Girlfriend Problems - A Transition Story - Part 5

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Author - Katherine LaRue

We were getting ready to get into the car when she went to the trunk and handed me a large pink bag that said ‘Victoria’s Secret’ on it.

“Come on, open it in the car."

I got in and opened the bag. Inside was lingerie of all different colors and fabrics. There were a few camisoles, corsets, rompers, garters, and stockings. All of them were very sexy and alluring. At the bottom of the bag, there was a small box that was gift-wrapped.

“What’s this?”

“Now that you’re going to wait until you get home to open it, I want you to call me after you open it. I think you’ll like it.”

I went upstairs to the apartment with my Victoria’s Secret bag along with the bag of Louboutins, feeling very good about myself and some new possibilities. I could feel my life changing before my eyes. The feeling that I had inside was one of contentment. It was a new feeling, one that I had never felt before. I had finally accepted the fact that I was born to be a woman.

I hurriedly put my bag down and started cleaning, cooking, washing out the tub, making Denise’s bed, and picking up her clothes and separating them. I didn’t get a chance to do laundry before she got home. I would do that after dinner, as it was getting close to the time she would be home. I went into my bedroom and opened up the gift-wrapped box with pink paper. I wondered what it was. In the box, there were two dildos.

I was in shock! One was of the vibrating type, and the other was softer and more flexible. There was a note inside that said, ‘This is for those lonely nights. Practice makes perfect. Call me when you open this! Love Janelle.’

I immediately called Janelle, “Girl! Why?”

She started laughing and I could tell she was still in the car. “You like?”

“Yes, I think,” I said, sort of laughing. “I’ve never had one of these before!”

“Honey, you’ll figure it out. You need practice. I’m glad you like it.”

“Thank you for your time and the presents today. I really appreciate it. And thank Richard for me.”

“I have a feeling you’ll be seeing a lot more of us. I’m on my way home now to fix dinner. Let’s talk tomorrow when you get a break at work.”

“Okay,”

“And don’t forget to practice walking in those shoes I gave you!”

“Okay, talk to you tomorrow.”

I put away the Victoria’s Secret gifts, put on the shoes that Janelle gave me, and went into the kitchen to tidy up and finish off the dinner I was making. Just then, I heard Denise come through the door.

“Hey, how are you?” said Denise, in a very tired, monotone voice, not looking at me but at the mail that I had brought in.

“I’m fine,” I answered. And then she looked up and saw what I was wearing on my feet.

“Oh my! Where did you get those, and why do you have them on?”

“Oh these. Janelle gave these to me. I’m wearing them just to practice wearing stilettos.”

“Wait, are those Louboutins?”

“Yes. You like?”

"Oh, I see. Janelle has never given me a gift like that."

I walked around and modeled them for her.

“Look at you! Wearing stilettos already. I’m very impressed. But you do need to practice. I’ll give you some tips if you’d like. Well, any help is appreciated.” I said.

“I’m going to take a bath. Do you mind drawing my bathwater while I take these scrubs off? Bob is coming over later, even though I don’t really feel like company.”

"Sure, anything for you, Denise.”

I drew her bath water while she changed her clothes. After her bath, we ate, and I even made a plate for Bob. I was in a good mood. Later that night, after I went to bed, I could hear Denise and Bob making passionate love in the next bedroom. Something about it made me aroused, thinking about the dildos that Janelle gave me. I quietly went to get them out of the box and started to penetrate myself. I imagined a fictitious man on top of me, driving his penis inside of me. I fantasized about having a vagina that became wet.

After about 5 minutes of that, I reached an orgasm. I hadn’t had one in a long time. Maybe over a year. I rubbed my budding breasts and nipples and then took the vibrating dildo and penetrated myself again and again, fantasizing about having a man inside of me. I did it again and again until I realized that I had spent over an hour masturbating. I went to the bathroom and cleaned off the dildos very quietly so as not to wake up Bob and Denise.

