It's a Hole Thing, Pt. 01

This will be at least a two part story, possibly longer. Enjoy!

Finding yourself has become about an unabashedly cliche concept in our modern parlance. It's the perfect cop out to relieve oneself from any preexisting obligation. But, this story uses this to our protagonists' advantage.

But enough ten-dollar-word stuffed preambles.

We begin in California's Bay Area. Silicon Valley, once the mecca of tech-bros and faux-cialist artists has been largely reduced to the butt of comedian's jokes of failed governance and much waxing about the collapse of technological progress.

In the South Bay (That would be the Bay Area's South Bay for all the confused Los Angeles readers out there) rests the overpriced suburb of Menlo Park. Nestled mere miles from San Jose, this town boasts high taxes, clean streets, and rents that are just too damn high.

This was the predicament found by two out-of-work tech-bro roommates: Jamie and Kenny. Both were male, twenty-five, would be readily described as nerdy, but, nerd-cute. Jamie was skinny, elfin features. Baby-faced, with piercing blue eyes, a brown curly mop of hair, which was the Gen Z style at the time, He had a lanky bod, not much muscle to be had. His nether-region wasn't much either, an average dick at best.

Kenny was a bit taller than Jamie. He was African-American, sporting a short haircut, glasses, just as scrawny as Jamie was, with a very similar physique to his roomie. His member was just as average. Both were basically hairless below the eyebrows.

Of course, where they both lacked in frontal appearance, they made up for it from behind. Both had curvy legs, and very bubbly asses. Jamie's cheeks were plump and round, with Kenny sporting a slightly more toned but still very curvaceous and feminine tushy.

Both rented a townhome in Menlo Park, a three bedroom with one car garage, and pathetic back patio with high raised wall that sported an odd feature: an in-ground hot tub; a feature that of course added equity to the property, and thus, the rent.

Jamie so desperately wanted to be one of those Silicon Valley nerds to get into the finance side of things and channel the likes of venture capitalists made famous in these parts. Kenny was a gifted coder and wanted to create the next biggest app that the guys whom Jamie wanted to channel could buy, re-engineer for a tidy profit, and Kenny goes and writes a book about his experiences and how he was ultimately screwed out of more potential money. Tis the American way.

Both became good friends while at Stanford. Jamie came from fairly rich stock raised in the Los Angeles suburb of Arcadia with three older sisters, and one step-sister, each with varying degrees of financial success and woe.

Kenny was originally from Vicksburg Mississippi until around middle school when his family moved to Seattle after his dad got a cushy accountant job and Kenny got a culture shock. He had a mild southern drawl that would escape now and then, but, he had mostly lost it. Both he and Jamie had been roommates since freshman year, so that had effectively spent their entire adult lives together. Both got employed at Cupertino-based tech companies, and both lost their jobs within days of each other when the inevitable AI bubble burst, sending the two into a tizzy of gig work, odd jobs, and economic uncertainty.

Kenny ultimately scored a plum work-from-home job while Jamie continued the path of Gen Z aimless gig work and the occasional mooching off his wealthier parents.

Their three bedroom townhome was supposed to be a two bedroom. There was the garage, living room, kitchen, and then a powder room and an office which they converted into a third bedroom. The second floor contained the other bedrooms and two bathrooms.

In order to offset the cost of living, rent, and crippling student loan payments, this is when the two decided to illegally convert the office into a bedroom and bring in another roommate.

This of course meant combing through a plethora of applications from what seemed like only the finest dregs the Bay Area could sling at them. Now, this situation could stress anyone out, but Jamie, aside from dabbling into copious amounts of cannabis, had his way of dealing with it.

Jamie was secretly into kink, specifically anything involving feminization, and humiliation. Being raised with three older sisters meant he was often subjected to wearing their clothes and makeup for fun-sies, and while he never saw a therapist, such would probably see this as a potential catalyst; not to mention, being raised with little problems, and add his already effeminate physique, and you have the makings of a future bottom.

Despite this being his kink, Jamie had few outfits. He had a few midriffs and crop-tops he pilfered from his step-sister, a pair of panties with SLUT written on the butt, and a pair of fishnet stockings. He made up for this with a more extensive collection of dildos, plugs, and vibrators. Knowing Kenny worked from home, he feared he had little opportunity to feel his oats.

One day, their first day of roommate interviews, Kenny was about to go out. Jamie heard the front door slam, and took this as an opportunity. In reality, Kenny was merely going to check the mail, where Jamie received a package.

Seizing this opportunity, Jamie threw off his shorts, threw on his panties and stockings, and got out a bottle of lube and a pink vibrator.

He hopped on his bed, his dick getting instantly hard from the rush. He slipped it around the crotch of the panties. With the lubed-up vibrator, he was in a prime position to fuck himself. He slowly forced the pink tip past his pink hole, which was more used to getting penetrated as of late. He threw on the vibrations, and gently stroked himself, not realizing the vibrations were drowning out the noise of Kenny climbing the stairs.

Jamie stroked harder as he rammed the dildo inside of him, moaning softly. Outside his door, Kenny was about to knock, but raised a confused eyebrow after hearing the sounds. So, Kenny barged in.

"Bro, are you drilling something... in... here."

The two locked eyes. Jamie blushed, not a word was spoken, the only sound was the still on vibrator. Kenny looked at Jamie in this most compromising position. He was more confused than anything, but there was something he couldn't quite shake. He snapped out of it.

"Uh, m-my bad. This-uh, c-c-cam---was in the mail for you. Oh uh, that guy, uh, what's-his-name is uh, g-onna be here in like a half hour, just uh... put something on."

Kenny hastily left the package on Jaime's desk, and promptly left. Completely embarrassed, Jamie fell on the bed. Fuck.

A half hour later, Kenny, and a more masculinely clothed Jamie sat in their living room on two easy chairs opposite one another, flanked by two couches. It would have made more sense for the two of them to sit on one couch next to one another, but the incident was living rent free in their heads.

Speaking of rent, on one of the couches sat Todd, an aging, full-figured, former quality control analyst for a tech company that laid him off after twenty years. He was balding, with a poor combover, sweaty, wore glasses, and an ill-fitting button-down and the ugliest tie he could find.

Confused, Todd looked at one, then the other while speaking.

"So, um, I uh, I need to reiterate that this application contains no, and I mean no credit check, right?" Todd asked.

No answer. Jamie was busy looking anywhere but Kenny, who couldn't take his confused thousand yard stare off Jamie.

"Huh, what?" Kenny snapped out of it. "Oh, nah, no credit check as long as we can see six months worth of pay stubs."

"Well, I, uh, I have it on the phone here, I drive Uber now--good honest work, business has been slow, but uh, I-I have a couple of job interviews lined up."

Todd droned while Kenny looked back at Jamie, extremely despondent. His memory kept on going back to that moment, watching his friend he knew on the down-slope of ten years fucking himself half in drag.

"Now, where do I keep my ass?"

"What?" Kenny snapped out of it again.

"My sax. I play jazz sax. Any of you guys play?"

Kenny shook his had. After some more tedious conversation from the closest real-life example of Gil Gunderson, the two bid Todd a fair well, who seemed like it went very good for him.

"You guys have my number!" He called. "Can't wait to get out of that Home 2 Suites!" They slammed the door behind him.

Jamie held a list of names on a file on his tablet, he scrolled a line past Todd.

"No. Fucking. Chance."

Jamie tossed the tablet on the couch and hurried to the garage. Kenny paused for a minute, then followed him. Inside the garage contained Kenny's car, and their washer/dryer. Jamie opened the dryer, a hamper waited above it for him. Kenny stood in the doorway.

