Part 1
Bill and Tracy met for the first time in Atlanta—at a hotel bar in Buckhead.
He had just finished two days of meetings and needed a hassle-free place to grab something to eat and a drink. Due to the late hour, the hotel bar was the best bet.
She was sitting at the bar working through the emails of the day on her laptop, and nursing a glass of wine. But for a couple of other patrons, the bar was empty.
He sat down two stools from her. The bartender took his drink order. Bill looked at the menu, and was having trouble deciding among the offerings—nothing jumped out at him. He couldn’t help thinking how much of a pain these out-of-town meetings were—even figuring out what to order to eat at a hotel restaurant bar was a hassle.
Tracy noticed his struggle—
“Excuse me. But if you are looking for something really good, you may want to think about the seared Mahi. It’s amazing!”
“Seared Mahi? I wouldn’t have thought about that. But now that you mention it, it does sound good. Thank you!”
“My name is Bill, by the way.”
“I’m Tracy. Pleased to meet you, Bill.”
Bill hadn’t noticed how attractive, rather beautiful, Tracy was. He immediately took note. At the same time, she was appraising him. The physical attraction was immediate and palpable.
Conversation was easy. Both were very bright, and accomplished in their professions. She was a systems engineer by training, but had quickly risen to a high management position within the multinational company she worked for. He was a highly successful transactional lawyer for a well-regarded boutique law firm—having made partner at a very early age.
They talked into the night—politely learning about each other. She was attending a conference at the hotel, and he shared a few details about what he was doing. There definitely was a glimmer of something there.
Bill had just come out of a bad marriage and a difficult divorce. He had yet to even think about beginning to date—both because of the marital unpleasantness from which he had just escaped and the demands of his job.
It had been a long day for Tracy—having started the day on a red eye from the West Coast. She too was consumed by work, though this trip was not work-related. She was there to catch up with some good friends who were also attending the conference. It had been quite a while since she had actually “dated”—finding a physically attractive and interesting person, given her standards, to spend time with had proven to be just too difficult.
They each considered taking it further—to one of their rooms, but separately reasoned that it would be inadvisable to follow that impulse. Things like that never went anywhere, and they both had early morning obligations—his to get the airport and then to work, and hers to get to the early conference session. While unspoken, they both understood that their night would end when they were done at the bar.
Still, they enjoyed each other’s time. Being a gentleman, he did walk her to her room. And she treated him to a wonderfully affectionate kiss goodnight.
He was up and packed early. As he checked out of the hotel he noticed on a screen in the lobby a meeting schedule for a conference—The Southeastern Leather Collective. From prior experience (and knowledge he had gained via the Internet) he knew of that group—and knew that it existed to educate and support those interested in dominance and submission—sexual power exchange. He thought to himself that there must be another conference being held there—she didn’t seem that type. Out of curiosity, though, he asked the clerk at the desk if there was some other event being held at the hotel. The answer caused him to pause—
“No sir. We are hosting only the one conference.”
He could barely speak. Once he regained his composure, he smiled and chuckled to himself.
“If she only knew!”
Part 2
The second time they met was several months after—again at a hotel restaurant. This time, at breakfast at the Hotel Nomad in New York.
She had just had her coffee served. He was being escorted to his table when he saw her—
“Tracy, is that you?”
“Bill? This is just too weird! I cannot believe it is you. Can you join me?”
“I would be delighted.”
And so they talked. Almost like old friends who had been long separated and could immediately continue their relationship after the separation. They both felt this, and independently recognized it as an omen of sorts, karmic, and that something more would come.
Bill was feeling bold—
“Don’t suppose you’re free for dinner tonight?”
Something swelled within her—
“I am completely free—what are you thinking? “
“Well, do you like sushi?”
“Absolutely.”
“I know just the place. Are you staying here?”
“I am. You?”
“I am too. That will make it easier—getting to dinner, I mean.”
(Smiling. Knowingly.) “Of course. Time?”
“7:30?”
“Perfect. Meet you down here?”
“Again perfect.”
“Well, then, see you at 7:30.”
Bill used a connection to get 8:00 reservations at Shion 69 Leonard Street, one of his favorite spots. It had been many years since he had been this excited.
The prospect of their date had awakened something which had long lain dormant within Tracy—evidenced by an anticipatory arousal which interfered with her concentration for most of the day. She chided herself for this, and forced herself to try, with limited success, to ignore the dampness and swelling being visited upon her below. By the middle of the afternoon, she was almost desperate from arousal.
She was relieved when her meetings ended early, giving her time to shop. At the least, she needed to buy a panty or two as she had only packed for a few days, and the one she was wearing would be unwearable by dinner. So on to Madison Avenue.
She first stopped at Agent Provocateur—which had been one of her favorite spots back before she had become so overwhelmed by work. She bought a few items, just for fun, and found the perfect thing—a strappy three-piece black Whitney bra, panty and suspender ensemble, for the night. She bought sheer black nylons to go with the suspender belt, so she needed to find the perfect shoes, and then the right dress. Time was getting short. Luckily for Tracy, she found the ideal little black dress and Louboutin heels, lined in red leather, at a nearby shop.
