Public Cross Dressing Experience Ch. 01


Don stirred in the hotel bed. He was uncomfortable, and he was unsure why. His head was pounding to the beat of his heart. He pulled his knees up toward his chest to try to squeeze into a sleepy fetal position. It was then that he realized something was very different here. He felt compressed and restricted. He was lying in a bed, but what bed? It wasn’t his. And he had shoes on.

He was confused. The room was dark, but where was he? Slowly his aching eyes focused on dark curtains at the window. Scanning the room he saw generic pictures of pastoral landscapes in cheap picture frames, and a small desk with chair. It looked like a hotel room. Alarmed, he tried to sit up but was immediately restrained by the tightness at his waist and chest.

“Jesus Christ!” he said out loud. He felt his waist and it was satiny smooth with a zippered garment running from his crotch up to his chest. He was tightly cinched in a corset. As his hands moved upward he found that at the top of the corset was a small padlock where the zipper ended, and above that was a bra filled with realistic, soft and squishy prosthetic breasts. Not only that, but his head not only ached but it felt enclosed in some way, and warm. Hair, long hair flowed from his scalp. How could this be? It was like one of those transformation stories that he read about in his fantasy searches on the internet, the ones where a man suddenly wakes up and finds that he has been magically transformed into a woman. His headache didn’t allow him to enjoy that fantasy at the moment.

“What the—? What the fuck is going on here?” He managed to sit up now, and dangled his legs over the side of the bed. How had this happened? His legs were encased in nylon and lycra stockings attached to his corset garters and he had high heeled shoes on his feet. He felt his “breasts” and they seemed quite large and were supported with a bra which allowed them to jiggle and bounce when he moved. Must be made of some kind of gel, he thought. They seemed to pull on his chest muscles on each bounce. Strange. Upon examination, they were attached with adhesive.

Fully awake now, he turned on the light and surveyed the room. This was scaring him. He had no recollection of going to a hotel or spending the day dressed up. Come to think of it, what day was it? Was it even day time? The clock beside the bed said 9:05, and just when he looked, the alarm went off, making him jump. As he reached out to find the alarm shut-off he noticed his hands, with long, fake manicured nails painted bright red. Jesus, he must have been drunk last night or something, he thought. He tapped his fingernails on the bedside table. Hard as rocks, those nails were not coming off any time soon.

Who was he with last night? Had Tessa and Jen been with him? They dressed him up lots of times and had fun with his cross dressing. Maybe they were in the bathroom, he thought and hoped. He decided to get up and try to figure this out, so he stepped out toward the bathroom in his high heels, walking the way they had taught him to walk over the past year. Catching a reflection to his right, he stared with disbelief at the image. Standing there was a very good looking blond woman, wavy hair down to her shoulder blades, dressed in a black bra, red corset and garters, black panties, and black stockings. The waist was drawn in severely by the corset to give an hourglass silhouette. He felt it now, to make sure he wasn’t dreaming. He had never been laced up this tight before, which explained his breath coming in shallow gasps. His breasts over hung the top of the corset and the bra struggled to support. Testing, he bent his knees up and down a few times resulting in the unmistakable feminine bounce.

Somehow he had been transformed into this “woman” without even knowing it had happened. His face was fully made up, and there was no residue of masculinity remaining to him. Except of course the penis rising in his panties. He had never been so surprised to be so turned on in his life.

The bathroom was empty but for an envelope with the name Donna on it. Before opening it he traced his bright red fingernails over the meticulous makeup job. It was all dry as well, with no smudging. Amazing. Ripping open the envelope he read:

Dear Donna,

By now you may realize that I administered something to you last night that hopefully dimmed or erased all your memories of the last eight hours. Your name is Donna and you are staying at the TransContinental Hotel on 5th Avenue and you are on the 16th floor.

You looked gorgeous when we finished with you at about eight o’clock this morning, but what we can hardly wait to see is you at the Metronome Restaurant at noon. You know where that is—it’s six blocks due south, just on the edge of downtown.

