In the first three parts, the local barista at Starbucks comes to the rescue of his favorite patron and secret crush. They begin an unusual relationship that spans their very different worlds. The Barista begins to experience many pleasureful changes to his previously dull lifestyle and wardrobe.

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Chapter 8--

All the way home in the car Charlie was expressing how wonderful I was going to feel with my smooth skin covered by nothing more than a satin nightgown. It seemed almost silly to even imply a desire to act more manly when we reached her home. I knew the pending encounter would be pleasant, but after today, I needed to resign myself to the expectation that with Charlie she expected me to be the the meek partner in our love-making and act mostly docile. Any attempt to insert control or defend my Y chromosome would be treated harshly.

Inside her home she made us cocktails and brought out some chilled chocolate strawberries. We wasted little time finding each others lips and making our way to her couch. She knew all the areas on my neck and ears to stimulate my entire body. I felt totally under her control and loved every second of it. After a period of time that passed in a blur we found our way to her bedroom.

We hardly missed a beat of our foreplay as we stripped off our clothes and only I was given a nightgown to change into. Charlie stripped down to only a silky pair of boxer shorts, while I slipped on the pink long nightgown. I was too aroused to even care about the wardrobe irony. We caressed, kissed and stroked each other until my body was nearly on fire with sensations. Charlie even massaged my non-existent breasts as if I were an actual woman. With my smooth skin and other changes I had a growing understanding of what it would feel like to be in a lesbian relationship with Charlie. I knew it was only role play, but the total emersion in the female style love making was a completely erotic experience. Charlie had previously made it clear to me that she was Bi, and in unconventional way I almost felt like her female partner.

The lovemaking followed a similar pattern as our last encounter. I was able to drive Charlie into ecstasy by going down on her orally. She had no interest in me entering her in the conventional way. In our last sexual encounter she had also satisfied me orally before concluding my orgasm with a dildo penetrating me from behind. Prior to meeting Charlie I had never so much as contemplated a rectal encounter, my first thoughts regarding the possibility of such an experience occurred as I was already in the process of receiving it. I still felt some guilt because there was no denying that I had exploded in sexual satisfaction when I first encountered her lubricated toy.

This time around Charlie simply manipulated my male appendage with her hands before aggressively flipping me over and once again impaling me with the sex toy. Charlie had strapped on the realistic looking device before impaling me with her multiple hip thrusts. I was turned on by the control Charlie exerted over me, but this time Charlie had not even made a passing attempt to orally reciprocate as a girl might attempt to satisfy her boyfriend. I did not resist her forceful move and quickly found myself squealing in satisfaction. As I rested feeling once again sore, a sense of satisfaction still flowed through me even though I had abandoned most of what was left of my masculinity.

I had no problems drifting off to sleep. My body's senses had gone beyond simply ecstasy and I was maxed out. Sleep was the inevitable conclusion. I slept like a rock for about 3 or 4 hours before waking from some strange dreams. My mind was immediately focused on my new found relationship status. I felt happy, lucky and confused. I had little experience in relationships, but the nature of our bond was so foreign and taking me deeper into the dark hole.

I knew that the gorgeous creature peacefully sleeping by my side made me feel special and loved, but in only a short time I had altered my daily lifestyle in ways I could not even explain to myself. Was Charlie bringing out aspects of myself that I had repressed or was I simply following her lead? Whichever it was, I had never felt such intense sexual gratification or ever the loving attention that I was receiving. I was not sure where I was headed, but currently sharing her bed felt right.

Despite lying awake in bed during the middle of the night I had not noticed that Charlie was no longer in bed. Once again she had gotten a jump start on the morning and had left me to sleep. When I discovered I was alone I knew I had to get up, but I felt so wonderful in her bed wrapped in my silky smooth nightgown covered up with her satiny smooth sheets. I felt like royalty, but would never be mistaken for a king.

