5 comments/ 25551 views/ 27 favorites Halloween Pool Party Pt. 01 By: sissymissyct The Dane Estate sat on 15 acres in the hills north of New York City with a view of the Hudson, plenty of trees and open space and an amazing pool. It was one of the infinity style pools and it looked like you could jump all the way to the river from it. Nearby sat an 8 person hot tub with hundreds of perfectly placed jets. It has a seasonal building around it with a retractable cover so you could swim if it rained, or year round. A bedroom, changing rooms, big screen TV's and a well stocked bar and grill completed this bit of heaven. Well maybe not heaven for a lot of people but it was for me. I stayed here about half of my time, and would spend the night listening to tunes or watching the TV. For 2 years I was the pool guy tasked with keeping the pool and tub clean and maintaining the pool building. I had worked on pools for a few other folks but the Danes' made me an offer to work full time for them. I would make more than all my pool jobs combined and plenty of time for myself to swim, chill out, or go to town. They traveled a lot to so that meant even more time for me. I kept my small apartment not far away. My few acquaintances knew me as Ron the pool guy, but I didn't hang out with them too much. I am a bit of a loner actually. I dated a few gals, but nothing lasted too long. I am considered good looking and at just over 5'6" have a decent body as I was a swimmer in high school and college, I guess that I often felt intimidated by the young ladies I went out with. Always so in awe of their beauty and feminine manners that I just seemed to get clumsy around them. Maybe they thought I was beneath them because I didn't have a fancy career after college like they all did. But I was happy. I made great money with very few expenses. I ate most meals free at the Danes, the only suit I needed was a bathing suit. And I spent most nights sleeping in the room in the pool house. My car was new and paid for, I didn't really have any family to speak of, and was free to travel if I wanted. So back to the Danes. Dr. Thomas Dane was a high profile surgeon in Manhattan. I would only see him a few days a month as he mostly stayed at their condo in the city. He was about 45, 6' tall, smooth shaved and handsome. His wife Maddy was here most of the time. She had her own Hypnotherapy and Acupuncture clinic here in the valley and was quite successful on her own. She was 5'10", about a size 12 with maybe a b-cup chest and long dark hair. Really a classic beauty. She swam daily and worked out often giving her a very strong and commanding presence. And wow, did she look hot in a bikini. I know because I would tremble just handing her a towel as she emerged from her daily swim. I think she enjoyed how she looked down at all 5 foot 6 of me as I handed it to her before getting her a glass of wine from the bar. I am so glad I had baggy swim shorts on. Lol So its early October and the Danes were away for a week. I finished my work and decided to take a swim. Even with no one else around, by habit, I went into the changing room to put on my swim shorts. As I was sliding them on I noticed one of Maddy's bikinis laying on the bench. It was bright yellow with a white heart print. I quickly imagined her in it and was seemingly drawn to it. I picked up both pieces and felt how soft they were. So much softer than they my baggy swimwear. I rubbed the panty against my chest, then brought it up to my face. I stretched them wide and pictured how pretty they looked on Maddy. I was getting more aroused and actually kissed the crotch thinking of my gorgeous employers pussy being in them. Getting to lick and nibble at her clit. It was too much and I quickly put them down on the bench and did my 20 laps in the pool. I went back to my place that night and had dinner, but couldn't help but think about Maddy and that yellow bikini. I went out to the neighborhood bar for a couple drinks, thinking maybe I would actually meet a gal and quit thinking about the days events. A couple of people I knew stopped in the bar but I couldn't clear my head and decided to go home and masturbate. Maddy's bikini seemed to be controlling my thoughts. I masturbated thinking about her in them and how soft it felt against my skin. I came a couple of times that night and drifted off to sleep with visions of bikini's in my brain. The next morning I went to work as usual, but with no one home I really didn't have much to do all day. Even the the Housekeeper that cared for the main house was not around this week. I turned on the stereo and with headphones in place fired up my laptop. I answered a few emails and then decided to surf around the web a bit. Not sure why but my fingers seemed to just type on their own, and I was soon looking at pics of young women in bikinis. I couldn't keep from getting hard looking at their beautiful fem bodies and how pretty their smooth crotches looked in the bikini panty. It looked so natural, and I felt like I was in a trance looking at them. I was rock hard in my pants and rubbing myself as I stared at page after page of pics. I'm not sure how long I was on the laptop but I finally gained enough of my senses to put it down and go for a swim. I went to change and there was that yellow bikini. I undressed and picked it up knowing I had to try it on. My hand shook as I fastened the bra around my chest and tied the halter top around my neck. It felt electric over my nipples and and I caressed both sides as it hugged my slight frame. Then the panty. My legs trembled as I slid it up and over my stiff 6" cock. It felt so right but looked so wrong with that big bulge. If the top felt electric the bottom was lightning. I tried to tuck my cock back so it would fit flat in front like Ms Dane and the women on the websites, but I was too hard. I gently rubbed the soft fabric. It felt so nice and I exploded in the bikini before I could stop myself. I felt so guilty about what I just did. Maddy would fire me if she found out. I quickly took the suit off and washed it in the sink. I took my swim and went back to my apartment. Not much to do at the pool-house anyway. I decided to take the next day off and relax in town. "Look Thomas" Maddy Dane called to her husband. "I linked into our home security system so even here we could watch our little project." Thomas joined his wife relaxing on the deck of their rental condo on the beach in Costa Rica. "Here is Ron on one of the pool cams. He finished cleaning and is on his laptop." "Is he wearing the headphones?" he asked. " Yes dear, and if he has been doing that as much as most young people use them my subliminal codes should have started to work on him." Maddy replied. "I told you I would win this bet. You will just have to pay up when the time is right" she gloated. "Ha, you don't really think that he's listening to the music you want do you. He probably has his own play list." he laughed back at her. "Don't be so sure" she said, explaining that her techie showed her how to run background feeds through anything playing in the house. "Well you better keep it out of my headphones if you know what's good for you" he teased. "I certainly know whats good for me and maybe I already have done it darling, and you just don't know it yet", she teased back, then leaned over to kiss him. "Oh look he's heading for the changing area maybe he's going to go for a swim. Well look at him naked Tom, he does have a cute little body." Tom agreed and before commenting they watched their pool boy putting on the yellow bikini. "Wow, maybe your hidden tracks are having an effect" Tom said as they both stared at the young man totally oblivious to their spying eyes. "I cant wait to see how the week progresses" Maddy said with a satisfied smile on her face. The night at his apartment was much like the last night, thinking of Maddy and her yellow bikini. Rubbing my stiffie with one hand and my chest with the other, my hair seemed much more noticeable that in the past. Remembering how I used to shave it all off when I was a competitive swimmer. (Not that I ever won, but all the guys on the team did it so I did too). "Might be time to shave again", I pondered, thinking about how much nicer that bikini would look then. But when I remembered all of the razor cuts I seemed to get and thought better of it. Maybe I would get some Nair in the morning and use that instead. I jerked off again thinking of wearing that bikini earlier and even swimming in it the next time. In my dreams I saw just that. Swimming in a pretty bikini with my own full breasts filling out the top, and a pretty, smooth line in the panty. I awoke the next morning with the remnants of a wet dream in my bed. After a leisurely breakfast I headed out shopping, I needed some groceries, and some socks and of course some Nair. I stopped first at the drugstore to get some the Nair. On the way into the Walgreen's I passed a nail salon with a sign out offering waxing. I was drawn to the sign thinking that might be easier than than the Nair but shook off the idea as too embarrassing. I strolled into the pharmacy and looked at the Nair and similar products. A young employe approached asking if I had any questions and I said I was looking for a hair remover. "Well any of those will work OK, but I will tell you something straight-up" she said. "They are all filled with harsh chemicals and that's like really yukky for your skin". "What do you recommend," I asked. "Laser is the best but really expensive. I go for waxing. It may hurt a bit but lasts much longer, and leaves your skin smoother. Why don't you get your friend a gift certificate to the salon next door?" she said. Happy that she didn't seem to think it was for me, I told her "thanks maybe I will" , and headed out the door. On the way back to the car I peered into the salon. "Maybe she was right," I thought and decided to do it. I would hate for an someone I know to see me in there. Maybe I should go to another town and do it. I have all day so I drove about a half hour away. Wow, every strip mall has a salon it seems. Well let me try here. The first salon said they didn't do waxing on men, and I left feeling a bit embarrassed. "Were they all like this?" I wondered aloud. The second salon would do men but the price seemed outrageous. Not wanting to go home hairy he decided to try one more. I spotted Lady Olga's salon in the next strip mall. At the reception counter I was given a fair price and told that they could do me right away. Admitting to never getting waxed before, "I just want my legs done" I told her. But then Olga reached over the counter and plucked a hair out of my chest just inside my shirt, startling me and making me jump back in surprise, and said "Chest Too!" Loud enough for all to hear "and maybe back". She pushed a buzzer and 2 women approached the counter."This is Myra and Portia, you will follow them and do as they say" she told me. I said "Yes Ma'am" and turned to follow them towards the back of the salon. I blushed as the gaze of about 6 or 7 female customers watched me following them. We got to a door and Portia told me to go in, take my clothes off and lie on my stomach, covering my ass with the towel. The waxing room had a padded table with the "required" tissue paper covering, a mirror and a few cabinets of supplies, and very bright lights. What they called a towel was really a hand towel and to me it looked more like a small washcloth. "What would that even cover" I thought? The waxing technicians entered a few minutes later and Myra explained what they were going to do and said it may hurt a tiny bit but that I was to stay still. As she checked the wax, Portia put my clothes in a cabinet. I wonder why she locked the cabinet with a key, but figured it was to help clients feel that their belongings were secure. They each started on a leg and I did wince a bit when after spreading the wax they rubbed a cloth on it and yanked. With my legs done almost up to my ass and my back done they told me to turn over. Not so easy to keep my package covered and turn over at the same time, I tried to do it as gracefully as possible. Although pretending to look away as I turned, I know Portia and Myra tried to steal a glance. Myra and Portia were both probably in their 40's, matronly but pretty like Olga and with the same accent. Probably Polish or Russian or something. They soon started on the front of my lower legs . The pain was hardly noticed down now, just that little bit of a wince. Especially when they both yanked a strip at the same time. A quick knock at the door and Olga stepped into the room and said something in her native language to my waxers. They both nodded and Olga said "okay" then quickly pulled up my towel, looked at me for a second, looked at my face briefly, and said, " Ya, do full treatment girls" and walked out. I asked what full treatment meant? Portia said "Miss Olga won't let anyone out that doesn't look perfect, and we are to see that you do." Still kind of shocked over Olga's actions I just kinda said OK and laid back on the table. My legs done up to my thighs and I started to get a bit aroused as they were working closer and closer to the towel. Portia moved to my chest, blocking my view as Myra slid the towel away and got up into my bikini line. I was not expecting that and it was definitely more painful. I started to move but Portia pushed my chest down to the table and told me, "It is okay. We have seen men before." It was to late to stop it and when Portia finished my chest she helped Myra by pulling and stretching my privates to make it easier to wax. She even held my legs up so Myra could wax my taint and around my ass hole. Well no way I was going to get embarrassed by being hard under these conditions. Far from it. I shrunk like I was swimming outside in winter. Finally done and Myra started rubbing a lilac lotion into my skin starting at my feet. She said it would help the skin feel better and had ingredients to help slow future hair growth and I would smell really pretty too. "Oh