Latitia Ch. 07

Story Info
Lady's Night at The Dark Side.
5.1k words
3.78
2.4k
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Part 7 of the 8 part series

Updated 08/01/2023
Created 02/10/2023
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Monday was quiet. I attended a meeting of the historical society, did some shopping, ran the vacuum, and dusted. Just a good househusband. I greeted Latitia with a Margarita and after dinner, I soaked her feet and did her nails. I brought her to orgasm as she watched the news and a second time after we went to bed.

Tuesday was the same. Tuesday is outdoor maintenance day so I mowed the lawn, weeded the flowers, and noticed the windows were dirty so I washed them too. Hot and sweaty, I took a shower, treated myself to a bubble bath, and put a roast in the oven. I greeted her, naked, margarita in hand and she smiled.

"Damn, I do love you, white boy," she said, ruffling my hair.

We sat for a few minutes, watching the news while I massaged her feet.

"You know what," she said, smiling, "I'm kind of tired. I think I'd like dinner in bed."

"Of course," I said and watched her walk up the stairs.

I laid out a tray then, the roast beef, veggies, a well-buttered slice of the Italian bread I'd purchased that day, and a fresh Margarita.

Upstairs she was reclining against three pillows. She was naked, her legs parted, and the little string showing between her legs explained why she felt tired. She's always like that on the first day of her period. I put the bed tray table across her lap and then set the plate, silverware, napkin, and drink on the tray.

She smiled as she cut the first piece of roast and popped it into her mouth.

"Go on, now," she said, "you know what I like."

I bent and pulled the string with my teeth, carried it into the bathroom, and dropped the tampon into the toilet.

Then, as she ate her dinner, I brought her slowly along with my tongue and my mouth.

As I started licking, enjoying her scent and her taste, I could barely remember why I had been reluctant the first time she asked for this. She was delicious and the aroma of her was close to heaven.

As she finished her dinner I had her close and she stretched, luxuriously, like a cat, belched a polite, ladylike belch, and came, the thick salty release of her orgasm was spiced with the mildly coppery taste of menstrual blood. I had her covered completely with my mouth, swallowing greedily, not wanting to ruin our sheets.

When her body relaxed I leaned back, slipped a fresh Tampon in, kissed her belly button, gathered up the dishes, took them down, and put them in the dishwasher.

I made it back to bed, hard and wanting her, but the smile on her face told me I wouldn't have her tonight.

"I'm tired, Honey," she said, her smile not reaching her eyes, "Go ahead and jack off, You know I enjoy watching."

I thought about begging but it didn't look like that kind of a night, so I leaned over, kissed her, and then crawled in beside her. I began masturbating slowly, with long easy strokes, the way she liked to watch.

Don't get me wrong. It's not like I didn't enjoy being watched. On some level I can't claim to understand, I enjoyed putting on a show for her.

I made it a good show. I would stroke slowly and then spread my legs and pat my balls, hard enough to make me grunt. I knew she liked that. Time doesn't really have much meaning at moments like that. I felt the first leakage, the natural lubricant of precum, and slowed my movements even more, extending her show.

In the end, as it always does, my body took over and I came. At my age, the days of hard pumps shooting semen to my chin were past me. But I did leave an interesting puddle centered on my belly button.

She dipped a finger into the puddle and touched it to her tongue.

"Mmmmm, dessert," she said and I was surprised when she rolled over quickly and slurped it up like a bit of oyster on the half-shell.

She was asleep before I had the light out.

All of that was wonderful, but it was Thursday night when our lives really changed.

She called early in the afternoon and told me it was date night so I didn't have to cook. Unexpectedly free for the day I went to the barber shop and allowed the manicurist to do my nails. If it was date night I wanted to look my best.

I wasn't sure what to wear since it was her date night, so I greeted her naked with a Margarita when she got home. She smiled and handed me the big bag she was carrying. It was one of those fancy, heavy-duty, paper bags with a sort of hemp rope handle and an imprinted name - Nice n' Naughty in this case.

"You look yummy baby," she said, taking a drink. Her eyes were a little shiny already and I thought she was excited. I wondered why.

"Come on now," she said, heading toward the bedroom. I followed in her wake.

"God," she said, giggling, "It's like Christmas and I'm a little girl all over again. I do like new toys."

