Leave with Jess

"I'll let you blow off work if you let me blow off the gym," you say, "Let's go workout at your place!" Jess lives in a college neighborhood, and she's practically tripping over guys every time she goes outside. Plus, she's a lot of fun to hang out with, and you haven't done much together in a while. Of course, it's the kind of fun where one of you ends up stranded someplace totally naked half the time, but definitely fun.

"Alright! Sounds like a hoot!" She steps out of line and heads for the door.

"No breakfast, then?" You look longingly at a banana and Jess catches your eye.

"Oh, don't worry, they're'll be plenty of phallic objects to fill you up today." She grins as she steps out the door and you follow her. She pulls out her cellphone and starts texting.

"Who's that?" You ask as you cross the street and head to her car. It's a nice, sunny day and the heat feels good on your mostly-bared skin.

"Oh, just my boss. Letting him know I'm taking the afternoon off. We're not doin' too great, bussiness-wise, so he doesn't usually mind not paying me for afternoons I take off." She sends the message and slips the phone back in her pocket, pulling out her keys and unlocking the doors to her car.

"You still drive this?" You ask as you climb in the passenger seat of her old junker Corolla. She rolls down her window a few inches to let out the stifling heat, and you do the same.

"Hey, this car is awesome!" She laughs as she starts it up and you drive off. "Besides, what do you drive?"

"Oh hush, you." You smile as she pulls onto the nearby freeway on-ramp. "Oh no..." Your smile fades as you recall her rule.

"Let's have'em." She holds out one hand, her other on the steering wheel, the wind from the cracked window tugging lightly at her hair.

"C'mon, Jess, I'm already hardly wearing anything." Jess's rule is that for a short ride, you have to lose one piece of clothing while in her car. Anything, like socks, are fine. But for a ride across town, say, from the gym to her place, you have to lose your undies.

"I'll give'em back, don't worry. Just for now." She smiles congenially across at you. "Besides, you did ask for the ride, you know."

"You know what? Let's do it!" You grin, pulling off the shoulders of your sports bra and top. You wriggle your breasts out of the sports bra and slide it up and off, handing it to Jess before pulling the straps of your shirt back into place.

"See? You're already having fun!" Jess smiles, holding your sports bra and the steering wheel in one hand, while waiting for your panties with the other. You lift your butt off the seat and pull both your panties and your shorts off at once, leaning down to snake them off your feet and bring them up.

"I am!" Your newly bared skin itches on the crummy fabric in Jess's car. You hand over the panties along with your shorts and she snatches both up at once. You shrug, comfortably bottomless for now.

"Oooh, I see you shave these days." Jess smiles at the smooth flesh between your legs.

"Oh, ya, well, you know." You spread your thighs and run your fingers along your readily warming slit. Jess jostles suddenly and drops your shorts and panties into her lap, reaching into her pocket with her right hand. She pulls out her phone and messes with it, still holding onto your bra, but keeping her legs together to hold your bottoms on her lap.

"Oooh, perfect!" Jess says as you, mostly ignoring her, spread your silky smooth lips apart and her phone clicks a shutter sound. You jump upright in your seat and turn a horridfied glare at her.

"You did not!" You say, snapping your thighs back together.

"Oh, hush, he'll love it." She slips the phone back into her pocket and you reach over angrily to grab your clothes back form her lap.

"I can't believe you did that!" You manage to snatch the shorts, but Jess pushes you back, swerving slightly.

"I'm driving! Don't go crazy!" She straightens out on the road with the hand holding your bra, and keeps you back with the other.

"Just give me back my clothes, Jess!" You say, reaching around her. She swaps hands on the wheel quickly, swerving slightly again, and picks up your panties. She quickly reaches her arm up and dangles them, along with your sports bra, out the cracked window. You freeze.

"I don't think you're in any position to make demands, sweetie." Jess grins at you as you sit back down in your seat, donning the one article of clothing you did manage to get back.

"You suck, Jess, seriously." You glare over at her, still wriggling a little to get your shorts on properly.