great, now will smell pretty too, and I still have to go shopping." I thought to myself. As she rubbed in the lotion my my skin felt immediately better. Portia was looking at my face and telling me to hold still, she started trimming my brows with a tiny scissor. I told her my brows were fine and she said she was just going to clean them up a bit. "We do men brows all the time, not to worry" she told me. Maybe I should have worried as I next felt her applying wax under my brow and ripping it off then another strip on top. I was certain there was nothing left but I could do nothing about it now. She finished my other side, plucked a few strays and pronounced me finished as Myra put some of the lilac lotion on my brows. I swear it felt like they were all gone but I couldn't see the mirror. My clothes were returned and Myra asked if I was getting a mani and pedi too? I told her I couldn't today but thinking I would not be doing this kind of thing again anyway, said I would be back next week for it. I dressed , then went and paid Olga and she smiled and said I looked and smelled great and asked me to come see them again soon. I said I would and left a large tip for Myra and Portia. I got in my car and realized I had spent almost 3 hours in there. As I looked in the mirror before backing out I caught a glimpse of my eyebrows. There were two delicate arches over my eyes. Oh my goodness, how am I going to explain that to anyone. Maybe I will shave the rest off or something. Or sun glasses, yes big sunglasses that will cover them up. I went to Target for socks and because the grocery was nearby. First I went to the sunglasses rack and found a pair that would cover my brows. They were a womens style but seemed pretty unisex to me. It didn't take long to get the socks but on the way back to the register I had to pass through the womens section and there it was. A whole rack of End-of-Season bikinis on sale. Something flipped in my mind and I knew I had to get one. I remembered that Maddy's was a size 12 and seemed to fit me, so I looked at those. No one seemed to be paying attention so I went through them looking for the hottest one. I found a soft pink with white lace trimming on it and had to have it. Then I saw a similar one in black and red and grabbed it too. I headed to the check out and the clerk rang them up saying that it looks like someone was going to get a nice present. If she only knew, lol. I got my groceries at the nearby supermarket and headed home. After putting the food away I couldn't wait to try on my new swimsuits. I decided to try the black and red one first. It felt so delicious against my now smooth and hairless body. I ran my hands over my body and the soft swim suit and it made me hard instantly. I hopped into my bed and stroked myself furiously thinking about how nice it would be to swim in the new pink one the next day. I fell asleep in my bikini and didn't wake up until 10 the next morning. Deciding that I couldn't wait until I got to work, after a shower and further examining my now hairless body I wore my pink and white bikini under my jeans and tee shirt, had breakfast, then headed for the Danes' home. It was a sunny and very warm for an early fall day so I hit the button to retract the roof over the pool and started my chores. "What the heck, ain't no one here but me", I thought and took off my outerwear and decided to do my work in my bikini. It felt so fun and a bit kinky to be working like this but I didn't care. I took a break and did a few laps then rested a while with some music and web surfing. Checked my email too, and there was one from Maddy that said she would be home Saturday. She mentioned that she had left a couple gallons of paint in the garage to repaint the bedroom in the pool house and wondered if I could take care of it before they returned. She said there was a roller and brushes and everything else needed with the paint. It was just Wednesday so I had a couple more days to enjoy my privacy. I replied that everything was cool here and I would take care of the painting and looked forward to their return. The sun was shining brightly as I surfed the web a bit more. Again drawn to pics of bikinis but this time it was guys in bikinis and they all seemed smooth down below. I read about how these "tranny" guys tucked there cocks to get a smooth look and knew I should do that too. It felt really odd at first, but once I ran my hand over my smooth crotch in the beautiful bikini I was wearing I was ecstatic. It felt so right and looked so pretty and natural. The snug bikini bottom hugged everything just right and the lace trim made it look even more fem. I decided to get in the hot tub to relax a bit and after setting the timer I enjoyed the pulsating jets over my body. Like a super massage, it felt so relaxing. I turned to my side and felt a couple jets directly on my tucked back cock. What an amazing feeling. I let it pulse on me for a while and soon had an amazing orgasm without even touching myself. Oh my how wonderful that was. I wondered if that was why Maddy loved the hot tub so much. It must excite her every time she gets in it. "Women are so lucky" I thought. The tub turned off automatically and I hopped out and swam a few laps before going back to the headphones for more tunes and played some online games that I liked enjoying the warmth of the fall sunshine streaming in through the open roof. Around seven I decided to change and closed the roof and locked up before heading home. "Thomas, It looks like our pool boy has his own bikini now. Take a look at these cam views." called Maddy. "Wow" the Dr. replied, "I guess your subliminal codes really are effecting him. That doesn't look like one of your swimsuits darling." "No its not. It really is sexy though. He must have bought it himself" she laughed. "And did you notice when I zoom in that his body is shaved smooth too? And check the arched eyebrows. How sweet is that? This is even better than I hoped for. I didn't think it would have such a strong effect on him this quickly. His mind must be very susceptible to hypnosis for it to work so well. He may be a "Pool Girl" quicker than I thought." The Dane's both laughed at that before turning off the cam feed. Halloween Pool Party Pt. 01 On the way home I stopped at Target again. I felt like I was in a trance as I headed right for the lingerie section and picked out a half dozen pairs of tight lacy panties. "If the bikini felt so nice all day then these must feel just as good", I thought." Gotta be nicer than boxers". The clerk gave me a funny glance as I paid but said nothing. Then as I passed a mirror on the way out I realized that my bikini top was showing a bit through my shirt. "Oh shit" I thought, I had better be more careful about that in the future. I should have taken it off before leaving work. I made a nice dinner and turned on the tube for a bit but I wanted to try on my new purchases. Stripping out of my jeans and tee shirt I admired myself in the bikini a bit. As I took off the top I noticed a bit of a tan line from all the days sunshine. I was annoyed with myself as I did not think that would happen. When I dropped the bottom off there was a tan line there as well. But now I was stuck like this. I figured it would just fade away and probably be gone by morning I consoled myself deciding no one will see it anyway. I grabbed my shopping bag and tried on my new panties, admiring how sexy they looked when I tucked. Finally I just jerked off and drifted off into a nice deep sleep. I figured I would get the painting done in the morning. I headed to the Dane's early Thursday anxious to get the painting done so I could swim. I found all the supplies in the garage as Maddy had directed. I moved it to the pool house and took inventory, Brushes, roller, cleaning supplies, drop cloths and a package of 10" wide lace wall trimming with a note that it would be a border around all the walls just below the ceiling. I moved all the furnishings either into the pool room or in the center of the room and covered everything with drops. The room was about 14x20 feet and it shouldn't take too long to finish. I cranked up some tunes from my play list and blasted it through the building. The work went easy and by 1pm I was placing the pretty lacy border strip along the top of the walls. After cleaning everything up and moving the room items back into place, I finally stepped back to look at it all and could only think "Wow, is that pink and girly". Then another thought struck me. I am the one that sleeps here so why did she want it so pink. Maybe she is going to get rid of me and have some niece or someone move in. Oh man she better not fire me, I don't want to work anywhere else. Well I can't do anything about it now. I went to change into my black and red bikini. As I undressed I noticed that my tan lines from yesterday were darker and more noticeable. Damn, I didn't want that. Well at least it doesn't show with this pretty bikini on I told myself and I strutted around like a giddy young girl a bit, and finally jumped in and swam some laps. After 25 or so laps I climbed out and was going to check my email when my phone rang. It was Maddy calling from Costa Rica. She wondered about the painting and I told her I had finished. "And what do you think about the color", she asked? "It is a very girly pink Ms Dane. It may take some getting used to if I continue sleeping in there" I replied. "Well, I am sure you will adjust to it. I think its the perfect color for you." And before giving me a chance to ask why she said "So what have your been doing while we were away Ronnie"? I said that I made sure everything was clean, that I did some personal shopping and mostly sat around listening to music and texting and web surfing. "Have you been using the headphones for the music Ronnie?" she asked. "Oh yes Ms Dane I can still hear the phone with them on. I hope its OK.?" I replied. "Yes Ronnie that's a good girl", she said. "Please continue to use them. Remember that Thomas and I will fly back to NY tomorrow and I will be there Saturday morning. I expect you to be there when I arrive and the housekeeper too. Please leave her a note to that effect for me". "Yes Ms Dane, I haven't seen her yet but will remember to do that for you. You can count on me as always Ms Dane." I told her. "Yes Ronnie, I'm sure I can. And another thing Ronnie, please call me Miss Maddy like Annie (the house keeper) does, I like the sound of it better than Ms Dane" she directed me. "Oh yes certainly Ms de. I mean Miss Maddy", I corrected myself. "I will see you Saturday morning". She hung up before I could say anything else and I wondered why she started calling me Ronnie? It was always Ron before. The rest of the day went mostly like the others. The new paint smell was still quite strong so I went home for the night. Thomas asked his wife about the call and was told that everything is going according to plan. "I do look forward to flying out of here tomorrow. And staying with you at the NY condo tomorrow night will be fun before heading back up the valley. I so love our time together when you are not at work dear". In fact I have something planned for tomorrow night that I am sure you will find exciting". With that she hugged him tight and seduced him on the veranda enjoying their last vacation night. Friday morning they caught their early flight to NY. A slow limo ride into the city and they were having a relaxing dinner at their favorite Hells Kitchen Bistro. An early evening and back at the condo they enjoyed the view of the skyline smooching on the patio of their 58th floor city home. Breaking away from a deep kiss after feeling Thoms' hard on through his pants Miss Maddy whispered the trigger word "Thunderbolt" into his ear. He stood motionless for a minute and then almost like a robot said "What may I do for you Miss Maddy?" "Strip and lie on the bed. You will not be able to move once you are there." In a trance he obeyed his wife's commands as she pulled a small box out of a dresser drawer. She climbed on the bed sitting astride her man with her ass on his face. "Lick it" was all she said. As she felt his talented tongue worshiping her bottom hole she reached forward and took his flaccid cock and soon had it encased in a metal chastity tube with a titanium lock through its loop. She released him form his trance and he continued to lick her. She moved so he could tongue her swollen, wet pussy and didn't get up until she had 3 orgasms all over her chastised hubby's face. She rolled off Thomas and when he reached down he felt the metal cage trapping his cock. "What the hell is this supposed to be Maddy?" he yelled at her. "Calm down Thomas you will wake the neighbors. That is your new chastity cage that you are going to wear while you are in the city. I know you still like to think you are still the playboy you were in college but that's going to change. You will only have sex when you come home to me as that's where the key for the lock is. And you will start behaving a bit better in the future if you want it off.. If you do then your sex life will be hotter than you could ever imagine. If not you will just have to suffer with it on. Do you understand what I am saying Thomas?" "Yes Maddy, but why couldn't we talk about this if you had a problem" he asked. "And what did you do to get it on me? Did you put some damn hypno trigger in me. I told you not to do that. Dammit!" "What you said and what I do aren't always compatible Thomas. Like your buying 2 thousand worth of drinks at a strip club for your doctor buddies last month. That's not compatible either. Its time for me to take proper control of this marriage like a woman should. And if you want that cock freed you better get on board with it." explained his beautiful wife. "Well we have things at the hospital to cut rings and stuff of of patients you know." said the Dr, trying to retake control of his marriage. "Go ahead and try darling but it won't work the lock is titanium. Your cutters won't work on it. And if I find out you have disobeyed me and somehow removed it without damaging your precious cock, you will be in real trouble. Do I make myself clear? Remember, the trigger phrase is always active for me! Now lets get some sleep I am tired after all the travel and orgasms." Not much going on Friday. A quick check of the house and grounds and time for me. I opened the roof as Indian summer was upon us and I wanted to enjoy the fresh air. Might as well enjoy it before Maddy gets back. I quickly dressed in my pink bikini again and took a quick swim. A nice burger on the grill for lunch and time for the headphones and some gaming. I could not concentrate on the game with Miss Maddy occupying my thoughts. Why was she calling me Ronnie? Why would she want the room pink? Too bad I won't be able to wear this pretty bikini until she goes away again. I soon drifted off to sleep in the lounger and it was sundown when I awoke. I hit the button to close the roof and remembered I needed to go back to my apt for some clean clothes and things as I wanted to sleep here tonight so I wouldn't be late to greet Miss Maddy in the morning. As I changed into my clothes I realized I had caught a lot more sun than I expected again and my bikini tan was now very noticeable. I couldn't worry about that now and made a quick trip to my place and it wasn't long before I was heading back to the Dane's for my first night in that pink room. I put on some tunes and the headphones and was soon fast asleep. Little did I know what effects I was subjecting myself to every time I turned the music on. And this time I had the headphones on all night. I was up at nine and put on a pair of white lacy panties as I couldn't wear my swim suit under my jeans and t-shirt. I told myself I should just wear boxers but couldn't seem to pull them on. I just somehow knew I should wear the panties instead. I seemed drawn to them like magic or something. But they did feel so nice and snug on my clit, I mean my cock. Wow why would I even think clit. That's weird. 