Dara, Entering the Family Business Ch. 01

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Fresh out of high school Dara joins the family business.
12.4k words
4.49
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23

Part 1 of the 2 part series

Updated 06/09/2023
Created 04/09/2020
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Jessie92
Jessie92
503 Followers

(All acts are legal where performed and all occur by persons 18 or older)

My mother is a whore. Well, these days a madam, or a pimp if you will, but you don't get to judge her. Her family moved from Laos when she was young and keeping with the family tradition, she married a GI in Japan who upon finding her pregnant with me dumped her in Nevada. My only knowledge of my father is a photo of them together on the beach, mom in a cute bikini from the late 80's or early 90's, and him in board shorts with a tattoo of a dragon on his chest, barely visible through his black skin. I used to stare at that photo and wonder why I wasn't good enough for him to stay around. That's my dad. I don't know him, and don't care to. Mom did the best she could and entered her own mother's old line of work, as other than speaking passible English she had no other work skills. Soon she was popular enough to leave the brothel and set out on her own and began booking other girls as well. She actually credits me with the knowledge of how to run her business as when her tummy got too big for her to sell ass, the brothel owner put her in charge of the books and running the house until she could get off her feet and on her back.

As far as I know, mom hasn't fucked for money in years.

An only child, I never did without. My mother made sure I had everything I needed, and I had a pretty normal childhood. She never brought work home and since I was a toddler, she was home every night, cooking dinner, helping with homework, watching TV (for a while in the teens we were both committed Gleeks, that will become important to the story in a bit) and generally just being a great mother.

As I said, you don't get to judge her. Mom is great.

I knew about sex early on. Mom was open and honest about it all. I knew the difference between sex for love, for pleasure and for commerce for as long as I can remember, and safety was always stressed. I knew about birth control, I knew about VD, condoms, and the importance of regular testing of both parties if you were going to go without, and why that was a risky idea, even in a relationship. All in all, I think my sexual education at home was far more thorough than that at school.

You might think mom encouraged me to have sex, that it was no big deal, but that was not the case. She urged me to wait until I was ready, and until I had a guy or girl ready and worthy of sharing my first time with. In fact, I think our openness meant I lacked a lot of the curiosity my classmates had on the subject who made such a big deal about it. Whoring was something my mom's employees did, not her daughter.

I did wait until I was with a special guy, and until I was 18, but you know how that ends up. With me on the bed, my legs wide open; panting at the edge of an orgasm I didn't have while my boyfriend cums too fast then strips off the condom awkwardly to leave a small puddle of seed on my bedspread. Oh well, my "have another human being inside your pelvis for the sake of love" ticket got stamped and I moved on with my life.

I guess she knew I had a bit of a wild streak, maybe that runs in the women of our family. When I turned 18, we talked about the family business in detail, but I didn't think I was ready or willing to sell ass and lacked the street knowledge to help her run it in any real way. I have been with exactly 2 guys a total of three times, plus a few bj's, since then. Mom assured me that was enough experience as it was a 'learn on the job' thing, but she didn't really want me to join her business in that capacity anyway. I did want to make some money for college however and there isn't a lot of opportunity in our town for a 4'11" half black, half Laotian waif of a girl that barely weighed 95 pounds, most of that in her butt. I was still in high school and mom didn't want me to work anyway. I thought about taking a dealer class to get certified to work at a casino once I graduated until I started college. The only problem with that was that it took several months to get certified, and I was probably too short to get a job working in the pits. They like their dealers to be able to see over the tables and that was a challenge for me.

"You know Dara, it's up to you, but if you don't want to work fast food, I do have calls for dancers. I'm not saying you should, but you have the looks for it and most of my dancers do pretty well. I get a cut from them, but you wouldn't have to pay..."

"Mom! You want me to be a stripper? Geez" I replied with a laugh to what must have been one of the weirdest family dinnertime conversations ever. Well at least she wasn't wanting me to suck dick for a living. Yet. I mean, I don't judge obviously, but I don't think either of us wanted me to go whoring. Me because I really just wasn't that sexual, and mom because she wanted better for me that she had in her youth. I liked sex, but wasn't driven to have it constantly, or even regularly. Education was far more important in my life.

