The View From the 23rd Floor Pt. 01

(fetish, FLR, cross-dressing, feminization, chastity, reluctant, lesbian, DS)

Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget the whole thing.

Synopsis: Daniel's cross-dressing fetish is discovered.

He'd purchased the condo for an obscene amount of money, but the views were phenomenal. He could see the city in almost all directions. And it was breathtaking on a clear day, and even more so at night.

After settling in, he had added a telescope on a tripod that stood in his living room in front of one of the big windows so he could look down at the ants wandering the streets far below.

Only his view to the West was blocked, by another similarly tall but larger building. But no matter, everything else was perfect.

When he bought the place, the builder wanted another, smaller fortune for designer window treatments. Sick of writing checks, he declined that offer, and, since he was too high up for anyone to really see what he was up to, and he didn't want to ever block his view anyway, he just left his windows clear and unobstructed. And that was what led to his downfall.

He was relatively wealthy, and single, and content with his existence.

Several years ago, he had divorced his wife, thankfully before they had started a family. After a couple years of wedded bliss, things had simply fallen apart. While he had seemingly become more attracted to sex, and kinky sex at that. She had become less interested and unwilling to experiment. Their differences in that one, important area had led to arguments, then fights and then to the split.

It had never been about money, because they both had plenty of that. They were both successful and well-paid attorneys, specializing in business and tax law. And that allowed him to buy his new home.

It was in the dry spell of a newly divorced man, that he really started experimenting, living out some of his previously repressed fantasies.

By the time he settled into his dream condo on top of the city, he had accumulated quite a collection of very adult toys.

He'd sampled a number of fantasies and kinks and with money to spare, he'd picked up quite a collection of bondage gear and chastity toys and latex clothing. All of it for solitary use. He hadn't had the energy or the inclination to try and find a woman who he might share those games with.

But, for some reason, buried deep in his psyche he found cross-dressing to be his favorite sex-driven past-time.

It wasn't simply because he was short and slight of build with long legs, and a smooth and thin face. Those aspects made it easier for him to purchase feminine things that fit him well. He had always envied women their ability to make themselves beautiful, and to use their beauty to get what they wanted, by controlling the men who reportedly ran the world.

He had certainly enjoyed the other kinks he'd tried; he'd found them enjoyable, too. He still played with those things, from time to time. But crossdressing was his favorite.

He attributed his focus on women's things, in part to his ability to enjoy his feminine side, alone, without a partner.

Before he'd become enamored with cross-dressing, he'd found self-bondage, or locking his cock up, to be enjoyable, but not necessarily addictive, solitary adventures. He always had access to the keys. There was no loss of control, which he deemed to be important aspects of those sex sports.

With his cross-dressing, he could enjoy the artistry of his successful feminine persona. He could work to master the fashions, the make-up, the hair styling, with wigs of course, and the mannerisms practiced in front of the mirror. And then he could enjoy his evenings imagining himself as the woman of his dreams, literally.

Over the last several months, alone in his high-rise, he proudly became very good at impersonating a woman. And he practiced his favorite fetish often.

So much so, that he had even ventured out, on a couple of occasions, to see how well he could pass.

Of course, he had kept those trips short, and after dark, and had avoided crowds or crowded places. He didn't have the courage for that. And even on those adventurous occasions he had been petrified of discovery and the humiliation that would surely be the result.

But, after each trip, he realized that that very threat, the idea of being discovered and embarrassed, in public, added a delicious spice to his outdoor adventures. He didn't have the courage to take those risks often, though.

Everything was going well. His life, both at work and at play, was happy and comfortable, even if it was a bit lonely. Until one evening when he came home after a long and productive day at the office to find a note slipped under his door.

Dear Daniel, I've seen you, and photographed you. You do look like a beautiful woman.

Oh shit!

Who? What? When? All traveled through his mind with the speed of light.

Someone knew of his cross-dressing games, and they had photos! Despite the current political and social climate, if word got out, he could lose everything. His stuffy and conservative law firm would never accept it. His humiliation would be epic. Shit!

