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For Womanhood

123

She moved closer to her lover, "But he is so beautiful too," she whispered as she ran her phallus along the moist skin of her lover's sex. She pushed into to her lover slowly, "I want to penetrate your husband too"

I had arrived at the Hotel on Fifth Avenue at 2pm and had a lot to do. The three storage cases had been brought up and I started to unpack the contents and check for any wrinkled garments. Most of the clothes that I'd had shipped in the garment bag were in perfect order but I set up the iron and quickly pressed each garment.

As I sorted the various undergarments there was a soft knock. I turned but I didn't answer. A soft pink envelope was slipped beneath the door a minute later. After I was certain the bellboy had retreated I stepped to the door and bent at my knees to pick up my instructions.

I knew I wasn't prepared nor dressed. I needed to shower and clean myself so I set the unopened letter aside. I'd been carefully instructed to complete my preparation prior to opening the letter.

The warm shower felt good and after I'd dried myself I completed the inspection of my cleft for any missed hair. I had only a small landing strip just above my small penis but was otherwise hairless. Yesterday I had shaved very close including my arms, legs and bottom. Afterward I spread the moisturizer over my very smooth body. I looked at my face with the magnifying mirror. I needed to spend ten minutes closely re-shaving my face. I went to the jewelry box I'd packed and removed the simple clip-on earrings. These were to help me adjust to the weight of the larger hoops I'd planned to wear later. Afterward I placed the short blonde wig into place on my head. I liked the simple short bob style and it helped me mentally prepare for I knew that within ninety minutes I would be leaving the Hotel room dressed as a woman.

- - - - -

Her speech was so attractive with a subtle English accent and her image on the big screen of my iMac had been how she had brought me to this Hotel today. She had been training me for more than four months each evening. Now her project had come to an end; she felt I was ready and passable. Callie was happy.

"But you must realize that any woman who stands taller than 69 inches is a bit unusual in the general public. In your 4" heels you are over six feet tall and there will be plenty of opportunities for other women as well as men to review your appearance Eliza."

"But Charlize is taller than I am Callie and she wears heels too,"

She cut me off, "That's enough complaining young woman. If I have to say another word you will be punished."

I ceased speaking. Her directions were very specific and she was well paid by my Mistress to complete my training.

"Giuliana will hear of this Eliza."

I had met Giuliana nearly six months ago in a chat room for consenting adults. I was attracted to her reserve and then her manner when we spoke on cellphone a bit later. She had allowed me to view her on facetime after a few weeks but only after I had agreed to be hers. It was a month before I'd understood and acquiesced to her exacting demands. Those early weeks were very difficult, as I had no idea how I was to act.

"You need training and help with these adjustment Eliza," she had named me that during our first telephone conversation.

"I will have a woman named Callie send you an email. If she agrees that she can work with you, that you can be trained, I'll confirm and you may just become my new pet and lover."

I wondered how we had become so attracted to each other. I was willing to adjust so much in my life for a woman whom I hadn't met in person. Giuliana was a few years older than me but almost as tall. Her personality was strong and she was motivating my changes.

"We will see if you can be good for me but first you must understand my needs."

She had directed Callie to help me and the time Callie spent wasn't covered by my small sums sent to cover the clothes and accessories. Giuliana had committed a great deal to bring me to this Hotel.

Callie had spent those first months getting my weight down and my skin smooth and yet I hadn't met her in person either. Later this afternoon I would visit the Hotel Bar and meet her for the first time, at four this afternoon. I had to get ready!

Months ago she had said while speaking on the telephone, "I demand that you purchase a specific computer and we will use the cameras to train you Eliza. If I'm unhappy, if you do not please me, I simply won't call back for several days. I will not inform you how you've displeased me. That will be for you to consider and resolve."

After the first month a package would arrive every few days. Skin care and hair products at first, than the initial wig. She was unhappy with my hair; it was simply too short. She directed me to cut it even shorter which would aid my wearing a wig.

Reviewing the first wig she had sent me, "I think that will not do. It makes you appear too old."

The next day a new wig was delivered.

Callie would review me each evening at 8pm via facetime so I had enough time to shower and prepare after I arrived home from work.

