Sissy in a Womens Prison, Pt. 02

Dear Reader,

In Part 1, Sissy Angela met his roommate and pimp, Mistress Wyatt. His new Mistress ordered the prison's beautician, Tiffany, to dye the sissy's hair and style it in a glamorous updo. Then she loaned Angela to a prison guard as payback for a favor. In this installment Angela services a prison VIP.

Sincerely,

Whippet

--

I awoke the next morning to the delightful scent of perfumed pussy. My face was covered by the hairy snatch itself, though, so I couldn't see who it belonged to.

"Is that you, Mistress Wyatt?" I inquired meekly.

"It's me, Sissy Boy," she replied.

"I thought you preferred girls," I ventured.

"A tongue is a tongue, Pantywaist. Now start licking before I get angry."

--

After Wyatt climaxed she wanted breakfast. So she ordered me to fetch her morning meal from the prison cafeteria.

"May I dress first, Mistress?" I asked.

"Do you want to feel my leather belt on your prissy ass?" was her retort.

So, I made my way to the cafeteria in my baby doll nightie and high heeled marabou slippers. The skimpy outfit was embarrassing enough but even worse was being seen without my makeup!

Other inmates whistled and cat called as I sashayed down the hall. One horny woman dragged me into her room and tore off my panties. Then she flung me onto the bed and jumped on top of me. When her roommate warned that I belonged to Wyatt, my abductor immediately released me.

"Please don't tell Wyatt," she begged as she handed me my knickers and hustled me out the door.

I told the cafeteria cook that Mistress Wyatt had sent me for her breakfast. Instead of dishing out food from the hot table, she prepared a special order of Eggs Benedict with Hollandaise Sauce. When I asked whether I could have something to eat, she added a half grapefruit to my tray.

While Mistress Wyatt savored her scrumptious breakfast and I nibbled on my grapefruit, she told me that I had an important rendezvous ahead.

"Your client will be a prison VIP," said Mistress. "So, I'm taking you to see Tiffany in the beauty parlor again."

--

"What can I do for you ladies today?" inquired Mistress Tiffany with a friendly smile.

"The Warden wants to see Sissy Angela dressed as a school girl this morning," answered Wyatt.

"The Warden herself!" replied Mistress Tiffany. "That's an honor, Angela!"

"What kind of hairdo goes with that?" asked Wyatt.

"I'd recommend a flip style," said Tiffany, "like girls wore in the 60s. The hair is curled outward and it rest on the shoulders. I'd tie a cute ribbon across the top of Sissy's head and give him bangs, too. Did Warden specify a color?"

"No," said Mistress Wyatt. "I'll leave that to you."

"Then I'll make him a lovely mocha brown. He'll look adorable with his brunette flip and the school girl outfit."

Mistress Tiffany sat me in front of her dyeing sink, buckled my wrists to the chair and placed a plastic cape over my shoulders. I relaxed and enjoyed the lovely ambience of the beauty shop while Mistress attended to my hair. After my tresses were dyed, Mistress put me in curlers and moved me to her dryer.

"If you promise not to play with your weenie, Angela," said Mistress Tiffany, "I'll give you some vintage fashion magazines to browse."

I happily agreed to her terms and contentedly flipped through issues of Elle and Mademoiselle from the 60s and 70s. I fell in love with the ravishing young models in their Pierre Cardin and Givenchy mini-skirts and peek-a-boo blouses. I wished that I were them!

Wonderful pictures of shapely misses in girdles and waist cinchers from Gossard and Triumph sent chills down my spine. Most exciting of all were the ads for PermaLift's satiny push-up bras and Vassarette's lacy garter belts. They made my little dickie stiffen in my panties.

When my hair was dry Mistress Tiffany brushed and combed me. I was delighted with my bouncy curls! Mistress removed my plastic cape and I embraced her warmly to show my appreciation.

"Good luck with the Warden," said Mistress encouragingly as she kissed my cheek.

--

Mistress Wyatt collected me from the beauty parlor and we returned to our bedroom. She had already gone through my apparel and selected a plaid mini-skirt and a sheer pink blouse for my rendezvous. She also picked out a lacy black bra that would show through the blouse.

"You can choose shoes and accessories, Angela," she said.

I was surprised that Mistress allowed me this freedom. Perhaps I was gaining her trust.

I chose a pair of patent leather flats with bows on the vamps. Then I added dangly earrings and an ankle bracelet to complete my look.

Mistress smiled at me for the first time ever. Then we proceeded to the Warden's office.

--

"He looks like a Radcliffe girl!" said the Warden merrily. "Come here, Sweetheart," she added warmly.

I timidly advanced to the upholstered chair where Warden was seated behind her desk. She smoothed my short skirt and played with my curls.

"He's adorable, Wyatt!" she said to my pimp. "You've done a great job."

Mistress Wyatt took that as a hint that she should leave. Then Warden addressed me directly.

"Guard Gerry hold me wonderful things about your orals skills. I'm looking forward to the same personal service. Now, crouch under my desk like a good sissy."

I crawled underneath while Warden hiked up her skirt. She was wearing open crotch garter panties with taupe nylons. The wonderful scene set my heart fluttering. Warden's shaved pussy was scented with lovely floral perfume, too. My head was spinning as I eagerly applied my tongue to her labia.

Just as I began licking, Warden's administrative assistant entered the room.

"Warden," she said. "I'm sorry to intrude but I need to remind you of the judicial telecon. It's already started."

"Oh, darn!" exclaimed Warden. "I had forgotten about that. Thank you, Millie."

When the assistant had departed Warden said to me, "Keep licking, Honey Boy. You're doing a swell job."

Warden dialed into the telecon and I heard voices from her speakerphone. She must have muted herself because she was now moaning and breathing deeply.

Then I heard a voice that I recognized. It was the judge who had sentenced me to prison.

"Warden Brown," she said, "how is that Nancy boy working out? I hope he hasn't been a problem."

"He's no trouble at all, Judge Wilson," replied Warden in a breathless voice. "In fact, I'm delighted to have him under me," she added mirthfully.

Then the judge asked, "Are you alright, Warden? You sound strange."

"I'm fine, Judge. I've been doing chair exercises," replied Warden.

Warden hit the mute button just seconds before she climaxed with a loud scream.

I thought that Warden was finished. So I attempted to crawl out from under her desk but she blocked me with her knees.

"Not so fast," she said in an authoritative tone.

So, I resumed licking until Warden Brown enjoyed two more orgasms. Then she let me out and sat me in her lap.

"You're a delightful little pantywaist," she said as she embraced me warmly. "I'm sure that you'll be a model prisoner, too, but don't expect an early release."

--

This story will be continued.