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Rated: 18+ · Interactive · Fashion · #1928522

A bunch of stories that all result in a man dressing like a woman.

This choice: He wanted you to visit the hairdressers.  •  Go Back...
Chapter #34

Come and Get Your Happiness

    by: Seven Author IconMail Icon

Your heart sank further with each word you read on James’s message.

Hey there Shirley! (Yes that is your name until I say otherwise) Any luck on your quest? I’ve been backing up my little photoshoot just in case you get any silly ideas of trying to escape.

With a pout, you sent your reply.

No, I’ve got them. Now I’m out a few hundred dollars…

Boo hoo. We both know you would have just blown it on more ST merch anyway. Now for your next job you need to head across the mall to Suzanna’s and schedule an appointment.

Suzanna’s? Isn’t that the hairdressers where Nora works??????

Yeah but come on dude. What are the odds she’s going to be there now? Plus whats worse? Visiting Nora at her job or her getting a tour of your room? Up to you!

.....Fine

I think you mean ‘Yes Master’ Now schedule a styling appointment ASAP. You know what name to give them ;)

Just as you were about to put your phone away, grumbling in frustration, a second message dinged.

I’m getting kind of hungry too, so make sure to stop at that fast food place on the way home. Pick me up a burger, you can get a kids’ meal. You know which toy to get, right?

You had decided you were officially no longer friends with James anymore as you picked up your shopping bags and trudged your way across the mall. Despite your pleading Suzanna’s was still open when you arrived, with more than a few guests already there. Thankfully you didn’t see Nora among the staff as you approached the counter.

“Hi there!” A woman with a bubbly smile and a blonde bob cut greeted you with a wave. “How can we help you? Looking for a trim?”

“No, thank you. I’m…I actually was…I wanted to schedule a hair styling appointment. When’s the soonest I could do it?”

“Hmm….” The blonde receptionist flipped through what you guessed was an appointment book. “I’m afraid we’re quite busy today but the earliest we can squeeze you in is Friday afternoon. Does that work for you?”

You mentally cursed. James hadn’t told you why he wanted you here, but if his plan was anything like you imagined, you hoped to be able to put it off for at least a month. That should be long enough for James to get bored of tormenting you like this. Instead, you only had a grace period of TWO DAYS!

“Sure.” You told the receptionist with a strained smile. “That sounds…wonderful.”

“Great!” She beamed with more than enough enthusiasm for the both of you. “I’m gonna go ahead and pencil you right in for Friday! What name should I put on the appointment?”

“Shirley.” The word felt heavy, weighted as it dragged itself past your lips. Like you had just crossed a line, made a decision that meant there was no going back. If the receptionist found your markedly feminine alias unusual, she gave no sign, her smile as broad as ever.

“Alright then, Shirley. Your appointment is at 4 o'clock sharp!” She chirped.

“Thank you. See you then.” Your voice was low and subdued as you turned and walked away, unsure how to feel about a pretty woman calling you by your childhood idol’s name. It sent a tingle down your spine, bearing the moniker of your favorite star, yet you felt shame proportional to the excitement it gave you. You’re a guy! You shouldn’t be getting excited using a little girl’s name! Plus, it wasn’t like you were worthy of it. Shirley Temple was a timeless star, a cultural icon, the voice of a generation.

And you…you were just Ryan.

Your mind was in a daze as you carried the shopping bags back out to your car, climbing inside and turning the ignition. As soon as you did “He Was a Dandy And She Was a Belle” was blasting out of your speakers, the familiar jaunty tune giving you momentary comfort as you pulled out of the parking lot and headed back towards your new life.

Halfway down the road you remembered James’s other request, pulling into the drive-thru. At least this was something you could do where nobody had to ask you your name.

—------------------------------------------------------------

“Alright Master, I’m back.” You called out in a faux happy tone as you closed the door to your house behind you. “I got the food and the clothes you asked for.” Well, most of the food anyway. You had gotten hungry and begun snacking on your little sister’s meal on the way home. At least, that was who you told the employee at the window it was for, thanks for the idea Amber.

The food was decent but you rolled your eyes at the toy. Seriously, a glow-in-the-dark Elsa? That movie came out forever ago, how were people still obsessed with it? You didn’t get the excitement about Elsa and Anna in the first place. Why were little girls so obsessed with these two bland stick figures when there were so many better idols.

You know, like Shirley! She was everything those little girls wanted to be, not to mention real! She was adorable, famous and able to charm anyone. It really didn’t get any better than Shirley Temple! You shook your head with a sigh as you realized where your train of thought had led you yet again.

Why were you like this, obsessed with a little girl from nearly a century ago?

“In here, sissy! Let me see the goods!” James called from the living room. You carried the shopping bags there and set them down on the floor. Your “friend” was exactly where you had left him; sprawled out on your couch like he owned the place, scrolling through his phone. With a frown you set his takeout bag on the table in front of him.

“Shirley! Lovely to see you again!” He sang with a tone absolutely dripping with pompousness. “Looks like you can follow at least one direction right! I trust you made your appointment too? Like a good girl?”

“Yes.” You mumbled, cheeks burning at those last two words as you suddenly found the carpet very interesting. “It’s on Friday…”

“Wow, sooner than I was expecting! We better start getting you ready then!”

You feared what Master James meant by that.

“Now, show me all the pretty dresses you bought for yourself!” James gestured as he opened the bag and began digging into his burger and fries. One by one you dug out the dresses, sailor outfits and petticoats you had bought at the costume shop. You felt more than a little humiliated, holding out each feminine garment for your Master to inspect, usually to nod approvingly between bites.

He nearly choked laughing as you presented the pair of mary jane shoes you had acquired, complete with the sets of ruffled tights.

“Well done Shirley! You’ve really gone above and beyond!” James congratulated you after finishing his meal, shamelessly wiping his hands on your couch. “But don’t worry. While you were out sissy shopping, I’ve been pretty busy myself. I got something I’ve been wanting to show you, and now is the perfect time!”


What does James want to show you?

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