While my sister in law, Jennifer, was visiting last summer from the east coast, she fell asleep in my bed one evening, next to my wife, Erica. I was working late into the evening as usual, and sat at the desk in my office, directly across the hall from my open bedroom door as they slept. Horny as always, I shifted my position in the chair I use to work at the computer, leaned over and got a long look at the edge of Jen's dark pubic hair, peeking out of her sleeping shorts. My cock began to stir, and my mind was suddenly far from the research paper I had been writing. After watching Erica and her oldest sister sleep soundly for more than an hour, I was abruptly seized by the hottest and most ill-advised plan of my life. I was going to try to screw Jen! I turned off the computer and walked across the hall.
Jennifer is very free and open about her sexuality, and is infamous within their family for her presumed and documented romantic indiscretions and youthful debauchery (although she's mellowed way down with age). Looking back on a dozen years of racy comments, lingering touches on the shoulder, and inappropriately intense goodbye kisses, I had long suspected that Jen might respond favorably to a sexual advance of mine, provided the chance of getting caught wasn't too great. I had scored numerous glimpses of her tits, ass, and pussy over the years, as she 'forgot' to close her bedroom or bathroom door, etc., and there was definitely some chemistry between us. Now, blurry-eyed with erotic desire, I decided this could be the moment, and quickly poured and downed a glass of red wine, for courage.
Staring at my sister in law's lovely dark bush was making me crazy, and, after a while, I said "Fuck it, if things go gunny-sack and I get caught by Erica, I'll just pretend to be surprised that it's Jennifer lying next to me, and play off my advances as me thinking that she was my lovely wife!" Easing around to the foot of the king-size bed, I climbed in between Jen and Erica, my heart pounding so hard I thought it might be audible. I lay still and stared at the ceiling as they slept, breathing evenly. After maybe ten minutes, I began to sense that Jen was awake, and scooted over beside her, settling in, 'spoon-style.' We lay there in silence, both listening to the other's breathing. Then, my hand, seemingly of its own accord, reached out suddenly and rested on Jen's left side, just above her butt, causing her to jump a little. I kept it there for a short time, and then went for broke. I began to caress her side and back; slowly at first, then with increasing speed. This initially tentative massage soon got a response, in the form of Jen turning her head my direction, smiling sleepily, and whispering to me: "Mmmmm, that feels good. Keep going."
After a few minutes of this slow, quiet, sensual rubbing, I got brave and started to move my trembling hand over her ass; "accidentally" at first, but then more determinedly. I thrilled to the sensation of feeling the rounded outline of her pear-shaped bottom through the fabric of her boxers, and then, slowly slipping my hand downward inside the waistband, I rested it squarely on the lower arc of her left cheek. Sensing this was getting her hot, I spread my fingers out, cupped her butt firmly and slipped my hand farther in, allowing my fingertips to brush across her pussy lips. As I began to lightly stroke Jennifer's hairy vulva, I felt a trickle of moisture snaking down her inner thigh! At this point, she was becoming extremely aroused, and demonstrated this by pushing her hips back and forth against my hand in a slow rhythm.
By now I was breathing heavily, and cotton-mouthed with lust and excitement. My heart pounding like a sledgehammer, I got bolder yet, and decided to go through with my insane plan to take Jen, right next to my sleeping wife! Jen moved her pulsing hips and ass closer, reached around behind her to caress my throbbing tool. At that moment, I took the ultimate chance, quickly pulling down her boxers and pressing my rock-hard member against her bottom, nestling it in her crack. My pre-cum lubricated her warm skin as I took hold of Jen's hips, sliding my cock up and down her ass. We moved like this for a while, both of us getting hotter by the second. Swallowing hard, and pausing for a moment to ensure that Erica was still asleep, I tilted my pelvis, and, using my hand, guided my painfully erect dick slowly between Jennifer's thighs, heading toward nirvana.
