First Day

“Time for bed, sweetheart.”

I’d been dreading this moment from the second the auctioneer banged his gavel and chanted “Sold, to the man in the fur coat!”

Would I be able to please Mistress?

Reality, the world is owned by the very rich, and laws have been changed to reflect the fact. “Work programs” are more cost effective to the taxpayer than prisons. Work program, a euphemism for ‘slavery.’

Today’s auction featured young men and women.

I was led off stage to a holding cell and my chain leash unhooked from my collar. There I stood with the previous six ‘offerings’, and we waited. Eventually the last one, a buxom redhead, was brought to the cell, and one at a time our number were called, we were leashed and led away.

“Number seven.”

The man in the fur coat stood. Tall, dark hair with some silver in it. On a couch sat an elegant lady. She wore a cream silk blouse and an ankle length tan wool skirt. Over her lap and left shoulder was a long white thick fur stole.

Also in the room was the guard who brought me, two other guards, the judge who sentenced me, and the auctioneer.

My chain leash and collar were removed. My wrist shackles and hobbles unlocked and removed. I stood there barefoot and naked except for the cotton prison shorts.

“Take the shorts off and put this on.” The man in the three quarter length silver fox handed the guard a full length mink coat. He held it for me to slip my arms into. Suddenly I realized the sleeves were dead ended. The guard fastened the front, which tapered as it went towards my ankles like a hobble skirt. He hooked the ring on the end of my right sleeve to the shackle on the end of my left, then pulled the ends of the collar together, joining their steel rings together with the snap shackle on the end of a meter long woven leather leash at my throat.

The lady stood. She was tall too. Maybe one eighty cm.? I stand to their chins in bare feet. I’m a fair complexioned, light brown hair, one fifty five tall twenty three year old man.

In the court’s parking lot I was put into the back of a KIA luxury sedan and belted in. The man drove, the lady beside him. The back windows were dark tinted.

Their condo consisted of two floors high up in the building. We were greeted at the door by a very shapely blond haired, milk chocolate skinned lady. She wore a light blue ankle length satin gown, with a deep ‘V’ front that barely held her magnificent set in. She took the lady’s stole and set it on the bench, then the gentleman’s fur. After she had hung them both in the closet, the man said, “Yvonne, this is our new toy. We’re calling him ‘Timmy’. Please take his coat.” I almost said ‘that’s not my name’ but thought ‘better keep my mouth shut.’

“Yes sir.”

“Timmy, you will address me as ‘Mistress’.”

“And me, ‘Master’.”

“Yvonne, take Timmy and find him some clothes, dear.”

“Yes Mam.”

I followed her, trying to cover myself.

“So, Timmy, how long will you be with us?”

“Um, twenty months. How about you?”

“Oh, dear, I’m not a criminal. No slight intended. I’ve a five year contract..”

“Oh.”

“So, here’s our dressing room. This closet is yours. That one is mine. Lets see, I guess something ‘one size fits all’ for now. Later we can sort your things out.

There were jail house rumors that decent looking young criminals were auctioned as household servants and sex slaves. I started to believe when I saw who I was being auctioned with. Now seeing the clothes in my closet confirmed it. All the clothes in ‘my’ closet were in different pastel shades of see through material. Well, at least Mistress was a good looking lady. Fairly old, forty, fifty (?)

but not some wrinkled old grandma, or ugly spinster who’d demand constant servicing.

“Here, try this on.” She handed me a pair of black gossamer culottes and a matching crop top that barely covered my chest.

“There are no men’s shoes.”

“No. Have you ever worn heels, sweetie?”

“No.”

“OK, lets try this set with the two inch block heels.”

Master and Mistress were in the den. “On your knees Timmy so I can collar you.”

“Yes Mistress,”

“Timmy, come.”

“Yes Master.”

We went to the main entrance hall. “Stand by the door.” Master fiddled with his phone. ‘beep’. “Come here” He pushed another few buttons. “Go to the door.” I did. “Damn.” He pushed more buttons. ‘Beep’. “Come here.” He pushed buttons and sent me back to the door. “God dammit! Margaret, dear, can you come here?”

“What is it darling?”

“I can’t get this to initialize.”

“Here, let me see.” she took his phone. “Timmy, sweetie, go stand by the door.” She pushed some buttons. ‘Ding.’ “Come here.” ‘Ding ding ding.’

“Go to the door.”

Suddenly my whole body twitched and I collapsed to the marble tiled floor. Master’s phone went ‘ding ding ding’. When it stopped Mistress helped me to the bench. “Sit here a minute Timmy.”

When I recovered Mistress took me downstairs. We went through the kitchen. “Greta, this is Timmy.”

“Hello Timmy.”

“Hello, um,er? Mistress.”

“No, I’m the chef, you can call me ‘Greta’, Timmy.”

“I’m just showing him the service entrance.”

We went through the pantry and utility room. “Stand by the door.”

“No. No please Mistress. Not again,” I whimpered.

