As our story begins, deep in beautiful foresty hills and mountains of Stepford, is a small town, that is very luxurious and almost gives a feeling of enchantment. A couple is just arriving at their new house giving the promise of a more pleasant life. Terry and his wife Anastasia couldn’t wait, even though this place was still a mystery to him, Anastasia looked it up and insisted they would both love it. They got to meet so many new people on the way here but Terry was wondering after seeing so many people how come they didn’t see any guys? They were all very cute and sexy women but he guessed there must be a guys club they all went to or something.
Suddenly they saw some of their neighbors coming to welcome them! It was two girls and they couldn’t keep their eyes off one of them! She was wearing a short, white, floral babydoll dress with matching frilly panties and they were very poofy. She was cutely hugging a teddy too! “Hi! I’m Jenny and this is my sweet sissy, Baby Doll.” Baby Doll gave a cute curtsy and blew both of them a kiss. Terry said “What is a sissy?” Then Jenny said “She is my lover I can dress up just like a doll and treat her like my little darling.” she said as she caressed her and they passionately kissed. “She will do anything I say” Jenny said for her to turn around as she slapped her bottom. Terry suddenly felt very turned on and thought we are living next to some very sexy people. He wondered that maybe he could persuade Anastasia to be his sissy.
Later that night Terry and Anastasia kissed each other good night and Anastasia turned on some relaxing music. Terry asked her what it was and she said she saw it at the Stepford gift shop and just had to have it, it is supposed to “relieve stress”. Terry did feel very relaxed. Jenny said “Don’t go to sleep just yet sweetie. Drink some of this to make you feel more comfy while you sleep.” It was pink juice and it tasted like strawberries. Terry loved it and drank it all then fell right to sleep.
The next morning Terry felt more wonderful than he has ever felt in a long time and thought what a lovely morning. Immediately he thought he needed to take a bath and skipped into the bathroom. As he was taking off his clothes he felt grossed out that he had so much hair on his legs. Which was weird because he never felt grossed out by it before. He took Anastasia’s pink razor and made him smooth as can be while bathing. Also found Anastasia’s shaving cream that made his legs shiny and smell like sweet perfume. Then he noticed that his penis seemed a lot smaller than before, like 2 inches but that can’t be he thought, it must be how water can sometimes make it shrink for a little bit. Terry loved the pink razor and shaving cream so much he used it to shave his face. He didn’t like those bushy eyebrows so he plucked them into a nice and sweet arch. He smiled at how lovely the results were and blew a kiss into the mirror.
Walking out he thought it was time to figure out what he was going to wear. When he looked in the closet he thought how drab his boy clothes are. He grabbed one of Anastasia’s white frilly bloomers and a lavender frilly blouse with puff sleeves and a bow in the back. He had an irresistible urge to put it on. He thought well maybe until I can get me some new outfits!
Anastasia saw Terry walk in the kitchen and giggled at how pretty he looks. She ran to him and they hugged and kissed. “You look so adorable sweetie! You should wear some of my outfits more often!” Terry blushed not knowing what to say. Anastasia said, “Be a doll and make me breakfast and then clean the house for me darling. If you are a good sweetie we can have some fun later tonight.” Terry had an irresistible urge to want to do those things for her. Anastasia wrapped in very frilly apron around Terry and he minced away in his pretty outfit.
Later that night Anastasia loved everything Terry did so much she took his hand and led him to their bedroom. She slipped off her dress to reveal lovely lacy lingerie. Terry couldn’t believe it but the second he was turned on he felt his panties getting wet. He looked down and saw his very tiny erection was cumming already. He thought “Oh no, how could this be happening!”
Anastasia looked back and saw the wet spot on his pretty bloomers. She giggled and said “Oh my, you are a sissy aren’t you. Sissies like you just can’t hold it in and look at how tiny it is! I don’t think you can reach into my pussy with that itty bitty peepee, do you want me to pleasure you by sticking a dildo up your sissy bottom from now on?” Terry was beat red from blushing now.
