Freebound

By the time I had negotiated the stairs Kay and Chloe had disappeared into Kay’s room. Pam stood holding my lead in front of the door to Kay’s room, she went to knock but stopped herself turned and looked at me, her eyes looked directly into mine then she lowered them looking at my semi hard cock in its plastic prison then on down to my feet locked in high heeled boots. It seemed as if she was trying to make up her mind, she said nothing turned back and knocked on the door this time seeming to have more conviction. The door was opened by a naked Chloe, she looked strange without her belt although the lines could still be seen where it had once been.

“Come in.” said Kay, who was lying on the large four poster bed. “Sorry its girls only, but we will allow you to stay once you pass our little initiation.” Said Kay as she got off the bed and came and took my lead and the remote from Pam.

“A gift for you to enjoy my darling.” Kay handed my lead and the remote to a smiling Chloe.

“Thank you so much mistress Kay.” Said Chloe a she curtsied.

It was the first time I had heard Chloe speak, a soft voice almost angel like not at all like I imagined it to be.

“Although he is yours for the duration of this role play, remember that you still belong to me and will do as I say. Do you understand?”

“Yes Mistress Kay, I understand.”

“Good girl. If he is to remain with the girls I want him dressed as one. Take him and dress him like a little tart.” Kay said as she turned and looked at Pam.

“As for you, I think you should be naked” Kay was standing facing Pam.

“Strip for me” Said Kay.

Pam started to undress as Chloe led me into the large walk in wardrobe. “Come on you lets get you dressed.”

The wardrobe was incredibly spacious and had a dressing area with a chair on stool as well as rows and rows of clothes. I had never seen so many boots and shoes each pair on its own little display shelf.

“You like those don’t you” Said Chloe as she watched me admiring the footwear display.

“I’ll get the key and unlock you so that we can find you a nice pair to wear. Sit here and wait.” Said Chloe as she sat me in the chair.

“Don’t move or I will punish you.” She said as she left to retrieve the key.

I turned my head and watched her walk across the bedroom. I could see a naked Pam standing with her legs spread wide, her hands behind her head. Kay was standing in front of her with one hand between Pam’s legs. “You feel very wet Pam. I think you like the idea of being my slave.”

Kay stopped rubbing Pam’s pussy and stepped back. Chloe was now standing motionless watching Pam and Kay.

“Bend over, hold your ankles with your hands.” Said Kay.

Pam obliged bending at the waist and grabbing her ankles, she was now displaying her arse and pussy directly towards me. Kay stepped behind Pam and placed her hand against Pam’s pussy.

I watched as Kay slid her finger into Pam, my cock again straining for release. Kay was now pushing her finger in and out of Pam’s juicy pussy. She stopped suddenly and withdrew her finger, bending down she placed her finger in front of Pam’s face. “Do you like pussy juice?” She said running her finger along Pam’s lips.

“Suck my finger, I want you to taste your sweet pussy.” Kay pushed her finger into Pam’s mouth and began to finger fuck her mouth slowly moving her finger in and out while Pam sucked.

“I think you do like pussy juice, you little minx.” Said Kay pulling her finger from Pam’s mouth and standing up.

“What did I tell you to do?” She said now looking at Chloe who had been standing watching.

Chloe removed her hand from her own pussy. “You said to dress him like a tart Mistress.”

“Is he dressed like a tart?”

“No Mistress, I came to get the key to unlock his boots and chains”

“So why where you standing watching me and playing with your pussy?”

“Sorry Mistress Kay I couldn’t help my self.” Said a very embarrassed Chloe.

“That is your trouble Chloe you just can’t help yourself can you.”

“No Mistress Kay, I am very sorry. I will do as you asked and get him dressed” Said Chloe as she hurried back to me.

“Chloe come here.” Demanded Kay.

“Position one please Chloe” Said Kay as she walked over to the chest of drawers and picked up a riding crop.

