Madam Molly Pt. 01

It all started in a chat-room, "Closet Sissyboys."

Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He loved the look and feel of it, he loved kissing it, rubbing his hands and face against it, jerking off with it and cumming all over it. In short, he loved everything about it. Just seeing a woman or cute fag dressed in corduroy could give Jesse a boner, and most of the time it did. Which meant he spent a lot of time walking around with a bulge in his pants.

His nine-year marriage ended for several reasons but his fetish wasn't one of them, in fact his ex-wife Elaine was pretty good about indulging his corduroy desires. When it came to his other kinky fantasies however, she was far less interested. Jesse was an attractive masculine guy but behind closed doors he liked to dress girly and be a wimpy effeminate sissyboy. He especially loved the idea of being forced to do so by a dominant lady. He really wanted to be humiliated for being a faggot, and in his fantasies if his Mistress wanted him to have sex with another fag for her amusement, he would. Elaine didn't like his fantasies, it just wasn't her thing. At times she tolerated his crossdressing, yet at other times she would use it against him. That pretty much summed up their marriage, they could connect on some levels but not on others, and over time the levels of disconnect won out.

In general when it came to the ladies he was pretty traditional and he'd never had sex with a mistress or any kind of dominant woman. Maybe because of that, as the years went by the fantasy of being a fag-slave for a mistress became stronger and stronger. In fact it'd become a fantasy he seriously contemplated turning into a reality, especially now that he was free to do so, but unfortunately he had no idea how to make it happen. He knew he could pay a professional dominatrix, but he could never bring himself to shell out two hundred dollars for an hour with a woman who really didn't understand what he wanted. He had no desire to be strung along to the tune of thousands of dollars and wind up totally frustrated. So he continued to jerk off with his corduroys and hold onto the fantasy that someday he would find a genuine dominant lady, a lady who would abuse and humiliate him for her own pleasure, not money.

When it came to guys Jesse wasn't queer, he knew that, masculine guys didn't excite him in any way. However he liked sucking cock and loved the idea of being forced to worship one by a dominant lady. There were times too, if he was horny and saw a guy in corduroys, he would fantasize about unzipping the guy's pants and sucking him off, but as soon as he looked up from the guy's corduroy bulge his fantasy would disappear and he'd get very turned off. Dicks were exciting, men were not.

During the years prior to meeting Elaine he did experiment with several crossdressing sissies. They were one or two-night stands in cheap motels with a lot of drinking and kinky sex, and even though he enjoyed the fag sex a lot, and loved being dressed girly in front of someone else, there were still many regrets the next day. Over the years as he jerked off and remembered those nights, he became more and more convinced that if he ever went down that road again there would be no regrets this time.

That basically summed up Jesse's situation. He was starting a new chapter in his life and trying to decipher what he really wanted, and how to go about finding it when he did. That's why Jesse hung around the chat-rooms, the anonymity made it fun to be totally honest about his kinky desires, and they provided a lot of good sexy reading to jerk off to. He had several "friends" in the crossdressing rooms, even a few who would give him some corduroy cybersex if he indulged them with their own particular kinks. He also spent a lot of time in the female domination rooms, like the one he was in that night, "Closet Sissyboys."

Since there were few real mistresses who ever showed up, and almost all of them were professionals looking for business, most of the time the rooms were full of closet fags describing their fantasies to each other. That was OK though because it often supplied good masturbation fodder, and a bit of a kinky kinship among the regulars. On that night however things were a bit different for Jesse, who went by the name Debbie in the rooms. A lady showed up by the name of Madam Molly. She popped up every now and then and as far as anyone could tell she seemed genuine, or at least she talked a good game. There were some rumors that a few fags had actually hooked up with her in real time, but rumors on the internet were about as useful as tits on a bull. The thing that made the night very special for Jesse was the fact that she focused right in on Debbie after only a few minutes. That got him very excited and inspired jealousy in all the other fags. She soon ordered him to a private chat-room, and of course he obeyed.

