Girlfriend Problems - A Transition Story - Part 1

ALL STORY LIST | PARTS - PART 2 | PART 3 | PART 4 | PART 5 | PART 6 | PART 7 | PART 8 | PART 9 | PART 10 | PART 11 | PART 12

Author - Katherine LaRue

Note - I am delighted to share with you today's Patreon post, which includes a story from one of our dear Patreon member, Katherine LaRue (A.K.A - Koko Jones), who shares with us a story detailing the experiences,

About a young boy who inhibits his desire to become a woman by dating a woman. Little did he know she would help him reveal the woman inside. This story took place around the year 2010 in a small town outside Philadelphia.

I was an 18-year-old virgin until I met my girlfriend Denise. As a youngster, I was afraid of girls and it seemed as if many of the girls I went to school with had no interest in me. Sure I had lots of girls that were friends but none seemed to want to date a scrawny thin little guy. I stood about 5 foot 7 and at 18 it didn’t seem as if I was going to grow any further. My parents were mixed race.

My Mom was Dutch, Italian, and Native American. My Dad was a mix of Creole, Black American, and French and some say that he was related to the Delta Mississippi Chinese. Our family was the most interesting-looking family in Blairstown, Pennsylvania.

My sister and I came out looking very similar in that we had a mix of hair textures that ranged on our heads from curly to straight in different places as well as olive-colored skin. We stood out in our small town as the population was 88% white and the 12% that was left was of varying ethnicities.

For the most part, I was a normal boy. I had a few friends from school and the neighborhood but once I started High School most of those friendships started to fade away. I became a loner in High School; mostly interested in video games and computers. I was too small to play sports as all of the other boys my age had growth spurts during their High School years.

By my Senior year most of the boys my age had lots of facial hair. I was considered cute while the other boys were handsome. Some of the girls would comment on how pretty my hair was even though at that time it was relatively short.

We lived in a mostly blue-collar, working-class community. There wasn’t much to do there for young boys besides playing sports or going to the arcade at the mall. A few of the boys in my High School took menial jobs at fast food restaurants or gas stations and the like.

Once I graduated High School and was ready to enter college a girl I knew from my neighborhood took an interest in me. She was a pretty girl about 5 foot 6 inches tall with a killer shape, curly brown hair, and beautiful breasts. Denise was about 4 years older than me and since she had been having sex for years I guess going out with me was a bit of a challenge for her.

School ended in early June in Blairstown and the summer heat was starting to kick into full gear.

Without a job, I would stay home and play video games most days. One day not too long after the last day of school, the doorbell rang and it was Denise.

“Hi Kenny, is your sister home?”

“Oh hey, Denise.

No, she’s not.” I answered. I stared at this beautiful woman who stood in my doorway. She was gorgeous! Wearing a tank top and cut-off shorts.

“Well, I wanted to talk to her. It’s something really important.”

“Oh well, I, I, I don’t know when she’ll be home.” I stammered due to the fact that her beauty was intimidating. My sister and Denise went to High School together and had known each other since they were kids.

“Well can I wait for her to come home?” asked Denise.

“Sure, come in,” I said opening the door wide for her to enter. “Have a seat. Can I get you something to drink?”

“Sure. What do you have?”

“We have iced tea, lemonade, water, and soda.”

“An iced tea would be great!”

Denise followed me into the kitchen and watched as I made her iced tea.

“So I guess it’s pretty important that you talk to my sister. What’s it about if you don’t mind me asking?”

“Oh, nothing much. Just wanted to get her advice on a guy I like,” answered Denise.

“Okay, so who is this guy? Maybe I can help. Do I know him?”

“I think you do know him,” she said with an impish smile. “But I’ll wait to talk to her about it.”

“Okay,” I said inquisitively.

I had music playing in the living room.

“Oh is that Eddie Short I hear?”

“Yep!”

“Oh I love him,” said Denise.

She walked ahead of me to the living room. Her daisy dukes were so high I could almost see the cheeks of her butt. She sat on the couch looking at my CD collection. Come sit with me until your sister gets home. Her beauty was intimidating. I always wanted to know what it would be like to be with a girl.

“You know, I don't think Kiera will be home for a while,” I said as I sat beside her.

“When does your Mom get home?” She asked.

“Oh, not until at least six o’clock.”

“Oh, that’s a couple of hours from now.”

As Denise got comfortable looking at the CDs so many thoughts ran inside of my head. This girl is so good-looking. I tried to put thoughts and desires out of my head. There’s no way this girl would want me. After all, I was just an inch taller than her and she probably weighed close to what I weighed. I was skinny; only about 110 pounds and had no muscles and I wasn’t athletic at all. But I continued to sit as she started to talk to me. I started to stare at her, enamored with her beauty.

