Truth or Dare with My Stepsister

Cindy drops another outfit in front of me, this one even more bondage-inspired than the last. But I’m not getting dressed up just yet. First, we need to invite Christine over and get drunk in my dorm room. The room is a mess, with beanbags, pillows, and blankets scattered all over the floor.

Cindy’s wearing a long-sleeve knit top in black, with a waist-cinching corset underneath that accentuates her curves. Her black mesh skirt is long and flouncy, with lace and ribbon at the hem, and a dark burgundy crinoline underneath that adds to the drama. Her stockings are black, and her boots are big and clompy.

As we settle in with a bottle of tequila, we start playing Truth or Dare. “Are you really brother and sister?” Christine asks Cindy.

“No, not really,” Cindy replies, a sly grin spreading across her face.

“Sister and sister,” Christine says, raising an eyebrow.

“What?!” I exclaim, laughing.

“Next!” Christine says, passing the bottle back to Cindy.

Cindy turns to Kevin. “Do you think Christine is hot?”

“Yes, and I’ve told her that,” Kevin says, grinning at Cindy.

“You didn’t say I was hot, you just said you liked me,” Cindy protests.

Kevin turns to Christine. “Has a girl ever penetrated you?”

“No, but me, with toys and stuff,” Christine says, her voice barely above a whisper.

Christine turns back to Cindy. “How old are you really?”

“Fifteen,” Cindy says, a mischievous glint in her eye.

“Woah! No Shit!? But that’s kinda hot though. You’re very mature,” Christine says, laughing.

“Gee, thanks,” Cindy replies, rolling her eyes.

Cindy turns to Kevin. “I dare you to kiss Christine.”

“Finally!” Kevin exclaims, grinning at Cindy.

“Yay!” I shout, feeling a rush of excitement.

As Cindy and Kevin start kissing, I feel like I’m not even in the room with them for a minute. But watching them is turning me on, and I find myself getting more and more turned on by the minute.

Christine breaks off the kiss and turns to Cindy. “Do you guys have sex?”

“As much as we can!” Cindy replies, her voice barely above a whisper.

There’s a long pause as we all process the question. Then Kevin speaks up. “Are you a virgin?”

“No, I’ve had sex with other people, girl people… and I’ve used dildos,” Christine says, her voice a little shaky.

“Indeed,” Cindy says, leering at Christine.

Cindy turns to Kevin. “I dare you to show Christine your underwear.”

“OK,” Kevin says, grinning at Cindy.

As Kevin strips off his jeans, revealing his burgundy satin panties with black lace trim, I feel a rush of excitement. “Wow! Are you always wearing that?” Christine asks, her eyes fixed on Kevin’s underwear.

“Sometimes,” Kevin replies, smiling at Cindy.

“I’m not looking at your dick by the way. Just admiring your underwear on your slim hips,” Christine says, her voice dripping with sarcasm.

“Dare me to kiss her again,” Cindy says to me.

“That will get it excited!… OK, kiss her again, more tongue this time,” I reply, feeling a rush of excitement.

As Cindy and I kiss, I lay back and watch them, feeling a sense of excitement and anticipation building inside me.

Cindy pulls back and looks at me. “I’m gonna dare both of you to touch my boobs. They really need touching.”

“Okay,” I say, feeling a rush of excitement.

As we both reach out to touch Cindy’s boobs, I feel a rush of excitement and anticipation building inside me.

Cindy pulls her tank top off, revealing her rock-hard nipples poking out of her underwire, push-up bra.

“Errrrrggggg,” she squirms and wriggles around as we both touch her breasts.

Christine bites her through her bra, and I pinch at her nipples, dipping my fingers inside the bra cups.

“Hey, that’s unofficial! Back to the game!” Christine says, laughing.

“OK, everybody breathe… Truth. Christine, have you ever touched a dick before?” Cindy asks, her voice mischievous.

“No, and I don’t plan to,” Christine says, her voice a little shaky.

“Dare! Just a little, over the panties,” Cindy says, grinning at Kevin.

As Christine feels my hard cock through my panties, I feel a rush of excitement and anticipation building inside me.

