I Dare You

When you're a boy named Kourtney, growing up necessitates you go by a nickname merely to survive. For the first fourteen years of his life, this went well. He got by with everyone calling him by the initials of his first and middle name. When sex education began, and all his peers became hyper aware of all things sex, suddenly that went from his name to an insult. Once the context was provided, he understood why so many adults held back a snicker when he said his name was KY for Kourtney York.

Just to add a slap in the face on top of the mockery that characterized eighth grade, his full name was Kourtney York Jolley. He's called himself York ever since.

York's later life was kinder, and the joke got old by sophomore year. He still went by York though. Graduating High School as Valedictorian he felt was his ultimate redemption.

York had been physically active for most of his life and fitness is how he put himself through college. His college ride was split evenly between academic and athletic scholarships in track and wrestling. In four years he had double majored in nutrition and premed with a focus in sports medicine. He was well on his way to becoming a doctor.

Graduate school was mostly supported by his hours as a physical trainer and part time as a cross fit instructor. York started cross fit as an undergraduate and it's during which he met Heather.

Heather Calhoun, architecture student, a year younger but in the same year as him. A tight strawberry blond, short at five three with the faint outlines of abdominal muscles. Her hair typically kept at mid back length, pulled into a pony tail with one or two bangs dangling in front of her face. The girl who came to the gym in full makeup and feints annoyance that people are checking her out.

Heather saw York first. As she was completing her eleventh lap around the college's quarter mile track, she saw him shirtless completing a set of pullups, then immediately dismounting the bar to complete a round of heavy tire flips.

York had looked like he was chiseled from marble since he was sixteen. Unlike her muscles, his were carved down to minute detail from scientifically going through phases of bulking and cutting. York was the David of college guys, the kind of guy you stare at as you pass, until you clothesline yourself on the slide of a trombone from a member of the marching band moving across the track.

A small crowd formed around Heather who assured them she was fine, which she was. She was more embarrassed than anything. After one last promise she was unharmed, she turned back, and York was at the edge of the grass before the track to check on her himself.

"You good?" York asked, and Heather was silent for a second, before finally nodding.

"I do that all the time," Heather said with a forced, awkward laugh.

York looked different at the distance of five feet. Neatly trimmed brown hair that went from one side burn to the other, across the chin, to the mustache, and under the chin to complete a well-groomed beard. Ocean green eyes with a symmetrical facial structure and squared chin that was very appealing to an architecture major.

Heather looked different at this distance as well. Lightly freckled cheeks flanking a wide nose. Wide brown eyes with long lashes, a blink having the same effect as a woman calling you over by pointing a finger at you and curling it toward herself.

They had a few dates that felt forced and difficult, nearly derailing the relationship from the start. Two college kids who both count calories and pre plan meals trying to go to a pizza parlor for a date just doesn't work. It's both people staring at their meal and talking over it, wondering when it'll be over so they could get home and grill the chicken and steam their squash and broccoli.

After the second failed date at an ice cream parlor, both wondering when they can go home and eat their plain yogurt with diced fruit or berries, York offered a third option.

"I can't help but notice, we can't do normal dates," York said to her over her shoulder, running to catch up as they were passing each other in the quad on their way to separate lectures.

"You think?" Heather asked. 'Stop being sarcastic!' she yelled to herself a moment later.

"Let me cook. I imagine we have similar diets," York offered, and Heather thought for moment before agreeing.

That night he cooked hummus chicken breast baked on top of a bed of zucchini squash and red peppers. This was served with garlic couscous and a sweet wine.

"I've been living off the cafeteria salad and soup, if you want to call that food for too long. I forgot what food tasted like. Thank you, this was amazing," Heather said, finishing a glass of wine, York offering her a second glass which she declined.

"You are very welcome," York said, and poured himself a half glass and corked the bottle.

"What kind of wine was that?" Heather asked.

"A Riesling from Germany you can find at any liquor store for about twenty-five bucks," York said, which made Heather laugh.

"Look at you, big roller," Heather said, letting her sarcasm slide this time.

