Chapter 13: Double Dates

Nine hundred dollars...

If you ever wondered how much it costs to fix a patio door with a body-sized hole in it, there’s your number, excluding tax and installation. I’d been a rich man only two days ago, but after paying for that goddamn door, and the much more reasonably-priced bump & grind from Lexi, I only had a few hundred bucks left, and I’d hoped to help Syl out with her books. I ended up giving her the rest, keeping enough to serenade Katie and the adorable Asians down the street before I could make some more cash at work on Monday.

Thank God Derek knew people in landscaping and construction. Before he left the party, he’d taken a look at the wreck and given us the number of a guy who’d fix it on the cheap. He also agreed to front the installation cost, though for what reason, I didn’t know. Maybe he was trying to impress Syl, or maybe he sensed that we needed the money, but whatever the reason, it was appreciated. He really was a stand-up guy.

Returning from the store, Syl pulled her Prius into the driveway as Derek’s handyman parked on the street. I took him around back and showed him the damage and he said he’d be done in an hour. And maybe when you’re finished you can help me haul a couch out of the swimming pool...

Driving around town with Syl had helped to take my mind off of the fight I’d had with Katie. I still wasn’t looking forward to dealing with it though, because I had no idea what I’d done. Should I apologize for having a boner? Or being alone with Lexi? I didn’t understand why she was angry.

In any case, I headed upstairs to seek out Lexi, not Katie. I’d been without a boner for almost three hours and was itching for a fix. I brought up the door locks I’d purchased at the hardware store with me, hoping that the prospect of privacy might provide a further enticement.

It struck me how quiet the place was. No one seemed to be around. The first sounds I heard were muffled voices coming from behind Lexi’s door. I’d assumed that it would be Bridget and Lexi talkin’ shit on people like usual, but as I pushed the door open like the inconsiderate douchebag I was, I discovered that I had been mistaken.

“What the hell?” Katie screamed. “Doesn’t anyone knock anymore?”

Katie was seated at Lexi’s vanity with her feet propped atop the desk, her toes separated by cotton balls and painted a pretty shade of metallic pink that went well with her skin. Lexi sat to her right, carefully painting her fingernails a similar color. Both of their heads were wrapped in a curious arrangement of towels and what looked like foil condom wrappers and seemed tied into place by magic. Katie’s face ... my God ... Katie was fucking gorgeous.

I hadn’t realized that I’d never seen Katie in makeup before, and my jaw dropped as I witnessed what I’d been missing. Her skin seemed softer and was a shade lighter than usual, her eyes were more vibrant than I’d ever seen before, and they were highlighted by thick curly lashes and just enough shadow to make them pop. Her eyebrows were tweezed and defined, her lips were a glossy color to match her nails, and it seemed as if all her features were chiseled out of marble.

I’ve always preferred natural girls to girls covered in paint, but that was because I’d never seen makeup done correctly. Everything on her face only amplified and accentuated the beauty that was already there, and my heart ached as I realized what a beautiful creature my sister had become. Oh ... and they were topless. It took me few seconds to realize it, entranced as I was, but there were definitely some boobs on display. Damn ... Lexi looks entirely naked.

Lexi turned around to see me and immediately stood and approached the door. Yep, definitely naked. “Nuh uh,” she said, “No boys allowed.” She gently placed her hands against my chest and pushed me back outside into the hallway. Just before she slammed the door in my face, she winked at me and whispered, “You’re welcome.”

For a second I didn’t know what to do. “I ... uh...” I looked down at what I carried. “I brought your door lock,” I called through the door, but whether or not they heard me, I didn’t know. What the fuck had happened after I’d left the house?

Syl came upstairs and saw me standing alone, staring at the door. She walked up to me before stopping. “Aren’t you going to knock?” she asked, looking quizzically at the door.

“No boys allowed,” I told her and she smiled softly in return.

“Well, I guess you better get lost, then.” She laughed and then she shouldered past me into the room. I caught a brief glimpse of the girls quickly pulling on some tops as she entered, but then she quickly closed it again in my face.

“Oh fun!” I heard her say. “I love makeovers. You look so pretty!” As feminine and as girly as the shit that was going behind that door seemed, I still really wanted to be a part of it. It was only halfway because of the boobs. I shamelessly flattened my ear against the door, straining to hear.

