A Sissy Slave's Autobiography Ch. 03

Writers note: OMG thank you for the kind words and support! I had no idea my first story would take off! This storyline is just getting started and there are many more adventures to come, if you'd like to help me edit or you'd like me to help with something you're writing please let me know!

I followed Amanda into the room. In one hand she held a very small plastic chastity cage. It was pink (of course it was pink) and no longer than an inch and a half. Big enough for me to fill it soft but would not allow me to get hard in the slightest. In her other hand was a chrome butt plug with a pink heart on the end. Honestly, I was surprised I'd gone this long without being plugged and caged like a real sissy.

"By the look on Greg's face, you have passed the first test," she said.

I looked over at him pouring a drink and rolling his eyes with a slight smile at Amanda's comment.

"We will continue the interview. If we choose you, you will always be plugged and caged unless we specifically allow you not be be for cleaning or emergency reasons."

I nodded to show my understanding.

"Face down ass up, spread your cheeks," Amanda's luscious voice calmly stated.

I dropped to the floor and I smiled again! I know it would anger them but I couldn't help it, I wasn't trying to be a brat, this was just such a huge moment for me, a decade in the making. This was the thing I've been dreaming of, finally becoming a reality.

"The little bitch loves this," Greg said, "but I bet that smile will turn to tears by the time we're finished with you,"

With the utmost submissive passion and defiance I pulled my face from the carpet and said "I hope so, sir."

With that he walked over, grabbed my face and spit on my face.

"Lick it up."

I did.

"Lick my feet," he was barefoot now, I did that as well.

As I was licking, I felt a lubed finger push my bud, then probe inside my asshole, then two as expected. Amanda took her fingers out and then finally the cold metal of the chrome plug began to be inserted. Slowly at first until my hole adjusted and took it all.

"Very clean and shaved ass, or should I say pussy! Looks ready to be fucked!" Amanda said. That compliment felt great.

"That didn't take long," Amanda said apparently satisfied with her work.

"The sissy loves having her ass played with," Greg said smiling. This was true, I smiled and wiggled my plugged ass for him.

He pulled his feet away and grabbed my face again. I had been buried in his feet this whole time. He had been very harsh so far and that is why what happened next sent me into such a deep sissy sub space words can't describe it.

He looked me in the eye, stroked my cheek and said, "good girl,"

"Thank you sir," I managed to squeak out, holding back tears. Tears of joy at his approval.

"Okay slave, sit up on your knees, time for your cage," Amanda said from behind me

She has some difficulty locking it in as I was incredibly hard. From the cold plug in my ass, the taste of Greg's feet on my tongue and his small compliment. I was ready to cum again.

Greg walked over with a couple ice cubes and rubbed them on my clit and balls, I yelped and my clit retracted in a matter of seconds.

Amanda locked me in and there was very little extra room, but I loved the feeling. It felt safe, like I was not my own, like I had no say over my sexual desires. It felt as if being locked meant Amanda and Greg would take care of me, it meant I had to trust them as my keyholders.

Amanda wriggled her white bikini bottoms off and crawled over to the bed, then she took the same face down ass up position I was in moments ago revealing her prize.

Her pink asshole, her gorgeous pussy lips, her Brazilian waxed butt and pussy, it was all too much.

'Don't fuck this up,' I thought. I was also full of envy, I didn't want to fuck her, I wanted to be her. That statement perfectly summarizes my suppressed sexuality for so long. I wanted to be just like her, a hot, curvy, powerful woman. I hoped they would turn me into one.

Amanda had a simple command.

"Eat me."

I crawled onto the bed and got to work instantly on her delicious pussy, within seconds I felt a sharp slap on my ass. It was Greg's strong hand.

"Her ass bitch not her pussy, you have to earn her pussy."

"My apologies sir," I wasn't at all disappointed to switch to the correct hole.

I licked and probed and poked inside her ass. I noticed her hand started rubbing her pussy as she quietly moaned.

I ate her ass for what felt like an eternity and an instant both at the same time. I could sense Amanda was getting close to cuming, she was playing with herself intensely.

In one smooth motion, Greg swooped in behind me, grabbed me by my legs and flipped me over to my back on the bed. He then pulled me to the edge of the bed, asserting his dominance. I felt tiny compared to him, my slim 5' 10" 175lbs compared to his muscular 6'3" 230lb body. He had me hold my legs up revealing my plugged sissy pussy to him. Amanda flipped around and sat squarely down on my face and yelled

"Make me cum sissy!"

