The Male Escort Ch 02

I have been out of college for almost four years now. After graduating at the top of my class and having saved so much money, I opened up my own computer service business. I did some repairs and installations of new units. My main goal was still teaching. I was afraid to apply in case the solicitation charge showed up again. The summer teaching job I lost during my sophomore year stayed in my mind all the time.

I was back in my hometown where I knew most everyone. Most of my family still lived there. I couldn't take a chance on them finding out about my past job as a male escort. I started the computer consulting service and went to different businesses to help them upgrade their systems. I also taught their employees how to use the various programs.

That's right! I was teaching people how to use the computers. Teaching the young people was what I wanted to but this was the next best thing. I was able to build a business on my computer knowledge and was able to teach others.

My sex life was nearly non-existent. I was somewhat burned out on having sex for the sake of having sex. If I felt the urge a few times a year, I was lucky. It's not that I didn't have the opportunity; I did date quite a few women. The problem was I couldn't find the right woman. I wanted to fall in love and maybe have a family.

I guess I had a distrust of marriage in general. All these older women I had been with; all were marriages that weren't working. Cheating for both husbands and wives seemed to be the norm anymore. Husbands wanted to watch their wives fucking another man. So many gays and lesbians were out of the closet. The world of love and marriage seemed to becoming extinct.

I guess people like me were part of the problem. I watched my parents and my sister in their marriages. They seemed to hold it together. Maybe there was still someone out there for me. Just maybe being in college and around sex for five years made me leery of women in general.

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I want to tell you about my grandmother. She's the one I love the most. Not the sexual or incest type love. She would be one of the last people in the world I would want to think about sexually. It's just that she is an outspoken woman, not afraid to tell you what's on her mind.

I loved and respected her my whole life. If I were to tell anyone about my past it would probably be my grandma. Just being around her would brighten anyone's day. My granddad, her husband, died three years ago. They were married over fifty years. She was still able to go on with her life.

She told me she often dreamt of the past. She had all her memories to keep her happy, but she told me to live for the future, that I had a whole life ahead of me. I don't know how many times she told me that I would find that one special woman. She would help me find her if I wanted her to. Grandma always made me laugh.

"Okay, Grandma, when you find her, give me a call and I'll even take her out for dinner," I laughed.

At twenty-eight and quite successful, everyone tried to fix me up. Of course, as I mentioned I did go on some dates but nothing clicked. I never led woman on and I treated them all with respect.

One day I got a call from my mom saying they took grandma to the hospital. Her diabetes was acting up. When I arrived at the hospital, grandma said she was glad to see me. She told me they had to get her sugar under control. She mentioned that she started eating too many sweets.

After I bawled her out, in a nice way of course, she told me that her feet hurt. "The doctor said I should walk a little every day but how can I when my feet hurt? He said I needed to get the blood flowing better to my feet."

I went to the end of her bed and pulled up the top sheet to look at her little feet.

"Jeffrey! What are you doing? Leave my feet alone." She was the only one that always called me Jeffery. I didn't mind, not from her anyway.

"Grandma, just be quiet and let me rub your feet. I took a massage class in college and this might help you."

I brought a chair to the end of her bed to sit on and began. I actually did it like a professional. I started rubbing the ball of the foot and then each toe. I squeezed and massaged the entire foot and then did the other one.

"Jeffery, you're not looking up my gown are you?" she smiled.

"No, Grandma, I'm just rubbing your feet," I laughed.

About that time, a nurse came in and said, "I wish I could get somebody to do that to my feet."

"Hi, Martha," my grandma said to the nurse. "This is my grandson Jeffery. He can do anything. He's smart, good-looking, owns his own business and can even give good foot massages."

"Easy there, Grandma. I'm getting a bit embarrassed. How do your feet feel now?" I asked.

"They feel much better, Jeffery. They don't hurt near as much."

Martha said she had to run some test but my grandma would probably be getting out the next day. I found out later that she was getting a home health care nurse to stop by everyday to make sure she was taking her pills correctly and help her out where needed.

