Transmogrification Ch. 01

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A bewitching night.
2.9k words
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Part 1 of the 7 part series

Updated 06/11/2023
Created 11/19/2021
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grgy56
grgy56
1,564 Followers

I like to dress up.

I really like to dress up as a female.

That said, I am a male but not gay. I just love crossdressing. I've been crossdressing for years and my wardrobe had grown extensively over that time. The taboo feeling of putting on women's attire was cock-hardening that never failed to result in mind blowing orgasms.

It started many years ago. Back then, the Sear catalogue was delivered to homes. I spent a lot of time staring at the bras and panties the models wore in the coloured pictorials. My Dad bought many adult rags like Playboy, Penthouse and Mayfair to name a couple. While I "enjoyed" the pictorials of extra-sexy, naked women, I was ecstatic when the pictorials included the models dressed in stocking and garters.

Like many young men, I started my fetish at home. While riffling through my Mom's dresser, I came across some very sexy lingerie. Don't ask me why I did it. I just did. While I loved her very much, I had no Oedipus desires for my mother.

In any event, I nervously laid out the entire sexy set: black lace bra, diaphanous, black nylon panties, black lace, four strap garter belt and black 15 denier RHT stockings with thick welts. Getting dressed, I started with the bra. I hooked the eyelets and spun the bra around so I could pull the straps over my shoulders. My cock was already hard. Panties were next. My erection tented out from the loose fitting undies. I hooked the garter belt and slide the silky-feeling stockings up my legs. Logic helped me solve the "attaching the clips to the welts" question.

Of course not being a woman, I did not realize panties should go over and not under the garters. But as my crossdressing continued, depending on the panties, I found it sexier to wear them beneath with the idea of restricting how far I could push them down my thighs.

With no one home, I pranced around but was very careful not to snag any of my new found treasure. The problem was, I had no idea when my sisters or parents would be back (BTW, I never had any thought of looking through my sisters' underthings). I laid on my bed and jerked off until I came on my belly. I needed to be careful not to "Monica Lewinsky" on any of my new outfit.

After moving out and away, the number of pieces increased. Initially, I would steal some panties and things out of the washing machines or dryers in the apartment's basement laundry room. By the time I got back to my own apartment, my heart was beating so hard, I thought it would explode.

In person shopping was exciting for me. Pretending to buy for my non-existing girlfriend, I bought a number of bras, panties, stockings and garters. Then when the concept of on-line shopping exploded into a massive industry, it was easy for me to make my purchases anonymously.

A couple of years ago, I came across a crossdressing site that sold breast forms. Up to now, while I wore my bras beneath some baggy sweatshirts when I went out shopping, the C-cups were unfilled. I ended up buying a fairly decent set of breast forms. They were equivalent to C's to fill the cups of my bras.

Later, C's went to Double-D's and today, G's. I just wanted bigger and bigger boobs. The G's were a lot better quality and more expensive, nearly a thou. They were much more realistic with big nipples and colouring. They were also self-adhering which eliminated them shifting around too much. If I glued them on, I could wear them continuously for a number of days if I so desired. Each side weighed almost two pounds and I loved the heavy feeling they gave me whenever I wore them.

I continued to dress up when I could but never had the guts to actually go outside en femme. The furthest I would dare was to my car in the driveway. And that was after making sure no one was around to see me (although I guess I secretly wanted to be caught).

A good friend of mine had planned to hold his annual Halloween party. Normally, my costume would be more male oriented like a monster or a ballplayer. This year I was determined to go dressed up. I bought a sexy nurse outfit and some new lingerie to go with. I was so excited. I wanted to do the whole nine yards, but my technique for applying make-up was less than desirable. I had planned to get it done professionally. I booked an appointment at a place and explained what I planned. I wanted to make sure people really had a hard time recognizing me.

Finally the party day had arrived. I started at home with some baby blue contact lens to cover up my brown eyes. I laid out my outfit, lingerie, shoes and stuff before having a soak in the tub. I made sure that every unwanted hair on my body and face was gone, leaving only my smooth, soft skin.

Then at the spa, the real transformation began. A mani-pedi with long, fake glue on nails painted a bright, sparkly red. My middle right finger had a fake crystal attached to it. Then they started with my lashes. Gluing individual strands to my existing ones was a long ordeal. Plucking my brow was pretty painful. They applied some heavy make-up that gave me sexy, smoky eyes and high sculpted cheekbones. Mascara made my long lashes, longer and thicker. I loved how they fluttered as I blinked.