"So... like... what in fuck was that?"

"That was a guy who will not be playing his jazz sax in our converted downstairs bedroom." Jamie murmured.

"You know what I fucking mean, J." Kenny crossed his arms.

Jamie sighed, hung his head, and looked over at his roomie. "I thought you left."

"To get the mail. And to drop off a package left for you--you're welcome, by the way, and it's not like we didn't know we had that interview scheduled. So, who gives a good fuck about you thinking where I was, I refer to my original, still unanswered question: 'what in fuck was that'?"

Jamie put his head in his hands, leaned on the dryer. Kenny took a step into the garage. "Alright. I... I was fucking myself. I was wearing panties, and fucking my hole with a vibrator, and jerking off to it."

"In fishnet stockings."

"Yes, in fishnet--... fuck you very much."

Jamie hastily threw his clothes into the hamper. Kenny blocked his way. "Dude, we've known each other for like... seven, eight years, all of those years we've lived together. I don't care what you're into, I dunno, I just thought you'd tell me about it, or something?"

"That I dildo my ass in panties? C'mon Ken, that's some 'take that to your grave, alone' type of shit."

He tried to bypass Kenny, no dice. "Talk to me, J. No shade, no shame."

Jamie sighed. He stowed his laundry upstairs and the two adjourned out back. Aside from their random hot tub, only a small outdoor table and two chairs were the only objects in their patio area. Jamie, reached for the table, on it is a small cigarette case, lighter, and an ashtray with two nubs filled with mostly spent roaches. He opened up the case, three rolled joints awaited him. He tossed one in his mouth, lit up, and took a hearty drag. There was a silence, while the high slowly began to overtake Jamie. Kenny stared blankly, a glass of ice water in his hands.

"It's not personal, Kenny." Jamie snorted, then coughed. "I've never told this to anyone. No online chatroom, no girlfriends. Nobody."

"So, like, what would you call that, exactly?"

Jamie shrugged, took another drag. "I dunno. There's just something liberating to me about getting poked in panties."

"Do you like... men?" Kenny asked.

Another shrug. "Sure. I like women too. Trans people."

"Think that's pansexual?" Kenny pointed, took a sip of his glass.

"Yeah. I figured that out about myself senior year."

Kenny sighed. "This is not a deal-breaker to our living together, or friendship... but... would you fuck me?"

"I'd... probably sooner have you fuck me. I'll never ask, so it never has to be that awkward. I'll keep my staring at your ass to a bare minimum." Jamie chuckled.

"Thank God for that. You ever get fucked by a dude?"

Another drag. "Nope. Never been penetrated by a real. Only had two girlfriends my whole life, only one so much as fingered me one time. Guess I coulda' said something, she was kinda freaky."

More silence, Jamie took another long drag. Kenny could see a boner forming in his roommate's shorts, probably from the frank sexual discussion. He looked at himself. Shit. He was getting a chubby. But why?

He liked women. He knew he did. But, why, oh why, could some part of his brain not let this Jamie-thing go? Oh right. Their predicament. Of course!

"Look, J. I'm glad we had this heart to heart. Reason I uh, wanted to parlay on this is cause', we got a problem."

"The roommate thing, I know, I know, Kenny."

"Do you? We got damn near two dozen applicants to comb over."

"No fucking, duh. Economy is dog shit and our place is reasonable for what it is."

"Background checks, pay stub confirmation, credit checks--"

"Kenny--"

"I've been doing this shit solo while you're busy getting it on with yourself!"

Jamie snarled. "So, that's it? Pry me for my deepest, darkest secret, just to chew my ass out?"

"Grow up! Deepest darkest -- we are already one full months rent behind. We got two good months left, we gotta pick one of these duds by week's end else we gotta go move back in with our folks!" Kenny reminded him.

"Can't. They sold the house, moved to some fifty-five plus down in some shitbox near Tampa."

"Your mom, then?" Kenny suggested.

"Two of my sisters are already living in her two bedroom apartment."

"So, we know the stakes, right?"

Jamie took another drag. "I'm handling it. That five-time loser wasn't it, though."

"Agreed. One down, nineteen to go." Kenny's eyes found themselves on Jamie's boner, unfortunately for him, Jamie noticed. "Don't flatter yourself. I love you too much to ever just rail you in your sleep."

"Why'd your brain go there? Freaky bitch."

They shared a chuckle. Jamie took a weak drag, coughed. "Seriously, you never get high? Ever?"

"Don't drink neither." Kenny winked, taking a sip.

"Yeah, I've seen."

"Addiction runs deep on my momma's side. Promised myself I'd be clean for her sake."

More silence, both men had eyes on the other's tentpole. "Look, I can admit my kink. What's your excuse?" Jamie asked.

"I dunno, it's all this tension and shit. Fuck it, we need to move on from this."

Kenny put his water on the table, stood up, and dropped his pants and underwear, revealing his half hard cock.

"What are you doing?" Jamie asked.

"Breaking the tension. Proof we can... you know, be adults about this. Take it off."

Jamie was confused. He took a look at his joint, then took one last long drag, setting the roach in the ashtray. He stood up, and lowered his pants, fully erect. Both men stood side by side, looking behind one another.

"We have the girliest asses in the world, bro." Kenny commented.

"Yeah, I know. So, like, what was the point to this exercise in awkward? Bottomless ass-staring?" Jamie asked.

"Uh, tension breaking."

"Nothing personal Ken, but it seems like pressure's building."

"I'm not gonna fuck you, dude."

"And again: no one's asking you to! This was my secret and I was fine with it, as is! You keep bringing it up, raising the stakes and bringing it back around to us finding a roommate."

"It's important, Jamie! You being all distracted with your pantyhose and dildos is going to cost us this house!" Kenny boomed. After a beat, he pulled his shorts up. "Fuck yourself. I gotta go grocery shopping." Kenny stormed off.

Jamie sighed. "We need TP!"

Kenny got in his electric vehicle and stormed off. He drove around town for what seemed like hours. Night had fallen. There was something Kenny just couldn't shake. His head just kept going back to how annoyed he was at how unserious Jamie took to adulting. Never mind the sexual proclivities, he hadn't had any real work in quite some time, he was usually high, and routinely neglected any pre-existing obligation he had. This was actually important. This, Kenny assured himself was why he stormed off in a huff.

It was now really late. Kenny found himself at his favorite twenty-four hour discount grocery store: Schmendricks, because no self-respecting real-life super market would ever want their price-gouging name in this story.

Kenny was no Michelin-starred chef. Ironically, cooking was one area Jamie excelled. No, Kenny's diet consisted of only the finest pre-packaged frozen poison one could easily microwave, or toss in your favorite metal-chipped skillet with just one glug of olive oil.

Kenny's piddling cart consisted of frozen dinners, off-brand soda, and...

"Dammit. TP."

At Shmendricks, you had your choice of one or half ply. Being frugal, Kenny reluctantly chose the latter.

Save for a few near-zombified employees who looked like they were one pay cut away from making 'going postal' a mood, Kenny was the only one in the store. Even the elevator music pumped into the store was cheap and sterile.

Kenny made his way to self-checkout, except, all were either closed, broken, or somehow miraculously; both. He put his hands into the cart and made his way to the only checkout counter with a human behind the till.

Her name was Ivy. She was fun-sized, nerdy looking, early-to-mid thirties. Glasses, a few piercings, strawberry blonde hair in a ponytail. Work outfit with apron, big boobs, hourglass frame with a round plump ass. Kenny was not aware at that particular juncture but Ivy was trans, whose dick was if not bigger than his, definitely more round... definitely bigger than Jamie.

