Ann: A Love Story Ch. 76

"Can you give me some examples?" I asked.

"Oh...I can give you all of them...but first, the requirements. I just took a shower before you arrived, and I prepared myself for the evening, just in case. You'll need to shower...alone. I don't shower with my clients...or bathe with them. And I will determine if you're clean or not. If I'm not satisfied, you'll be asked to shower again, a little closer to the soap, if you know what I mean. Do you agree with that?"

"Sure...if I decide I even want to do this."

"Well...yeah, that's what we're talking about, right? Look, we'll make this easy. When I ask you if you agree, I'm only asking if you understand what I'm saying and accept it. That way, IF you decide you want to continue our evening together, we won't have any misunderstandings later. I'm just setting the ground rules. Alright?" I nodded, and Ann continued, saying "Good. Next, you will have to wear a condom, which I will provide, if you want to fuck. That is not negotiable...and again, it's because you haven't been screened. Do you agree?"

I was a little stunned, but at the same time, we were role playing, and Ann had a way of making things so real that I totally got it. Nodding again, I said, "Yes...of course."

"Lastly, the party ends at 3AM. That's when my half a day is up. At that time, you will politely be asked to leave my room."

"Your room?"

"Safety, Mr. Thomas. You should know by now that the screening my agency does is very thorough, and it's a huge part of what I do, and why I do it. But when I step out of the comfort zone that the agency provides to have a little fun on the side, I always have to think about safety first. Face it...what I do for a living can put me in very vulnerable positions. So, I have to think that way. I hope you understand."

"Yeah, I suppose."

"Look Neil, I want to make the evening enjoyable for you, but I have to be comfortable for me to be able to do that. So, just like now, I have things in my room that I can get to at any time for my protection. Besides, Heather said your room is on the top floor, and it's at the end of the hallway so you can have privacy...she said something about it being because you're staying there a while. But that also means it's out of earshot of a lot of the hotel. My room is on the first floor near the lobby, again...for my safety. Are you okay with that?"

They were actually really valid points. Ones I never would have thought of. And by planting the seed, Ann was letting me know that Barbara had thought those things out, along with likely a lot of other things. "Sure...your room would be fine. And 3AM is fine too."

"That's good. Now, let's get to the fun stuff. Here's what I'm willing to do tonight. Again, if I list something that's off the table, it's because of safety, and I'll tell you. But I'm going to list them all, okay."

"Sure...fire away."

"First, orally, I can deep throat almost any sized cock. And I will, if that's what you'd like. You can also fuck my mouth...I'll let you know if you're too rough, but I've yet to have that happen. You won't have to wear a condom if I'm sucking you. You can cum in my mouth, and yes, you can cum on my face if that's something you like to do. Any questions about that?"

"Uh...no, I think I've got that."

"Good. Next, fucking. You can fuck my pussy as long and as hard as you want, again, as long as you wear a condom. Same goes for my ass. If you want to fuck both, that's fine...but you'll need to change condoms to do that if you're going to go back and forth. You can cum inside me, with the condom on...and if you'd like, I will eat your cum from the condom. In fact, I will clean up any pools of cum that you'd like me to clean up. If you'd like to cum on my body, you can cum anywhere but on my pussy, for safety. Any questions about any of that?"

Shaking my head, I said, "Uh...no. We're still good."

"Okay. There's no water sports of any kind, or anything involving the back door, if you know what I mean. And that's both giving and receiving. I'd rather not have to be too graphic, but I will if I have to. Do I need to be clearer on that?"

"Uh...NO...and let's not go there again," I said, my eyes wide open.

"Well, I hate to bring that up, Neil, but I don't know what your bent is, and I have to spell that out. I don't have to do that with the agency...and it doesn't make me comfortable to do it now, but now we know."

"Yes we do. Next," I said, moving my hand to tell her to go on.

"Okay...groups and threesomes, both men and women. Gangbangs are a no, for obvious reasons. Too many people create too many variables. I can, and will do threesomes...but not tonight. I wouldn't know the third party any better than I know you, so that's out. The same goes with any kind of bondage involving me being the Sub. I can't be tied up if I don't know you, and you haven't had the background screen. I AM willing to be a Dom if you like being submissive. I have everything I need with me if that's something you enjoy. Any questions there?"