“Timmy.” Her voice was stern. “Never, ever, ever say ‘no’ to master or me. Ever!” Then her soft normal voice returned. “I won’t shock you this time.I just need to program this door into the phone.”

Back through the kitchen. “Greta, we’ll have lunch in the yellow dining room.”

“Yes Mam, Master already told me. Nancy is setting the table now.”

“Thank you. Come Timmy.”

Master and Yvonne were already seated and the maid, an older woman in a simple dove grey work dress was handing out salad bowls.

After lunch Yvonne was assigned to show me around. As we roamed she asked me if I were a virgin.

“No.”

“Been with a girl, or a boy, or both?”

“A girl, of course.”

“Never a boy? Even kissed, or petted?”

“No. Yuck.”

She smiled and dropped the subject.

After showing me the downstairs, then upstairs to the formal part of the condo, I asked where my room was.

“What do you mean?”

“Like, where do I sleep?”

“We’re just about to the bedroom wing. Come.”

She led me into the master suite’s sitting room. It has pale beige patterned wall paper, hardwood flooring, and an oriental rug surrounded by a roundly padded couch and two matching wing back chairs. In the middle was a round mahogany coffee table.

There were two open bedroom doors. We went through the one on the right.

The bedroom was painted a very pale pink with white gloss trim. There were erotic oils and charcoal prints on the walls. The king size bed was on a one step pedestal that was carpeted in the same rich thick soft beige carpet as the rest of the room. It faced a floor to ceiling glass wall that had thick gold and beige drapes that were pulled back.

“Come around here Timmy.” She led me to the foot of the bed. The gold velvet skirt ended, and the pedestal ended at the end of the sides too. Below the mattress was an twelve cm chrome bar grill with a padlocked door.

“If they don’t want you, or if you deserve punishment, you will be locked in there.”

“Oh.”

“Do you understand? You need to keep them pleased.”

“Um, yes, yes.”

“Good. lets look at the other bedrooms.”

We went through a door to an en-suite. bath, shower, vanity, toilet and bidet, then through it’s far door to the other bedroom.

it was similar to the first, but decorated in shades of blue and there was no cage under the bed. Back through the sitting room to the hall. Into a smaller very girly, fluffy bedroom. “This is my room.” From it we went to the changing room where our closets were. Next we peeked into the three guest rooms.

We ended the tour in the intimate wood paneled den where Master and Mistress were reading.

“Just in time darlings. Yvonne, why don’t you mix a big pitcher of Caesars? Timmy, come sit with me.”

“Yes Mistress.”

Yvonne sat with master. He held her hand. Mistress lay her arm over my shoulder. Very nice. I forgot my shyness, wearing see through culottes. Mistress talked about the book she’s been reading. Master talked about their upcoming trip to Spain, saying he’d ask his lawyer if I could get a passport.

“Dinner is ready any time Mam.”

“Thank you Nancy, we’ll eat in half an hour.”

“Very good Mam.”

We ate in the much larger formal dining room on the top floor, then lingered over coffee and conversation.

“Time for bed sweethearts.”

We slid our chair back and stood. My performance anxiety returned as we followed Mistress and Master to the suite. We all kissed ‘goodnight’ in the sitting room.

Then everything flipped.

Mistress took Yvonne’s hand and they went to the bedroom on the right.

Master hooked a finger through the ring on my collar and led me to the one on the left.

Oh no! That’s why Yvonne asked. Tears started down my cheek. How can I get out of this? Will I spend my very first night in the cage under the bed?

Master pulled me down beside him on the love seat. With the back of his finger he gently wiped my tears away.

“Don’t be afraid. I know how to be gentle with virgins. You’re not my first.

“I remember my first time. It wasn’t nice. I had a summer job on my uncle’s farm. One of the farm hands cornered me in the loft and took me. He was a rough brute.

It wasn’t gentle. So I know. I’ll be very gentle with my sweet little virgin.”

His left arm went over my shoulder. I was shaking, and crying. His right hand stroked the soft chiffon on the top of my thigh.

“Just relax Timmy. That’s a nice outfit you’re wearing. Did you choose it?”

“N-n-no M-master. Y-Yvonne d-d-did.”

“Isn’t she quite the sexy gal? I bet you’d like to fuck her. Let me tell you, that young lady is quite the wild ride. Mm.”

“Uh.” I whimpered as his hand slid up to my stuff.

“Now relax. This doesn’t hurt, does it?”

“N-n-no sir.”

His hand moved up under my skimpy top. Thumb and forefinger gently rolled my nipples until they were hard as marbles.

“You are a very handsome young man. Has anyone ever told you that?”

“N-n-no sir.”

“Call me ‘Master’ dear, ‘Sir’ is too formal, don’t you think?” As he talked he undid the three clear plastic buttons down the front of my top. “Stand up sweetie.”

Master stayed seated. He turned me to face him standing between his legs. He reached up and brushed my top off my shoulders. It slid down my arms and fell to the carpet. He smiled a warm smile, looking up into my eyes. Without breaking eye contact his hands slipped from my side down to my hips. He hooked his thumbs on the elastic waist band of my culottes and walked them down ’till they fell to my ankles.