She started off by instructing him to call her Madam Molly at all times, and he was to do anything she told him to. If he didn't she'd block his screen name and he'd never converse with her again. She surprised him right off the bat by telling him she wasn't there for cybersex, instead she was interviewing him for a possible real-time hook-up. She then asked him if he was serious about finding a mistress, because if he was only there to be a jerk off she didn't want to waste her time. He wasn't sure what to make of her, in all likelihood she was full of shit, but he told her yes and decided to go along and see what happened. At minimum she'd probably turn him on enough to make him squirt.

She asked him to provide a land mark in the general area of where he lived, and after a few minutes they established that they were close enough to make it a reality. She told him that she saw him talking to another fag about his corduroy fetish, she found that both amusing and interesting and she wanted to know more. He liked that, and from that moment forward Jesse was completely under her spell. She seemed very real and he was surprised that there was very little standard mistress/slave cyber-talk. Throughout their conversation she managed to maintain an air of authority and dominance without ever sounding contrived, and that kept him mesmerized. She was his Madam Molly and he was her obedient turd, they both knew it and he accepted it right from the get go. It was understood.

They chatted for about two hours primarily focusing on two things, his love of corduroy and what their relationship would be like if they ever hooked up. He told her everything, every little thing about corduroy, details he'd always been afraid to tell anyone else, and she amazed him by asking many questions and appearing to be very interested. She in turned explained that she was very real and had a cuckold husband named Tracy. She had to explain what a cuckold was because Jesse didn't really know, but once she explained what a pathetic wimp Tracy was, that, and the fact that he was much younger, made Jesse warm to the idea of abusing the guy and fucking his wife right in front of him.

However, being a closet sissyfag who craved humiliation too, Jesse was a bit confused. So waiting for the right moment he respectfully asked her why she was looking for a fag if she wanted a guy to dominate her husband. She told him she was looking to experiment with new things, and his being a closet fag wouldn't be a problem so long as he was capable of acting masculine when she wanted him to. She said she would explain it all in their next conversation. She gave him a time and private room name to meet her in the next night, then she was gone.

Jesse was very turned on and jerked off with one of his corduroy skirts while going over the transcript of their chat several times. Part of him believed it was all bullshit and he'd never hear from her again, but there was another part that thought (perhaps hoped?) the whole conversation was just too sincere to be a sham. Eventually he splattered a huge load of gooey jizzum all over his skirt, and being as horny as he was, he imagined it was her husband's sperm and she'd ordered him to lick it up. He obeyed his fantasy mistress, then called it a night and vowed he would at least see if she showed up the next night.

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He spent all day at work trying not to think about Madam Molly but it was a hopeless cause, and several times he had to discreetly adjust himself to minimize the bulge in his corduroys. The fact that the little sissy was wearing stockings and a garter belt under his trousers didn't help the situation either. That night, after dinner, he put on a bra with breastforms and his light blue, mid-wale corduroy dress before sitting down at the computer with a drink. He also had a pair of his ex-wife's wide-wale corduroy dress pants that he stole from her when he moved out, and for several reasons he really liked jerking off with them. He felt like a pathetic little sissy sitting there a half an hour before the scheduled time rubbing his dick with Elain's pants, especially since he full well expected that no one would show up. But he was damn well going to make sure.

About five minutes before the prescribed time he put down the corduroys, sat up straight and fixed his outfit, as if she was going to see him. He knew he was being silly but he was hoping so badly that she was for real that he didn't care. At 7:00 sharp he entered the chat-room and his dress turned into a circus tent when she entered the room two minutes later. She told him he was a good boy and it was a damned good thing he showed up on time, she then asked him what he was wearing and he was honest with her. Hearing that, she spent a few minutes telling him what a dickless wimp he was without getting overly dramatic about it, which of course made it sound that much more sincere and humiliating. When the initial excitement had passed she proceeded to explain that even though he was a closet fag he could still be dominant over her husband.

