Jill and Jack

Jill and Jack

Jill is introduced in Road Show 6 Debut where she and her husband Jack are top bidders and become Mickie's first paying tricks. The Road Show has two more chapters but I want to see if many readers would like to follow another wayward wife in the road to becoming a whore. Email me!

Jill's birthday will become a bang-up celebration starting a new life as a whore

Juliana Irene Lucile was named after several of her very successful female ancestors. She always disliked the excessively formal sounding Juliana and hated Julie, Irene and Lucile were different branches of a wealthy family tree that did to get along well, so the whole family settled on Jill as a nick-name. Never Jilly! Mind You! Jill had a mind of her own and was able to impose the persona she preferred on family and friends through High School and College. That was where she met John Smith at a sorority mixer.

He was shy but cute, and no match at all for the domineering personality Jill presented. The only problem was John Smith as a name is the all time plain vanilla moniker. Jack? Well Jill could live with Jack! Not that John Smith had much of a choice in the matter; Jill generally got what she wanted and the rest of the world better step aside.

Now that she had found a satisfactory name for him, Jill set about to completely corral him and before their junior year was complete they were 'an item' on campus. Her parents approved, his parents were bemused by the dynamo who had undertaken the transformation of their youngest son. Jack's point of view is not on record but stood as much chance as a sapling resisting a glacier anyway. The nuptials occurred right after Jack received a BS diploma in computer science (would you believe the university insisted his given name be spelled J O H N -- the nerve of some people.) and Jill ("Juliana Irene Lucile") got hers in French Literature. The bride was beautiful! The groom was present.

Jill enjoyed seven happy years as a bride and wife. No one asked Jack how he felt, but he clearly adored his wife who clearly adored being adored.

In most respects the marriage was a happy one. Sex was important and enjoyed by both but was unadventurous. Jill worked out at the gym weekly and kept her 5'7" 34 24 34 figure trim and tight. Jack played ball with colleagues from work and was a respectable weekend golfer. Jill used her biweekly beauty shop appointments to keep her blond 'do' shaped to the current fashion. They were an attractive but normal appearing couple.

All that changed as Jill approached her 30th. Birthday.

Much to Jack's dismay, Jill would flare up at inconsequential events and would turn hyper loving at other inappropriate times. Jack wondered about his wife's health because his ability to predict her wants and moods was shot to hell! As a result he seemed to always do the 'wrong' thing. As a remedy he proposed they take a leisurely road trip east and spend a couple of weeks just exploring the byways and stopping whenever the mood struck, but 'early to bed' was a central feature of Jack's intentions.

The distraction of new vistas appealed to Jill and for several days they enjoyed nice meals comfortable beds and shopping for souvenirs. As the 'big 3 0' was going to arrive in two days, Jill became agitated again and Jack resolved to do anything to restore a calm sunny disposition. The last night was even a disappointment in bed when Jack fell short of Jill's expectations and breakfast was sullen.

Looking back it should have been clear that Jill was anxious about aging and losing her sex appeal. Anything less than an ardent stud performance was going to reinforce that fear, and Jack stumbled.

The couple had passed through a little down a few miles from the interstate when Jill saw a steakhouse. It was in the gap between lunch and diner service so there were no cars in the parking lot and the dining room was not going to be open for dinner for 30 minutes. Rather than drive on, Jill noticed a small store they could visit behind the Road Show restaurant. Once they drove to the store front Jack realized that this was an adult toy store, and tried to explain to Jill she would probably not be comfortable in such an establishment.

Jill did not react to Jack as a protector seeking to shield her, but as a man saying she was over the hill and therefore uninterested in sex and sex toys. Jill overrides Jack's concerns and determined she is going into the store -- alone if he won't come, so they both walk into the store.

The reality of what merchandise is for sale astonishes Jill. She was pretty sheltered up to now, but she will be dammed if she backs out in front of Jack so she starts to explore the books and toys on display. With increasing embarrassment and increasing determination Jill handled dildos, looked at vibrators, examined restraints, took revealing lingerie off the rack trying to feign genuine interest. The salacious nature of the merchandise did plant the seeds arousal in Jill and Jack as each imagined the items being put to use. There was a bustle in one of the show rooms that caught the couple's attention.