This time I instinctively went into her closet and grabbed a silk robe before going on a search for Charlie. I sashayed down the hall in my lingerie on a hunt to retrieve my dream-girl. I took the long route to the kitchen to check out more of Charlie's home and because walking in the silky clothes was so enjoyable. At the far end of the hall was what appeared to be Charlie's home office. It definitely looked like a very functional work space and lacked some of the stylish touches of the rest of her home. It was designed with work in mind and had sparse distractions beyond the high tech computer setup. The only non-business items that adorned the room were two framed photos of attractive twenty-something women. I had never seen them before, but they looked professional like Charlie. I knew she did not have any sisters so I guessed they were past relationships. There was an empty frame next to them, and my racing mind speculated about a past affair that she could not bare to be reminded of. These thoughts were all pure fantasy and not really my business since I was snooping around.

I could only dream of living in a house like this. My parents did ok, but I would never inherit enough to even consider anything along the lines of Charlie's place. My work career was off to a slow start and at it's current pace only provided me with my basic living standards. If I was going to continue my relationship with Charlie it would have to be mostly on her nickel. Seeing how wonderful it felt on the other side of the fence made me contemplate my own past employment decisions. Maybe it was time to consider something more career oriented or at least something that paid more. Charlie's emergence into my life had me thinking about a lot of things.

I finally made it to kitchen and knew she was inside because my nose could smell the distinctive aroma of fresh coffee. I ran my fingers through my hair so that I would look good for Charlie. I had a big smile on my face as I entered the room expecting to find Charlie.

I found her, but she was not alone. Her friend Tania from Bloomingdales was sitting at the table with her. They both greeted me with giant grins. I froze in my tracks about 10 feet from them.

"Brooke dear, don't be shy, say hello to Tania. She stopped by before work to discuss a few things. Please join us for a cup of coffee."

"Yes Brooke, I am so glad to see you again so soon. Plant your pretty little butt over here at the table."

I wanted to flee. I couldn't believe that someone besides Charlie had seen me dressed like this. I had a hard time forming any words. "I am sorry to interrupt, I will leave you two."

"No no, Tania and I were done with our business. Please join us. She won't bite."

"Hi Tania. I am surprised to see you so early this morning."

"I just stopped by for a short while. I am sorry to invade your personal morning."

"It's Ok, I was going to be leaving soon anyway." I really had no plans to leave yet, but it seemed like the right thing to say.

"I will be on my way in a few minutes too. I have to be at Bloomingdales before they open to set up the displays."

"You work at a very classy store."

"It is nice. Charlie is going to have to get you in soon to pick up some chic clothes."

"Charlie has already done enough for me, but thank you."

"Honey, Tania is right. We do need to get you some stylish things of your own. We will just have to make some time in the near future."

"That's nice Charlie, what ever makes you happy."

"Brooke I see that both you and Charlie are wearing your matching earrings. They look lovely with your pretty ensemble. Doesn't satin feel heavenly in the morning?"

"Yes it does feel nice, it was the only thing here for me to sleep in."

"Of course it was."

I managed to maintain my composure until Tania left which was very challenging. After she left, I asked why she did not warn me that Tania was coming over.

"She is my good friend and already knew about the two of us."

"She must have thought it was strange to see me like this."

"Hardly, she had already mentioned to me after meeting you how cute you were. I told her not to get any ideas."

"Charlie, this is all so confusing for me, and has become surreal."

"If we are happy that is all that matters... don't over think things."

"I love what we have too, but..."

"But what Sweetie?"

"Well, the first one of either of our friends that have seen us together, see me dressed like this. I know we currently live in different worlds, but doesn't that seem strange?"

"Not really, but you are right. Are there some friends that you want me to meet?"

"No one specific, but it would be nice if I introduced you at work or if I even met some of your friends or colleagues."

"If that is what you want. Have you been keeping us secret? Are you embarrassed being with me?"

"No way. I just didn't want you to be uncomfortable in the Starbucks."

"Nonsense! Your friends are my friends."

"Thank you."

"You and I have not been been together all that long, but I will come up with an appropriate opportunity for you to meet more of my acquaintances."