The next day, I went to work, wishing I had a boyfriend. I spent the day evaluating every man I saw. Some were hot, and some were not. I was hooked. I never wanted to be with a woman again. How did I ever think that a woman could satisfy me? Janelle changed my life with that gift.

Janelle,

The weeks went on, and the weather became significantly colder. Pennsylvania weather can be psychotic. November was warm, but now that we were in December, the dress code called for boots, coats, scarves, and hats. I continued to work at Starbucks, which became monotonous, and I wasn’t so happy.

Denise began to spend less and less time at home, and I was often home alone. My sister, who I hadn’t spoken to since I began my transition, called me, which was a surprise. I had been avoiding talking to her because I didn’t want to explain my situation or tell her that I had broken up with Denise.

“Kenny?”

“Kiera?”

“Yes, it’s me, your sister, Kiera. You know, the one you forgot about?”

“I know it’s you, I said.

“What’s wrong with your voice? You sound like a girl," she asked.

“Nothing.”

“Anyway, how’re you doing?”

“I’m just fine. Everything is going great.”

“Well, that’s not what I heard. I talked to Denise yesterday, and she told me you all broke up. What happened?”

“It’s a long story,” I said, as my voice started to relax and become more normal but much higher and more feminine than it was before. This was due to my speech therapy and my daily interactions.

“Do you care to enlighten me?”

“Not really, because I don’t think you’ll approve,” I said with a little harshness.

“You know it’s almost Christmas, and Mom and Dad want to know if you’re coming home.”

“I doubt it very seriously, Kiera.”

“Why?” asked Kiera.

“Because.”

“Because what? What aren’t you telling me, Kenny?”

“Kiera, please don’t be mad.”

“I promise. I won’t.”

“Well, I’ve transitioned.”

“What do you mean you transitioned?”

“I think you know what I mean.”

“No!” Kiera exclaimed.

“Kiera, I’m no longer Kenny Hunter. My name is Kathy Hunter. Or more exactly, Katherine Hunter.”

“You mean you finally did it?”

“Yep.”

“Wow, I knew all those times playing dress up with you was going to give you problems.”

“Kiera, you never forced me to dress up or play with your dolls. This is just the way I am. I was born this way. Denise couldn’t deal with it, so we broke up. I skipped school this semester, and I’m now working at a Starbucks a couple of miles away from where I still live with Denise."

“You still live with Denise?"

“Well, she helped me and didn’t want to see me in the street. Plus, she encouraged me. We actually get along much better than we did when we were a couple. I’m just her roommate now. Just two girls living together.”

“Well, I want to come see you and make sure you’re okay. I guess you shouldn’t come home for Christmas. Is it okay if I come to see you after Christmas? I’ll make the trip down from Blairstown.”

“That’s fine. And how are things in Blairstown?”

“Pretty boring. Mom and Dad still go to the Christian Reformed Church every week and do church activities. I have my own place with Jim. I’m working. Things are pretty much just as they were when you left.”

“So I’m not missing much?”

“No, not at all.”

“Well, come on down. I’ll ask Denise if it’s okay and call you back.”

“Kenny, just be careful out there. I don’t want anything to happen to you. I love you.”

“First of all, it’s Kathy. And I will be careful, and I’ll call you back tomorrow after I talk to Denise.”

"Okay, I love you, Kathy!”

“I know it’s hard, but I love you too.”

That night, I texted Denise and asked her if Kiera could come for a visit, and she said it was totally fine. I thought that this would make for an interesting dynamic. It felt good to hear from my sister. I just hoped that she respected me enough to be happy for me.

The days passed quickly leading up to Christmas week. I had no intention of any kind of celebration. In the meantime, while I was at work, one of the regular customers approached me late in the afternoon. He was a white guy, maybe around 30 years old, and in good shape.

He would often come in almost every day, order a decaf latte, and sit and work on his computer for a couple of hours. He was always very nice. That day, he ordered his usual and then asked if he could talk to me when I wasn’t busy. So when it slowed down, I came over to his table and stood.

