Come on in! Welcome to the Kink or Treat Halloween party! You’ve just come from Mistress Hadley’s blog, and oh boy, wasn’t that exciting! If you missed it, go back and check it out, or better yet, go back to the beginning of the blog train.
Now that you are all caught up, come on and grab yourself a snack and a beverage and meet some of the other guests. I see you missed the part on the invitation where it’s a costume party, but we can get that all straightened out before too long. Oh, a friend invited you? I wonder why they didn’t tell you to dress up! She’s not here yet, but stick with me, we’ll have you winning “best dressed” before the night is over! How? Oh, you’ll see, I have a special treat in store for you!
What you don’t realise is your friend didn’t tell you about the costume party because she knows I’ve got tricks up my sleeve for transforming you from Dapper Dan from the office into someone entirely different. We can decide who after you’ve mingled a bit. You can check out some of the other costumes to get some ideas, and then I’ll take you on a tour of the house.
Listen to the introduction here.
As we walk through the twists and turns of the house, the sounds from the party recede, and soon you feel as if you have lost your way. Finally, we come upon a closed door, and I tell you we’ve come to the costume room. You’re excited about that because you really do feel out of place with everyone else in elaborate yet kinky costumes. So excited that you don’t even notice the click of the lock as the door shuts behind you. I flip on several lamps to add to the light of the overhead chandelier, and you see several open closet doors, sliding doors, it looks like, on three sides of the room. As your gaze travels over the clothing you can see, you realise there is an abundance of pink, purple, yellow, and floral dresses. You slowly turn, looking for where the male costumes may be, and that’s when you see your friend sitting at the vanity watching your reaction to the sight of the clothes. You ask where the male costumes are, and she pipes up, telling you that’s why you say “Kink or Treat” at this party! You ask, and we get to pick, and tonight we pick our kink!
Your friend rises and goes to the closet, pulling out several lovely dresses. You sputter, flustered, that you aren’t going to wear a dress. She steps right up beside you and whispers something in your ear, and suddenly, your entire countenance and stance change to one of submission. You look almost delighted by the words whispered in your ear. You look at me and agree to wear whatever I pick out, knowing that with your strong jawline and short hair, people will see it for a joke and not believe you deliberately attempted to impersonate a female.
The outfit I select is a traditional black maid’s uniform, with a white apron and white petticoats. You think it will look ridiculous on you and be a good joke, and whatever your friend whispered to you makes you somewhat lighthearted in your agreeable submission. I lay it on the bed and instruct you to strip down. You take everything off but your boxers, and when you turn to me, you see I’m holding up a pair of pink satin frilly bloomers. You start to huff a bit, but with a look from your friend, you drop your drawers and take the pink panties in hand, quickly sliding into them.
From there, we make quick work of getting you into the petticoats and dress, zipping you up, fluffing your skirt out, and tying on the crisp white apron. You start to slide back into your loafers when I stop you and tell you you aren’t done yet. I hold up a pair of sheer black thigh-high stockings and a lovely pair of low pumps in black patent leather.
Although you mutter under your breath, you take the stockings and sit on the edge of the bed to put them on. You then step into the shoes, which miraculously fit you. I laugh at your astonishment, and that is your first indication that this has been carefully planned ahead of time, not just thrown together at the last minute.
Once the shoes are on, you think you are ready to go, but your friend assures you that you are only halfway there. She opens the cabinet next to the vanity, revealing a large selection of wigs. You are again taken aback by the realisation that we are not done with you, but you still think your masculine face will let others at the party know this is a big joke. What you actually find out as you sit down at the vanity is that we are far from done. The drawers on the vanity are pulled out, and as I prepare you for the placement of the wig, your friend begins to apply a full face of makeup, from concealer all the way to a finishing mist. You are contoured to perfection, making it look like the shape of your face is softer and more feminine. Once I add the wig, the transformation is complete. You sigh in relief, thinking that at least you can go enjoy the party now, maybe meet a nice lady who appreciates your willingness to make a fool of yourself.
As we put our things away and straighten up the room, you notice that your friend is gently smiling. You think you’ve pleased her, and maybe she’s the one you’ll get lucky with after this party. Before the door is opened, I stand in front of you, and I let you know that while you are dressed as a maid, you will not be expected to perform the duties of a maid. You are free to mix and mingle at will, enjoying yourself as much as you want. 
Then I pause and tell you that now that you’ve fulfilled the kink part of the party, we have a treat for you. You are instructed to lift your skirt and petticoats, and, thinking a quick handjob is about to happen, you do so quite willingly. I tug your bloomers down to reveal your penis and balls. What happens next happens so quickly that you are shocked. Before you can even try to take a step back, a ring is placed around your dick and balls, startling you. Then I hold up a flash of bright pink plastic, telling you that your treat is a new toy! I place a chastity cage over your dick and take the tiny padlock out of my bra, firmly locking you in place.
