Not for minors. If you are under 18 please do not read this story.
Love of My Life
by Cindy Johnson
© 2/1/02 - cuteypy@aol.com
Kelsey McDonald was a brilliant man and an even smarter businessman. In 1996 he founded a dot.com company and took it public putting over $50 million into his bank account and another $50 million when he sold it just before the dot com bust. So with $100 million in cash Kelsey was celebrating his 36th birthday with his beautiful girlfriend Camille at the most expensive restaurant in Los Angeles.
In appearance, Kelsey had it made being a well-built, handsome 36-year-old man with millions of dollars and not a care in the world. He had Camille his girl for over 15 years still as pretty as the first day they met in college. But underneath Kelsey was not a happy man. Kelsey was bored and needed a new business adventure. Kelsey also kept a deep dark secret that was driving him crazy. He knew that secret could never be revealed because it would ruin any future business dealings for him forever.
There were several times he wanted to confide in Camille, however, he never took the chance and kept it to himself and his assistant Walter. Walter was a life long friend of Kelsey and knew about his desires and stayed true to Kelsey due to their friendship, the perks, and money he earned being with Kelsey.
When Kelsey was young his mother used to dress him up as a girl and tease him on how pretty he was and how he really should have been born a girl. Kelsey hated it back then, however, when he grew up he experimented with cross-dressing several times. He found a desire to be with a feminine cross dresser that could satisfy his desires. From time to time Walter found one to spend some the night with Kelsey when he was on trips. These "girls’ were all high quality girls, ultra feminine and submissive. They were all paid handsomely to meet his needs.
Since Kelsey took extraordinary precautions and was not a national image in the magazines so he was never at risk at discovery from these "girls," however he always worried about being caught. He also felt uncomfortable every time he had an encounter and felt he would never be truly satisfied.
Almost a year earlier Kelsey told Walter that he would like to establish a full time relationship with one of these "girls" that he could go to whenever he pleased. Some one to be on call full time and only for him. Walter knew exactly what Kelsey wanted which is why they were such an inseparable pair.
Kelsey was about to learn from Walter that his request had finally been fulfilled and that he would meet the new "girl" next week when he flew to Phoenix to meet with some investors about a new project. The meeting was set for next Thursday at 7:30pm. It was to be an initial meeting and if all went as planned Kelsey would have what he always desired. Two lives, one with Camille and the secret life with his new "girlfriend."
That’s where my story begins….
My name is Jason, I am 24 years old and live alone Oakland Ca. I am an only child and was very close with my mom before she died when I was 18 years old. My dad left us when I was very young and she and I became very close. From an early age I always admired my mom and how nicely she dressed for work. She was an administrator for a large company and made a decent living, enough to give us a nice lifestyle.
When I was growing up I found myself going through her drawers and fondling her lingerie when she was at work. I even masturbated in some of her silk slips on several occasions. That silky lingerie was driving me wild.
This excitement let to further experimentation. I started putting on some of her under garments. I would wear one of her lace bras with matching panties under a sheer pair of pantyhose and the step into a full-length slip. My orgasms got very intense and these occasional experiments became quite frequent.
I got home from school every day by 2:30 and by 3:00pm I was dressed up in front of the mirror admiring myself. Mom didn’t get home until 6pm every day and that gave me lots of time to dress up, do my home work, make dinner and clean up the house before she got home.
This went on for almost 6 months straight without any incidents. I was getting quite comfortable with dressing up and my confidence increased. Soon I was wearing my mom’s skirts, and blouses with a pair of heels over her sexy lingerie. I could hardly wait to do the daily chores dressed in these clothes.
One afternoon around 4 pm I was sitting at the kitchen table dressed in my mom’s red sweater dress with her matching heels I was doing my homework as the roast cooked in the oven. I was concentrating on a math problem and didn’t hear her come in the house. My heart stopped when I heard my mom giggle from behind my chair. I froze in fear and embarrassment.
"Well, now I know who has been in my lingerie drawer. How long have you been dressing like this?" I felt totally humiliated and didn’t want to move or talk.
"Get up, let me have a look."
I slowly stood up and kept my eyes focused on the floor.