I heard a few “greats” and something from Katie that sounded like a verbal lack of self-assurance, but then I heard Syl pose an interesting question, something I’d completely forgotten about in the sexual whirlwind since the party.

“Has Kleio come back yet?”

“Oomph! Never. Ooomph! Stop. Oomph! Fucking. Oomph! Me...” Drew kept up his blistering pace, trying to satisfy her wishes in spite of the rapidly building ache in his balls. He knew that he would have to quit eventually. “Never” was a tall order. He’d already been beating up her pussy like Mohammed Ali for the better part of an hour.

He gripped Kleio’s hips and bit his lip to delay the encroaching climax, his lower torso becoming a wet slapping blur beneath his glistening chest. He wasn’t used to getting so tired and weary in the act but having sex with Kleio was like bedding down a wild horse There was fair number of girls who’d said the same thing about him, however. Not all women were as appreciative of The Infinity Hammer as Kleio was. He continued to drill her from behind, his comically-huge penis stretching her lips, causing them to grip and tug on his shaft each time he withdrew.

“Oh my God,” Kleio said, arching her back like a cat while her juicy butt cheeks rippled from his collisions like drops in a bucket. She was nearly bent over backward and getting the business end of the monster cock for the fifth time, but he was so damn big that it still kind of ached like her first time, all those years ago. “Fuck, you’re so hard.” Drew smiled and blew a kiss to the camera.

The wall of the hotel room rattled as Drew repeatedly drove Kleio into the headboard, and the laptop sitting across the room buzzed with activity as it recorded it all. A browser window was open to a camera feed, and Drew grinned as he watched himself annihilate Kleio’s vagina. A chat room window next to it scrolled down steadily, as more and more perverts from around the country tuned into their performance.

Soon Kleio’s demands to never stop fucking became troublesome, as the load Drew felt bubbling up seemed determined to make an appearance. “I’m gonna cum,” he grunted, his strokes becoming longer and deeper. “Oh Jesus, I’m gonna cum.”

Kleio stopped bucking against him and instead slowly began to roll her backside against him, twerking in slow motion and effectively massaging his dick inside her. She turned to the camera as well. “Three hundred tokens to choose where he cums...” she said, winking. “Mmmm, I hope I get to take it in my pussy again.” She practically moaned the line, but Drew didn’t mind her theatrics.

He took a deep breath, watching Kleio’s pussy lips methodically swallow his penis. “And please, choose quickly,” he added. He wasn’t sure how much longer he could keep this up, before his dick blew like a volcano. He didn’t care where the viewers wanted him to cum, but the tide waits for no man, and neither did The Infinity Hammer.

The chatroom exploded in little chimes and dings as faceless names like TuffLuvv69 and Kingboner33 jockeyed to be the first to choose the location of Drew’s imminent whitewashing. Tokens were spent, and suggestions considered, but BonerPrince14 - the likely heir to Kingboner33 - quickly ended the bidding war with a generous donation of a thousand tokens and the words of a poet: “CUM ON HER FACE! GET IT ALL ON HER FACE!”

“BonerPrince takes it,” Kleio announced, and spun on all fours to face Drew’s penis. He started to jack himself off but she slapped his hand away so she could do it herself. “Real girls finish the job.” She stared up into his face while she pumped his cock with both fists, swirling her tongue against the tip. He could feel his release approaching, snaking little tendrils of pleasure starting to fire across his body.

“DO IT!!!” the audience cried.

“ON THE FACE!!!” Another loudly typed.

Drew closed his eyes, trying to concentrate. He’d heard that performing in front of an audience increased the stress, and it was true. Banging strange women had never been a problem for him, but for some reason, busting his nut in front of virtual strangers gave him little stabs of panic. “What if I can’t cum to standards?” He’d asked Kleio when they did their first show the previous night. “What if I cum disagreeably or in bad taste?”

Kleio had responded by taking her top off to show him how easy it was to make the audience happy. They all applauded and donated coins. “Just relax,” she’d said. “They want to see me anyways, not you. As long as you manage to cum at all, you’re gold.”

And so Drew was gold, and he stayed gold, ponyboy, all through the night, pumping a total of four loads inside her before the night was out, letting his deposits slowly leak out onscreen and make all her chat room peeps happy. He supposed that “cum inside her” guy had run out of money because “ON HER FACE!” guy seemed to be calling the shots for the moment. Drew didn’t mind either way, and slowly clenched his teeth and held his breath as his cock ballooned to maximum hardness.