Now you panic a bit, thinking we’ve carried the joke too far. Again, you start to stammer and stutter. That’s when your friend pipes up and reminds you of what she whispered in your ear. You agreed to full compliance in exchange for meeting the woman of your dreams. What she didn’t tell you, though, is that the woman of your dreams will become your Mistress, keeping you locked and sissified from this Halloween Kink or Treat party forward. She remembered your late-night confessional conversations about how you rarely get second dates, and how women never ever sleep with you a second time. She remembers the way you call her ma’am when she gives you directions or asks a favor of you. She remembers your willing compliance to almost any shenanigans she’s come up with over the years, and most of all, she remembers my desire for a new chaste sissy to play with.
Now you’ve been turned into the prettiest part of my kink, you’ve received your treat, and it’s time to hop back onto the blog train to see what special treat Ms Constance has for you
Talk to you soon!
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Hey there Stephanie, you’ve got such a beautiful home! Thanks for welcoming us in to see Dapper Dan’s transformation. Happy horny Halloween!
Ms. Veronica! It was a delight having you, and I hope we can do a transformation together some day!
Awww, I can see many of our sissy friends reading that post and on the edge of their seats! Those in cages and those not, swelling with trepidation and/or envy, imagining themselves in the position of the unsuspecting party guest!
And there’s a bit of the “friend” in all of us Mistresses, I think! 😉
Ms. Rachel- I wish this kind of transformation for any of our callers who are seeking it, even just temporarily. I agree, I think we Mistresses can be a feisty bunch!
She listened and saw him for exactly what he was. I love it! There no hiding and I bet this is going to be the best Halloween of his life. What a wonderful story!
Ms. Luna-thank you! I think this Halloween is the start of an amazing journey for this sissy.
Ohhhhh Ms. Stephanie…what a delicious tale you wove! I loved every second of this and was hanging on every word! I so enjoyed his manly nature trying to come out at each turn, only to be reminded that this is what is happening! 🙂 And honestly, I am not sure which I enjoyed more…the kink or the treat!! Both soooo very yummy!!! 😉
Ms. Mandy- thank you for stopping by! I love a tale with twists and turns, and coerced sissification and chastity is surely a treat for us all!
Those friends who listen carefully are the best ones to have, even when at first you don’t think you’re going to be happy with what they come up with. But I think the narrator of this story is now in exactly the right situation to get maximum happiness!
Ms. Sascha- I think the hostess and the friend are going to receive maximum benefit from having a transformed submissive- oh the roads they will travel!
When the surprise costume is a little too convincing😈😂🎃
Isn’t it interesting Ms. Eden, that the “costume” fit perfectly, as if it was all pre-planned!
Very sexy, indeed! I do so love a nice trick, Ms Stephanie, and you certainly fulfilled the promise here.
Thank you, Ms. Becky! I think many people see the transformation as a treat, long term.
Are you kiddin’ me? Once I got to the costume room I would immediately go for a ball gown, just like the tulle one on the pic above; she is standing in between 2 trains. Put my hair up just like her’s and then with a princess tiara! Let’s Go!
Absolutely adore your enthusiasm Evelyn! You’ll have to get a tiara soon.
This was so much fun to read! I love it when a Halloween Treat turns out to actually be a trick. Especially when it’s such a devious and possibly permanent one! 😺
Ms. Roxie- thank you! I am of a mind to believe it does turn into a permanent treat!
I love it when a treat turns out to be a trick – especially when it’s such a devious one! What a fun story!
Ms. Roxie- I’m hoping it all turns into a fantastic treat in the end!
begs at the sight of your key
Ravyn, I suspect you would beg in such an enchanting manner that I’d have to give you a try!
Oh how delicious Stephanie! I love some bloomers as part of a ‘kink or treat’ outfit!
Putting someone in bloomers is always a good time all year round!
Getting the perfect chastity and denial Mistress? … sounds perfect!
Definitely a treat for all of us to have a chastity pet!
Oh, this was fun!! She knew! And this was not just a costume for kink or treat…I suspect this will be his new reality in chastity from now on!!
Ms. Delia, I suspect the party is not over for the newly minted sissy!
Ooooo, surprise sissification & chastity? Yes please! I loved reading about the subbie’s transformation from Dapper Dan to feminized & chaste French Maid. If they need any help adjusting to being under lock & key, I have a devoted sissy chastity slave I could introduce them to 😉
Ms. Lilly- I think the sissy chastity pets should have a group to share in, maybe a monthly tea party to discuss tips and hints on how to better serve their Mistresses. Wouldn’t that be fun?
Looks like the treat became the trick… and this is what happens when you ask for what you want and don’t specify how you’re going to get it. But it is Locktober right? I’m sure that maid will have plenty of chores to keep their mind busy. 😈🎃
Ms. Willow- chores will definitely be undertaken, but also proper training-I’m not going to deny her so much as change her wiring so she gets pleasure as a girly girl!
Oh Ms Stephanie I was waiting for a ” frilly” kink stop on the train lol. Why am I not surprised and yet still delighted that it is your stop? You pulled out all the stops (kinks & treats) plus… petticoats lol Love that.
Ms. Kay Marie- I am a big believer in the transformation opportunities given to us by Halloween. I’m glad you enjoyed my adventure into frills!
ooooh, soooo fun! I love how they thought it was just a joke only to find out that they were being transformed into the perfect, kinky treat for you to play with all year!!