“It’s kind of friendly. Still a little intimidating but it’s you so it’s not so bad,” Christine says, her voice barely above a whisper.

I lock eyes with Cindy in a knowing stare. “I dare you to give our friend a cock sucking demonstration.”

“I will! And you’re gonna give a Jizz shooting demonstration!” Cindy says, her voice dripping with sarcasm.

“And Christine gets to help, but she only has to use her hands… and I get to touch her boobs,” I add on all my demands.

There’s a long pause as we all process the request. Then all together, we say, “DEAL!””

Cindy gets down between my legs and peels my panties away from my straining hard penis.

She mouths all over it noisily, telling Christine what she’s doing, and Christine gets a hand on me and slides it around on my spit-wetted dick.

I draw Christine up toward me for some kissing, which she seems to respond well to, and I get my hands on her voluminous tits over her black knit top.

I tug her nipples to attention, but she breaks off the kissing and returns to assisting Cindy, who’s trying to swallow my entire wang down her throat.

I settle for having one hand on Christine’s tit and the other on Cindy’s head.

Cindy’s doing the back of the throat thing and gagging, and everything is coming to a climax for me.

My legs start to tense up, and my voice rises to girly levels, and Cindy draws off and strokes me with one of her hands and one of Christine’s.

“Now Shon… Shon is gonna show you just how turned on you’ve gotten him,” Cindy says, her voice dripping with sarcasm.

“This beautiful cock is going to shoot some creamy fireworks for us!” Christine says, her eyes fixed on my dick.

“ohhhhhh!” I look at Christine’s dark eyes and little glasses, and my hand on her billowing breast, and at Cindy’s eager face grinning up at me.

“OOOOHHHHHHHHHUUUUHHH!” The cum blasts two feet in the air, no lie, and rains down on their hands and arms and Cindy’s forehead.

I buck uncontrollably and squeak like a little girl, and subsequent shots of hot semen leap out and land on Christine’s skirt and my belly and Cindy’s shoulders like a jumping firehose out of control.

“Wooooahh! Ya!” Christine exclaims, her voice filled with excitement.

“Wow! Eeeeek!” Cindy says, her eyes fixed on the cum dripping from my dick.

“awesome baby!” Cindy wrings out my dick with both of her hands, milking every last drop.

Christine looks up at Cindy, her eyes fixed on the cum on her hands. “Ew,” she says, her voice barely above a whisper.

Cindy scoops up some of the cum with her fingers and dabs it right on Christine’s tongue.

“Mmmm! Good girl’s been taking her vitamins!” Cindy says, her voice dripping with sarcasm.

Christine winces at first, but then tastes the cum. “Well…” she says, her voice barely above a whisper.

Cindy has more globs on her fingers from my belly and brings them up to Christine’s mouth.

Christine sucks Christine’s fingers clean, and Cindy looks at me, a mischievous glint in her eye.

“Who’s Shawn?” she asks, her voice dripping with sarcasm.

“Truth?” I reply, feeling a rush of excitement.

“Truth,” Cindy says, her voice barely above a whisper.

“Shonda is her name and she’ll always be my big sister. That’s never gonna change,” I say, my voice filled with emotion.

“I see. Dare,” Cindy says, her voice dripping with sarcasm.

Cindy turns to Christine. “I dare you to kiss some more cum lipstick off of my lips.”

Cindy reapplies a coating of my semen to gloss her lips, and they kiss some more.

I mop myself up with a towel, watching them rub their jutting breasts together.

“Well, it doesn’t taste like pussy,” Christine says, her voice barely above a whisper.

“Pussy tasting! That should be next!” Cindy exclaims, her voice dripping with sarcasm.

Christine looks bright red and laughing, and Cindy shouts to me, “Shonda, you should get a dare next! I dare you to show your special friend Christine how good you are at eating pussy!”

“Ummmmm???!!” I exclaim, feeling a rush of excitement.

I crawl under Christine’s long skirt to show her how good I am at eating pussy.

Her knit stockings end mid-thigh, and her creamy skin goes up to her black panties. Her mound is hot and moist when I get there, and I nuzzle my nose and chin into her crack, through the silk, and then drag and bite with my teeth.