He was tempted to dump all of his feminine things to get rid of the evidence, but if they already had photos, it wouldn't matter. And he enjoyed those things too much to just throw them in the trash.

He drank too much Scotch that night in a futile attempt to reduce his worrying and get some sleep. But nightmares haunted him anyway. In the morning, feeling crappy, he went to work with no idea what to do, other than just carry on, worry, and quit his cross-dressing escapades, at least for a while.

A few days later, another envelope showed up, and this time it included photos of him in full feminine attire. Shit! Shit! Shit!

He poured himself a huge drink and sat down to take a better look.

The first one he examined was taken out on the street in front of his building, on one of his rare trips out, en femme.

But the rest of the shots were obviously taken through the big windows that provide him with his wonderful views of the city.

For a moment, he forgot his situation as he examined the picture. He did look good, just like the woman he dreamed about being. But shit! He had trouble; this was no time to get caught up in his fantasies.

Studying the details of the pictures, he realized that they were taken from the high-rise building next-door. The one that blocked his view, Westward.

Of course, he couldn't determine from what location. It had to be from a condo close to the level of his floor, but that still left a couple dozen possibilities.

He stepped hurriedly over to his telescope and repositioned it to look out at the other condominium tower.

He was able to clearly see into those condos and with the magnification his instrument provided he could see very well. But as he scanned from window to window, nothing caught his eye. Many of them were dark, no lights within. And most of the rest had curtains or blinds that prevented him from seeing much of anything.

Damn! He should have purchased those cursed window treatments!

Then he remembered that there was a note in amongst the incriminating photos. He hurriedly stepped back to where it had fallen onto the table and opened it.

Dear Daniel, I think we should talk. I have so many photos of 'Danni', I'm not sure what to do with them all. Meet me, tonight at 'Jennie's Room' on Front Street at 10:00. You should be comfortable there as it's a gay bar, and there will be plenty of lesbians and Gurls. Of course, you must come as the pretty and well-dressed woman that you are. Impress me, and don't be late.

Shit! Shit! Shit! He thought. He looked over at the clock and saw that it was already seven. He'd have to hurry and get showered, dressed and made up in time to get over to Front Street. And even then, he'd have to drive or take a cab to get there in time.

He looked quickly at an on-line map; he'd never been to 'Jennie's Room' before. He wasn't gay. Just a cross-dresser, he mumbled to himself derisively. A caught-out one, at that. Based on the views, he concluded that there would be no parking anywhere nearby, and he didn't want to walk around in that neighborhood, while dressed to impress. He'd have to take a cab. Actually, 'Danni' would have to.

He'd never created a name for himself, when he was a she. It hadn't ever been necessary, and on the one occasion when he thought about it, it had seemed a step too far. Once she had a name, his female persona became too real. At least that's what he'd uncomfortably decided at the time.

But now, she had been assigned a name, by whoever it was who was badgering him.

Hurriedly, he stripped off his suit and tie and showered before starting to dress as a woman. He pulled on a pair of panties, and tucked his cock back between his legs. A padded girdle held it firmly, gave him a flat front and its padding gave him hips and a rounder ass. A bra with breast forms built out his chest.

Black pantyhose finished his underthings. He'd recently started shaving his legs, and his groin, to improve his looks. And the satin panties and smooth nylons felt wonderful.

A slip and a pretty navy-blue dress finished his outfit. He added pumps a gold neckless and bracelet finished it all off, and he stepped into the bathroom to struggle with his make-up. He'd been practicing a lot, but still had trouble achieving the proper feminine look. He'd slowly thinned his eyebrows a bit, over the past few months, so as not to draw a lot of attention to the change, but they still appeared too thick and manly, at least in his opinion.

It took him almost an hour to achieve a decent look. His nervousness didn't help.

Finally, he pulled out his brunette wig and fit it tightly to his head.

