Jo blows the pimp

In the condominium complex where lovely JoAnne had lived since she was a young girl, there was one woman whom she always had admired. A single mother now of two teens, one boy and one girl, Tiffany somehow always had managed to work out daily, maintain a spectacularly trim and fit figure, and otherwise look so amazing all the time. Even now, in her late thirties and with a daughter age nineteen and a son of seventeen, she could pass for early to mid twenties. Jo once remarked, years ago, that it was Tiffany’s job to look amazing. She didn’t realize, quite then, how true that statement was.

Tiffany had long light brown hair which always was perfect. Her make-up always was perfect. And her clothes always were so elegant… so many nice tops and nice pants and always new (and very tight) designer jeans, as well as a seemingly endless array of sexy high-heeled shoes. Even when she was just putting out the garbage, guys all through the complex would stare, wantonly, out of their windows, or find numerous not-so-clever reasons to check for something in the trunk of a car. Watching Tiffany bend over in those pants or those jeans was like a dream come true for these horny men.

Tiffany also drove a very sexy and sporty little car, not overly expensive but always in perfect repair. The auto mechanics tripped over each other providing her service. Why not? She had serviced them all, many times.

Tiffany’s condo was beautiful inside; nice new furniture and nice prints on the walls; and lots of cute ‘things’ everywhere. Jo had been inside once and discovered that Tiffany had an almost endless supply of teddy bears she had been given over the years, that decorated every room except her son’s; her daughter had claimed a few.

“Who gave them to you?” Jo asked once when, at age 15, Tiffany had invited her inside.

“Men,” Tiff answered quietly and smiled… but explained no more. But then she added: “One day you could be getting teddy bears like this too.”

And Jo smiled happily. She loved getting gifts from the boys at school, who apparently thought she was very pretty. Tiffany, too, had long since noticed how pretty Jo had become, with great interest. And now that Jo had just turned 18, she decided to invite Jo over to ‘talk a bit’.

It was an invitation that Jo had been waiting for. Tiffany’s daughter, Bronwyn, had assured her it was coming. 

“She thinks you’d be perfect at it,” she said.

‘It’, of course, meant prostitution. For that was what Tiffany did in order to afford all the nice things she had. Oh, she told people she worked at a large local life insurance company, but everyone in the complex knew that this only was part time, at most 2 afternoons a week. But no! Tiffany was a prostitute, an escort, a hooker, a whore. And Jo was so excited about becoming one too.

Bronwyn had started almost a year ago, and told Jo all about how fun it was and how much money she was making. Although she still lived with her Mom and brother, she now had a car of her own, and lots of nice new clothes. 

“How much do you make?” Jo had asked her. 

“It depends how many tricks I do or calls I get,” the older girl explained. “and whether I’m taking calls by phone or working the street. But I can make over $1000 in a night.”

“You get to keep all that?” Jo asked, her jaw dropping open.

Bronwyn laughed. “No… I only get to keep 30% for now.”

“Who gets the rest?” Jo asked, puzzled. “Your Mom?”

Bronwyn laughed again. “No,” she shook her head, smiling. “My pimp does.”

In fact, that was why Tiffany wanted to meet with Jo today, only a few days after Jo’s eighteenth birthday. Already Bronwyn had told her Mom that Jo definitely was interested in all this. The next step was for Jo to meet Tiffany and Bronwyn’s pimp, Sly. Jo was nervous, but excited, as Tiffany explained everything to her.

“Is it really as fun as Bronnie says?” she asked the woman she admired so much.

“It’ll be lots of fun for you,” Tiffany assured the younger girl. 

“Is Sly nice?”

“He is nice,” Tiffany assured her. “But he also is a businessman. You’ll have to impress him into hiring you.”

“How?” Jo asked nervously.

“I’ll show you,” Tiffany said, so motheringly. “The first thing we need to do, though,” she smiled, “is take you out shopping.”

For Jo, it was like Christmas. Tiffany loaded both Bronwyn and JoAnne into her car and off they headed to the mall to buy Jo an outfit ‘to make Sly cum in his pants’. It took a while and visits to several stores, but finally Jo had her outfit… a tight short-sleeve, pink top; a matching pair of pink, satin bikini panties (“In case Sly wants to see you with your jeans off, Honey”); the tightest pair of navy blue jeans Jo ever, ever had worn (so tight she really had to pull to get them on, and too tight for her to use any of the five pockets – three in front, two in back); and 2 ½ inch black spike heels (or ‘pumps’, as Tiffany called them) that were so high Jo actually had to practice walking in them.

It was Bronwyn’s idea that Jo put on and wear the full outfit now, in the mall, while they finished shopping.

“Shop for what?” Jo asked.