Ivy put on a big, fake smile, and spoke in a falsetto voice. "Welcome. Did you find everything okay?"

"Somehow, I always do." Kenny sighed, placing his various junk onto the conveyer belt. He scanned through the tabloid magazines which had even more bizarre and libelous headlines than the usual supermarket rag.

"Would you like to use your cheapskate card? Average savings is three and a half percent?"

Kenny dug into his pocket, took out his keys, and held up a keychain grocery store rewards member card. Ivy scanned it. Kenny threw his keys back into his pocket, and his eyes scanned around from the braindead magazines, to the supermarket drudgery, and finally on Ivy, who at least had a nice set for him to casually gawk at while she scanned his items.

Tits. Kenny thought to himself. Finally, something to take my mind off you-know-who. Not that I needed that, but, damn, double d's.

"Do you have our digital coupon for the Schmendricks Fresh Frozen Orange chicken?" Ivy asked. "You get two more free."

"That would involve returning back into that place I'm sure y'all have convinced yourselves is hell."

There was a pity chuckle. "Frozen section?"

"Nah, I meant the whole store."

"Oh yeah, the fun and nuanced world of grocery retail is always a huge thrill." Ivy mocked. She kept scanning, getting to the toilet paper. "Half ply? Jesus, Whose tush are you punishing with this dreck?"

"Mine, and my roommate. Self-preservation and frugality aside, his ass deserves it. Pardon my French."

"Sounded like English." Ivy quipped.

"Now look who's making jokes?"

"You are aware, less coverage equals more product used... thus, frugality loses." Ivy reminded him.

Kenny was about to quip back... but son of a bitch. She was right. "If I told you I graduated from Stanford, would you believe me?"

"If you went right for the non-existent Schmendricks soft and absorbent, no, I wouldn't." She kept scanning.

Their eyes stayed on one another. Kenny felt relieved, a small chubby was forming in his shorts. Whew, he thought, homo-erotic crisis averted... right?

"Roommate tussle, eh? None of my business, but drinking the local tea is about the only benefit this job affords me."

"No tussle... a spat, you'd call it?"

"Lovers quarrel?"

"N--wait, what?" A defensive Kenny asked.

"Shmendricks Own double-dipped chocolate chunks. Lovers quarrel: cherry and dark chocolate. These are my fav." Ivy beamed, holding up a box of chocolates Kenny was treating himself to.

He sighed of relief again. "Oh, well, they are pretty good."

"But seriously. I'll put my fake therapist hat on. It's way late, and I'm sure you'd rather be home... but me thinks something about this 'spat' is wanting to keep you from confronting it?"

"Dr. Melfi over here."

"I'm just saying, love. You can't hide out in a drab discount supermarket forever."

Kenny facepalmed. "Ain't that the truth." He looked up and saw Ivy staring intently at him. He sighed. Screw it. Odds are, he'll never see her again, at least in a setting as intimate as this, and who says he has to get graphic?

"Financial insecurities." Kenny began. "We were in tech, now we're not, rent's still due. We have renovated some space into a bedroom. We're tryna' find another roommate; which has become a whole thing. My roommate is... very... distracted, and I need him to get his proverbial head out of his proverbial ass and help me else we're gonna be on the street."

Ivy shrugged. "Hobbies can help focus."

"Believe you me, he got one, and it ain't helping."

"Drugs?"

"Weed mostly, pills now and then... actually not really since college, but the boy does smoke like a factory, sometimes."

"Tell him to put up or shut-up?" Ivy asked.

"Till I'm blue in the face. Deaf ears." Kenny shrugged, annoyed. "And now..." he trailed, stopping himself, lest he reveal too much.

Ivy leaned in, hanging on Kenny's every word. "Now...?"

Kenny paused, facepalmed again. "It's not really a-a-a topic to be spoken in polite society."

Ivy boomed. "Eeeee! Tell me, tell me, tell me now!"

Kenny groaned. He looked around, literally they were the only two people in the store it seemed. Certainly the only ones within earshot. The soulless music was the only noise for a few beats while Kenny confirmed it was only them around.

"Alright, he's a kinky guy. But, see, I didn't know about it." Kenny whispered

Ivy muffled her screams. "Oh my God! Every. Detail. Now. Please."

Kenny shh-ed her. "You got the headline, now read the matter." He insisted. "I knew him since college, we been roommates ever since--ever. But today, I walk in on him... I walk in on him..." Kenny trailed.

He stalled. He looked at Ivy leaning in with baited breath. He couldn't do this, betray Jamie's trust and let his secret out, even if he was upset with him.

"No, I can't. J-J-Just ring me up."

"No-no-no-no-no-no." Ivy begged, hands clasped. "You can't leave me like that."

"I seem to recall you saying "none of my business", ring a bell?"

"Please-please-please! I'll go on break, we can talk it over in your car, no one around!"

"I said no."

"Comp your groceries?"

"You can't do that."

"Fine. Mr. Picky." Ivy reached into her pocket, and pulled out a wad of bills. Kenny was surprised. "I seem to recall you saying "financial insecurities", ring a bell?"

"I'm no whore." Kenny snapped.

"For a story?" Ivy questioned. "Five hundred."

"No."

Ivy groaned, and counted out the bills. "Nine... sixty. That's literally all I have right here." Kenny scratched his chin, mulled it over. Ivy sighed heavily. "And I'll comp your groceries."

Kenny smirked. Moments later, Kenny and Ivy sat in his car. Kenny rolled the windows up. Ivy held up a weed vape. Kenny shrugged. Ivy rolled her window down a crack, took a puff.

"They gonna miss you in there?"

"Please, I practically run that bitch." She reached into her pocket, handed Kenny the money. "Now then, you walked in on him...?"

"He was on his bed, legs spread---legs in fishnet stockings, and a waist in panties, one hand jerking it, the other shoving a dildo up his butt. Satisfied?"

"Hmm, feminization, you say?" Ivy quipped. "Shoulda' guessed, that's practically boilerplate for the garden-variety tech bro of the now. Why was that so hard? Shame on me for losing nearing one large on that nothing-burger."

"Nothing-burger? Girl, this ain't some drifter I picked up yesterday, this is my best and only friend of nearly ten years." Kenny explained.

"And you're upset that he hid this from you, right?"

"Well, yeah, b-but it's more than that."

"You wanted in?" Ivy raised an eyebrow.

"Fuck no, my whole entire fucking point is-is not the what. The what is a massive distraction from our situation that he refuses to take seriously!"

"Jesus, how many times a day is he doing himself?" Ivy asked. "If it's consuming that much of his life--"

"I don't think it's all day all night, buuuuuut it's enough. I need him-us to be a unit, not me doing most of the work."

Ivy smirked, listening to Kenny stumble over his self-righteousness. She glanced down at his shorts, a boner was definitely forming. She took another hit from her vape. Kenny looked over at her.

"What?"

"Did I say anything?" Ivy asked

"Your face is so loud it could stop a rock concert."

"While I'm sure this news adds to your roommate's distraction, you've said so yourself there are other things. Pot, right?" Another hit.

"Yeah, so?"

"Why is this event getting all your attention?"

"What do you mean?" Kenny asked.

Another hit. "Oh, come on, Mr. Stanford, I gotta spell it out for you?"

Kenny narrowed his eyes. "Put that shit away and listen to me very closely." Kenny demanded. "I. Do. NOT. Want. To. FUCK. MY. ROOMMATE!"

