Deborah; To A Brighter Future

I had lost my true love five years ago, since that day my life has been reduced to just getting by. I lived alone in the home that Caroline had planned and supervised during its construction. The memories often caused tears, but I couldn’t stand to part with the place. I retired three years ago, my retirement and what the two of us had saved would provide for me no matter what I chose to do with my life.

My oldest daughter Jennifer, assumed the duties of looking after me, since she lived the closest. Her husband had left her two years ago, an affair with his secretary. It didn’t last long and he had the nerve to ask Jennifer to take him back. We had raised her right, he was served with divorce papers the day after he had made his request. She decided to not go the marriage route again, dating some, but up front with them that it was a one time deal, enjoy it, for there most likely would not be another date.

She had met a couple of them that almost made her rescind her promise, but luckily she was not tempted that much and the feeling passed. In both cases her instincts were right, the duo turned out to be quite unworthy, as she followed their lives from a distance.

Jennifer spent time with me, had me over to dinner twice a week, went with me to doctor’s appointments and generally tried to fill the void that the passing of Caroline had caused. Caroline had died of cancer, a long drawn out ordeal, hard on her and all that loved her. Jennifer had tried all matter of ideas on me to get me interested in something to take my mind off of being alone. I had good days, but in general it was just one day after another, all of them okay, but lacking any kind of meaning or purpose.

My sixty-second birthday was coming up, I could tell she was planning something, the hushed phone calls, the written plans that were quickly hid when I appeared, just two indicators of her scheming. I tried to get her to just ignore my birthday, I certainly did not want to celebrate it, much less be in the company of others as they felt they had to. Since my wife’s death, I had not made any friends, the few that my wife and I had shared, I managed to piss off, so they were no longer in the picture.

I did manage to make her promise that there would be no party, no guests other than her, and no presents that could be held in your hand. I should have been wary as she agreed to that last one, her wording a little too specific. She had agreed only if that exact wording is used. She had me stay at her apartment the three days before my birthday, to make it easier on her, the excuse she used. She was gone quite often, things for her work were mentioned, but I doubted that was what she was doing.

The dreaded day did arrive eventually, I was in a foul mood, not looking forward to any of it. She fixed me a nice breakfast than had me get dressed. What she had laid out for me is just some casual clothes, so my radar was lulled into a false sense of security. She dragged me out the door, into her car and then an hour drive to our destination.

When we pulled up in front of the salon, I swallowed hard. I had indeed been her before, quite a few years ago, and had thought that part of my life had been safely kept secret. Caroline had known, of course, she had been the one to set up the appointment for me, a part of our married life that I was sure had been buried with Caroline.

I turned sideways in the seat to look at Jennifer and she smiled. I stared to protest and make a scene, but she gave me a huge hug and my resistance just melted. “Ever since Mom died you have been miserable, I have tried everything that I can think of to snap you out of it. All of it has failed miserably. Mom and I have talked about this ever since you told her about your other side. Mom made me promise to not bring it up, as she treasured your trust in her to keep this side of your life a secret.”

“Desperate times require desperate measures. Your birthday present awaits you inside, a gift from Mom for her lover and her best friend. She had stashed money away, for just this type of moment, telling me what to arrange and what to schedule you for. You have no male clothes at home, I have given them all to charity. Your home has been redecorated as per Mom’s desires and wishes. When you enter that salon you last day dressed as a male has ended. Have fun, don’t worry, your new life awaits. I love you Deborah, I want nothing but the best for my new Mom. When they are done they will call me and I will come and pick you up.

I kissed her, tried to get her to let me stay the way I was, but she put her fingers to my lips to stop talk. This is what Caroline wanted, so get inside. I opened the car door and walked the short distance to the door of the salon. There were definitely tears in my eyes, my secret no longer, but the fact that Caroline had set something like this up before her death, so like her. I turned to look for Jennifer’s car, but she had already left getting ready to pull out on the highway. I let out a deep sigh and walked in.