He did have a purse, a small one he'd picked up, just for those few occasions when he did bravely go out, as a female. So, he was able to grab his keys, phone, ID and some money, as well as a mirror and a tube of lipstick.

Then he headed out, just in time to make his Ten O'clock appointment.

He called a cab on the way down.

The cabbie didn't seem to notice anything amiss, and Daniel, now Danni, arrived on time at the bar.

He walked in to find the place to be better than he expected. It was quietly subdued and dim inside. Couples were scattered about, mostly girls paired with girls and men with men, chatting quietly. There were a few tables with four or more people, laughing and adding background noise.

But to him the place seemed more cozy, than hectic and brazenly 'gay'.

He walked slowly into the abyss, until he spotted a woman waving at him. He took a deep breath and walked over.

"Hi Danni," the girl said loudly as he got close.

It spooked him, but he carried on, holding out his hand to shake, as people do.

She smiled and stood to greet him and shake hands.

"I'm so glad to finally meet you. You look lovely. I'm Audrie, by the way."

He sat down, carefully across the little table from her, while he checked her out.

She was tall, pretty, attractively dressed, and clearly outgoing.

Just then a waitress showed up. "What can I get you two ladies?"

Audrie spoke up first, "I'll have a glass of the house Chablis. Please."

"I'll have that too." Danni added. He didn't really care for wine, but it always seemed to be the norm for the women he had dated.

They chatted like two people who had just met on a blind date, for almost an hour before Audrie finally got down to the important topic. Daniel realized that in all of that time, he had learned virtually nothing about the girl sitting across from him. She was obviously intelligent, and a well-educated professional. And she was confident and witty, too. He really would have liked to be dating her.

At that point in their 'date' she reached out and rested her hand, warmly on his.

"I'm really glad that we were able to meet like this. And I'm sorry if my little notes upset you. I'm sure that it was a shock. But I find you fascinating. At least what I've seen of you." And she paused to chuckle.

He couldn't help but find her to be pleasant company, but...

"I contacted you because I want to get to know you better, I think you and I can have some fun, together."

She paused again to take a drink from her glass. While he sat confused and fearful, trying to figure out what she meant.

"You need to understand that I have no evil intent, here. I am not trying to shake you down out of avarice or greed. I don't need your money. But I am intrigued by you and your, ah, personal games, and I want to participate. Okay?"

He wasn't sure how to answer her. 'Hell no.' seemed too crass. 'Sure, why not?' too cavalier and dishonest. But he couldn't refuse her, she did have those pictures. And she was attractive.

"I guess. I'm still not really sure what you're looking for. You must know that I'm uncomfortable with those photos you have."

"Oh, don't worry about those. They're very private. Just between you and me. And you'll find out more and hopefully get more comfortable with me, when I come over on Friday evening."

"Oh?"

"Yes, don't worry, it will be after dinner, say around seven? It will just be for a visit, and a chat. I really want to get to know you better."

She flagged down the waitress, indicating to him that they were done for the evening.

"Oh, and please give me your cell number. I'll be calling you."

He felt he had few options, so he rattled off his number and she punched it into her phone. She didn't offer her number, and he didn't think to ask for it. He should have, but he was still too distracted by events.

After she paid for their wine, she stood up and he did too. She actually leaned over and gave him a kiss on the cheek. It surprised him, only adding to his confusion.

"I like your scent. That's something you can share with me on Friday. See you then."

Then she stepped back, and started to turn away, but paused.

"I'm going to the ladies' room. I don't imagine you'd like to accompany me. You know us girls always go off together to pee." He could see a devilish gleam in her eye, he would have found it charming, if he wasn't dressed as a woman, in a gay bar.

"Um, no. Thanks anyway, but I think I'll wait until I get home." He said casually, and he was even able to add a quick wink to acknowledge her little game.

She laughed and walked away, as he watched.

He got up and moved toward the door, in a bit of a trance, calling a cab as he worked his way through the tables.

