Ann: The Married Years Ch. 56

Tamara disappeared into the back, leaving Ann to daydream about her and Neil's experiences at the hotel. In particular at the moment, she was recalling the tale her husband had shared with her about how he'd fucked Heather behind the very counter she was standing in front of.

Ann had given him a second chance at fucking Heather's ass, something her friend had never done before. He'd refrained from taken advantage of the veiled green light Heather had given him the night before at her apartment. It was just before Neil was going to move out of the hotel, and Ann offered her then fiance to Heather as a way to thank her for all the things she had done for the two of them. Neil took advantage, but didn't take he anal virginity liked she'd hoped because of mixed signals he'd interpreted wrong.

Given that second chance, he ate out Heather from underneath the counter while she was dealing with a late night check-in, and when the coast was clear, he bent her over the top and took her from behind. It was a watershed moment for Heather, and it solidified her friendship with the Thomases.

She came out from the back, a smile appearing as she made eye contact with Ann. "I'm Heather Watkins, manager of the hotel. How may I help you, Miss?"

"Green. I believe I have a reservation."

Heather froze, a look of concern coming over her face. She looked left and right, checking to make sure no one was nearby. Leaning over the counter, she whispered, "Seriously? I thought he was kidding."

"You thought... who was kidding?"

Heather put her finger over her mouth. "Ssshhh! Keep it down."

Ann looked over her own shoulders, confused about how their interaction had started. Lowering her voice for some unknown reason, Ann played along. "Okay. Why?"

"I can't believe he's going to make me do this. I'm... fucked!"

Ann knew it was part of the set up. One of the amazing things about the group of friends she'd cultivated in her years living in West Virginia was they all seemed to become very good, even comfortable, with naughty roleplaying. It was like she was one of the lead actors in a local theater group that put on elaborate erotic productions, specializing in improvisation.

Unsure of exactly where the premise was heading, she instinctively knew enough to play along. She also made an educated guess that while Neil had set up whatever was about to begin, him dropping her off like he had meant he was setting her free. He'd said as much, telling her he wouldn't see her again until Tuesday. Putting that information to use, she tapped into her honed improvisational skills, asking, "What are you talking about? Who are you talking about?"

Heather smiled inside, happy that Ann was playing along. She felt certain she would, but it was always the very beginning of every Thomas production that caused concerns. Most of the people involved in one of those scenarios were cast ahead of time, and understood their particular roles. But the star of the show was almost always in the dark at the start, and had to pick up on the plotline as things were unveiled. How those first interactions were performed and perceived would determine the ultimate success of the staged play. With Ann being the one without benefit of the script, it was up to Heather's acting ability to set things in motion.

She nodded toward the sitting area of the posh lobby. "Go have a seat. I've got to do a few things to get ready for you. I... I've got to get in front of this so I don't lose my job."

"I don't understand."

"I'm not sure I do either. I never thought it would come to this. Like I said, I'm fucked. I... I've got to make a couple of calls. You know what? Have you eaten?"

"Uh, no actually."

Heather picked up the phone and dialed an extension. "Hello, Leia, it's Heather. I'm sending a hotel guest your direction. Her name is Miss Green. She's an early check-in, but I need to get her room ready. Get a secluded booth and take her order. Veeeerry secluded. I don't want anyone near her. The bill is on the hotel because we weren't ready for her like we should have been. Yes. The back room is perfect. Wait on her yourself and don't let anyone else back there except me. No, just take care of it for me please. Thanks."

She hung up and looked at Ann with a nervous smile.

"Are you okay?"

"No," Heather answered. "Like I said, you aren't supposed to be here. I've been played."

"By who?"

"Who do you think? Andre. That's who."

Ann held her tongue. While she didn't know who Heather was referring to, she was certain she was supposed to based on the way her friend had said it. She responded with a pensive, "Oh."

"Oh is right," Heather shot back. Turning, she went to the counter against the back wall, smiling out of Ann's view that the hook had been set. Her sexy playmate had bought into the narrative perfectly. Picking up a sealed manilla envelope, she handed it to Ann. It was labeled for 'Miss Watkins'.

