Beginnings

by Carolyn

Beginnings

 

It started out in such a simple and harmless way. Some friends were having a Halloween party for a Girl Scout Troup and I agreed to provide some entertainment by telling fortunes. For fun, we decided it would be best if I wore a costume so I agreed to become Caroline the fortune teller for the night.

I had never worn women's clothing before so it seemed like quite the lark. I did some exploring on eBay and found I could shop anonymously as long as I knew what size to buy. Being single, I had no clue about this and frankly, wasn't close enough to anyone to broach the topic.

For reference, I'm 60 years old, nearly 6 feet tall and weight 200 pounds. You can see why determining what size clothes I'd need was problematic. I work from home and have no reason to keep my hair trimmed so it falls down to my collar.

I ultimately solved that problem by going to the Goodwill store and trying on some skirts and tops behind discreet doors. If anyone saw me carrying the clothes into the changing rooms they certainly did not react. I discovered my dress size is a size 1X

After looking at the internet for hours I finally decided on a midcalf black dress that was described as Gothic. I bid on it and won it for less than $30.00! It was purported to be new and when it arrived it still had the tags.

As I opened the box I realized that I was committed to this project. I also realized I was more excited than I expected I would be. My hands actually shook as I held up my new dress. My goodness – up to three weeks prior I had never even thought about owning a dress and now I was about to try it on!

I stripped naked and slid the dress over my head. The sleeves came down to my wrists and the skirt fell about two inches below my knees. Having never worn a dress before, I was amazed at the feelings the silky material gave me. I remember thinking "this is going to be quite a night".

I decided to wear the dress for a bit to get used to the feeling. I looking in the mirror and my heart sank. It was painfully obvious that I was a 60 year old man parading around in a dress. This would not do. I realized that I had two choices – either make it a complete farce and just go looking like this or take the time and effort to do a complete job of it.

I went back to the internet and did some exploring. I wasn't ignorant of women's clothing – I had been married so I've seen a woman get dressed before. I looked at underwear and shoes. The choices were staggering.

I found a site that showed how to measure for bra size. I quickly followed the instructions and learned I wear a size 42 bra. Apparently the cup size was my choice.

Since I wanted to present a realistic persona without being too attractive (as if I could be!) I decided on a B cup.

Shoes are a different issue. I learned that men wear 1 or 2 sizes larger in a woman's style than in men's shoes. As I looked at shoes on eBay, I realized that this was going to be a key decision in the look I was going to portray. I knew that a pair of flat heeled shoes would be easy to walk in. However, much to my surprise, I found myself looking at 3 inch heels almost all the time. Hmmm – perhaps I was looking forward to this more than I knew.

I finally decided on my outfit. I went to the website of Just My Size and ordered a one piece garment hoping it would hold in my stomach a bit. Of course I ordered it in black!

On eBay I found a classic full black slip so I bought that as well. I even ordered a pair of panties from a cross-dressing site.

When these items arrived I couldn't wait to try them on! Stepping into the garment and slipping my arms through the straps was the most sensual sensation I'd felt in months. My goodness! I stuffed the cups and just stood there in front of the mirror checking myself out from all angles.

Then I slipped on the panties and pulled the slip over my head. With trembling hands I grabbed my dress and put it on. What feelings coursed through me! I looked in the mirror and, were it not for my face and legs, I saw a woman standing there.

Needless to say, I wore the outfit for a few hours before I finally took it off to go to bed.

As I lay there in the dark, I wondered how to complete the image. Of course I still hadn't purchased shoes as I wasn't sure what size to buy. I remembered seeing a website for Payless Shoes and, since there were a number of outlets nearby, it dawned on me that the only way to find out was to try a pair on.

The next day I went to a Payless store in a strip mall. I entered the store and browsed a bit. There weren't many people and the aisle for women's size 12 and 13 shoes was in the back along one wall. Well, I thought, in for a penny, in for a pound.

Quickly grabbing a nylon foot socklet from the box I picked out a pair of short heeled pumps. I slipped on the socklet and tried on a size 12W. It fit! I was so nervous I didn't dare put on both shoes. I loved the feel of the shoe. I quickly took it off and put my loafer back on, replacing the shoe in its box.