I watched with a mixture of excitement and trepidation as she reached deep into the bag.

She came out with a box, carefully wrapped in a bright pink paper with red hearts on it and a bright red ribbon. It wasn't big, think three packs of cigarettes, or maybe three decks of cards, stacked.

"Well," she said, visibly excited, "Open it."

So I pulled the ribbon and began taking off the paper, carefully splitting the tape.

Inside was a box, like an oversized ring box, black velvet covered, and embossed across the top in a fancy script was - He Will Beg.

I felt a sudden rush of adrenaline as I opened the box and saw what was in it.

It was beautiful in its own way. Highly polished chrome wire ended in a little cap almost like the top of a salt shaker but with an oversized hole in the middle. Two other loops gave it an odd sort of Mickey Mouse standing on his head look.

I knew what it was. I enjoy pornography as much as anyone, and had seen them before although I had never imagined wearing one.

It was a cock cage, and a "stubby" at that that would hold my cock to a small bump above my scrotum, and the two loops were ball separators.

"Well," Latitia said, a glint in her eye, "put it on."

"I don't think I can," I said, looking down at where I was fully erect.

She smiled then, and said, "Go ahead and drain it, white boy."

So I did, as she watched, I masturbated quickly, my semen falling to the floor between my feet. This wasn't romance or some sort of kinky foreplay. This was a purely mechanical/biological process and I found myself blushing furiously, embarrassed for some reason.

"You can lick that up when we get home," she said, and then with a sort of feral grin, "Now. Put. It. On." Each word a separate sentence.

It took me three tries to figure out how to put it on. My fingers were trembling under her watchful eyes and it turns out there were at least two ways to get it wrong.

She was literally tapping her foot in impatience and that was making my fingers tremble harder.

The way it worked was this -

First I had to work each of my balls through the rings, one at a time. The rings were a bit undersized and I groaned. "I'll do it if you need me to," she said, "but you probably won't like it." The way she said it scared me and I pushed my balls through the rings. I took a deep breath when I was done. My balls were separated and pushed forward.

Second, the little hinged cap was pressed toward my body until three holes lined up and the little brass padlock hooked everything together. Even soft, the cap was hard to latch and I was left with only a little chrome bump.

"Do you like it?" she asked.

I figured there was only one answer to that so I said, "Yes. I love it." And on some level I did.

"Now help me get ready," she said and started undressing.

I watched, and the stirring in my groin was painful against the cap of the cock cage.

I still enjoy looking at her, and when she moved, the lingering litheness of her basically athletic body was a thing of beauty. She stripped, naked, and came to me, and kissed me, a good kiss full of promise and the ache as my caged cock tried to respond made me groan and her smile.

"Sadist," I said, smiling.

"Oh, white boy," she said, her voice a little breathy, "You ain't seen nothin' yet."

I watched as she lifted her arms and sniffed, but frowned when she noticed the white residue of the deodorant she used.

"Get a washcloth," she said, so I did. I went into the bathroom, pulled a washcloth from the linen closet, ran the water until it got warm, and soaked the cloth.

I LOVE performing little services like this.

I carefully washed her armpits until none of that white residue was left.

I kissed them when I was done, making her giggle softly and pat my head.

"Good boy," she said.

She held up something black. I watched with interest as she stepped into it and realized it was a true corset, something I had only ever seen in movies and pictures. It fit snugly but there was still a full four inches open at the back where a series of laces crisscrossed from her shoulder blades to her ass.

"Okay, white boy, cinch me up," she said, turning her back and grabbing onto one of the bedposts.

The next several minutes were a scene out of Gone With the Wind or maybe Downton Abbey. I would grab the cord, starting at the bottom, and pull the lacing tight enough that the edges of the material touched before working up to the next pair of eyelets. She had to suck in her breath and I had to pull hard enough that I worried about the strength of the material.

Once I had her laced in, thought, it was worth it. Her small breasts would never show cleavage, but they were lifted interestingly by the underwire of the corset's top. Her waist was cinched in to 20 inches. She looked like I could span it with my thumbs and forefingers. And it put that gorgeous ghetto butt on display beautifully.

I stepped back, whistled, and groaned as my locked-up cock tried to get hard.

I watched then, as she finished dressing. Well, if you can call a black silk vest and a skirt barely covering her ass along with spike-heeled boots that laced almost to her knees dressing.