The store clerk appeared from the back of the store and room called for attention. "In a moment Mickie will ask your assistance in picking a club dress so let us help her out. The first is a pink fishnet item zk3311 which is on sale for $50. One size fits most guys so think of someone you would like to see wearing this. Our model is wearing a collar accessory package which is part of a set. A virtually naked woman was being led out into the main showroom!

The clerk continued." The collar wrist restraints and leash are all color coded. The complete package includes a white set, another in red, and this golden set. For the very truly adventurous lady, a faux diamond set can also be acquired. The colors are significant. White is intended to indicate that the lady can be looked at to your heart's content but not touched. The red color is supposed to signal that the holder of the leash invites the audience to touch the wearer's body including her erogenous zones but externally only. "

A well built strawberry blond lady was standing proudly before this small crowd the clerk continued his 'orientation'. "The golden collar and leash indicate an offer to the audience to actually digitally penetrate the vagina and anal cavity of the submissive with fingers or toys." He finished.

"What about the diamond collar?" One of the males in the audience called out.

"Unlimited public penile penetration! Condoms at the option of the leash holder!" Joe calmly announced. "Diamonds are for gangbangs."

Jill stifled a gasp at that moment because the sudden vision of her being the woman led to a gangbang on a leash threatened to cause her to climax right there and then.

The model reappeared with another skimpy dress. "Imagine that you are dancing with this vision, gliding around the club." The clerk's spiel rang out. "She expects to be held and fondled. The ensemble is designed to you can display your dance partner. The halter straps move easily aside so that the treasure chest can be discovered and uncovered."

Obviously striving to top the sexual impact of the last ensemble, the model appeared one more time wearing a net fabric 'cover up' ensemble that did nothing of the sort. Worn without the bra or thong for that matter, her breasts pussy and ass were on perfect display and the top was just a vest made of the same net material. During her parade, the model first stripped the net top completely baring her breasts, and then unwrapped the bottom and stood completely naked. She weaved her way through the hushed audience, stopping frequently to look more closely at one or more of the video packages or sex toys on display. Stopping at a locked display case she bent at the waist and examined a large glass phallus. "Let me see this one Joe." She demanded.

The clerk responded immediately and soon Mickie was holding the glass dildo and measuring it against herself... It was about as long as her forearm and just about as big in diameter with knobs and ridges scattered along the surface. "My God do you think that is what I think it is? Jill gasped clutching Jack's arm

"Do you people think that I could take something like this?" The model teased her rapt audience. "Joe, add this to my 'shopping cart' I am sure these fine men and women will find a way to help me pay for toys. But right now I'd like a bottle of lubricant."

Leaning back on a covered bench she lubricated the dildo and worked the tip into her vagina, spreading her legs and stretching her vaginal opening. Then she pushed the device further and further into her cunt until 75% of the 18 inch total length was buried in her pussy. Panting with exertion and arousal she looked around at the stunned audience. "I didn't think I could do it either." she laughed.

An older man now took center stage. "Well gentlemen and ladies, to get things started I want all of you to know that the order in which Mickie satisfies your demands will be up for auction because this is her first professional encounter; her debut so to speak. The high bidder will always know he (or she actually) will be Mickie's first 'john' or 'joan.' The bids will be for 30 minutes of service. Your choice of positions, holes, toys and restraints. You can also elect privacy or public sex. As many as three can team up but each team member pays the bid price." Randy outlined the auction process.

Overwhelmed by the sexuality of the display Jill blurted out. "$100!" She the hissed to Jack " Do This! Buy her for us to play with! This is my birthday present and this is what I want." She growled in a determined voice.

When the bidding slowed to a stop the Jill and Jack team bid $225 each.

Settling the logistics, the couple decided to use a padded platform in a sex show room surrounded by peep-show booths. Joe, ever the entrepreneur, offered the ladies a wigs and Mardi gras masks to disguise their identity if he could let the other customers use the booths on a pay-per-view basis. Jill and Jack accepted an offer of one quarter of booth receipts with another quarter to the whore and the remaining half was kept by the house.

In the sex show Jill disrobed and locked clothes in a locker. Jill gave Mickie directions. "Jack is my husband and this is Jack's gift to me so I will call the shots. You may call me Jill. First, Jack will lie on his back and you will straddle him facing his feet." Jill said. "Jack, I want you to lube up that tool of yours so when this delightful creature straddles you, she can take your cock up her ass. Then I want to see you bounce on him honey so your boobs shake."

In just a few moments, peep show window blinds rose in most of the surrounding booths. The whore's husband was watching, but not from a booth. He was in front of a series of four monitors showing the video feed from cameras fixed around the sex show room. Since the system was the same as in their motel suite, he was practiced enough to zoom and pan to capture the action in detail as DVD's saved the feeds for later editing.

After getting her feet and arms placed to ride Jack. Mickie picked up the pace till her tits really did start to bounce. Lost in these sensations Mickie almost missed Jill next directive. "Enough of that! Keep him rammed up your ass and lean back so he can grab your boobs and pinch your nipples. I also want you to lift your legs and hold them elevated and apart."

Jill pressed the glass phallus up against Mickie's waiting vagina and pushed the tip past the new whore's vaginal lips. The dildo slid smoothly deeper and deeper up Mickie's vaginal passage. Mickie groaned as the glass phallus added to the pressure of Jack's cock rammed up her ass. Mickie was enjoying the experiencing the extra sensations of a double penetration. This time she could simply relax and enjoy the moment because Jack and Jill were doing all the work.

Mickie starred up at Jill's face. "That gal is really into this." Mickie realized. "I'll bet she wishes it was her laying here, taking it in both holes." In a whisper she tried to get Jill's attention. "Honey, you have no idea how wild I feel right now. Your man's tool is wedged up my ass and you are ramming that huge toy up my cunt. I feel like a sex goddess!" Louder. "Keep it up Honey. I want all you can give me." Louder yet! "Oh please don't stop either of you. I am getting close." Very Loud Now! "Please fuck me both of you. I really want to come! You are driving me out of my mind!" Shouting! "Oooh Fuck! Fuck Me! Ohhh FUCK ME HARD" Mickie screamed just before her whole body twitched in orgasm.

Coming down a bit Mickie reached down and grasped Jill's wrist holding the dildo at full penetration. "Honey, Thank you. You and your man have given me an experience I will never forget." Seeing the glazed expression on Jill's face Mickie was struck by an inspiration. "The only way for me to thank you properly is to return the favor... Help me up and lay down in my place!" Mickie coached the distracted Jill. Jack do you have enough lead in your pencil to ass fuck Jill here?"

In the office fresh DVD blanks in three recorders for Jack and Jill and one was kept for continuity of Mickie's own adventure.

In a daze Jill responded to Mickie and found herself impaled on her husband's cock which, encouraged by the eroticism of the turnaround, had developed new lease on life. Jill pulled her legs apart so Mickie could lube her pussy and put a fresh coat on the dildo. As Mickie started pushing the giant dildo into Jill, she noticed the count-down timer had only five minutes left. "Fuck the clock!" She decided. "Jill is going to have the experience of a lifetime, and my next appointment will just have to wait."

In the end, Jill was able to take all but the last couple of inches of the Dildo. Since this was the first time Jill experienced a DP the extra sensations brought her to a screaming climax after only fifteen minutes but by the time everyone had become untangled and Mickie was ready for her next 'appointment' slightly less than an hour had elapsed.

Mickie left to satisfy the next auction winners while Jill languished naked with Jack.

"I guess that went farther than I expected, but I feel very desirable right now, and that is a feeling I relish very much. Do you think I am desirable Honey?" She purred to her husband.

"Desirable is a gross understatement. I had no idea how beguilingly sensuous and erotic it is to see you naked and have nearly public sex while paying customers peeped at us. We were safe in here but those men paid a lot of money to watch us have sex with that whore. If I knew in advance how this would happen I would have freaked, but no it is over I think reminiscing about this adventure is going to keep us warm at night for many years." Jack admitted.