As time went on I lost track of what she was talking about. All of a sudden she stopped talking. She said to me, “You know the boy I wanted to ask your sister about was you.” After that, she started kissing me. Things got hot and the next thing I knew we were undressing each other. All of the while I was filled with anxiety. One thing led to another and we were having sex.

I was a novice and she had to show me how to do everything. I was so self-conscious about my male parts being so small that it caused me to struggle a bit. But Denise assured me it was fine. I couldn’t believe that this grown woman, who was 4 years older than me, was showing me what to do in the midst of this encounter.  She left before anyone got home and that’s how I lost my virginity.

Denise and I continued to see each other and it blossomed into a full-blown relationship. I now had a girlfriend. I often wondered about not being able to have a girlfriend. I wondered many times if I even liked girls. You see, when I was young I would often wear women’s clothing and dress up. It never really stopped altogether but subsided from time to time due to the fact that my parents became very strict Christians. I was often in fear of my father because he was known to fly off the handle if he wasn’t obeyed. I often questioned myself. I took it as a phase or a fetish that was something to be enjoyed from time to time.

Denise and I became an item. We often socialized with friends and on the surface, things seemed pretty normal but there was trouble brewing below. I continued in school and worked and Denise who had finished her Nursing degree worked full time as a nurse. After a couple of months of dating, we eventually moved to a small-bedroom apartment together in the suburbs of Philadelphia. Our hours didn’t match up very well.

While she was working a 9 to 5, I was in school part-time and then worked late into the night. I would often be asleep when she left in the morning and be either at work or at school when she got home. We did see a lot of each other on the weekends. She would often invite her girlfriends over on Saturdays and Sundays which prevented us from spending a lot of quality time together. I liked her friends but it seemed like I was seeing more and more of them. Many times they would have a girl's night out and I was left at home by myself. Being a computer science major I was often doing work on the computer so it didn’t bother me too much as I would just spend many nights at my desk at the apartment.

One night I came across a website while surfing the web that talked about and featured crossdressers and transgender women. Denise was out with her girlfriends at a club so I figured no harm in looking. I looked at it only for about 15 minutes and turned it off. For some reason, it triggered something in me. I had tamed my desire to crossdress for a long time but suddenly something exploded inside of me. I got up from the computer and looked through Denise’s drawers.

I took a pair of her panties and put them on. Since she was almost as tall as me I tried on one of her dresses. I anxiously put them on and stood in front of the mirror and admired myself. Being cautious I stopped myself from going any further to not get caught. The feeling though was euphoric to me. Denise came home that night and did not suspect anything.

This behavior continued for a while. Every time she went out with the girls I would crossdress in her clothes. After a while, I would get excited when she told me she was going out with her girlfriends clubbing. She would go clubbing and I would crossdress. I started to visit those transgender websites more and more often. I started to get bolder and bolder with my crossdressing.

I even started to go and buy my own female clothing and hid it in a storage container in the storage unit connected to the apartment. I even went as far as buying my own makeup. I would stand in front of the mirror and admire myself. My thin, 110-pound body looked great in the fashions I tried on. I tried all kinds of looks; from glamorous to bohemian.

I started to wonder what it would be like if I was to transition from male to female. I collected all kinds of women’s clothing. I even wore some of Denise’s clothing if I was trying to get a certain look. All of this I kept hidden from her. I started to become addicted to the exhilaration of crossdressing and modeling in front of the mirrors in the bedroom. It gave me comfort and reminded me of my childhood when I would crossdress with my sister Kiera. From the time I was about 5 or 6, I would play dress up with Kiera who was 4 years older than me.

She would make my face up and do my hair and tell me I would make a great little sister. I believed her and started wishing I could become a girl like my beloved sister. I would pray at night that one day I could grow up to become a beautiful woman.

But all of those dreams came crashing down when my parents became involved in the Christian Fundamentalist Church. They became stricter and one time my mother had noticed that I hadn’t gotten eyeliner completely off around my eyes. I was told to “toughen up and be a boy.”

One night I crossdressed while Denise went out and by 4 a.m. she still hadn’t arrived home. I went to sleep a little worried. In the back of my mind, I felt that she would be home eventually. If there was any problem I knew she would call me. I woke up the next morning and she still hadn’t come home.

About 9am the next morning I heard her coming through the door.

“Denise! Where were you? Are you okay?”

“I’m sorry honey. I drank a little too much last night and spent the night at Sheila’s.”

“Oh okay. I thought something might have happened to you.”

“Yeah, I just didn’t want to drive in that condition.”

That was a Sunday and the rest of the day Denise slept while I cleaned and cooked dinner. I woke her up and served her dinner.

“What a beautiful thing. I have a boyfriend who can cook and clean. Now would you be a doll and draw me a hot bath?”

