Girlfriend Problems - A Transition Story - Part 11

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My New Life.

I finally was able to go back to work and things went smoothly despite the occasional trips to the bathroom to dilate my vagina. I would have to continue to dilate for over a year with less and less frequency. I continued working at Richard’s office as the Office Manager. Janelle’s business was taking off. As promised she only served rich elite clients with escort dates with no sex involved.

It was over a year after my surgery that Janelle threw a cocktail party. It was in early June. There was a medical convention in town and Richard and Janelle decided to invite some of their colleagues and friends over to their home for a party of about 50 guests. Janelle insisted that I come.

“Kathy, you need to come. Get something nice to wear and get your hair done. I would really like it if you were there.”

There was no way I could deny Janelle after all she and Richard did for me. Although I was tired from a long week at work I obliged her.

“Is this a formal party?”

“Yes, I would suggest an evening gown and stilettos.”

“That I can do! I’ll be there. Don’t worry.”

I went shopping that day and bought a beautiful evening gown that was gold with a plunging neckline that showed off my cleavage. I didn’t have any trouble with stilettos. I have acquired plenty of shoe choices over the past 3 years. I managed to get an appointment at Marisol’s for that Friday after work and of course, she did an amazing job on my hair. That Saturday came and I got ready and did my makeup flawlessly. I arrived at Janelle and Richard’s home around 5pm. There were only a few guests there as Richard and Janelle busied themselves making sure all of the details were just right. They had a tent set up in their spacious backyard, valets to park the cars as well as a catering service for the evening complete with bartenders. They even had a string quartet playing. As I entered the house a young lady was standing there holding a tray with glasses of champagne and handed me a glass. I had never been to a function like this and didn’t really know how to handle myself. I must admit, it felt good walking into a function and knowing that I looked good. Soon more and more people started arriving. Richard and Janelle started introducing me to some of their friends and colleagues. I met doctors, lawyers, businessmen and women, and a few of their neighbors.

Janelle made sure she made her way around the room to introduce me. “This is Katherine, Richard’s Office Manager,” she repeated over and over again. Eventually, I made small talk on my own with a few of the guests until Richard came and introduced me to James.

“James, I’d like to introduce you to my Office Manager, Katherine. Katherine, this is James Stafford, I’ve known him since we were at Yale. He was thinking of becoming a doctor but thought better of it and became part of the Wall Street crowd. He owns Stafford & Barnes. Perhaps you’ve heard of it?”

“No I haven’t,” I answered. “It's a pleasure to meet your acquaintance James.”

“Likewise, Katherine. I must say you look stunning. Richard, where did you find such a beautiful Office Manager?”

“Well, Katherine is a friend of my wife’s and since I met her she’s been like part of our family. We call her Wonder Woman at the office. She saved my practice from ruin. She’s an IT expert and can do just about anything in our office. Look, you two chat while I circulate amongst the guests.”

“So Katherine, how long have you been working as Richard’s Office Manager?”

“About 2 years now. Richard is wonderful to work for. And what is it that you do at Stafford & Barnes?”

“We’re an investment firm. We provide counsel to wealthy people and how to manage their financial portfolios.”

“I see. It must be stressful managing people’s money?”

“It can be but it’s not if you know what you’re doing.”

James and I continued to talk and kept noticing his eyes wandering around my body. It made me a little nervous and at the same time, I was riveted to his chiseled face and his athletic-looking body. He was a very handsome man. I would have guessed he was in his mid-thirties with a very athletic-looking body. We talked for about 20 minutes or so and I may have told my entire life story; all except for the parts of me being a trans woman.

I mingled for a bit and stayed for the entire party. I even offered to help Janelle clean up. She wouldn’t let me though. I went home thinking of James and how he asked me so many questions. I was sorry that I didn’t ask him more. But it was obvious that I was attracted to him but I wasn’t so sure about the attraction being mutual.

About a month later I got a call from Janelle. “Kathy, Kathy, Kathy, Miss Katherine. I need you.”

“Sure, what do you need?" I asked.

“Do you remember Richard’s friend that you met, James?”

“Yes, of course! How could I forget him!”

“Well, you know he’s a client of mine through the service.”

“No, really?”

“Yes, well he has a function that he’s attending and needs a date. But here’s the catch: he wants you to attend it with him as his date,” said Janelle, excitedly. “Would you be willing to do this?”

“Willing? Of course, I am.”

“Okay, so here’s the thing. The function is in New York and it’s next Saturday. It’s a very formal function so you’ll have to dress nicely. If you agree, he'll send a private car for you.”

“I’ll be more than happy to. Shoot, a man that fine, I’m more than willing. But why does he need a date?”

“He’s divorced and doesn’t have time to go about looking for dates.”

“What about him going on a dating site?”

“What and get some crazy slut that wants to just get into his wallet? He specifically asked for you.”

