Category: Transsexuals & Crossdressers Stories

Eve Quest Pt. 02

by JJ Neal©

Chapter 6

I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and filled the bag with a smile. Once I had the bag full, the system purged and the bulbs in place, I pranced around the room holding the bag above my head. I liked having the pumps hanging down from my body and slapping my bare legs. My playtime over I assumed the position and accepted the first load. At the proper time I dumped it and took the second one. Putting a tampon in my pussy was always a kick. That morning it seamed even more special.

The bath was luxurious. I added bath oil to the bubbles and soaked before running a razor over my body. My nails were fine. I smoothed lotion over my entire body and powdered my genitals. Jenny was right I needed to lose some weight. It was a real struggle to get the corset on. It included full cups and adjustable straps, so my cute new breasts were held firmly in place. The panties were layer on layer of lace with a lot of spandex in their body.

I sat at my vanity, pulled on my stockings and attached them to the corset with white lace garters. My heels were single banded sandals with a strip of leather connecting the heel to the ankle strap. The leather strip had a built in “D” ring. The ankle strap was held closed with one of the small silver locks. As I stood I almost swooned. It’s such a charge to be on heels, especially 4” heels. Then I noticed the time. It was 5:46 and I needed to get moving.

The crinolines were in a set, five layers to a set. The French maids outfit had a scoop neck and a very short skirt. Over the crinolines it covered nothing. My garters, ruffled panties and lacy stocking top were visible. The apron was shorter than my skirt, but the bodice and straps were layers of ruffles and improved on the stark cut of the dress. I did the best I could with my makeup and wig then clipped the cap onto my hair. From the head down the gal in my full length mirrors was hot. Every guy on the planet would want to get into those ruffled panties. Unfortunately, there was no time to prance around. It was 6:04.

I had two places set at the table in the sunroom; hot tea prepared and toasted bagels ready when I heard the patter of bare footsteps down the hall. I had even set some fresh flowers on the table. I was beaming with pride. The breakfast was served; I was a vision in pink, and I had four minutes to spare.

Jenny was naked, her hair disheveled and she was rubbing her eyes as she entered the dinning room. She said, “Toilet.” Then she turned and headed for the bathroom.

I’d been primping for an hour and a half and she hadn’t even looked my way. She was going to make me do that disgusting job before Mistress Sheila even got to see me. Up the stairs and down the hall, I got my sheet out and lay down. Jenny flopped her lovely pussy on to my mouth and started without so much as a fair thee well. With my tummy full I licked her a couple of times, but she was unmoved. She stood and left without a word.

I fixed my makeup and hair, brushed my teeth and hustled back to the sunroom.

“Hello, Sissy.” Sheila said.

I knelt between the two of them, eyes down. “Good morning.”

“Did you enjoy your breakfast?” Sheila asked.

Breakfast? I thought, but I’d learned my lesson about questions. Instead I said. “Yes. Thank you.”

“Don’t thank me. Thank Jenny she prepared it.”

I finally tumbled to the deal. “Thank you, Miss Jenny.”

After I’d cleared the breakfast dishes and loaded the washer I knelt before Sheila in the sunroom. She said. “Jenny is waiting in the living room. She’ll go over your household duties.” She held a steak knife loosely in her right hand. I didn’t remember setting it out, but her manner didn’t seem menacing.

“This whole operation was mostly about taking your money, but there’s a potential here for you to find happiness. Make no mistake, every time you fuck up I’m going to discipline you and I’m going to enjoy hurting you.” With that she placed the point of the knife on my left inner thigh, just above my stocking top. She pressed it to the point of pain and a trickle of blood.

“Yes, Mistress.” I said, eyes down, jaw clinched.

“Get out of here.”

Jenny had a day-by-day list of duties most of which were domestic in nature. I would be doing laundry, cleaning, polishing and vacuuming. I’d be responsible for breakfast and dinner every day. On weekends and holidays I’d serve lunch.

“At this point we don’t want you to go outside, but that day will come. We’ll also do the shopping until you are more passable as a girl.”

“Thank you, Mistress.”

“I hope Sheila made it clear that our policy with you is no toleration. You make a mistake we’re going to hurt you.”

I rubbed my inner thigh, but she didn’t seem to find the event significant.

“We’ll enjoy taking our sadistic tendencies out on you. Of course, if you have little masochistic urges then all you have to do is fuck up.”