“Cum for me, baby,” Kleio whispered, her tongue serving as punctuation, and then everything seemed to become muted around him, and he was he was cumming again. He grumbled something indiscernible as he crescendoed, and then began to fire gooey ropes of jism across her face, the pearly fluid dripping down her cheeks and onto her chin. The next blast took her in the right eye, and she closed it before taking another shot into the other.

Other girls might’ve stopped at that point, or at least gone blind, but Kleio forced her eyes open and continued to pump Drew’s meat, sticking her bar-belled tongue out as far as she could. Once she was sure he was completely dry, she held her head steady and climbed off of the bed. Then she knelt in front of the camera so everyone could get a close-up view of Drew’s masterpiece before she wiped it off with her fingers and licked them clean.

As Kleio began to type her goodbyes to her fans, Drew laid back on the bed. The previous night had been taxing, even compared to his usual routine. He was in excellent shape, and his penis was perpetually DTF, but as soon as Derek dropped them off last night, Kleio proceeded to break his shit off by fucking him in front of a live audience for no less than three hours straight, blowing him back to life after each explosion.

He’d never cammed before, but there was something exciting about fucking in front of internet strangers that he kind of enjoyed. He’d also enjoyed the sense of duty Kleio had exhibited during these fucking sessions. She’d been very thorough in coaxing each and every load out of him, and insisted that she was the hardest-working camgirl on the site. As he lay there sweating, panting, and out-of-breath, he believed her.

“You OK? You look a little wrecked.” Kleio strode up to where his feet dangled off the bed. She was nude and had been for the past sixteen hours or so, but Drew was still impressed with how amazing she looked in the buff. Now that she was shiny with perspiration as well, he’d knew that he’d had to hit that at least one more time before they headed their separate ways. He’d never tasted “punk-rock tattoo chick” before last night and he’d come to appreciate the flavor.

“I’m approaching my limit,” he said, craning his head to look at her. “The last time I felt this wasted was when I chased Chastity Devons out in the street and got hit by a truck.”

Kleio smiled before stepping up onto the bed, perched over Drew on all fours. “Hmmm ... trying to steal away Chastity’s chastity were you?”

“Well we were both seven,” he said. “But yeah, pretty much.” Kleio smiled while leaning over Drew, her chubby breasts hanging down nearly to his chest. She smiled but instead of reaching for his dick, as was her wont, she simply collapsed on top of him, resting her head on his chest.

“I’m so fucking tired...” she said.

“A likely story,” Drew said. “Chastity tried that excuse when I caught her, too.”

“We should sleep,” Kleio said, closing her eyes.

“The last time we tried that you woke me up after an hour to fuck again.”

She purred against me. “I remember last night differently. I remember sleeping quite soundly before you pried my legs apart.”

“That was my dick. I had no say in the matter.” He turned his head to the side in shame. “I tried to stop him but he’s very insistent.”

“Mmmm, I’m sure.” She shifted position, snuggling against him till she found a comfortable spot to nest. “This was way more fun than my usual cam shows. Not many boys are cool with letting my viewers watch us bang.”

“I can get that,” Drew admitted. “It’s a little strange.” Fucking becomes a lot more high stakes when you realize a bunch of inconsiderate assholes are going to critique your performance. He sadly shook his head. “I apologize again for blowing that double axle in the second round. I’m fucking better than that.”

“We could have been medal contenders,” Kleio said sniffling. She didn’t bother to even open her eyes. “I knew I should have gone home with that other guy.”

“You mean Derek?” he asked. “Please, that guy is vanilla as they come. You wouldn’t like him. He’s so straight-laced, by-the-book, and competitive that...” He thought about it. “Actually yeah, I guess that is how people win medals.”

Drew was truthfully a little envious over Derek’s work ethic. They may have had done the same job, but Derek seemed so much more collected, present, and driven. He was more passionate. Drew, rather, floated through life on a raft of apathy and laziness.

“I was actually considering him for Syl to be honest. They seemed to hit it off and that girl needs to get laid in the worst way. Is he seeing anyone?”

