tagTranssexuals & CrossdressersHigh Heels and Stockings Tryout

High Heels and Stockings Tryout


High Heels and Stockings - First Time

I blame Literotica, or credit it, as the case may be. I've always been excited by women's sex clothes -- high heels, stockings, panties, and skirts, and have shot lots of loads fantasying about how hot women look all dolled up.

Then I came across Literotica, and started reading all the nasty, filthy stories about cross-dressing and trannies. I copied the best stories to my laptop, and would stroke my hard, throbbing cock in my sexy wife's black satin panties. My pre-cum would drip out like a faucet, soaking the soft material with my sticky juice. After an hour, I wouldn't be able to take it anymore. Every stroke of my cock would almost make me shoot. I'd flip open a porn mag, state at a hot photos of some slut with cum all over her face, and just soak the page with my spunk.

I guess it was inevitable what would happen. I'd bought my wife some sexy, slutly clothes -- black fishnet stockings, pink panties, a short plaid skirt, and a corset top. She looked so hot, all dolled up in the slut's costume, on her knees sucking my stiff cock. When I finally came in her wet mouth, I'd shoot so much sperm that it would overflow out of her lips, dripping down onto her tits.

One morning, she'd left for work, and I had the day off. We'd had sex the night before, and her slut clothes were strewn all over the bedroom. I'd woken up with a stiff cock, and stroked it with the soft sheets, while I thought about how tight her pussy had felt when she came all over my cock. I also thought about how soft and sexy her fishnet stockings felt against my legs, and how her pushed-to-the-side panties rubbed against my cock while I fucked her from behind. My mind raced back to all those filthy cross-dressing stories from Literotica, and I thought to myself, "Why not? I'll try how it feels".

I rolled the stocking up my legs first, repeating how I'd watched my wife do it. A forbidden thrill rushed me as I felt the silky material wrap around my legs. By the time I'd gotten the first one on, a drop of pre-cum had dripped out of the tip of my dick. I smeared the juice over my finger, and licked the sweetness away. I slid the other stocking on, and looked own at my swollen, purple cockhead, and sexy, fishnet wrapped legs.

I picked up her pink panties next. They were a bikini style, with a full bottom, all the better for rubbing my leaking cock against when they covered my wife's ass. She'd had them on when I fucked her, and they were soaked with her juice. I pressed them against my mouth, and sucked the wetness from them. One stocking clad leg, then the other, slipped into them, and I pulled them over my ass, wrapping my balls in the pussy-soaked satin. The pressure from the small size squeezed my cock, forcing out a stream of pre-cum, which I greedily licked off my fingers. My pre-cum tastes so sticky and sweet.

The plaid skirt came next, and as I stepped into it, I started to look like a hot bitch from the waist down, and least until you saw my rock hard cock tenting out the skirt. The skirt barely came down over my stocking tops, making me look like a total whore. My cock needed to be stroked, but I wanted to finish the filthy cross-dressing fantasy before I gave it a good squeeze. The black lace corset wrapped around my chest, giving me a soft, feminine look. Just one more thing I thought. I went into the closet, and found my wife's sluttiest high heels. As I slid my stocking clad foot into the front strap, and fasted the back strap on, I let out a moan. My heart pounded as I put the other one on, and stood up in my new high heels. I slowly walked out of the closet, totally enjoying how the heels made my legs feel so long, and how they stuck my hot ass out. I swished over to the full length mirror on wardrobe, and gasped when I saw my reflection.

There I was, the same face as ever, but with my body dressed up in the sluttiest outfitt imaginable. What is it about cross-dressing that's so hot? Is it the nastiness of dressing up in your woman's sex clothes? Is it the forbidden thrill of doing something so nasty and perverted? Is it that you can create the hottest piece of ass that you've ever jerked off about? I don't know, but I knew I had to concentrate not to spill my load all over the front of my skirt when I looked at myself.

