With My Best Friend

I still remember this clearly because, well, it's not easy to forget! Throughout my teenage years (16-18) I had a very close girl friend. Things between us started in a romantic nature (as most boy-girl relationships do), however we grew to become friends. Although I was pretty disappointed as I still very much liked her, I enjoyed her company nonetheless. Her name was Emma, and she had strawberry blonde hair, and blue eyes. She was gorgeous, and her boobs were out of this world. Although I can't remember the cup size, they were bigger than DD. She was slender though, with a nice ass, so as you can imagine, I drooled over her in my spare time. I'd like to think there was always sexual tension between us, but I can't be certain. Anyways, let's carry on with the story. Over spring break, we hung out quite a bit. One particular day, we were at her house, and we let time get the best of us. As I lived pretty far away, it was hard for me to get back to my house, and so she told me to simply stay the night and leave in the morning. Her parents loved me, so they didn't have any problem with it. They went to bed pretty early, leaving us to hang out in her room and talk. By midnight we were both pretty tired, so I asked her if she had a sleeping bag for the floor, as I assumed I would be sleeping there. Instead, she told me to just sleep in the bed with her. That was absolutely no problem for me, so as she got changed into her sleeping wear, I climbed into bed. She slid in and cuddled up next to me, before asking why I was still wearing my jeans and shirt. I explained I didn't have any sleeping clothes, and didn't think she'd want me to strip down into my boxers. She laughed, and then grabbed a pair of sweats for me to wear. So there I was, wearing only a pair of sweats, and no shirt, with this pretty girl snuggled up next to me. Now, I wasn't a virgin by a long shot (I'm a good looking guy, and had my fair share of ladies), but this girl was different. Anyways, she begins to straddle my leg, and of course my body decides this is the proper time to get an erection. Her leg is right over my hard-on, and I assume she feels it, but she didn't say anything so I didn't either. Finally, after a few minutes, she says, "I can feel your dick poking my leg". Now we often joke with each other sexually, and the way she said it made me think this was just more joking, so I laughed and said "yeah, sorry, it does that". We laughed for a bit, and then went back to cuddling. After another few minutes she says "you can take care of that if you like, I know that's what guys do". I went a little red in the face, and although it was dark, I swear she could tell I was embarrassed. Playing dumb, I said "what do you mean"? "Jack off" she laughed back at me, "I can turn around if you want me to". At this point I was way too embarrassed to do anything at all, so I said "Uh that's okay..." and laughed a bit, still red in the face. "Whatever you say!" she said back to me. From there, the conversation drifted over to sex, and I was pretty horny, but I wasn't sure if the offer still stood. Finally, I said "so... did you actually want me to jerk off?", to which she replied "yeah, I don't care". I tentatively agreed, and made excuses to justify doing it, like I was too horny to sleep. So, in the dark, I pulled my dick out of the sweat pants, and begin to stroke it slowly. At this point, she was still cuddling me, with her head on my chest. It was a weird sensation, to be masturbating so casually. I noticed that she had slid her hand off my chest, and down towards her legs, and had a pretty good idea why. "What are you doing?" I laughed at her, "what, since you're doing it, can't I?" she said back to me, and so I told her to please carry on. As I stroked my cock, I felt her hand moving inside the fabric of her shorts, and it turned me on even more. I switched hands, and put my arm over her, and begin to stroke her back. Both of us were breathing pretty heavily, when she snaked her hand out of her pants and onto my leg. From there, she slowly, as if testing to see if it was okay, slid her hand towards my dick. She stopped just at the base of my cock, and so I decided to man up. I stopped stroking, and picked her hand up and placed it on my dick. Right away she being tugging on it, stroking up and down, all the while grinding her pussy into my leg through her shorts. With my hand now free, I slowly moved from her stomach downwards, and stopped just at her shorts. She sped her stroking up a bit, and so I took that as a sign to keep going, and slid my hand into her shorts, and panties. As I slid my hand down, I noticed she was completely smooth, no hair at all, which I loved. I could feel her warmth, and I began to slide my hand over her mound and down through her wet pussy. She made a tiny little moan, and gripped my cock even harder. I begin to finger her rapidly, and she moved her head upwards and kissed me. We stayed like this for a few minutes, making out and masturbating each other, until I began to feel like cumming. I told her I was about to come, and she moved her head back onto my chest, inches from my cock, while continuing to stroke faster and faster. As she felt my dick begin to move, in one swift, surprising movement she moved her mouth onto my cock and I came into her mouth. She swallowed all of it, and continued to suck my off for a few more minutes, before stopping. Now feeling obligated, I rolled over on top of her, and pulled her shorts down. I began to eat her out, and after a few minutes, she came as well. We fell asleep a few minutes later, too tired to put our clothes back on. The next day I was pretty confused as to where this left our relationship. Where we still friends? Where we more? I had no idea, and so I asked her. She was just as confused as me, and she admitted it was fun and she'd like to do it again. Although we (and by we I mean her) decided not to date, every now and then we still have our little late night sessions, some of which eventually ended in sex (which I can't talk about on this forum). Thanks for reading!