She’s very very wet and musky, and I’m getting charged up, rustling around beneath her skirt and crinoline.

Her lips are hairless around her honey hole, and while her bush is cropped fairly short, it widens out into a V going up her abdomen.

She spreads out some more and gets in a very receptive position. I’m finally getting to eat her cunt! I splash and slather around in the wetness.

“Oh God! Oh Fuck!” Christine exclaims, her voice rising to a crescendo.

I’m batting her clit with my lips and gently sucking it, and she’s moving and undulating with my ministrations.

“Oh Jesus! Oh my fucking God!” she exclaims, her voice filled with ecstasy.

It’s getting a little suffocating in there, so I push her skirts away and come up for air. Cindy’s beside her, running her hands over her boobs and nuzzling into her ear.

When I pull away from Christine’s dripping pussy, Cindy’s hand goes right down and her fingers dance around Christine’s bloated clit.

“Let’s finger it AND lick it!” Cindy says, her voice dripping with sarcasm.

“Unnnhhhhhh. Fuck!” Christine exclaims, her head thrown back in ecstasy.

Cindy covers Christine’s mouth with a kiss from time to time, and I go high, working the clit with soft but rapid fluttering of my lips and tongue.

“Oh Gaaaaaad! Oh Fuck!” Christine’s voice rises to a crescendo, and her breathing picks up speed.

I keep working around her button, and Cindy’s two fingers are driving up inside her. We’re fighting for space down there, and my face is getting all sloppy.

Cindy draws out a fluid from Christine’s vagina that tastes different than before – like love. Tangy love.

“Oh GoD Oh Jesus! Oh JESUS! OH JESUS! FUCK!!” Christine exclaims, her voice filled with ecstasy.

She’s definitely cumming now, thrashing and holding both my head and Cindy’s hand jammed against her and humping into us.

“Fuck! Jesus!” I exclaim, my voice rising to a crescendo.

I never knew she was so religious!

Awwwwwww God!” Christine exclaims, her body finally going slack and lying there panting and wet.

“Thank you Thank you thank you” she says, her voice filled with gratitude.

I slide up her body to where Cindy is and plant a massive wet pussy juice kiss on her lips.

“I want some too!” Cindy kisses my lips and face, getting girly essence on her too.

“Clean my fingers,” Cindy says, her voice dripping with sarcasm.

She puts them in my mouth, and I suck the tang right off of them. She gets up and brings back two more shots.

She straddles me, and we drink them. Then her bra comes off, and the two most perfect orbs are once again in my face.

“Mmmm, big sister, give me that luscious cock that I see poking up,” Cindy says, her voice dripping with sarcasm.

She’s astride me, and my hardon is very lively between her legs. It got hard while I was sucking my friend’s pussy, and now I’m going to get to stick it in my sister.

She’s quite moistened and engorged, and she stands up quickly and peels off her panties and then lowers herself down onto me.

Her tits bounce like taut balloons as she rides me like a cowgirl. She gets my cock pointed at just the right place and thrashes about and makes a lot of noise.

“Give it to me! Give it to me! AAAAHHHHHH!!” she exclaims, her voice rising to a crescendo.

She’s so fucking hot! Her orgasm sounds vibrate my flesh and make me shoot off.

“Ahh Shon,Shon,ShonDAAAAA!!!”

“Ooohhhh Cindy!” I bridge up and lift her in the air on my hips and my dick and my second load of the evening fills up her tight, clinging cunt.

I give her multiple gushing thrusts before she flops on top of me, sweaty and panting.

“Stay, stay… stay in,” she mews.

I stay hard for another five minutes inside her hot clench and she nuzzles and coos and relaxes on top of me until finally her body pushes me out along with a slimy dollop of cum.

“I think Christine’s passed out,” Cindy says, her voice dripping with sarcasm.

“Ya, we wore her out,” I reply, feeling a rush of excitement.

“You could probably fuck her now…” Cindy says, her voice barely above a whisper.

“No, that wouldn’t be cool,” I reply, feeling a sense of unease.

“Ya but Mom wanted it. I don’t want to violate her,” I add, my voice filled with emotion.

