Madam Molly Pt. 01

As they did he sensed she was looking for a definitive answer, but Jesse still had butterflies in his belly and decided to err on the side of caution. He very nicely told her he wasn't quite ready to commit and asked her to please be understanding while he gave it a little more thought, he promised her it wouldn't be a long wait. She was a bit disappointed but told him she understood. She had invested a lot of time and effort into Jesse and didn't want to blow the opportunity by getting impatient. She did however ask him if he would at least consider coming to her house one night so they could meet. She promised him there would be no commitments required, she just wanted to meet face to face so she could show him a few things. She seemed very sincere and he liked the fact that she was taking the risk of exposing her location, so he agreed to stop by the following night. She gave him directions and they ended their session with him feeling both nervous and very excited.

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Jesse arrived at Madam Molly's house at seven. She lived in a neatly kept two story home on a large lot in a quiet suburban neighborhood. He pulled in the driveway and parked behind the house as she instructed, then ascended the rear stairs and knocked on the door. He was very nervous and he wondered if he was crazy in the head for doing what he was doing. He had no idea what he was walking into, but at the same time he had to find out if reality was anywhere close to the online fantasy.

What did she have in mind for him? What would she be wearing? What did she want to show him? Would her husband be there? She never said one way or the other. A hundred questions were going through his mind right before the door opened revealing Molly, and being almost his height they were literally face to face. Her blue eyes and steely stare captivated him for a moment, but he quickly snapped out of it.

"Madam Molly I presume?"

A sly smile formed on her pretty face.

"I like that Jesse, you sound like a good boy, but for right now Molly will do."

Since she was not in character he let his eyes drop and wander all over her mid-wale corduroy overalls. They were light brown, looked a little rough and covered a red t-shirt. She was barefoot and had left one of the straps of her overalls undone and hanging down, which made her look like a pretty country girl looking for a roll in the hay. It was obvious she decided not to get dressed up, but it was also obvious she had corduroy on her mind. He was actually quite turned on by her simple outfit and it made him happy he didn't try to impress her with fancy clothes himself. He'd thought about wearing his three-piece corduroy suit but decided against it, it would have made him look like he was trying too hard to impress her. So instead he went with a simple pair of black mid-wale corduroy jeans, a thick black belt and a grey mid-wale corduroy work shirt. Even though she knew all about Debbie and his crossdressing he didn't want to be effeminate in any way on their first meeting, so he decided to emphasize his corduroy fetish rather than his sissy side.

"Molly is fine with me, it's a pretty name. By the way I like your outfit, it's very sexy."

She chuckled and thought. Hell, if corduroy overalls can turn this little pervert on, his obsession is going to make him very easy to control. Not even noticing her chuckle he rudely kept his eyes glued on her overalls instead of her face, but she didn't mind, she'd have been more upset if he wasn't ogling her.

"Thank you Jesse, I'm really glad you showed up tonight."

"Why, did you think I'd be a no-show Molly?"

He raised his eyes to hers and they shared a timid chuckle. He liked that she seemed a little nervous too, it made him feel better about the butterflies in his belly.

"I don't know Jesse, you just never know sometimes, you know what I mean?"

"Yeah Molly I do."

"Oh God, where the hell is my head at, please come in."

She stepped back and let him enter.

He walked into a medium sized kitchen and she immediately offered him a drink. After giving her his preference she told him to go sit in the living room while she made the drinks. The living room wasn't very large, and the furniture made it look a little cramped. There was a large sofa done in a mustard yellow mid-wale corduroy on one wall and a black leather recliner next to it at ninety-degrees. The sofa sat across from a 50-inch TV and some stereo equipment on a large hutch, and in front of it was a coffee table that looked old. What immediately caught his eye however was the attractive mistress on the TV. She had a large strap-on dildo sticking out of her shorts and was fucking the ass of some sissyfag. He liked that. The sound was off but his mind supplied the squeals of the pantyboy, she was giving it to him hard and fast.

