearing the girl you're inside of squeal and ask for more.

We kept going, my thrusts picking up speed as I spanked her like a horse that needed to giddy-up. Eventually I leaned forward, laying on her back and holding her. My hands squeezed her bouncing tits, twisting her nipples (which I quickly learned was the easiest way to turn her on). I kissed her back and neck, whispering dirty thoughts into her ear from behind. I could tell from her face she was in a place of pure pleasure. This had been something she dreamed about for a long time, and I was happy to give it to her.

Eventually, our two non-athletic bodies ran out of stamina, and we decided to call it an afternoon. We took a breather and then hopped into the shower together (which has since become a tradition for us). We were both amateurs, but we could still tell we had gone pretty hard. Jamie could barely walk right the next few days and winced whenever she sat down. Being a bit squeamish, I was traumatized by the blood spill, which we later found out through friends was far more than normal (likely due to the relentless pounding). Believe what you want (frankly I barely believe it myself), but as far as we could tell I hadn't cum that whole time. I call it a fluke (I've never had that much stamina again), but I was more than satisfied. I could tell she was too, because her interest in other boy toys slowly began to fade. She could have slept with anyone after that (we agreed on it), but she kept coming to me. I was safe but fun. I didn't ask for much and gave her what she needed. I was still her best friend, but now I was also her Daddy, and there was plenty more in store.

Hopefully you guys found that entertaining (I sure had fun writing it). I have plenty more to share if you guys are interested. Either way, thanks for reading!