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The Gigolo Chronicles VI - Tina, Part 1

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A casual coffee shop meeting turns into a more intimate meeting later on!

Tina is a very sexy woman who really loves the attention I give to her breasts when we get together. Like most of my other ladyfriends, she usually cums several times with me, but what makes Tina unique is that she can cum simply from stimulation of her large and lovely breasts, especially their very sensitive nipples.

She gets the most enjoyment from our love-making when her first climax is from my caressing, licking, and sucking her glorious tits so that is how we always start out. Of course, that isn't the only kind of sex she likes, she goes for all the usual things–oral sex, straight sex, even anal sex on occasion. She is pretty open-minded, so long as "the girls" get the first attention!

When she and I hook up, she always wants me to make the girls happy first, which always gives her the first orgasm. Then I will go down on her and she usually cums the second time from my eating her pussy, and then we decide from there what else we want to do until her last orgasm and she always has her own special way of taking care of that.

Tina and I met at this little coffee shop we both frequent when I'm in town. It was almost three years ago now, I guess. I was sitting at one of the tables reading the afternoon paper one day when this beautiful woman comes up to me.

"Um… excuse me… would you mind terribly if I joined you?" she asked, pointing to one of the chairs at my table. I looked up at her and then took a quick (and discrete) look around. The place didn't seem that busy, but she was attractive and I wasn't expecting anyone else…

"Of course, please," I said, standing up for her.

"Thank you. My name is Tina. This may sound strange and I feel a little like a junior high school girl, but I have seen you in here many times and always thought you might be someone I wanted to meet and get to know better. I have finally got the nerve up, sort of, to come and introduce myself," she said, blushing and looking at her fidgeting hands.

"Well, I am glad you did, Tina. My name is Tony. Would you like something to drink?" I asked.

"I would love something to drink - and help with this dry mouth! But I don't know much about the different kinds of drinks here. I don't know the difference between a latte, a cappuccino, or a mocha!" she admitted.

"Well let's see… do you like your coffee to grab you by the throat and slap you awake, or are you more the sit by the fireplace on a cold rainy day drinking your coffee while you read a book type?" I asked.

"I am the sit by the fireplace reading a book type. Strong coffee upsets my stomach actually," she said.

"Then might I suggest an Americano then. It is smoother and not a strong as some of the other drinks here," I said.

"Sounds delicious, thank you," she said. I motioned for the waitress to come over and I ordered our drinks. Once she headed off to put the order in, I turned to my unexpected guest.

"So tell me a little about Tina," I asked. I know that people, especially women, love to talk about themselves and if prompted, all I need to do is listen to them and I will find out a lot–many times I will find out more about them than they are realizing they are telling me.

Such was the case with Tina. She began with the basics; her age, her job, how long she had lived in Dallas. As she talked, though, I noticed she had the ambiance of a woman who has been repressed and subdued. I know this because it is a common thing in my work. A lot of my ladyfriends have the same comportment, at least at first.

Unfortunately, I make my living off of women who have, for one reason or another, had the wind taken out of their sails and need to be uplifted. Whether it's by their husbands, boyfriends, ex's, or parents, these women have been stifled and made to think their opinions and sometimes their whole worth is of no value. And Tina had that same demeanor about her.

After she had given me her basic biography, it was my turn. "Okay, that's enough about me. I came over here to learn about you. So what is Tony's story?" she asked.

So I began telling her about myself. She seemed fascinated and hung on my every word. I don't know how long she had been watching me at the coffee shop, but now that she had taken the step to make herself known to me, she wanted to learn more.

"What do you do for a living?" she asked. This was going to be a bit hard to say. I would have to be tactful and discrete–I couldn't tell her too much since my "job" wasn't exactly welcomed in social circles.

"Well, my job is a bit difficult to describe. I guess the best way to put it is that I am part entertainer and therapist," I said.

"That's rather an odd combination. What is it you do as this entertainment therapist?" she asked.

I thought about her question for a moment. I hadn't given her my last name yet. I hadn't given her any way to contact me. All she knew about me that I was Tony and I came to this coffee shop once in a while.

I looked around and there was no one sitting at any of the tables near us. And I thought this woman might just be a potential future client… she had the air about her of a woman unsatisfied with her life.

I crooked a finger at her indicating I wanted her to lean in closer. When she did, I dropped the news on her. "Tina, I am a male escort. A gigolo. Women pay me to have sex with them. My ladyfriends call me up when they are feeling down or neglected, and I come over and make them feel better–make them feel they are important, that they matter.

"And yes, I take care of their sexual needs, too. But mostly, these women need validation. For whatever reason, they feel that they have been dismissed and ignored–that they are just decorations and their opinions, ideas, feelings, and needs are of no consequence. I show them that they do matter. I make them feel like they are valuable and important and needed. Because they are.

