It was a cold early morning in New York. I was walking briskly and quickly toward the boarding gate for my flight to Miami. I was heading for a business conference, and I'd be spending my time in Miami for the next 4 days. Since a weekend was coming up, Mistress Victoria mentioned that she would be traveling to Miami as well and that she would be reaching out on Friday evening. The thought of that in itself made my cock throb. I was gonna have a kinky and thrilling weekend.

I boarded my flight and settled down in the business class seating in the aisle. It was gonna be a 3-hour flight and I planned to rest well. Next to me was an elderly man who looked like he was into a white-collar finance job. I just smiled at him, gave a warm nod, and had a small chat. The flight took off, and after the seat belt signs were off, I quickly checked my emails, and the stewardess asked me if I needed anything to drink. I looked up at her, and she was a hot woman in her mid-30s or early 40s. Her uniform was tightly holding her structured body. I shook off the thought and told her that I'm fine with some water. After a while, she went back to the front of the plane. That's when I checked her back. Damn! What an ass! It was big and curvy. I got an instant boner, and the guy next to me noted me checking her out. He was doing the same. I just smiled at us "men"...

It was time for me to rest as I had a long day ahead lined up with back-to-back meetings. I slept off for the rest of the flight.

I reached Miami and quickly checked into the hotel, freshened up, wore a metal chastity on my cock as Mistress Victoria instructed me, wore a crisp Italian suit, went through my agenda, and walked over to the venue. While I was heading to the conference hall, I saw a very familiar face. I instantly recognized her. It was Deborah! Deb was my ex-boss. Deb, as we called her, was in her mid-40s. She had dark hair cut into a sharp bob. She was a confident woman and had honed her posture, which was straight, assured, with a natural air of dominance that never required raising her voice. She was around 5'8" and always wore tailored outfits to show off her strong figure. She would easily be a 38D, full and heavy breasts with rounded hips and a firm ass that filled out her skirt in a way that nobody would miss. Overall, she was my dream Domme! I've jerked off imagining her using me multiple times when I worked at my previous company. I've always been professional with her and have shown my submissive side in my conversations with her.

Deb recognized me instantly as well, as we worked together for a good amount of years. She was also rushing to a meeting.

"It's nice to see you here!" I exclaimed.

"This is a nice surprise! Finally, I'm meeting someone I know and someone who is still surviving in this industry!"

"We will catch up later, Deb. Hope you have the same number. I'm heading to a meeting," I mentioned.

"Yes, I'm a bit busy too. Let's catch up later," she mentioned.

With that, I hurried to my meeting and damn, it was an exhausting day! I reached back to my hotel at 5:30 PM and crashed on my bed. I slept for a good 45 minutes and felt super fresh. While thinking about dinner plans, I recollected my conversation with Deb, and I just dropped her a message.

Q: Hey, Deb!

D: Hey man. What's up?

Q: What are your dinner plans?

D: None. Just resting in my hotel room. What are your plans?

Q: Let's go for dinner? Where are you staying?

She was staying at the same hotel as me.

Q: Let's meet in the lobby at 7:30 PM. Making a reservation at a nearby place.

D: Cool! Let's catch up.

I took a hot shower, groomed myself, wore a casual shirt and trousers, slipped on my sneakers, and headed to the lobby. Deb was sitting on the lounge chair waiting for me. She was wearing a mild blue shirt buttoned down enough to reveal her cleavage (classic Deb!) and grey pants. I assumed she hadn't fully changed from her business attire. We exchanged greetings and walked up to the restaurant. It was just a block away. We were chitter-chattering about work, where the industry was heading, office gossip, and then reached the restaurant. Since I was no longer her subordinate, she was very chill and outspoken with me. We ordered some steak and a bottle of wine, along with some Brussels sprouts. Midway through the dinner, after completing one glass of wine, the topic moved on to relationships.

"How's Clara?" she asked me.

"Well, that was over a long back, didn't work out," I smirked, pouring the next glass for both of us.

"Ouch, sorry about that!" she responded.

I just smiled and nodded.

"How's Jim?" I asked. Jim was Deb's husband.

"Well, Jim is Jim... you know... engrossed in business. Traveling around the States, closing deals."

"Good to know," I complimented. At that point, my eyes went to her breasts. Her cleavage was so hot, and I don't know if it was the wine, but I couldn't take my eyes off her. Deb saw me. I was scared that she might get offended.

"Apologies, Deb!"

She just waved her hand at me... "Ah! Fuck it. It's not new for me! I show it off for a reason. I love the attention," she said.

I raised my eyebrows and just nodded. Well, that was new. I'd never seen Deb being very upfront and outspoken like this. She was like this when it came to business. But this was totally new.

