Girlfriend Problems - A Transition Story - Part 7

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Brand New Experience,

As we drove towards downtown Philadelphia, I looked at the lights from the buildings reflecting on the ground that had a little snow on it. I was filled with a bit of anxiety since Janelle never told me exactly where we were going. Since she recommended I wear a short mini dress I assumed we were going to some sort of club. I wondered a bit about Janelle’s life but was hesitant to question her. But I did anyway.

“Janelle, can I ask you a question?”

“Sure, sweetie. What is it?”

“I hope I’m not being too invasive. How old were you when you got your bottom surgery?”

“I was young, around 22,” She said.

“Did it hurt?”

“I was asleep when they did it. So it didn’t hurt at all,” She laughed. “It’s afterward that’s the hard part. You’re drugged up for several days and once they wean you off of the pain medication, that’s when it becomes difficult. The hardest part of the entire procedure is when you need to dilate.”

“Does it hurt when you dilate?” I asked.

“Yes, it does, but only at first.”

“Oh, I see. Were you able to have orgasms?” I asked. Then feeling like that was too much to ask, “I’m sorry. I didn’t mean to be invasive.”

“No, no, not at all. Honey, you can ask me anything. I’m an open book.” She said, giving me comfort. “Of course I have orgasms and they’re wonderful! Better than having anal sex. You see now surgeons have the ability to take the nerves from the male genitalia and use them in the clitoris. But all of that is down the road for you my dear. What you should be thinking about is getting your face done first and then working your way down the body. What people see first is your face and then when you speak.

That’s how people determine what gender you are when they first meet you in public. If you have a gravelly voice and strong male facial features, you’re not going to pass in public very well. You don’t have any of those, so don’t get me wrong. Your face even now is pretty feminine. I just don’t want there to be any question whether you’re a boy or a girl.”

“I see,” I replied, soaking in all of this knowledge.

“Secondly, you need to work on your walk and your feminine ways. You’ve only been living full-time as a woman since about April of last year? So it’s been only about 9 or 10 months. That’s why I had you practice walking in those stilettos I gave you. I can see you’ve been practicing but you need a real-life test.”

“Yes, I have been practicing. Even when I’m home cleaning I’ve been wearing the Louboutins you gave me.”

“Good! Keep it up!”

We pulled into a parking lot behind a set of buildings a couple of blocks from Broad Street. There were very very few people on the street. It was dark but I noticed a homeless man sitting on the ground in front of a storefront. I saw 2 Gay men walking holding hands and a woman walking her dog.

“Okay Miss Kathy, let’s go in.”

We walked toward a building that had a high heel and a sign that said, “The Gold Slipper”.

Janelle opened the door and was greeted by a bouncer who was Black must have weighed 270 pounds and was about 6 foot 9 or so. “Hi Miss J! Good to see you”

Janelle replied, “Thank you! This is my little sister Kathy. Kathy, this is Benny.”

“Hi Benny,” I said, holding my hand out very delicately.

We made our way into the club slowly. House music was blaring over the speakers. And it seemed as if the further we went in more and more people were saying hello to Janelle. It was as if she knew everyone in the club. There was a mix of people. A lot of Gay men and a lot of trans women. All of them were dancing, drinking, or snuggling up with someone. As we walked further into the club, a very handsome middle-aged Gay man who was impeccably dressed and groomed came out to greet Janelle.

“Miss Janelle!!!!” He screamed and came over and hugged her, almost picking her up.

“Hi honey,” she said, giving him a kiss on the cheek and leaving an imprint of her bright red lipstick.

“Come, come this way.” He said.

As we walked she introduced me, “Kathy, this is Juan. A dear old friend of mine.”

“Juan, this is my little sister Kathy.”

“Oh, it's such a pleasure to meet you, Kathy,” as he held my hand and kissed me on the cheek. “You look wonderful,” Juan added.

Juan walked us to the back of the club where it was somewhat quieter to a roped-off VIP section.

“Here you are, ladies.”

Juan clapped his hands and pointed to the table we were sitting at. As Juan and Janelle talked for a few minutes a topless waiter came to the table with Champagne in an ice bucket with two glasses. He was young and Hispanic with a very nice physique and six-pack abs. As he stood there popping the cork I admired his body; thinking, “Wow! He is fine!”

“Don’t get your hopes up, honey. He’s Gay,” whispered Janelle in my ear.

“Oh okay,” I answered and Janelle laughed.

After the waiter poured us each a glass, we picked up our glasses and Janelle said over the music,

“Here’s to my new little sister, Kathy.”

