2.0: Sissification
Chapter One
Captain Tim Tillis’ job was to fly sissies to a resplendent mansion owned by a secretive man known as Xavier.
The sissy sashaying toward the Learjet Global -- at a private runway about 100 miles west of Kansas City -- was different from the others. Captain Tillis was puzzled. She wasn’t pretty in pink. She was pretty in black.
Not just pretty. Absolutely fucking stunning in a shiny black sissy maid dress.
Captain Tillis checked the flight’s manifest. The sissy’s trainer, Mrs. Bartley, had listed her name as Natalie. Captain Tillis sent Mrs. Bartley a text.
Mrs. B, just wondering. Why is Natalie not in pink?
There was no response. Captain Tillis put down his smart phone and peered through the cockpit window at Natalie. She wore a custom-made black PVC French maid dress with white trim on the hem of the short skirt. The long-sleeve dress featured a high neck with a lockable function, a boned removable cincher, and matching PVC panties that were ruffled, with a zip crotch and a lock.
Captain Tillis had the keys in his breast pocket, but he’d need only the one for her panties. Greeting Natalie warmly at the top of the stairs, he informed her she was the sole passenger and could pick her seat. When she did, he handed her a flute of champagne. She thanked him politely and asked if there was anything he needed, displaying her impeccable manners.
“Oh, I can think of a few things, but let’s get to Phoenix first and safely, young lady,” he replied with a wide smile.
Shortly before takeoff, Mrs. Bartley replied to his text.
Captain Tillis, as you know, Xavier is demanding. For some time, he’s been looking for a ‘bad’ sissy – one who accepted her training, but also was rebellious and willing to do things that other sissies would not. That’s why she is in black. You may get a glimpse when you land :.) Mrs. B.
Captain Tillis chuckled. A retired 69-year-old Air Force captain from Texas, he worked for Xavier for a nominal salary. His compensation came in a different way. Each sissy transported by Captain Tillis knew that once they landed, he would be their daddy for one hour, more or less. It wasn’t an option. Xavier required it. It was the final step of the training before he took title to the sissy.
Given Captain Tillis’ ruggedly handsome looks, no sissy ever had complained. Behind locked doors at sleepovers in Xavier’s mansion, they referred to him as “slow hand” and blushed when they described how a thick cock can downright “wreck” a sissy.
Natalie spent most of the three-hour flight lost in thought or asleep. Her farewell with Mrs. Bartley had been highly-emotional. Natalie had cried, but she also was excited about leaving. Mrs. Bartley could sense this confusion. After Natalie wrecked her make-up with tears, Mrs. Bartley re-did it and gave her a pill. Natalie became tranquil. Her thoughts about Mrs. Bartley and her husband, Dick, were conflictive, in large part because of her numerous sexual encounters with Dick as his wife had watched silently.
Now, as the private plane taxied at the small airport, Captain Tillis stopped in the hangar that Xavier owned.
He walked to the cabin and joined Natalie on the couch. He asked if she would like another glass of champagne. He poured two glasses and offered a toast to her new life in the valley of the sun.
“Thank you, Daddy.”
Captain Tillis smiled. Occasionally, he had to remind sissies to address him properly. She struck him as not only well-trained, but also well-bred.
“I hope the flight went well. Are you excited to see your new home?”
“Very much so, Daddy.”
Captain Tillis kissed Natalie and before long, their tongues touched. Her perfume immediately caught his attention.
“I love that scent,” he whispered in her ear, “what is it?”
“‘Touch of Seduction’ by Christina Aguilera.”
Captain Tillis felt intoxicated by the smell. He steadied himself by staring into her blue eyes, her blonde bangs brushing her eyebrows. He kissed his way down her neck. Her body, lithe like a ballerina’s, opened to him. She kept his captain’s hat on (she liked the look of uniforms on gentlemen) but she unbuttoned his shirt, running a long black fingernail through his thick grey chest hair. He wore a crucifix on a chain.
“Thank God for silver daddies.”
“Natalie, I want you to get into a table top position.”
She did so without hesitation. Her obedience pleased him. Captain Tillis reminded himself of Xavier’s number one rule. The dress does not come off.