We resumed our conversations and eventually finished dinner. She was a bit tipsy by now, and we were slowly walking back to the hotel. I got a closer look at her boobs when we were walking and I got an instant boner. And my cock pained a little. That's when I remembered the chastity cage that I was wearing. My thoughts went back to Mistress Victoria, whom I was planning to receive tomorrow evening.

We entered the elevator. And playfully, Deb tried to hold my cock! This was the impact of my flirting at the restaurant. And she clearly felt my chastity cage. I froze for a few seconds, and the air felt thick suddenly! I swallowed some air, and I asked her, "Which floor are you on?"

"7th please," she said.

After a pause, she said, "Breakfast tomorrow at 7:30 AM?"

I said, "Sure." By then, the 7th floor came, and she left. "See you," and she left.

I reached my hotel room and was having mixed feelings about what happened. I didn’t want to react, and then I slept off for the night.

Breakfast with Deb

The next morning, I got up around 6:30 AM, freshened up, put on some linen trousers and a half-sleeve shirt, and was down at the hotel restaurant by 7:30. Deb was already there at the table, dressed in an elegant olive dress with sunglasses pushed up on her head and some minimal jewelry. Her cleavage was showing just enough.

We greeted each other casually and ordered breakfast. She picked a bowl of Greek yogurt with berries and some scrambled eggs. I ordered a croissant and coffee.

"So... did you sleep well?" she asked me, smiling.

"Yeah, after all that wine, I passed out!" I replied, sipping my coffee.

She smirked. “You seemed... a bit distracted on the walk back.”

I paused. “Yeah... I mean, you did grope my crotch in an elevator, Deb.”

She laughed. “Oh, come on, that was a gentle tap. I was curious.”

I looked around to make sure no one was listening. “Well, curiosity killed the cat... or in this case, clanked against the cage.”

She leaned forward a bit. “So, you’re the submissive type, huh?”

I froze. This was Deb, my ex-boss. But also someone I had fantasized about controlling me. She was staring straight into my eyes now.

“Yeah. I am,” I said softly.

She smirked again, knowingly. “I always suspected it, you know. The way you’d obey without question. The posture. The quiet little yes-ma’ams... You were a good little corporate sub.”

I just blushed and looked down.

“You still have that cage on?” she asked.

I nodded.

“Who's your Domme now?”

I hesitated. “Mistress Victoria.”

Deb raised her eyebrows. “Is she here in Miami?”

“She’s arriving this evening.”

“Well, well, well…” she said, finishing her last spoonful of yogurt. “So you’ll be busy this weekend.”

“Yes,” I replied.

She stood up and adjusted her dress slightly. “We might have unfinished business... from your old appraisal days. Share Victoria's contact information after getting her permission.”

I swallowed hard and nodded.

Mistress Victoria Arrives

After Deb left the breakfast table, I sat there for a few more minutes, collecting my thoughts. The interaction had stirred something deep. It wasn’t just the casual dominance—Deb meant it. There was hunger in her eyes. My cock, still caged, was throbbing hard, straining against the cold metal. I adjusted myself slightly, took a sip of coffee, and stood up.

The rest of the day went by in a blur. The final conference sessions were intense. A few networking meetings, two back-to-back panels, and then I was done. By 4:45 PM, I made it back to my room.

I washed my face and quickly shaved my face, chest, and crotch clean. The cage stayed on, obviously. After freshening up, I headed to the rental desk downstairs. I had booked a sleek black BMW convertible in advance. Picked it up from the valet and headed straight to the boutique wine store I spotted the day before.

I picked a 2019 Napa Pinot Noir—Mistress Victoria’s favorite—along with a bouquet of fresh red roses and a luxury spa voucher I had pre-booked as a surprise.

By 5:50 PM, I was at Miami International Airport, pacing near the arrivals gate.

At exactly 6:02 PM, I saw her.

Mistress Victoria walked out of the terminal like a queen returning from war. She had her sunglasses on, hair tied up into a sleek bun, wearing a figure-hugging black loungewear set that showcased her curves with elegance and authority. She noticed me, gave a half-smile, and walked over.

I opened the passenger door for her, where the bouquet and the gift card were laid neatly. She looked at them, picked up the wine, and gave me a nod.

“Good work, boy,” she said coolly.

“Thank you, Mistress,” I replied, trying hard not to leak inside the cage from just her voice.

The drive to the hotel was mostly quiet. She rested her hand on the armrest and just watched the city pass by. I couldn’t help glancing at her thighs every now and then. She noticed but didn’t say a word.

I had booked her into the corner suite—top floor. Valet took care of the car while I carried her luggage and walked with her to reception. The staff greeted us politely, and I made sure everything was smooth. We entered the elevator, and I hit the 16th floor. Once we reached her suite, she walked in without a word.

