The devil on my shoulder prevails again [m/f] | 2016

My first post was received positively so I decided to write another story, and as requested it's about my other act of indiscretion.

It was a Sunday night and I was visiting my former college city on a work trip. Instead of staying at a hotel, I decided to catch up with a few friends and stay at their place. It was a house of 3 girls (we'll call the girl of note Sarah) and one of my best guy friends (James) was also in town and crashing at their place too. We were staying with these girls moreso as a free place to stay and for us to catch up, but we also wanted to hang with the girls.

We sat around drinking wine until about 10pm, when everyone decided to call it a night except myself, James, and Sarah...we all had work or flights out of town early the next morning. One important piece of background: James had had a couple makeout sessions with Sarah in the past, and he was hoping to seal the deal that night; I had slept with Sarah a number of times in college, but she has always been much more attached to me than I was to her and wanted to seriously date.

Sarah is a tiny girl, a brunette with an adorable face and bubbly personality. She's about 5'7" and has an incredibly tight body. As of her senior year of college (the first time we had sex), I was only the third person she had ever had sex with.

Now back to the story: Sarah and I had been exchanging flirtatious glances and comments, and my stomach was in knots wanting to see her naked again and rekindle our formerly wild sexcapades. Unfortunately, I was in a serious relationship and Sarah was (/is) friends with her as well. Around 1am, James is pretty drunk (much moreso than me or Sarah), and he passes out on the sofa. Sarah and I decide it's time to call it a night, but not before exchanging an extended, emotionally charged glare with each other. I knew Sarah wanted me, and she knew I wanted her, but we both knew it was wrong.

Nonetheless, she retreats to her bedroom (which she shares with another girl). About 20 minutes pass, and I can't stop thinking about the way Sarah looked at me, and how much I want to rip her clothes off. So, I send her a text with something along the lines of "That was tough." And she immediately responds: "what?"

And I say "going our separate ways." She agrees, and we go back and forth for a while with mildly forward text messages. There's a break in the conversation, and I take it to the next level and texted her: "This sucks. I want you. And I know exactly what I would do to you."

About 3 seconds pass and she calls me, whispering so her roommate doesn't hear, and asks me to explain my text. I tell her that I want to grab her and rip her clothes off, turn her around, and fuck her from behind until she screams. This gets her going because she's loves being told what to do during sex, and she walks back out into the den (where I'm on one sofa, and James is asleep on the other). I'm still fully clothed but she's now wearing a tshirt (no bra) and those short, tight, cotton-like shorts that girls sometimes wear. She nods for me to meet her in the kitchen. We chat for a few moments about how horny we are, and keep staring at each other, me looking her up and down with the "i want to fuck you" look, and she keeps biting her bottom lip in the sexiest of ways.

By this time, it's about 3am and we decide to step outside on the screened-in porch so we don't have to talk in such low whispers. She sits on one chair, and we reminisce of one particular New Years Eve night when we had sex in a room filled with about 7 of our friends, and someone woke up and asked what was shaking the bed.

As we're on the porch (she's sitting, I'm standing), I keep taking deep breaths trying to control my horny-ness levels, as well as my raging hard-on. We methodically tell ourselves we can't do anything; it's not right. The more we try to resist, the harder I become, and the harder it is to fight back the urge. Finally, as we're locking eyes, I reach over and cup my hand around her pussy. She gasps and trembles, and grabs my wrist. I slowly start to move in a circular motion, and she's moving her hips around. I move my hand away, position myself even closer to her, unzip my pants, and pull out my cock and ask "do you want it?" (which sounds so fucking corny now but I swear in the moment it wasn't at all)

She replies yes and I grab the back of her head and push her mouth on my cock. Her familiar tongue and lips felt amazing licking and sucking my cock, and I let out a loud, satisfying moan as I look around at the nearby busy road and neighbors' houses not 100 feet away. She sucks my dick for about a minute, and I grad her from underneath her arms to stand her up, and I aggressively rip down her shorts and thong. As soon as they're completely off of her, and with my jeans still on and my dick through my zipper, I pick her up off the ground and she wraps her legs around my waist.

I reach around and grab her ass and stick my fingers in her pussy to discover how wet she is. I immediately grab my dick and thrust it into her in an unbelievable moment of lust and pure pleasure. We both exhale deeply as my dick moves around her tight, wet pussy. After who knows how long of this (I'm guessing 2 minutes), I put her back on her feet, drop my jeans and boxers to around my ankles, and tell her to step over to the patio table and to bend over. She dutifully obliges and I get behind her and slowly insert my dick back into her beautiful pussy. This time, I'm able to watch myself enter her and can respond better to her movements and what is obviously amazing for both of us. I give her ass a couple hard slaps and she gives a slight, erotic scream each time I do so.

I slowly build up tempo, and I recognize that she's about to cum. I have one hand on her hip and the other on her shoulder as she places her hand over her mouth to hush her screaming orgasm, and her eyes roll to the back of head. Quickly thereafter, as I've lasted as long as I possibly can, I pull out and cum all over her lower back and ass. We both nearly fall over as our knees give out, and stand there trying to catch our breath. Afterwards, she mentions that that was the hottest thing she's ever done, and I agree.

Anyway, I felt immediate regret, even before I pulled up my pants or cleaned up my cum. However, it was an amazing experience and I still think about it often and it's a common memory in my spank bank. (please dont think I'm a too terrible of person for cheating. But actually, to top it off, I'm still dating the girl and she's never found out about either of my indiscretions...so maybe I am a shitbag)