Wearing a Thong and Skirts for the First Time

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The first task Miss Lois ever gave me was to wear a thong for the first time. When I started talking to Miss Lois several months prior, we didn’t really dive into anything. I was a bit suspicious because I struggle to trust people online because of things that have happened in the past. We’d exchanged messages every now and then, with sometimes breaks of weeks in between until it slowly started to become more serious? (not sure if serious is the right word.)

The transition was still fairly slow. I was a complete newbie if you want to call it that. It’s kind of like I’d been living under a rock, in a way. I’d never worn a thong (didn’t really realise what it was lol), didn’t wear heels or dresses and skirts. In fact, I spend most of my time in sports kit of which I had loads (thanks to the university forcing me to buy it). So one of the first things I remember she told me to do was buy a red thong. I had to google where to get them and felt nervous about actually getting them.

I was about to move to a different place at this time, literally having maybe three days left, and the following thing she told me to do was to wear only dresses or skirts in those last days and to also wear a thong.

This must sound ridiculous to everyone I’m sure, but I was very anxious about 1. wearing a skirt or a dress and even more anxious about 2. wearing a thong with a skirt or a dress. Why? Because I felt like all the people I knew were only used to me wearing sports kit (in fact, they all did the same) and I thought they’d look strangely at me if I suddenly wore a dress. And as for the thong… I wasn’t exactly used to the feeling of the wind potentially blowing it up and potentially exposing me.

So I went to the shop with my best friend who was living with me at the time, and who also identifies as a submissive and knew about me. (In fact, I’d gotten his BDSM desires out of him, hehe). It was only a 10-minute walk to the shop from our house and I was wearing a skirt but without a thong, which we were going to buy (because I had packed the other one I’d already bought – I know… stupid.) All the way to the shop I kept on saying things like how I was feeling uncomfortable or asking if it really looked okay. I told him I should wear a thong underneath it though, and that I was technically almost breaking a rule right now (although it couldn’t really be helped because my packed stuff had already been shipped away). So he made some jokes, teasing me and suggested I buy the thongs and then change in the shop. But that idea freaked me out enough that I didn’t, lol. Which then, might have been breaking a rule… but I didn’t actually tell Miss Lois and pretended I hadn’t really done anything wrong. Guess that shows I wasn’t a well-trained slave yet.

However, in order to do what she’d told me, I went out with my friend again that night, wearing a skirt and a thong this time and we walked along the promenade (yay for living next to the beach) and watched the sunset. I felt as uncomfortable as I’d done earlier on the day, but even more, so that evening because my skirt kept blowing up… Enough that my friend pointed out he’d seen… well… lol. And then he made a joke that it would be actually terrible if I didn’t wear anything underneath my skirts and dresses anymore, which he was sure would be the next thing Miss Lois would make me do. It was very embarrassing and scary, but it also felt good, deep down, to wear something nice for once. Before I had moved to this place for university, I used to buy skirts and dresses and liked the idea of dressing up nicely (but simply never dared to). Being told to do it now pushed me to actually do what I’d always wanted to do. It just seemed like it might take a while before I’d feel comfortable doing it.

Then the day after, my friend and I went to a beach in a different place, which put my mind at ease a lot more. I still felt a bit nervous because I chose to wear one of my new dresses which was kind of short. Loads of blowing up potential, haha. So we walked around for a few hours and the longer we did, the more comfortable I felt to the point that I started enjoying it. It was kind of a freeing experience. But then on our way back, we ran into two people from my football team that I wasn’t particularly close with. They looked completely surprised to see me in a dress and I felt my cheeks redden. I tried to pull my dress down, afraid that it was somehow too short or that they could somehow see I was wearing a thong. We made some polite conversation and then I walked away as quickly as I could, my heart beating in my chest.

I guess, looking back, I must have looked good, right? Let’s just say that that is why they looked so surprised. It’s quite funny now. I could go back and wear whatever nice thing I want and feel completely comfortable now (although I guess that doesn’t include high heels quite yet, ha).

Slow steps, I guess. Very slow steps.

Xx MLSlavePuppet

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4 Replies to “Wearing a Thong and Skirts for the First Time”

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