The Conductor Ch. 02

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Milf and sissy maid.
1.4k words
4.75
4.4k
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Part 2 of the 4 part series

Updated 06/15/2023
Created 02/15/2023
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Willem and Martha lay together while they recovered from their exertions. After a quarter of an hour, Martha got off the bed and stood surveying the room. "What a mess! And look at these wet panties!" she exclaimed. Willem didn't know how to answer, so he just looked at Martha in her slip and basque. A damp patch on the slip was down to Willem, and there were two pairs of cum soaked panties on the floor, but what did she expect him to do about it?

"This is a job for the maid," she declared.

"What maid?" asked Willem.

She crossed to the draw that Willem remembered containing some frilly petticoats. She selected some things from the drawer and announced, "My new maid. Willem - ina!" Before he could react, she produced a black satin maid's dress, some frilly white panties and a fluffy white petticoat. She handed these to Willem and ordered, "Go to the bathroom, wash your sticky cock, and put your uniform on, Wilhemina. In the top drawer, you'll find black stockings and a suspender belt."

Willem usually didn't take orders from anyone, but this might be fun. So he went into the bathroom, removed his slip and stockings, and then the basque. He placed them to one side and then used the bidet to wash Martha's drying juice from his cock. Returning to the bedroom, he found Martha reclined on the bed. She had removed her slip and retained just her black stockings. She lay on her back with her legs slightly apart. Nothing was hidden was Willem's view, not her glorious chest nor her hairy pussy. His cock was rising again.

Martha went into her offended mode, "Wilhelmina!" she scolded, " How can you perform your maid duties with that thing sticking out?

Put on your suspenders and stockings, and then we'll do something about that!"

Willem selected a plain white satin suspender belt from the drawer and put it on with a pair of black seamed stockings. He was really rampant now. Martha climbed off the bed, gravity giving her large breasts a sensual and slightly pendulous swing. Her stockings slipped only slightly down her thighs. Rummaging in her drawers, she said, "Let's get that clitty under control," as she pulled a pair of black Directoire knickers out of the drawer. "These are on the small side," explained Martha, "they'll hold your clitty in close."

Feeling that he needed to keep some control, Willem said, "No, it's a cock, not a clit!"

"Are you sure?" she asked, "I didn't think girls had cocks."

"I'm not a girl; I am a man who loves female underwear."

"Well, I want a maid, and maids have clitties. But if you don't want to wear that maid's outfit..."

"Okay, you win. It's my clitty, but can we cut the Wilhelmina stuff?"

"Of course we can, Mina. Now, do you want your clity strapped up or down? It is a very nice big clity, by the way."

Accepting Mina as a minor victory, Willem allowed Martha to pull the big tight knickers up his legs. Tucking his clit upwards against his lower stomach. The knickers were rather old, and the satin had snags and runs, but they felt terrific on Mina's thighs and clit. They stretched from her waist to several inches below her stocking tops. "That'll keep you from showing off your tentpole, Mina. Now put on your silky ruffled panties."

Mina pulled the lovely panties on; they reminded her of Betty Gable's maid's outfit in the movie "My Blue Heaven". She wished he could feel them on her clity, but the Directoires prevented that, although they were fabulous to touch. Then the petticoats, a smooth satin one and a net one. Martha handed Mina a skimpy white bra that just fitted her masculine chest but had small cups that held her little man-tities very well. Obviously not Martha's, he thought.

"Sit down!" ordered Martha, pushing her dressing table stool towards Mina. Martha stood behind, and as she reached around to pick up her make-up paraphernalia from the dressing table, her breasts rubbed against Mina's back and neck. Mina luxuriated in the caress of Martha's nipples and made no protest while Martha applied lipstick and eyeshadow to her maid. From somewhere, she produced a short blond wig, which completed Mina's transformation.

"Now, Mina! Get this place tidied up and sort out my undies for washing. After all, you made them all wet and sticky, and you've always shown an interest in my washing," ordered Martha. "Don't worry; you'll be well rewarded." So Mina got to work. She was a little resentful at first, but she loved the maid's outfit, especially the feel of the petticoats, which, despite her two layers of panties, were exciting her cock, no, her clitty!

While the maid got on with her housework, Martha got dressed again. Retaining her stockings, she added a deep suspender belt, matching black bra and panties and a lace-trimmed black slip. Mina was hard as a rock again, and the constraining knickers were simultaneously both exciting and a little painful. Martha left the room.

Willem, couldn't give a sod about tidying up, but he decided to humour Martha. He loved the maid's clothes but not her duties. Martha had other ideas. She returned to the room and announced, "Mina, you dirty, lazy tart, if you don't do a good job, I will flog with my riding crop!" Mina didn't like the sound of that and wondered what he had gotten himself into. This cross-dressing and shagging Martha was fantastic, but he didn't want to get into S&M. Then Martha purred, "But good maids get rewarded with a good fucking. Tell me, Mina, have you ever been fucked in your sissy cunt?" It took Mina a second to realise that Marth meant her arse.

"No, never," said Mina, with a touch of indignation.

"So, you're a sissy virgin!" exclaimed Martha. "We'll have to do something about it. It was always the master's privilege to deflower the maids. You have a mistress, not a master, so I suppose I'll have to do it."

Mina almost went into panic mode; what had she gotten into? Then she noticed a tent pole in Martha's lovely black slip and what looked like the tip of a penis showing under the lace trim of the hem. Mina was confused, excited and a little afraid. She realised that Martha had a strap-on cock over her black panties.

It had meant to have been an illicit wanking session with Martha's undies, but it had gone crazy. Mina had gotten in deeper than she had ever wanted to. She had had fantastic sex and been dressed in wonder feminine garments that alone would have brought her to orgasm. That was a dream come true, but being buggered had never been on Mina's bucket list.

However, it didn't look like Martha would take no for an answer. "You need some training Mina. You'll thank me later, my dear," said Martha as she pulled Mina towards her. Standing in front of Mina, she reached under Mina's skirt and pulled her silky panties down to her knees. Then she ripped the old directoire knickers apart, exposing Mina's clitty and virgin bottom. Spinning Mina around, Martha ordered her to bend over a chair arm. As she did so, she felt Martha dollop a load of something cold and creamy on her arse. Thank God for that thought, Mina, lubricant!

Martha reached around with one hand and took hold of Mina's clitty, which was hard as iron despite her frightened state. Mina liked that. With her other hand, she guided her plastic penis into Mina's bum.

It hurt, but not as badly as she had expected, and because Martha was wanking her clit in time with her anal thrusts, it was a captivating cocktail of pain and pleasure. Mina came in a very few minutes, all over Martha's hand. Martha withdrew, and Mina dropped into the chair while Matha licked Mina's spunk off her fingers. Martha bent down and kissed Mina's clitty.

Stroking Mina's face, she gently said, "Well, you've had a surprising time today. I'm sure you've enjoyed it, but I sense you resent the loss of control. Would you like to assert your dominance by pissing on me?" That was going too far for Mina. "No, thank you! Let's shower together and clean each other up?"

So, that was Willem's introduction to Martha's world. She was obviously very experienced, and that included cross-dressers. Willem realised that she had been pushing the boundaries to find out how far he would go as Mina.

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