by doormat
Alan was a very successful business man, who at thirty was well on his way to achieving his life dream of owning his own company. He rose up the corporate ladder swiftly and was well respected among his peers.
At home, however it was an entirely different matter. Nancy, his wife of nine years, controlled the purse strings as well as their sex life.
From the very moment after they exchanged vows, the lovely lady with reddish brown hair that hung to her shoulders, took charge. On their wedding night he had to endure an over the lap red butt spanking before he was allowed to consummate the marriage, which he accepted without protest.
Alan truly loved Nancy and would do anything reasonable to please her, which meant sucking her pussy every morning before he left for work and every night before bed. He was required to strip naked immediately upon entering their spacious home each evening. He’d be punished, which meant anything from a severe whipping to cock and ball torture for the slightest screw up. He was required to address her as “Ma’am” at all times. He was also required to be on his knees anytime she entered a room he was in. Despite all this, he relished the idea of giving up control to his very attractive wife.
It created a much needed balance in his life.
But now, nine years into the marriage, the healthy attractive red-blooded male was about to endure the most humiliating night of his life so far. They were going to visit some of Nancy’s female friends with Alan wearing a dress! When she first suggested it, Alan thought she was kidding. Yet, the thought of parading in front of these women wearing all feminine apparel made his cock stir. He’d worn Nancy’s panties before at her behest, but that was behind closed doors. This however, would be something else again.
Exiting their vehicle and walking toward the house, the gentle tugging of the soft nylon on his freshly shaved skin combined with the pinching of his lacy bra and the three inch pumps only increased his humiliation and excitement. His heart pounded as he took the last feminine step towards the door and saw his wife push the door bell.
“Come in Nancy,” lovely brunette said as she extended a hand toward her guest.
“Hello Donna,” Nancy greeted. “It’s nice to see you again.”
“Oh Nan, Alan…I mean Ann looks just adorable,” Donna said in a gleeful tone. “The ladies are going to love you.”
“Well, he’s taken quite a few years to train,” Nancy replied with a smile.
“Well, you’ve done a wonderful job Nan. He looks so feminine.”
“Yes she does,” Nancy said with a leer. They both laughed out loud.
“Well come on in, Lisa and Jennifer are already here.”
As he looked at the two attractive young women sitting side by side on the couch, one part of Alan could have died, while the other caused his cock to push further into the silky white panties that entrapped it between his legs. Alan involuntarily blushed through his make-up as they greeted him with giggles and laughter.
“Curtsey Ann,” Nancy instructed and the feminine man blushed crimson and dutifully lifted the hem of his powder blue, knee length frock and gracefully complied. Louder giggles and laughter followed.
After properly introducing himself to all the ladies, he waited patiently for his dominant wife to instruct him further.
“Ann,” she said, “be a dear and show the ladies your sexy little wiggle.” The five-foot nine inch slender slave did as told and began parading across the living room with soft mincing steps. He felt his humiliation and his cock grow as he went, suggestively swaying his hips back and forth.
Nancy then began explaining to the group. “My husband can be a very virile man in bed.” She demonstrated her point by pressing the front of his dress tight against him so the outline of his rigid manhood revealed how much his cock was pushing his panties. “Yes I see,” Lisa replied with a leer. “Oh I could ride that piece of meat for a long time,” the red headed Jennifer added.
“But,” Nancy continued, “from the moment I met him, my sole aim was to turn him into my panty slave.”
“He let you?” Lisa asked.
“Actually he took to it rather quickly. Once I got him into a pair of panties, the rest was easy. He loved to dress up and play house, and it really made him excited. Of course, ‘Ann’ pretends to hate it, but I’ll show you it’s all an act.”
After he had wiggled his way around the room sufficiently, Nancy addressed him sternly. “Ann, be a good girl and lift your dress up.”
“Do I have to?” the male voice protested.
“Don’t disobey me in front of my friends Ann!”
“B–But…”
“No buts! Do as I told you!”
Feeling mortified, he slowly began to obey her command, exposing the tops of his white nylons and white lacy garters they were connected to, as the ladies smiled and giggled.
They’re going to see my hard-on, he thought in horror as he gingerly continued to raise his dress, allowing the women to see the white nylon panties with the lacy front and the little bows that snugly covered his stiff maleness.
“Such pretty panties!” Lisa exclaimed with a laugh. “You look so feminine,” she teased.
Alan’s cock twitched at the mocking words as his mistress reached for the waistband of the delicate undies, causing him to take a step backward in retreat. In an instant he felt two surprisingly powerful hands pin his arm behind his back, causing him to release his hold on his dress. The next thing he knew, he was being forcibly bent over the cherry coffee table by Donna as another pair of hands abruptly yanked his panties down to the middle of his thighs. Now his fully erect six inches, adorned with the pink bow his mistress had tied there, obscenely bobbed between his frilly garters. Uncontrolled feminine laughter filled the room.
There was more laughter as Alan heard the click of returning heels from the kitchen and he yelped from the blow of what he recognized all to well as a wooden spoon. Again and again the spoon landed heavily on his upturned bottom, which reddened his ass cheeks and shrunk his manhood.
Then he heard his mistress. “You’ve been a bad little girl! And bad little girls get their bottoms spanked!” After a few more meaningful swats she asked, “Are you sorry?”