Anastasia said for Terry to lay on her lap with his bottom sticking up in the air. Terry shyly minced over to her and laid down as Anastasia caressed his pantied covered bottom then she spanked him. “I want you to say in your most high pitched bimbo like voice, I’m a pretty little sissy and I wet my panties.” Terry shook his head no and Anastasia spanked him some more and said “Say it sissy!” Terry said “I’m a pretty little sissy and I wet my panties.” in a very high pitched bimbo like way. Anastasia caressed his bottom and said “That is a good sweetie. I want you to talk just like that from now on or I will give you another spanking on your pretty bobo. Now you can pleasure me with your tongue.” Terry moved in between her legs and started licking away until she had many amazing climaxes. As they went asleep Anastasia turned on the music and gave terry the drink again. Terry felt even more at peace listening to it.
The next morning they awoke and Anastasia said “Morning sweetie” Terry said “Morning…” but suddenly was in shock because he couldn’t help but speak in a very high pitched bimboish voice. “Like oh my god, how come I can only speak like this??” Anastasia said “Because your a cute sissy from now on and thats how cute sissies like you talk. You can even only say sissy words from now on sweetie. Just try to say my name.” she said grinning. Terry tried to say it “Ana..an..mmm..Mistress, Anas….Mommy. Hi Mommy dear how may I please you?” Terry covered his mouth. Anastasia said “See, since your my sissy cutie you will call me Mistress or Mommy, its so adorable how you say that!”
Terry pouted sticking his lips out and said “Imma sissy!” Anastasia hugged him and said “Aww there there, you will love being a sissy. It will be so much fun being cute and pretty for your Mommy! Now today all the neighborhood girls are giving us a welcoming party. So let me get you dressed.”
At the party everyone was dressed in beautiful petti dresses and gowns. Terry could have sworn he started to feel jealous but tried to push that thought away. Terry found out that all the wifes here had sissies just like their neighbors and they were dressed darling in little girl dresses but oddly he still didn’t see any guys. He kind of felt relieved as he couldn’t imagine what they would do if they found him dressed so pretty, talking and acting like a sissy. “They would probably treat me like one of the girls” he thought. Then it dawned on him and he gasped. Anastasia said “Have you figured it out yet sweetie? All the sissies here used to be guys and the music you have been listening to has been making you into a lovely sissy just like them and the drink has been causing your little pee pee to shrink.”
Terry was in awe but thought “She must be kidding I mean they would have to have advanced genetic engineering to turn guys into those cute bimboie bombshells, they would have to..would have to…umm.” Terry used to know all about that kind of stuff but now he was blanking. His mind kept urging him to think of more cute and pretty things. “She must have been hypnotizing me to act like a sissy.” He thought.
Still kind of confused, they all gathered in a circle around Terry and Anastasia. They all got drinks and one girl gave him a drink. They said “Cheers to our new lovely neighbors!” As they all said cheers Terry took a drink and a wave of light appeared around him! Terry started to shrink, he felt his hips flare out and his, now her, waist tighten, her little stub went inwards and turned into a vagina. Then she felt his chest expand and turn into two large breasts, then her bottom inflated giving her a cute and pert bubble butt.
“Eeep Imma girl!” Terry said and then suddenly feeling a wave of sissy pleasure come over her new highly sexual body. “Oh baby!” she shouted while feeling her new breasts and then she blushed when she realized everyone was watching. Anastasia shouted with glee “Yay! Terry your a bimbo girl just like the other sissies now! You know how I’ve let you know that I’m bi before but the more I was with you the more I realized I liked girls more. Now we can be two love birds together and you can be my sissy girl. I want to call you Sissy Tiffany.”
She took Tiffany by the hand and showed her to the girls dressing room. “I’m going to show you the fun of being a sissy by playing dressing up with you! I only want to see my sissy in the most slutty outfits.” They tried on all the most adorable and extravagant outfits that made Tiffany look like the cutest dolly. Then they slipped on a short fluffy pink tulle dress with ruffles along the breast and sleeve lines. They had cute pink maryjanes with lacy white knee high stockings. The dress was so short you could see her frilly panties! “Oh you are so pretty! I think I’ll keep you in this outfit for now baby.”