We had a second cup of coffee together before I changed and went home. Charlie mentioned how grateful she was for the past 24 hours because she was entering a very busy stretch at work. She had some very high powered and intense divorce proceedings coming up and one of them was likely headed for a trial. She was very good at her job, but she did not think she would have much personal time over the next month.

Charlie told be how much I meant to her and that she was hopeful I would be understanding if we did not see a lot of each other during this period. She said she would sneak some time in here and there, but that was all she could promise for now. I was sad that just as we were getting closer that our time together would be limited. I just told her that I would try and stay flexible if she had any time or needed some comforting. In reality Charlie was the only real thing in my life outside of Starbucks.

Chapter 9---

Charlie and I did not see a lot of each other over the next month, which then extended to 2, 3, and then nearly four months. She always seemed busy with big divorce cases and her numerous duties managing the firm. We did see each other, but mostly it was for an evening cocktail or over a spa treatment and was never more than once a week. We did follow up a few of those drinks with some playing around, but our quality time together never seemed enough. Our infrequent sex typically followed previous patterns and I was gradually getting used to being entered from behind. I had pretty much accepted this as the norm for our sexual encounters and no longer even held out hopes for a more traditional position.

I became a regular at LuLu's Salon and Beauty Clinic. Charlie insisted that I go there every other weekend to keep my skin smooth, nails manicured and hair conditioned. About once a month we shared a massage, but mostly I was there by myself. LuLu took her marching orders from Charlie, so I was still treated like royalty and all of my treatments were pre-scheduled for me. I continued with the full body waxes followed by the Laser treatments. Beginning with the second treatment they also lasered a very small patch of hair that I had on my chest. By the time month four rolled around there was really no need for me to shave anymore. There were only a few odd hairs remaining and even those would be gone soon.

My hair treatments were mostly just maintenance, trimming and tending to the few split ends. I had previously left my hair very long, but now it was significantly longer than I had ever let it grow before. Even working in a Starbucks, I was starting to wonder if it was too long for a work place. Charlie always complimented me on how it looked and not surprisingly told me how sexy she thought long hair was. Not that the stylist ever asked me, I did not dare suggest to have it shortened.

Other than our time at the spa, and visits to her place, Charlie and I did not go out. Charlie still insisted that when I came over that I dressed more to her tastes, but at least I did not need to parade through restaurants dressed in the feminine selections that she always insisted on. Most of the clothes were soft sweaters, shimmery tops that were paired with matching slacks, but she did mix in a few maxi skirts and even once had me wearing a halter style one piece pleated dress.

At work my feminine slacks collection grew even larger. More than half of the bottoms were obviously women's pants to even a casual observer. My collection of lingerie and shoes also grew. I now wore a camisole daily that was color coordinated with my panties. Having my penis tucked under the gaff became almost second nature. Many of the slacks were long and now I had three pairs of shoes that had varying degrees of heels in excess of two inches. I began to wear pantyhose on days that I needed to wear the higher heels. Charlie even bought me a couple of padded briefs to wear with some of the slacks to give them a better fit. On the rare days I had both the heels and padded brief on, my derrière was very prominent.

My nails were also carefully groomed with a small amount of added length with oval tips. The clear polish eventually was replaced by a natural tint that had a hint of pink color. The color was not obvious, but I was always aware of it.

Between my altered grooming and the decidedly feminine fashion touches, I was treated by my co-workers more like one of the girls than a male co-worker. I never expressed any girlish desires at work, but rarely made any effort to defend my manhood. There was not much of an explanation I could concoct to justify my appearance. I considered on numerous occasions whether to stop with the avant-garde look or whether to tone it down, but I still had great hopes for me and Charlie. Even the small amount of quality time we shared felt so good that I was not ready to risk that.

