u/sissyfucktoy20

It all started for me when I was a teenager. Whenever I could I would find panties and small women’s clothing items to wear. I’d read stories on Literotica and watch porn and rub myself until I came in the panties. This was something that went on until I left for college as often as I could.

Things really died down for me once I left for college as I never really had an opportunity to dress. My roommate, and closest friend, was around most of the time and would definitely have found out and is unfortunately quite homophobic and even though I’m straight(ish) it would not register that way to him. Meanwhile, I also had a long term girlfriend who would visit me in college and didn’t know about my desire to dress up at all.

After college my girlfriend became my wife and I tried my best to keep my desire to be a sissy quiet. I dressed a couple times during the first years of our marriage but always felt bad about being so secretive around her.

Then in January of this year, for better or worse, I told my wife everything. I admitted to wanting to dress up and do my makeup, wanting to be a sissy, and wanting to play with my ass. She was hesitant but decide to try supporting what I wanted and basically just said she isn’t ready to see me in fem yet. Fast forward two months and my wife is supporting and even encouraging me to be caged little sissy slut. While she still doesn’t want to see me in full fem she has become more involved through chastity and teasing me endlessly. But many things have changed, including the fact I wear chastity and panties almost every day and take care of most things around the house which my wife has always done. And then almost every night after she goes to bed I go pick from my sissy closet full of heels, lingerie and dresses, most of which she has bought for me, and dress up. Then I do my makeup and practice sucking and fucking dildos as much as my sissy heart desires! I’m only two months in to exploring this and both my wife and I have become substantially happier and now even she can’t imagine going back to before. So I guess it really always was my destiny to become a sissy…

For as long as I can remember being home alone the first thing that came to mind was dressing up in my sisters clothes
One time when I was 18 but looked freakishly young do my age was home alone I went into my sisters room and specifically knew what I will put on today as I saw it in the laundry basket 2 days ago it was a pink checkered skirt pink frilly panties and pink stockings with a crop top which has a love heart cut out on the top
I put it on I felt amazing so pathetic and need to be used
Then I heard the door bang but it was only 3 o’clock my sister shirt be home until 5
She came home early and saw me in a mini skirt with my hard 5” dick poking out from underneath just slightly showing off the pink panties
She doesn’t say anything except for “come on”
She runs upstairs and I follow her unsure on what will happen next
I sit on her bed as she picks out outfits for me to wear
First was this black short dress I put it on and she does my makeup and gives my a blonde wig that she wore for Halloween
I do some model walks and in the corner of my eye I see a flash
She has been videoing me this whole time
She then said when ever we are home alone you will do exactly as I say when I say it
That hour later a black man she works with arrived but it wasn’t for her

What would a new sissy with a 3”soft fuck need as a starter chastity I keep seeing people have different ones some flat some plastic and others metal and quite long
I think I would like a tight plastic one but I don’t know if it is healthy an how to take care of it