2.2: Sissification
Chapter Three
It did not take long for Eve Bartley to make up her mind.
An hour or so after Natalie performed fellatio on her husband by the swimming pool, Eve met with Dick to inform him.
“Natalie has to go,” Mrs. Bartley said as they sat in Dick’s office, the door locked. “I can’t tolerate this. It wasn’t just that she violated one of my biggest rules. She seemed to relish the drama surrounding it, the blowjob right in front of my face, and fighting with me.”
Dick didn’t respond. He poured two tumblers of Tom Collins and handed the stronger one to Eve. He had anticipated his wife’s snap decision and chose to hear her out. If he disagreed immediately, she would dig in and not listen to him, he thought.
Eve sipped her cocktail. “As you’ll recall, I’ve thrown two femme bois out of the training program for rule violations – one for snorting cocaine and the other for being an annoying bitch. I don’t see any way to make an exception for Natalie. This was the most egregious violation, because it violated the trust I had in her.”
Dick nodded, waiting for his wife’s focus to shift to what he did. He didn’t have to wait long, although it sounded more like curiosity than anger.
“Have you been fucking Natalie?”
“No, you told me Xavier wanted a virgin sissy. So that was out of the question. I had no inkling she would bury her sweet little head in my crotch by the pool. Up to that moment, I had kissed her, but had not gone any beyond that. I promise you that. And I apologize for not telling you that I kissed her. I should have done that. And I should have shared with you my interest in having sexual relations with Natalie.”
Dick and Eve had an open marriage. The terms were simple. If they wanted to play, they had to be completely transparent. Both had enjoyed multiple sex partners in their 31 years of marriage. They felt strongly that an open marriage had strengthened their relationship, providing “spice” -- a variety of lovers -- while maintaining their own sex life.
“You weren’t attracted to the other femme bois I’ve trained. Why Natalie?”
Dick drained his drink and poured another.
“It’s the innocence; her sexual desire contrasted with her lack of experience. She’s also prettier than the others, with those blue eyes and blonde hair. I told you that Leigh-Anne wanted me to fuck her, and I told her no.”
“Did you ever kiss Leigh-Anne? Did she ever suck your dick?”
“No and no. Leigh-Anne scared me, to be completely candid. She often talked about her goal of becoming Xavier’s favored sissy. I had a weird feeling that she considered me a notch on her belt; that in some bizarre way she would benefit from fucking the husband of Eve Bartley in her own home. It would give her street credibility.”
“I wonder if Natalie feels the same way,” Mrs. Bartley suggested.
“No, that’s not the way she’s wired,” Dick scoffed. “She’s a sweet teenager. If Xavier becomes her master, that sweetness will remain – but she will become a woman; desirous of the dominance that a man will hold over her, the sexual love that she needs and deserves.”
Xavier, a multimillionaire, was the cousin of a drug cartel kingpin in Mexico. He had a mansion on the outskirts of Phoenix, staffed by 19 sissies trained from across the nation. Eve was among those trainers. She had met Xavier through her husband, an attorney who laundered large sums of money for Xavier.
Leigh-Anne was the first femme boi whom Mrs. Bartley had trained to become a sissy for Xavier. Like Natalie, she had undergone hypnosis with Mistress Xi.
“Are you aware that Leigh-Anne is not wearing the red dress anymore?” Eve asked.
Dick shook his head no. The last time he had visited Xavier’s mansion, Leigh-Anne wore the red satin sissy maid dress that signified who was Xavier’s favorite sissy. She had flirted with Dick, a dangerous game given Xavier’s jealousness. Dick had tactfully not responded to her.
“Xavier wouldn’t tell me why. He said Alexis is wearing that dress now. Have you met her?”
“I have, but just briefly.”
“And?” Mrs. Bartley inquired.
“Well, I met her in Xavier’s office. He had put out a bowl of milk for her. Like a pussycat, she moved on all fours through the ballroom to his office. We watched her lap it up, and then she left. Xavier was pleased by her demeanor. I’m not surprised Alexis is in the red dress now.”