I watched as the dance floor got packed and Beyoncé’s music played over the speakers to a house beat. Lights flashed, red, blue, yellow, and green. Young trans girls moved on the floor; some with men, some with other trans girls. All of them looked like cis women. Some were tall, some short, some heavy, and some thin.

Some were Hispanic, some were black and some were white. Almost all of them were very beautiful. I watched very carefully how they carried themselves. The entire scene was something completely new to me. I watched as gay men carried on voguing across the floor; some in the booths along the wall were kissing. As a young kid from semi-rural Blairstown, it was an experience I will never forget.

“Kathy, let’s take a picture. Do you have your phone?”

I took my phone out of my purse as Janelle waved Juan back over to our table.

“Juan, would you be a doll and take a picture of us? I want to make this night memorable.” Janelle asked, handing Juan both of our phones.

Soon a couple of the women came over to our VIP section. “Que pasa mami? How are you?” one of the women asked Janelle, kissing her on her cheek. “Fine. I want you to meet my little sister Kathy. Kathy, this is Giselle.” Giselle leaned over and kissed me on my cheek. Giselle stood about 5 foot 9 or so, very thin with gorgeous skin and long dark brown hair that reached the small of her back. She wore a mini skirt and a halter top.

“You’re very pretty Kathy. It’s nice to meet you” she said as she slid next to us onto the small couch.

“Thank you, Giselle,”

Leaning in, Janelle said, “Kathy, Giselle is my confidant. One of my closest friends. You can trust her. But you can’t trust every girl in this place. Some of them are ruthless children,”

“You know that’s right,” said Giselle, high-fiving Janelle.

Oh, and this is Chelsea, one of Giselle’s friends, introducing us. “Chelsea is about your age Kathy.”

Chelsea was another beauty. She stood only about 5 foot 4 and had beautiful olive-colored skin, about my complexion. I couldn’t tell whether Chelsea was trans or not. That’s how real she looked.

As the music played I watched as the 3 of them talked. I couldn’t make out what they were saying to each other but the conversation became a little serious for a moment. I looked out on the dance floor and saw a woman who was obviously Trans.

“Oh boy, there she goes,” said Janelle.

“Oh no, it’s Jenny. The surgery queen,” said Janelle.

“I told that girl to go to Richard. But she was hard-headed and claimed she didn’t have any money,”

said Janelle. ‘Now look at her. Overdone!”

Chelsea and Giselle shook their heads as they watched the woman they called Jenny dance on the floor. She had an enormous ass but it was out of proportion with the rest of her body. Her lips were huge and had cheekbones that made her look like a caricature of herself. They just shook their heads. I was astounded. I understand why Janelle wanted to make sure I got the best treatment for my transition.

Chelsea chimed in, “That’s what happens when you cut corners and go to those back alley doctors. Of course I didn’t need anything. Look at this gorgeous face. Made by mother nature.” she said while caressing her own face.

Janelle all of a sudden was summoned to another room by Juan. “I’ll be right back ladies.” Janelle got up and went with Juan. I spent my time chatting it up with Giselle and Chelsea. After a while they took me around to meet some of the other girls; each of them seemingly more beautiful than the others. I met Candy, Vanessa, Miasha, Amber, Ashley, and a number of other girls that I couldn’t remember the names of. Giselle treated me to a drink as we sat at the bar and eyed some of the guys.

“I can’t believe I’ve never been here before,” I mentioned to Giselle.

“You have to come more often. All the girls look out for each other here. For instance, you see that guy with the blue shirt on,” said Giselle, pointing out a guy with a blue shirt on.

“Yep.”

“Well, he’s what we call a “Bugarrón”

“What’s that?” I asked.

“A Tranny chaser.” she laughed. “Basically a man who has sex with us. They’re always at the top and don’t consider themselves to be gay. And most of all don't want to pay for it. Those are the guys that will never take you home to momma or be seen with you in public unless it’s in here.”

“Oh, I see.”

“If you don’t have time for me after screwing me. Then you have to pay me.” Explained Giselle.

“That’s pretty sleazy,” I responded,

“Yeah, I don’t have time for that,” said Giselle. “You need to hang with us more often, girl.”

“I will. But I would never come here by myself. If you or Chelsea are here then. I’ll come out.”

Giselle and I traded numbers and went back to the VIP section where Janelle was. She had returned and was stuffing an envelope in her purse.

“Giselle, how do you like our little sister?”

“I love her! She’s so cute and innocent!” said Giselle, kissing me on my cheek.

“Good. Now you’re gonna take care of her, just like I took care of you,” said Janelle.

“Don’t worry Momma. We’ll take care of her,” said Giselle, with her arm wrapped around me. “This one's a keeper. She’s gonna be one of the good ones.”

“Now we’re going to have to leave. It’s almost midnight and Kathy needs to go to work in the morning,” said Janelle.