"It is fun to hang out together again." She grins at you and you can't help but smile slightly back. This is kinda fun. "Oh!" She jostles and swaps her hands on the steering wheel again to dig in her pocket after her phone. She gasps slightly and freezes, staring straight ahead.

"What?" You puzzle at her bizzare pose, one hand shoved in her pocket and the other holding the steering wheel. Then it hits you. "Oh my fucking god, are you serious?" You look back, and are fairly certain you can make out your panties and sports bra still floating in the wind, disappearing behind the car.

"Sorry?" Jess smiles pitifully, pulling out her phone and holding it against the wheel, not catching your eye.

"Oh my god, Jess, you suck so hard right now." You sit back, crossing your arms agaist your chest and staring out the window, the amicable atmosphere gone as suddenly as it had snuck up.

Jess starts clicking the buttons on her phone. After a pause, she pokes your shoulder. You nudge her off, and she pokes again. "What?!" You say, angrily throwing your arms down as you turn back toward her.

She stifles a giggle and shakes her head. She types into her phone again, takes a picture of your glare, and looks back at the road, smiling.

"What?" You say, still angry.

"Nothing, just something my boss said." Jess grins. You both sit in silence for a moment.

"Did he comment on my shave as well?" You lean back in your seat and look away from Jess.

"Actually, he was more interested in your nipples." She hands you the phone. "He noticed they were unusually visible in that top, and I agreed."

You take the phone, looking down at your chest. You dark nipples show clearly through the thin fabric. "Oh god..." You sigh, "my bra..." You stare blankly at the phone for a moment. It buzzes in your hand and Jess reaches for it. You bat her away.

"Give it!" She says as she starts to pull off the freeway. You bat her away again.

"No, I'm gonna send him a pic now." Your angr turns into a smile as she starts to negotiate traffic and has to stop fighting with you. You reach across and pull at her top, twisting it around her. She fights you, but only half-heartedly.

After a meager struggle, she lets you pull her top up over her tits and snap a pic of her tan-line-free perky little breasts with their incredible skin-tone-matching nipples. You play with the phone and send it to her boss. After a few quiet seconds of Jess driving with a vaguely annoyed expression and mostly bare tits, the phone vibrates in your hands.

"What'd he say?" She asks tersely.

"He says yours are much less visible..." You manage to keep quiet for a few seconds, but Jess bursts out laughing first, and you join her.

After college, Jess moved back in with her folks while she got her career off the ground, which isn't that unusual these days. Of course, with Jess's particular habits, it can be... awkward, at times. They live near the local college, so pretty much everyone around her for quite some ways goes to the school or works there (like her dad). A couple of guys who live across the street are out in their front lawn as you two drive up. Jess waves to them from the drivers seat, grinning like a fool with her tits on display.

"Oh, jeez, Jess!" You shake your head at her nonchalance, and she smiles at you.

"That's nothing." She shakes her head, "Besides, they've both seen me naked plenty, I'm sure." She smiles. "But they haven't seen you," She parks and rolls up her window, motioning for you to do the same, "Yet."

"Ha ha," You smile back, glancing at the two cute, fit guys, not totally certain you'd hate that, "As long as we don't start with jumping jacks in the front yard," You say as she opens her door, her top still up over her tits.

"Hey guys!" She shouts to them, fixing her top after a few steps in their direction. They wave back, and she gestures for you to come out.

"You're crazy, Jess." You say, keeping one arm over your 'very visible' nipples as you climb out of the car. Following her to the front door, you blush as you wave at the friendly neighbors with your non-nipple-covering arm.

"Party pooper." She says, unlocking the door and swinging it open, motioning for you to lead the way.

"Your boss certainly wouldn't say that," You smile as she follows you in, pulling the door closed behind her and following you to the livingroom.

She has big picture windows in the livingroom, but no curtains or blinds on them at all. Of course, why would Jess want that? Crossing to stand directly in front of the window, she peels off her top, baring her perky little breasts. Then she slips off her skirt, throwing them both on the table and putting her totally naked body on display. You wave out the window and both guys wave back.

