Hot Tomboy Little Sister Ch. 04-05

For Women


[In which 18-year-old Caitlin undertakes incestuous covert operations on a family road trip]

For Christmas we drove to Chicago to stay with my Dad’s parents, about an 8-hour trip. Caitlin and I rode in the back seat, and after a while Cait pulled a blanket over herself and stretched out across the seat, resting her pretty head on my thigh. The warmth of her against my lap was beginning to turn me on, and when she rolled over to get more comfortable, she must have noticed my arousal, so near her face, and it spurred her to mischief.

She pulled the blanket up further, covering her head and my crotch, and I wondered what she would try next. I was both titillated and worried by the thought that we could get busted so easily, but the ‘rents were oblivious, grooving to their old Police and Simple Minds CDs on the stereo.

First I felt only a pressure against my crotch, but then I could tell that my fly was being unzipped, and Caitlin began to stroke my hard-on like the expert she had become. Next the warmth of her mouth engulfed me, and I even felt a little painful-exciting brush of her teeth.

I held the blanket up a little so that the bobing of her head wouldn’t be too obvious through the rear-view. The thought that my little sister was gobbling my penis right here in the family car was thrilling, but of course I had to try not to make any obvious noises, and Cait was clearly enjoying my struggles. from time to time she’d give my head an extra hard suck or even a nibble and then giggle in her breathy girlish way as I suppressd a yelp.

It wasn’t long before I felt my climax approachin, and hoped my sister knew what she was doing; I didn’t know how we’d explain a big old semen stain on the seat and blanket. But Kelsey had it figured out: she kept pumping my cock deep into her mouth as I spurted what felt like a pint of cum between those sensuous lips. She let out a couple of muted gagging sounds, but managed to swallow most of it, letting the rest dribble in a sticky (and oh so sexy) trail down her cheek. I fished out a Kleenex and helped wipe her off as she grinned up at me.

Caitlin was just sitting up, with her best innocent-schoolgirl expression on her face, when Mom turned around and asked, “Hey kids, are you up for something to eat?”


[Depraved cousin Erin helps the siblings explore some kinky territory.]

My Dad’s relatives were all very nice, but the main attraction of the trip was the chance to see our cousin Erin, who was 21 and a big-city college sophisticate. She was even shorter than Cait, urfa escort maybe 5-foot-1, a red-headed fireball of energy and adventure. She had lots of black leather clothes and arty tattoos, and every time we saw her she seemed to have a new piercing. This time it was a tongue stud, which I couldn’t stop thinking about.

The first night the family played Trivial Pursuit, and Cait and Erin were a team. Erin sat on Cait’s lap so they could confer more easily…all perfectly innocent, I’m sure. Cait did seem to be having a very good time, and her cheek had a few incidental brushes with Erin’s generous breasts (Erin is short but quite three-dimensional). Then we headed off to bed; the girls were sharing the basement bedroom, and I had to settle for imagining what they might be getting up to down there.

Next morning Erin and I were the first up, and when she greeted me with an affectionate hug I could feel her curves loose under the oversized T -shirt she wore for pajamas. Her body still had the musky warmth of bed, and I pictured her sea of copper curls spread out against a pillow.

“So, did you guys behave yourselves last night?” I asked with a leer.

“Wouldn’t you like to know. Actually, we mostly talked…it sounds like you two have been up to no good at all out there in the wilderness. What a bad, bad boy and girl!”

She said this, of course, with eyebrows raised in mock horror and disapproval. Cait and I had agreed we would let Erin in on our secret, knowing that she would be cool.

“She really loves you and her girlfriend…Megan?…and the things she’s done with both of you. But she told me something she says she hasn’t shared even with you.”

“Oh? Do tell…nothing bad, I hope.”

“All depends on your attitude. She has this fantasy of taking a woman the way a guy does, of penetrating a girl and pumping deep into her.”

“Wow, that sounds super hot! If we can find a way to let her act it out, I’m soo on board. As long as I get to be there.”

By the time we finished our Cheerios, we’d thought of a gift for Caitlin that she definitely wouldn’t find under the tree.

Cait had to go do some last-minute official Christmas shopping with Mom, so Erin and I headed into town on our mission. She had on a black leather jacket over a tight shirt that didn’t quite come down to her miniskirt and black leather boots; I enjoyed seeing other guys turn their heads and think, what has this random dude got that I haven’t? Why is this luscious babe acting so happy to be with him?”