“Yes, Mistress.”

We went through every room in the house except the master suite and she covered what was expected in every area every day.

“We don’t intend to trap you. We just want the work done and we want you to learn to be an excellent maid.”

“Yes, Mistress.”

“Like most servants you will be expected to perform sexual favors for your master and in your case that includes toilet service.”

I nodded in compliance.

During the next couple of weeks I learned exactly what was expected of me. It had always been fun to sashay around in high heels. I found it was quite another thing to work in them for eight or ten hours. At the end of every day my feet and legs were killing me. To make things worse, the first time Jenny caught me with my seams crooked, she removed my shoes and beat the bottoms of my feet with a bamboo cane.

There were dozens of violations that drew various degrees of discipline. My first attempt at doing the laundry was a typical disaster. I hand washed several pairs of panties, but I mixed the colors. Everything ended up some color of red. I didn’t get the connection, but for the next two days they added Tabasco sauce to my second morning douche.

I had no training as a cook so it should have been no surprise when I overcooked some steak for dinner one night. They cut the steak in chunks and watched me remove my tampon and jam the pieces up my pussy. I wasn’t allowed to remove them until I retired.

Of all the outrageous tests, Jenny checked the baseboards in the den with a white glove. They didn’t pass. They didn’t even come close. I spent the afternoon in the corner, bent at the waist with my wrists attached to my shoes. They didn’t beat me, but it was the next morning before my back quit hurting.

There was something every day. It was obvious to me that a satisfactory job on my part was a pipe dream. They always found some minor infraction and delighted in punishing me. Their favorite targets were my nipples. The hormones had them puffy and sensitive. Over time, using tit clamps, they attached everything but the front bumper from a car to them.

After breakfast everyday I was given a hormone injection and four different pills. I had no idea what the pills were and wondered if they were poisoning me, but I decided they had everything I owned so what would be the point.

Each mistress used me as a toilet once a week in lieu of one of my meals. When they had visitors I was the entertainment. They would show me off then Jenny would piss in my mouth. Before they left, I would service every pussy or cock in the place.

My diet was a startling change. We used the sunroom on the backside of the house for most meals. The slanted ceiling and three outside walls were glass and the floor was a rich brown stone. There was an immaculately manicured garden surrounded by a high brick fence. I normally ate with my mistresses. The big difference was that I sat crossed-leg between them on the floor for my meals.

They had continental breakfast most mornings. If they ate meat it was in small portions. I had a delicious diet shake. They ate lunch away from home except on weekends. On Saturday and Sunday I served a half a deli sandwich with cold slaw, potato salad or a fruit cup. I had a delicious diet shake every day in my choice of flavors. Their evening meal was planned well in advance and included steaks, seafood and pasta, but the portions were tiny. I had a small salad with low-fat, low-cal dressing. Once a week I might get a small piece of chicken or fish. I was allowed a diet snack bar or a piece of fruit at 10:00 and 3:00. I kept fresh veggies cut in the refrigerator for all our use. My choice of beverage was water or water and I could have all I wanted as long as I wanted at least a gallon every day. They even had a bottled water chiller installed in my bedroom.

Sheila and Jenny jogged together most afternoons. While they jogged I changed into a two-piece yellow swimsuit for an hour or so of sunbathing. The bottom to my suit was T-backed and the top was similar to a normal back-closure brassiere. My tan lines became very obvious. When they returned home we all did aerobic exercises, which meant I had to change clothes again. My exercise outfit consisted of a white gaff, white tights, a pink short-sleeved leotard and white sneakers with pink trim.

At the end of the first two weeks the bloom was off the rose. My feet hurt. I was hungry. I needed some sleep and most of all I was isolated. I needed a friend. When I signed away my manhood I was sure I wanted to be a girl. At that point I wanted a hamburger, a beer and the television clicker.

My plain cotton gown felt extra soft and comfortable that Friday night, but I was resolved to escape at the next opportunity, perhaps the next morning.

Chapter 7

The strong resolve of the night before seemed to dissipate in light of the morning sun and the Bardex in my twat. I had to admit to myself I was a sissy, a coward and a slave. I was dressed and setting breakfast on the table when Sheila walked into the kitchen.

“Sissy, make me a Bloody Mary.”