I was greeted immediately. “How nice to see you again Deborah, my name is Jessica and I am your stylist today. Please come with me and we will get started. She takes my hand and I am led to a room in the back of the salon. I try to see all of the things going on in the salon as we pass through, but to no avail. The salon is larger than the last time I was here, and a lot busier.

The appointment that Caroline had arranged for me so many years ago, was there makeover special. False breasts, wash and set, makeup, and a total wax job was the included features. I received female clothes, and a few lessons in walking in the new heels that I was given. I had just started my vacation, so I had two weeks in the female persona. I think Caroline had more fun with the feminine me than I did, but it was a very enjoyable two weeks never the less.

Jessica helped me to remove my clothes, then asked if I wanted some wine. As she retrieved the wine for me I noticed my clothes went with her, so I officially had no choice now. For the third time today I let out a deep sigh, my nerves just about to twist me inside out. When Jessica returned, she massaged my shoulders a little as I sipped on my wine. The two actions causing me to relax some. She told me that I would be here all day finishing round ten tonight, so relax and enjoy. I shivered a little, I can’t imagine how I will look after twelve hours in the salon, I am quite sure there will be no male left.

She took my glass, laid me back on the table and went to work on my body hair. She used a cream applied to the body and left in place for thirty minutes. While it is working on my front side she worked on my nails, rounding the nails into an oval, and adding extensions to each nail. Both hands were under separate UV lights as she wiped off the cream and all my hair from the front of my body. As soon as my nails were dry, she helped me to turn over and did the same thing to my backside.

While the cream is working she busied herself on a nearby counter preparing my next treatment. When the cream is wiped off I am turned over once again, my feet now placed in stirrups and my hands on an arm rest that had been raised by the side of the table. She gently placed straps to hold them there, for some reason I didn’t react. I knew that this new life is mine now, Jennifer spending all of this time setting it up, she would require me to go through with it no matter what. Besides my clothes had been given away and the home redecorated so what is the use of fighting things.

My inner feeling that Caroline had a hand in this somehow, is the determining factor though. We always got along, able to read each other’s thoughts, share our happiness and console each other in our sadness. I laid there as Jessica worked between my legs, there was some feeling at first, but a couple of sprays of liquid and I lost all feeling down there. I pretty much zoned out, thinking back of my life with Caroline, wondering if there would be times like that in my future.

Almost an hour later there was no sign of junior. Instead I now possessed two lips with a delicate slit running between them. Just like Caroline there was no hair there to spoil the view. I briefly wondered about what I do now, I am positive that by tonight I will look like a woman, my male clothes are gone that leaves very few choices. That conundrum was interrupted as she started on my breasts.

Two hefty sized clear plastic forms were place on my chest and then sealed to it by some adhesive. She removed two hoses from under the table and attached a hose to each form. A syringe of fatty liquid was added to each form and the pump was turned on. It was cycling off and then on, pulling a little more excess skin into the cup on every cycle. I could tell I would be here for a while, so I tried to relax some. My mind went somewhere, not sure where, but I was not coherent. That was suddenly brought to the here and now as she pierced my ear. Then before a rational thought escaped my mouth a second time in the same ear. The other ear suffering the same fate.

Hair washed and conditioned then placed in curlers, heavily sprayed before the hair was wound around the curler. I imagined I would end up with a curly hairstyle laying around my shoulders since my hair was down to my shoulder blades in male mode. Eyebrows waxed pencil thin even if the current fashion is for bushier brows. Nails were next as she affixed some wicked looking extensions on my fingernails. Coat after coat of nail polish was applied to my fingernails, plus my toenails. As I looked at the lengthy nails my hands now sported I realized that my time doing yard work or repairs around the house were most likely gone forever.

