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."
