Lady In The House Ch. 14

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
MicheleNylons
MicheleNylons
3,982 Followers

I pulled a pair of white satin full-cut panties up my legs and smoothed them around my buttocks and over the suspender belt and then stepped into a very small white satin half-slip. My penis was becoming erect because of the scintillating feel of satin and nylon on my body. I reached down and adjusted it and concentrated on finishing getting dressed.

I took the charcoal grey suit from the robe and laid it out on the bed. I stepped into the skirt; it had a pleated front and side vent. It looked both professional and sexy, but as the hem only just covered my stocking-tops it couldn't really pass as a business suit. I buttoned myself into a white, long-sleeved, blouse and tucked it into the waistband of my skirt and closed the zipper on the side. I adjusted the waistband of my skirt and pulled the hem down over the hem of my slip. The skirt was tight and the hem sat high up on my thighs.

I picked up the black high-heeled sandals, sat back down on the bed and stepped into them, fastening the ankle straps. Standing up I went back to the dressing table and opened the drawers until I found a small collection of jewellery. The jewellery that I had worn this morning was part of the collection and would accessorise my outfit perfectly. I slipped the gold anklet on my right ankle and adjusting it so it fell below the strap and buckle of my high-heeled sandal. I clipped on the gold drop earrings and put the gold ladies watch and gold bangles on my wrists and the gold chain necklace around my neck.

Finally I gave my face another dusting of finishing powder and put another coat of lipstick on my lips. I sprayed my favourite perfume 'Poison' on my decolletage and another modest spray under my skirt, a trick Carmel had taught me all those years ago in this very place. I picked up the suit jacket off the bed and put it on and walked back to the mirror to make any final adjustments.

Once again Steve had dressed me so that I looked like a businesswoman or high-class secretary who had the dress sense of a trollop. My skirt was too short and tight and the side vent showed bare thigh so the outfit was actually a parody of business suit. Sophisticated but slutty; if that was possible.

I was again reminded how much I was dressed to look like my sister Angie, this time even the brunette bob matched her hairstyle.

I looked at my watch: 2:52pm.

I heard the clatter of heels on the tiles again and Carmel reappeared with Steve trailing along.

"Perfect!" they both said at once, Carmel smiling and Steve with his familiar evil grin.

"Ok Michele we're going over to the conjugal visits section of the visiting unit," Steve said.

"We need the privacy of a conjugal room; even I can't get away with parading you openly around the rest of the prison dressed like that," he said.

The conjugal visit section was provided for inmates who had conjugal rights; usually those who had committed lesser crimes or were coming to the end of their sentences and were being rehabilitated. It was located inside the visiting unit adjacent to G block; the minimum security section where I had been housed until recently.

"How are you going to get me to the conjugal section?" I asked, worried about being dragged around Chelmsford Prison dressed as a woman.

"Well honey; you're going to love this; the Warden is going to escort you!" Steve laughed.

I was stunned! How were they going to pull this off?

But that's exactly what happened. Steve took me to the entrance to E Block where the Governor was waiting. He escorted me to the conjugal section of the visiting unit. The Governor remained closed mouth during most of the journey only speaking to explain to me that the cover story was that I was a member of the Prisons Board conducting a routine inspection. He made sure that we took a circuitous route that kept us out of the eyes of most of the prison so that we were really only visible from a distance.

From a reasonable distance it would look like the Warden was escorting a businesswoman with poor dress sense around the prison. When we arrived at the visiting unit I was handed off to a prison officer who was obviously in on the scam as he was to lead me into a private room in the conjugal section.

"Enjoy your visit," the Warden offered cynically as he handed me over.

The conjugal section was actually just a freestanding prefabricated demountable divided into four rooms. The guard led me to one of the four private rooms assigned for conjugal visits. The rooms were austere but fitted out for their intended purpose with a table, two chairs and a double bed. A small shower and toilet unit was also provided in each of the rooms. Although private and unable to be monitored by the prison authorities by law, the prison joke was that if you stood outside and listened hard enough you could hear the prisoners humping their wives. It was rumoured that the guards kept score on which of the inmate's wives gave the best performances.

I sat on the hard seat at the cheap Formica table, adjusting my skirt trying to reveal as little as possible with little success. Now I was shivering with shame and regret knowing that soon my sister was going to see me dressed this way and having to explain to her that I was responsible for the vicious attack that she had suffered in the hands of Steve's henchman Danny.

