Carrie Ann's Delight

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Closet transvestite is cuckold and dominated.
7.9k words
4.27
93.5k
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Chapter One

It was a Friday afternoon that seemed of little consequence. I got up, shaved, cleaned and pampered my body. After my underwear was in place I wore my usual boots, boot socks, jeans and a plaid shirt. The bar at Fulton Street was busy that afternoon when I arrived about 2:00 and everybody including Lori (the owner) seemed glad to see me. Joe and I took on all comers in partners pool. We drank Budweiser long-necks, sang poorly at the top of our lugs and flirted with the girls. Two redheads from out of town were the main attraction for the afternoon and while I am truly harmless it seems to be my manly duty to flirt.

I was in the middle of just such a duty when the front door opened to a collective moan – sunlight and heat crowded into our cave. I couldn't tell who it was because of the glare, but she was wearing a long brown peasant skirt of very thin material. She wore high heel boots and a forest green halter-top. Hugh bare breasts jiggled provocatively beneath the loose fabric. They looked familiar and they should have they were Rachael's – my wife.

She had firm, natural "C" cups and she loved to show them off in public. She walked by me with a contemptuous glance and not one word. Every eye in the room was on her as she slid her long slender frame onto a stool at the far end of the bar.

She ordered a Scotch neat looked at me through the mirror behind the bar and tapped a beautifully manicured index finger on bar twice as if she were making a command on her computer.

I could barely stand, week with fear. I was a few minutes late getting home, but she had never made an issue unless she had instructed me to do something. This time she was pissed. Right here, in this most sacred of places for me, the shit was about to hit the fan.

"Hi, honey" I said as bravely as I could.

Rachael slapped me firmly and said. "Don't hi honey me you slut and don't eyeball me."

I was never supposed to look at her eye to eye, but I had never been around her under these conditions and in public. "Yes, Mistress Rachael" I said dropping my eyes to her feet."

My friends that were not stunned into silence were snickering between themselves. The big bad Carl was a wimp.

Rachael took a sip of her drink and said. "Remove your boots."

This was going to be the pits, but she and I both knew I was going to do her bidding. I pulled my boots off.

"The socks." Was my next command and there I stood, my manicured French tips shining through charcoal hose.

Rachael reached in her bag and handed me a short black pleated skirt.

I pulled my jeans off revealing a black silk garter belt; smooth shaved legs and charcoal hose with seams up the back and little red bows at the top. My thin charcoal panties revealed I was wearing a CB6000 chastity device. My genitals were shaved smooth but for a narrow strip of neatly trimmed hair above my clitty stick.

I was beyond embarrassed and in tears as I slipped on the skirt. At least, it covered some of the humiliation. Some of the guys, former-drinking buddies, were cat calling and asking for more.

As if to answer their requests Rachel reached in her bag and came out with a black lace front-closure bra dangling from her right index finger.

I removed my shirt to reveal a black silk teddy with spaghetti straps. I pulled it over my head. My chest, tummy and pits were smooth shaved. A piercing, that had been my first, dangled from navel. I put the bra on to an increasing chorus of howls from my "friends". I inserted mastectomy pads into the little 36 B bra cups, and donned a sheer white blouse. I was beginning to wonder if Rachael had our kitchen sink in that bag when she produced black patent sandals with 6" stiletto heels.

Rachel finished her drink and ordered another, indicating this ordeal was not near over. She stood, gathered all my male clothes, walked over to the trash bin and dropped them in, including my boots. She turned on her heels and without a word returned to a seat at the table nearest where I was standing. Before she took a seat she reached under her skirts and removed her white lace thong.

From her chair she held it to my nose. No further instruction was required. I dropped to my knees, lifted her skirt and crawled underneath.

It was safe between her legs. The light filtering through the thin material was just enough to see my prize. Her fat outer lips engulfed her inner lips and hid her clitty. She was smooth shaven but for a sliver of hair above her opening.

Using the flat of my tongue I lapped, like a little puppy, up and down her opening. She was moist and delicious. There is only one thing that tastes better than Rachael's hot moist pussy.

