I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star.
After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of college and my second son is a bartender with his only aspiration to fuck as many young coeds as he can dip his dick into.
But I'm getting ahead of myself. After the divorce, I spent a lot of time surfing porn on the internet. I started out pretty traditionally, jerking off to hot bodied sluts, wishing I still had what it took to bed these beauties. But over time, I started viewing kinkier and kinkier stuff; anal sex, bdsm, pegging, bisexual, gay, and finally sissy porn. Sissy porn gave me a raging boner every time, which as a middle-aged man was no easy feat.
I tried dating a few women, but the times I was lucky enough to get them in the sack, I found the only way to get and keep a boner was to wish I was her. When she was on her knees, sucking my dick, I fantasized I was on my knees sucking a dick. Just typing this makes me feel dirty and depraved, but then again, I'm only starting to come to terms with my new sexual feelings.
I started going to an adult store in a town about 30 miles from where I live. I bought my first dildo at that store and spent a month just stroking and sucking it before I got up the nerve to push it up my virgin backdoor. As I struggled to get it buried ball deep, lathering on a gallon of lube, my cock throbbed like a teenager's. And when I started bouncing up and down on it, my cock leaked like a broken faucet. I blew the biggest load that night and I realized I had some issues to work through.
I ordered cross dressing gear on-line, behind the relative anonymity of Amazon. My first pair of fuck-me high heels came one Saturday morning and I spent the entire weekend walking around my house, learning how to strut my stuff, my cock in a constant state of rigidity.
Other items were ordered; panties, garters, stockings, silk nighties, a wig, breast forms, bras, and even some costume jewelry and makeup.
Now mind you, I'm 5'10" and nearly 200lbs of hairy masculinity, including a three-day beard that takes about 2 hours to grow. I'm an architect by training and I work on construction sites as the project lead. I wear jeans, boots, and flannel to work. Even as I started dressing the part of a sissy in the privacy of my own home, I knew it was way to late in life for me to ever resemble a "passable" gurl. I was never going to trap anybody.
My jerkoff sessions became long and orchestrated. I'd dress up, spend hours gooning over big, juicy cocks on the internet, fantasizing about being the slutty little pornstars in the videos, and often shoot a huge load of cum on my chest or face with one of my growing collection of rubber dicks stuffed up my ass.
I started wondering if I would ever act out any of my fetish urges, and even went so far as to post a few ads on Craigslist, looking for a willing partner. I had a few back and forth email conversations with some likely candidates, but it just never materialized. I was looking to stay super discreet (God knows I didn't want the kids or ex-wife to find out about my kinky perversions) and to be honest, I usually ended up chickening out. I was the definition of a Craigslist "flake."
One weekday I took the afternoon off from work to get some stuff done around the house. But by about 2pm, I was craving to dress up and take my new dildo for a spin. It was a beauty, big and black with huge veins and a heavy-duty suction cup base. I put on a long red wig and made a ponytail, applied some slutty lipstick, clipped on my long dangling hoop earrings and then pulled out my slut locker. I keep all my lingerie in a box locked in a big steel cabinet in the garage. I have another box for my heels and one for my dildos. The garage is often where I end up playing as it just feels dirtier and more industrial, the perfect mood setting for a cheap whore like me. I mean a sissy has tools too, and the garage is the perfect discreet place to store one's tools, right? Plus, the big steel cabinet has a set of steel drawers, which are just perfect for sticking my suction cup dildos on and going for a ride.
I put on some black fishnet stockings with a lace garter, my red 6" heels, a slutty camisole over my red lace stuffed bra, and my tartan ridiculously short school-girl skirt. Admiring myself in the full-length mirror I kept in the garage, I may not have been passable, but I instantly had a sissy boner. Times like this, I wanted a real man's throbbing tool so bad.
I got down on my knees and worshipped the black rubber schlong, taking it down my throat and getting it good and lubed up (I'd already generously applied some slippery stuff to my man pussy). I fought my gag reflex, still not a true pro at deepthroating a dick as big as this toy.
When I couldn't stand it any longer, I turned around, spread my ass cheeks and backed up onto the big black rod. With every inch I took, my sissy clit dropped another dollop of precum on the cold concrete garage floor. I started slowly and worked up a good rhythm, fucking that steel cabinet door and its big, fat dick like a whore possessed.
And about that time, my life took a very unplanned change.
"You look very pretty, Senor Jenson," I heard from the side door to the garage.
Frozen in mid stroke, I opened my eyes to see my gardener, Jose standing framed in the open door, his hand still on the key in the lock.
"Jose, uhhh, ummm," I stuttered, shocked beyond embarrassment. "I thought you were scheduled for tomorrow."
"Si, si," he snickered. "But I finished up early and thought I'd knock your yard out today. But I see you are busy, heh?"
"Its not what it looks like," I started. But who was I kidding? It looked like I was dressed in drag, buttfucking myself on a big rubber dick. And that is exactly what it was.
"Sure, sure," he chuckled. "You are not really a sissy slut and that little rubber dildo is not really buried up your sissy man cunt."
Little? He hurt my feelings with that one. This was the biggest dildo I owned.
"We keep this private, right Jose?" I almost begged.