"Don't need to convince me. I'm just some gal who bags your groceries. Look, real talk, you got three options..." Ivy began, holding up three fingers with perfectly manicured nails. "One: start fresh, bite the bullet, go your separate ways. There's clearly tension and if this is how you're gonna carry it, it shall only spiral, and the end result satisfies no one. Two: embrace it, use his kink to your advantage, you might feel the stress fall off and maybe he will find the will to not be a lazy twink."

"No, and definitely no."

"Well, that leaves only three: look yourself in the mirror, man-up, and find some way to meaningfully live with it in a mature manner while gently pushing your roommate to do the same."

"Tried that."

"How well?" Ivy asked. Kenny mulled it over for a moment, shrugged. She had a point. While he looked away, Ivy took a peek at Kenny's tentpole. She herself was starting to form, and she crossed her legs.

"It wasn't like Jamie was begging for my dick." Kenny sighed. "Three it is."

"Your hour is up. That'll be nine-hundred and sixty dollars please?" Ivy smiled holding out her hand.

"A fu-fu-fu-fuck you." He gently flipped her off.

Ivy scoffed at him. "Listen, I don't want to get all up in your pseudo-macho head-space about your preconceived rejection of gay love, but, you're young, your twenties are prime time for experimentation, would it please the court to one-night stand the guy just to get this piano off your back?" Ivy asked.

Kenny crossed his legs. "I-I really don't think I can."

"Your shorts say otherwise."

"I just... can't get past that."

Ivy sighed. She looked over at Kenny, giving him a little once over. She scratched her chin. She shrugged. "I saw you staring at my breasts. Fair to say you may or may not have some attraction to me?" Ivy asked.

Kenny got defensive. "Hey, look, I--"

"No complaints. You're cute. Nerdy guys are my type."

"Mine too--women, nerdy women."

"But what if I told you..."

Ivy sat herself up, and unzipped her fly, after some finagling, she pulled out her flaccid member. Kenny's mouth dropped.

"Surprise."

He was stunned. But, now his dick was ready to jump out of his pants. Literally Kenny couldn't speak even if he wanted to. Ivy smirked, and zipped her dong back inside her pants.

"Your orange chicken is melting. Spoiler alert: it's mostly sinew and bits of sawdust. My shift ends in an hour. If you're serious about working this out with your roomie, I'm willing to help you... but it's definitely going to involve some tushy stuffing and mini skirt wearing on your parts. The dunes past Willow and the Expressway. Hopefully I'll see you then." Ivy gave a kiss on the cheek and left the car. A stunned Kenny watched her bubble butt walk away. Kenny laid his head on the steering wheel. His dick dripping.

He returned home. It was super late. Kenny quickly stuffed the packed freeze full of more processed poison. He filled the empty toilet paper rolls in both bathrooms, lazily leaving the bag of TP in the upstairs hallway. He threw his hands on his head, looked at his smart watch, about twenty minutes went by. Kenny stood at the hallway edge near the stairs, which was open to the first floor below. He stared at the walls above the living room, seeing two spider webs on the top corners.

He mulled this over. He couldn't deny it, until he saw Ivy's Johnson, he could have fucked her on the spot, and that's even counting her persistent prying into his personal sexual dilemmas.

Still, nerdy hot trans-woman aside, Jamie still crept his way rent free into Kenny's mind, yet again. A boner slowly built in his shorts. He sighed.

"Learn to live with it." he whispered, then huffed.

He walked over to Jamie's room, and knocked this time, the door was ajar. Kenny heard a grunt. Good enough for him. He opened up. The place reeked of weed. Pop music played on a smart phone. Jamie was in bed. Face down, but turned towards the room. He had on a midriff, and his stockings, but nothing else. His ass was up, the base of a blue butt plug stuck out of his crack, hugging his cheeks. Kenny's eyes locked onto Jamie's round plump orbs. He snapped out of it, grabbed Jamie's computer chair, and sat next to him by the bed.

"Get the TP?" Jamie slurred, half-asleep and eyes beet red.

"Yeah, I got the TP, don't you worry your pretty little lazy head about it."

"Come to insult me some more, huh?" Jamie asked.

Kenny sighed. "Not entirely, but will I ever miss a chance if one slaps me across the face? Hell no. Seriously, I mean this: we are going to move past this."

"How?" Jamie asked.

"I'm working on that. Safe to say, your kink is welcome in this space."

"Joy." Jamie deadpanned.

"You don't believe me?"

"You yell at me. Insult my maturity, then you cock-bait me; mind you, I made no advances nor solicitation in any meaningful way towards you, then you spit in my eye when I confront you on it."

"Don't mean you can't do you, bro." Kenny promised him.

"With all due respect, my friend, your word isn't much to me right now on anything."

Kenny sighed, facepalmed, then looked at his watch. He looked at Jamie for a moment, his glance back to his roomie's rear. His chubby erect for Jamie to see. There was no hiding it.

"'Aight, I'm in a rush and want us to settle this like men, what's it going to take for us to at least squash this night's beef?"

Barely awake, Jamie raised an eyebrow, and strained himself to look at his smart alarm clock. "Rush? It's two-thirty in the morning."

"Never you mind what my schedule looks like. What'll make you take my word?" Kenny asked.

Jamie shrugged. Fuck it. He shook his cheeks. "Make an honest woman out of me."

"Try again." Kenny crossed his arms.

Jamie snickered. "Cum buns."

Some blush. "You want me to spank off on your booty?" Kenny asked.

"Yes, doctor, I do declare that is the definition."

Kenny shrugged, but made a dramatic snarl. "Fine."

"Seriously?"

Kenny dropped his pants and waddled over so his cock was perpendicular to Jamie's awaiting ass. He started to jerk it.

"Yo, Ken, I was joking."

"Fuck yourself, you knew you weren't."

"Okay, fine, but I-I-I didn't think you'd do it."

Kenny kept stroking. "You thought wrong, bitch."

His brain went right to thinking about Ivy, whose hanky-panky rendezvous he was most likely now going to be late for. His brain kept on her, and her rack, but yet, his eyes couldn't take themselves off Jamie's cheeks.

Kenny huffed. "Sp-spread them for me."

"Yeah, you bet."

Jamie reached his hands around back, and spread his ass wide, revealing his hairless pink hole stretched around the plug. Kenny bit his lower lip as the constant edging made him ready to burst, and it didn't take long from there, He grunted, and let out a shot, right across the bow, landing diagonally in Jamie's crack. Jamie let go of his ass, and Kenny shot two more loads, each landing slightly closer to himself but still on Jamie's cheeks. The last dripped right down Jamie's hip. Kenny stopped, and looked at his pearly spunk dripping so beautifully on Jamie's tushy, the overhead light catching the ropes of cum perfectly.

Kenny sighed, took another moment to admire his work, then pulled his shorts up. "Gotta go, bro." He quickly darted for the door, but saw the open box from earlier, next to it was its contents, a green vibrator, about five inches by two inches, two double AA batteries were next to it, Thinking fast and thinking horny, Kenny grabbed the dildo and batteries. "And I'm borrowing this!" He ran out, slamming the door behind him, leaving a befuddled Jamie in a puddle of his roommate's cum and confusion.

Kenny hopped in his car and sped away, not at all thinking of tomorrow's inevitable conversation with Jamie of the last eventful fifteen minutes. But his mind was definitely elsewhere, and that elsewhere was offering him gratuitous intercourse, but in a more taboo setting... while he had the thought of also being offered gratuitous intercourse in a perfectly safe and intimate setting moments earlier, Kenny put that thought out to pasture.

