Mistress Deborah's Cuckold Sissy Maid
Chastity Cuckold Tales
Mistress Deborah lives the life of a pampered Goddess, thanks to her cuckold-sissy-maid-husband Tim/Tami. Deborah enjoys the amorous attentions of her young lover Sean, and both Mistress and Master take their turns in tormenting the hapless Tami. Things don’t get any better for Tami when the simpering sissy is ‘milked’ before Deborah’s guest, Miss Sandra, and when wicked sissy maid Amanda is added to the household.
Tim minced in his incredibly short steps, teetering on his stilettos to her bed, carefully placing her expensive black high heels in her suitcase. "Who is he?" he asked.
A crop across his thigh delivered the answer. "None of your business; you know better than to ask!"
He started to curtsy and offer an apology, but the crop landed again. "I-I'm sorry Mistress."
"Finish packing," she ordered.
He dropped to his knees to gently kiss the tips of her stiletto-heeled ankle boots. "I'm sorry, Mistress, I—" The boots disappeared from his view, moving across the floor as Mistress Deborah, his wife, reposed in her dressing chair.
"Finish...packing," she ordered.
He rose and made his way to the bathroom to gather her toiletries.
"If you must know, and I am not obligated to tell you anything, he's a lawyer; his name is Sean, Master Sean to you. He’s young, divorced, who likes no-strings sex with different older women. Alexandra fixed us up."
He silently bobbed a curtsy to acknowledge his understanding; there was no need for him to speak. They were going to Columbus for another date weekend; he would make the hotel and dinner reservations, and serve as the designated driver, ferrying the loving couple from hotel to restaurant, to whatever destination they wanted and then back to the hotel where they would make love. He was a chauffeur, butler, maid...and chastity cuckold.
"This is what you wanted...right?" Her voice held a teasing, mocking tone. "Tell me you don't want to go; that you want us to stay here this weekend and you can lick me to orgasm. Or...that you want to take me on my date weekend so I can be fucked with a real cock. Well, which is it?"
Tim stared down at the floor; his cock twitching in its chastity device. It always excited him when she talked like that.
"Crawl over here...tell me what you want me to do."
He carefully placed her cosmetic bag in the suitcase and closed it; the packing was finished. As he had been so thoroughly trained, he dropped gracefully to his knees and crawled to his wife. "Please, Mistress, allow me to serve you on your date weekend."
The pointed toe of her boot probed at him with light, teasing kicks.
"Serve?" She kicked harder, "Serve who?"
"You, Mistress, please, you and your lover."
"Better," she leaned forward, stroking his hair, "remember, you were the one who asked for this." She leaned back in her chair, lifting her foot, and smiled as he began to lick the sole of her black boot. "I have to admit, it doesn't suck," she laughed, "well 'you' do. Alexandra said my stud doesn't mind getting his cock sucked by a submissive, cuckold, hubby. Ready for some good cock sucking this weekend, slut?"
Tim heard the ringing bell and immediately straightened his apron and cap, picked up the silver tray and sissy-minced into the living room, stopping to curtsy before the two women as he placed the tray on the end table and poured more wine.
"Do you always keep him so feminized?” Miss Sandra asked. “I mean the dress, those long earrings and high heels?"
Mistress Deborah nodded and smiled, "Almost always, I find that the more feminized she is, and if she's always kept in chastity, that she becomes quite obedient, docile and compliant." Deborah reaches out to stroke her sissy maid-husband’s nipple as he bent forward to pour the wine, "She likes being my sweet little girl and wearing heels, don't you?"
He bobbed a delicate curtsy and trembled at Mistress's caress. "Oh yes, very much, thank You, Mistress."
Miss Sandra arched an eyebrow, "David would love it if I spent all day in fuck-me shoes."
"My boyfriends do like it," Deborah replied, "my little slut even has her little book that has which shoes my lovers like. She has her special outfits and shoes to wear for each of my guests."
"That's convenient," Miss Sandra eyed the sissy maid from her six-inch black patent heels to the black bob wig with the cute white lace maid’s headpiece.
"It is," Mistress agreed. "Then again, my slut needs to multi-task; clean and do housework and turn on my boyfriends, keep those cocks nice and hard for me."
As Tim bent forward to pick up the tray he felt a hand on his leg, slowly caressing the seam of his fishnet stocking.
"Cute stockings, Tami," Miss Sandra said.
As trained, Tim/Tami wiggled his bottom in acknowledgment and appreciation, "Thank You, Miss Sandra."
"I can't believe what you've done, how feminine he is," Sandra said, "and how well trained. He's a real maid, or at least..."
"No," Mistress said, "you're quite correct; she has developed into quite the useful and efficient servant; haven't you, darling?"
Tim straightened up and curtsied, still holding the tray he’d used to serve drinks. "I hope so, Mistress; I'm trying very hard."
Mistress snapped her fingers and motioned him to her side. He made his small, mincing steps in his six-inch stilettos to get in the required position.
"Let me see them," Mistress ordered.
He balanced the tray in one hand as he lifted his maid dress and petticoat to expose his chastity device. Mistress reached out to tug on the chastity device, testing its security and pulling him forward, but he fought to remain in position. Satisfied the device was secure she began to fondle his balls, squeezing them, smiling at their fullness.
"He's always locked up like that?" Sandra asked.
"Twenty-four-seven" Deborah replied, "and please refer to "her", male pronouns simply seem to confuse the poor dear anymore."
"Yea, well..." Sandra nodded, "after meeting Sean last evening I can see why. That's one serious piece of young man-candy."
"Sean" was Mistress Deborah’s newest young lover, barely thirty. Last evening Mistress and Sean and Sandra and her husband, David, had made it a foursome at a local restaurant while sissy-maid Tim/Tami remained at home, doing Sean's laundry, ironing his shirts and shining the box of shoes he'd left.
"Yes," Mistress smiled, "everyone has their place and duties in my house, both Sean...and little Tami." She squeezed his balls and he flinched. "I think someone needs a milking," Mistress teased.
"No, Mistress, I—" The mistake had been made; he’d contradicted Mistress, challenged her, and in front of a guest. "As you say, Mistress." He knew it was too late; he'd be disciplined severely later.
“Milking?" Sandra asked.
"I do believe a demonstration is in order." Mistress released his balls. "Go get the items," Mistress commanded.
He curtsied and backed away; performing a second curtsy before he left the room.
"Men need to relieve themselves of their semen, either through sex or masturbation," Deborah said. "It's a matter of health, as much as pleasure." She smiled, "Except for my Tami; who is allowed no pleasure."
"So..." Sandra shrugged, "she's 'milked'; how does that work?"
“You'll see; it's absolutely wicked," Deborah chuckled, "especially humiliating in front of an audience."