And balıkesir escort indeed, her usually-pale skin was flushed with excitement and the chilly air and her green eyes sparkled as she skipped ahead, gesturing wildly as she told me about some band she was into, then came back and threw an arm around my waist. I’m an OK-looking guy, six feet or so and wiry rather than buff, but I felt pretty lucky.

Plus, there was our destination to think about, and before I knew it we were at the sex shop and comparing the strap-on dildoes (for that was our scheme to fulfill Cait’s fantasy). I was a little intimidated by the size of some of them, and relieved when Cait went for a big but not enormous wang…she was going to have it inside her, so it was really her call. We picked up a few other things, including lubricant, and my mind wandered hopefully, thinking about what we might do with that.

That night we were “too tired” for board games, and as we hoped, the oldsters retired at a reasonable hour. When the coast was clear, I sneaked down to the basement. Cait could tell already that something was up, and was dying of curiosity, so we handed her the package and told her to open it. When she figured out what it was, at first she turned beet-red, which just made her more adorable, and held it out like it was going to bite her. But with our encouragement, she warmed to the idea and even became jittery with anticipation, bouncing up and down on the bed like a kid.

“OK,” said Erin, “now we need to get you dressed for the role.”

As she removed her T-shirt and torn jeans, Cait replied, “You know high heels and garter belts are totes not my thing. My hockey uniform is pretty butch, but kinda awkward.”

“I fished out a baseball cap and flannel check shirt from her stuff, and finally her clunky steel-toed boots. “You’re going to be the butchest hottie in town now!”

We all worked together to get the dildo hitched on; it was kind of ludicrous, but also very kinky.

Erin and I knelt in front of Cait and she really started to revel in her new self. She ordered us around: “Erin, you filthy slut, worship my cock, lick it like a lollipop! Oh yeah, yeah, swallow that shaft!”

I took a turn too, which felt a little weird but cool, and I loved the heat already coming off Cait’s body and the smell of her already-fragrant sex. I let her push my head down on the smooth, now-warm dildo and even made some gagging sounds as she said, “Take it all, you little nancy-boy! Am I too big for trabzon escort your little throat?”

I had to suppress a giggle at the sight of my shy, cute little sister strutting her stuff like a dominatrix. I was tempted to stand up and ruffle her hair, but that would have spoiled the mood.

Now it was Erin’s turn again to work on the dildo, and I turned to her, kissing her soft ivory belly sucking on the gold ring in her navel, taking one breast into my mouth through her flimsy shirt and squeezing it with my hand. I ran my other hand between her thighs and up under her skirt to feel the wetness in her lacy panties. The girls were clearly ready for the next step, and Caitlin commanded me, in her piping but husky voice, to bend down and take off her boots.

She lay on her back and Erin crouched over her, gradually lowering herself onto Cait’s new big dick. Erin had shaved down there, and I watched in rapture as the shaft disappeared between her puffy,, swollen lips. She let out a few grunts, “Unk, nnk,” and then “Ahhhh…”

It took Caitlin a little while to get the hang of moving her new appendage by thrusing her hips, but once she did, she threw Erin down on her back and climbed on top, pumping her in classic missionary style. Erin egged her on, muttering, “Ooh, ooh, give it to me hard, you big butch dyke. Oh, fuck me, fuck me, make me scream!”

I lay beside the girls, cheering them on and stroking Caitlin’s back and ass, feeling her strong muscles clench with each thrust deeper into Erin. Then I kissed Erin, my tongue fascinated by the little ball of her tungue stud, while she fondled my cock and balls with a free hand, bringing me close to eruption.

As my sister and her cousin approached orgasm, their dirty talk subsided into cooing and sighs, and the theatrical thrusts were replaced by squirming and wriggling as each girl tried to get just the right friction on her sensitive vulva, plus a “Ooohhng…uuhhng” from Erin when Caitlin kneaded her breast or sucked on her distended nipples.. Finally I could sense a long series of quivers and twitches and gasps, and I knew they had come.

As Caitlin withdrew, I kissed Erin deeply and she intensified her strokes until I exploded onto her lovely white belly and smooth pubis. Cait saw an opportunity; she rubbed the tip of her dildo in the semen and then commanded us to lick it off:

“Lick my cock clean like the nasty sluts you are, you little bitches!”

My cousin and I lapped our juices from the smooth head and shaft, then shared them as our lips and tongues met.

And then she took off the belt and was our old Caitlin again, saying, “You guys are the best! This was like the sweetest gift e-ver!” and even beginning to weep as she smothered us in kisses. We passed around a bottle of red wine and curled up together like a basket of puppies until it was time for me to sneak back upstairs.

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