Looking up I saw a pair of black patent 3 inch heels with an exaggerated pointed toe in the same size. I tried one of those and it fit. I actually stood up and found that it wasn't as uncomfortable as I had thought it would be.

I made the decision right there to buy those shoes. Now I had to figure out what to say at the checkout! I decided to come clean and tell the girl they were for me for a Halloween party. When I did I was shocked at the lack of surprise on her face. I was further stunned when she asked if I need panty hose for my costume. Of course, I did but I hadn't planned on being that daring.

She went to the display and asked if I wanted black or tan. I had no clue, of course. She told me that since my shoes had an open toe; it might be good to go with the tan. Ok, I replied quickly. At this point, I just wanted to pay and get out of there!

I went directly home and, you guessed it, immediately put on my pantyhose and new shoes. Oh – you cannot believe the rush. I sensed feelings I'd never felt before.

I kicked off the shoes and put on the whole outfit. When I finally put the shoes back on and went to the mirror I was pleased with my progress. My legs are pretty nice and look feminine in nylons and heels. Wow.

I wore the outfit for a few hours that night. It wasn't too hard to learn to navigate in heels. I especially enjoyed sitting and crossing my legs to admire the shoes.

I remember going back to the mirror and giving my ensemble a critical look. Yes, the dress and heels worked well. The hose didn't hide the hair on my legs but I knew that could be fixed. My hands looked out of place and, even with my longish hair, there was no question that a man's head sat on the apparent body of a woman.

That night as I lay in bed I pondered an approach to finalizing my disguise. I have a good friend who cuts my hair. She is also a hairdresser for her lady clientele. I decided to ask her advice.

The next day I made a date for coffee on the coming Saturday morning. When we met I told her what I had committed to. She squealed with delight. Apparently she has an uncle that did this for Halloween one year and the whole family had a ball with it.

She looked at my hair and told me that she could give it a female style for that night. Since I was due for a cut she told me to just wait the month and then there would be more than enough for her to work with.

She asked if I was going to have my nails done. I, of course, hadn't gotten that far and told her so. In her shop was a girl that gave manicures who would be more than happy to help out. She would even put extensions on them for me. Again, in for a penny…..

Finally she asked me about make up. This I had thought about. I had dated a woman who is a Mary Kay representative. Our relationship remained on friendly terms and I had planned to ask for her help.

Suddenly the plan had fallen into place. I grabbed my cell phone and made the call to Suzy, the Mary Kay woman, and she readily agreed to give me a makeover. She said she would have a surprise for me. I didn't pursue that.

At any rate, sitting in the coffee shop that morning, the plan was set in place. The day of the party I would get dressed in my Carolyn costume and go to Cindy's salon. When she and her manicurist were done with their tasks I'd go to Suzy's house for the final touch.

I went home with my head spinning. I had invested quite a bit of time and money into this adventure and couldn't believe how much I was looking forward to that night.

After making a few more trips to the Goodwill store and thrift shops, I had accumulated 4 long necklaces, 5 bangle bracelets and 4 rings with big, colorful stones. I also had a pair of clip on earrings that hung about 3 inches from my ears. I had found a suitable purse and even bought a woman's coat with a fake fur collar. I had become quite brazen after my experience at Payless!

The day finally came. I got up early and took a long shower. I sat in the tub and shaved my legs. I could see no reason to go through all the other steps I had ahead of me that day and have unsightly leg hair showing through my hose!

Since I had open toed shoes, the night before I had painted my toenails the same color Suzy had picked out for my nails. It was quite titillating to see those red nails at the bottom of my newly shaved legs!

I shaved extra close and used a hairdryer and brush to tease my hair. I had to be out in public on the way to the salon and, although I'd just be in my car, there was no sense in not trying to make my hair look ladylike.

Then I began my transformation. I put on all the clothes, slipped into my shoes and voila, Carolyn was ready to face her day.

Suzy had provided some basic make up to use in the pre-makeover time. I applied a light toner to my face, put a touch of eye shadow on and then put on some lip stick and lip gloss. It wasn't going to fool anyone close up but perhaps no one would give me a second look in the car. I certainly was going to avoid eye contact.

I put on my coat, grabbed my purse and went to my car in the garage. I backed out, looking to see if anyone was around. The coast was clear and before I knew it, I was driving down the street in full drag including a pair of three inch heels.