"My job may seem on the surface to be one of taking advantage of a woman in a fragile state, but when I leave them, they are feeling much more empowered, much more self-confident and much happier. I find them broken and glue them back together again–at least for a while" I said.

Tina looked at me in silence as I told her about my work. I wasn't sure if she was shocked speechless or just trying to understand, but when I was finished she sat there for a couple more moments, digesting what I had said.

"I-I see," she said finally, "Can I ask… how much does something like that… cost?"

It was a question I can honestly say I wasn't quite expecting from her. But she was already in this far so I told her. "Well it depends on what is involved and what she wants," I said. I gave her a range of costs for the average date.

"Oh my goodness, that's kind of pricey–you must be very good at your job!" she said, wide-eyed.

"Well, unlike most of the 'entertainers' in my field, I don't get paid by the hour. I get paid by the experience. In other words, it's a set price we decide on, and I don't leave until the client is happy with what they got. Sometimes that can take a day, sometimes it takes two or three. But I don't leave until they feel they got full value for their money. I very rarely go out for a two-hour date," I explained.

"Well, I don't know you very well, Tony, but I can see that in you. Just by the way you explained your work to me, I can see you do care about your 'client' and want them to have the best time possible.

"It is a rather unorthodox way to make a living, that much is true. But there is a need for your services–I know that personally. And it's good to see that there are still a few men out there that value women as people not as objects or trophies," she said.

It was that statement "But there is a need for your services–I know that personally." that caught my attention.

"Do I detect something in that statement, Tina?" I asked.

She paused for a moment. I don't think she expected me to see through her. Evidently, she had been ignored for so long that she thought it was standard practice. Then it dawned on her that I had noticed and she hung her head."Yes," she said softly.

"Tina, if you aren't doing anything really important, would you like to go for a little drive?" I asked her.

Her head raised up a bit. "A drive? Where to?" she asked.

"Oh, I don't know, just a drive. That way we can get to know each other better. Just a simple drive is all," I said.

"I suppose it would be all right," she said. I got up and helped her with her chair and offered her my arm. She smiled and wrapped her arm in mine and we walked out of the coffee shop to where my car was parked.

Once we were in the car and we left the parking lot of the coffee shop I spoke up. "Tina, do you believe friends should be able to talk freely between each other?" I asked.

"Sure. I mean if you can't talk to a friend, who can you talk to?" she answered.

"That's the way I feel too. Do you think you and I are friends? Would you like to be friends?" I asked.

"Um… yeah. I would like to be friends…" she said, not sure where this line of questioning was leading.

"Well then, Tina, as your friend, tell me what it is that you were hinting at back at the coffee shop," I said.

"Oh, it was nothing. I was just… oh never mind, please, it's okay," she said.

Just at that moment, we were passing a shopping mall so I quickly pulled into the parking lot and into a parking spot in the middle of the lot with no cars anywhere close to us. I stopped and turned off the car.

"W-what are you doing, Tony?" Tina said, a bit alarmed at my sudden move.

"Relax Tina, it's okay. It's just that in my line of work I have to be able to read my ladyfriend's silent language as well as her spoken one. And right now my senses are telling me that there is more to this than just 'nothing'. I could sense from the moment you approached me that there was a reserved and timid quality about you–which was directly opposite of someone who just wanted to get to know me as you claimed.

"Now, I want to be your friend, Tina. I want to get to know you. But I need to know what has you so guarded. I can't get in if I don't know where the door is, now can I?" I said.

That was too much for her. She broke down sobbing, "Oh Tony! I don't know what to do! I love my husband, I really do. He's a good man and he works hard to support me and my daughter and give us nice things.

"But in doing it, he's forgotten who he is working for! He works late into the evenings and goes to work early in the mornings. Sometimes he doesn't come home for dinner. My little girl hardly knows who her Daddy is anymore.

"And as for me… well, he has forgotten me too. I hope you don't think I'm a terrible person, but I haven't felt like a woman in so long. Tony, our sex life is non-existent. I can't even remember the last time I was properly kissed! It's just a peck on the cheek as he goes off to work and…" she said, as I cut her off. I'd moved closer to her and gently turned her face towards me as she talked, and then I put my mouth over hers.

At first, her kiss was stiff and hard as if she was trying to resist me, trying to be a "good girl" and maintain her virtue. But it only took a couple of moments before her walls came tumbling down and she melted into my kiss. She moaned soft and low and put her arm around my neck, pulling me closer. This woman hasn't been properly kissed in a long time, I thought to myself, then proceeded to remind her that some of us still knew what a proper kiss meant and how to give one.

