Chrysalis of Kirsten Ch. 03

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am.

A special thanks to Shy Girl Whore for her help with polishing this story!

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Into the Looking Glass

The next day, around 10 in morning, the phone rang. Julie handed it to me.

"Hello?" It was Greg.

"Hi Kirsten, I want you to come by today." he said. It was more of a command than an invitation.

My first impulse was to say 'no', but I couldn't.

"Sure, what time?"

"How about after lunch," He answered.

"That's fine, see you then."

He gave me his address and I hung up. I didn't know what I was thinking. I told Julie and she mentioned to me that he was into domination and submission. Just keep that it in mind she said. I dressed in a floral pleated skirt, a pair of black tights and a turquoise Cowell neck sweater. My makeup was nude eye shadow, eyeliner, mascara and a nice apricot lipstick. I hailed a cab. Greg had a nice house in the Richmond district with a view of the ocean.

His house was nicely decorated and extremely well kept. It appeared that he traveled from all the native artwork he had. He did have a couple of H.R. Geiger prints which I found interesting. He offered me a drink and I chose a glass of red wine. We sat on a couch in a small den off the living room. He showed me the grave rubbings from Hungary that he spoke of at the gallery opening.

"So what do you like to do Kirsten?"

"Much of my time is spent on my artwork and working at the gallery. I need to come up with a portfolio for the academy."

"What do you do, work wise?" I asked.

"I'm a software engineer. I work as a sub-contractor from home."

"That must be nice, to be your own boss."

"I definitely has it's advantages." He replied.

An hour had passed and he went into great detail about the adventures he had and the places he had been. He was very interesting. He spoke of his adventures in a genuine fashion, truly fascinated about the cultures he experienced speaking without braggadocio. We moved to a leather couch in his living room.

"I noticed you have a very subtle accent. Where are you from? I don't mean to be intrusive." I asked.

"Not at all. I was born in Trondheim, Norway. My father was a fisherman. His brother moved to San Francisco in the '60's and started a fish wholesale company. He asked my father to move here and help him run the company. I was 8 years old when we moved here and didn't know any English. I was held back a year in school because of it. My accent has never completely disappeared." He replied.

"Come over here and stand in front of me." I did so without any resistance. I started feeling the weakness in my knees and butterflies in my stomach.

"Kneel down."

I knelt without resistance. I was wondering if he was some kind of Svengali casting a spell on me! He unzipped his trousers and pulled out a huge cock! It was about 9" long and 3" in diameter. The glans had a pronounced flair that was very sexy! He had a curved barbell, 10ga Prince Albert piercing and a small ring behind his scrotum I later found out was called a Guiche piercing.

One of the ball of the PA was right in the end of his urethra. At the base was a large steel cock ring. He was completely shaved which made him look larger. Without thought, I took it in hand and started run my hand up and down the shaft. In an instant, he was fully erect. Without prompting, I took the head in my mouth and swirled my tongue over the head. As I did, I played with the Guiche piercing. Greg was hard as a rock!

"Take it deeper into your throat." He said softly. I tried but I started gagging with about 5" in. I sucked his dick for about 5 minutes and he lifted me off. He stood up, took my hand and led me to a room.

The room had a bed that was made out of 4x4's painted gloss black and an overhead frame work with eye bolts in various places. There were racks with cat-o-nine tails, riding crops, leather waist belts, leather wrist and ankle cuffs, hoods, ball gags, etc. There was a chain hanging from a large eye bolt in one corner.

Most of the wall space was covered with mirrors, including the ceiling. In the corner opposite the hanging chain was another room, hidden by a curtain. I was kind of anxious. He sensed it.

"Don't worry, the first time is easy." First time? I thought What have I gotten myself into? I asked myself.

"Take off your clothes." He said and I complied without resistance. He lead me over to the hanging chain. He took a wide leather belt with multiple D-rings and fastened it around my waist. As he did, he looked me in the eye gauging my reaction. I felt like a mouse cornered by the cat. He then placed a wrist and ankle cuffs on me.

The cuffs and belt were fur lined and comfortable. He fastened my wrists to a couple of rings on the side of the belt. Greg attached the ceiling chain and adjusted it to a point where I was flat on my feet but had very limited movement. He then attached a spreader bar between my ankles. He put a collar on me and attached a chain that was connect to the floor. I couldn't stand up.

Greg made a point of walking around me and occasionally pinching a nipple and squeezing my cock. He put on a pair of rubber gloves. I felt something cool and slippery on my asshole. Then he inserted one finger, working it around. Then there were 2.

"Relax and don't fight. It will be more enjoyable." he said.

Finally he had 3 fingers working around in my ass. He pulled them out and I felt his cock forcing it's way in. It was large and straining my sphincter to the point of pain. He stopped and I heard the open and closing of drawers. He placed a blue dust mask on my face that had a piece of cotton with something that smelled like solvent: it was Amyl.

Amyl Nitrite is a cardio-vascular dilator used for heart conditions such as angina. It was quickly discovered it would intensify anal sex and help relax the sphincter muscle. It became very popular with the gay community. I became very light headed. He removed it and immediately started to push his cock into my ass. My rectum just sprung open! He slid the shaft in balls deep and started stroking in a slow rhythm.

This was pleasure beyond belief! Greg increased the rhythm and was hammering my ass! After about 3 minutes, he stopped abruptly. Then he rolled me over.

"Please don't stop," I said in a meek voice.

He then place a clover clamp with small weights on each nipple. It was intense and another level of sexual excitement. He then placed the mask with Amyl Nitrite on my face. I took a number of deep breaths, to the point I was really spinning and my ass dilated. Greg mounted me and started to stroke fast and hard.

My asshole was warm and I could feel how much it was stretched. I was overwhelmed with how relaxed I was! My cock was rock hard! He could do this to me all night and day. I don't know how long he fucked me, but I was limp! He pulled out and appeared in front of me. He loosened the chain on my dog collar.

"Suck it." he commanded. I took him in my mouth and a couple minutes later, I could taste the pre-ejaculum. He suddenly pulled out, much to my frustration.

"Go on and get dressed and come into the den."

I dressed, fixed my makeup and went out to the den. He poured us glasses of wine and I sat down and lit a cigarette. My ass was going to be sore! He took out a note pad and wrote out a note and handed it to me.

"Go to this shop and get those 2 items. I want you to wear the butt plug for at least a couple hours each day and use the dildo to practice deep throat. Buy some numbing throat spray to help you along. I expect you to take my whole cock down your throat in about 3 weeks." he said in an authoritative manner.

"I guess you think I'm coming back?" I asked

"I KNOW your coming back. I have been dominating CD's for about 12 years. I know a sub when I see one. You want to see what's on the other side of the looking glass." he said.

I went to leave and as I did, he grabbed my arm and kissed me. His hand was like a vice on my bicep and his kiss passionate. It made my knees weak! I hailed a taxi and went downtown to the shop he specified.

I talked to the owner and he went over to the rack and returned with the with the dildo and butt plug. The butt plug was kind of a long cylinder rather than a 'Christmas tree' shape. The dildo was silicone, about 2" in diameter and almost 2 feet long. The salesperson suggested a cream called 'Anal Eze'. He said along with the Amyl would help smooth the process.

The cab ride home had me deep in thought. I didn't know what was happening to me. I took a long shower and sat down with a glass of wine. I was still kind of sore from my experience. I had the next day off so I thought I would do some anal and deep throat work.

I worked a glob of the Anal Eze into my sphincter and immediately felt a warm sensation. Laying on my bed, I put some KY on the butt plug and slowly pushed it in. I was resisting and I could get relaxed so I took a small hit of Amyl and I instantly relaxed. I really liked the fullness.

The thin neck part of the base made it difficult to pinch out. I put on my Kimono and started to move around the house. Every so often, I would have a small spasm, but a small hit of the Amyl would relieve it. I understood why the gay scene liked this stuff!

I managed an hour and a half with the plug in the first time. I took the plug out and started to work my throat with the dildo. I took it in my mouth and pushed it to the gag point. I couldn't seem to get past it. My eyes were watering and salivating. I took the anesthetic throat spray and gave myself 5 or 6 healthy shots. It helped considerably. I managed to get past the throat opening by about a half inch.

I kept repeating throat spray and pushing a little deeper. I finally managed to get 7" inches down. That was enough for today. I developed a daily routine. In a 3 weeks time, I was able to keep the plug in for 3 hours and get 11" of dildo down my throat. I was hoping the next time I saw Greg he would be happy with my progress.

It was about 3 weeks later, Greg called and told me to be at his house at 6 pm tomorrow. He said he wanted really heavy makeup. He also said I needed to smoke 120mm all white cigarettes when ever I was with him. He said to go to a specific website and use this one girl in particular as a guide. I looked up the website, found the person he spoke of.

Wow! Her makeup was on the edge of drag queen/show girl. Heavy upper and lower eyeliner with long wings, blue and white frost shadow on the lid and brow with a bright blue in the crease. Her lips were outlined way outside her lip line with a dark red and filled with a pink frost. She had full coverage foundation on with heavy coat of powder.

This was a little outside my skill set and I would need Sophie's help.

Sophie agreed and came over the next day. I showed her the picture I printed out. She was a little taken aback! I told her it was for a special date. I told her of my plan to use my green frost eye shadow 3 shade pallet. I purchased House of Lashes #026 false eyelashes that were thick and flared and a high end foundation at the CD shop just for today.

She spent some time thinning my eyebrows even more and then penciled in my eyebrows. She placed a couple pieces of scotch tape at an angle from the outer corner to the edge of my eyebrow to keep a crisp shadow edge. Sophie worked her magic. She put the heavy lashes on me and I almost felt like I had weights on my eyes. She finished with a generous coat of powder.

"Ok...go look." she said.

I went over to the full length mirror. I was again taken aback! I did look like a Chola! The 'Chola' style was unique to the Mexican-American women. They are the girlfriends Cholo street culture. The style is a tough as nails femme in heavy makeup. The often wear tight jeans, a flannel shirt over a tight muscle t-shirt. Over the years, the Chola look has been adopted by other street cultures.

My eyebrows were drawn with a high arch in dark brown. The heavy eye liner made my eyes really intense. On my lower eye, she used a turquoise frost on the lid line that really set off my eyes. She had used a dark red lip pencil to line my lips. The outline was way outside my normal lip line, emphasizing 'cupid's bow'. My lips were very sexy and provocative.

"You can call me if you get picked up for prostitution!" Sophie said with a laugh.

I got dressed. I put on a waist cincher I had recently purchased that was black accented with red lace. My stockings were black stay-up's with a 6" wide lace top. The last time I was at Elaine's, I bought a brief style panty that would fit my pads.

I would be able to wear shorter skirts. I put on a leather skirt that was 4" above my knees. I had a burgundy sleeveless turtle neck that worked well. I finally had an opportunity to wear my cuff top leather boots. I finished with a pair 4" wide gold hoop earrings and 4 or 5 bangle bracelets. I walked out into the living room.

"It looks like you mean business! Who's your date with?"

"Greg."

"I'm sure he'll love it! Everyone knows how he likes his women." she said with a wry smile.

The last step was the new nails I bought. They were long length, rounded tip in a bright red. Sophie did them for me and they went on quickly. I opened the pack of Max Menthol 120's. I lit one and they tasted much better than the VS 120's. I looked at my hand with the long white cigarette and long red nails. It's always been a turn on for me.

Sophie drew one out of the pack and lit it. She was always sexy and sophisticated smoking. I was getting very aroused. Watching her manipulate the long cigarette with such grace was hitting all the marks. Thinking about seeing Greg again, the makeup, long nails and the slutty outfit I was wearing tapped into some hidden exhibitionism part of my psyche.

I hailed a cab and gave the driver the address. As we drove, the driver was shooting glances back at me. I knew it was the makeup. I was very comfortable that I was passing as a woman now. I wonder what he was seeing. I arrived at Greg's place. I paid the driver and went to the door. Greg answered and I went in. I stood in the living room waiting for his reaction.

"Very nice! I like that makeup look on you. That's going to be your style from now on. I like my sissy 's to look slutty." He said in a matter of fact tone.

"I'm your sissy now?" I said more as a statement than a question.

"Of course you are! Why do you think you came back?" He did have a point. I became acutely aware how much I wanted to surrender to him.

"First, take off your skirt and girdle. Leave your tits, cincher, boots and stockings on. Go into the kitchen and pour us some wine." he ordered. I took of the skirt and padding and realized I had a throbbing hard-on!

I returned from the kitchen with my hard dick bobbing up and down. Normally, I would feeling awkward but for some reason I felt excited with the exhibitionism. I retrieved the pack of cigarettes from my purse. I with drew one and held it up my lips. He lit it with his Calibri lighter. I took a long drag.

"Very nice. Elegant." Again, I swelled with a bit of pride. Looking at the long cigarette in my beautiful nailed hands made my cock throb. Greg was wearing a satin bathrobe and I could see the 'tent' that was formed from his hard cock. We talked for a bit and he asked me how long I've been a CD, what kind of sexual experiences I've had, etc.

He finally told me to go into the play room and get the waist belt, wrist and ankle cuffs and he put them on me. He parted his bathrobe and his beautiful pierced cock was hard and fully erect. With out prompting, I knelt down in front of him and started sucking his dick. I started with lip action on the glans, keeping my eyes looking into his. I worked my tongue around the head, then pushed the head into my throat. All the dildo work paid off because I swallowed him completely. The piercing felt a little awkward, but I pushed through the gag reflex.

I worked his cock in and out relishing the feeling of a real cock rather than a piece of silicone. He pushed me off and stood up. He grabbed the back of my head and started thrusting into my mouth hard and deep. The muscles in my mouth and my throat were getting sore. He did this for a couple minutes and withdrew his dick.

"Can I keep servicing you?" I asked in a docile voice.

"In a while." he said. "Freshen up your lipstick" I took out my compact and lipstick and and evened out the color. I freshened the lip liner. I wanted him to face fuck me again.

"I don't cum from a blow job too often. When I do, I will shoot my load on your face and you won't wipe it off. Wearing my cum is a point of pride...Understood?" He said in a forceful fashion. It sounded really exciting.

He took me by the hand and we went into the playroom. On one side of the bed, there was a chain hanging from the ceiling. From the rack on the wall, he picked out a black wooden bar with latches on the end.

"Spread your legs," he commanded. I widened my stance and he hooked the bar on each cuff that were around my boots. He then hooked my wrist cuffs together, attached the chain and started pulling up. My arms were now pulled up behind my back in a strappado position, tight but not uncomfortable.

On the wall in front and at the side were wide, full length mirrors. Looking at myself in the mirror, with the heavy makeup, made me realize there was a different person emerging. I felt Greg's fingers going into my ass with a large amount of lubricant. I immediately relaxed waiting for his cock.

"So Kirsten...tell me what you are and why are you here?" He said as he moved his fingers around in my sphincter.

"I'm your bitch, your personal slut! I am here to please you!" I said. It sounded like it came from somewhere else, but it came out of my mouth.

"What do you want?" he asked in a teasing voice.

"I want your cock in my ass...PLEASE, PLEASE fuck me!" I whimpered. My words sounded like they came from someone else. He then pushed his rock hard cock in my ass. I pushed backwards to take it all.

"Slow down you greedy slut!" He said with a slap on the ass that stung!

I liked it! I was becoming acutely aware of how much I liked being called a slut, sissy, whore and bitch. They fit! I held still and allowed him to slide in and out. It felt like nothing I had have experienced before! His rhythm was slow and I just let myself go and enjoyed every second.

I would glance up and look at myself in the mirror and my cock would throb! The mirror to my side allowed me to see his cock working in and out of my ass. He started pounding hard! My hips matched his rhythm. I could feel cum dripping from my cock! He finally slowed and stopped, then pulled out. I thought about whining for more, but I thought better of it.

He took a long thick dildo and pushed into my ass. I could feel that I was gaped and had no reflex to push it out. He loosened the chain so I could raise some and stood in front of me with the head of his cock just in tongue range. I couldn't believe how much I wanted to suck it. He moved forward just enough to rub the head on my lips. I kept trying to strain forward.

"You want this cock?" he asked.

"Oh God yes!" I said with a gasp.

"I'm going to slide it in and you need to show some restraint. I didn't realize what kind of slut you are. It usually takes a couple months to get one of my sissies to this point." He said it with a certain satisfaction.

I relaxed and let him take control. He slid in and out slowly. He was going to the back of my throat and I was surprised I wasn't gagging.