"That dress looks much better on you that it does me, I guess you might as well keep it, then. And your legs look nice in those nylons and it looks like we are the same shoe size. That’s convenient, isn’t it, sweetheart?"
I remained silent. Was she just teasing me and trying to humiliate me even more?
She put her hand under my chin and gently lifted my face until our eyes met.
"Don’t worry, Sweetie. Let’s just keep this our little secret. No one has to know."
From that moment forward I felt closeness with my mom that I had never felt before. She was someone I could trust and I knew she understood. It was the most profound moment of my short life.
That evening mom made me stay dressed as we sat and talked. She served dinner as we sat and talked about my dressing in her clothes. We talked about why I dressed up and how I felt when I was dressed up. She made some rules and plans for the near future.
"First of all, you must never leave the house or go near the windows until I say otherwise. Second, you will not tell anyone about your little secret, I would not want to see you hurt. Third, you must stop using my clothes. They are too expensive and not suitable for a girl you age. I will purchase you some of your own things for you to wear. Do you understand?"
"Yes," I blurted out almost with too much excitement.
"One more thing, you need a name if you are going to be dressed like this. We had a girls name picked out in case you were born a girl. We chose Courtney, after you great grandmother. From now I will call you Courtney."
I just smiled and didn’t say anything, but I loved the name. It sounded feminine and girlish.
"One more thing, you must continue with your chores and keep your grades up. If either start to slack off we will have a discussion about this, OK?"
Up to this point I was responsible for cleaning the house, vacuuming, laundry and cooking dinner. I quickly agreed.
It was now almost 11 o’clock and we were both getting tired.
"Come with me," mom said as I followed her up to her room.
"Take off my dress," she said as she went to her dresser.
"Don’t be shy, Courtney. You will have to get used to dressing up in front of me from now on. Now get out of those clothes."
I slowly stripped off the dress, lingerie and heels and carefully laid them on the bed. I stood there naked in from of her as she handed me her full-length pink nightgown.
"I want you to wear this tonight and tomorrow when you get home I will have an outfit laid out for you on my bed. Wear that and then wait for me when I get home. Off to bed with you now Courtney."
The Pink nightgown slipped over my hairless body and felt electric against my skin. I hardly slept that night between the felling of the nylon across my entire body and the events that just took place.
School went by quickly and I rushed home to find a note on the table reminding to be ready and have dinner ready by 6pm. True to her promise there was 5 presents on the bed with Courtney’s name on each one.
I stripped off my clothes and opened the boxes. The first one had 5 pairs of Panties and 6 pairs of pantyhose in different color and shades. The next box had a cute little leather knee length skirt. The small box had a pair of 3" matching heel in my size. The other box contained a pullover sweater. The last box had a cute pink lace bra in my size that was heavily padded.
It took me less than 5 minutes to get completely dressed and an hour to admire myself in the mirror. Before I knew it I had little time to do the housework and rushed to get everything done before mom got home. I couldn’t wait to show her my new outfit and thank her.
When she arrived she casually said, "Hi Courtney, the outfit fits perfectly and it looks great on you. Do you like it?"
"Yes, it is great. Thank you."
"After dinner I want to show you how to do your make-up."
For the next year mom helped me dress. She taught me the complete art of make-up. I had to practice every night until she was convinced I had it right.
We spent entire weekends together as she taught me how to act like a woman. She showed me how to make the proper feminine movements, how to sit correctly, cross my legs and fix my hair. We even talked about men and boys and how they treat girls and what the boys expected from the girls. I felt like her daughter, which I think she truly wanted. She never made me feel uncomfortable as Courtney. I only felt her love.
Over that year I had a very nice collection of dresses, skirts, blouses, lingerie and shoes. I even had my own make-up kit and hair supplies.
On the weekends I would get up early and apply long nails, paint them the same color as my toes and then spend the morning doing my long hair into a feminine curly look. I was always ready by lunchtime and wanted to go out with mom in the worst way. She said I wasn’t ready to go out just yet but she would tell me when. So week after week, month after month, I continued to dress every day an all weekend. During my 18th summer I spent most of the time as Courtney. I
Mom said I was ready to go out and she planned on taking me to dinner at some fancy restaurant that Friday evening. Just before I walked in the house to start getting dressed the phone rang and that second changed my life forever. It was mom’s friend calling to tell me some bad news. She said mom was in a bad accident and I need to go down the hospital.
I raced to her side and grabbed her hand. The last few minutes I spent with her I will always remember. Just before she died and looked up at me, smiled and said, "Remember I will always love you, Courtney."
Her passing shook me hard. It changed my life. I had to grow up instantly right then and there. I told myself all kind of things. Guilt filled me and shame came over me. I swore I’d never dress up again; I was going to be a man and suppress all those feelings forever.
I sold the house and went to college and used the rest of mom’s money from the estate
to get me through the four years of school. I got great grades and studied hard. I dated
several girls and had some good times, but not like the time I had with mom.
After graduation I got a job as a teacher in a local school. Barely making enough to get by but I felt I was helping the children. I had a small apartment and my old car with very little money in my bank account and my prospects no looking too bright.
My life had turned dim; I think I was even depressed. I went through some old things in the guest room and came across some of Courtney’s old things. Without much thought I slipped into one of the outfits and felt at peace. I cried myself to sleep in her pink gown and woke the next morning feeling like a new person. I couldn’t explain it, but the clothes seemed to heel me.
For the next few weeks I dressed up after work and I was feeling great. I continued to date and dress in my free time, keeping it a secret hobby.
Two years went by and my dressing progressed to the point that I was now going out on the weekend during the summer. I found a small club that accepted "girls" like me and I felt at home there every Fri and Sat night. It was a magic and wonderful healing experience. I felt quite comfortable as Courtney. In fact I was so convincing most people had no idea I wasn’t a girl. My confidence grew with my wardrobe and new hairstyles. I knew what I wanted from that time forward but didn’t know how I would afford being a girl full time. I started dating men from the bar that summer. That turned out to be a great adventure. Men loved the way I looked and acted and were always trying to pick me up at the club. I accepted dates under the pretense that I wasn’t interested in sex but only companionship.
The guys that took me out treated me like a lady. Opening doors, holding my chairs, paying for dinner, holding my hand as we walked were all part of the evening. All I had to do was look pretty, act feminine and be attentive. Whenever they tried to get forward I reminded them that I had no interest in sexual relations. I did give most of them goodnight kisses and let them feel me a little, however, we never went any further.
Even being shy and not a bragging individual I have to admit I looked very good as a girl. Anyone who saw me knew I really was a girl and never questioned my feminine motions or soft voice. All the years of practice paid off along with my slender body, long hair and feminine features. I also knew how to dress to call attention to my body and the guys just love it. I had a date every Fri and Sat evening and I loved being their girlfriend.
My reputation grew and I had more boyfriends and male admirers than I could handle. Even the other "girls" at the club were getting a little jealous and I totally understood. I wasn’t even trying to get their attention but my body and ultra feminine movements were what the guys were looking for.
They wanted to date a Feminine Girl that was ALL girl on the outside and had an extra something between her legs. Each one had a fantasy about dating a girl like me and I understood.
Near the end of my 23rd summer I met Walter. He was a very nice professional man that sat down and offered to buy me a drink. We talked for over an hour mostly about my and my life. For some reason talking to him was very easy and I told him all about my mom and my dressing. I explained how natural it made me feel and how much I enjoyed living like Courtney. He quizzed me on my family and ties to Oakland, which I found curious, but I answered all his questions.
He asked me out to dinner the next evening by saying he wanted to discuss a business idea. I explained how I was trying to cut down on my dating and that I wasn’t interested in sexual relations at that time.
He responded, "Courtney, please trust me. The opportunity I would like to discuss will change you life forever. Please give me an hour to explain over dinner. You pick the place and I’ll meet you there if it will make you feel better. I won’t take no for an answer."
He seemed safe and honest so I accepted and agreed go meet him at Nora’s Café at 7pm.
DINNER
That evening I wore a red velvet skirt and white blouse with my nude pantyhose and red heels. I fixed my hair in a French Braid and put on my evening make-up. I took a cab over to Nora’s and met Walter in the bar. We both had a martini and went to our table for dinner.