"Only if you are interested. I don't have many young dancers, and if you do the fast food gig you might be able to save what? $1500 a month for school? And you have 2 and half months before you leave for college? Some dates get my dancers that much a night. I know we've never talked about it, and you know my feelings on you getting a health card (the card that was required for me to sell pussy, yeah mom and I talk about everything), but it's an option. If you wanted to, well I wouldn't judge. You know that. And I can send Damon as your escort so you would be safe. Just think about it."

"Uh, okay. I... I'll think about it. I don't really know anything about dancing though that I didn't learn from watching Glee."

"Truthfully, that's probably enough, they aren't really watching for your dance skills, and Clara can teach you the rest. There's really not that much to it. There's not even a lot of dancing to it. The guys are like an ATM that you have the PIN number to."

I did think about it for several days. It was an interesting offer in that I was a bit of an exhibitionist anyway, I liked being the center of attention, and although I had never been naked in front of a group before, I wasn't shy about my body with the guys I had dated. If I had a fetish it was for lingerie, I think that maybe the only real side effect of mom's work on me, she always had pretty underthings in the laundry and when I was old enough, I started my own collection. Even though no one else saw me in it, I felt pretty and girly when I had lacy underthings on.

I had no moral or social qualms about stripping either, in fact I had considered talking to mom about doing some cam shows like a friend of mine was doing but decided not to as video and photos on the web never really go away and I hoped to graduate in three years and go to dental school. Being a porn girl, even a mostly amateur one, would not help my chances of getting accepted to a good dental school. That said, if a dude wanted to see me naked bad enough to pay me, and the money was right, I probably wasn't going to turn them down.

Finally, with Damon as my escort I had no qualms safety wise. He was big enough and ripped enough to intimidate anyone. He had worked for mom for years and got paid to go with girls and make sure they were safe with new clients. Most of mom's clients were vetted, some being repeat customers for years, but when a new one came along Damon was just outside the door to make sure they were safe. With him as my escort I knew guys wouldn't get too pushy, and if I had sex with a client, it would be of my own choosing. I had no boyfriend at the time so I didn't have to worry about what one would think, and I hoped to spend the summer single and free, so the timing was right as well. Still, it all made me very nervous as it came out of nowhere and was not something I had previously considered, other than via an internet connection.

At breakfast, the Saturday after my graduation the night before, I brought it up with mom again.

"Okay, I'll try it, but Clara has to help, and Damon has to be there, okay?"

"Okay" was her only response before talking to me about wardrobe and make up.

Mom had never danced a lot, if at all, but after running a string of ho's for a couple of decades she ended up scheduling enough bachelor parties that just wanted a stripper, or couldn't afford a real ho, that she rounded up a bunch of sluts to get naked too. Mom's ho's were all high dollar escorts. She didn't fool with street whores as according to her there wasn't as much money and they were a pain in the ass to put up with. There wasn't as much money in providing strippers as there was in escorts, and mom's escorts were quite expensive, but there was no reason not to provide both services. Mom liked the money, and the money was good.

Clara was her most popular stripper and did okay as an escort as well. I had known her for a couple years and we always got along. Mom called and asked if she would mind me going to a bachelor party with her that night and she agreed quickly. Clara and I could not look less alike. While I was short, mixed and tiny, she was a tall red headed white girl with some serious tits. I wasn't sure if they were real or plastic, but she looked fabulous, even if she did dress a bit slutty. It comes with the job.

My "costume" for the night was simple. A two-piece party ensemble not unlike what every other young woman on the strip would be wearing, with sexy underthings beneath, and some spiked heels that in Sin City didn't really set me apart. Mom stressed that the upper part, a top that just barely met up with the top of the skirt, had to be something that could be removed separately from the skirt so I would have more to take off. She also went over my lingerie choices and told me the best order and sexiest ways to remove them and expose myself to strangers. Yes, that is an awkward conversation to have with the woman that raised you, even if she is a pimp.

