Girlfriend Problems - A Transition Story - Part 12

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Breakfast.

The next morning came. I awoke a little tired but the excitement I felt to see James overpowered my tiredness. I swiftly got ready by pulling my hair up in a ponytail on top of my head leaving a piece of hair in front to swoop to the side in a bang. A little light makeup and some lip gloss and I was ready to meet him. I wore a simple pair of jeans with an ankle boot and a flowered blouse. I brought a short jacket with me because it was a little cool that morning. I had started to pack my bags to get ready for the trip back home to Philly.

I came downstairs at 10:20 and waited in the lobby. To my surprise, James walked into the lobby a little early. He started toward the front desk but I intercepted him before he got there.

“Good Morning!” I said, causing him to turn around facing me with a smile.

“Oh, there you are!” He said, giving me a hug and a kiss on the cheek, “How did you sleep?”

“I slept but honestly, not too long,” I said, as he grabbed my hand and led me to the door.

“Why not?”

“Well,” I said, shyly. “I was kind of thinking about you.” My meek face looked down at the ground as I carefully negotiated the steps.

“That’s nice to hear. I kind of felt the same way,” James said, smiling at me. “I hope you don’t mind walking.”

“Not at all,” I said.

Off we went into the New York morning. James held my hand as we walked a couple of blocks, stopping every now and then to look at some of the window displays along the way. I was fascinated by them. We soon made our way to a Diner/Coffee shop-style restaurant. It was a very non-pretentious environment. This made me relax and feel more comfortable. James also seemed to be more relaxed and comfortable as well. A waiter approached us almost immediately and poured water into our glasses and asked if we would like coffee. We ordered some food and drank coffee. I remarked, “This coffee is awful!”

“Well my dear, it’s Diner coffee,” said James.

“Yeah, I guess you’re right. I’m spoiled when it comes to coffee. I used to work at a Starbucks a couple of years back.”

“Really?”

“Yes, I did it for a while. It wasn’t my most prestigious job,” I said, laughing.

“Everyone does what they have to do at some point. I worked as a dishwasher during part of my college years at Yale.”

“I suppose you’re right.”

I wanted to find out more about him so I asked him some poignant questions. “James, I hope you don’t mind me asking this.”

“What is it? Ask away,”

“You know, you’re a very handsome and well-off man. Any woman would flip head over heels to be with you. Why do you feel the need to hire escorts to attend these big functions?”

James took a sip of his water and then looked me in the eyes, “I went through a very bitter divorce. Like I told you last night I have two young children that I share with my ex-wife. It’s better right now if she didn’t know anything about my private life. She could use it against me in terms of an ongoing custody battle that we’re having. In my case, it’s best to be discreet when dealing with my relationships. The other reason is, as I alluded to last night, I haven't met anyone that I would necessarily fall in love with yet. Attending these events is strictly a business move. It’s a networking opportunity for me. Not really a date.”

“I see,” I said to him, looking down and slightly despondent.

“I will say this, spending time with you last night was very different than any of the other escorts that Janelle has provided me with or any of the other women I’ve dated.  They’re all very beautiful but you’re not like them. You’re different. You’re real. You’re funny, down to earth, and someone that I actually like spending time with.”

“Do you normally take them out to breakfast after they’ve fulfilled their duty?”

“Never. Most of these women are gone and on the next train home the following morning. And then the dates I’ve had have asked me questions about my net worth. You know, how much money I have. And that disgusts me. You haven’t once asked me about my finances or how much money I make a year. I find that an attractive quality in you,” explained James.

“I’m not here to find out about your money. First and foremost, it was a favor to Janelle because she has done so much for me. She’s almost like a sister. Secondly, after meeting you at that party I found you extremely attractive.”

“You know I asked Janelle if she would ask you to come.”

“Well, we could have cut out the middleman and you could have asked me yourself. I would have come,” I said, sparkling with sparkling eyes.

“Can we do that in the future?” James asked.

“Of course! I’d love that.”

“Okay, how about next weekend? Would you come up next Saturday afternoon?”

“Sure, I can do that. But you don’t have to put me up in a fancy hotel or have your limo driver pick me up. I’m a very self-sufficient woman. I can take the train and meet you somewhere.”

“Okay, deal. See that’s what I like about you. You’re not trying to use me.”

