Date: March 22, 2019

Author: Kirsten Addison

Subject: Chrysalis of Kirsten Chapter 1

Chrysalis of Kirsten


Kirsten Addison

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

Chapter 1: Youth and Confusion

I grew up in San Francisco. The 'City' is a haven for personal freedom and expression which made my lifestyle very easy. Ever since I can remember, my demeanor has always been effeminate; I acted more like a girl than a boy in my facial expressions, voice and gestures. I think I was more in touch with my feelings than most of my male peer group. I was target of bullies and made fun of, but learned to avoid harassment with my quick wit. I didn't like sports, war movies, cowboys, etc. I tended to have more girl friends than boys. I guess I was 8 or 9 when I realized I had a fetish for wearing women's clothes. When I was around 12, my need to dress really took hold. It was a compulsion I couldn't ignore. Like many do, I started with wearing my mother's undergarments when my parents would go out for an evening. All this slowly progressed to me actually buying pantyhose, panties, etc. and storing them under lock and key in an antique steamer trunk I had in my room. My mother had a degree in art, saw that I was a bit more emotionally sensitive and tended to support me. She was part owner of a high end art gallery and an accomplished artist in her own right. My father was a tenured professor of history at UCSF and emotionally closed off. We never did have much of a relationship. He thought that I was kind of a wimp and without sports, we had no common ground. I had little respect for him because of his philandering.

When I was 12, my parents divorced. It hit me pretty hard. It was decided that I would stay with my Mother because my Dad was moving to New York. I was supposed to go out and spend time with him in the summer, but that never happened and over the years, we completely lost touch. It was OK by me. The first few months were tough, but my best friend Sophie, had experienced the same thing and was always there for me. I'd known Sophie since about 4th grade. Right around this time I started to realize that I wasn't attracted to girls physically. Sophie was very beautiful for her age, but I just didn't find myself attracted to her in a physical fashion, or for any other girl for that matter; she was just my best friend. I also didn't find myself attracted to boys either. It was a confusing time. One avenue I did find for channeling my emotions was art. I started sketching when I was about 10 and slowly included other mediums such as a pastels and paint. Most of my teachers saw that I had promise, as did my mother. She started giving me exercises in composition, perspective and shading. When I started cross dressing, another part of me was unlocked. Those who saw my artwork could see the difference. My artwork demonstrated much more emotional depth and passion.

Mom worked nights at the art gallery which left me a large chunk of time to stay dressed. I would come home from school around 4 and I would immediately put on panties, a half slip and pantyhose. I would wear a long denim skirt I found at a consignment shop and a baggy knit sweat that was mom's lounging 'about the house' sweater. Both my parents were good looking. My mother looks like the actress Jenna Stern with a smaller nose and lighter hair. She has a beautiful completion with faint freckles on her nose and cheeks along with green eyes. I probably inherited my porcelain white skin from her. My father looks a little like Viggo Mortenson with blondish hair and steel blue eyes. I look more like my mother. I'm 5'6” about 118 pounds, a swimmers build and sandy blond hair. It wasn't a problem finding women's clothes that fit . The big issue was my slender waist and hips and not much of an ass. My small wardrobe wasn't much, but it allowed me to indulge in the feeling of nylon on my legs. I had been shaving my legs on a regular basis for about a year and I felt like my body was a sensory organ. I especially love Legg's Sheer Energy pantyhose with a control top panty. The compression of the nylon was a completely different dimension in sensation! The tightness the panty really helped with keeping my cock in place, which was always hard when I was dressed!

By the time I was 14, I was getting more adventurous with dressing. On the weekends, I would wear nylons or tights under my clothes. I usually wore sweats or a nylon track suit. One summer weekend, Sophie and I were hanging out with some friends at a local park just talking. I was leaning against a tree and I guess the leg of my track suit rose up over the top of my sock and it was obvious I was wearing black nylons. The others in the group left, leaving Sophie and me. Sophie took a box of Marlboro Light 100's out of her bag, withdrew a cigarette and lit it. She had started smoking on a regular basis about a month ago. I always liked the way she smoked. She is always sophisticated and elegant with out trying. Sophie didn't have all those twitchy habits like continually flicking the filter with their thumb, etc. that so many girls have. Sophie didn't have to try to look cool, she just was! I think the long, white cigarette helped also.