I have long, straight, black hair, typical for a half Laotian girl, and mostly Asian features, the main one being that I'm so tiny. Oh and gigantic tits? Nope, not in this story. I'm a small C cup on a day when I'm really bloated, so a push up bra is both a must and mostly a waste of time. Still, I'm told I'm pretty and aside from my darker than Asian but still not black skin, the features I got from my father's genetics is my wide smile and full lips, as well as a decent booty that was definitely my best feature. I wasn't that sexually experienced but the two prior boyfriends that had managed to get their dicks in my mouth pronounced that I gave the best blowjob ever. I think they say that to all the girls though. The other girls had not learned BJ secrets from their mom though I bet. My ass on the other hand, was admired by all who stared at it, which would have made me uncomfortable I suppose, except for the aforementioned exhibitionist streak. As the day wore on, I daydreamed about finally showing it off in a way that might really feel rewarding to me; shaking it in a cash customer's face.

Just before 8 pm, Damon and Clara pulled into the driveway to pick me up. I was so nervous, especially since mom was looking me over as I walked to the door.

"You look great Dara, remember, it's a fun job and with Damon there, you're safe."

"Thanks. I'm... uh, pretty nervous but..."

"Excited?" She smiled.

"Yeah, in a way, I guess I am," I admitted.

"Here, don't forget party hats for the boys," mom said as she handed me a bunch of condoms.

"Oh, I don't need them I won't be doing anything like"

"It's a weird business and it plays with your body and your mind. Always be ready. Right now, you're thinking it's not sexual for you, but that can change. You never know when the right person or situation can turn your thinking." She smiled.

I took the rubbers and put them in my clutch, filing it to the brim. 'Geez, how many guys did she think I would fuck? Well, if it makes her feel better.'

"Oh, and you better take this too," mom said as she handed me a small bottle of lube.

"What? No way am I letting some stranger give it to me in the butt mom! Geez," I nearly shouted. Mom and I were completely open about sexuality and I had made it clear in our discussions that my ass was exit only and not a playground for filthy minded guys. For her to think for one minute that dancing naked would somehow change my opinion was shocking to me, but she rolled her eyes and answered like I was a moron.

"Hand jobs Dora, a stripper's best friend. Are you sure you're ready for this?" She grinned.

"Oh."

A kiss on the cheek and I was gone into the night.

"Hey girl! So you wanna be a dancer too now?" Clara grinned. She was seated beside Damon in the front, so I sat behind her in the back. "You'll be great!"

"Well, I'm thinking about it. I really don't have any idea what I'm doing, I... I'm kind of nervous."

"Oh, don't be, that's why this is a ride along, so you can see how it works. Tonight, we have a bachelor party at a hotel on the strip. It's a good one to start with. The call they made to book us and the hotel they are at tells us a few things about our johns. First, they have the money to get a suite on the strip so they aren't college boys; those are the worst. Second, they have to money to hire us instead of going to a club. That's good because they will have the cash for extras and hope to get some or they would have just gone to a club, and extras are where our money is made. These guys know it will cost more, but a club stripper isn't going to do the things we do.

This is a good first gig for you to watch, I'll handle everything."

"Oh, so I won't be dancing?" I asked, somewhat relieved and somewhat disappointed.

"Maybe, maybe not. Here is how it will work. We'll come in, check the place for cops, that's the first job. Then start the music; you and Damon will hide in the corner while I work. Seriously, just stand there, clap your hands, wiggle your hips a bit and go 'woohoo' when something comes off. I'll be working them for extras. These guys always want to fuck us, but usually settle for getting the bachelor laid. There's always another guy, the money guy, he expects to get laid too, but charge him more. If you've never done a threesome, you probably want to just stick to the bachelor."

"Oh, so you plan on fucking them? That's what you mean by 'extras'? I figured you meant more dancing; I got the impression from mom that doesn't often go on and"

"Your mom knows exactly what goes on. Who are you kidding? I try to get by with a blowjob or hand job honestly. Usually they are so worked up they cum pretty fast and if I can take care of them the easy way, I can go work another party later."

"Or fuck your driver," Damon added.

"Right, or fuck Damon, which I usually do anyway," Clara laughed.