 

 

When I got to Cindy's salon I began shaking like a leaf. It was one thing to play dress up at home and fanaticize about being Carolyn. It was quite another to open the car door and walk into her shop. With a deep breath, I stepped out of the car and clicked into her salon.

Cindy gasped with glee when I entered. She was amazed at my outfit and carried on about all the jewelry. She told me I was dressed just as a fortune teller would be.

With that, she took my coat and sat me down in the chair. She rewashed my hair and did a few small styling cuts, assuring me it wouldn't look terribly different when I washed it out in the morning.

Then she set my hair in big curlers and put me under a big dryer. While I sat there drying, her manicurist, Gloria, started on my nails. She soaked my fingers and filed my nails evenly. Then she put on fake nails that were just about a quarter inch longer than mine. After the glue set, she applied the polish I brought with me. She put on two coats and covered them with a clear coat.

I couldn't take my eyes of my fingers – they were beautiful!

By then my hair was set so Cindy went to work. She styled it in what she called an "80's" style. It turned out to be BIG hair. I was startled at how the whole plan was coming together. She seemed to be using quite a bit of hairspray.

When I stood up and looked in the mirror I saw a fashionably dressed woman of indeterminate age staring back at me. I knew I needed better make up but my hair, nails and outfit were stunning. I was thrilled and hugged both women tightly.

When we went out to my car to drive to Suzy's I was so much more confident. Sitting at stop lights instead of avoiding eye contact I tried to initiate it! I was having such fun.

Suzy came to the door and swooned appropriately at how ladylike I looked. She reminded me that she had a surprise for me as we walked into her living room.

We rounded the corner and there were at least 10 women sitting there staring at me.

Suzy introduced me as Carolyn and informed me that his was part of her Mary Kay team and that today they were having a meeting and were going to observe my makeover. Oh yes, they also know I was a man trying to look like a woman.

They were all delightful and we chatted like a group of women. They made me so comfortable I felt as though I was a Mary Kay lady myself!

The makeover was tremendous. I still don't know what Suzy used but when she was done I was certain no one would guess I was anything but a 50 something woman.

Of course, my day which had been so eventful was only just beginning. In three hours I was due at the party. Suzy said we should all go to lunch. While I was feeling pretty confident, I balked at going to a restaurant. "Posh!" Suzy said. "You look and act like one of the girls. No one will assume differently."

So there it was. We went to a local restaurant and had a nice Saturday lunch together. Suzy was right, as always. No one gave me a second look…well no one but one older gentleman at the bar who seemed to be checking me out on more that one occasion. I said nothing to anyone about that!

It wasn't long before I became accustomed to my outfit. There were times when I was just chatting with the girls as if I were one of them. They asked me about telling fortunes. I explained that I had purchased some Tarot cards and learned enough about reading them to fake it rather well.

Of course, it wasn't long before they were insisting on having me read the cards for them. I dug the box out of my purse and sat across from Suzy as she was to be my first victim.

To the surprise of all, when I began to lay out the cards I affected the Russian accent I had been practicing. I spoke in a quieter tone and actually had a passable voice using the accent. I resolved right then to speak in that tone for the rest of my day.

The time flew and before I knew it there was only an hour left before the party. As I was preparing to put the cards in their box, the bartender came over and asked if I would read his fortune. He had just come on shift and was curious about the hushed conversations I had been having with the other ladies.

I consented but inside I was pretty nervous. Goodness, here I was talking to a perfect stranger in this alien accent fully disguised as a woman. He seemed to think nothing of it but was transfixed on the cards as I lay them out on the table. I went through the routine and we began to talk about how I learned to read Tarot cards.

I thought I'd really play it out and told him I learned it from my grandmother. I told him that she had told stories about how Tarot card reading was a gift and that one had to be in a nearly altered state to sense what the cards were saying. I went on to say that many gypsy fortune tellers were really men who affected a female persona in order to transcend to an ethereal state to read the cards.

He was surprised to hear that. (So was I – I just made it up on the fly!) He asked if any men still did that. I couldn't believe my ears. He actually had simply accepted that I was a woman. I winked at him and told him that he was talking with one.

