Girlfriend Problems - A Transition Story - Part 2 (Patreon)

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Author - Katherine LaRue

My parents were strict, born-again Christians. They weren’t so bad at first, but as time went on after they converted from Catholicism to the Christian Fundamentalist Church, it was all fire and brimstone with them. I was beaten as a child so many times about my crossdressing that I would have bruises and welts on me.

They were also strict with my sister Kiera when it came to her dating boys. She had to sneak around with her boyfriend, and Denise would cover for her.

As I cried, Denise came down to the floor and hugged me. “That’s alright, dear. I’m doing this for both of us. Just roll with it.”

“But I don’t want to be a freak. I don’t want everyone staring at me. What kind of job could I get dressed like a woman?”

“Don’t you worry about that? I will help you. I do love you. I just can’t get over your femininity. You must have gone through a lot when you were young. Kiera explained everything to me. That’s when I realized I made a mistake in trying to love you as if you were a man. I promise I won’t let anything happen to you. But!! I am still a little pissed at you for not being upfront with me."

“But I still love you, Denise!” I said, half crying.

“I love you too, but I have to do what’s best for me as well.”

Denise hugged me, her curly brown hair stuck on my cheek as she got up and continued putting the finishing touches on the room while I went and checked on the food.

Soon the doorbell rang. Denise went and answered it. It was her friends Jennifer, Sheila, and Janelle. They all came in cackling and laughing. Jennifer, who is a young, light-skinned African-American woman and a financial advisor with Prudential, asked, “So is Kenny here?”

I overheard Denise say, “Kenny doesn’t live here anymore, but Kathy is!”

I heard them all laugh. I suspected that Denise invited her girlfriends over just so she could embarrass me.

“Oh, Kathy!” Denise yelled. “Come out of the kitchen and say hello to the girls!”

My heart raced. They all knew who I was, as they were Denise’s best friends. I didn’t want to leave the kitchen in the attire that I was currently dressed in. I looked at my jeans and the flowery top I was dressed in and felt a rush of anxiety. Then I thought, ‘What the hell? It’s obvious that they already know that.

I came out to the living room, where the four women sat, inspecting me. My head was down as I stared at the floor, still completely embarrassed.

“What’s the matter? Why are you looking like that?” Sheila asked.

Sheila, a heavy-set white woman, worked with Denise as a medical assistant.

I didn’t respond verbally. I just shrugged my shoulders.

“Oh dear, why don’t you come and sit down with us, honey?” said Jannelle. Janelle was a Hispanic woman who was very pretty and always dressed to the "nine." Her effect reminded me of Ana Cabrera (the news anchor), except that she was much more gorgeous than her. She was married to a doctor, and she looked like money. I could tell her clothes were very expensive and very well made. She wore a diamond ring on her hand that shone so brightly that it could hurt your eyes just looking at it.

“Come on, sit by me.” Janelle insisted as she patted her hand on the little bit of couch she had where she was sitting. I squeezed my thin frame next to her. I could smell her expensive perfume (which was probably Bulgari or Michael Kors).

“So Denise tells us that you want to be a woman now. I think that’s mighty brave of you!” said Jennifer.

“I guess,” I mumbled.

"Oh, just stop it!” Denise yelled. I stared at the rug while Denise went on a rant. “Let me tell you; this one right here had two storage bins full of women’s clothes. I went on the computer and found all of these websites on how to transition from a man to a woman, how to crossdress, and how to do your makeup. And created an entire female identity on social media! And!!! Had pictures posted of her in drag!"

"Oh, really?” asked Sheila. “A real sissy, isn’t he? Or should I say she?”

“Yes!” said Denise. Then she turned toward me and said with venom, “So stop with the mumbling. You know that’s what you want!"

I wanted to start crying again. My eyes turned red even though I was doing my best to hold back the tears.

“Denise, calm down now. Don’t get yourself upset," said Janelle. “You all need to stop with the putdowns. People who are transgender can’t help the way they were born. I don’t know if Kenny is transgender, but he gave it the old college try, but I guess it didn’t work out.

People who are gay or transgender can’t help the way they are. Richard has plenty of transgender patients at his practice. And I must say, he makes them look good. My Richard is the best plastic surgeon in the business."

I was shocked. I never knew Janelle’s husband was a plastic surgeon.