"No...we wouldn't be going anywhere near there anyway," I said laughing.

"Handjobs and footjobs are obviously okay. You can also fuck my tits, or any other places on my body you think you would want to put your cock. Anything we haven't covered that comes up unexpectedly will be talked about when you decide you might want to. I only ask that you respect me, and my respect my wishes if I say no to something."

"Absolutely. Anything else?"

"Only that I guarantee you will cum at least one time, provided your equipment works properly. And you can cum as many times as you can get it up, up until 3AM. And I'm serious about that time, Neil...if you're hard, and we're doing something...come three o'clock, I will stop and ask you to leave no matter what."

"Harsh...but okay," I nodded.

"Okay. Two more things, and then were done. One...there will be absolutely no kissing on the mouth...at all. Two, there will be no cuddling or sleeping together. This isn't an overnight stay, and I'm not your lover. When I'm with a client that goes through the agency, they actually have to pay extra for that kind of attention, and affection. The truth about this is, sex is sex, and I hope you'll find that I'm not only professional, and I'm VERY good at my job, but I also enjoy my work. I like to think it shows, and that my clients get their money's worth. But when it comes to things that can be more emotional...I have to work myself into that mentally. Frankly, sometimes I think it would be easier just to be on my own and not go through the service. Guys tend to get attached to escorts...but they don't so much to every day, run of the mill hookers."

"So why do you do this?"

"I'm not going to answer that, Neil. It's part of my personal life...and that's private. Do you have any other questions?"

"Yeah...I'm wondering where the damn check is," I said as I looked around for our waitress.

~*~*~*~*~*~

Driving back to the hotel, Ann was looking in the lighted mirror on the sun visor over her seat, applying a fresh coating of her dark red lipstick. She made the process look so sexy I'm surprised that I didn't have an accident. I had to force myself to watch the road, and all she was doing was freshening her makeup.

She checked her look in the mirror, running her fingers through her long red hair, and puckering her lips seductively, before flipping up the visor and sitting back in her seat. Ann then crossed her legs, making her dress move, her entire left leg coming into view all the way up to her hip. She started moving her leg up and down slowly, as if to make me catch it out of the corner of my eye. But more often than not, I'd just blatantly take a quick look, fighting to keep from moaning inside.

Ann face had a sexy smirk on it as she caught me looking, and she moved a little in her seat, facing more towards me.

"So, tell me Neil. Is that your way of window shopping?" she said with a giggle.

"Sorry...it's hard not to look," I said, actually embarrassed. It was a strange reaction, considering that it was my fiancée sitting next to me. But I'd gotten so into playing the part that I honestly felt a little guilty for staring at that gorgeous leg.

"You don't have to be sorry, Neil. I just don't want you to think I'm trying to entice you or anything like that. Like I said earlier, this is really unusual for me. Most of the time, I know what I'm doing by now, and I'm into the moment. I don't want you to think that I'm trying to sell myself, even though that's what it really is, isn't it?" she laughed. "You know, sometimes I forget what it is I really do. I'm sure that sounds absurd, but I rarely think about my job. I just get my assignment, and then I go and do what I'm paid to do. So it's really different for me to have to sit here and wonder."

"Wonder...about what?"

"About whether I'm going to be working tonight or not. But I understand. You've already spent five hundred dollars just to be with me and then paid to take me to dinner. Another five hundred is a lot of money, and you have to decide if that's worth it. It can't be an easy decision for someone like you."

"Someone like me...what's that mean?"

"You're obviously in love, Neil. I can tell. So this has to be a struggle for you. Most men I meet in my job, they don't have feelings like you have. They might love someone, but not like I can feel that you love Ann. The truth is, more often than not, my clients USED to love someone, but they don't anymore."

"That's sad."

"That's life, Neil. People grow apart if you don't work at a marriage. It happens with successful men a lot. In fact, I see that all too often, which is why this is different. I'll totally understand if you decide not to continue tonight. But then again, Ann sounds like such an incredible woman, so I can also see why you WOULD do this. After all, she loves you so much that she hired me, all because she wants you to be happy tonight...that's pretty rare too."

