Helena Macneil: a Femdom Story
Copyright© 2025 by JohnMurray4173
Chapter 24: Brian Becomes a Sissy, Part 10 and Final
Erotica Sex Story: Chapter 24: Brian Becomes a Sissy, Part 10 and Final - The story of FemDom Mistress Helena MacNeil, who first came to our attention in my story Slut Babysitter: MILF Hunter, and her sissy husband Brian Parker. It details how a young Helena learned her roll as a FemDom and how she chose Brian to be her husband and then broke, subjugated, and sissified him to make him what she needed him to be. It tells of Brian's resistance to Helena's demands and how he broke and learned to enjoy being Helena's cocksucking sissy boy.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fa/Fa Fa/ft Ma/Ma Teenagers Coercion Consensual Reluctant Slavery Gay Lesbian BiSexual Heterosexual CrossDressing Fiction Cheating Cuckold Wife Watching Wimp Husband Incest Mother Son Brother Sister Father Daughter Niece Aunt Nephew BDSM DomSub Humiliation Light Bond Sadistic Spanking Torture Group Sex Orgy Anal Sex Analingus Cream Pie Facial Fisting Oral Sex Pegging Sex Toys Squirting
True to his word, Brian phoned Helena on Thursday night and asked her to go out on Friday. He’d booked seats at Oxley’s on the Wharf for 8:00 p.m. She promised to be there and then hung up.
Helena stared at her phone, shaking her head. Janey sat beside her on their couch.
“You’ve got it bad for the wife-beater.”
“You’re the one who said I should give him a second chance,” Helena said defensively.
“I did,” Janey replied, nodding. “At Sporties, I stuck the knife in and twisted it pretty hard, and all he did was admit he fucked up, apologise, and promise he wouldn’t do it again. I will admit that he impressed me.”
“What if he’s like Dad and becomes progressively more and more unhinged as the years go by?”
“Yeah,” Janey said thoughtfully. “I don’t remember Dad punching Mum around much until I was a teenager and beginning to assert my independence. Then when you turned sixteen, he seemed to go completely nuts. Poor Mum got it most weeks when we went out.”
“Yeah. I’m glad she finally bailed on him. He would have killed her if she hadn’t.”
“Are you prepared to forgive her and let her back into your life?” Janey had. She took their mother to dinner most Thursday nights and for lunch on Saturdays. Jenna, their mother, lived on a pension in public housing in Woodridge, Logan. A poor community mainly made up of housing commission homes and people with low incomes. Janey helped out with extra cash when she could.
“I’m not ready to make nice,” Helena joked, quoting The Dixie Chicks’ song that was her current favourite. “I probably need to. But I still get enraged every time I remember that she never intervened when Dad bashed us.”
“Yeah, but whenever she did, he bashed her instead. I can understand why she stood and cried rather than trying to stop him.”
“You copped it worse than I did,” Helena said.
Janey shrugged. “When he was about to lay into you for mouthing off, I’d say something worse to shift his attention to me.”
“I remember.” Helena looked away, feeling guilty. “I never thanked you for doing that.”
“How about thanking me now by coming to bed and fucking me with your strap-on?”
“Sounds like a plan,” Helena replied, agreeing. “After I do, maybe we can try the new double-ended dildo you bought last week.”
“Sounds good to me. Let’s do it.”
The sisters put their arms around each other’s hips and walked to Janey’s bedroom. Janey had a king-size bed, which was significantly larger than Helena’s double.
Friday went well, with Brian offering his cock cage key to Helena at their dinner’s end. Because of the memories of her father’s abusive ways towards her mother, Helena took some time to decide if she was ready to accept him back into her life. However, she eventually realised she wasn’t ready to give up on what they had yet. More than anyone before him, Brian made her motors rev. Although she’d had sex with Janey and Shelley, and had revisited Tracy, Helena hadn’t fucked another guy since she and Brian had broken up. The guys she’d met just weren’t up to his standard.
