Halloween Pool Party Pt. 02

Maddy Returns

I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why don't you show me what you have done before I take a swim dear?"

Ronnie again, and "dear", a kiss on the cheek? What is going on I wondered as I told her everything was fine and led her to see the newly painted room. "Oh its marvelous Ronnie. Don't you just love the pretty color?" she asked.

"Well yes Ms Dane, I mean Miss Maddy, If you think its nice then I am sure I will learn to love it too" I replied, though not sure how much that would actually be.

"By the way Ronnie, just so you know, don't make any plans for Halloween coming up, I am throwing a costume party for some of my friends here in the pool house and I need you to help me decorate it and serve at the party. You don't mind do you sweetie? she asked.

"That shouldn't be a problem Miss Maddy, no one has asked me to any other parties anyway. I am sure I can help serve your guests", I replied.

"Yes I am sure you will serve them well dear", she said catching me a bit off guard with the innuendo.

"Well I am going to change and swim dear, please have my wine ready and then join me in the pool if you like. I will have Annie bring us lunch later." Miss Maddy returned from the dressing room in a new leopard print bikini that looked amazing on her. I caused me to get hard immediately. Hope she doesn't notice. "Do you like my new suit Ronnie? I got it in Costa Rica."

" Oh yes Miss Maddy its quite attractive on you Miss." I told her.

"Are you going to just stand there or are you coming in"? she asked.

"I think I have a bit of swimmers ear Miss Maddy, maybe I will just listen to some music for a while" I lied knowing my tan lines would be exposed to her if I went in. She would probably fire me for being some kind of freak I worried.

"Be sure to use your headphones Ronnie" she told me as she started her laps.

I put on the headphones and checked some emails but was worried about how long I could hide my tan lines from my employer. She soon finished her swim and I handed her a towel and a glass of wine before she went to the dressing room.

In the dressing room she found my black and red bikini that I had forgotten and knew it was the perfect time to spring her trap on her soon to be sissified pool boy. She came out with a loose cover-up over her suit and stood looking at me with a sly smile. "Ronnie, did you have a girl over here to swim while we were gone. You know that's against the rules don't you?" she asked.

"Oh no Miss Maddy, I know the rules and wouldn't do that without your permission, I don't even have a girlfriend right now. Why Miss Maddy?"

She brought her hand out from behind her back holding my black and red bikini. "Oh shit" I thought to myself, "I must have left that in the dressing room the other day. What am I gonna do?"

"Then this must be your bikini I found in the dressing room Ronnie. Care to explain?" And she stood there holding it out to me. Maybe you would like to put it on and model it for me?

"Please Miss Maddy I don't know how it got there are you sure it isn't one of yours or Annie's?" I said trying to think of something.

"Its not Annie's size. Now don't try to lie to me young man or should I say young lady?" she prodded. "Now I want the truth or I may have to call the authorities. So now, Ronnie tell me whats going on and it better be the truth". Of course she knew it would be the truth because part of his subliminal programming would prevent him from lying to her.

"Oh please Miss Maddy I'm so sorry. Its just that seeing how pretty you are in your bikinis, and then I saw your yellow one you left and when I touched it it was so smooth and soft and I tried it on and knew it was wrong so I took it off and tried to forget about it. But I saw some in the store and bought a couple cause something just made me want to wear it and think how nice it would be to be pretty like you I couldn't help my self Miss Maddy, I am so sorry Miss Maddy. Really I won't do it again Miss Maddy, Please don't fire me", I ranted and begged hoping to save my job.

"Well what a touching tale Ronnie. Lets think about this a bit. You want to look pretty like me so you bought yourself a pretty bikini. That is flattering Ronnie, but I want to see it on you, Now Strip young lady", she commanded me.

In fear for my job I did as she told me. When I was down to just my lacy white panty she started to laugh at me and told me to stand still. "What a pretty tan line across your breasts Ronnie. I guess you were wearing it, and such pretty panties too. Is this really something new or have you always worn them Ronnie?"

"No Miss Maddy. I just started wearing them when I didn't have the bikini on Miss Maddy. Really I never did that before Miss Maddy."

