✈️ Sky High Confessional #4 – The First Time I Discovered Thongs

It might surprise you to learn that I’m actually pretty new to thongs — it’s only been just on four years since I first put one on. In fact, before 2020 I hadn’t even thought about it. It wasn’t until that year that I first dabbled with trying a jockstrap, and even that felt daring at the time.

Then, in 2021, I met this sexy Spanish guy at the gym while visiting Sydney who had a thing for thongs. We later chatted on insta and he suggested I try one, and I remember thinking how wild that sounded. There was something about the femininity of a thong that made me hesitate at first... but eventually my curiosity clearly prevailed :-p

I ordered two Joe Snyder ones (in red and creme in the pics in my home garage gym!) and it felt so naughty, almost obscene, like I was doing something I wasn’t supposed to. COVID was a period of real sexual exploration for me (maybe a topic for another confessional), but up until then, I’d never really played around with how different clothing or underwear could make me feel.

When they finally arrived, I remember feeling nervous just opening the package. I didn’t even want to hang it up on the washing line: it felt too risqué. But when I put it on… wow. I loved how tight and secure it felt, the way it hugged my body, and how the strap sat between my cheeks, brushing against me all day.

It was surprisingly sexy, empowering, even. At the time, I was deep in a bulking phase and had built up a serious butt, and the thong just framed it perfectly. Before long, I wanted to show it off.

Within six months, I started posting my first thong shots on Instagram ... the very early beginnings of what you see here today. That tiny piece of fabric ended up changing everything.

Now over to you...
When was the first time you put something on that made you feel sexy, bold, or completely yourself?
Best answer gets a personal reply from me 😈✈️