Even though I had a couple at home, I had asked them to find a wig for me; long, blond and big. After putting on a hairnet, they secured the wig to my head. Even with hard yanking, it would be difficult to remove. And then finally, they did my lips with some fiery red lipstick and liner protected by a shiny gloss. I looked in the mirror and even I had a tough time seeing the male me.

The final price was pretty costly but with the job they did, I thought it was worth it. And I gave them a huge tip. They gave me a hair kerchief to protect my hair before I pulled over my hoody to hide everything.

At home, I entered the hallway and smiled as I spied myself in the mirror. I was really pleased and amazed at the result. But the transition job wasn't done.

While the forms were self-adhering, I didn't want to take any chance with them coming loose or moving around and so I glued them in place. The colour match was pretty good but blending make-up made them look a part of me. I took time to play with them before cradling them in a red, lacy, push-up bra. The hi-cut, bikini panties were similar colour but were made in satin. They were tight and held my man package securely. The red garters had the same lacy pattern as the bra had. I clipped each of the thick, straps to the six inch, lace welts of my black fishnet stockings. I made sure each of the eight straps were straight (Like I said, I love wearing my straps over my panties. So much more sexier to me.).

The nurse's uniform was white with some red trim and a red cross over the bosom pocket. I did the four front buttons; difficult with my new long nails. The hem was higher than mid-thigh. With my big "G" boobs attached, the uniform was a tight fit around my chest and strained the buttons. The top button was actually below my nipple line and the wide, open Vee neck exposed my deep cleavage and some bra.

The shoes were red patent leather, open-toed pumps with a one-inch platform. The six inch, skinny, steel stilettos heels ended in a pointy point that made sharp clacking sounds as I walked on any hard flooring. There was no way I'd be able to drive there with these shoes on and since I was planning to drink, I ordered a limo for the evening. There was still an hour before it got here so I while I waited, I poured myself a double of single malt. I nervously sipped it and found the glass empty pretty quickly. "One more before the car get here!"

By the time I was half finished my second glass, the limo arrived. I gulped the remaining amber liquid and clacked my way down to the waiting car. I was wearing a red lined, black cape with a hood to cover myself up. It was cold and dark out as I slid into the back seat.

"Good evening, Miss." The driver greeted me. "I'm James."

"Oh my god! Does he actually thinks I'm a woman!?" I thought. Of course I opted to go with my alter-ego name. I giggled my response. "Good evening, James. I'm Roxanne!"

"Just to confirm the address, Miss Roxanne." James now in the driver seat, turned to face me. He was quite good looking. "2-8-1-4 Balling Boulevard. Is that correct?"

I always laugh at that number. I chuckled my response back. "Yes, 2-8-1-4 Balling!"

I had planned to arrive a bit late but traffic made me even later. When the limo pulled up to the house, the music was blaring and the party was obviously going hard. James held the door open for me. I slipped my right foot out the door knowing my hem would probably ride up and show off my stocking welts and garter clip. I wasn't sure if he could see my panties though. To his credit, James made no remark or reaction as I placed my other foot outside and slide my bum off the leather seat. "Please enjoy your evening, Miss Roxanne. And let me know when you would like to return home."

I took positive strides to the front door. I rang the bell but I doubted it anyone could hear it over the blasting music. The door was unlocked anyways.

Inside, I looked around for the host, my friend Brady. There was a sudden gargantuan laugh. I knew it was him. He was dressed in a white, Buc's jersey with the number 12; his favourite player. We locked eyes. He gave me a semi-unsure look but couldn't recognize me in my outfit. Brady made his way over to me. In a slight uncertain voice he said. "Hi! I'm Brady. And you are..."

"Me. Brady. It's me." I told him. He stared at me as if we were strangers. "Me. Geremy!"

Suddenly, it struck him. His eyes popped and his chin dropped. "Holy... Holy shit! Gere! Holy shit! I didn't even recognize you."

"Yeah, it's me. That was my plan. Don't tell anyone else though." I told him. "I want to see their reactions."

The night continued and the alcohol flowed freely. I floated and flaunted around and laughed to myself as some good friends had no idea I wasn't a female. A couple of them even flirted with me. One gave me a hug; another put his hand around my waist and then on my bum. I was having so much fun.

I went to the bar to get another drink. As I turned back around, I found myself face to face with an Anne Hathaway "The Witches" doppelganger. She was dressed in black hound tooth and she was very pretty. We locked eyes; I was paralyzed by her gaze. I felt her fierce, dark stare deep into my sole. I blinked and she was gone. I looked everywhere for her but nada.