I stopped by every couple of days for at least half an hour to see my grandma. She had lots of family and friends that stopped by, too. They were all reminded not to give her any more sweets.

One day I got a call from grandma at my office. I was worried at first because she never called me there. "Grandma, is everything okay? Are you alright?" I asked.

"I'm fine, Jeffery," she said. "I called you because I found her."

"Found who, Grandma?" I asked.

"The girl you've been looking for and God has for you. Remember you told me to find the right girl for you. Well, I found her; she's my day care nurse. Her name is Amy. When can you come and meet her?"

I was dumbfounded. I remember telling my grandmother she could find me a woman but I honestly didn't thing she would do it. She was so happy that I had to go along with her for a while. I told her I would be over the next day at lunchtime since she told me that was when Amy would be there.

I got to Grandma's house a little earlier the next day so I could talk to her first. The last thing I wanted to do was hurt her feelings, but I had to let her know that Amy might not be the woman I was looking for.

"You'll love her, Jeffery. She has the two cutest kids and she is so pretty and nice."

Every woman was pretty and nice to my grandma. As I mentioned, she doesn't have a mean bone in her body.

"She has kids, Grandma? She's not married, is she?" I said.

"Jeffery, you know I would never condone you going out with a married woman. She's a widow. She lost her husband two years ago in that war. Look, Jeffery, I know everyone thinks I'm just a nice old woman but believe me, you and Amy will make a great couple."

Grandma relaxed in her chair and asked me if I would rub her feet again. I smiled and sat on the floor in front of her and did my magic. She had a lap blanket laying across her legs. About fifteen minutes later, I was sitting on the couch and grandma had left the room for a moment.

There was a light knock on the door and I saw it open. I heard a woman's voice saying. "Emmie, it's just me, Amy."

She stepped into the living room and I got my first look at Amy. She was absolutely beautiful. The first thing I noticed was her eyes; maybe a greenish hazel in color. Looking at them just drew me in. She had on a white nurse's outfit and her hair was in a ponytail. I could see she had a nice figure.

"Oh, excuse me. I'm Amy, Emmie's home care nurse. I'm sorry to barge in but Emmie told me to just walk in."

I was finally able to speak. "I'm Jeff, Emmie's grandson. She mentioned you would be by around noon. It's nice to meet you." I stood up and held out my hand.

Why was I stuttering? I felt so nervous for a guy that was supposed to have it all together. I was so glad that grandma came back into the room.

"Hi, Amy," said grandma. "I take it you met Jeffery? He's been waiting to meet you," smiled grandma.

"Waiting to meet me?" asked Amy. "Whatever for?"

I thought I'd better speak. "Amy, my grandma wanted me to meet you."

"So Jeffery, are you going to take Amy to dinner?" asked Grandma.

"Grandma, she doesn't know me or anything about me. I can't just put her on the spot like this. I will say she is a very beautiful woman and maybe someday we can go out to dinner."

Amy spoke and smiled at the same time. "On the contrary, I know a lot about you. I know that you peed your pants when you were in kindergarten. You ran cross-country and made it to state. You were in the top five percent of your class in high school and would have been valedictorian if they still had one.

"You went to college in Miami and majored in both education and computer science and hold a degree in both. You also graduated in the top of your class there too. You own your own computer business and you're the best grandson that any grandma could want. Oh, I almost forgot, you give great foot massages," laughed Amy.

I looked over at my grandma. "So, Grandma, is there anything you didn't tell her about me," I smiled.

I looked over at Amy. "Amy, would you have dinner with me? You can choose the time and the place. I'm not just asking to keep my promise to Grandma. I find you very attractive and would like to get to know you."

Amy thought for a few seconds. She was thinking very seriously about this. She looked over at Grandma who was smiling at her. "Okay, this Friday, you can pick me up at my house at six." She wrote her home address on the back of a card and handed it to me.

I had to leave to go back to the office so I kissed my grandma goodbye and told Amy that I would see her Friday. It was three days away.

I don't know why but I didn't sleep good the next couple of nights. I would lie awake and think about Amy. Why, I wondered. I knew very little about her since I just met her.

I couldn't get the picture of her out of my mind. All I saw were those beautiful greenish eyes staring at me. I knew I had to find out more about her. I was sitting in my office on Friday morning when I received a phone call. It was Amy. I was worried at first that she was canceling our dinner engagement.

"Jeff, it's me, Amy. I'm here at your grandmother's and I needed to talk to you. Emmie gave me your number so I hope it's all right to call. She said you wouldn't mind."

"Feel free to call me anytime. What can I do for you, Amy? Is our dinner engagement still on?" I was trying to act calm but I wanted to see her again.

"Yes, the dinner is still on," I could hear a smile in her voice. "I was just wondering if you could pick me up at my parents' house. Mom is watching my kids and she spends all day at my house. She doesn't mind watching them but she has things to do at her own place."

"No problem, Amy, just give me her address and I'll be by at six."

Truth be known I was scared shitless. I didn't want Amy to know about my fear of meeting older women that she knows. I'll try and explain how this fear started.

It all began after I was out of college about three months. Some old friends of mine asked me if I wanted to go down to Cincinnati. They had a gambling casino on a boat that cruised the Ohio River. We went down and were having a great time. I met a woman on the boat and we started talking.

She was a student at the local university and was out with her girlfriends. It was nice just being with a younger woman and we went into the lounge and danced. I used some of my old charms and before long, I was squeezing her ass.

It wasn't long before we took a walk and ended up on the third deck. It was where the lovers or at least people wanting sex went. I sat down and Diane unzipped my pants. She lifted her short skirt and slipped off her panties.

She straddled my lap and lowered herself on my hard cock. I wasn't thinking and didn't put on a condom. I was pumping her pussy and she was riding me hard. Thinking back, I never even kissed her lips. I guess it was part of my past. She started squealing and I felt her pussy lips start to grip my cock. I knew the spasms meant she was starting to orgasm.

It went on for a few minutes before I let loose with my own orgasm and shot a load up into her very hot pussy. I felt her coming again. She sat there with her head on my shoulder for a few minutes. She looked at me and said we had better get back downstairs before our friends missed us. I took my hanky out of my pocket and she held it against her pussy while she got off my lap.

She caught most of my cum from going all over by shoving the hanky into the opening of her pussy. As she slid her panties back on, I put my wet cock back into my briefs and zipped up my pants.

After going back into the lounge, I went to the mens' room and cleaned up. I figured Diane went to the ladies' room and did the same but I don't know for sure. Later I apologized to her for not wearing a condom. She told me she didn't like them and was on the pill. She told me that no man made her come the way I did, multiple orgasms in a row.

Before docking, she gave me her phone number and told me to call her when I was in the area. I didn't think I would be back but I saved her number anyway. She was the first woman I had sex with since leaving the business. It felt good to be with a young woman but sex for me still wasn't that important. I think I fucked her because I wanted to know I was still all right and not burned out since sex wasn't that important to me.

It was about a month later when I got a call from a firm in Cincinnati that asked me if I could do a teaching seminar on their particular program. I would be holding three classes showing the employees how to use it. I would be gone for two nights.

On my second night there, I called Diane. I was surprised she remembered me. She told me that there was no way she would forget the way I fucked her. I had to wonder how bad the men in the area fucked their women. All I did is give her a little more attention and not come until I felt her coming. It was a simple task of putting the woman first.

I explained to Diane that I was in town for one more night and wanted to know if she would like to go out. She told me she would love to. She gave me her address where she still lived with her parents. They lived in a gated community where a guard would let you in the gate if you were on the guest list.

I arrived and told the guard that I was Jeff Little and he scrolled through his list and opened the gate and told me which house to go to. I came to Diane's house and rang the doorbell expecting a butler to answer the door. Instead, there was Diane with a micro-mini skirt on and a low cut blouse.

She was smiling. "Hi, Jeff. Come on in for a minute while I get my purse." She turned to walk away when a woman entered the room.

"Oh, Mom, this is my date. He's Jeff..." her mother cut her off.

"Zack, Zack Stone, what are you doing here?"