He was vaguely familiar with Menlo Park's dunes. A long stretch of marshy terrain jutting out into the south Bay. He parked the car a safe and legal distance away and walked the dunes, a line of earth between a still estuary. At some point, he was pretty far out, and was about to wade into a marsh, surrounded by shrubs. He felt a presence.

"Boo!"

"Gah!" Kenny turned, it was dark but he knew it was Ivy approaching. The moon was nearly full so she was lit once she got close enough. She pointed to her watch and shrugged. "Que pasa?"

"Taking your advice. I'm gonna make it work with my roommate, but, I need to take it slow."

"I thought you needed this squared away due to your financial troubles?" Ivy asked

"Yeah, and by slowly, I mean, in about a week."

"Then we best get started."

"If it makes you feel any better, I came on his ass before I got over here. Hence me being late."

Ivy's jaw slacked. "What the fuck? Here I thought we were going to have some fun." She pouted.

"Hey-hey, I got more loads." Kenny assured her. "That's the easy one too, my thing's been ebbing and flowing all night."

"Lucky me." Ivy rolled her eyes.

"What? I'm surprised no quip about me doing a sex thing with the guy I swore up and down I wouldn't have sex with?"

"Okay, no shade, sweetie, but you're about as predictable as a butt funnel making an appearance at a frat party, and, no offense to your openness, but, in the grand hierarchy of kink, cum buns without any sex preceding it, is pretty innocuous." Ivy explained.

"You here to coach me, or fuck me?"

"Hmm-hmm, cutie, if you don't already know the answer is both, I've already failed you."

"Whatever. Any particular reason we're out here and not at your place, say? Hell, or my place for that matter?"

"I don't invite strangers into my house, and, you invite strangers into your house?"

"Okay, but the fucking dunes?"

There's an eerie romance to it. Dontcha' think?"

"I think, were out on the fucking dunes about to have our dicks out." Kenny deadpanned.

"Then we best get to it, then, shouldn't we? Pants off."

Kenny dropped his shorts. Ivy did the same, both had their dicks, nearly hard. "Done and done."

"I'll suck that cock of yours while getting a finger inside of you to start you off easy."

Kenny shrugged. "I like that."

"As for me, you have two choices, each will involve my jizz on your pretty face. You can simply blow me, or..." Ivy turned around, sticking her ass at him. "You eat my ass, then I jerk off on your face."

"Sign me up for some ass-eating." Kenny shrugged without thinking.

"Hmm, that decision came quick."

"Never ate a dick before, but I your ass is pretty."

"I'm gonna like you."

Ivy sauntered over and knelt down in front of Kenny. "She stopped. "You know, I am inches from giving you a world-class BJ and I don't even know your name. Where are my manners?"

"What's good? Name's Kenny."

"Ivy, but you knew that, you saw the name-tag." She planted her hand right at Kenny's shorts, where the dildo was sticking out. She grabbed it. Kenny shrugged.

"There was no game plan. I just brought it, thinking... I don't know what I was thinking."

"Chekov's dildo... we'll Definitely use this." Ivy smirked.

She reached for her bag and pulled out a bottle of lube, drizzling a liberal amount all down the shaft. Kenny had put the batteries in it some time before his journey to the marsh.

She dropped the dildo right into Kenny's downed shorts and started to lick just the tip. Kenny moaned as his erection had Ivy's attention. She slowly licked around, until finally slowly sucking it in, using her lubed hands to jerk him.

After a moment she stopped briefly. "I hope you're watching, cause there will be a test." She winked and got right back to work.

She sucked down a little harder, getting deeper and deeper on his cock with each suck. She took this opportunity to use a free finger to slowly go and find its way to Kenny's hole, and it slid right in. Kenny grunted. It was a strange feeling, but nevertheless a good one.

A moment later, Ivy slid another finger inside of Kenny, while sucking as deep as she could. Kenny looked down and watched Ivy with her lips basically touching his crotch.

"So..." he moaned. "You gonna put that dildo in me, or what?"

Ivy released, a thin line of spit went from his tip to her lips. "I'm liking the eagerness."

She went right back to work, taking her other hand out of Kenny's ass and grabbing the dildo, She rested it by his hole, it was stretched out just enough for her to slowly inch it's way inside of Kenny's formerly virgin ass. Kenny grunted, after the first inch or so, his rectum accepted the rest. Once it was in, Ivy turned on the vibration and jabbed it inside of Kenny. He grunted, as Ivy had her mouth deep on his cock.

"Gonna... cum--fuck." Kenny bit his lip.

He came, and with the same force as the one from earlier. Kenny moaned as he could feel the shots going deep inside of Ivy's throat, she kept on sucking, taking in every last drop, not a morsel was missed.

After a moment or two, she released. "Not bad. But you keep that baby in your tushy until we're through, you need to get used to taking some dick." She ordered. "Kneel, please."

Kenny nodded and got down on his knees, his hand reaching around, keeping the dildo inside of him.

Ivy stuck her ass right into Kenny's face. Ivy had one hand spreading a cheek, the other stroking herself. Kenny used a free hand to spread the other cheek, he stuck his tongue out and licked around Ivy's bum.

"Ooh, good work." Ivy moaned.

If only Jamie could see him now... he'd be jealous, which in some small way pleased Kenny. He kept licking around Ivy's hole while she was definitely getting close. Right as Kenny used the tip of his tongue right at her opening, that did it, Ivy was ready to fire.

She turned around quick and a fresh shot of cum hit Kenny right in the face, then another, then another, the last drops hit the ground. A tiny bit hit Kenny's glasses.

Before Kenny could quip about the lukewarm jizz on his face, Ivy bent down, licking it all up herself, even on his glasses, before giving him a kiss, snowballing some residuals into his mouth. Kenny gulped down the backwash.

"Good start. I'll be at register seven for tomorrow's shift." Ivy said before grabbing her things, then turning around. "There's a sale on Schmendrick's prepackaged fruit salad! It'll make your cum taste better!" She shouted a bit too loudly, nearly out of eye shot.

Exhausted, and completely turned on Kenny fell to his side, finally taking the dick out of his ass. He looked up at the moon and starry night sky, baffled at the day's events.

That next Kenny had an uneventful and monotonous day at work. He kept shifting in his computer chair, his ass sore from being stretched the night before. He kept to himself, even on his meal break, doing everything he could to avoid Jamie.

Unfortunately, after work the two had roommate interviews. Kenny made sure to enter as he heard their doorbell chime so as to avoid any awkward face time with Jamie until the day's interviews were over.

This time, Jamie and Kenny sat next to each other on a couch, opposite them were twins Whitney and Quinn Philbrickensham, both about thirty-five, with unkempt hair.

"We have reservations about the--" Whitney began.

"--Bathroom situation." Quinn finished their sentence.

Jamie and Kenny gave a small glance to one another, their tell that this was already gonna be a hard pass, but, they weren't going to be intentionally rude.

"There's a half bath right next to the room you'd be renting." Jamie explained.

"But, no shower." Whitney added.

"You can just knock, one of us would gladly let you use our shower." Kenny explained.

"we're friendly guys." Jamie added. Kenny smirked.

"I thought I saw something about hers and hers sinks?" Quinn asked.

"We get ready for work at the same time." Whitney added.

"Again. Friendly guys. Just give a knock." Kenny reiterated.

"As we are two." Quinn began.

"And each of you are one, why can't we have the room with a shower?" Whitney added.

"We also both like to shower at the same time." Quinn continued.

Out of patience, Jamie and Kenny gave each other a deadpan look, then turned back to them.

"Oh, darn." Kenny said.

"It appears that the..." Jamie added.