"Eliza you must send me another twelve hundred dollars. Use the same bank number and be sure to do this by 9am tomorrow."

Eight weeks into my training she told me that she would have a shipping box delivered the next day. I had forwarded nearly $2,700 dollars during the past three weeks.

"Do not open it until we see each other Eliza," she had instructed.

Chuck carried the large cardboard box and left it for me to bring inside. He was my local brown truck agent and he saw me at the door as he approached the stoop.

"You get a package almost everyday now Mr. Clark."

There was only my address and a prepared return on the outside, 'SpeedMail'. The return was from a province somewhere in the State of Maryland.

As I prepared for Callie's facetime that evening I was excited. She now required that I apply a foundation and makeup including mascara, soft brown eyeshadow and lipstick. My wig had become easier to wear and I'd learned to comb it out each evening. Actually there were three wigs and I was to select one each evening and style it so that she could review my effort and comment.

"I think the pony tail is too much Eliza. Take the band off now," she said when we started that evening the big box was delivered.

"That's better, now you may open my package. Please realize that Giuliana has reviewed all of these for you. Oh but stop! I must confirm your weight. Get the scale an the dress tape."

I had been on an aggressive fasting diet and my weight was now one hundred forty-one pounds. The loss of twenty-one pounds had caused my workmates to comment but I'd explained it away as due to a new exercise regiment. In truth I hadn't found the switch to mostly salads and protein drinks to be an issue. Though the change had made me less strong. Now just moving the large forty-pound box about the Living Room to be near the iMac proved a challenge.

"Direct the camera Eliza, oh my, you're only one hundred thirty-eight today."

I wrapped the tape about my narrowing waist.

"And the tape says twenty-eight and a half inches. That's impressive for a change. Three pounds in two day!"

I hadn't slipped off of her diet previously but over the last ten days I'd settled into just eating less. Forget the burgers and pale ale; I was changing. Giuliana was excited to hear of my progress when we spoke every other evening but only with me having been prepared and now dressed with Callie's help.

Speaking with Giuliana later that evening on the facetime, "Callie suggested that you be corset trained Eliza. This is what will happen until you can keep your waist below twenty-five inches. She will have a special garment prepared and sent to you within a day."

Callie hadn't spoken of the corset but I'd guessed the reason for the extra measurements last week.

"She also spoke of your gait training very strongly. Her view on such matters is more than I'm aware of but she has trained three other during the past five years."

I considered asking Giuliana whether these three were still in her life but knew she won't share the intimate details.

"Only when Callie is happy will you and I actually meet. Then I will decide, and only then will you know me Eliza. So keep focused on the lessons. Your speech is still quite rough though the tune of your voice is much improved."

I had started to record her facetime calls to watch her over again. She was so beautiful. Why had this woman come my life? How had she led me to this?

- - - - -

The box from Callie had a second box within and inside that were several other smaller boxes and packages.

"There, the pink one. Open that please Eliza."

Inside were two soft but heavy breast forms, "Show me one please."

She was happy, "these are a second set. Find the other pair, smaller. They may be at the bottom of the box. You need to find those please."

I recovered the second pink box and found inside a slightly smaller but similar pair of breast forms.

"There's an adhesive there. Spray it on the backs of the B size and we'll set them on the marks we made yesterday."

She had spent thirty minutes having me prepare my chest yesterday. First I re-shaved and then measuring carefully and marking my smooth chest. This was difficult to do by myself. I'd had to remove the marks twice to meet her approval.

"Start with the right one Eliza," then I placed the left silicone form into place.

"Lye down for four to five minutes."

I wondered while I waited where Callie might be living as she hadn't shared her home location. I'd noticed that the sunset was typically later for her location since her camera showed the back wall of the room from which she had instructed me for nearly two and half months.

Returning she had me open the zippered fabric lingerie storage bag.

"These are your first bra and panty set Eliza. Please try and put the bra on while you sit on the floor."

I had been prepared during the past weeks for the underwear change and the fake breasts but it still took me a few minutes to get the lovely simple white bra clipped into place and my new breasts settled.

"Can I ask how I'll get these breast forms off later tonight?"

She chuckled, "Not tonight Eliza. I will have you call in sick to that engineering firm for tomorrow we will be busy all day."