She put her hands on the back of my head and pushed me into her. That was my signal to get more serious about my task. I slipped my right thumb inside her and kissed the sensitive places where her thighs met her smooth flat tummy. I blew a little breeze across her clitty the flicked it with my tongue. She lurched and moaned. I sucked her little bead of nerve endings into my mouth and started flicking it with the tip of my tongue. She wrapped her legs around my head, crossed her ankles and started to squeeze. She was crushing my head as she bucked and wiggled, but I was on her clitty like a leach. She would climax before I released it.

"Would anyone like to fuck this bitch while she is on all fours?" I heard Rachel ask. She had climaxed and my face was wet. She pushed me away from her clitty, but kept my head in a grip.

The best I could tell nobody moved, so she asked. "How about a blow job? This bitch can suck the nails out of a two by four."

Again nothing stirred. I guess my friends decided to take pity on me that one time.

Rachel released me and pushed me back hard. I fell backwards on my ass. "You worthless bitch." She said as she stood, straightened her skirts and left.

I couldn't believe the condition I was in. Silently I crept behind the bar and wiped my face with a wet towel. I retrieved my clothes. My keys were gone. I searched the trash bin, but no keys.

Looking at the floor, I asked. "Could anyone give me a ride home?"

George Cotter, whom I'd known for fifteen-years said he would and asked if I wanted to change. I didn't see the point so I declined, anxious to get the hell out of there. I followed him out to his car like a whipped dog.

As he pulled out of the parking lot he said. "I'll take that blow job now."

I was stunned, what an asshole. At least I wouldn't have to talk so I unzipped his pants and got his cock out. It was small, cut and slender with an upward curve. He was wet with pre-cum when I put him in my mouth. It didn't take much work on my part and he filled my mouth with his cream. A few drops spilled on the seat. I swallowed the rest and then without a second thought I scoped the drops off the seat with a finger and placed them in my mouth. Waste not want not even if the guy was a first class jerk. I licked his cock clean, put it back in his pants and sat up in my seat. Not a word was spoken, not a glance exchanged. When we got to my house, better make that Rachel's house, he pulled up the drive, I got out and went inside.

Chapter Two

Rachel was sitting at the bar sipping on another neat Scotch, a thin black cigar burned in the ashtray next to her. Her skirt was bunched above her knees reveling her long beautiful legs.

"I hope you enjoyed your trip to the bar. You will be spending a lot more time between the legs of a real woman and often it will be in public. Do you understand?"

I didn't really. I'd been cuckold for a couple of years, but she had never suggested there could be female lovers for her or for me. However, I said. "Yes Mistress."

How did you get home?" Rachel asked.

"I couldn't find my keys so George Cotter brought me."

"For a price?" She asked with a sly grin.

When I didn't reply, she dismounted and walked over to where I was standing and slapped me very hard. My eyes were down and I didn't see it coming. It staggered me; I fell against the couch and hit the ground.

"I asked you a question, Bitch."

"Yes Mistress. Yes he made me suck his cock."

"I know." Rachel said. "I paid him." She pointed to a corner across the room and said. "Kneel in that corner."

I heard what I assumed was Rachel return, but couldn't determine what she was doing. I'd been in the corner for 30-minutes or so when she said. "Go to your room and follow the instructions on your bed."

My room was the former guest bedroom. It had been redone in pink with white trim. Ruffles and lace were everywhere and the walls were covered with pictures of male strippers, their flaccid cocks hanging provocatively from their perfect tanned bodies. There were no doors on my room. Carrie Ann was not allowed privacy and there were lots of mirrors not for vanity, but to shame me for what I had become.

The first item on the list was – Clean yourself. Not referring to a nice warm bath, of course, but to an enema. That was a frequent daily chore.

I stripped out of my clothes, hung up the skirt and blouse, put the bra, panties, hose and garter in the dirty close bag. I hand washed these items every other day.

I filled the 2-quart bag with a scented oily ingredient that mixed with warm water to for a milky cleanser that went in me smoothly most of the time. I used a double Bardex. I put it inside me, pumped the balloons up and laid down on a large bathmat next to the tub. There was always pain and cramping, but the Bardex offers no options. The full two quarts was going in me and it did so fairly quickly. While I held the solution for the required five minutes, I brushed my teeth, combed my hair, and applied White Shoulders lotion to my hairless body, put on deodorant and White Shoulders perfume. I'm not required to smell strongly of perfume, but I use the scent in its various forms and it is not "Old Spice". Once the fluid was expelled, I put a super tampon in me and returned to the list.