“Make-up for you,” Tiffany explained. “And then we have Jacques over at the Hair Salon scheduled to do your hair at 3. He’ll help you with your make-up too, so that you’ll look like a real little street hooker when we go see Sly at 6. If he likes you, he might put you to work on Dundas.”

“Tonight?” Jo asked, amazed at quickly things were moving.

“Wouldn’t you like to get started?” Tiffany asked.

Jo nodded her head, excitedly. They found a changing room where Jo changed into her panties, top, jeans and heels, and then headed off to the big Pharmacy where Tiffany and Bronwyn helped Jo pick out some ‘perfect’ make-up… bright red lipstick; pinkish rouge, purplish eye shadow; and nice eyeliner. Jo wondered how the combination of colors would look on her face, but Bronwyn assured her that Jacques definitely knew what he was doing, and that the combination would be perfect for the street.

“The guys who pass by have to know you’re tricking,” she explained.

Sure enough, Jacques was an artist extraordinaire. He added a bit more blonde to Jo’s long, light brown/blonde hair and treated it so that it was silky soft. He let Jo apply her own lipstick, but then carefully took over to apply the pink rouge to her cheeks, the purple eye shadow and the lip and eye liner. At about 4:30, Jo stood up and regarded herself in the mirror. There was no doubt about it… she DEFINITELY looked like a street hooker now. The pumps were so high. The jeans were so tight they showed the crack in her ass. And she had an amount of make-up on only a hooker would wear. It was PERFECT! 

“Oh… thanks so MUCH, Jacques,” she said sincerely.

“Perhaps you can thank me with a nice blowjob?” he asked her, ever so calmly. “I can be your first customer.”

Jo quickly glanced at Tiffany to make sure this was alright. Tiffany smiled and nodded. This was going precisely according to plan.

“Sure,” Jo answered happily, and sank to her knees at the man’s feet. He was gay, she had been told, but still loved the girls he worked on to give him an occasional blowjob. Jo felt honored he would ask her. When he told her that, just two hours earlier, his cock had been buried 8 inches into some ‘ugly guy’s ass’, and that he thought it was so funny that it now was deep inside such a pretty girl’s mouth, she giggled inside.

Tiffany ran out for a minute and returned with a guy from a camera shop across the way so Jo could pose for a few pictures, and Jo thought that was very fun.

“Hmm hmm?” she asked him sweetly.

“Perrrrrrfect,” he told her, and she felt very proud.

She also was so proud as she and the others walked back through the mall to the car. Everyone was staring at her, and she knew it was because they all knew she was on her way to work as a hooker. A couple of guys even asked her what corner she’d be working. She didn’t know, but Tiffany told them to look for her on “East Dundas around Elizabeth Street” and the look on their faces told Jo she had some sure customers. Again, it was so fun to have met these guys she was pretty sure she’d be blowing later. She just hoped they brought friends along so it would be even more fun for her.

Jo waved to them from the back seat as Tiffany’s car sped off. It still was not quite 5, so they were headed over to Bronwyn’s boyfriend’s place. 

“Why are we going there?” Jo asked.

“Two reasons,” Tiffany explained. “First, Mark is going to post some of these nice pictures of you on the internet, because there’s a site there that Johns often go to, so they can check out what girls are working in town.”

“Does that mean for sure I’m working tonight?” Jo asked, hopefully.

“Probably, Dear” Tiffany answered. “Sly knows I’m bringing you and he usually likes getting his girls on their knees right away.”

Jo laughed. It was cute the way Tiffany had just put it.

“And, second, there are a few blowjob techniques I want to show you, and Bronwyn has kindly offered Mark for you to practice on.”

Jo glanced at her 19-year old neighbor and thanked her.

“He’s looking forward to it,” Bronwyn assured her.

Mark turned out to be an internet whiz. He not only knew how to post several pix of Jo in action on the net, he also managed to send those pix automatically to anyone who had accessed the site over the preceding month, and have one of the pictures (Jo’s favorite) automatically as the desktop picture on their computers. 

“Over 10,000 monitors in and around town have your pretty picture on the screen as we speak, with instructions of where to find you tonight and when” he smiled.

Jo kissed him.

He had entered several great pictures of Jo onto the net. In all of them, she was on her knees with Jacques’ cock deep in her mouth. In most, she was looking straight into the camera with her big, beautiful brown eyes wide open. Some pictures showed her full profile, from the tip of her head to the tip of her toes (in those sexy shoes). In all, she was fully dressed. Several of the pix showed how great her little bum looked in those amazingly tight jeans. They all were so flattering of Jo. The picture she chose for the desktop was a combination of two pix, side by side. One was a full profile showing Jo in her entirety, kneeling there with her big eyes, sucking mouth, cute tush and sexy shoes all showing as she stared straight into the camera, her eyes wide open and at least 3 or 4 of Jacques’ thick inches inside her mouth. Next to it was a close-up of her face, taken less than a few seconds later, with her again looking straight into the camera. Jo had a playful twinkle in her eyes and, even though her mouth was wrapped around a big cock, she seemed to be smiling.