“Really?”

“Yes, so get yourself together this week. The car will pick you up at your place at 10am. You’ll stay at The Plaza Hotel on 59th Street in Manhattan.”

“So what should I bring with me?”

“I would bring a different evening gown and shoes. I do have a few gowns here that’ll fit you. They are very expensive so don’t fuck them up, girl.” Janelle laughed.

“No I won’t,” I answered.

“I would also bring something casual in case he wants to see you the next day on Sunday. Your pay will be $1000 for the weekend.”

“Janelle, you don't have to pay me.”

“Of course I do. I know we’re friends but business is business.”

“Okay,” I said with a sour tone.

The next day after work I went over to Janelle's house and we picked out a couple of different options for evening wear. After about an hour of trying different gowns on we settled on a beige off-the-shoulder sequined evening maxi dress. The dress hugged my 24-inch waistline and was slightly revealing at the top; showing just a bit of cleavage. I thanked Janelle and went home excited for this experience.

Saturday came and I was packed and ready by 9:30 in the morning. At exactly 9:55 the bell rang and I came downstairs with my bag. Greeting me was a middle-aged black man wearing a black suit, tie, and hat.

“Miss Hunter? I’m Mr. Stafford’s chauffeur. He’s sent a car for you ma’am.”

“Yes, that’s me!” I said delighted.

He took my bags and put them in the trunk and then opened the door for me. The limousine had cold sparkling water and mints in a tray. I sucked on a mint and opened a bottle of water to sip on the way. I watched as Philadelphia disappeared from view as we crossed the river into New Jersey.

Before I knew it we were in midtown Manhattan. As the chauffeur made his way through the midtown traffic my stomach got a little nervous. Thoughts crossed my mind like, “What if he’s a crazy man?” and “What if he wants to have sex?”. Then I thought that I might have watched too many episodes of Law and Order and Criminal Minds. We soon pulled up in front of the Plaza Hotel. A bellman arrived to take my bags. I thanked the driver. He responded, “I’ll be back at 5:30 to pick you up with Mr. Stafford.”

“Okay, I’ll be ready.”

The hotel was spectacular just like it was in so many famous movies. I felt like a movie star as I walked into the lobby towards the front desk with my sunglasses on.

I approached the front desk and said, “There should be a reservation for me for Katherine Hunter?”

“Yes, Miss Hunter, your room is ready. We’ve been expecting you. The bellman will show you to your room.”

I thought this was how the other half lived. No lugging heavy bags to my room. The elevator went to the 20th floor which was a suite overlooking Central Park. What a view. I never in my life thought I would be able to stay in a 5-star hotel in Manhattan. I was now 24 years old and living my best life. I relaxed for a while after checking out the amenities in the room before getting ready.

I ordered a chef’s salad from room service and then started to get ready. The phone in my room rang. “Hello?” I answered.

“Hello Katherine, this is James.”

“Oh hello, James. How are you?”

“I’m fine,” he answered. “I hope everything is to your satisfaction with your accommodations.”

“Certainly, it’s fabulous.”

“Good,” he said. “I want to thank you for meeting me and going with me to this function.”

“It’s my pleasure, James. I was hoping that one day we could meet again.”

“Well, the car will be there at 5:30. We’ll wait for you out front.”

“Okay! I’ll be there. Don’t worry.”

I hung up and my heart started racing. I wanted to not only look my best but be measured and not seem like I was a young chick from the sticks of Pennsylvania. I started by taking a shower and then putting my hair up in rollers. I sat in front of the vanity in my room and did my makeup perfectly just as Janelle taught me. I made sure that even my eye shadow matched my dress. As I did my eyeliner my hand shook slightly. My mind was on James. Our short meeting made me have a visceral attraction to him. His chiseled features kept popping up in my dreams when I went to bed ever since I met him. I thought about what I was going to say to him if he asked me about my past. Tonight I didn’t want to be a transgender woman; but a woman. I called Janelle once I got dressed.

“Janelle, I need to ask you something.”

“What is it, honey?”

“Does James know that I’m trans?”

“No, that’s for you to work out. All of my girls that work for the service are cis women.”

“Do you think he can tell?”

“Girl, would you stop with this foolishness? No one can tell you were ever some guy named Kenny. Richard, Denise, and I made sure of that.”

“Thank you, Janelle. Now I just want to make sure of the rules. There’s no sex on these escort dates, correct?”

“That’s right. Now if something happens outside of your date, that’s on you two.”

“Okay, because I’m a little nervous. Are you sure he asked for me specifically?”

“Yes Girl, he did.”

“Okay, because you know I’m very attracted to him.”

“Just be yourself Kathy and see what happens. You’ll be fine. Don’t be someone you’re not. Okay?”

“Okay, sis.”