His jaw dropped in disbelief. The ladies began to howl and I'm afraid he felt rather foolish. Without changing character I patted his hand and told him not to pay any attention to them. I smiled ever so sweetly and thanked him for the compliment.

He smiled back and effusively congratulated me on my performance. He even said he was about to call one of his older friends and insist he come to meet me. He went on to say that I made an attractive woman and that he would enjoy seeing his friend's reaction to me. I told him that I had to leave for a party and he asked if I would come back afterwards.

Well, what a dilemma. Part of me said run like the wind and another part of me thought, why not? I told Nick that I would think about it and if I weren't back by 8:00 I would not be coming.

With that, I stowed the cards into my purse and stood up to leave. Suzy brought over my coat and Nick helped me put it on. I was enjoying the attention. Maybe being a lady wasn't so bad.

Suzy reminded me I should touch up my makeup before I left for the party. She escorted me into the ladies room. I was pretty nervous but she put me at ease saying that only the girls and Nick knew I wasn't what I appeared to be. So I primped at the mirror, relieved myself and set out for the party.

As I drove through town, I enjoyed the feeling of being viewed as a woman. No one gave me a strange look and I was reveling in the experience.

When I arrived at the hall I was surprised to see that no one was there. There was a note on the door saying that the party had been cancelled and no one knew how to reach me.

I was so disappointed I nearly cried. What a strange reaction.

I climbed back into the car thinking here I am, all dressed up and no place to go. What the heck, I thought and headed back to see Nick. Maybe I should meet his friend.

When I walked in the girls were still there. I explained what had happened apparently looking pretty disappointed. Suzy took my hand and walked me over to a corner table.

She asked me if I was enjoying being Carolyn. I looked down, staring at my red nails and bejeweled wrists. I hesitated to admit how much fun this was.

Finally I looked up at her and told her that this may have been the best day I'd had in years. She grinned and announced that it would be the best night as well.

She called Nick over and told him we all would meet him and his friend Harry at the club at 8:00. He was very pleased – I think he had taken a liking to Suzy. I asked him if he had spoken to Harry about me.

Indeed he had and Harry had been hopeful that he could meet me. I was confused – why would a guy want to meet another guy who was dressed as a woman? Nick explained that Harry was a little kinky and loved to have fun. He was right in thinking that Harry would get a kick out of hanging out with someone like me.

Of course, that set my mind reeling. What would he expect from me? I was still a guy and didn't fancy men. I had to admit that there was a growing part of me that thought it would be a blast to be on a date dressed this way. So, as always, in for a penny, in for a pound. I agreed to go.

As we entered the club, I was not nervous at all. Three glasses of wine certainly helped plus I had been pretty convincing throughout the late afternoon. We had been at the bar and no one seemed to think of me as anything but one of the women laughing and drinking our wine.

We looked around for Nick and suddenly he was behind us. He introduced me to Harry who was a very nice looking man in his early 60's. He was dressed very well with a soft cashmere sweater and charcoal slacks. He smiled and took my hand, pressing it to his lips.

"Carolyn, you are as striking as Nick promised. I hope you'll spend the evening with me."

What could I say! My heart was pounding and I fear my hands began to shake. He put his arm around my waist and escorted me to a table in the back of the club. We ordered our drinks, still wine for me, and began to talk.

He explained that he had dated a cross dresser years ago and had never forgotten how much fun they had. I was not sure about dating – this was supposed to have been just a lark and here I was, sitting in a dark club with a man telling me I was beautiful.

"I'm not sure about this, Harry. This is my first time in public dressed this way and I really haven't though about doing it again!"

He smiled, "That is fine, Honey. If after tonight you want to box up Carolyn so be it. However, let's have some fun with her for a few hours, OK?"

I couldn't resist his charm (I really couldn't!) so I agreed.

He grinned broadly and asked me to dance with him. They were playing some old classics that night and most of the songs were slow. As we stood I reminded him I had never danced with a man before. As we walked to the floor I looked at how the other girls were positioned and facing him, placed my arm on his shoulder as he took my other hand. He pressed me to him and I felt quite strange- delightfully strange.

I just lay my head on his shoulder as we slowly moved across the floor. It was wonderful. I let myself fall into a woman's role and simply followed his lead.