“James, I have my own money. I’m independent. I have a good job. I actually have 3 sources of income and I want for nothing. As a matter of fact, I can drive myself here.”

“Wait, you have 3 sources of income?”

“Yes, I’m Richard’s office manager, I’m also the IT person for the office as well, and I also built and maintained Janelle’s website. I get a check for each of those every month. So I’m not doing bad for myself.”

“That’s incredible! You’re a remarkable woman Katherine.”

We left the diner and walked to Central Park, holding hands. We talked and laughed and then sat by the fountain and watched the people go by. Some were jogging, some were skateboarding, and some were parents with strollers. As the morning turned into the afternoon we walked to a bench that was a little more private. It gave us one more opportunity to make out. He kissed me and held me in his strong arms. He started to feel my breasts and became aroused. His hand then journeyed between my legs.

He rubbed my vagina. It was at this point that I felt so glad that I had gotten my surgery. Then, out of the corner of our eyes, we saw a young couple with two young kids about the same age as James’ children. So we stopped. Several thoughts crossed my mind. One being, could my next step be becoming a stepmother? I quickly erased that thought.

“Well, I think it’s best if I go get ready to get back home. I have to prepare myself for Monday morning.”

“Yes, you’re right. I do too.”

James walked me back to the hotel. He held my hand much tighter than before. It was as if he didn’t want to let go. There was something that told me that he had been hurt badly by his divorce. It’s just something that gave me that feeling. I guess it was just my woman's intuition. He texted the limo driver to let him know that I would be ready in a half hour.  I quickly went to my room packed my things and headed back downstairs. James and I sat in the lobby together on one of the luxurious couches. Soon we saw the limo pull up. The driver got out took my bags and put them in the trunk while James and I embraced in hugs and long sensuous kisses. Finally, he let go.

“I’ll see you next Saturday?” He asked.

“Definitely,” I said with a sparkle in my eyes; my heart beating a million miles a minute.

The limo finally pulled off into the Sunday midtown Manhattan traffic and made our way to the tunnel. I asked the limo driver, “I’m so sorry sir, what is your name? I didn’t ask when you picked me up.”

“Oh ma’am, my name is Percy.”

“Hi Percy, thank you for picking me up and taking me. I really appreciate it.”

“Percy, how long have you been working for Mr. Stafford?”

“A little over 5 years.”

“Wow!”

“He’s the best ma’am. I love him like family,” the older 50-something answered. His brown skin glistened in the afternoon sun as we made our way to the New Jersey Turnpike heading south. I sat back and enjoyed the ride thinking about James and what the future could bring.

After arriving home, I called Janelle immediately. I couldn’t hold my excitement. I had to tell her all about the trip.

“Hey Janelle, I’m back home.”

“It’s kind of late. I thought you might be back early in the morning. So tell me, how did it go?”

“It was wonderful! James is a wonderful man.”

“So I take it you had a good time?”

“Good time? First of all, that man is gorgeous. Second of all,l he was a perfect gentleman.”

“Did you just get back home?”

“Yes! After that fundraising event, we went out to a little quiet members-only bar for a nightcap. We stayed up until 2am talking and laughing. Then this morning we met early and he took me to breakfast and then we walked in Central Park.”

“Whoa! He must really like you! He has never done that with any of the girls I’ve sent to him.”

“Yes, he told me. I hope you're not mad but he and I fooled around a little bit. Just kissing.”

“Why would I be mad? After all, he asked specifically for you.”

“I felt like Julia Roberts in Pretty Woman. You know he asked me to come back on Saturday. He wants to see me again.”

“You should go! Don’t hesitate.”

“I’m definitely going to go. But this is the only thing that’s bothering me. Should I tell him that I’m trans?”

“I’ll say this. You should definitely tell him but you should do it when the time is right. It’s only fair to him.”

“How did you tell Richard?”

“As things progressed and before we made love I told him.”

“What was his reaction?”

“He didn’t care. It didn’t bother him one bit.”

“So what should I do? It’s something that’s been on my mind the entire ride back home.”

“You’ll know when the time is right. But definitely tell him before you have sex; if it comes to that,.” said Janelle.