There were people close to Xavier who resented Captain Tillis’ perk. He thought about them for a moment as he grasped Natalie’s ankles and slowly spread her legs farther apart.
Jealous little people. My perk is a reward for being so loyal to Xavier.
Raising the hem of Natalie’s dress, Captain Tillis felt his pulse quicken. Like the dress, the rest of her outfit was black -- pumps with a stiletto heel, silk hose with a seam up the back, and a garter belt. He reached into his pocket for the key to her PVC panties and unlocked them.
Bunching the lower part of her sissy dress at her waist, Captain Tillis began to lick along the seam of her right silk hose, starting at her ankle. He felt her body shift in response. Reaching the bare skin below her panties, he kissed it, pleased by its feel. She had no tattoos and had not been branded.
“You have the softest skin, Natalie,” he said.
“Thank you, Daddy. Did you know this dress is called a candy cupcake?”
“Very fitting for a sissy as delicious as you, Natalie.”
As with the other sissies, Captain Tillis had one objective – total pleasure. That usually meant a long, slow fuck. The sissies often marveled at how a man his age could stay so hard for so long. Captain Tillis had decided to do something different with Natalie, though.
Slipping her panties down her long legs, he placed his right hand on her hip as he used his left to keep her dress at her waist. He then slowly slid his tongue into the entrance of her derriere-pussy. She gasped as he slid his tongue a few inches inside her tight channel.
“Oh my God, Daddy. You’re such a bad boy.”
The words pleased him.
A bad sissy in black calling her Daddy a bad boy.
“Daddy, I’ve never been tongue-fucked like this.”
Captain Tillis moved in deeper. It did not take long for Natalie to lose control from the sensation of a gentleman’s tongue deep inside her derriere-pussy.
She reminded Captain Tillis of a lyric from Britney and will.i.am: “Scream and shout and let it all out.”
He watched the thick cream shoot out of her clitty in long ropes. There was so much cum. It appeared Mrs. Bartley had kept Natalie in chastity for quite some time.
Captain Tillis looked out the window and saw the two black SUVs speed toward the plane, the occupants in sunglasses and black suits with guns drawn.
He put Natalie’s black PVC panties back on her. He assured her everything would be OK.
These feds will regret fucking with Xavier.
One year earlier
Eve Bartley poured herself a Diet Pepsi and dialed Robin Everett’s number.
Robin had become a friend over the past 20 years, although not a close one. They spoke on the phone occasionally and ran into each other at social occasions. Mrs. Bartley thought her first name fit her well. Robin was a short woman with bird-like features. Robin was divorced and the rumor was that she was an alcoholic.
Mrs. Bartley was calling about Robin’s only child, a 19-year-old named Nathan. They chatted for 20 minutes before Mrs. Bartley popped the question that had prompted her phone call. Could Nathan house-sit for a few months while she and her husband were on vacation in Cancun? They would pay him above the minimum wage, Mrs. Bartley told her.
“Oh, I’m sure he would,” said Robin, without any hesitation. “He has no plans this summer except for taking some courses.”
Mrs. Bartley thanked Robin. She had chosen Nathan out of curiosity. Mrs. Bartley volunteered at the high school and she had encountered Nathan a few times. Like his mother, he was short with a slight build – 5’ 4” and about 120 pounds. She had heard he was bullied mercilessly. At an early age, it was his shortness. Later, it became his effeminate appearance. His nickname at the high school was PW, short for panty-waist.
At the time of Mrs. Bartley’s phone call, Nathan was attending art school part-time and living with his mother to save money. When he returned home that afternoon, Robin asked him if he remembered Mrs. Bartley.
“Name does not ring a bell.”
“She lives on Pemberton Drive, her husband is Richard, but goes by Dick. You met her once when you were about eight years old.”
Nathan said he had no recollection. Robin said she was a friend of hers.
“She has asked if you can house-sit in July and August while she and her husband are on vacation. I told her you could.”
Nathan gave her an eye-roll. Robin frowned at her son.
For the next two days, Robin and Nathan sparred over Mrs. Bartley’ request. Nathan complained his mother was presumptuous. Robin said her son should consider the money he would make.
In the end, Nathan did what his mother wanted.