Her explanation went as follows:

She was their supreme Madam Molly, their Queen, their Mistress, and they were both her sniveling slaves no matter if they were dressed as boys or girls.

"When it comes to me there should be no confusion about anything, when I speak you obey, or I'll slap your sissy little balls around and make you cry like a baby. Got it?"

He said he did.

"When it comes to my husband, he's my full time bitch slave, and if I allow it, yours too. That means that within my limitations you'll be free to use and abuse Tracy. Half the time I'll expect you to man-up and treat my fag a little rough, make him be a bitch for your cock. You will also fuck me right in front of him. If you prove good at that, then the other half of the time you'll get your chance to be a sissy bitch too."

It took a little more explaining but Jesse finally understood that if he played his cards right, not only would he get to fuck her and make her husband be his bitch, but at times she would force him to be a fag and humiliate the shit out of him. She might even make him suck her pathetic husband's little dickie for her amusement. So as long as he always remembered his place, he could be both dominant and submissive, sometimes both at the same time. The more he thought about it the more he liked it, then she delivered the zinger that would seal the deal completely.

"I have several items of corduroy clothing and Tracy does too. In fact Tracy has always liked corduroy, not in the same way you do, but he likes wearing it. He presently has half a closet full of corduroy clothing, that's the reason your fetish caught my attention. If you become my slave we'll start by having two or three regularly scheduled sessions a week. However, in between and provided you called first, you can come over here and play with our corduroy clothes."

He started jerking off with Elaine's pants and read what she said several times. After he didn't respond for a minute she guessed what he was doing and clarified things.

"To be clear sissyboy, you'll be free to play with Tracy's boy corduroys any time you want, but you'll only be able to play with my or Tracy's lady's corduroys with my permission. That, you will have to earn."

Actually, putting restrictions on it kind of made it more exciting, and even though he much preferred playing with girly clothes, the idea of being able to go in some fag's closet and jerk off with his corduroys whenever he wanted was turning him on like crazy. She teased him a little more with their corduroys and by the end of their chat session she had him right where she wanted him, and they both knew it.

It was at that moment that he suddenly understood how she operated. She was a dominant lady to be sure and he was certain she would give him what he wanted in that respect, but her way of controlling her slave was to create a situation so exciting that he couldn't disobey her, or ever walk away. She gave her slave too much to lose. It was fucking brilliant. Then she put the icing on the cake.

"Also Jesse, whenever you come over to play with Tracy's corduroys you can order him around and make him be your own personal corduroy slave. You can make him be your servant and fetch you drinks, or make him wear or do whatever you want with corduroy. The only rule is that you can't touch each other's dicks or use each other to make yourselves cum. There will be no sucking or fucking outside of our sessions, you can only cum by jerking yourselves off."

As he read her words Jesse was horny as hell and shot a load of jizzum all over the front of his dress. When he didn't respond for a couple of minutes she simply instructed him to be in the same room at the same time the next night, then disappeared. She knew she'd hooked her fish, now she would simply allow his corduroy obsession to do the rest.

They met in the same private chat-room several times a week and they comfortably fell into their roles, her as Madam Molly, and him as her slaveboy Jesse or fagslave Debbie. He would serve either role. That went on for almost three months and they eventually reached a point where they pretty much knew everything about each other's likes and limitations when it came to kinky sex, and amazingly there was very little discussed that posed a problem for either of them. In addition to all the crossdressing/fagslave kink she seemed to like how receptive he was to enemas, analingus and golden showers.

Somewhere along the line they exchanged non-sexual pictures by email, she also insisted on a few pictures of him in drag, which he supplied with his face obscured. She wasn't a raving beauty and he really wasn't expecting her to be, but she was attractive and looked very much as she described herself, she obviously wasn't trying to bullshit him. He liked that. She had previously told him she was thirty-four years old, five-foot eleven-inches tall and a hundred and fifty pounds with medium sized breasts, and the photos proved her description to be accurate. Her long blonde hair was wavy and her cute face reminded him a little of the actress Hilary Swank. She looked big boned and her body was slightly muscular, she was in good shape. Her hips were full and her ass was a little fatter than it should be for her body, but he immediately loved the idea of being ordered to kiss it when it was caged in a pair of corduroys. The whole package was one of a cute and playful tomboy who could easily be an attractive, no-nonsense, dominant woman when it suited her.

