It was January in Chicago and winter was coming on strong. But it was warm inside "The Heart of Darkness" and it was filled with people trying to forget about the bleak months to come. I was somewhat of an insider there as much as any male sub could be. I had paid my dues by volunteering for clean-up duty on Sundays. I also had had professional visits to some of the resident Dommes so I was kind and was given opportunities some of the other newbies where envious of. On that particular night I was going to be on stage with a popular woman named Mistress Ava. Before the club opened I spent three hours cleaning bathrooms, vacuuming, setting up various play stations and putting out the antiseptic cleaning stuff. Another sub and I were the only ones there until around 7 (the club doors opened at 9) when the organizers and performers started to show up. Most nights it was pretty much a play party but once a month or so they had a show night. This was going to be my first time as part of the show. Yes I was scared a bit. Mistress Ava was not known for her softness. But I am somewhat an exhibitionist when in the kink world, the exact opposite of what I am in the rest of my life where I happily blend into the background. At about 8 Mistress Ava showed up. She pretty much ignored me, I would have expected nothing less, and disappeared into the changing room.. We continued our last minute prep work and a little before opening time I was sent for by Mistress Ava

She had changed from her fairly racy street attire to full pedal to the metal Dominatrix. Working our way up from the bottom she was wearing a pair of suicide high heels boots, shiny black leather of course, they were laced up each side, no zipper cheats. I saw another male sub kneeling in the corner who must have done the lacing. The ugly red welts he had on his bare body from a handy nearby tawse made me suspect she wasn't happy with his work. Bloused into the top of the boots were her skin tight leather pants. A thick leather belt with the word "NO MERCY" spelled out in pointy chrome studs surrounded a solid waistline Her shirt was black, transparent showing a black corset with exposed nipples. It mostly unbuttoned and tucked tightly into her pants. Her black hair was pulled into a tight bun, her makeup was dark and she had an imperious attitude that said it all.

She was smoking a cigarette, a long black one. She took it out of her mouth, looked at me and said "Come here grub". I stepped in her direction but the look she gave me dropped me to my knees and I completed the trip on all fours. I didn't know if I was expected to kiss her boots or wait for instructions but my time subbing taught me better to do nothing than do something wrong. Well usually. So I waited.

"Stay down on your hands and knees and remove your clothes."

Not a simple task if you ever tried. The room was small and I was in cramped area of it. But I accomplished it without too many slaps for being slow and stupid. She told the other sub to put my clothes away and then told me to get up and follow her. We left the changing room and went into the main area. He doors weren't open yet but there were a dozen or so people milling around. I was the only naked person and secretly found the situation to my liking. Most of the people watched as the leather clad goddess and the little wimp of a guy went over to a standup cage. The cage was made out of prison like steel bars. It was 78" high, 25" wide and 16" deep.

"Turn around and put your hands behind your back," she said. I did and she took a pair of metal thumb cuffs from her belt and snapped them on my thumbs. "Get in," she aid and I stepped into the cage. Grabbing my arm she spun me around and then closed the cages door. A serious looking lock was put in place. I would need the key or a cutting torch to get out. She then left me and I thought she was done but she returned a minute later with a few more things to make me uncomfortable. The first was a humbler. Two pieces of wood when screwed together had a home in the middle with the victims balls pulled through. I had always seen these used with the humbler positioned behind the subjects thighs but she had something else in mind. Once she had it on my balls she twisted it so that she could pull it between the bars. When she was done the humbler and my balls were on one side of the cage the rest of me was inside. Next she took a bright red lipstick and wrote "Grub" on my chest, a name that has stuck with me ever since. And as a final touch she put a hood over my head. It was black, stretchy material like nylon. It was easy to breath through but mostly opaque. The lights were turned down and I could only make out outlines of things a foot or two away. And that is how she left me for what seemed a very long time where I was pinched prodded and teased by anyone who cared to do so. As far as the show went I will just say that the beating was pretty severe with a variety of tools and from my point of view it went on for a very very long time.

After the show she released me and I decided there was nothing more for me there that night and headed for the door.

"Hi," a female voice said behind me.

I turned around to see a young African American woman walking towards me. I had seen her in the audience standing fairly close to the small stage I had been on. Her skin was smooth and dark, her hair was long, kinky and streaked with a lots of blond highlights. Some of the strands were twisted into thick coils giving the appearance of a multicolored rope. She was wearing blue jeans, a black t-shirt and black, low heeled shoes. I wouldn't say she was a little plump, just voluptuous. Her breast were straining against the shirt, her nipples sticking out from them. She was smiling and when I said hello back she said;

"You OK. A couple of the hits made you jump."