As I licked, her delicious juices ran down my face. The taste, the smell, her divine womanhood overwhelmed me.

My little cock strained against its cage, precum steadily leaking out of the hole in the top of the cage.

Greg stood at the end of the bef and pulled the plug out of my ass. He replaced it with his hard cock while my ass still gaped.

His rock hard dick filled me. Both figuratively and literally

He held his cock inside me for a moment while my ass could adjust.

It burned. It hurt like hell. But the warmth of his throbbing cock inside me was comforting. I felt safe with him.

Amanda was grinding my face like crazy, making breathing a challenge. She held her head back and her long brown hair fell down her back. The godess ran her hands all over her tanned hourglass body. I noticed for the first time now that her top was off that her nipples were pierced and her breasts had the sexiest tan lines as well.

This was the sexiest woman I have ever seen in my life.

Greg began fucking me. Slowly at first then harder and harder. It still hurt, it was uncomfortable but I had never had a real dick inside me. The dildos and vibrators my ex wife didn't know I used were fine, but a real dick was like night and day better.

He didn't just take my sissy virginity as he fucked me, he fucked the masculinity out of me. With every thrust he was turning me into a girl, into his little cock whore.

"Ever have a sissygasm?" Greg asked

"Nuh uh," I kind of said with a mouth full of pussy.

Greg was behind his wife, rubbing her pierced nipples, kissing her neck, her hands leaning back holding his thighs. Their movements on my body in sync with each other.

Amanda fucked my mouth with her clit moaning and making primal noises.

Greg impaled me, clearly making me his bitch. He fucked me hard but with rhythm, clearly enjoying the feeling of my sissy pussy.

Then Amanda came. Hard. Without warning, I learned she was a squirter. Her juices exploding into my mouth and in my nose, running all over my face. I quickly swallowed so I wouldn't choke. She didn't get off but turned around to face her husband. She stayed mounted on me but moved slower still enjoying the waves of her orgasm. She deeply kissed Greg with more love and passion than I've ever seen from a married couple.

I didn't feel jealous, or envious. I didn't wish my failed marriage had this kind of connection. I felt proud. Proud that I helped make that happen, I provided this moment for them to connect on such a deep sexual and spiritual level.

Then, in the middle of this passionate moment my useless sissy body helped provide, For the first time in my life I sissygasmed. As Greg's cock grinded my prostrate the ooze of precum turned into an orgasm for me through my cage. I didn't ask permission, so I began to panic but I was so overwhelmed with pleasure.

I moaned and squirmed but didnt hear Greg say anything, he continued to pound me and his tongue was intertwined with Amanda's.

Shortly after, Greg came too, in my ass. His warm seed filling me, warming me, claiming me as his slave.

He pulled his cock from my ass and we all slumped down on the bed together panting.

Nobody spoke for some time, we were all a tangled mess of limbs and body parts and sweat.

Amanda gently kissed her husband and whispered

"I love you, Greg."

"I love you too, baby." He replied. Their love powerful and thick in the air.

Amanda then turned to me and kissed me on the cheek and said, "good girl, your tongue is very talented,"

Greg then added, "that asshole is tight, the interview committee is very impressed so far,"

We all kind of chuckled.

"But," Greg said,

I thought he didn't notice that I came but the sticky mess on my tummy was hard to miss.

"You will be punished for cuming without permission. Not now but before the sun rises in the morning you will regret cuming without permission."

I felt a lump in my lump and a knot of nerves in my stomach. But I was excited, this was part of being a sissy, the punishment and humiliation were a major part of what I craved about this lifestyle.

Greg got up and went to the closet, he pulled out 2 tiny sequin dresses, one black and one silver. The stereotypical 'hot girl in Vegas dress.' He pulled out two pairs of black 5 inch high heel shoes, the larger pair obviously meant for me.

"Amanda you get to pick," he said, "sissy gets the other one."

The sun was setting beyond the balcony, and anyone who knows Vegas knows that this is when the city comes alive. The clubs, bars, casinos and streets would be buzzing soon.

"It's time for your final test," Greg said smiling as he looker out over the balcony to the strip.

No turning back now? No turning back now.