Beginnings – Day 2 – Shopping!

by Carolyn

   

I awoke slowly the following morning. When I had arrived home I was tired but exhilarated. What a wonderful night. From having never dressed as a woman before to coming home from my first kiss from a man, it certainly had been an eventful day.

I remember coming into my house and thinking about going directly to bed. I took off my coat and looked into the mirror in the hallway. There stood a 50ish woman looking back at me. I smiled to myself and decided I did not want to take these clothes off yet!

I imagine the first thing a woman would do in this situation would be to kick off her heels but there was no way I was going to do that! I wanted to be Carolyn for as long as I could.

I poured myself a glass of wine and sat in the half light, thinking of Harry: how his mouth felt on mine and how he felt when he was in my mouth. Certainly there were conflicting feelings but strangely, as long as I was Carolyn, I felt being with a man was entirely natural.

I turned off the light and clicked on the TV. As I curled up on the couch as I finally took off my shoes, I watched an old romantic comedy and fantasized about playing the female lead.

When I awoke the next morning, still on the couch, I felt the sensuous feel of my pantyhose and reveled in my newfound womanhood. I sat up, put my heels back on and went into the kitchen. I made some coffee and called Suzy.

We talked for over an as I recounted the events of the night before. When I told her about Harry's offer to manage his club as Carolyn Suzy was quiet for a moment.

"You've really gotten into this haven't you?" she asked. "I can't help but notice you've been speaking in your Carolyn voice complete with accent."

I explained that I hadn't felt this alive in years and that I was seriously considering his offer. I also told her that I needed to shop for an outfit for my date with Harry that coming Wednesday.

"OK, Carolyn. I have a plan. You take a shower, shave closely and see what you can do with your hair. Then get dressed in your underwear, slip and hose and throw on a robe. I'll be there in an hour and we'll decide how to proceed. I'll bring a supply of Mary Kay makeup with me."

What a neat friend and how serendipitous to have such a close friend who was a Mary Kay director! I did as she told and waited, rather impatiently, for her to arrive.

When she came in she had her Mary Kay tote and three shopping bags! She explained that in order for us to shop for an outfit for Wednesday we may as well do so as two women. I must have looked surprised.

"Carolyn! If you are seriously considering working full time as a woman and plan to go out in public on a dinner date Wednesday night, you may as well begin now."

Of course, part of me was gleeful at the thought and another side of me was petrified.

"Look, you've already played the part quite convincingly. I have brought all the makeup you'll need and also I have a surprise for you."

With that she opened the first bag. It contained a simple dark brown dress that buttoned down the front. It was soft light wool. She opened the next bag and showed me a pair of low heeled brown shoes. She remembered that I had shopped at Payless Shoes and that I wear a size 12W.

"Put on this dress and wear these shoes. We're going shopping. I chose this dress because you can change in and out of it easily when you try on clothes. We're going to have some fun today!"

Of course I complied at once. The dress was divine. My black slip did not show through except a touch at the bodice. It was rather sexy peeking out above the top button. She shoes fit perfectly. I didn't look glamorous but I certainly looked quite like a lady.

She went to work on my make up insisting that I learn what she was doing.

"If you are going to be a woman, you'll need to do your own makeup! I'm certainly not going to be available at all hours to make you beautiful."

As she packed up her tote, she retrieved her final bag. It contained a huge amount of Mary Kay product.

"You must start a regimen of moisturizing. It is important that you use the makeup remover every night. The lotions are for your legs and body. I've included three scents for you to experiment with until you decide which one(s) you like."

There was so much stuff! I must have looked puzzled at the array before me.

"Listen, Carolyn. If you are considering taking a job where you'll be in character publicly then you need to be completely comfortable as a woman. I suggest you test it. Since you have your dinner date with Harry in three days, why not spend those days entirely as Carolyn? We'll shop for a few outfits today including underwear and sleepwear. If you can't handle that, then you'll know that this adventure is not for you."

It certainly made perfect sense but it suddenly seemed a daunting task.

"Don't worry, honey. Today I'll be with you. Remember how your confidence grew throughout the afternoon and evening yesterday. You can afford to buy what you need and if it doesn't work out, we'll just donate everything to the Goodwill."

"Ok, Suzy. Let's do it. I think I'm up for the challenge and I must admit I love my look!"

"Oh wait" I cried. "I am supposed to call Harry and give him my address. Please let me do that because I promised him I would."

Of course she agreed and I made the call. Sadly I got his voice mail but I left my address for him and promised to call later that day.

With that we were off. I explained I didn't have a lot of cash and was hesitant to use my credit cards. She was happy to charge everything on her accounts and let me repay her by check at the end of the day. That settled, we drove to a Lane Bryant store.

"A lady that works here is one of my Mary Kay customers. She's a great gal. I suggest we come clean with her, explain what you are doing and let her help us. I'm sure she will be understanding and will provide you with excellent advice."

What a great idea. I was already feeling confident and we hadn't even gotten out of the car. We went in and Suzy pulled her friend Annie aside. When they came to me Annie was grinning until she saw me.

"Oh my goodness! Carolyn, you look tremendous. Suzy, you are amazing. I would have never guessed she was anything but a total woman!"

Well, that erased any lingering fears and we commenced with shopping. I must have tried on 20 outfits: dresses, skirts, tops, underwear and sleepwear. Suzy suggested I upgrade to a C cup. While my B cup was fine, moving up one notch wasn't overstated and frankly, I had to agree that my figure did look noticeably better.

Annie was great. When we were done I had run up quite a tab. Frankly, I think it was well worth her time!