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." 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. 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 "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 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 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." Halloween Pool Party Pt. 04 Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answered reaching down to try to alleviate the pain from by morning wood being punished by the spiked chastity". Then realizing I couldn't stop the pain there I rubbed my sore bottom as Mistress directed me to the shower. A nice warm shower would have me fresh for the days shopping. I found new shampoo, cleaner and body soap all with a lovely lilac scent. After lathering myself all over, I enjoyed the warm water soothing my soreness and too soon I was drying myself with a nice fluffy towel. Miss Annie handed me my satiny sheer pink panties and smiled as she saw how my bruised bottom showed through the sheer material. And pulled me into the main house kitchen handed me some coffee and told me to make breakfast, giving me a handwritten note on what to prepare and how to cook it while she went to help Miss Maddy get dressed. When Maddy entered she was dressed in what would be described as standard business attire. A white tailored shirt, dark blue slacks, low matching pumps, her hair in a tight bun and perfectly applied makeup. My heart fluttered at her beauty, and I curtseyed before handing her a cup of tea and placing her breakfast on the table. She told me to place Annie's plate at the table as she would be in shortly. I was told that today I could join them at the table, and as I turned to get my plate she noticed my bruised bottom through my panties. Before I sat next to her she caressed my still sore bottom. "Did you enjoy having your sissy pussy stuffed and stretched all night Brenda dear?" "It did make it hard to fall asleep at first Mistress", I responded, wincing from her touch. "I bet it did baby girl, but we need to start getting you stretched and loose down there so you can be a perfect bimbo you know. It will make things easier for you to fill your role as a bimbo. I know you will get used to it soon". "I realize you have no clothes so after breakfast I will lend you something to wear so we can go shopping today. We will get you some nice lingerie, and dresses and skirts and blouses for day wear and some pretty things that only a ditzy bimbo would wear. Won't that be fun Brenda?" "Yes miss Maddy but I am a bit nervous about it cause I still look so much like a man and have this ugly bulge in my panty" I blushed. Yes sissy, I understand and you will feel very humiliated before the day is over I promise!" she chuckled. "I was going to but you back in a trance but I want you to learn how for yourself that you no longer have choices of your own. If you were in a trance you would just accept everything I do. And Annie and I really do enjoy when you make mistakes so we can punish you like last night. It really makes us so hot to do that, and its so much better when you bring the punishment on yourself I think. But don't worry, I will be putting you in a trance quite regularly over the next few days to make you a totally ditzy brainless bimbo who dreams of nothing but sex and pleasuring others in ways you could never imagine. Now eat up girl". Annie came in and joined us at breakfast wearing a tank top and yoga pants. Her breasts practically spilling out of her top. Before eating she handed me my girlie vitamins and watched as I submissively swallowed them. After eating, Mistress told me to meet her in my pink room after cleaning up the dishes. I found Mistress in my room and she had some clothing waiting for me. A cream colored blouse similar to hers and a pleated plaid skirt that looked like a schoolgirls skirt with suspenders that went over my shoulders. But at least my panty bulge didn't show under it. A pair of black "Mary-Janes" with a 2" heel that were about a size too small and a small purse for my Id and things. A touch of lipstick and she said we were ready to go. In Mistresses' new Lexus we headed out. We stopped first in a strip center with a high end lingerie shop, as Miss Maddy explained that I really needed a bra before I could shop for outerwear. There were a few customers in the shop as we entered and I gasped in awe at all the pretty and sexy clothing all around me. We went to the brassiere section and the older saleslady asked Mistress if she would like some assistance selecting something. Pointing at me Mistress simply stated, "my sissy needs a whole new wardrobe starting with new bra's." The saleslady looked me over and let out a laugh, and said "well dear you brought her to the right place. I'm Sara and will be pleased to help you emasculate her" "That sounds perfect Sara, thank you so much. Lets start with a some nice D-cup bras in a 38. 1 or 2 functional support styles and at least 6 or 7 very sexy and sultry that would suit a naughty bimbo." "Will she be needing breast too. We have some nice ones that will glue directly to her chest". "Yes, but really just some inexpensive ones. She will only need them for a few days. She will be given implants this Thursday so they are just temporary", explained Mistress. "Wow that's going to be such a permanent improvement for her. I hope you will come and show me when she's healed. In the mean time Missy go into that dressing area and take off your blouse and skirt" she commanded. "Yes Miss Sara" I blushed and did as she said. The dressing area was in the center of the store and had a couch where Miss Maddy could sit and watch and a couple of large curtained areas for changing. Miss Sara returned with an armload of bras a few minutes later. "Lets start with the support bras" she said fastening the first one around my chest before turning me around and putting the soft forms in them. She opened the curtain for Miss Maddy to see and a few other customers and staff saw me as well. As if my face wasn't red enough she then said, "It's too bad about that bulge in her panty, but the bra fits quite well in the 38d." Maddy explained that the bulge was just caused by my chastity cage, and Miss Sara asked with a smile, if that was going to be "fixed" when I got my implants. Miss Maddy told her that it would be fixed but not removed. "We want our sissy to always remember what she was". Miss Sara then recommended a nice firm support girdle to help hide it in the mean time, and Miss Maddy said that we would get a couple after finding some panties. Maddy had approved 8 of the nine bras that I tried on. 4 were shelf bras in red, pink, white and black lace that would show off my breasts. 2 had fuller cups but still covered with lace all over. They were all so pretty and made my chastity start to bite into me. The other 2 were plain support bras that Mistress said I would need to wear as my implants healed. Next Miss Maddy selected some panties that would match my bras including a couple of open crotch styles "for easy access" Maddy stated. She told me to remove my panty and try on the crotchless pink pair. My chastity hung out for all to see and I cringed when I saw so many people in the store looking at me. I was totally red faced and when an unknown shopper said loudly, "What a pathetic sissy" a tear fell from my eye in total humiliation. Mistress Maddy chose at least a dozen pairs of panties and Miss Sara returned with a couple of panty girdles. One long leg white Rago brand , with a high waist and the other a high waist panty style. She told be to take the pink panty off and try the long leg one first. I struggled to pull the tight garment up my legs and she stopped me before getting it all the way up. Miss Sara then grabbed my cage and pushed it back between my legs and then pulled the girdle tight over my hips and waist. It was so tight and my bulge was gone but it caused the spikes to dig cruelly into my clitty. I removed it and tried the black one and again Sara forced my cage back, knowing how it pained me in the other one, and proceeded to pull the girdle up snugly over my hips and waist. "That does look lovely on her Sara. I think I will let her wear that out if its OK with you?" said Miss Maddy. Does it feel as nice as it looks Brenda"? Mistress, I do look pretty and smooth now, but it makes the spikes hurt my sissy cock more, can I please wear my panties? "That's just what I was hoping for sissy. You will wear it under your skirt while we shop today". Mistress then explained to Sara about the tiny pin spikes inside my chastity. Sara said she wondered why I winced like I did. " Would you like a nice corset for her Maddy? We just got some nice new back-lace styles in?" "I think we will wait until after her breasts are healed for them thanks Sara" Mistress responded. "Sissy you have a seat on the couch now while I pick some sexy nighties for you. I want to find some naughty styles for you, and maybe I will get some new things for Annie and myself too." I sat on the couch and realized just how much the cage could hurt as I sat with it trapped under my legs. At least I was dressed now and my blouse did look better with a bra on under it but I couldn't believe how big the D-cup bra looked stretching the fabric out in front of me. "They are such big breasts. What is happening to me. How did this happen, I used to be a guy. Why did I ever pick up that dam bikini." Mistress had finished making her selections and called me up to the counter where after wiping the tears from under my eyes, she paid for everything. I couldn't believe it when it totaled over 6 hundred dollars. Miss Sara thanked us and gave Mistress a hug, and handed me all the bags. "By sissy, come entertain us again soon", she smiled. I put the bags into the trunk of the Lexus and we headed to a nearby shopping center going directly to Forever 21. Mistress walked me through the store picking lbd's, mini skirts, stretch pants, and more. All of it sexy as heel. She directed me into a dressing room and had me come out and model it all for her. We ended up with 3 mini skirts, stretch pants a couple lbd's, and 3 lace covered blouses and a really hot and diaphanous flowing flowered dress. After a light lunch in the food court we stopped at a Piercing Pagoda kiosk and she told the sales girl that her sissy needed her ears pierced. The girl showed her the choices for new piercings and I was surprised when Mistress chose 3 sets. Two small diamonds and a pink pearl. I was told to sit on the un-padded bench and cringed as my chastity was firmly crushed into my bottom as I sat. Seeing me squirm the sales girl ordered me to sit still and with a fierce glance form mistress I knew I had better comply. She marked my ears with a pen to insure that the placement was correct. Taking her piercing gun, one by one she loaded the posts and shot them through my ears. She discussed the cleaning and care procedures with Miss Maddy and myself and we were on the way out. Me with six holes in my ears and another armful of clothing bags. It was time to head further up the valley to Lady Olga's Salon. I almost forgot, and after my last treatment there I kinda hoped that Mistress had as well. We arrived in time for my 3:30 apt. Upon entering Olga greeted Mistress Maddy warmly. After glancing over at me she looked a bit surprised. She immediately called Myra and Portia up the the front. They both saw me and started laughing. "Well what a coincidence", exclaimed Myra. Portia just bet me that we would never see the young man that we waxed in here again and all of a sudden you appear." "Yeah, you haven't won yet Myra. This isn't a young man I say its a sissy so you don't win." The women all laughed as I stood there blushing. "I'm so glad you called Maddy. We cleared our schedule to take care of her for you. Are you really turning her, I mean this, or whatever into a Bimbo" asked Olga? "Oh yes dear. I started a few weeks ago with some hypnotic tapes. That's why she came in for her waxing. She really couldn't avoid it. Oh, and I loved the way