I hung up the phone and looked in the mirror once more to make sure everything was just right with my look. I put on my shoes grabbed my clutch purse and headed out the door. It was 5:20 when I arrived in the lobby. I looked outside to see if the car was there to pick me up but it hadn’t arrived just yet. I sat on a cushioned seat in the lobby to check my makeup one more time. The concierge watched me and smiled as well as some of the other gentlemen that were passing by. After 5 minutes I stood up and walked through the doors. I didn’t want to keep him waiting while I was in the lobby. About two minutes later I saw the same limousine pull up. The chauffeur popped out from the driver’s seat and opened the door. In the car waiting was James. He got out of the car to greet me dressed in his fitted tuxedo.

“My you look marvelous Katherine,” he said and kissed me on the cheek.

“Why thank you, James,” I said with a huge smile on my face.

“Please get in,” James said, holding my hand and helping me into the waiting car.

Once we were in the limo. James started asking me all kinds of questions. “How was your ride up here?”

“Oh, it was lovely. Your driver is wonderful.”

“So tell me, how has your day been going?”

“It was pretty eventful. I ran out to New Jersey to see my children this morning and left there enough time to get back to Manhattan and change.”

“Oh, you have children?”

“Yes, two children, a boy and a girl. Peter who’s 4 and Susan who’s 6,” he said, quite proudly.

“If you don’t mind me asking; what about their Mom? Are you still married?”

“No,” said James, holding up his left hand with no ring on it. We were divorced a little over a year ago.”

“I see. That must have been hard.”

“Well, breaking up and divorces are always hard, especially on children. That’s why I try to make every effort to carve out time for them in my busy schedule.”

“I know about breakups. Believe me!”

“What about you? Are you married or in a relationship?”

“No, not anymore. I’ve been through a few. Some of them were nice, some of them not so nice.”

“Isn’t that how it always is?”

“You’re right,” I said, with a half-kidding laugh.

“So you’re single?”

“Yes, very much so.”

“You know with my schedule it’s hard to make time for a relationship. At least a serious one.”

“I can imagine it must be difficult between your job and making time for your children.”

“Yes, well there’s always the golddiggers that want to start something because I’ve accumulated wealth. And then there are the women that come on to me that are shallow and have never been through anything in life. You know, the ones that have been sheltered.”

“Well, I certainly haven’t been sheltered.”

“Tell me about where you grew up.”

“I grew up in Blairstown, Pennsylvania. It’s a small town about two and a half hours northwest of Philadelphia.”

“So going towards State College?”

“Yes but not that far. My father is an assistant manager at a local hardware store and my Mom works at ‘Michaels’; you know the hobby shop.”

“Yes, yes. I know the chain.”

“We didn’t have much growing up. But we managed.”

“I guess leaving Blairstown and going to Philadelphia was kind of a culture shock for you.”

“Yes, it was at first. But I found that I like it much more than Blairstown. There’s so much diversity there. The Art and Culture is fabulous and you meet all kinds of different types of people.”

“So you like Art?”

“Oh yes, very much so. I love anything cultural and artistic. I also love food. I love cooking and taking walks in nature too. See I’m not just a computer geek.” I laughed.

“What about music? What kind do you like?”

“I like all kinds of music. Of course Pop but I love Jazz and Classical music. Sometimes a little Hip-Hop but I have to be in the mood for it.”

“What kind of Classical music do you like?”

“Ravel, Chopin, Beethoven.”

“Oh? What piece of Chopin?”

“Nocturne #2. I think that’s the most soothing. There’s nothing like spending a quiet evening at home with a glass of wine, staring out of the window with Chopin or Ravel playing in the background. Or some soothing Jazz.”

“Who’s your favorite Jazz artist?”

“I would have to say John Coltrane or Miles Davis.”

“Wow! You really do have good taste! Okay, favorite Jazz album?”

“I have two. John Coltrane’s Ballads album and Miles Davis, Birth of the Cool.”

“Now I know you have good taste!”

“Now you. What do you like to do in your downtime?”

“I like to exercise, I also like to relax with a nice bottle of wine and stare out of my window while listening to music.”

“Interesting, last year I started working out a bit and joined a Yoga class. What type of music do you like?”

“I like Classical, however, I don’t go much for Hip-Hop but I also love Jazz too. I love the traditional New Orleans music. I think it’s hot.”

“I’ve never seen that before.”

“Well, maybe I have to take you one day.”

“I would love that,” I said. Then I continued. “Can I ask what kind of function we are going to?”

“Oh, I’m terribly sorry. It’s a fundraiser that some of my colleagues are putting on. It’s for the New York Persons with Disabilities Association. They do their annual fundraiser around this time every year.”

“I see. Well, that’s a great cause.”

“Oh look, we're almost here. It seemed like we just got in the car. Usually, it takes us so long.”

