Like a lot of sissies, I’ve felt various periods of shame related to crossdressing and sissy training. I’ve taken long breaks, gotten rid of clothing and toys, and felt depressed at times over what’s ultimately a fun and harmless kink. The last couple of years I’ve worked hard to be more accepting of my sissification story. As part of that, I wanted to start writing about my personal sissification journey, which started with a love of thongs. 

My thong & whale tail obsession didn’t really start until high school when I ended up sitting behind this girl, Sabrina, in most of my classes because our last names were right next to each other.

She was a smart, bookish blonde with small breasts and a gorgeous ass that seemed to come from nowhere for how thin she was. She dressed like Evan Rachel Wood in Thirteen with these super low-rise jeans that tightly clung to her incredible ass. And with low-rise jeans came copious thong slips and whale tails. Every week I was treated to so many beautiful thong slips until, sadly, we stopped having classes together after freshman year.

The Thong That Started My Sissification Journey

Towards the end of my senior year of college, I had just finished doing laundry and dumped out the clothes on my bed to put away. Tucked in between my clothes was a small girl’s thong.

It wasn’t particularly sexy: a simple, floral-pattern cotton thong with a skimpy back that looked like it had seen a lot of love. I wondered who in the dorm it might have belonged to. Were they missing their thong? Had it made them feel sexy? Did they ever admire themselves and how cute it made their booty look?

I don’t know what compelled me, but I took off my clothes and put on the thong. Clearly meant to be worn by a small girl, I barely fit in it and my “future clitty” of course couldn’t be contained by the small front triangle, but I still felt cute and sexy. I pulled the straps high on my hips and the thong went deeper and deeper into my ass. The feeling was incredible and I started to touch myself and quickly came all over the thong.

So without knowing much about anything, I looked up where to buy thongs for men thinking that’s what I was into. The only place I saw in my area was one of the last few crumbling k-marts. Like there were literally weeds growing all over the parking lot. The place was a total mess, really rundown, but I found a pack of plain men’s thongs (they had a pretty big back, so maybe closer to Brazilian cut underwear).

Of course, they didn’t have a self-checkout and the only cash register open belonged to a teenage girl. I couldn’t get through with it, left my cart, and walked out. I didn’t have the courage to go through with it in person, but the desire was still there to own a thong.

As fate would have it, I happened to come across an article on a major news site about a designer’s lingerie brand for men. I had never considered that such a thing existed or that there might be other people like me looking for men’s thongs. The brand was too expensive and didn’t ship easily to where I lived, but poking around the internet I found a company called Body Aware.

They carried all types of men’s underwear from silky boxers to thongs and g-strings. Body Aware even had what looked like sports bras for men which seemed pretty out there. Some of their style was classy, sporty, or more feminine. The site wasn’t sleazy either. Very professional with muscle-y male models displaying these sexy panties like it was just another day at the office.

You’d have thought I would have picked something that was more masculine for a first thong, but no: I went all in! I was drawn to this satin pink thong that had a really thin band in the back leading up to the cutest thong triangle. The kind I had seen sticking up from my classmate Sabrina’s low-rise jeans back in high school.

Each day seemed to last forever waiting for my first real thong to ship until suddenly I was holding an unmarked small, padded envelope. I tore her open and she was in my hands. I couldn’t wait and tore my clothes off. I started sliding the thong up, the cutely ruched side straps sliding up my legs. Though this thong didn’t have a pouch for say I disappeared into the front of it with only a cute bulge showing. Lastly, I slid the thong up even higher feeling the pressure build on my tight little hole, and raised the straps as high as they could so it looked like I had hips. This thong felt made just for me.

I admired myself in the mirror. I’d never thought about what my own butt looked like before, but now it was adorable and sexy. Next, I grabbed a pair of skinny jeans. They weren’t mid-rise, but I had hiked the thong so far up that I had a whale tail. I didn’t think at all about what this might mean other than I felt like I was getting a taste of how sexy those girls looked to me walking around with their whale tails.

To Be Continued…

I ended up buying many more thongs from Body Aware and started to push it a little further in my first foray into crossdressing buying stockings, a garter belt, and a bra. I’ll save that for part 2 of my sissification story! If you’re looking to start your sissification story, take a look at my Sissy 101 guide.