I was so appreciative to Janelle for her guidance through these last couple of years. She took me from a skinny little cross-dressing boy to a beautiful woman. She and Denise had given me a new life which I was so thankful for. The biggest hurdle early on was acceptance of myself. Ultimately, it came down to whether I could truly believe in myself as a woman instead of a confused little boy who liked to crossdress.

The week went on as usual at work. I would often catch myself daydreaming of James when it was slow at work. I thought about how I would tell him of my past. It made me feel anxious because of the prospect of rejection. On Wednesday of that week, a delivery person came and Cynthia called me out front. At the reception desk was a bouquet of 2 dozen red roses. The note attached said, “To Katherine: I await the time when I see your beautiful face again. James.”

The note even more than roses meant more to me. My heart raced in anticipation for Saturday. Cynthia teased me a little saying, “You have someone that really likes you!”

I sat the roses on the shelf behind my desk. The bouquet took up way too much space for them to be on my desk.

Saturday came quickly. I didn’t know what plans James had for us over the weekend so this time I packed a few different changes of outfits. I left Philadelphia early in the morning, around nine o’clock. James said he would call me while I was on the way there to let me know the arrangements of where I would be staying. I was halfway to New York when he called me.

“Good Morning Katherine! How are you doing this beautiful morning?”

“Hey, James! I’m fine! And you?”

“I’m doing great. I’m actually out with the kids this morning. I took them to the playground out here in New Jersey.”

“Oh, that sounds like fun.”

“Yeah, my kids are lots of fun. I love being with them.”

“So James, what should I do? Where am I going? I can always go and book a room at a hotel somewhere in New York.”

“Well, that’s why I’m calling. This might be a little forward of me and I won’t be offended at all if you say no. Would you be okay with staying with me at my place? I just haven’t had the time to search for another hotel. I have two extra bedrooms there.” James asked.

“No, not at all. I’m not offended in any way.”

“Great. I figured this would be a good way to get to know each other a little better and spend a little more time with each other.”

“That’s fine with me. And don’t worry, I’m a big girl. I can take care of myself until you finish your visit with your kids.”

“Oh, thank you so much.”

“Just text me your address and I’ll meet you when you finish.”

“Okay, it’s 115 Central Park West. But I’ll text you the address. It’s close to 71st.”

“Is there a reliable parking lot there?”

“Yes, right on 71st Street you’ll see an Edison Parking lot. That’s the closest to my building. It’s just a half block away.”

“Okay, I’ll park my car and go walking until you call me.”

“Great! I can’t wait to see you.”

“Me too,” I said and hung up the phone.

I arrived at the parking garage and left my suitcase in the trunk of my car while I was walking around the neighborhood. It’s kind of a relatively quiet street compared to most New York streets. I spent an hour or so perusing some shops on Amsterdam Avenue and on Broadway. I finally decided to relax at a coffee shop on Amsterdam Avenue and read the New York Times while I waited for his call. Around two o’clock the phone rang and it was James. He decided he would meet me at the coffee shop. James came in with all smiles on his face wearing a jogging suit and sneakers. Very much unlike the way he dressed on the two days we were together. He gave me a hug and kiss on the lips and sat down.

“I hope I haven’t kept you waiting long.”

“No, not at all. I’m fine. I did a little window shopping and then decided to give my feet a rest so I’ve been sitting here only about a half hour.”

“Good, are you ready to go?”

“Sure baby, I’m ready.”

I left the remnants of the tea I was drinking. We left the shop holding hands as we walked to get my bags from my car. We walked towards a majestic building on the corner where a doorman was waiting.

“Good Afternoon Mr. Stafford,” said the doorman.

“Charles, let me introduce you to my friend, Katherine. Katherine, this is Charles,” said James in a very formal way.

“It’s a pleasure to meet your acquaintance,e Miss Katherine,” said Charles, tipping his cap.

“Thank you! The pleasure is mine.”

We went up in the elevator to the 7th floor. The building was very well kept with high ceilings and the hallways were spotless. We walked around a corner and James put his key in the door. The door opened to a beautifully decorated apartment with huge windows facing Central Park. His place was well kept. All very neat and tidy. I looked around and he had art of all types on the wall in the living room.

“Let me show you around,” said James. “This is the kitchen obviously.”

I saw the kitchen was clean and neat except for a cup and a small plate in the sink. He had a juicer and a giant bowl of fruit next to it.