It was Thursday evening, "In fact, you and I will work on many details over the weekend. The removal is quite simple but they will remain with you until Monday early morning."

That meant I would be trained for four days and nights. What could we possibly find to do during that span of time?

- - - - -

I had thought we were going to grow old together. Amy was a beautiful woman and though small in stature she was full of life. Our sex was good but turned interesting near the end. The divorce was the conclusion of fifteen months during which we didn't fight but drifted apart.

Amy had a close friend named Debbie and one night I came home earlier than anticipated. I found them in our bed making love. Amy didn't even know I'd watched their love making for five minutes before leaving the house. The following morning she asked me to participate in a threesome with Debbie.

"But I want you to watch. Please join me and my other lover."

After we talked and she pushed further I accepted the request but was surprised that night when Debbie said to me, "Hand me the insertable dildo."

I watched her fuck Amy to orgasm two times with her stiff long false dick. Yet their tongues and pussy were so beautiful to me. Afterward Debbie came over to me. My excitement was intense watching them.

Walking naked toward me while I was sitting beside the bed Debbie said, "I want some cock and Amy says that though you're not too big you can fill a girl's mouth. She say you love to watch us."

She sucked my cock and stopped after making me harder than I was; I hadn't cum.

I turned to watch these two women lick and suckle each other. I was intensely aroused. I became very hard and stayed hard even after I'd orgasmed without touching myself.

"Amy says you love watching two girls. Let's do this again soon. We won't need you with us each time. Together I'll enjoy the best of both of you."

A week later Debbie told Amy that she wanted to fuck me.

"She said that, that she wanted to stick her toy into my ass?"

I resisted her and Amy for a period and they became less interested in having me join them in bed. They seemed to be together all day. On many days when I came home the two were loosely dressed. Occasionally Debbie would tell me of their sex filled afternoon.

"I fucked Amy's tight bottom," she said grabbing my ass. "Can you let me inside here?"

After a difficult discussion one night after I watched them licking each other with a dual dildo in their pussies, Amy smiled as she looked to me and said, "He doesn't get soft and his cock can get me off. I was hoping that he could learn from our sex play. He just isn't that adventuresome."

Speaking now to me Amy said, "and I do want her to fuck us both. I want Debbie to fuck us both in the bum."

I wondered about her sexual interest in this woman. Debbie had a different body type from Amy, thin with smaller breasts, and she seemed to never be sated. Could I compete for Amy against this aggressive female lover?

- - - - -

Sunday afternoon Callie had me make a facetime movie for Giuliana. I was dressed in an elegant off the knee petal pink A-line dress made of soft silk with a twisted waistband shape and a surplice V-neckline and floaty skirt. My very tall heels were silver with narrow straps but I had spent the past three days learning to move in similar tall shoes.

"Your movement is much improved Eliza but you must spin more slowly and speak as I've instructed you so that Giuliana can see and hear your progress."

She had directed me made a three minute clip of me walking and moving about the room. Three times were necessary to make her happy with the video clip.

"I'll add the video study we prepared Friday morning so that she can understand the improvement Eliza. The changes are remarkable."

I had received the custom built corset and had spent most of the weekend wearing it. The method of snuggling up the laces by myself was now understood and the garment pulled me to a twenty-five inch waist.

"You will not wear the corset for this segment Eliza. I want Giuliana to see how the weight loss has made your waist evident. Next time you'll wear the corset but we'll see now your training goes."

A few weeks later Callie had me call in sick on a Monday. We had spent another four days of intense practice. The focus this time was mostly on my makeup and the styling of the new long length wigs. She required another $2,500 dollars for the additional clothes, wigs and makeup.

I now had seven pairs of high heels and eight wigs of different length and color. The nine different dresses, plus the skirts and blouses and even a pair of dress pants were filling my closet and dresser. She had sent me so many different bras, thongs and support garments. There were fifteen to twenty packages of pantyhose and stocking as well.

"We're almost half way done with your wardrobe now that your weight is at one hundred and twenty-nine pounds. I'm happy to tell you that Giuliana has approved your new waist at twenty-five inches but she has insisted that I keep you in the new tighter corset for the remaining training sessions."

