Eve Quest

“In case you’d like to know, you look like a chubby transvestite fag. Have you ever sucked a cock?” Jenny asked.

Deflated, I answered. “Yes, Mistress. Once when I was in college.”

“Just once. Does that mean you’re not really a cock sucking fag?”

“No, Ma’am.”

“Let’s see what Sheila’s up to.” Jenny said.

She was up to or maybe it would be more appropriate to say down on a young Adonis. The object of Sheila’s attention was a tall, muscular blond. I’d lied when I said I only had sex with a man once. After the first time I dropped to my knees, subservient to a cock I was hooked. My collage friend had let me dress in my female clothes and service him regularly. I would’ve probably done it in front of the administration building if he had asked me to, but he didn’t.

I’d always been attracted to men in the sense that good looking ones would give me a hard on. I’d fantasized about them and beat off to their pictures almost as frequently as I did women. My favorite masturbation fantasies involved slender young Asian she-males with flat-chests and long uncircumcised cocks.

Looking at Sheila’s hunk, there was no question in my mind I would suck this guy’s dick and offer him my ass. He was a wow! Sheila was on her knees sucking on his dick. It was as long as a polish sausage and half again as big around. It had been circumcised. The big beautiful head was a mouthful and Sheila was working it over.

“Your ex-wife is quite a cock sucker.” Jenny said. “When she has a real cock to suck.”

Ex-wife, Real cock, I thought. At some level I was embarrassed even angry at what she was doing, but the bottom line was envy. My gaff was getting tight.

The stud said nothing, never cracked a smile. He indifferently pumped away. Sheila sucked, slobbered and moaned both hands partially wrapped around his pole.

“Get on your knees.” Jenny said in a low tone.

I was sure I wasn’t supposed to watch, but Jenny didn’t say anything and I was mesmerized. I’d seen stuff like this in porn movies, but it wasn’t my wife and it wasn’t so close up. He stiffened, she became still and after a moment he popped out of her mouth.

Sheila walked over to where I was kneeling, leaned down and kissed me depositing the load in my mouth. It had been a long time, but I hadn’t forgotten the taste, the smoothness. I rolled it on my tongue, pushed it through my teeth and took a deep breath.

“It’s called snowballing.” Sheila said. “How do you like it?”

I didn’t know from snowballing, but I said. “Thank you.”

“Clean my friend up.” Sheila said.

I crawled over and positioned myself in front of him. As if an expert, I started at his balls and licked my way up the shaft cleaning as I went. I loved his musky odor and inhaled deeply. I pressed his meat to my cheek then kissed it several times moving toward its head. Opening wide I slid him into my mouth.

This prompted Sheila to grab a hand full of my hair and jerked me back. “I’ll let you know when I need your help. Besides, the entertainment is over for tonight.”

That’s when I noticed Jenny was recording my performance using a digital recorder.

“Your sissy friends on the internet will love this movie won’t they?” Jenny asked.

My face begged for mercy, but I dared not ask for it.

“You know where all the best Tranny sites are, don’t you?” Jenny asked. “Will you help me post this movie in the morning?”

“Yes, Mistress.” I said then added a tentative, “Please.” It sounded like a plea for permission, but I hoped she recognized a veiled plea for mercy.

Ignoring my condition, she continued. “This will be the before movie. As we feminize you we will take some more. Do you think the members of your board of directors would like a copy?”

“No, Ma’am.”

“We can always send them a copy later.” She said. “If we change our minds. For now you can get to bed. See you in the morning.”

The lights in my room would turn down low but not out. It appeared I would have no privacy at all in my new life. As I stretched out in my pink bed, in my pink room, in my short cotton gown, the thought of a shot of Scotch entered my mind. I needed some help to sleep. For years I had used masturbation as a sedative, but I was confident that would be a mistake.

Chapter 3

I awoke the next morning, as if kissed by the proverbial Prince. I was dressed in women’s underwear and a soft cotton gown and it took me a moment to remember the source of this little miracle. I used the restroom, arranged my clothes and went to the sunroom. Sheila and Jenny were eating.

I dropped to my knees and said. “Good morning, may I have some breakfast?”

Sheila whirled around to face me. “Rug, you stupid bitch.”

I ran to the den. It was twenty or thirty minutes before they joined me. Sheila had a wide leather belt in her hand. Jenny tossed my gown over my back and pulled down my panties.

“You spoke without being spoken to didn’t you?” Sheila asked.

“Yes, Mistress.”