She smiled at me, a predatory smile, and then did a slow turn.

"Well, white boy, what do you think?" she asked, batting her eyes.

"I think I may be the luckiest man in this city," I said and she smiled at that.

She smiled at that and kissed me quickly before handing me another box from her bag of goodies, this one about the size of a shirt box.

"Put it on," she said.

I opened the little box and my breath caught. I shook out the garment there and the rush of combined excitement and, well, fear I suppose is a good word. What I was looking at were loose, shapeless pajamas, not white but a pale grey with dark grey horizontal stripes. They were chain gang uniforms straight out of O Brother, Where Art Thou? or pretty much any movie about the Nazi concentration camps.

"Go on," she said, her foot tapping to demonstrate her impatience, "put it on."

I can't even say I know why I was crying as I pulled the loose-fitting trousers on, pulled the drawstring tight, and then let the loose shirt fall over my head. The material was very coarse, almost scratchy, and I was itching almost immediately. I put the little cap on my head and stood before her, crying softly, my nose running, wiping it on the sleeve of my shirt, and waiting.

And I was surprised when I felt a stir in my groin followed by a sharp pain as I tried to come erect against the cage she had me in.

"Oh my goodness, yes," she said, looking me up and down, and then, "That will definitely do."

She reached into her bag one more time. By then I was beyond surprise so when she handed me a pair of oversized handcuffs connected by about two feet of bright chrome chain, and said, "On your ankles," I didn't hesitate. I just bent and put the cuffs on my ankles.

"Okay, white boy, time for your debut," she said and headed into the living room. I didn't need to be told to follow her.

She called an Uber and we waited in silence.

The driver smiled when he saw his fares, but didn't say anything. Just started out when Latitia gave him the address.

I felt my first rush of real fear when I realized where we were going.

"Latitia," I said, "what's going on?"

"Lady's Night at The Dark Side," she said, smiling a sweet smile.

I couldn't stop the soft moan.

"Don't worry, sweet cheeks," she said and the sweet smile morphed into her predatory grin, "I won't sell you."

I shivered when she added, "Probably."

"Right here is fine," she said as the Uber pulled into the big parking lot. There were few cars in the lot and I wondered if that meant there wouldn't be many people inside or that they had taken Ubers like we had.

Latitia touched her credit card to the little gadget on the driver's cellphone, it beeped, and we got out.

It took me several steps to settle into a shuffling walk that allowed me to more or less keep up with her.

I was still a few steps behind her when she got to the front door and stopped, waiting, tapping he foot to demonstrate her impatience.

"If you cannot do better than this, it is going to be a hard night," she said, and there was something about her tone, the way she didn't use any contractions, that scared me.

"Yes, ma'am," I said, moving to open the door for her.

The hostess who held court at her station set the tone, somewhere between Goth with her black nails, lipstick, and hair, and Dominatrix with her thigh-high boots showing stiletto heels, a corset cinching her waist into a true hourglass, and an Indiana Jones bullwhip hanging from her belt.

In the main room I heard, "Latitia," and watched as a small, fat woman, she made me think of Janice Yellen, the Secretary of the Treasury, approached, followed by a Black boy, I say "boy" not as a racial insult but as an observation, he had to have a fake ID to get served, wearing nothing but a heavy iron collar, at least it looked like iron although I suppose it might just as well have been a lightweight plastic. His most obvious feature was at least a foot of soft dick hanging between his legs, stretched by the weight of a heavy padlock, its shank locking it to a brass ring that pierced the glans, the head of that outsized cock.

The thing is, I knew her. Well, I had met her at a couple of the faculty events Latitia had taken me to. I didn't know her first name but I knew she was Dean Fredericks although of what she was "dean" I never knew. I watched, fascinated, as she and her boy approached. She was almost comical except that padlock made it clear she was serious. Her white hair was done up in a spike, standing straight up from her head. She was completely covered in a catsuit that showed everything. Through the sheer material, I could see the rings through the nipples of her fallen breasts, the heavy belly button ring, and the amazing giant spider tattoo centered on her belly button with a tracery of spider web running around, evidently to her back.

I was captivated.

"Latitia," Dean Fredericks said, smiling conversationally, "do you allow your boy to eyeball his superiors?"

