Jenny the Whore

AUTHOR'S NOTE: This is a work of fiction. All characters are over the age of 18.

*

"You know what you're asking right?"

"I know, Dave, I know."

"When people borrow money from me, they pay it back. One way or another."

"I fucking know alright!"

"And you're willing to do what you need to for this money?"

"Yes! I wouldn't be asking if I had other options OK! I'll do whatever I have to for this money."

"...OK then. I'm at the club right now, come on down and we'll talk more there."

"Fine."

"See you soon Jenny."

I hung up the phone and looked across the bank of monitors that showed me multiple angles of every room in my club. It was still early so we weren't open for the night, but the girls were filtering in and getting dressed in the back and the guys were busy cleaning and stocking for another night of debauchery. I saw one of the front-of-the-house girls heading my way and poked my head out of the office. "Hey Candy, you busy?"

Candy turned around, startled. "Oh, hey Boss! I was just grabbing the cash drawer for the front. Need anything?" I gave her a quick look up and down. Candy was one of the smarter girls at the club and I could trust her to run the entrance. She was one of the few full-time employees I had. Being a "front" girl had a lot of advantages, like steady pay, health insurance and not having to strip. She still dressed the part though. She was tiny at only 5'2" and wore a low-cut top that showed off ample cleavage, and a short skirt that flashed her panties any time she so much as moved, with her blonde hair done up in pigtails. She had one of the easier jobs in the club, just smile, take the cover charge, and check IDs. It was nice having at least one woman around the club that I could rely on.

I smiled and opened the door wider. "I've got a new girl coming in for an interview and I need to clear my head. Could you grab me a drink and someone to help with that?"

Candy bit her lip and stepped in close to rub her hand up my inner thigh. "Will do Boss. Anyone in mind?" She said with a wicked grin. I shook my head and leaned in closer to get a whiff of her perfume. Most of the girls wore overbearing scents, something to mask their own sweat and to give their regulars something to remember them by. Candy was different though, her perfume was light and floral, a little sweet. I couldn't place it, but it wasn't cheap. Just having her this close was already getting me hard and I could feel the tips of her fingers tracing along the bulge in my pants. Candy was off limits though, no fun with the "front" girls. God she knew how to tease me though. Her fingers found my cockhead through the fabric and gave me a quick squeeze. "Some stress relief coming right up Sir."

Candy walked off towards the bar, making sure to put some extra sway in her hips since she knew I'd be watching. I grinned and sat back down at my desk, unzipping my fly to release some of the pressure I closed my eyes and leaned back in my plush leather chair. A few minutes later I heard a knock on the door and opened my eyes to see Cho standing in the doorway, glass in hand and not wearing a stich of clothing. Cho was a skinny Thai woman who learned quickly to play up certain stereotypes when she was with clients. So many guys just wanted their "Asian Sensation" and were willing to pay for it, so she played along, broken English and all. With me she could drop the act. Cho closed the door behind her and set the drink on my desk. "I heard you needed some help Sir. How would you like me?" She hadn't finished speaking before she had taken the initiative and knelt in front of me, freeing my cock from its cloth prison.

I groaned as Cho licked from the base of my 7-inch cock up to circle the head and took me deep in her throat. I pushed her back with a grunt and held out a condom. "You know how much I love your mouth, but I need to be quick here." Cho almost pouted as she tore the wrapper open and stood up to straddle my lap. I squirted some lube into her hand from the bottle I kept on my desk for exactly this purpose and she quickly coated my cock before guiding it to her pussy. Cho wrapped her arms around my neck as she sank into my lap, with a shudder. I felt her warm walls envelop my member before she pulled her knees up to tighten even more around me. Feeling her pussy flex and stroke my cock was downright magical no matter how many times I had felt it.

I moaned at the sensations and saw Cho smile as she ground her hips into mine. "Oh yeah baby! Fuck me with your big white cock!" I gripped her thighs and frowned but didn't stop her motion. "Sorry Sir. I got carried away. I do love your cock though." As if to emphasize her point she lifted her hips up, grabbed the back of my chair and started fucking me even harder. "Mmmmmmm. That's the good shit right there! I want to make you cum sir. Are you going to give me your cum?" I slid my hands further up and held her hips in place as I fucked up into her from beneath, pounding her pussy mercilessly. "OOOHHHH FFFFUUUCCCK!" With a grunt I unloaded my balls into Cho and saw her eyes fly open as she felt my cum flooding the condom. Cho moaned and leaned into me, kissing me lightly on the neck. "Feels so good to have you in me Sir. I think I'll have to get myself off before I get on stage." I grinned through my post orgasm haze.