I looked at the cars that were lined up ahead of us. Couples were getting out of the cars with magnificent-looking outfits on. It was old money that I was seeing though. As the car pulled up a valet wearing a red coat helped me out of the car. James stuck out his arm and I grabbed it holding on to him and walking towards the entrance to Cipriani’s Downtown. I held on to him rather tightly as we made our way inside. There was a cackle of people talking and saying hello as we made our way to our table. Folks were coming up to James and saying hello and he would introduce me, “I’d like for you to meet Katherine,” and person after person I would hold out my hand softly and say, “It's a pleasure to meet you too.”

I felt like I was in a fairy tale. Did this once little boy turn into a real Cinderella? There were hor d'oeuvres, cocktails, and a million people chatting away. Finally, it was time to take our seats. We were seated at a table where there were five other couples seated. All of them were much older than me. I felt slightly like a child next to them. They finally served dinner; a choice of Filet Mignon or Rosemary Chicken breasts. It was presented all very fancy. Then there were the speeches. The Mayor, Bill De Blasio spoke followed by a bunch of bigwigs who I don’t remember their names. After dinner was served and finished and the tables cleared they had a Silent Auction; something I had only heard about before. While James was talking with some of his acquaintances one of the wives leaned over to talk to me. She asked me a million questions.

“What’s your name?” an older lady of about 40-something, dressed in an expensive evening gown asked. She wore heavy jewelry and I could still smell her perfume. It looked like she overdid her makeup; heavy mascara and eyeliner. Almost everything was heavy including her foundation.

“Katherine,” I said with a smile.

“And yours?”

“I’m Lois. I’ve known James for quite a long time. How long have you known James?”

“Oh, we just met a couple of months ago.”

“You know James is a very nice young man. I must say you are very beautiful.”

“Oh thank you very much.”

So how did you meet him?”

“I met him through my boss, Dr. Levine.”

“Oh, which Dr. Levine?”

“Richard Levine. He has a Plastic Surgery practice outside of Philadelphia. I’m his office manager.”

“Oh, I see. So you live in Philadelphia?”

“Yes.”

“It must be difficult dating someone who lives in New York?”

“Oh, we manage somehow,” I said.

Just then James came back to the table. I was so happy. I felt like I was being interrogated by this woman. She probably wanted to get the ‘411’ on me so she could gossip to the rest of her girlfriends.

It was soon time to leave. As we headed back uptown toward the hotel in the car. James asked, “Would you like to stop off for a nightcap someplace?”

“Sure, why not?”

The chauffeur pulled over somewhere in midtown and James helped me out of the car. He took my hand and held it as we walked toward a small very intimate bar that was members only. Just before we got to the door he looked at me and said, “I hope you don’t mind smoking. This is a cigar bar.”

“Oh, I don’t mind at all. I used to smoke but only cigarettes,” I said, thinking I would go anywhere with this man.

“Well, we’ll just have one drink. And there’s also a section where it’s non-smoking so we’ll sit there,” he said and smiled.

The maitre’d greeted him at the door, “Good evening Mr. Stafford. Right this way.” He led us back to a section of the bar as the bartender yelled out, “Stafford my man.”

I commented, “It seems like everyone knows you here.”

“Yeah, this is a place I go at times to blow off a little steam.”

“Everyone needs to blow off a little steam every now and then.”

“You know you’re easy to get along with. I’ve been on dates and none of them ever wanted to come in here. Either they didn’t drink or they hated the smell of cigars. A little too picky for me.”

We sat and had drinks. He had a highball and I had a glass of wine. We talked and talked about all kinds of things. We laughed and it didn’t even seem like the time had passed before the bartender called last call.

“Look at the time! It’s 2 am. I need to let you get some rest. You must be tired.” said James.

“Just a little,” I answered.

James paid the bill and we walked out of the bar with him holding my hand.

The chauffeur pulled the car up and we got in. As we made our way uptown towards the hotel, James leaned over and said, “Would you like to meet me for breakfast in the morning?”

“I would love that!”

“Okay, it’s set. Is 10:30 too early for you?”

“No, not at all,” I said gazing into his eyes.

Just then he leaned over and kissed me. I was surprised at first. I wasn’t expecting it. But I was glad he did. It was a long kiss which turned into a bit of groping. I became aroused very quickly. His breath, with the slight scent of scotch on it, made me crazy. But I didn’t care. As the car pulled up in front of The Plaza. James hopped out and opened the door for me and then walked me up the stairs and stood at the front door. He kissed me one more time passionately and said, “I want to thank you for a wonderful evening. You are everything Janelle said you were and more.”

“I should be thanking you. I can’t wait to see you tomorrow.”

“Me too,” said James, as he let go of my hand.

He waited and watched as I walked toward the elevator. A true gentleman.

I went to bed thinking about him and what could be.