Ms. Demi- I certainly think she’d be a year round treat for me! It’s so much fun to play with a sissy in chastity, isn’t it?
What a treat indeed to have a mistress like you and a pretty new play toy for you as well Happy Kink or Treat! So good and a treat every mistress deserves!
Thank you, Ms. Bianca! I do love a new play toy or just a sissy friend. Frequently it is both, though, I find!
I also really love it when they’re all dolled up and pretty. It’s when they clearly love it, but are still struggling to accept that it’s who they truly are that I love most!
Yes, Ms. Hadley! that line between “eww” and “Oohh” when the happy side wins is always fun to watch.
LOVE this!! I bet he’s absolutely shocked at how pretty he is when he finally sees a mirror!! I firmly believe we all need to spend some time rocking a look that questions who we really are. This was so fun to read!
Ms. Hadley- thank you for stopping by! I like the idea of an outfit outside of the norm, maybe outside of our comfort zone. I’ll have to ponder that a bit to figure out what that would mean for me personally!
🎃 Oh Mistress Stephanie, that was such a wicked delight! 💕 I loved the playful twists and the slow, teasing transformation — pure Halloween perfection! ✨ The mix of charm, submission, and surprise was just delicious. What a fabulous “kink or treat” party — I’d happily RSVP to that one! 💋🖤
Thank you, Ms. Laurel! I think slowly sneaking up on a transformation is so much fun, almost catching the “victim” by surprise! We love having your sexy self at the party!
Love this sexy sissy story, Miss Stephanie! That’s a Halloween she’ll never forget lol.
I think it’s a Halloween of definitely new beginnings!
He or should I say she, definitely got what she wanted *giggles*. Love the treats and tricks of this story!
I think it’s what she wanted, too, because she could have left, right? But no, she stayed to play!
This falls into the category of “be careful what you wish for” — because you just might GET IT! And let’s face it, you picked the kink and that petticoated sissy is going to get the TREAT — oh maybe not exactly what ‘he’ planned on originally … but hey, you Ms Stephanie are obviously the one in charge!
Ms. Olivia- I wonder how the sissy will feel as the party goes on and “she” catches the attention of some handsy gentlemen (plural!). I hope it turns into an even better, kinkier treat for her!
Oh, Stephanie! I just love a fun feminization story and the twist at the end! hee-hee What a kinky treat!
Thank you Ms. Andi- I would love to be able to do this year round as a kinky treat for us, wouldn’t you?
A Mistress with a padlock in her bra is and a memory like a steel trap is not someone to mess around with!!! Ms Stephanie, I love how you crushed his hopes of a handjob for Halloween lockup! It’s perfect!
Ms. Audrey- what would hopes of a handjob be without a Dominatrix to crush them? Sometimes, every so often, I do like to lock up a sissy!
I am always up for a party just like that I wouldn’t object to any of it
kristi- thanks for stopping by! I think it would be a fantastic party with a retinue of sissy maids in chastity!
What better time than Halloween to explore.
Amazing read
Ms. Gigi! Yes, explore and maybe exploit a little? Unsuspecting sissies are so fun, especially when they do so well as a sissy!
Halloween is the best time to explore a little gender fuckery! I love helping sweet sissies take their first feminization steps for a nice Halloween party, it’s the perfect excuse for some public crossdressing! And if there’s a pretty pink chastity device hidden in their panties? Well that’s even more fun!
I agree, Ms. Harper! Halloween is indeed the best time. I would think the pink chastity device is rather like the cherry on top, isn’t it?
Oh Ms Stephanie, what a wicked tale you weave! Tricked , treated and transformed!
I wonder, how many who read this blog would LOVE this to happen to them?
Hum? 🤔🤔
Ms. Erika- definitely a transformation! I’m pondering the after party at this point – will he stay a maid? I think so!
Oh, man! You know you’re in for it when you show up to a costume party with no costume. Great story, Stephanie!
Thank you Ms. Meshelle! Wicked friend not giving him a heads up, right?
Oh Mistress Stephanie I must confess I have jumped ahead and missed a couple blog train stations in order to peruse your contribution!
Also, I must confess I purposely arrived sans costume, praying that you may do this exact thing to me!
It was so difficult maintaining that poker face, while inside I was in heaven with every layer of femininity draped upon me!
Now, just an amendment to the tale, if you’d allow.
When the panties come down, you step step back, pause, and state, “Hmmm, I don’t have a cage small enough for you. I’m afraid you’ll have to leave”
“Wait Mistress Stephanie” I blurt out.
“Check my pants pocket…please!”
You seem puzzled.
I continue, “I’ve been a naughty pet and removed my cage. It’s much smaller!”
You reach into the pocket and search around until you pull out the tiniest cage you’ve ever seen.
You burst into hysterics as you instruct me, “Put it on and grab a tray”
little peg- thank you for jumping ahead, I’m flattered! I love your alternate ending, it’s perfectly charming!
Oh boy or should i say oh girly! hehe. They really did a service for women everywhere! If you can’t perform then you should take on a new role lmao!!!! Great job Stephanie!
Definitely girly! Thank you for stopping bye, Ms. Krista!