you did her brows." "We can tattoo the brows like that if you like" stated Olga. "No that would be too easy for her. She needs suffer through what most women do and deal with waxing for a few years first. I think it will make her a better bimbo. Anyway I'm not thrilled with the tattooed brows I have seen" said Mistress. "Why don't you take care of the items we discussed and I will come get her when you call." I was so happy to here her say that but wondered what was in-store for me. "Sure thing Maddy, probably about 7 or 7:30". she told her. Before leaving Miss Maddy turned and kissed me on the cheek and told be to be a good sissy girl, "or else!" "Ok sissy, head to the pedicure station and lets get started." Olga demanded. I did as told and popped off my heels and sat in the soft pedicure chair. Placing my feet in the sweet smelling basin. Again I felt my chastity crushed in my girdle as I sat back. At least there is some padding I thought. As my feet soaked Olga pressed some buttons and the chair seemed to come alive. It massaged up and down my back to the top of my neck. It felt so nice and comforting. But then the seat started to vibrate under me and soon caused a hardening in my chastity. Olga asked what was wrong and I told her about the chastity design and the girdle. "Stand and show us sissy' she demanded. "The shop is closed so don't be shy." When I hesitated she yelled "Now Sissy"! Or your Maddy will hear about it". I stood immediately and lifted my skirt so the 3 of them could see my girdle, and was told to pull the girdle down. I struggled to pull it down and my locked cock swung out from between my legs. Portia grabbed it and pulled it a bit causing me to double over from the pain showing my red face with tears coming down. "Very nice and fitting for a sissy that thought he was a man. Now tuck it back and pull that girdle back up and sit back down. You will have to deal with the pain because I can't have you squirming while we do your nails. If you do I will have to secure you to the chair, and I know Maddy won't be happy to hear that" "There was that threat of reporting me to Miss Maddy again", I thought. "I hope they don't say anything my ass is so sore from last time still." Olga began to work on my nails while Portia and Myra each worked on one of my hands. They had finger bowls on the armrests for me to soak them in. As Olga did something I kind of moved a bit knocking a bowl over. I apologized profusely but Olga was annoyed and told Portia to secure me. After wiping what I spilled she pulled a strap across my chest above my false breasts and tugged it tight, as Myra did the same with one below them. "These straps are here to help some customers with medical issues to enjoy a pedicure with out issues. But for you, they will bind you securely." Olga said. One more strap across my upper thigh and I was going no where. It was pulled so tight they had to know it made the chastity punish me even more. I tried to stay still and enjoy my treatment. It was my first pedicure and Miss Olga was making my feet feel wonderful. Myra and Portia had trimmed my cuticles and shortened my nails to a uniform length. Then they started fitting some kind of plastic extensions to them and trimming them an odd cutter. They would match each finger to the others and then started putting some chemical stuff that really smelled on them. They told me that I was getting gel nail extensions, that they were really strong and last a long time. But I would need to get a "fill" every couple weeks. They were almost a half inch longer than my fingers when they were done. My fingers were then polished a deep pink, almost matching my bedroom, and had white tips at the end. They looked so girly and pretty I just loved them. Miss Olga was had finished painting my toes the same color without the white tip, and took a small black bottle and extracted a tiny brush. She told me to look away because she wanted to surprise me. When she said I could look I saw on my left big toe it said "Sissy" and on the left "Bimbo in small fancy letters. The black was highlighted with silver and a tiny crystal next to it. "Now every one can see what you are and every time you look down you will be reminded that you are not a woman or a man. Just a sissy Bimbo"' she said with a smile. I was released from the chair and led to another. It was lowered so my hair fell in a sink and Myra gave it a thorough cleaning. Soon in a hairdressers chair with a pink plastic smock fastened around my neck, Olga stood looking at my face for a minute. She took some equipment from a drawer as one of the other ladies pulled a scarf around my head and secured me to the headrest. I was turned away from the mirrors and when Olga turned to me with a tattoo gun. "I thought mistress Maddy said I wasn't getting tattooed Miss Olga?" "This isn't a tattoo gun sissy, its the newest technology for adding collagen to your lips. Maddy did say they needed plumping. Especially the upper one. What was the term she used? Oh yes, "Cock Sucker Lips", perfect for a sissy bimbo."! They all laughed as I sat there red-faced. My lips stung as Olga reshaped them. I couldn't see what it looked like, but it felt like they were 2 inches thick when she finished. "Don't worry they will feel almost normal by the time you leave, But now its hair time", Olga informed me. My head was released and my shoulder length hair was sectioned off trimmed lightly. Some kind of chemical was added, and after about 10 minutes I was led back to the sink and my hair was rinsed. I could tell it was now blonde but hadn't really been allowed to see it. Led back to the salon chair, Olga had wheeled over a cart full of rollers. She carefully placed what I understood were large rollers at the bottom and slightly smaller ones throughout the rest. I was brought over to a dryer, handed a copy of Allure and left. I couldn't see any mirrors so I just read for a while as Olga, Portia and Myra relaxed, occasionally looking over and laughing at me. The dryer turned off automatically and I was brought back to the chair, positioned of coursed not to see any mirrors. Olga removed the rollers and brushed out my hair. It tickled my neck and eliciting giggles from me. A knock at the front door and It was Miss Maddy, right on schedule. She came in and with a smile that would light up a room exclaimed to all "I love that color. She looks fantastic." "Do you like it Brenda?" "I haven't been allowed to see yet Miss Maddy" "Well take a look sissy" I gasped at the light blonde waves cascading to my shoulder. "Oh my Mistress, I look , I look , I look like a, a, a " "Bimbo is the word you are seeking", finished Miss Maddy. "Yes Miss, I look like a bimbo." Olga, I want to keep this color for her in the future. What is it called?" "That is Barbie Blonde dear, and it's always in stock." "How wonderful, goes perfect with her Barbie sheets", she laughed. I suppose the lips are a bit swollen still?" "Yes the will be her new normal in a couple more hours. Do you like them?" asked Olga " How could I not like them, they are just as we discussed. And the nail extensions and your Sissy Bimbo nail art are so perfect for her. Thank you so much Olga and you also Myra and Portia. You know I am having a Halloween pool Party on the 31st. I do hope the 3 of you will come. It will also be kind of an unveiling of our pretty Bimbo. "You couldn't keep me away Maddy, and I am sure they will be there too", she noted pointing at Myra and Portia. "Wouldn't miss it", they said in unison. "I will send her in for a nail fill on the 29th,, and she wont have her breast forms in then" Mistress teased. "Why not? asked Myra she looks cute with boobs. Halloween Pool Party Pt. 04 "Go ahead and tell them Brenda" Miss Maddy demanded. Trying to talk for the first time with my monster lips I said, "becauth Mithreth is getting me bweast impwants Thurstday to make me pwetty" I lisped as a full blush came to my cheeks. The all laughed at me and Mistress paid Olga handsomely and we headed out. It was only 7:15 so Mistress decided on a quick stop at Macy's. "You still need some make up Brenda." and she led me to the Cover Girl counter. The heavily made up beauty adviser asked what she could help with. Mistress told her that her sissy needed all new makeup so a full makeover was in order. Jillian told me to sit in a high stool that seemed to be in the middle of the store and studied my face. Trying to keep a straight face she asked Maddy what type of look she was going for?" "I think a club look would be best hun, something fitting for a man hungry bimbo" she told her. Then turning to me said that I better pay attention as I would need to be doing it myself, unless I wanted Olga to tattoo my make up instead." I cringed at that thought and decided to try and memorize what Jillian did. A small crowd gathered around as Jillian started in like an artist on fresh canvas. First a foundation applied all over and set with powder. I heard some bystander say loudly, "I hear that's really a man" causing a gasp from many that were watching. Eyeliner and eye shadow, and a plumping waterproof mascara were next. Some rouge to highlight my cheekbones and a bit of blusher, all claiming to be semi permanent, whatever that meant. And then a lip stain in a dark pink over my collagen cock sucker lips. Mistress was thrilled and gave Jillian a hug, then told her we will take one of everything including brushes and 2 of the lip stain along with a dark red one. Certainly thrilled with what her commission would be she said I would get 2 bonus gifts with the purchase, a make up bag, and perfume. She gave me a spritz of a perfume called "sissy" and placed the bottle in the bag. We hugged and after Miss Maddy paid we made our way home. To be continued. Halloween Pool Party Pt. 05 We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about my task. The new clothing would practically fill my closets and drawers. I carefully unpacked my new panties and bras and placed them in the drawers along with my skirts. I hung my dresses and night gowns in the closet and put my makeup in the bathroom. Finally a chance to take off the damned panty girdle that had been crushing me all day, I chose a pair of red open crotch panties, thigh high lace-top stockings, and a flared skater skirt with black 3 inch heels. On top I had a matching red shelf bra to hold my padded tits up and a sheer blouse that tied above my navel. My makeup was still perfect so I just touched up my lips and was ready to join my Mistresses for dinner. I had to pose for Miss Maddy and Miss Annie before I was handed an apron and told to serve them their meal. I was famished after a long day of shopping but was not allowed to eat with them. Instead I was told to crawl under the table and service them as they dined and enjoyed a nice steak and fine wine. I started with Miss Maddy, beginning with her feet. After a day of shopping they needed a good cleaning and I bathed them with my tongue and slowly made my way up her legs and thighs. The delicious aroma of her pussy was intoxicating me and I longed to clean her and suck on her beautiful lower lips. But it was not to be. She pushed me away and I moved to Miss Annie. She, had other ideas than Mistress and immediately pulled me up to her cunt and rode my face as she ate. I savored her taste as I was totally addicted to the taste of pussy. It drove me wild. I could lick and suck her all day. All to soon they finished eating and commanded me out from below the table. I was told to clean everything up and then I would find a salad and beverage for myself waiting in the fridge. After eating I was to join them in the pool room. I quickly cleaned up and found a scrumptious green salad with shrimp in the fridge and a large glass of juice. Well it wasn't really juice. It was a full glass of golden champagne from my owners. I savored it as I ate my salad, cleaned my dishes and wiped the table clean and headed to the pool room. Miss Maddy and Annie had moved the lounger to face the big screen TV and had some other equipment near by. I was directed to strip down to my panties and stockings and recline in the lounger. Maddy said the crotchless panty was a great choice as she wanted access to my caged clitty. I was told to bend over and my butt plug from the previous night was reinserted and inflated but not as much as last night. Miss Annie lit a joint and we smoked as Miss Maddy told be what was going to happen. "You will be here for quite a while so we will try to make you comfortable. We are going out for a while but can check on you by cam feed on our phones to be sure everything is OK." It was really good weed and we were all pretty mellow as Miss Annie attached some large cups to my chest with hoses attached to them. She flipped a switch on a box on the floor and my breasts were sucked deeply into the cups. After a minute the pressure released a bit then sucked deeply again. "The Dr. said will help stretch your skin and help your implants fit in you better"' she said. Miss Maddy then attached something to my chastity but I wasn't sure of its purpose. "I hope you are ready to enjoy a nice long movie tonight Brenda. You are going to be in this chair for a long time as we need to step up your programming my dear bimbo. You will not sleep. You will remain still and keep your eyes open. You will not be able to close them or look away from the screen, no matter how hard you try. You will love how it makes you feel. You will not look away. You will not sleep. You will love how you feel. You will not look away. You will not sleep. You will love how you feel." she spoke these words so softly to me. I felt entranced by them. Miss Annie was putting a hose of some type around my face. It was like an oxygen hose that you see people using that feeds directly into their nose. "As you will be here for quite sometime you may become thirsty. If you turn your head slightly you will find a straw to sip some water through." She touched the straw to my cheek so I would know where it is. "If you need to pee do not worry as there is