Chloe lay on her back and lifted her legs in the air, she then grabbed each ankle exposing her pussy.

“Turn around so that you show our guest your pussy”

Chloe let go of her knees and shuffled around so that her pussy was facing me she then raised her legs and re-gripped her ankles but not before showing me the remote in her hand. Her pussy looked very aroused, puffy and very wet. Totally hairless everything was on display. My cock strained, I was hoping I would get to experience the delights of Chloe’s pussy.

“How many strokes do you think you deserve Chloe?” Asked Kay as she stood over Chloe.

“Three Mistress.” Said a very nervous Chloe.

“Only three, I am disappointed Chloe I think you deserve more than that.”

“Six Mistress.”

“What do you say Chloe?”

“Mistress I have been a bad girl and deserve six strokes.” Said Chloe  her legs now beginning to shake.

Kay was obviously enjoying making Chloe wait for her punishment.

“And where do you think you deserve the strokes?”

“On my arse Mistress” Replied Chloe.

“No I don’t think you would learn not to touch your pussy without permission if I where to administer six strokes to your lovely arse. Do you?”

“No Mistress.”

“Then where should I administer the strokes Chloe?”

“On my pussy mistress.”

“What do you say Chloe?”

“Mistress I have been a bad girl and deserve six strokes on my pussy.”

“Good girl, don’t forget to thank me for each stroke. Now are you ready?”

“Yes mistress.”

Kay bought the crop down in the middle of Chloe’s pussy. My bollocks received a sharp shock

Chloe fighting back tears cried out “Thank you for stroke number one mistress.”

 

Again Kay bought the crop down on Chloe’s pussy. Again I received a shock to my bollocks.

“Thank you for stroke number two mistress.”

Kay delivered the strokes with great accuracy ensuring no stroke landed where another had previously landed. The last stroke landing directly on Chloe’s swollen clit. For each stroke I received a shock to my now aching bollocks.

Chloe dutifully thanked Kay for each stroke although it took her a while to get her breath back after the last stroke.

Pam was still bent over holding her ankles, her pussy juices could be seen trickling down the inside of her thighs. My cock had leaked pr-cum over the chair I was sitting on.

Kay stood over Chloe. “Will you touch your pussy again without my permission?”

“No mistress” Said a snivelling Chloe.

“Ok now wipe away your tears and go and do as I asked you too.”

“Yes Mistress” said Chloe as she stood and walked over to the dressing table.

Kay stood behind Pam and placed her hand between her legs. “Wow you are very wet Pam. Did you like watching Chloe get her punishment or are you wet thinking about being punished?”

Kay placed the tip of the crop against Pam’s pussy and gently rubbed her juicy lips.

“I asked you a question” Said Kay, now pushing the tip of the crop in between Pam’s swollen pussy lips.

“I am not sure” replied Pam.

Kay removed the crop from Pam’s pussy and delivered a short stroke to Pam’s arse, Pam rocked but stood firm.

“Is that the correct way to answer your mistress?”

“No mistress” replied Pam.

“That’s better, now answer my question.”

“I liked watching but could not help imagining that it was I who was being punished Mistress.” Replied Pam, who seemed more surprised by her answer than I did.

Chloe returned closing the door of the wardrobe behind her. She was holding the remote, a small bunch of keys and a ring gag. She used the keys to remove the chains and the boots from my ankles and feet, she left my arms cuffed behind my back but removed my gag and replaced it with the ring gag.

“I want your tongue and mouth available.” Said Chloe as she clenched her legs and wiggled her hips thrusting her pussy in my direction.

“You had better clean that mess up before Kay sees it” Said Chloe pointing to the gooey mess I had made on the chair. As I looked around for something to clean it with Chloe grabbed my hair and forced my head down. “Use your tongue stupid” she said pushing my head down onto the seat of the chair.

