A Chance Encounter Pt. 01

Story Info
A chance encounter leads to a new life.
2.1k words
4.33
8.6k
8
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I was sat in the lobby of my hotel, wondering what I was going to do for the rest of the night. I ordered a drink, and sat watching the comings and goings in this fancy hotel lobby.

Then I saw her, tall blond, tight figure, with breasts just the right size. She looked directly at me, and our eyes met, causing a ripple through my groin.

She walked over to my table, and sat down "I'll have a scotch on the rocks," she demanded. I called over the waiter and ordered her drink.

"You're going to be my slave for the rest of the evening, doing exactly as I say, when I say it, understand Bitch?"

"Yes, Ma'am," I instinctively replied Not sure why, but it seemed the right thing to say.

Her drink arrived, and she said" drink it down in one, we have somewhere to go."

I obeyed, and swallowed the the fiery drink in one quick swallow.

"Now, take one of the ice cubes, and put it in your ass," she ordered.

"What, here?" I said not believing what she said.

"Yes, now, Slave, no is watching."

I did as instructed, the ice cold numbing my ass.

"Follow me, we are going to my club."

We hailed a taxi, and she gave the driver directions.

He looked at me in the rear view mirror, with a smirk on his face, and giving me a wink. "Can I play with him after you've finished with him?" he asked.

"Don't be impertinent," she scolded, "besides, when I've finished with him, he may be worn out."

We arrived at a car park, and she led me over to a black door. it was just a plain black door, no lights showing, nothing, it looked like it was closed. As we approached, the door suddenly opened, and an extremely large man, stood there, and greeted the woman, "Good evening Mistress Violet, just the one guest this evening?"

"Good evening Charles," she answered, "just the one."

"Will he be participating this evening, Mistress?"

"He certainly will Charles, maybe when your off duty?"

"Yes, please Mistress."

"Charles certainly is an eager beaver, and he really enjoys his job."

We entered the club, the lighting was very subdued, there was a bar area, and many booths, several of which were occupied.

"You find a vacant booth, while I order our drinks."

I searched for a free booth, they all seemed occupied, the people in the occupied booths, all seemed to be very involved. The first couple were kissing very passionately with the man caressing the girls breast. The next table I saw a man on his knees under the table, whilst the woman was groaning in ecstasy. I eventually found an unoccupied booth, just as Mistress Violet returned with a waiter carrying our drinks.

"Tip the waiter, kiss his crotch," she commanded.

I hesitated, (it was not something I usually did, Im not into men).

"Do it," she commended sternly.

I got down on my knees and kissed his crotch.

"That's better, " she said, "but in future you do exactly as your told, immediately."

"Yes, Mistress,"I said. we seemed to have crossed a threshold. I started to get up.

"Stay where you are, I have a use for you," She commanded.

She sat down in the booth, and motioned me to get under the table. I assumed she wanted me to kiss he feet or something.

As I got under the table, she lifted her skirt, "Lick it she commanded."

I looked up, and under her skirt, in her panties, I could see the outline of a cock. Fuck she was a transvestite.

"Take out my cock. and put it in your mouth."

I did as instructed, and wrapped my lips around her huge cock. She immediately pulled my head down unto her cock, effectively fucking my face. The head of her cock pushed at the back of my throat, causing me to gag.

"Take it, slut, take it down your throat, swallow my cock, you dirty cock sucker." The language she was using was really turning me on, that and the cock planted deep in my throat.

"That's it Faggot, take my cock, you are going to get your first load of the night."

She vigorously fucked my face, until I could feel her tense up.

"Here comes your first load, Faggot." Her cock began to pulse in my throat, I felt the cum spurting down my throat. She then pulled out slightly, so the last of her load swilled into my mouth. "Hold it in your mouth, slut, let me see it" I did as instructed, and showed her the cum on my tongue. "Swallow it, Faggot, now." I let the cum go down my throat.

"You can get up now, slave, you did well, I assume that was you first load, don't worry, it won't be your last."

I sat on the seat next to my beautiful Mistress, (or was it my Master, I was very confused).

"You did well, slut, I knew as soon as I saw you in the hotel, you would be the perfect Faggot."

I drank the drink she had bought, and the waiter immediately appeared with another. "Tip him." I got down on my knees again and kissed his crotch, Mistress seemed pleased.

I was confused, one minute I'm in the hotel lobby, checking out all the beautiful women, hoping to get laid, when suddenly I am being called a Slave, a Faggot, and a cocksucker, (although as I had just sucked my first cock, I couldn't complain about that one). Didn't know what was happening to me, all I knew was that wanted another cock in my mouth as soon as I could.

"You're mine for the night, and anyone elses who I allow to have you." "Yes. Mistress," I replied. I drank my second drink, and again the waiter came with another. "Tip him properly this time, tack his cock in your mouth and thank him properly."

I did as instructed, and got on my knees and pulled out his cock, and started to suck long and hard on it.

"That's enough," commanded Mistress.

I returned to my seat, disappointed.

"You have earned a reward," she said softly. She reached in to her purse, and produced a little brown Bottle, she unscrewed the cap, and gave it to me. "Take a sniff from this bottle, block one nostril, and sniff deeply through the other, then do the reverse."