It was Wednesday and her statement surprised me, "But Callie do we have to?"

She ended the call.

Three and a half months and I still hadn't learned the lesson. I knew I had the evening ahead and went to the mirror. Her training had made me appear as a female, a woman. I stood there for a few minutes thinking. I was a thirty-one year old divorced male with a good salary but somehow I had slipped into this adventure. Seeing myself reflected in the mirror it was all I could do to resist dancing. I loved the narrowness of my frame and arms. I wondered if Debbie would like to sleep with me now. Would Amy enjoy my new body and feminine manner? My submissiveness was clear to me and Debbie had seen to it that I would forever love the sex woman can have with one another. I thought that Amy had left me because I was moving toward the feminine. I had spent so much time with her and Debbie. Now Giuliana was moving me toward womanhood for some purpose. I might be hers yet.

- - - - -

"She is nearly ready for your meeting. Eliza looks lovely and carries herself beautifully."

Giuliana looked at Callie on the facetime chat, "She is lovely, but he was beautiful before you started Callie. She has told me of her marriage and the failure. I need to know, can she still become hard? I don't want just a woman with a penis. I want a woman who can fuck me."

"She has been penetrated and she can become stiff even after her own release. Should we set the visit for this month?"

Giuliana considered the possible dates. "No I can't meet her until I'm certain. I don't want this one to runoff with her ex-wife."

- - - - -

I knew what my mistake was. I wasn't allowed to question any instruction, especially since she had told me this one had come direct from Giuliana. I considered the new narrower corset. I removed my dress and placed it about my waist. I pulled the laces very tight and reached for the tape. I wasn't breathing comfortable yet but the measure was twenty-three and a quarter inches.

Callie had restricted my sexual activity but had allowed me to play with myself once a week. Now I had some time and her last package had contained two sex toys. I released the corset and slipped on my chemise. Her instructions had advanced to teaching me to accept the medium toy into my body. I was in bed with the toy when I received an alert.

It was Giuliana on the iMac, "Eliza can you be any more patient dear? I have seen your amazing changes and I'm anxious to meet you. I just need another week okay?"

I moved closer to the screen camera, "Mistress you know best."

"Seeing you this comfortable is exciting but did I interrupt your play? I see moisture on your inner thigh."

I clamped my knees together, but my toy slipped out of my body to the floor, "I apologize for this Mistress. My body needs you soon."

She smiled, "Eliza show me your stiffness."

I slipped the chemise I was wearing to the side and my very rigid penis was inches from the screen. I could see her joy.

"Eliza did your wife's friend ever fuck you?"

I looked downward, "Yes Mistress. They both fucked me."

"Callie will call and make the arrangements in the morning. I must see you soon Eliza."

- - - - -

I had traveled to the Hotel dressed as a male but with a hat and sunglasses to conceal my eyes. Only the holes in my ears were apparent and I'd worn a winter coat to cover my evident breasts and a thin glove to conceal that my nails were deep ruby and quite long, too long for a boy. The room key had been handled by Callie and she had left me an envelope at the Concierge desk. A tall man with soft brown skin and a baldhead handed me the envelope.

Entering the elevator I removed the glasses and studied my face in the mirrored door. I didn't look like a boy any longer. Anyone near would not guess my gender because of how I was dressed; a college student heading to a room on an upper floor. Later today I might meet the woman who had changed my life, for better or worst. I was excited and had to get ready.

Dressing and doing my face would take an hour plus so I put on some soft music and completed my cleaning and had a warm shower. Wearing the fluffy white rode I slipped on the heeled slippers. I walked to the bureau and selected the short blonde wig. I wore this to help me focus on my face. The deep shadows I was taught to use for an evening look required three different tone of eye makeup. Then the triple mascara took another fifteen minutes since I paused to allow the Chanel Inimitable to set. The result was a more intense lash look but patience was necessary. Between coats I slipped on the new LaPerle bra in stretch tulle and the matching brazilian brief in black. I returned and spent five minutes preparing a applying the lipstain in deep red.I reached for the Freesia suspender and the enjoyed the taut but subtle restriction of the perfectly sized waist-defining garment. The hose slipped up my long smooth legs and I recalled Callie's awe when she had me measure my legs.

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