"Ha...you sound like you're in sales," I said as I turned the car onto the road the hotel was on.

"I'm not trying to be. I'm just letting you know that I understand how this is different from what I normally do, and I'm willing to be patient while you decide."

"How patient?" I laughed.

Ann looked at her watch, which made me check the dashboard of the car to see the time as well. It was almost 8:30. Ann turned to me and said "If you'd like, we can go to the bar and you can buy me another drink to give yourself a little more time to figure this all out. At nine, I'm going to go to my room. Hopefully by then, you've decided whether you want to join me there or not."

~*~*~*~*~*~

The band was another good one, and the bar was as crowded as I'd seen it. I'd had to park far away from the entrance again because of the lack of open parking spaces near the entrance, but Ann didn't seem to mind. I think she enjoyed the way she was dressed, and how that made her feel. With the frame of mind she was in because of the role she was playing for me, she had an air about her that was amazing. I'd never seen Ann look the way she was acting. She had a confidence and sexiness about her that was different, and it was really intriguing to me...not to mention a huge turn on.

There was no place to sit in the bar, so Ann stood near the back wall next to a tall table; she with her wine glass in her hand, while I had a bottle of Heineken in mine. Taking a sip of her wine, Ann's eyes were blazing as she stared at me, her body moving and swaying to the beat of the music.

"Would you like to dance, Barbara?" I asked.

"No thanks," she said politely as she took another sip, the reflection of her engagement ring sparkling from the stage lights, reminding me that it was on her right hand instead of her left.

"Are you sure?"

Ann gave me a sweet smile, and said, "Neil, you're such a gentleman. I love that you treat me with such respect. And I know you're being polite, and doing what comes natural to you. But at the end of the day, I'm a professional businesswoman. And this, for me, is a business meeting. If you'd like me to dance, it will cost you five hundred dollars. But, I promise, for that price, I'll dance here or in my room any way you want me to. I don't want to seem pushy, or cold, or make you think I don't appreciate what you just offered. As a woman, I love it. But this isn't a date."

I looked at my watch, and it was a quarter to nine. There was little doubt that I was going to make Ann's fantasy come true. Actually, there was no doubt. Hell, at that point, it was becoming MY fantasy. But I loved the way she was drawing things out. The whole thing was like mental foreplay, and it was working. I was so hard, and so turned on, and it wasn't just because Ann was actually with me. It was also because of what we were doing. It was more exciting than I ever would have thought it would be...and that was because she was making it seem so damn real.

"May I ask you a question, Barbara?" I asked with a gentle smile.

"Sure...although I can't promise that I'll answer it," she said with lilting laugh.

"I was just wondering...you seem so confident and self-assured in what you do, how long have you been doing this?"

"Long enough to be confident and self-assured," she smiled.

"Seriously, Barbara. I'm curious."

"And curiosity is a good thing. But I'm afraid I'm not going to be more specific than that."

"Why not?" I pressed.

"I suppose I could just say it's none of your business, and leave it at that. But here's the real reason why...appearances."

"Appearances?"

"Yes...it affects how I'm perceived by my clients. If I say that I've been doing this for years, and I've been with hundreds of men, then I go from being perceived an escort, to being more of just a whore. And that is certainly not who, or what I am. But if I say that I've just recently gotten into the business, then I look like a novice, and suddenly clients are wondering why they're paying so much money to be with me if I don't know what I'm doing. So, all I'm willing to say is that while I'm not new to this, I haven't been doing it so long that I've become jaded. I'm very good at my job, Neil...for a reason. And I still enjoy it most of the time. Does that answer your question?"

"That one. Have you ever been in danger doing this?"

"Every time I'm with someone new, it's dangerous, Neil. Especially on the few occasions like tonight when I'm technically on my own. But I'm very careful, and I take lots of precautions."

"Like what?"

Ann looked at her watch again. It was almost nine, and she took her glass and finished the little wine that was left in it, setting the empty stemmed glass on the standing room table nest to us.

"Thanks for the drink, Neil...and the dinner. I had a great time," she said politely as she grabbed her clutch off the table. "It was wonderful to meet you."

