Black Guy Uses Me As His Chastity Slut (Cross Dressing)

Cross Dressing Chastity

I should preface this story by saying I’ve never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with cross-dressing, I must admit to some fantasies involving other men.

I never expected anything to ever actually happen, and it’s my own fault really. I had been paying a beautiful, very sexually fetish driven woman for her chastity services online. She had a pretty good system. She had me mail her one of the keys to my lock and then she sent me an envelope with a personalized stamp on it for the second key. The second key was for emergencies only, in case I needed to go the hospital or something like that. The deal was she would ask to see the envelope every single day via webcam to verify it hadn’t been open.

Once a week she’d allow me to perform self cleanings under her webcam supervision. She had it timed perfectly that the key would arrive on a certain day of the week and would get back to her as long as I mailed it the day after the cleaning. It was pretty convenient given the fact I hadn’t found anyone locally to do the services she provided. Plus, she would randomly send pictures of herself to my phone to tease me. She knew I had a huge pantyhose fetish so I could expect random pictures of her feet, her feet wearing sexy shoes, or even her with another guy all dressed up in sexy outfits and pantyhose. All the while, her text would remind me I was her chastity slave.

Needless to say, I both loved and hated it. At my weakest, I wanted to break the envelope, let myself out and masturbate like I had been used to, but I knew if I did that, there would be no more online Mistress. She had a strict rule. If the emergency envelope was ever broken without her consent/justifiable cause, then she was done. She would mail back the other key and that would be it. No more services from her. It kept me honest, and I had been locked up for several months without an orgasm, save the occasional wet dream, which she understood was natural, but still punished me during our webcam sessions by instructing me to fuck my own ass with a dildo she had me order.

So there I was, locked up for months, enjoying and hating the torturous services of my online Mistress when it all happened. It was late at night, I was dressed up in black pantyhose, a mini leather skirt, black tank top, red and grey mid-drift sweater, and my tall black boots. I couldn’t help but feel sexy. I had been looking at online porn and enjoying a few drinks when I suddenly had an urge to smoke.

The decision to smoke caused everything else to follow. I really didn’t want to change out of my outfit just to change back into it after I came back inside. I lived in an apartment on the second floor with a balcony, and the balcony was relatively safe from view from the other tenants. I figured it wouldn’t be a huge deal to step outside, fully dressed, for a quick cigarette.

It was chilly outside, and I loved the feeling of the cool breeze against my pantyhose clad legs. My skirt was short, just covering my upper thighs and locked up cock. I hadn’t bothered with a wig or make-up, as I just enjoyed the feeling of the clothes. And then it all happened.

Suddenly, a car came around the corner of the building, its headlights shining directly on me. As quickly as I could, I tossed the cigarette and tried to dart inside. I had closed the sliding glass door to prevent smoke from entering my apartment, so it took me longer than I would have liked to get back inside. I hoped the driver hadn’t seen me, or if he did, thought I was just a chick having a late night smoke.

Nervously, I locked the glass door and closed the blinds. No harm, no foul. No one would be the wiser.

Except there was a knocking on my door a few minutes later. And then more knocking. I went to the door to see who it was. Through the peep hole, I saw the face of what appeared to be a very large black guy. Holy fuck, what did he want?

Again, more knocking. And then words.

“I saw you outside and unless you want me yelling at the whole apartment complex, you better open up,” he said in a deep, baritone voice.

Shit, was this really happening? There I was, in my women’s clothes, locked up in chastity and a black guy was crashing down my door. I really didn’t want him yelling at the top of his lungs to my neighbors that he had seen me dressed up like a chick outside.

But I was scared to let him in. What the fuck did he want? Why was he insisting on coming in?

Quickly, I texted a co-worker and asked them to call the cops on my behalf if I didn’t text back within an hour. Maybe I’d get robbed or worse, but at least backup would arrive.

Putting on my most confident face, I went ahead and opened the damn door.

The guy looked at me, scanning me up and down. He didn’t seem surprised, shocked, or disgusted. Quite the opposite.

“Would you invite me in, please?” he asked.

His voice was rich, deep, and had the essence of manliness. He was wearing designer jeans, black shoes, a sharp button down shirt, and an expensive leather jacket. Needless to say, judging strictly by his clothes, he wasn’t a poor person by any means.

I wasn’t terribly tall, only 5’7″ and just over 6″ when wearing heels. This gentlemen still towered over me, despite my tall boots.

“I, uh, sure, um come in,” I said, stepping aside, very unsure what to do.

He came into my apartment. I never dressed in front of other men. I just never have. I’ve dressed in front of girls, and girls claiming to be into it, but never, ever, in front of another dude. It just felt awkward, wrong, and secretly arousing.

Being the polite host that I am, I of coursed asked, “Um, so can I get you something to drink? Juice, water, maybe beer?”

“Have any wine?” he asked, taking a seat on my sofa. Who the fuck was this guy and why was I suddenly serving him so naturally?

“I might, let me take a look,” I said, rummaging through my cabinets. I found an old bottle of Menage Et Trois I had purchased at one time but never drank. With my hands shaking, I uncorked the bottle and poured two glasses.

“I hope this is alright, it’s all I have,” I said handing him his glass.

He didn’t drink right way, but he smelled it. “Ah, Menage Et Trois. Not bad for cheap wine,” he said taking a sip.

Argh, his voice was almost seductive in of itself. It was so vibrant, it almost made the air around him move.

“My name is Damien and I bet you ask why I’m sitting here. Well, I saw you smoking on the balcony in all your glory. It takes guts to step outside when dressed up like a woman, I’m sure. I think some part of you wanted to be seen.”

I sat next to him, nervously sipping my wine.

“You have a great body for a guy trying to dress like a chick,” he said. “You have great legs, good shape at the waist, and you don’t over-do the breasts part. All in all, very sexy.”

I wasn’t sure where this was going, but I sipped some more of my wine, clutching my cell phone in the other hand. What was he going to do with me? He was a huge guy, and could overpower me very easily. I was a slender white guy with little to no muscle, dressed up like a girl. I couldn’t do anything if he suddenly became violent.

He took another sip of his own wine. “Hmm,” he hummed, “Cheap doesn’t mean the wine isn’t good,” he said. “”So I bet you are sitting there, scared, probably have a text out to a friend, and are wondering why a big black guy is sitting on your couch? Might as well get everything out in the open.”

“You are correct on all accounts…my friend will call the cops in an hour,” I admitted.

He chuckled, “And that’s not even racist, just practical. I’d want the cops coming if some random white dude crashed my place, too,” he said.

His teeth were so white when he smiled and laughed. Maybe it was just that his skin was so dark that his teeth stood out. In any case, he had nice teeth.

“So what do you want? You found me out…you saw me…and now, why are you here?” I asked, feeling a little more confident.

“Because I am a Dom. I know what you are. A cross-dressing male, maybe even a sissy male. I like men who dress up as chicks. It makes them that much more easy to control. I’ve got several guys and women under my current dom-ship. When I saw you outside, I couldn’t help but be interested in your situation.”

Was this really happening?

“I, uh, already have a Mistress,” I managed to stammer.

“Oh, well, she is a lucky lady to have you for a pet,” he said, sipping his wine.

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