 I closed my eyes and pocked my tongue out through the ring gag and started licking as best I could. I was imagining it to be Chloe’s juices I was licking and not my own. I was surprised that it didn’t taste as bad as I thought it would.

“Ok that’s enough.” Said Chloe pulling my head up. “Let’s get you dressed; now it’s my turn to get off on watching you suffer.”

Chloe turned and called out “Mistress Kay, may I have a word with you?”

“Yes. What do you want Chloe” came the reply.

“May I prepare his arse in case you may wish to fuck it later Mistress Kay?” Shouted Chloe.

“What a great idea Chloe, I may even let you fuck it if you are a good girl. Now get on with it and do not interrupt me until he is ready.”

“Yes Mistress.”

I didn’t like the sound of this although my cock was yet again straining and leaking a gooey mess down my legs.

Chloe led me through a door at the other end of the wardrobe into a spacious bathroom. It was tiled floor to ceiling with a shower in one corner, and a large Jacuzzi in the centre. A small cubicle in the other corner was occupied by a toilet.

Chloe unclipped the lead from my collar and attached one end to a towel rail that was high up on the wall. She then grabbed my cuffed arms and pulled them up behind my back forcing me to bend at the waist finally she attached the lead to the cuffs which forced my head down between my legs and my arse in the air.

Chloe then exited the bath room leaving me chained helplessly to the wall. It was pointless trying to struggle I was going nowhere.

Chloe returned holding a small black holdall which she placed on the floor behind me.

“Ok let’s get you clean and ready for use” She said as she removed a pair of latex gloves and put them on. Next she took a tube from the bag, unscrewed the top and squeezed some of the contents onto her latex clad fingers. She then placed her hand on my arse and started probing to find my hole. Because all my hair had been removed her fingers slid effortlessly up and down my crack until finally her finger came to rest against my arsehole. I tried to squeeze my cheeks closed denying her access.

“It will hurt more if you are tense.” she said applying more pressure. I felt my sphincter relax slightly and her finger entered my arse. She started slowly massaging my arse first with one finger and then with two. I have never had anything up my arse before but the feeling was rather pleasant.

Chloe withdrew her hand and picked up a small plug from the holdall, she then proceeded to rub lubricant all around the plug before placing it against my sphincter.

It looked much bigger than a few fingers and I tensed my arse anticipating the pain.

“Relax and it will be fine.” Said Chloe, “This is nothing compared to Mistress Kay’s dildo.”

I tried to relax and then suddenly I felt the plug enter my arse, it felt as if it was stretching beyond its limit and then suddenly it felt ok again as it slid deeper in and my sphincter was able to relax around the narrow part of the plug.

Next Chloe removed some tubing and pushed one end into the hole through the centre of the plug. She removed a water bag filled with a soapy looking liquid and pushed the other end into the hole in the cap of the water bag. After securing the water bag to the towel rail she undid the valve on the cap of the water bag. I felt a warmish sensation in my arse.

“This is a two litre bag; I doubt you can take it all but we will leave it flowing for a while.” Said Chloe as she gently squeezed the bag.

“It will get your arsehole nice and clean for when it gets fucked later.”

My stomach felt very full and still the contents of the bottle where trickling in through my arse. Within a short while I felt as if I wanted to have a huge crap. My stomach began to cramp as if constipated.

“You will have to hold it for a short while to give the cleanser time to work” said Chloe.

I had no choice but to wait until permitted to release the liquid that had been emptied into my arsehole.

Chloe was busy behind my back and I could smell a familiar smell butt I just couldn’t place it.

“Don’t move or I will keep the plug inside your arse for longer” Said Chloe who had now bent down to my left foot and begun to paint my toenails bright red.

Looking at my smooth hairless legs and red toenails, I felt my cock growing again causing even more discomfort than I was already in.

“I think you are going to like being a little whore.” Chloe said as she finished painting my last toenail.