On the few times I went to see my mother after work, I made a concerted effort to dress more manly. Even on those visits I still had on my gaff and panties, but I did not wear obviously girlish slacks. It was also the only time I did not wear my earrings. Despite that, my mother commented on the holes in both of my ears. When she saw me during the fourth month of my relationship with Charlie, she asked me what was up. She asked about my beyond shoulder length hair, my pierced ears, the noticeable weight even I had not realized I had lost, and the softer looking face I was now sporting. She said I looked younger, but wanted to know if everything was ok.

I told her I had met someone that liked me more stylish. I was stunned a bit when she asked if that new flame was a girl or boy. When I became startled she said all she wanted was for me to be happy. I immediately told her it was a girl, but I was not ready yet to introduce her. After the uncomfortable exchange we had a nice visit. Nothing more was said about my subtle changes until I was getting ready to leave. Mom asked if I needed help with my style changes.

"Honey, if you like I can go shopping with you. I am sure it is a little awkward for you to shop in some places. Having a woman accompany you can help looking for the special styles easier."

"Mom, that's OK I am doing fine. My friend Charlie has been helping. Is he also dressing 'Stylishly'?"

"Charlie is a she, and yes she is very stylish. I am sure someday you will meet her."

"Alright, but the shopping invitation is always open. I am sure the new experience would be enjoyable for both of us."

"Thanks Mom. I'll let you know."

Even my own mother was questioning my manhood. There was no longer any daily part of my life that resembled my pre-Charlie world. My altered personal image changed gradually and almost too easily.

At work I had introduce Charlie to a couple of my female co-workers. They were excited to talk with her, but I never felt they took our relationship seriously. They hit it off and mostly talked about how much of a cutie I had become since we began hanging out. In our conversations they mostly referred to her as my friend. I knew Charlie and I had something special and that was enough for me. Boasting about my stunning girlfriend was not in my nature.

It had been nearly 4 months since Charlie said she was entering her busy work stretch. I was happy during our sporadic times together but finally decided it was time to inquire about seeing each other more. Other than the girls at LuLu’s there were no acquaintances of Charlie’s that I had ever met. We had never gone out with any of her friends and I had never met any of her work associates. We had talked about her office and even some of her co-workers, but I never actually met them. With the way Charlie preferred I dressed in her presence, I had not pushed hard to change that and even repressed my desire to interact with others.

Maybe I was getting used to our routine and the androgynous fashion changes or just growing a thicker skin. Either way, I was getting anxious to be less secretive and isolated. I knew it might lead to some additional scrutiny, but I was willing if Charlie was.

It was during one of our very brief after work cocktails that I pushed the subject.

“Charlie, you mean everything to me and I would never want to jeopardize what we have, but I would really like to meet some of your friends. We see each other at my Starbucks and other than that, only about once a week. If we somehow had more mutual friends or our worlds crossed more often, then I know I would be happier.”

“Am I not making you happy?”

“Of course you make me happy. I want to also make you happy.”

“So what are you asking then?”

“I am not asking for anything specific, just thinking that it would be nice for us to find more things from our individual lives to share.”

“You know how busy I am.”

“Yes yes. I am just trying to make it easier for us to spend time together.”

“Most of my time lately has been spent on work related issues with only occasional gaps.”

“I am not trying to add any stress. I would do anything for you. I just wish there were ways for us to share other things in our lives that are important or just spend more quality time together.”

“Brooke, let me give it more thought. I know I said that before, but maybe you are right and we should find some ways to do other things. We will talk about it more real soon… OK?”

“That would be great. Thank you.”

We went another week before we had a rendezvous other than at Starbucks. It was a glorious evening that included dinner out at the same restaurant we went to on our first formal date night. Charlie was in a particularly good mood which I did not want to ruin by objecting to her fashion selection for me. I always relented to her envelope pushing androgynous selections and tonight she was no different with one exception.

Charlie had me wearing black leather pants that fit almost like tights. On each side was a long gold zipper which were challenging to zip over the hip and derrière pads that Charlie insisted I wear. My contrasting white sweater covered over the lace camisole, but not the decorative zippers. The leather pants extended to just above my ankles, which did little to cover up the open toed pumps that Charlie handed me. These were a very sexy pair of heels and without long pants to cover them they were unequivocally all girl. Charlie and I had continued to get matching toe colors and with these shoes they would be on full display. I wasn't even sure I would be able to walk in the pencil heels.