"It's a basic courtesy of the job," Damon grinned as he turned his face briefly towards me.

"Right, anyway, while I'm taking care of bachelor boy, you can entertain the room if you want, but don't dance for free. Just don't. They have money. They brought money to drink and gamble with and there are ATMs in the lobby if they run out. Don't do shit for free, understand Dara?"

"Got it," I replied, now more nervous than ever. I had no idea how to ask people for money to see me naked, especially if they had already paid to see someone else naked and then there was the whole fucking Damon issue on top of what the customers might want beyond a dance. See, I had known Damon a half dozen years at least, probably more if I thought about it. He was in his 40's and had worked for mom for as long as I could remember. Yeah, he was fit as all hell and super nice, the idea of banging him was foreign to me. I'm pretty sure he had fucked mom at one time or another, and now from the way he and Clara talked, he had probably fucked every whore that worked for her. Just... it was weird. Damon was never a perspective partner to me, and it seemed unnatural, like fucking my childhood babysitter or something.

I had to put it out of my mind; the night had plenty of weirdness without worrying about fucking Damon. Besides, what could I do? Call mom and say 'Hey! Damon wants to fuck me and it's creeping me out!' I'm pretty sure that would have no effect. Damon's a guy, he wants to fuck everyone, and mom knew it was sex work when she gave me the job. I knew it was sex work, of a type anyway, when I asked for it. If during my week of contemplating the job it didn't occur to me that people I might not want to have intercourse with would be expecting to part my labia with their blood engorged erections I was a fool for not considering it. At that moment, I felt like a fool and wondered if I was in over my head. I had thought about dancing and stripping and showing off my nakedness to anonymous strangers and how cool that would be, not that all of them would develop a desire to stick things made of man meat into my body with an aim towards climaxing because of, and without regard to, me or what I wanted and felt.

I couldn't stop at this point though for a couple of reasons. I told mom I would try it, and I was determined to do so if only for the common experience with my mother and as a step towards being a grown ass woman. In my family women paid their own way, used their bodies for profit, and did so without shame. We separated romance from erotic pleasures and mom had provided me a great life by doing so. I was 18 and it was time for me to stand on my own a little more. The second reason was between thinking of getting naked for strangers and Damon now seemingly intent on banging me either tonight or sometime in the future, using what I could only imagine was a big ebony cock to split my tiny girl bits apart and toss me around like a fuck toy, I was starting to get a bit moist. And as nervous as I was, I was beginning to feel the power of that slit between my legs. Besides, I reasoned, if I didn't like it I would just not do it again.

Before I could over think it anymore, we mercifully arrived on the strip and were soon in the casino hotel's garage. I was admonished to never use valet parking in case I had to leave fast. Before we got out of the car Damon went over our safe words, the words we would shout if we needed him to come in and rescue us from a bad situation. It had to be something that wouldn't normally come up in a sexual situation and Clara used 'banjo.' It took me a minute until I came up with 'bookmark.' Then it was a long walk of shame where I felt like everyone was staring at us and judging me, in their minds saying 'She's a whore! Just look at that whore walking in here to sell her whore ass to men she doesn't know! She's going to suck 20 dicks and let them cum on her face and use her ass like a whore, because she's fucking whore! Whore!'

In truth though, we looked a lot like everyone else wandering the casino at night, and less sleazy than many. I got stuck carrying an oversized bag that held the small MP3 player 'boom box' and I just stuffed my clutch filled with condoms and lube into it. The cool hotel air drifted up my skirt and around my bare upper thighs as we entered, reminding me of just how sexy I was underneath mid length mini and cotton blouse I wore. From outward appearances I could have been there for a teenage banking seminar, if there were such a thing, but get rid of the skirt and top, and I was dressed for sin. The more I walked my confidence built, and I began to hope that sinning would start sooner rather than later.

Clara and Damon both had the room number and we were right on time. Both seemed familiar with the layout of the casino hotel, a knowledge born on the job I suspect. We took the elevator to the 15th floor, found the room, and Clara knocked.

"Is this where the party is?" She announced with a grin as the door cracked open.

Jessie92
Jessie92
503 Followers