“Kathy, could you go get us something to drink? What do you girls want? We have wine in the refrigerator, or if you want something harder like cognac, we have that too."

“What kind of wine do you have?" asked Sheila.

“We have a Merlot chilled in the fridge as well as a white Zinfandel.”

“I’ll take the Merlot,” said Sheila.

“I’ll take the Zinfandel,” said Janelle.

""Zinfandel,” said Jennifer as I looked at her.

“I want a cognac, dearest Kathy,” said Denise.

I went and got the ladies their drinks and continued to prepare dinner. I overheard Sheila and Jennifer saying, “We’re here to support you, Denise. It must be hard for you. I can’t imagine finding out that my husband was gay. I set the table for the four of them. I served them all dinner once it was ready and went to my new room. I didn’t want to eat with them, as I felt judged and out of place. I could hear them laughing in the bedroom of our apartment.

I just sat on a bed that Denise made for me to sleep in, as I had no bed in that room yet. I thought perhaps Denise was right. Maybe I wasn’t cut out to be a man. After all, as a child, I used to dream of being a beautiful woman when I grew up. Denise was the only woman I had ever been with. I suppose that my desire to fit in within society, coupled with the upbringing I had, made me think that living as a woman was wrong and against not only the norms of the society but also “God’s Law”. Just as my thoughts started to stray, there was a knock at the door.

“Yes, come in!” I yelled.

It was Janelle, "Hi, sweetie”, she said as she opened the door. “How come you’re in here by yourself?”

“I wasn’t hungry. And honestly, I felt out of place and judged.” I said to Janelle

.

“You know, honey, you’re going to have to grow thicker skin than that if you’re going to make it in this world,” said Janelle as she sat down in the lone chair in the room.

“I’m just trying to figure out my life, Janelle. I really love Denise. At least I thought so. But she’s made me rethink some things. I’ve lost everything; my job, my girlfriend, and my family rarely talk to me. I feel like I have no support.”

“If it’s any consolation, I think everything happens for a reason. I personally think you would make a beautiful woman. If you need a friend, you can call me and we can hang out a little. I think Denise is just angry right now, and I’m sure she’ll calm down.”

“But what about Denise?”

“Don’t you worry about Denise? She has bigger fish to fry."

“What do you mean?” I asked.

“She’s involved with someone else, sweetheart. And he’s a piece of work! He thinks he’s God’s gift to humanity.”

My heart dropped when she said that. In the back of my mind, I held out some hope that I would somehow be able to win her back as long as I did what she said.

“So I guess there’s no hope for us to reconcile our differences?”

“I doubt it. She’s told me a lot about what was going on in your relationship, and she’s quite bitter. I’m actually surprised she’s letting you stay here.”

“Oh?”

“Yes, honey. She’s been quite hot and heavy with this guy, Bob. He’s quite the hunk. You’ll see it eventually. You should just go and chart your course forward," said Janelle. “Now let me see something. Stand up.”

I stood up as Janelle instructed me. “Turn around,” she said. And I followed her instructions.

“Now sit in the chair,” she instructs me further. She took the scrunchie out of my hair and ran her fingers through it.

“Now lift up your blouse,” she said as she examined my body, putting her hand on my waist. “My God, you’re so thin! Do you eat food?”

Janelle gently put her hand on my face, turning it from side to side. "Well, you have great bone structure and not too much facial hair. Do you have any Asian blood in you?”

“Not for certain. But there was a rumor in my family that we had Delta Mississippi Chinese in our blood.”

“Because usually, Asian men don’t have much facial hair,” said Janelle.

.

“Well, then the rumor in our family is probably true.”

“Okay! I see it," she said as I sat back down on the palette on the floor. “This is going to be easy. You keep on doing what you’re doing. I’m going to take you and treat you to getting your hair styled as a gift.

What are you doing on Monday next week?”

“Nothing. Probably look for a job."

“Do you have an interview yet?”

“No, just here searching for jobs online,” I replied.

“Well, I think you should get yourself together first so you can work as Kathy. Listen, take my phone number, and you call me around ten o’clock next Monday, and I’ll pick you up.”

“Okay, that sounds good. I’d like that.”

“Now come on out of this room and join us before we all leave.”

I got up and followed Janelle down the hall to the living room. Her beautiful light brown hair flowed down her back, and her bracelets clanged around her wrists. Janelle was very much a woman’s woman. She dressed impeccably, even when it was a casual affair. Janelle was about 3 or 4 years older than Denise and Sheila and 8 years older than me.