When the door opened I jumped and to my surprise Steve stepped into the room. I looked at him startled.

"Oh yes Michele I'm going to be here for the visit. I want to make sure you tell Angie everything. I also want to give you both a final warning," he said, sitting down across the table from me.

Then the door opened again and again I jumped. This time Angie stepped into room and I was absolutely gob-smacked! Not only was she dressed identically to me; she was in the company of Danny! He closed and locked the door and led Angie over to the bed where she sat with a stunned look on her face. She looked like she was in a trance. Danny sat on the bed opposite Angie and suddenly the room felt very crowded.

"Let me begin proceedings," Steve said.

"I've had Danny escort Angie here today after making her an offer she couldn't refuse, so to speak."

"She was provided with her outfit today courtesy of me, and we've had special arrangements made with the prison authorities to get her in here with Davey as her chaperone."

"Angie here has had the situation explained to her in some detail," he continued.

"She knows what you're dealing with Mike, and she knows what will happen to her should you not comply with the terms that I have placed upon your future existence here in Chelmsford Prison."

"She got a taste of that from Danny the other day and she also knows that should she attempt to go to the authorities or try to run away that she, or even worse her daughter, will receive more of the same. She also knows that you will also be made to suffer further," he summarised the situation.

"Now Angie, you can see the position that Mike here is in. A picture paints a thousand words; and there is nothing better than seeing the living proof is there?" he finished.

"I can't believe that's my brother Mike sitting there," she said, "he looks more like my sister than my brother!"

"Well perhaps to avoid confusion we will just refer to Mike as Michele from now on. Is that ok with you Michele?" he asked defiantly.

I nodded my head compliantly.

"Ok Michele; this is your chance to tell Angie all about your life in Chelmsford. Tell her about your first prison term here, what happened to you and how you survived; and then tell her about the recent stretch," Steve ordered.

And I did. I looked into my sister's heavily madeup eyes with my own and told her the whole sordid tale.

I explained to her about how during my first term in Chelmsford I became the accountant and confidant of Eddie McManus who had me transformed into Michele, a transvestite prostitute who was forced to service other inmates and prison officials and kick up my earnings to Eddie.

I told her of how an inmate named had Davey 'rescued' me from Eddie's clutches and how he kept me as his willing concubine for the remainder of my prison term. I explained that living in servitude as the transvestite 'wife' of a prison inmate to escape constant violation by prison thugs was my path of least resistance and pain. I also admitted that by then I had been brainwashed into accepting my life as a transvestite and was a willing participant and even enjoyed my role as a woman.

Then I explained that for the ten years following my release I saw a psychiatrist who convinced me that I suffered 'Stockholm Syndrome' and that I had taken the only course of action open to me at the time. My psychiatrist and I worked together trying to mend the effects of the abuse, both physical and mental, that I had undergone during my prison term. We agreed that I had succumbed to the world of transvestism as a means of survival whilst I was in prison. He convinced me that I was in fact a heterosexual male forced to do what I did only because I had no choice.

I then went on to explain to her what had happened to me during this period of incarceration after I was transferred to F Block. I also explained honestly that although I was revolted by what I am now being forced to do, I know that it is the only way for me to survive the rest of my sentence. I also admitted that recently I was getting sexual gratification from dressing as Michele; that I was becoming the same person who had previously succumbed to a life of enforced transvestism in Chelmsford Prison.

Angie listened to the whole story without interruption. Occasionally I would see a look of surprise or sympathy on her face; but she remained silent until I finished my story.

"So you see Angie, Michele here has agreed to work for me in my little enterprise and Danny here will be keeping tabs on you every now and again on the outside to make sure that you keep your end of the bargain," Steve said.

"Ok, I know what I have to do to keep us both safe. Although until I saw Mike, err Michele here today I hardly thought the story Danny had told me was possible," Angie said incredulously.

"Oh its possible Angie; and just to prove to you how possible it is, as a final demonstration, Michele is going to provide Danny here with his conjugal rights!" he sniggered.

I was dumbfounded and shocked.

"No Steve please! Please spare me the humiliation!" I begged.

"Well sugar you both agreed to the deal, and Danny needs to get a conjugal visit; otherwise he would be here in the prison under false circumstances," Steve joked evilly.