He made it to the lobby first. When she came down in the elevator she near took his breath away. His reaction made her throb below. So much for the dry underwear.
Dinner was fantastic. Lots of saki, and a very nice Japanese scotch after. Neither one of them wanted to rush, but both felt what was coming.
While waiting for a cab on the street they kissed a long passionate kiss. The foreplay was almost over.
Her room. Anticipation and urgency were in control. He about lost it on the spot when he discovered what she was wearing for underwear. She came, for the first time, upon penetration, and for the second time when he orgasmed not too long after. Their needs and passion were unrelenting—continuing through the not so early hours of the night. They finally rested. Exhausted and, at least for a short time, still coupled together, until the dawn.
Part 3
Morning brought more need, but this time their lovemaking was measured, tender, and more lovingly passionate. Afterward, both were sexually spent, fully satisfied, and felt a tremendous closeness. They just held each other for the longest while. Neither had work commitments until later in the day, so they called for a large room service breakfast and just talked, mostly about small things, and took pleasure in each other’s company.
He was curious about one thing—the conference. But how to ask her about it?
Their conversation paused for a little, so he thought he would give it a try.
“I’ve been meaning to ask. That conference in Atlanta, I know a little about that group. How did you come to be there?”
A look of concern flashed across her face, and he saw her trying to think of how to answer. Finally, she took a deep breath—
He is hoping the spell hasn’t been too completely broken.
“I was going to have to share this with you at some point, and wasn’t quite ready, particularly after last night—which was absolutely amazing! (She takes his hand and squeezes it.) So here goes.”
“I was, several years ago, well, a professional dominatrix. I am retired from that now, and will never go back, but that is how I paid for college and graduate school. I still have friends in the scene, and several were at the conference, so that’s why I was there. I am also well-regarded, reputationally, in those circles, so I sometimes sit in on seminar panels. I was very, very good at it. If I went back to it I could probably make as much or more than I’m making now. But I had to get out. And I never ever had sex with any of my clients—male or female. While I did take pleasure in certain aspects of it, it was all business.”
“I hope this doesn’t ruin things for us.”
Bill takes a few seconds to take in what Tracy just said, and thinks about whether and how her revelation might have changed things. He responds carefully, not wanting to put her off—
“I don’t think that changes anything. It’s actually kind of exciting in a naughty, taboo kind of way. If you don’t mind me asking, why did you retire?”
“A lot of reasons. One, I kind of started liking it a little too much, and found the sessions frustrating. Not because I wanted sex, but because it was really the subs who had control. You would do to them what they asked, not what you wanted—I started feeling that I was the submissive. I would research and study, learning things that could have taken those interactions to the highest and most extreme level, but couldn’t put them into practice. So when I started excelling at work, I gave it up. I quit. Cold turkey.”
“You are the first one I’ve been with since.” I hope that’s okay?”
“Yes that’s okay.” (Kissing her tenderly.)
Tracy sighs, relieved.
“But wait, how did you know about the Collective?”
This takes Bill off balance, and he blushes noticeably.
“Well, I did have an interest in those kinds of things. The interest actually took a great toll on my marriage—it may have even caused the breakup. My fault really. We tried counseling, but it didn’t work. She admitted after the divorce that she had been jealous. That she thought I lusted for that more than I lusted for her, and she couldn’t handle it. This wasn’t true, but she felt it anyway. The breakup was very difficult, and I learned that those kinds of things have little to no place in a relationship.”
“So I too have quit. Never to go back.”
“Out of curiosity, were you the dominant?”
(He blushes again.)
“No. I was the submissive.”
(He looks down.)
“Hope that’s okay.”
“Of course it is. It’s kinda like we’re a pair of recovering alcoholics or adicts or something.” (Laughing and smiling.) It’s more than okay.”
As she say this she reasons that he was probably into the feminization aspect of the scene—his features even had almost a delicate quality to them. But she doesn’t ask. Those tendencies never do fully go away. She feels a twinge between her legs. He continues—
“Well I’m glad we got that out of the way. Last night was evidence that neither one of us needs that kind of thing.”
“Agreed! Completely.”
“Now where were we?”
Part 4
It was quite the whirlwind romance. They were able to see each other frequently, this in spite of the demands of their jobs and living on opposite sides of the country. Paris for a few days, Sonoma and Napa for a few more. New Orleans, Miami, Rome, London, and of course New York, among others, for a weekend.
Their passion for each other deepened and intensified with each visit. Neither wanted things to change. But sometimes, changes result from inadvertent or unintentional actions.
They hadn’t spoken about their respective pasts since that morning in New York. But if they were being completely honest, he would have admitted that having sex with a real life dominatrix, even a retired one, was exciting in and of itself, and she would have admitted that being intimate with someone who was vulnerable and susceptible to the dark arts she had once mastered was equally thrilling. In fact, they each fantasized from time to time about what it would be like if they relapsed together and went back. By the same token, they both feared what might happen to their relationship if they did. All this was unspoken.