“Have a seat,” he said.

“What’s your name?” he asked.

“Kathy. See, here it is on my name tag.” I said that and laughed.

“Silly me,” he said, “I kind of knew that. I just wanted to break the ice.”

“Ice broken." I came back.

“What’s your name?” I asked.

“Bill.” He stuck out his hand to shake mine. “You know, I’ve been coming in here for months now working on my book, and I can’t help but notice you. You know you’re very pretty?”

“Awww, thank you!” I said that and blushed.

“What else do you do besides work at Starbucks?”

“Well, I was in school for computer science. I was working for an IT company before I got laid off. I figured since I don’t have a car, I would find something that’s close to my home. So here I am.”

We continued the small talk for a while until he popped the question. “I was wondering, Kathy, would you like to go out to dinner sometime?”

“Sure. I’d like that. As long as you’re not a serial killer!” I said as we laughed.

“Do you work tomorrow?”

“Unfortunately, yes, I do.”

“What time do you get off?”

“I leave here around 4 p.m."

“That’s perfect. If you want, I can meet you here or meet you at your house. Do you live close to here?”

"Yeah, I do. I live about a mile and a half away. Not too far.”

“What about seven o’clock?”

“Seven is good. Where are we going?”

“I know a little Italian restaurant not too far away that has really great food. Does that sound okay?”

“I’m not a big eater, so I’ll be a cheap date.”

"Well, this place is very nice, but it’s casual attire. No need to get formal.”

"Okay, that sounds good.”

I looked into his eyes, and he seemed to be sincere in his intent. His chiseled facial features made him seem very manly. If I had to guess, I would say that he was either Italian, Greek, or Spanish—some sort of Mediterranean mix.

"Okay, then, it’s set. Can you give me your number so we can text or call, and you can give me your address?”

We exchanged information, including his last name, which was Bill Demarco. He gave me his card, and on the card, it said author and food critic. I thought, well, at least I know dinner will be good!

I was excited and immediately called Janelle when I got on the bus home to let her know. Janelle and I talked almost every day.

“Girl! I just got asked out on a date!”

“Kathy, that’s great news!”

“Who is he, and what does he do?”

“He’s an author and a food critic! So I know he must be well connected. He gave me his card.”

“Wait, I've read his pieces before. He has a blog and occasionally writes for the Philadelphia Enquirer.”

“Really?”

“Yes, now you should prepare for your date tonight. I want you to figure out what to wear tonight so you don’t have to rush when you get home from work tomorrow. I want you to be very ladylike. Let him open the door for you and pull out your chair. Don’t go head over heels for him right away. Play is a little hard to get. Now, is he handsome?”

“Yes, he is. He has a very svelte body and a chiseled face. I can tell through his clothes. He comes in to shop a couple of times a week.”

“What kind of place is he taking you to?”

“He said it’s a little restaurant not far from my job.”

“Find out the name of the restaurant and let me know. I want to know where you are in case anything happens to you. And you call me the minute you get home tomorrow night.”

“Okay, I will.”

First Date.

The next day, after I finished work, I took the bus home. Denise was putting a few things in an overnight bag.

“Denise, are you going out?”

“Yep, I’m going over Bob’s tonight.”

“Oh okay. Well, have a great time.”

I busied myself as I prepared myself to take a shower and do my hair.

“And where are you going, my dear?” asked Denise.

“I have a date.” I said this as I started to take off my work clothes.

“DATE!? Wait a minute. A date with who?”

“Somebody,” I said very curtly.

“Somebody, who?”

“A guy I met,” I said swiftly, trying to get into the bathroom.

“You’re going on a date with a guy?”

"Yes, I am. And a very handsome man. Now please let me get ready, Denise.”

"Oh, this is something I want to hear about.”

“I’ll tell you all about it tomorrow.”

“Okay, well, I didn’t know you were into guys now.”

