My bestfriend makes a damn good Tomboy
- 1 year ago
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Hot Tomboy Little Sister 1 free porn video
I always thought my little sister was pretty hot, but my fantasies began to become a reality when she was sixteen, 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 five-foot-three 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 stretch 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 Michigan 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 really 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.
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. I found that she was already wet to the touch, 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, and 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. When she had come, I raised my face to hers so that she could taste her own juices on my lips and cheeks.
Then we headed to the bathroom and finished undressing. 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 exposingTo continue reading this story you must be a member. Join for FREE here.
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