I looked at my watch, and there was still a minute or two to go before nine. "I thought I had until nine," I said with a smile.

"Neil, I don't believe for a second that you're this indecisive. You knew what you wanted to do back at the restaurant. So, I'm going to my room. And the only question right now that either one of needs to answer is...are you coming with me, or not."

Ann smiled as she started to walk past me, brushing her sexy body up against mine. I inhaled, catching another whiff of the perfume that was most definitely Ann's...the same one her alter ego, Barbara, was apparently borrowing.

Gently touching her arm, Ann stopped and looked at me. "I do have this wad of cash burning a hole in my pocket. It would be a shame to ruin this jacket," I said as I pulled out the money.

"Not here, Neil. If this is what you want, we need to do that in my room," she said, her eyes showing me that she wasn't happy about my taking out the money in public. It was a narrow, icy stare...one that I felt in the core of my body. One I actually hoped I'd never see again.

Slipping the money back into my pocket, I said, "Sorry, Barbara...I didn't mean..."

"I know, Neil. But you never know who might be around us, especially in a crowded bar. A place like this can attract regular hookers too...and I can't get lumped in with them. I've never been arrested before, and I don't intend to start tonight. Now, are you going to come with me?"

"I'll do the best I can...but you're the one that says you're good at this sort of thing. I've always found it kind of hard to time it that well, but I'm sure if anyone can get us close to cumming at the same time, you can," I said with a smile.

Ann took my arm, and said, "I'll see what I can do...I love a challenge. And I love that you're thinking about pleasing me too...that doesn't happen with every client I'm with, or men in general, for that matter."

Leading me out into the hallway, Ann didn't head down towards her room. Instead, we headed to the lobby, which surprised me. Before I knew it, we were approaching Heather, who was busy with another guest. We waited in line in silence for a little bit while Heather finished up, and then Ann led me forward to the counter.

Heather's smile was as wide as the lobby, and she seemed excited. "Hello Barbara. Hello Neil. What brings you two to see me?"

Ann looked at me, and then she turned to Heather. "I believe Neil's made a decision, and he's agreed to the terms of tonight's arrangement Heather. So, we're going to go to my room now. Do you have everything set up for me like I asked?"

"Yep...and you picked a good night. Stacy is off tonight, so Meredith and I are splitting her shift. I'm here until 4, so I've got you covered, so to speak."

"Oh...good, so I won't have to deal with anyone else, then," Ann said with a little sigh of relief.

"Yep...you're good to go. Have a good time, Neil," Heather said with a little wave. Then she looked at Ann and said, "And remember what I said, Barbara. Watch out...that cannon of his can really go off!"

Ann snickered. "Thanks Heather. I'll try to remember. Come on, Neil. Let's go get better acquainted," she said as she led me along.

Seconds later, Ann was using her key to open the door to the room, and when we stepped inside, I was stunned once again. Ann had put up some kind of curtain between the little hallway, and the bedroom, cutting off the front door and the bathroom area. That was why the light was so dim when she'd opened the door when I'd first knocked. The cloth was diffusing the light from the other side.

Ann closed the door behind us, and said, "Don't worry about that...I've just got things ready on the other side, and I didn't want you to see them earlier."

"Why?"

"Because, you weren't sure about this, and I didn't want to scare you off."

"O...kay," I said, suddenly unsure of what Ann may have in mind.

Sensing my trepidation, Ann reached out and touching my hand. My reaction seemed strange, considering all of this was just a staged thing. But Ann was so real, so convicted in how she was portraying Barbara, that my reaction was what it was...just as real.

"There's nothing to worry about now, Neil. You already know all the rules, so to speak. My job now is to make you happy. There's just one more thing we need to do first."

"What's that?" I said, forgetting already.

Ann held out her hand, and smiled politely. "This is a business before pleasure profession, I'm afraid. I need the other five hundred now if you want to continue."

I reached into my coat pocket, and pulled out the bills, counting them off in her hand like some kind of teller. Ann smiled as I pressed each bill into the palm of her right hand, and I was sure she shook a little as the feeling of getting paid for what she was about to do sunk in. Even though it was all pretend, it hit her in a way that seemed to make her weak in the knees for a moment.