“Denise, everything must change. There is no sense of you having all the fun.”

“But…”

“But nothing. Isn’t this what you wanted? You said you wanted to help me become a woman. So now I’m becoming a woman who has a guy who wants to take her out on a date.”

"Okay, then, have fun and be careful.”

“See you tomorrow?” I asked.

“Maybe,” Denise answered as she left the apartment door.

I didn’t care if Denise was hurt or surprised. I was ready to live my best life.

After I showered, I did my hair and makeup and got dressed. I picked out some black tights, a red pleated skirt, and a black blouse with red that outlined the sleeves. I figured that it was almost Christmas, so I would go with that.

I wore a black winter coat that Janelle had given me, saying that I needed something a little dressy. I put on some black knee-high boots that I had bought recently at Marshall's. I had a black purse that I acquired during my cross-dressing days that was perfect for the occasion. Not dressy, but not too casual either. I checked myself in the mirror, and I looked quite good! I would date myself.

Bill texted me, saying he would be there in a few minutes. I didn’t give him my apartment number, only the address of the building. I was being cautious. I waited downstairs in the cold, nervously, for a few minutes. I was anxious and wanted to smoke a cigarette, as I did when I got extremely nervous. But I refrained, not wanting to have cigarette smoke on me while on my first date.

Soon afterward, a black Nissan pulled up and flashed its lights. I walked to the car feeling pretty confident about how I looked and, at the same time, anxious about going on my first date with Kathy. As I approached the car, Bill jumped out and opened the door for me. I acted as if to expect it, just like Janelle said. He kissed me on the cheek as he held the door for me and closed it gently.

“You look very nice tonight. It’s good to see without the green smock and black pants on!” He said.

"Oh, thank you. You look rather dashing yourself.” I responded.

“Dashing! I haven’t heard that word in a while!”

"Well, I think it’s better than ‘you look good’.”

We made our way to the restaurant, which was only 15 minutes away. Bill pulled into the parking lot, got out, and opened the door for me. Those little actions endeared him to me. I thought it was sweet of him. The thoughts in my head were running fast. “Suppose he doesn’t know I’m trans? Suppose he gets violent if he finds out. All of these things were of concern to me.

We walked into the restaurant, and again, Bill opened the door for me. He was treating me like a queen!

“Reservation for DeMarco for two.” Bill said to the maître d.

"Yes, Mr. DeMarco, right this way."

We walked through the restaurant, which was darker than normal. I scanned the room to see what other women were wearing. Some had on jeans with boots or shoes; others looked as if they were eating at Applebees. In other words, it is not very dressy. But I was determined to look better than most.

Bill spoke up: “This restaurant isn’t really fancy. But the food here is out of this world!”

“Is that what you do? Write culinary reviews?”

“Yes! Exactly! How did you know?"

“Well, it says it on your card. But I have seen your name under a review in the Philadelphia Enquirer.”

“So you know my work?”

“A little. I’m not an avid reader of newspapers, but I have seen your name and your picture.”

“So Kathy, tell me, are you seeing anyone romantically? Do you have a boyfriend?”

“No, not at this time. What about you?”

“I date occasionally but don’t have a steady girlfriend right now.”

“So I take it that it’s both a yes and a no?”

“Kathy, I’m a man and do have needs and desires. I mean, do you blame me?” He questioned.

“I want to make sure I’m not getting into anything that I don’t agree with. I think you’re a handsome man and certainly a gentleman. I just want to know if I have competition.” I said it with a sly smile.

"Oh, I see. You want to eliminate any chance of getting hurt.”

“Yeah, that’s basically it.”

I was trying to be as adult as possible. I had only been on a date with Denise, and she controlled everything. In my mind, I wanted to be as demure and womanly as possible, but thinking about the words that Janelle left me with, I was on guard. The waiter came and took our orders, and Bill and I continued to make small talk.