"No, Mom, his name is Jeff."

I didn't say a word. It was Helen, one of my regular clients when I was in the business. I must have had sex with her over ten times in the four years I was an escort. There is nothing I hadn't done to her including spanking and anal sex.

Helen looked at her daughter. "Diane, come with me, we have to talk." She was telling her, not asking her.

A few minutes later Helen came into the room and told me to leave. Diane wouldn't be going out with me. I'd have to find my sex elsewhere.

I wanted to apologize but Helen asked me to leave and never return. She said her husband was in the next room and that I had to leave now.

When I got back to my motel room, I decided to hell with women. I was afraid that if I ever got close to a woman that the same thing might happen. I actually became paranoid when my dates wanted to introduce me to their families.

Oh, I forgot to mention that about midnight that night I got a call from Helen asking if she could come and see me. It took some nerve, kicking me out of her house and then wanting me to ball her.

"Helen, I'm no longer an escort. Why don't you take your ass back to your husband and try fucking him for a change? Please don't call me again."

Now here I was a few years later when my date wanted me to pick her up at her mother's. I shuddered as I went to pick up Amy at her parent's house. Luckily, Amy was standing on the porch and came down the stairs when I pulled up. I quickly got out and opened the door but not before I complimented her on how beautiful she looked. Her hair was down around her shoulders and her sexy green eyes stared at me.

We went to a nice restaurant and lounge where we sat in a booth for a little more privacy. This was a bit weird for me. I was on an actual date with a beautiful woman and I really wanted to be here. I knew I should start some kind of conversation since it felt a bit awkward.

"So, Amy, why did you accept the dinner date?" I smiled.

She looked at me with those enticing eyes. "Well, after you asked me, I looked over at Emmie and there is no way I wanted to disappoint her."

"So the only reason you're here is because of my grandmother?"

Amy laughed. She even had a cute laugh. "Of course not. Every time I would go by your grandma's house, she would always talk about her family. For some reason the conversation always got around to you. After listening to her talking, I decided I wanted to meet what your grandma considered the perfect man.

"I was surprised to find you at her house in the middle of the afternoon.. "Your grandma smiled when you asked me out. I accepted because I knew I had to find out more about you."

"You do understand that in my grandmother's eyes I can do no wrong. She probably has told you everything there is to know about me," I smiled. "So tell me a little about your life."

We ordered dinner and some wine to go with it. While we were waiting, Amy asked me what I wanted to know.

"Whatever you want to tell me, but for starters, did you ever pee your pants when you were five years old?" I laughed.

Amy burst out laughing, "Okay, I didn't pee my pants when I was five but I did accidently pee the bed when I was four. So there, both of our secrets are out," she laughed again.

Secrets: I had so many that my mind was half spinning. What should I tell Amy? After all, this was only our first time together. I wanted to know so much more about her. I asked her to tell me a little more about her life and family. I was a great listener and I waited for Amy to respond.

"Let's see, I met my late husband while I was in college. We dated for about six months before we got married. Ten months later Gina was born. Dave had joined the military and I was studying to be a nurse. I figured we could live most anywhere and I would be able to get a job. He was set to go overseas and I thought I'd live here till he got back. We would live wherever he was stationed. He never came back."

I could see tears in her eyes. I held her hand while she continued her story.

"After he left for overseas I found out I was pregnant with our son. I wrote to Dave and he was really happy about it. He never got to meet his son. Ryan was born two months after a roadside bomb killed Dave.

"I know the media said that at the time we only lost three-hundred or so American GI's which was supposed to be a great thing during war time. But, if the loss is your spouse or a loved one, it doesn't make any difference if it was ten or three thousand. Your life will change forever. I went on and got my nursing degree. Gina and Ryan are my life and I live for them.

"Jeff, I do need to tell you that I'm not looking for a fling. I've dated a few guys since Dave's death and they thought I was looking for a lover. I wasn't then and I'm not now. I wouldn't mind having a good friend to talk to and a shoulder to lean on. Your grandmother said you were a great listener and she was right. So, if you're just looking for sex you probably should be having dinner with someone else."