Chapter 7: Present Day 4

A body sliding into the bed from the bottom and a warm, wet tongue sliding along her slit onto her clit woke Helena up about an hour after she’d laid down for her nap. She was momentarily confused because of the vivid dream about meeting Brian and how they’d come to be. However, the tongue circling her clit before soft lips surrounded it brought Helena back to the present, and she sighed with delight when the tongue changed from circles to battering Helena’s button.

“Hmmm,” Helena sighed as she lifted her knees and lifted the quilt. Haley’s mischievous green eyes looked up at her, and Helena moaned as an orgasm approached.

Feeling her mother’s climax approaching, Haley sucked harder and battered Helena’s clit more firmly. She grinned when Helena orgasmed before kissing her way up her mother’s slender body. She locked lips with Helena. However, the kiss wasn’t passionate, but full of love and respect instead.

Helena stroked her daughter’s long, dark-brown locks before asking, “What do I owe that to?”

“For letting me work out my sexual frustrations with Brian. Most mothers would freak out knowing their daughter and husband were having sex.”

“Did he do a good job?”

“Yes! I made him put on my strap-on and fuck me with it. It was so much fun! He kept groaning because his dick was still in its cage and it was trying to go hard.”

Helena chuckled before saying, “I bet that frustrated him!”

“It did! Especially when I ruined his orgasm.”

“How did you do that?”

“Just like you showed me. I took off his cage and let him masturbate with a pair of my silk panties. Then, when he was on the edge and about to cum, I banged his balls with the heel of my palm.”

“That’ll do it,” Helena chuckled, sharing an amused grin with her daughter. “What time is it?”

“Nearly five. That’s why I woke you up.”

“Thanks for that. Would you like me to return the favour and eat your pussy?”

“Nah, I’m all good. I just wanted to do that for you.”

“Did you send Brian to dress?”

“Yeah. I told him to wear a bra, panties, breast falsies, and a pinafore. He and Kennedy will look alike except Kennedy will have his chest plate on.”

“Kennedy’s complaining he doesn’t have as many chances to learn his role as he’d like.”

Haley considered before pointing out, “That has to be on you and Janey. I’m not ready to search for a man to sissify yet, although I love helping you and Janey with yours. And letting him watch me play with Brian would just be weird.”

“Weirder than sneaking into bed and eating your mother’s pussy?”

Haley laughed before saying, “From about the time I turned thirteen, you’ve treated me much more like a friend than your daughter. I guess there were a few times you came down on me, usually because of something inappropriate I did to Kennedy. I mean, I see you as my mother for sure, but also more like an equal than a mother bossing her daughter.”

“This world has to stop infantilising teenagers!” Helena groused. “Did you see the latest bullshit they’re talking about? Under sixteens can’t walk a dog on their own? What a load of crap! You know I’m a feminist, and proud of it, but the left have lost their collective minds! They’re infantilising teenagers at the same time they’re sexualising preteens! What are they trying to do? Create a paedophile’s paradise?”

“Geez, Helena! Why don’t you tell me what you really think? Because I’m not sure I understand.”

“It’s alright for you because I never treated you like an infant. Pretty much as you showed you were being more adult, I released the reins and allowed you to grow. Sure, I had to tighten them back up a couple of times, but neither you nor Kennedy ever caused or got into much trouble.”

Haley nodded. “Treating your kids with respect and allowing them to take responsibility for themselves seems to be the key to avoiding the typical teenage rebellion kids show. With every one of my friends at high school or uni, the more their parents tried to control them, the more rebellious they became. Those with parents who allowed them to grow and explore caused far fewer problems.”

“It’s a balancing act because teenage boys especially tend to make dumb decisions, but usually you have to allow them to make them whist trying to ensure they don’t make life-threatening ones. Personally, I blame the mothers for not teaching their men to be subservient to them.”

“Like sissifying Brian and teaching Kennedy to serve?”

“Precisely!” Helena affirmed. “Anyway. Let me take a quick shower, and I’ll see you in the dining room.”

“Wine?”

“Yes, please.”

After a quick shower, Helena donned her diaphanous white robe again and made her stately way to the dining room. She paused at the kitchen door and smiled as her two men worked together to make dinner. She thought about the previous forty-eight hours and realised Brian had performed his tasks perfectly. He deserved to be rewarded, so Helena wondered how to do so. Her nether region pulsed, reminding her that her night with Manon still had her motors running.

Brian had been a selfish lover when she first met him, but she’d swiftly broken him of that, and now he was attentive and skilled. She’d take advantage of that at bedtime and reward him at the same time. ‘Other than when Brandon let him stick his dick in Jenny, I wonder when the last time Brian had his cock in a pussy was?’ She wondered. ‘It would have to have been mine, so maybe nine years?’

Helena thought that number must be about right because she’d sissified him before she married him. However, it took a few more years before Brian completely accepted his role as a sissified cuckold. As he travelled along the path towards sissification, Helena used access to her sweet, tight pussy to control him and to drive him towards being a feminised man. She did not want a trans woman as her husband because she preferred her partner to look like a cross-dressed man instead of a woman. It was more embarrassing and demeaning for him, Helena thought. Embarrassing Brian turned Helena on more than anything else other than forcing him to dress as a sissy and fluff her bulls.

Brian and Kennedy serving their dinner broke into Helena’s reveries. She looked at her husband of nearly twenty-three years and smiled, remembering how he was and how far he’d come. To her surprise, remembering and dreaming about their early lives had her sweet little nubbin pulsing, and the thought of riding his cock later caused her sex to flower open and leak womanly fluids. Helena vaguely regretted that being constantly encased in a chastity device had wilted Brian’s once 7-inch cock to less than five inches. However, doing that was partly how she explained the need for a bull with a bigger cock—Brian’s wasn’t big enough to satisfy her anymore. Helena admitted to her close friends and daughter that despite having an incredibly tight pussy, honed by many hours of Kegel exercises, she’d always been a size queen.

Dinner followed its typical progression with Brian and Kennedy sitting at the separate sissy and remaining quiet while Helena and Haley sat at the main table, talking animatedly. The cross-dressed men took turns fetching the things Helena or Haley wanted, including refreshing their drinks and then bringing a light dessert of a passionfruit cheesecake made with cream cheese and a crushed biscuit base. The dish was a special dessert that Brian had learned to make for Helena.