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Chapter 3
by KirstenEclipse
What's next?
Chapter 3: Into the Looking Glass
The next day, around 10 the next morning, the phone rang. Julie handed me the receiver.
“Hello?” It was Greg
“Hi Kirsten, I want you to come by today?” he said. It was more of a command than a invitation.
My first impulse was to say no, but I couldn't.
“Sure, what time?”
“How about after lunch.”
“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 it in mind she said. I put on my favorite denim 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. I rang the bell and he answered. 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 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 last night.
“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?” 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, without braggadocio. We sat down on 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.” 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.
“Knee 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 pronounce 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 balls 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 pushed 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. 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 took a wide leather belt off the rack and fastened on my waist. He then placed a wrist cuffs on me. The cuffs were fur lined and comfortable. He fastened my wrists to a couple of rings on the side of the belt. He lowered me face first on a thick cushion on the bed. 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. I started getting really 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. Then he rolled me over.
“please don't stop” I said in a meek voice.
He put a pair of cuffs on my ankles and connected chains that hung from the overhead frame on the bed and spread my legs wide. He then place a clover clamp on each nipple. It was intense and a turn on. He then place the mask with Amyl Nitrate 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 couldn't believe 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 took the chains off. He sat me up on the edge of the bed. He took the condom off his cock.
“Suck it” he commanded. I took him in my mouth and a couple minutes later he started to cum, but pulled out.
“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 manor.
“I guess you think I'm coming back?” I asked
“I KNOW your coming back. I been dominating CD's for about 10 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. 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 specific items. 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 a foot and a half long. The salesperson suggest the 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. 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 the about 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 over at 6 pm tomorrow. He said he wanted really heavy makeup. He also said I need 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 to help me out and came over the next day. I showed her the pic I printed out. She was a little taken aback. I told her it was for a special date. I told her of my plan was 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 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! 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 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 with kind of a pouty, pursed shape. She filled with a bright pink frost.
“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. With wore my favorite emerald satin blouse with puff sleeve. I finally had an opportunity to wear my cuff top leather boots. 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 was hoping they didn't taste as bad as the Virginia Slims. I lit one and they tasted much better. 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 really 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 in 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, 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, 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 meek 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 jiz 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 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 thrusted 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 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 had 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 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.
“You do have a cock suckers mouth.” He said in a whisper. I felt a wave of pleasure being called a cock sucker!
“I think were going to take the next step.” I wondered what that was. I felt like I was on **** I was so relaxed. I really wondered how my pink lips looked like stretched around his cock.
He pulled his cock out then proceeded to unhook me. He pulled out the dildo and inserted a butt plug.
“May I have your cum?” I asked in a contrite voice.
“No. Only my collared slaves get my cum.” he said.
He took the cuffs off and we went into the living room and sat on the love seat. I was still o
“What does it take to become a ****?” I asked as I lit a cigarette.
“First, you have to commit to my collar. There are other requirements.”
He handed me a two page print copy. The first paragraph was about giving my will over to him. He would be responsible for the journey into my body and psyche. I would do anything asked of me. Next, there was a list of piercings required. A septum, tongue, nipples, a Prince Albert and a Guiche. I would also have to be his maid, cook and entertain guests as he saw fit. While I was at his house, I would wear his collar. We would also go to various clubs with my collar on. I would also need to sign a contract. “I wonder what that means?” I thought to myself
“Is this something you want to do?” He asked with already knowing the answer.
“yes.” I said submissively.
“Why?” he asked looking at me.
“I think you've shown me who I really am.” I said in a meek voice, averting his eyes.
“Are you ashamed? Look at me and repeat what you said.” I did so and felt a sense of self-honesty.
“Good. You have nothing to be ashamed of. We are who we are.” he said.
“We'll talk again a week from now. In the mean time, you have some tasks to show me that you have some level of commitment. I want you to get your tongue and septum pierced. I also want you to start enlarging your nipples. They need to be larger to take a 10ga piercing. Go see Barry about your septum and tongue piercings. He pierces all my slaves and he knows what I want.”, he ordered.
He jotted down a note of couple items I would need. One was a vacuum pump to start enlarging my nipples. Greg recommended a shop downtown that would serve my needs. I had unnaturally large nipples for a male. I always wondered what they would look like bigger.
I got dressed and was getting ready to leave.
“Think about what we discussed. We are not going to have any sex for a couple weeks while your tongue heals. Work on your nipples and ass. Keep that butt plug in on your way home.” He ordered.
I arrived home and changed. I forgot about the makeup and sat down in the living room, listening to music. Julie came home with some groceries and I got up to help her.
“My god..this is different!” she said in mild shock.
“Oh, I'm trying a new look”
“I'd say so! What happened to the shy, self-conscious girl of about a year ago?” she asked as she looked closely at my face.
“Broadening her horizons.” I said with a laugh. “I could do your makeup if you like, we could go out together”
“Thank you no, honey. I did the 'Go-Go' girl thing in the late '60's! Once was enough!” she said with a laugh.
I decided to take off the makeup and just relax. The butt plug was still in and surprisingly comfortable. Every time I would move, I would feel a little back pressure on my sphincter that was really enjoyable. I liked what was happening to me. I had the next 2 days off of work and made an appointment with Barry. He could get me in the next day. I called Sophie to come with me and she asked Sandy to join us. She had the afternoon off and we went over to the shop about 4. I wore my favorite denim skirt, black tights, a navy Cowell neck sweater and a pair of penny loafers. I felt kind of naked with out my padding on now. On the way over, Sandy told me what to expect with the tongue piercing. She had her done about a year ago. At Barry's shop, he had told me he heard from Greg and showed me what I was getting. The tongue piercing was a 12ga barbell with a larger ball on one end. He explained the whole process and was always calming in his demeanor. I paid then went back to his booth. I sat in the chair as he prepped his equipment. Sophie sat next to me and held my hand. Barry clamped the loop end hemostat on my tongue. Eyeing the placement, he took the sharp, which was setting in a dab of ointment on his left glove and hovered over my tongue.
“Deep breath and let it out” Sophie squeezed my hand. BLAM! A microsecond of intense pain! Again, he put a cork on the sharp then prepped the jewelry. It was a really odd feeling sitting there with a skewer through my tongue.
“That's a nice look on you. Keeps you from talking so much.” Sophie said laughing. I flipped her off. Barry was getting set up for the septum piercing. He tilted the chair back and used a gauze pad with ointment and cleaned out my nostrils. Weird feeling. He explained what was going to happen and he showed me the tools. A sharp with a tube that would receive it. Finally set up, deep breath.....microsecond of sharp pain and a strange 'crunch' as the sharp went through the cartilage. I was a little more painful than the tongue. He put in a 6mm gold anodized 14ga captive bead ring. He handed me a mirror and I liked what I saw. The girls did too. I was really high from the endorphin rush. I gave him a nice tip and he explained what to expect and the after care process. On the way out, I stopped in the ladies room to touch up my makeup. I'm still amazed how natural it is to go into the ladies room.
We decided to go to a coffee shop and relax. I wasn't supposed to smoke or drink coffee, but I did anyway. Sophie talked about how great Sandy's tongue piercing felt on her clit. I said I was wondering what Greg would think. Sandy asked my how my 'date' went with Greg. I told her it was some of the best sex I ever had.
“We know he likes kept CD's. Is that were your going with him?”, Sandy asked casually.
“Yeah..I think so. He asked me to get these piercings.”, I said reflecting.
“Well the septum looks good on you!”, Sophie added.
“Sophie told me about your new look. I would like to see it sometime” Sandy dropped in.
“Sure...I would love it!”
“It's been fun watching you change from insecure crossdressing boy to who you are now!” Sophie observed.
“It has been fun.....I wonder where this is going?” I replied
We parted ways. The girls wanted to do some shopping and I just wanted to go home and relax. Greg called and I told him I got the piercings and bought the nipple pump. He seemed pleased that I was serious about becoming one of his women. I read the directions on how to operate the pump and used it for the first time. I kept the cups on my nipples for 2 hours the first time. I noticed the size difference taking it off. After a few hours, they shrunk a bit but they were still larger than before. I did this daily and after 2 months, my nipples were getting big!
About a month after the piercings, Greg called and invited me over. I felt like a teenage girl waiting by the phone. I had bought some expensive eye shadow in prismatic turquoise/aqua just for this occasion. Greg wanted me at his house about 2 on a Saturday and told me what he wanted to me to wear. He wanted me in a 6 tab garter-corset, stockings with seams and 5” pumps. I had the pumps, I would have to go to Elaine's to get the corset. He also told me to completely shave from the eyebrows down. I wasn't sure how shaving my groin would go, but it was a lot easier than I thought. Having fine blonde hair and a wet/dry electric razor helped. I really liked the way my cock looked with no hair! I used a moisturizer and didn't much of a problem with razor bumps. I had to wear the heels around the house for a few days to get used to them. They were a bit more of a challenge than the 4” pumps. They did make my ass move in a sexy way and I loved how my calves looked! Greg said he wouldn't be home until around 5 and just be ready when arrived. I decided to pack everything in duffle and dress at his place. I arrived around 1:30 poured a glass of red wine and started on my makeup. I was becoming very adept at putting on makeup. I applied the contour and foundation with a bit of blush on my cheeks. I used the turquoise/fuchsia frost on my lids, a liquid medium brow gel that made my brows even more arched and defined. A thick swath of eyeliner with long wings on my lids and thick application on the lower lid. I had purchased 10 pairs of House of Lashes #026 because I knew I would be needing them. I had bought a gel lip liner with matching velvet 24 hour lipstick in cherry red and a shiny clear top coat. The high quality lipstick really stayed on! I wouldn't have to keep touching it up or getting it all over Greg's cock. A nice dusting of loose powder. I stood back from the mirror and really liked what I saw. I am becoming a whore, I thought to myself and I had to admit I liked it! It fit. The cincher I picked up from Elaine's was very pretty! It was turquoise satin with black lace panels on the front. The garter straps were wide turquoise satin with turquoise bows on the garter straps. I had purchased a couple pair of off-black stockings with seams just for this day. Getting the garters adjusted and the seams on the stockings straight took a little doing. I slipped on the 5” pumps and had to get used to walking in them. I did like the small steps that made my ass look tight. I went into the kitchen to freshen my wine and I noticed a device sitting on the table. With it was a simple note: 'put this on' .There was a set of instructions. It was a chastity cock cage in stainless steel. It was kind of a puzzle, but I figured it out. All that was left was nails and they went on in 5 minutes. I had read the instructions a couple times, but I finally got in on and the lock in place. I liked it! I started getting an erection that became very tight. It was a nice feeling. I was ready. I sat down and lit one of the 120's savoring how elegant they looked in my fingers. I did miss the lipstick stain on the filter though. I guess the lipstick was really smear proof.
I heard Greg's car pull into the garage. I felt butterflies in my stomach! The car doors and I heard Greg's voice, he was talking to a man and a woman. I tensed. I wasn't ready for this but there obviously no turning back. I went to the garage door waiting for him to come in. The door opened, he walked in with a couple. I kissed him lightly on the mouth. We walked into the living room. He and the couple handed me their coats and I hung them in the closet. I stood by the wall waiting for instructions.
“Come over here Kirsten.” Greg said. I stood in front of Greg while he looked me over. He played with my nipple for a second. I gasped for a second with the intense feeling.
“Go get the clover clamps with the chain.” I turned and left trying to look sexy with my walk. I returned and handed the clamps to Greg. He placed them on my nipples. They were tight but really pleasurable. I liked the feeling of the chain swinging.
“This is my new sissy, Kirsten. Kirsten this is Susan and David.”
“Hello” I said in a demure voice.
“Let them look you over.” Greg said. Susan and David were sitting on the couch. I stood in front of them both. Greg and Susan stood up and looked me over. It was awkward but really arousing. I knew it was pleasing Greg.
“Very nice! I love the makeup!” Susan said with approval. “Did you do it yourself?” she asked.
“Yes ma'am.” I replied.
“Have you been cross dressing long?” she inquired.
“About 5 years ma'am. I've been going out in public as a woman for 3.”
David sat down and told me to turn around. He rubbed his fingertips gently up and down my stockings. I though I would shoot into the roof!
“Spread you ass for me.”
I did so as if he was asking me for the time.
“Looks like you've been working on your asshole too. Very good!” he said.
He finished and I stood up.
“May I get anyone a drink?” I asked without any prompting.
“I'd like a Scotch and rocks.” said David.
Susan asked for a white wine and I brought Greg his usual Bourbon.
I walked into the kitchen aware of the eyes on me. I really loved it. I returned with the drinks on a tray, served them and sat down next to Greg. I lit a cigarette and took a sip of wine. The three started in on a conversation. As I sat there, Greg started caressing my leg which made my compressed erection even tighter. I was overwhelmed with how much pleasure I was feeling!
“Why don't we all get comfortable.” Greg interjected.
Susan ,David and Greg disappeared into the bedroom. A few minutes later, they all returned in satin robes. Greg sat in his easy chair and open the robe to reveal his large erection. This was my cue. I knelt down and took him in my mouth. I started to work my new piercing around the head and I could feel his pleasure. I used the ball on the stud to manipulate his PA. He groaned. I slowly started to push his shaft down my throat and when the head passed my throat, I began swallow, hoping the feeling of my throat would pleasure him. I could tell he loved it! I then pushed his cock balls deep and worked it up and down in small strokes. He started to pull out and I was going to resist, but thought better of it. I've already been smacked for being too 'enthusiastic'! He finally came out completely.
“I'm really impressed with your progress. Where did you come up with the throat technique?” He asked.
“I don't know, I just thought it would be pleasurable.” I said in my best fem voice.
“Dave, you have to try this! You want to get sucked off?” Greg asked.
“Sure. I'd love to stick my dick in that mouth!”
“Go suck Dave off.” Greg said in a commanding tone.
“Do you want me to make him come?” I asked with a level of excitement.
“Yes. I want you to drink it. None on your face, understand? Your face is my property!”.
“Yes sir.” I replied submissively.
I crawled on hands and knees where David was sitting. David was straddling the armrest of the couch. He opened up his robe to reveal a medium sized uncut cock. The foreskin was exciting! I took his flaccid cock in my hand working up and down. I was really fascinated by the foreskin sliding up and down reveling the head which kind of rounded. The rim of the glans wasn't very pronounced. As I did, I looked him in the eye with a very sultry look. I had my mouth open, ever so slightly licking my lips. He became hard as rock in very short order! I started rubbing the head all over my red lips and at the same time, pressing the ball on my tongue stud on the glans. I shot a glance at Susan. She had fingers in her pussy! Excitement overtook him! He straightened up slight and thrust the shaft in my mouth halfway. I pressed my face down taking him all the way into my throat, which wasn't difficult. I started the swallowing technique and he shuttered. I slid him back out, then swallowed him again completely. I did this about a dozen times and I started to taste pre-ejactuate on my tongue. I knew he was going to cum soon but I wanted to keep him on that edge as long as I could. The longer I stayed there, the bigger the load. I worked over his glans with the stud ball until he was shuddering. All of a sudden, he thrusted forward and in about 3 contractions, filled my mouth with cum! The load slopped out of my mouth onto the shaft of his cock. I swallowed his load! It was kind of salty-bitter. I licked up what was left on his cock. He groaned and slid back on the cushion, kind of slumped.
“Did I please you?” I asked in a sultry voice.
“Jesus girl, you can suck dick!” he gasped. I got up and sat down in my spot by Greg. I could see he was obviously pleased with my performance. I lit a cigarette noticing David looking at me. I drank some wine to help wash down the sperm left in my mouth.
“You should be proud of her.” David commented.
“She doing really well for such a short time. I'm thinking of collaring her pretty soon.” Greg said looking at me.'
Greg told me to go into the playroom, put the waist belt, ankle and wrist cuffs on and wait. I did so and stood by the bed with my fingers laced in front of me. All three walked in. Greg took my arm and led me over to the ceiling chain. He hooked the wrist cuffs to the rings on the side of the belt and placed the spreader between my legs. He hooked me to the chain and hoisted me just high enough to keep my feet on the floor. As he did, Susan strapped on a rather large dildo and made a point of making sure I could see it in the mirror. Susan put on a pair of rubber gloves, squirted a large glob of lube her hand and proceeded to work her fingers in my rectum.
“Has she been fisted?” Susan asked Greg.
“Not yet.
“Do you mind if I stretch her out some? Susan asked.
“Please do!” Greg said with approval.
“If you relax, this will feel good.” She whispered to me.
I allowed myself to relax, don't think and let go. Her fingers moving around my sphincter felt really good. She finally worked 4 fingers and was pressing forward then pulling back out. I was just focused on relaxing and going with the flow. She finally pressed and I was stretching to the point of pain. All of a sudden, the pain passed but I could feel something large in my ass.
“I have my hand in. Not bad for the first time.” she said. The whole time, Greg was taking pictures with his digital 35mm. Susan moved her hand backwards and forwards gradually going little deeper with each stroke. I was in a semi-conscious bliss. Every so often, I would glance at the side mirror and saw that her forearm was in my ass. She slowly withdrew her arm and lubed me up with more jell. The dildo on her strap-on was about 12” long and 3” in diameter. Susan positioned the dildo and pushed in. I was so gaped that I didn't notice until the dildo was a quarter of the way in. She slowly stroked back and forth. Susan finally pulled out. Greg stood behind me and put the head of his dick in my anus. This is what I have been waiting for! Greg pumped my ass hard for about 3 minutes! His cock felt so good I wished he would go on forever! I knew better to whine about more. Greg slid in a large butt plug to keep me gaped. He unhooked the chain, the spreader and told me to stand. As I did, I noticed that Susan had large diameter 10 ga rings in her nipples. I really liked the look! I wanted some of my own.
In one of the corners of the 'playroom' was a leather sling sex chair with an electric winch for adjustment. Susan sat in it and put her legs in the stirrups. She was spread eagle and her vagina fully exposed.
“Kirsten, service Susan.”, Greg ordered in a nonchalant voice.
I knelt down in front of her pussy, not sure how to perform oral sex on a woman. Greg used the control box position her at the right height. Susan had large inner labia rings. Greg unhooked my wrists from the waist belt. I leaned forward and started to lick her. I knew the basic female anatomy and started to rub the ball of my tongue piercing on her clit. She started groaning. I swirled and flicked my tongue on the clit, licked the inner labia and went deep into her vagina. She was writhing with pleasure! She was becoming incredibly wet and though unfamiliar (I never went down on a woman before) I was enjoying the musky taste of her. As I was giving her pleasure, I was moving my ass around enjoying the fullness of the butt plug.
“My clit, my clit!”, she shrieked. I moved the ball of the stud and rubbed with pressure. She grabbed the back of my head and pushed her pussy into my face. She exploded with orgasm shrieking the whole time. She gently pushed my head back and I crawled off to one side of the chair. I had pussy juice all over my face. David had recovered from his first orgasm. He used the control box on the chair to reposition it. He took a position between Susan's legs and started to slide his hard cock in side her. David started to stroke her, building his rhythm until she had another orgasm. David was shuddering. He thrust forward and let out a guttural scream as he came a second time! He slowly pulled himself out and cum was pouring out of Susan.
“Clean her out.” Greg ordered.
Without hesitation, I started to lap and drink all the cum I could. I tried to be gentle because I knew her pussy was really sensitive. I know what my cock feels like after I cum.
They all dressed and Greg told me to fix my makeup. We returned to the living room. I sat down with Greg and lit a cigarette then held his arm. He put his hand on my thigh, gently rubbing my stockings. The feeling was electrifying and shot straight to my groin.
“You really need to take her to Eric's, Greg. She needs to perform!”, David commented.
“She needs a collar first. We still have some work to do before that happens. She needs the rest of her piercings. She also needs to know what commitment to a collar means.”, Greg replied.
I knew better to say anything in front of others. From what little I knew about being a submissive, I knew enough not to speak unless spoken to. Their conversation wandered into what was happening friends, who had new slaves, politics, etc. With all the talk of slaves and submissives, I became quite aware that I was indeed heading down the rabbit hole!
After about an hour, David and Susan got up to leave. I went to the closet, got their coats. David kissed me on the forehead, which I thought it odd. Susan kissed me on the cheek, squeezed my hand and smiled. Greg said he was taking them home and he would be back in about an hour. I drank a little more wine and reflected on the day. I was trying to digest the personality that was emerging. I started to believe that this submissive sissy slut is who I've always been and just need some 'cultivation' to grow. I really didn't care. I was loving who I am! I touched up my makeup. I had to wipe off the 'pussy juice' and touch the foundation and powder. I always wanted to look my best with Greg. Greg's car pulled in. He went into his bedroom changed and then sat down in the living room. I stood by the kitchen door, fingers interlaced in front of me waiting for instruction.
“Freshen my drink please.” I did so. He patted the seat next to him. I sat down.
“You did quite well today. I'm pleased.”, he said as he sipped his Bourbon.
“You handled meeting new people well. You knew what you supposed to do and did so with enthusiasm.”, he said looking at me.
“What are your thoughts? What did you feel being told to service David and Susan?”, he asked.
“I loved sucking Davids cock! It was such a turn-on knowing you were watching and I wanted to make you proud!”, Servicing Susan made me nervous because I've never had sex with a woman.”, I answered.
“I'm impress with your lack of hesitation, no nervousness with strangers and you carried yourself with pride. You used 'Sir and Ma'am' without prompting. I think you're getting very close to committing to the collar. What needs to be done now is the rest of the piercings. The enlargement work you have done on your nipples is quite pronounced. I think you can get 10 gauge barbells with room to spare. I'll talk to Barry. I have a specific way I want them pierced. I want you to see a woman for your PA and Guiche. Her name is Zoe. She's very good.”
“I really want to please you!” I replied in a demure voice. As I ran my nails gently up and down his arm. I was surprised with my sincerity. The evening wound down. I took off my makeup and put on my sweats. Greg gave me a ride to the gallery. I laid in the bath tub pondering the events of the day.
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Chrysalis of Kirsten
Chapter 1: Youth and Confusion
Chrysalis of Kirsten
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- crossdressing, Bondage, Dominance, Submission, Gay, Oral, Anal, Fisting, Sex Toys, Blow job, Shemale, makeup, transformation
Updated on Apr 2, 2019
by KirstenEclipse
Created on Mar 23, 2019
by KirstenEclipse
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