After a few heated moments of kissing, I let her up and she sat there with her head on the headrest of her seat, gasping for air. "We should probably be getting back so you can get home. Wouldn't want hubby to start worrying and come looking for you," I said.

"Yeah," she said, sounding a little disappointed that this had to end so soon. She straightened herself up a bit and checked herself in the mirror on her visor. I drove her back to the coffee shop and walked her up to her car.

"It was very nice meeting you, Tina. I hope we can get together for coffee or something again soon. Here is my card. If you ever want more than just a kiss, give me a call," I said, pressing the card into her hand. She put it in her purse, then looked up to me.

I could see in her face she didn't want to go but knew she had to. She looked into my eyes for a long moment, flicking back and forth between them. She wanted me to give her a reason - an excuse not to go home just yet. Then she turned and glumly got in her car and drove off.

I had a feeling this wasn't the last I would see of Tina.

I was right in my assessment. It took about a week, but one day when I got home there was a message from my answering service. I called them up and they told me a woman named Tina called and said to call her sometime before 4:30 that afternoon.

Since it was only 3:00 at the time, I called the number they gave me. "Hello?" the woman on the other end said.

"Hello, is this Tina?" I asked.

"Yes it is, who is this?" she said.

"Tina this is Tony, you called my service?" I said.

There was a long pause on the other end. "Yes," she said in a softer tone as if she didn't want to be overheard.

"Is this a bad time? Is your husband home?" I asked, not wanting to cause trouble.

"No, he's at work. I'm here by myself," she said, still speaking quietly. Then I knew she was being quiet for her own benefit… she didn't want to admit to herself what she was doing.

"Well, what is it I can do for you, Tina? Why did you call?" I asked.

"I was wondering… um… could I… Oh god, could I see you? You know… what you were talking about the other day," she said. She didn't want to say it directly, or she didn't know how to properly ask for it, so I helped her.

"You need my services, Tina? Is that what you are asking?" I said.

"Yes please," she said.

"Of course. But I don't discuss business over the phone. Can you meet me at the coffee shop in say a half hour and we can talk more about this?" I asked.

"Okay," she said.

"All right, I will see you there," I said and hung up. I smiled to myself a little bit and then got ready to go to the coffee shop.

The coffee shop has this little room on the side where you can sit at the table and the waitress can close the sliding glass doors to give you some privacy. They use it for business deals, private parties, and so on. I was sitting in the little side room when the waitress brought Tina in. After she showed Tina to my table, she shut the doors quietly so we could talk.

"Hello, Tina. I was hoping I would hear from you again," I said.

"Thank you for seeing me," she said.

"Of course, it's my pleasure," I said, "Can I get you something?"

"No, thanks. I can't stay long right now. I just wanted to meet with you and talk about… hiring you, is that the right term?" she asked.

"Well, I prefer dating… it sounds more romantic and intimate," I said.

"Oh, well then I would like to talk about our date then," she said, blushing a little.

"I like to see you blush, Tina… it looks good on you," I said.

Which made her blush more. "You are good for a girl's ego Tony," she said.

There was a pause in the conversation and then she got down to business. "My husband is going out of town on business next week. He will be leaving Sunday evening and be gone until Wednesday or Thursday. Could we get together… for a date… while he's gone?"

"I'd be more than happy to, Tina. Just give me a call when your husband leaves and I will tell you where I'm staying. I will get a hotel room so your neighbors won't see a strange car in the driveway and ask too many embarrassing questions. There are a few hotels here in Dallas with their own private parking areas," I said.

"That would be fine. Um… how much will this cost?" she asked a little embarrassed.

"Well, it kind of depends on how long you would like the date to last. Are we talking an afternoon or are we talking overnight or multiple nights?

"Let's start off with an afternoon and take it from there, okay? I'm sorry, but I've never done anything like this and I'm a bit…" she said.

"That's perfectly fine, Tina. Every one of my ladyfriends has had their first time and been nervous. It's okay," I said. "Tina, I can see that money is a little bit of an issue here. Your comment about it when we first met and now. Can you put together say $500.00? For that, I can promise you an afternoon you won't forget!"

"Yes, I can do that. I have some money put away," she said.

"Good. Then I will call you Sunday night and we can make plans to get together Monday if that will work for you?" I asked.

"That will be fine. Is there… um… anything I need to bring with me?" she asked.

"Well, this is a date, Tina, so just dress as though it was a date and I will take care of all the rest," I said.

"Okay," she said, blushing and looking down at her lap again.

We finished our drinks then she went back home. I made a couple calls on the way home and secured a reservation at a decent hotel with off-street parking.

That Sunday night around 8:00, I called Tina up. We talked for a bit and I could hear in her voice the excitement that she had for our upcoming "date". She said that her husband had left about a couple hours earlier and that when he did leave, he only gave her a cursory peck on the cheek, even though he would be gone for four or five days. I made a mental note to make sure she got lots of real kisses on our date. She said she had been to the bank and had the money I had told her.