"Charlie you know how much I want to please you, but these shoes are so totally feminine. Couldn't I just wear some low heel clogs or flats?"

"Brooke, the shoes are what makes the look. I really don't think that a different pair of shoes would make a meaningful difference in anyones perception of you. However, it would take away from how sexy you look."

"I just think I'd be crossing over the appearance line."

"Brooke, you need to face truth. You have been crossing that line for a while and enjoying it."

"It's just..."

I was quickly cut off. "Are we going to fight, because if so, this is not how I want to spend one of my rare free evenings."

"If I brake my ankle you are going to have to nurse me back to health."

"I am sure you will be a natural. You have been every step of the way so far."

"OK then, let's go before my nearly bare feet become cold. I almost hope no one realizes I am a guy."

"Come here my lovely and let me give you a kiss. You are such a good sport. I will make it up to you later."

With the heels strapped to my feet I still was no taller than Charlie. The kiss melted away my last doubts. Before we headed to the door Charlie added one more twist to my ensemble. She painted my lips with the same crimson red lipstick shade that she was wearing. For a half second I began to protest, but at this point it seemed almost pointless.

"Brooke dear, this will help clear up any ambiguity people might perceive."

We were out the door with little pretense of a man and a woman dating. I may still have considered myself male, but that was not going to be the image I reflected for the evening. I also knew that I was better off not trying to act the male part under the circumstances.

The evening went without incidence. With Charlie as my wing girl we did get a lot of looks. I am not sure how people gendered me, but I knew having such a gorgeous woman at my side made it bearable.

Back at the Charlie's house we could not wait to attack each other in bed. My public deception excited Charlie and I could feel her enthusiasm. I even played along by begging her to come and get me. I completely took the vixen role and even found myself making feminine gestures in an effort to entice my pursuer. Charlie even called me her little babe at one point of our encounter. In the end I brought her to multiple orgasms with the tip of my tongue before she mounted me from behind and rode me wild with a new vibrating dildo. She made every effort to make my orgasm last by adjusting her rate and depth of my penetration. I kept panting "Charlie, Charlie, Charlie" as my sexual intensity reached it's apex before exploding.

I knew that our further exploration into roll play had lit a fire in both of us. I was totally satisfied but scared at the same time. Charlie's passion and desire for me increased the more feminine I became. I wanted to please her, but to what end. I knew I was not faking my enjoyment, but the roll play still had me confused.

Chapter 10--

I had to slither out of her house early in the morning to ready myself for work. I had accumulated so many of Charlie's slacks and lingerie that confiscating more of her things at this point seemed ridiculous. I had a closet full of her clothes and they took up almost as much space as my entire wardrobe. My collection of her shoes were easily more than my own stash.

I saw Charlie later that morning at Starbucks. When she made her way to my barista station she gave me one of her mesmerizing smiles. She leaned over the counter and whispered to me that she really needed to get me some of my own lipstick. Maybe even some daytime shades for me at work.

Her whispering tone was very seductive, but her suggestion that I consider wearing lipstick to work was unnerving. I just told her in an equally soft whisper that she was silly.

As much fun as we always seemed to share did not change the infrequent nature of our get togethers. When I saw Charlie in the store she would only say that she was working on making more time for us and that she would have an idea to share with me shortly. Nearly two more weeks had passed before she asked me to meet her on Saturday afternoon at the spa. She only said she wanted to talk to me. I already had the scheduled appointments that Charlie arranged for and would welcome spending some of that time with her. I was a little nervous that she would't tell me about what she needed to say. It even crossed my paranoid mind, since it had been so long since our last fun that she might want to break up with me. Charlie also mentioned that she was entertaining clients that evening in a skybox at Wrigley Field for a Cub game. I would have enjoyed going with her, but that apparently was not the plan.