I can’t tell my wife what happened the next day. Xavier told me he had a ritual for his closest confidants. He considered it a loyalty test. I had to fuck a sissy, his current favorite. It would be an honor for me, he explained, and of course I agreed. We went up to Alexis’ bedroom. Xavier told her to take off her red satin sissy maid dress and put on a red rubber catsuit. We made out on her bed for an hour. I thought I literally was going to explode. She would suck me for ten minutes and then stop, and we’d kiss more. I decided to play along, to show her my stamina.
When she pleaded with me to fuck her, I slowly unzipped the back of the catsuit, lubricated her derriere-pussy and fucked her like an animal as Xavier videotaped. It was my first sissy fuck. “If that’s how I need to show loyalty, I’m all in,” I told Xavier later over brandy and the best cannabis I’ve ever smoked.
Dick steered the conversation back to Natalie.
“I’m not justifying what Natalie did. But do you think there’s a link to Mistress Xi’s sessions?”
“Well, I don’t know how we could tease that out. It’s not like Mistress Xi trained Natalie to suck your cock in full view of me.”
“How do you know that?” countered Dick, who noticed that his wife had finished her drink. He poured her another. “How many sessions did she have?”
Mrs. Bartley said there were 12, each lasting half an hour.
“Eve, I’m not trying to overturn your decision. I would only ask that you talk with Mistress Xi about Natalie’s training, the hypnosis, the behavior modification, and whether part of Natalie’s brain was washed.”
Mrs. Bartley told Dick that Mistress Xi, shortly after the hypnosis sessions had ended, recommended that Natalie be placed in chastity to try to prevent hyper-sexualization. Mrs. Bartley had followed her advice.
“Well, there you go,” said Dick. “Isn’t that a sign that something was awry? I know it’s going to sound self-serving, but I would run what happened by Mistress Xi before you make a final decision on removing Natalie from the training program.”
Dick didn’t have to mention the $200,000 that Xavier would pay for a sissy who was a virgin. Mrs. Bartley thought about the money but she also considered that there would be future sissy bois to train. How could she retain her credibility if rules were not followed? In the end, after hearing Dick out and debating the issue with herself, she agreed to meet with Mistress Xi.
But Mrs. Bartley thought the chances of her not booting Natalie out of the program were slim to none. Even though she was voyeuristic, Mrs. Bartley was troubled by the memory of Natalie’s lips pressed against Dick’s penis, his semen flowing into her mouth.
It took a few days for Mrs. Bartley to get a return call from Mistress Xi, the dominatrix who also worked for Xavier. Originally from Beijing, her specialty was behavior modification. She was a subcontractor to sissy trainers across the nation; someone Xavier respected deeply.
They met in Mistress Xi’s office on the second floor of her Victorian-style house. As usual, Mistress Xi’s long black hair was parted in the middle, but she wasn’t dressed as a dominatrix. It was a business day without any sessions, and so she wore a violet silk blouse, a tight black pencil skirt, and black leather pumps with a high heel.
Mrs. Bartley recounted what happened by the swimming pool between Natalie and her husband.
Mistress Xi asked if Natalie was in chastity.
“She was. It’s a CB 6000 and she didn’t seem happy about it,” Mrs. Bartley said.
Mistress Xi made a small notation in her notebook. “So, what do you want to know?” Mistress Xi asked. “Can I call you Eve?”
“Of course. Did your training sessions cause Natalie to have sex with my husband?”
Mrs. Bartley struck Mistress Xi as bizarrely naïve, almost uninformed about what Xavier wanted or what was happening around her. Her judgment was reinforced by Mrs. Bartley’s outfit – a low-cut black and white polka dot sun dress that showed off her big tits.
I don’t need this chick showing off her rack in front of me.
Mistress Xi scrolled through her phone and found an email she had received from Xavier.
“Eve, did you send this to Xavier recently through the encrypted messaging app?”
Mrs. Bartley leaned forward to read the text she had sent about Natalie.
<She’s adept at taking orders and obeying, but I don’t know if she has the ability to bend or break rules when needed. Didn’t you say you were looking for a ‘bad’ sissy – rebellious and willing to do things that other sissies would not?>
“I did send this,” Mrs. Bartley said, as Mistress Xi deleted the email.
“Then why the fuck would you be surprised that she broke a rule?” Mistress Xi asked, her voice raised.
Mrs. Bartley was startled. Her face flushed with embarrassment.
“I think it’s because she violated the rule about sex with my husband.”
Mistress Xi laughed. She had no interest in concealing her scorn.
