Anal

Prequel: Life before "Meeting Jim"

A transformation complete.

Spankmasters
Jul 17, 2024
11 min read
fetishescdPrequel: Life before "Meeting Jim"gay male
Prequel: Life before "Meeting Jim"
Prequel: Life before "Meeting Jim"

Prequel: Life before "Meeting Jim"

I met Jim Moon online in a chat room, in April of 2002. It was my first time in a local chat room, after I moved to Florida from Virginia. We chatted online a couple of times, and ultimately decided to meet. We spent a wonderful weekend together.

By the end of the weekend we had committed to going steady. This was uncharacteristic for me, I was always cautious and guarded. My genetic disorder would make a steady, intimate relationship difficult, and knowing this made me hesitant. But the way he made me feel, and the intense pleasure I felt when he was inside me, was too great to resist.

I had been sheltered growing up, so my experience with men was limited. I was in my early twenties, the first time I ever went on a date.

In the small community I grew up in, my dad was the town cop. My mom was an armed guard for a coal company. I had an older brother who resented me from the day I was conceived. He was three years older, and though we grew up together, our lives were very different and separate. I had to have several surgeries in my early childhood, the final one being done when I was seven.

Being from a small community, everyone knew everyone, and a great many of them were related, or descendants of prominent families, or both. So when I was born with Kallmans Syndrome, a rare and unusual genetic disorder, the community was respectful to my parents and family.

I don't know if it was because my grandmother, a former Mayor, was a wealthy and somewhat sharp and respected or feared Irish politician. Or if it was genuine compassion for the plight my parents and family were confronted with. Either way, I was protected by the community. No one mentioned, or made fun of my condition. Not other kids or adults.

I made friends with all my classmates in kindergarten, and we all went through to graduation together. The boys were nice to me, but my closest friends were girls. My best friend was Karen Smith. I missed a lot of school due to medical appointments, but when puberty came I missed most of my eighth grade year.

The issue with my puberty was that my body was maturing, and began producing large quantities of Estrogen. As it turns out, because my genitalia was deformed at birth, and unrecognizable, my parents were given an option of male or female. They chose male, because that surgery was not as complicated and detailed as the surgery for a female choice. They were trying to avoid the pain and suffering of a long recovery I would endure with a female choice surgery.

As puberty arrived my voice was getting higher, my legs and hips were getting long and slender, and I was developing breasts. After several tests it was determined that my brain was female. There's more science and other terms to further explain it, but that's basically what it boiled down to. Since I had already had surgery. The only option at that time was to adjust the hormone therapy and allow my brain to dictate how my body developed. By the time I was sixteen, I had B cup breasts, and very little body hair. I wrapped them until I graduated, and a few times through college.

I never crossdressed, my parents raised me as a boy, and called me Mike. Though, rather than naming me Michael, my mom named me Mykaela. She always told me it was a Gaelic name, to remind me of my Irish heritage. I later learned she was also thinking ahead and giving me future options.

Dating, intimacy, those things just weren't part of my life, and it didn't bother me. No one ever showed a romantic interest in me. I liked guys, and I had my secret teenage crush's on male tv stars. My first date was with a guy, I was twenty two. It was set up by my best friend Karen. His name was Joe Kemp. He was her college tutor, he was twenty eight, and he was openly gay.

The date with Joe was awkward from the beginning, and stayed that way throughout. When it was finally over, and I turned to open the door to get out of his car, He grabbed my hand and said.:

"Wait a minute, I want to talk to you."

My eyes were already welled up with tears because of how awkward the date went. And I didn't want him to see me crying. With a cracked voice, I apologized for how the date turned out and opened the car door. Joe gripped my hand tighter and firmly said.:

"Mykaela please! Sit down and close the door."

I wiped my eyes and cleared my throat and did as he told me. He took hold of my other hand and said.:

"Listen baby, you're a beautiful girl. I know you're a guy, but sometimes people come in the wrong package. In your heart, and in your mind, you're a girl. Its quite obvious, even your body tends to agree! You have to accept yourself and surrender to your true nature and be the woman you are."

Through sobs and tears I said: "I don't know how."

Fully crying now, sniffling and sobbing I repeated.: "I don't know how!"

"What do you mean you don't know how?"

Joe responded inquisitively.

I'm sitting in his car pounding my legs with my fists as I began to list all the ways I'm inadequate:

"I'm not complete. I'm not a man or a woman and I never will be. I don't know anything about makeup, or women's clothes. Who is ever going to want me anyway? I can't date women because I'm not equipped. Even with gay men I have to be equipped, otherwise they wouldn't be gay. So I'm a useless...Creature and I always will be."