Now the details, at least as much as you need to know at this point, in case you don’t know it, your corset is locked on, with the laces coiled in a pocket which covers the laces in the back. Just so you know, it was a bitch of a job getting you into that Kurtköy Türbanlı Escort thing! Your breasts are glued on with a surgical adhesive I got from the hospital and cannot be removed without a solvent chemical designed for that. Your makeup is all long-lasting waterproof stuff. It shouldn’t be smudged, but before you go, you might want to refresh your lipstick. Oh, and brush your hair. Your head has been shaved and we applied the wig with the same surgical adhesive, so don’t worry about the brush pulling the wig off. It won’t. In fact we shaved your entire body, so no need to worry about any masculinity showing through. LOL

It was truly strange to see you seemingly awake and conscious as we did anything we wanted to you all night. We took some pictures which we can show you at lunch. The pictures go on your Facebook page if you somehow manage not to show up. Are you having fun yet?

Now for the truly interesting part. There are no male clothes for you to put on. I left a beautiful form-fitting dress on the chair by the balcony window. It should suit you just fine. It has enough body that it should hide the fact you are wearing a corset. The neck is high and frilly so your Adam’s Apple will not be visible. I also left you a light coat that you can wear if it is colder than the forecast predicted. The matching purse contains only your lipstick, other makeup, hair brush, and cell phone, nothing else. You have no credit cards or cash. What a shame, huh…giggles, no taxi for you! Checkout time is eleven o’clock and I have prepaid the room so you can leave when you get up enough guts…LOL. The room is booked by someone else for early occupancy today (what a coincidence eh?), so you can’t simply tell the maid to leave. She WILL ask you to leave.

I figure it’s probably about 9:30 now as you read this, so that leaves you about an hour and a half to get ready to join us for lunch. By the way, it’s Tuesday, and the downtown lunch-goers won’t really notice another well dressed woman going about her business—or will they? That depends on you I guess. I know you have never tried to pass in broad daylight before. Just remember to walk and carry your purse like we taught you, you’ll be fine. And for God’s sake, if it is hot, do NOT wear the coat or you’ll become a sweaty man in drag, and you definitely do not want that, do you? LOL

We have a reservation at the Metronome and we’ll be waiting for you.

Love, Tessa and Jen

PS: Take the pills on the bedside table to get rid of your headache. And I almost forgot, no lady is complete without jewelry. You have bangle ear rings (cheap clip-on ones but they’re pretty good) and a bangle bracelet and a fine gold necklace. They’re in the purse too. Have fun sweetie!


Don put the letter down on the countertop and stared at himself in the mirror. His heart was pounding and he felt slightly sick. They had outdone themselves this time. Sure they had tried to embarrass him before, but never like this, and never in broad daylight.

It had been fun getting hooked up with these two last year. He had met them at the fetish club over on 17th Avenue and at their request he had moved in with them as the third “girl” in the 3-bedroom condo. Tess, a medical doctor with questionable ethics, and Jen were lesbians and were amused by his fetishes for women’s clothing, dressing him up and doing him up as best they could. He loved it of course and in return all he had to do was pay his portion of the condo fees and do all the housework. It was a perfect symbiotic relationship. Until now.

He looked at the clock. It was 9:43. He pulled his panties down to the garter tabs and sat on the toilet to pee. The corset was impossibly tight and it restricted him so that he had to sit up straight. The tightness plus the new anxiety with his predicament gave him a light headed anoxic feeling. With his sharp manicured fingernail he dislodged some “sand” from his eyes and brushed it away. He decided he didn’t dare mess with the makeup in any way, as it was flawless. His head was pounding, so he went to the bedside table with a glass of water and took the pills. Sitting on the bed he waited, hoping beyond hope that they worked instantly. They didn’t.

What the hell was he going to do, he thought? He could remove everything except his corset and wig and wrap himself in towels while calling a cab, but that would still look nutty, a guy with boobs secured to his chest, a long blond wig to his head, and a corset locked on. Oh, and he remembered the letter said he had no means to pay the cab anyway. Shit! He looked around in panic, hoping to find something, anything, that could remove him from this quandary. Tess and Jen’s plan seemed foolproof. There was no way out of this.

Call the police? No way. His uncle was a police officer. Word got around.