Chloe Reached up and removed the bag which was now empty. She then pulled the tube from the plug in my arse and replaced it with a tiny bung, trapping the contents of the bag in my arse.

“Now I need you to walk so that the cleanser can really clean you out.” Chloe released the lead holding my arms up and allowed me to stand. I hadn’t realised how much my body was aching, but it was nothing to the pain in my fully bloated arse.

Chloe attached the lead to my collar and led me around the room. I just wanted to get rid of the pain in my stomach as soon as possible so followed her eagerly round and round the bath.

Eventually Chloe led me over to the cubicle and unlocked my hands.

“I want you to go in there and remove the plug. You are then to wait until you are empty before coming out again.”

I couldn’t wait to remove the plug and empty my load. I expected it to gush out but it came out in dribs and drabs for what seemed like ages.

Chloe then made me clean the enema kit with antibacterial wash and replace all the components back in the holdall.

“Now let’s go and get you dressed you little whore.” Chloe led me back into the wardrobe and started selecting clothes for me to try on. After trying on various items of women’s clothing Chloe decided to dress me in a red leather dress that finished just below the cheeks of my arse, it was long sleeved and had a zip running up the front, from top to bottom. She also managed to find some prosthetic breasts to fill out the dress giving me a rather nice figure. The outfit was finished off with a pair of black seemed hold up stockings and a pair of very high heeled red leather sandals.

“My you do look the part.” Said Chloe as she stepped back to admire her creation.

“Just a bit of makeup and a wig and you will be ready to present to Mistress Kay”

Chloe sat me down in the chair that she had placed in front of the make up mirror and begun to apply make up to my eyes and cheeks she the applied lipstick to my lips. After a few moments I did not recognise the face looking back at me in the mirror. I looked like a whore; the ring gag forcing my lips apart reminded me of a blow up doll, the effect was truly remarkable I looked and felt like a complete slut, I just hoped I would get used like one.

“Come and see yourself over here” said Chloe as she led me over too a full length mirror on the wall. I stood and looked at myself although I hardly recognised the person in the mirror; my legs looked longer more feminine, I had a cleavage the only thing missing was a women’s wig.

Almost as if reading my thoughts Chloe said “I will present you to Mistress Kay in a moment but first I need to borrow one of Ambers many wigs”

 My cock was now straining so hard I thought it would burst out of its tiny prison any moment and I would bend Chloe over the stool and fuck her madly with it, shooting the load in my very heavy balls deep in her pussy, I felt wonderful.

“Wait here while I fetch you a wig” Said Amber as she headed towards the door that led to the bathroom.

I stood looking at myself in the mirror, then started walking up and down the wardrobe watching my reflection mimic my every move.

Chloe returned with a long blonde wig. “Here let me put this on” she said as she beckoned for me to sit on the chair.

With the wig on I felt complete. I stared at my reflection and did not here the door open.

“Let me see you then” Said Amber.

Startled I turned around.

“That is one pretty whore.” Said Amber

Chloe beckoned for me to stand. “Show Mistress Amber your lovely outfit.” She said as she made a twirling motion with her finger.

“What’s her name?” asked Amber as she eyed me up and down.

“I don’t know Mistress Amber, I had not thought to give her a name.”

“I think she should be called Penny” Said Amber.

“Yes I think that suits her Mistress Amber”

“Would you tell Mistress Kay that I would be very interested in seeing Penny in my room when you two have finished with her.”

“Yes Mistress Amber”

Amber looked at me “Have you ever been fucked in the arse before?”

I shook my head.

“Chloe find a large but plug and stretch his virgin arse, Mistress Kay will appreciate that.”

“Mistress Kay has asked me not to disturb her until he.. I mean she is ready for her. Do you have a but plug I could use?”

“Yes come with me and I will loan you one, Penny can bring it back later.”

Amber looked back at me “I hope to see you in my room later Penny and don’t forget to bring my but plug back” She blew me a kiss and left with Chloe following close behind.