He asked me all kinds of questions about my life, including my life in Blairstown, my family life, and how I became interested in computer science. I didn’t want to tell him that I was once an online gamer. That didn’t seem too feminine, but I eventually told him about that aspect of my life. I did tell him of my love for cooking, and that really peaked his interest. The food eventually came, and it was delicious. I ordered chicken piccata mainly because it was difficult for me to make at home. Bill ordered beef with truffle oil over pasta.

He offered me a taste, which endeared me more to him. The meal ended, and we had a dessert and a glass of wine to end the meal. Since I wasn’t an avid drinker, the wine made me a little tipsy and uninhibited. But there was a feeling of uneasiness that remained. I wondered if he knew I was trans. Suppose he wants to go further than a kiss. Suppose he finds out and goes berserk on me.

I had read about cases where some trans women were murdered because they didn’t tell their dates (and in some cases, their clients) that they were born male. I felt it was best to tell him before we left the restaurant. At least I would be in a public place, and there was less chance of him getting violent with me if he reacted negatively to the news.

The waiter brought the check and handed it to Bill. We still had a little wine left in our glasses, and I sipped mine one more time as he looked at the check. I decided to talk to him about it.

“Bill, I want to tell you a little something more, which might be important.”

“Okay, what is it?”

“I don’t know how you’ll react, but I feel like we should get started on the right foot.”

“Tell me what’s on your mind."

I took a deep breath and said, “I’m flattered that you find me attractive enough to take me out on a date. But you should know that I wasn’t born as a girl. In fact, I’m a transgender woman.”

“Is that all?” He said he was smiling. “I knew that. That’s why I find you attractive. You have an alluring look and a very feminine, delicate body.”

“So you knew?"

“Of course, I knew,” he said.

I didn’t know if that was a compliment or a put-down. He continued, “I’ve dated transgender women before. I happen to like trans women. You all are often more feminine than regular women. I find it exotic!"

“Okay, so you’ve had experience with girls like me?” I asked.

“Yes, I have, and I’m not ashamed of it. I think transgender women are beautiful.”

"Okay, but I don’t have much experience with men at all. As a matter of fact, I’ve never been with a man.”

“It’ll all come naturally. You’ll see,” said Bill as he winked at me.

At that point, he got up and held my hand as we departed the restaurant and walked to the car through the cold night. He opened the car door for me and then walked around and got in on the driver’s side. He started the car to let it warm up. I was shivering. And then she asked, “Are you cold? Here, let me warm you up.” He then put his arms around my neck, leaned over, and started kissing me on the lips. Before long, he stuck his tongue inside my mouth. I had never been kissed by a man before that.

The feeling of not having to perform for a woman relaxed me. He soon started to put his hands around my body, touching my thighs, and then his hands proceeded to slip underneath my blouse and up to my small breasts. He lightly rubbed my nipples, which made me hotter than hot. I started to moan, and I could feel my arousal increase. We calmed down a bit, and then he said, “Let me take you home.”

He drove slowly down the street in the direction of my apartment, all the while keeping one hand on the wheel and the other hand on my leg. I was still vibrating from the make-out session just minutes ago. Just then I realized I hadn’t texted Janelle, and she had texted me three times to see if I was alright. I texted her back, saying, “All is well."Dinner was wonderful. Bill is a perfect gentleman. I'm heading back home now. I will text you back once I get inside.”

Bill pulled up outside of my building and left the car running. I was torn about whether or not I should invite him in. The temptation was there because I had the apartment to myself.

“What’s the rest of the night like for you?” asked Bill.

I caved. “The night is still young. My roommate is out for the night. I guess I’ll just stay up and watch a movie.”

“Would you like to have company?” asked Bill.

“Sure, you want to come in and see where I live?”

“Absolutely!”

"Here, park the car over there in front of this garage.” I pointed to the garage, which had the number 52 over it.

I led Bill up the set of 4 steps to the door and then up a flight of steps to our 2nd-floor apartment. Once inside, I hung up our coats on the hook by the stairway.