“Aw.. you really like her,” Cindy says, her voice dripping with sarcasm.

Christine high-tails it in the morning as we lay sleeping, smashed together on the floor.

Cindy calls me Shon’ sometimes by accident. “Oh, Shawn’s my middle name,” I say, my voice filled with emotion.

“She avoids calling me Kevin or even referring to me as ‘HE’,” I add, feeling a sense of unease.

But for now, I’m just happy to be wrapped in Cindy’s arms, feeling the warmth of her body and the love that we share.

We sit in a cozy booth at the student center’s cafe, surrounded by the hustle and bustle of students going about their day. My companion’s hand slips under her skirt, and I feel a rush of excitement as I realize there are no panties to separate us. I gently caress her, and she begins to point out the different people passing by, speculating about what they might be like in bed.

She whispers to me, her voice barely audible over the din of the cafe, “I bet he’s a wild one, all that confidence and charm. And her, she’s got that quiet, introverted thing going on, I bet she’s a total wildcat.” I listen intently, taking it all in as we continue to explore each other.

A Frat boy catches her eye, and he makes a lewd comment, but she quickly shuts him down. “I’m fifteen,” she says firmly, her voice rising above the noise.

Saturday night rolls around, and we invite Christine over for a date. I’ve been transformed into a vision of femininity, thanks to my sister’s gifts: shiny white stockings, a white garter belt, and a pink satin bustier with intricate lace details. I still need to find some heels to complete the look.

Christine arrives, looking stunning in a black pea coat, her hair straightened and cascading down her shoulders. She drops the coat to the floor, revealing a black lace demi-cup bra with extra ribbons that accentuate her curves. Her garterbelt is open, showcasing her lace-topped fishnet stockings and the ribbons that trail down her thighs.

We both can’t help but be drawn to Christine’s sumptuous breasts, and we begin to explore her curves and crevices together. The air is electric, and we’re all breathing heavily as we lose ourselves in the moment.

Cindy asks Christine about her sexual experiences, and she reveals that she’s never been with anyone but herself, and perhaps a few fingers and tongues. “And a very pretty girl,” she adds, smiling at me.

Cindy turns to me and says, “I wanna fuck her,” and Christine’s response is immediate: “Ooo ya!”

Cindy begins to prepare for our little show, removing her cage skirt and fastening her strap-on. I get down on my knees in front of her, and she asks me to suck her cock. I take it in my mouth, gagging slightly as I try to accommodate her size.

We put on a show for Christine, making sure she sees all the best angles as I suck Cindy’s cock. I make little girl sounds and exclamations, and Cindy poses lasciviously, slapping her dong against my lips.

Cindy asks Christine if she wants to try, but Christine declines, saying she’d rather watch. “I probably want you to fuck me though, later. After you give it to sweet little Shonda.”

Cindy enters me from behind, and Christine begins to jack me through my panties. The sensation is overwhelming, and I’m spooging in no time. Cindy then cleans herself off and takes Christine doggy style, with me still crouched next to her.

We share some knowing looks and kisses as Cindy pounds away, and I play with Christine’s breasts as they hang down and rock with Cindy’s thrusts. Cindy demands that Christine roll over, and they go to missionary, with Christine getting several loud orgasms.

Finally, it’s my turn, and Christine invites me to climb on top of her. I wait as long as I can, and when I’m about to cum, I pull out. High-pitched wailing moans escape my mouth as ribbons of pearly cum arc from my dick and splash all over Christine’s exposed tits!

Cindy dives onto Christine and starts licking off the semen, and Christine looks a little shocked but also turned on. “Oh God, OK, Ok…ya! Shit ya! Suck my tits!” she exclaims.

Cindy takes a long time licking Christine, who’s enjoying every second of it. “Fuck, I wanna do you so bad! I’ll do anything you want me to. Tell me what to do! I’ll do it!” Christine says, her lust and desire palpable.

Cindy commands her to eat her pussy, and Christine obliges, going to town on Cindy like there’s no tomorrow. I lie curled up on the bed, watching the spectacle, and eventually doze off, exhausted but also exhilarated.