Custom Maid Mistress: Genesis

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A shemale mistress is made.
9.5k words
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Part 3 of the 3 part series

Updated 08/31/2017
Created 10/23/2012
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My name is Jamie; I am freelance photographer and a masseur. I am 21 year old guy but look to be about 16. I am four feet and ten inches tall and now weigh 110 pounds.

It had been an awkward time growing up being as short and thin as I was at the beginning of last year. I have never had to shave and have looked like a young high school kid for many years now. I have, despite my slight stature been blessed with two endowments that seem to endear me to what women with which I have been romantically close. I have the good fortune to have an extensive manhood and long tongue that I can extend four and a half inches past my lips. I have always been of a different mindset than most people. I have always been creative, entrepreneurial, free-thinking, and non-judgmental.

I actually have a very good massage business going. I have loyal regular customers that are almost exclusively women. I suppose that I am very non-threatening and trustworthy. One of my best customers changed my life completely beginning early last year. My customer's name is Monique; she is a plastic surgeon with a deep purse and spends grandly.

The day my new life began, I was at Monique's palatial residence and had just began to give her a very long attentive massage up in her beautiful spa room. She told me to undress and massage her without my clothes. She tipped well for the extra attention, so why not. She lay down in a prostrate position and closed her eyes and enjoyed my manipulations. I worked her back down to and including her luscious ass. I went down each leg on the outside then back up the inside up to her upper thighs, almost to her pussy.

I then moved around to her head and massaged her shoulders. As I moved up to her neck, I felt her hand upon my slightly stiff member. As she began to squeeze and stroke my stiffening cock, I heard her gasp. She had opened her eyes and was examining my penis in her hand.

"How long is that gorgeous thing?" she asked. "It is very impressive, young man. It looks absolutely huge on your small frame."

"It is eleven and a half inches and about five inches around." I said. If you like my penis, check this out." And I slowly stuck my tongue out until all four and half inches were beyond my lips.

She then flipped over onto her back and spread her legs over the sides of the table. "Massage my clit and pussy with your tongue. Stick it deep into my pussy." she demanded.

I complied. I began to tease her two inch long clit with my tongue and worked my way over to her pussy. I fucked her pussy with my tongue, wiggling and snaking it around until she creamed from two orgasms. She sat up, told me to stick my tongue out, and began to suck my tongue in and out of her mouth. She then suddenly sat upright and had the look of being struck by a brainstorm.

She said to me, "I would like you to come here and live with me. I have an idea on how I could give you a gift and tweak you to perfection. You would be one the sexiest creatures alive."

"It sounds nice," I replied, "but what's the price? There is usually a catch." "All I ask is this," she detailed, "You live here, let me craft you, my sister will be moving in shortly, help her however needed, you are free to socialize as you wish and work as you wish, sex as required, I will pay for your needs, and do work that I require of you. Move your things in tomorrow. We can call it a session for this evening."

"Okay," I agreed, "I will do it, what the hell." I went home and got to work packing things.

When I arrived at her house the next day with my things, she took me up to my new room and I placed my things down. She told me to come with her into town; we were going to the salon. We arrived at the salon she uses and sat down with her stylist, Georges. Monique showed him what she wanted to do to my hair and he nodded. He went to work, chatting constantly. After a brief time, he was finished. He spun my chair around so that I could see the result. My jaw dropped, my hair was done in an androgynous short punk style that made me look hot no matter what sex I was. I was then escorted into the back where they did ear piercing. I sat down, Monique communicated what she wanted, and then they pierced both of my ears and my navel.

When we returned to her house, Monique pulled a syringe and vial out of a drawer, drew out some of the contents into the syringe, and injected it into my ass. She told me that it will help me out immensely. I continued to work my massage appointments for the next few days like nothing had changed. I received regular injections like it was a normal routine thing. I didn't ask. One day, Monique took me to her office and led me to an operating room. She sat me down in the operating chair, leaned it back, and injected my tongue with Novocaine. She propped my mouth open and proceeded to probe around my tongue.

Telling me to relax and trust her, she called in her nurse who then immobilized and held my tongue. I saw a scalpel go in my mouth and could tell that she was doing some cutting. After she had finished, she shot me up with pain killer, cleaned up my mouth and took me home to her abode.

