Road Trip - Part 1 - Sex Stories

Road Trip - Part 1

When I was a senior in high school, I was obsessed with sex like most boys my age. I jerked off several times a day, usually concentrating on Mary Ellen’s big tits, or at least my image of what they looked like. I knew I would never get my hands on them, but I spewed gallons of cum pretending she was standing in front of me naked and letting me play with them.

I never thought much about my sixteen-year-old sister Ann. She was a pretty girl with blond hair and blue eyes, but tiny, barely five feet tall, and almost no tits. She did have a nice ass that looked good in a pair of shorts, but back in those days I was more of a tits man, or so I thought. That all changed the night I walked into the bathroom as she was getting out of the shower.

Ann was as shocked as I was, both of us frozen in place for several seconds. She stood in front of me completely naked. I had never seen a naked girl except in magazines. I stared at her pussy which puffed out from between her legs like a peach covered with blond curls and a dark gash down the middle. Her perky hard nipples poked out from the small swells on her chest.

My cock immediately grew hard. After a few awkward moments, I mumbled an apology and left. I went to my room and spewed a huge load into one of my tee shirts. I lost interest in Mary Ellen’s tits and masturbated to images of my naked sister. I began hiding in her closet to see her naked again, and quickly discovered her firm ass cheeks separated by a dark cleft were ...

... just as appetizing as the rest of her, particularly when she bent over and exposed her pussy.

Ann might have remained a masturbation fantasy if it hadn’t been for the family vacation that summer to Cape Cod. On the way there, we stayed in a motel in a single room with two double beds. My dad was too cheap to spring for another room. Ann and I had to share a bed while my parents slept in the other one.

Ann came out of the bathroom wearing a nightshirt without a bra, oblivious to the effect it was having on me. It was difficult to keep the hard-on making a tent in my pj’s from showing so I quickly slipped under the covers. Ann bent over to pick up her towel. Her nightshirt rode up and exposed a pair of blue cotton panties wedged into the crack of her ass. Pre-cum was already leaking from my throbbing cock.

I needed relief in the worst way. Once the lights were out, I rolled onto my back and gently began stroking, trying not to disturb Ann. I didn’t expect what happened next. She shifted on the bed, and her ass cheek pressed against my thigh. Pushing caution to the wind, I rolled onto my side and draped my arm over her body pretending to be sleeping. My hard cock wedged between her ass cheeks through her panties.

When Ann didn’t move or respond, I assumed she was asleep and hoped she stayed that way. I slid my hand under her nightshirt and slowly inched it up her stomach. My cock jumped when I touched her hard nipple. I rubbed it with my fingertip and slowly moved my ...