We danced four or five times that night before he asked me to walk with him. He took my hand and led me into the corner of the bar where there was a door. He opened it for me and we walked in. It was an office.

"Oh, Harry – should we be here?"

"Why not, Carolyn? After all, this is my office. I own this club."

Well, I was stunned. I had no idea. I think I looked pretty surprised but not nearly as surprised when he slowly turned me to face him, took my face in his hands and kissed me ever so tenderly. I stiffened but didn't resist. Somehow, it felt right. Ok, I'll admit it. It felt fantastic.

I gently pushed him back about a foot from me. "Harry, I've never been kissed by a man before. I'm rather confused at how you are making me feel."

He put a finger on my lips and drew me back to him. As his kissed me again I kissed him back…hungrily. Oh my, this was beyond anything I had felt. As our lips massaged each other's I pulled his head tightly to me.

After what seemed like minutes we broke apart. I couldn't look at him – I was embarrassed at how aggressive I had been. He put his hand under my chin and made me look into his eyes. I liked what I saw – tenderness and eagerness blended exotically.

Carolyn, I have a proposition for you." I must have looked petrified because he laughed. "No – it's nothing ill mannered. I need a manager for my club and I'd love to hire you. Of course, I will introduce you as Carolyn to the staff. Would you like a job where you would be dressed as and acting as a woman all day?"

This was way too much for me and I told him so. Of course, he knew that on the surface it was a preposterous offer. Then again, below the surface it had quite an appealing potential.

"Kiss me again and then I'll think about it," I said pensively. He pulled me to him and our embrace was hot! His tongue darted into my mouth and I reciprocated. We moved to the couch and necked like teenagers for what seemed like an hour. It was apparent he was reacting to me as a man should be a woman.

Without realizing why I reached down to touch him. I was surprised how happy I felt to feel how hard he had become. I stared into his eyes and I undid his pants. He stood up and it stood out! I had never been that close to a penis before but for some reason I knew what to do. Placing his balls in my hand I licked the tip and began to run my lips over it.

I couldn't stop! I opened my mouth and pulled it in. If I had felt like a woman earlier, I felt like a total woman at that point. I knew how a blowjob felt from the other end so it wasn't difficult to provide him the pleasure I knew he wanted.

It minutes he spurted and I swallowed deeply. His groan of pleasure was all I needed to hear. I was certainly a lucky lady that night!

We were quiet for an eternity. My head was reeling with conflicting thoughts. Hi arm was around me as we both relaxed on the couch. Finally he leaned over to kiss me. Again, I was surprised at how ready I was to have his mouth on mine.

It wasn't much longer before I realized I had some cleaning up to do. He had his own bathroom so I grabbed my purse and went in. My face was a mess but the first order of business was to work on my hair. Suzy's had put a small can of hairspray in my purse along with a brush. It didn't take long for me to repair the hair and begin working on my make up.

When I finished, I felt pretty enough to face Harry. He was waiting with glasses of champagne. As we sipped them he brought up his proposition. I hadn't been able to stop thinking about it and told him so. The idea seemed sublime in his office, sipping champagne but the details were daunting.

Harry had thought it through more than I. He told me that, while the concept was exciting for him, there were many things to consider.

"Why don't you just take a few days to think it through, write down you questions and concerns, and have dinner with me on Wednesday?" My first thought was "what will I wear?"

I pondered a bit before agreeing. He smiled, kissed me again and announced it was time to go back into the club. I looked at his watch and realized it was nearly midnight. How long had we been in here!!!!

As we walked out of his office, none of the people who were there when we left remained except the bartender. A few people looked up as we came into the bar area but then looked away. I honestly don't think they saw anything but Harry and his lady.

Harry helped me with my coat and walked me to my car. As we kissed goodbye I caught myself thinking that I absolutely HAD to have more of this. He held me closely and I softly whispered into his ear that I would indeed meet him on Wednesday for dinner.

"Oh no, my dear," he said. "I'll pick you up. Here's my cell phone number. Just call me tomorrow and let me have your address. There is no way you'll ever have to drive to meet me for a date!"

With that, I got into my car and drove off. What a wonderful night. What a curious future lay ahead.

  

  

  

*********************************************
© 2008 by Carolyn. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.