“I see you like to juice?”

“Oh yes. I’m an avid juicer. I have to keep my body fit. Let me show you the rest of the place.”

James took me around his apartment which was charming. He showed me to the extra rooms where I put my bag and my purse. One of the rooms was obviously the kid's room when and if they stayed over. It had two twin beds and a bunch of toys which were neatly stacked in one spot.

“This is a fabulous apartment! I just love the view.” I said

“That’s why I took it. I used to live out in Saddle River with my wife but she kept the house in the divorce.”

“Are you hoping to one day gain custody of your kids?”

“Well, that’s the plan. I was asking for partial custody. I would have them in the summer and she would have them from September through June during the school year. The courts only allow me weekends with the kids for now.”

“Can I ask what happened between you and your ex-wife?”

“My ex-wife came from money. I mean old money. She is part of the Rothschild family. She got the best family attorneys in the business. We broke up claiming irreconcilable differences. She also claimed that because I was at work so much I was having an affair with my Administrative Assistant. That was the farthest thing from the truth. I just spent long hours at work. Which I will admit was wrong on my part. In return, she started having an affair with someone. We split and now she’s living with this guy, in the house that I pay for. It’s not a good situation at all.”

“Wouldn’t you have a leg to stand on if she was actually seeing someone else during your marriage?”

“Yes, but I couldn't prove it. Anyway, I thought I was in love but as it turns out she wasn’t who I thought she was,” said James.

We sat on the couch in the living room as we talked. “You know James, everything happens for a reason. You’ve moved on now and maybe better things are on the horizon for you.”

“That’s true,.” he said looking down. “Let’s change the subject. Where would you like to eat tonight?”

“I have no idea. I don’t know about any of the restaurants in New York.”

“Well, what would you like to eat? Italian, Japanese Sushi, Greek?”

“I’m easy. How about Sushi? I think I’d like something different tonight.”

“Okay, sushi it is. I’m going to take a shower and get out of this jogging suit. Make yourself at home. You’re welcome to anything in the kitchen.”

James took a shower while I unpacked my clothes. I walked back towards the living room and James came out of the shower; hair wet with just a towel around his waist. His tall, muscular body made me stare.

“Oh, James! My what body you have!” I exclaimed.

“So sorry. I’m so used to living alone. I didn’t mean to startle you.”

He hurried to his room and shut the door. I sat on the couch for a hot minute thinking about laying down with him and feeling his touch and body rubbing against mine.

I decided I would get dressed to go out. Since we were going to a Sushi restaurant. I decided to wear something casual but nice. I chose a pair of white slacks with a white and black ruffled half-sleeve top. I quickly did my hair and put on some subtle makeup.

When James finished getting dressed I asked, “Is this okay for where we're going?”

“That’s perfect! You look beautiful.”

We left his place and went to midtown to a sushi restaurant on 9th Avenue. As we walked into the sushi restaurant he put his arm around my waist. It made me feel closer to him. We talked and talked and sat there eating for an hour and a half. We enjoyed ourselves having a bottle of Saké. As we talked our eyes never left each other's gaze. I wanted him so bad! I think he felt the same. He grabbed my hand and said, “I have to be honest with you Katherine. I really want to make love to you tonight. I find you so attractive. But not only that, I love your spirit; your kindness, your thoughtfulness, your truthfulness, and honesty.”

His saying that made my heart melt. I wanted to tell him. My mind was racing back and forth. “Should I tell him? Maybe I shouldn’t. I should because I want this man!”

I took a big gulp of Saké. “I’ll be honest with you James. I want to make love to you too but there’s some things I need to let you know before that.”

His face turned puzzled, “What’s that?” he asked.

I took a deep breath, “If I tell you this, I would understand if you’re completely turned off by me. It’s a little; or maybe not so little secret that I keep from almost everyone I meet now.”

“Okay, try me,” He said enthusiastically.

“Okay, okay,” I said, “Let me say this the right way.” I paused. “James, I’m a transgender woman.” There I said it. Let the chips fall where they may.

“Okay, is that what you wanted to tell me?”

“I’m sorry,” I said, on the verge of crying.

“Don’t be sorry. There’s no need for that. You know I talked to Richard and asked about you. He alluded to that but didn’t tell me the entire story. I wanted it to come from you.”

