Helena Macneil: a Femdom Story
Copyright© 2025 by JohnMurray4173
Chapter 5: Present Day 3
Erotica Sex Story: Chapter 5: Present Day 3 - 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
Haley, eighteen-years-old and Helena and Brian’s eldest, walked in, followed by Kennedy, sixteen. A leash from a leather cuff around Kennedy’s balls led to Haley’s left hand, and his hands were cuffed behind his back. Although Haley was dressed like a typical eighteen-year-old girl, all Kenedy had on was a pale pink silk nightie. They’d been staying with Helena’s sister, Janey. Janey, after several disastrous heterosexual relationships, had come out as gay in her early thirties. She was an avowed FemDom who worked as a Financial Domme and earned a mid six-figure income every year.
“Kennedy’s been wanking without permission again,” Haley said haughtily, which explained the cuffs and lead. “I caught him perving on Janey when she was with a client.”
“Is that true, Kennedy?” Helena asked, her anger clear as she undid Kennedy’s wrist cuffs and placed them on the bench.
“Yes, Mistress Helena,” Kennedy answered. Helena did not allow her kids to call her mum or mother. Haley simply used her name. Kennedy called her as he had above.
Helena stared at her son coldly before saying, “Fetch your cock cage, strip and return.”
Kennedy suppressed a sigh because he knew it would anger his mother and walked to his bedroom quickly. He returned naked and with his cock cage a short time later. Helena jacked her son’s cock until it was hard and throbbing in her hand and then used the heel of her hand to bang his balls, causing Kennedy’s cock to deflate immediately. Helena jacked him to full erectness again before repeating the process. She did this twice more before locking Kennedy’s cock and balls into a clear plastic chastity cage. She snapped the padlock in place before saying, “Naughty little boys wear a French maid’s uniform. Put yours on and return to me.”
Kennedy returned about thirty minutes later. He’d showered and shaved all the hair on his body and then done a full makeup of his face. Kennedy had trimmed his quite thick eyebrows and plucked them to create a higher arch, and he’d used an eyebrow pencil to draw them even higher. He’d painted his lips, which were drawn to the extreme to create the illusion of full pouting lips, with whore-red lipstick. False eyelashes adorned his eyes and fake nails his fingers. Kennedy’s blush was also exaggerated for effect as opposed to trying to look good.
Helena cast her eyes over her son, admiring the chest plate he’d put on to create the illusion of having breasts. She especially admired how his ‘breasts’ seemed to overflow the scant push-up bra he wore. Over the chest plate, Kennedy had on a fetish French maid outfit complete with a layered, frilly mini skirt. Suspenders, fishnet stockings and high-heels completed his outfit. He stood before his mother looking morose but respectful because he knew his mother would punish any sign of defiance immediately.
“Start your house-cleaning duties. Work from high to low, cleaning all flat surfaces before you vacuum and then mop. Snap to it! Return to me once you’ve finished so I can inspect your jobs.”
“Yes, Ma’am,” Kennedy replied before hiding a sigh and fetching cleaning materials from the hall closet.
Helena returned to the kitchen, where Haley waited. She made coffee using their espresso machine and sat at the breakfast table beside her daughter. “How was your time with Janey?”
“Way cool!” Haley said enthusiastically. “She let me help whip a client who is right into pain. It took me a little bit to build up my courage, but I welted him good by the end.”
“You’re still planning to complete your law degree and become a lawyer? Or are you taking after Janey and becoming a FinDomme?”
“I’ll maybe do a bit of FinDomming on the side, but I want to be a lawyer. You know how I feel about family court and how fathers get screwed out of seeing their kids.”
“It does appear biased against them,” Helena conceded. “Personally, I blame the women for not controlling their men adequately. Brian would never cheat on me because he knows the cost if he does. Besides, I give him plenty of opportunities to play, so why would he cheat?”
“Only with dicks, though, right? No pussy for him?”
“I warned him that if he ever laid hands on me again, he’d never stick his cock in another cunt again. He did, and he hasn’t.”
“You still can’t find a surgeon prepared to remove his cock and balls?”
Helena chuckled. “I forgot I’d told you about that. There are plenty who will do the gender reassignment surgery, but he has no more use for a cunt than he does for a dick, so what would be the point? Oh, Brandon did let Brian stick his dick in Jenny, his submissive. But he wasn’t allowed to move, and Brandon fucked his ass until he came in him.”
“So close and yet so far,” Haley tittered.
“Nah. Brandon didn’t understand that Brian isn’t allowed pussy, and he let him cum in Jenny’s cunt.”
“Hmm,” Haley said, looking thoughtful. “I suppose Brian’s been very obedient for quite some time, and it’s been years since he’s tried to rebel, so I guess he deserved a reward.”
“I agree, but it would have been better if you or I had given it to him.”
“Yeah, that’s true,” Haley agreed. “But he was in an impossible position. One dominant telling him to fuck and cum in a pussy, and his Mistress’s standard rule that he isn’t allowed to. If you didn’t countermand Brandon’s order, Brian had to obey it.”
“So now you’re the Mistress and I’m the student?” Helena said teasingly.
“The student has become the Master!” Haley teased back. She bit her bottom lip before saying, “I’m quite horny because none of Janey’s clients did anything for me even though it was exciting to watch her work with them.”
“Brian or Kennedy?”
“Brian, if you don’t mind.”
“I’ve worked him pretty hard over the last couple of days. But that’s a him problem and not yours. Therefore, take him and enjoy.”
“Where are you, worm?” Helena asked.
“Here, Mistress,” Brian replied, stepping in from the hallway where he waited.
“Mistress Haley requires your services. Follow her to her room and obey her as you would me.”
“Yes, Mistress. May I have the key to my cage?”
“Mistress Haley will decide if you’re to be released. She has a key.”
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