Mistress Sylvia Pt. 01

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergency on his part, but as far as he knew there were no emergencies tonight. When she requested he dress as Debbie at the end of their last session his maroon dress immediately came to mind. It was pretty, feminine and very soft, and he loves the way it felt against his sissy skin.

Debbie had a fetish for the fabric corduroy. He loved wearing it, he masturbated with it constantly, and seeing other people dressed in it excited him tremendously. It also made him absolutely crazy with lust when someone wore it specifically to turn him on. In general he was a horny little pervert when it came to corduroy. However, unlike most of his corduroy wardrobe, which consisted of both masculine and feminine attire, he loved the maroon dress so much that he never jerked off with it or soiled it with his sissy sperm. He would rather worship it like the dress of a mistress than ever treat it like some dirty jerk off rag.

Laura Ashley was his favorite designer, she made very beautifully feminine clothing that always had a slightly Victorian accent. This particular dress was actually a bit on the heavy side, being a thick wide-wale, and it was perfect for the fall weather. It had long sleeves, a mandarin style collar and two large patch pockets on the skirt. The bodice buttons down to the waist and his bra and breast forms fill it out nicely. Underneath he felt like going all out (how many times does your therapist request you to cross dress for her?) so he had on a pair of dark-gray, silk, seemed stockings and a red and black garter belt. On his feet he donned a pair of black corduroy Mary Janes. Not the best pick for that outfit to be sure, but they were the only corduroy shoes he owned.

His pink panties had lace trim and barely contained the boner he'd been sporting since donning the dress. His blonde shoulder length wig was cute, and it too would have to do because it was the only one he owned. He would've preferred being a red head in that dress. He thought his face was painted nicely, although he knew his skills in that area were limited. His previous mistress, Mrs. Monroe, had taught him some basic applications but he still had much to learn.

Oh, and by the way, Debbie loved being a sissy-fag. In fact, even dressed masculine he looked like a dickless wimp. He loved crossdressing at every opportunity, and tonight he'd be dressing in front of his therapist for the first time. He was excited to say the least.

At eight o'clock sharp the office door opened and Anne stepped into the waiting room. She stared at him momentarily, taking in the whole picture, then catching herself she smiled warmly and invited him in. They assume their normal places, he on the sofa and her in her arm chair. Feeling very effeminate Debbie crosses his legs like a lady and tried to act as girly as he could. Anne maintained eye contact when she spoke, not wanting to draw attention to his attire. She didn't want that yet, and told him so.

"First of all Debbie you look very nice, that's a very pretty dress. I'm sure you're curious about our special circumstances, but if it's alright with you I'd prefer we have our normal forty-five minute session first, then we can address the other reasons why we're here tonight. OK Debbie?"

Being horny and eager to discuss his sissy feelings he was a bit disappointed, but the fact that she was using his girly name for the first time excited him a lot. So he agreed and they proceeded to discuss his life over the past few days and the issues he'd been dealing with. After the forty-five minutes were up, which to Debbie felt like hours, Anne said.

"OK Debbie that was a good session, thank you. Now let's talk about the reason why I asked you to get prettied up tonight."

He immediately felt his boner wake from its slumber.

"As you know we've talked at length about your crossdressing, your corduroy fetish, your sissy disposition, your bisexuality, your past mistress experiences and your masochistic desires. I've given your situation a lot of thought recently and I've come to a conclusion that I'd like us to explore.

Even though I believe you had a genuine desire to change, and you sincerely tried to work with me, you've still made no improvements in those areas whatsoever. I'm not going to rehash it all now, I think we both know what I am talking about. However, I want you to consider this. When it comes to your desire to be a sissy slave for a mistress and all the other kinky perversions along those lines, I no longer think you should try and change any of that. I think in here we should now concentrate on some of your other issues, such as your desire to crossdress in public, or your fetish and compulsive masturbating."

He was initially stunned, but as it sank in he began to feel very aroused.

"So I guess what I'm saying is that even though you don't presently have a mistress I think you should let your mind freely explore those desires. From what I can see from your past you certainly seem destined to serve a dominant woman in the future. If you'd like we can occasionally discuss those fantasies just so I can keep an eye on where you're going with them. In fact I think that would be a good idea. In my opinion you need to get in touch with all those submissive desires and find out where they're coming from. Perhaps if you have more masochistic experiences in the future, safe ones of course, we may gain some valuable insight.

I also think that we should switch the time of your sessions to the evening, that'll make your dressing as Debbie a little easier to facilitate. Would that be OK with you?"

They continued discussing it for another ten minutes or so, and Debbie happily agreed with his therapist on all counts. The idea of dressing in drag in front of her twice a week made little Debbie so fucking horny he almost asks her if he can lick her pussy in gratitude, but he stopped himself. Mrs. Monroe would've certainly expected such an offer after giving him a reward, and this definitely felt like a reward, but he quickly realized his therapist might not appreciate it. So instead, without thinking, he said.

"Thank you Miss Annie, it makes me feel so much better knowing that when I'm with you I can dress and act like the sissy-fag I really am."

There was an awkward pause and the words just hung in the air, waiting for an explanation that didn't come. She finally asked.

"Did you just say Miss Annie? Why Miss Annie? What do you mean by that dear?"

He got red in the face and sheepishly replied. "I'm sorry Anne, I didn't mean anything by it. I just felt so much gratitude, and since I can't call you mistress, I guess my desire to show respect made it come out that way. I won't say it again, I promise."

She looks off into space and momentarily pondered, then said.

"Actually Debbie, I find that kind of interesting, and no, you didn't offend me in any way so you can relax. I guess as long as you realize that I'm not your mistress, and you only say it during a session, then I don't have a problem with you addressing me as Miss Annie."

Again he was stunned and totally thrilled all at the same time. They exchange a few more niceties, then Debbie headed out the door with a boner straining his panties. His mind was already preoccupied with thoughts of next session's outfit.

************************************************************

Reaching the parking lot Debbie noticed there were only two cars left in the lot. One was the old clunker his Aunt Jessica bought for him the previous month, and the other was a new Mercedes parked a few spots away. Walking toward his car he saw a tall woman leaning against the Mercedes smoking a cigarette. As he passed the first thing that struck him was her height. Debbie was six foot tall and the woman looked a few inches taller than him. She turned and looked at him as he went by, giving him a polite nod and a pretty obvious once over.

She wore a simple shift dress that went to mid-calf and the top portion was covered with a matching jacket. The outfit was a dark color he couldn't make out in the dim lighting of the parking lot, but the boots sticking out from under her dress definitely looked black. The two most memorable things about her, were the loose fitting head scarf hiding her face and her long cigarette holder. You didn't see many cigarette holders these days, and the whole package made her resemble a 1930s movie star, like Betty Davis or Kathrine Hepburn.

Although she was an interesting woman he didn't pay her a lot of attention because his thoughts were filled with fantasies of dressing for Miss Annie. Being a horny little sissyboy, he was already planning to ask if she would watch him jerk off and shoot his sperm all over his corduroy dress. He would fucking love that. And even though it seems like a long shot, he reminded himself that just a few days ago the thought of dressing in front of Anne was a long shot too.

As he opened the car door he was startled by the woman's voice.

"Excuse me dear, could I trouble you for a moment please?"

She was standing on the other side of the car, and that surprised him a bit, but he quickly realized he'd been lost in his thoughts.

"My name is Sylvia and my automobile has apparently died. I don't live far from hear and I was wondering if you could be a dear and give me a lift home."

Suddenly remembering he was in full drag he began to panic. Keeping his voice as soft as possible, he said.

"I'm sure you'll be able to make a call from somewhere inside the building."

"I did try that dear, but at this time of night the door locks behind you when you leave, and unfortunately I wasn't paying attention when you came out. By the time I saw you it was too late."

She took a drag of her cigarette.

"If you're concerned about your safety, which is perfectly understandable, I'd be glad to show you many forms of identification. I'm a well-known woman in this town with an impeccable reputation."

She then slowly pulled the scarf back from her face, and let out a slight chuckle.

"Besides dear, as you can see, at my age I hardly present much of a concern, especially for a big girl such as yourself."

Now that his eyes had adjusted some, and with her face in clear view, he saw she was a woman of about fifty, possibly older. And the voice now fit much better.

"No Sylvia, that won't be necessary, please get in. I'd be glad to give you a ride home."

He realized he might be making a mistake, but the idea that he was passing turned him on like crazy. So much so, that while getting in the car he made sure is boner was still firmly encased in his panties, he didn't want it turning his dress into a circus tent and giving away his secret. Once they were both seated he was glad he did too. In the light he saw that her pretty dress and jacket were done in a plush dark blue mid-wale corduroy. It wasn't a cheap outfit by any means. In fact it looked fitted and the fabric was to die for. When he managed to get his eyes to her face he noticed her beautiful scarf was made of the same fabric, but in a lighter blue. He stared for a lot longer than he should have and she simply smiled.

Letting the moment pass, she said. "That's a very pretty dress you have on dear. As I said, my name is Sylvia."

Snapping out of it he realized he was being rude, and keeping his voice as soft as he could, he replied.

"I'm sorry Sylvia, thank you, my name is Debbie, and I was just admiring your beautiful corduroy outfit."

Sylvia cocked her head slightly and smiled, giving Debbie a sly look.

"Thank you Debbie. I noticed you called it a corduroy outfit, emphasizing corduroy. I find that a bit unusual. Are you just a very observant girl, or do you have a thing for corduroy?"

Alarm bells started clanging in his ears and his pulse began to race. A hundred thoughts flooded his mind at once with the main one being. How the fuck did she know? He then tried to convince himself it was just a coincidence, and bluffed.

"No, no Sylvia, I mean who would ever have a thing for corduroy? That would be ridiculous!"

He tried to punch it up with a laugh but even to him it all sounded lame, it also didn't sound very feminine.

Sylvia let the words hang for a few seconds while Debbie's face reddened, then gently corrected him.

"I think you're mistaken dear. Over the years I've met a few people who became sexually excited by just the sight of corduroy. It just goes to show you never know what turns some people on. Maybe we should get going Debbie."

Recovering a bit, he started the car and headed out of the parking lot. Sylvia asked him a series of innocuous questions and offered some small talk to put him at ease. Then at one point, in an offhanded manner, she asked him why he was at the professional building that night. Without thinking he blurted out, "oh I was there to see my therapist Anne", immediately wishing he could take it back.

Again she let the words just hang a bit before saying.

"Anne? Do you mean Anne O'Malley? I know Anne very well, have known her for years. She's a fine lady and a wonderful therapist, you're a very lucky boy indeed."

At first it went right by him as she continued to make small talk, but after a minute it finally registered. "Lucky boy?" Did he hear her right? He wanted to believe he didn't, but he was pretty sure he did. He then debated whether to bring it up or let it go and pretend it never happened. He was brought back to Earth when he realized she was repeating a question. She then asked.

"Are you alright Debbie Dear? You seem a bit pale."

"Debbie Dear?" Another jolt.

"How the hell did she know that's what his former mistress always called him? He panicked and pulled to the side of the road.

Once stopped Sylvia said. "What's the matter dear? You look as though you've seen a ghost."

He took a deep breath, folded his hands in his lap and said in a very meek voice.

"How did you know that I liked to be called Debbie dear?"

"How did I know? I didn't know anything Debbie, it just came out. Why does it bother you so much?"

He kept his eyes in his lap and after a long pause he asked in a whisper.

"You said lucky boy. How did you know I was a boy?"

Sylvia sighed deeply.

"Alright Debbie, I'll explain all of that in a minute, I promise. However, before I do will you please drive me home, it's only a few miles away, and then I'll explain everything. OK? Will you please do that for me?"