I spent the next few days recovering, consuming liquids making sure to move my tongue around. Monique checked my mouth regularly. Something seemed really strange, it was moving around in strange ways. When it had healed, I finally got up the courage to take a look at it. When I opened my mouth, I was still shocked at what I saw. My tongue had been bifurcated for about three inches. I began to experiment with moving it around. I was finally able to manipulate each of the thin three in tongues somewhat separately. The real challenge was to keep them acting as one in order to speak properly.

My nipples began to itch quite a bit all of the sudden. I had to grab them and manipulate them to alleviate the irritation. I had to do it many times a day. I could not figure out why.

I was finally able to master my speech with the split tongue again. I was also getting pretty good at moving each tongue half independently. It actually seemed kind of cool to move it around twist each side around the other. I was now able to hold my tongue up and tap both sides of my nose.

Monique came into my room topless while I was watching some TV. She asked to take a look at my tongue, so I stuck it out and moved it all around. She smiled and said, "Lick my nipples and play with them with your tongue." I leaned forward, taking an ample breast in my hand and began to tease the nipple with my tongue. I alternately teased it with the tips of my tongue and ran it back and forth between both halves. Take her other breast in my other hand, I licked and manipulated her both of her nipples for a long time. I then took a breast in my mouth and began to suck on it. When I drew on the nipple and areola a sweet liquid poured into my mouth. I lifted my up head momentarily to see what was going on with it. Milk was leaking out of the beautiful mound. I resumed my drinking from her until that breast was dry. I switched to the other one in order to finish my liquid lunch.

When her milky tits finally ran dry, she said, "Eat my pussy, I'm so wet that I am almost flowing." She laid back and spread her legs, gently guiding my face into her slit. I licked her clit like I had done to her nipples and she to scream. She then slammed my face into her pussy and I thrust my "tongues" deep inside her. I deeply tongued her pussy like a whirling dervish. She bucked and screamed so much that one would think that she was having a seizure and a Tourette's episode at the same time. She came several times during the short time that I was eating her. She was running her juice into my mouth constantly. When I finally came up for air, she collapsed, just breathing deeply and sighing.

"You see why I had your tongue done like that?" she moaned. "I have never had anybody go down on me so greatly before. She then pulled me over to her mouth and kissed me deeply where I made intense love to her tongue with my long split one. We broke our kiss and she feebly stood up, gave me a kiss, and struggled her way out of the room and said "Thank you."

We had almost daily eating sessions and at least twice daily breast drinking sessions as a matter of routine. The routine injections that Monique had been giving were apparently having an effect. I guessed that she had been giving hormone injections. My nipples continually itched and had grown to a half inch long and slightly wider than a pencil. My chest had been tingly as well and between the hormones and my massaging the irritation away, I now apparently had at least A-cup breasts. I had finally figured out what she had been doing. It actually looked kind of cool. I am now wearing loose, heavy shirts when I go to do massage appointments.

Monique's sister finally arrived to live with us. It was very apparent that she was actually pregnant and due in a few months. She looked very much like Monique only she was a brunette instead of a blonde.

Monique introduced us, "Michelle, dear sister, this is Jaime. Jamie, this is my sister, Michelle. You two should get along just smashingly. You will all get to know each other well enough before too long. Michelle, Jaime has the most amazing tongue that you could ever hope to meet. Jaime, give her a deep, passionate, welcome kiss, would you, my dear?"

I pressed my lips to Michelle's and pressed open her lips with my tongue. I massaged hers with mine, running both halves all over and around her tongue. I massaged the inside of her mouth all over with my split tongue. When we broke our kiss, I whispered to her, "You should see what I can do for your nipples and your pussy." She smiled devilishly.

I commenced a daily workout and toning routine in the workout room the basement. Monique actually had great equipment in her gym. If I was growing breasts, I want them to be as perky, prominent, and defined as they can be.

Michelle is a very successful and dedicated realtor who makes a lot of money and spends a lot of time working. I did not see much of her for quite a while as I was keeping a very full massage schedule. It was mostly hum-drum, run-of-the-mill type stuff, but it kept money in my pockets.

Over the course of the time leading up to mid-summer, I had a regular routine of injections, massaging my breasts and nipples to relieve the itching and irritation. By this time, my chest had grown to an impressive B-cup. Now, I switched to wearing low-cut tops, tank-Ts, bikini and tube tops. I started walking around the neighborhood on a daily basis. I began to meet a lot of the young women and guys nearby.

I started hanging out with some of the neighborhood kids and going places and shooting the breeze and getting to know each other. We hung out behind my friend Rachel's house all of the time and occasionally in her basement. On the one occasion that started the whole sexual thing rolling, Rachel told me a tremendously funny joke and I was rolling on the floor laughing. I was laughing hard with my mouth wide open. She was looking right at me and I was off my guard. She was staring right at my mouth and her eyes were wide open.

"What?" I asked her surprisingly. "What are you looking at?"

"Is something wrong with your tongue?" she asked. "Or is it my imagination?"

"No, nothing's wrong with it" I said. "Look." I ordered, sticking my tongue out. I wiggled it around and doing all sorts of tricks with it. "Watch this." I pulled my tube top down, lifted up my right tit, stuck my tongue way out and teased my nipple with both ends of it.

Rachel said, "That looks amazing and hot as hell."

I stopped licking and teasing my nipple and reached over and pulled her top off her shoulders and down her torso. I reached over to her and took her tit in my hand, leaned down and licked and tongued it, slipping the halves of my tongue over and around it. I worked and sucked on first, one nipple and then the other while massaging her tits simultaneously. I continued for a while until she said that her panties were getting soaked from her pussy juices.

I then let go of her cute breasts, lifted her skirt and pulled her panties off and cleaned her pussy off with my tongue. I teased and worked her clit and labia, occasionally thrusting my tongue deep into her pussy. After she came a couple of times, I stopped and gave her a quick kiss on the lips and sat beside her.

She turned and played with my tits, occasionally licking my nipples and sucking on them. She continued until silently, our friend Tim walked in. We startled, Rachel pulled her top up and straightened herself.

"Hey, it's cool!" Tim exclaimed.

"Come here and feel and play with my tits, Timmy" I said, patting the couch next to me. He sat down and worked over my tits and sucked on them. This continued uninterrupted until Hank, Chris, Frank, and Gabe walked in.

"Join in and enjoy my tits!" I told them. My tits were worked over and sucked on for long while until I told them that the time's up. I had a hard on under my skirt that was almost painful. I pulled my top up and straightened my outfit.

We continued the "cop and feel" sessions quite regularly. It saved me a lot breast self-manipulation.

By the time late summer had rolled around, my breasts had grown to a C-cup and my nipples were now the width of a dime and three quarters of inch long. I decided to start using a breast pump to get myself producing milk. I figured that I would be enlisted into wet nurse service any way when Michelle's baby was born.

Aside from the somewhat regular task of emptying Monique's lovely udders, Michelle now was having me help express her breasts. When Michelle's breasts began to flow, I emptied them of milk at least twice daily. I have been enjoying a large diet of fresh, warm breast milk. It has actually helped me get my breasts to begin to produce the sweet white nectar.

Monique mentioned to me one day that she had a friend who had a son who was gay and that he was trying to stay under the radar. Monique said that she had mentioned to her friend that I would probably be willing to accompany him to his senior prom to help propagate the illusion of normalcy. She said that he was a really nice kid and he was a member of the football team. I agreed to do her the favor and help out.

I was now attending all of my massage appointments dressed in a relatively short white skirt and low-cut tank top t-shirts made of slightly heavy fabric that was thick enough not to be translucent since I wear them mostly braless. I look pretty hot when I am dressed for doing massage work, if I do say so myself.

I went to do a massage for a couple who lived nearby who are in their 30s who wanted back-to-back individual massages. I arrived and rang the doorbell. After a brief wait, a gorgeous, raven-haired woman answered the door. She introduced herself as Sheri and bade me to enter. I brought my kit inside and she led me upstairs to the bedroom where I set up my table. She said that her husband Pete would be along shortly. I asked if she wanted to get started right away or wait. She said that she wanted to start directly. She went to the bathroom to change and returned momentarily with only a towel wrapped around her body.

I had her lay on the table face down and I undid her towel. Sheri's beautiful body was spread out in front of me. I applied oil to my hands and began to massage her neck and shoulders. I moved next to her arms, doing one and then the other when she turned to look at me and said, "Take your clothes off and work on me while you are nude. I will pay you extra."

"I really don't think you want that." I replied. "I, ah, am not sure that, you..."

She cut me off, saying "Do it! It's nothing that I haven't seen and I want this."

"Okay." I said. I stripped my clothes off and laid them on the bed. I then went back to work on her. I went down to her feet and worked my way up her legs. I then bellied up to the table and proceeded to massage her shoulders and work my way down her back. I worked my way down her back and worked her tight ass intently. I massaged the insides of the thighs and groin. I then stopped and asked her to roll over. As she rolled on to her back, I scooted around behind her where she would not see my stiff rod standing outward.

I massaged her face and when I moved on to her neck, she opened her eyes and beamed an excited smile. She reached up and began to feel my bare breasts, creating a huge distraction for me but not for my member. I worked on to her arms, first working her left one and then her right one, staying tight against the table. I then began a dedicated massage of her chest and breasts. As I methodically massaged her breasts, she began to massage mine.

My cock was rock hard and throbbing. It was all that I could do to pull away from her grip on my breasts. I was finally able to massage her stomach and legs. When I hit the upper end of her thighs, I massaged, fingered, and manipulated her pussy. She asked me to come up to her head. She took my arm and drew me down toward her face. She pulled my breast to her mouth and latched on to my nipple while holding my breast with both hands. She was tonguing and stroking the nipple with her tongue, driving me crazy and making me harder.

I could tell that she was suddenly drawing milk into her mouth as her mouth switched to only a deep suckling of nipple. She moved one hand to my other breast and was kneading and squeezing it. When she finished with my breast that she was drinking from, she quickly moved to the full one and continued nursing from me.

When she finally let go of my nipple, I moved around between her legs and down between her thighs. I began to tease and lick her clit. Shortly, I began to eat her out very intensely. She started moaning and yelling. As I came up for some air, Sheri pulled my face up to hers and kissed me deeply. It occurred to me that the end of my cock was rubbing against her clit and pussy. She was unconsciously grinding against my member.

I reared back until my cock was pointed at her pussy and pressed at the entrance and slowly thrust it in. I pushed until I reached the hilt with her crying out a continually parted her insides. I began a slow rhythmic fuck of her while occasionally kissing her and licking and sucking on her tits. Just as I was approaching my orgasm, I felt a tongue on my cock and balls as I fucked Sheri. It was too much to endure and I slammed forward, burying my almost foot of meat in her pussy and poured a torrent of cum into her uterus until my python ceased its spasms and with it, the flow of sperm and semen.

I slowly withdrew my organ from her love canal. As the torrent of my seed followed my cock out of her vagina, Sheri's husband Pete's tongue replaced my cock in her pussy. She tapped Pete on the head and pointed to the king size bed and they got up, went to the bed, and took up their previous positions, as did I. Sheri told me to lie so she could suck my "huge meat" and that she wanted me to suck Pete's. What the hell, I thought, she's paying for it, so I got in position and got ready for my first time.

I took his eight inches of meat in my hand slipped both halves of my tongue around it and fucked it with my tongue. I ran it through my tongue for a little while with him constantly moaning in the background. I then wrapped my lips around it and repeatedly took it deep into my mouth. I continued the mouth fuck for a few minutes and then I began to deep throat him while running my tongue around his cock. He let it be known that he was going to cum. I felt his rod stiffen and I took it all the way in my mouth and throat and it began to pulse and spew his cum down my throat.

I then released his cock from my mouth and cleaned it off. She motioned for Pete to come over and fuck her and let her put some lube on his asshole. She told me to fuck him hard while he fucked her. I got up behind him and slowly put my cock in his asshole while he entered her now gaping pussy. I pushed my meat deep into him and then when he had adjusted to me, I fucked him hard, steady, and fast. I pounded his ass hard until I came, letting loose another torrent of cum. I pumped it deep into his ass causing him to blow off his cum into Sheri.