Joe listened intently as I cried and wished I had never been born. He gently held my face in his hands and wiped my tears off my cheeks as he shook his head and said:

"Oh baby don't ever wish that. You're a beautiful woman with a beautiful soul. You have a kind, loving, gentle heart. The Creator put you here for a reason. There's a man out there that's going to be very lucky to have you. And he's going to love you. You just have to try."

I was still sobbing and sniffing, but gaining my composure.:

"I still don't know how."

"We can fix that, I have a friend that can teach you everything you need to know."

I gathered my composure and thanked him as I got out of his car. I apologized for losing my composure.

A few days later, Joe called me and asked if he could come by and pick me up. He wanted me to meet his friend. When he came by and picked me up, he drove in silence until we came to a bar/nightclub called "The Castle." As we pulled into the parking lot Joe said.:

"You're going to like Terry, I told her about you, she'll know what to do."

We went in the back door, so as not to attract attention. He led me through a narrow hallway to the back stage dressing rooms. Terry was sitting at her dressing table putting on lipstick. She looked up in her mirror as he introduced me. Then he handed me off to her, stating that he would pick me up later.

Terry was a heavyset lady. She had thick long curls, dark eyes and a perfectly smooth white complexion. She was wearing a purple and blue flower print floor length dress. She was very classy, and very pretty.

To my surprise, Terry was a gay man. His day job was as a hairdresser, but She headed up the nightly drag shows at "The Castle," which, as you have guessed by now, is a gay nightclub.

I was a little embarrassed and definantly shy. Everyone around the community knew "The Castle" was a gay bar. I had never been in there before, but admittedly I had driven by it a few times. Though I could never work up the courage to go in. I was a very shy and timid twenty two year old.

As she looked at me in her mirror, her first words to me after introducing herself were.:

"Joe says you don't know who you are."

She put her lipstick down firmly and swiveled her chair around to take a closer, direct look at me.

"He brought you to me to find out...We're going to find you in there."

She said as she pointed at me.

"So lets get to it. What's your ethnicity? I need to know, to choose the proper makeup."

"Well, my Dad is pure Mexican, and my Mom is pure Irish."

"Ah that explains the olive complexion, and the red tint in your hair."

She instructed me to go to the changing room and strip down to my underwear. I did as she instructed. When I came out in my wrinkled boxers and a white sports bra that was two sizes too small, Terry rolled her eyes and shook her head.:

"Good grief, are those comfortable, and what's with the tourniquet around your chest?"

"No it isn't comfortable, but it helps me look like a normal guy. The boxer shorts wad up in my pants and make my inner thighs raw, but it gives me a bit of a bulge. The sports bra compresses the breasts my disorder developed so they're not so noticeable."

"Yes Joe mentioned that...And before you get upset, Karen told Joe. She just wants to help you. Now, lets get that tourniquet off."

Before I knew it she grabbed a pair of scissors and cut it off. My breasts flopped loose, they were red with deep marks from the pressure of the sports bra. She reached over and put her hands on them, massaging them to smooth out the compression marks as she said.:

"Just think of me as a massage therapist or a Doctor."

She continued to squeeze and massage my breasts, when she finished she measured them and said:

"Those are a B cups."

She measured my waist which was about twenty six inches, and determined I was a size two.

She got up and walked over to a clothing rack and thumbed through some bras, plucking one out. Then she opened a drawer and pulled out a pair of thong panties. She instructed me to put the outfit on. I went into the changing room and put them on. They fit perfectly, and they were so comfortable. I was amazed how free and comfortable I felt!

Soon, I was changing clothes and trying on different things. She gave me tips, and taught me about "Tucking" though I didn't have much to tuck.

My undeveloped testicals were removed when I was an infant. There were undeveloped ovaries left inside me. I do not have a scrotum. My penis is about three inches long, maybe four inches when excited and about as thick as a woman's index finger. It is functional, to urinate and cum, but I had sit to urinate since childhood, because my mom got tired of sitting on a wet toilet seat. I tried to clean up after myself but I was a child, so my mom strongly suggested that I. "Sit to pee."

I already had long hair because that was the popular style. My hair was thick, jet dark brown, with a red tint, and rested heavily on my shoulders. Everyone around my age had long hair. We all got our ears pierced, around the same time, guys and gals both.

She put makeup on me, and showed me how to use it. Base, blush, powder, eye liner, lip liner, lipstick, eyeshadow, mascara, false lashes, false nails and body tape. She took me to the sink and taught me how to shave my legs. By the time she was almost finished, my head was spinning trying to remember everything she said about all this makeup, and everything else.