He nodded but said nothing, then pulled back out on the road. As it turned out she wasn't lying, because in less than five minutes he found himself parked in the driveway of a beautiful mansion. He felt a little like he was in the Twilight Zone. Twenty minutes earlier he'd been sitting in Miss Annie's office, happy as clam to be dressed in drag in front of her. And now, twenty minutes later, he was sitting in front of a fucking mansion with a very mysterious woman dressed in corduroy who seems to know everything about him. It was all very fucking weird.

She asked him to turn off the car and he complied. She then turned in her seat to face him more directly and spoke in a pleasant but matter-of-fact tone.

"My Name is Sylvia Bartolo and this is my primary residence. I'm a very wealthy woman Debbie, and I tell you that not to impress you, I say it as a matter of explanation. You see dear, I'm a mistress, and I'm aware you know what that means, so I won't waste time elaborating. Without trying to be immodest, I say with confidence that I'm an attractive woman, especially for my age. Again, this is not a boast, just an observance of reality.

With my looks and money I'm capable of having any kind of man I want, whenever I want, and I often do. But I also derive a lot of pleasure from, and take great pride in, my ability to create well trained sex slaves, primarily of the sissy-fag variety. I've been training fag-slaves for many years and always have a small stable in each of my homes, usually no more than a half dozen or so. I believe in quality, not quantity.

My training techniques have withstood the test of time are well proven, but my best asset in creating a sissy slave is my ability to size up a new prospect right away. This saves me a lot of time, as I can usually tell after just a brief conversation if a faggot has the potential to live up to my standards. As it happens, I currently have an opening for a new prospect."

She paused to light a cigarette, then rolled down her window. She looked very out of place in Debbie's beat-up clunker.

"Having said all that, I'll now answer your questions as promised. First of all, I'll admit that our meeting wasn't entirely by chance."

"I knew it. It was Anne wasn't it? I bet she told you everything. Isn't that against the law or something?"

Sylvia cut him off. "Wait a minute Debbie, I said no such thing. This has nothing to do with Mrs. O'Malley, and any connection we may share with her is purely coincidental."

Debbie whined. "Bullshit, then how did you know all those things about me?"

She gave him an icy stare and spoke in a sharp tone.

"Hold your tongue faggot. I said I'd explain things and I'm keeping my word. So I strongly suggest you shut your mouth and keep it shut until I'm done. Am I making myself crystal clear you little turd?"

For several seconds his face was riddled with confusion, then she saw what she was looking for. He blinked several times, then dropped his eyes to his lap, his submissive instincts were kicking in and that pleased her. She waited him out and after several more seconds she heard.

"Yes Madam Bartolo, I understand."

She liked hearing that, and after taking a long drag of her cigarette she continued in a softer tone.

"Now, as I was saying before I was so rudely interrupted, our meeting wasn't by chance. As you probably know from your past experiences with mistresses, many of us belong to clubs and online networks. Without a lot of explanation, suffice it to say that word gets around. In your case Debbie, I received a few reports about you that led me to believe you might be a good prospect. I asked around and found out you were no longer serving Mistress Monroe, I also discovered that you were currently seeing Mrs. O'Malley for therapy. That's how I knew you'd be at the professional building tonight. So I simply drove over to the parking lot and set things up.

So to answer your question directly, that's how I knew you were a boy, and it's the reason I'm dressed in this corduroy outfit. I hoped the corduroy would get your attention, and maybe even give you a sissy boner. As far as the "Debbie dear" thing, I have no idea what your problem is with that. I simply used a term of endearment."

She took another drag of her cigarette and looked out the window for a minute, purposely ignoring him. Debbie kept quiet and waited patiently. She liked that. When her cigarette was done she threw it out the window and asked matter-of-factly.

"Do you have a boner Debbie?"

He looked at her puzzled.

"Answer me fag. Did my corduroy outfit give you a boner?"

"Yes Madam Bartolo, it did."

"Good sissyboy, because if it didn't I'd be very displeased with you. Now, I want you to take your sissy little boner home and think about this. I've decided you have possibilities and may be worthy of my training. So if you're interested in this one time offer, and fag, I never give second chances, then you'll report to my front door tomorrow morning at ten o'clock sharp."