My momma knew real early on that I was going to be a lot more than she could handle. Her solution was to ship me off to an all-girls boarding school- as if nothing bad could ever happen THERE...
I thrived there in so many ways, and by the time I had graduated and was going through my choices of colleges, I figured I already had myself a degree-level education in eating pussy and riding cock.
My first two years of college had their share of adventures, but in my junior year I found a soulmate in my new roommate, and things really took off. Charley had never so much as sniffed a wet cunt before I met her, but she brought me off like nobody else ever had the very first night we roomed together. We were lascivious, voracious and inexhaustible- we habitually shared any and all of our conquests we could drag back to the room- male, female or somewhere in between, and, with one memorable exception, always to the delight of the lucky third party. If I had been a master at cock-sucking before, Charley's patient tutelage brought me to the level of artistry.
We both hated labels- especially when applied to us- and decided that we weren't hetero, lesbian or bi-sexual: we were simply purely sexual.
At the end of our junior year, her family invited me to accompany them on a summer trip to Orlando- a celebration of her younger brother Robbie's graduation from High School, and I eagerly accepted.
We stayed at a semi-luxury resort hotel just outside of Mouseland, with non-stop shuttles running to and from the various theme-parks and attractions in the area. Her family had 2 separate suites, each with a pair of king-sized beds, joined by a center common area with a pull-out sofa, which is where Charley and I were designated to sleep. Her extended family consisted of an older sister and her husband, who had a couple of roughly 10 year old kids that worshipped both Charley and Robbie, and by extension me.
Robbie and his high-school buddy Tony also stayed with them in suite to the right of the common area. In the left-hand suite, Charley's mom and step-father Bill shared a room with Bill's brother Todd and his wife Gina, along with a couple of Gina's kids from a previous marriage- a pair of spoiled rotten young pre-teen monsters.
So the sleeping arrangements were pretty tight.
Charley could tell right away that I was sizing Todd up. He was quite a few years younger than his brother- Charley's step-dad was going to celebrate his 49th birthday during the trip- and Todd had a sort of rugged masculine quality to him. He had a certain mischievous twinkle in his eye when we were introduced that made me purr. For some reason the fact that I instantly disliked his wife Tina- which was certainly a shared response- only made me take another long glance at him.
"If you just have to fuck Todd, at least try and keep it on the down-low, huh?" Charley whispered to me a little while later- proof positive that we were always on the same wavelength, and I giggled. I figured Todd to be mid-to late 3o's or so- nearly twice my age. He was pretty well-kept though, and funny and charming no matter if he was talking to the hotel staff in the lobby or the kids. I had dabbled with older men- and women- a time or two, and they had their uses, but as a rule I generally preferred younger, more energetic lovers.
The first few days of the trip everyone was sort of going their own ways, doing the theme park thing, and even though there were all kinds of beautiful people all about, Charley's mom usually had us scheduled to meet somewhere or watch the kids, or something, so to our mutual amazement we weren't able to get laid. Other than a few quick kisses, ass-pats and the occasional subtle grope with fellow tourists, we didn't get to do more than flirt and tease a little, exchanging a few phone numbers but bringing nothing to a conclusion. So by the fourth day Charley and I decided we would circle back to the hotel early in the day and pick up something to fuck around the hotel if we could. At the very least we could get more done than just the quiet stroking of each other we were limited to on the sofa bed.
We hit the hotel pool in our bikinis and to our dismay found Robbie and Tony there. "What the fuck?" Charley asked her little brother. "How come you two aren't out chasing down some pussy?"
Her brother's jaw dropped to the ground, but his friend Tony just grinned. "Maybe that's exactly what we're doing." He said smugly as his eyes travelled up and down our bodies.
Charley glanced at me briefly and we knew exactly what each other was thinking. "So Robbie," she asked. "Have you ever been with a girl before?"
He flushed. He shared her shock of honey-blonde hair and light brown, almost golden eyes, and had the body of an athlete. He recovered quickly and angrily said. "C'mon, Sis- I'm eighteen years old. You had fucked half the football team by this age."
She laughed. "Only the ones I wanted. I liked the baseball team better," She stepped close in to Tony and dragged a slow finger down his muscled chest. His confident grin grew, and she winked at me.
I moved in to wrap my arms around Robbie's neck. I stared deeply into those almost familiar eyes as I slipped an ankle around his right calf, rubbing lightly. "Well, I think we have the makings of a decent morning ahead of us. What do you all think?"
Within seconds we were heading for the hotel room. By unspoken agreement Robbie and I headed towards the left-hand room while Charley and Tony went into the other. I wondered idly how far Charley was going to be willing to take this: I didn't have any siblings of my own, but thought that if I had one as hot as Robbie was I'd probably be eager to fuck him- but for the first time since I met her I wasn't sure.
But just the notion of watching her with her brother was enough to make me leave our door open. I was a slightly disappointed to note that the opposite door was closed, though.