I really wanted to say – Zap You’re a Bloody Mary, but I settled for fixing her drink. A late night no doubt, I thought. By the time I served the cocktail, Jenny had joined her and they were disposing of the morning meal. I sat the drink by Sheila and knelt between them. To my amazement they were jabbering about me.

“His Mother had to know he was wearing her clothes. He’d have stained every piece of lingerie she had.” Jenny said.

“But she never said a word to him.” Sheila said. “Or at least that’s his story.”

“Denial?” Jenny asked.

“I guess. His Dad took a more positive approach. He gave him a good talking to, sent him to a shrink and tried to fixed him up with a couple of young girls.” Sheila said.

“You can lead a horse to water.” Jenny said.

Sheila interrupted. “But you can’t change its spots.”

“You think he was born a transvestite?” Jenny asked.

“Beats me. I guess he could’ve been, but if makes any difference, I think he was abused as a kid.” Sheila said.

“Sexually?” Jenny asked.

“Yeah.” Sheila said.

“His Dad?” Jenny asked.

“More likely an Uncle or a neighbor. By the time he got to college he was wearing panties every day. He never missed a chance to suck his roommates cock.” Sheila said.

Jenny nodded along as Sheila continued with stories about my college days until they were finished with breakfast. Of the many forms of humiliation I was experiencing, having intimate details of my life discussed in front me might have been the cruelest.

Sheila turned to me and said. “When you’re finished with the dishes, there’ll be an outfit on your bed. Comb your hair, don’t wear a wig and wash off your makeup. We’ll be ready to leave in thirty minutes so get moving.”

My outfit consisted of a gaff, white pantyhose, pink short shorts and a short pink open-mesh tee shirt that didn’t hide a thing including my belly. Tit clamps connected by a heavy chrome chain lay on top of the outfit. I assumed the white leather collar; white bracelets and white heels were appropriate.

Jenny and Sheila were waiting on me in the living room. They wore halter-tops, jeans and tennis shoes. They looked great. I looked like a shameless, transvestite slave and that status was accentuated when Jenny attached a leash to my collar. We were going outside and I had nowhere to hide.

The cowgirl outfit had been one thing and not a very good thing, but this outfit was way over the top. You could see my bare tits for Christ’s sake. I’d been to Bourbon St. and Frisco. I’d see transvestites and public bondage, but in those circumstances the people seemed more like entertainers than freaks. In this outfit I’d engender disgust and loathing on the part of the observer. I fell to my knees and said. “Please.”

Sheila didn’t hesitate. “Rug.”

I did as instructed.

After a few moments Sheila said. “Up on your knees.”

Using two short chains she attached my bracelets to the “D” rings on my shoes. She held my tee shirt up, increased the pressure of my tit clamps then scared me to death. She clipped a wire to the chain between my tits. She unzipped my shorts and pulled them down to my knees followed by my hose and gaff.

“I’m going to help you bend forward so you don’t hurt your face.” Sheila said.

My dick was hard as a rock and there was a pronounced tremble in my voice. “Thank you, Mistress.”

My face and upper chest were on the rug. My ass was in the air. Sheila pulled the wire from my tits back between my legs. She removed my tampon and pushed a cold cylinder into my pussy. I couldn’t see it, but the cylinder had a wire coming out of it and both wires terminated in plugs. I heard the plugs being pushed into receptacles on the wall and I heard the front door open. I didn’t see Sheila signal Jenny to push the doorbell.

My body snapped hard. The electricity ripped a path through me causing me to thrash around in pain. Inside I was screaming, but the sound didn’t come out until Jenny let up on the button.

Sheila slapped my ass with her open hand then asked. “On what basis do you think you have the right to refuse me anything?”

“Nothing, Mistress. I’ll do anything you ask.”

She signaled Jenny. I was on my side jerking spasmodically against my chains unable to escape. My shrieks came in waves.

The electricity stopped and Sheila said. “Your damn right you will. You’re anxious to go with us now aren’t you?”

“Oh yes, Ma’am.”

“You’re a fucking liar.” Shelia screamed. She accented her point by ordering a short burst on the button.

“Oh please, Mistress. I’m confused. I don’t know what you want me to say.”

“The truth.”

“I’m embarrassed and afraid.” The truth was rewarded with another series of zaps.

“You have no self, so how can you be self conscious? You exist only for our pleasure and if you’re not certain we’ll take care of you then you’re in deep shit. Clear?”

“Yes, absolutely.”