“You’ve a beautiful body. You should be proud of it.”

My tears were falling freely. I had no choice. I was his property for the next twenty months.

“I think I know what Timmy needs about now.”

I flinched even though Master cupped my balls so gently. He gently fondled them as he swallowed my limp dick. God! I felt his tongue doing things as I grew hard in Master’s mouth. I looked down. His head moved back and forth. I closed my eyes and tried to pretend it was Yvonne swallowing me. I didn’t know what to do with my hands. God, he’s good! I rest my hands on his strong shoulders.

What a blow job! I came with a gasp. Master smiled up at me. He pushed me back, turned me and pulled me to sit sideways across his lap. My hands were crossed trying to cover up my still hard cock.

With a finger he gently turned my head to face him. He kissed me on the lips. I didn’t want to but I knew when his tongue was pushing on my lips, I must.

His hand gently held the back of my head. ‘so that’s what cum tastes like’, I thought as we kissed. The kissing was kinda nice.

“Young and beautiful AND a great kisser too!” He stroked up and down my back. “Pretty Timmy.” We kissed and I relaxed to the sensation of my first man kisses.

“I’ll get undressed, you turn back the bed and get in.”

Well I THOUGHT I was ready. “Y-yes Master.”

I slipped off my heels and climbed up onto the hard mattress. Master climbed in beside me, naked and hard. Big and hard. I began shaking again.

“Just relax. Here, lets sit together and enjoy the view.” We leaned against the diamond tufted gold satin headboard and looked out across the city. Master had his arm over my shoulder.

“Don’t the city lights look nice twinkling like that. dear?”

“Y-yes M-Master.”

“They’re pretty and so are you.” He kissed my cheek. He nibbled my ear lobe. “Pretty boy.”

I turned to him and we kissed. Kissing is good. I slid my tongue into Master’s mouth. We kissed some more. His hand gently roamed as we kissed.

There was a recessed shelf in the headboard. From a small bowl on the shelf Master took a foil package and handed it to me. “Kiss me Timmy, then put it on my cock.”

I knew where he meant me to kiss. I bent down and kissed his shiny knob. I began shaking and the tears started again as I rolled the ‘Trojan’ down his member. ‘I can do this’, I told myself.

Master pulled me back up to himself and held me so gently. “Shh Timmy, it’s alright.” Kiss. “I won’t hurt you.” Kiss. “We’ll go nice and slow.” Kiss.

‘Sniff’ I calmed down a bit.

“Here.” Master dabbed my tears with a Kleenex. he handed it to me. “Wipe your nose, dear.”

“It’s just that I’ve never……”

“I know dear. Just relax.” Kiss. “You’ll like it.” Kiss. “You’ll see.” Kiss. “We’ll take it nice and gently.”

We kissed some more.

“Roll onto your hands and knees facing the window, dear.”

Master stroked my back. He kissed my shoulders. “Down on your elbows….Good boy. Now spread your knees a bit more.” He gently squeezed my buns. “So pretty. Just relax.”

“Ah!” The first dollop of lube surprised me as it dribbled down my crack.

“Easy baby, easy. Let me work it in.”

His finger slid the slippery lube along my crack. He pushed it at my hole. “There, good boy, just relax.”

“Uh!” His finger pushed in. OK,OK, not bad. Oo, right in. I felt more lube dribbled on my crack. Oh! Two fingers in. OK, sort of nice, I guess?

Master’s left hand was holding my left shoulder. His fingers slipped out. I knew what was pushing at my sphincter. I knew. It pushed and spread. It hurt. Would his big, hard, cock actually rip me open?

Oh! It’s all the way in. It quit hurting. Oh, he’s pushing right into me. Both his hands are holding my shoulders. He pushed in ’till his thighs were against mine. Oo.

“Good boy.” Deep in me, he moves his strong hands to either side of my waist, then pulls most of the way out.

“Ah.” He pushes in, then back.

“Mm.” He pushes in again. Interesting sensation!

He steadily strokes.

He changes the rhythm. Slow out, thrust in.

Thrust. “Uh.”

Thrust. “Uh.”

Thrust. “Uh.”

“Good boy.”

Thrust “Uh.”

Thrust. “Uh.”

He slows down and gives me nice long strokes of his cock. It is nice.

Stroke. “Mm.”

Stroke. “Mm.”

My cock is hard from the stimulation of my prostrate.

Stroke. “Mm.” Oh Master!

Stroke.”Mm.”

His arms wrap around my tummy and he holds me tight, his cock deep in, and he quivers.

“Baby!” Master cums. He cums deep in my butt. Oh my God. I felt it when Master came!

His cock still buried in my ass, Master pulled me onto my side and spooned me.

“See, Timmy? I knew you liked it when you started pushing back to meet my thrusts.

“Lets cuddle for a bit, baby.”

The End