"It's either you or Angie, Michele. You decide!" he demanded.

I looked into the shocked face of my sister and knew what I had to do. I stood up and kicked back my chair.

"Well come on honey," I flicked a long red painted fingernail at Danny beckoning him to me.

Angie looked astounded and stood up herself and yelled, " Mike don't do it; please don't do it!"

"Shut up and sit down Angie," I commanded, "let me do my job!"

Angie sat down on the bed staring incredulously at me.

Danny stood and walked over to me and I took in him my arms and kissed him. I drove my tongue into his mouth and lifted my leg and wrapped it around him, rubbing my nyloned calf against his thigh. Danny's hand stroked my thigh, high up where the reinforced welt of my stocking gave way to bare skin.

"Oh my god!" Angie gasped, "I can't believe you're doing this!"

I ignored her and concentrated on kissing Danny deeply and passionately. I felt him harden in his trousers and he pressed his erection against my body and pulled me closer returning my kisses.

"See Angie; Michele knows what she's doing; she's a natural," Steve whispered.

"I just find it hard to believe that is my brother kissing the arsehole that raped me," Angie said.

"I hate to say it, but dressed like that, Michele looks so much like me, that it's almost like watching me kiss him."

"I can let you do that if you wish," Steve smirked at Angie and she pulled a face at him and turned back to watch me.

I slid my hand down to Danny's flies and I unzipped him and slipped my fingers inside. His cock was hard and warm to my touch and I slid my fingers along the sleek shaft and felt it begin to throb, and Danny groaned.

Danny pulled his face away from me and gently pushed down on my shoulders. I knew what he wanted and I slowly dropped to my knees, kissing his neck and chest on the way down. When I was on my knees before him I opened his belt buckle and pulled down his jeans until they puddled around his feet. Danny's cock stuck up proudly above the waistband of his jockey shorts, the shaft was thick and veiny, the glans swollen and purple.

"Oh my," Angie gasped.

I pulled down Danny's jockey shorts and slowly stroked his thickening erection; his glans disappeared and reappeared between my fingers as I caressed it, my painted fingernails contrasting with the smooth pale skin of his shaft.

"Oh my," Angie gasped again, and this time, there was no doubt by her throaty groan, that she was becoming aroused.

I bought Danny's phallus to my lips and kissed his swollen purple glans, my lipsticked lips sucking up the little beads of clear pre-seminal fluid that formed on the eye of his member.

"Well I never!" Angie groaned.

"I bet you have!" Steve laughed and I heard the unmistakable sound of a fly being unzipped. I looked sideways and saw that Steve was standing in front of Angie with his erect penis wobbling in front of her face.

I opened my mouth and took Danny's glans inside my hot wet mouth and licked at the swollen flesh. I gripped his thighs and slowly started rocking back and forth on my knees and heels as I fellated him.

"Oh Michele; you are naughty!" Angie said, and absent-mindedly reached out and took Steve's hard penis in her hand.

I licked at the bulbous flesh of Danny's cock, slaving at it with my tongue whilst my lips slid up and down his shaft. With a free hand I stroked his testicular sac and with the other hand I stroked the shank of his penis as it slid in and out of my lipsticked lips. I heard Danny whimper in pleasure as he thrust his groin forward and back in rhythm with my ministrations.

"Oh my Michele; that is so very naughty," Angie whimpered and I looked over to see that her eyes were locked on me; watching intently as I provided Danny with oral pleasure.

Her manicured, nailpolished fingers stroked Steve's cock with a slow sensual cadence whilst her other hand disappeared under her skirt and inside her knickers. My naughty sister was obviously not shy in committing herself to lechery when it suited her.

"My god Michele; if you tell anyone about this I'll die," she said.

The irony of her statement was not lost on all present. Here was a woman masturbating the man who forced her brother to become a transvestite prostitute and was currently fellating the man who had recently ravished his sister! The situation was only made more absurd because these acts were taking place inside Her Majesty's Prison Chelmsford!

Steve, Danny and Angie all giggled at her outburst.

"Never mind about that; Michele is hardly likely to tell anyone anything about herself. You just concentrate on what you have in your hand," Steve replied.