He decided to sit on the sofa, what the hell it was corduroy, but he also wanted to see if she would sit next to him or go for the recliner. He was a bit surprised she'd have a video like that on when they first met, but then again it did kind of set the mood for why he was there. He wondered if he was going to meet her husband, even though he knew he was a wimp he still felt a little apprehensive about meeting him. A few minutes later she came in with a big smile and put his drink on the table using a cheap coaster, then sat down at the other end of the couch. She was staying close but at the same time allowing a safe distance. They both sipped their drinks and their eyes were drawn to the neutrality of the TV.

She giggled. "I can't believe I put on something like that, I just thought we could use a little atmosphere. If you want I'll turn it off."

She picked up the remote.

"No, it's OK, actually she looks like my kind of lady."

They both chuckled nervously again and things felt very awkward. She ran her hand over the top of the sofa cushion between them and said with a sexy smile.

"I just want you to know that the corduroy sofa is a coincidence. I'd really like to explore your fetish and would love to take credit for the gesture, but we've had this for a long time."

They again chuckled and he said he understood. Although hearing her say she wanted to explore his fetish both broke the ice a little, and turned him on a lot. They started out slowly with some small talk and the discussion soon evolved into one of their chat-session. For an hour or so they felt each other out as they revisited subjects they had discussed many times before. After she brought in the second round of drinks they sat a little closer, held hands and began to get down to the nitty gritty. She asked him if he had made any decisions yet and he politely said he was still thinking about it, so she quickly steered the conversation in another direction. With all the corduroy in the room, the porno video and the kinky conversation Jesse felt like he was in a dream, like it all couldn't be real. But every time his hand rubbed against her corduroy clad leg it drove the reality home, and he loved it.

When it got to be ten-thirty and they had finished their third drink, the conversation stalled and Jesse thought maybe it was time to go. When he suggested it however she told him she hadn't shown him what she wanted to show him yet.

"Come with me Jesse, it won't take long and I really think you'll be glad you did."

She got up, tugged on his hand and he followed her down a hallway to a bedroom. She then led him to a closet and showed him all of her and Tracy's feminine corduroy clothes, there were many. She told him that she makes her husband keep his girly clothes in her closet so he won't crossdress without her permission. The bulge in his pants told her he was very turned on by her clothes, and that pleased her a great deal. After letting him get a good look she pulled him close and wrapping her arms around him.

"I just wanted you to see how serious I am about exploring your fetish. If you decide to join us for some fun you'll get to play with all the corduroy you see, and a whole lot more."

Her smile was very seductive. She let go, stepped back and took him by the hand again.

"Come with me lover, I have more to show you."

His boner started leaking pre-cum in his pants as she led him into another bedroom and opened its closet. It was filled with guy clothes and about 75% of them were corduroy. He was a bit shocked by the reality of it and a lot more turned on than he thought he would be. She gave him a few minutes to ogle the wardrobe and this time he couldn't help feeling up several of the garments. She liked that.

"As you can see I wasn't exaggerating when I said he really liked corduroy, and when I told him about your fetish he went right out and bought some more. About a third of those corduroys he bought in the past month or so, most of the corduroy girly stuff too. I told him to wait, to make sure you were interested first, but he was so turned on by the idea of being your corduroy slave that he didn't listen to me."

Jesse was horny as hell and didn't know what to say, so he pulled her to him and kissed her passionately for a few minutes, and she returned the kiss with equal enthusiasm.

When they came up for air she said. "To be honest Jesse, when I tell my cuck you were feeling up his corduroy clothes I bet he'll cum right in his pants."

He couldn't believe what was happening and his senses began to feel overloaded. After a few more minutes he told her he had to go or he was going to push her on the bed and fuck her brains out. She told him in a nice but firm tone that there would be no fucking without a commitment. He sighed deeply and said he needed to think about it a little more. She seemed deflated by the rejection and asked him if he wasn't interested.

"Hell no! Are you kidding me? I'm not saying that at all. I just need a little time to absorb it all. I'll meet you on line tomorrow and give you my answer, but quite frankly Molly, I don't see how I could ever walk away from all of this."