It was 9:51. He periodically sipped the water and waited for the pills to work so his head would clear and he could find an honorable way out of this. He could just Kurtköy Otele Gelen Escort explain to the front desk that some people had tricked him into dressing this way and that he needed them to call a cab for him. He could just see the smirks. No, after creating several different scenarios in his head, there was only one way, and Tessa and Jen knew it. He had to play this out and walk the six blocks to the restaurant, eat lunch with them, and depend on their mercy to get him home some time in the afternoon.

It was 9:59. One hour and he had to be out of there. He went to the chair at the balcony window and examined the dress he was intended to wear. It was somewhat heavy in weight, but light in texture, red with some black trimming in a sexy but business style, with traces of red and black lace at the neck and the ends of the sleeves. He unzipped the back and stepped into it, pulling it up and with difficulty did up the zipper. While it was tight and stretchy at the waist and upper hips, the skirt portion hung free and swirled outward when he turned. His male bulge could not be seen. The hem was about at the knee. There was a stretchy black belt accessory with a bold gold colored interlocking buckle that he did up and adjusted to fit his corseted waist. Picking up the purse he checked it for contents and it was exactly what she had said. The ear rings were easy to attach, but they felt strange as they swung around, weighty on his ear lobes. The necklace was harder to put on, especially with his fingernails so long. He placed the purse over his shoulder and put the coat over his arm and went to the mirror, standing and turning, looking this way and that way, the ear rings jingling slightly as he turned.

10:15. His heart was pounding, but his headache was gone. He didn’t dare wait until the maid knocked on the door, as he didn’t want anyone to see him up close. He had to leave soon and hope he met no one. He powdered his face slightly and reapplied his lipstick. Walking back and forth he practiced the female walk just as they had taught him, elbows slightly in at his new waist, steps short and one foot almost directly in front of the other like walking on a railway track. He was contemplating his figure and looking for flaws but he couldn’t find any. Last item—he had to start believing he was Donna, not Don.

He stared at himself and said, “Well Donna, you’re in quite a pickle aren’t you?” Just then his cell phone rang inside the purse and he screamed like—well, like a girl. Being unfamiliar with his new nails he tried unsuccessfully to press the answer button, finally getting it right and saying, “Hello?” The ear rings clanked on the phone.

It was Tessa. “How ya doin Donna? All set for your walk?”

“Jesus Tess. What the hell do you think you’re doing? I’m dressed to the nines here. How am I supposed to get to the restaurant without drawing attention to myself?”

“Welcome to my world Donna. Most women have to deal with that all the time. You better make sure they notice you for the right reasons though. A man decked out like that creates negative attention, wouldn’t you say? Now, if you’re a good girl and act like one, that will create some positive vibes. Keep your head up and for God’s sake look confident. Don’t shift your eyes around to see if anyone is making you.”

“Shit!” He paused, trapped, “Tess?”

“Yes Donna.”

“You have to come and get me! I’m scared shitless here.”

“Aww, poor baby,” she said with sarcasm. While she always encouraged him to dress up, she never hid the fact that she believed him to be a feminine sissy. It was part of how she got enjoyment out of the relationship. Rather sadistic, but no harm done. It was what everyone wanted in the triangle, thus the symbiosis was complete. Ignoring his demand, she said, “It’s 10:35 Donna. You better get moving. We girls are going to have a wonderful lunch, aren’t we? I’m even going to order some light white wine to get silly with. See you soon.” Click.

Oh God, Donna thought, while still holding the phone to his ear. He put the phone back in his purse and took as deep a breath as possible in the corset to calm himself. “Now,” he said out loud, “I’m going now. I have to go now. Shit!”

One last check in the mirror and then he opened the door to the hallway, peeking around the frame checking for people. Seeing none, he stepped out. The open door hovered behind him like the edge of a cliff. He let it go with a surge of fear and adrenaline as it clicked and locked behind him in as final a sound as he had imagined it would be. He was on his own now. There was no place left to retreat.

His breathing was shallow as he walked neatly to the elevator. Short steps, heel in front of toe, elbows at waist, hand on purse. He was trying to control his breathing as the elevator door opened. Nobody there. Thank God. He pressed the Lobby button and waited for the door to close. Please let me have some luck here, he thought. Please. 15—14—12—11—10, the floors Kurtköy Ucuz Escort went to history above him, and then the elevator slowed and stopped. The doors parted and two thirty-something business men walked on, briefly looking Donna in the eye before scanning and staying at breast level for what seemed like an eternity. “Fuck off,” Donna wanted to say, “Eyes up HERE!”