The Taxi showed up surprisingly quickly and he was gone before she came out. That was a relief, not only because he didn't want to talk to her anymore, but because he really did have to pee. That was another aspect that had always vexed him when he thought about going out dressed as he was. Of course, he couldn't use a men's room. But using a lady's room, and the close scrutiny of women in there with him, would expose him to discovery. It was a daunting situation that he didn't want to have to face.

He arrived home with no issues, and after relieving himself, collapsed, mentally exhausted on his couch. He stayed in his feminine things, inattentively watching the television until he started drifting off. Then he stripped off his clothes, and his make-up and went to bed.

For the next couple of days, he tried his best to focus on work, and forget about everything else. There was nothing he could do to change anything. So, just carrying on, was the easiest thing to do. All the while, though, in the back of his mind, a clock was ticking away the hours until Friday evening, when he'd have to face Audrie once again, this time in his home.

As soon as he walked into his door that Friday night, he started getting nervous. Very nervous. This was a big night. He hoped that things could be smoothed out and he could go back to his solo pursuits. But he suspected from their initial conversation, that wasn't going to happen.

After he put down his briefcase, he headed into his bedroom to change. He stripped off his suit and took a quick shower, shaved, and then began the ritual of turning himself into a woman. Danni, he now called her.

As always it was a long process, taking most of an hour, despite his hurrying. It gave him a better understanding of why the girls he knew always seemed to be late. And they'd had a lifetime of practice.

Fully dressed, made-up and with his wig in place he poured himself a stiff drink and waited for her arrival.

From the moment she walked through the door, it was clear to him that she was in charge. She looked great, in a pretty floral dress and sandals with three-inch heels. In the light he could see how pretty she was, and her make-up made her look sexy, too.

He got her a drink and they sat down on his couch, angled toward one another. He was careful and compliant, while she was friendly and in control.

Without prelude, she began pumping him for his life story, and from there she began questioning him for the details of his sex life. To him it seemed more like an interrogation, but he did his best to satisfy her demands for personal and often embarrassing information

She's really good at this, he thought. And also good at determining when he's not being truthful or forthcoming.

And it doesn't hurt that she's pretty, and confident and fun to be with.

He tries to figure out who she is, what she does when she's not stalking him. But it's difficult. Based on a couple of her comments she's either a businesswoman, or perhaps a psychologist. He can't really be sure. In any case, she's intelligent, confident and clearly understands human nature.

At one point, impatient and annoyed, he interrupts her questioning. "But how did you find me? And why? Really. Why are you here?"

"Well Daniel, I'm a people watcher. That's my hobby and part of my work, too. And I have a telescope in my place, just like that one." And she waved toward the one he had over by his windows, before continuing with her explanation.

"I use mine differently. You look at the scenery; I've seen you. I look at the people. And I get the best view, and the easiest, looking at this building. And one night I spotted you, and you fascinated me."

He shook his head in wonder, "so you're a stalker? Or a peeping tom -- or is it, Tammy?" He didn't say it angrily. He had a slight smile on his face.

And she didn't take it as an accusation. "Well, perhaps a bit of a stalker. When it comes to you, I guess I am. But I'm not spying on people to see nudes, tits or cocks. I'm doing it more as a study of human nature."

She paused, and chuckled. "And your human nature, attracted my interest. So here I am."

"I'm not sure if I should be flattered or frightened. Actually, I'm pretty sure I'm still frightened."

"Oh, sweetie, don't be. I like you, and I think you're intriguing and attractive, too. As a girl, that is." And she laughed, while he blushed.

But then she resumed the interrogation. And while they talked, he drank, trying to calm his nerves and come to terms with his situation.

Unbelievably, they carried on like that all night, and by then, he had admitted to everything. Shared far too much information. Including the details of past sex life, and all of his fantasies.

The always impressive sunrise was just starting to appear, when she finally ran out of questions and stood up, stretching sexily.

He thought she was going to finally leave, but he was concerned that there had been no discussion over the photos.