Cho reached down and held the condom in place as she climbed off my lap before carefully slipping it off and tying it closed before tossing it in my trash bin. Without looking she reached up for a wet wipe from my desk and gently cleaned my crotch. She took her time wiping every sticky drop up from my cock, balls and thighs before stroking me lightly to milk the last few drops of cum from my shaft which she dutifully wiped clean before giving my cockhead a kiss and tucking it back in my pants. By the time she had gotten up from the floor I had gotten five crisp 100 bills from my wallet and set them on the desk. "Good girl Cho. Wish I had more time for you today." Cho took the bills and folded them neatly into her hand before sauntering out of my office to go get cleaned up before her shift. I left the door open and sipped my whisky as I prepared myself to deal with my sister.

About 20 minutes later Candy reappeared in my doorway with Jenny close behind. "Thanks dear. Close the door and handle things for a bit would you?" Candy nodded and left my sister and I to our business. "Hey there Jenny. Gotta be honest, I was wondering how long it would take for you to come to me for help." Jenny didn't say anything, she simply crossed her arms and scowled. "Take a seat and let's talk business." Jenny rolled her eyes and looked at the chair across from me in disgust before sighing and sitting gingerly down. Jenny wasn't exactly prim-and-proper, she was just kind of a bitch. She was almost 6' tall, more than that in heels, which she really didn't need since she already had long, shapely legs. With her long, dark hair and high cheekbones she looked like she was ready to step out on a runway and didn't have any reason to be in a strip club. But all the same, she was here. "Alright, I'm going to start talking, let me know when you're ready to say your piece."

I took another sip of whisky and sat back in my chair. "You tried to divorce your hedge fund manager ex-husband when you found him cheating on you with his secretary. Then you hired a bunch of high-priced lawyers but in the middle of things he revealed that he had proof you were cheating on him first with your yoga instructor. Suddenly your prenup is worth nothing and you're out on the street with basically nothing. Then our oh-so-lovely parents disowned you because they figured it would be better to suck up to your ex and his senator brother than to support their only daughter. Which, as an aside, maybe makes you think about why I cut ties so long ago. Now you're out of money, owe a shit-ton in legal fees, and because you dropped out of college to marry that asshole, you have essentially nothing in job prospects. Did I miss anything?" Jenny mumbled something, uncrossed her arms and shook her head. "Alright, give me a number, what do you need?"

Jenny leaned forward and rocked a little, her eyes staring intently at my whisky. I slid the glass across my desk, which she took and gulped, coughing. "I- I need about $25,000." She drained the glass and set it back on my desk.

I shrugged, stood up and went to my wall safe. A quick combination later and the door swung up to reveal piles of cash in addition to some documents, hard drives, and other important things. Pulling out a few wrapped stacks I tossed them on the desk. "This'll last you what, a month? Two?" Jenny shook her head and shrugged. "Jesus Christ, you really never had to deal with money have you. Alright here's what's going to happen: I'm going to give you this loan as a favor, in return you're going to work for me, here at the club."

Jenny's eyes shot open wide. "I can't do that!"

I crossed my arms. "And how do you plan to pay it back? I'm not a fucking charity here. Even if I give you this money you're still going to need more to live off of. Where's that money going to come from Jenny?"

Jenny choked back tears. "Fucking hell Dave! Can't you cut me a break? I'm your sister for fuck's sake!"

I crossed over to the other side of the desk and offered Jenny a tissue. I wanted to be angry at her, and I was, but she was still my sister. "When I left home it wasn't just Mom and Dad that cut me off, you did too. I literally haven't heard from you in 10 years. The only reason I know what happened was because you can't seem to stay off of Instagram. The only reason I'm even hearing you out is because you're family. Now I'll be fair about things. More than fair. Hell, I'll make you a really good deal and if you work hard, then you'll be paid off in just a few months. Who knows you might like the work and want to stay."

Jenny dabbed her eyes with the tissue, careful not to let her mascara smear. "But I'm your sister. You want me to work at your filthy club?"

