My Sissy Adventures

After a near-miss that almost cost me my whole world, I'm sharing my true stories of degradation, sissification, chastity, and anonymous sex in an attempt to purge it from my life.

These stories will come in no particular order.

The older I got, the less I cared what people thought of me. I didn't worry about asking to try on bras in Layne Bryant or Victoria's secret. My only worry was that they would think I was only doing it to get off, so as long as I stayed in chastity, there would be no outward displays that might give that impression.

I never asked to try on panties though. There were hygiene considerations that I didn't want to think about. Besides, I was almost always wearing thongs and panty liners to absorb my leaking boy-clit.

I went to a sex toy store to buy the stripper heels, a fetish store to buy the corset, Spencer's Gifts at the mall for the garter belt, Claire's for the jewelry and wig, and JC Penny for the pantyhose and thigh-highs, I decided to try and find a dress at Kohls after the usual spots didn't turn up what I was looking for. I did all of my shopping during the day as I drove around town for work, I was fully butch when I went in and dressed in the men's dressing rooms.

I finally found a purple skater skirt with a black satin long-sleeved top. The skirt gave me the appearance of hips but I wore it high on the waist so you could just make out the tops of my thigh highs when I moved. Nothing above my waist was feminine in shape anyhow, my legs were my most feminine features I wanted them to be the main attraction.

I was ready to drive half-way across the country entirely in drag.

I would leave the house dressed normally, stop by my work truck to grab my gurl clothes, change into them at the first truck stop outside of town, and then drive to the east coast in chastity and drag. As a bonus, I loaded my phone with Bambi Sleep Hypnos to listen to. My mind raced with possible scenarios I might encounter; would I get pulled over and have to explain my dress? Would I get hit on at a rest stop? Would I get beaten? Would I get raped? Would someone recognize me and tell my wife? Or would nothing happen but the thrill of actually doing something so different from what my normal behavior had been my entire adult life.

The day came and I stuck to the plan. Kissed my wife goodbye, drove to where my work truck was parked, grabbed my hoe-bag, and headed to the first stop with decent bathrooms I could find, a Flying J truck stop. This was it. Aside from walking out to the mirror in the changing area, this was the most public arena my inner sissy had ever experienced. In broad daylight. The scenarios again fired off in my brain. Homophobic rednecks attacking me, being notified by a familiar face, being accused of perverted behaviors, etc... I was shaking as I stepped out of my jeans and into my lingerie. Shaking still as I shimmied my hips to get the skirt over my ass. Sweating and shaking as I snapped my lacey bra into place and pulled the blouse over my head. The percussive sound of my heels hitting the tile as I stepped around the stall almost certainly gave me away to those outside the relative safety of my impromptu changing room. Precum strings roped to the floor because despite the nerves, the swimming thoughts, the very real consequences, and the fear, this little Bambi-bimbo sissy slut was about to have her debutante debut.

I steadied myself and added my final touches; jewelry, my wig, and over-sized sunglasses. I reached for the door and with a deep breath stepped out of the stall.

Panic set in and my eyes dropped to the floor immediately in front of me. As carefully as I could stride out on the very high heels I made my way to the door, navigating by my peripheral vision, my eardrums throbbing from the blood rushing to my head, clutching my backpack with white knuckles, my inner-Sissy still cut through enough to swish my hips and place each step carefully in line with the last. That rhythm carried me out the door and safely into my truck. I had jumped off the high dive. The worst part was over.

It didn't take long for the high to wear off and the desire to be seen again take over. This time my Bambi's brain convinced myself I needed to save money on drinks for the trip by stopping at a grocery store and buying a case of bubbly water. This time my head wasn't down at all and Bambi kept reminding my shoulders to pull back, forcing my tits out, and pulling the heel of one foot past the toe of the other to give my hips a real swing. I put my keys, credit cards, and ID in a clutch and stepped out. Halfway to the store, I had a wicked thought, I should take my panties off. I turned around and went back to the truck. I looked around quickly and opened the door. Without actually getting in, I hiked up my skirt and thumbed the straps of my thong down my legs and over my heels. Anyone looking would have certainly seen more of me than they wanted to. I stepped out of the panties and bending over at the waist like a good slut I picked them up off the ground and threw them into the truck.

The air felt cool on my swollen testicles as I walked into the store like the brazen hussy I wanted to be. I felt like Christina Ricci in Black Snake Moan, only twice as horny. The more people stared at me, the more ashamed I felt. The more ashamed I felt the hotter I got. My thighs were slick with precum that was practically pouring out of my chastity cage as I went all the way to the back of your local Walmart to get my sparkling water and up to the register. I needed to force myself to interact with someone, and self-checkout was not going to increase the high I was riding.

(Should I continue?)

Thank you.

"Happenis is a new cock in my sissy-cunt."