They did have an entertaining relationship, though. Cathy enjoyed wearing leather and Mike enjoyed their role playing, and both had agreed to a completely monogamous relationship.
Derrick was a tall, well built athletic type who worked in a high class health spa. His live in girlfriend, Lisa, didn't work and stayed at home as a housewife.
While Cathy and Derrick spent their days at work, Mike and Lisa spent their days keeping their respective houses in order, occasionally visiting each other for coffee and chit chat. Then, for Mike, things started to go terribly wrong.
Lisa had come over that afternoon and Mike couldn't help but notice the strappy high heels and seamed stockings under her long raincoat. Only it wasn't raining... She slowly sidled up to Mike and in a timid, shy voice said " I was playing this morning and my batteries died before I was done". As she spoke, she removed her raincoat, revealing to Mikes amazement that she was only wearing a very sexy red satin corselet with black ruffled lace trim, and garters, matching satin panties, and a sexy wanton smile.
"I want an orgasm, Mike, and I want you to give it to me. I need you to give it to me. Right here, right now!"
Mike started to refuse because he and Cathy had played the night before. She had him shave all of his body hair before a night of sex in satin sheets (which he enjoyed immensely).
Before he said three words, Lisa was on her knees unzipping his pants. Her eyes widened and she smiled broadly at his clean shaven member. "Ooh, honey, I like this!" she purred...Fifteen minutes later they were on the floor fucking like two people who had never had sex when Cathy opened the door. "What the hell are you doing!" she screamed at Mike.
She heard a car door slam, looked behind her and called "Derrick, come in here and get your slut of a lover out of my house!" Derrick came in the door and looked angrily at Lisa, who started to whimper, saying "I'm sorry" over and over.
As the door closed behind the departing Derrick and Lisa, Cathy glared at Mike. “You insolent bastard! After giving you all this, a home, money, and my love, you do this to me!"
Mike was pale in shock. He started to stutter an apology but was cut off with an abrupt "shut up!" Cathy was fuming with anger. "Get some clothes on and stay in the guest room til I'm ready to deal with you and your treachery.”
He did as she said and stayed in the guest room for almost three hours before she called him through the door. "I want you naked and on your knees in my bedroom in two minutes!"
He naturally did as she said, as he'd always done. Cathy walked into her bedroom five minutes later clad in a tight leather dress with high spiked heels, looking like the most luscious woman he'd ever seen...
"You will be punished, you realize that, don't you?"
"Yes" he replied.
"Yes, Mistress!" she said.
"Yes Mistress.” he said, meekly, starting to tremble at what might happen.
“You're going to pay for your infidelity by doing exactly as you're told, no questions, no hesitations, any refusal and I'll throw your cheating ass out for good. Is that understood?"
"Yes, Mistress" barely came out of his frightened lips.
"Good. Now, sit at my vanity table and be quiet."
He sat and she started to apply makeup, then nail polish on his fingers and toes, then put his hair in a high ponytail. He was seeing a pretty girl in the mirror and could not help but start to become aroused.
"Follow me" Cathy told him.
He followed her to the guest room and learned that she had gone shopping for his punishment. On the bed she had laid out a delicate and pretty pink satin maid's dress and apron, with all the feminine underthings that he knew he would be forced to wear for her.
She laced him first into a tight pink satin corset with garters, then white seamed stockings, then strapped on pink stiletto high heels. He was already blushing a deep red.
"You're enjoying this, aren't you?" she asked.
He tried to say no, but yes came out of his pretty lipsticked mouth instead. She then had him step into a pair of pink, lacy ruffled panties that incredibly fit him perfectly. The feel of satin and lace on his clean shaven genitals caused an instant erection. She allowed him to masturbate, then placed his genitals in a chastity bag, tied tightly, that would prevent him from another erection. She pulled his panties back up, then finished dressing him in his new and sexy, short maid's dress and apron.
When she stood him in front of the mirror, he gasped at how feminine and girlish he looked.
"This is to be your punishment", she started. "From now on, you're to be my sissy maid, my concubine, and it will be your new responsibility to cater to your Mistress' every whim and command. You will be trained to walk, talk, sit and speak in a very feminine manner fitting a proper and sissified young lady. If you fail to meet my expectations of a sex slave and sissy maid, you'll be thrown out forever. Do you understand, Melissa?"
"Yes, Mistress". He was shocked to hear himself already sounding like a shy, timid little girl.
"Wonderful, darling, and from now on you'll address me as Mistress Catherine. Is that clear?"
"Yes Mistress Catherine" replied the little sissy that he was already becoming.
"Good. Come with Mistress, little girl.”
She took her sissy into the living room, then using long pink ribbons, tied Melissa to a tall, arm-less straight back chair. " Your going to get your first lesson in sexual servitude, and you're going to learn to perform as a feminine little sissy maid should", she told him.
Just as Melissa's Mistress finished speaking, the door opened and in walked Derrick. His mouth at first dropped at the sight of Michael wearing makeup and a sexy maids dress, then smiled broadly and said "Who's this sexy little girl?"
Catherine informed him that Michael was now Melissa and was becoming her feminine, sexy handmaiden. Then she looked into Melissa's eyes and added the word "forever.”
Melissa wiggled in her ribbon-ed bondage and blushed a deep red. Derrick then told Catherine that he had dressed Lisa as a whore and taken her to a dominant lesbian couple that he knew..she was to become a lesbian sex slave...
"And Melissa is going to become my gay sissy maid" Catherine said with a mischievous smile. "Would you like her to give you a blow job, Derrick?”
“I think I'd enjoy that quite a bit" he said. He started dropping his pants while Catherine held Melissa's prettified face up and said "You will suck his cock, young lady, and you'll do it just like a good sissy maid would. Now look at his big, hard cock, darling".
His pendulous rod was thick and must have been a full seven inches, his testicles swollen and looked like a very ripe pomegranate, ready to be eaten. Catherine spent the next twenty minutes teaching her little girl to kiss, lick, then beg for the pleasure of sucking Derricks massive cock, which Melissa did, moaning like a girl, undeniably enjoying every moment, even when Derrick shot his cum into Melissa's sissified mouth in an orgasmic explosion that almost drowned her. She managed, to the delight of her Mistress, to swallow every drop.
During the next two weeks, Melissa was kept in pretty dresses, petticoats and panties, and had adopted to walking in high heels and wearing corsets quite nicely. Her Mistress had trained her to walk, talk, sit, curtsy and had almost completely feminized her into a proper sissy maid. Mistress had Derrick over often, and had trained Melissa to have sex with him in whatever manner he desired. . . whatever manner. Lisa had been turned into a lesbian sex slave and now lived with her Mistresses.
"Time to make this transformation permanent, little girl." Mistress Catherine informed her sissy. She then took Melissa, wearing a pretty black satin maids dress replete with petticoat and panties, to a beauty salon, where her long brown hair was dyed blonde and cut, giving her very feminine bangs which made all the women in the shop smile, and made Melissa smile and blush like the little girl she had become. Mistress also started her on hormones and electrolysis and, three months later, minor cosmetic surgery to enhance her feminine features.
Just over one year since being caught with Lisa, Melissa stood in front of her mirror, primping and preening in a new, sexy maids dress that Mistress Catherine had just bought. She had learned to accept her new role and had been trained extremely well in providing Mistress with a completely feminized, sissified, and totally domesticated maid service.
Melissa checked herself once more, then allowing herself a smile, went to greet her husband Derrick home from work, as Mistress had trained her to. She adored her new life as a girl, and all the male thoughts were now gone from her mind, only existing as a faint memory.....
The End
(of Michael, the beginning for Melissa)