I sat back in my chair. "First you come to me for money, then you balk at paying it back, and now you're calling my business filthy. You can leave if you want." I reached out for the stacks of money but was beaten to it by Jenny's hand snatching them up and pulling them closer. "Alright then. The club opens in less than an hour, so let's get you up on stage and see what you can do."

Jenny sat back, stunned. "You want me to strip? Right now?"

I got back up and opened the door. "No time like the present. I need to see if you're cut out to work here." Jenny followed me out of the room looking like a deer in headlights. I caught Candy's eye and motioned her over. "Jenny's going to have an audition, can you lock her purse in the safe and get me another drink?" Candy winked and started to walk off before Jenny yelled after her that she wanted one too. Candy whirled around and blew a kiss at Jenny to let her know that she heard the order and sashayed back towards the bar. I guided my sister towards the stage and waved at the DJ who was setting up. I took a seat front and center as the music started and my sister walked out onto stage.

Jenny obviously hadn't planned on any of this happening today. She had worn a short, black dress and sensible heels with her hair pulled up into a ponytail. Honestly it looked like she was still trying to appear professional for court. Jenny stood frozen in place, barely moving and after half a song I signaled for the DJ to kill the music. "Alright, get down from there." I sighed as Candy approached with our drinks. "I'm going to take the new girl to the back, check on the rest of the girls and come get me if anything comes up." Candy nodded and headed back to the dressing room as I took my sister back to the private booths. As we passed by the guard, I gave him a discreet signal and pulled the curtain around the booth. Jenny and I set our drinks on the side table and I sat next to her. "Ok. Let's be real here, you can't dance, or at least you're going to need a lot more practice before you're ready to be on stage, so that limits your options. You're willing to do anything right?"

Jenny nodded, a tear rolling down her cheek. "Y-yes. I'll do whatever it takes. I just... I don't know what else to do."

I pulled my sister closer and ran a hand along her back. "It's OK Jen. I know, you're in a bad place right now. Getting out of this mess isn't going to be easy, but I'm going to give you what help I can. You do your part, I'll do mine, and soon you'll be back on your feet. OK?" Jenny nodded and took a drink. I slid my hand further up her back, grabbed the zipper on her dress and pulled it down before she could object. Reflexively Jenny reached up to cover her chest, I gently, but firmly gripped her wrist and pulled it away. "If you're going to work here, then you're going to have to get a lot more comfortable with being naked. Shouldn't be hard, I've seen your Instagram. Now let's see what you're working with."

Jenny got up from the couch and let the dress fall. Her bra and panties were mismatched cotton. No lace or lingerie, just my sister standing in front of me in a pair of plain cotton panties and a padded bra. I knew she was capable of being sexier, I had seen it online plenty. "Come on Jen, you can do better than that. Take a drink, pretend I'm someone else, whatever you've gotta do. Right now, I'm your client and you're here to give me a private show." Jenny bit her lip and took another drink. Music started to filter in as the DJ started up a playlist and Jenny took the cue to start dancing.

Jenny looked away and started to move her hips slowly to the rhythm. Turning around she bent over and pushed her ass towards me. Even if the rest of her was skinny and awkward I had to admit that Jenny's ass looked incredible. A part of me wondered if her ex had paid to have some work done at some point because I was pretty sure that she didn't have an ass that round or full when we were growing up. I reached forward and put my hands on her thighs, which caused her to freeze for a moment but she kept going. I pulled my sister closer and felt her shift her weight to my lap. Running my hand further up her body I slipped a finger under her bra and whispered in her ear. "This is usually where you take this off." Jenny licked her lips and leaned forward, letting her hair fall in front of her face. Her hands wrapped behind her back and undid the hooks in a quick flick. Standing back up Jenny turned, her hands clasping the loose bra to her chest, saw my face again and froze. Once again, I reached up and took her hands away, letting the bra fall free, my sister's naked breasts mere inches from my face.

Jenny's tits were smaller than most of the rest of the girls, I wasn't about to check the tag but I was sure she was only a B-cup because her bra was padded. Still though, the skin was smooth and flawless and her areola were comparatively large with nipples that stood straight and proud. I smiled and rubbed my hand up from her thigh to cup her breast and lightly roll a nipple between my fingers. "Very nice Jen." She looked away and blushed before she licked her lips and started to dance again. Climbing back in the seat my sister straddled my lap with her knees on either side. The song changed and Jenny matched her tempo to the new song as she picked up speed, grinding her hips against me. My sister arched her back pushing her chest into my face, her breasts brushing past my lips. After a few moments of her dance Jenny climbed off my lap and swayed her hips in front of my face again as she hooked her thumbs under her panties. With a playful bounce of her ass Jenny teased me for a moment before finally sliding her panties down her legs to her knees exposing her dripping pussy. Jenny looked back grinning before seeing my face and freezing again, apparently having forgotten that it was her brother she was stripping for.