Are you wearing nylons?”, she asked out of the blue.

yes.”, I said meekly feeling myself flush a bit.

Why?”, she asked, taking a long draw on her cigarette.

I like to cross dress.”, I said, Looking at her eyes for her response.

Really! How long has this gone on?” She asked with curiosity.

Since I was about 9. It's been much more serious the last 2 years.”

Why haven't you said anything? I'm your best friend! You really think I would run away screaming or try to shame you?”, She said, placing her hand on my arm

Well it is a little off the beaten path and I wasn't sure what you would say. I'm still coming to terms with it myself.” I said with a sense of relief.

I guess I can understand that.” She leaned over and kissed me on the cheek.

I love you no matter what! I guess since we are doing true confessions, I have something for you...I think I'm gay.”

Wow...I didn't see that coming!” I said in surprise.

Neither did I. Sandy and I have kind of been together for a couple months now.”

That's great! You feel relived speaking about it?” I asked.

She thought on it for a minute.

I'm relieved I told you. I know romance has never really been part of our relationship. I can sense you're kind of relieved.”

Sophie had always been intuitive, especially with me.

I have to admit it does take some pressure off. I was always afraid of having to go into that place with you. I don't know if I like men or women. Right now, I just like crossdressing. It puts me in an emotional place I don't know how to describe. A level of relaxation, contentment and arousal. If that makes any sense. As for sexual identity, I guess I will figure it out when the time comes.”

So what's your wardrobe like?” She asked, taking a draw off her cigarette.


Well, maybe that's something I can help you with.” she said with her Sophie smile.

I finally started smoking. It started with taking an occasional drag off Sophie's cigarettes and finally started smoking a whole cigarette on my own. Initially, I was just kind of feeding a habit until I smoked a Benson & Hedges Menthol. I loved the effects of the menthol seemed to add to the arousal of cross dressing. In hindsight, watching women smoke has been a fetish for me. My own smoking is kind of tied into my female identity. It's kind of hard to explain. Breakfast was a ritual with mom and I, due to not seeing much of each other during the week. About a month earlier, I finally admitted to her that I started smoking and I wanted her blessing to smoke freely without having to sneak around. She really couldn't lecture me because she started when she was 12. We were always fairly honest with each other. That being said, I wasn't sure how I was going to tell her I was a cross dresser. Having coffee and cigarettes had become morning ritual. My 16th birthday was coming up. At breakfast, Mom asked me what I wanted for my birthday. I told her I wanted my ears pierced. In the mid '90's, everyone had their ears pierced.

So do you want to go to one of those jewelry shops in the mall?”, she asked taking a sip of coffee.

Not really. I would rather go to a body piercing shop. I really don't like those cheap imitation gem posts they use. I rather have hoops. Seems like everyone I know who has them done in one of mall shops ends up with an infection.” I said.

I'll talk to Barry” she said. Barry was one of many interesting friends she had. He worked at the Gauntlet, the body piercing shop. She set up an appointment and I asked Sophie to go with me. About a week later, we drove over to the shop. I spoke with Barry at length about what I was looking for and we decided on a 12 gauge, 12mm captive bead rings. I was a little anxious and Barry was very calming and reassuring. He had a very large gauge plugs in his ears and a couple other facial piercings. I sat in the chair as I watched him set out all the instruments, trying not to be nervous.