“Are you mad at me?”

“Mad at you? For what? Being honest? No, not at all!”

He came to my side of the table, grabbed me, and hugged me. “It doesn’t bother me at all. You’re a beautiful woman! Your femininity shines in you. You’re the most attractive woman I’ve ever gone out with.”

I wiped a tear from my eye as he started to kiss me. Then stopped. “Quick question though. What’s down there?”

“Oh baby, I have a vagina. I had surgery a couple of years back.” I assured him.

“Not that it matters to me. I just wanted to know what to expect.”

As it turns out James was not as conservative as I thought. My thinking was because he went to Yale and was surrounded by these ultra-rich folk he might have been jaded. But to the contrary, he was very progressive in his thinking. That night we went back to his place. I was a little nervous but he made me feel at ease. He led me into his room and took off my clothes one item at a time; all the while kissing me and caressing my body. When he took off my bra he kissed my nipples and ran his finger around my areola.

I grabbed his now stiff penis and rubbed it up and down with my soft hands. I loved feeling his muscular body; his shoulders and thighs were rock-hard. He entered me with loving care; eventually thrusting himself inside of me. We managed to go through different positions. I orgasmed multiple times until finally, I made him orgasm as well. It was the most rewarding sex that I've ever had. We held on to each other all night. I could feel his love surrounding me in his loving arms.

The next morning we woke up and kissed each other. I offered to cook breakfast while he showered. We sat gazing out of the window over Central Park while eating eggs, bacon, and French toast. We spent the rest of the day together walking and talking in Central Park. It was getting late so he treated us to some takeout at his place. It was almost 8pm before I left for home. I had to get back and get ready for work the next day.

This went on for months. I would take trips up to New York almost every weekend, except for the weekends he had his two children staying there. We would call and text each other incessantly. Our love affair grew strong over the coming months. He even came and stayed with me for a couple of weekends.

The summer months turned to fall and eventually winter. In early December James decided it was finally time for me to meet his kids. I came up and stayed with him and we all went to the Rockefeller Center Ice Skating Rink to skate and see the Christmas tree. I wasn’t a fantastic skater but I could hold my own. I let Peter hold on to me to keep his balance while Susan did figure eights by her Dad. The tree and the atmosphere were intoxicating.

It felt so good to be around his children who were complete dolls. After skating we went to the Hard Rock Cafe to eat and then home to James’ place. We sat up and watched Christmas movies. The kids really took to me. I was surprised because a lot of children take a lot of time to warm up to a partner of a divorced parent. While watching television on the couch, Peter fell asleep next to James, while Susan started to doze off as well with her head on my shoulder. James carried Peter to the bedroom, while I had the task of waking up Susan.

“Come on Susan. You’ve got to go to bed now sweetie.”

“I don’t want to go to bed. I want to stay here with you and Daddy.”

“I know honey, but it’s late and you need your rest,” I said.

Susan got up and asked half asleep, “Can you be my second Mommy?”

“Sure honey. I’ll be your second Mommy.”

I've never felt so loved. A child’s love is like no other. I believe that children are the most honest human beings. They say a lot even though they have limited knowledge at times.

It was a fun-filled weekend and soon I had to go back. I really didn’t want to go. It was getting harder and harder to leave James. As I left New York and James’ loving arms I felt like I was leaving home.

I arranged to spend the entire week before Christmas this year in Blairstown where I was able to get my birth certificate changed. Not seeing James that week was like getting hung by my fingernails. We became very attached to each other. But having that birth certificate changed would have an even deeper meaning.

Christmas with my family was joyous. I attended church and didn’t feel the same anxiety as I felt before. I was solid in my new life and my life as a woman. No one questioned me and if they did I had no problem telling them who I was. Being that I had the support of both parents and my sister made such a big difference.

Months passed and I was able to get my passport changed. I told James and the next day he surprised me.

“Honey, can you get off the Friday of the second weekend of May? I have a surprise for you.”

“I’ll ask Richard,” I said.

I ran into Richard’s office requesting that day off.

“Of course, you can, Kathy,” he said, without hesitation.

I called James back immediately. “Richard said yes!”

“Well get ready. We’re going to Paris that weekend.”

“Paris?!”

“Yes, honey. Paris.”