“Yes Ma’am,” he replied meekly as his ass cheeks burned.
As she witnessed the humiliating punishment, Jennifer, the red head, began to feel the warm fluid in her pussy. It excited her to see this feminized man with a crimson butt and quivering like a leaf. Yet, what excited her the most was the submission in his eyes and the way his limp cock, with the cute ribbon was beginning to grow again. She recognized that he actually liked this treatment and she inched closer to him, so that her long legs were only inches from his face.
Then Nancy lectured him anew. “If you think Ann, that you can behave like a proper young lady, I’m sure one of my girlfriends would gladly help you with your panties.
“I think she’s learned her lesson for now,” Jennifer eagerly responded as she rose to a position behind Alan.
As she stood behind his well spanked bottom, Jen noticed how truly feminine he looked in the heels and white nylons that shaped his slender, hairless legs and the matching garter belt that defined his girlish and pink butt. She couldn’t resist running her long fingernails over the cute roundness and then she firmly grabbed him by the hips, like a man would.
“A virgin, uh?” She said with a wry grin. Everyone but Alan laughed uproariously.
“Careful, you might get her excited,” Lisa cracked.
“Are you getting excited little girl?” Jennifer teased as she reached a hand between his thighs and tickled his smooth little balls. Alan tried unsuccessfully to stifle a moan.
“Bad girl!” Jennifer said loudly and then roughly pulled his erection back between his shaking legs. Smack! Her hand landed firmly on his fiery butt. Again the man moaned. The woman held his cock in place as she carefully pulled his panties up and when they were snug, she gave the waistband an extra tug to make sure his member would remain in place.
“I usually keep her in spandex or a girdle,” Nancy remarked dryly.
“You may stand now Ann,” Jennifer said as she received an approving nod from Nancy.
The ladies then played with Alan/Ann the rest of the night. They stripped him and tied him face up on the coffee table, teased his cock until it got hard, then they’d whip him until it shrunk. Then they’d tease him hard again, only to pinch his balls until he lost his hard-on again. They kept this up for a while, getting him hard then doing something dastardly to him.
They pinched his nipples, bit them, pulled on his cock, slapped it and took turns sitting on his face. They spread his legs wide and back and then jammed a cucumber up his anus. They got tweezers and began pulling out his pubic hair. Someone got a set of tongs from the kitchen and she squeezed each one of his balls until he yelled and squirmed. The ladies had a ball torturing the she-male.
Then Lisa spoke up. “I know what I’d like to do to him ladies.”
“What’s that?” Donna inquired with a raised eyebrow.
The blonde haired Lisa gathered the four of them in a huddle out of ear shot from their feminized man. She whispered and they all broke out in laughter. Then Donna ran up to her bedroom. She returned holding a strap-on. It was ten inches in length and an inch and a quarter in diameter.
Alan gasped when he saw it, but when Nancy ordered him to his knees on the rug he did so immediately. She then commanded him to bend over so that his forehead touched the floor. They all laughed at the sight of his red butt sticking up in the air. Then Jennifer laid on her back so that Alan’s face was right at her open pussy. Since it was Lisa’s idea, she strapped on the bulbous dildo and pointed it at feminine man’s butt. Donna assisted by pulling his hind cheeks apart, exposing his anus.
“Suck that pussy, Panty slave!” Nancy ordered as Lisa touched his open ass with the hard cock. Nancy did take the time to grease up the dildo with some Vaseline just before Lisa pushed inward. Alan’s tongue found Jennifer’s clit about the same time the hard plastic stretched his sphincter muscles. The red head moaned in delight and Alan groaned in hurt. Over and over the bent over man licked her little love button as Lisa steadily pushed in.
“Keep fucking him until she comes,” Nancy beseeched her friend. Jennifer, who was in the throes of animal lust shrieked her song of joy as she went over the top, while Lisa kept fucking the man’s ass.
Then she pulled out. Next it was Donna who took Jennifer’s place on the carpet, while Nancy strapped on the dildo. The brown headed Donna was soon in her own little heaven as the butt fucked man tongued her to a glorious orgasm. His mistress fucked him over and over knowing he really liked this. Alan did not have a virgin ass and she should know.
Then it was Lisa who got her pussy eaten while Donna butt fucked him.
Lastly Nancy herself had the pleasure of feeling her slave’s tongue touch her drenched pussy and Jennifer had the honor of giving Alan his fourth butt fucking of the evening.
Finally Nancy allowed her panty slave to get dressed. They all agreed that they should hold parties like this at least twice a month.
Lisa told Nancy that she thought he was wonderfully trained and it was fun seeing him punished, but she’d need a stud of her own whom she could really punish. Donna chimed in to tell Lisa she didn’t think she had it in her.
“Oh I’d love to reduce some macho asshole into a groveling wimp. I’d keep him in a collar and a harness, like a slaveboy should be kept.”
“Well,” smiled Nancy, “until you’ve found your stud, you may play with my little panty slave.”
“Okay, well my apartment room needs to be cleaned,” Lisa said with a wry smile.
“Oh good, I’ll bring him over tomorrow for maid service and of course you may punish him if he doesn’t do a good job.”
“See you then.”