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Finally the day arrived when I was on vacation so I dressed in sweats and 3 layers of disposable diapers with plastic pants then filled my duffel bag with extra diapers and put my clothing in my gym bags then I loaded my jeep and left home. I stopped on the way to get gas and to fill my ice chest. As I drove the 385 miles to Ann’s house I drank several sodas just to keep my diaper good and wet so when I finally arrived 7 hours later I was soaking wet but hadn’t leaked.
After grabbing my bags I knocked on the door and expected her live in maid to answer but it was Mistress Ann who answered. When I entered Ann told me she no longer had her tranny maid witch made me disappointed but she said she was hoping to fix that soon.
Then she ordered me to strip down to my diaper so she could change me because she knew I must be wet. After stripping down to my diapers and plastic pants she said I guessed you would be wet but she didn’t realize I would be that wet then she marched me into her nursery she had last year then had me get up on the changing table.
After she removed my diaper she cleaned me up with wipes then she re-diapered me and placed a pair of pink teddy bear plastic pants and then a bib on me and told me it was dinner time. When I got up she made me crawl into the dining room and get into the adult sized high chair as I climbed up and sat down she restrained my hands to the arms then she placed a strap around my waist to secure me. Then she fed me 4 jars of baby food and 2 bottles of Simulac baby formula then she unstrapped me and had me crawl to the couch for a nap while she watched her movies and talked to several people on the phone after about a half an hour I fell asleep.
I woke up with Mistress Ann yelling at me that I had wet her couch and she had company coming over the next day and now the couch was wet so I had earned a ass whipping for it so I might as well march my ass into the dungeon and get ready to be punished. As I waited Ann came in and told me “strip down sissy” after I was stripped down she placed my wrists in leather cuffs and fastened them to a cross that was fastened to the wall.
As I stood there facing the wall I could hear her going through her wall cabinets where she kept her collection of whips and paddles when Mistress seen me trying to look she yelled for me to close my eyes. Then she placed a leather hood over my head and placed a penis gag in my mouth and fastened it.
Then she started to give me one of 50 swats on the ass with a leather-covered paddle. After she was finished she placed a rubber apron around my waist then had me hang by my wrists as she slid a small child’s pool under me then she had me stand up when I stood up she turned out the light and left me by myself for about 3 hours.
When she returned she removed the hood and released my wrists then my apron and had me step from the pool witch had a puddle of pee in the bottom. She then marched me into the nursery and had me get back in the changing table so she could re diaper me as I laid there she pulled a big bundle of pink diapers and several soaker pads then proceeded to heavily diaper me. After the diapers I could tell that I would be diapered for a long time then she pulled some pink bloomer style plastic pants over the diapers then had me climb into the adult crib and into the rubber sleep sack. As she fastened the sleep sack she told me she had some shopping first thing in the mourning and this way she could leave me without having any more wet couches then she gave me a large bottle and turned the light out and left.
The next mourning I woke to the sound of Mistress Ann as she shut the door on her way out as I laid there in my sleep sack I could tell I was in very wet diapers and wondered when Mistress Ann would be returning. About noon Ann returned and entered the room holding several baby bottles of formula for me as I greedily sucked them all dry she asked if I was sorry for the night before and would I like to be changed.
When I finished I told her how very sorry I was and that I was so wet I could feel my diapers leaking inside the sack so would she please change me and she told me ok she would but she was planning a dinner party that night and since she no longer had a maid I would have to do. As Mistress Ann removed my diapers she had picked up some things for me to wear as her maid then she led me into the bathroom and placed wrist restraints on my hand then she connected them to a hook in the shower. After I was secured she removed from a cabinet an inflatable Bardex style enema nozzle and proceeded to give me an enema then she sealed off the hose so I had to retain the emena. As I stood there with my painfully distended belly Mistress Ann started to shave my crotch clean (I normally stay shaved but she said the hair was to long. After she finished she released the enema and I emptied my bowels she turned on the shower and started to scrub me clean then she released my hands and toweled me dry.
After she dried me she marched me into the nursery and rediapered me in triple thick diapers then she applied glue to my chest so she could apply a pair of breast forms then she sat me up and fastened a black satin bra. After the bra she pulled a white crinoline slip up my legs then pulled a black satin maids dress over my head and fastened the buttons up the back. As she adjusted my slip and dress so the bottom of my plastic pants would show then she dug a blond Dutch girl wig with pigtails out of a bag and adjusted it on my head till it was just right. When she was happy with my hair and dress she had me sit down in front of a mirror to apply lots of makeup so I looked like a slutty whore.