We toted everything out to the car and went to Payless. There I picked out 7 pairs of shoes! I purchased some low heeled shoes for work (assuming I was going to go through with that) and some pretty sexy heels. One pair I really liked was a 4 inch black patent pump with an ankle strap and a pointed toe. I needed a 13 for that one, probably because it was so high.

When we got back into the car it was time for lunch. I was starving and we went to a rather upscale restaurant. Seated, we each had a glass of wine and a salad while we chatted about our shopping adventure.

"You can always go back to Annie when you want to shop. She'll take good care of you. I think you became great girlfriends today."

"Suzy, I can't thank you enough for all you've done for me. I promise to give it a full try for the next few days. I consider you a close friend and will be there for you if you ever need anything!"

We finished our lunch and went back to my house. There we emptied my closet and put all my male clothing into the guest closet. I unpacked my new things and had such fun arranging everything. My bathroom was all girl with makeup, lotions and powders everywhere.

 

Suzy left and I was exhausted. I undressed, put on a long white satin nightgown and climbed into bed. Then I remembered what Suzy had told me so I got up and dutifully removed my makeup. I would practice putting it back on after my nap.

Before I went back to bed I called Harry on his cell again. This time he answered. It made my heart flutter to hear his voice. We chatted for a few minutes, confirmed our date and then he had to go. I could have talked for an hour!

Reveling in the sound of him on the phone put me in a luxurious mood. At the same time, I had odd thoughts about what had transpired in the past two days. After all these years never even considering wearing a dress, I was now at the stage where I had to decide whether to accept a job that required me to assume a female role. Also, I had just confirmed a date with a handsome man who thought I was terribly attractive!

I lay back and imagined Harry's kiss and his arms around me. The satin of my nightgown rubbed gently on my chest. I had to admit I was one happy girl!

Sleep came quickly. I dreamed of Harry and my new life ahead. It had been quite a day.

When I woke it was getting dark outside. The straps of my gown played games on my shoulders. I was feeling very sexy and wondered what it would feel like if Harry were with me. Yum.

I got up and decided to get dressed for the rest of the evening. First I went to my closet and picked out a cute flared grey skirt that fell just below my knees. I selected a darling V-necked maroon sweater that complemented the skirt. Rather than a full slip, I laid out a half slip and a grey camisole. I decided on a skin toned all in one garment and charcoal pantyhose. I had a stylish pair of maroon sling backs that I had purchased to match my sweater.

Going into the bathroom I drew a bath and added some oils. I slipped off my nightgown and eased into the water. It felt glorious. As I shaved my legs I realized I would have to do something about the hair on my arms. I was hesitant to shave them and thought I should check with Suzy later to see what she recommended. I did shave under my arms and even that gave me tingles.

After toweling off I put on my garment, stuffed the cups and stopped. That makeshift stuffing was fine for a one night costume but I would have to talk with Suzy about breasts as well.

I put on the camisole and stepped into the half slip. I sat on the bed and carefully pulled on my panty hose. Suzy had warned me not to walk around in them for fear of catching a run so I donned a pair of mules we had picked out for just this type of situation.

Now transformed from the neck down, I began working on my hair. The set I had at the salon was long gone but the cut was perfect. I was able to play with it, teasing and spraying until it actually looked pretty nice.

 

Then I attacked the makeup task for the first time solo. It took a few tries, especially around my eyes before I began to get the knack of mascara and eye shadow. I was glad Suzy had included eye makeup remover in my packet. I went through three tries before I felt my blue eyes were passable.

It was time to complete the outfit so I put on my skirt and sweater. (My skirt! Can you believe it??) Finally I slipped on the shoes and went to the mirror. Carolyn was looking quite good that night!

I went to the kitchen for a glass of juice. Wine was tempting but I had vowed to shed a few pounds so I'd look better for Harry.

Sitting at my desk I began searching the internet. I found a company that sells cell phones on line and decided to order one that would be just for Carolyn. When that phone rang, I would know someone was calling for a lady with a soft Russian accent. Delivery was arranged for overnight and I was excited to think I'd have my phone on Monday. I could give Harry my number!

There were many sites about cross-dressing. I learned that it was not uncommon to obtain breast forms and found a local store that catered to men seeking help with these. I sat back and thought about it. Apparently they are affixed with an adhesive that lasts up to 10 days. If I were to do that I would be committed to being Carolyn for longer than the five day test in progress.

I thought about asking Suzy's advice and decided not to but rather check it out and perhaps surprise her.

This led to my planning of the next day. There would be a trip to a few stores, including Cindy's salon, if she could take me on short notice. Since Suzy had been such a dear helping me, wouldn't it be nice to make dinner for her? I wondered if she would be free and then laughed out loud. "Silly girl – just call her!"

So I did and she was happy to hear from me. "How has your afternoon been, Honey? Did you try on all of your new clothes?"

"No Suzy, actually I took a rather long nap and then showered before getting dressed. I've been on the internet for the last couple of hours and would love to talk with you tomorrow about some questions I've been writing down."

"Oh Carolyn, I'd love to come for a girly evening. I'll bring the wine and we'll have a nice quiet time together."

That settled, we chatted a bit longer and then hung up. It was nearly 9:00. I decided to change for bed and watch a movie. Of course, I remembered to take off my makeup and put lotion all over my body before slipping on yet another satin gown. This one was dark green and came with a matching robe. I loved it! I wore my mules and just had to put some lipstick on before heading to the couch. Again I found a romantic movie, this time from the 40's. Again I fanaticized about playing the female lead. The kissing scenes were quite arousing.

It had been a full day – my first as Carolyn! I didn't know how long this would last but I certainly knew the first day would not be my last. No by a long shot!

  

  

  

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