The Grass is Greener

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Drew wasn't supposed to get back until the following Monday, but Jesse surprised me when she came through the door on Thursday afternoon, a day early. I was in the dress.

She took one look at me. "So are you our maid then?"

"Maid?"

"The pink..." She smirked. "Sissy maid?"

"I hadn't really thought about it..." I said, and she glared at me until I added, "Mistress."

"Well," she nodded, "you are now. I'm going away again this weekend, so I need to make some phone calls." She pointed around. "Do maid stuff for now... sissy."

An hour later, Jesse tapped me on the shoulder, "Hey Sissy, I need a drink. Make me a drink..." then added with a sigh, "a stiff one."

After a trip to the kitchen, I handed her a tequila sunrise. She took it and sipped, looking glum. "The pink does look nice," she said.

"What's wrong?" I asked. When she didn't immediately answer, I added, "Mistress" and she smiled half-heartily.

"Oh, Sissy..." she moaned, trying to be playful, but it ended up sounding even more disappointed, which somehow reminded me how much work my enslavement-slash-emasculation really was for them. "Fine, look, my umm... personal trainer flaked out on me, so my weekend is off." She looked into her drink.

"Personal trainer?... Mistress," I asked.

"Yeah, well it's a 'special' kind of weekend. At least it was."

"Anything I can do?"

She sighed again, shook her head, and flicked the end of my tube with her fingernail, making it ping. "Not really." She took a gulp of her drink and added, "I mean I guess I'll have to settle for torturing you all weekend. Tying you up more and more, and making you do progressively harder chores until it becomes ridiculous, and all you can do is squirm around on the floor, so I guess that's something." She shrugged.

I just about choked, feeling tingling in my crotch from what she had said. "Yeah, that's too bad..." I stammered out.

"Unless..." she chewed her bottom lip. "Unless?" Her eyes looked up at me.

"Unless?" I asked.

"Would you want to give it a try?"

"Give what a try?"

"Being my ah... personal trainer?"

"What would I have to do?" I asked, apprehensively.

"I can't say."

"Why not?"

"Because," she pinged my tube again, "It's a secret."

"Would I need to fly... like this?" I asked, thinking of going through airport security in my sissy dress.

"No... it's a road trip. But I would make you drive up there like that. Though you would need some other clothes too."

I wasn't sure if she was suggesting I show up to some sort of marathon... in a frilly pink dress... or what. "Maybe... is it... public?"

"No." She chortled. "You don't have to worry about that."

"Would you tell me what it is?"

"No, I don't think so." She looked at me flatly.

"Okay..." I gulped.

So we spent the next morning driving up the coast with me fully sissied out, and Jesse sitting next to me. She'd pick at the ruffles of my dress, at my bright fuchsia hair, and dab more lipstick on me at stoplights, just to remind me of how I was dressed.

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⏰ Last updated: May 25, 2022 ⏰

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