“Eve, I don’t want to be overly disagreeable. But let’s review the facts. Your husband has emerged as a top lieutenant to Xavier, who has paid him millions of dollars in fees for financial work. Dick has shown enormous loyalty and that is everything to a businessman like Xavier. Xavier has wired you $300,000 for the training of two sissies. Do you want to fuck that up for you – and your husband?
“Did my training cause Natalie to suck Dick’s cock? I believe the answer is yes, but there is no way to prove that. This is what I do know. There’s a much bigger picture here. Your rule about femme bois being barred from having sex with your husband was absolutely fucking irrelevant to Natalie.
“Part of her brain has been washed and it’s irreversible. You can call it whatever you want – dick, cock, penis. She wants what alpha males have between their legs and as long as she is alive, she will want cock. Wasn’t that your goal in having me train her?”
Mrs. Bartley was speechless, a rarity. Mistress Xi couldn’t suppress her smile.
“I hope you’re not thinking of removing Natalie from your training program,” Mistress Xi added, breaking the awkward silence. “Xavier wouldn’t want that. Do you agree?”
Mrs. Bartley didn’t respond. It was the end of the meeting. Later that day, she texted Xavier after thinking about Mistress Xi’s words.
<Good evening, Xavier. Did Mistress Xi tell you what happened with Natalie?>
<She did. Have you made a decision about whether to keep her in the training program?>
<Yes, I’ve decided to keep her enrolled>
<That’s a wise decision, Eve. It’s easier said than done, but you have to separate your personal life from business. You’re very close to delivering something very valuable to me, and as you know, you will be compensated handsomely. I know the ego is powerful, but I’m glad that you’re not letting your selfish interests get in the way>
***
Natalie didn’t know what to expect when Mrs. Bartley asked if she had time to talk in the kitchen. Mrs. Bartley had chosen this time because Dick was not home. He had gone to his downtown office to handle a transaction.
“We need to talk about what happened yesterday,” Mrs. Bartley said. Her voice was not stern; it was matter-of-fact but tinged with emotion.
“I’m so sorry,” Natalie said. “I was so out of control.”
Mrs. Bartley asked what happened.
“I was angry about being placed in chastity, but it was much more than that. When Dick asked me to spread that suntan oil right above that sexy swimsuit he was wearing, I could hear Mistress Xi’s voice – ‘I want dick. I am a girl.’ I had to have his cock in my mouth. It was the first time I had sucked cock.”
“I know, Natalie. It’s a special moment for a girl,” Mrs. Bartley replied, her hand playing with Natalie’s blonde hair.
Natalie couldn’t control the tension that had been building. She began to cry. Mrs. Bartley embraced her as Natalie’s body shook with emotion.
“I can’t resist your husband. It’s almost like a gravitational pull,” Natalie said, her mascara streaked from her tears.
“My husband is a dominant – and very controlling. He’s always been that way. I’ve shared him with other women, but I do have a problem with jealousy. I supposed it’s a fear I’m going to lose him to another girl, someone young and beautiful like you.”
“Are you going to kick me out of the training program?”
“I strongly considered that option, but no, Natalie. It would be hypocritical for me to do that. I initiated your sessions with Mistress Xi to find out if you would bend or break rules. You did. How could I punish you for that? It would be an emotional response; nonsensical. And there is a school of thought that rules were made to be broken.”
“Thank you, Mrs. Bartley.”
“We do need to come to an understanding about my husband. If you’re going to have oral sex with him, I have reminded him that he needs to tell me. We have an open marriage. I hope that doesn’t bother you.”
“No, not at all, Mrs. Bartley.”
In the evening, the Bartleys invited Natalie to join them for dinner. As usual, Dick sat at the head of the table, with Mrs. Bartley and Natalie at his sides. Dick’s appearance distracted Natalie. He had changed from his business suit to a white button-down shirt and black leather pants. The pants were tight enough to show off his big, manly ass. Natalie couldn’t keep her eyes off of it when he stood.
The conversation was pleasant and ranged over several topics. Dick had made a large real estate investment in a company and it had paid off spectacularly earlier that day. He had invested $1 million and the deal had netted him $10 million.
Natalie didn’t understand most of what Dick and Mrs. Bartley discussed. She admitted that to Dick when Mrs. Bartley left the dining room to fetch a bottle of champagne.
