Eve Quest

Chapter 1

My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy.

My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company in Nashville, TN. I spent my college years in Nashville and liked the town so I moved there as soon as the estate was settled. I bought an elegant existing home in the Belle Meade area and accepted a do nothing job with the insurance company.

My sex life was pitiful. At six-feet tall and 168 pounds on a slender frame I was no Adonis. I had long blond hair, green eyes and a pale complexion. I didn’t participate in outside activities, like golf or tennis, gravitating instead to upscale bars, indoor sporting events and invitation-only parties.

For millions of reasons some girls were attracted to me, but I was shy and self-conscious around women. I ran with a group of guys that liked to drink and party, but none of them were real lady-killers either.

My friend Luke and I were at the Tennessee Bar late one evening when a short blond beauty came drifting in. She was with two other gals, also knockouts. They drank, played the shuffleboard and danced together to some Latin jukebox music.

An hour or so after they arrived the blond walked over to where I was seated. She wore a sheer pale blue blouse leaving her navy blue camisole clearly visible. Her nipples were prominent. Her breasts shimmied as she walked.

Standing very close to me she asked, “Do you dance?”

“No, Ma’am.” I stammered out. Her face was thin, Scandinavian. Her eyes were as blue as a summer sky. She wore little makeup, but her full lips were a delicious wet red.

She leaned over and whispered in my ear. “Do I look old enough to be your mommy?”

I was starring down her blouse at her beautiful bare breasts and it occurred to me that there would be some advantages to being her baby.

“No.” I said and almost added ma’am again, but I caught myself. “I mean I don’t dance to this kind of music.”

She smiled and leaned over to whisper in my ear again. “Do you fuck?”

I turned bright red and looked down. She turned and I watched her walk back to her seat. A navy blue, knee-length skirt corralled two fluid orbs. Her legs were full, smooth and bare. She had a classic, voluptuous body and a swing to her hips that would stop traffic in Times Square. When she reached her table she said something to her friends and they all laughed. My friend Luke asked me what she said. I tried to blow it off, but he kept on and on so I finally told him.

“Damn, son. If I were you I’d take another look at that dame, get over there and tell her yes.”

Easy for him to say, I thought. I hated aggressive women, but Luke just wouldn’t let it go so I finally agreed to send her a bottle of champagne and see what happened.

I watched as my beautiful blond poured two glasses. Her stiletto heals assaulted the dance floor as she walked over to where I was sitting and offered me one of the glasses. Although she spoke in a normal tone, it seemed to me she used a bullhorn. “Here’s to fucking.”

I was sitting there holding my glass like a bump on a stump. She clinked her glass on mine and sipped the bubble wine. I might have been mistaken for a statue.

A broad smile revealed beautiful teeth. She waved her hand in front of my face and said. “Hello, anybody home?”

I snapped out of my trance, downed my drink and said. “Cheers.”

She sat her glass on the bar and extended her hand. “I’m Sheila. Sheila Taylor.”

“Hi, Sheila. I’m Andy Moore. Pleased to make you, I mean meet you.” I’d almost gotten a complete sentence out without making an ass out of myself.

She flashed another lovely smile and said. “Andy, that’s some line.”

I laughed, still in the grip of her delicate hand. “Let me buy your dinner and I’ll promise to come up with something better.” I said.

“I’ve eaten.” She said and handed me a card. “Call my cell tomorrow and we’ll see.”

Her card said she was the president of Cumberland Investments.

Our courtship lasted only ninety days. I learned she had an MBA and had parlayed a six-figure income with one of the Wall Street firms into a brokerage company of her own. She and her parents didn’t speak and mine were dead so we weren’t likely to have any in-law problems. She was adamant that she wanted no children, but she was a sexual machine with a voracious appetite. I, on the other hand, had limited sexual experience. My first time was with a neighborhood girl when I was fourteen. She was seventeen. My second experience was with a gay friend in college. I didn’t tell Sheila about the later experience, but it was obvious I was sexually inexperienced.

We were married in a civil service and honeymooned in Hawaii for a month. We returned home and settled into a comfortable routine. An outside observer might have called it normal and but, for those occasions when I dressed up in women’s clothes, it might have been.

I’ve been “dressing-up” since childhood and I never told Sheila. Like most transvestites, sneaking around to dress just added to the excitement. I shopped the Internet for hours before selecting the perfect items and had them shipped to my secret post office box. There was a small hidden room off the garage I had converted into a closet and dressing room.