I just looked so fucking good, and felt like such a dirt slut. I swished some more around the bedroom, wiggling my ass, looking over my shoulder to the mirror to see my legs and skirt bounce around. When I get really turned on my ass gets horny. Usually my wife takes care of it my sliding a lubed finger in my tight ass. Today I'd have to take care of it myself, and I knew just how.

My wife's vibrator is so fucking hot -- 7", not too thick, soft, pink, and curved like a real dick. I walked in the sexy heels over to her panty drawer, where she kept it, feeling like a horny girl who needs a good fucking up her tight ass. The vibe felt smooth in my hands, and I moaned like a whore as shoved it in my mouth. My wife had fucked herself with it yesterday afternoon, and it stille tasted like her pussy. A pussy tasting cock. What could be better?

I went back to the mirror, and watched this wanton bitch suck the jelly vibe cock clean. As good as it felt with my lips wrapped around the cock, I knew it would feel even better sliding up my hot, tight ass. I got some lube, pulled my panties down to my ankles, and lubed up my fingers. My asshole was so hot and sensitive that I groaned as I lubed it up. I slowly slid a wet finger inside my ass, and stifled my slutty moan by sticking the vibe back in my mouth.

I was filled front and back, split-roasted like a complete whore. When I felt my ass relax a bit, I pulled my finger out, and smeared lube all over the pink cock, giving it a kiss for luck.

I like talking dirty during sex, so I gasp out "Do you want that hard cock up your ass bitch?"

"Oh yes, slide that prick up my virgin ass!"

The tip of the vibe found its way to my tight asshole, and I moaned in total pleasure as my asshole kissed the head of the cock.

"Fuck me. Fuck my slutty ass," I groaned, sliding the slick head up my ass. Sliding the vibe up my virgin ass was the hottest feeling I'd ever had. It literally took my breath away.

There I was, a straight, normal guy, dressed up in strappy high-heels, fishnet stockings, pink panties around my ankles, plaid skirt and lace top, sliding a pink jelly vibe in my ass, my cock feeling thicker and harder than ever before. More groans escaped my mouth as the rest of the cock slid into my aching ass, until I had it all the way in. A twist of the base turned the vibe on, and the vibrations made my cock leak like a faucet, dripping out a constant stream of sticky lust. The vibe drove my ass wild, throbbing through me into my cum filled balls.

I was the sluttiest bitch I'd ever seen in the mirror, a nasty slut getting her ass fucked, while her throbbing cock stood out from under her skirt, dripping pre-cum onto the carpet.

My moans were non-stop now, and I knew I was so close to blowing my cum. I pushed the vibe in and out of my ass while I squeezed my cock as hard as I could, feeling it so thick and solid in my hand.

"Make me cum! Make my slutty ass cum," I screamed, and felt my cock go rigid. A squirt of pre-cum flew out of my dick before my orgasm hit. My ass gripped the vibe tight as my balls emptied their load. Sperm shot out thickly and wetly, splattering the reflection of a cross-dressing slut blowing her cum. The cum hit the mirror with such force that I heard the splatter, even as my own moans of filthy pleasure spilled from my lips. 5, 6, 7 spurs rocked out of my swollen head before the pressure lowered, and the cum began to just flow out of my cock.

My heart raced in my ears as I came down from my cum. I slid the vibe out of my ass, and the massage of the cock head against my slutty asshole caused my knees to buckle. I collapsed to my hands and knees in front of the mirror. Thick, sticky cum was splattered against the glass, and I knew what I had to do. No good slut, after getter her ass fucked that good, could let that cum go to waste. I stuck my tongue out and licked up the sperm. The cum felt warm, sticky, and sooo nasty. I licked up a tongue full and collapsed on my back, smearing the cum all over my lips and sucking it up. My sex life had changed forever.

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by Anonymous

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by Anonymous03/18/18


First time I had her stocking on I ripped them close to my crotch! When I finally got out of them I ran to the store to buy her another pair! Put them in her drawer. Though I had no problem. The nextmore...

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