“We’ll take you out in any condition we please, but we will stay within the law. If you see a woman keep your eyes on her feet. Look every man in the eyes, and then stare at his crotch and lick your lips.” She pulled the cylinder, unclipped the wire to my tit clamps and said. “Get cleaned up and put in a new tampon. We are late already.”

We drove to a medical building near the hospital. They paraded me across the parking lot, up the elevator to the third floor and into a large waiting room. I was embarrassed, but I sat in a corner starring at the crotch of a man directly across from me. After an interminable wait I was shown to a dentist’s office. The doctor was very beautiful. She made no pretence about her passion for Jenny.

“Can we go to my office while Angie takes the impressions?” She asked Jenny.

Jenny didn’t answer. She just led the dentist away. Angie made x-rays of my mouth and took impressions. Sheila just sat in a chair and observed. When Jenny returned she told Sheila that everything would be ready in two weeks. I wasn’t allowed a question, but I sure had some.

Our next stop was a small strip mall near the University. Shelia and Jenny walked hand in hand looking in the shops. I trailed along behind a freak on a leash. When we were near the end of the mall they walked inside a shop, a tattoo shop. We were greeted by a short trim male with a ponytail. He was a walking billboard for his trade and sported a wide smile as he greeted my wife.

“Shelia, Jenny what a treat.” He put his arms around them both, but kissed Sheila on the mouth. Jenny stepped away and Shelia straddled one of his legs. As they embraced, she humped his leg like a dog in heat.

She whispered something in his ear and dropped to her knees. Jenny locked the front door. Sheila unzipped his leather pants and pulled them down to his knees. He wore no underwear. His legs were smooth shaven and there was an elaborate tattoo crawling up his left leg. His dick was long and slender, but the attraction was his Prince Albert. It clanked on Sheila’s teeth as she dropped his limp meat in her mouth. It didn’t stay limp long.

She slurped and bobbed running him down her throat and burying her nose in his pubic hair. I had no idea she could do such a thing, much less enjoy it so much. She moaned, rubbed his ass and played with his ball sack. He put his hands on her head and stiffened. She slapped his ass hard and took his load. He flopped out of her mouth; she walked over and gave me my second snowball.

The Tattoo man pulled up his pants, jerked Sheila away from me and kissed her again. “Thank you.”

“It’ll be your turn soon.” Sheila said with a smile. “But for the moment, we’re here on a mission.” Glancing my way she said. “The slut with your cum in her mouth is Sissy. She needs some work.”

“Great. Let’s get to work.”

Jenny led me to a sort of chair. “Take off your top and shorts. Pull down your pantyhose and gaff.”

I complied and she pushed me back into the chair.

My clothes were embarrassing. My shaved nakedness was worse. Jenny released the clamp from my right nipple and rolled the nipple between her thumb and forefinger. The pain was staggering. I would have never believed it would hurt so much. I grabbed at her hand trying to stop it, to no avail.

“That really hurts doesn’t it?” Jenny asked.

Pain sealed my lips.

Jenny attached my bracelets to the arms of the chair and ran a bungee cord from the right side of my collar behind the headrest to the left side of my collar. It effectively locked my head in place. She unlocked the ankle straps of my shoes and removed them, then pulled off my pantyhose and gaff. The chair had adjustable stirrups for my feet and Velcro strips to restrain my ankles and calves. To that point the restraints seemed non-threatening. When she buckled a leather strap across my lower chest panic set in.

Jenny put a sleep mask over my eyes before she removed the left nipple clamp and started rolling the nipple between her fingers. I jerked against my restraints and screamed. The most I accomplished was some big old crocodile tears.

I overheard Shelia say. “Yes, in 12-gage.” A few moments later she said. “This is for her navel.” There was some rustling of pages and then she said. “That’s it.” Moments later she said. “Let me show you.”

The chair flattened back and my legs were mechanically forced back and apart. Something touched me just to the right of my scrotum. I flinched, but wasn’t hurt. They touched me several times and then moved to the left side.

Tattoo man said. “Give me till 5:00.”

I heard the tumblers for the front door turn twice and the room went quiet.

Tattoo man wiped my ears with something then stabbed me. It startled me more than it hurt and I realized he was piercing my ears. He put a stud in that hole and stabbed me again. He repeated the process three times in each ear and said. “Keep very still I’m going to work on your lips.”

Category: Transsexuals & Crossdressers Stories