I anxiously awaited Saturday. I had to endure my waxing and laser treatments before I even saw Charlie. We had a Mani-Pedi together before we had any opportunity to speak privately. Despite my worst fears, Charlie was not in a dour mood. If she was going to tell me that we were breaking up, it was not apparent in her mood.

"So Brooke, I have been thinking about what you said about socializing with others in my world and I think you are right."

"Thanks Charlie, I've been looking forward to that."

"I think I came up with a great opportunity to introduce you in low pressure way."

"What do you have in mind?"

"It will take a little effort on your part, but it will be for a good cause."

"What do you need?"

"I think I mentioned to you that I am Chairperson for the Dream Foundation."

"Yes that is such a wonderful cause."

"Well the third Saturday night in October we always have our big Gala."

"If you are asking me to go, I would love to. Is it a formal event?"

"I would like you to join me there. I think you would enjoy it. There's food, dancing and a silent auction. We raise a lot of money that one night."

"I will gladly buy a ticket. Maybe even bid on somethings."

"I don't expect you to buy your own ticket. Besides I already have a table. You can always bid on things if you like any of the items."

"I am excited to finally meet some of your friends and associates. You said it would need a little effort on my part. Do you need me to do anything special for the event? I would be honored to attend and help in any way I can."

"Since we moved the Gala to late October three years ago we have used the Halloween theme for our inspiration. The decor will include pumpkins and other seasonal items."

"That sounds fun, do any of the guests dress up?"

"That's what I wanted to talk to you about."

"What did you have in mind?"

"I hope you are game. It would mean a lot to me and I am sure a lot of fun for you."

"I'm listening."

"I would like you to come as a Lawyer."

"Sure. I can look professional if you like."

"I think it would be the perfect time for you to go all out from head to toe."

"That should be easy enough."

I am not sure you completely are absorbing this. I want you to come as a woman attorney like me."

"WHAT!"

"Think about it. You have been experimenting with this idea for the last few months. This would be the perfect time for you to experience the full effect."

"You want me to come to your Gala dressed completely like a woman? Seriously? Charlie I am not sure I am ready to do something like that."

"I am glad you said ready instead of not willing."

"I know you are ready. I also know you will pull it off with panache and be a hit."

"It's one thing to go places that I don't know anyone and push the gender envelope, but another to go to a big benefit dressed that way."

"Brooke, first off, you probably won't know anyone there and secondly you will be with the Chairperson of the event. If that's not enough remember the Halloween theme."

"Even for Halloween that is a big stretch. I can't imagine anybody else would consider something so extreme. I could end up as the butt of your friends jokes."

"I remember last year at least one person did the same thing. That person came as a female paralegal. The year before someone came as a female accountant. I think you have the potential to out do them both."

"I will never live it down with your associates or friends. First impressions are hard to get over."

"For all of those attending from the firm I am the boss. They would NEVER laugh at you. Besides, that is why I want you to do it right. I told you it would take some effort. I am not just going to dress you up and send you out the door. When you make the first impression, it should be an impressive one."

"What are you suggesting? I am already dressing in your work slacks."

"This is one of my most important days of the year. I want every detail to look perfectly prepared. That includes you. I understand that this is a big jump from our past fun, but I would need you to be all in on this."

"All in?"

"The Gala is in three weeks and if you want to make the right first impression it will take some preparation. This may be asking a lot, but the week prior to the event I would like you to take off work and move in with me. The guest room would be all yours, but we would spend a lot of time together that week. We would get you the right clothes and accessories. It would also give you time to practice. When you finally make it to the Gala on Saturday you will have perfected your Lawyer image."

"You want me to move in with you and take off work? All this just for a costume."

"If you think you are doing this for a costume, people will see right through your presentation. I want you to do this for both of us and to hopefully experience more of what we have had together."

"I have not taken any vacation time in ages so that should not be a problem, but that Thursday is my father's Birthday and my mother and I have gotten together on that day since he passed away. I really can't miss that."