“You’ll learn about money, Natalie,” Dick told her. You’re only 19 years old. It’s all an inside game. You’ll have many teachers if you become a sissy.”
“Will you teach me?”
“It depends. You’re being trained to work for a businessman who is an alpha.”
“You’re an alpha male too,” Natalie offered.
“Not like him. If you become a sissy, your Master would be several levels above me. He would decide whether I could talk to you, let alone teach you about money. He’s fought men and beaten them severely to win access to sissies. He doesn’t fuck around.”
Mrs. Bartley returned to the dining room. Popping the cork, she poured three glasses of champagne and offered a toast to her husband’s successful investment. Dick had told his wife – per their agreement – that he planned to have sex with Natalie that night, but he didn’t say how it would unfold.
After a second round of toasts, Dick told Natalie to stand up. She was wearing a white dress with a mini-skirt hem, sleeveless, with an attached lace-up panel at the midsection that gave the dress a corseted look; a racerback with a hidden zipper in the back that led to a collar for a choker-like look from the front. As she stood in front of Dick, he raised the front of the hem to reveal the chastity device that kept her little clitty off limits.
“This must be tough to live with, Natalie.”
“It is.” Natalie did not look at Eve across the table.
Dick ran a finger over the edge of the cage.
“Your clitty is limp and obedient.”
“I have been trained that way, thanks to your wife.”
Mrs. Bartley smiled at Natalie’s kind words. Her pussy was getting wetter as Dick and Natalie continued this dialogue.
“Why is it tough to be in chastity?”
“I want to masturbate, to just run a single finger over my little clitty.”
“Has my wife taught you that you can’t masturbate like a man, pumping your shaft until you come?”
“Yes, Dick. She calls it ‘choking the chicken.’ I can’t do that anyway because my clitty is so small.”
Dick paused. “Why do you want to masturbate, Natalie?”
“I have fantasies about cock, about your cock, how hard it is, Dick.”
“Has Eve bought you a butt plug and an anal toy?”
“No, she hasn’t – not yet.”
“Do you understand that you will masturbate using an anal dildo, to prepare yourself for your master?”
“I do, Dick.”
“Do you fantasize about sucking cocks other than mine?”
“Yes, I do.”
“Who?”
Natalie didn’t respond immediately.
“Would it anger you if I said who?” she asked demurely.
“No, Natalie. I need to know.”
“It’s Rodrigo.”
Dick slowly unzipped Natalie’s dress and it fell to the floor. She had begun to wear a bra because she was undergoing estrogen treatments. Dick removed it, along with her panties, stockings, and pumps so that Natalie was nude.
“I’m going to restrain you. Do I have your consent, Natalie?”
“You do.”
Dick removed a pair of silver handcuffs from his pocket and, gathering Natalie’s arms behind her back, he attached them to her wrists.
“Rodrigo is waiting upstairs for us,” Dick whispered in her ear.
Turning toward him as Dick began to guide her up the stairs, she looked excited. He told her that his wife wanted to watch and asked if she objected. She said she did not. Mrs. Bartley followed them up the steep staircase, noting how careful Dick was with Natalie who could not use the railing because of the handcuffs.
Rodrigo smiled as Natalie entered the master bedroom. He rested on the bed, his nude body a light shade of brown. It contrasted with Natalie’s creamy white skin as she lay next to him and Rodrigo French-kissed her. Dick watched them, knowing how desperate Rodrigo was to have sex with Natalie. Dick was impressed how Rodrigo didn’t go fast, like other twenty-somethings who didn’t know shit about pleasuring a woman.
Dick fastened a white leather collar around Natalie’s neck and attached a matching leash. He undressed quickly. As Dick and Rodrigo knelt on the bed, Natalie took turns sucking their hard cocks. Mrs. Bartley sat on a sofa nearby. Unbuttoning her blouse, she ran her hands over her 38DD tits, the sensation thrilling as she tugged on her nipples. She reached back to unzip her skirt and made quick work of her lace thong. Spreading her long legs, she began by pushing a few fingers between her folds.
Natalie and Mrs. Bartley had talked about bukkake. Mrs. Bartley didn’t know if she was ready for it. As Dick came first, Mrs. Bartley watched several ropes of semen cover Natalie’s nose, eyes, and her forehead.
