Jessica's New Life Ch. 04

The Second Challenge

"Good work recruiting those new young studs," beamed Jenny, "I've had two of them already but the big one, Dashawn is it, I think I'm going to have to see what he's made of. Wish me luck!"

James smiled at Jessica's expression. He knew just what she was thinking. The young men she'd 'persuaded' to join the club were all just 18. Jenny was a bottle-blonde running to fat who looked like she wouldn't see 50 again.

He explained, "Just like we recommend female prospects, current and past Taylor girls get to recommend new male members for the Cock Pit. Word soon gets around. If a young Black man wants to reach the land of unlimited bareback fucking with the finest white pussy then it pays him to show Jenny and the others a real good time. It's a little reward for the girls' past services."

"Taylor girls..."

"What you'll be when, or if, you meet all your challenges. Which reminds me, you'll be picked up on Saturday afternoon at three. Dress real classy and real expensive. Talking of dress rules - what about Rule One."

Jessica swirled up her mid-length skirt to reveal her naked pussy.

"Passed that test," smiled James, "now go find yourself some fresh Black cock."

***

Jessica prepared herself carefully for her challenge on Saturday. She bathed and then lightly misted her body with her most expensive perfume. She wore a simple but extremely exclusive designer dress. It essentially left one shoulder and most of her back exposed. The ultra-sheer red material was kept in place by thin black sequined straps and stretched tight over her chest. It was not a dress that you wore a bra with. Besides, she was proud of her pert well-formed 30Ds and today she would enjoy showing them off. The dress was tight around her ass, clearly showing the curves of her buttocks, and then flowed loose down to just above her ankles. She wore modest heels and decided to wear her classic long black leather coat for travelling.

Her ride arrived on time and she easily identified it by the booming bass blasting out from the car's speakers. She looked in the window and hesitated - it was a man she didn't know. He asked, "Jessica?", and flashed a 'Cock Pit' card at her. She saw his picture, that month and the name 'Antwan'.

Antwan drove some sweet wheels and was well turned out himself. A well-cut suit jacket with a heavy gold necklace over his black shirt. His hand as he waved Jessica into the car showed a couple of heavy gold rings.

As soon as he had driven out of her neighbourhood Antwan turned down his radio to a background level, "Been to H-town recently?"

H-Town was the nickname for the neighbouring city, now largely connected by sprawling suburbia. H-Town had always been the poor neighbour and the decline of heavy industry hadn't been kind. While Jessica's city was fairly prosperous, with pockets of poverty, over there it was a ring of wealthy suburbs round a city that had just about managed not to go the way of Detroit, but only just. 'H-Town' referred to a major heroin epidemic that had hit the inner city there in the 70s just as the economy was headed down the pan and most of the whites were packing up to leave. 'H-Town' pretty much always referred to the inner city rather than the suburbs and Jessica somehow knew that she wasn't going to any nice leafy suburbs.

"Never been," she admitted, "you from there." "Born and bred," Antwan smiled, "my man Tyrone suggested I show you some sites over there."

'I bet,' thought Jessica.

It was a 2-3 hour drive to H-Town and Antwan spoke in his leisurely way most of the journey. He'd made a lot of money in 'retail' and 'import/export' until 'outside pressures' made it a good idea to quit that game. Jessica immediately thought 'ex-drug dealer' and then blamed her racist upbringing for making such an assumption. Antwan went on to say that he'd met Taylor who'd persuaded him to try new ventures just four months before his main competitors in 'the market' had each got twenty-to-life. 'Ex-drug dealer' thought Jessica and this time she didn't feel guilty about it.

Antwan had gone into 'entertainment'. 'Pimp?' thought Jessica. But no, Antwan had gone into clubs. Dance clubs and smaller swingers clubs. "Got establishments in every big city over four states," Antwan boasted, "not bad for a man just past 40. And every club, either weekly or monthly, has a 'Zebra night' for promoting racial harmony, know what I mean."

Jessica knew what he meant.

"At every club I got staff used to be with Taylor at the 'Cock Pit'. They manage or work bar or watch the doors - but as well as that they talent-scout. Taylor covers any deficit from running the 'zebra nights' and in return I send him women who're interested in what he does. To his Club down in the city if they're close enough. Otherwise I let them know what 'special activities' Taylor can lay on for them."