"We will just plan around that. I would not want to interfere with something so important to you. So are you in?"

"I like the idea of staying with you, but the rest is so over-the-top. I guess I will do it."

"Brooke, this is not an I guess kind of thing. I will have to adjust my plans too and you will have to be focused and committed. I don't want to deal with a reluctant boyfriend."

I think that was the first time she ever referred to me as a boyfriend. I was a bit reluctant, but this was going to be my chance to move in with her and show my devotion.

"Charlie, I will do my best."

"If you do your best, I know you will be perfect."

"So are we going to get a massage together now?"

"I wish we could, but I am going to schedule your special appointments now for two weeks from today and then be off to my Baseball game. I have to go because it is with important clients. I hope there are other woman there. You know how men can be at sporting events."

"What kind of special appointments?"

"Just the type of stuff you need to look pretty and more convincing."

With that I was once again alone at the spa. I was treated to an extra long massage today and was greeted by LuLu when it was over. She asked me how early I could get to the salon on that Saturday and I told her in the morning. She spoke to me in an extra friendly tone.

"Brooke, I am so happy for you. Charlie has brought friends here before, but you are the most special. Charlie obviously saw something in you and we have loved helping you to bring it all the way out. I really think you are going to make a very lovely young woman. Everyone here will be in your corner to make that happen."

When I had arrived at the spa I was concerned Charlie wanted to break up with me. I was now getting ready to leave knowing that I was going to be moving in with her and upping the ante on our gender bending games. I wasn't sure it was the best outcome, but I knew it was not my original fear.

_____________________________________________________

Chapter 11--

Outside of Charlie's visits to Starbucks, I did not see her until the last day at work prior to my week off. We did chat a few times, but there was no intimate times between us. Charlie had set up a meeting for me with someone I assumed was her tailor. She told me it was to get my body measured so she would have the correct sizes for when I moved in.

Charlie arranged for that meeting at the LuLu's incase I was nervous about it. I expected to meet some stereotypic looking man with a tape measure, but instead was greeted by an attractive woman named Roxy. Roxy was completely filled in on the unusual plans and enthusiastically took to her task. She measured me in every direction and from head to toe. She determined my woman's shoe size and jotted down other sizes that meant nothing to me.

Roxy sensed my uneasiness and tried to make me feel better. "You are going to look magnificent. You were lucky to be born with such naturally feminine bone structure that eventually no one will ever suspect you were ever a man. You are going to be so much happier looking in the mirror. Charlie told me all about your desire to look your best for the Gala and I plan to help you become the envy of every man at the event."

That was not my desire, but it really didn't matter. Roxy was hired by Charlie to help me get the proper fit and I was happier dealing with a upbeat woman than a traditional old male tailor that might have made me uncomfortable. Roxy indicated that Charlie was arranging a follow up for us to meet again on the first Saturday of my preparation for the fundraiser.

The day before I was to move in with Charlie I asked how much room I would have for my clothes and if she wanted me to bring over anything specific. Charlie told me not to bring anything. I knew that week was going to include a lot of dressing, but I wrongfully assumed I would have some boy time. I also wanted to have some of my stuff at her house incase Charlie's desire for me to move in extended beyond the Gala. I was hoping this was the beginning of our next step in our relationship.

I arrived at Charlie's house on Friday as planned. Charlie pulled me inside her foyer and planted a kiss on my lips. It was the ideal way to start our time together. I almost expected her to drag me to the bedroom, but that was not the case.

Following our brief moment of passion, Charlie was mostly all business. She showed me to the guest room which was at the opposite end of the house from Charlie's master suite. It was a very nice room with a decidedly feminine decor. It had a modest walk in closet, a poster bed and a modern style vanity. Next to the vanity was a full length three sided mirror. It was similar to the type you would see in upscale department stores. Charlie told me that in the top drawer of the clothing chest were fresh nightgowns, panties, camisoles, and gaffs. Everything else I need would be provided starting tomorrow.