The third song started and Jenny looked away, swaying her hips again. She turned back to me, kicking her panties off and letting me see her fully nude for the first time. I ran a hand up her inner thigh, feeling where she had left a trail of wetness. Even if her brain was telling her that it was wrong to do this for her brother, her body wasn't getting that message. Jenny straddled me again, looking over my shoulder as she focused on her dance. She ground her hips into mine and I could feel the wetness soaking through my pants. I slid my hands behind her and gripped her ass cheeks, not restricting her or guiding her, just feeling the motion of her round, juicy ass bouncing up and down on my lap. Through the rest of the dance Jenny moved wilder and wilder, still pointedly not looking at my face, but giving me a hot, wet lapdance all the same.

When the third song finally ended, I put a hand on her thigh and told her that time was up. Jenny stood back up and fumbled for her clothes. As she was pulling her panties back up I pulled a $50 out of my wallet and handed it over. Jenny looked at it, blinked and shook her head. "Wait, just 50? All that and all I get is 50 dollars?"

I nodded and straightened my shirt. "Actually 10 of that goes to the house, but I'll go ahead and put that against your loan. It was just a lapdance Jen. It was a good lapdance..." I fished out another $20 "It was even worth a tip, but let's face it Jen, a lapdance is really just a sales pitch." I let her think about it for a moment before I say anything else. "You're really willing to do anything?" Jen clutched the money tighter and took another drink. I pulled another $200 out of my wallet. "Oral?" Jen looked at the money, briefly flicked her eyes towards my face and then downed the rest of her drink before pushing me back on the couch. I grinned as my sister laid on the couch next to me and fished my cock out of my pants.

Tentatively Jenny reached out and grabbed my cock, before she could start, I tapped at my watch. "We have 15 minutes before the club opens. Make me cum before then and you'll get a good tip." Jenny didn't need any further encouragement and went to work licking and stroking my cock. I had to admit that I never would have expected to see my sister stretched out on the couch next to me, stuffing my cock in her mouth all because I offered her money to do so. As my cockhead hit the back of her throat Jenny gagged and coughed, spit covering my balls. She pulled back to catch her breath but kept stroking. I reached over and gripped her ass letting my fingers slide under her panties to run along her slit. Jenny moaned and swallowed my cock again, stopping before she gagged and rubbed my spit covered balls.

After another few minutes Jenny pulled back, gasping for air. She looked up at me, this time with no hesitation. "Are you close?" I grinned and shook my head. She was good, but I knew at least two other girls who were working tonight who were better. I gestured to my wrist letting her know she only had 10 minutes left. Jenny bit her lip and thought for a few seconds. "How much will you give me for sex?"

I reached over to my wallet on the table and pulled out and started counting out hundreds. "$200 for oral, $500 for pussy, $800 for anal. The rougher and freakier the more you can charge. If they want the weird shit, you can pretty much set your price. There's a guard right outside in case things get out of hand. There's condoms, lube and wipes in the drawer there." I put the money back in the wallet and set it back on the table before Jenny jumped me.

My sister pushed me down on the couch and climbed on top, pulled her panties to the side and guided my naked cock to her dripping wet pussy. Feeling a naked pussy wrapping around my cock stunned me for a moment. It had been literally more than a decade since I'd had unprotected sex, but something about it being my sister made it feel so fucking right. I wanted to stop her, to push her off and scold her for not using protection, but right then my brain was short circuiting. I couldn't speak, couldn't move, couldn't think, I just knew that I wasn't going to last long. Jenny's hips started to move as she fucked herself on my cock. I looked down to see her pussy lips swallowing all 7 inches of my cock over and over again ash she bounced up and down on my lap. It was only a few minutes before I felt my orgasm building. My eyes shot open and I looked my sister in the eyes. She leaned down and kissed me, hungrily before whispering in my ear. "It's OK, cum in your little sister's pussy. Do it for me big brother." I couldn't hold on any longer and came deep inside my sister.