Two days before she and her husband left on vacation, Mrs. Bartley called Robin to arrange for a time when Nathan could drop by. She wanted to tell him what she needed him to do. They scheduled it for Friday morning.
Mrs. Bartley was somewhat distracted as she invited Nathan into her home. A business associate named Xavier had called her that morning with some troubling information. She tried to keep it out of her mind as she began to give Nathan a tour of the two-story house, located on the edge of a new subdivision popular with soccer and hockey moms.
She handed him a to-do list and expounded on each item.
- vacuum once a week and dust.
- cut the grass and water the plants inside and out.
- make sure the pool boy does his job every week.
“Please park in the front so people know someone is in the house,” she added. Nathan took notes. Mrs. Bartley added more items to the to-do list.
Mrs. Bartley’s appearance had caught him off-guard. He blamed his mother for not telling him.
She was 59 years old. Nathan had looked it up on the internet, but she looked like she was in her 40s. She had ‘big hair’ – dark brown with light streaks that brushed her shoulders. Her face was pretty because of two features – her green eyes and full lips, emphasized by her pink lipstick. She wore large hoop earrings like younger women.
What surprised Nathan the most was the low-cut, short sleeve green blouse that presented her large breasts. The rest of her outfit struck Nathan as odd; tightly-fitting camouflage pants and sneakers.
A native of Alabama, Mrs. Bartley spoke with a thick drawl. He had to ask her a few times to repeat herself.
“Do you have any questions, Nathan?”
“No, ma’am.”
“You can use the pool and bring your art supplies if you want to.” Mrs. Bartley waited for a response. When she didn’t get one, she said he seemed very quiet.
“I just get nervous when I meet new people,” he said.
Mrs. Bartley reached out to touch his left hand. She felt him move back slightly. Young men usually didn’t do that. They usually had their eyes planted in the cleavage of her big breasts. She was glad that Nathan didn’t do that, but she didn’t get a clear vibe from him either.
That night, she wrote in her journal:
I don’t know if I made the right call in recruiting him for sissification. I can’t tell if he’s clinically depressed or repressed by gender confusion. Hopefully, it’s the latter. He’s different from Leigh-Anne, though. She showed glimpses into her effeminate nature; in the early days, she wore some jewelry and grew her hair out. Nathan seems like a blank slate, like a white piece of paper before someone draws on it.
Xavier called this morning. He said in coded language that we should not talk on the phone anymore because of the feds. I told him I could not make any promises about a delivery. He thanked me for being straight with him.
A few weeks after Nathan began to house-sit for Mrs. Bartley and her husband, he explored more of the large house.
One day, after vacuuming the master bedroom, he entered the large walk-in closet and turned on the light. Mrs. Bartley had told him he didn’t need to vacuum it.
The closet was used solely by Mrs. Bartley, Nathan discovered. He had limited experience, but he never had seen anything like it. There was row after row of clothes – dresses, skirts and pants. An entire wall consisted of her shoes – everything from patent leather boots to running shoes. There also were five wardrobes, perhaps added as Mrs. Bartley acquired more outfits.
Nathan gently opened the top drawer of an antique dresser that had caught his eye. Half of the drawer was filled with panty hose and the remainder with panties. He closed the drawer.
I can’t do this.
Nathan walked out of the closet and left the bedroom. In the family room downstairs, he curled up on the couch and fell asleep.
In the morning, Nathan drove to the pharmacy and used the self-checkout. He returned to Mrs. Bartley’s house and placed the items on the counter of the bathroom that he used on the first floor. He took a long shower and applied the shaving cream on his left leg, spreading a thin, even layer. He didn’t have a lot of hair on his legs, but he wanted none.
I never wear shorts, so no one – including my mother – will know.
Beginning at his ankle, Nathan slowly shaved upward. He had read in a women’s fashion magazine that you got a closer shave by going against the direction of hair growth.
Nathan felt his penis harden. It usually was only two inches long and just an inch longer when erect. It also did not resemble a typical penis. Uncircumcised, it resembled a wisp of pink skin, unformed, a snippet. His testicles were tiny.
He returned to the shower to rinse his legs off. Nathan ran his hands over them to make sure he didn’t miss any spots. He dried off and, putting his robe on, walked upstairs to the master bedroom.
