Cross-dresser Blackmailed - Pt. 01

This is a fictitious story; however, it is partly based on a real-life fantasy of mine.

I live on the fourth floor of a prestigious 20-floor residential block. I have a very large double door, floor-to-ceiling, that opens onto my large balcony, which sits beneath the balcony above me. Opposite my block, an office block stands about 15-20 meters away; it's also high but mostly glass. Although the glass looks reflective, I can see inside the offices from my flat.

There are about 150 residences in my block, and those on the upper floors get larger the higher you go.

The residents are completely mixed, but because rents and purchase prices are high, they tend to be professionals of all colours and religions. Some are only occasional residents, and some live here all the time. There are three lifts that go to all floors, and I meet many people coming and going.

My girlfriend stays with me about 2-3 days a week, and I am very much in love with her. We enjoy a great sex life and like to experiment with bondage every now and then. I am in my early 40s and virtually hairless except for my head of course, which I keep buzz-cut.

I work in software, remotely, and can work when I choose, to a certain extent.

But I have a secret: I enjoy occasional cross-dressing. I am not gay and am not attracted to men or trans people in any way, but I do like dominant women.

Sometimes, when I am on my own, I dress in black stockings and suspenders, heels and a tight-fitting black dress and go about my business in the flat. Of course, I have vertical blinds across the balcony and draw curtains so nobody can see me.

CAUGHT

My girlfriend went home to her place that morning, and I sat in my flat wondering what to do with myself when I heard something sliding on the floor near the entrance. I got up and went to the door, and there was an envelope. It must have been slid under the door. I picked up the envelope and opened the door to see who it was, but I couldn't see anyone outside.

I opened the envelope, and a letter and some photos fell out. I picked up the photos, and to my horror, they showed me mopping the floor in my flat, dressed in my black stockings and suspenders. The photos were quite grainy, but it was clearly me.

I read the letter:

"Dear Fellow Resident

As you can see, I have photographed you in a precarious situation. Actually, you look very good in black :-)

You may be wondering how I took these photos! If you want to find out, come to my apartment 1002 at 6 pm this evening. Bring ALL your women's clothing and accessories.

Don't worry too much. I do not wish you harm, and I don't want any money. As long as you follow my instructions, your lovely girlfriend will never know your, or should I say, OUR secret.

I look forward to meeting you properly later.

Best wishes

Cynthia.

I wracked my brain to think who this Cynthia was, but I only really knew who lived where on my floor. SHIT! I'm in big trouble. What on earth does this Cynthia want with me? I don't have much money, and if she lives on the tenth, she clearly has a large, expensive apartment. What if she wasn't the only resident in the apartment? My mind was racing. I didn't have any choice. If I wanted to keep my secret from my girlfriend, I would have to go to 1002 at 6 pm as instructed.

I put a limited amount of my 'gear' in a bag but left out some kinkier stuff like latex and some bondage gear, and waited for 6 pm.

I dressed in jogging pants, a T-shirt, and trainers and rang the bell. After a short while, the door opened, and a woman invited me inside. She locked the door behind me and told me to put my bag by the huge sofa and sit down.

"Hi, I'm Cynthia. Welcome to my apartment."

She looked Chinese and was maybe 5 feet 7 inches tall. She wore tight purple gym bottoms and a matching top. She had quite large tits for her size, and for a Chinese woman. She had long black hair, and her lipstick matched the purple of her outfit. She wore expensive-looking trainers and looked quite athletic. I guessed she was about my age.

The apartment was very big. The main room we were in had a large lounge area and led to a modern kitchen with a good-sized island and stools on one side. I could see at least 4 doors that most likely led to other rooms.

"Do you live here on your own then?' I said, trying to be casual.

"Yes, don't worry. Nobody else is going to jump out and surprise you. I am the only 'holder' of our secret."

Cynthia wore a smug, wide smile, and I guess she deserved it. I was there at her command, and she had caught me, the cross-dresser.

"As I said in my letter, I do not want any money from you and do not want to harm you. I don't even want to tell your girlfriend our secret."

When she said "Our secret" again, I felt a little palpitation. Where is this going?

"As to how I got the photos. You see, I am an amateur astronomer and one day I was adjusting my telescope, the big one over there in the corner. I was playing with the focus on the office block and noticed the sun's position was making it reflective and I could see this block in the reflection. I was curious and saw that your apartment had the blinds closed, but when I looked closely, they weren't completely closed at one end, and when I played with the focus, I could see partly inside your flat.

I didn't set out to snoop, but I couldn't help but notice you were, how should I say, 'dressed up', so I took some photos with the built-in camera.

I have lived here alone for some time now, after my divorce three years ago from a complete bastard. I am not looking for a new boyfriend or husband. I just like to have fun, and you, hopefully, will be part of that.