"This is for you. I just can't believe I'm having to hand it to you. Like I said, you're not supposed to be here."

"And yet here I am. But I'm not Miss Watkins. You are."

"Yeah. No kidding. Look, take that. Go have breakfast. I've got to get your room ready... myself. I can't have anyone know you're here or what you're doing. This isn't that kind of hotel. Like I said, I could lose my job over this."

"I... I'll be discrete," Ann replied instinctively, unsure if that even made sense since she had no clue as to what was supposed to happen. All she did know was that the answers to a lot of her questions were now literally in her hand. It was just the kind of thing she'd do to clue Neil in on something she'd planned.

"I'm praying you mean that. Go to the restaurant. Leia is waiting for you. I'm going to take your things to the room and get it ready. I'll meet you in the restaurant once I get things settled. You and I need to come to an understanding before this gets more out of hand than it already is."

"Anything you say, Heather. I guess I'll see you shortly."

~*~*~*~*~*~*~

Ann sat in a booth in the back corner of the restaurant... in a part that was roped off. It would have been packed on a weekend, the breakfast buffet the hotel put on being the best in the area. But it was only available on Saturdays and Sundays. On Fridays the place was busy, but not overflowing.

She was reminded of a morning when she and Neil had eaten there the week she came out. It wasn't the same booth, but it was close, and in the same part of the restaurant. And it was just as private. They'd visited in just their robes, and they'd toyed with each other... and precursor to one of the many days of fun they had during her visit.

Waiting on her omelet and hashbrowns, she nursed a cup of strong coffee as her fingers played with the metal clasp holding the envelope closed. Finding the nerve to open it, she pulled out a couple pieces of paper. It was a letter, written to Heather. It wasn't in Neil's handwriting, but it was definitely written by a man. She smirked, loving the lengths he was going to. That is until she started reading it, her hand covering her mouth in shock.

"Oh my God! Is he... serious?"

~*~*~*~*~*~*~

Miss Watkins,

By now you must be questioning your decision. Unfortunately, the consequences of it are likely only now becoming real to you. The debt is due. Since you've offered no reasonable solution to resolve it on your own, we'll be using my plan.

I'm going to be sending over one of my girls early Friday morning. Her name is Rachel Green. She'll be working Friday through Sunday, but she'll be staying there until Tuesday morning. Monday is her reward for all the hard work she'll be putting in. Seeing as you're in charge of the facility, I expect that you'll cooperate and make things go smoothly. It is, after all, in your best interest.

The following are my expectations, and they are not negotiable:

You will set Rachel up in your biggest suite. If it's already booked, you're going to have to make the arrangements to change them.

When she's not working, Rachel will be allowed to use the entire facility. This will assist you in setting up her nightly schedule. Being seen is a subtle way of advertising, but you have my assurance that she will not approach any guests. I need yours that she will be treated as any other hotel guest during her stay. If she is approached by a guest, she will engage, and flirt, but politely decline any serious advances.

Breakfast and a late night dinner will be served in her room. I want the same person each night to deliver her dinner, as this will be during her working hours. For your sake, make sure that person has your trust. She will tip this person at the end of her stay for their discretion.

Rachel will be using the workout facilities, the pools and likely the jacuzzi every day. Her exercise regimen is an important part of her daily routine, and she'll need it to maintain her strength. She will have lunch by the outside pool, weather permitting. If not, she'll have it by the indoor pool. You will also provide a masseuse for her daily after her lunch.

As I alluded, you will be responsible for filling her schedule each night. I've provided a list of services and pricing. The base rate is $100 per hour, with additional costs for what's available on Rachel's personal menu. Not all my girls will do the same. Familiarize yourself with her particular offerings. I don't need any messy scenes when they're in the room with her. Make copies, and have the client with the appointment select, a la cart style. She'll need fifteen minutes to prepare for each client. The balance of the time paid for will be spent with them.

Rachel is going to be available from 5pm until 3am, with an hour dinner break from 10 to 11. The better job you do at filling her schedule, the quicker you'll be out from under your debt. It's unlikely that can happen in just one weekend. I'll have other girls on standby for the next few weekends. Variety is key. Keep the suite available just on case. Or, you could always agree to my alternative solution. You'd be free and clear from the start.