"Anything to drink?" She cocks her hips, modelling the bare backside of her tan-line-free body front and center in the picture window.

"I'm good," You step around the couch and sit down, "You should go get dressed for our workout." She sticks out her tongue and climbs up the stairs, shaking her tight little butt as she goes.

As Jess heads upstairs, you hear something from the other room. Heading off to investigate, you stifle a giggle as you suddenly recognize the noise. Peeking into the cracked-open door of her dad's home office, you get a full-profile view of him sitting at the computer, hand furiously pumping at his cock.

He must have no idea you and Jess are here. You were hardly being quiet when you came in, but you didn't exactly announce yourselves either. You lick your lips, watching him, and remember being in sixth grade, having that huge crush on him, thinking about him at night, in bed...

You bite your lip. Maybe it's time to turn those fantasies into reality!

Pushing open the door, you step in. "Oh my..." You say, grinning as he jumps up, hurriedly trying to close out whatever he was looking at on the computer, dick still sticking out of his fly, waggling around wildly.

You walk up to him as he tries to tuck himself away, but immediately grab his cock, holding firm, his eyes wide. "Jesus..." He mutters, shaking his head as he stands before you, "I didn't..."

"Didn't what?" You look coyly up at him, your hand beginning to move gently up and down, squeezing him softly, "Didn't know I've had a crush on you since sixth grade?" You raise an eyebrow, lips tight. "Didn't know I've pictured this cock in every hole of my body?" He swallows as you lower yourself to your knees in front of him. "Every. Hole." You emphasize, your tight lips turning to a smile. "Didn't know how I've dreamed of tasting your cock?" You kiss his head, then slip it just inside your mouth, teasing your tongue around it. "Mmm... better than I'd even imagined..." You push back on, sliding him deeper in, your neck pushing two, then three soft strokes, your hand still gripping the base of his shaft.

You pull off, stroking his spit-slick shaft gently as you look up at him, his eyes locked on yours. "Didn't know that as soon as I spied you through that open door, the first image that flashed into my head was you finishing and cumming all over my face?"

At that instant, he bursts, a spray shooting across your eye, and you drop your hand, another burst splashing across your cheek as you open your mouth. You catch the third partly across your lips, the first of it to shoot into your mouth. You can't help but grin, leaning in to close your lips around his head, sucking softly as he fills your mouth with the sticky white goo. Your neck pumping gently, your hands on your knees, you hear Jess's footsteps coming down the stairs. As he finishes you stand, and he tucks himself in.

"We probably shouldn't tell Jess about this..." He says softly, and you raise an eyebrow, nodding, not wanting to swallow just yet. "Um, so you should probably clean off your face."

You **** back a laugh, and he smiles at you as you scoop the cum off around your lips, sucking it into your mouth with the rest, then off your cheek.

"Oh, here you are!" Your back still to the door, Jess comes in behind you, "Hey, dad, I didn't know you were here!"

"Yup. Just saying hi to Cindy." He scratches pointedly at his eye, and you grin, quickly wiping your hand down your face until it feels like there's no more left.

"Well, we don't want to bother you, let's go Cindy!" Jess grabs your shoulder, and you smile, briefly gaping a cum-filled mouth at her father before swallowing the sticky stuff down and turning to his daughter, following her out to the living room.

Jess managed to find a workout outfit that might actually draw attention away from your nipples. Her cut-off sweats are made of a tight, thin material that sticks to the curve of her flesh quite well, particularly right between her thighs. Her top fits nicely along the underside of her breasts, but is of a reasonably thick and supportive material. From here, though, you can plainly see that both of her skin-tone-matching nipples are poking out of the upper hem ever-so-slightly.

"There," She turns her back to you, her front now facing the picture window, and pulls down the very tight cut-offs, "Now I've got no undies too!" She turns around, turning her bare ass to the window, and her smoothly shaved pussy to you.

"And we both shave!" You comment. She grins, pulling the shorts back tight to her skin.

"So," She raises her eyebrows. "What shall we do?"