The rest of the evening was a blur. Honestly, I'm not sure when it ended or how I got home. I awoke with a groggy head, an aching jaw and a throat full of sand. I was on my back, on my bed. Every muscle and joint ached. My chest, groin and butt felt strangely sore. "Oh fuck! What a night!"

I struggled to lift myself up. I was still dressed in my nurse's uniform although the white was now smudged with hand prints. A couple of buttons were missing and my fishnet stockings were shredded. "Phhtt!" I spat my hair from my mouth. I tried to remove my wig but "Yeow!" It felt like I was pulling off the top of my head.

I undid the remaining buttons and found I no longer wore my bra or panties. Knowing they were securely glued, I carefully tried to remove my breast forms. I cradled my left side. It felt strange. I could feel the warmth of my hand on the skin. I guess I did a great job gluing them on because I couldn't find the edge to peel the form from my chest.

"I guess I'll just have to wait until the glue gives out a bit more or use the glue remover." I flopped back on the bed. A hand involuntarily started to fondle my boobs; and then the other. It felt really good. I pinched my nipples. The shock went from my chest to my groin. My other hand searched for my dick. I couldn't find it. There wasn't one there. Instead I found a slit... A wet slit. I bolted back up and looked between my legs. "I have a cunt!"

The shock of my prick being replaced by a pussy shot adrenalin through my body. I was wide awake now. "What the fuck?"

I placed my feet on the floor. The fact that I still had my stilettos on was the least of my concern. Standing up, I was a bit wobbly but made my way to the mirror. I had that "just been fucked" appearance. Again, I carefully tried to remove my breast forms. Nope! With a closer look, it seemed that they weren't just attached, they were part of me. The silicon boobs were now skin and fat like firm, real, big breasts.

There was some wetness leaking down my inner thighs. It was coming from my cunt and asshole. I used my fingers to collect some and sniffed it. It had the odor of stale pussy juice and cum and shit. "Fuck! What happened? I don't remember a thing!"

I thought a hot shower would help. It did. I felt a lot better. My hands caressed my body with the soapy suds. I played with my huge, hard nipples for a while. My pussy was tingling. A finger found my clit. I came hard as soon as I touched it. A little bit of spray came out.

I washed out any remaining cum from my butt and pussy before rinsing and drying off. I looked in the mirror and was a bit taken aback. Rather than being scrubbed away, it looked like my make-up was still freshly put on. I tried a bit of make-up remover but it did nothing. My lashes were still long and thick and my eyes were still baby blue! Of course my body was still hairless since I shaved it off but my skin was silky soft and smooth. The reflection in my full length mirror showed an image of a hot shapely babe with huge tits and legs that went on for ever. My bum was nicely rounded and firm but giving to the touch. I looked like something I would definitely hit on... if I were a male.

I needed to find out what happened. I called Brady.

"Aauuu... Hello..." Brady sounded like shit. "Wha... What!"

"Brady! It's Geremy!" I said excitedly.

Suddenly, he seemed to pick up but his response was really strange. "Roxanne! Wow! Hi!"

"No. Brady. It's Geremy! Gere!" I repeated.

"Yeah. Roxanne!" He seemed oblivious. "Wow! You were great last night! Thanks!"

No, it's Ger... Never mind! What the fuck happened? I don't remember anything!"

"Well near the end of the party, there were only a few of us left. Your head was in Bob's lap sucking on his dick. You insisted I fuck you from behind. What a tight cunt you have!" Brady related.

"Wait! What! What the fuck are you talking about?" I asked unbelieving. "No! No...no...no!"

"Oh yeah! Then after you were finished with me and Bob. Gary and Dick took over followed by Rod and Harry! Then Bill and Cornell started corn holing your ass. We all rotated until we couldn't get it up any more." Brady continued. "And you still wanted more. You found a banana and started using that until we recovered enough for one final cycle! I don't know how many loads you took."

My mind was stunned at the unbelievable fact I had my friends all fuck me while I sucked them off. "How... how did I get home?"

"We stuck you in a taxi!" Brady continued. "Wow! You were a real slut!"

I tried to process what Brady just related to me. At least now I understood why all my holes were so sore. "There was a girl dressed up as a witch. She looked just like Anne Hathaway. Who was she?"

"What! What are you taking about?" Brady answered with a question. "There was no witch there! Certainly no one that resembled Anne Hathaway. Yeah, Hathaway is hot! I'd fuck her if she let me!"

"Brady, you'd fuck anything." I hung up the phone. "Last night just proved it!"

grgy56
grgy56
1,564 Followers
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