"That clerk guy is inspired. I never would have thought how much being observed would spice up our screwing. Mickie seemed to have a good time when she took you up her ass, but nowhere as good a time as I had. I get your cock whenever I want it. I was foolish not to have tried some playing around with new things we could do in the bedroom. I also would have freaked out If I wasn't so worked up when she laid me on you and you slid your cock up my ass. I also would never have believed how good that dildo felt while she was working in my pussy, "Jill added.

They dressed leisurely and after leaving the booth were met by the clerk, who handed Jack a DVD. "This was recorded during your session in the booth; there are four tracks each with time codes so you can edit this into a really excellent video. Here is your portion of the booth receipts." He said handing Jill $45 in cash. "I will double this in store credits if you want to make a purchase, In fact the glass dildo sells for $100 but I'll cut is price to your store credit."

"Jack Baby, I really want that glass cock, so I am going to spend our 'earnings' on this." Jill wheedled her husband. Who, needless to say, agreed.

The couple were window shopping when Mickie, still naked, walked up and took Jill by the elbow a few steps away. "I will run out of time before I can finish this lot. Do you think your birthday celebration might include turning a trick or two? Tell Jack that you are going to fuck a couple of guys. They have already seen everything you have and will pay for some toys as a side benefit. Do you think he'll go along?" She whispered.

The suggestion Jill prostitute herself hit like a ton of bricks. The outrageous suggestion triggered Pretty Woman fantasies which were dormant in Jill's subconscious. The suggestion that men would pay her for sex was a tribute to her sex appeal and refuted again Jill's feelings of undesirability. Her knees sagged as the fantasy and reality collided, but the adventure won out as she turned to walk back to where a puzzled Jack was standing.

The couple put their heads together, and had an intense discussion. After speaking to the clerk, they settled on a strategy of pricing to capture market share where the couple would charge $50 and the store a further $25 to provide a venue for the encounter. Further Jill and Jack set a time policy of 'fuck till you come."

Most of those waiting impatiently for Mickie took the bargain offered by Jill and switched 'allegiance.'

One of the first of Jill's johns pressed her on the 'fuck till you come' offer. "What happens if I don't come and she does in 30 minutes?"

"The session will continue." Jack promised.

"OK but suppose I get her to come twice but I am not done?" The john countered.

"Since the 'house' gets part of your fee, I cannot give all your money back, what do you suggest?" Jack temporized.

"I will take a rain check. I will come to your place and you let me have her for an all night all holes fuck session. I pay for the motel. You have to bring her to me. She is to be dressed to please. You buy the three of us dinner. When I am done, you can pick her up." The john demanded.

Despite having two anal fuck sessions in the prior 90 minutes, the prospect of having to deliver his wife, scantily clad, to some guy who had already bought her gave Jack an almost painful erection. After swallowing nervously he said "I am sure she will agree to that."

Realizing he had won the negotiation the john, we will call him Mike, pressed his dominance. "That is not all, if I get her to come three or more times before she finishes me, she will have to give me a weekend. That means she may have to take Friday and Monday off if she works, to drive or fly to my location to be there before 6PM and not leave till 6 AM Monday. She is to commit to doing anything anyone and anywhere I say, with the only restriction is that her health will not be endangered." Mike paused and recognizing that Jack was not resisting, finished with: "Jill will be wearing a diamond slave collar all weekend and she is to bring the matching leash."

Jack had heard the clerk explaining the color coding of collar/leash ensembles "Diamonds are for Gangbangs." and he remembered Jill shivering as she visualized the circumstance described.

At that moment Jill returned from satisfying her first trick. "Oh baby, that was quite a session, that stud screwed me thoroughly before I got him off. He really did a number on me. I came twice! "She happily gushed. Then seeing a strange look on Jack's face asked. "I hope you are not mad, because I want to do this. I am having fun."

"Jill these guys have a guarantee of performance which I agreed with Mike, and you better understand the implications." Jack said as he reviewed the performance guarantees that might commit Jill to weekends as a sex slave all around the Midwest while Jill's eyes grew wider and her imagination expanded the scope of the potential adventure ahead.