‘His nuts are coming off if he ever lays a hand on me in anger again,’ Helena assured herself after she’d agreed to go with Brian to a show at QPAC and dinner the following week.
Helena’s relationship with Brian continued to grow and evolve until, after about six weeks, she slept with him again. Well, in saying slept, I meant ‘had sex with him again.’ It was as good as she remembered, with Brian doing his best to please her despite being caged and without sexual relief for many weeks. Yes, he orgasmed when she took him in her hand after freeing him from his cage, and he climaxed as soon as she guided him inside her. But both times, Brian immediately got to work with his mouth, tongue and fingers, bringing her to several will-crushing orgasms.
It was nearly 3:00 a.m. when Helena, feeling superbly satiated, slid from his bed. As she put her clothes back on, she said, “I’ll meet you at The Wickham next Friday night. I’ll bring Janey and Shelley.” Helena bit her bottom lip before she took a leap of faith. “I want you to dress girly for me and do your makeup.”
Feeling better than he had for many months, Brian nodded happily and got up to escort her outside and into the cab. He showered, put his cage back on, and went to bed. Brian woke up later that morning feeling fresh and invigorated. He went to golf, excited by his chances, and as was often the way when expectations were high, he played like he’d never held a club in his hand before teeing off.
After the round, Brian and his partners went to the bar to get something to eat and to do their usual post-round postmortem. Brian laughed ruefully when his three mates, after finishing the round Brian had just bought, put their glasses in front of him. His was by far the worst score for the day, and as such, he had to shout the first four rounds again. It was the first time since Helena had caged him and made him wear panties that he had performed so badly that he’d had to shout an entire round.
At work, Brian had continued to overachieve, regularly topping the trades and building an irrefutable case for partnership. He and Harry Mills had dinner every few weeks to discuss their finances and when they could desert Strange and Partners Stockbroking to branch out on their own. Together, they were close to the magic two million dollar mark they believed they needed to be immediately financially viable. They were only short around $200,000. But that amount kept being unobtainable because, in Brisbane’s CBD, where they’d need to base their firm, office space rental prices had climbed astronomically.
Brian considered asking Helena if she was still willing to buy a share of the firm to raise the remaining money. When Harry and Brian thought a million was enough, Helena offered to buy a fifth share of the firm for $200,000. That amount would only purchase a tenth share under the new paradigm.
Helena had earned her Doctorate of Philosophy and was currently lecturing at Nathan University. Brian did not know how much money she earned per year, but he suspected it was a lot. He wondered if she could offer more than she had earlier to get his stockbroking firm operational. He was unsure how to approach her about it, though.
Then it hit him. Helena’s specific words were that she was prepared to invest that much money in her husband. He was not her husband. Did he want to change that? Too fucking right, he did! Was it time to ask? Probably not. But maybe after this weekend, if it progressed as he thought it would.
Looking in the mirror, Helena smoothed her dress for the umpteenth time and asked, “You sure I look okay? This dress isn’t too short? It has a deep cleavage vee, and I’ve got no tits. Are you sure I shouldn’t wear something that clings to what I do have?”
Janey shook her head. She wasn’t denying that Helena looked good; she was amazed her sister was acting like a love-struck teenager. “Helena, suck it the fuck up and remember you are a FemDom for fuck’s sake. You’re acting like a virgin who’s about to go to the School Formal (Australia’s version of The Prom), knowing she’s losing her virginity that night.”
“You two are ready to fuck him too, right?”
Shelley laughed. “Jaysus, Helena! Janey’s right. Staunch up, baby. You’re not a blushing virgin bride!” She stared at Helena, who paced nervously. “We’ve both packed our 6-inch strap-ons, and we’re ready to spit roast Brian as you torture his balls.”