Angie stroked Steve's throbbing penis with long slow strokes and concentrated on pleasuring herself with the same ardour. I continued to suck and slaver Danny's engorged phallus and stroke his scrotal sac. My own member was hard inside my panties; the feel of the sleek satin gusset against my cock sensuous and arousing. I decided to enjoy the sensation of my silken lingerie whilst I fellated the sleek hard member, but not to bring myself to orgasm. I knew I could easily achieve climax with a minimum of stimulation, but I was happy just to enjoy the sexual tension created by the current circumstances.

It was obvious that both men were now close to coming; they were both groaning and panting and gyrating their hips in time with the women who were pleasuring them. I could see that Angie was also close; she had hiked up her skirt and I could see her fingers were busy inside her knickers.

Danny put his hands on my head and pushed my face into his groin and I knew what was about to happen. I put my hands on his buttocks and pulled his groin hard against my face and swallowed as much of his cock that I could fit into my mouth and sucked at the base of it and slavered my tongue over the glans encouraging him to climax.

He bucked against my face and my mouth suddenly filled with hot musky semen. His cock convulsed and more of his seed flooded my mouth as I swallowed stream after stream of ejaculate. I couldn't swallow fast enough and rivulets of warm spend seeped from my lips and dripped down my chin. I felt a gob of the sticky spunk drop on to my leg and soak into my stocking. My own cock throbbed in my panties begging for release.

"Oh yeah suck it baby; swallow that come. Yeah suck me dry you dirty slut!" Danny moaned as he came.

"Oh Michele you are a dirty slut; how could you? How could you?" Angie cried, but her entreaty was obviously a cry of passion as she reached her own climax.

Her orgasm was intensified by the spectacle of the lovely transvestite fellating a man to climax right there in front of her. As Angie orgasmed she drummed her fingers against her mound inside her panties and at the same time she massaged Steve's member harder and harder, squeezing and caressing the organ in time with her own climatic convulsions.

Steve groaned, "Oh yeah baby; milk that cock; wank that man-meat you bitch!" and the first stream of ejaculate shot out of his throbbing member spraying a thick rope of white semen across Angie's blouse and jacket.

To my surprise Angie turned her face away from me and engulfed Steve's ejaculating member with her mouth and sucked on the tumescent organ until she drained it dry. She swallowed and gagged but didn't allow a drop of Steve's issue to escape her mouth while she stroked and fondled her own sex until both of them were sated.

I gently eased Danny's slowly deflating penis from my mouth and Angie did the same with Steve's. Angie adjusted her panties and straitened her skirt; she was blushing and looking very abashed. Danny patted me on the head and jibed.

"Good girl Michele. Steve you've got a keeper here mate," he said and then surprised me by helping me to my feet and gently kissing me on the cheek.

"Good girl Angie," Steve said, mimicking Danny by patting her on the head and then helping her to her feet and kissing her cheek.

"Now ladies, I can tell you are both embarrassed and probably more than a little surprised by what has just happened here and the way that you have just behaved."

"But let's just keep this between all of us here. You both know the situation; what has just happened does nothing to change your respective predicaments. It's still business as usual." Steve went on.

"Now I'm going to get you both out of here. Unfortunately there is no more time left for you two to visit but I promise you both that next visitors day I will organise a longer visit." he finished.

I looked sheepishly at Angie and she looked back at me the same way. We were both really glad that we wouldn't have to talk about what had just happened until we had had time to think about the implications.

"Bye Angie," I said and kissed her on the cheek.

"Bye Michele," Angie said and kissed me back.

Steve opened the door and passed me off to a prison guard, who escorted me over to E Block, again we maintained the ruse that I was visiting government official inspecting the gaol. It was only later that day when I though about what had happened that I realised that Angie had called me Michele and not Mike when we said goodbye.

To be continued...

MicheleNylons
MicheleNylons
3,982 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 16 years ago
Great Story

What a great story. I shot loads and loads of come reading it.

Love your work Michele

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Sissy's New Daddy Billie is forced to be a sub-sissy.in Transgender & Crossdressers
Forced Entry Transvestite caught in her hotel room is forced into sex.in Transgender & Crossdressers
Catia Becomes a Ladyboy Escort Mateus is trained as a sissy, used as a slut.in Transgender & Crossdressers
Blackmailed by a Bitch A straight man is blackmailed by his fiancee's shemale bossin Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories