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This is a followup to "Belle of the Boutique."
It was a great job. My eyes had been opened to a whole new world of sex and sissiness and my ass had been opened up as well. I used t o think of girly dresses as a worthless waste of time and money fit for bimbos and sluts. Now I actually have dreams about being a bimbo and a slut in a pretty dress.
But as much as I love the dresses I have been modeling at the boutique and the photographer who took pleasure in fucking me when I did, it was the diapers that really turned me on and turned me out. Jim and Ms Johnson both noted how much I liked wearing them and so practically every dress I modeled included a diaper underneath. I was even allowed to take some diapers home from time to time.
Then Finagle's law shoved it's cock right up my ass.
Finagle's law: "Whatever can go wrong will... at the worst possible time." Yeah, you've heard of Murphy's law? Well Finagle's law is Murphy's law on Viagra.
I was at the boutique about ten or eleven weeks after I started working there and was modeling a pretty pink princess style ball gown that was becoming popular with crossdressers. It had ultra full floor length skirts, puffy shoulders, short sleeves and I was wearing one of my favorite ball gags for the video shoot.
And of coarse I was thickly diapered.
The room I was in was the same one where I had spied on my sister a couple months before, the same room where I wore my very first dress and where Jim had popped my cherry. And again as on that day, my sister was on the other side of the two way mirror for her final fitting before her wedding which was only a month away now. She must have taken an Uber since I had a job and couldn't chauffeur her around anymore. The emphasis of her fitting today was her shoes. She was prancing around in her bridal heels and other assorted bridal lingerie which along with stockings and a garter belt also included a thick bridal diaper.
And wouldn't you know it, right when I was on my hands and knees with Jim's cock planted deep in my diapered ass, my sister tripped in her heels and flung herself right into the mirror popping it out of its frame and shattering it on the floor in front of me while my sister stared in disbelief at the scene before her.
Even with the ball gag in my mouth my sister recognized me.
"Chris, is that you? OH... MY... GOD..." she exclaimed.
Jim pulled his cock out of my ass so quick I practically came right there. I pulled the dress down to hide my diapers and quickly got to my feet when Jim asked us both, "Is everyone okay? No one cut?"
The glass on the floor seemed like a minor inconvenience compared to being seen like this in front of my sister. She was embarrassed as well, both by being caught half naked and for wearing the thick bridal diaper.
"I'm fine, I just tripped and hit the mirror but I'm fine." my sister said as she held her hands alternately first over her breasts and then over her diaper then added, "Chris, what's going on here?"
I turned and despite wearing heels of my own, picked up the huge skirts of my dress and bolted out of the studio.
I was mortified.
Jim and Ms Johnson came to check on me in the room I used as a changing room when I did modeling.
"Well we cleaned up everything and no one was hurt and fortunately, your sister never realized the mirror was a two way mirror but she did see you and knows you saw her. I'm sorry kid, I dont know what to say. How are you holding up?" Ms Johnson asked as I pulled the gag out of my mouth. I had left it there since wearing it gave me comfort.
"I have no idea how I'm gonna explain all this. My sister is gonna tell everyone from here to hell what she saw. No one knows what I do here, no one." I said half pouting.
"Why don't you take the rest of the day off to calm yourself. Tomorrow is Friday so go ahead and have a long weekend and we can reassess on Monday okay honey?" ms Johnson offered.
I accepted and wondered what the hell I was gonna do.
Just one thing I had to do before I could leave for the day. Jim still needed to get off and so before I took off the dress, he plowed my ass one more time. It felt like a pity fuck but I took it.
I chose to wear a diaper under my boy clothes for comfort when I left to go home but wouldn't you know it, my sister was waiting for me.
Why can people leave things alone?
"So, this is the job you've been doing for the past what... three months now?" Cindy asked as she walked with me toward my mini van.
"Can we not talk about this?" I asked as I tried to walk fast to get away and avoid the conversation.
"No, no we cannot, not talk about this. I know what I saw. You were in a dress on your hands and knees while some naked guy was making love to you and I'm pretty sure you had a diaper on too. I know you had a ball gag in your mouth." she said.
"Look, it's just a job. I get paid to model things for crossdressers and sometimes we have sex. Don't tell anyone please." I said almost pleading.
"I'm not mad at you little girl. I'm so excited. Now we can be sisters and try on clothes together. But I gotta tell at least one person okay? I gotta tell mom." she said.
"O... M... G. No, no way in hell. Mom would have a fit if she knew what I've been doing." I said angrily.
"No she won't, she'll be as excited as I am, trust me sis. Mom will be in heaven. Besides you dont have a choice now do you. Btw, what did you do with that dress you were uh... modeling? It just screams fairy princess." she asked.
"They dont sell used dresses so I get to keep what I model but I have to leave them at work cause I got no place at home to hide them." I said and trust me that was the wrong answer.
"Fuck no!!! you get to keep them? Show me, I gotta see." she demanded.
And so I was forced to march back into the warehouse and back to the makeshift dressing room so my sister could see all the accumulated garments and sex toys I had modeled since I had started this job.
First I was forced to endure comments like, "I bet you looked so pretty in that one." and, "OMG that one is so slutty." and, "Wow, you took that one all the way up your ass? Impressive." and, "Can't wait to see you diapered."
Then I was forced to help load all of my shameful things into the minivan to take home. I was mortified the whole ride home.
My sister was giddy as she helped me unload all the stuff into my bedroom and gleefully shoved all my regular clothes aside to hang my dresses and gowns in my closet. She unceremoniously dumped the contents of the top drawer of my dresser onto my bed and replaced the contents with my assorted sex toys. My shoes and boots were shoved aside in my closet to be replaced by the assorted heels, flats, slippers and sandals I had modeled. Lingerie filled out the next two drawers of my dresser and my nightgowns and nighties were left to hang on a hook in the bathroom.
