Halloween Pool Party Pt. 02

With that Miss Maddy motioned for Annie to ride my cock.

"Oh my goddess it feels so hot and soft in her. So amazingly good. I hope I can last the full 5 minutes," I thought.

"Begin", Mistress said and I felt Annie's pussy muscles clamp down on my engorged cock. She rode it up and down squeezing it and letting go. Squeezing and letting go. This must be what heaven feels like.

"Enjoy it Brenda. It's probably the last time you will ever do this in your life!"

"No not the last time its just my first" I cried out but mistress said that "fucking is a privilege for women and males not sissy bimbos. But you will get to enjoy being fucked regularly."

Annie reached forward and started kneading my flat chest and tweaking my nipples. I reached up to hers but Maddy swatted my hands away.

I wasn't sure what she meant and before I could think about it Mistress Maddy straddled my face and lowered her crotch to my mouth commanding me to lick her like I licked the bikini crotch in the video. I reached my tongue to the soft fabric covering her pussy. Her intoxicating smell and taste combined with Annie pinching my nipples as her pussy muscles enveloped my cock was too much and I came with a loud cry muffled a bit my Mistress Maddy's crotch on my mouth. Wave after wave of pleasure overcame me as I unloaded into Annie's glorious pussy. I almost passed out from its power. I finally was no longer a virgin I was a man.

"Maybe that talk was just a lot of foreplay and Maddy didn't mean all those things she said she was going to do", I thought. But I really didn't care at the moment I finally got to fuck a woman and it was awesome. I couldn't wait to do it again.

"You actually made it 4 minutes sissy. I guess its only D-cups for you. They will look so nice with your pretty long hair and arched brows. Don't you agree Annie" asked Miss Maddy?

"Yes they will be much more fun to play with than that", she said pointing to my flat chest.

"And when her girly vitamins kick in they will probably grow another couple of cup sizes for her, but that will take some time" added Mistress Maddy.

Mistress had moved to the side and told Annie to slide up and have me clean her. She lowered her face to my mouth. " Suck her pussy clean of all your sissy cum Brenda", demanded mistress. It felt a bit wrong somehow but I could not resist as I licked and sucked until Miss Annie was clean and had a nice orgasm of her own.

I was totally spent when Mistress said we had one other quick chore to take care of. She whispered something to Annie, then turning her attention to me reminded me that I was supposed to let Annie know when Mistress was returning home and I had forgotten to do that and must be punished. She pulled me up and had Annie lie on her tummy on the lounger with her legs spread wide. I was pushed to my knees and my face was at Annie's ass with my ass in the air. Annie told me to start licking her bottom hole and not to stop. I heard mistresses' sandals as she walked away and shortly returned.

"You keep that tongue deep in her ass sissy. You are going to be punished with 20 cane strokes. If you remove your tongue or make a sound you will receive 3 additional strokes for each instance. I felt the cane as she gently brushed it over my ass. Then I heard a whoosh and felt a strike like being hit with lightning on my ass. I yelped in pain and pulled my head up. "That's 6 more sissy. You better bury your head and wiggle that ass like you want it." she laughed. I wiggled my bottom giving her a pretty target and tried to be remain quiet for her. When she had finished Annie told her I pulled my tongue out at least 3 more times. That and one loud moan that Miss Maddy heard meant another 18 strokes. I vowed to do better for those and soon had 38 crisp stripes across my ass and the lovely taste of Miss Annie on my tongue. For some reason I bent down and kissed Miss Maddy's feet and thanked her for correcting me.

Now that you know what your future holds Brenda, fetch us some wine. The lady's sat as I went to the bar to get and serve the wine. "And bring me that little gold box from the bar and an empty glass as well Sissy", Mistress ordered.