Latitia slapped the back of my head hard enough to send the little cap flying and said, "On your knees, boy."

I didn't hesitate, I dropped to my knees.

"May I discipline him?" Dean Fredericks asked.

And I felt a rush of adrenaline as I was truly frightened by her words. I could picture her boy's pierced cock and had an instant when I knew that was my future as well.

"Of course," Latitia replied and I couldn't stop the moan that escaped my lips.

"I think a night on the doll stand will do him good while I introduce you around," Dean Fredericks said.

"You'll have to show me," Latitia said but I noticed she did not say "No" to that.

Dean Fredericks reached out with surprising quickness and grabbed my hair, forcing me to look up, my neck bent painfully.

"Boy," she said, her voice calm but her face showing, well, I don't think "madness" would be a bad word, "lessons must be taught. Now follow me."

I followed her, noticing that each ass cheek had a palm tattooed on it, and an oversized skull grinned at me from between her shoulder blades making me think of Sons of Anarchy ink.

Along what I thought of as the "device wall," an old man, and when he seemed old from my perspective that means probably 70 plus, was in that contraption of pipes and pulleys that had his back arched painfully. Tied to the X-shaped construction was a ridiculously overmuscled bodybuilder with the terrible complexion and shriveled cock and balls of a steroid abuser. In the stock, a young man was locked, his head and hands showing, bent at the waist as he writhed slowly trying, I imagined, to ease a cramp in his back or his belly. Between his feet a pile of shit made me wonder how long he had been held in that device.

She led me to that pole with its big dildo and I moaned. I realized what "doll stand meant."

She bent, loosened a thumbscrew about halfway down the pole, and lowered the dildo.

"Shirt off, boy," she said.

I looked at Latitia, pleading with my eyes.

"Shirt off, boy," Latitia said.

I moaned and pulled the coarse shirt over my head. And I was aware, as I hadn't been in years, of the pot belly I had developed, the incipient man boobs as I lost muscle mass, and the wattle under my chin. All of those signs of my age were on display and I blushed.

"Pants," Dean Fredericks said and I just pulled the bow tie of the drawstring and let them fall, again, my body making me ashamed, the way my skin sagged and I knew my ass had, well, pretty much disappeared. And, of course, the shiny chrome cage that held me.

"Now, boy, here's the deal," Dean Fredericks was saying, drawing me back to reality, "we don't believe in lubricant here at The Dark Side, but you've been a good boy so you've got 60 seconds to do whatever you think would be a good idea."

I wasted about 10 of those precious seconds trying to process what she had said and then started working my tongue to get saliva running. I was beyond embarrassment by now, and used my finger to close first one nostril and then the other, blowing my nose, trying to lubricate the dildo with snot and then bending and taking it in my mouth, trying to wet it, make it slick, with my saliva.

I pushed harder, thinking if I retched a little my body might produce more saliva or drool or something. That thing was big and I wanted it as slick as I could get it.

I was slobbering on it when I felt a slap on my ass and stood.

"Feet here," Dean Fredericks said, pointing to two little dots painted on the floor.

I stepped onto the dots, unable to stop the tears of shame and humiliation.

Latitia's smile gave me a stirring in my groin and a fresh stab of pain as my cock tried to respond.

"Spread your cheeks, boy," Dean Fredericks said, and I reached back, the feeling of utter helplessness and surrender causing another of those sharp stabs as my cock strained against the steel of the cage.

At the first touch of the dildo, my body tensed automatically.

"You really should relax, boy," Dean Fredericks said.

I tried to relax.

"Now squat, boy," she said, "you know how much you like fucking us up the ass, now it is your turn."

I did as she said, bending my knees slowly, feeling the pressure on my asshole building.

"OH JESUS," I cried as it penetrated. The pressure was immense. It felt like I had just shoved a goddam football up my ass. I wondered if something had torn.

"Oh God," I moaned, as my body accepted it.

"Good boy," Dean Fredericks said, "Now take it all,"

I moaned again but let my knees bend a bit more, feeling it going deeper and deeper until I felt it bottom out against the top of my rectal vault.

"Two more inches," she whispered in my ear.

"I can't," I said.

"Of course, you can. Now adjust yourself or I will do it for you," she whispered.

I moaned and rocked back and forth at the waist and suddenly felt the dildo find the entrance to my bowels and I accepted that final two inches.

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