A car horn sounded from Janey’s driveway. The girls, Shelley and Janey, still teasing Helena, gathered their handbags and went outside to get in the cab. They arrived at The Wickham and asked for a table for four in the restaurant. The greeter said there’d be a slight delay because they were busy that night and the customers with reservations needed to be seated first. The girls nodded and took seats at the bar, from where the greeter said she’d gather them.
Helena checked her watch again, noting Brian was late, which was unlike him. She wondered if he’d chickened out, but then spotted him coming through the door. She waved, and Brian changed direction to walk over to them. Helena examined Brian as he came closer. His makeup, while not horrid, was nothing like the carefully blended masterpiece it had been when she’d met him at Sporties. Then, Brian resembled a masculine-looking woman, but a woman nevertheless. Tonight there was no doubt he was a cross-dressed man. Strangely, Helena’s pussy pulsed and became damp. She was way more attracted to Brian made-up as he was than when he was with Tim.
Helena greeted him warmly when he pulled up a barstool, explaining there was a delay, and the greeter would fetch them when they had a table. Brian ordered a glass of white wine and was shocked when Helena winked and suggested he order a beer. She smiled. “I made you order wine because you fought me feminising you. Now that you’re accepting my wants and needs, I have no need to continue to force you.”
“I guess that makes sense,” Brian said doubtfully. He remembered Shelley’s advice, sighed, and added, “I still don’t like having to dress as a woman. I really don’t understand. You have many women you’re dating already, so if that’s what you want, why make me one?”
Shelley’s head came up, and she grinned at him. Helena looked at Brian almost pityingly despite her pussy foaming at his words. “Because it turns me on. The reward for your continual defiance is having to dance with every man who asks you to tonight.”
“But I came out to be with you,” Brian protested mildly.
“And if you want to go home with three red-hot women instead of by yourself, you’ll do as I say.” Helena studied where Brian’s skirt front bulged. A knowing viewer, believing her to be a woman, would think she had a prominent pudendum. Helena knew it revealed that he remained caged. Helena’s hands strayed towards her small, tight, conical breasts as she licked her lips.
Brian sighed, but the restaurant greeter came to take them to their table before he could respond. Helena sat next to Brian, with Shelley beside him and Janey across the table. Brian felt a stocking-covered foot sliding between his thighs, and his head shot up to look at Janey. His sudden movement made Helena and Shelley look to see what was up. They saw Shelley’s foot between Brian’s thighs and under his short skirt. Helena smiled knowingly, while Shelley snorted with amusement. Brian’s eyes widened as Janey planted her heel firmly against his caged balls.
“You will accept your punishment, Brian,” Helena said quietly but firmly. “You will never be late for a date with any of us again.”
Brian gulped, forcing himself to stay still despite the increasing pain from having his balls crushed. The pain was almost too much when he felt hands on his cage. Helena released it and let Brian’s dick and balls fall free. She gripped his shaft and pumped it firmly as Janey’s foot pressed against his nuts harder. The combined pleasure/pain confused Brian’s pain and pleasure receptors. With them sending conflicting messages to his brain, Brian didn’t know whether to groan with pleasure or moan in pain. What he did realise was that he was about to cum.
“Going to cum,” he gasped quietly.
Helena grabbed her serviette and covered his cock’s head with it. Janey pressed even harder against his balls, and the sudden increase in pain shot Brian off the edge. He clenched his jaw to stifle his groans and came copiously into Helena’s serviette-covered hand. She grinned at him before releasing his dick and tucking it back away. She looked at the mess in the serviette, and her smile widened.
“Like that, did you?”
“I did,” Brian shamefully admitted. “The pain/pleasure combination was intense. Combine that with the illicit thrill of being jacked off in public, and it was an exciting experience.”
“Good. A portent of what’s coming tonight. Trust me, you will be worshipping us all night!”
The waitress, who’d seen the action at their table and had waited until it ended, arrived to take their orders. Brian wanted the steak, but before he could order, Helena took the menus off everyone and handed them to the waitress. “We’ll have four chicken Caesar salads, please.”