“Kathy, you have a job?” asked Chelsea.

“Yes,” I answered.

“Where?” asked Giselle.

“Starbucks. But it’s just for the time being.” I answered.

“Next time I see you I want you to bring me a half latte mocha chocolatay!” laughed Giselle. We actually all laughed.

Janelle and I sashayed our way to her car looking and feeling good as we didn’t even feel the cold air on our legs. I was feeling a little tipsy from the champagne and the drink that Giselle bought me.

During the drive home, Janelle asked, “So what do you think of my friends?”

“I like them. Especially Giselle. She’s fun.”

“Giselle’s a good girl,” Janelle confirmed. “Some of those other girls, not so much.”

“Is Giselle a working girl?”

“What do you mean?”

“I mean does she do sex work?”

“Yes, she does. Does that bother you?”

“No, not at all. I’m pro-sex work. Especially for us trans women.”

“Well, I’m glad to hear that,” said Janelle. “I did it at one time. But it’s dangerous. You meet all kinds of weirdos. Unless of course it’s done on a high level and it’s underground.”

“I understand.”

“I’m glad you brought this up. This website that I want you to construct is going to be a website for high-end escorts. Is that something that would bother you?” asked Janelle.

“No, not at all! I want to help. Just because I haven’t experienced certain things in my life, I’ve read so much about the history of transgender women and the resilience one must have to live our authentic selves.”

“That’s good darling. I’m glad you understand.” Janelle continued to explain. “I wanted to come up with a plan for both of us. First of all, although Richard makes very good money, I want to contribute to our amassing of wealth. In other words, I want to have my own money too. Don’t get me wrong, Richard treats me very well. When I need something he never says no. And I am certainly very appreciative to have what I have. For a once little sissy boy that grew up in Puerto Rico and came from nothing, I am certainly indebted to my husband for giving me the life I’ve always wanted. Now all of this will be perfectly legal and above ground.”

I looked at Janelle with loving eyes, as she stared straight ahead keeping her eyes on the road.

“What I want to do for you is to give you a leg up. You’re a good, sincere, loving person, Kathy. You deserve much more than that. You just didn’t get a chance to be able to develop and be your true self. I’m sure growing up in that little town with the parents you had didn’t aid you in seeing who you really are inside. When Denise told me about you and revealed the secrets you were trying to hide I developed some empathy for you.”

“Thank you, Janelle.”

“So this is the plan. We can start working on this website on your days off until you leave. I will front you a portion of your pay so you can get by in the meantime. Once the site is up and running I’ll give you the rest of the money. Now as far as working at the office for Richard, he’s going to handle that. He’ll talk to you about that in the morning. But I believe that once you install the new system for him. He will do all of your facial surgery first and be entirely healed, then he’ll hire you full-time to work there. Does that sound like a plan to you?”

“Sounds fantastic to me! I can’t wait to get started. I’ll start visiting some other websites to see how they’re set up. I can make sure that the website looks good and it’s secure. Will the clients need to pay upfront?”

“Yes, of course.”

“I know how to set it up to make the payments secure.”

“I’m sure you do.”

The gate opened and we pulled into the long winding driveway. As we pulled into the garage I said to Janelle, “Janelle, thank you so much for helping me. You’ve given me so much. I really love you.” I said to her, reaching over to her, and hugging her with tears in my eyes.

“Oh don’t cry, sweetie. I love helping people; especially people that deserve it.”

We went inside and retired to bed pretty quickly. I put on my nightie and slept well through the night with a smile on my face.

New Job.

I awoke early the next morning to get ready for work. I put on the drab black clothes and grabbed my green smock that’s required of all Starbucks workers. I grabbed the presents that Janelle got me and I went downstairs where Janelle, with her robe on and Richard were sitting around the island having coffee.

“There she is! Miss America!” laughed Janelle.

“Good Morning,” said Richard, being more formal.

“Good Morning Janelle. Good Morning Dr. Levine,” I replied.

“Ah, ah, ah. Here, it’s Richard. Dr. Levine hasn’t gone to the office.” said Richard.

Janelle came and gave me a hug. “You want some coffee? I’m sure you might need some after last night.”

“I see and smell coffee all day. Normally I wouldn’t, but this morning; that’s a definite yes.”

Janelle handed me a cup of coffee. “Flora’s gonna fix us a quick breakfast. I’m going upstairs to get some clothes on. You and Richard need to talk.”

“Kathy, I want to say you really saved our asses that day you came to the office. I want to first thank you for that.”

“It was nothing, Richard. It was an easy fix. The system they’re using is way outdated,” I said.