Although the boob machine was still doing its thing, and my hair was still drying under the dryer hood, most of my male features had already been done away with. Some makeup and Deborah would be the only image in the mirror. Maybe I should spend some more time with my daughter Jennifer, other than Caroline she has shown me love and acceptance for five years now, quite a feat since I have been far from cooperative. A cruise maybe, a skiing trip to Colorado, maybe I can help her find someone to love her as much as I do. Thinking of all of this I noticed I had a smile on my face, a smile that had been absent for so long.

The hair finished drying, the boob machine shut off and I was helped into some gorgeous lingerie, then a cute sweater dress. My hair styled just as I thought it would be, then my makeup applied, Deborah now the only image in the mirror. They were getting ready to call Jennifer, but I asked them to hold off a few minutes. I retrieved my cell phone and called one of Caroline’s and my old friends. I apologized for past words said to her, and told her I was living full time as a female now. About time was her only remark.

I asked her if she was still setting up cruises and vacations. She was so I told her what I wanted, and a starting date if she could get it all together fast enough. She saw no problem telling me she would call in the morning with the details. Then she asked if after I return from the cruise could I see my way to having lunch with her, her treat. I actually cried a few tears, a future life was there all the time, just waiting for me to embrace it.

“Deborah would be thrilled to have lunch with you, but I insist on paying to make up partially for the way I treated you.”

“How about we go dutch on the first lunch, then make it a weekly thing after that?”

“Deal, I am so happy you don’t hate me.”

“All of your and Caroline’s friends knew what you were going through, so we just waited, knowing that Deborah would eventually emerge and all would be right again. Now hang up and tell your daughter the two of you need to go shopping for new clothes and I will call tomorrow and let you know when you will sail.”

I saw Jennifer coming into the salon and walked over to meet her. I gave her a huge hug, then told her we have a lot to talk about tonight and suggested we head home so we can start to get things together. I got a puzzled look, as she was trying to appraise my new looks and also trying to figure out what I was talking about. We walked out of the salon arm in arm, a dismal past now looking to be a brighter future.

We talked into the night, it was past two in the morning when we finally headed to bed. Jennifer was so happy that I had reached out to some of our friends, and that they were just waiting for me to do so. Right before we donned our nighties I mentioned that we had to go shopping for clothes today, since it was already well into the next day. I got a puzzled look from her, then a wallop on my arm as I told her we were taking a cruise together, leaving in the next few days. I also received a big hug, happy to be included in her new Mom’s life and excited about taking a cruise, something she had no exposure too in her life.

We spent most of the day shopping, although I was sorely missing the sleep I had missed last night. Most of the clothes were way too brief, but exactly what I needed according to Jennifer. I swear I spent most of the time in dressing rooms trying on the clothes. Then modeling them for Jennifer’s approval. We got back to her apartment around seven that night, laden with way too many bags. Jennifer insisted we try everything on again, marking items that needed to be altered. Then I had to hang all of my new purchases before I was allowed to sit for a few minutes. Within a few minutes of me settling in her most comfortable I was sound asleep, the mind might have been willing but the body was pooped.

My friend managed a departure date of next Monday, I was thrilled since I was sure that would keep Jennifer busy, allowing me some time to relax and enjoy my new gender. Wrong, I was included in everything she did, by the third day I was joining in the planning looking forward to the cruise. I even day dreamed about maybe meeting someone special on the cruise, someone to love and able to love me back. But first I had to find someone special for Jennifer, she is way too young to be alone, having to take care of me, while appreciated is not a life for a young caring female.

Another full day at the salon for me, any last trace of my masculinity annihilated by the techs at the salon. I did trick Jennifer into going with me, she getting the works also, now to find her a lover to treasure and care for her.

The cruise was wonderful, Jennifer on the first day meeting up with a young crew member who was definitely infatuated with her. They met many times on the cruise when he was not on duty, her smeared lipstick a tell tale sign of her interest in him.