York offered to walk her back, but she said she'd be just fine. They kissed at the door to his apartment, and that developed into not needing to walk her home at all. The door shut with her inside, pushing him backward toward his room as he tried not to fall over objects or crash into walls. York cracked his elbow on the door frame to his room, but that was a minor discomfort.

Heather pushed him onto his bed and pulled her top off of her body, then discarded her bra on top of it. She hooked her thumbs on the sides of York's shirt and pulled upward, licking and kissing his stomach muscles as she climbed. The shirt was pulled all of the way off and she did the same on the way down, her hands arriving first to undo his zipper and pull his pants and briefs down enough to grip his already hard cock in her hand and drop her mouth on top of it.

York wanted to reach down and play with her, but the only thing in reach was her head so he kept her hair out of the way. For minutes he watched her suck his dick, the sensation of a lick or a pull occurring micro seconds before he saw it, making him flinch and gasp in shock like he was watching it happen to someone else. If she kept this up, he'd orgasm before he got to truly enjoy her to the fullest.

Not wanting to miss that, York pulled her up to him and twisted her as she fell so she'd land on her back. He kissed his way down her body, taking a few extra seconds to flick her nipples with his tongue to firm them. After he unfastened her belt and pants, he pulled them off with only a few tugs and went to the task of returning the favor.

Heather squeaked when he applied pressure to her clitoris, which York found adorable so pressed it like it was a piano key. York slid his tongue into her pussy to moisten it, then fingered her with his middle and ring ringer while he licked her clitoris. Heather was very sensitive and orgasmed quickly. York was able to provide her with three orgasms in the time she had spent trying to make him cum and failing.

After inquiring about protection that York rolled onto his penis, he entered her from missionary position, holding her legs up at the ankle and sinking his pelvis down into her. He was slow and firm in his thrusts, only increasing speed when asked to, a request she made. Within five minutes her legs were over his shoulders and he was ramming her so hard the sound of his balls swinging sounded like applause.

The position of woman astride allowed her access to her clit that she rubbed to facilitate an orgasm as she rode him and twirled her hips. He admired the way her abs looked as she twisted on him. As they began to get sweaty they admired each other more. York then flipped her into doggy style, reaching around to fondle her breasts as she continued to work her clit.

"I'm about to cum," York said mid thrust into her from behind.

"Just not my face or mouth," Heather replied. Thankfully he was penetrating her from behind, otherwise, she would have seen the visual disappointment on his face about not being able to facial her. He instead pulled out, pulled the condom off in such a way it actually made a distinct snapping noise, and jerked himself off onto her back until it began to drip into her crack.

For the next few years, he'd try and fail to put his cum on her face or in her mouth. It sounded petty, and it was, but that disappointment would never dissipate.

Near graduation, Heather did do something he expected to be amazing, but even that he felt cheated out of. Heather had meet a girl willing to do a threesome. Only problem was, he couldn't touch the other girl, but she could touch Heather and vice versa. York wasn't about to complain about a girl licking her pussy while she sucked his dick, so wasn't bothered by the arrangement, that didn't stop at a one time thing.

It happened again. And again, until he was having as much exclusive sex with Heather as he was with the other girl in the mix in some capacity. Her name was Madison Somerton. Most people called her Mads.

Mads was one of those girls who men took a look at and made bets with other men and whether or not she was a lesbian. The answer according to her was yes. Mads when compared to Heather was bigger by twenty pounds, a chubby stomach, and bigger thighs, though relatively muscular.

She had seventeen tattoos: One on her neck of a black scorpion with a tail that extended to her ear lobe; the back of her shoulders had eight small tattoos, each a phase of the moon with new moon moving into waxing crescent on her left side, a full moon in the center, and waning crescent on the right shoulder; Her right arm was a sleeve, starting with a caterpillar climbing up her wrist, her elbow a cocoon, until it emerged as a butterfly on her front right shoulder; she had a black spider web around the areola of her left breast; her left arm had a tadpole that swam up her forearm, grew legs at her bicep, and was a frog on her shoulder; the last tattoo was donkey from the movie Shrek, on her right ass cheek from a best she lost.

Mads had very short black hair that would stand two inches up if she spiked it, which she never did. She just styled it right of center. She wasn't a fan of needles of sharp objects, so didn't have any piercings besides her ears.

She wasn't bi, or queer, she was a lesbian. She didn't hate men, she even let them watch. She just didn't like them sexually. Nothing attracted her to them.

Mads is a biology major and is pursuing her doctorate while York is getting his MD. Heather was already well at work with as an architect. Not long after graduating with a bachelors, they all moved in together. Heather and York dating with Mads supplementing the fun.

This had been their arrangement for two years.

-

It looked like Heather had four arms, and York was satisfying an Indian deity. He could feel the knees of a second body on either side of his thighs, their hands reaching around Heather to fondle her breasts and massage her clit, the finger sinking low enough on occasion to touch his shaft that was entering her. Looking up he saw Mads mouth kissing Heather's neck as she moaned, tilting her head back to kiss her back.

York grabbed her free breast, only for Mads to change it up and touch his hand on accident. Instead of making it weird, she grabbed his other hand and held them both to Heather's breasts. Heather advertised her orgasm by a drastic change in volume. York moved her into doggy style began to drill her as she leaned down and licked and fingered Mad's pussy.

York tried to look at only the back of Heather, but couldn't stop the gaze up to Mad's body. She wasn't as fit and compact, but something about it. The tattoos, the extra weight that made the tits fuller and more perky. It all just felt forbidden.

Mads caught him staring, so blew him a kiss and gave him a wink that made him cum a few seconds later. He managed to pull out but not fast enough to mostly splash it on Heather's sopping slit. He felt bad because he ruined her for Mads.

"Really dude?" Mads asked, Heather now dripping with a substance Mads wouldn't touch.

"Sorry," York said, falling back onto his pillow, soon followed by Heather to hers.

"No after game tonight," Mads said, leaving the room, York following her ass, and the ass on it. It was firm, and even though her thighs were larger, light could be seen between them, and one lean would reveal her lips.

"Still dropping you off at the airport at seven tomorrow?" York asked.

"Breaking ground on my building in Denver, so need to be there to oversee that," Heather said, and York nodded and curled her up under his arm.

"Does a five story apartment building really call for you being gone for a month?" York asked, and Heather assures him it is, and tries to explain but he stops listening to say he gets it. He had plans this month.

Looking at his sock drawer, York thought about the engagement ring wrapped in a sock. He had to cancel reservations when she announced the trip, and was now considering just proposing at the airport.

York knew he loved her, and that she loved him. They have a really unorthodox relationship with Mads where definitions are incredibly vague. The more he thought about it, Heather was the one in two relationships, not him. Does that go away? Does Mads become the aunt who lives with them and sleeps in the same bed as mommy and daddy occasionally.

This proposal created many more questions than just whether or not Heather says yes.

The next morning when Heather was out of the room, the case of the ring created too much of a bulge in his pocket so he took the ring out and slid it into his right pocket before returning the case and closing the drawer. When he stepped out of his room, Mads stepped in front of him and spilled her coffee on his jeans.

"God damn that's hot!" York shouted, Mads laughing and apologizing at the same time. Heather took a few paper towels and tried off the hard wood floor of the apartment, then wiped it with a wet rag to prevent it from sticking.

"I'm doing laundry today, throw them on the pile," Mads said, and pointed at her laundry next to the machine that was in the hallway between the second bedroom and the bathroom.

York groaned and emptied his pockets, accidently pushing the ring deeper in as he pulled out his phone and wallet out. Because he was so flustered about it, he had already completely forgotten about the ring. He pulled his jeans off and tossed them on the laundry pile and grabbed a new set.

The drive to the airport was fairly quiet on York's part. Heather talked for most of the trip about her first building she got to design. Her enthusiasm made York smile. Seeing her with this much energy after her career began to see some legitimate traction. He was a year away from his medical degree. It felt like the right time to get married.

When York parked the car on the curb of the air port drop off, he popped the trunk and pulled her bag out for her.

"See you in a month," Heather said and hugged him tightly. "Love you."

"Love you too," York said and fished into his pocket for the ring, then mouthed 'fuck' to himself.

"You okay?" Heather asked, seeing frustration on his face.

"I'm fine, I'm just going to miss you," York said, making her smile and kiss him again. 'FUCK!'

"I'm going to miss you too. I gotta get through security. I'll call you when I land," Heather said, kissed him one last time then rolled her bag into the terminal.

York sat in the car, and banged his head on the steering wheel five times, each head butt harder then the one prior before he hit it low enough to honk the horn.

"How did you forget the ring!? You fucking idiot!" York shouted as he drove down the highway back to the apartment. He imagined it tinging around the inside of the dryer next to Mads bras and panties. "Fuck!"

Arriving back the apartment he ran straight to the dryer and opened it, only to see Mads had already pulled it out. Looking into his room he saw his jeans on his bed folded neatly for him. She went against the crease but that was fixable with an iron. He pulled the pockets inside out and the ring was not there.

"Where is it!?" York shouted and stomped back to the dryer and felt around, then checked the lint.

"Looking for this?" Mads asked from her room, holding the ring with two fingers. York walked over and took it from her, Mads grinning. "Holy shit, you're going to pop the question."

"I had a different plan. I had reservations and everything, but then her trip came up and messed all of that up," York explained, Mads looking at the ring.

"Nice ring. Simple, elegant design. Princess cut, you know her well," Mads said, asking to hold it again, and was handed it back. "I might have to move out."

"It would be weird if you didn't," York said, taking the ring back again and walking to his room to place it back in the box. With his sock drawer open he pulled out a pair of new socks and closed his door to change for his workout before he instructed a cross fit class.

York stepped out of his room to see Mads on the couch, not watching television but with her school work spread out on the coffee table. Mads looked up at him and shook her head.

"Why do you work out, before you teach a workout?" Mads asked.

"I don't work out when I instruct. Left overs from last night are in the fridge still if you want that," York said and left without another word.

Prior to the gym opening he completed a regiment of box jumps with burbees and lunges between. He polished that off with several kettle bell exercises then opened the gym for the students. Today's class was double unders to get the heart rate up, then eighty percent of one rep max for bench press.

There was only one shower in the apartment, and thankfully Mads wasn't in the bathroom when he got home and needed a shower. York had always showered quickly, and when he opened the door to leave Mads left her room to use the room after him. York paused at the door to ensure his towel was tight, and was blocked by Mads at the door.

"You're so cut, it's kind of gross," Mads said and York tried to step around her but she moved in his way.

"What?"

"Hold on," Mads said, walked to the washer where her second load was ready to move to the dryer. She pulled out one of her shirts and began to rub the wet fabric against his stomach.

"What are you doing?"

"My laundry," Mads said, and after a moment of thought, he got the joke, snatched her shirt away and tossed it into her face before stepping around her.

"That was funny," Mads said with a laugh then shut the door to use the restroom.

Taking the lotion from his side table he dropped the towel and began to rub the lotion into his and shoulder. He had one foot on the bed to rub it into his legs when the door opened.

"I'm ordering food you want anything?" Mads asked, saying nothing about his dick and balls dangling in front of her with his leg stretch out to apply lotion. York flinched and covered himself up. "Stop feigning modesty, I've fucked your girlfriend in the ass with a strap on while she rode you. I didn't know straight dudes used lotion for something other than their dicks."

"I'm cooking tonight, thanks though," York said and Mads giggling. "What?"

"Nothing, you're still gross. I have more laundry though," Mads said.

"Take your shirt off, it'll give you something to hang it on," York said back, and she called his bluff and started to take her shirt off. "Stop."

"You can't play chicken with me, you'll lose," Mads said, and pulled her shirt off, revealing her bra that she unstrapped and dropped to the floor. He felt like the fly about to get stuck in the spiderweb on her breasts.