Don't worry, this really doesn't hurt. The gun used in jewelry shops are a 100 times worse! Those studs they use aren't even sharp. They're more or less hammered through the earlobe!”, He said in a calm demeanor. He marked each lobe with a blue plastic surgeon's pencil. He handed me a mirror and the placement looked good. He then showed me the 'sharp': it was a piece of tubular stainless steel that was cut with an acute angle. He said it was razor sharp and would go through quickly without resistance. Sophie took my hand. Barry took a pair of hemostats with large loops on the end. They kind of looked like cooking tongs, but smaller. He clamped the my left earlobe with the hemostats, check the alignment, then told me to take a deep breath in and let it out. Sophie squeezed my hand as I let my breath out. A microsecond of pain and it was gone! Barry immediately put a small cork on the tip of the sharp so it would cut me.

Is it through?” I asked.

Yep...told you it wouldn't hurt.” He prepped the the ring and pressed one end on the sharp and it slid right into the fresh hole. After putting on the captive bead, he did the other side which was much easier for me because I knew what to expect. I looked in the mirror and I really loved what I saw! My lobes were a bit sore. There wasn't any blood. I thanked Barry and gave him a tip. Leaving the shop, I was feeling a rush of endorphins. It was an energizing high. One that would come to haunt me.

Mom gave me a generous allowance for taking care of the house, grocery shopping and making meals. I stayed under the radar, out of trouble and was responsible for my age. This allowed me to by clothes and work toward my goal of eventually going out in public as a young woman. Sophie and I would go to different consignment shops, Goodwill and some of the nicer places. We both had a great deal of fun. She had an eye for style and seemed to know what I would like to wear. I finally decided that I wanted to do a full transformation for a day. Mom was going to LA for a long weekend in August and I decided that was going to be my coming out day. The last hurdles were body shaping, breast forms and a nice outfit. I had saved up enough to buy a set of quality breast forms. They weren't cheap, at least the decent looking ones. Fortunately, there was a boutique for cross dressers in the city. One afternoon, Sophie was hanging out with me as I did my daily chores. I was wearing nylons, the denim skirt and a flowered top Sophie picked out for me. It didn't look right without breasts.

I think I want to take the leap and do a complete transformation.” As I sat down on the couch with her and lit a cigarette.

You have a date in mind?” She asked.

In the middle of August, Mom is going to LA for some business and will be gone about 4 days.”, I said.

Sounds perfect! If you're going to be serious about this, we have to go to the boutique and get you some boobs and padding. There's also makeup.” She said. She pulled her foot out of her sandal and rubbed it along the nylon on my leg. It was electrifying! She laughed. She liked teasing me like that.

Ok, how about this Saturday we go down to the boutique. I have about $500 saved. I think I get what I need for that much.”

We can go down to Walgreen's right now and get makeup if you want. Bring about $100, it's not cheap!” I changed into a pair of sweats leaving my nylons on. We walked over to the local Walgreen's and I grabbed a hand basket. We went over to the makeup isle and she started to choose what I would need to start. My blond hair, blue eyes and fair complexion made it easy. First was foundation base, foundation, contour sticks, loose powder, blush, a compact, a number of different colors of eye-shadow, mascara, eyelash curler, eyeliner, lipstick (a couple of colors, including a nice fire engine red!), eyebrow pencil, lip liner, a large set of brushes, makeup sponges, a pair of precision tweezers and a travel case so that I could store everything in my steamer trunk. I was really having fun! I realized that I really didn't care what people might have been thinking.

About a week later, we took the bus to the 'Elegant Lady'. This was a specialty shop for cross dressers. I felt kind of anxious as we walked into the shop. We were greeted by Elaine. It took a few minutes to realize that 'she' was indeed a 'he'; a very attractive 'she'. Sophie, always the bold one, introduced us and explained our mission. Elaine took us into the dressing area of the store.

I need to take some measurements to figure out how we're going to feminize your body. Why don't you slip off your track suit.” She said in a matter of fact manor. She noticed the hesitation.

Let me guess, your wearing pantyhose underneath? Let me tell you something honey, all of us started by trying on mom's clothes and spent many years on the down low! It wasn't until I was 26 before I decided to be myself. You'll be just fine. You're among friends.” She said in a comforting voice.