"You will be spending the rest of today and tomorrow clearing out your apt. and moving your things here. Your male clothes and anything you don't absolutely need should be given to charity along with your furniture. On Monday you will be going back to Lady Olga's and have your hair done and nails. I will discuss it with her before you go there. I will arrange for Dr. Dane to have your breasts enlarged by Thursday, as we need you healed before Halloween. Now hand me the box. I hadn't noticed it on the bar earlier and wasn't sure what it held. She told me to lower my bikini bottom and stand facing her.

Opening the box she took a metal ring out and fastened it behind my cock and balls. With seemingly practiced ease she then slid a metal tube over my softened cock and snapped a padlock through a hole locking it all in place. "There now sissy, pull up your panty and have some wine. That cage will keep you from playing with my property until I allow it again, if I allow it at all. And I suggest you avoid getting hard in it. There may be a surprise hiding inside. Ha ha ha"

Annie now stood next to her and she handed me the empty wine glass. She told me to kneel and offer up the goblet with both hands to my mistresses. Mistress Maddy stepped forward, pulled the crotch of her panties to one side and let go a steaming stream of pee into the goblet. When it was half full she stopped and stepped back. Still naked,Miss Annie then stepped up, her pussy still a bit puffy and glistening, and filled it to the top.

They both held there wine glasses to my large goblet and Mistress Maddy spoke. "you are under no hypnosis at this time Brenda. Of your own free will I want you to pledge your devotion to me and to Miss Annie. Please repeat after me."

"I, formerly Ron the pool boy, now Sissy Bimbo Brenda."

I repeated with a trembling voice and an ache in my chastity cage. "I, formerly Ron the pool boy, now Sissy Bimbo Brenda."

"Pledge my love and devotion to Mistress Maddy and Mistress Annie."

"Pledge my love and devotion to Mistress Maddy and Mistress Annie."

"And upon my drinking your golden champagne."

"And upon my drinking your golden champagne."

"Offer myself to you forever."

"Offer myself to you forever."

"To enjoy as your chattel, that you may use, alter, train and enjoy."

"To enjoy as your chattel, that you may use, alter, train and enjoy."

"As I know from the depth of my heart and soul."

"As I know from the depth of my heart and soul."

"That I wish to belong to you Forever and Always"

"That I wish to belong to you Forever and Always"

I moved the goblet to my lips and looking up at the loving faces of my Mistresses I knew that my fate was sealed as I drank their nectar.

My Mistresses had to have spent some time planning for this moment because they lifted their glasses and in unison said. "We accept your pledge of submission Brenda. You will become nothing less than our pleasure toy and we will keep you as our Bimbo sissy always."

The clinked their glasses and drank their wine.

My fate was sealed.

We hugged as a group for at least 5 minutes. My Mistresses in a warm embrace as I knelt and hugged them each around their legs, My face between their pussies.

Finally breaking away Mistress Maddy pulled me up and said " its late afternoon Brenda, you have work to do. Get dressed and go take care of your apt and anything else you need to take care of in town. Be back here by 5 o'clock tomorrow and do not be late, or early." I need some private time with Annie.

Nervously I said "Yes Mistress, but before I go, well, it's just that this metal cage makes it so I cant look pretty and smooth anymore. Can you take it off please? It looks funny."

Annie and Maddy both laughed at my statement and Miss Maddy finally spoke up. "I'm sorry sissy, you know I can't just take it off and leave you all that temptation of playing with your sissy clitty. We will just have to keep it locked for a while. At least until we are ready to make you look pretty and smooth all the time. But don't worry it wont be to long for that to happen."

"I don't want to lose my dicky Mistress" I cried, "I just wanna look pretty".

"Yes baby don't you worry, you won't be losing any parts. And I guarantee you that one day soon you will have a nice smooth look that will be perfect for a sissy bimbo. You know you won't be able to stroke it like a man after its fixed though but you will definitely look smooth and pretty in tight clothing. I am sure it won't be too long before you are begging for that. That chastity will drive you mad sooner than you think".

'Yes Mistress, thank you Mistress. And You too Mistress Annie. I will see you both tomorrow.