Hot Tomboy Little Sister Part I

I always thought my little sister was pretty hot, but my fantasies began to become reality when she was a junior in high school. I was two years 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 I loved the way the fabric of a tight t-shirt would pucker between her tits.   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: no makeup, no skirts, no coquettish mannerisms. As for me, 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, I’d want more than a handjob for my turn…if I was going to go down on her, would she do the same for me? She made an adorable little croaking sound, the way she always did when she was unsure of herself, then said, “…uh, OK, I’ll give it a try.” I conceded, “You can always stop if it’s gross…and we can take a shower before you do it, so I’ll be nice and clean!”

I went down first again this time; now that I had some practice, I had her breathing hard in no time, and as I licked and probed with my tongue 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 as I turned the water on, she bent over to pick up some shampoo, showing off the sleek muscles of her thighs and calves, and exposing to view a little tuft of hair in the gap between her legs. She put a dollop of shampoo in my hand and I started to lather up her tits, bringing the nipples to attention before moving down to her taut belly, inviting little navel and pubic mound.

Meanwhile she was giving a gentle but thorough shampooing to my ass, balls, and now-hard cock, with a look of intense concentration on her childlike face.

When we were all rinsed off and the bathroom was hot and steamy, she cut off the water and got down on her knees, taking my yearning 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 heaad 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.


Caitlin’s best friend Megan was taller and more slender, with shiny black hair that fell to her back like silk. She was more of a girly girl; unlike Cait, she wore makeup and short skirts that showed off her gazelle’s legs, and she also took advantage of her petite breasts by going braless. The two of them would snuggle and cuddle and hold hands the way girls are allowed to do without anyone thinking they’re lesbians, but I knew now that Cait harbored fantasies about Megan. I didn’t know what Megan would think of that. I thought she was pretty sexy, and when she came over, I always hoped for some ‘innocent’ wrestling with those two lithe and supple bodies.

One night when Megan was sleeping over, they let me watch Netflix with them in Caitlin’s room. Cait and I were wearing sweats, Megan a sort of risque teddy that made me wonder if she was putting on a show for me or my sister or both of us. In any case, I was enjoying the view as I sat on the floor and Megan sat on the bed with her knees pulled up.

She was telling us about breaking up with her latest boyfriend, and how selfish he was, only interested in his own pleasure.

“Wasn’t he any good at eating you out?” asked Caitlin.

“OMG, no way would he do that.”

“Oh that’s too bad..I’d miss that.”

“Oh, Miss Virgin? Have you had lots of guys go down on you?”

“No,” said Caitlin, then she made some sputtering sounds and a little squeak before she came out with it. “Just one.”

“Who??? Aw come on, I tell you everything, now you’re holding out on me? What kind of a friend are you?”

“Well, you have to promise to never never tell anyone, or I’ll have to kill you.”

And so she told Megan. At first I was embarrassed, but it was also a turn-on, and Caitlin said how cool I was and how good I made her feel.

“I bet,” she said, “He’d do it for you too, if you ask him nice. He thinks you’re a hottie.”

“Well, so do you, Cait!” I shot back.   That turned her pretty red, but Megan didn’t seem to mind.

“OK, dude, if you’re up for it, let’s see what you got.” And she began to pull off her panties. So I crawled up on the bed and buried my face in Megan’s trimmed black bush, licking first around the edges of her vulva, hen inserting my tongue and lapping up towards her clit, and after a little while adding a couple of fingers, searching out her G-spot. She got into it, grunting encouragement and digging her long, polished nails into my hair.

And then I heard wet sounds coming from above, and I looked up to see Caitlin’s mouth welded to Megan’s. Caitlin had one hand rubbing circles around one of Megan’s dainty small tits, and muffled moans were coming from both of them. The next time I looked up, Caitlin had her sweats off and was kneeling next to Megan, burying Megan’s face in her breasts, while Megan had one hand cupping Caitlin’s crotch and was thrusting two fingers into her cunt. Between gasps, Cait was talking to her:

“Ooooh, fuck me, fuck me you dirty little bitch, you naughty naughty girl!”

Just then Megan’s juices began to gush over my face, dripping down my chin, and she convulsed in a racking orgasm that must have distracted her from Caitlin. When it was over, I rested my head on the tender creamy flesh of her inner thigh.

“Wow, Cait was right, you are a cunning linguist. But what are we going to do about that?” (Pointing to my raging hard-on.)

“Well, last time Caitlin gave me a blowjob, but what I’d really love is to put my money where my mouth was. And you know, when I go down on Cait, she calls out your name….so maybe you could help both of us out at the same time.”

Megan gave me a crooked smile and turned over onto her knees while Caitlin lay back on the pillows and brought Megan’s face up between her thighs. I crept up behind Megan and gazed down at her beautiful heart-shaped ass. I reached down to the gap between her legs and found her, of course, already wet and relaxed as I rubbed my cock-head up and down around her entrance. She said something I couldn’t understand because her face was buried in Caitlin’s twat, but it sounded encouraging, so I slipped my head in. The sight of my dick penetrating that hot cunt, and the feel of my hands gripping her hips almost pushed me over the edge right there, but I managed to hang on. I leaned forward and cupped one of her tits, which were hanging down in little triangles with her hard nipples at the points, jiggling back and forth with each of my thrusts.

I looked up into Caitlin’s face and saw how flushed her cheeks were, her mouth open, lips trembling, eyes closed. Then she opened them, saw me in my ecstasy, and smiled blissfully.   I grabbed Megan’s long black hair and twisted it between my fingers, then reached down and gave it little tugs, at which she let out little whines of mingled pain and pleasure.

It was hearing Cait’s telltale gasps and whimpers as she approached orgasm that drove me to mine. I held Megan’s hips and thrust deeper and deeper, then shot my load into her with desperation. I collapsed onto my side, pulling her over to me wrapping my arms around her and pressing a B-cup tit under each hand. Caitlin lay on her other side, bathing her face in kisses, tasting her own juices.

At that moment we heard a knock on the door, and Mom’s voice asking, “Are you girls all right in there?” “Oh, yes, we’re just goofing around,” they replied as I dove under the covers. Good thing they were making most of the noise, and not me, or we would have been toast.


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