You see, I also have a secret.

I get horny, and I'm quite attracted to cross-dressers. Not all cross-dressers, you understand, but those like you, I guess. Not gay, with a good body, who like to dress up and maybe play games. So when I saw you, I hatched a plan, and now I am executing it!"

"What do you want from me then? You already know I have a girlfriend."

"Actually, I think I can help you in a weird kind of way. I want you to be my occasional cross-dressed sub. We can arrange a time that fits into your working schedule and personal life, and you get to live out your fantasies by cross-dressing for me, here in my apartment."

I was stunned and needed a moment to process it.

"So, you want me to cross-dress for you here? When? What if I refuse?"

"As I said, I don't want to ruin your current relationship, but maybe you would enjoy dressing up for me here and playing some games. You can even keep your stuff here. That way, your girlfriend will never find it."

"What if I say no and go back to my flat and never speak to you again?"

"All I ask is to give it a try. I don't want to give your girlfriend copies of the photos, and I know you don't want me to."

"No, please don't do that. Can I think about it a little bit more, please?" I tried to play for time, at least for now.

"I am willing to let you take a little more time to consider your situation; after all, it's quite a revelation. Or could be! First things first, though. Let's go to your flat and get the rest of your gear. Once I have all your stuff, I will give you 24 hours before I decide whether or not to leave your photos in plain view in the lobby of this block."

"This is all of my stuff, I'm afraid," I said, slightly scared.

"Nonsense. If I were you, I would not bring everything. I want to keep everything you have here. Call it part of getting to know your kinks better so we can have as much fun as possible."

Cynthia got up, went to the door, and beckoned me to follow her. She actually had a great figure. Curvy and in all the right places. Maybe this could be fun after all. What am I thinking? She is blackmailing me and could do something terrible.

"By the way, what is your name?"

I saw no benefit in lying to her. "James," I said.

"Nice, come on then, James and bring your bag."

I let her into my flat. She bounced over to my sofa and sat down.

"Right, James. Fetch ALL your stuff."

I went to my big cupboard in the bedroom and took a case from the top shelf. I unlocked it and started to open it.

"Bring it over to me, here."

I put it in front of her feet and opened it. She started to look through my stuff.

"See, you have collected lots of stuff. Oh my, look at this!"

She held some of my bondage stuff in her hands and lifted it up.

"Delicious, James. So you like bondage as well, huh!"

"I guess so. My girlfriend and I occasionally like to do some light bondage, but I like to experiment with some self-bondage when I am dressing up."

"What fun. I think I would like to tie you up as well, but I think I will order some special stuff that we can play with in my apartment."

Cynthia went through everything: corsets, gloves, short skirts, pencil skirts, latex, PVC, stockings, suspenders and two pairs of shoes. One pair was a type of court shoe with a fairly big heel and the other a stiletto, both in black.

"Right, James. Let's put this all in the case, and I will take it upstairs with me and put it away for you. I will order some more stuff over the next week. It will take a little while for all this to sink in for you. As I said, you have 24 hours. Download the Signal app, look up my account, cynthia10024U, and message me before the 24 hours are up, or things could go differently for you. Assuming you decide to cooperate, I will message you when I am ready to see you again."

She got up and closed the case. Pulling it along, she headed for the door.

"I'm so glad we met, James. I'll see you soon, and don't worry, our secret is safe with me, for now at least"

She left the apartment and closed the door behind her.

I sat on the sofa with my head in my hands. What on earth could I do? How can I get out of this situation?

For an hour or more, I racked my brain, trying to find a scenario where this would all go away, and my life would return to normal.

My mind started to wander, thinking, picturing what Cynthia might want me to do with her. I pictured myself dressed up in front of her, waiting for her command. My cock was getting hard just thinking about the situation, and the more I thought about it, the harder I got. Dammit!

I downloaded the Signal App and searched for her account, cynthia10024U. I found it, and there was a little Chinese girl memoji pic.

Dear Cynthia. I have considered my situation and have decided that I will go alog with this 'game' of yours, at least for now. Please do not show anyone the photos of me.

"My girlfriend is coming over later this week, staying here Thursday and Friday night and will go back to her place Saturday lunchtime. I most likely will not see her again until later the following week because of her work commitments.

Please be nice to me and understand that I am very nervous about meeting you again.

I pressed send.....

Within about 10 minutes, I got a reply.

Dear James.

I am so glad you decided to do the sensible thing. I would hate to ruin your relationship with your girlfriend, or anyone else, for that matter.

Like I said. Our secret is safe with me, for now.

I need to order some stuff that will make our time together more fun. I will message you as soon as I want you to come up to my place, most likely Sunday lunchtime, but wait for my instructions.

Cynthia.

Christ, what had I done? What might she want to do with me? I felt my cock hardening again.