Sure enough the second item was put a tampon in you. It always struck me as odd for my wife to insist I wear a tampon. Oh well, I wasn't the sharpest knife in the drawer anyway.

Down the list I went. The white spandex high-cut briefs were closer to a girdle than panties. They had the additional duty of holding my CB6000 back between my legs. They were trimmed in lace and had breather panels down both sides. The bra matched the panties, was made of spandex and was front closure.

The blouse was of a very thin material with a larger open collar and three button sleeves. The details of my bra were clearly visible.

The gray trousers had pink pin stripes and were elegantly tailored in year-round wool with a side zipper. My waist is fairly small for a male at 32" and my caboose is a shapely 38". In most cases I wear a size 10T. These trousers had been lengthened in the crouch to provide additional space so my clitty stick cage wouldn't ruin their drape. The belt was thin pink leather with a delicate silver clasp.

I have a narrow foot for a male wear a size 9.5B or 10B in ladies shoes. The shoes for this outfit matched the belt. They were pink leather, open-toe, wedge sandals with I.5" heels. The strap between my big and index toes featured the same delicate clasp.

There was no jewelry and all my identification, credit cards, keys and cash were in a stylish pink clutch purse. Rachel had thoughtfully included a delicate lace handkerchief and a spare tampon.

I never really used makeup and while my hair was on the long side it was cut in a male style parted on the right.

When I entered the den, Rachel turned and took a long look. Pointing toward the fireplace she said. "Walk over there, turn a couple of times and come back. You know runway style."

When I had done as instructed. She said. "I want you to practice putting more up and down motion in your hips as you move. It will help if you try putting one foot down directly in front of the other. Otherwise, it just the look I wanted." She picked a lipstick up from the bar and said. "Put this on and we will be ready to go."

Go exploded in my head. I had reached for the lipstick, but I froze. I momentarily looked at Rachel, terror in my eyes. I quickly dropped my eyes, but the damage was done.

"Listen you fagot, don't even think about disobeying me – ever. From now on you are my sissy sex toy. If I say jump, don't bother to ask how high, just jump as high as you can. Right now I'd like to take my cane and turn your ass into hamburger. I don't have time right now, but if you do one more thing to piss me off and I'll take the time. For the moment, let me give you a taste of one of the ways your punishment will take in the future.

Rachel turned and pulled her skirt up. She had not put her thong back on. She bent forward and said. "Clean it."

I went to my knees, spread her ass checks and began licking her anus.

"French it." She said.

My tongue went deep inside her rectum.

After a moment she stood and asked. "How did you like that Carrie Ann."

Still on my knees I responded the only way I dared. "Thank you Mistress Rachel. It is a pleasure servicing your beautiful ass."

"Just remember, you displease me and I may never need another piece of toilet paper. Do you clearly understand?"

"Yes, Mistress Rachel."

"I hope so, the next time I need to pee I'll elaborate." She said, offering the lipstick again.

This time there was no delay. I accepted the lipstick, stood and went to the mirror behind the bar. I wiped my lips with a napkin and wished I could brush my teeth or gargle. I applied the coating to my lips. It was a wet pink and caused my lips to glimmer.

We drove to the Springdale Mall in silence. Rachel parked close to the front entrance and waited for me to get her door. She preceded me through the mall leaving a trail of discussed onlookers in our trail. She was in her element, a rich bitch with her sissy trophy-husband in tow. I really embraced this role, but I had just never been so exposed before. My clitty stick was drooling as I practiced my hip swing.

Our arrival at Victoria Secret caused quite an initial commotion. Rachel was calm and deliberate about her task. Because of the problem between my legs she started with panties. She asked the salesgirl to join us in a fitting room to show her the problem. I wiggled out of my trousers. The thin, tight fitting panties left no question what the problem was. The young woman was more embarrassed than I was, but recognized a big sale in the making. Her nametag said Sheila.

Rachel and Shelia carefully inspected the inventory for panties with a wide crouch that also had a matching bra. Every time they found a match, Rachel took every color they had, but not before I held them to my body to be sure "the color looked good on me".

They had a limited selection of garter belts they thought looked good with the panties. Rachel added them to my pile.