"Yeah a few. But generally speaking I'm fine. I don't remember seeing you here before, but I don't always come I'm Matt. Who are you?" I said smiling.

"My name's Charlotte. This is my third time. I usually come with someone but I came by myself tonight. I live out in the burbs"

"Brave girl" I said. "Pretty young ladies in a place like this can be a little iffy.

"I know some people here." She mentioned a few names, all male Doms. Then she said "Are you leaving?"

"Yeah" I said. "I'm done for the night."

"No friends to hang with?"

I laughed and said:

"You know as popular as a single woman is in places like this male subs are the opposite. You see them huddling in the shadows. I come when I can. Sometimes I work Saturday nights.

I found Charlotte very easy to talk to and I did something I never do. I said:

"I'm hungry so I am going to go get something to eat. Then I'm going home, shower, veg out a bit and then go to bed. You're more then welcome to join me in any of those endeavors if you care to." Was I really hitting on this beautiful black woman? One who just watched me get whipped and then get down on my hands and knees and lick the woman's boots? What the hell was I thinking?

She looked me in the eye for a second and as I prepared for the inevitable rejection she said:

"Yeah. I'm a little hungry. Let's start with that. Let me get my stuff."

OK. That was an incredibly good start. Her stuff consisted of a backpack a long black leather coat. I took her to a bar I knew. It was near a big college filled with seniors and grad students. It had a good crowd that night but we managed to find a booth. We had beers and burgers and split some fries. We told each other about ourselves. She was a year older than me, did something I didn't understand with computers, traveled a bit for work and was working on an MBA. I told her I worked in a hospital, would like to travel but hadn't done much yet and I love to eat so I learned to cook. Yeah earth shattering shit. Of course there was a subject that I would have liked to have brought up but it was too crowded to talk kinky so I thought I would wait and see what happened next. We finished our food, we finished our drinks I called for the check and while we waited for the change she said:

"So what's next on your itinerary?"

"Go home. But I can take you anyplace you want to go."

Her eyes stared at me. Her smile was Mona Lisa-esque. "No. I'll go home with you."

I got a little boner then.

My apartment was perfect for a single person with no social life. They call it an alcove studio. One room with a place for the bed that was kind of out of the way. I had a bed big enough for two people (hope spring eternal), a sofa, a recliner and a small dining table with 4 chairs. The dining table was used for a lot of things but never dinning. Dining was done on the sofa in front of the big TV. It was a comfortable apartment and I liked it so I didn't clutter it up with stuff, always did the dishes and made the bed everyday; so that when we arrived I didn't have to scurry around picking up underwear while making a joke that it was the maid's day off.

"Nice" she said looking around. She went to the sofa and sat down. "I think a shower was next. No?"

"Yeah. Will you be joining me?" I said only half joking.

She smiled at me for a good ten seconds then said "No."

Just a tiny bit deflated, my ego not my dick, I said OK and headed into the bathroom.

Ever shower after a whipping? Ouch. Water not too hot. No soap. Not too much pressure. Granted this wasn't a terrible beating and no skin was broken but some caution was needed. If I was alone I would have just rinsed off but I had a lady caller so I had to put some effort into it. Since Charlotte had seen my naked body for almost all evening I didn't feel a need to be overly modest so I just wrapped a towel around myself and stepped out of the bathroom to get some more clothes. Things had changed.

Charlotte was still seated on the sofa but had taken off her t-shirt revealing a black leather corset that pushed up her breast but did not cover her dark pointy nipples. She had removed her flat shoes and had replaced them with a pair of spiked open toed high heels and she had put on a deep red lipstick. In her hand she held a heavy 18" long wooded ruler.

"We're not going to veg out now are we?"

"No, we are not. Lose the towel and crawl over here" she said.

"Yikes!" I thought. I won't say that unusual sexual activity never occurred in my apartment. But this would be the first time that it involved more than just me. I tossed my towel back into the bathroom dropped on all fours and crawled across the room to where she sat. My face was down and a small wiggle of her foot told me what I had to do. My lips went to those open toed shoes. The toes were long and perfect with their blood red polish. My lips made contact and a shiver went through my abused body. I kissed each toe on her right foot then started working my way up her foot. She allowed this until I got to her ankle then told me to start on the other foot. I moved over to her right foot. After I kissed each toe I got a little daring and stuck out my tongue and ran it over some exposed skin. She allowed this for a couple of seconds then brought the ruler down hard on my already abused ass.