This normal life was to change completely one afternoon about ten months after we married. I arrived home after work, threw my keys on a table in the foyer and walked into the den. It was a beautiful; richly appointed room with dark paneling, honey oak flooring and Turkish rugs. Sheila was lying naked on the floor. I recognized the woman next to her to be her former college roommate Jenny Renee Wilson. They were locked in a sixty-nine position, lapping away at each other’s pussies. I stood transfixed, both shocked and intrigued. After a few moments, Jenny looked up and said, “Get the fuck out of here.” Then she returned to work on Sheila cunt.

To this moment I’m not sure why I didn’t jerk her up and kick her skinny little ass. It wasn’t really about Jenny. It was about Sheila. I realized I was afraid to rile her and something deep inside me caved in. A newfound subservience guided my steps as I turned and left the house.

I drove to a small bar down the street and drank a couple of beers. An hour or so later it dawned on me it was the first of April, April fool’s day. I called home and Sheila answered the phone.

“Hello.” She said in a cheerful tone.

“April fools, right?” I said.

“Come home immediately.” She said.

As I traveled home, my April fool supposition gave way to a feeling of impending doom. My hand rattled the front door knob as I entered the house.

Chapter 2

The sight as I entered our den was almost as shocking this time as it had been a few hours earlier. As before, I found them in the den. Sheila sat atop a barstool. Her soft shoulders and ample 36C breasts fell gracefully to a 22” waist and 38” hips. She was dressed in a white on white brocade corset. It was a straight-line design without cups, so it flattened her breasts against her chest and caused them billowed over its top. She wore no panties and sometime since I’d seen her last, her pussy had been shaved. Smooth and fat it protruded from her pubic bone like a flesh-colored peach. Her white stockings were attached to the corset with three garters to a side. She wore white single-banded sandals with 4” spike heels. Her nails flashed red.

Jenny stood beside her, 5’ 7” tall and very slender. Her short platinum blonde hair and the ringlets across her forehead gave her a severe 1920’s look. She wore a black leather waist cincher. Her bare B-cup breasts sat firmly on her smooth chest. Each long, thick nipple sported a silver barbell. Black leather garters supported her black fishnet hose. Her polished black, high-heel boots were laced up to just below her knees.

Haltingly, I stopped and faced them.

Sheila’s tone was businesslike. “You may strip, kneel and await our orders or you may pack and leave forever.”

The scene was surreal. I rubbed my chin, looked at Jenny and then at Sheila “Why are you doing this, darling?”

Sheila slid down from her stool, slowly sat her drink down and deliberately walked over to face me. She slapped me hard across the face with her open right hand as she said. “Strip bitch.”

I towered over her, rubbing my check. After a long moment I made the last free-will decision I would ever make. I began unbuttoning my shirt.

“Fold you clothes carefully and place them on the coffee table.” Sheila said, as she returned to her seat.

“I told you the little fag would do it.” Jenny said looking at Sheila. She was absolutely giddy with excitement. “You can’t imagine how much fun this is going to be, our very own slave.”

I undressed and stood before them. My eyes were on Jenny because in my mind she had to be the catalyst for this unbelievable turn of events. She was very pretty, but at that moment, her pointed chin and small mouth struck me as shrewish.

“Get on your knees sissy and don’t eyeball me.” Jenny said.

I obeyed, starring at the floor.

In an ominous tone Sheila added. “It’ll be in your best interest not to ever look a woman in the eyes again, and I damn sure better not catch you looking at their tits or asses. My suggestion for you would be to develop a foot fetish.” She walked over and stood in front of me, cunt to nose so to speak. “Do you understand?”

“Yes.” I said.

“Yes. Is that how you address your superiors?”

“No. Ah, Ma’am. Ah, Mistress. I mean yes I understand, Mistress.”

Sheila continued. “We know about your girly clothes and your fag magazines. So, I’m sure you’ll be pleased to know you’ll be spending the rest of your life as a girl. You'll be a maid and a slut, but a girl nonetheless. Do you understand?”

“Yes, Mistress.”

“What, no thank you.”

“Oh, thank you, Mistress.”

“Thank you, Mistress my ass.” Jenny said. “Look at his weenie. He’s getting hard.” She pounced on me, grabbed my face and forced me to look at her. “You love the thought of being in panties don’t you, bitch?”

“Yes, Mistress.” I said. I couldn’t turn my head, but I tried to avert my eyes from her.