After getting dressed and made-up I was ordered to clean the rooms then help Mistress Ann set the table and decorate for her dinner party. As the guests arrived everyone was commenting on the sissy maid and my diapered state as I was serving one couple was rubbing my chest and my diapered rear then talking to Mistress Ann. After the dinner was finished I had to serve dessert and clean up. Then Ann announced that it was time for the play party to begin as everyone went into the dungeon I was led in and Mistress Ann announced it was time she punished for making a mess the day before then I had my dress pulled up and pinned to the collar of my dress and my wet diapers and plastic panties pulled down and Ann started to swat my ass then let everyone take a turn. After my diapers and plastic pants were pulled up I was told to sit in the corner as everyone punished their slaves as was needed.
As everyone had it was late and the guest’s were wanting to leave I was made to kiss everyone goodbye till almost everyone had left but the couple and Mistress Ann who were in hushed conversation then Ann announced that she had rented me out to them for the weekend. Then Carol and Mistress Ann went into the nursery to put together my wardrobe. When they returned I was led into the nursery I was stripped of my maids outfit and laid down on the changing table and they proceeded to change my wet diaper. After my diaper was stripped off Mistress Carol used a wet washcloth to clean me then slid a small vibrating egg into my asshole and then powdered and oiled me then taped a disposable diaper on me and had me step into a pair of pink satin panties that were lined with plastic.
At this point Ann pulled some white thigh length stockings up my legs and then placed a pair if white leather sandals on me then they sat me back up and removed my black bra and with Carol commenting on how nice my false boobs were Ann hooked a white satin bra on me. Then I was stood up and told to step into a very short but full crinoline skirt that was adjusted to show half of my diapered state then they pulled a light pink satin party dress over my head and zipped it up. After I was dressed they rubbed my body down with Johnson’s baby lotion so I smelled sweet then covered my blond pigtailed wig with a pink bonnet and marched me out to present me to Tom for his birthday.
As Tom saw me he was saying how nice I looked and how much fun he would have with me Carol turned on the vibro-egg in my rear and Tom wanted to know from Ann if I was any good for anything besides petting when she said she would show them. I was ordered to my knees in front of Tom and told he had a long pacifier for me. As I kneeled there tom unzipped his pants and pulled out a hard 9” cock that was about 3” around and told me to start sucking.
As he moved forward I started to lick and kiss that cock Tom grabbed my pigtails and told me he wanted me to suck not lick then pulled hard so the cock was forced into my mouth after a minute or two I could feel his cock start to swell up and Tom started to pump his cock in and out of my mouth then he sprayed his baby juice in my mouth and warned me I had better drink it all and not leave a drop. As I struggled to swallow all his salty cum and suck his cock clean Tom said that the pigtails were like the handlebars of a cock sucking machine and he couldn’t wait to get the baby home to play with some more.
After I had licked him clean Tom put my pacifier away and Ann had me stand up so she could fix my makeup and she applied a heavy coat of bright lipstick then told Tom and Carol to take their play toy home but they were supposed to have me back in 48 hours. After I was marched out to there van I was strapped in the rear seat and Tom got in next to me and Carol said to Tom not to wear his new toy out to much we still had a lot of things to do at home. While Carol drove us home Tom kept turning the vibro-egg up and down while rubbing the front of my diaper till I started getting hard and finally came in my diaper then he told me that if u was a good sissy baby I would get to do many more “stickies” in my diaper over the next two days.
When we arrived at the house Carol grabbed the bags and Tom carried me into the house and sat me on the couch then Carol finished putting away my diapers and clothing then she walked up to me and lifted her dress part way and told me it was her turn to have the baby service her. As I kneeled down she pulled her panties down to reveal a small cock and ball sack I then realized she was a tranny and she then dropped her dress over my head as I started to suck her cock witch never really got hard but after a few minutes it started to squirt some cum into my mouth.
Carol then announced it was time for the baby to get ready for bed so I was marched into the next room and as Tom fed me a bottle of milk Carol stripped me down to my bra and diaper then she noticed my diaper was wet she had me lay down on the bed she removed my diaper then Tom raised my legs above my head so Carol could lube up a large butt plug and as she slid in my sissy pussy I yelled it was to big she said that that was too bad and announced that now she would not have to clean any messy diapers in the morning she then re-diapered me and pulled some bloomer plastic pants up over my diaper and then pulled a baby doll nightie over my head and tied my hands to the bed posts and walked out after shutting out the lights.