When she was finished, I was wearing a white pleated mini skirt and a cropped tee shirt. My recently liberated breasts lifted the front of the shirt. and raised the bottom of it, exposing my navel. She covered my eyes and guided me to the mirror. When I saw myself in the mirror I was in shock. I looked nothing like I did when I arrived. In fact I barely recognized myself in makeup. She had cut and styled my long hair into a feminine cut, that laid halfway down my shoulders. She picked up her phone and called Joe,

"I'm finished for today, come and see what you think."

Joe arrived about five minutes later.

"Wow Myka! You're beautiful. Do you like it?"

I nodded yes, as he spoke to Terry: "Good job Terry, she looks fantastic!"

Terry agreed, and smiled, "She's a natural. She has a sexy abdomen, she should get her navel pierced."

Terry began packing the makeup in a box and gathered a few clothes. She handed the box of makeup and the clothes to me.:

"These will get you started, You're a girl, you need to practice putting your makeup on. Shave your legs and body on a regular basis, I know its just peach fuzz but smooth looks much better. Also stop and get tools, You'll need nail clippers, scissors, and a lighted magnifying makeup mirror to start with."

When Joe and I got in the car, he said.:

"We'll stop at the store and pick up the things Terry mentioned. Then we'll go to your house and show your mom how good and natural you look."

I panicked! "No way! I've got to stop somewhere and get this makeup washed off and change clothes!"

Joe abruptly pulled the car over and put it in park and turned to me and said.:

"Look Mykaela, You're twenty two years old. You still live at home with your parents. They already know you have an issue, and in my opinion, it's partly their fault. If they don't like it, or if they throw you out, you can move in with me. But you have to do this."

I hesitantly agreed. Joe put the car in drive and pulled out. When we got to my house, Joe suggested I just knock on the door, and see how it unfolds. So I went to the door and knocked. My dad was sitting in his recliner, reading the paper. I heard him yell to my mom that some girl was at the door, "Probably peddling magazines."

My mom came to the door and opened it.

"Yes?"

"It's me mom."

At that moment time slowed down. I saw her eyes widen, first with curiosity, then immediate recognition. She opened the door wider and grabbed my arm:

"Get in here! as she jerked me into the house."

She looked at me a few seconds, then wrapped her arms around me and hugged me tightly. She started crying. My dad heard her crying as he walked into the foyer.

"What the hell's going on?"

My mom turned me toward my dad.

"What do you think?"

It was a double meaning question, My mom was good at that.

I saw my dad recognize me. He looked me up and down, gave a small smile and said:

"Alrighty then. Is this to be a permanent change?"

"Yes, If that's okay?" I said timidly.

"I don't care, if this is what you want. But I have to say, I don't care for that outfit. If this is your choice, then you conduct yourself like a lady, and dress respectably.

My mom chimed in:

"I think she's beautiful. She looks like me when I was young."

"Yeah, She's pretty, she just better be sure this is what she wants."

Mom hugged me again, and offered to teach me about makeup. She told me we would go shopping for some clothes. Then asked me if I was going out with Joe.

"No, we're just friends."

That was five years before I moved to Florida and met Jim. By the time I moved to Florida, my wardrobe consisted of jeans and tee shirts, and white leather sneakers. I could still be feminine, but tom boyish. I still had a few feminine things I wore around the house, and some other things packed away.

While my parents were supportive and completely understanding, I didn't want to attract attention. I moved in with Joe, as a platonic roommate. Over the course of time and events, Joe met and married a guy named Perry. Joe come to view me as his little sister.

I lived the next five years with them, working, saving money and quietly maintaining my body, learning to use makeup, and learning how to walk gracefully in heels. I would go on a date maybe once or twice a year. So at twenty seven, when the opportunity to take a position as a bookkeeper, in a small Pagan art and book store in Florida came, I took it. Joe and Perry, convinced me this was the opportunity to start a new life, living as the woman I was meant to be.

My parents bought me a white, 2002 T top Camaro Z28, with all the bells and whistles, To start my new life.

In the piquant world of his fetishes, Joe introduced Mykaela to Terry, a drag queen and hairdresser at a gay nightclub, who helped Mykaela discover her feminine side. This was a significant departure from the prequel's narrative: 'Life before "Meeting Jim"'.

Embracing his gay identity, Mykaela attended drag shows at 'The Castle', becoming an ardent admirer of Terry's charisma and flamboyance. This fascination led him to amass a collection of CDs featuring female impersonators, showcasing his ever-growing fascination with the drag scene.

Read also: