tagGay MaleDiscovered by a Black Guy

Discovered by a Black Guy

bychastity_sissy©

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 crossdressing, 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.

"I guess she's more of a keyholder," I blurted without thinking.

Damien looked at me curiously. "So you're locked up in chastity right now?" he asked.

"Yes," I admitted.

Why was I going along with all this? I should have been on the phone with the cops, but part of me wanted to see where this was going.

"How long?" he asked.

"Over a month...she is very strict," I said.

"Good, chastity slaves need to be kept locked up for their own good," he said.

My cock instantly began straining against its cage by the fact he was talking about it.

"Well, here's what I propose. I don't want to over-Dom your Mistress, but it's a huge difference having someone real life. She can keep your chastity domination all to herself, but I can offer something else. Tell me, have you ever fantasized about sucking cock?"

I nearly spit up the wine I was drinking.

Holy shit, was this guy serious? In the past, I had asked my girlfriends to let me suck their dildos after they had used them, and secretly always had wondered what a cock would taste like, but being confronted with the real thing was a whole different story.

"Well?" he asked, looking directly at me.

"Yes," I admitted, "but I liked girls. It's just when I'm dressed up and locked up. I don't know."

"Ah, well, if you'd like the opportunity to see if you do like it, I got a nice cock right here just waiting for some attention," he said, sipping more of his wine.

For some reason my cock instantly engorged itself in its cage with his words. Without really thinking about it, I slid down to the floor, on my knees, and put myself between his legs. Before going further, I stopped and sent a quick text to my co-worker letting her know everything was fine and not to call the cops.

"Good, good," Damien said. "Now, you can unbuckle my jeans."

I did as he commanded, slowly removing his belt from the occasion and unbuttoning his jeans. He wore Under Armor underwear, tight against his black cock.

When I finally got to it, I was incredibly surprised by its size. It was huge. I hate to say stereotypes are true, but in this case, his black cock was enormous. It was twice the length and twice the girth of my own pathetic dick. And it was still growing.

"I knew it. If you hated cock, you wouldn't be doing this. You would have politely asked me to leave, which I would do if you wanted. But I think you might like some cock," Damien said.

He was right. I pulled down his underwear and was staring at the enormous black cock in front me, with both hands wrapped around it, still trying to come to terms that this was really happening.

Damien moaned with the pleasure of by fondled. Like a curious virgin, I stroked his cock, moving my hands up and down his impressive shaft. It must have been at least 9 inches. I caressed the tip, knowing just how I used to like being touched. He was cut, and tracing his head gave me immense arousal.

My own cock was straining desperately in its cage, wishing it could be touched the way I was touching Damien's cock.

"That's it," he instructed. "Do you like touching it?"

"Yes," I said meekly, kneeling before his giant manhood, my skirt riding high on my thighs and my cock cage preventing any satisfaction of arousal on my own part.

It had long since been a secret fantasy of mine to suck the cock of a man, but I had always been too scared to actively seek it out.

"I think you should kiss it now," Damien said.

I looked up at him. He had such sincere, dark eyes. I couldn't help but trust him.

Timidly, I brought my lips close to his huge cock. A breath's away from his head, I took a moment to myself. And then, I brought my lips to his cock. It was rock hard, yet still warm and soft. Giving in to my innermost desires, I kept kissing it. My own cock strained against the cage, wishing it could experience the same attention.

"Good, good," Damien said. "Why don't you put it in your mouth?"

Cautiously I opened my mouth to receive his huge member, and then I knew I was a cock slut for sure. I loved it. I loved the contours against my tongue, and the knowledge of how this felt on the receiving end with my own cock denied any pleasure at all.

Damien let out a long moan of satisfaction while I explored his enormous cock with my tongue. Before I knew what I was doing, I was vigorously moving up and down on his head, hoping to please him.

"You are such a cock virgin," Damien said, "and it's so very hot. I love teaching sissies how to suck cock. Can you try to take the whole thing?" he asked.

I knew what this meant. Previous girlfriends had made a show of taking my own cock completely in their mouths, gagging as they did so.

Even with my mouth open as wide as it was, it was still difficult to fit his girth into my mouth, let alone swallowing the whole thing. But, I still wanted to please him and tried my best to take the whole thing in my mouth.

It felt like swallowing a bottle of beer. Trying to suppress my gag reflect, I took more and more into my mouth and throat, both loving and hating the experience at the same time.

How could a straight guy like this? I couldn't fathom the mental complexities at work. Maybe it was being locked up in chastity for so long and enjoying the vicarious pleasure I was giving Damien, or maybe it was the fact that I genuinely liked sucking cock and just never admitted it to myself.

Either way, Damien moaned with pleasure.

I tasted precum dribble out of this tip as I continued to suck on his cock, stroking it up and down with my free hands.

"Have you ever had cock in your ass?" Damien asked.

I groaned into his cock. He appeared to know me better than myself. I had secretly always wondered what a real cock would feel like in my ass.