Brian opened his mouth to change his order, but Helena’s glare shut it again quickly. He felt Shelley kick his ankle, and he said, “I would prefer a steak.” He realised Shelley wanted him to object, as per their earlier conversation, but not to fight.
Helena sniffed disdainfully, ignoring her pulsing pussy, and said, “You’re a girl out with the girls. You’ll eat a salad and drink white wine.”
Brian picked up his beer, thinking, ‘But you told me to get a beer.’ He shrugged and took a hefty swallow, finishing the glass. He signalled for a waitress and ordered a glass of house white. Helena nodded approvingly and returned to her conversation with her sister.
Shelley asked Brian about his week. He said it had gone well and then realised he knew nothing about what she did.
“I’m a chemical engineer for Incitec on Gibson Island,” Shelley said in response to Brian’s question.
Brian asked about her work, and they chatted about what Shelley’s duties included until they’d finished their meals. They shifted to the beer garden and took over a table for six that had only two people on it. This couple engaged the girls in conversation, staying at the table with them. The man, Ian, kept eyeing Brian speculatively. While his girlfriend, Annie, seemed enthralled by Shelley. When the band started, Annie dragged Shelley to the dance floor, and the girls began dirty dancing, with Annie’s hands roaming over Shelley’s lush assets.
“We’re both bisexual,” Ian explained. “We find this place a brilliant spot for picking up like-minded individuals or groups.” He put his hand on Brian’s thigh. Uncomfortable, Brian stared at Ian’s hand. He was about to move it when he saw Helena glaring at him, and he settled for fidgeting instead. Getting no opposition, Ian asked, “Do you want to dance?”
A quick look at Helena confirmed she expected him to obey her earlier command, so Brian sighed and replied, “Sure.”
Ian took Brian’s hand, and they shifted to the dance floor beside Annie and Shelley. Helena and Janey joined them. Remembering what Helena had taught him, Brian leaned back and let the music take him. He rocked his shoulders in time with the beat, and let the music move his feet. Then, turning in time with the music, Brian leaned over and let his lean, tight ass move, shaking his admittedly delectable booty at the massively surprised Ian.
“Wow! You go, girl,” he said, while doing the typical Aussie male shuffle.
Ian’s words released Brian, and picturing the female dancers he’d seen in music videos, Brian did his best to imitate them. The dance floor slowly cleared, leaving only Janey and Helena, who could keep up, with him. They were a beat behind initially as they copied his moves until they learned the sequence. Once they did, the three swept across the floor looking as if a professional dancer had choreographed their moves.
The band saw how avidly the crowd watched the dancers, and the extended their set. However, all good things must come to an end, and the lead singer announced they were done for the night. As the music died, Brian returned from wherever his mind had taken him, and he was surprised to see only the three of them on the dance floor. The surrounding crowd’s raucous applause also shocked him. He looked around to see what they were clapping for, and was amazed when Janey and Helena took his hands and held them up.
“What was that for?” He asked as they returned to the table to get their bags.
“You, silly,” Helena said proudly. “Your dancing had them enthralled, and they cleared the dance floor to give you room. Only Janey and I could keep up with you. Your friend was so intimidated he took his girlfriend and left.”
“I don’t even know what I was doing. I just kind of got lost in the music and let it take me where it would.”
“It was like fuck-awesome,” Shelley gushed. “I tried to follow along with Helena and Janey, but your moves were too complicated for me.”
“And everyone else,” Janey interjected.
“Oh,” Brian said, embarrassed. He could dance. Had been able to since high school, where he learned the dance moves from the popular music videos as assiduously as he had his lessons. Brian was a rare student in that he wasn’t a jock, having little interest in sport, but got plenty of aerobic exercise and was leanly muscular. Wasn’t classified as a nerd because he was too outgoing and gregarious, but he scored in the mid to high nineties on the various tests all students have to take.
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