Sissy in a Womens Prison, Pt. 01

Dear Readers,

I appreciate all my followers and I want to thank those who've recently left comments. Lazy Diogenes, JT, JoyceCD and Sissy Lucy, your thoughtful postings are most welcome!

Sincerely,

Whippet

--

I was peeping into a woman's bedroom window and marveling at the shapely lady inside. The pretty gal was just unclasping her Playtex bra when a policeman apprehended me. I begged to watch a little longer but the cop promptly led me away in hand cuffs.

A jury of 11 females and a guy in drag found me guilty of criminal voyeurism. Since this was my third offense the judge sentenced me to prison. I was allowed to serve my time in a women's institution because I'm a pantywaist.

The minimum security facility allowed inmates to supply their own apparel. So, I brought in 19 garment bags filled with dresses, skirts and blouses, 5 suitcases of lingerie and 2 trunks filled with high heels.

I was unpacking when my roommate returned from lunch. She was a statuesque woman with a crew cut, wearing camo slacks and a matching hoodie. My dream girl!

"Hello, I'm Angela," I said brightly.

"I know who you are and what you are," said the big woman in a flat tone of voice. "Now, let's see what you've got under that dress."

The authoritative tone of her voice was exciting but I was put off by the impertinent demand.

"Excuse me," I said in an insulted tone, "but may I at least know your name?"

"I'm Wyatt," she replied. "Mistress Wyatt to you. Now lift your skirt, Angela. I want to see what you have to offer."

I knew that she meant business and that she wasn't going to say please. So I obediently raised the hem of my pleated miniskirt while Wyatt pulled down my Bali Skimp-Skamp panties.

"I figured that you'd be caged," she said when she saw my chastity device. "That's why I smuggled these in. Sit on the bed."

Mistress Wyatt sat next to me and snipped away the cage with wire cutters. She chuckled when my little sissy rod sprang to life.

"I'm glad that you like me, Angela," she said. "Unfortunately for you, I'm not into Nancy boys."

"So, why did you free me?" I asked naively.

"For business reasons," she said with a smirk. "I'm your pimp."

--

Mistress Wyatt wanted me to have a special look for my first customer. So, she took me to the prison beauty parlor.

The hair dresser, Tiffany, was a petit brunette with lovely blonde highlights. She showed my pimp a brochure illustrating the most feminine styles. Wyatt selected a beehive with side swept bangs for me.

"That will look pretty on Angela!" said Tiffany. "Is there any particular color?"

"Do I get a vote?" I squeaked.

"No," replied Wyatt. "Make him flaxen blonde," she ordered the beautician. Then she left me alone with Mistress Tiffany.

The beautician sat me in front of her shampoo sink, tilted me backward and put a pink plastic cape around my neck. I loved her personal attention.

"Are you comfy, Sweetie?" she asked, resting her hands gently on my shoulders.

I felt more than just comfy. The feminine aura of the beauty shop and the plastic cape made my weenie stiffen.

"Yes, Mistress Tiffany," I answered happily.

Mistress bleached my hair, rinsed it and then applied the flaxen dye. Her gentle fingers working in my long tresses felt wonderful. When she held up a mirror I fell in love with my new hair color!

"I'll be gone for a few minutes while the dye soaks in. Be good," she cautioned.

I tried to be good. However, my flaxen blonde hair and the pampering I'd received from Mistress Tiffany had stirred delicious girlie feelings inside me. Soon I was holding the mirror with one hand to admire myself while joyfully stroking my boy clitty with the other. I was breathing hard when Mistress returned.

"I'm sorry but that's not allowed," she scolded mildly. "Wyatt wants you to be full of juice for your first client."

"I'll have to secure you with these," she added, taking restraints from a drawer. Then she buckled my wrists to the the chair. Bondage makes me feel marvelously submissive, so I was even more turned on than before.

Mistress Tiffany proceeded with my styling. She coiled most of my blonde tresses into a glamorous beehive. Then she trimmed my bangs and brushed them to the sides of my face. Finally, she moved me to a chair under her dryer and secured me in place.