I slid off the track suit and she took a dress makers tape and measured my chest, waist, inseam and hips. She disappeared into the store and returned with a black waist cincher, a black elastic with plastic stiffeners. She also had a high-waist, mid-thigh compression panty and a number of silicone pads. First, she put the cincher around my waist and hooked it in front. In the back were laces.

Sophie, are you going to help get him dressed? Let me show you how to lace this cincher.” Elaine said.

Hang on Steve, this is going to feel weird!”

She started pulling on the laces working her way from bottom to top. I kind of gasped, it was tight and hard to breath, but snugness was strangely agreeable.

Sit down on the stool and slip off your nylons. I know it's a little difficult bending over. This is the price for a slender waist.”

Elaine put hip and butt pads in the panty. I stepped into it and pulled up and slid it over my black high waist panties I was wearing. Elaine worked the pads into the proper position.

Go look at yourself in the mirror.” Elaine said. I looked at myself in the mirror and was taken aback with the change!

I used the medium pads on the hips and the larger ones on his butt. You don't have a lot of butt to work with.” she said with a smile.

What do you think Sophie?” Elaine asked.

I think she looks hot!” Sophie said as she ran her hands over the girdle.

Now we need breasts. Have you given any thought to cup size?

I was thinking C.” I said.

C but no larger. I don't want you looking like a big rubber tit drag queen!” Sophie chimed in with a laugh.

Elaine left and returned with a bra and a couple sets of breast forms. She handed me the bra.

I assume you know how to put this on?” I hooked the bra in with the clasp in front and turned it around.

Don't pull the straps up yet.” Elaine slip a form into the inner pocket of the cup.

This is our high end form. They look great, but they're a little expensive.”

How expensive?” I asked

$380 a pair.”

That's a little out of my price range. What do you have for under $200 that look good?”

This is our lower end set that still look good. They have a nice weight and move naturally I can let you have them to you for $130”

She slid them into place and I look at myself in the mirror. I really liked what I saw and wished I could wear everything home. We went up to the register and payed. Elaine pulled out a index card.

I fill out a card on all my clients with their measurements and what they have purchased. Have you chosen a femme name?” She asked.

Kirsten.” Sophie blurted out. I looked at her.

I don't know, it seems to fit.” she said smiling at me.

Ok, Kirsten it is” I said.

By the way, your new measurements are 42C-30-38. That's very sexy and proportional.” Elaine commented.

My new persona was put into a nice but nondescript shopping bag. I wandered over to look at the other clothes. I found this blouse I just had to have! It was an emerald green brocade satin with puff long sleeves. I also found a black plain pencil skirt that was perfect. This is what I would wear on 'coming out' day. I asked Elaine if she could put them aside and I would pick them up in about a week.

We left the store and stopped at a coffee shop up the block. We chose a table on the patio. Sophie, as always was tuned into my feelings.

What are you feeling right now?” she asked as she lit a cigarette.

Kind of high, kind of overwhelmed.” I said.

Your taking big steps in becoming yourself.”

Thanks for doing this with me.” I said looking at her.

She reached over and squeezed my hand.

It was mid-July and I still had to get a number of things for the big day. I wanted a pair of wide gold hoop earrings, a flat serpentine necklace and a gold serpentine belt for the skirt. I also need a pair of leather 4” pumps. I wanted a pair of D'orsay pumps with an ankle strap and 4” heels, but they were out of my price range for right now. As the days ticked off, Sophie helped me with 'prep'. She would come over after school and start working on my eyebrows. My blond eyebrows were easy to work with. She was shaping them slowly, once every other day so it wouldn't be overly noticeable. Mom did notice something different but couldn't put her finger on it. After about 2 weeks, I had fairly well arched eyebrows that would look great when she penciled them in. Over the next couple weeks, I bought the jewelry and the belt. Sophie and I went to a discount shoe store and started looking at pumps. I found a female to male size chart on line and I needed to get a size 8. I found a pair of V throat 4” black leather pumps that fit perfectly. I wanted to stand and admire them in the store, but I thought it best to get them and go. Everything was set for tomorrow.