"... Offer has expired." Kenny continued.

"Thank you for your interest."

"And we wish you the very best of luck."

Then in unison they both said. "Forever, and ever, and ever." So, maybe they were a little intentionally rude.

Moments later, the twins left in a huff. Kenny slammed the door shut, and locked it in two places.

"At least Mr. Jazz sax probably wouldn't watch us sleep at night." Jamie groaned.

"Suck it up, buttercup, we got three more today. Kinda sucks though, double trouble means double rent." Kenny sighed

"Nooooo, that means two paying half their end of rent."

Kenny stopped, realizing he just had a senior moment. Fuck, was his mind ever elsewhere.

"So..." Jamie finally asked.

"Yeah?"

"You gonna stop avoiding me and talk about last night. I was fucked up, not passed out."

"Did it make you feel any better?" Kenny asked.

"A little."

"Good."

"But like... what does it mean, Ken? What does all this mean? I'm getting the absolute worst mixed signals from you, and I am not exaggerating."

"It means, I want to do what I can to help you get passed our awkward so you can best focus on what needs to be done about our finances."

"Well fine, I would like my ass fucked."

"And I'd like to win the Powerball." Kenny countered.

"Alright, I promised myself I wouldn't ask you, but, circumstances seem to be... kind of changing?" Jamie shrugged. "If you can't see yourself fucking me as me, what if... what if I went full drag? Wig, makeup, the whole bit. It'll help me focus, big time."

"I'm not going to give you a definite answer. But, if I don't see some credit checks, it's a definite hard pass. Signal clear enough for you?" Kenny asked.

Before Jamie could interject, the doorbell chimed. "To be continued."

"Ah, sweet music." Kenny chuckled.

The next two interviews were a veritable cavalcade of creepy and destitute, with the right amount of pathetic to gently smooth over the creepy.

So far, all their perspective roommates were not panning out. Twas later, and Jamie was making dinner. He was at the stove while Kenny was at the breakfast nook.

"By the way, since I don't have to hide this shit anymore, where's my dildo you "borrowed", the one from the package?"

"Mine now, and it's up my ass." Kenny joked.

"They're not cheap, Kenny."

"I'm guessing you have plenty. Besides, it's being put to good use."

"Probably threw it in a landfill somewhere." Jamie muttered under his breath. "Stupid jerk."

"Beg pardon, roomie?"

"Ugh, we're out of heavy whipping cream." Jamie quickly countered. "I was going to make eclairs."

"I got you! To Schmendricks!" Kenny quickly grabbed his keys and wallet, and darted for the door, as if Jamie wasn't already confused over last night.

"What the fuck." He groaned, going back to cooking. "Gotta be the only organism in history happy to be going to Schmendricks."

At the supermarket, Kenny got the one thing he came there for, and made a beeline for register seven, where a seemingly disinterested Ivy was lazily flipping through a magazine.

"Welcome! Did you find everything okay? I'd like to remind you, our valued customer, about our sale on Schmendricks fresh fruit salad."

"Just this here borderline expired heavy whipping cream and a moment of your time."

Ivy looked up. "That wasn't just canned cashiers banter."

"And that shit gives me the hot poops. What else'll make me taste better--not that you, or my roommate particularly deserve me at my most delicious." Kenny quietly huffed.

"Oh, by the way you've described him, he can go fuck himself, which by now I'm sure he probably is, but uh, I would like you to taste delicious." Ivy snarked. "Pineapples are pretty good, but dear God, get them from someplace else."

"Message received."

"Also, I'm going to need all your measurements."

"What for?" Kenny asked.

"Might be psychological, but, me thinks you'll stop the macho head-games if you were dressed a bit more daintily. Also, we need to invent a reasonable pre-text for me to come over your house, I want to get a look at this Jamie of yours."

"Ah, that's no trouble, we doing roommate interviews right now. But uh, what happened about the whole strangers thing?" Kenny asked.

"That was before we swapped fluids and you acquainted your tongue with my tushy. Alright, I'll fill out an application. Not that I need a new place to live."

"Girl, and I know I'm speaking for the both of us, but we wouldn't mind you being around every day to fuck us both."

"Oh, I fully intend on fucking you both, what I need is you two being comfortable to fuck each other. That'll fix all your tension." Ivy explained.

"So, what's tonight's "lesson" gonna be?" Kenny asked.

"Eager, aren't we? Measurements, measurements."

"No sex?" Kenny asked.

"You want sex? Train yourself on that dildo of yours. Right now, I wanna see some--"

"--Measurements, yeah, yeah, yeah."

"Pay for the cream." Ivy hissed.

"Already feel like I'm paying for your cream. You uh, didn't ask me for my cheapskate card." Kenny smirked, holding it up.

Ivy sighed, flipped him off, then scanned it. "Ooh, you saved thirteen cents. Whoopee."

"What's this attitude? You couldn't wait to jump on me last night. What gives?"

"Foreplay's over, guy. I want you and roomie to rest up, cause what's coming next ain't food play and anallingus."

"Ivy, I told you, I don't have all that much time."

"Then you'd best get me some measurements, then." She sighed, then looked at her watch. "Alright, I live in Palo Alto, I rent an ADU from a rich dude I promise you I'm not fucking, mostly because he's a sweet old guy. 54390 Mariposa Court. Get me those numbers, and we'll, uh, work something out after my shift, k?"

"Can do." He grabbed his receipt and ran off, forgetting the--

"Cream!" Ivy called. Kenny ran back, grabbed it, and sprinted away. As he left, Ivy grinned big, almost as if this was according to plan.

Kenny drove back, and stormed into the house, tossing the cream right at Jamie's forehead while he was eating. "Got the cream bro think fast! It hit Jamie right in the face. Kenny ran upstairs.

"Gah, dammit, Kenny! What the fuck?"

Kenny called from upstairs. "Yo, you got some of that tape seamstresses use to measure shit?"

"Uh... what?"

"You know, like when they take measurements and shit? I'm getting a suit fitted! Gotta be done now!"

"Um, yeah, got one in my drawer, somewhere?"

"Which drawer, Jamie? Dresser? Desk? Nightstand?"

"Nightst--Kenny, it's late, what tailor is even open at this hour?"

Upstairs, Kenny had gotten the tape measure and was stripped down to his underwear. Jamie had a full standing mirror that Kenny stood in front of to take his measurements.

"A real good one!" Kenny called.

Jamie entered his room moments later. "How good could he be if you gotta go take your own damn measurements, then give them to him by what? Hand? Snail mail? Not to mention it's past ten pm."

"You know, you make an excellent point, J. And just for that, I am going to get you a fitted suit, no money down. Shirt and pants off!"

"What--uh, okay. Free is free."

Not to mention he got to be nearly nude in front of Kenny. Both had chubbies forming. Jamie stood at attention while Kenny took his measurements.

"How do you know which measurements to take, even?" Jamie asked.

"Worked summers at a dry cleaners near Pike's Place." Kenny explained. "Never could figure out the particular name of the tape measure, though. Plus, boss hated me."

"Then why stick around, and why didn't he fire you?" Jamie asked.

"Needed money, never called out."

"O-kay, so, we gonna have a real discussion on the whereabouts of my dildo?" Jamie asked.

"Got put to good use."

"You've said." Jamie crossed his arms.

"Maybe I used it, what do you know?"

Jamie blushed. "Oh, really? You weren't fooling?"

Kenny interrupted his bliss. "Ah-gah-gah. I said maybe."

"S-Sure-sure. Um, hey I sent some numbers to that credit checker, did a background check on a few others, even the twins for fun-sies."