"No, Mister," I said, continuing to suck on his huge cock.

I loved the way it felt on my tongue, lips, and the roof of my mouth. I loved knowing how much pleasure he we getting while being kept denied any pleasure of my own due to the tiny cock cage keeping my penis from getting hard.

"I think you should go get a condom, I'm sure you have some," Damien said soothingly.

I extricated myself from his cock and stood up, nearly falling over in the high heels of my boots. Shaking with nervousness, I walked to the bedroom of my apartment while Damien followed, his huge cock leading him.

Digging through my top drawer, I found an unused condom and presented it to Damien. I also found the lube I usually used for the dildo my Mistress occasionally made me use.

"Well, are you going to put it on, sissy?" Damien said, taking a more authoritative role.

Carefully, I opened the condom package and proceeded to slide it down Damien's shaft. He could have used the magnum sized condoms, but this was all I had and it covered at least half of his dick.

Damien carefully pushed me over the bed with my ass sticking in the air. My skirt was hiding nothing at this point, and I could feel my cock dribbling little bits of cum in my panties.

Without a second thought, Damien unzipped my skirt and let it fall down to my ankles. He pulled down the pantyhose and panties that were hiding my asshole and let his cock tentatively touch my ass opening.

"You have such a virgin little ass," he said, slowly pushing his cock inside me.

I gasped. The dildos were one thing, but a real cock was an entirely different thing. His cock was warm against my ass, and larger than the dildo I had been using. I was scared to have it rammed into my ass but excited at the same time.

"Just take a deep breath," Damien said, slowly pushing the head of his cock into my ass.

Just as he instructed, I breathed deep. The initial head, although larger than the dildos I had been using, was larger than I was used to, it wasn't too bad. My ass we being stretched, but I knew what to expect.

Damien slowly pushed more of his cock into my ass, and soon he had his balls touching my ass cheeks.

I could barely breathe. I had never had such a large amount of anything in my ass before. I could feel his head resting on my prostate, causing my cock to dribble even more with the intense sensation.

And then, he started fucking me. Slowly at first, making sure I wasn't going to scream, but then he started picking up speed after he realized my moans were of pleasure.

His head consistently rubbed against my prostate, making me even more horny than before, which I didn't think possible. Over and over again, his head rubbed against my gland.

Suddenly, I wasn't myself and grinded my hips into his, welcoming his cock into my ass.

"Yes, you like this, don't you little sissy slut?" he said. "You like dressing up like a little slutty girl but want huge black cock to fill your sissy hole, don you?"

I moaned in response, unable to control myself any longer. My own cock was dripping cum like crazy with Damien's head constantly rubbing against my prostate. I had never felt pleasure like this. It was still teasing, my cock was still locked up, unable to get hard, but the constant rubbing of the prostate increased the teasing to a whole new level.

Damien became more physical, grabbing my shoulders and pushing himself in and out at faster speeds. I didn't know how much more my asshole could take until I felt his hot cum spurting inside me. The condom had obviously broke, and his cum filled my asshole. I couldn't deny loving the fact a huge black guy's cum was inside me, filling me, and making me his little sissy bitch.

"Oh, you are such a bad girl," he said, slowly removing his cock from my ass.

He exited to the bathroom to clean his cock while I continued to kneel on the floor, enjoying the feeling of his semen swimming inside my ass, unsure whether to follow him in the restroom or stay put. I decided to stay put.

"So that's what being Dom'd by me feels like," Damien said returning from the restroom. "I don't want to interfere with your chastity training because it sounds like she has you locked down pretty good. But see if she minds a huge black cock that needs sucking and fucking. Will you do that?"

"Yes, sir," I said, still kneeling.

"Well, I live just a few doors down. I expect you to show up at my door, dressed, and kneeling when I call," he said as we exchanged phoned numbers. "The other tenants will just have to deal with me if they see you and complain."

"Yes, sir," I said. "Thank you for letting me suck and fuck your cock," I added in surprise to both Damien and my own self.

"Good. You will get more of it. I might even invite some friends of mine over to enjoy your nice, tight asshole. But for now, have a good rest of the night," he said exiting my apartment.

I still knelt there, holding his cum in my ass, unsure what to do. My chastity cage kept my own cock from having any pleasure from the experience, but I was still intensely aroused. I emailed my KeyHolder Mistress to let her know what had just happened. I couldn't believe it. I had just sucked and fucked a huge black cock...and I loved it.

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by Anonymous

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by Anonymous12/05/17

Good but

SO a sub doesn't call his mistress to see if it is ok to take on another Dom. Let alone sick dick and fuck without permission? Not gonna happen. Then he take a 9" Dick with zero lube zero fingering. Zeromore...

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by Anonymous09/18/17

love white sissy pussy

Need a white sissy slut

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by Anonymous06/06/17

i

I love being a cock sucker and love being fucked, but I could never dress like a woman to entice a man. I do not feel I am submissive---I just enjoy servicing men.

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