Halloween Pool Party Pt. 03


I soon headed to town and told the apt manager that I was sorry but I would have to move out immediately. It was a family emergency and I would be leaving the area the next day. I asked if he knew anyone that would purchase my furniture, appliances and household stuff, and he asked to see it. It was all quality furniture and he said he would take it and offer the apt as furnished if I took out my clothes and stuff. He asked if $6k would cover it and I said I could live with that. I spent most of the evening packing things up and went out for a late dinner around 10pm.

In the morning I took all my males clothing to the local Goodwill store. Why, because they were open Sundays. I grabbed my gaming gear, some speakers and a few sentimental items and loaded them into my car. The jeans and t-shirt I wore would be the last male clothes I would own. I spent a couple hours cleaning the apartment and the landlord came by and gave me a check for the furniture. Satisfied that I had everything loaded I prepared to return to the Dane’s home. I realized that the checks I received were from drawn on the same bank as mine and the supermarket branch was open Sunday’s. I had a great idea and stopped and cashed the checks and headed to the mall. I shopped a couple of jewelry stores and found what I was looking for. A pair of matching gold and diamond tennis bracelets. One for each of my Mistresses. They were about $5000 each but when I said I was paying cash on a slow Sunday, I was able to get them both for 6K, and had them gift wrapped.

The mall stop was going to make me a few minutes late getting back to the Danes’. I hope Miss Maddy wouldn’t be too upset, especially when she saw why I was delayed. It was only 10 after 5 anyway, no big deal. Bringing my first load into my new room I noticed my bed had been replaced with a new one. This was a super twin with a canopy above it. The frame looked kind of like a hospital bed with side rails and there was a full length mirror in the canopy. The sheets were now a “Barbie” print and on the pillow was a new nightie and panty set with a note saying Maltepe Escort “for our special bimbo”. I quickly finished unloading my car and put everything away before taking a quick shower.

In the shower I finally had a chance to examine the chastity cage. I fiddled with the lock then tugged and turned the cage trying to find a way out. “Dam no way to get out of this thing. That’s a drag” I told myself. Finishing up I grabbed a towel and before wrapping it around myself I glanced over my shoulder into the mirror to see the 38 well spaced welts that rose slightly off my ass. A full day later and they still showed. “No wonder it hurt sitting to drive” I laughed to myself. With a groan I went to get dressed. I realized that all I really had to wear were the dirty jeans and t shirt I had worn the last 2 days so I slipped on the panties and dropped the nighty over my head. It barely covered my ass. They felt so soft and special my cock tried to get hard in its cage. “Owww” I cried out. It feels like little pins poking into my cock head when it tried to harden. I can’t believe I haven’t felt them before this, Has it really been that long since I got a hard on? I better try not to get hard again with that.

It was only about 8 pm but I was tired. I put on my headphones to listen to some music before going to sleep. Laying down on the soft mattress I looked up and saw myself in the mirror above. What I saw wasn’t a 28 year old man, but it wasn’t a woman either. Long hair and a sexy nightie, flat chest and a chastity cage making an ugly bulge in my panties, a hairless body and hi arched eyebrows. My sissy cock tried to get hard again and the tiny spikes dug into the head causing me to yelp.

At that point the door opened and both of my Mistresses walked in, smiling at me. “I see you like your new bed Brenda, but you should have told us you were home.”

“I would have Mistress but I was so tired from moving things today, and then I realized that I didn’t have any clothes to wear so I figured I would just go to bed.”

“Now Brenda, I did notice that you were Ümraniye Escort late getting back. Didn’t I tell you 5pm?”

“Yes my Mistress”

“You arrived at 5:12 by my watch. Being late you should have come to me and asked for your punishment as soon as you arrived. That’s what a good sissy would do Brenda. You should have come to me when you got home and apologized for being late and asked for your punishment. “Annie please get me a paddle so we can correct our sissy” Miss Maddy demanded.

When Annie left the room Mistress told me to turn over in the bed and put my hands towards the headboard. From a slot between the headboard and mattress Mistress pulled up a pair of handcuffs and quickly had my hands bound. I was too tired to resist, and wouldn’t have anyway. A pillow was stuffed under me and when a strap was pulled over my back it crushed my chastity into the pillow. My feet were cuffed to the other end of the bed when Annie returned with the paddle.

“We really need to start keeping some tools in here Maddy'” Annie joked and they both agreed to do that.

“Now Brenda, 12 minutes times 5 is 60 swats. I would normally add more for your forgetting to tell us you were home but as you are new we will let you off easy this time.” Miss Maddy stated very matter of factly. Annie dear you may have the honors tonight. And sissy, not a sound out of you miss.”

Annie showed me the wooden paddle. It was about a foot long and had small holes drilled through it.

She then pulled down my sheer panty and admired the welts that remained from the previous day. She smacked me with the paddle and I buried my face in the pillow to keep from crying out. After a few hits she stopped and caressed my burning ass with her cool hand. I started to get excited when her hand moved away and the blows started again. 12 or maybe 15 more and she stopped and felt the heat rising from my ass again. She trailed a finger nail between my cheeks and down between my legs. Tickling my perineum. My clit was straining it its cage and the spikes were digging deep into its head.

She İstanbul Escort stopped and resumed her swats. Another 20 or so and she stopped again. This time tickling my balls then trailing her finger up and around my rosebud. My clit was straining again and I was feeling a constant pain in my ass and sissy clit. I turned my head enough to see Miss Maddy sitting in the chair watching the action with her fingers deep in her panties. Miss Annie finished paddling me and I felt her spread a cool lotion on me working it into my bottom hole as well.

Mistress Maddy came to the bed and put her juicy fingers in my mouth and commanded me to suck. I opened my mouth and gently licked and sucked them making my caged clitty hurt even more. As I sucked I felt Miss Annie press something against my asshole. Thoroughly lubed and unable to resist it slid past my muscles with a plop. I felt Annie fiddle with it and felt it expand inside me. It wouldn’t be the last time I felt the blow-up butt plug in my sissy ass. When I thought it would explode in me she un-hooked the pump leaving it full inside me. It made my ass squirm uncontrollably forcing me to hump my painful chastity even more as I finished cleaning Miss Maddy’s wonderful pussy juice from her fingers.

Annie kindly released a tiny bit of the pressure from the plug and released my bonds. I crawled off of the bed and kissed both of their feet thanking them for their mercy and training.

“May I arise Mistresses?” I asked humbly.

When told that I could I went to my top dresser drawer and retrieved the wrapped gifts I had bought earlier. On my knees I presented them to my Mistresses and told them that I was late because I stopped to get them a gift.

Upon opening the gifts they were both thrilled with the bracelets and I explained how I was able to sell my furniture and wanted to do something special for the 2 of them. They put each others bracelets on and had me stand and gave me a warm group hug. “They are so lovely Brenda, thank you so much, but now you know there is still no excuse for being late”.

“Yes Mistress”, I replied, “I know I was wrong.”

“Well get some sleep now darling, as tomorrow we need to take you shopping for clothes then you have an appointment at Lady Olga’s at 3pm.” Miss Maddy informed me.

“Thank you Mistress, I am so tired.”

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