“And what is our position on rules violations?” Sheila asked.

“Our position is zero tolerance.” I said.

As I spoke Sheila rained the first blow on my upturned ass.

The second blow followed quickly and seemed to energize her. I was screaming in pain and begging for mercy. More than a dozen blows fell before she stopped.

“Take her upstairs and get her ready, would you please.” Sheila said looking at Jenny.

Jenny escorted me to my room and told me to undress, bath and shave. She watched my every move and when I was finished she handed me the lotion.

“Every morning I want you up by 5:30. For breakfast you’ll find some diet shakes in the refrigerator. Drink one then get a bath and shave paying particular attention to your face. You’ll wear a gaff, panties and a bra. We’re going to allow you some latitude in your dress. There are four pairs of women’s dress pants in your closet. They’ll fit you perfectly. There are four woman’s long-sleeve silk blouses. You can mix and match the colors. You’ll find a pair of women’s loafers in the closet. Get dressed now and meet us downstairs.”

“Yes, Mistress.”

“If you’ll hurry you can grab a shake for breakfast.”

I put my underwear on and selected a gold blouse. It had covered buttons and wide tight cuffs with three buttons each. It had a large floppy collar that was open to just above my bra. It screamed classy lady. My dark brown trousers were tight at the waist and wide at the hips. They had a side zipper and button. I slipped my bare feet into a beautiful pair of backless loafers.

From the neck down, the look was that of a very sophisticated young lady. From the neck up I was a young man. Overall, I was a transvestite or a submissive fag or both, but at that moment I really loved how I felt. I ran to the bathroom so I could get a good look and whirled around and around.

Downstairs, Sheila was dressed in a light gray suit with a white blouse similar to mine and high-heel pumps. “Let’s go.”

Go never entered my mind till then. I was dressed in woman’s clothes. I had no identification or money. However, the most important fact was that I had no choice. Not even a choice to speak. I trailed behind her like a rag doll.

“You’ll make it through the day if you keep you mouth shut. You dig.”

“Yes, Mistress.”

Our first stop was a beauty shop. Sheila knew everybody. They gave us adjacent spots and Sheila ordered manicures and pedicures. I was way beyond embarrassed. I sat like a mannequin starring at my knees just barely able to resist the urge to run or cry. The women working on me conversed with Sheila as if I didn’t exist. Sheila had her nails done in bright red. My fingernails and toenails acquired a smooth coat of frosted pink. I admired my fingernails. They looked longer and gave my hands a delicate appearance. That aside, I was never more grateful for anything than to be leaving the place.

Our second stop was a doctor’s office. Again, Sheila knew everyone. I was sure the people in the waiting room were starring and whispering, but we were shown back quickly. I stripped and put on a gown. The doctor came in, kissed Sheila and asked how Jenny was doing. After she checked my temperature, blood pressure etcetera, she took blood, stool, urine and sperm samples.

When she returned she said. “He’s fine. Did you give him the first dose?”

“Yes.” Sheila said.

“I’d like to give him some stuff intravenously. When are you going home?”

“About two hours.”

“Okay. That’ll work, but he’ll probably be very sick tonight and he’ll get sick right after you give him his injection the next couple of days. The cocktail we have him on is going to work quickly, but his body will resist.” The doctor said.

“I don’t care how sick the gets. Will he be okay?”

“Absolutely. It’ll be like a sugar overdose. That’s all.”

“Put the stuff in him.”

She filled two hypodermics and emptied the contents into my arm. Then she put a third into my hip. Finally she gave me a small container of sweet clear liquid. It was psychosomatic, of course, but I felt sick at my stomach immediately. I got dressed and we left.

I recognized the office building we parked in front of to be that of my accountant. My supplication to God almighty went unnoticed and Sheila led us into Bill Carlisle’s office.

She kissed him on the cheek and said. “Hello, Bill.”

“Hi, Sheila.” He said and reached around to greet me. “Hi.” He got out before he assessed my condition. “What’s with the outfit?”

Sheila said. “Didn’t you know Andy was a transvestite?”

“No, I didn’t. I’ve never seen him like this.” Bill said.

“He always wore the underwear. He’s just getting a little bolder.”

“Bolder hell. He’s got tits.” Bill said.

“An under wire bra works miracles.” Sheila said.

Nausea overtook me. I lunged for the wastebasket and vomited.

“Shit, Andy. What the fuck is wrong with you?” Bill asked.