“And it’s still not working correctly. I’ve spent roughly $162,000 to implement this electronic health record system, with $85,000 in annual maintenance.”

“For what they gave you Richard, they are fleecing you for your money. I could set it up and maintain it for you for less than half of that. Of course, the equipment would cost some money but you would save at least $80,000.”

“Well, I need to get that up and running soon. It’s still causing us havoc in the day-to-day operations.”

“How do you feel about working full time for me?”

“It certainly would beat working at Starbucks,” I said, as we both laughed.

“I do have a strict policy about who I hire and you would have to certainly dress a lot differently than you do at Starbucks.”

“I have no problem with that. I hate looking like this every day.”

“Do you have any experience working in a healthcare setting?”

“Not really. My ex is a nurse. So I’ve been around it a lot.”

“For what you’ll be doing you won’t need a lot of experience. You’ll have to familiarize yourself with medical terminology, diagnostic and procedure codes for billing.”

“I really don’t think it’ll be a problem. I can do that.”

“Good! What I’ll need you to do is to submit your resume to our office manager. You’ll be assisting her as well as doing some batching to send out to our billing office.”

“It sounds good to me.”

“Now, I’m going to have to run. I won’t be able to wait for Flora to fix breakfast. It’s a pleasure to have you around.”

With that, Richard grabbed his briefcase and hurried out of the door.

After Janelle and I ate breakfast, she dropped me off at work. The day went slowly as it wasn’t that busy. I kept thinking about last night and all of what Janelle and I talked about. Although I was tired, I was still excited about getting my facial surgery. The time was drawing closer.

Thursday rolled around, my usual day off. I started working on Janelle’s website as soon as I woke up that morning. This was a fairly easy start for me. Janelle came over around 11am. When she came upstairs to my apartment she remarked. “Well, this looks different!”

I still had no furniture in the living room as Denise had taken everything with the exception of the TV. I had a lone chair with a TV tray next to it. Only pictures that I had collected over the years hung on the wall. I did move my twin bed into the room I once shared with Denise along with the furniture that Kiera bought me for Christmas. Leaving the room that I was sleeping in for my office.

“This is quite a spartan look, girl. We have to get you some furniture here.”

“I know. I’m trying to save my money. And you know that Starbucks money doesn’t go far.”

“Well, you should try to get out of here. No sense in getting furniture for an apartment you’re not going to stay in.”

“Why do you say that?” I asked Janelle.

“You’re better than this neighborhood. Now let’s get to work.”

We sat at my desk in front of my 2 computers while Janelle explained what she wanted. “First of all this is not a sleazy prostitution service. This is not about hiring out-call girls. This is a non-sexual business. It’s mainly for clients with big money who come into town and want to have a beautiful woman in their arms for private functions or a date night. Richard knows and meets many of these clients in his business. Many of them are corporate executives, doctors, investment bankers, and the like. Some are single due to being widowed, separated, or divorced. We just offer a service that gives them companionship. We will also offer escorts to our gay clients; either gay men or gay women. Now if something transpires outside of the contracted time, that’s on them.”

“I see. I feel better about that. I just don’t want to be in any kind of illegal enterprise.”

“No honey, I wouldn’t do that to you. And God forbid any of this would backfire and cause Richard and I in some sort of legal trouble.”

Janelle stayed for about 2 hours so consequently we ordered lunch and ate in. Afterwards, she left and I worked all through the day and into the night. At the rate I was working I guessed I would be finished in about a week. By the following week, I was finished. As promised Janelle paid me the $5000 for the work getting her website up and running. I must say it was a work of art and probably the best website out of all of her competitors. With $5000 extra in my account, I decided to move to a better apartment close to downtown Philadelphia. Since I didn’t have a car this was a better move.

Plus there had been a rash of break-ins and robberies in my old neighborhood where I used to stay with Denise. It helped me heal from the old memories of my relationship with Denise and the way it ended. I was able to find a reasonably priced, converted loft space close to shopping and an express bus route that would drop me to my new job at Richard’s office. It was also only an 8-block walk to the Golden Slipper. The loft was right in the heart of what they called Philadelphia’s “Gayborhood”.

I asked Bill to help me move. I had been seeing him off and on ever since that first date. Our relationship was mostly sexual in nature. I never did find out too much about his home and private life. I guess you could say we were just “fuck buddies”. He rented a small Uhaul van and helped me move what little furniture I did have. After all the furniture was moved.

We fooled around that day and made love on my little twin bed and then ate some Chinese takeout sitting on the floor, putting our plates on top of the unopened boxes. I was appreciative to Bill for helping me. However, I didn’t really see a future with him as a real boyfriend. I had a suspicion that he had a steady someone that he wasn’t telling me about.