a tube on your chastity to relieve yourself through. As I looked down I saw my feet with the message on my toe nails. "Sissy Bimbo" they reminded me. "We have a special treat to help you enjoy what you are watching. It will also help imprint the messages deep in your mind. Have you ever heard of "poppers" Brenda?" "No Mistress" "Well think of it kinda like laughing gas for sex. It will make you tingle all over and your sissy pussy will feel excited as you breathe it in. It will make your senses more acute to what is happening and make you want it that much more. And it will leave your mind helpless to resist the messages you receive". She turned a valve and I smelled something sweet entering my nose. "Take a nice deep breath of your sissy sauce Brenda", she whispered in my ear as I felt Miss Annie bind my wrists and legs to the chair. With the first deep breath I felt my body floating and my clit begin to harden. "That's a good girl Brenda." Mistress said in a soothing tone. "Let it envelop you. Let it make your mind a blank page. Accept that you will be a bimbo. Love what you are to become". And then headphones were placed in my ears, my Mistresses left, the lights went out and the TV screen came on. I saw beautiful girls on the screen, pretty, pretty girls, and they all had little clit cocks like mine and oh so pretty breasts. Some of there clits were locked away, some hanging softly. Words flashed across the screen but I could hardly read them they went by so fast. The girls were so pretty. More words on the screen. Then with the music in my ears was Mistress Maddy's voice. "You are a sissy girl. You love to be a sissy girl. Sissy girls don't have cocks. Sissy girls have sissy clitties. Breath deep. Again. You are my sissy now." I was floating as I felt a vibrator start up on my cage and plug. My cock, I mean clitty became hard in the cage. I could feel the spikes attacking it. I felt my ass trying to squeeze my pluggy. " You love being a sissy girl. You love to please. You love being a sissy girl." The pictures were flashing rapidly on the screen. Now there were pictures of cocks. Big and small but all of them hard. "You love looking at cocks Brenda. You will love cocks. Sissy bimbo's crave cocks. Breathe deep Brenda. Poppers take you deeper. Poppers make you want to suck mens cocks. Breathe deep." I tried to tell myself that I didn't want to suck cocks but the pictures were bombarding my mind. The sissies were sucking cocks and had big smiles. They were so happy so suck. I wanted to be happy too. "Sissies love cock. Sissies were made to please mens cocks. Sissies love the taste of cum. You are a sissy Brenda. You love cocks too. You love to suck a cock and please Mistress. You are a bimbo sissy Brenda. You will always be a bimbo. You will love to suck cock. Poppers make you want to suck" You are a popper bimbo sissy". The pictures just kept flashing in front of me. I could not help but get hard. The spikes were digging into my clitty and all I wanted was to feel them more. To feel them punish my clitty. I wiggled on my pluggy hoping my cock would get harder and force the spikes further into it. I was intoxicated by the poppers as my mind began to melt. More pics flashing. Pretty sissies sucking cocks, getting fucked in there sissy pussies. Cum squirting on their faces. Pussy asses left gaping as the cocks pulled out and moved to their mouths for cleaning as another cock filled there bottom hole. Pretty sissy breasts, large and bouncy and covered in cum. More tiny sissy clits. More sucking. More words flashing across the screen. Mistresses voice seductively talking me through it. "You are a bimbo. You love to suck and fuck. You must have cock. You must have cum. You love your poppers . You love cum. You need to suck. You need to taste cum daily. You live to drink cum. You are a sissy bimbo. You love to please men. You want cock deep in your ass. You cant resist cocks. You want to suck. You are a cum sucking Bimbo. You love to feel your useless clitty hurt. Its pain brings you pleasure. Its pain brings your owners pleasure. Your pain brings your master pleasure. You are a sissy bimbo. Your mind only thinks of serving and suffering. You were never a man. You are only a sissy girl. A bimbo to serve. You love cum. You want to please cocks. Cocks are as beautiful as pussys. You will serve all. Breathe deep Brenda ind tell us what you want. Breathe deep and proclaim your love of cum and cocks. Breathe deep and tell us you live to serve and suffer. Breathe deep and tell us you are a bimbo. You know this is what you want." I breathed heavily on loving your sissy sauce. Loudly you spoke. " I am a sissy bimbo, I want to suck for Mistress. I am a bimbo cock sucker. I want my ass filled with cock. I want to suck them clean. I need cum in my mouth. I need cum on my face and breasts and in my ass. I want to suck. I want to me fucked. I want my clitty to hurt for masters and Mistress. I am a sissy cum slut. I am a bimbo cock whore. I am a sissy whore. I want big breasts. I want to be pretty. I want to be a bimbo." The vibrator kicked up a notch and the spikes dug deeper into my clit. I breathed in more poppers and felt myself fully submitting to the pain. It felt so good to suffer and hurt. "I am a sissy pain slut. I want to please I want cock. I need cock to suck. I need to please Mistress. I need to pleasure cocks. I am a bimbo". The images kept getting faster before my eyes. I was breathing heavily lost in a trance. I drooled over the pics of cocks pumping sissy asses. Smiling happy sissy bimbos like me. Sucking on cocks sucking on pussies. Sissies tied to beds sucking cocks. Sissies tied to toilets sucking cocks. Drinking pee from cocks, serving cocks. Sucking pussies and asses. Faces covered in cum. More cum for sissies. Mistresses voice in my ear" Succumb to it Brenda. Be the bimbo. You love cock. You love pussy. You love to serve them. You are the bimbo. You love being a sissy bimbo. You love the pain in your useless clitty. You love having a useless clitty. You want do serve. You need to serve. You want to be a pretty sissy girl. You want to obey. You must obey. Your love cum. You want cum you love to taste it. You are a sissy bimbo. You will never resist. You only want to please cocks and pussys." I don't know how long it had been going on. I was so hot. My clitty wanted to explode but I knew it wouldn't in my chastity. By breasts were large and puffy from the pumps. The spikes were so hard. I wanted to feel them harder. My mind was adrift. Mistress Maddy and Miss Annie had returned to the house and were watching me live on their TV. 2 men were with them. Dr. Dane had returned with Dr. Atkins. "So what do you think of our pretty blonde sissy Dr's" asked Miss Maddy? "I wouldn't believe it if I wasn't seeing it", said Dr Atkins. "She will look lovely with her new breasts I assure you. Are you certain her programming is working?" "I promise you it is. In fact, we will join her soon and see just how well it works. I bet Thomas would love a chance to cum wouldn't you darling?" said Maddy as she stroked her hubby's cock through his pants, causing his chastised cock to strain in its cage. "She will be the worlds best bimbo when we are finished", added Annie, her breathing getting harder as Dr Atkins reached around her chair and gently massaged her breasts. "we should go in and see her soon. It was very early in the morning and the sun was starting to rise over the river valley as they quietly entered the room. The TV had turned off as had the music, breast pumps and vibrator. Sissy was lying in place staring at the blank screen. We heard her as we entered. " I am a sissy bimbo, I need to suck cock, I need to drink cummies, I want to be fucked. I want to be a pretty sissy. I need cum. I love cocks. I love cum. I want to lick pussies. I want to suck cock. I want to please Mistress. I want to worship cocks. I want Mistresses pain. I want to be a bimbo I will be a pretty sissy bimbo. Mistress Annie turned on the lights as Mistress Maddy gently brought Sissy's attention back to reality and released her bonds. Sissy stretched a bit after the long confinement and knelt and kissed her beautiful feet. Looking up he saw the two doctors standing with Miss Annie and a smile crossed her lips. "How are yo my bimbo?" asked Maddy. "I am fine Mistress I watched a nice movie last night." "Oh really sissy, what was it about? "Um, I don't remember Mistress" "That's OK sissy, I know remembering is hard. Is there anything you need right now sissy?" After glancing over at the doctors sissy looked at his Mistress and said. "Please Mistress I would like a cock to suck please Mistress." Mistress Maddy's face lit up like the morning sun and said yes my bimbo I would love to see you suck my Thomas' cock" She walked to her husband and told him to strip as she took the key for his chastity off of her necklace. She unlocked her hubby and said he would go clean up a bit first. "No need Thomas darling that's what our sissy is. Just have a seat on the lounger." "There you go sissy, your first cock" I was told to kneel and mistress held a small bottle to my nose and told me to breathe. The poppers put me in a trance where all I could do was lean forward and take the masters cock into my mouth. It was soft and warm and as I took it in I felt it start to harden and tickle the back of my throat. It tasted like a sweet cherry lollipop as I bobbed up and down on it. Sucking the shaft then running my tongue around the head. I couldn't get enough of it. I looked up at the Dr. as I sucked up and down, stroking the shaft with my hand. "Try to hold back Thomas said Maddy. I know its been a while for you but I want her to work hard for it Don't cum until I say or you will be locked back up I assure you." she said calmly, Knowing how difficult it would be for him. Especially the way Brenda was trying to devour his man meat. Dr. Atkins had taken down his pants and showed an impressive 9' cock. Annie rubbed some lube on it and stroked him till he moaned and led him over behind the cock sucking bimbo. "There ya go Dr., a nice virgin sissy pussy for your pleasure." Sissy moaned as she sucked, then wiggled her ass when she felt him pull out the plug. He slid in to her stretched bottom and started pumping as the two Lady's caressed each others pussies and watched their creation in action. Sissy increased her pace as her bottom was pounded, feeling one set of balls slamming against her bottom and another set on her chin. When Miss Maddy told Thomas it was time, Sissy felt the cock swell a bit in her mouth and the first stream of cum splashed into her throat. She sucked harder loving the taste and wanting to taste all of it. Thomas was bucking up and down as his pent up balls released more and more tasty cream into the sissy bimbos mouth, finally pulling out as the last bits splashed into her still made up face. Dr. Atkins was now ready to go as sissy's ass had clenched him tight as she thrilled to the taste of Thomas' cum. He soon let loose with a loud orgasm of his own deep in the sissy girls ass. He pulled out with a plop and demanded the bimbo clean his now dirty member. Sissy hesitated a bit but knew she must obey and needed more cock and went down on the dirty cock and sucked like it was a last meal. She soon had him hard again and kept stroking the fat cock as she brought him to another orgasm. Dr. Atkins wiped his spent cock on her face and said "what a good cock sucker sissy." Sissy sat back on the floor and said thank you for your tasty cum sirs. I loved sucking your cocks. Cummies taste so nice. I hope I have pleased you too Miss Maddy and Miss Annie." "Yes Brenda, you did a good job for your first time." "Thank you Mistress, I hope I can do it again soon the cummies are so sweet and tasty, almost as good as you Mistress." "Well thank you sissy, and yes you will get a lot more cocks to suck for us. Now you have had a long night and need some sleep as it is almost 9 AM. We are going to breakfast and have some planning to to for your breast surgery tomorrow. Now off to your Barbie Bed and get some sleep. "Yes Mistress, I am kind of sleepy. "Oh wait one more thing before you sleep Brenda" said Annie holding the now cleaned but plug. Lets put this back so you don't leak and cummies out on your pretty sheets." As I bent over she easily popped the plug back in and gave it a few extra pumps before removing the tube. I smiled and thanked her and headed to bed exhausted. Halloween Pool Party Pt. 06 I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets get you showered and dressed now". "Oh but Miss Annie, I had such a strange dream. It was almost a nightmare. All sorts of things were being done to my body, and then I was sucking men's cocks, and they fucked my ass and came all over me. And I was begging for more. And you and Miss Maddy just smiled and watched me and the Drs. kept calling me a bimbo. I was even smiling as they squirted their cum on me. Then some voice said I was a man and shouldn't do those things and I was frightened Miss Annie." I babbled on as she helped me out of bed and walked me to the bathroom. "Brenda you look in the mirror ant tell me what you see. Do you see a man's cock anywhere in the mirror?" "No Miss Annie." "Do men have pretty Barbie blonde hair like you?" "No Miss Annie." "And what about those pretty pink cock sucker lips? Do real men have pretty pink lips like that?' "Oh no Miss Annie, men don't have painted lips." "And look at your finger nails and toe nails Brenda. What does it say on your toes?" "It says Sissy Bimbo, Miss Annie. You could have read that," I giggled. "So are you going to believe a silly voice that says you are a man, or are you going to believe what you see Brenda?" "Oh you are so smart Miss Annie. I must be a sissy girl cause men don't look like me at all," I exclaimed as if I just figured it out. Miss Annie then reached around me and cupped my slight breasts in her hands and whispered to me "Yes you are a sweet sissy Brenda, and you soon be a perfect ditzy bimbo with the prettiest titties very