Drew twirled a piece of her hair around one finger. “Kind of married to the job, actually. Come to think of it, I’ve never actually seen him with a woman outside of work.” Derek had never expressed interest in dating. He was probably too busy.

“Pool cleaning?”

“No,” he said, a little agitated. “I told you last night. We’re whores.” He never even tried to keep it secret anymore; no one believed the truth.

Kleio smiled and snuggled closer. “Yeah, you tried that line on me last night.”

“How is that a line? How does telling you “I’m a whore” get me any closer to having sex with you?” Kleio opened her eyes only to roll them. She probably meant that gesture to imply that it worked on her, but Kleio had been so ready-to-go that he could have admitted to leprosy and still gotten a twirl. “But it wasn’t that job I was referring to. He’s got another thing ... kinda on the side.”

“Yeah, he mentioned that to Syl last night when discussing the door,” Kleio said. “Landscaping and construction or something like that?”

“No, not that thing.” Drew forced a chuckle. “The other thing.” Drew thought his own double life was complicated, but Derek’s intricate situation was like the Gordian Knot of lies and secrets. He’d only managed to figure out what was going on a few weeks ago after they’d been working together for six months. He still refused to speak of it.

Kleio again shifted her body atop him, all her sweaty naked body parts slithering against his. “We should take a nap before we have to check out.” Drew giggled to himself. How many hours did she think were in a day?

“Checkout? Kleio, it’s like 6 pm. It’s dinner time. I think we missed checkout.”

She sighed, closing her eyes again. “Oh well ... shit. Syl wanted to stay another day anyways. Really needs to talk to her mom.”

“Oh, I didn’t know you guys were sticking around,” Drew said. “You staying here again?”

She nodded. “I guess I am now if we missed checkout.” She raked her nails lightly against his ribs. “You have to stay and have more sex with me.” She dipped her arms around his back and squeezed him, claiming him as her property.

“Well if I have to,” he said. “I’ll let my mom know I’ll be missing dinner.” Kleio maneuvered her thighs until Drew’s slick flagging length slipped in between them while he went for his phone. He hadn’t been joking, and sent a quick text to his mom.

“I think it’s adorable that you and your mom are on such good terms.”

He smiled at her. She had no idea.

Drew: Won’t be home till tomorrow. Bangin a hotty. =P Mom: XD

“We understand each other,” he told her.

She pushed around his chest, trying to mold his pecs into a more comfortable pillow. “Well, we can go again, but you have to do all the work.” Her words spoke of passion but of her lifeless, spent, tired body, there was only sleep. “ ... or we can just sleep...” An ultimately better idea. He grabbed the corner of the sheet near their feet and tugged on it until it covered them.

He then tried to fall asleep but it wouldn’t come. He hadn’t been able to get a good night’s rest in several weeks, because he couldn’t stop thinking. It’s like his mind set aside all of his worries and doubts about the future and only considered them when he tried to sleep. He knew it was related to Derek and his other job, but there wasn’t anything he could do about it.

“Hey, you like camming, right?”

“Sure,” she said.

“But at some point, you realize that you’re going to have to stop. Like, you’ll get too old, or viewers will start dropping off, or whatever right?” She opened her eyes and sleepily looked up at him. “I mean, maybe not for years, but still you know that it has to end at some point, right?”

“Sure.”

“It’s just that ... I figured that’s why you’re studying to become a nurse.”

She turned her head forward and rested her chin on his chest as they conversed. “I’d like to be a nurse someday,” she said. “Or a doctor. But right now, there is a ton of money to be made in front of that camera. Studying is tough, and sometimes it’s just easier to get naked and diddle myself.”

“Right, can’t argue with that,” he said. “But you know it’s only a matter of time and so you’re preparing yourself for it.” He exhaled. “I just keep thinking that I should be doing the same thing.”

Kleio nodded. “Probably a good idea,” she said. “I’m sure pool cleaning is a terribly competitive market. There’s always someone newer and younger with a shinier penis trying to steal away your limelight.”

Drew laughed. “You jest,” he said. “But trust me, there are serious reasons why I believe my job can’t continue for much longer. I really need to be thinking about other avenues of employment.” Kleio nodded.

“Why don’t you come up to Stanford some week or something?” she asked. “I can ask my professors if they’d let you sit in on a class to see if it’s your thing. Or you could just sneak into freshman lectures. Nobody notices when classes are that large.” Drew thought about it. Maybe.

