Chapter 4: Adventures in Wonderland

As I relaxed in the bath, I reached down and stuck a finger in my anus. It was still stretched open to a certain degree. I couldn't really feel my finger much. I was going to give it a break from the butt plug for a couple days. My cock was semi-erect after being released from the chastity cage. Part of me wanted to jack-off and cum. I decided to stay in that state of semi-arousal. I finished the bath, completed my facial regimen and applied a pore cleaning facial mask. I was emotionally exhausted. I just wanted to be comfortable and relaxed, so I put on a flannel night gown and a terry robe. The loft had been partitioned off in to large spaces; art studios for both Julie and I, bedrooms, a kitchen area and a large TV/conversation room. I sat down in one of the leather over-stuffed chairs and turned on an old movie. Julie came up from the gallery, changed and sat down with me. I still had a green mask on my face. I asked her about her day. She said that she was trying to rope in a new artist, bills, employee problems, etc. After a long pause, she took a sip of wine.

“You know, I can't remember the last time I've seen you dressed as a male. How do you feel about who you are?”, she observed.

“I love who I am. Why?”

“Have you given any thought to HRT?”, she asked.

“You mean starting sex change?”, I responded.

“Yes. It seems to me that in your soul, you're a woman. Your demeanor, how you think and talk and dress. All the pieces are there.”

“I haven't given it much though to be honest. I have to admit having real boobs, a nice ass and hips would be great! I don't know if I would meet the criteria for 'body dysmorphia'. I think much of what I do would be considered 'fetish'.”, I replied.

“Like what?”, she asked.

“I love to smoke, but I smoke long, all white cigarettes because of how they look in my fingers with nails. My makeup is a on the heavy side.”, I reflected.

“Well think about this: we wear clothes and makeup we like but we also like to see how it's perceived by others, especially men.”, she offered.

“Well I have found many men really like heavy makeup! Greg loves that new look of mine. He's also really turned-on by the way I smoke. When I'm with him, he want's me to smoke 120's!”, I commented. I found it a little strange talking to my mother about arousing men, but it's been pretty obvious the last couple years that I'm sexually oriented toward men.

“Well I love you for who you are. If you want to go the HRT route, let me know. My insurance will cover it.”, she said touching my arm. I went to the bathroom and removed the mask and returned.

“You haven't commented on my new piercings.”, I said.

“The ring in your nose is a little unusual, but if you like it, that's what counts. Does Greg like it?”

“He's the one who suggested it.”, I answered.

“So what's he like in bed?” she asked coyly.

“I'm sore!”, said with a laugh.

We talked for about another hour. She talked about her friend Teri who she had become very close to. Intuition told me that there was more going on, like sex, but I didn't press it. I wanted to extend her the respect that she did for me. She's very open minded and liberal, but it can be different when it hits home.

I really started to like working at the gallery. With my growing wardrobe I was able to put together outfits that were stylish and attractive. I avoided the 'kooky' artist look, I wanted to project professionalism. Many collectors wore Brooks Brothers suits and Carolina Herrera dresses: big money! I always wore skirts or dresses, pantyhose or tights were a staple. My makeup always consisted of foundation, powder, eyeliner and false eyelashes as a bare minimum. Sophie taught me I could bright ,colorful eyes or bright red lips; never both for day wear. I worked at keeping the image Julie wanted to project for the gallery. Our office was in a big room accessed by a door in the corner of the gallery. She would often have agents come in to arrange showings. I would sit in these meetings that were in a living room type of arrangement, in the center of the office that had a couple of leather over-stuffed chairs, a large coffee table and matching couches. I would just take notes, get drinks or sometimes canapes I would purchase a local deli. My main job was help Julie land clients and basic accounting. I would offer ideas or suggestions. I also realized that sometimes I was just eye-candy for men, which I didn't mind at all! Men are very easy to lead around by their cocks.

I had spent a lot of time on the computer searching out everything I could on the BDSM lifestyle. Subs, slaves, femdom, Domination, sissy sluts, punks, object slaves, corporal punishment, etc. I was trying to get a read on what Greg wanted. Through emails, I asked him what my place was. He said I was going to be his sissy slut sex toy. I will sexually satisfy him and anyone he chooses and he will be in charge of my sensory awakening. I wasn't sure what 'sensory awakening' was, but I was very curious. The next 3 weeks, I put enlarging my nipples forefront. I took a picture with my cheapo webcam and sent it to Greg. The day after, Barry had called me and set me up with a nipple piercing appointment. I got really anxious! This was a major step, but I knew I had to follow through. Sophie and Sandy were more than happy to come with me. Sandy was thinking about getting hers done and wanted to watch the procedure. We met at the gallery and took the bus to Barry's shop. I was in sweats with minimal makeup. We met Barry at the shop and he led his back to his booth. I took my sweatshirt and T-shirt off. He took a pair of calipers and did some measurements.

“I don't usually do a 10 gauge piercing, it's something I would rather gauge up. With your nipple size, it won't be a problem.” He said.

“Kirsten, your nipples are bigger than mine. I'm jealous!” Sandy commented. Barry marked my nipples close to the aureole. Barry said this is a special piercing that Greg requested. Again with the clamp, deep breath and Sophie holding my hand. I slowly let my breath out and BLAM...and intense flash of pain. Barry quickly inserted the barbell and screwed on the end. In a instant, the other side was done.

“Here, stand up and take a look.” Barry said as he and Sophie helped me over to the full length mirror. Looked, turning side to side.

“These are gorgeous!” I said still feeling wobbly. “I feel like I just did a line of coke!” I said.

“It's the endorphins. It will last for a while.”, Barry said. He went through all the after care; salt water soaks, moving the barbells, cleaning off the 'crusties', etc. I gave him a tip and thanked him.

We ended up back at the loft. I think my nipples were in a state of shock. They didn't hurt, except for a mild burning. Sophie had her high-end 35mm digital camera and she took some quality pictures of my new nipples. I downloaded them on my computer and sent them to Greg. He immediately responded to how much he liked them! I was elated!

“So what does your big stud have to say?”, Sophie gibed.

“He loves them!” I responded, not letting her get my goat.

Sandy said she wanted to get hers done. She was going to keeps tabs on me to follow the healing process first. In the evening, I did my first salt water soak described in the instructions. I thought it would really sting but it didn't. I used a shot glass and held it on each nipple for about an hour. Barry said the more I did the salt water soaks, the faster they would heal. I was doing about 4 a day. I searched out others experiences online. A number of people recommended Tea Tree oil to keep the skin from drying out.

I was going over to Greg's place about 3 times a week. I would take my makeup case and a an overnight bag with my intimates, wearing a pair of sweats. I bought 3 pair stay up stockings with a 5” lace top in black. I finally bought the D'Orsay's with 4 1/2” heels, red soles and an ankle strap. I bought another cincher; black with red lace and 6 garters. I was really grateful that I made such a good salary at the gallery...being a woman is expensive! Arriving at his house, I would take off my clothes, go to into his office and he would put on the cock cage while I was still flaccid. I would go to the spared bedroom where I had set up a makeup table, then put on my makeup, do my hair then put on the cincher and stockings and and a pair of slippers. Doing house work in heels was impossible! I always wondered how woman in the 1950's did it. When finished, I would put on my heels and report to him. He always loved my makeup look! I had bought a number of new shadow colors. I now had a teal frost, an apple green frost, a MAC pallet collection in bright matte colors. I kept the 'chola' look that he like so much. He never kept much food, so we would order out. I would usually answer the door and pay. At that time, I was still allowed to wear my kimono. I did get some unusual looks from the delivery guy and I surprised myself with my lack of embarrassment! I was at the place where I didn't care what people thought. I had a feeling that answering the door in a kimono would stop when I became his collared ****. Sometime during the day, Greg would ask me for a drink. After bringing it into his office, and sometimes have me grab the back of a chair and he would fuck me. Other times he would come out into the kitchen, have me lay face down on the table and he start banging me. He still wouldn't cum in me. He would finish work around 4 and sit down in the living room in his bathrobe. I would bring him a drink, get on my knees and go to work on his cock. I started by rubbing the ball of my tongue stud all over the head. I then wrapped my red lips around his glans and would cast a sultry look into his eyes. As I did, I could feel him stiffen with excitement. I took him into my mouth, slowly taken the shaft down my throat, pressing my face into his groin. I would slowly stroke his shaft up and down, pressing the ball of my tongue stud on his shaft. It didn't take long until I could taste pre-ejaculum. Right about that time, he would pull out. I felt like calling him a tease but thought better of it.

Most days I would go into the play room put the wrist and ankle cuffs on and lay down in the sling chair. Laying in the sling chair, becoming acutely aware of how uncomfortable my swelling cock in the chastity device. Greg would come in. He hooked the wrist cuffs on the chain supports by my head. He maneuvered my legs around the chains at the foot and latched them high on the chain. I was spread eagle and totally exposed. I really loved the vulnerability! From the toy box, he withdrew a long, wide smooth silicon dildo. I like smooth dildos the most. The ribbed ones or ones with the molded veins made me sore. He sat down on a stool, used the control box to adjust the height, put on a pair of surgical gloves and applied a generous application of lube inside and around my rectum. He then moved his fingers in and out of my ass. He then inserted the dildo and pushed it in. He stroked it slowly in and out, going a bit deep each time. Above the chair on the ceiling was a large mirror. I let myself indulge in the erotic picture of myself, my makeup, stockings and heels in a totally **** position. I let go of all judgment of myself. I realized how much I loved who I had become. Greg pulled the dildo out and started to work his hand in. He would push until I felt pressure and backed off. This went on for a couple minutes until he pressed so hard I thought something was going to tear! This was the first time he fisted me!.It immediately passed into feeling of something large in diameter, his hands are huge! I looked up at the mirror and saw his arm in my ass. This is so hot! I thought to myself as I laid there in total bliss and contentment. For the next 20 minutes he moved his fist in and out of my ass. He would often rub my prostate, which is an unbelievable feeling! He stopped and took off his gloves. He then got his digital camera and take a number of pictures of my ass. He repositioned the chair so it was about waist height. He slide his cock in with virtually no resistance. He began to stroke in and out. Due to my gaped asshole, I didn't feel the 'fullness' I normally did. As he fucked me, he was hitting the spot that was putting me into orbit! Even with my cock caged, I could feel cum making it's way out! Greg reached into his robe, withdrew a key, unlocked the cock cage and took it off. My penis became immediately erect and hard. Greg reinserted his cock and stroked my ass slowly, fully aware of the spot he was hitting. Cum was slowly coming out and running down the sides of my hard dick. My groin muscles finally contracted and I shot out a large glob of cum. My cock and shaved groin was covered in sperm. Greg did something I really didn't expect. He leaned over and licked up the cum! He ran his tongue gently up and down the shaft, lapping up what was left.

“I didn't know Dom's did that.”, I said in a whisper.

“I'm not most Dom's!”, he replied.

He unhooked the wrist and ankle cuffs and I sat up. I cleaned myself off with a towel. Greg pressed a few buttons on the camera.

“Take a look.” There about 4 photos of my sphincter stretched open about 3”.

“Oh my god! Will I close back up?” I exclaimed.

“You'll be just fine.” he said with a smile.

“Go in the bathroom, clean up your cock and join me in the living room.”

Greg was sitting on the couch and I sat down beside him, kicked off my heels and curled my feet up

“Two more piercings and I will be eligible for your collar.” I said looking for his reaction.

“Is that why you had those piercings done?”

“At first. I then started to realize that they were changing my perceptions, kind of altering my consciousness. I can't wait for my nipples to heal fully. I have already noticed how sensitive they're becoming!” I replied.

Greg reached over and lightly rubbed the tip of my right nipple with his finger. I gasped with the intense pleasure! I had goosebumps!

“I guess they are.” he observed with a wry smile.

“Why would I want to collar you?” he asked.

I wasn't sure if he was being a tease or trying to keep me off balance. I decided to return his 'serve'.

“I'm the fully sissy package! I fully pass as a woman, you love how I dress and you know that I will commit fully as a sub.” I replied giving him the sultry look that always made him hard. I wrapped my arm around his bicep, which about the size of my thigh! I ran the tips of my nails up and down the inside of his forearm.

“Yeah, your definitely in the running.” he said coyly.

The next couple months went by fast. I only saw Greg once. He was busy on some project. I was really involved with helping Julie get a show together. My nipples were healing well. I would wear large band-aids on them so the weren't irritated by the breast forms. I kept doing the soaks morning, noon and night. My tongue was fully healed and I had finally became used to it. The septum healed in no time at all. I stopped by Barry's shop and asked him when I could get the nipple jewelry changed out. He looked at my nipples closely to see how they healed. When he touched my nipples, I almost shot a load! A shutter and recoil!

“Sensitive huh?” Barry commented stating the obvious.

“They had become really sensitive!” I answered.

I liked that. He told me it was a little early, but I could go to rings. I was overjoyed! I picked out a pair of 10gauge, gold anodized captive bead rings. I took about a minute for Barry to change out the jewelry. I looked at them in the mirror and immediately got hard! I loved the look! I wondered what the Sophie and Sandy would think. Later that evening, Sophie called me. Her and Sandy had been frequenting a group called “Aphrodite”. It was a group of Lesbian women who would get together once or twice a month. It was also open to select CD's and transgenders on invitation. Sophie asked me to attend, she wanted me to meet some of her friends. I told her I would attend and thanked her for asking me. The next get together was the next day at 7pm. I went to bed and slept until about 9 the next morning. Sunday mornings were pretty laid back. Usually, it was a time for Julie and I to get caught up. She made a simple brunch and we chatted over coffee.

“So, you've been seeing a lot of Greg.” she commented

“Yes...I really like him a lot!” I replied with a modicum of excitement.

“You like the dominate type?”

“I like him. He happens to be very 'assertive'. I like how he's helping me discover myself.” I replied in contemplation.

“How is he helping you discover yourself?” She asked with a touch of sarcasm. How do I describe this? I thought to myself. Do I tell her about being bound, fisted, fucked with dildos and told to suck off strange men?

“He knows a lot about physical sensation. Here, let me show you something.”

I opened my robe and unbuttoned my satin pajama top and showed her my nipple piercings.

“Oh wow!” she said, bending over to get a closer look. “I don't remember your nipples being that big!”

“I used a vacuum pump to enlarge them. What do you think?”

“I have to admit they are kind of sexy! Did it hurt?”

“Not half as bad as you might think. The first month they were sore. Now the sensitivity is enough to launch me through the roof!” I responded.

“Really.” Julie replied with curiosity.

“I'm still getting used to your nose ring.” She said laughing. “Anymore piercings you haven't told me about?”

“I'm getting ready to get a Prince Albert and a Guiche.” I explained what and were those piercings were.

“I have a book for you.” I got the Fakir Musafar book from my bedroom and handed it to her.

“Read this. It will give you some insight into body modification.” I offered. She took it and leafed through it.

“This is interesting!” She commented

“I had to ask myself why can't the body be a canvas? I think it's a good thing to question our preconceived notions” I remarked.

“I have to agree. I'm going to read this.” Julie offered as she read some of the pages.

The conversation drifted into a new medium Julie wanted to try. She wanted to work in copper and presented a small piece she was working on. Our conversation eventually landed on Teri. She became kind of tight lipped. Once again, I didn't **** the topic.

It was 4:30 and I realized I should get ready. I poured a glass of wine and did my makeup. I was amazed how good I had become. I was wearing the usual heavy eyeliner, false eyelashes, green frost eyeshadow, foundation and powder and a matte red lipstick. I put on a white satin blouse with chiffon sleeves and lace cuffs and collar. I added an above the knee leather skirt. A wide black leather belt with a brass buckle completed the look. I put on my black 'stay up' stockings and a pair of 4” heels and I thought I was set. At Macy's, I bought a pair of 3”, 2” and 1” wide gold hoops and kept the same 'look'. I liked the weight on my ears. I looked at myself in the mirror. Leather and Lace It doesn't get much hotter!