As we entered the living room, Denise spoke up, “So what were you two girls talking about?”

"Oh, nothing,” said Janelle. “Just consoling, Kathy.”

“Consoling Kathy?” asked Denise.

“Girl, stop being so hard on this one,” said Janelle.

“Not being hard. But she has a debt to pay to me.” Denise clapped back.

“As a matter of fact, these dishes have been on the table for over an hour. She needs to go and clean up.”

I rose from the couch and started to take the dishes off the table. It's a job that I'm used to doing. So it didn’t bother me at all.

Soon the ladies left, and I was left cleaning the last of the wine glasses. Still shaken and confused, I thought about everything that had transpired and made the decision that I was going to roll with this new identity. What did I have to lose?

I had already lost everything. But not only was I going to change my identity, I made up my mind that I would transition and become more beautiful than Denise. I decided to go all in. After all, perhaps Denise was right; I was probably never cut out to be a man. The next week, I had a lot to process. What was I doing with my life?

Am I gay? Am I a woman? Each day, I got used to the idea of truly becoming Kathy. Getting up in the morning and putting on pants, feeling my smooth body, started to feel good to me. I went outside a couple of times just to see people’s reactions to seeing me dressed in women’s clothing. Most of the time, I was just ignored by those who passed by.

Yes, some gave me strange looks, but for the most part, venturing outside was uneventful. The positive thing was that I virtually knew no one of consequence in this new town outside of Philadelphia.

The New Me,

The following week, on Monday, I woke up early and made Denise and me coffee. I made her a quick breakfast and a sandwich for her lunch to take to work. She thanked me and was out the door by 7:30.

I took a shower and found some leggings and a long top to put on. I put on some flats that I had bought and kept in the trunk that was now laid out with the rest of the shoes that I had bought previously. I sat and put on a little foundation, eyeliner, and some lip gloss that Denise had bought.

My hair was curly and came down to the nape of my neck. Not very long, but just enough to put into a ponytail. I started to vacuum and dust a little bit and made up the bed in what was now Denise’s room. I called Janelle at exactly ten o’clock. She said she would be right over.

I found a small purse in Denise’s closet to keep my wallet and my lip gloss in and set out to wait outside on the steps to the building. I was a bit nervous, as I had not been out dressed like this except once. I had taken a chance one night when Denise was out with the girls and walked around the block in some of my drag.

I took a deep breath, went outside, and sat on the steps. It had been an entire week since the episode with Denise. Since then, I have gotten a little more used to being completely dressed in women’s attire, even if it is of the casual sort. But I hadn’t been outside completely dressed yet, except to maybe take out the garbage or walk around a block or two.

I sat there and smoked a cigarette. I was an occasional smoker, mainly when I drank or got a little stressed. I thought about what others would think of me. A few of the neighbors walked by and stared at me with a puzzled look. I had seen most of them, but none of them very rarely spoke. Just the occasional nod or hello.

Even so, I didn’t care at this point what anyone thought of me. I was at the lowest point in my life, with no money, no friends, and the specter of becoming homeless. It was a good thing that I wasn’t completely a novice at dressing up. I had spent hours as a child and then as a teenager trying to make myself look female.

Soon, a gray Mercedes-Benz pulled up and honked. It was Janelle. As I made my way to her car, I walked as I had practiced whenever I cross-dressed around the house. I held my elbows close to my waist with my wrists turned out. I was sure to walk in a straight line with almost one foot in front of the other, slowly but very determined.

“Hey, girl! Look at you!” said Janelle as I opened the car door.

“Hi, Janelle. Thank you for picking me up.”

“Not a problem. I wanted to," said Janelle. “Plus, I’m not working these days, although I do want to start my own business. You look great, you know; very feminine!”

“Really?”

“Yes! Really! I can see it. You’re going to be on your way after today.”

We drove and talked for about 15 minutes and ended up on the other side of town, where it was mainly a Spanish neighborhood. Janelle pulled into the parking lot in front of “Marisol’s Beauty Shop”. I looked at the sign, which was slightly worn.

“Come on. Let’s go, Miss Kathy.” Janelle said as she turned off the car and got out. I followed her into the shop, where two women were organizing their booths. There were no clients there as of yet. After all, it was a Monday. It was not a busy day at a hair salon.