The door closed and the elevator went to floor nine where three more men and one woman got on. The woman looked at her and scanned her with an even more aggressive eye assault, shoes to top of head. She was fat and not dressed that well and it was apparent Donna made her uncomfortable. She went to the far side of the elevator to avoid direct comparisons by the men. Nobody spoke and everyone stared at feet, men occasionally stealing a glance at breast or legs. It was so freaking obvious.

The smallest of the men happened to be standing next to Donna. The man glanced up at the advertisement monitor above the elevator doors and then cast a look directly sideways into Donna’s face. The look lasted a bit too long for Donna’s liking and he returned the glance fearfully. Their eyes met and held briefly and then the man smiled and turned away. Instinctively Donna reached into his purse simply to display nonchalance. The man knew.

Donna tried to control his knees while standing in the high heels. The breathing was the hardest, and he thought he felt slightly light headed, like he might faint, but no one else entered the elevator, and when the doors opened at the lobby no one moved out. Suddenly it dawned on him that the men were letting her exit first. As he left, he could feel the men’s eyes on his ass. Being a fully heterosexual cross dresser, he found that this was the most difficult thing to deal with. What if they hit on him?

Stepping into the lobby was like walking on to a stage completely naked in front of thousands. Or worse, stepping on to a stage dressed in women’s clothes. He felt vulnerable and alone, and struggled to walk with a feminine stature. He caught the reflection in the mirrored walls to his right and saw himself, feminine, poised, beautiful, and with a thousand eyes following his every step. Was this the way a woman felt all the time? Did they ever get used to this? Or were they looking at a man in drag?

His knees were still shaking but at least the shoes were quite comfortable. Even though the heels were about four inches high, maybe five, he walked easily down the street. People on the sidewalk parted for him. It was unbelievable, and he started to allow himself to believe that he was a she, and addressed himself accordingly in “her” mind. Donna had entered the world of womanhood and the thrill was almost orgasmic as she walked, flicking her hair back over her shoulder as she went, the wind blowing it back.

It was warm and she didn’t need the coat so it hung over her left arm. Her breasts bounced embarrassingly and the heat under her wig was unpleasant. She hoped she would not sweat. If she did, she would smell like a man, she knew. Tess had forgotten that one detail. Female perfume would have been nice.

As he walked, he fantasized. He felt as though he could live this way full time, it felt so exquisite. He could quit his job at the bank and maybe even become a receptionist, but then he remembered his voice. That could never change—or could it. He resolved to work on that and find that female tone so that passing in public was complete. His thoughts were his own as he went, with full confidence, block after block.

It was 11:35 and there was the Metronome, just on the other side of the intersection. The light was red. He had made it.

“Excuse me miss. Could you help me find this address? I’m new in the city.” A well dressed senior perhaps in his sixties blasted his way into Donna’s tranquility and feminine smugness.

Donna was going to have to find that voice, and now. He delayed as long as possible, glancing at the red light, his feet, and then his eyes. His eyes. They were not looking at Donna’s eyes at all. Again, the male stare, flicking from his face to his breasts and back again. God this was uncomfortable, he thought, and so fucking unfair. I am a person. A woman is a person, look at me, look at my face, he wanted to say.

Donna decided to just do his best. “Of course, where do you need to go?” The voice somehow came out neutral, deep, but like a Bea Arthur. But the feminine appearance he cut, with long fingernails pointing at his map, and hair flying across his face, overwhelmed any doubt the old fellow may have had, if he had even thought about it. After a brief flurry of instructions and hand waving, the man said thank-you and went on his way, glancing backward only once to look at his feminine legs.

The light had gone green and back to red in the time it took to help the man, so Donna had to wait out the red again. He felt the eyes of seemingly every man on the street, even those from cars whizzing by. This was crazy, he thought. He tried to maintain His balance between his opposing viewpoints as to why they were staring. Was it because they saw a woman, or was it because they saw a man in drag? Despite his doubts, he was now ecstatic with the ride, and barring getting beaten up by gay-bashers, he was now okay with either vision of his gender.

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