When my hair was dry, Mistress sprayed it with jasmine scented perfume. Then she fitted a lovely jeweled hairband between the updo and the bangs.

"You look like a debutante at her coming out party, Angela," said Tiffany with a satisfied smile. When she turned my chair toward the mirror I was spellbound by my own beauty.

--

Tiffany unlocked the restraints and walked me back to the bedroom. When we arrived, there was a prison guard with Mistress Wyatt and they were looking through my closet. The guard was a tall black woman with an afro. The taser on her belt stirred up punishment fantasies and I felt weak in the knees.

"Gerry," said Mistress Wyatt to the guard, "this is Sissy Angela. He's the reason that I needed your wire cutters, and he's yours to play with as a token of my appreciation."

I curtsied and smiled sweetly.

"He's cute," replied Mistress Gerry with a crooked grin.

I was tickled pink that the guard liked me. Then she walked over to me and turned me in a full circle. She admired my hairdo and brushed my bangs with her finger tips.

"Nice work, Tiffany," she said to my hair dresser. "Blonde pansies with updos make me really hot."

Then Mistress Gerry put a manicured finger under my chin, lifted my face to hers and said softly, "Are you going to show me a good time, Sissy?"

"Yes, Mistress Gerry," I said eagerly. "I want to be your play thing!"

"Good girl," said the guard. "Let's pick out something appropriate for you to wear."

I heard the bedroom door close as the other women departed.

--

"I want you in a pink dress," said Mistress Gerry obviously enjoying her dominance.

"I have a pink sundress that you might like, Mistress," I offered.

"No, I want you in something more refined."

"Then maybe my pleated mini with puffed sleeves?" I asked.

"Show it to me, Angela," said Mistress. She was smiling and it was the first time that she used my name. I loved the rapport we were building.

I removed the little frock from its hanger and held it up in front of me. The color of the dress matched my nail polish and lip gloss.

"Nice!" said Mistress Gerry.

Then she turned me around and unzipped my sheath dress. Embarrassment at being seen in my lingerie turned my cheeks red. I was wearing a Maidenform push-up bra, my sheer Bali panties and lace top nylons.

When Mistress circled her strong arms around my narrow waist I melted into her embrace. Then I sighed with pleasure when she kissed the nape of my neck.

"Put on the dress and lay on the bed for me, Sweetie," said Mistress. As I complied, she removed her trousers and underwear. Then she straddled my chest while holding a pair of hand cuffs in one hand and her taser in the other.

"These are for bad girls who don't obey," she warmed. "You're not a bad girl are you, Angela?"

"No, Mistress Gerry. I'm a very good girl and I'll do anything you want," I said in a nervous voice.

"Then we'll get along just fine," she said. Mistress moved forward and settled her pussy over my mouth.

Her muff's was scented with delightful lilac perfume and she was already wet. I applied my tongue to her labia and slowly licked up one side and down the other. When I glanced up she nodded her approval. So, I kept licking at a steady pace.

Mistress closed her eyes and a look of serenity came over her lovely face. She was moaning softly and exuding delicious feminine nectar into my mouth. When I quickened my tempo her breathing became faster and deeper.

As Mistress's passion built I tested her clitty with my tongue. It was fully erect and ready for my oral devotion. Her ardor soared as I stimulated the sweet little nub. Soon she was pounding me with her fists and then she climaxed with a loud scream.

Without a word, Mistress shifted down to my pelvis. She slid my knickers down to my knees and gobbled up my little weenie with her hungry snatch. Mistress stroked me hard with her wonderful hoo-ha until I reached a crescendo of sissy bliss.

When she shouted, "Give it to me, Angela!" I unloaded my hot spunk inside her ravenous coochie. Mistress Gerry climaxed again with an even louder shriek.

Then she laid down on top of me and kissed my lips.

"I hope the judge gave you a nice long sentence, Sweetheart," she said warmly.

--

This story will be continued.