“Yes, Mistress.” She said in a singsong, mocking tone. She released me, returned to the stool and added. “You best keep that thing in control around me or I’ll have it cut off.”

“Let’s establish a few ground rules.” Shelia said. “Never speak unless spoken to. You won’t need to ask questions because our instructions will always be perfectly clear. When addressing Jenny or me, you’ll refer to us with respect such as ma’am or mistress. Do you understand?”

“Yes, Ma’am, but.”

I didn’t get my question out. Sheila leaped from her seat and backhanded me across the face, knocking me off my knees. “But is not a part of your vocabulary ever again.” She calmed down, pointed to her left and asked. “Do you see the rug in that corner?”

All the floors in downstairs area of our home were honey oak and there were numerous fine rugs. The particular one to which she referred was a small silk Turkish. I looked first at the rug and then at my beautiful young wife. “Yes, Ma’am.”

She kicked me in the stomach. “Don’t look at me, bitch.”

“Yes, Mistress I moaned.” Clutching my stomach with both arms.

“When Jenny or I give you the command – Rug, you are to go to that rug and kneel down with your face on the rug and your ass in the air. You’ll most likely be punished. Do you understand?”

“Yes, Mistress.”

“Make him go now.” Jenny said in a playful tone. “He looked. He looked at you.”

“Go to the garage, get me a ping pong paddle and go to the rug.” Sheila said.

Naked, I headed toward the garage.

“Move your ass.” Sheila added.

Returning from my errand, like an obedient puppy, I handed the paddle to Jenny and assumed the position. I faced to the wall so I couldn’t see what was coming, but I heard the paddle on its downward swing. The pain was astonishing.

“Your turn.” Jenny said, apparently handing the paddle to Sheila.

After delivering two hard blows to my ass, Sheila placed the paddle on my ball sack and told me to spread my legs. Fearfully I complied.

“Do you think you can be a good girl now?” She asked.

Girl was my thought, but I was in the absolute wrong position to ask questions. “Yes, Mistress.”

“Then go back where you were and see if you can convince Jenny that you really want the life we’ve described.” Sheila said.

After I was kneeling in front of Jenny, I clamped my hands as if in prayer and looked at Jenny’s feet. “Please, Miss Jenny, please sissify me and humiliate me any way you wish. I’ll obey your every command.”

“My bet is you’ll live to regret those words.” Jenny said, then speaking to Sheila she added, “Get on with it baby.”

Turning to Jenny, Sheila asked, “What shall we call her?”

“What’s wrong with Sissy?” Jenny said.

“Nothing at all. As a matter of fact, I think that ‘s perfect, but we’ll need something for her ID.” Turning in my direction she asked, “What do call yourself when you are dressed in women’s clothes?”

“Jamie, Mistress. Jamie Jo.”

“Very well then. We’ll make everybody happy. Your ID will carry the name Jamie Jo Moore. Jenny and I will refer to you as, Sissy. Are we agreed?”

Resigned to my fate, I nodded in recognition not that I think they really wanted my approval.

Sheila laid a form on the ground in front of me. “This form will give me complete control of your money and your life. Signing it will be your last act as a man. Of course, you might prefer a nice divorce where all your transsexual inadequacies are made public.”

I signed it in two places and initialed it in two more.

She squatted in front of me to pick the papers up and kissed me on the forehead. “I did love you to a point, but my body requires a massive dick and you can’t help me there, can you?”

“No, Ma’am.” I said. She had never complained about my dick before. It wasn’t very big, but she had never complained.

“You’ll be an integral part of my sex life and you’ll be my obedient slave. I’m sure you’ll make me very happy.”

Sheila was still in a squat when Jenny walked over, put a hand on her shoulder and said, “I don’t have a massive dick.”

I’m sure I was not supposed to look, but Sheila kissed Jenny’s pussy and ran her tongue between the puffy outer lips. Then she said, “But you have the world’s most delicious pussy.” Moving up Jenny’s body Sheila kissed her tummy then cupped her left breast and put a metal filled nipple in her mouth. She stood, looked up at Jenny and said, “I wouldn’t trade you for a hundred dicks or a hundred of their stupid owners either.”

Turning to me Sheila said, “Rug.”

I wasn’t sure what I had done to aggravate her but I quickly assumed the position.

