Author’s Note: This takes place before part 7.
The Shopping Trip
I bounce around the pet carrier in the back of Mistress’s SUV. I don’t know where we are going. Mistress said it would be a special surprise. I hope it’s not Dominique’s. It’s snowing out. I can see the flakes land on the back window before melting and gently rolling down.
I feel the car slow down and come to a halt. The rear gate pops. I climb out and open Mistress’s door. We are in the shopping district parked in front of an upscale sporting good’s store. I’m familiar with the store. It’s the kind of store that rich people shop at. People who can afford things like kayaks that they may use once a year for a day and go on ski vacations on a regular basis. They carry designer sports apparel and everything is full retail price. Mistress takes lots of ski trips. She loves the brisk, clean air and to wear her furs outdoors. But Mistress always has her coats made at her shop.
My nerves unsettle. I’m outside in public in my maid’s dress, full exposure. Besides that, the shop is closed and the shutters are already down. I shiver, more out of fear than the cold. My eyes plead with her. She reads me easily.
“I know you think that the public humiliation experience from your fantasy was taken care of at the VIP showing, but that was a safe and controlled environment, slave. You were simply bait that I knew Dom could never resist.”
My face burns a bright shade of red. The lock on the door turns. I hold the door for Mistress and pause. I swallow and follow her inside.
A woman leads us. She’s young. We head straight into the women’s clothing section. In its midst we find a platform display that has been cleared of its mannequins in front of a large leather chair. 2 more women stand beside the platform. I want to run away.
“slave, I’m paying these girls a lot of money to stay after hours to get you some proper attire for our trip. Obey them as you would me.”
My heart sinks. I nod.
“Please introduce yourself, girls.”
The first woman steps forward.
“I’m Melinda. You can call me Mel. I’m 21 and a college student. We’re all in the same sorority.”
The second woman moves up.
“I’m Britt. I’m also 21 and a college student.”
The third moves forward.
“I’m Shannon. I’m 22 and a college student. I’ve known Britt and Mel since their freshman year.”
“Thank you girls. My name is Cassandra. As we agreed on the phone, I’ll be paying you each $1,000 an hour to be our shopping assistants and you’ll split the commission evenly 3 ways. This is my slave, fs. You can call him whatever you like. We have a ski trip coming up and this will be his first year going as a sissy, so he’ll need some complete outfits both for indoors and outdoors.”
“Will he need skis too, Cassandra?”
“Skis won’t be necessary. My girlfriend and a few other friends and I will get to enjoy the skiing. fs won’t be skiing, so the outfits don’t have to be practical for movement. He will be outside for hours at a time, so it should be warm enough where we don’t have to worry about frostbite. fs waits for us at the bottom of the run while we ski and carries our skis to the next lift. If we go into the chalet, he stays outside and watches our equipment.”
“That doesn’t sound like much fun,” says Mel.
“Someone of fs’s status doesn’t require fun like we do. He’s happy as long as he serves our purpose. Carrying our bags, cooking our meals, or maintaining our gear.
“Cute, a slave boy. Our sorority house could use a couple of those. I’d love to have someone do my laundry.” Shannon says with a smile.
“What would you like the outfits to be like?” asks Britt.
“Good question, Britt. We will be gone for 7 days, so we will need 7 outfits. I want him to be dressed so that he doesn’t get cold, but I want it to be frilly enough where he’s uncomfortable in other ways.”
“Precisely. The more humiliating it is, the more I enjoy watching him squirm. If it’s frilly enough, he knows that he’ll grab plenty of attention, especially from the other women and maybe even some men. He’s so cute when he’s on the verge of tears from embarrassment.”
I blush. Mistress continues.
“A good place to work from is this: You all seem like stylish girls. When you see a girl trying so hard to be ‘cute’ that it makes you want to gag and laugh at how awful it is.”
All 3 look at each other and speak in unison.
“Like Sarah.” Laughter follows.
“slave, come here and get ready to strip.”
I approach Mistress slowly. my face is on fire. I present her my wrists, she turns forward the cuffs and releases the locks. This catches the attention of the 3 women. They are soon right on top of me. Their verbal interplay makes my head spin.
“You actually lock him into his dress? That’s terrible.”
“The dress itself is terrible. We should get one for Sarah.”
“Such a cute little gay boy, it’s a shame we can’t turn him on.”
Mistress continues releasing my locks one by one and steps in.
“Oh, fs isn’t gay. He’s not a transvestite either, or a cross-dresser. He’s a maid in my employment and I require him to wear this uniform. I can assure you he is straight as an arrow so feel free to flirt and tease all you want.”
Mistress pulls the dress over my head.
“But just to warn you, turning him on may prove difficult, he is ill-equipped.”
Their eyes widen. Mouths open. They inhale together and whisper.
“Is that a real chastity belt? I’ve only ever heard about them, I’ve never seen one.”
“Yes, Britt, it’s very real. He gets released once a week for cleaning, but it’s been a couple hundred days since his last orgasm.” I hang my head in shame. My face continues to burn.