I realize this arrangement puts you at a disadvantage, and that you are at risk. The cost of playing games you can't afford, I'm afraid. However, I'm hopeful that this might be something that can prove lucrative for all parties involved. Rachel will cover the cost of the room and the food. I'm sure $200 per night will be acceptable. In addition, my girls earn their keep. She'll split her take with me, fifty/fifty. Ten percent of my take will go to you for your efforts.

I'll be there at 4:30pm on Friday. I'll expect you to have the first few hours of Rachel's schedule available when I arrive. I will be with her the entire time she's working for safety reasons, but I expect you'll choose clients that are more amenable than what she's used to. Higher end hotel, higher end pool of clients to draw from. Don't disappoint me.

Andre

~*~*~*~*~*~*~

Ann read over the letter; twice. Then she glanced at the 'menu' of her so called services, the reality of what Neil had set up landing in her chest.

"Fuck... I'm actually going to be a prostitute," she shivered.

Yes, she was certain it was a ruse of sorts. She was just as certain that all of her normal sexual limits would be in play. She couldn't imagine any scenario where she'd be fucking another man. The menu didn't confirm that, but it was there between the lines.

She actually reasoned that Neil would be portraying the mysterious Andre, and that the familiar cast of characters normally called upon in their sexy shenanigans would be participating. She didn't know who exactly, but she was anticipating a wonderful weekend ahead of her.

The premise was elaborate, and she found the part she going to portray very exciting. Hell, less than an hour before she was waxing poetic about her fondness of fantasizing about being a prostitute. Not an escort. Not a hooker. A bonafide prostitute. Neil had found a way to give her that experience away from the legendary former brothel where she worked selling happiness in the way of lingerie and other sexy items.

To that end, she looked at an envelope marked Rachel that was with the other papers.

"I can't believe he named me Rachel Green," she snickered, thinking of the TV character from Friends, brilliantly portrayed by the sexy Jennifer Aniston, whom she now slightly resembled because of her hairstyle and some of her facial features. Hell, their bodies were damn near identical, although Ann was actually a little buffer from working out the way she did.

Opening the envelope, she pulled out another letter. Or more to the point, a daily itinerary.

~*~*~*~*~*~*~

Rachel,

You're going to be working here all weekend. Your hours are 5pm to 3am. You'll get an hour dinner break at 10pm. If this works, you'll be safer and dealing with more reputable clients than you're used to. But there will also potentially be a lot more each night. You won't have to troll for them. I have someone setting up a schedule for each night. I've raised your rates because of that. I've set all the pricing. Do only what's requested. Nothing more. They don't get what they don't pay for.

You're paying for the room and meals. The schedule coordinator comes out of my portion. It's still fifty/fifty, so you need to clear $800 on your end this weekend to cover all your expenses. I figure you're working the first night for free, but you should be making a killing Saturday and Sunday.

When you're not working, you need to adhere to a routine. You need to stay fit, fed and hydrated. Breakfast will be delivered to your room at 10am. By 11, you need to be in the fitness center. Do your workout routine. One hour. Then, a half-hour in the pool doing laps. Outside if weather permits. Inside if not. Lunch will be served poolside at 12:30pm. You get a half-hour in the jacuzzi after. Then a couple of cool down laps before heading back to your room. You will wear one of the supplied bikinis. No drying off until you get to the room. Anytime you're out in public, that sexy body of yours is advertising. Don't hide it.

Do not come on to any guests. You can flirt if approached, but no freelancing. Do not take anyone to your room on your own. I cannot stress that enough. This is a high profile hotel. Getting pinched would ruin any future plans I have there. I've got the hotel manager in a very compromised situation and I intend to take full advantage of it.

You'll have a half-hour massage scheduled for 1:30 every day you're there. After that, take a shower and then take a nap. A wake up call will be made at 4:30. I'll be arriving at the hotel then. I'll be in your room shortly afterward. Be ready for me.