It was a nice room, but I was hoping to spend most of my nights with Charlie. She seemed intent for me to know that this was my home base...not her room. I was surprised with her need to make that known immediately.

Following the room assignment we did share a cocktail and light meal around the fireplace. Every time I thought our shared passion was moving towards a sexual release our kissing would back off and the conversation would move us away from love making. It was only about 8:30 when Charlie told me I should probably get myself ready for bed. She told me that tomorrow would be a big day and I should be rested. My heart felt a little empty when she said that she hoped the bed in my room would be to my liking. There was certainly time for us to play a little, but Charlie was not in the mood for that. I did not want to start off my stay in a pushy way so I retreated to the guest room.

I was not really tired, but there was not much for me to do. Outside of playing around with my iPhone, bed seemed the only option. I changed into a nightgown from on top of the pile in the drawer and then just spent a few minutes exploring the rest of the bedroom. I looked through the remaining drawers of the dresser and discovered many additional items of lingerie including a wide selection of bras, some unopened pantyhose and other miscellaneous pieces. The bottom drawer had accessories including belts and scarfs.

On top of the dresser was a small chest that was loaded with all types of jewelry. The closet was equally full of clothing. The racks were full of garments and there were many pairs of shoes on the lower shelves. The person that Charlie said moved out had obviously left most of her wardrobe behind. Like Charlie's closet and room, most of the apparel looked to be high quality and meticulously organized. I felt a little like I was staying in some strangers room.

For lack of an alternative I slipped under the sheets at about 9:00. The clock on the nightstand began beeping at 7:30 the next morning. I was already awake, but still lounging in bed. A few minutes later Charlie spoke from outside my door and told me to shower, but not wash my hair.

When I re-entered the bedroom and found my bed made and some clothing awaiting me. The items were very soft and satiny, but the items were not much more feminine than anything else Charlie had selected. Over my panties and gaff I put the black pajama style pants and on top I slipped over my head the eggshell blouse with 3/4 length sleeves and crewneck top. It all was very simple and feminine, but not such that I would standout. I brushed out my hair before slipping on the simple wedge saddles at the foot of the bed. My toe colors actually looked nice as they peaked out from under the wide pant legs. I had great reservations about what I had agreed to, but for at least a few moments the clothing felt nice against my skin.

When I found Charlie in the living room she handed me an energy bar and a light coat.
"You are going to be at LuLu's for quite a while and should eat this so your stomach doesn't growl. They will get you some coffee and probably have some snack for you later."

"Good Morning Charlie. How did you sleep?"

"Not really enough. I went out for a while last night and should have come home earlier."

I had no idea she had left after sending me to bed. She also had not mentioned any other plans.

"I see. Any problems?"

"No, nothing special, just let the time slip away. Is my Butterfly ready to spread her wings?"

I just accepted the reference to being a her and tried to put on a small smile.

"As ready as possible, God Help Me."

"You will thank him later I suspect. I can't wait to see you later. I plan to pick you up when you are done so we can celebrate."

I was happy to know we would have fun together later, but surprised the spa day would not include Charlie.

"You are not joining me?"

"Brooke, you have a full day of treatments and people to see at the clinic."

"If I get my work done I may come over later for a touch up on my nails, but today is all about you. I hope it is everything you might fantasize it could be."

"Charlie, making you happy is my fantasy."

"That's sweet, but focus on yourself today. If anyone asks any questions, you need to tell them what kind of girl you see yourself as. Don't answer anyone's questions 'because you want to please me'. I have always seen more in you than you allow yourself to admit. When I see you later I want to see Brooke, not someone trying to please someone else. "

"I am not sure how I can respond to that."

"Relax and be yourself. If you like I can give you another pill to take with if you need help relaxing. I don't think you will need it."

"No, I should be fine."

"Everyone there will be catering to you. They are experts on this and will always be there to help you along."

"LuLu is very nice."

"Hop in the BMW pumpkin, my future princess."

"Cinderella I'm not... that's for sure."

"You may be right. Her fun ends when the party is over."

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