A few moments later Jenny told me to be still. I smelled alcohol as she wiped a place on my butt. She gave me some kind of injection then told me to sit up. She handed me two pills and a glass of water. As I swallowed them she laughed and said, “Hormones, Sweetie. You’ll love what they do for you.”

I’m sure they meant this treatment to be cruel, but I had dreamed of being a girl all of my life and I was willing to pay the price to be one. Any price.

Sheila said, “There are some empty boxes in my bedroom. Pack all your male clothing. We’ll give them to the Goodwill. You’ll be moving to the spare room on the right at the end of the hall.”

The way the upstairs was laid out, a curved front staircase lead from the entrance hall to the double doors of the master suite. Down the hall to the left are the four guest bedrooms two on each side of the hall, each with a private bath. The rear stairway led downstairs to the kitchen.

Sheila continued. “Jenny and I’ll share the main bedroom. You’ll have some household chores, but never and I mean never go into our bedroom without Jenny’s or my permission. Do you have any questions?”

“No, Ma’am.”

“We’ve setup the guest bathroom for your use. If you have anything left in my bathroom, put in the trash.”

I took me nearly an hour to get everything packed. I placed the boxes in the hall, disposed of my toiletries and returned to the den to find Jenny and Sheila sitting on the couch. I stood quietly with my eyes down.

Jenny said, “I think you’d be smart not to stand when we are seated unless you’re serving us.”

I sank to my knees. “Thank you.”

“Sheila, why don’t you call your hunk of meat? I’ll take Sissy to her room and get her acclimated.” Jenny said.

“That’s a plan.” Sheila said. “But just introduce her to phase one for the moment.”

Jenny saluted as if accepting a command.

I followed Sheila into my new bedroom and found they had been busy. The door to the room had been removed. The walls were painted a soft pink. There was a pink satin spread and several satin pillows on the bed. The dressing table, bureau of drawers and nightstands were white enamel. Framed pictures of nude male dancers dotted the walls, but the most startling change was the mirrored ceiling and recessed lighting. The room was very bright and very feminine.

“We’ll start in the bathroom.” Jenny said.

Someone had been busy there too. The door was gone. Everything was either pink or white. The ceiling and two opposing walls were covered in mirrors. As in the other room, it was very bright. My nakedness and Jenny beauty filled the room.

“Between electrolysis and hormones, shaving will not be as big a problem in the future, but for now I want you to start with a depilatory. Have you used one before?”

I was embarrassed to all hell and wanted to lie, but dared not. “Yes, Mistress.”

She winked and said. “Then you know it’s hard on your skin. I wouldn’t use it everyday.”

She retrieved a large pink bottle from under the sink and handed it to me. I applied the smooth pink liquid to my arms, legs and torso. After the appropriate time expired I got in the shower. When I stepped out I was hairless from the neck down except for my genitals.

“I assume you’ve shaved as well.” She said handing me a can of feminine shaving gel and a razor. “Every morning I want you to carefully shave your legs, underarms and pubic area.” She touched the back of my leg, high and on the inside. “This area is hard to reach. You may find it easier to shave your underarms and back there while looking in a mirror, as you can see there are plenty available. She started a warm bath and added bubble bath. “Now get in the tub and shave.” She sat on the toilet and watched as I carried out her instruction.

When I was finished, I stepped out of the tub, accepted a large fluffy towel from Jenny and dried off.

“Your lotion is in the blue bottle. Put some in every pore of your body. Okay?”

“Yes, Mistress.”

“You’ll sleep in a plain cotton nightie?” Jenny said. “Have you ever worn a gaff?”

“No, Ma’am.”

She handed me a garment that looked like bikini panties. “Put this on.”

I had it three-quarters of the way up my legs.

“Hang on.” Jenny said. “Push your balls up into your body and pull your dick and ball sack back between your legs.”

I did as instructed.

“Now pull the gaff up and use it to hold everything in place.” Jenny said.

I followed her instruction again. It felt really good, like a girdle, but less restricting.

“You might as well wear these.” She handed me pair of white high-cut briefs. They were thin and stretchy with two lace accent panels on the front. I held them to my face. They smelled of powder like my mother used in her underwear drawer. The reminiscence caused pre-cum to dribble from my dick. The bra was a sheer, white 36A cup with a front closure and matching lace accents.

It was probably obvious how much I enjoyed putting the outfit on. How much I enjoyed putting it on in front of a real woman. I’d never been dressed in front of a real woman before. As I stepped into high-heel mules, I creamed my new gaff.