I have to make sure everything looks the same when Mrs. Bartley returns.
Nathan opened the dresser drawer he had seen the day before. There was a pair of silk panties on the left side, the color of champagne with white lace trim. He used his smart phone to take a picture of how they were positioned and did the same with the pantyhose. Nathan removed them from the drawer and sat on the edge of the bed.
I can’t do it.
His body was shaking. He thought he was going to throw up. He fought the words in his head. Slipping the panties up his legs, he felt the luxurious silk against his skin.
Nathan felt a powerful mixture of excitement and relief. He carefully stepped into the panty hose and experienced the first rush. The sensation was surprisingly powerful.
Is this how a fetish feels?
Nathan walked over to the floor-length mirror and examined his reflection. Without touching himself, Nathan experienced his first hands-free orgasm. His cum covered the gusset of the panties and he could see a large wet spot on the panty hose too. He panicked. He told himself to calm down. He simply would wash them.
After that, Nathan cross-dressed daily with panties and hosiery. The following week, he tried a pair of black high-heel pumps from Mrs. Bartley’s closet. He thought they were timeless. He had seen them on women in films from the 1930s. They were still in fashion today.
He was practicing walking in the five-inch heels when he heard someone pull into the driveway. His heart skipped a beat or two or three. Grabbing his robe, he rushed into the hallway, which offered a view of the driveway where a black pick-up truck had parked.
It’s the pool-boy. I should have remembered he comes every Wednesday afternoon.
He wasn’t a boy, of course. Rodrigo was in his late 20s, Hispanic and handsome.
Nathan watched as Rodrigo unpacked his pool-cleaning equipment and walked to the back of the house. Mrs. Bartley’s home was located at the edge of a new subdivision. There were no houses on the adjacent lots or behind. The in-ground pool was set in the middle of a huge lawn. An eight-foot-tall fence offered privacy.
Nathan watched Rodrigo clean the pool for a few minutes. He returned to Mrs. Bartley’s closet. He had found a box of her stuff from what looked like the 1980s. He wondered if the skirt on the top would fit him.
It was a short mini-skirt. Nathan didn’t own a gaff, but he did his best by tucking his small penis. The skirt was made of red spandex. It fit perfectly, zipping up the back.
Nathan decided to check on Rodrigo. Standing at a second-floor window in the hallway, he did a double-take.
Rodrigo was taking off his tank top. He had his back turned to the house. Nathan could tell that Rodrigo worked out a lot. His back was muscular. Rodrigo slipped his shorts off and he wasn’t wearing underwear. Nathan stared at his big ass, but he didn’t get to check it out for long as Rodrigo dove into the sparking blue water.
Over the next several weeks, Nathan couldn’t wait for Wednesdays to roll around. Standing at a second-floor window at the back of the house, dressed en femme, and confident he could not be seen, Nathan would masturbate as Rodrigo undressed to skinny dip in the pool. Afterwards, Nathan would take a long shower and try on another outfit from Mrs. Bartley’s closet.
He was trying on a pair of her thigh-high black boots one Wednesday when he heard the bedroom door open and watched Rodrigo walk in. Nathan usually cross-dressed in the closet, but today he was standing by the side of the bed. There was no place for him to go. He screamed and scampered into the walk-in closet. He had noticed how wide Rodrigo’s eyes had been at the sight of him in kinky boots, hose, and a black leather mini-skirt.
Rodrigo smiled at Nathan’s attempted disappearing act. He waited a minute to end the silence
“Are you Nathan, the house sitter? I’m Rodrigo, the pool guy.”
There was no response.
“It’s OK, Nathan. I won’t tell Mrs. Bartley – or anyone else. Can we talk?”
Nathan said yes. Rodrigo opened the closet door. He saw tears in Nathan’s blue eyes.
“It’s OK. You look better in that outfit than Mrs. Bartley. Don’t tell her that.”
Nathan smiled as Rodrigo laughed.
“Are you new to drag?”
Nathan nodded. Rodrigo said Mrs. Bartley never would know.
“I promise, Nathan. It’s our little secret.”
Rodrigo sensed that Nathan wanted to say something.
“Do you need a hug, honey?”
“Please.”
Rodrigo embraced Nathan, who seemed to melt in his large arms.
“Nathan, have you been watching me skinny dip?”
Nathan whispered yes. Rodrigo asked why.
“I like how your body looks.”
Rodrigo smiled. He could not see Nathan’s face, which was buried in his chest. Rodrigo stroked Nathan’s blond hair, which had grown to frame his face. Rodrigo said he had to leave to clean another pool. It was frustrating. He was confident he could seduce Nathan.
Rodrigo texted Mrs. Bartley before driving away.
He’s the prettiest sissy you’ve worked with, very innocent and virginal
She replied:
I’m glad you think so, Rodrigo
Mrs. Bartley checked in with Nathan by phone or email every week. Shortly before she and her husband were scheduled to return home, she sent Nathan a text message.
Nathan, my husband and I have had a slight change in plans. I’m going to return as scheduled, and he will remain in Cancun for an additional month. I’ll see you the evening of the 20th
Nathan worked hard to make sure the house was extra-clean. On her return, she thanked him profusely for his work and gave him a $100 tip.
A few days later, she sent him a text.
Nathan, could you drop by my house around noon?
Nathan said he could. Mrs. Bartley invited him to sit at the kitchen table with her.
“Nathan, I want to thank you again for your work. I’m reluctant to bring this up, but I feel I must get an explanation. Did someone wear a pair of my pantyhose while I was gone?”
Nathan’s face flushed red. He broke eye contact with Mrs. Bartley.
“I found a run in the pair that is on the top of the dresser drawer. Did you have a girl over?”
Mrs. Bartley watched the tears begin to stream down his face. He shook his head.
“Did you wear them, Nathan?”
He began to sob. Mrs. Bartley leaned forward to embrace him. He was shaking, but managed to talk.
“I’m so sorry, Mrs. Bartley.”
“It’s OK, Nathan. I needed to know whether someone was in the house without my permission or approval from my husband. We had talked about that, do you remember?”
Nathan said he did.
“Are you going to tell my mother?” he asked.
“Why would I do that, Nathan?”
“I don’t know. I don’t want her to know. She would kill me. She has asked me if I’m a faggot, and I hate that word.”
Mrs. Bartley said she understood.
What Nathan didn’t know is that there was a closed-circuit television system in every room of the house. She had watched some, but not all, of the footage when she returned home. There wasn’t a run in the panty hose. She just couldn’t tell Nathan she had been spying on him. He was too sensitive to handle that intrusiveness.
“I will keep your secret, Nathan. But you must do something for me. Come upstairs to my bedroom.”
Nathan asked why.
“No more questions, Nathan,” she said.
He took her hand and they headed for the master bedroom. She told him to sit at her dressing table.
“You have beautiful skin; just a little highlighter needed.”
Nathan began to cry again.
“Why the tears?” Mrs. Bartley asked, her voice showing a glimpse of impatience.
“I’m not sure I’m ready for this.”
“Nathan, you were wearing panty hose. What else did you wear? Be honest with me.”
“Panties, stockings, high-heel pumps, boots, and skirts.”
“We’ll go slow. I promise,” Mrs. Bartley said.
It didn’t take long for Mrs. Bartley to transform Nathan’s face – eye shadow, lashes, pencil, and pink lipstick. A blonde wig reaching to his shoulders completed the makeover.
“Meet Natalie,” Mrs. Bartley told Nathan, holding up the mirror so he could study the reflection. “Aren’t you pretty?”
Nathan nodded. “I look like a girl.”
“I’m proud of you, Natalie,” Mrs. Bartley said.
Mrs. Bartley called Nathan’s mother and said he would be staying the night. His mother, who was drunk, didn’t ask why.
Nathan did query Mrs. Bartley when she ended the call.
“Are you interested in becoming a sissy?” she asked.
He thought about Rodrigo. Nathan often fantasized about Rodrigo kissing and undressing him.
Without waiting for Nathan’s answer, Mrs. Bartley added: “Tomorrow, I begin your training in how to become a sissy. We’ll see if it’s the right life for you, sweetie. Do you understand what I’m saying, Princess?”
“I do, Mrs. Bartley,” Nathan said.