Kenny smiled. He was learning. "That was a good start."

"I uh, I have a mini skirt, and a wig coming. Blonde. Should be here tomorrow." He chuckled. Kenny stared blankly at him. "But, you know, no pressure, if it's a no, it's a no. No big."

Kenny typed the numbers into the notes of his smart phone. "Good, you chew on that, and keep growing, I need to see a man about a suit." Kenny started for the door.

"Hey!" Jamie stopped him. "How uh, h-how was it? The dildo?"

Kenny shrugged. "Was alright." He made his exit.

Jamie threw his hands on his head. He fell back onto his bed, whipped it out, and started to jerk.

Kenny returned to the market, parking as degenerately as was humanly possible to do so. He dashed inside, Ivy had just finished up with a customer.

"You know, if I had your damn number, I coulda' texted this shit to you."

"Wait... you got them? That fast? How do you even know which measurements to--"

"--I worked summers at--who cares, not relevant. Here's my measurements, and here are Jamie's. Airdrop, baby." Kenny Airdropped the attachment to Ivy's phone.

"Well, I am impressed. However, I can't just leave work in the middle of my shift."

"What happened to you 'practically running this bitch'?" Kenny asked.

"That was a quick break, not another rendezvous, you should recall that was after my shift. Tell you what, you have my address, you know your measurements, go try on a couple of things, I'll be along after. Gate code is on the side, #2698, go all the way back, ADU is across from the pool. Shouldn't be locked."

Kenny smiled. "See you over there." He left again, while Ivy smirked, steepling her fingers.

"Excellent."

Kenny drove a hop skip and a jump away to Palo Alto, finding the address in question, he even got to park next to a public charger on the street out front, what luck. Everything went right, even the gate code. Kenny briefly marveled at the one percent manor while quickly making his way to the back of the property, a sort of bland back yard complete with concrete swimming pool, turf lawn, no character to it, some lawn chairs near the pool, a patio with a covered BBQ area at the back porch, and of course the ADU, a modest concrete structure resembling the main estate.

Kenny opened the sliding glass door and entered. "Hello?" He called. He reached around for a light, and found one.

It was a one bedroom, complete with full kitchen, living room, and large primary bathroom. Kenny looked around, finding a walk-in closet between main area and bathroom. Inside, was a treasure trove of femininity in various sizes, as well as a makeup chair and table.

"Whew. Alright, let's uh... give it a shot." He mumbled.

For what some hours, Kenny had himself an 80's montage of outfit hopping. After several failed attempts for what seemed like an eternity, Kenny settled on a sequins cocktail dress that was just too short, silk stockings, and a lacy thong. He looked at himself in the mirror in the closet.

"Damn--" he began

"--You look hot!" A voice finished his sentence.

Kenny turned, standing there in the doorway was a woman. Her name was Harper. She was Chinese-American, skinny and cute, with a dark pixie cut, B-cups, a tight body and a very tight ass. She was about thirty-two. She grinned and crossed her arms, Kenny tried to cover himself up, and boner poked through the bottom of the dress.

"Oh shit, look-look-look, this isn't what it looks like?"

"Ha-ha, relax. You're Ivy's friend Kenny, right?" Her smile then faded. "Right?"

He sighed of relief. "Then it's exactly what it looks like." he shrugged.

"I'm her roomie, Harper, she told me you'd stop on by, and I told her I'd keep you company." She grinned again, holding up a bottle of nail polish in one hand, and mascara in the other.

Smash-cut to Kenny in a makeup chair while Harper made him look pretty, not to mention the man-pedi that went with the treatment. Kenny, of course, over-shared his grievance filled story about his and Jamie's predicament... both financial and sexual with his specious reasoning as to how both are directly correlated.

"Annnnnnnnd your hope is having sex with your roommate in drag will get you guys a new roommate?" Harper asked.

"At this point, whatever gets his lazy-ass from the weed and whatever else. He did show me something today. Did a couple of things for our background checklist for some applicants."

"See, he learns." Harper nodded. She took off his glasses briefly and threw on a pair of fake lashes.

"This was after I busted on his butt." Kenny deadpanned, putting his glasses back on. "I feel like I opened the damn floodgates. He started to ask if he was in drag, would I fuck him."

"Didn't say no, eh?" Harper winked.

"Didn't say nothing. Maybe that's worse, I don't know? I thought maybe... thought maybe if that got him motivated, he'd get himself a real job, wise-up and stop asking me, or..." He trailed.

Harper giggled. "Or maybe, just maybe... you like him."

"I'd like us not to be on the street."

"Seems to me like every time some intimate vulnerability might come up, you retreat right back to this being a specific mission. You're already dolled up, you've proven you're not squeamish to taking some dick, and actively in training to pound this twink-y roommate of yours."

"God, no wonder your Ivy's roommate. So, what?" Kenny asked.

"So, seems like an awful lot of trouble to get your friend to act seriously when maybe he may not even pull through." Harper explained.

"I told you, I saw growth. The system is working." Kenny insisted.

"We'll see." Harper said. She left the room for a moment, and returned with a long dark wig. She fitted it onto Kenny's head. "Perfect, stand up." He did as told, and Harper gave him a once-over. She lifted up the dress, and played with his ass. "Speaking of twinks, this is one fuck-able tushy."

"Ah, you mean it wasn't just makeup and wigs?"

"Oh no, babe. That ass is mine. But, look at it this way, you should get your cherry popped before your roomie."

"Unless you got a dick in those shorts." Kenny replied.

"I'm just the pregame. Ivy wanted you nice and stretched out for when she gets home."

"That dirty bitch had all this planned out."

Kenny took a moment to grumble and marvel at Ivy's foresight with this training. Harper took him by the land and led him to the bed, bending him over and lifting up the dress. With her were a few dildos of various sizes and a strap-on harness and dildo.

"It should go without saying, but you need a female persona to go with this look." Harper insisted.

"Hmm, Jasmine."

"Really? That was quick."

"Always liked that name."

"Well, I like that, but we need to work on your girl-voice."

Kenn--er, Jasmine sighed, and took her voice up a few octaves. "Okay." It was stilted and awkward, but it got a chuckle from Harper, who knelt behind Jazmine's ass. She pulled down the panties, and gave her cheeks a slap.

"We'll start you off light."

Harper kissed both cheeks, then stuffed her tongue in her hole and gave a quick rim. She then lubed up a finger, and slipped into Jasmine's ass. After a moment or two, Harper slipped in another digit, stretching out her hole more.

"Okay, let's try a little dildo, here."

It was a small one with a base that had two finger holes, not much bigger than Harper's own fingers. She slipped it inside of Jasmine's hole, and stretched it out just a little bit more. Jasmine herself, was getting used to this bottom life, and softly moaned.

Next, Harper tried a marginally larger dildo, slightly smaller than the dildo that was borrowed from Jamie. By now, after some slight resistance from her sphincter, the dildo went right in. Jasmine could feel her cock grow as the dildo got deeper and deeper into her ass.

"You'll be ready for Ivy's cock in no time at this rate."

"Think she'll cum in me?" Jasmine asked, trying out the feminine voice more.

"That'll cost extra, doll." Harper chuckled, giving her cheeks a pat.

Harper then got out a larger vibrator and rammed it inside of Jasmine, who moaned and squirmed, but quickly accepted the anal invader.

"Oh, you bitch." Jasmine groaned.

"Bottoms can take it."

Harper stuck the cock in as deep as she could before leaving it inside of Jasmine. Harper took off her shorts, and slipped on the strap-on harness and dildo. She took off her shirt. Slowly, she pulled the dick out of Jasmine, and hopped on the bed, laying on her back, the strap-on facing straight up.