The fumes from the bottle coursed through my brain, causing me to go light headed.

"Again, take four more deep sniffs." I did as instructed.

I felt a rising euphoria, as I inhaled the fumes.

"That and the drug in the drinks, will help you through the night, are you feeling the drug's effects?"

My head started to swim, and my dick was clawing to get out of my pants.

"Take out your cock, I want to see what we are playing with. Better yet, take off all your clothes."

I slowly took of my clothes, in the middle of the nightclub, nobody seemed to take any notice, not that I cared, my mind was swimming with the drugs. I stood in front of my Mistress, naked as the day I was born. She looked at my cock, and shook her head in disgust. "That's a pathetic excuse for a cock, it's no bigger than a woman's clitty, we'll have to lock it away." She produced a pink, plastic appliance,( it looked a bit like a little cock). She took the appliance apart, and put a large plastic ring around the base of my cock and my balls, then she put the dick part over my cock, and then locked the two parts together, locking up my cock. "There," she said,"we won't have to worry about the again."

She gave me the little brown bottle again, I sniffed away merrily. "Not too much, we don't want you out of it completely."

I noticed a stage over to our right, and there were two Men gyrating with each other, touching each other.

They started to get serious, sucking each other, then one started to kiss the others ass.

"Would you like to join them?" my Mistress asked.

"Yes please Mistress"

She led me up to the stage, and addressing the two men, 'my faggot would like to play if he may, but be warned, I take his cherry, no one else."

They reached for me, and pulled me onto the stage, they started kissing me all over, playing with my cage, and teasing me, making me hard, but the cage was stopping me growing, causing me intense pain.

There ministrations, were driving me crazy, tongues searching for every part of my body. I started to join in using my tongue on their bodies, taking a cock deep into my mouth.

One of the men started to lick my ass fervently, pushing his tongue deep into my crevice, opening it up, licking deep as his tongue was able to go, I pushed back against his tongue.

I heard my Mistress shout "use the dildo, open him up for his Mistresses cock."

One of the men picked up what looked like a real cock, and started to suck it. He then put it to my lips, and I eagerly started to like it, and suck it, I was in a frenzy, he pushed the dildo deep into my mouth, into my throat, I was making love to it. He then pulled it out of my mouth, to be replaced with a large cock, which I started to suckle. He poured lubricant on the dildo, rubbing it all the way down the shaft. Then he rubbed the end of the dildo against my hole, gently teasing, pushing against my hole, probing gently, opening my ass a little then releasing the pressure. then he pushed a little harder, pushing the head into my ass, opening me up gradually, the head passing into my hole with a plop. My ass stretching over the dildo, getting comfortable with the intruder. He then worked the dildo, until the entire length was in me. After a pause, he began to work the dildo in and out of my ass, gradually speeding up. I was backing up onto the thrusts of the dildo.

Suddenly, my Mistress was standing in front of me, her enormous cock pointing directly at me.

"Lubricate my cock, Slave, take me into your mouth."

I sucked my Mistresses cock for all I was worth, coating it with my saliva.

"Enough," said my Mistress,"he is ready for me, put him over the fucking bench, fasten him down, and lube his ass."

I was lifted up, and carried over to a bench, and laid across it, and bent over, straps tied around my thighs and across my back. My hands were locked into cuffs attached to the front legs of the bench.

"Now my pretty Faggot Slave, time to achieve your destiny."

She went round behind me, and I felt the tip of her cock pushing at the opening of my ass. With one hard push, she rammed her cock into my ass balls deep. I let out a little scream, but then relaxed to a satisfied moan, as my Mistress started to fuck my ass. She started to up the pace, plunging deep within my bowels. I tried to push back against the thrusts of my Mistress, but I was fastened securely to the bench. The pressure was building up within me, but I couldn't get hard, but I wanted to shoot my load. How could i have an orgasm without touching my cock. It was building up in me whilst Mistress was pounding away, at my sissy cunt, (as that was what it was now. I had found my place in the world, I am a cock loving, chastity Faggot). The Pressure built an built and built into the most fantastic, mind blowing orgasm I had ever had in my whole life, and that with no-one touching my cock. As my orgasm blasted through me, my Mistress was pulsing, and filling my man-cunt was her load. I felt the cum gushing into my sissy cunt. My mistress pulled out of my ass, leaving me gaping, and her cum seeping out of my ass.

The crowd cheered as My Mistress stood over me, with her dripping cock. She pushed her shit and cum covered cock straight into my mouth.

"Clean me bitch, clean all the cum and shit off my cock."

I suckled on her cock, taking off the shit and cum, and licking her cock clean.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
louiseacdlouiseacdabout 1 year ago

my god I'd love to be him

AnonymousAnonymousabout 1 year ago

Sure, he was straight when they met at the hotel.

Share this Story

Similar Stories

Bully's Mom Tricked Me Ch. 01 But she is making me a mindless sissy bitch instead.in Transgender & Crossdressers
The New Girls Femboy gets turned into a sissy by the New Girls in school.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
Pretty boy to Sissy girl Married pretty boy enjoys being cuckolded.in Transgender & Crossdressers
Sissy Date Turns Serious Sissy is physically feminized.in Transgender & Crossdressers
More Stories