Jessica had only the vaguest notion what those 'special activities' were but she had a feeling she'd probably be finding out in due course.

"The other string to my bow is organising events for Spring Break, Fantasy Fest, etc. A real good earner and if you locate a 'zebra event' right you get plenty of talent showing up. Hook 'em up to my clubs or just let them know what the big city has to offer. Taylor won't take girls under 21 as prospects but it's surprising how many women contact him and say they first heard about him years back at Spring Break. Anyway, how'd you hook up with the folk over there?"

The journey passed pretty quickly as Jessica explained and then the two just chatted. Jessica found Antwan could be charming and very easy company. She wasn't naive - it was pretty clear that Antwan was not a man to cross. You didn't survive where he'd come from unless you could look after yourself. She liked the aura of self-confidence and authority which seemed to radiate from the man beside her.

To Jessica's surprise they stopped at a restaurant in one of the wealthier suburbs.

"Nothing up to scratch in the city any more so I figured we'd try here. Got a very good write-up in the 'Times'. You can leave the coat in the car."

That was an order rather than a suggestion. Jessica obeyed and enjoyed the smile on Antwan's face as he saw her outfit. The big man gave a slow nod and offered her his arm as they walked to the restaurant.

"Booked a table for Mr Dale Anstruther and guest," Antwan told the maitre d' as he studiously ignored the man's surprise at his appearance. The little man scampered off and Antwan nodded, "If I tried to book as Antwan the restaurant would be full but it's amazing what a nice white name can get you...Ah, here comes the Manager."

Another man hurried up and smiled smoothly. "Perhaps you would like to come this way, er, sir and we will make a table up for you."

"Make me up a little table by the john, no thanks, we'll take that empty table front-and-center. I understand that your food is first-class here."

"We are proud to say..."

"Good," Antwan fixed the manager with a baleful eye, "I'll hold you personally responsible for that, OK."

The manager suddenly looked nervous, "Most certainly, I will supervise preparation personally."

"Very reassuring and I used to be a waiter so don't think I won't notice any little tricks." Antwan chuckled as the man scuttled off and took refuge in the kitchen.

Antwan hadn't been quiet in making his wishes known and Jessica was aware that they had everyone's attention in the restaurant. Antwan kissed her hand and pulled her chair out for her. As they sat and talked Antwan's hand moved under the table to stroke the leg exposed by the slash in Jessica's dress. Jessica could almost feel the eyes fixed on her from every side.

Their meal arrived and was very good, excellent in fact. Antwan 'entertained' the other diners by deeply kissing Jessica between courses and loudly stating that he was, "looking forward to getting her out of that dress."

When it was time to go, Antwan took out a thick money-roll and flicked a few notes to the manager. Then he pushed his big hand through the slit in Jessica's dress so it could come to rest on her bare buttock beneath. He gave a little squeeze and they left the restaurant to almost total silence.

Antwan laughed almost the whole way to the car. "You're a bad man," giggled Jessica nervously, "you shocked them!"

"Fuck 'em," said Antwan, "they need to get real. See a classy white woman with a Black man and they fair shit their pants."

"They didn't know what to make of me," she said.

"They knew you was a white woman who went with Blacks, whether out of inclination or for money, and they didn't like it."

"Like you say...fuck them."

Antwan saw the flash of anger in her eyes and knew that, under the brave exterior, their treatment in the restaurant had upset her. Well that could go one of two ways - she'd either retreat to lick her wounds or she'd come out fighting. Time to find out which way the wind was blowing.

"Want to go into H-Town or do you want to call it a night?

"I'm having fun - show me the city."

"We'll go where good white girls don't go. Won't be no nice decent folks like back at the restaurant."

"Thank fuck for that - half of them thought I was your whore and so I don't much feel like being a 'good girl'."

Antwan smiled and took a right turn into the city itself. It was time to tell Jessica the next rule and he knew just how to do it.

A Glorious Discovery

The first stop was a large car-park next to a low one-story building with glaring neon signs. "XXX DVDs", "GIRLS, GIRLS, GIRLS", and, "VIDEO BOOTHS HERE."

"About the last mainly straight sex shop left in the city," Antwan said, "survives pretty much the same way the gay ones do. It's a place for a little action as well as just a place for retail."

Walking in, Jessica didn't notice much action. There were a few guys, mostly Black given the shop's location, shuffling about looking at the racks of DVD cases or examining the sex-toy displays or reading the posters advertising personal appearances and feature dancing.

As she walked round the store in her red dress she paused at the interracial section and looked at some of the lurid covers. Then she went on to the toys and giggled at a huge black dildo modelled after a famous porn star's penis. All the time she was very aware that every man in the store seemed to be watching her - perhaps natural as she was the only woman there - and waiting. It was a weird feeling but she sensed that the men were looking at her in appreciation and anticipation and so it wasn't unpleasant.

Finally she reached a small sign into a back corridor which said 'Booths.' Is that for watching videos?" she asked.

"Well yes," answered Antwan, "but nowadays they are mainly used for other things. You ever heard of a glory-hole."

Jessica's eyes widened in shock, "Oh my God, I saw videos on my ex-husband's computer but I didn't think they really existed."

Antwan watched as Jessica was slowly drawn towards the booths like a moth to the flame. "Give me fifty in tokens," he ordered the clerk. The other men in the shop began moving towards the cash desk and placing similar orders but Jessica didn't hear them. She was already in the right-hand booth.

She didn't know what she'd expected but this place was NASTY. Thin construction board walls covered in scuffed paintwork. The sounds of pornography showing in other booths echoed in her ears and in the right hand wall was a hole with its edges smoothed off. The booth was relatively clean but Jessica noticed the tiled floor and that the paint below the hole was almost worn away as if it was regularly scrubbed clean.

Antwan joined her, "Pretty freaky, huh?" He slid a token into the machine and selected a channel. The screen half-way up the wall began showing a movie, a blonde woman surrounded by ten thuggish black guys in stereotypical gang attire. One grabbed her arm and the others began striping off her clothes.

"Yeah, I guess," said Jessica as she idly watched the screen. Then she heard a thud as the door to the booth next door clothed. Her eyes widened and she looked at Antwan.

He gave a little shrug. "You wanna try it?"

Jessica nodded.

"Best take that fine dress off and give it to me or it'll get ruined." Then he moved the booth's chair next to the wall, "That'll save your knees."

She smiled at him as she removed her dress - one good thing about this dress was that it came off very quickly. In seconds she was naked, save for her shoes, in the nasty video booth of an H-town porn store. She looked at Antwan as a little knock sounded on the wall.

"Stick your fingers through the hole to tell him you're ready and then just do what comes natural."

She put two fingers through the hole and almost immediately a sturdy black cock punched through. She giggled and wrapped her fingers round it.

"I'll tell you your next rule as you suck that cock," said Antwan. He watched as the redhead wiped off the chair, sat down and bent over to take the stranger's dick in her mouth."

"Cocks come in three sorts. First, inferior cocks. White cock, Mexican cock, milk chocolate cock, Arab cock, Asian cock, Indian cock, damn Martian cock - they don't get in you, ever. If you have to, then you put a condom on it and give it a handy. Understood."

Jessica pulled off the cock and whispered, "Just as well this one's lovely and black." She smiled at the phone Antwan was using to film her, she'd got very used to being filmed, and then went back to work.

"Second type of cock is untested black cock. In today's world you can't just fuck it as nature attended. But you can give him one of them killer blow-jobs or put a condom on it if he wants sex. If he's good tell him to get down to one of my clubs and get himself tested."

Jessica stopped moving her head on the cock. The man withdrew and Antwan snapped, "Show us what you got." Jessica opened her mouth to show a small pool of thick white semen . Her eyes sparkled with the wildness of her actions. "What do you do with that?" She closed her mouth and swallowed, then opened it again to reveal the semen had gone. She giggled into the camera and then waited.

Soon a fresh cock came through the hole. Longer and thinner but just as Black. Jessica was already blowing it before she really knew what she was doing. "They come in all shapes and sizes," instructed Antwan, "but that don't matter. Your place is to give pleasure to the Black man and by giving pleasure to him you give pleasure to yourself. You understand? Now let me see you work that dick."