The weeks passed quickly towards May and the second week was finally here. I called James and asked, “James, I’m trying to figure out what to bring with me to Paris. Are we going anywhere formal or are we just going sightseeing?”

“No honey, we’re not going any place formal. Maybe a few nice things if we go out to dinner somewhere. But yes, just bring a few nice things and a few casual things.”

“Okay, baby. I love you.”

“I love you too, Kat,” said James. He started calling me “Kat” for short in recent months. I thought it was cute and I enjoyed it. It was less formal than Katherine's. Although I did like for him to call me Katherine in public. It was more regal than Kathy.

James sent Percy with the limo to pick me up on Thursday afternoon. I had bags packed and I was excited to leave the country for the first time. He brought me to New York where I had been given the key to James’ apartment months ago. Yes, He trusted me that much.

I rolled my bag upstairs. I felt like I overpacked since we were only supposed to be staying 3 days. Soon James came through the door from work. I made him go and take a shower while I fixed him dinner. We had spent so much time together that we started to become like one person. We knew each other's tendencies; likes and dislikes.

Our flight was the first one of the morning so we needed to be at the JFK airport before 4am. We ate and then slept fast. 3am came before we knew it. We went downstairs with our bags in hand where Percy and the limo awaited. Tired but excited we boarded and were on our way to Paris. We checked into the Hôtel Plaza Athénée around 3pm Paris time. After we rested we went and found a decent restaurant to eat. James ordered for the both of us.

I asked James, “Honey, are we here on a business trip?” It all seemed very mysterious and vague to me.

“It’s sort of business. Business I feel I must take care of. But that’ll wait until tomorrow.”

The next morning we woke up and went sightseeing a little, visiting the Louver Museum and a couple of other places. We walked to the Champs Elysées where James said, “Isn’t it beautiful?”

“Yes, very much so,” I responded. “I can’t believe I’m in Paris. Oh my God! It’s like a dream come true.”

“You see this arch,” pointing to the Arc de Triomphe. “It represents everything that we are as a couple. It’s the arch of triumph.”

“Yes, I agree,” I answered.

“That’s why I brought you here because I want to walk triumphantly through this arch with you.”

I asked myself “What is he talking about?”

James got down on one knee and said, “Katherine Michaela Hunter, would you marry me?”

I almost fainted. I covered my mouth almost in tears. I was speechless.

“Yes, Yes, Yes! I’ll marry you.”

“Then take this ring and wear it as a sign of my desire to make you my wife.”

James slipped on a huge 2-carat diamond ring on my finger. I was stunned, happy, anxious, joyous.

“I love you, Kat,” James said, as he stood up and kissed me passionately.

“I love you too James Stafford,”

I felt like I was living in a fairy tale again. Not only did this man see past me the fact that I was born a male but he saw something in me that was hard to see myself. That I had value as a woman. That he saw the kindness in me despite coming from humble beginnings. I’m so happy I said Yes.

We decided on a date in October. It was enough time to organize a wedding and for invitations to go out.  It was a whirlwind next couple of months. I gave my notice to Richard so he had enough time to find and for me to train another office manager. Janelle helped me find the perfect wedding dress.

We got married on October 20th at a Unitarian Church in New Jersey and had the reception at the Rockleigh Country Club in Rockleigh, New Jersey. My bridesmaids were Janelle, Kiera, Giselle, and yes, Denise. My parents came and my father walked me down the aisle. It was like a fairytale wedding, complete with a string quartet for the ceremony and the reception was complete with a DJ and a Band.

James and I found a place in Alpine, New Jersey not far from Saddle River. He was able to go back to court and get shared custody of Peter and Susan. His ex-wife eased up after realizing that having two sets of parents was better than one. I honestly think that raising two children on her own was a lot of work for her. We became cordial and even friendly to each other and now share tasks of making sure that the kids are raised with the right amount of attention. This once, skinny little boy from a little town in Pennsylvania turned into a beautiful wife with two kids and a loving husband.

James’ business continued to thrive while I stayed at home and took cooking classes eventually opening up a catering business. Janelle and Richard continued to thrive with their businesses as well. Denise ended up having three children with Bob. Peter and Susan are now in middle school and high school respectively. They both call me Mom and I love them very dearly. James and I are still madly in love with each other.

The End.