But the worst was yet to come. My sister with a couple swipes of her hand emptied the shelves of my bookcase which had been filled with all my sci-fi books and Star Wars memorabilia and replaced everything with diapers. Every shelf full of diapers.
"Okay little sister, I wanna see you in a diaper before we do anything else so get naked." Cindy almost commanded.
"Well, actually..." I said leaving it unsaid but indicating my nether regions.
"I gotta see, come on, strip baby. Pretend I'm that cute guy you were letting fuck you and model for me." she said with such joy.
I took off my shirt trying to stall but no matter how slow I went I eventually found myself standing in my room about all the clutter and mess my sister had made wearing just a diaper.
Come with me little sister." My sister said grabbing my hand and leading me out of my room and down the hall to her bedroom. She then stripped naked and then removed a strapon from her top dresser drawer and put it on.
"Wait, I can't do this. Not without something girly to wear and I have to have my gag. I need my gag when I have sex. I wore one when Jim fucked me the first time and I like it." I explained and added, "I always wear a gag for sex."
Wearing just her strapon, she bolted out of the room and returned with one of the nighties and my ballgag.
The sex was awesome. She didn't tire like a man when he gets off, no when she orgasmed she kept going driving me wild. First she pulled my diaper aside and did me doggy style, then on my tummy, then on my back. She came three times and I shot cum into my diaper twice.
When she was done with me, she collapsed on the bed next to me. We were both exhausted and fell asleep in each others arms.
We were in the spoon position with her in my arms and my hand laid over her and my fingers wrapped around the rubber dong of her strapon that she had plowed my ass with. We were asleep when I felt my nightie being lifted and opened my eyes to see mom checking my diaper.
I was still gagged and couldn't really say anything but I heard my sister say, "It's okay mom, Chrissy didn't touch my vagina. I'm still a virgin and will be when I get married."
"I see your sister isn't a virgin is she?" mom said but not in a disapproving way.
"I just found out today that our little Chrissy has been modeling dresses for the same boutique where I'm getting my wedding gown and she has a boyfriend. I even caught them doing it." Cindy said as I lay there all diapered and in a nightie.
"I see, well I just came up to tell the two of you that dinner is in fifteen minutes. Might as well keep the nightie on Chrissy." mom said and then left.
Cindy got up and quickly put on a nightgown of her own for dinner while insisting that I keep my diaper on under my nightie. I removed the gag and together we went down to dinner.
Typical dinner. Chicken and taters with a salad. I was always amazed at how mom worked and still made a dinner almost every night. As soon as we sat down, mom looked over at me and said, "All right now, lets hear it and I mean all of it. Especially the part where you decided to hide all of this from me?"
I told mom everything that happened except the parts about watching clients like my sister naked in the changing room.
"So do you like wearing a dress then?" mom asked.
"Yes, I guess I do. I mean well..." I left it there not sure how to have this conversation.
"I see, and this Jim, are you in love with him?" mom asked continuing her inquisition.
"God know. It's just sex I swear and nothing more. I mean I kinda liked the idea of being with guys and all but not love." I said wondering if I said too much.
"And the diaper which by the way you look cute in?" mom inquired further.
"The brides use them and some of the crossdressers like them so I model them." I answered trying to avoid the question I knew was coming next.
"But do you like them?" and there it was.
"Yeah, I guess." I said holding my head down.
"And why hide all this from me?" mom asked.
"How come you don't wanna know all about Cindy and her strapon huh? I bet she doesn't share everything with you." I countered and I knew this was dangerous ground but deflecting seemed the only weapon I had left.
"You big sister has always shared everything with me and if we had known you were a girl too we would have shared with you too. That's what mommies and daughters do sweetheart. Now why the secret?" She said taking me by surprise with the admission.
"I was embarrassed and didn't know what people would think." I said almost under my breath.
"No need to be embarrassed with me, I'm your mother now lets get this straightened out. You like wearing pretty dresses... yes?" mom asked.
"Yes."
"You like having sex with boys?" she persisted.
"Yes." I said still humiliated even though mom was trying to be understanding.
"And you have a job as a model for a boutique, basically working as a woman?" she asked and I hoped this was going somehere quick as it was mortifying.
"And when your not modeling and just working in the warehouse packing orders and stacking shelves, do you wear a dress then?" she continued.
"Sometimes, I mean when it's convenient. Once I model a garment they can't sell it so I get to keep them and no need to change right away if I have work to do." I answered.
"And last question baby, do you like wearing a diaper? Be honest?" she said a bot more sternly than her other questions.
"I guess. It's just sex play and all." I said.
"Well that settles it then, you are a girl, a baby girl and you should start acting like one. First no more pretending to be a boy or wearing boys clothes and second, no more hiding things from me or your big sister and third, if your gonna wear a diaper then you will use them, at least for wettings anyway and either I or your sister will change you, and forth, you can get a dress to wear for your sisters wedding instead of your tuxedo." mom explained.
"Why do I have to pee in a diaper?" I asked completely ignoring the fact that I had just been ordered to wear a dress at my sisters wedding and everywhere else for that matter.
"Several reasons, one reason I want you to and the second reason is you need some sort of punishment for keeping secrets from me and your sister and finally, you look so cute in a diaper so I want to take time to change you." mom said utterly humiliating me.
"O. M. G. mom, you should see his, I mean her closet. It's chock full of dresses she models. She gets to keep everything."
What the fuck had I gotten myself into? Wearing a dress all the time. Not only was that going to be horribly humiliating but my dick will be hard all the time.
Fuck me... Fuck me upside down.
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