The next mourning I was awoken by Tom and Carol and Carol removed my diaper and butt plug then told me I should use the toilet because she didn’t want to change any messy diapers. As I finished she walked into the bathroom with a double bardex balloon enema catheter and proceeded to give me an enema just to make sure I was cleaned out she said. After the enema she removed my bra and breast forms and had me get into the waiting bubble bath. As Carol washed then dried me she told me that today was Tom’s birthday and I was his play toy for the day and he wanted me all pretty for his poker party later.
When I was all clean and dry I was led into the other room and Tom had laid out my diapers and clothing when I was laid in bed to have my diaper changed Tom slid a diaper under me and Carol then pushed my knees to my chest and then Tom got on the bed and told me it was time to be treated like a real sissy then he grabbed the tube of K Y jelly.
As Tom greased up his hard cock and my asshole he told me to relax and he would treat me like his ex-wife on their wedding night. Then Tom showed me why he was divorced as he shoved his long fat cock in my ass the full length I screamed and Tom just started pounding away. Just when I started to enjoy myself then he tensed up and groaned and shot his warm load of cum deep in my ass. Then he pulled out and as I lowered my legs I was told I was a great fuck and as Carol taped my diaper on Tom stood next to the bed and made me lick and suck his cock clean. After he was clean he picked up a pair of pink nursery print plastic panties for me to wear then Carol applied the glue and breast forms and put a cotton bra on me like a young girl would wear then pulled a pair of white tights up my legs then produced a green girl scout uniform for me to wear. As I was dressed I looked into a mirror I could see a young girl scout that was in diapers then Carol placed my pig-tailed wig on me then made me help her get the house ready for the party. As me and Carol got the house ready Tom went to the store and as I set up the card table Carol left the room and as I spread out the poker table cover Carol walked up behind me with a strap on dildo then had me lean over the table then she pulled my tights, diaper and panties down and proceeded to grease my sissy pussy hole then she shoved in the dildo then started to slowly fuck me and told me that I should get fucked slowly so I could enjoy it.
As Carol fucked me I could feel the dildo rubbing my prostate and really started to enjoy it then I felt myself cum in my diaper and carol told me she hoped I enjoyed myself because it would probably get rough later. As she rearranged my diapers and clothing I told her I loved it and would she like me to suck her to thank her when I said that she lifted her dress and I kneeled to suck her cock as I pulled her panties down I noticed she had a hard on so I slid my lips over it and as I started to let her fuck my mouth she lowered her dress and told me how good it felt to suck a transvestite off with her dress over your head as I nodded (she was right it did feel real kinky) I felt her cock swell up and greedily swallowed all her cum then pulled her panties up and raised my head from under her dress then stood and kissed her.
Carol then told me that she was a sissy that Tom had found on the streets years ago and he had her breasts implanted and turned her into a tranny so she had started helping him at his poker games and she had survived his games and hoped I would like it too. When Tom returned he had a friend and when he saw me his friend started laughing telling Tom he was finding younger and younger sissies to play with. Tom told him you haven’t seen nothing yet and he lifted my scout dress to show my well diapered state when his friend asked Tom explained that I had hurt my back years ago and now have to wear diapers the rest of my life. Tom’s friend asked if I was good for anything else Tom told him to wait till after whoever wins the first hand and he would see. When the others showed up Tom said before the game started he had to check the sissy scout’s diaper and when he lifted my back of my dress and found my diaper dry he pulled his cock out and proceeded to piss in the rear of my diaper and I started to blush and giggle with the feeling of someone else’s warm piss running down my ass cheeks and pussy crack. Tom then announced as he lowered my dress that the winner of the first hand would get a present from the sissy and she was fully prepared just like a good scout.
As the game started I was told to serve drinks and as I did everyone was enjoying them selves feeling my wetly diapered ass and rubbing my tits and whispering to me what they wanted to do to me. After the really big friend of Toms won the first hand Tom had me get on my knees in front of him and pull his cock out then lick and kiss it as it started to get hard and he was really getting exited and I could see he had the biggest cock I had ever seen. Just as I was getting ready to start giving him a blowjob Tom stopped me and told everyone now lets see who wins the game and wins the sissy baby. While the game continued I was made to lick and kiss the cock of everyone who had the winning hand.
As the game ended Tom was laughing as he was winning every hand because everyone was so horney they couldn’t concentrate on the game. After the game finished I had made 6 cocks very hard and 6 men so horney that Tom told me to just start at the end and make everyone happy while I was giving everyone a blow job Tom counted his money and announced he had won enough to pay for my rental. After I had given 5 blow jobs Tom lifted me to my6 feet then carried me to the next room and laid me on a table face up and raised my dress then removed my diaper and tossed the guys a tube of K Y jelly and told them to have fun. The biggest guy with the biggest cock said he would wait till last cuz’ when he fucked me my pussy would be so stretched out I would be ruined. Then
everyone grabbed me and started to fuck me and I found what it must be like to get gang raped. As the last guy stepped up he just shoved his cock in and started to deep thrust in me and although it really hurt and I started to cry like a baby Tom shoved his cock in my mouth to keep me quiet and I could feel the big guys cock rubbing against my prostrate till I started to get hard and felt a orgasm starting the big guy started to spray what felt like a quart of cum in me at the same time I had one of the best orgasm’s I ever felt. Then the guy leaned over and started to kiss my boobs and lips as his cock got soft then he pulled out and I saw blood all over his cock from my pussy and Tom told Carol to come clean the sissy and change his diaper.
When the others went into the other room to have drinks Carol started to clean me and as she did she told me that the same had happened to her many times and I told her it wasn’t bad but I would have liked them to gentler but she told me that they all thought that a sissy has no choice how they get treated. She then powdered and oiled me then put a soft pink cloth diaper on me and some pink rubber pants and removed the scout dress and the tights witch had holes in the knees by then and dressed me in my pink baby doll teddy. Carol then had me kiss every one goodbye and thank then for showing me what a sissy was put on earth for as the men left Tom told me that he was glad I was such a good sport and as a reward he was going to let me sleep with him that night. While me and Carol cleaned the mess I could feel the cum running out of my asshole and absorbing into my diaper. When we finished Carol said it was time to get me ready for beddy bye and she took me into the master bed room and added perfume and more lipstick then tucked me into bed to await my daddy.
Later I felt Tom get into bed and he started to kiss me and feel my boobs then he pushed me down and told me to kiss and lick his crotch as I was pleasing him Tom told me he had found a gift that day and I would love it as soon as we got back to Mistress Ann’s then he rolled me on my back and removed my rubber pants and un pinned my diaper and gently pushed my knees up and slid his cock in me commenting that with all the cum I still had leaking to lubricate me real nice. As Tom slowly and gently fucked me I could only smile and kiss his nipples and neck then when he came in me and then he re-pinned my diaper and pulled my rubber pants back on then he kissed me goodnight.
The next mourning I woke and found Tom still asleep but he did have a hard cock for me to play with and as I sucked him awake he told me had to pee before he could cum and I told him my diaper was only damp and he could piss in it like last night I stood up next to the bed and tom got up and had me lean over slightly then pull open my diaper and rubber pants and start to piss as I felt his warm mourning piss on my ass crack only he pissed a lot more than the night before and I could fell it puddle around my cock and balls. As he finished he started rubbing the front of my diaper till I came in my diaper then he had me turn kneel and presented me my first cock of the day as I sucked on his daddy’s bottle Carol walked in and told us that that was not a very nourishing breakfast and when we finished she had breakfast ready.
When we walked into the dining room I told Carol that I was really soaked and desperately needed a change because I was starting to leak then carol said she had seen why I was so wet so I was marched into the next room and laid on the floor. As Carol changed me into a 6 layer thick diaper and my nursery print diaper she fed me a bottle and hoped that I had had fun because I had to go back to Mistress Ann that mourning. After fed me my bottle she removed my teddy bear nitey and then removed my bra then pulled out a pink plastic print romper with little bears and balls on it after I stepped into it she pulled it up and had me put my arm’s in the sleeves she zipped it up then made up my face and packed my things for the drive to Ann’s.
I told Carol I really didn’t want to walk outside dressed like this because it was way to embarrassing I was told I had no choice just like a baby I was taken out in public just the same Tom walked in to get the bags and Carol told him that the sissy baby didn’t want to be seen in public like this so he just grabbed me and drug me outside and marched me to the car. As we walked outside several people were outside and were pointing at me in my baby attire and obviously diapered state. After Tom buckled me into the van he went back inside to get Carol and my bags then we drove about 30 minutes to Mistress Ann’s house. As we pulled up Ann’s long drive I was very happy to see that no one was there to see my diapered state. When Carol knocked on the door Mistress Ann answered and told Tom she hoped he had a wonderful birthday playing with the baby he said yes now he wants one of his own. Ann then announced that she had received my present but I wouldn’t get to play with it till later that day at the play party.