She smiled from ear to ear, then playfully patted his bottom.

"OK lover, you go home and think about it, and just remember the part where you can play with our corduroys whenever you want."

He took a deep breath, gave her another long kiss and then left.

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The next evening at their regularly scheduled time Jesse entered their chat-room and waited, a few minutes later Madam Molly entered as well, and as soon as she did she saw the following comment:

"Madam Molly, I thought about it all day and decided that if you will allow me to be your slave in whatever manner you desire I will be most grateful, I wish to serve you as both your boyfriend and your sissy slave, please command me as you wish."

There was no response for several minutes but she remained in the room, so he just waited and held his breath. Finally, after what seemed like hours, a one-line response appeared.

"Four o'clock tomorrow turd, and don't you dare be late. Park in the rear again."

When he finished reading he sighed deeply and debated whether he should respond or not, but after a few seconds she was gone. He stared at her comment for a couple of minutes while rubbing his corduroy bulge and wondered what the hell he was getting himself into. He exited the chat program and was about to shut down when he noticed he had mail. It was from her.

"I want this understood right from the start my new little turd. As of this moment you will remain monogamous to me, and that means both girls and boys. Being with me you'll have all your sexual needs met both by a woman and someone with a penis, so there is no reason for you to be having sex with anyone else. It will not be tolerated, and any violation of this rule will cause everything between us to cease and destroy the one chance you'll ever have of finding corduroy heaven. So you better listen turd, because there will be no second chances. Tomorrow night you are to be dressed as my boyfriend Jesse, you will not be a sissy on our first night together."

That was it, no hello or goodbye and no room for rebuttal. It seemed pretty obvious she was establishing the tone of their relationship right from the beginning.

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The following day was Saturday and he spent the whole morning puttering around the house with butterflies in his belly and a boner in his pants. He wanted to jerk off several times but something told him he should wait, something told him she wouldn't approve, then all of the sudden he realized she was already controlling him. He liked that. About three o'clock he picked out his, it consisted of a pair of navy blue mid-wale corduroy jeans, a plain black t-shirt and a corduroy jeans jacket that matched the pants. She said she wanted him looking masculine and he thought the outfit would probably please her.

Just for the hell of it he decided not to wear any underwear, it would make things easier if she wanted to pull his cock out through the zipper of his trousers, she said she thought it was cute that he liked dicks sticking out of corduroy pants. He also decided to bring Madam Molly a gift, something to start things off on the right foot, so in keeping with the mistress/slave theme he opted for giving her his cock cage. He'd purchased it several years ago hoping his ex-wife Elaine would use it to spice things up, but other than putting it on to show her how it worked it sat unused ever since. It was still in the box. He was sure Madam Molly could find a use for it, or at the very least she would appreciate the gesture of submission.

He checked his email to see if she had sent him any more instructions, but there was nothing. He took an extra pair of corduroy trousers and another shirt with him just in case, you never know. He got in the car and headed for her house making sure to be on time. Parking behind the house he arrived five minutes early, and this time he noticed a very large Great Dane sitting quietly in the middle of a dog run, he seemed very well behaved and hardly paid Jesse any attention. Molly answered the door wearing a pair of gray mid-wale corduroy dress pants and a pair of red corduroy ankle boots. The trousers were snug but not tight and they made her slightly fat bottom look even more pronounced. He liked that. On top she wore a matching gray corduroy vest with nothing underneath it. Her hair was tied up in a loose bun and her face was made up very pretty.

She stood with her hands on her hips in a very commanding pose, appearing to be in no mood for any nonsense right from the start. In short, she looked sexy as all hell. They eyed each other for several seconds and she broke the silence.

"You look very nice Jesse, come in. What's in the bag?"

He stepped in and handed it to her.

"Madam Molly, in gratitude for allowing me to serve you I brought you a gift that I thought was appropriate, I hope you will enjoy it."

She stepped over to the kitchen table, put down the bag and pulled out the cock cage. A smile slowly formed across her face.