"Okay young lady, lets see you in the bikini now" Maddy demanded. She retrieved her phone from the bar and started taking some pics of my tanned body as I stripped off my panties. I was so humiliated being naked in front of my beautiful boss. As I changed she noticed my smooth legs. "I see you shaved your legs too Ronnie. I think it looks pretty."

"Well I used to in school when I swam on the team but I always hated shaving them", I told her.

"So what did you do this time" she asked.

"I had them waxed, Miss Maddy," I told her, and went on to tell her about wanting to buy Nair, and what the clerk said about the chemicals and all and I must have been blabbering as I finished putting on the bikini.

" MMM turn for me Ronnie dear" she said and directed me with a twirl of her finger as she clicked more pictures. Looks like they did your tummy and eyebrows too. Don't you think the eyes are a bit girly for a young man?"

"They didn't really give me a choice Miss Maddy. I mean they just said to trust them and this is how they ended up."

"Don't you worry Ronnie with your shoulder length hair they fit your new look just fine. Where did you get the waxing done dear?"

" I ended up at a salon near Carmel. I think it was called Olga's something or other." I told her.

"Oh you must mean Lady Olga's. She used to be a client of mine. I have only heard wonderful things about her place. I just know you plan to go back and keep it smooth. I will call her and tell her how good the job looks on you?'

"Oh please Miss Maddy, you don't have to do that, I don't know if I will stay hairless after this" I begged her. How could I have picked a place that she even knows with all the damn salons out there I thought.

Changing the subject a bit Miss Maddy said, "Ronnie that suit looks so adorably sweet on you and with your pink room maybe I should just keep you as a girl. Would you like that Ronnie dear"

"Oh no I can't do that Miss Maddy. My friends and all might be a bit weird-ed out about it and I just don't think I could"

"Don't be so sure honey, I'm sure you will learn to like it and I think it might just do wonders for you personally. Just look how pretty you are in these pictures", she stated. Before I could see them Annie entered with lunch and laughed out loud at me in my bikini.

"Annie dear, stop laughing at my new pool girl and set the lunch out on the table and come here." commanded Miss Maddy. Annie did exactly as told and on her return gave Miss Maddy a long deep kiss as they embraced.

Turning back to me Annie said, "gee it looks like your pool girl is a sissy Maddy. And it looks like she is having a bit of a problem in her panty!

"Yes, I noticed darling. We will have to deal with that after lunch.

We sat down to a nice lunch of a salmon salad and iced tea. There were a couple of pills on my plate as well and Maddy mentioned that I should take my vitamins with the tea. I did without thinking to ask what they were for and she went on to explain that Annie was much more than a housekeeper, but was her long time lover as well.

I thanked Annie for the tasty salad and said to Miss Maddy that I felt a bit woozy and wanted to lie down for a bit. She said to go lay out in the lounger while she and Annie finished chatting about her trip. I did as suggested and tried to listen to them but couldn't seem to focus on their words. When they were done Miss Annie cleaned up, changed into a blue string bikini and then sat next to me as Miss Maddy took a seat on my other side.

Miss Maddy held my hand and talked softly to me. She explained how that I was to move in permanently and serve not just as her pool girl, but in anything that she required. She told me about the hypnotic messages she had been using subliminally through my headphones and the stereo and how she has been programming me to be her little bimbo sissy maid. "Lets watch some videos" she said picking up the remote for the big screen TV. The 60" screen came to life and showed my activities throughout the pool house the past few days. As shocked as I was I couldn't move from my seat. I felt like I was glued to it and compelled to watch the screen. There I was prancing around in my bikini, swimming web surfing and everything else I had done during the week. Miss Maddy explained that she and Dr. Dane enjoyed watching the live feed from their vacation condo, and enjoyed watching how the hypnosis was affecting my thought patterns.

As she spoke softly and clearly into my ear Miss Annie was rubbing her hand over my bikini bottom making me squirm a bit as I became hard in my bikini. The video ended and I was panting with desire being between to beautiful women touching and talking so sweetly to me. I wasn't even shocked by the video. It just all seemed so surreal but also so correct. "You do like looking pretty don't you Ronnie?" Miss Maddy asked.

As Annie rubbed me a bit quicker, I replied seemingly in a trance "oh yes Miss Maddy. I like looking pretty like you."

"And do you want pretty breasts and a nice smooth panty line and makeup and dresses and panties all the time?" she probed deeper.

"Oh yes Miss Maddy, please Miss Maddy, I so want to be your sissy girl. Please help me Miss Maddy!" I cried feeling like my cock was going to explode any second.

Maddy turned off the TV and snapped her fingers and I suddenly seemed awake and alert. "Now that you are a bit more focused I need to explain some things to you Ronnie. Do you like it when I call you Ronnie?"

"Well my name is really Ron not Ronnie" I said meekly. "What name would you want if you were a girl Ronnie?" she asked me. Well actually I think Brenda is a cute name for a girl Miss Maddy" I said with a bit of a blush. "Oh that is a sweet name. Brenda Bimbo it is then", she said eliciting a laugh from Miss Annie.

"Let me explain to you what the future is going to involve for you Brenda." Miss Maddy said turning her seat so she was looking straight into my eyes and explained her vision to me. "I have programmed a trigger word deep into your mind Brenda. If you are ever disobedient, I will use that trigger and it will cause you enough pain to correct your behavior immediately. That way you will always be in my or Annie's control without question. Other times we may punish you in other ways to insure your proper behavior. Is that fully understood Brenda?

"Yes Miss Maddy. I am to obey you always or I will be punished." I answered.

"Good girl Brenda. Why don't we try it so you can see how effective it is" Miss Maddy said with a glance to Annie.

"Oh no please don't hurt me Miss Maddy" I cried.

"Oh that's ok Brenda, just a little test so we know it works. Annie would you like to be first to try it?

"Why thank you Maddy," said Annie and she turned to me and said "Fillmore".

I immediately doubled over in pain as it felt like Annie had smacked me in the balls. Tears came to my eyes as I cried out from the shock and then it stopped and Annie again gently rubbed my sore crotch back to its previously excited state. "Just so you know Brenda, the louder it is said the more it will hurt. If she had yelled it you might have lost consciousness from the pain. But don't worry, your trigger words will only work when used by Annie or myself." she explained. "Another trigger word is "Stiffie" said Miss Maddy, and my body immediately froze in place. I couldn't move a muscle. Maddy then said "release" and I was back to normal.

"Mmmm, so nice to see how well those work. Don't you agree Annie?"

"Definitely Maddy, she is going to be such a fun little bimbo now" replied Annie.

"But why cant I be a man like I am supposed to be? I don't want to be a, a, a bimbo Miss Maddy?" I stuttered.

"Well now Brenda, would a real man try on his bosses bikini and then go buy one for himself?"

"No Miss Maddy" I replied.

"And would a real man have his body waxed and eyebrows arched high? Would a real man come to work wearing pretty white lace panty with his cock tucked down?

"No Miss Maddy" I replied. "I guess a real man wouldn't. But you hypnotized me to make me do it"

"You know Brenda, hypnosis will only help you do things that you want to do. It wouldn't make you do those things if deep inside you didn't really want to. So no Brenda, a real man wouldn't, but you did didn't you?"

"Yes miss Maddy"

"So what does that make you Brenda? Does that make you a real man?"

"No Miss Maddy I guess it makes me a sissy man?" I volunteered.

"Let's try some more questions. Brenda how many women have you had sex with?

" Er, um Miss Maddy there have been, ohhh I haven't Miss Maddy I am a virgin" I cried and they watched tears rolling down my cheeks.

"Annie do you see how well her programming works, she can't help but giving truthful answers no matter how hard she may try. Isn't she the sweetest sissy bimbo you ever saw?" asked Miss Maddy.

" And have you ever kissed a pussy Brenda. Like how you kissed the crotch of my yellow bikini in the video we just saw."

"No Miss Maddy"

"And have you ever had a blow job Brenda?"

"No Miss Maddy"

"Have you ever sucked another mans cock Brenda?

"No Miss Maddy."

"Do you like my breasts Brenda, or do you prefer Annie's much larger ones?"

" You both have such beautiful breasts Miss Maddy, I really like they way both of you look, but Annie's are very exciting Miss Maddy."

"Well Brenda darling your life is certainly going to change starting now. Here is what is going to happen. You are going to give up your little apartment in town and move in to your pretty pink room here. You will be made over into our sweet little sissy bimbo while continuing to work as you have been these past 2 years. And yes you will still be paid. We will make changes to your appearance as we see fit and you will be accepting of that. You will soon have your own pretty breasts to fit into your bikini tops and bras. You will remember to take your girl vitamins everyday. You will become more and more feminine just because it pleases me. Would you like that Brenda?