Jess put all her technique into pleasing the man in the booth next door. The man who's face she had never seen. The man who was reduced for her to about six inches of hard black meat. It didn't take long. He shot a good load and she leaned forward as some of his cum dribbled out of her mouth onto the floor. She gulped the rest down and said, "Oops," to the camera with a giggle.

Man number three had Jessica holding her hand to her mouth to stifle her laughter. There appeared to be a mass of grey pubic hair with perhaps half an inch of cock hidden in it.

Again Jessica looked to Antwan for advice. "What colour is it?" whispered Antwan. Well it was a Black cock so Jessica did her best with it. It was very awkward because the man barely made it through the hole but some skilled finger and tongue work finally had him at his full proud inch and a half. Just enough for Jess to work with and apparently the man wasn't used to such attention. He came quickly. The cock withdrew and a thin wrinkled Black hand came through the hole and stroked Jessica's bare breast.

"Thank ya baby," came through the hole, "best I've felt in years. You come back, OK."

"Thanks for the cum," replied Jessica, and the man removed his hand.

After a couple of minutes Man Number Four made his appearance. It was a contrast to the last one. A solid eight inches of well-proportioned hard meat. A pussy-pleaser any man could be proud of. Jessica only wrinkled up her nose in disgust. Pale pink pricks no longer did anything for her. Antwan reached into his jacket pocket and handed her a condom. She put it on and then began to mechanically jack the prick off.

Of course, the man didn't do the decent thing and come quickly. He was a real chore and Jessica's arms were both very tired by the time he squirted a load into the end of the rubber. Jessica pulled the condom off and carefully dropped it into the trash bucket.

"You ready to go?" asked Antwan.

"One more," said Jess, "I want to end with a real one." Antwan chuckled - it was all coming naturally to the lovely woman in front of him. She wasn't playing for the camera she was just doing what came naturally to her. Time to continue her lesson.

Man Number Five was, well, pretty average, But what mattered was that his cock was a beautiful coal-Black. Jessica gave a little squeal of delight and went to start sucking. But Antwan took her shoulder and then gestured to her to get up. He moved the chair and had her bend at the waist to take the new cock into her mouth.

"Third type of cock is tested Black cock. No reason not to do what nature intended so you give up your mouth or that pussy, whatever he wants and wherever he wants and however he wants. Won't be no condoms. Birth control is your business not his and he'll cum where he wants to cum. Into your mouth, over your body or deep in that pretty white pussy. Now how do you know tested Black cock."

Jessica paused her sucking, "Card," she said.

Antwan held his card on the wall in front of her as she returned to sucking the stranger. "Like that one?" he rumbled. She nodded and at that moment felt him push into her. Antwan rode her hard and fast as she grunted and tried to keep up a rhythmn on the cock in front of her. She finally gasped once more and the man came, showering her chest and the floor in his jizz. Antwan gave a satisfied grunt and gripped her ass for a second or two before pulling out of her.

Jess knew that Antwan had come in her and that she had neglected to put in her diaphragm. Having just come off the pill she couldn't be 100% certain of her cycle but she thought she was probably OK. She remembered that she'd been told that birth control was her responsibility. Antwan clearly hadn't given it a second thought. He'd wanted to fuck his hot new slut and so he'd fucked her and planted his seed just where nature intended. The momentary fear of the possible implications quickly passed; the warm glow of Antwan's desire for her stayed long.

They left the store to demands that Jessica come back real soon. Then Antwan drove her to an all-night supermarket so she could clean herself up in its washroom. She'd expected her date to run all night so she'd brought a change of clothes for the morning and now she made use of it. Her new outfit was nothing like as sexy - just smart and comfortable for being round the house.

"Fuck," said Jessica when she got back into the car, "that was the most amazing night of my life! I never thought I'd ever do something like that."

"You tired - you want to go home or you want to try something else."

"I've never felt less tired or more alive. Let's go."

An Evening's Dancing

The next stop was another run-down shabby building with signs advertising 'GIRLS',

H-Town seemed to specialize in them. As they walked in Jessica saw the big central stage with poles and a couple of black girls busily gyrating. Men sat around the stage watching the dancers and another moved round the table collecting cash. "Tips," said Antwan, "strict no-touching rule for public clubs in this state."

There were a few cheers as the girls got naked and a few more when after a few minutes dancing they left the stage.