"Hop on."

Jasmine cooed, then jumped on the bed and crawled over to Harper. She took off her panties, and lifted the dress up a bit more. She straddled the cock cowgirl, it was very awkward at first, with multiple false starts before the dick found it's way inside of Jasmine's ass, and sat right down on it. Jasmine practically came as she took every inch of it at once.

She started to bounce on the dick while Harper stroked Jasmine'c cock as it flopped right in front of her. They stared into each others eyes for a moment, forgetting one was in drag and getting pegged by the other.

Of course, little did they know, but by this point they were being watched from the sliding doors by Ivy, who smirked. She already had her clothes off and was stroking it to the hot scene taking shape on the bed in front of her.

Jasmine moaned as she bounced harder while Harper stroked just as hard, Jasmine knew she was close, she sat down hard on the dick while a shot of cum hit Harper square in the face, sticky ropes subsequently getting direct hits on her mouth, chin, and finally neck. They caught their breaths while Jasmine got herself off the strap-on and fell next to Harper while Ivy approached, and slowly clapped.

"That. Was. Hot. As. Fuck!"

"Enjoy the show?" Jasmine asked in the girl voice.

"And uh, did we choose a name?" Ivy asked.

"Jasmine." Both said in unison.

"Love that for you. Unfortunately, what I don't love is you laying there when my cock is all the way over here and not balls deep inside of your sissy ass." Ivy pouted.

Jasmine moved her way to the edge of the bed, and bent over it from the side. Ivy sauntered over, and lifted up the dress, giving her cheeks a slap. She lubed up her dick, and poked the tip right at Jasmine's more well-seasoned entrance.

Harper slipped off the strap-on, and crab walked over towards Jasmine's face, getting her pussy right in her face. Harper motioned to Ivy.

"She called you a dirty bitch."

"You flatter me." Ivy cooed.

Harper licked some cum from her lips. "By the way, you should eat more fruit, makes it taste better."

Jasmine smiled, but deadpanned. "Be quiet."

"Ho-hum. Nobody listens to me." Ivy sighed, her tip slowly opening Jasmine's hole. "No matter. You did want to learn quickly, so we'll skip the hygiene advice and go right to the gratuitous ass pounding!" She then slammed into Jasmine with all her might.

Jasmine moaned loud, but it was quickly muffled by Harper shoving her pussy in Jasmine's face. And boy was Harper's tightness dripping wet. Jasmine was floored by how tight and hairless she was.

She licked around Harper's clit and she moaned softly while Ivy huffed as she picked up her pace, slamming her crotch into Jasmine's ass.

"God!" Ivy panted. "I hope your roomie is as tight as you!"

Jasmine thought a big 'doubt it'. She could feel her ass tightening around Ivy. She hastened her licks around Harper's vagina.

"Oh fuck me." Harper huffed. She started to rub herself. She was close.

"Yeah, and this virgin tushy was just what the doctor ordered." Ivy purred, biting her lower lip.

Harper rubbed faster, but as she did, Jasmine's tongue found her sweet spot. Harper bit down on her free fist and clenched her thighs. She came. Her body spasmed with each push.

Simultaneously, Ivy was ready to fire, after getting as deep as she could go inside of Jasmine, she quickly pulled out and fired her load on top of her ass, letting the last bit drip down her thighs.

There was much huffing and puffing. Harper and Ivy collapsed on the bed. Jasmine laid there bent, and spent, but she could not have been more satisfied.

Moments later, the clothes and wig were off, she was Kenny once again. He washed himself off in their shower. It was a nice modern shower, with glass doors and marble flooring. He turned, the doors opened, Ivy joined him, smirking.

"Round two?" She winked.

"More like three. Jasmine's ass is closed for the night." He insisted.

"Suit yourself." Ivy shrugged, joining in the shower. "So?"

"What?"

"In this evening alone, you have been feminized, and ass-fucked twice. There will be no more--and I mean this, Kenny; there will be no more ambiguous head games. No more mental gymnastics. You like cock, you like to dress-up, we both know you have at least some sexual attraction to your roommate, and you know what you have to do, yes?"

Kenny sighed, and nodded. "I like cock. I said it. Doesn't mean I don't like women."

"Oh, you've made that abundantly clear to Harper. I'm jealous actually, I can't even make her orgasm like you did. Now, now we go fuck that prissy roomie of yours like the bitch we both know he is."

"No, we don't. At least, not yet." Kenny smirked.

"Huh? What the hell was all this for, then? And what happened to needing all this by week's end? Why the hell do you think I planned this tonight, we skipped like... three lessons of bottom-bitch school for this!"

"You weren't listening. True, I was beating around the bush. But Jamie's still a lazy fuck who, despite showing me something, isn't off the hook."

Ivy smiled. "Punishment?"

"Only the best kind. Let's face it, he won't think of it that way yet we all get satisfied."

"Hmm, dolled up and boned one time and suddenly you can take charge. I've trained you well."

The door opened again, it was a naked Harper, wearing the strap-on. "Speaking of punishment, I stayed up way too late for all this." She smirked, and lathered some body wash on the dick. "Against the wall." Kenny and Ivy rolled their eyes, and leaned against the wall as instructed, pushing their asses out.

"What happened to 'no round three' huh?" Ivy asked. "'Jasmine's ass is closed'?"

"She's hot." Kenny shrugged. Ivy glared. "Fine, your thing's a little too big for another round at this moment. Better?"

"Good answer." Ivy nodded before she was interrupted by Harper standing right behind her and smacking her ass.

"Kenny's ass is still open." He smiled.

"Wait your turn." Harper hissed before stuffing Ivy's ass with the strap-on, Harper then used a free hand to finger Kenny.

Later, Kenny was all washed, showered, fucked, and clothed, literally in that order. He was about to leave.

"Five pm tomorrow, bring everything." Kenny insisted.

"Just be 100% sure Jamie won't chicken-out." Ivy raised an eyebrow.

"If he do, the limited amount of respect I have for him will evaporate as my anal virginity has in this past week." Kenny shrugged.

"It's really been a whole thing with you two." Harper sighed.

"Girl, you don't know the half of it." Kenny deadpanned.

"I think we do." Harper chuckled, putting an arm around Ivy's shoulder.

"You see, Kenny, we're not just here to femme and fuck you. That helps get me to cum." Ivy explained. "We wanted you to listen and learn, even if it's from a bitchy little shit like that Jamie of yours."

Kenny shrugged, ws she right?

He got a kiss from Ivy, followed by an ass slap, and a bigger kiss from Harper, and he was on his way.

He drove home confident. Jamie was asleep. Kenny snuck in, saw him passed out, completely naked of course. He dropped off the dildo he borrowed from earlier.

He did notice something catch his eye. On Jamie's desk, was a semi-organized stack of potential roommate portfolios complete with all the background information Kenny required of him.

"Son of a bitch. He actually did it... like, all of it." Kenny whispered, though it was loud enough for Jamie to stir for a moment, then fall right back to sleep. Kenny smirked, then shook his head. "Almost breaks my heart for what's coming tomorrow."

Kenny set everything aside and left. He walked to his room and sighed. It was a long process, and yet, not even done. Did he find himself? Perhaps. Did he get Jamie to give a shit? Definitely. Kenny smiled, he fell on his bed and rubbed his pants, excited for the day ahead.

Thanks for reading part I. Part II available soon! Feedback is appreciated! Un til next time, I've been Hugh Jass, and it's been my pleasure to present you with this story.