“A couple hundred? I’ve never met a guy who can go more than a day or two without jerking off.”
“Please do tease him. slaves aren’t real people, so don’t worry about his feelings. I should add that his nipples are deliciously tender.”
My sex strains against the belt. Mistress knows how to push my buttons. I soon feel their hands along my waist line. A fingernail tapping on the belt. A finger slipped between the waistband and my skin. Gasps, whispers, giggles.
Mel straightens up and grabs my nipples in her fingers. I moan. My penis attempts again but is rejected.
“Look at that face, girls. Memorize it. That is him trying to get hard. That is the closest he will get to turned on.” I want to hide my face. I know that will upset Mistress. She continues.
“I want each of you to create 2 outfits for him. fs will model them and we can talk about anything that was your favorite. At the end I want the 3 of you to work together and create the final outfit. Don’t worry about the cost.”
The women depart to various parts of the store. Mistress has me kneel on the platform. The lights blind me. Melinda arrives first and helps dress me. I’m put on display in the outfit to Mistress while Mel gives her “presentation.” I can’t remember feeling more humiliated in my life.
“I went with a mini skirt since pants just didn’t seem right. Thermal leggings under the skirt. I tried to coordinate colors with his maid’s dress. I went with some huge fluffy Ugg boots since I felt they contrasted well with the skinny leggings, making him really stand out. I chose this turtleneck sweater since while it’s plenty warm, these sold terribly because the wool is way too rough and scratchy. An hour or two in this and his nipples should be raw and tender. I went with a jacket with a fur collar since I didn’t want anything that would cover the skirt. Some fur trimmed mittens. On top, a fur headband. He should look like a total mess out there.”
“Bravo, Mel. Excellent work.”
Mel reaches forward and pinches my nipple through the sweater. It’s so prickly it feels like the punishment lining.
Britt goes next. My head fills with despair as I’m undressed in front of them. Mistress rubs herself through her coat.
“I was going to avoid pants but then I remembered these. They were from a collection called “Ski Bunny” that took things to the extreme. They’re tight fitting thermal stretch pants with a big fur bunny tail.” She pats the tail. I blush harder.
“A tight ribbed turtleneck to keep his nipples entertained. This one has jingle bells on it which should be sure to draw attention to him out there as he moves. Some chunky knit mittens. A cropped jacket with a fur collar and cuffs. I didn’t want anything to be able to cover up that adorable little tail. A knit scarf with fur pom poms and more jingle bells seemed perfect. Rubber boots with a big fur cuff at the top and this cute little beanie with a huge fur pom pom and “Ski Bunny” embroidered on the front. It just seemed perfect.” She pinches my cheek.
“Very good, Britt. I love it. I’m sure he hates it just as much.”
The humiliation is painful. My body feels weak, like I can barely stand. My stomach twists and turns in knots. I undress for the next torture.
Shannon is third.
“Two years ago we got in these awful snow suits. They are adult sizes but are styled like a little girl’s. Even after being marked down a dozen times they still haven’t all sold. This one is a neon pink and very puffy. It has straps and buckles to cinch it tight at the waist, neck, wrists, and ankles. The sleeves are topped with large fur cuffs and there’s a hood with a fur ruff that can be cinched really tight, framing his face. The knit hat is to give him that “bundled up” look. The mittens actually have built in clips to secure them to the sleeves. I wanted to gag when these came back into style, but here they seem perfect. Matching moon boots.” My knees shake. The suit restricts my movement. It’s awful.
Mistress laughs and claps. The torture continues for more humiliations. One by one they strip away my dignity and put me on display as comic relief. By the end, my face no longer reacts. My cheeks may as well have been tattooed red. My frown feels permanent.
I brace myself for the final outfit. They are all extra proud.
Mel speaks for them.
“We pulled this from the figure skating department. A pink stretch dress with fur trim at the collar, cuffs, and hem. A sequined heart splits the cleavage and it’s actually quite warm. Sheer leggings. Fur leg warmers. Wedge ankle booties. A white fur-trimmed vest with “Ski Bunny” spelled out across the back in sequins. Mittens, a matching fur bonnet, and a white fur muff. This one is designed for skaters so it fastens around the waist with a belt. This was just adorable.”
My eyes fill with tears. Mistress laughs a hearty laugh. The women high 5 each other and giggle together. After a couple of minutes I undress again. Mistress has them help me back into my uniform. The women anxiously assist and love every minute of it. The locks click. My face burns. I’m so mentally exhausted I barely feel anything except for shame.
They bag and box up our purchases and Mistress pays for them. She gives each an additional envelope. Mistress turns to me.
“What do you say to the nice girls, slave?”
I kneel and bow in front of them.
“Thank you, ladies, for being so helpful in picking me clothes. It’s always nice to get this much attention from such pretty women.”
I rise and they cycle past me, pinching my cheeks and telling me they can’t wait to see me again next year. The thought makes me shudder.
In the back of the car I collapse in the pet carrier from exhaustion and stress. We drive home. My thoughts revolve around one thought: I hope Mistress had fun today.