Just as I turned to leave, she finally spoke. “Wait for my instructions. Be ready tonight.”

I bowed my head, “Yes, Mistress.”

It was 7:30 PM. I headed to my room.

I knew tonight was going to be something else.

I prepped. Cleaned up. Groomed again. Trimmed and shaved everything around my cock and ass. Used an enema to make sure I was spotless inside. Then, I lay down on the bed, still in my boxers, and set a phone alarm for 9:45 PM.

Ding.

The alarm went off. 9:45 PM.

I sat up, heart pounding.

The message was already on my phone.

“Head over to my suite at 10 pm. Wear a pink lace panty over the locked cock, wear a white vest. Your choice of shirt and pants. Bring the keys to your chastity cage.”

I followed her orders precisely. Picked a linen white shirt, slim grey chinos. Underneath, my locked cock bulged under the soft pink lace. The key was tucked into the small leather pouch I always carried when traveling for Mistress. I sprayed a little cologne, took a deep breath, and stepped into the elevator.

The ride to the 16th floor felt eternal.

I reached her door. Took a breath. Knocked.

The door opened.

Mistress Victoria stood there in a leather bra and thong set, black heels, her hair now loose and wild. Her eyes burned into mine.

“Strip,” she commanded. “Keep the panties and vest on. Crawl in.”

I dropped my clothes instantly, got on all fours, and crawled into the suite.

And there… on the couch… sat Deb.

She was watching me with a calm smile, legs crossed. She wore a sheer black kimono over blood-red lingerie.

My heart skipped a beat. My body froze for a second.

“Good evening, bitch,” Deb said.

Mistress Victoria tugged on my leash. “Move.”

I crawled past the threshold into the suite.

“You were a good slut in Manhattan,” Mistress Victoria said. “Let’s see if you’ve kept your standards. Tonight, you’re our toy.”

“Yes, Mistress,” I whispered.

Shared Ownership

The suite was lit low, scented with jasmine and wood. A leather paddle rested on the coffee table. A second leash was coiled by the armrest. A bottle of Pinot Noir is already uncorked. Two glasses, half-full.

Deb looked right at me.

“You look good in pink,” she said, crossing her legs. “I missed that ass.”

Mistress Victoria handed her the leash.

“I’ll let you have the first round,” she said, taking a seat in the armchair across from Deb. “He’s already been edged three times this week. Didn’t let him cum once.”

Deb stood up, walked over, and yanked the leash, pulling me close.

“Kneel,” she said.

I obeyed. Her hand slid under my vest, across my chest. She traced my collarbone with a single finger, then gripped my jaw hard.

“Still locked up, huh?” She looked down at the bulge in my panties and grinned. “How pathetic.”

She walked behind me, her fingers trailing along my shoulders.

Then a sharp smack on my ass.

I jolted.

“Did I tell you to flinch?” she said.

“No, Miss Deb,” I replied quickly.

Another slap, harder.

Mistress Victoria chuckled behind her wine glass. “I’ve trained him well, no?”

Deb ran her hand across my cheek. “Very well. Now let’s see if he remembers how to beg.”

She crouched in front of me, looked me in the eye.

“Take off the vest.”

I peeled it off. Now I was down to just the pink lace panties, the chastity cage underneath clearly outlined.

She stood, walked to the couch, and sat back down.

“Crawl to me.”

I did. Slowly, deliberately. The leash slackened, then tightened as I reached her feet.

She grabbed a handful of my hair. Pulled me up to kneel between her legs.

“You don’t get to touch me tonight,” she said. “But you’re going to make me cum anyway.”

She pulled my head forward, pressed my face into her soaked panties. She was already wet. I could smell her arousal, feel the heat between her thighs.

I licked. Gently. Teasingly. Just the way she liked.

She moaned.

“Faster.”

I obeyed. The leash tightened behind me. Mistress Victoria was standing now, circling us like a predator.

Deb gasped, hips grinding into my face. She was grabbing my hair, pulling hard, fucking my mouth through her panties.

Then suddenly she stopped.

“Enough.”

She stood, walked around me, and whispered into Victoria’s ear. I couldn’t hear what she said.

Mistress Victoria smirked.

“On the bed,” she ordered. “Ass up, face down.”

I obeyed instantly, crawling across the suite’s plush rug, up onto the bed. I arched my back, presenting my ass as they liked.

I heard a drawer open. A snap of gloves. The unmistakable sound of lube being squeezed out.

Mistress Victoria approached first. She ran a gloved finger down my spine, across my hips, between my cheeks.

“You prepped well,” she murmured. “Good boy.”

Then the cold press of a lubed finger at my entrance. She slipped in slowly. Then another.

