Hot Tomboy Little Sister Ch 01

I always thought my little sister was pretty hot, but my fantasies began to become reality when she was an 18-year-old high school senior. I was just a year older, still living at home and working at the local hardware store to save money for college.

She was 5-foot-3 with dirty blonde hair cut short enough to stand up, nerdy hipster glasses, and full soft lips. Her narrow hips gave her a boyish figure that was belied by her full breasts. You could see a bit of cleavage when she wore a tank top, and her tight jeans revealed firm, athletic legs and a compact rounded ass.

Caitlin was such a tomboy that she scared off the guys at her small-town high school, and I was too shy to ask the girls out, so we spent a lot of time hanging out at our house in the woods,. Sometimes we'd rough-house, I'd pretend to let her pin me and tickle me into submission, squeezing her powerful little thighs around my torso and leaning her boobs perilously close to my face while I tried to keep my throbbing hard-on out of her way.

And sometimes I would pin her,. It was thrilling to feel her wriggle and writhe beneath me,, to hear her squeal as I poked and prodded and once in a while 'accidentally' brushed the side of a tit. I spent many an hour reliving these sessions as I jerked off late at night.

Often we watched TV together. We'd sit on the couch and she'd put her feet in my lap for me to massage her delicate arches and small toes, prompting sighs and groans of pleasure. Or she'd sit across my lap; the best part was when she'd adjust position, squirming a little and, I think now, pretending not to notice my arousal.

One night we were watching "Six Feet Under," the episode where Claire thinks she might be a lesbian but can't deal with cunnilingus, and Caitlin said "I wonder what that would be like, having a girl go down on me." I said I'd wondered the same thing, though I guessed it'd be different for a guy. Neither one of us had any experience to go on.

"Well, you could pretend," I said.

"What, what do you mean?" she asked. Her voice was always soft and a bit breathy, like a flute, and now she was also hesitant.

"It wouldn't really have to be a girl. If you close your eyes, what's the difference?"

"And where would I get a guy to do it? Some joker from school that I don't even trust?"

"Um,...I'd be willing to try. If it gets all weird, you can just tell me to stop, and I will. You trust me, don't you, Cait?"

"Yeah, sure I do. But really, you'd reallly do that for me? Doesn't it gross you out?"

"Never know until you try. But I don't think so. You know, you're the hottest girl I know."

"Aw, you're the best big brother ever!" She gave me a big hug, straddling me on the couch and pressing her boobs into my face, consciously or not.

When she sat down again, I said, "Let me help you with these" and unbuttoned her jeans, then pulled them off as she held each leg up for me. I knelt on the floor and helped her remove her brief-style panties; she was already wet, so I knew she had been having dirty thoughts too.

The taste was rather strange at first, but I soon got used to it, and her little breathy whimpers turned me on. I grabbed her slender hips as I licked, then started to probe with one finger while I reached my other hand up under her shirt to feel her firm breast and stiff nipple. As I licked her labia and gave the clitoris an occasional flick, she began to clamp down on the sides of my head with her muscular thighs and grip my hair with her small hands.

"Oh, Megan! Oh, Megan!" She cried out the name of her best girlfriend. "You are such a dirty slut! Fuck me with your filthy fingers!"

After a few minutes, her whimpers became long, soft high-pitched moans, and her vulva began to quiver; this must be what a girl's orgasm is like, I thought. It went on and on, not like a guy's—when she finally subsided, I was tired but felt a sense of triumph that I could make her come.

I sat back on the couch, and she snuggled against me, saying, "Wow! That was so awesome! You are the sweetest." Then she noticed the tent in my pants and said, "I owe you big time. I should really do something in return... I'm not sure I can put it in my mouth, but would you like me to stroke it with my hands?"

I didn't wait for her to change her mind, but unzipped my pants and let my dick spring free of its painful confinement. I had to do a bit of coaching, but she spat on her little hands and started to milk my cock, up and down. With my encouragement, she made sure to caress the sensitive underside of the head with each stroke.

Soon a dab of pre-cum emerged from the tip of my cock, and Caitlin bent down to get a closer look. "Did you come?" she asked, and I explained that it was just lubricant, so she rubbed it around the head and resumed pumping, while I reached down to cup a breast in my hand, then rubbed the fuzzy hair on her head. She was really getting into it, peering closely at her work, when I began to moan and tremble, and finally exploded, sending jets of semen into her surprised face, onto her luscious lips and the lenses of her glasses, where it dripped. At first she shouted "Eek!" but then she wiped some off with her finger and tasted it. "Mmm, that's kinda funny tasting, but not too bad."

"Gee, that was totally fun!" she said with a smile. In my amazement, it was all I could do to reply "Uh-huh," and suggest that we could do it again sometime. My mind was racing with visions of what else Caitlin might let me do.

The next time our parents were working late, I suggested that we pick up where we had left off...but this time, I said, a handjob wouldn't quite do it. If I was going to go down on her, she'd have to do the same for me. But we could do it in the shower, so I'd be nice and clean. I went first, though, and now that I had some practice, I had her breathing hard in no time, and as I worked I kneaded her beautiful compact ass cheeks, working a finger now and then into the crack between them.

Then we headed to the bathroom and got undressed. This was the first time I'd seen her topless, and I gazed at her perky young tits with their large puffy aureolae. We stepped into the shower and I turned the water on as she got down on her knees, taking my hardening cock in one hand. To see her blue eyes looking up questioningly at me as her tongue made its first tentative flicks at my glans almost made my knees buckle with desire, and I leaned against the wall for support. Seeing her power over me seemed to turn her on, and she quickly became less self-conscious, putting the head into her mouth while she pumped with her hand, pressing my cock between her tongue and the roof of her mouth as she licked the bottom of the shaft. She let out a little "Ooh!" this time when the pre-cum appeared, and redoubled her efforts.

Finally, as my orgasm approached, I was so overcome that I had to sit down on the edge of the tub. Caitlin leaned over to continue sucking, and now I could reach down and massage her slippery tits, pinching the nipples between my fingers. When I knew I was about to come, I grabbed her head and tilted it back so that I could see my jizz spray her lovely young face, from her chin to her eyebrow ring.

I pulled her head up to mine and kissed and licked her face, tasting my cum on my little sister's sweet, warm lips. She put her arms around me and pressed her boobs against my chest as I tried to catch my breath.