I hovered over his wastebasket, retching. Bill offered his handkerchief. I accepted then went to his private bathroom. When I returned Sheila was speaking.

“Our taxes are due in two weeks and I can’t keep him out of my panty drawer long enough to help me. Can you help me get our affairs in order.”

“I just can’t believe my eyes, but I’ll be glad to help. Let me get a couple of things from the other office.”

While Bill was gone, Sheila gave me some instruction.

“These lists will help guide you through the various accounts. Do you have the checkbooks?”

“I think so.” Sheila said.

“Call Paul Carter down at First Bank. He knows Andy’s finances well. I’ll help you put the expenses together. I don’t believe there’ll be any problems.”

Following Sheila’s instruction I stood walked behind Bill’s desk and sank to my knees. “May I suck your cock?” I said looking into his eyes.

“Andy, we’ve been friends a long time so I’m going to ignore that question, but I wish you’d leave and not come back till you get some help.”

Sheila stood and said, “I’m so sorry, Bill. He’s incorrigible.” Then she shook his hand and added. “I’ll call you tomorrow.”

I followed her out like a pull toy on a string, but I wasn’t the least embarrassed. It was a kick. My nipples pebbled from the sheer sluttish kick of it all. Of course, Mistress was not going to be happy I hadn’t accomplished the blowjob. Of course, I wasn’t happy about that either. It had been an awful long time since I’d worked a cock over and I was hungry for the experience.

Chapter 4

The lower floor of our house was centered on a large entrance area. Double doors to the left lead to the den and a game room. Double doors to the right lead to the living room and a private office. Double doors in the center lead to a formal dining room, kitchen and sunroom. There were three bathrooms downstairs in addition to the five upstairs.

After breakfast the next morning, Sheila took me to the office. She fired the old computer up and had me help her load some digital pictures in a file named Sissy. She didn’t really need my help. She just wanted to shame me and have me understand her, not so veiled, threat. The pictures were from the night before. I was on my knees servicing her boyfriend. When she was finished she got up and told me to sit at the computer.

“Send an e-mail to your office and tell them you won’t be in anymore. Ask them to send proxy forms here so I will be able to control your stock.” Sheila said.

It seemed like a goofy thing to do, but after all I was a young millionaire. Maybe this was exactly the kind of flighty action they would expect from me. Sheila had been busy. She had a list of my financial accounts. She guided me through them. I transferred some and closed others. At the end of a couple of hours work, she assumed I was broke. She was just about right, but she hadn’t found two accounts. I had $250,000.00 in a Costa Rican account. The same bank held a $250,000.00 line of credit on the house in Nashville. Next she had me help her change all my passwords to ones only she knew.

“I’m going to take care of you, but like most women you will live in fear of financial insecurity.” Sheila said. “Your life will be a series of mundane, repetitive tasks and if you find any satisfaction it will be as a result of my accomplishments or Jenny’s.”

“Thank you, Miss Sheila.” Referring to my former wife in cold subservient manner brought a tear to my eye.

As nonchalantly as if she were discussing the weather she said. “We’ll be leaving for Bangkok in the morning. Your surgery will be done there.”

“Surgery?” I said without thinking.

Sheila stood, pulled off her panties and stuffed them in my mouth. “Are you ever going to learn not to speak unless spoken to?”

I nodded dramatically. For a moment the fear erased the shock, but reality returned. I was aware of sex reassignment surgery and I knew it could be done in many places around the world, but I didn’t want to lose my dick. I wanted to look like a girl, but I wanted my dick. There had to be some way to object before it was too late. Maybe Jenny would help. I became woozy and purged, including Sheila’s panties.

“You stupid fucking bitch.” She said as she popped me on the back of the head. “Get that cleaned up and get rid of the panties.”

I scurried away grateful for the opportunity to get out of her presence. When I was finished cleaning up the mess I went to my room. When Jenny arrived I was still fully dressed.

“Get out of your pants and blouse.” Jenny said.

I did and sat on the bed.

“Lay down on your tummy.”

When I did, she pushed my panties aside and injected me with my hormones. I felt really sick at my stomach. She gave me some cold fruit juice and a hand full of pills.

“You better rest for a while. Put on your gown, I’ll get you up after lunch and we’ll get you packed.”

“Thank you, Miss Jenny.” I managed.

It was actually closer to 4:00 that afternoon when Jenny rousted me. Packing was certainly no challenge. Gaffs, panties, bras, pants, blouses and loafers joined cotton gowns and my toiletries.

“Where’s your passport?” Jenny asked.

“It’s in the safe in the office.”

“Go downstairs and look in the refrigerator. There’s a strawberry shake in there for your dinner. After you eat, set your clock for 3:00 and try to get some rest. I’ll leave an outfit out for you.”

“Please, Mistress.”

She grabbed a hand full of gown and tit then gave it a twist. “Keep your damn mouth shut.” Relaxing her grip she added, “Please what?”

“Please don’t let them cut off my dick.”

“Go get your dinner.”

I had a edgy night and got up with the alarm. The bath was wonderful. I shaved and washed my hair. I decided to wear it combed back in a wet look.

I don’t know why, but the outfit was a shock. I put on my normal white gaff, panties and bra. The first new item was white cotton knee-high socks. The shirt was a white silk cowgirl shirt with pink roses and piping. The pants were low-rider jeans in pink leather. My footwear was a pair of pink cowgirl boots. The belt was white leather with a big silver buckle. It read Sissy in big gold letters. A white cowgirl hat with a large pink rose in the hatband completed the outragious look. I couldn’t have stood out any more if I were wrapped in a flashing neon sign that read FAG.

Shelia and Jenny were comfortably dressed in jeans, short-sleeve shirts and backless sneekers. They’d arranged for a lemo and we were off. The trip to Los Angeles took six hours and once we made our connection it was nineteen more hours aboard Thai Airlines to Bangkok. One of the passengers pointed out that another name for Bangkok was Krung Thep. It was Thai for City of Angles. We were flying from the City of Angles to the City of Angles. Oh well, maybe that wasn’t important, but when you wear pink leather pants you need to know some interesting shit.

We were in first class and the flights were as comfortable as possible. I rested and was allowed to drink and eat normally although I still didn’t feel to spiffy. My appearance was a constant source of embarrassment, but by the time we arrived in Bangkok I think everyone had grown accustom to the show.

It was 1:00 AM local time when we checked into a suite at the Royal Orchid Sheraton. The rooms were opulent. The great room featured a domed skylight with chandelier. The furniture was French colonial. The entertainment center included satellite TV and a state of the art audio system. There was a long, well stocked bar with a huge balcony behind it. There were two bedrooms with canopied beds and Jacuzzis in the bathrooms.

Sheila and Jenny decided to get up at 7:00 to minimize the effects of jet lag. I was startled and disoriented when my clock went off. I was literally clutching my dick and probably had been all night. With no regard for the consequences I ran to my bathroom and masturbated. I was in the tub when Jenny walked in. She was already dressed.

“Breakfast is served. You need to get moving.”

“Yes, Mistress.”

I dressed in charcoal pants and a pale pink shirt. I ate a small breakfast on the floor by Sheila’s chair.

They gathered their belongings and Sheila said. “Let’s go.”

I was shaking with fear and they kept pushing me along. I looked like a prisoner in custody. By the time we got a cab I was crying, but they made no attempt to console me. We pulled into a clinic not far from the hotel. It was clean and the people were very nice, but of course they weren’t having their dick cut off. I sat sobbing with Jenny while Sheila made the arrangements. I was taken back to a private room and told to undress. Shelia and Jenny left without saying a word. Alone and afraid I felt like an abandoned child.

The day creep by interrupted by poking and prodding and tests. Late in the afternoon they put me on an IV. They either put something in the IV or I finally gave in to exhaustion.

I think my clock read 5:00 when they started moving me. My next recollection was numbing cold and then my room. My arms and chest were tied down. I couldn’t move and I hurt everywhere. There was a young nurse in my room. I tried to ask her about my condition, but the most noise I got out was a squeak. There was something wrong with my throat. She came to my side and offered me a drink through a straw. I accepted it and drifted off again.

I’m not sure what day it was, but I clearly remember the event. There was a bedpan between my legs and I was pissing through my dick. My dick was still there. This wonderful event triggered my complete and rapid recovery. My little nurse helped me get up and explained what they had done.

They had cropped some material off my earlobes to make them smaller. They had shaved my Adam’s apple and worked on my vocal cords. They had done a breast implant and removed some material from the bottom of my rib cage. They hadn’t touched my dick. I was so excited the nurse became concerned I’d bust a stitch.

I think it was the afternoon of the fifth day that Sheila and Jenny showed up. One of the doctors was with them. The three of them talked about me like I was an expensive pot. The bottom line was I would move back to the hotel. The doctor wanted to see me before I returned to the United States.