I moaned into the pillow.

Behind me, Deb stripped out of her lingerie and pulled on a strap-on—thick, dark, slick. She climbed onto the bed beside Victoria, her eyes locked on my trembling form.

“Ready for both of us?” she asked.

I didn’t even get a chance to answer.

Mistress Victoria moved first, fingers stretching me wider, pressing deep.

Then Deb climbed behind me, aimed the head of the strap-on against my hole. I moaned louder now, hands gripping the sheets.

Victoria kissed my back. “Take her cock like a proper slut.”

And Deb thrust.

Slow at first. Stretching me open. Then deeper.

My body shuddered.

Mistress Victoria was at my head, fingers gripping my jaw. “Look at me. You’re not allowed to cum. Not a drop.”

Deb was pounding now. My whole body rocked with every thrust. Her hands were firm on my hips, fucking me like she owned me.

Because she did.

They both did.

And I loved it.

I was fucked so hard and I started moaning loud. Mistress Victoria sat in front of me with legs wide open and asked me to lick her pussy. I licked it as I moaned hard. I was getting close to cum and in a few seconds I blasted my cum screaming over the pillow.

"That's a good bitch!" Mistress Deb said.

I was squirming from my ejaculation. The chastity cage was unlocked now.

The Shower

Mistress Victoria came near me and asked, "Aren't you thirsty?"

I nodded.

She gave an evil smile and signaled to Mistress Deb. I was first given some water, and then I was asked to lie down on the bathroom floor. The floor was very cold.

"Keep your hands above your head. Open your mouth with your tongue fully out, and close your eyes," Mistress Victoria said.

I understood what was going to happen.

Within the next few seconds, I felt the warm piss hitting my torso, and I could feel my cock getting erect again.

"Thank you, Mistress," I said, then went back to opening my mouth with my tongue out, eyes still closed.

Within seconds, I felt piss directly filling my mouth. I started coughing due to the unexpected gush of warm piss.

"Don't you think of spitting it out. Swallow now!" shouted Mistress Deb.

"This isn't new to him," laughed Mistress Victoria.

I swallowed the piss and thanked the Mistresses. By then, my cock was fully hard.

"Ha! Look at this piss slut! His clit is hard again!" exclaimed Mistress Deb.

"I've trained a good slut, Deb," said Mistress Victoria.

"Open your eyes," Mistress Victoria said.

I opened my eyes and saw both of them fully nude. Oh my god, what a view it was. My cock started twitching.

"You have five minutes. Clean up and come back crawling. Here's your glass of water. Drink it," said Mistress Victoria, and they left the bathroom.

I cleaned myself off, took a warm shower, dried myself, and crawled back on all fours.

The Orgasm

I saw Mistress Deb licking Mistress Victoria's pussy. Mistress Victoria held tightly to Deb's hair and moaned in ecstasy, eyes closed. I was watching everything, and my cock was fully hard by then.

"Good boy," Mistress Victoria said, looking at me, as Deb kept licking. Both of them stopped making out in five minutes. They were still naked.

Mistress Deb sat on the couch with her legs spread wide. She filled her glass with wine and started sipping it as she fondled her pussy.

"Get on the bed and get in the doggy position," said Mistress Victoria. I immediately obeyed.

A lubed-up, large vibrating dildo was pushed into my asshole. I let out a gasp. In the corner of my eye, I saw Mistress Deb smiling as she enjoyed the show. She was fingering her pussy.

The dildo was turned on, and I was asked to turn around and lie on my back with my legs up like a whore.

"Arch your back, legs above your head. You're going to drink your milk tonight!" said Mistress Victoria.

My cock was rock hard from the vibrations. I could feel my prostate getting stimulated.

I arched my back and tried to put my legs over my head. Mistress Victoria held my legs onto the bed, spat on my cock, held it tightly, and started jerking. My cock was very close to my mouth. The vibration level was turned up a notch, and my body started trembling, my muscles tightening.

"Open your mouth wide!" screamed Mistress Victoria.

I closed my eyes and let myself sink into what was happening. I started breathing hard and was getting into a trance. My mouth was wide open. I gripped the blanket tightly, and my whole body started to shake. I let out a loud moan as my cum ejaculated into my mouth. I collected all my cum in my mouth and was still shaking from the orgasm.

"Swallow," Mistress Victoria commanded.

I swallowed instantly and opened my eyes. My eyes were automatically closing again from the effect of the orgasm. I noticed Mistress Deb and saw her fucking her pussy with a nine-inch dildo, heading toward orgasm. The wine glass was empty by then.

"You did well. Rest now," Mistress Victoria said.

She kissed my forehead, gently brushed my head with her hand, and walked away.

I closed my eyes and drifted into sleep.