“If these don’t bring the Johns out,” Mark said, “Nothing will.”

And both Tiffany and Bronwyn agreed. These were WONDERFUL pictures of Jo. Jo, herself, was EXTREMELY pleased and proud.

All of this good work had been accomplished in less than 15 minutes, so Jo still had a comfortable half hour or so to practice on Mark. After he stood up and led her to the living room, she happily settled down on her knees at his feet, and Tiffany kneeled right next to her.

“Let’s see you start,” Tiffany prompted her.

A little, nervously, Jo leaned forward to take Mark’s still soft cock in her mouth.

“No, no,” Tiffany stopped her. “Be playful. Talk to it. Introduce yourself. Kiss it. Lick it. Play with it like it’s a fun new toy. Guys like that.”

“We do,” Mark’s voice sounded from above.

A little self-consciously, Jo introduced herself to the cock. “Hi,” she said. “My name is JoAnne and I am going to suck you now.” She laughed nervously.

“Not bad. But tell it you want it to cum in your mouth so you can swallow it.”

Jo turned back to the cock. “If I’m a real good girl, will you cum in my mouth?” she asked, ever-so-sweetly.

“That’s better,” Tiffany smiled. “You’ll think of even better things to say with practice.”

Jo nodded, and then leaned forward to kiss the cock, ever so gently. Then she slipped down below it and ran her tongue along its entire length, all the while staring up at Mark, who stared down at her with great interest and delight.

“Can I suck you now?” she asked the cock, playfully. Aided by Mark, the cock nodded. Jo smiled, opened her mouth and then leaned forward, her eyes watching Tiffany’s expression.

Today’s blowjobs were not the first Jo ever had given, but no one expected her to be as talented as she was. Within a minute, her naturally gifted mouth had Mark moaning with ecstasy as she slowly and rhythmically slid her mouth to and fro along his shaft. What amazed him was how amazingly soft and gentle, and yet titillating her mouth was. What amazed Tiffany and Bronwyn both was how calm and comfortable Jo seemed to be with a stranger’s cock in her mouth. She wasn’t just sucking Mark’s dick; she was savoring it, like it was the tastiest treat she ever had had. This boded very well for her in her new profession, since she soon would be getting thousands of cocks in her mouth. Mark was very well-endowed. Bronwyn admitted her mouth often felt stretched when blowing him. But Jo opened her mouth wide with ease. And then she started to take more and more of him into her mouth.

Tiffany glanced over at Bronwyn and nodded. Then, one time when Jo was leaning fully forward with at least 4 of Mark’s inches buried, Bronwyn reached up to take hold of the back of Jo’s pretty head and firmly pushed Jo forward. In horror, Jo felt Mark’s huge cockhead pop past her tonsils into her throat, and then felt the thick member sliding down her throat.

“Hmmmmmmmmmm,” she squealed helplessly.

Tiffany quietly told her to ‘just breathe deep and relax the muscles in her throat’ and Jo did her best. Soon, although she was gagging continuously, she had resigned herself to the firm hand on her head and no longer was fighting it. Tiffany wondered when Jo would suddenly just jerk her head back or use her hands to push away; but Jo did neither. Once she had decided that she could handle the gagging, the full feeling in her throat and having her nose buried in belly fat, she rested her hands calmly on her thighs and just stared straight ahead at the hairy belly not one inch away. Tears streamed down her cheeks, and every few seconds her entire body convulsed with gagging, but she did not pull back.

Tiffany couldn’t believe it. Most girls took years to learn how to deep throat, and Jo already was a natural at it.

“Are you okay, Jo?” she asked her.

“Hmm hmm,” Jo said, cheerily. Despite all the gagging and whole body heaves, this was fun. 

Finally, Jo felt Bronwyn let go. Jo resumed sliding her mouth back and forth, as if nothing had happened, except that she was taking Mark deeper into her mouth than before and everyone knew that she was, at the very least, bringing his cock tip all the way to her throat with each thrust. Several times, she took Mark deeper down her throat and held him for a moment or two before sliding back.

“This is amazing, Jo,” Mark sighed, breathlessly.

“Hmm hmmm,” she cheerily thanked him.

It took only eight minutes before Mark was spewing out the most cum ever into Jo’s mouth. She kept sucking him, sliding to and fro even while her mouth filled with semen and sperm. It wasn’t until he was fully soft, several minutes later, that she let his shrunken cock slip out of her mouth.