"Thank you for coming tonight Courtney. I have to admit I can’t believe how good you look. You are the prettiest girl in the restaurant and that is saying something, I kid you not." Nora’s Café on Friday night is a pick up spot and the women are dressed to kill so I really appreciated his compliment smiled and said thank you in my soft feminine voice.
We talked about a variety of subjects through supper about all types of topics. Walter was quite interested in my future and seemed to care about me almost like a big brother. After dinner as we were having our coffee he started to explain the real reason he was having dinner with me.
"Courtney, I would like to explain my interest in you and why I have asked you to dinner. First of all I love having dinner with a beautiful woman but the main reason is about the man I work for. He is closer to me than my own brother and I care for him greatly. I have spent the last year looking for someone like you and now I will explain."
"Kelsey McDonald is a very wealthy young man that has a secret desire that cannot be filled with his public life. He dates Camille, a wonderful companion. The problem is Kelsey yearns for time with a "girl" like you."
"So what are you trying to set me up on a blind date, Walter? What is this about?" I asked a little angry.
"Please be patient and hear me out. Kelsey has a vacant penthouse suite in a very plush high rise near Phoenix AZ. He is looking for someone like you to be his girlfriend whenever he gets in town. To become close and meet his needs, all his needs. It would not be frequent, maybe only twice a month for a few nights."
"Do you think I am a whore, that I will sell myself like some cheap tramp?"
"No, nothing like that at all. If you agree to our terms the penthouse would be come yours. You would live there and receive all the perks that come with the penthouse…fitness room, steam room, personal trainer, spa and much more." He paused as the waiter poured more coffee. He could see I had not interest in this at all.
"Look Courtney, Kelsey is a very good man, generous and gentle. For your affection and feminine charm you would be rewarded. He if willing to open an account for you with $250,000 and pay you $30,000 per month with all expenses paid. You would live full time as Courtney and have the most expensive wardrobe, the best help, and anything your little heart desires."
That really rocked me. That was a lot of money and I for the first time I was considering his offer. I would be able to live as Courtney full time and the lifestyle sounded quite nice.
"What would be expected of me?" I asked.
"Good question, Courtney. You would quit your job and then move into your new home in Phoenix. You would be given a new identity as Courtney Barron. Then you would spend the next month getting your new wardrobe and whatever else a girl needs in place. Soon after I would arrange a dinner for the three of us and introduce you to Kelsey."
He continued, "After dinner I will give you the deed to the home along with your new banking accounts. You will be asked to sign a non-disclosure document that states that you will never reveal your relationship with Kelsey. From that point forward you and Kelsey will become very close. He would expect you to be his committed girlfriend and do what ever he desired."
Walter opened a manila folder and showed me an 8 x 10 of Kelsey. I was not expecting someone that handsome and was a little surprised. He showed me Kelsey’s net worth and a check made out to me for $50,000. The check was to be given to me when I moved into the new home and competed my ID change.
"As an incentive the $50,000 is you’re the moment you arrive in Phoenix and get your new ID. No strings attached. If you don’t like Kelsey or the arrangement after our meeting you can move back to Oakland keep the $50,000. No harm no foul."
"Wow, that’s a lot to think about, Walter."
"You have 2 days to make a decision. We’ve done a lot of research on you Courtney, and we know you have no ties here in Oakland, your friends think you moved to NY for a new job. No one will look for you and your life will become what you always dreamed about. You are his first choice, however, we have some other candidates that I am sure would love this opportunity. So yes, please think about it Courtney. But this is the chance of a lifetime, a chance to fulfill all you dreams. Please call me and let me know your decision. If I don’t hear from you by Noon on Monday I will understand."
Walter said he was on the way back to Oakland and the private Jet was waiting for him at the airport. He paid the bill and gave me $50 for cab fare.
"Thank you for spending the evening with me, Courtney. You are a very nice girl and I hope I will see you again. Goodnight."
I sat there in shock. This couldn’t be for real, could it? Could this really happen to me. What would I do????
Comments???
Write me at: cuteypy@aol.com
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