“Yes dear,” I complied.

I drew her a nice hot bubble bath while she talked on the phone with her friends laughing and sometimes whispering. It seemed odd that we were in this situation. She really hadn’t been having much conversation with me. But she yakked it up with her girlfriends. Most of the time we were together there was dead silence.

This continued for weeks. She continued to go out with her friends and even stayed out until the morning many times. To make matters worse I was laid off from my job. Which made the strain on the relationship even harder. I tried to make amends by doing all of the cooking and cleaning. I made the beds and always had the house spic and span. While she was away at work I continued to crossdress.

One morning she came home after partying and hanging out and she went to sleep. After her nap, I went and talked to her.

“Hey baby, is there something wrong?” I asked.

“Wrong? What do you mean wrong?” she answered defiantly.

“I mean it seems like we’ve been growing apart for the past couple of months and we barely spend time together anymore. And when I talk to you, you don’t have much to say.”

“Well, I don’t have much to say because I don’t want to hurt you.”

“What do you mean?”

“I mean I love you Kenny but I just think we should just be friends and roommates.”

“What? Why?”

“Kenny, I know about you.”

I was stunned as my heart raced.

“What do you mean, I know about you?”

“I know you’ve been at home crossdressing. Dressing up like a woman. I’ve looked at your search history on your computer. I saw all of the transgender websites you’ve been looking at every day for months now. I mean how stupid of you as a computer science major, to leave your search history open like that. Plus, you haven’t touched me or had sex with me for months now.

I talked to your sister Kiera about it. She told me you’ve had this issue since you were a child. I also found your storage bins with women’s clothes. Why didn’t you tell me this when we first started dating? I tell you it hurts me, Kenny. I’m a woman and I don’t want to be with another woman. You’ve lost your job and I’ve been carrying you for over 2 months now.”

“But Denise! I can stop. I can get a job. I’m so sorry. I didn’t mean to hurt you.” I cried in desperation.

“Why should you stop? Stop what? Dressing up? Stop wanting to be a woman? I think it’s too late for that.”

I was shaken.

“I’m sorry Kenny. I started seeing someone else. A real man. A man who has a job and can take care of me. AND WHO CAN SCREW ME LIKE I NEED TO BE SCREWED. NOT LIKE SOME LITTLE BITCH! Moaning and sighing like a little girl when we were having sex. That’s not what I want. I don’t want to be with a sissy; a faggot.”

I sat there in tears. Maybe she was right, maybe I’m not a man at all.

“Kenny, I want you to take the spare room where your office is. Tomorrow we’ll go get a little small twin bed and you can stay in there until you can get on your feet. I love you and don’t want to put you out in the street. In the meantime, I will do as I please in this apartment that I pay for.

You will do all the domestic chores and do as I say as long as you're here. And while you're at it, since you want to be a woman so bad as long as you're here I will do you a favor and help you achieve your dream of being that woman that you want to be. From now on I will call you Kathy. After all, isn’t that your name on your fake Facebook page?”

I sat there crying. I had no words.

“And don’t just sit there crying, get your ass up and start dinner for me. Little girl,” she said angrily.

I was in a state of shock. I didn’t see this coming. I really wished we could have at least talked it out. I really was in love with Denise. I wanted to marry her once I finished school. But all of my dreams were crushed at that moment.

I cooked us a quick dinner and served her while she sat on the couch in the living room. I got ready to sit with her on the couch but she stopped me.

“No, missy. You eat in the kitchen by yourself.”

‘Missy’? I thought to myself. Why is she doing that?

I sat there in the kitchen not really hungry while Denise watched television and talked on the phone with her friends.

“Kathy! Come get my plate. I’m finished eating!” She yelled from the living room.

I quickly ran to the living room and got her plate, washed the dishes, and cleaned the kitchen. By the time I was finished. She left the living room and went into the bedroom and closed the door. I stayed out in the living room until it was time to go to bed. I went to the bedroom only to find the door locked.

I knocked on the door, “Denise? Honey?”

There was no answer but I could hear her on the phone. I knocked again and she finally answered the door. “What?!” she snapped at me.

“Can I come in and get my pajamas?”

“No! You’re sleeping on the couch tonight.”

“But what about my pajamas?”

She came to the door and opened it. “No, you can’t have your pajamas. But you can sleep in this.” She handed me a pink nightgown and a pair of cotton panties. “We’ll talk in the morning.”

I got a blanket and a pillow out of the linen closet and fell asleep on the couch.

I felt so bad and started crying feeling like this break and misunderstanding was all my fault. The next morning I woke up and started to make coffee. Soon I heard Denise stirring as she must have heard me clanking around in the kitchen. Denise soon walked in.

“I made coffee. Do you want some?” I asked.

“Sure,” said Denise.