soon." " Now lets remove your plug so you can shower. "She turned the water on nice and warm for me and I soaked a bit before lathering up with my pretty lilac soap. I used the hand-held to clean out my cage after squirting some soap in it. I shampooed and conditioned my hair, and then as I was washing my face off I opened my eyes and Miss Annie stepped in with me. She was totally naked and my heart melted as I gazed upon her beauty. I wasn't sure if its because I loved her and Miss Maddy so much, or because I wanted to be as pretty and smooth as she was. She attached a long tube with a nozzle she had brought in with her, to the shower. After pulling out the drain stopper she told me to bend over and started working the nozzle into my bottom. She would take it out and let me release and then did it a couple more times. As if I wasn't feeling the spikes just from seeing her luscious body, now it really started to hurt. She finally stopped and told me, that was to teach me how women clean up after a good fucking. We got out and she brushed out and blow dried my pretty blonde hair and helped me touch up my semi permanent make up. "You need to look pretty because Miss Maddy has a visitor coming over this evening. We want you to make a good impression Brenda. And remember too, that tomorrow you get your pretty new breasts sissy." "Oh Yes Miss Annie, I cant wait to see how pretty I will look," Can I wear a sexy dress too?" "Certainly Brenda. Now let's go pick something nice for you." and we headed to my room. "Lets start with a pair of those pretty crotchless panties again, you look so pretty with them. Maybe the pink one's today for my little girl, and matching pink thigh high stocking with the little bows at the tops. Oh you do look delicious like this baby girl. And these pink ballet flats I got you will look adorable too. I am really liking this little girl look on you, so no bra tonight. Lets try this little ruffled blouse and this pink satin dress with the black petticoat under it. Oh that gives my little one such a naughty look" "Oh Miss Annie I do look so pretty like this, thank you so much for dressing me up. "I'm hungry can we eat soon Miss Annie?" "Yes my darling little girl. Let's go and see if our guest has arrived and then we will eat." Miss Annie said treating me more and more like a child." Miss Maddy had of course been watching all of this on a large screen TV in the main house while Dr. Dane massaged her feet. Dr. Atkins was seated next to her and she was rubbing his crotch as she enjoyed her husbands efforts. As Miss Annie brought me into the room and I saw the 2 doctors with Mistress Maddy, I hesitated and pulled her hand to stop her. "Is something wrong sissy" prodded Miss Annie. "Miss Annie, those are the men from my dream that were fucking me and cumming on me Miss Annie." Everyone in the room laughed and Miss Annie told me everything was ok. "You are right Brenda, but it wasn't a dream, sweetie. It was very real. You can even watch the video if you like. You really did beg to suck them and fuck them and drink all their cummies. And that voice you heard saying that real men don't do those things is because that was a tiny piece of your old brain trying to reach out to you. But Miss Maddy and I won't let that happen anymore so you will be safe from those voices. But you know sissy, once you were a man and wouldn't have done those things. But now that you are a pretty little sissy bimbo its perfectly alright to suck them ok? "I guess so Miss Annie." "That's a good little girl, now go do a twirl for them and show them how pretty you look." "Oh yes Mistress." and I danced in front of them so my dress flipped up to show my pretty panties. They all clapped and said what a good little girl I was. We all went to the dining room and there were only 4 chairs at the table. "Where is my seat Miss Maddy?, I asked with a pout. "I want you under the table right between my legs baby girl. I will let you lick me while we eat and then you may have dinner after we are done if you are a good girl. When you are done with me you can lick the doctors and then Miss Annie to, but only if you promise to be good or no dinner for you after." I crawled under the table as instructed and started to lick my owners beautiful pussy. It tasted so wonderful. I immediately felt my spikes doing their job. It made me lick and suck her heavenly juices until she came all over my face. It smelled and tasted so sweet. I so wish I had a pussy too. She pushed me over to Dr Atkins and his man cock was pointing at my lips. I knew I had to obey Miss Maddy so I took him in my mouth and ran my tongue around the large head of his cock. I felt him harden and and started to take him deeper. As I got it all in my mouth he held a bottle of poppers by the base of his cock. Every time I went all the way down on it I got a strong sniff of that sissy sauce. I was soon reliving the previous nights training and getting more and more excited about sucking on his cock. Even after he removed the bottle I continued sucking and licking and teasing his balls. "That's right little girl, just pretend its a sweet lollipop and lick it up and down. Yes Brenda, just like that. Oh yes. Baby girl is gonna get a nice mouthful of cummies for dinner." Dr. Atkins cried out as I spurted over and over into my mouth. I moved next to Dr. Dane and treated him much the same. As he was about to cum Miss Maddy told me to stop, as her hubby hadn't earned it yet. "I said I wanted more cummies but she wouldn't let me. At least I would get to make Miss Annie cum and I really loved to taste her. She was so wet when I got to her she only took a few minutes to flood my mouth and face with her lady juice. I was told I could now sit at the table and eat my dinner then clean up the dishes as the "adults" retired to the living room. I finally finished cleaning everything and went to the living room. They were all talking when I got there and all of a sudden the doorbell rang. I was told to answer it and I opened It to see a rather handsome young man with a large briefcase. He said "Hi, I'm Mike Pierce, and I am here to see Maddy. I invited him in and for some reason found myself staring at his crotch as I pointed to Miss Maddy and said "she right over there." Maddy stood to greet him then turned to me and asked what I was staring at. "I was just letting him in, I wasn't staring at anything." Now Brenda, don't try to lie to Mistress. Tell me what you were looking at." I was, I , I was looking at his crotch Mistress", I said feeling embarrassed from being caught. "Well there may be a punishment in order later for a lying little girl, Brenda. "Yes Mistress Maddy, I'm sorry Mistress. It's just that sometimes I forget things lately, I don't know why." "I am sure you do Brenda, I'm sure you do," she smiled knowing how well her programming was working. Turning to her husband and Dr. Atkins she said, "Any doubts about my programming methods now boys" with a smug smile. The men just laughed a bit and Mistress went on to introduce Mike as I fetched drinks for everyone. Mike was highly recommended professional piercer, hence his name. They talked briefly of what they were going to do that evening and Dr. Atkins was quite interested in hearing it. He even described an additional treatment that he would be able to do after doing my implants. I really couldn't follow much of what they said. Miss Maddy arose and said she needed me to do something. "Do you want me to suck his cock too Mistress?" I asked with a little curtsey. "That's not what I had in mind Brenda but I bet Mike would enjoy that," she said "Yes I surely would," Mike said, "but after my work is done." Miss Maddy excused herself and led me down the hall to a room I had not been in before. It looked like a medical exam room. She explained that Dr. Dane used to see patients at the house. She told me to take off my dress and blouse and sit up on the exam table. I complied without hesitation and soon found my self bound to the table with my feet up in stirrups raised higher than my head. "Mistress are you going to fuck me like this" I asked. Mistress jokingly told me "don't go anywhere sissy" With that she left the room and returned shortly with the other 4. "Now missy, its time to unlock that sissy clit of yours". She pulled her key from her pocket and removed the spiked chastity from my sore clitty. Miss Annie stepped up with a warm wet cloth and cleaned me thoroughly as Mistress Maddy said that Mike needed to check some things with my clit before we proceeded. Mike opened his brief case but I couldn't see what he had in it. He was holding my clitty down between my legs, stretching it towards my ass and popped my sissy eggs up in side me. He made some marks on my taint with a sharpie and then a couple more con the end of my clitty. He then looked closely at them and said they would be no problem. Mistress stepped up and stroked my sissy clit until it rose to its full 6 inches. The tiny spike marks were visible all around. "Sissy you did something that earned you a punishment didn't you?" "Yes Miss Maddy, I told a little fib before." "What was it about sissy?" "About my looking at Sir Mikes' crotch Mistress" "Do you like looking at mens cocks and crotches sissy?" They all watched as a slight bit of resistance left in me tried to form the word no, but all that ended coming out was" yes Mistress I like looking at pretty cocks." Still stroking me slowly Mistress asked Miss Annie to bring her a riding crop. "Is this a cock I am holding Brenda?" "No Mistress, that's a sissy clittie." "And this sissy clitty is going to be punished for lying about cock little girl. I expect it wont happen again after I am done." She took the crop from Annie and I felt the first strike on the tip of my clitty. Then holding it by the tip added 5 more hard strikes up the tender bottom of my clit. I was howling in pain and Annie warned me to be quiet or I would get double the amount. I immediately stopped making noise but the tears were falling from my eyes as Mistress continued with my punishment. 5 on the top, 4 on each side and the hardest of all on my balls causing me to cry out. I tried to reach for them to try and ease the pain bough was securely bound. "Well you just earned another 20 by crying out sissy, I will let Miss Annie administer them in a minute. First I will stroke you up nice and big again so she has a better target." Her hand felt so soft and loving now that I couldn't help but to get a little stiffy. Mistress Annie stepped up and said. "You know I am really going to miss doing this in the future so I am going to make it worth while this time" She would follow the same pattern as Mistress Maddy. The first on the head was twice as powerful as Maddy's 1st blow. The rest were as well and though crying inside I knew I had to remain silent as I felt the last blow on my sissy eggs that almost caused me to pass out. A cool cloth on my forehead helped revive me as Miss Annie caressed my sore eggs and licked my clitty, restoring it to its previous stiffness. "Do you remember when you got to lose your virginity in Annie's beautiful pussy last week sissy. I know you do. Wasn't that the most wonderful feeling you ever had?" teased Mistress Maddy, as Annie continued to stroke and lick me. Would you like to feel that good again?" "Oh yes, please Miss Maddy, that would be wonderful!" "Yes it would Brenda, but sissy's don't get to enter vaginas and I promise you that you never will again. But I know you used to love stroking it so maybe will make it squirt that way one last time, because it may not do that anymore either." Mistress Annie was keeping me on edge as Maddy spoke. This one last time to squirt like a man. To feel that wonderful orgasm one more time. That excites you doesn't it sissy, knowing I won't ever let you do this again?" "Oh yes, I think, but maybe I shouldn't, I mean I don't know Mistress. I'm so confused. I wanna squirt but sissies aren't supposed to squirt. And cumming is for real Ladies and men Mistress. I don't know what to do. It feels so nice, I wanna squirt again but I want you happy mistress. Please decide for me Mistress, It's so hard to think about. Mistress nodded at Annie and she shoved a finger in my bottom, hitting on my prostate and my cum started leaking out with out an orgasm. With an evil laugh Mistress said "now we can continue the party." Miss Annie poured the cum into my mouth and wiped me clean. Mike stepped up asked Mistress if she wanted a PA piercing, or an ampalang, explaining how it would go sideways through the clit head and would offer more security. Miss Maddy though a bit and decided on the PA because che liked the look and that it could be a smaller ring. Mike showed her his new design of permanent piercing ring. "For the breasts I recommend a 10 guage but for this an 8 will be heavier and better. He continued by showing how the ends are reverse threaded so when twisted into place it would pull both ends together inside it. They were gold plated titanium, and could not be cut. He cautioned that if he put the sealer on the threads it would be a lifetime sentence. I could see in Mistresses eyes that this excited her no end. I swear I cold smell her woman scent coming from between her amazing legs. I cas her toy and she wanted to play. Mike said he was ready and Dr. Dane stepped forward and I shrieked a bit as he poked me with a syringe and I slowly felt my cock head and perineum go numb. Mike placed a pair of forceps in position and Miss Maddy held them for him with a huge smile on her face. My view was blocked by my petticoat, and all I felt was some yanking and pushing as Mike shoved his large needle through my taint. The ring was put in and the forceps released. Miss Annie then held a mirror and demanded I watch as my sissy clit head was then pierced in the same manner. I watched as the single ring was then slid through my clit head attaching it between my legs and Mike srewed the ball in place. "How does that look to you Maddy?" asked Mike. "I love the look . Its perfect. Look how flat she is