On the other hand, her husband Tracy looked a little different than he'd envisioned, but again her description was accurate. For some reason Jesse assumed she'd been exaggerating his wimpiness, he was expecting a smaller guy probably a little less masculine than himself. But in reality, if she'd exaggerated at all, it was in calling him a guy to begin with, Tracy was a total fucking pussy who made Richard Simmons seem like John Rambo by comparison. He was a young twenty-six, five foot six inches tall and maybe a hundred and ten pounds if that. He had a small thin frame and was rather effeminate, not a flaming faggot mind you, but he was the kind of guy women pitied and guys ignored because he was a pathetic wimp.

He had shoulder length wavy brown hair parted in the middle, and if he did in fact have a little five-inch penis like Molly said, it wouldn't have surprised Jesse in the least. Hell, Jesse would be surprised if the wimp had a dick at all. He also had a large pair of lips and Jesse immediately fantasized about having them wrapped around his dick. Looking at his picture, the character from the TV show "The Middle" came to mind. He looked like the daughter Sue's faggy friend Brad, a total fucking wimp, the kind of guy you just assumed was a queer. The fact that Tracy was an emasculated pansy was what tipped the scales and made Jesse seriously consider committing to Molly. On top of his desire to be Molly's bitch, the idea of that pussy being his corduroy slave was just too exciting to pass up, and he was pretty sure he wanted to give it a shot.

In addition to the pictures of himself, she'd required him to take pictures of every item of corduroy clothing he owned and write a little explanation of what he liked about each one. As their chats progressed she began telling him which corduroys he was allowed to wear and when, she also told him which corduroys he was allowed to jerk off with and cum on, and oddly enough he obeyed. She was attempting to take full control of his fetish and he liked that a lot. He requested pictures of their corduroy clothing in return but she flatly refused, she told him he would get to see them when she decided he could, and not a minute sooner. She was obviously trying to train him even before they met, and that was OK with him.

Molly told him right from the start that if they ever got together it would be a little while before it happened, she was in no rush. She was very serious about it happening, and she wanted it very much, but experience had taught her to be cautious and go slow. Part of him was a little disappointed because he obviously wanted it to happen, but in truth another part of him was fine with the slow approach, he had his own fears about the reality of it as well. In the meantime though he enjoyed the hell out of their cyber sessions. He sensed right away that she really enjoyed being dominant so he acted very submissive and adoring at all times. For her part she sensed how strong his corduroy fetish was and she indulged him with it constantly. They both really enjoyed turning each other on and they were pretty good at it too. In fact, after a week or so they even admitted to each other that they masturbated during their little sessions. Finally, one day out of the blue she approached the subject of taking things a bit further, and although he tried to act noncommittal she sensed his excitement.

"I've thought about it many times Ma'am, and I really like the idea, but I could never go through with it unless your husband was serious about wearing and using corduroy to turn me on."

She found that amusing. "Take another look at Tracy's pictures. My husband will do whatever the fuck I tell him to do, so if you want my little cuck in corduroy it won't be a problem. Provided of course, you are a very obedient slaveboy and keep me happy."

She often referred to Tracy as her cuck, short for cuckold.

She then confessed that she'd told Tracy about him and informed him she was thinking about making Jesse her boyfriend. She also told her husband about his corduroy fetish, and ever since she did the little wimp has been wearing corduroy pants. Jesse liked hearing that. She made it quite clear that Tracy was excited by the idea of a new guy fucking his wife, he was also very horny at the prospect of being Jesse's corduroy slave. He hadn't been a cuck in a while and was really looking forward to it. She was very convincing and they discussed the possibilities and logistics of their tryst for a long time.