A middle-aged woman came up to the front. “Janelle!” she exclaimed. And I almost ran and hugged her.

“Marisol! Hola!”

I stood there as the two exchanged pleasantries and spoke in Spanish to each other.

“Mira Marisol. This is Kathy, my friend.”

“Hello, it’s a pleasure to meet you,” said Marisol with a heavy accent.

Janelle spoke up: Marisol, hazle un pequeño corte y unas mechas rubias. Quiero que peines su cabello con un pequeño flequillo. También necesita enhebrar, dar forma, y arquear las cejas.” "Marisol, give it a little cut and some blonde highlights. I want you to style her hair with little bangs. You also need to thread, shape, and arch her brows."

Marisol answered,”¡Perfecto! Ningún problema. Ella está en buenas manos conmigo.”

(Perfect! No problem. She is in good hands with me.

I had no idea what they were saying, but for some reason, I trusted Janelle, as she was the only person in my life who cared about me.

Marisol sat me down in her chair and got to work. She started cutting the ends of my hair as she spoke to me in half Spanish and half English.

“See just a little,” she said, showing me the clippings in her hand. She continued to clip and speak to me. “Que hermosa,” she said, and I understood it to mean “how beautiful”. I did know that much. “You have beautiful hair. Very strong. You know dura.” continued Marisol in broken English.

Marisol finished cutting, mixed this white paste together in a container with a brush, and applied it to my hair. She then got another container, applied it to my hair, and then wrapped it with aluminum foil. She then covered my hair with a plastic cap and brought me over to another chair, where Marisol spoke to the other woman there. “Vale, ¿puedes hacerle las cejas? Haz el arco alto.” Está bien, no hay problema.”

The woman, whom she called Isabel, started to clear out my eyebrows. It hurt at first, but then I got used to it. She spent about 10 minutes and stopped. “Bueno! Mira!” said Isabel, handing me a mirror. I was in shock at how just raising my eyebrows feminized my face.

Marisol then brought me over to the sink and rinsed out the dye in my hair. She got some rollers out and rolled my hair. These weren’t normal rollers. They were thick spiral twists. Marisol put me under the hair dryer, and I read the annual thick special edition of Vogue as my hair dried.

After about 20 minutes under the dryer, Marisol took me back to her chair and took out the spiral rollers. She took a picture and fluffed my spirals out. She then took a roller brush and a blow dryer, blew out a small bang, and combed it to one side over my forehead.

She teased my hair all while spraying a light hairspray over my entire head. Marisol handed me a mirror so that I could see both the back and the front.

“You like it?” she asked.

I was astounded at my transformation. Marisol had dyed my hair a medium brown with blond highlights. With the bang and my newly formed eyebrows, I looked very feminine. I even got a little excited looking at myself in the mirrors at the salon.

“I love it!” I said it with a big smile.

“Perfecto!”

I hadn’t smiled in over a week since Denise broke up with me and gave me this ultimatum. I sat on the small couch and waited for Janelle to come back to pick me up. I sat and read the huge Vogue magazine while I waited.

After about 10 minutes, Janelle came through the door.

“Oh my! You look gorgeous, my sweet Kathy,” exclaimed Janelle.

“You like it?” I asked.

“Like it? I love it! Janelle said, touching my hair lightly. “See, I told you I would help you get it together.”

That made me feel good inside. Since I had moved to the suburbs of Philadelphia from Blairstown, I had no real friends. I didn’t have many friends to begin with, even in semi-rural Blairstown. I left my hometown because Denise found a very good-paying job there as a nurse. But now I was feeling close to Janelle after her kindness.

Janelle and I got into her Mercedes and rode off.

“Are you hungry?" asked Janelle.

“Sure, yes, I am. But Janelle, I don’t have much money to eat out.”

“No worries, I got you, girl.”

Janelle was endearing herself to me as the hours we spent together that day rolled on. It felt good to have a friend.

“Let’s stop at Panera. Is that okay with you?”

“Sure,” I said.

“Then we need to stop at the mall real quick. Then I’ll take you home. Okay?”

We stopped and ate at Panera. I ordered a Caesar salad with chicken, while Janelle ordered a soup. We sat, ate, and talked.

“I’m curious about your employment situation. Why don’t you go out and get a job, Kathy?" asked Janelle. ‘You know you should be trying to be more independent from Denise.”