when I tuck her sissy eggs away." She was right. It did look smooth and pretty. I couldn't believe this was happening to me. But it really was. "Mike, that is so right like that. Please unscrew the ball and put the permanent sealer on the threads." "Would be happy to do that for you Maddy." I watched as he sealed me shut forever. A tear rolling down my face as I knew I would never act as a man again. Mike moved to my chest and less than ten minutes and a couple of yelps later I had matching rings in my tits as well. Dr. Atkins examined my crotch and spoke to Miss Maddy. "With her eggs tucked up I could fold this excess skin from her scrotum over the top and stitch it to look like outer labia lips. It would give her a bit of a camel toe and insure that her eggs wont appear again either. I can do that when I finish her breasts tomorrow." "Oh that would be an awesome look for her doctor. She will forever be nice and flat, almost like a real girl. And, we no one will even notice there is a sissy clit left under it. It may make it difficult for her to rub it and squirt but I think that will be ok." Mike the jewelery is just plain beautiful. Her new breasts will look so much better with the gold rings too. And knowing she is locked permanently will be so humiliating for her. I really cant thank you enough. But I know someone who can thank you. Lets untie our girl so she can give you that blow job she promised." Everyone got a laugh at that and Miss Annie untied me and had me on my knees. With a little prodding from her boot I sat up and said "please Sir Mike may I suck your cock to thank you for piercing me sir. I want to make you feel as good as you made Mistress feel by taking my clitty away. Please sir?" He smiled down at me and dropped his pants. I leaned forward and took him deep in my mouth and sucked him into my throat. I bobbed up and down as I felt the Novocaine wearing off. My clitty tried to get hard as I sucked and moaned savoring the taste of his cock and soon had a mouth full of cummies. Mistress told Mike he was welcome to come by anytime for a repeat performance by me. As he packed his tools up Dr. Atkins came over and filled my mouth with his cock and Dr. Dane, with Miss Maddy's permission took be from behind. I was spit-roasted and worked both ends as best I could bringing them both to a quick orgasm. Annie stuffed a tampon in my bottom so I wouldn't leak. Mike was on his way out. Miss Maddy told Annie to put me to bed before joining her in her bed. The Doctors went to their rooms as well. It had been a long day. Annie made sure I was ok and tucked me in saying, "you were such a good little girl sissy. Mistress and I both love you so much for becoming our baby girl. Life is gonna be so much more fun know." With that she put my headphones on me , turned off the light and left for Miss Maddy's bed. I fell asleep listening to music and wishing I could be there licking them both to climaxes. Halloween Pool Party Pt. 07 I was allowed to sleep in late the next morning. Probably so there was time to get the medical room set up for the day's events. When Annie came in to get me up it was past noon. I was allowed a couple sips of water but that was all. My nipples and crotch were sore and that was to be expected. I couldn't see my sissy clit pulled back snugly and permanently between my legs. Annie helped me into the shower and stripped and climbed in with me. After washing each other's body. I was allowed to kneel and lick her beautiful pussy as the warm water cascaded over us. While hugging before stepping out she whispered to me how much prettier I looked now and how she could hardly wait to play with my new breasts soon. She dressed me in a lace black and red night gown that barely reached my thighs, a pair of feathery open toe mules and nothing else. I was led to the exam room where the doctors were waiting for me. Dr. Atkins had me standing while he examined my chest again, using a marking pen to outline where his work would be done. He explained the procedure thoroughly to me and said that Dr. Dane would be handling the anesthesia and assisting him. Miss Maddy had told me that Dr. Atkins was known to be one of the best "breast men" in the city and that I was in very good hands. The Dr. also explained he would be placing the implants from the side through my armpit so no scars wouldn't show after healing. He said what the healing time should be and what I should expect. I was informed that I would spend at least 2 days in bed and bandaged and he would leave some pain medication with my owners. When he was done he went to wash up as I was placed on the exam table and secured as Dr. Dane started an IV drip in my arm. I counted backwards from 100 and didn't get too far before waking up in my bed with a throbbing pain in my chest, neck, face and and crotch. As I awoke Annie and Maddy were sitting beside my bed. Annie told me not to talk, removed the seemingly ever present headphones, and fed some ice chips. Miss Maddy asked if I was in pain and I nodded yes. She released a bit of liquid from a separate tube into my IV feed and the pain started to subside. I saw what looked like two mountains on my chest and could not see past them. "We will show you a video of the operation when you are more awake Brenda, but I want you to know it was a huge success. After finishing with your new breasts, Dr. Atkins did a bit of a tracheal and vocal chord shave. Your voice should be a bit higher in tone when you can speak again but please try not to until tomorrow at least. Annie and I can't wait to hear it either." Maddy informed me. "We also decided to fix your nose a little, not too much but he did thin it out a bit. Finally he tucked your sissy eggs up into their sockets and stretched your scrotum up and over your sissy clit and made it look like outer labia lips like we discussed previously. I'm sure that as your brain capacity has faded a bit since this whole adventure started and you may not remember that discussion. But, for a few days you are not to try to rub your clitty, and after you are up and about again you could wear your panty girdles with a nice thick soft maxi pad inside for comfort." Thanks to the painkillers I was drifting back to sleep and felt them each kiss me on the cheek as they left. Late the next afternoon I finally saw the video. It wasn't that exciting I thought. Glad I slept through it. The following morning I awoke to Dr. Atkins voice. "Well sissy its time to take your bandages off and get a shaping bra on you, he told me. After first removing the IV set-up, he unwrapped my chest and I saw 2 pretty and perfect D-cup breasts stretching up from my chest. "Be gentle, but you can touch them if you like." I reached up and felt my breasts for the first time. The first touch was electric and felt like it touched a chord all the way to my sissy clitty. I let out a soft shriek and everyone laughed at my new higher pitched voice. I couldn't believe it myself. "Oh My" I cried out, "is that really my voice? I sounded like a little girl. "I love it!" said Maddy it's a perfect bimbo voice for Brenda. Dr. Atkins has done some wonderful things for you because he is a friend of mine. But I think as a bonus for him he will have full use of your mouth and pussy whenever he wants for at least the next 2 years. That's fair don't you think?" And in my new sissy bimbo voice I squeaked, "Oh yes Mistress, I love his pretty cock." Miss Annie then fitted an industrial looking support bra on me and got me out of bed. She said I needed to get my legs moving again and get some food in my belly. The others quietly left and Annie assisted me in eating and I went to rest a bit. After all we did have a big party coming up and I need to get my strength back. Annie said she and Maddy could hardly wait to get their mouths on my new breasts. Halloween Pool Party Pt. 08 Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and could not feel anything through my girdle, well-padded with a thick maxi pad. I felt so smooth and pretty. I laid back and enjoyed their ministrations with a huge smile on my face. "Told you we couldn't wait to do that sissy," any stated with a big grin. "does it feel good baby?" "Oh yes yes Mistresses. It feels like high voltage shooting through my body. I love it. My clitty was trying to get big too" Miss Maddy was so thrilled with my new voice she teased my breast even more just to hear me moan. She was so excited that she hopped on the bed and lifting her short skirt straddled my face and lowered her luscious ass to my mouth and started fingering herself as Annie continued to massage my breasts. The stimulation was almost too much for me and I pushed my tongue deep into her bottom hole wanting nothing more than to please her. She squeezed her thighs hard around my face and I soon felt her juices flowing onto my face as she screamed out in orgasmic bliss. Annie helped Mistress off of my face as I cried out for more. That didn't take long as Annie then hopped up and lowered her pussy to my face and rode me through a loving climax of her own. Maddy said she had things to do and Annie would be helping me with the party decorations, and she left us alone. After straightening her clothing Annie helped me out and took me into the bathroom to clean up. With all my bruising healed up I finally got to see myself in the mirror. My breasts were so perfect. I had no adams apple showing, and my nose was thinner and had a tiny little up-turn at the end. My oh so plump cock sucker lips had me gasping as I wondered if it was really me. I cleaned my face and Annie watched as I tried applying my makeup. I could hardly remember how the lady at the store told me how to do it, and Annie was annoyed with how it looked and made me do it again. "It's so hard Annie. I am really trying, honest I am", I almost cried to her. "I know you are sissy, but if you can't get it right it will be back to Lady Olga's to have it made permanent, ok?" "Yes Miss Annie" We had a small breakfast and I asked Annie for my girly vitamins. She said I didn't need them now as Dr. Atkins had given me a shot that would last 6 months and keep me full of special the hormones to make my breasts grow even bigger. "But they are so big already Miss Annie, I can't even see my feet anymore." "Yes and they look fantastic too sissy. Tell me darling, did you mother have big boobies?" "Yes Miss Annie, why did you ask?" "Well if hers were big, then the hormones will really make yours bigger. Maybe even a G-cup by the time you finish filling out darling. You will look so beautiful. Everyone will love them. And the guys will just love to put their cocks between them for a titty fuck." "Do you really think so Miss Annie?" I don't just think so Brenda, I can promise it." I just giggled at that, and then giggled some more hearing my new voice. I could hardly believe how I sounded now. It will take a while to get used to it. Well let's get to work on decorating this place. She opened up boxes of Halloween decorations and instructed me where and how to hang them. I never could have figured it out for myself. But some little voice told me I used to know how to do it. It took most of the day, but when we were done the room looked great. There were spider webs with huge spiders all around, and scary witches and goblins that would jump out at you. Vampire bats hung from the rafters. There were a couple of dead bodies floating in the pool and blood stains all over. It was totally terrifying. And we were finally finished around dinner time. Maddy returned with Her and Annie's costumes and food, drink and treats for the party. I put it all away and then we fired up the grill and cooked steak and veggies for dinner. As they wanted my strength to build after all the medical procedures I was allowed to eat with them. It was all so good. We enjoyed some wine and Miss Maddy turned on the TV. "Look Brenda, do you see that young man in the video. He was supposed to be cleaning his bosses pool," said Maddy. "Is he cleaning it in the picture Brenda?" Look at him as he picks up that pretty yellow bikini for the first time. He is certainly being naughty. That's not something a young man would do is it?" "No Miss Maddy. He should be doing his work." "And look at him now. He actually licked it and now he's even trying it on. What a naughty young man. Or maybe he isn't a young man. Maybe he was pretending to be a boy, but was really a sissy all along Brenda. What do you think?' "I think he was being bad Miss Maddy. He should have been working cause he would get in trouble for sure Miss Maddy." "Should his boss have fired him, or just punish him. What do you think Brenda?" "Well if he was a good worker maybe he should just have been punished a little." "Go closer to the TV Brenda, and see if you recognize that naughty boy. "Maybe he should be made to wear pretty sissy clothes all the time. Do you think that would be a good punishment Brenda dear?" "Hee hee hee, that's funny Mistress, he would probably be so embarrassed if you did that." "What if we made him into a mindless little sissy bimbo Brenda? Would that be a good punishment for playing with his bosses bikini like that and squirting his cummies in them?" As Brenda got closer to the screen something clicked in her weakened mind. "Oh my goodness Miss Maddy that was, that's, that boy, that was me Mistress?" "Yes Brenda, my little bimbo. That was you. And that's why I made you our bimbo. And now look at you, a pretty little bimbo because you were too weak to resist the pretty yellow bikini I left out for you so many weeks ago. And, like you just said yourself, he did need to be punished didn't he. Are you happy with how your punishment turned out sissy. "Yes Miss Maddy, I'm sorry I did those things in the video but I just couldn't stop it. I didn't think I would end up like this, but I know it is best for me Miss Maddy. I love being your and Annie's little girl Mistress. Please don't show anyone that video Mistress. I don't want people to know I was a naughty boy." "I can't promise that Brenda. I may have it playing during the party tomorrow. And if I do, well that is up to me not some little sissy. Remember that." "Yes Miss Maddy." "Annie dear, before we leave her for the night, please get her pluggy ready. I think we will leave her on the lounger tonight with a nice stretched bottom and that fun cock training tape she watched the other night. I will set up her breather tube for the poppers so she will dream of cock all night" "But Mistress please don't you have a nice pussy training video instead of all those cocks?" '"How sweet my sissy but we know you already love pussy. We just need to help you love cocks more too. I do love watching you suck and fuck them. Annie and I certainly don't want to bothered with them anymore. That is your job now, and after tonight you may never have enough" she told me with an evil laugh. Annie had me bend over and forced the plug in my ass. It was pumped more than I had ever felt before. I was quickly bound to the chair and with the poppers and headphones started, the video changed. 