Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 31 by PrincessAriana PrincessAriana

What's next?

Join the Club

It's too late to back out now. You walk to the intimate attire store next to your stepdad, blushing and wishing you were anywhere else. You can't see him because you really, really don't want to lock eyes with him on the way into the horniest clothing store yet, but you can sense the grin on his face.

When you get to the entrance, you grab Jeff's sleeve to stop him. "Actually, I changed my mind. I, um, don't need anything here after all." You turn abruptly to walk away, but a firm hand grabs your wrist to stop you.

"Wait a second, sport. You're the one that made us walk all the way over. May as well at least browse some." He cocks an amused smile at you, obviously enjoying how flustered you are, and drags you into the store by ****.

The interior of Divine is like a dimly-lit clothing cavern. Soft sensual music is piped in from hidden speakers. Fake rocks and large screens line the wall, playing scenes of waterfalls and tropical jungles. The whole ambiance is like something out of a perfume commercial.

Jeff pulls you past the checkout counter and into the depths. You find yourself among racks of lace and leather, bright costumes and sultry sundries.

"Daddy!" you hiss, too embarrassed to move after he releases his grip on you. You're vaguely aware of the silhouettes of other shoppers gliding around in and among the racks of clothes, but it's too dim to really focus on anyone. You're grateful for the faux privacy, though still **** to be in this sort of store in the first place.

Jeff ignores you, already rifling through the articles on the rack nearest to you. "Ooh, what about this?" he says teasingly, holding up a set of black lace fabric. The tag depicts a stunningly beautiful model wearing crotch-less thong panties, a sheer bra, intricate lace stockings and a garter belt. The naughtiest bits are blurred, but only barely.

"Stop!" you accidentally squeak the word out, voice cracking from embarrassment as you snatch the hangar from him, putting it back before anyone can see. "Don't touch anything. Don't even look at anything! What if someone I know sees us?"

Your stepdad makes a derivative little snort and shrugs. "Who could possibly see us here? Wouldn't they be in the same boat as you? Besides, we're supposed to be learning how to not care what other people think, aren't we?" He reaches out and tugs the strap of your bra, letting it snap back against you.

You blush and stammer, "N-no! I mean, yes about that, but... It's too embarrassing. Can't we just go home? I got so much already..." You look up at him as sternly as you can, but shy away behind him when you think another shopper is coming towards the two of you.

He shakes his head. "You wanted to come in here, not me. How about this - I'll wait outside and let you try a few things on? Let's say... five, okay? I'm not asking, Aiken. I think you know what to say."

You fume and cross your arms, feeling so juvenile to be pouting in the middle of a public place, but say, "Yes, Sir..." You even make sure to look up at him and enunciate. A brief but terrifying image of you getting spanked in public is enough to make you very well-mannered.

"Good!" Jeff smiles and pats you on the back. "Then take your time in here and I'll wait for you outside. Oh, and Aiken, just as a little incentive to get you out of your shell... How about for every dollar of the total you spend here, I'll give you half that much in cash. Call it your allowance for this month. Remember, I'm paying for the clothes too, so this is a tremendous deal for you."

You're a little stunned at his offer, staring as he winks and starts to leave. You gulp and manage a nod, and are turning to go deeper into the store yourself when you feel a sharp slap on your ass. You jump and make a noise like 'Eek!' rubbing at your behind.

Jeff laughs as he disappears from view.

He definitely went under your skirt for that one!


Megan's face heaves with exasperation on the screen of your smart phone. You watch her roll her eyes as you pull your knees up to your chest on the bench in the changing room of Divine.

"I don't see what the big deal is," she says shortly, "weren't you literally already at the mall to buy lingerie?"

"Not this kind of lingerie!" you half whisper, half whimper, trying to keep your voice down. "It's like, sexy stuff... like bedroom lingerie..."

Megan huffs yet again. "Aiken, you are literally wearing panties, a bra, and a miniskirt right now. Who cares if they're lacy or sheer or whatever. You aren't even the one paying for them! Just get a load of stuff and start modeling. I'm ready to see slutty Aiken!" she laughs and sends a pic. It's a screenshot she took from an earlier call. You're in a changing room trying on a pink cheetah-print bra. She's added the caption 'trying on clothes for Daddy! think he'll like? <3'

You gasp and cover your mouth. "Megan! What the hell is that?! You took screenshots? Delete that right now!"

"Nuh-uh, no way! I've got a whole album full of these. And I'm about to get some sexy ones, too. Unless you want me to send this to your stepdad. Oh wait, I mean to your daddy!"

You groan in disbelief. "You are such a... ugh! How do I even pick out what to buy though? Like should I just grab whatever or go for the expensive stuff only? Dadd- I mean, Jeff said he'd pay me half of whatever I spend here, so shoul-"

"Oh my god, Aiken!!!!" You have to put your thumb over the speaker of the phone to mute Megan's wail. "Are you kidding me? He's paying you to shop and you're whining about it?! Get out there and get ten- no, twenty outfits. RIGHT. NOW!"

"But-!"

"No 'buts'! Did you already forget that I'm taking time out of my day to help you dress, help you put on your makeup, and even help you shop?" You can see fire in her eyes and know she won't back down. She scares you when she gets this way, and you can't say no.

"Bu- I mean... Why shou-"

"BECAUSE I SAID SO!" Megan yells so loud the phone audio peaks and cracks.