He’d even considered asking Derek about working with him on the other gig, but he wasn’t sure if it would be his thing, or even whether it was possible. Derek was different. It was as if he knew exactly who he was, and where he was headed. Drew didn’t have his assurances or his conviction.

“I might just do that,” he said. “After a nap...” Kleio seconded his motion by snuggling under his arm while he reached for the bedside lamp. He grabbed his phone as he did so. “1 missed message” was displayed on the face. It had probably been during round three or four, after he managed to land his triple lutz. He tapped it open, read it, and frowned.

“Is it your mum?” Kleio asked. “Begging you to come home and eat your vegetables?”

“Not exactly,” Drew said, exhaling. “Fuck.” He gently rolled Kleio off to the side and sat on the edge of the bed. “Goddamnit, I knew that party was a bad idea.”

Kleio stared at his back. “Who was it?”

“That was one of my coworkers.” He put his phone facedown onto the mattress and cradled his head in his hands. “Fuck, fuck, fuck,” he chanted, not knowing what else to say.

“Bad news?”

He shook his head. “Damn it,” he repeated. He rose to his feet and moved toward the bathroom, typing into his phone.

“Looks like I might need to look for another job sooner than I’d hoped.”

Babs rang the doorbell and waited. As a reflex, she smoothed down her skirts one last time and glanced down to make sure her cleavage was popping. She’d gone out and selected the dress earlier that day, a sleek, tight black number that strode the perilous line between class and ass.

It was tight, there was no denying that. The way the dress clung to her curves and pulled on her tits was constricting, and it hugged her butt so tightly that it would ride up several inches if she even thought about bending over. But on the other hand, it practically oozed sex. She’d even gotten a little excited staring at her reflection on the Uber ride over, and she still felt a warm tingling sensation knowing what she was there to do. It was just so naughty.

But it was also a little dangerous and she knew that. The other feeling that bedded with her excitement was anxiety, and the scant information that she received from Dana hadn’t helped to assuage it.

All she was told was that it was a single young man named Mackleroy, that it would be a private affair, and that additional services could be arranged at her discretion once the initial contract was fulfilled. She’d been sent a basic price list: $25 for a lap dance, $100 for a blowjob, and also an NDA with some additional forms to sign. She’d filled everything out and faxed it over while shopping, and took a little twisted pleasure in selecting a wet shiny shade of lipstick that made her lips look perpetually fresh from cock-sucking. She hadn’t ruled out a few additional services after all. She needed the money.

The door opened finally, and a wave of air conditioning spilled out the doorway along with booming rock music and the buzz of dozens of young people conversing. The clamor inside didn’t surprise her. As soon as she’d noticed the Greek letters posted above the door, she’d realized that this was a frat party. She’d been to her fair share in her day. She and Dana had even met Clarence in a place just like this one.

A bleary-eyed young man with an impeccable haircut and a pink polo shirt answered the door, and he openly allowed his eyes to wander over her entire body before he spoke. “Whoa,” he said. “Are you with the tri delts?” he looked at his watch, before seeming to realize that Babs was older than a typical college student. She appreciated the mistake. “You don’t look like a tri delt.” Yeah, that’s exactly what those cunts told me when I tried to pledge twenty years ago...

“I’m here for the Mackleroy party,” she said. She caught herself fidgeting as she clutched her bag in front of her. She felt as nervous as if she’d been there as a student, trying to meet boys. “I work for...”

“Oh, you’re the hooker!” he said, slapping himself in the forehead. He swung open the door and several groups of partygoers all turned in the direction of his voice. She fought the urge to turn now and run away. “Jesus Christ,” he said, again openly examining her. “You’re way hotter than that little bitch deserves. Got a real Stiffler’s mom thing going on. Aren’t you supposed to be a little younger though?”

Babs opened her mouth and closed it. Hadn’t Dana said they’d requested an older woman?

Before she could respond, another well-muscled young man in a crew cut stepped over and shoved the first boy out of the way. “Sorry,” he said. “Our pledges kind of suck this semester.” He smiled and Babs returned it. He was very handsome. “I’m Tim. Mackleroy is upstairs. Follow me.”