As Mistress Ann’s friends started to show up the women who had subs marched them into the dungeon and secured them so everyone could talk and plan meanwhile u was kept in a corner of the room with my pacifier gag. Then Mistress Ann announced that she had invited everyone to see her new sissy baby and to se a strap-on dildo demonstration as Mistress Ann told everyone what kind of demo it was she had me stand up for everyone to see. Then she had me go to everyone and show them my diapered state then she led all of us into the dungeon and then told two of the women to remove my romper and fasten me face down to a padded bench. As I was getting my wrists fastened to eyebolts on the bench Ann was going through cabinets and removed several strap-on dildos.
After Mistress Ann had selected her favorite dildo (pink straps and a doc Johnson’s 10” pink jelly dildo with lots of bumps) and strapped it on then she pulled my diapers and rubber pants down then she pulled on rubber gloves and a tube of K Y jelly then she stood behind me and lubed my pussy and told everyone that they should massage their subbie’s prostrate to get them ready at the same time then she lubed up the dildo and slowly worked the head in my asshole. Then she slowly worked more in as she did she instructed everyone that at first they must be gentle at first till the victim gets used to having a cock in them then she slowly pulled back till only the head was still in my ass then grabbed my hips and shoved the dildo in to the hilt. As Mistress Ann quickly fucked me I was trying to cry because I was still very sore from the day before but with the penis gag I could tear up and groan a lot then after 4 minutes she finally stopped and pulled out then showed everyone my wide-open hole. After all the ladies had a chance to see how wide open I was Ann then pulled out extra strap-on’s and asked if anyone else wanted to fuck the sissy baby when no one accepted she pulled my wet diaper back up and announced that she had to change the baby. As Ann released my wrists and marched me into the nursery and while the others watched she removed my diaper and cleaned me at this time Tom remarked that this was the best time to fuck me. While the others laughed Mistress Ann pulled a pair if rubber pants out of a drawer and showed everyone that was a pair of pants with a hole shaped like a pussy to cover my asshole then she pulled them up my legs and adjusted them into place.
After adjusting my new rubber pants Ann showed everyone several kotex and told them that since her sissy baby cant seem to stop wetting that they would soak up any wetties then she shoved them in front of the panties and stood me up then pulled a short crinoline skirt and then helped me into a young girls cotton dress. When I was fully dressed Mistress Ann told everyone she had a surprise and led me into to dungeon when everyone entered Tom went to a corner and pulled a large covered object. As Tom removed the cover and showed everyone an adult sized rocking horse but it had a very large dildo attached to the seat. Now everyone and I knew why Ann had placed the special rubber pants on me then Mistress Ann lubed up the dildo that was 12”long and 2 ½ “ around then Tom and Ann lifted me up and guided my new pussy over the dildo and lowered me slowly at first my hole was still to small but slowly it stretched open more and the gradually lowered me till it was fully inside me and my butt was all the way down to the seat.
While I sat there with tears running down my face because it hurt so much Tom started to rock the horse and at first it hurt even more then gradually as the dildo was massaging my prostrate I started to really enjoy the feeling. Then as Tom rocked me faster I started to have a really nice orgasm then as I came in my rubber pants Ann said now that everyone had seen the babies new toy the could all try the strap-on style’s on their subbies while I rocked on my horse everyone took turns with their subbies and finally after everyone had perfected their style Ann announced that it was time to get the baby ready for bed and it was time for them to go home. As I was lifted from the rocking horse and carried into the nursery Tom sat me on the changing table and I thanked him for the present and kissed him after Ann had removed my dress and rubber pants she said I must have really enjoyed myself because it looked like I had cum several times in my pants.
While she pinned me into my thick night diaper and pulled my plastic pants on me she told me that Carol had asked about borrowing some diapers and dresses so she could be a baby to seeing how Tom seemed to enjoy it so much. As Ann laid me in my sleep sack Carol came into the room and told me that seeing how I enjoyed acting as a sissy baby so much she wanted to try it and she hoped she and Tom would enjoy it in the future. While she and Ann fastened the sleep sack Tom walked in then everyone kissed me goodbye then Tom and the future baby Carol left and as Ann fed me a bottle she said she hoped I had enjoyed myself but not to forget my new rocking horse when I left the next day or Carol might wear it out before I returned. Working on more bit that in the future
Sissy baby Timmy