"Did I tell you to lick my foot?"

"No Mistress." She brought the ruler down again.

"Your tongue is disgusting." Whack. "You do not do anything unless I tell you too." Whack. "Do" whack "I" whack "make" whack "myself" whack "clear?" whack whack whack.

These whacks hurt a lot. I was barely able to squeak out a "Yes Mistress."

"Good. Now remove my shoes and start licking my feet."

This want on for some time. I was able to work my way to almost her thighs before being told that was high enough by her wooden prompt. Eventually she told me to stop and stand up in front of her. I am not a very hairy person but I do have a nice pubic bush. Mistress Charlotte did not approve.

"What do you call that shit?"

"Mistress?"

"That cock fuzz." She said pointing . "That's for men. You're a slave. I want you to go back into your bathroom, get in the shower and shave off all that nasty shit." Looking at her phone she said "And your time has already begun."

I immediately turned around and headed to the bathroom. She waited until I got there before saying:

"Who said you could walk. Crawl back over here, ask permission to go, then crawl back to the bathroom."

Once again I complied. I probably wasted a minute of the unspecified time I had. I jumped in the shower and turned it on. It was only lukewarm but that was good enough. I tried to go as fast as I could, without missing any hairs or cutting my dick off. When I felt I had done a good enough job. I exited the shower, gave my self a quick toweling off and crawled back to her feet. When I got there she looked at her phone and said:

"Not even close. Close your eyes and put out your hands, one on top of the other palms up."

She hit it with her ruler. She hit it very hard and I almost cried when she told me to switch hands. I did and she hit that one too. They burned for a long time. Next she had me stand so she could examine the job I did shaving. She found five hairs that she plucked out with a pair of tweezers. She made me eat them. She thought this was very funny.

"OK. Now go get your toys."

That caught me by surprise and for a second or two I didn't know what she meant.

"Toys?" I said.

She grabbed my ear and twisted it hard. She pulled my face close to hers. She looked pissed and she scared me a bit.

"I know you've got fucking toys. You know you've got fucking toy. Now crawl over to where ever you have them and get them here before I get really pissed and hurt you."

All the while she continued twisting my ear. The problem wasn't that I didn't have any sex toys to bring to her the problem was that I had a lot. A whole lot. As I crawled away I thought about all the things I were going to give her how humiliating this was going to be.

I crawled over to my bed and pulled out a 24"x36" inch Rubbermaid container from under it. I pushed it over to her.

"Is that all?" she said.

"No Mistress," I said.

I went back and got the second one. Both were filled with floggers, whips, leather and wooden paddles. Also various butt plugs, pumps, vibrators, tubes of lube, gags, cock torture toys etc.

"Is that it" she said raising her eyebrow at me."

"No Mistress." I went to the nightstand next to my bed. I took a vibrator, butt plug a pair of nipple clamps and some more lube out of the drawer, my favorite jerk off toys at the time and laid them at Mistress Charlotte's feet. Before she asked I said "One more." And went to the closet and got another container. This would be the most embarrassing. Still on my hands and knees I pushed it back to where she sat. "I believe that is everything."

"So what's in this one." She said tapping the last box with her toe.

I opened the box. She looked in and her face lit-up.

"Oh sweetie" she said "you just made my day."

Twenty minutes later I stood in front of her wearing some of the items she had selected from the box. I was wearing what can only be described as a sissy maid's dress. It was pink with lace around the collar and at the end of the long sleeves. The skirt was ridiculously short with a built in petticoat so that it flared out. It too was the white lace. If I wasn't wearing any underwear I would be completely exposed. But I was wearing underwear. I was wearing a pink thong I had bought from a cross-dressers website. It was very feminine but it was designed with a pouch for my junk. White stockings held up by matching garters completed the outfit.

"I always wanted a maid. I'll get you an oversized dog bed and you can sleep in the corner of my room. I'll have a little bell I can ring when I want my coffee or something. Yeah this is going to work out just great." She pulled me closer to her so her lips were up against my ear and said "So tell me little sissy boy, have you ever eaten black pussy?"