Finally, you're working the weekend, but you'll be staying at a the hotel on Monday as well. It's a reward for all the hard work I know you're going to be putting in. The morning and afternoon routines remains the same. Breakfast, workout, swim, decompress with lunch, the jacuzzi and cool down, and then a nice massage. After the massage, you time is yours until dinner. I'll have something special for you Monday at 7pm.

I'm counting on you, Rachel. Don't let me down. You know what will happen if you do.

Andre

~*~*~*~*~*~*~

"My God... I've got a pimp! I'm actually going to have a pimp!" she moaned excitedly. She felt her pussy already getting wet just from what it implied. That and the realization that she was going to pretend to be a prostitute. She knew it was purely coincidence that she'd professed her fantasy of that exact scenario to him on their way to the hotel. There was no way he could have planned for her to think or say that. Then again, he'd taken her to Henrietta's House on the way. She often brought up using the room that had been preserved as it was when the place was a brothel whenever they were there together. She'd do it whenever he'd stop by the store while she was working, feeling like she was one of Henrietta's girls back in the day.

Thinking that Neil had done so much to set up the adventure she was about to begin, she wondered if he'd taken her there to plant the seed in her mind.

"He could have picked up whatever he got for me anytime. Did he want to take me there to make me think that way?" she wondered. "Nah. That's silly. He knew it was on the way. He wanted me to see the bags so I'd know he's been planning this for a long time."

Taking a bite of her delicious omelet, she checked the time on her watch. It was a little before ten. Reading the letter again, she realized she was ahead of schedule. Plenty of time to get to her room, change into some barely there swimming attire and head to the gym. She was already looking forward to putting in a good workout. She smiled, thinking of how it was all a part of Neil's plan. And if that was the case, she intended to follow his directives point by point.

She was going over the documents a third time when a thought occurred to her. She was back where it all started. She'd had a fantasy about being a call girl for years. She'd confessed to Neil that it stemmed from when she'd seen The Owl and the Pussycat as a young girl. It didn't manifest itself until she became of age and learned about sex, but it stuck with her. So much so that when she finally got to live out that erotic dream with Neil as an escort, she dubbed herself Barbara. She loved Barbra Streisand, and it was a much sexier name in her mind than Doris, the character she'd played in the movie.

And that was her revelation. Her first appearance as Barbara had been there at the Sheraton. She'd only portrayed her once since then, but she'd pretended to be a prostitute in her head countless times. Many of them were when Neil fucked her in the bordello suite in the former brothel her store was located in. But because she worked in a lingerie store, and she always dressed up in some sexy risque outfit designed there, using herself as a human mannequin, she often daydreamed of being a working girl while working. That was particularly true whenever some handsome man purchased a gift for his wife or girlfriend and paid with cash to hide the credit card statement. The physical exchange of money would make her pussy tingle. Even more so when she was told to keep the change, which happened often.

And then there was the time she paid for sex, being a part of another couple's fantasy game. She'd pretended to be Stacy Jennings, a female industrialist that was on the verge of a messy divorce. In the scene it was based on, Stacy was forced to look to a prostitute in order to alleviate pent up sexual frustration caused by suddenly being cut off from what she thought was a healthy and active sexual relationship with her husband. Instead, he claimed she'd had numerous affairs and filed for divorce in a ploy to gain control of a part of her fortune. Her lawyer suggested a prostitute instead of caving in to the never ending lawsuit, and she decided to meet an attractive woman in a motel in Maryland and spent a torrid night with her satiating all of her carnal needs.

That was the plot of an X-rated novel; the third in a series that new friend Janie was living out with her husband Terrence. Neil and Ann had met them on a mountain hike, the two of them in the very beginning of an adventure that would take them over a month to live out. When Ann discovered that, she had to admit she was a bit jealous. But she was also surprised it was Terrence that had called her to ask her to help. He wanted to surprise his wife with a plot twist, as Stacy Jennings was a man in the novel. Ann literally jumped at the chance, her excitement unable to be contained. After all, it was rare that someone called her to be a part of a sexual fantasy. She was usually the one that set them up.