"That's fine Tina, but this is a date so that's the last talk about money or cost or anything like that until it's over. I don't want you feeling like you bought a date with me. We are going to meet like we are lovers, not paid performers, okay?" I told her, "I don't talk money when I'm with my date - it cheapens the experience and makes it less intimate and personal."

"Okay," she said.

"All right then, I will see you tomorrow, say 1:00 pm?" I said.

"Okay," she said, "I'm looking forward to it."

"So am I honey," I said. I gave her the name of the hotel and the name I would be going under... Tony Harris.

The following afternoon, I was sitting in my hotel room waiting for Tina to arrive. Right at 1:00, I hear a soft knock on the door. I opened the door to a true angel. Tina had taken my words about dressing as if it were a real date to heart. She looked amazing.

She was wearing a black lace over a purple chemise that had a lace hem at the bottom and across the top of the cups. It was short enough the tops of her stockings fell a few inches below the bottom of the hem and were held up by garter straps. She wore a matching lace panty under the chemise and her leather coat over it so that she could walk outside and no one was the wiser for it.

Her makeup was understated but applied with a critical eye for perfection and she looked lovely. I stood there in the doorway for a long moment just drinking her in.

"Come in," I said when I finally found my voice again.

She stepped inside and I took her coat. That's when I got the full vision of Tina. "I wasn't really sure about what I should wear. I haven't been on the dating circuit in some time, and this isn't the usual kind of date. So I wasn't sure what or how much to dress up in," she said, waving her hand over her outfit.

"You look spectacular, Tina, don't worry about that at all," I said.

"Thank you. I'm so relieved that you like it!" she said letting out a deep breath.

Remembering what she said on the phone the previous night, I didn't hesitate to confirm her attractiveness. I pushed her gently back against the door and leaned into her pressing myself against her as I leaned down and kissed her soft red lips. Tenderly at first–I didn't want to overwhelm her right off–but then harder and deeper as I felt her responding, the next thing I knew she was fumbling at my shirt.

"Oh, Tony, I hope you don't think I am some slut or something, but I have been thinking about this since that first kiss back at the coffee shop when we met. And once we made our date for tonight, it's ALL I've been thinking about! Tony, I want you to make love to me, please! Please show me what it's like to feel again!" she said.

I could hear the wavering in her voice. If there was ever a woman who needed reassurance and validation, it was Tina. I pressed my lips harder to hers; I wanted this woman to know she was being kissed. She wasn't going to get a cursory peck on the cheek from me! As I held the kiss, Tina wrapped her arms around my neck and I felt her running her fingers through my hair. In return, I pushed a knee between her slightly spread legs letting her know I was there and pressing into her crotch a bit.

Tina felt my leg pushed against her and with my mouth covering hers, she moaned into it. Subconsciously, she began rubbing her needy pussy up and down against my leg, literally humping my leg and showing me she didn't come here for mere kisses and conversation. I slid my hands down her sides to her hips and hiked up her short chemise so she could rub her panty-clad pussy against my leg easier. Keeping my left hand firmly planted on her ass, my right hand wandered upwards and found an eager, but neglected tit.

I hadn't been mauling her ass and tit for more than a minute or two when she pulled away from my kiss. She lay her head back on the door, "Wait! Tony please…" she gasped for breath. I gave her a little time to regain her composure while continuing to give her neck and shoulder tiny little kisses. She held onto my neck and guided me where she needed the next kiss and I followed her lead.

When I had worked my way to her collarbone, I began moving down the center of her chest. She knew where I was planning on going and her panting got heavier. As I kissed my way slowly downward I slipped the thin shoulder straps of her chemise off her shoulders so that when I got there, I could slip her top down a bit.

I reached her full, creamy and heaving tits and kissed the top of each one. Another louder moan escaped from her lips as she felt my hot kisses on her tender flesh.

"Take me to bed… I really love what you are doing, Tony, and I want you to keep on doing it. But take me to bed–I know it will be so much better when we are both lying naked in bed," she said, in a voice so soft it was almost a whisper.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © © Copyright 2013-2018 by Master_Jonathan
All rights reserved, including all copyrights and all other intellectual property rights in the contents hereof.

The compositions and contents herein are not to be copied, reproduced, printed, published, posted, displayed, incorporated, stored in or scanned into a retrieval system or database, transmitted, broadcast, bartered or sold, in whole or in part without the prior express written permission of the sole author. Unauthorized duplication is strictly prohibited and is an infringement of National and International Copyright laws.

All names, characters, businesses, places, events, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters portrayed in this story are over sixteen (16) years of age.

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