In front of Rachel and Sheila I tried on teddies, nighties and gowns. Each of the other salesgirls was offered, and accepted, an opportunity to act as a judge. By the time we were finished each young woman got to see a sissy up close and personal. Giggles and red faces turned stories of female domination with Rachel as the queen bee.

Rachel selected a couple of tube tops and a couple of sheer lace tops. Glancing at her watch she noted it was getting late. We checked out and Shelia helped us get our loot to the car.

We went back in with Sheila, who had confessed to being a lesbian during the process. She and Rachel kissed unabashedly for several minutes in front of the store and agreed to meet for dinner the next Tuesday. I had a feeling I would soon be between Shelia's lovely legs.

Rachel escorted me to a kiosk near the food court and informed the young man she wanted my ears pierced. He smiled obligingly and I took a seat. Rachel stood and watched as he put three holes in each ear and filled them with silver studs. He took every chance to feel my crouch and finally got to the cage. Looking at Rachel he said. "You have the sissy caged."

Rachel acknowledged in the affirmative and asked him to step over to where she was standing. They whispered back and forth and then he returned to where I was seated.

With Rachel on my left shoulder and the young man blocking the view from the other side, he undid my blouse and unsnapped my bra. With practiced skill he cleaned and pierced my left nipple. After the quick stabbing pain he put a barbell stud in the wound, kissed the nipple, kissed my lips and then applied a small dressing. They swapped side and repeated the process on my right nipple only this time the kiss lingered and he pushed his strong tongue inside my mouth. When he broke away, I was ready to suck his cock on the spot. Alas it was not to be, Rachel paid him, I arranged my clothes and we left for home.

When we got home Rachel told me get undressed and join her in her bathroom. She was wearing a sheer white gown and was stunning. At such moments I longed for our early relationship. I was the man of the house and we fucked with hot passion virtually every day. I knew I would never fuck her again, much less be a man.

She had me lie down in her shower stall. She removed her gown and lowered her sweet slit toward my mouth. When the yellow stream began to flow It finally dawned on me that she intended to keep her promise from earlier. The piss was scalding hot and coming in buckets. I tried to swallow a mouth full, gagged and spit up. There was no time for thinking the second mouthful went down, but the torrent continued. My face was drenched. It was up my nose and stinging my eyes. She grabbed my hair and pulled my mouth up to meet her tiny hole. I convulsed and this time voided my stomach. I was an incredible mess, but still the hot liquid kept coming. Somehow I managed to gulp a couple of mouthfuls down before she finally stopped.

"How was that?" She asked.

"Thank you." Was all I could muster in response.

"Clean me." She said.

I began licking her; apparently the submission was all she wanted. She stood and started the multiple shower-heads. Urine and vomit ran off us and down the drain. She washed her hair as I soaped her body clean.

Dressed in long flannel gowns we had a pleasant evening together, watching TV and having a light dinner with wine. We shared some Scotch before retiring and I enjoyed a deep sleep.

Chapter Three

The next morning I awoke refreshed. My nipples hurt, but not all that bad and my ears were fine. I made breakfast of French toast and peppered bacon while still in my flannel gown. Rachel was pleasant and kept up a pleasant conversation talking about articles in the newspaper.

As she finished her breakfast she casually said. "I'd like you to quit your job and become my maid."

I was stunned. I had to say something quick. I had to accept the ultimatum. I wasn't sure I wanted to be maid. It would mean I could live as a girl full time. I wanted to be a girl. I wanted to be a girl.

"Yes Ma'am." Came out as casually as had her statement.

"After you clean the kitchen, clean yourself and take a shower. I'll put some clothes on your bed."

I didn't mind cleaning the kitchen. As a matter of fact I couldn't think of what I didn't like about being Rachel's maid. Maybe I could be called her domestic assistant. After all when you drink a woman's piss it seems silly to object to cleaning her toilet.

Having sold myself on my new station in life, I went to my room and put the Bardex in me. It's strange I guess, but I love to prance around with the bulbs banging the backs of my legs. I love the pressures and pains of the fluid going in me and the release is orgasmic. Being told I have to have an enema is like being told I have to have a hot fudge sundae.

My next fun for this magic morning was to shave my legs in he shower. There is something especially feminine about shaving your body hair. Smooth skin looks and feels total different – different better.