My soul mate came along just a day before the cruise ended, we met at the party ending the cruise. We lived in the same town, just on opposite ends of it. She had met Caroline earlier in life, they even had talked a little about me, although no mention was made of my name or that I was married to Caroline. She gave me her address, insisting that I come to dinner tomorrow night and bring a bottle of wine. I tried to refuse, but she was adamant about me showing up. I was told that if I failed to be there by seven she will come to my place and raise holy hell with me. She had the look that Caroline used on me often, daring me to refuse her or deny what she wanted. I learned quickly to do as Caroline wanted, her ways of getting even very wicked and novel, believe me. I imagine Helen might be the same way.

Later that afternoon I mentioned that I have a date tonight, my embarrassment at doing so showing on my face. Jennifer was thrilled for me, then I questioned what she was going to do while I was gone, she immediately blushed red, I smiled but told her to say hi to Josh for me. Another even darker blush appeared, I just hugged her and told her to have fun. That night was the first of many dates for us, both Josh and Helen frequent visitors to my home. I had talked Jennifer into moving in with me after the cruise, that way we not be as lonely as before.

Josh had found employment is his preferred career, the cruise ship job to help with expenses while he finished his schooling. it was three months later when he asked Jennifer to marry him, of course Jennifer said yes, she would be nuts to refuse his advances. Even as they were dating one could see the deep love between them, something she had never experienced before in her life. A love like Caroline and I experienced in our marriage.

With my daughter moving out I decided it was time to ask Helen to marry me, I had arranged a romantic dinner at a private restaurant, all in anticipation of asking her to marry me. I picked her up, at her place, she was sporting a huge smile, bigger that I normally saw on her face. The valet got our doors for us at the restaurant, and we were seated in a private area usually reserved for special parties. This was not what I had arranged, but I kept quiet not knowing what was going on. The waiter ignored me only consulting Helen on what to drink and our food orders.

I was about to say something when she rose from her seat and knelt in front of me. She reached for my hand, and placed a ring on it, it was gorgeous, very similar to what Caroline wore that we had picked out together so many years ago. She looked into my eyes and asked if I would marry her. I was crying by now, tears cascading down my face but I did manage a yes. She pulled me to my feet and took her hands to hold my face right in front of her. She leaned in and planted a sensuous kiss on me, my tears mixing with our lipsticks as the kiss lasted forever. I heard some music, then a band playing Helen’s and mine favorite song. Another round of tears, I am sure by now my mascara was not on my lashes anymore. Probably smeared all over my face. We did finally take time to eat our food, I had no idea what I ate, too wrapped up in my feelings for Helen and my love for her. I remembered the ring I had got for her, slipping it on her finger, causing a few tears to adorn her cheeks too. We must have looked a sight as we headed to the ladies restroom to try and fix our faces, it did take us a while to make repairs.

Helen wanted a simple marriage ceremony but insisted I wear a white dress. Nothing elaborate, she was mainly interested in making it legal so she could take me home and ravage me, nothing more. Jennifer and Josh decided on a quickie trip to Vegas, then a honeymoon in Alaska, somewhere it was so cold they would have to stay in and keep each other warm. Josh took her to his parent’s home after the honeymoon, now vacant as they had moved to Florida. Jennifer loved it, cozy and with enough room for a family later.

As she was telling me about their wish for a family she looked my way often, a ready made duo of baby sitters at her disposal. I poo pooed that, it will not cut into our bedroom time, maybe during the day but no night time baby sitting ever. We both dissolved into fits of giggling, an unusual conversation for a former father and her daughter.

I laid in bed, cuddling Helen as close as I could, thankful for all that has happened, a dismal past now gone, a bright and wondrous future now awaits. I lean over and kiss Helen on the lips, she pulls me closer and kisses my ear, the only part she can reach with the way I am holding her. The goose pimples spread all over my body, to be loved and cared for so special. I close my eyes, and drift off to sleep, dreaming of future kisses and special times together.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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