That he had been into the feminization aspect of the scene was still merely a suspicion on her part, though she was quite confident in her ability to make those kinds of judgments. But something inside here told her that she had to find out for certain. But how?
She came up with a plan. So what harm would it do if she “sissified” herself and offered her sissified self to him to do with what he pleased? She could buy an outfit from one of those sites that cater to sissies for her to wear, and test his reaction. At worst, he might think it silly, but it would still be sexy. And at best it would confirm her suspicions. And either way it would be fun.
Tracy’s ability to plan and her obsessive thoroughness and attention to detail had been the key characteristics that made her an incredibly talented systems engineer and had enabled her rise up the corporate ladder. These were the same qualities that made her a superior dominatrix—almost fetishistically pursuing the fetish. So if she was going to present herself as a “sissy”, the presentation would have to be perfect in all respects. She well knew about sissies and all the little whistles by which they could be manipulated—playing with them was probably the most erotic thing she had done in that prior life, and her favorite part of that life. So what she had in mind for Bill would be planned and designed to perfection.
She knew from experience that the whole sissy fetish was full of contrary and intersecting ideas and fantasies. It was the existence and management of the conflicts that made it exciting on both ends. For the male, femininity becomes erotic, thrilling and humiliating at the same time. The imagined construct is pure fantasy, yet highly addictive. But once the male ejaculates, the fantasy is over, at least until the next time he gives in to the temptation, and a period of guilt and denial typically follows.
Her interest was deeper. To her, helping the male to indulge in the fantasy was only the first step, the enticement, in a process which she thought, if done correctly, would lead to the male being wholly and completely enslaved by the femininity.
Due to the nature of the male’s fetish and fantasy, this end result wouldn’t be foreseeable, and he could easily be led helplessly down the path.
That was one of her frustrations in her prior life—only being able to help consummate the subs’ fantasy, and unable to realize hers. The end of her imagined path was complete emasculation and enslavement, both in fact and in femininity, something no horny male would expect.
But the purpose of this was not to explore her fantasy, but to figure out his. And as her plan entailed neither domination on her part or submission on his she reasoned that it would be safe for both of them.
So, what to wear? After some time on the computer she settled on a Pretty Ribbons Uniform, in pretty pink, from an online store, complete with matching pinafore, panty, petticoat, bra, suspender belt, stockings and shoes. Just looking at the outfit on the site made her throb down below. And she couldn’t resist the matching mincing ribbons.
She was off to a good start.
Now is where her perversions and imagination took hold. She thought about how she would create the perfect fantasy sissy. His perfect fantasy sissy. She thought about how she would have to prepare herself. The sissy would need to not have body hair—so she would have to attend to her arms, her mons and the other places where she might have even fine body hair. That would be easy.
The sissy would need to be pierced. Multiple in the ears—already covered. Nipples? God she would hate that—but necessary. The same with the tongue—but it would only be temporary and she could take it out. On the fence about the nose, and her belly button had already been done. Which left her nether parts—about which she was also undecided. Usually those piercings were for practical purposes—to support chastity and inhibit masturbation. She would have to think about that.
And then there was chastity management itself. Her sissy would have to be controlled. Self-stimulation made impossible But what about her? Her session preference in the prior life would have been a ball trap device, but she didn’t have balls to trap. And besides, while those devices were effective for sessions, they were nowhere near inescapable. She realized that she hadn’t before thought through what type of chastity her sissy would wear. Maybe something to ponder for the future?
Back to the question at hand, what kind of chastity would she wear? If it was her own female submissive, the answer, a pierced-on permanent shield, was easy. But she wasn’t going to do that to herself. It ultimately came down to two options, both of which would involve a belt Option one would be a male belt with a penis tube. Even if she didn’t have a penis it would still create the illusion of a sissy front. The other option would be a true female belt. She had worn a female belt before, and while it didn’t completely prevent her from achieving orgasm, it did a reasonable job and was incredibly frustrating to wear.
She chose the second option, both because no dominant would allow their sissy to orgasm freely and because she had, stored away with her toys, a vintage Tollyboy female belt, custom fitted for her to wear, that was as effective as they get. It would also allow access to her ass courtesy of the attaching chains. And she would need a jeweled plug for her ass.
Method of chastity decided, she began to work though the last details. This would be the hardest part—where the “devil” dwells.
Makeup and hair? She could have hers done to look like the model on the web site. Surely Bill had been on that site, so that had potential. She would need a wig. And she was sure one of her girlfriends would be more than happy to help her with her hair and makeup.
Perfume? Something feminine and submissive smelling. Maybe something from Chanel? She would shop for that at a department store.
Collar and restraints? Shoe locks, of course. And for the collar and cuffs, 30 mm polished steel with d-rings and click locks. She loved those locks—a sub could be completely restrained in a manner of seconds. Terrifyingly quick, as she thought about it. Merciless and inescapable.
But then when? And how would she offer herself to him?
Oh my. Brilliant!