Then Anastasia led Sissy Tiffany over the make up vanity to how her how to put on make up. “I’m only letting you know how to put on make up to make you look like a bimbo, I’m going to show you how to put on lipstick to make your lips look full and pouty.” After putting on make up Tiffany indeed saw she looked like a bimbo with very few but fun things on her mind. She blew a kiss to herself in the mirror and felt herself get turned on. Anastasia said “I’ll bet my sissy bimbo even thinks like one too now. Doesn’t she? Oh Tiffany can you tell me what two plus two is?” Tiffany thought for a second and said “Like thats hard *giggle* Lets like talk about more fun stuff.” Anastasia giggled and said “Okay don’t you worry your pretty little head. Now kiss me!” They passionately kissed but then Anastasia decided not to make Bimbo Tiffany too turned on because she wants to save the fun for showing her off to the girls.
Anastasia led Tiffany back to the party room and they all awed and gawked at her. They all gathered around looking at how cute and sexy she looks in her outfit. Tiffany was giggling and loving all the attention! It was making her so turned on! One of the girls said for Tiffany to say “I’m a sissy bimbo who likes to be treated liked a cute babydoll.” Tiffany said it in her sweet high pitched voice “I’m a sissy bimbo who likes to be treated liked a cute babydoll.” They shouted “Yay!”
Anastasia patted Tiffany’s bottom and said for her to go play with the other sissies. The other sissies were learning how to do the “I’m a little teapot” dance. She did it perfectly and as cute as can be with the other sissies. Then one of the girls told the sissies to show everyone what slutty girls they are and lick their mommies lollipops. Tiffany perkily moved towards Anastasia, seductively moving her hips and already feeling her mouth watering and getting more turned on with every step she made towards her. She happily placed her head into her Mistresses pussy, giving their Mistresses so much pleasure, she looked to the other sissies next to her and then looked at what she was doing. She felt like a pretty sissy slut just like them which made her turned on even more. They licked their Mistresses pussies that gave them waves and waves of orgasms.
Later that night Anastasia dressed Tiffany up in a cute lingerie cami and tied a bow in her hair. As they went to sleep Anastasia mentioned she had some new things she wanted to hypnotized Tiffany with. The next day Sissy Tiffany came into the kitchen in a sexy french maids outfit. She gave a cute little curtsy and giggled when she saw Anastasia. Anastasia awed at how adorable she looks and ran to kiss her.
She said since Tiffany has been such a good sissy girl she wanted to show her something. She led her to what looked like a little girls room and said “This is your new room!” It was filled with little baby toys and dolls! There where so many cute things that filled her sissy heart with joy! Tiffany squealed with glee and kissed Anastasia and said “I wub my lovely room and dollies to play with Mommy!”
Anastasia said “Also that isn’t it darling. I want my sissy baby to get her pert bottom up on her pretty bed and I will be right back.” Anastasia returned with a ten inch strap on dildo “Sissy is going to get her pretty sissy cherry popped. Bend over with your pretty bottom up in the air sweetie.” Anastasia said. Tiffany lifted her bottom and felt the thick ten inch fill her new pussy. She let out high pitched moans of pleasure. “This is how my baby will pleasure herself from now on. Okay sweetie? You will just be yearning for mommies strap on all day. Would Sissy Tiffany like me to place lots of lovely toys for her to play with both of her sissy pussies in her nursery?” Sissy Tiffany in the middle of an orgasm excitedly shouted “Yes Mommy!” Then Sissy Tiffany spat out loads of pussy juice all over.
Anastasia said “Oh baby made a mess everywhere, I’ll just have to get you some diapers to wear. *giggle*” Sissy Tiffany blushed at that thought. And so Anastasia and Tiffany lived happily ever after in the town of Stepford with Tiffany as her sexy sissy baby bimbo and she played sexy french maid when they had guests. She got to pleasure them in anyway they wanted and that is….