“I know. All of this is very new to me, and I’ve almost run out of money. But Denise wants me to be more like a live-in housekeeper.”

“I know that’s what she wants, but if you’re earning your own money, you won’t have to be tied down to all of her rules. I mean, it’s a little bit crazy what she’s doing. Although I do agree with her that you two shouldn’t be a couple, I mean, I think what you’re doing now suits you much better than trying to fake being a man.”

“I know. I realized that this past week after you left, This is something that’s been with me since I was around 5 years old. My sister, Kiera, used to dress up with me as kids, and I never stopped. Although, in high school, I did try to fit in, I couldn’t stop myself. I thought perhaps if I had a girlfriend, it would put an end to crossdressing and wanting to be a woman secretly. But I just couldn’t help myself.”

“I totally get that. And probably you and Denise hit it off because you and her were more like girlfriends than the usual heterosexual relationship, I’m guessing.”

“That’s true. We talked a lot together over the phone for hours. Even when we went out, we went to see movies that were dramas and love stories. At home, when we watch TV, we watch the Housewives of New Jersey, Atlanta, New York, Orange County, and the other ones in that series.”

“Yes! I do too!” Oh my God! I’m addicted to those too! Isn’t Teresa Guidice crazy?”

“Yes!!! I think the New Jersey Housewives are my favorite.”

“So tell me, my dear Kathy, have you ever thought about dating a guy?”

I was taken aback by the question. What should I tell her? I wasn’t sure about my sexuality.

“Well, I have thought about it. But only when I get dressed up.”

“Hmmmm, so you’re kind of dressed up now. How do you feel about guys right at this moment?”

“I would consider it,” I said.

“I see. Have you ever been with a guy?”

“No. I’m afraid.”

“Afraid of what?”

"I was afraid that anal sex would hurt.”

“It doesn’t hurt once you get used to it. My husband and I do it every now and then.”

"Yeah, but I would rather wait on that,” I said.

“Wait for what?" asked Janelle. ”

“Wait for,  Um, I don’t know,” I said, not sure how to put my words together.

“Oh! I know you want to go all the way. Do you want to have bottom surgery?”

“Well, the thought crossed my mind.”

“Hmmm, I bet you do. That’s all I’m saying. If that’s what you want, then you should go for it!”

“This is all very new to me. I’ve been thrust into this position by Denise.”

“Well, you're on this path now, for sure. You know, I checked out your body when I was there last week, and I think you’re petite enough to do this and do it well. What do you weigh? About 115 pounds or so?”

“Actually, a little less than that. More like 110 pounds.”

“Uh-huh. And how tall are you? 5’ 6” or 5’ 7’?”

“Yep,” I answered.

“Well, I’m 5’7”. So we’re about the same size. It’s not like you’re some 6-foot-tall guy with muscles. Most women are about 5 feet 4 or 5 inches. You won’t stick out. Look at me, and I wear heels a lot.”

“True.” I agreed with her.

“I think you should go for it," said Janelle.

We finished our meal and headed to the mall. We got out of her car. And I walked into a place where they sold jewelry.

“Come on, Miss Kathy. You’re going to get some earrings today. I saw those ugly clip-on earrings in your room last night, and that just won’t do. You need your ears pierced so you can have some options for your ears.”

I sat down in the chair as an Asian woman came with a small gun. She started on my left side. “Wap!” The sound was right in my ear and surprised me. She went to my right side and said, “Wap”. The Asian woman blotted my ears with alcohol and then put these pretty diamond studs in my ears.

Janelle paid the woman, and we left.

As we walked out of the store, “Janelle, why are you doing all this for me? You must have spent over $200 today!”

"Look, honey, that’s just a drop in the bucket for me. I couldn’t see you as miserable as you were last week. Plus, I like that you like this. With you, it’s like having another girlfriend or sister I can roll with. I just don’t want to see you running around like some crazy drag queen. There’s much more to come. Trust me. I’m on your side, even though Denise is a dear friend.”

“Thank you, Janelle. I appreciate you.”

Janelle dropped me off at our apartment, and I immediately went inside and started dinner for Denise and myself. It was summer, and it was hot that day, but there was a nice breeze that kicked up and blew through the kitchen curtains.

There weren’t enough leftovers from last night to make a meal, so I started a new one. I made some ravioli with sauce and then went to my room to browse for jobs online.