“No Christmas decorations?”

“No. Things haven’t been too holly and jolly around here. Plus, I’ve never been into religious holidays. I think Christmas is a farce. It’s just another way for people to earn extra money and for the government to stimulate the economy.”

"Yeah, but it doesn’t have to be that heavy. I just celebrated the winter solstice. I grew up Catholic, but I don’t go too hard with the holidays. Just a time to reflect on the year and mentally prepare for the long winter ahead.”

“That's a good way to look at it,” I replied. “Would you like a glass of wine?”

“Sure.”

“White or red?" I asked.

“Red,” he said immediately.

While I went to the kitchen to get two wine glasses and the wine, he perused the pictures in the living room. Luckily, Denise had removed all of the pictures of her and me together.

“Wow! This is your roommate?”

“Yes, that’s Denise,” I said no more. I wasn’t about to give him ammunition for the future. The less he knows at this point about our relationship, the better.

“She’s a good-looking woman!”

“Yes, she is,” I said with resignation.

“But you’re just as good-looking!" Bill said as we both sat down on the couch very close together.

I turned on the television and looked for a movie on our cable menu. “What would you like to watch?” I asked.

“You’re the one who said you wanted to watch a movie.”

“Well, I was just saying that because I didn’t think I was inviting you in.”

I left the television on the regular local station as he slid his hand around my thin waist.

"Here, come closer,” said Bill as we started to kiss.

I put my wine glass down and started to kiss him back, feeling the slight stubble on his face. As he stuck his tongue in my mouth, my body started to quiver a bit. My head rested on the arm of the couch as he gained the upper advantage over me. My hands ran over his muscular body. My arousal was quite palpable, as I could feel his hard penis up against my leg.

I grabbed it with my hand and started to massage it through his pants. He continued to kiss me with more and more passion. He then whispered in my ear, “Let’s get more comfortable.” I agreed and led him down the hall to my bedroom. “I’m sorry, I only have a twin bed.”

“That’s all we need," we said as we threw off our clothes.

I stayed only with a bra and my pants while he completely undressed, letting me see his hard, stiff penis, which was at least 9 or 10 inches long. I grabbed it and started to lick it, tasting his pre-cum in my mouth. I put one hand on his penis and the other in my mouth.

Soon I released my hand and let him stick the entire hardness down into my throat. We then lay down next to each other as I stroked his still-erect penis. I heard a wrapper of some sort and then figured out that he had brought a condom with him. I took off my bra and pants but covered my privates with my hand.

“You don’t have to be shy,” he said, rolling the condom down his thick, hard penis. “I won’t hurt you,"

He turned me over before reaching for a jar of Vaseline that sat on my vanity. With two fingers, he rubbed vaseline over my rectum and then pulled my waist up. I could feel him slowly and steadily push his penis inside of me.

“Just relax, baby. Daddy’s here.” as he pushed it further and further into me.

Soon, he thrust himself back and forth inside of me. I moaned with light, intermittent screams until I heard him let out a grunt and then a sigh.

The lovemaking ended gently and softly with kisses. We got up and showered together, then fell asleep on my little twin bed. We spooned and fell asleep, my small body up against his roughly 160-pound muscular body next to mine. Bill awoke early, kissing me on the side of my face. I made him coffee and then bid him goodbye around 8 o’clock that morning.

Making love to a man was an entirely different feeling than when I made love to Denise. I didn’t feel the pressure to perform. Having a man inside of me was a lot easier and more satisfying than the other way around. I felt giddy as I went about the day. Later that day, Denise would come home to get a fresh set of scrubs and get ready for work.

She asked me how things worked out with my date. I only answered, “It was nice,” and I said no more. Inside, I thought to myself that I wanted more. I retired to my room for the rest of the night and dreamed about Bill and the first experience of making love to a man. This was another major turning point for me. All of a sudden, I dreamed about what it would be like to get married to a man.