'You are a sissy cock sucker. Poppers help you love cocks. Breathe deep Brenda. Feel your mind fill with cocks, your mouth loves to taste cum. You want to suck for Mistress. You want to be a dirty popper slut. You want to feel cocks fuck your dirty pussy. Your cock sucking lips feel so good wrapped around a big dirty cock. You want to suck cocks clean after they fuck you. You must please Mistress Maddy. You must please Mistress Annie. You must suck cocks. You love poppers because they make you want to suck more cocks. You want to suck cocks for Mistress. You are a cock whore for your Mistress. You love the taste of cum. You want to make men cum. You are a sissy forever. You will always suck cocks for Mistress. This would continue all night. It never stopped. It never changed. Pictures of pretty sissy girls sucking and fucking flew through my mind all night. I couldn't think on my own. All I could think about was being a pretty cock sucking sissy. In the morning my mistresses returned, turned off the TV, and released me from the chair. I immediately knelt and kissed their feet. Thank you for loving me my Mistresses." "You are so welcome sissy. Would you like to do anything special before the party today Brenda?" "I want to suck cock for you Miss Maddy." I begged. "How sweet Brenda," she said with a knowing smile towards Annie, but I think that will have to wait until the party. Now go shower up and take a nap in your bed after putting this equipment away. We will wake you for dinner and then get ready to greet our guests. I woke up around 4 and put on a pretty gown, then met my Mistresses in the kitchen for a light dinner salad with some wine. Annie discussed with mistress how I was having problems with my makeup came in and worked on my makeup for me. After thinking about it for a bit Miss Maddy spoke up "Brenda, tonight I want you to ask, no, I want you to beg Miss Olga do permanent makeup for you when you are at her salon next time baby. Do you understand?" "Please Miss Maddy, I will learn how if you give me some time." I replied, then barely heard her say the word "Fortress". I immediately doubled over with pain in my sissy eggs. I reached down to sooth them and could not find them anywhere. I was sobbing softly when I turned to Miss Maddy and begged her, "please Miss Maddy I will beg her in front of everyone for you. I will beg to have my face look like a pretty girl for you always Mistress." "Yes you will sissy. And in the future your answer will always be yes when I command something wont it?" "Yes miss Maddy, always." "I need to get ready sissy. Miss Annie will get you ready and then you will put out the food and greet our guests as they arrive." "Yes Mistress." With that, she left the room and I cleaned up the dishes. I then followed Miss Annie back to my room and she started on my makeup. When she had finished I had dark "little girl" pink lips, glittery purple eye shadow, bright pink blusher on my cheeks, and 2 pretty pink bows in my Barbie blonde hair. After finally removing my pluggy, (yes from last night) She then had me wear pretty pink panties with lots of lacy ruffles across the seat. There were so many ruffles you could hardly tell there was a hole exposing my sissy pussy in the back. I loved how they looked so pretty and flat in the front with just my newly made pussy lips pressing against the soft fabric. A matching pink shelf bra held my pretty breasts up for all to see. I was then given a soft white apron that hid almost nothing and pretty sparkly pink open toed pumps with 4 " heels. "Aren't you glad you don't have to wear some silly costume tonight sissy?" said Annie. "But isn't this a costume Miss Annie", I asked with a frown. "Sissy, if I put you in a man's suit it would be a costume." Then motioning towards me with a sweep of her upturned palm she continued, "this is your new normal. Her laughter seemed to fill the pool room as it brought even more pink to my cheeks." Now go get working on your chores. I headed to retrieve the food platters from the kitchen fridge and set the buffet table with napkins, utensils and condiments. The beer cooler was stocked, and plenty of wine and drink was available for the guests, as they were now arriving. I curtseyed as I led them in and hung their coats. The costumes ran from the usual, like Dracula. and his bride, wonder woman and Batman, to the bizarre and sexy. Like sexy red riding hood and a man in a leather body harness and ass-less leather chaps. Oh my that is Dr. Atkins in the chaps I realized. Next 2 cheerleaders entered with a handsome football player. On closer look I realized it that the football player was Lady Olga and Myra and Portia were the cheerleaders. Olga said she was looking forward to playing ball with me later. There were about 30 guests present when the lights dimmed slightly and in walked the most beautiful "Wonder Woman" ever. Miss Annie looked so awesome I knelt at her gold booted feet and kissed them. She stood in the center of the room and having everyone's attention said " And now please welcome your hostess, Miss Maddy Dane. Everyone applauded as Miss Maddy entered. She was dressed as a "Huntress" in a wild green and black leather top that accentuated her best assets. Skin tight leather pants and short boots. She had a bow with arrows in a back quiver, A sword at her side and daggers hanging from her belt. Also hanging from her belt were 3 scrotums and balls (like the ones rednecks hang under their trucks) that appeared to be dripping with blood. She looked so amazing, and I am certain it put a scare into many of the male guests as many of the woman were elated with it. Oh, in her hand was a leash leading her husband on all fours, in a full leather body harness and chastity cage on his cock. After greeting everyone and having a few drinks the buffet was opened and the attendees all ate dinner. As they were eating Miss Annie turned on the TV so all could watch my transformation from pool boy to bimbo. As the guests finished eating Miss Maddy arose and spoke to the gathering. "I do have some special announcements." First costume prizes for my friends. Best female costume goes to Little Red Riding hood. She handed a nice vintage wine to her old college girl Leanne. The best male costume must go to Dr. Atkins for his sexy leatherman. He received a bottle of Johnny Walker Red. And the best costume for couple of more goes to the football player and his cheerleaders. Mistress was handing them each a gift-card when the footballer said, "I would rather get to use Brenda, Maddy. "Oh don't worry you will get that too, and so will everyone else that wishes to use her tonight." I tried to count how many were attending but somehow I just couldn't seem to count so high. "As tomorrow is also Miss Annie's 35th Birthday, Brenda will be taking her birthday spanking for her. And I will be picking 3 guests to help give it to her. And don't worry those chosen will all get to give her 35 each." Now as you know this is also Brenda's coming out party in a way. She is now a full fledged air headed Bimbo to serve and please. You may have seen how she started and how she became a bimbo on the TV screen. Some of my guests have played a role in this including the wonder and handsome Dr. Atkins, my husband, and Olga and her crew. Do you have something to say to Olga sissy?" I took off my apron and moved to the center of the room and knelt down in front of Olga in her football costume. I kissed her feet then looked up batting my eyelashes and said, "Miss Olga, will you please give me permanent makeup when I visit your salon again. I'm can't seem to remember how to do it right all the time and need to look pretty for Miss Maddy and Annie. Please Miss Olga." I kissed her feet as she assured me she would take great joy in it. And isn't there something else you wanted to say to everyone Brenda", asked Miss Maddy. "Something Annie taught you maybe. I stood in my pantie and bra with everyone looking at me and recited a verse similar to the child's song, "I'm a Little Teapot" in my new high pitched voice: "I"m a little sexpot, I have no spout. I used to have a handle, but I won't pout.When you want to use me ya don't have to shout. Just bend me over and I will suck your cummies out." "I must have done a good job because everyone applauded for me. I turned so red from blushing. And I smiled and curtseyed to everyone. Mistress patted my head and called me a good little girl then led her hubby over to a hook in the wall and attached his leash to it. Meanwhile Annie had "Batman" help her move a bench to the middle of the room. It didn't take long before I was secured to it with my panties drawn down and a chin from one nipple ring to the other passed through the wooden frame. I wouldn't be moving for a while. Miss Maddy stepped in front of me and announced she had a present for her sissy. She held up a clear rubber looking tube and called it a "tunnel of love". Showing the room she showed how the almost 2' diameter tube could not me squeezed any smaller than it was but easily stretched out quite wide. Almost double its current size in fact. She spread what I thought was a lube on it and started working in into my bottom hole. It soon popped into place and I could feel how wide it stretched me. In five minutes the fixative will cure making it permanent inside her" she told the gathered guests. She will always have easy access now. Then after Annie's birthday spanking she will be open for business, so to speak." Everyone laughed and Annie approached with her favorite paddle. A cock gag was placed in my mouth and the paddle struck hard and often on my ass. Everyone sang Happy Birthday to her as she laid 35 hard ones on my sissy ass making it glow bright red. Miss Maddy stepped up next and with her favorite rattan cane added 35 stripes to it. I was crying into my gag and tears rolled down my cheeks but the gag kept me silent. When she had finished 3 guests took their turns at my ass. One with the crop, another with the paddle and the last with a very strong hand. The gag was removed and Miss Annie wiped away my tears and kissed me and thanked me for taking her paddling for her. She then held some sissy sauce under my nose and told me to breathe deep asking me what I wanted. She of course knew what I would say after that and she was right. "Please Miss Annie I want cummies, I want to suck cocks for you and taste there cum. Dr. Atkins was behind me in a flash And I felt him shove his 9" cock into my ass. He slid in through my "Love tunnel" with no resistance and pounded hard. I felt his cock just barely brushing the head of my locked clitty as he thrust. It made me squirm on him and just before he came a cock entered my mouth. I has helpless to resist but wouldn't anyway. I just wanted as many cocks as I could get. Miss Maddy then dragged her hubby over and told him to suck Batman's cock. His first refusal brought a quick slash with her cane. She told him to look at me and try again knowing what she is capable of. "Do you ever want that chastity off Thomas?" "Yes Mistress, Please Mistress, I will do as you ask," he begged and crawled over to the Batman. "Please Batman sir, may I suck your cock?" With a nod Batman opened his pants and the doctor, on his knees, sucked it deep. "You may not cum in him Batman. That gets saved for sissy Brenda." The Dr. got him right to the edge and as he was ready to shoot his load he turned and sprayed it all over and in the bound bimbos mouth and face. Miss Maddy told her hubby to stand and unlocked his cock cage. "Mouth or ass" she asked him. "Ass please" he said and she led him behind me as another cock filled my mouth. After I think all the men had cum twice Mistress asked how I felt. "Thirsty Mistress" I replied. A funnel gag was placed on my mouth and Mistress Maddy stood over it and filled it with her golden champagne. I savored her treat and was soon taken off the bench and laid on the couch. Miss Annie sat on my face and I serviced her ass with my tongue as the football player removed her pants revealing a 12"x3" dildo. As I sucked Miss Annie, Miss Olga lifted my legs and positioned the giant strap on at my bottom hole. One quick thrust and the tunnel stretched out allowing her to impale me fully. I cried into Miss Annie's ass. I drove my tongue deeper as Miss Olga pounded me. My clitty head could definitely feel her cock thrusting and pulling back, and thrusting again. I was on sensory overload when she finally pulled out after having had 2 orgasms from the end hidden in her womanhood. Miss Annie came as well and as she rose off of me Mistress Maddy climbed aboard. Halloween Pool Party Pt. 08 I could never forget her wonderful taste and licked her pussy lips and and gently sucked her clit. One by one our guests kissed her good bye and made their way out as I treated her as best I could. After she had enough she put a cap on my tunnel of love to keep me from leaking, took Annie's hand and led her out dragging her husband behind them. I would clean the room in the morning I thought as I to got up and went to bed.