Michelles New Profession Ch 03

This story follows directly after Jacqui's Wedding, Chapter 2. Thank you very much to Shygirlwhore for editing assistance.

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Monday after I got home from work, Michelle and I had fun going through her escort service e-mails. If they had the words 'fuck', 'cock', or anything comparably crude in the subject line we deleted them. Michelle loves romance. She wants to be romantic and see what follows...hopefully a very enjoyable evening, then a night of fantastic sex. I love going through them with her, to see the type of man she wants to spend the night with. It's hot as hell for me!

There still weren't many, seven to be exact. Two caught her attention, one said, "Hi, love your site. I'm hoping you can help us out with our son." She clicked on it and we both read, "Our son is twenty. His 21st birthday will be next week. He's extremely shy, but a very nice young man. We know he's never been on a date and probably never even kissed a girl. Your profile sounded very interesting to us. We know you're older than him but that's part of what attracted us to you. We were wondering about hiring you for a date with him on his 21st birthday." Then it went on to give their contact e-mail information.

"He sounds a lot like me when we first started going out. I was twenty-one and you were my first girlfriend." I really, really wanted her to delve into this one further.

"It does sound kind of intriguing. I wonder how far they'd want a date to go. There's a lot of difference between a simple date and what I'm planning for my dates. Besides that, he's kind of young, don't you think?"

I laughed at the understatement about her 'dates'. "Yeah, he's young but it sounds like it could be fun to me...going out with a 'never been kissed' guy. I think you should e-mail them back and see what happens." She typed out a brief e-mail. "I might be interested in a date with your son. Can you please tell me a little more about him and what you might be expecting from me? Amber." Then she hit send.

It was less than ten minutes later that she got another e-mail. "Thank you for answering us. We'd almost given up hope." We looked at the date of their original e-mail and it was the previous Thursday. No wonder. It went on, "Jeremy is a physics major at the University of Washington. He's very intelligent but so shy. He gets flustered whenever he's around one of our friend's daughters and complains that they're so immature. I think he's too shy to approach one of the girls at college. I've attached a picture of him. As you can see, he's a nice looking young man. We're very proud of him but would like to see him open up a little more. As far as what to expect from you, we'd only hope for him to enjoy an evening with a beautiful girl, someone experienced enough to help him get past his shyness. Judy." She gave Michelle her phone number and asked if she could call.

She clicked on the picture file. His mom was right, he's a pretty good looking kid. Brown hair, thin, has a nice smile. We couldn't tell a lot about him because it was a portrait, not a full photo.

I asked her, "Well, what do you think?"

"I think I could help him. Besides, it might be fun. I'd like to do it."

"Okay then, why don't you call his mom."

Michelle picked up her cell phone and dialed the number Judy had given her. "Hello, Judy? This is Amber." I couldn't hear the other side of the call.

"I think it's very nice what you're trying to do for Jeremy."

"No I haven't, but I'm sure we'd get along very well. Actually, he sounds a lot like my husband when we first met." She smiled at me and tried to tell me with her lips what was being said on the other end. I wasn't getting it so well, but was pretty sure just from her end of the conversation.

"Yes, I'm married, and yes my husband knows all about what I do. He's very supportive." A brief pause then, "Would like to speak with him?" I gave her my hand, to hand me the phone, but she shook her head no.

"I think that'd be a fantastic idea. How about Ellensburg? That's about halfway."

"Okay, it's a date. I'll see you then. Oh, maybe I'd better ask, when is Jeremy's birthday?" She listened for a moment longer, thanked Judy and hung up the phone.

"She'd like to meet me, tomorrow in Ellensburg at Denny's at six. His birthday's this coming Friday. Lucky I answered their e-mail first before scheduling something for Friday night."

The other e-mail that she was interested in was a businessman from Chicago that was going to be in Seattle over the weekend and was looking for someone to keep him company for an evening. She answered his e-mail and after a couple e-mails back and forth had set a date with him for Saturday evening.

The next day I took off work a couple hours early. It's about a two-hour drive to Ellensburg and we got to Denny's about five-thirty. Michelle didn't know if they wanted to meet me or not, so she walked in alone and I followed about ten minutes later. I wanted to sit where I could overhear their conversation, but there weren't any booths open near them so I had to sit at the opposite end of the room where I couldn't even see them. Michelle did see me walk in and where I sat though.

I ordered a cheese-burger and chocolate milk shake (yeah I know - health food), and nibbled at it for probably forty-five minutes. Finally, after what had seemed like an eternity, Michelle walked over to my booth and said they'd like to meet me. I left the rest of my food, paid my bill and went with her to their table. Apparently, the dad, I hadn't heard his name yet, had taken Jeremy to the car so Judy and Michelle could talk business a little more freely.

When I approached their booth, I was a little surprised. Jeremy's mom looked like she was probably in her late fifties or early sixties, kind of old to have a twenty year old son. She extended her hand and took mine with a very nice smile. Judy spoke first, "We're very impressed with your wife. Jeremy seemed to like her too. You're sure it's okay with you if she goes out with our son?"

"It's very okay with me. We've talked about it quite a bit and I know she was looking forward to it before we got here." I went on to tell her, "The way you described Jeremy in your e-mail sounds so much like I remember being, scared to death of girls, before Amber and I started dating. She was fantastic with me and that was almost twenty years ago. I know she'd be good for him."

Judy blushed just a little, apparently not quite sure how to ask, "And if they, you know," She hesitated a bit, before I jumped in, knowing what she was trying to ask.

"Whatever happens is fine with me. We're open and honest with each other."

I guess that seemed to satisfy her. She turned back to Michelle, "Your fee, how do you want us to pay you?"

Michelle smiled at her, that sweet smile that's so irresistible. "There won't be any fee. I want to go out with him."

Judy's face got a very surprised look, "But your website said..."

Michelle interrupted her, "My website wasn't talking about Jeremy. I don't want him to ever have to say that he had to pay a girl for his first date. I want this to be a real date, with a real girl that likes him for who he is, not for his money."

Judy was totally taken aback, "But we have to pay you something."

Michelle was more than adamant, "Then I'm not your girl. I'd love to go out with Jeremy but if you're going to have to pay me to do it, I won't." I couldn't have been prouder of my wife. I knew she had several e-mails from guys she could make fifteen-hundred dollars from that night. Instead, she was trying to make a night out extra special for a young man.

Judy finally smiled at Michelle and put her hand over Michelle's on the table and squeezed it. It looked like she was almost going to cry. Michelle told her, "I'll get a hotel room and let you know where. He can pick me up and take me to a nice dinner, dancing if he wants, and we'll see what happens from there. No more promises than that."

Judy looked a little hopeful then, "Can we pay for your hotel room then?"

"No, this will be my birthday present to Jeremy." Judy told her thank you, and as she got up to leave, Michelle added, "I know we'll both have a wonderful time."

Michelle and I waited a few minutes after they left before we did. Judy's husband had already paid for Michelle's dinner. After we saw their car pull out of the lot, we left. Michelle said she didn't want Jeremy to see me.

Michelle told me a little more about them on our way home. Jeremy is an only child and was a surprise when he came along when Judy was forty-one. They'd given up having a baby years before and by then had decided they were too old to adopt. They suspected their age was partly why Jeremy was so shy with girls his own age, as he'd grown up among their older friends and didn't have much contact with people his own age. They also thought that was why Michelle might be perfect as a first date with him, since he could relate with her age a little more.

They were hoping that if he could gain a little confidence with her, then a relationship with a younger girl would be easier for him too. Michelle said he really seemed like a nice kid and she hoped they were right.

After we got home, Michelle called and made a reservation for two nights at the Sheraton, the same hotel she'd been to with her first extra-curricular lover, Mike. She'd had a honeymoon suite with a hot tub with him, but she was disappointed that all their hot tub rooms were already booked, so took the next best room, king bed with walk-in shower. She thought she might want to make use of a big shower. It cost two-hundred-thirty dollars a night, but she thought it'd be worth it. I suspected so too.

She already had another date for Saturday night, a paying customer, so needed the room for both nights.

Thursday, Michelle went all out to make herself look special for Friday night, kind of like she had before her first extra-curricular date with her old college boyfriend a couple years ago. She went to a spa, and had herself waxed, her finger and toe-nails done. She looked spectacular when I got home from work. When she'd done this before her date with Mike, we'd been abstaining from sex to make the weekend with him even hotter for her. This night, we didn't abstain. God, was she hot! Between being so soft and smooth and the thought of what might happen the next night with a young virgin, we had some of the best sex ever. I couldn't even imagine what Jeremy would think if their date went far enough for him to get into her pants.

The next morning before I went to work, Michelle showed me what she intended to wear with Jeremy. She held up a light blue silk blouse and white leather skirt that fell a good six inches or so above her knees. She said that young people especially like leather so she thought it'd be perfect. Her shoes were a pair of high heels that strapped around her ankle. Her welded-on anklet would slip down over the strap.

Then she showed me her lingerie; a dark blue, matching lace bra and thong panty set. I told her that I understood that when a girl wears a matching panty and bra set it meant she wanted to get laid. Then I commented, "It seems like you've been wearing a lot of matching sets lately."

She laughed and told me, "I guess that proves what they say about a matching set is true then doesn't it." We both laughed and I couldn't help but kiss her.

"I hope you won't mind, but I've decided what I want to wear if I take him back to my hotel." She held up her little silk nightie...the one from our wedding night. "It was your first time and this might be his first time, so I thought it'd be appropriate." A pang of jealousy went through my body. That was ours, just meant for the two of us. Of course to be honest, I'd let another woman wear it once for me so I didn't have much room to complain. "I think he'll like it, don't you?"

How else could I answer that, damn right he'd like it! It had little silk, transparent, bikini panties that would look and feel so good over her smooth, waxed pussy lips.

Michelle finished packing her bag. She packed another outfit for her 'paying' date Saturday night and I finished getting ready for work. I knew she had an appointment with her hair dresser later that morning. The one thing I hadn't thought about was that her Saturday night date would be getting all the sexy benefits of her preparation for Jeremy as well.

About four-thirty, Michelle called and let me know she was at her hotel. Jeremy was planning to pick her up about seven. She knew how badly I wanted to be there to follow her on her date with him, but it wasn't possible. We had made arrangements for later so I could at least listen in. Until then I just had to wait.