The Slippery Slope

As this is a continuation of the story from my last post, i will very quickly just mention the time and event that triggered this downward spiral into my sissyhood.

It was in the middle of college, totally moved on from my previous escapades that i brushed off at the time as "experimentation", and all of a sudden, when going home from a night of drinking with friends, saw a woman sports bra hanging from a branch on a bush, and took it home with me.

In my drunken state, i decided to try it on, you know...just for fun, in the confinements of my room. And while it was hard to put it on, since it was obviously a couple of numbers smaller than my size, but i still managed somehow.
While i did have a fetish for sexy lingerie, I mostly looked at the stockings and garter belts, not so much as bras, so wearing a bra was not as exciting in itself...but...

There was a very strange feeling that i can vaguely describe as arousing. not by the bra itself, but the tight feeling it encased my chest. The form fitting goodness that somehow felt very, very right. having an article of clothing that , in spite of being a couple of sizes too small, felt incredible. The fire was lit, passions rekindled, and forgotten memories returned combined with the stress of the time i was in...i wanted to feel more...i NEEDED to feel more.

Then my secret missions began : to obtain sexy lingerie for myself, but the ultimate goal at that time was to get some sexy stockings(probably fishnet) for myself. The plan was to just enter some local stores or supermarkets and "casually" buy them. But in the beginning, i always chickened out, and just went to multiple stores to see if they even have such stuff. Luckily for me, they did, it was so exciting but at the same time nerve-wrecking to see that my goal was very close. but i always was too scared at how i would look like, buying woman's articles, a young man. some local mini-market even had multiple variations of sexy stockings!!

So after reconnaissance of multiple stores, i finally took the courage by being super horny and drinking a beer before to go to the store, and bought my usual groceries, and very nervously just took the nearest stockings and put it in my shopping basket. and tried to act casual while going to the cashier, already my mind was brewing up a scenario of how the cashier would look at me with disgust as to what i have in the basket, or that it was a mistake of some sorts...but to my surprise, and my sanity, the cashier was on the phone. What luck! and when i came with my basket, she just automatically checked everything , I payed, and casually went home, with my heart racing and my mind dazed at what have i done, i could not wait to get home sooner.

Finaly home! I quickly put the groceries in their place, rushed to my room and can finally take a good look at the pair of stockings i bought...and JACKPOT! Fishnet lacy tops holdem ups! This was it, it should feel perfect, so i took a shower, and returned to my room and unpacked them from their packaging. then i carefully examined them, feeling the texture and firmness of the material and prepared them to put them on. I gently slid the stockings on my naked body, in a sexy way i saw women in porn do it. Amazing! adrenaline was rushing. it felt better than expected. MY legs transformed into something sexy! something desirable! even for myself! I could not get enough of looking at my own legs from different poses and angles. so now instead of seeing this fetish on women, i had it on myself. And i could not help it by getting an throbbing erection! just by wearing stockings! After lounging in them for a while and pretending i was a hot babe , i decided to jerk off to porn while wearing them. And ended up nutting a hard load that was saved up for quite a while, and had a weird sense of accomplishment(?). As like i just ticked a mental checkbox of some kind.

After the masturbation session, the daze went away, and clarity returned (the so called "post-nut" clarity) so i removed the stockings, but instead of purging, i decided to hide them and keep them for later uses...
After that, i started to occasionally buy other types of stockings and pantyhose, and panties to see how they feel and experiment to see what works and what doesn't. As sequential times were less and less stressful to buy the things. Even started to order some things on-line and one thing very quickly led to another...
Not much time would pass that i had an urge to try to see if my butt was feeling lonely so my masturbation slowly changed (a story for another time). I was then secretly buying skirts, tights, tight turtlenecks, high heels (a fun story for another time), and a wig and makeup. That in the end i had to have special boxes for my femme stuff and a suitcase(with padlocks) just so it could all fit. So there i was at the time, a pretty chill dude, that had a secret suitcase of woman's clothes.

In my next post i will probably cover something that also played an important role in all this that i barely mentioned, and that is the porn i watched and my eventual discovery of the phenomenon called "Sissy".

p.s. - Now that i had time to recollect and organize my thoughts, and fondly reminiscing of the innocent past, i think this could actually be fun for me to document it in this way. I hope you liked it and you can look forward to more diving down the rabbit hole pretty soon ;)
kiss, Dora