I sat at the kitchen table staring out the window. Denise got her coffee and sat down at the table with me.

“Denise, I’m so sorry. I had been meaning to tell you about this but I just didn’t want to lose you.”

She just sat there in silence not saying anything. “I promise I can stop dressing up.”

After a long pause, Denise finally spoke, “Look I’m sorry I talked to you the way I did last night but that doesn’t change the way I feel. When I found out I got mad and wanted to hurt you. I still love you but I just think it’s for the best if we take a break.

This way you can explore yourself and think about what you really want. If you’ve been crossdressing and secretly wanting to be a woman all of this time then I think you should go ahead and do that. So I’m going to make sure you do. For now, I still want you to take the spare room that you call your office.”

“Okay, whatever you say. Do you think we can still get back together?” I asked.

“Honestly, I think you’re a woman inside. I don’t date women. Let alone have a serious relationship with one. Now I want you to get a few things from the store while I straighten up around here.”

Denise sent me to the store with a grocery list a list for the pharmacy and her debit card. I picked up the groceries and then headed to the pharmacy part of the store. She had a specific list of items that took a very long time to find.

She had me pick up Nair, red nail polish, polish remover, pantyhose, foundation by Covergirl, mauve lipstick, new eyeliner, and facial moisturizers. It took me almost 2 hours to get everything. When I got back I took everything to her and gave her back her debit card.

“Okay this bag is yours,” she said, handing me the bag with toiletries and makeup. “Now take off those clothes and strip.”

I slowly took off my clothes. As I stripped she picked them up and put them in a large garbage bag.

“Now go take a shower and use this before you get in.” Handing me the Nair. Then afterward put these on.” she demanded as she handed me a pair of panties and a bra.

“But”

“Sshhh!” she said. “After you finish I want you to put on these jeans and this top,” handing me a pair of women’s jeans that fit very snug and a short-sleeved women’s top. “Go on and wear these. We’ll figure out the rest later. I’ll be right back,” said Denise as she took the large garbage bag out and threw it in the garbage. When she got back I had done what she said.

“Okay, that’s better,” said Denise.

“What did you do?” I asked. “I did you a favor and threw away all of your male clothing and those God-awful Men’s sneakers and shoes. From now on if you stay here you’ll wear only women’s clothing.”

“But what am I gonna wear outside?”

“If you go outside, wear the clothes you have.”

“But.”

“Don’t “but” me my dear Kathy. I’m doing you a favor.”  She said, “I’m going to make your wish come true. And I'm doing this only because I care about you.”

I did as she said and went to the bathroom and applied the Nair on all of the hairy parts of my body. My legs, underarms, and a little on my chest where there were just a few hairs. I then proceeded to dress in the clothes that Denise ordered me to wear. Having no hair made my skin feel smooth and it gave me a bit of exhilaration. However, it felt weird. She had never seen me in women’s clothes before. It felt humiliating.

“Now, I’m going to finish your room while you start to prepare Sunday dinner. We’re going to have guests so make enough for 4. And do something with that hair for god's sake!”

I went into my room and changed, making sure I put on the panties and tucked my private parts just to ensure that I had no noticeable bulges. I understood this from all of the crossdressing I had been doing from when I was a child up until the present. I brushed my hair back into a short ponytail; which Denise would describe as a “Man bun” previously. I then went to the kitchen and started to make dinner. I had already defrosted an oven-stuffer chicken. I decided to make saffron rice along with roasted vegetables.

While I prepared dinner Denise busied herself by fixing my room into my own separate bedroom. The feelings of shame and sadness started to overcome me. I felt alone in a place where I had no friends or family. I really did love Denise and she was really the only person I knew. I had known her since my early teen years through my sister. I soon started to become overcome by emotion and tears once again streamed down my face as I cooked.

After I put the chicken in the oven and the rice in the pot, I took a break to go to the bathroom. I passed by the room which was once my office with just a desk and some books. Denise had put up a makeshift vanity as well as shelving out of milk crates and a few boards that held a few clothing items on one side of the room and a large mirror on the other side of the room that sat on a piece of plywood covered with purplish material to hide it. Close to the mirror were my own makeup nail polish and other toiletries that she had bought me.

“See what I did? Do you like it?”

“Yes, I guess so,” I said meekly. I was still hurting inside.

“Well, this is the way it’s going to be my dear. I can’t see you out on the street. The only option you have is to go back home to live with your parents in Blairstown. I know you don’t want to do that.”

I started crying again. I sat on the floor sobbing in front of Denise. I was angry with her as I saw it was a cruel punishment.

But most of all, I was angry with myself for having these tendencies, this fascination, or better yet the yearning to be female dating back to when I was at least 5 years old. My crossdressing had always gotten me into trouble as far back as I could remember.