You spend the next two hours trying on lingerie and getting laughed at by your only female 'friend.' Some low points include a cheerleader uniform with the word 'Daddy' printed where the team name would go; a french maid uniform with poofy skirt and full lingerie set underneath, a Playboy-style bunny costume, slutty schoolgirl roleplay attire, and several sets of lacy, stringy, sheer things you could barely figure out how to put on.

By the end of your ordeal, you were so emasculated you could barely even remember the days when you used to just roll out of bed and play games. Your brain was now completely occupied with thoughts of women's clothing. You were sure your masculine brain was slowly turning pink. Well, pinker.

You end your call with Megan and make the walk of shame to the checkout desk to pay for your haul with Jeff's card. As you complete the transaction, you remember the whole reason you wanted to go there in the first place.

"Um, does someone named Jenny work here? I was told to ask for her... Jessica said I should."

The woman behind the counter was edgy by any interpretation. Dyed black hair, piercings in her lip, nose and eyebrows. Black lipstick and heavy makeup. She blatantly looks you up and down as if sizing you up. She wasn't exactly feminine, except for her chest, which was enormous. "Jessie sent you, huh? Oh..." she laughs and smirks as if realizing something. "And what can I help you with, boy?"

You cringe at hearing her call you a boy out loud. And the intensity of her stare made you feel somehow small, diminished under her judging gaze."W-well I'm not sure. Jessie just said to ask for-"

"Jessica," the woman corrected harshly. "I get to call her Jessie but that privilege does not extend to you. You may call her Jessica, and me Mistress. Understand?"

"Wh- really?" You laugh like it's a joke, and look around to see if you were being pranked, but no one else was around. Jenny crosses her arms tersely. Something about the way she looks at you makes a chill crawl up your spine and you answer with a painfully awkward half-smile. "Y-yes, Mistress..."

"Hmmph. Good boy. I see why Jessie sent you now. Here, fill out this form and I'll throw in a special gift for you to take home." She draws a simple clipboard out from under the counter and pushes it towards you. The sheet on top asks for normal information like your name, age, email, and some other things.

You fill it out and push it back to her.

She looks down at the sheet as if to verify you did as you were told. "Great, welcome to the club, Aiken!" and smiles at you. Maybe it's the fact that it was the first time she'd actually smiled at you, but it felt good, like a reward for your effort. She tosses a small cube-shaped box into your bags and waves you off without another word.

As you're walking to meet Jeff at the benches, your phone pings with a new email. The notification reads;

[MisstressJ@ClubSissyDivine sent you a message: Welcome to the club, new sissy! Enjoy the daily newsletter and exclusive deals on all things sissy; from lingerie to toys, hypno files, and more. To opt out, ask your Mistress and be prepared to beg.]

Club... what?! You quickly stop in your tracks and set your bags down. You fish out the box Jenny had put in your stuff and open it. Inside is something that looks like a little metal tea strainer, except the space between the concentric rings is too big. The shape reminds you of a...

Oh god! You realize what the contraption is when you see a small lock and key in the box with the metal enclosure. A little note tag inside reads: Clit Trainer, 'Beta discipline' model, size 5.

"Everything alright there, tiger?"

You snap the box shut and whip it behind your back as fast as you can. Jeff is walking towards you. You must have been lost in thought and not noticed him get up and make his way over from the benches.

"Yeah, nothing! I mean, I'm alright. I mean..." You mumble and mutter, words sliding off your tongue like sheets of ice as you try to form coherent thoughts.

Jeff laughs and throws his arm around you, walking you both towards the escalators. "Haha, calm down, I'm just teasing. Looks like you got quite a haul in there! Anything sexy?"

"N-no, just uhm, more underwear..." you lie, tossing the box into one of the bags and closing it tight.

"Want me to hold tha-"

"No!" You clench your fists over the top of the bag and refuse to give it to Jeff. "You have enough already. I'll carry this one."

By the time you reach the car, you breath a sigh of relief. A whole day in public dressed as a girl... You sink into your chair, running a hand under your skirt to keep it straight and modest, and close your eyes the whole way home.

When you pull into the driveway, you let Jeff get out and open the door for you, then bring in your one bag while your stepdad gets the rest.

"Well, what'd you think of today, sweetie? Anything you want to say to me?" Jeff asks as he brings in the last load of clothes-laden bags. He winks at you teasingly. "Cute bra, by the way," he adds, brushing the exposed strap on your shoulder with two fingers.

You smile and feel an odd giddiness well up inside you. It had been a long, stressful, and very, very embarrassing day for you, but now that it was over, you were overwhelmed with... something. A kind of pride, or excitement, or thrill. Something that threatened to burst out of you.

You smile and giggle and look up at your stepdad. Then you prop yourself up on tippy-toes and lean in, closing your eyes and letting your lips meet his for several long seconds. Your arms wrap around his solid back and you feel him clutch your body to his with his big, comforting arms.

"Thanks for taking me shopping, daddy. I had fun."

Before he can reply, you turn and run up the stairs, leaving Jeff stunned. You're too shy to stay there where he can see you for even a second longer.

You spend the rest of the night on your bed clutching your pillow and trying to sort through your many, many emotions.

What's next?

Comments

      Want to support CHYOA?
      Disable your Ad Blocker! Thanks :)