How I Became a Sissy Slut

Babes

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 casino şirketleri 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.

“Probably,” he sneered, as he walked over to where I was impaled doggy-style, the cabinet still with its plastic penis pushed up my stretched hole.

“I did not know you were such a sissy slut,” he laughed. “Why are you “making love” to that little rubber toy instead of servicing a real man?”

He reached down and squeezed his crotch and I noticed for the first time the huge bulge in his jeans.

“I, well, umm, this is just…” but I couldn’t form a coherent thought.

“I keep your secret, but I sure could use your services. You see Senorita Jose is off visiting her mother this week and my “Little Jose” is very casino firmaları lonely,” he grinned.

To say I was speechless would be the understatement of the year. My dick, which had instantly gone soft when I heard Jose’s voice, was now rock hard again. I had assumed my life was ruined, or at the very least, I’d be giving Jose a huge raise and a life-long position as my gardener.

“You like sucking dick, huh Mr. Jenson? Or maybe I call you Cissy. You’d like that huh, slut?”

Actually, I referred to myself as Jamie, a feminization of my given name James, but I wasn’t about to argue with Jose.

“Or maybe I just call you bitch,” he laughed as he grabbed my head and pulled it into his crotch.

I felt the heat radiating from his tool and smelled the manly muskiness of a guy that had been doing yard work all day. I mouthed his thick rod through his denim jeans and a loud moan escaped my breathless throat.

“Yes, you are a very hungry cocksucker I see,” he said. “To be honest, you are not pretty at all Cissy. But I hope you make up for it with effort. Ugly girls make the best fuck sluts, they know they have to try harder. Will you try hard for me, Cissy?”

“Yes Sir,” I croaked, my mouth literally watering. I was finally going to suck a big, juicy, REAL cock.

Jose unzipped his blue jeans and reached inside, fishing out his thick, uncut tool. Pulling it out, he gave my face a hard slap, before yanking out his huge, low hanging balls too.

“You will love my cock, Cissy,” he grinned. “Make it nice and hard, and I’ll show you what a real man dick feels like up your tight little man pussy. You want me to fuck you, huh bitch.”

“God yes,” I moaned.

“Then say it,” he insisted.

“I want you to fuck my ass with your big cock,” I begged.

“The gardener fucks his boss,” he laughed. “That sounds like a story that needs telling. Maybe they turn it into a blockbuster movie, huh?”

“Can I please suck your cock, stud?” I asked, eager to taste his fat dick.

“Yes you may, Cissy,” he replied. “Show me what a good little slut you are.”

I’d practiced on my rubber dicks for months, trying out all the tricks I’d seen in the pornos. I knew I could do this, and I had no hesitation in taking his uncut tool into my mouth.

“Never knew you were a flaming faggot, Jenson,” Jose said letting out a low moan as I took his cock into my mouth. “I’d have used that queer mouth of yours sooner if I’d known. Guess I understand why you are divorced now.”

The words faggot and queer stung, but they felt so right. I was finally getting a chance to be a queer faggot and I was in heaven.

“You do a good job, and I’ll let the yard crew know. You’ll have more Mexican dick than you can shake a rake at,” he said. “Does your ex-wife know you like dick so much?”

A look of real fear crossed my face as I shook my head no. While the thought of my secret getting out was worrisome, the idea that a string of gardeners filing into my garage to get their big, sweaty cocks serviced made me horny as fuck.

“Let’s see how much of this brown dick you can take,” Jose demanded as he put his dirt caked hand on the back of my head and forced me down on his growing boner. I felt his bulb pop down my throat and I inhaled deeply, swallowing his cock like a practiced whore.

With his nuts resting on my chin he ordered, “Stick out your tongue and lick my balls, Cissy. Make me happy and I won’t let your little secret be known around the neighborhood.”

I happily güvenilir casino obliged and he moaned approvingly. “Damn, you are one horny slut.”

I continued to suck him, taking a brutal face fucking in the process. He had some real aggressive tendencies, things I assumed Senorita Jose would never stand for, but I loved his rough treatment.

Pulling his spit covered rod from my tortured throat, he gave my face a few wet whacks. “Damn honey, you’ve gone and made my dick all hard,” he chuckled. “You ready to have me pop your cherry?”

“Yes Sir,” I pleaded. “I want you to bend me over and pound my hole with your big beautiful cock.”

“I’m gonna breed that sissy hole and fill you with my seed,” he said.

I stood up and bent over the workbench, offering him my hole as I spread my hairy cheeks. Thankfully, my ass was nice and stretched out from riding my rubber dick and I was already well lubed.

“Damn, you sissy sluts can’t get enough cock can you?” he smirked as he grabbed my hips, lines up his rocket, and with one big thrust, drove his long spear into my ass, not stopping until he was buried to the hilt.

I was pinned up against the workbench, so I had nowhere to hide as his fat prick stretched my hole even wider. I felt like screaming, but he saw my problem and grabbed my panties off the bench and stuffed them in my mouth.

“That will keep your pie-hole quiet while I fuck you like a cheap slut,” he said.

And he did, he pounded me like a man possessed, driving his cock in and out of my ass, sometimes fast and sometimes slow, but always deep. My ignored cock was still hard as stone and was leaking uncontrollably as he milked my prostate with his expert fucking.

I lost track of time, but I think he fucked me for a good 15 minutes until he announced, “OK bitch, I’m about ready to breed that pussy. Gonna fill you up with my 7 day load.”

I could feel his cock stiffen and pulse and hot jets of man cream shoot deep into my bowels. I’d never felt more like a sissy slut in my life than as I took this alpha male’s semen in my cunt. I swear he shot 8 or 9 jets of cum before slowly pulling his thick rod from my butt.

“Clean it up, slut,” he demanded as he whirled me around and forced me down to my knees.

I eagerly lapped up his cum, sucking the last few spurts from his piss hole and taking him back down my throat to clean off my ass juices.

“Fuck Cissy, you are one seriously depraved little slut,” he laughed as he wiped the sweat from his brow. “Love how you took it like a pro and never complained. The boys are gonna enjoy banging you.”

“Thanks,” I meekly offered as I slurped down the last of his load, already feeling his hot cum leaking from my gaping asshole.

“I gotta go mow your yard, but Ricardo will be here in 30 minutes to pick me up. I’ll call him now and tell him I found some hot sissy pussy if he is interested. And trust me, Ricardo is always interested in fucking a willing hole. Oh, and if you think I was rough, I hear even the sheep are scared of Ricardo when he has a boner,” Jose laughed as he left the garage.

Ricardo showed up shortly with his apprentice, Felipe, and they took turns spit roasting me. Jose even dropped another load straight down my throat after he finished mowing the yard. By the end of the day, I’d taken five loads of cum and was well on my way to being a true sissy slut. My cock had leaked what felt like a gallon of milk, and I’d blown my load twice without every touching my ignored sissy clit. When I finally stripped off my lingerie, limped into the house, and took a hot shower, I had a smile on my face that wouldn’t stop. Oh, and a burning in my ass that took days to subside.

Trust me, I’m not complaining!! And my yard has never looked so good.

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