The frat house was organized almost like a hotel, with larger party rooms, beer-pong tables, pool tables, sofas, and even a stage for dancing all on the ground level. Tim guided her through these rooms and toward the stairwell at the end. The second and third floors were the brothers’ rooms, with larger public bathrooms for use on each, and stairwells at each end. There were partygoers on the upper levels as well, but fewer, and the boy led the way all the way up to the corner room of the top floor, where he assured her Mackleroy awaited.

He explained on the way that Mackleroy was a virgin, and was an anxious nervous wreck around girls because of it. As a birthday present, his pledge brothers had chipped him and purchased him an escort for an hour, in hopes that his social skills would normalize once he popped his cherry. Babs was shocked to learn that she’d be deflowering a virgin boy, but not altogether displeased. The idea sounded more fun and playful than entertaining a stuffy old businessman or a husband like she’d expected. Also safer. With him not knowing anything, Babs would be free to call the shots and control the situation.

The room was like so many that Babs remembered from her school days, a 16ft by 20ft rectangular shoebox with a little bit of closet space. On the walls, she spotted all the regular decorations: the movie poster for Reservoir Dogs, the old “Beer, helping ugly people get laid since 1862” placard, and of course, a blown-up image of Scarface. It was all so delightfully nostalgic and tacky, and she wondered where the lava lamp was. On the bed sat Mackleroy.

He wasn’t a bad-looking kid. He was tall and thin and wore the same pink polo as the punk downstairs. It was probably their pledge class uniform. He had the downcast and suspicious look of a loner, with short ruffled hair and the soft peach fuzz look of a boy not yet old enough to grow a good beard. Babs smiled at him, but he seemed too nervous to look at her, and kept glancing from Tim to the other boy in the room, who sat on the desk.

The other boy was obviously a full-fledged brother, because his polo was black instead of pink and he swaggered like an asshole. Babs had known plenty of boys just like him when she’d gone to college, even slept with a few of them. One of them had been named Clarence. And like Clarence, he was also tall and muscular, and seemed the type of tough guy that always walked around with his arms crossed. He stood up from the desk, arms crossed, and nodded at Babs. “You’re a little late,” he said, before looking her up and down. “But you’ll do, I suppose.”

Babs bristled inside at being judged by some pubescent millennial dickhole, but didn’t show it. People like him were to be expected in this line of work. In fact, she’d thought that she’d have to fuck someone like him or the other guy who’d brought her upstairs, not the cute little virginal dork sitting on the bed.

“The hour doesn’t start until I arrive,” she said to him, forcing a smile. “You’ll get your money’s worth, I promise.” She beamed at Mackleroy, but as soon as she made eye contact with him, he looked away like some scared puppy. No wonder his friends bought him a girl, she thought. Ben has more self-confidence than him and he’s only fifteen.

“See that we do,” the arms-crossed douche replied, and then he ruffled Mackleroy’s hair and laughed. “Hopefully a little ass will loosen Mack up.” He glanced at her body. “Well I guess it’s more of a big ass but it should still do the trick.” He stepped over to the door, laughing along with Tim.

“I beg your pardon?” She said.

He opened the door and glanced at his watch. “We’ll be back in an hour. Make us proud Mackleroy!” He stumbled through the door drunkenly and the other followed. Babs walked over to the door, locking it behind them.

“Finally,” she said. “I thought they’d never leave.” She then approached the bed to stand in front of the boy who still refused to look at her. She hadn’t expected such reluctance. Every man she’d been with had been assertive enough to make the first moves, and she’d never considered that her John might not have even wanted this. Luckily, she was equipped with a body capable of encouraging him.

“So,” she said, a bit unsure how to proceed. “My name is Natasha.” She tried not to laugh, because inside, she was dying.

“I’m Mackleroy,” he replied, still staring at the ground. He sounded so downtrodden, she half-expected him to kick at a stone and gripe “Awww shucks.”

“Hey!” She snapped her fingers loud enough to catch his attention and he glanced up, seeming to see her for the first time. “You can look at me, you know. Aren’t I pleasing to look at?” His eyes seemed very tired, like he hadn’t slept in a week, but he did take a second to appreciate her curves, the roundness of her breasts, the ample bounce in her allegedly “big” ass. She took a few steps closer while she held his gaze. “ ... and Mackleroy? Why don’t you tell me your first name.” She leaned closer to him. “ ... so I’ll have something to scream while you’re pounding me.”