“That’s a good cum slut,” Dick said as Natalie kept her mouth open as he sprayed more of his seed over her face.
Rodrigo then emptied his load, glazing the rest of her face with his hot spunk. Dick let Rodrigo clean up, using a silk handkerchief to dry her face and then letting her inhale the aroma and lick the surface.
That night, Mrs. Bartley wrote in her journal:
It’s almost time for Natalie to fly. I need to teach her more of the vocational stuff – the finer points of being a maid, how to pace herself during an eight-hour shift, the proper etiquette during a dinner party, etc., etc. She’ll be working hard, especially for the first few months. It’s not easy vacuuming in high heels. LOL
Watching Natalie with my husband and Rodrigo was exhilarating. She has come so far in nearly one year. The pretty boi who sneaked into my panty drawer while I was away has become a confident young girl on the brink of sissyhood.
But only Xavier can make that decision.
In the FBI office in downtown Phoenix, Agent Rick Blair handed his boss a thick file and plopped down in front of his desk.
“So have we confirmed that Xavier is Hector’s cousin?” Special Agent in Charge Tom Smith asked. Smith referred to the leader of the Mexican drug cartel, whose code name was Hector.
Agent Blair said he had, adding that he was working with an agent from the Drug Enforcement Administration.
Smith was new to the job, transferred from the FBI’s Chicago office to Phoenix two months ago. He had a lot of questions for Agent Blair. He pulled out one of the few pictures ever taken of Xavier and one of his mansion.
“How long has he lived in Arizona?”
“It’s been five years. He got a master’s degree in business from the local university and then had that mansion built in 2019. It’s about 125 miles northwest of Phoenix.”
“What else do we know about him?” Smith asked.
“The Drug Enforcement Administration has a theory that he is in the United States to launder cartel money. It’s logical, but there’s no evidence of this. He could be a legitimate businessman. We have no probable cause to intercept his communications. We’ve done some work, but the results mainly have been about his kinks. You’ll see the pictures in the file.”
Smith moved to that tab in the file. There were a dozen or so pictures of young women in maid dresses.
“These were all shot at the private airport near Chandler. We talked to a source at the airport who said the flights arrive from all over the country. These are sissy maids – biological males who become women to work for Xavier at the mansion. Our source identified the pilot as Captain Tim Tillis, a 69-year-old Air Force retiree from Texas.
“We’ve tailed Tillis. He lands here, drives these sissy maids to Xavier’s mansion, and leaves. Our source has tried to talk to Tillis about them, but he’s tight-lipped. He lives in a modest condo in Glendale and is divorced. The private jet he uses is registered in Bermuda and owned by a shell company, ostensibly owned by Xavier.
“Xavier rarely leaves his residence. The sissy maids are driven occasionally to Phoenix, mainly to shop and to attend small parties. We don’t know any of their names. It’s not a lot to go on,” Agent Blair said.
Smith looked out the window, lost in thought for a moment.
“I think we need to take a closer look at Tillis. He’s bound to make a mistake and if he does, we can pick him up and ask some questions. That’s about all the advice I have for you now,” he told Agent Blair.
***
In the final month of Natalie’s training, she shared Dick’s bed. Mrs. Bartley slept on a cot in a corner of the master bedroom.
It was Dick’s decision, and he told his wife it obviously was a temporary arrangement. He anticipated that Natalie would be leaving soon to live in Xavier’s mansion.
At Dick’s request, Natalie had begun to wear white spandex outfits – either pants with a top or a short skirt or dress. It was among Dick’s fetishes. Natalie was insatiable. She couldn’t get enough of Dick’s cock. It was not unusual that she sucked him off four or five times a day. He often had erections when he woke up that he called “morning wood.” Lunch often came with a blowjob. Nighttime was when romantic kissing eventually turned to Natalie performing fellatio on Dick, often twice or three times.
Mrs. Bartley wanted to know if Natalie would become arrogant or haughty. It would be tempting, given the attention she received from Dick. But she didn’t display any of those behaviors.
Relaxing one night with Natalie on the veranda, Mrs. Bartley noted that it had been eleven months since her sissy training had begun.
“Have I graduated?”