"That was very thoughtful of you slave Jesse, I'm quite impressed, and I'm glad to see you know who owns your penis."

She put it back in the bag.

"Being on time and bringing a thoughtful gift was very smart, it's kept you off my shit list and has given you a good start."

Then in a reversal of their previous meeting, she pointed to the cabinets over the refrigerator and told him to make them both drinks and bring them in the living room. He did as instructed and his dick was as hard as a rock in response to her outfit. He brought the drinks in and found her sitting in the recliner, and on the sofa sat a small guy he recognized as Tracy. He was wearing a pair of red wide-wale corduroy pants and on top he had on a dark pink mid-wale shirt that really looked more like a blouse. It had long sleeves, a Peter Pan collar and ruffles running down the front, it was definitely not a guy's shirt. He looked just as petite and wimpy in person as he did in the pictures.

Jesse put down her drink on the coffee table and remembered to use one of the coaster. She liked that, and she liked the bulge in his pants too. He remained standing with his drink and stared at Tracy, who avoided looking back.

"Mistress, I thought you said you didn't want any sissy stuff on our first meeting, I'm quite sure that's not a man's shirt."

She just shrugged. "Trust me Jesse, that's about as butch as it gets with my cuck, and don't call me mistress. My name is Madam Molly, I'm not some cheap dominatrix."

"Yes of course Madam, I'm sorry."

There was an awkward silence and Jesse remained standing. After several seconds Molly said.

"Hey cuck, he's waiting for you to move so he can sit down next to me, move your ass down to the other end of the couch. Hurry it up bitch."

He did as told without saying a word and Jesse caught him eyeing the bulge in his pants. Jesse sat down. In one way he envied Tracy's predicament, he was getting to be the sissy bitch Jesse loved being himself. However, he found being in a position of dominance over another fag quite exciting too, more so than he ever thought it would. Once again there was a porno movie playing on the TV with the sound off, it wasn't the same one but the theme was similar, ladies with strap-ons fucking faggots. Jesse eyed Tracy for a long moment as he sipped his drink, he really liked Tracy's outfit. Tracy could see Jesse ogling him but the wimp kept his eyes glued to the TV, he looked very intimidated. Molly cleared her throat loudly and Jesse turned to look at her.

"Alright Jesse, seeing that it's Saturday I assume you don't have to be anywhere tomorrow morning, am I right?"

"No Molly, I mean, Madam Molly, I'm sorry."

"Good, I just wanted to make sure because our first session might last all night."

She winked at him with a smile, he swallowed hard and his expression remained blank. He was obviously nervous and she told him to relax. To help the situation she asked him several questions about what was happening in the video, just to get him talking and break the ice. She complimented his outfit and began talking to him more as a boyfriend than a slave, but there was always an air about her that demanded respect. They made small talk for about a half an hour, and between that and the alcohol Jesse began to relax. He found it odd though that she didn't introduce Tracy or even acknowledge his presence the whole time they talked, it was as if he wasn't even there.

A few minutes later however, as if reading his mind, she asked. "Do you like my cuck's outfit Jesse?"

"Yes Madam very much, he looks like a wimpy sissyboy, the kind of mamma's boy who gets passed around in a prison cell-block."

She chuckled. "Excellent! That's exactly what I had in mind when I picked out his outfit. I didn't want him in ladies clothes, I didn't want you getting a girly image of him the first time. I wanted him to look like exactly what he is, a pathetically emasculated little wimp."

They both stared at him, and even though he wouldn't look back the humiliation was written all over his red face. That emboldened Jesse.

"Oh I can see that Madam, I can imagine him being my prison bitch in his corduroy uniform. I'd make the pussy suck my dick every night and pimp his ass out for cigarettes during the day."

Tracy swallowed hard and almost looked like he wanted to cry, but Jesse got the feeling he really liked what he was hearing. Even more surprising though was how much he enjoyed saying it. He never fantasized about being the one who dished out the abuse, instead it was always him who got humiliated for being the bitch.

He looked at Molly. "Madam, may I ask a question?"