"Yes Miss Maddy, but will I be a sissy all the time?

"Of course you will my darling. You could never be anything else once you have your own beautiful breasts you know,"

There will always be a voice in the back of your brain that knows you were once a male and should be upset about where your life is taking you now. It will never be able to stop you from obeying, but it will make you feel like a helpless humiliated sissy as you become more of a bimbo. We will control your sex always. Controlling how, and when, and with whom you can have it. Or if you get to have it at all.

You will lose the ability to think for yourself, but, your knowledge and skills will remain locked in your brain so you can call upon them when needed to complete tasks safely, like driving, or cleaning the pool or in an emergency situation. But your everyday focus will be to be the best sissy bimbo you can. Always awaiting the next command from those around you. Always wanting to be the best sissy you can. Always wanting to please your Mistresses. You will always a address Annie and myself with Mistress or Miss before our name. You will address all women as Miss and males as Sir.

You will always obey, and expect to be punished for any disobedience or wrong doing. You will dress as directed and preform all tasks with a smile no matter how humiliated your old male self feels about it. You will be bound and punished sometimes just for our pleasure and you will thank us when we are done. And you will serve any guests to our home as if it was Annie or myself directing you. Do you understand all of this Brenda?"

Hardly remembering all she said, and being so excited from Annie stroking me I softly said "Yes Mistress I do".

"Louder please, I could hardly hear you Brenda. Tell me what you desire."

"Yes mistress Maddy", I practically screamed. "Please make me your sissy bimbo so I may please your desires Mistress."

"Much better Brenda. Yes I will do all of this to you and more. But first we much take care of the fact that you are still a virgin. Annie please stand and strip for us." she commanded

Annie immediately complied and I saw her beautiful body before me. I had not even seen her in a bikini before. She was my height with a perfectly formed 34C chest with dark nipples that begged to be sucked. A tiny 24" waist and lovely wide hips. At 37 years old she had the body of a 22 year old model and a face to match. And a perfectly hairless pussy glistening with moisture. My erection got even harder in my black and red bikini bottom seeing this magnificent sight. I thought I would cum any second.

"Isn't she pretty Brenda? Look at her beautiful breasts and lovely smooth pussy. Don't you wish you could be smooth like that too. I know you do. Maybe someday you will be. And those gorgeous big breasts. I bet a bimbo like you would love to have pretty breasts like those wouldn't you"

"Oh my Miss Maddy, she is so pretty and smooth, and her breasts are so hot to look at. I am afraid I may cum in my panty Mistress Maddy."

"Calm down Brenda girl. I have something better in mind for you. You are about to find out that Annie has the most delicious and tightest pussy you will ever find. And you are going to get to fuck her and lose your virginity. Would you like that Brenda?"

"Oh my yes please Mistress Maddy and Miss Annie please take my virginity from me please let me fuck?"

"If I told you that you may never be allowed to fuck a woman again would you still want to do it Brenda?

Allowing my virgin sissy cock to think for me I begged her again, 'oh yes please Mistress I don't wanna be a virgin any more, Please Please!

"Ok Brenda but there is a catch. Because you are a virgin I am betting you won't even last 5 minutes inside her before you squirt your sissy juice. Now to encourage you to take your time and enjoy your first fuck here's whats at stake. Since you liked her larger breasts better and since you will be a sissy bimbo that needs her own breasts Brenda dear, if you can last 5 or more minutes you will get pretty C cup breasts of your own to match Annies'. For every minute under 5 you will go up a size. You better make at least a minute if you don't want to make Dolly Parton look small Brenda. You actually get to trade your virginity for new breasts. Isn't that a wonderful trade?"

"Yes please Mistress, I want pretty breasts too Mistress," I moaned too aroused to think things through.

You need to pull your cock out of your bikini and Miss Annie is going to kneel over you and take you in to her warm inviting pussy. The time starts when you are fully inside her. Remember 5 for a C, 4 for a D, 3 for E and so on. Are you ready?"

"Yes Mistress, please have her fuck me now."