“Not yet. The businessman who would be your master makes that decision, not me,” Mrs. Bartley said. “He’s asked for one more thing in your training. He’d like me to interview you. I would videotape it, and send him a copy. We’ll do it tonight.”
Natalie was confused. “Why is he requesting this?”
“I don’t know. He doesn’t share his reasons with me.”
Mrs. Bartley set up the equipment in the Sissy Trainee Bedroom.
“Just be yourself,” Mrs. Bartley advised before she turned on the camera.
Q. Please state your name.
A. Natalie Everett.
Q. And how old are you, Natalie?
A. I’ll be 20 in one month.
Q. How would you describe yourself?
A. I’m in training to become a sissy maid. I’m hopeful I will start a new life soon.
Q. Why do you want to be a maid?
A. I want to serve a male master. I believe it is my fate to serve at his pleasure, to help operate his residence as he sees fit. I’ve been trained extensively in house cleaning – dusting, hand-washing dishes, and sweeping floors.
Q. How would you describe your living arrangement?
A. I live in the Bartley residence.
Q. I mean at night.
A. Like now?
Q. Yes.
A. Um, I sleep in Dick Bartley’s bed.
Q. Who gave you permission to do that?
A. Dick did.
Q. Do you have your trainer’s permission?
A. I do not.
Q. Why?
A. I never asked for it. Dick is an alpha male and he has the power to decide who will be in his bed.
Q. Has Dick ever penetrated you?
A. No.
Q. So you are a virgin?
A. Yes, I am.
Q. What would you do if Dick said he wanted to fuck you?
A. I would give up my virginity for him.
Q. Why?
A. He is an alpha male. Men are superior. You don’t question their decisions.
Q. Do you have romantic feelings for Dick?
A. I do.
Q. Please describe those feelings?
A. It’s not easy to describe. I feel very close to him. He’s a kind and thoughtful person, but he also has enormous power over me. When I suck his cock, I feel the vitality coursing through his body. He transfers that to me through his semen. It fills me with life and I’m indebted to him.
Q. Do you consider yourself a cum slut?
A. Yes.
Q. Are you in love with Dick?
A. I am.
Q. Do you consider sissyhood as a third gender, separate from male and female?
A. I don’t know enough about that. I’m not sure. I can only speak for myself. I’ve always felt that I was born as a girl in a boy’s body and now I’m pursuing womanhood as a sissy.
Q. So you identify as female?
A. Yes.
Q. Do you want gender correction surgery?
A. I don’t know. I want to become a sissy first. That’s the only thing I’m thinking of.
Q. But I’ve referred to you as a femme boi. If you don’t identify as a boi, why didn’t you say something?
A. I wanted to be polite.
Q. Is it polite to steal a woman’s husband, like you did with Dick?
A. I didn’t steal him.
Q. OK, borrowed him.
A. You know full well that your husband wanted me. You and Mistress Xi trained me to be a sissy. Your words were ‘men are superior and sissies live to make them happy.’ I’ve made your husband happy, and I didn’t need your permission.
Q. What if your Master said you could not have sexual relations with Dick Bartley?
A. I would obey my Master. I no longer would have sex with Dick.
When Xavier watched the video the following day, he texted Mrs. Bartley.
<You’ve done a wonderful job with Natalie. I can’t thank you enough for bringing her to this point. You might want to check your bank account now>
Mrs. Bartley logged in and saw the wire transfer of $250,000.
<Thank you very much, Xavier. More than I anticipated>
<$200,000 for a virgin and $50,000 for how you handled this delicate training. Most trainers would have thrown Natalie out on her ass:.)>
“I appreciate those kind words, Xavier>
<There’s one more thing. I’ve decided that Natalie will wear a black satin sissy maid dress instead of a pink one. As you know, I’ve been looking for a ‘bad’ sissy – one who has accepted her training but also was rebellious and willing to do things that other sissies would not. That’s Natalie>
Mrs. Bartley couldn’t wait to give Natalie the good news. They shared tears of joy and sadness. The dress would arrive in the mail in a few days, and then Natalie would be flown to Arizona to start her new life with Xavier, the businessman who would be her Master.
“Why would it be a black dress?”
“The businessman who will be your master says you are special. And you are, sweetie. I see such a bright future for you as a sissy.”
“I’m so appreciative of what you have done for me, Mrs. Bartley. I owe everything in my future to you.”