tagTranssexuals & CrossdressersDuped by a Cross-Dresser!

Duped by a Cross-Dresser!


I don't brag about much, but I do have to say that I am a damn good cross-dresser. When I slip into a dress, no one can tell I have eight inches of meat hanging between my legs. I've had relationships with more than a dozen men who never knew the difference.

It helps that I have a girlish face with a small nose and innocent, blue eyes. Glamor and Cosmopolitan magazines have taught me to apply make-up. My slim body is like a piece of clay waiting to be molded by sexy skirts and flimsy blouses.

My weekends are filled with feminine pleasure. I dress like a slut and find some cock to suck. I get it wherever I can find it. Sometimes, it's night clubs. Other times, I pimp myself out to long-haul truckers at the local truck stop-- not for money but because I like it.

But I'm not all female. That is why I consider myself a cross-dresser and not a transsexual. I live most of my life as a man. I watch sports. I don't ask for directions when I'm lost. When I go to the construction site in the morning, I wear jeans, T-shirts and work books just like all the other dudes.

I like fucking men, but I prefer to date women. I'll do anything legal with a transsexual.

Despite all the weird sex I've had, I never saw Julie coming.

Julie lives next door to the house I'm renting. She is a total MILF with long, blond hair, healthy hips and double-D tits.

We were neighbors for nearly six months before we ever said a word to each other. Over the weeks, I gathered that she was married to a beefy linebacker-type with a military-style buzz cut. They didn't have any children and drove sensible cars-- a Volvo station wagon for her and a Dodge pick up for him. She favored flimsy dresses and liked to work in her flower garden. He mowed the lawn twice a month. They seemed nice enough and waved when they saw me. Both were tall. Julie must have had half of a foot on me.

I came home from work one day to find Julie sitting on the top step of her front porch. She was hunched over with her face in her hands. I could see she was crying.

I walked over to the property line.

"You OK?" I asked.

She didn't respond, so I asked again.

"I'm fine," she snapped. "Just go away."

There was nothing else I could do, so I went into the house. After taking a shower, I decided to cross-dress and head to a local adult book to see if anyone wanted head in one of the private video booths.

I went to a hall closet where I keep my collection of slutty clothes. My outfit started with a lacy black bra and matching boy-short panties. I tucked my cock into a special holster sewn into the crotch. My legs were clean-shaven and looking good, so I decided to skip the thigh-high stockings and garter belt and went right for my black miniskirt. A tight pink T-shirt and blond page boy wig topped off the ensemble. After checking myself in the closet door mirror, I decided that only my sluttiest shoes-- a pair of black six-inch heels-- would go with the outfit.

My heels click-clacked on the bathroom tile when I went in to do my makeup. I laid it on thick. Sparkly pink lipstick, gray eyeliner and blue eyeshadow. I finished off the package with two squirts of CK One perfume.

I looked like a total whore.


On my way out the front door, I saw that Julie was still sitting on her front porch step. Her head was up and she was blankly staring off into the distance with reddened eyes.

"You doing any better, hon?" I asked.

I didn't realize it, but I had instinctively switched to my feminine voice. I had been cross-dressing for so long that it came automatically as soon as I put on a bra.

Julie snapped out of her trance. She looked over at me and smiled sheepishly, wiping her cheek with the back of her hand.

"Yeah, I suppose so," she said. "I'll be fine."

She sniffed and looked away. She was about to break down again.

"It looks like you could use some company," I said. "Can I come and sit next to you for a minute?"

She was barely able to squeak out an "OK" before bursting into sobs. I ran across the lawn as quickly as I could and wrapped my arm around Julie as I sat next to her.

"Oh, you poor thing," I said. "What is it? Man troubles?"

"How did you know?" she asked through the tears.

"It always is, dear," I said while rubbing her back. "What happened?"

"It's my husband, Ray," she said. "He's cheating on me."

Her face fell back into her hands. She shook with sobs.

"There, there," I said. "It's going to be all right. You know what? A lot of times these things are big misunderstandings. You could be getting all upset for nothing."

"No," she said. "I'm positive. He forgot his cell phone at home today. When I first saw it laying on the kitchen counter, I was glad because I needed his Aunt Mildred's number. I opened the phone, but I don't know how to work it very well. After punching a bunch of buttons, I accidentally found some text messages from a girl named Roxy. I don't know any Roxy, so I read a few. She and Ray were writing to each other about where they were going to meet and how they couldn't wait to suck on each other. All kinds of nasty stuff. The messages go back almost a year. They've been getting together almost every week."

"That does sound serious," I said. "I'm so sorry."

Julie sighed.

"Oh, whatever," she said. "Fuck it."

Julie looked up at me, and a smile broke across her face. We both giggled.

"I feel so silly," she said. "We haven't even met. My name is Julie."

She extended her hand. I took her soft flesh in my own.

"I'm Stephanie," I said.

We shook.

"Are you dating that guy next door?" she asked.

At first, I didn't understand what she was talking about.

"Huh?" I asked.

"Oh, I'm sorry," she said. "I didn't mean to pry."

Then it made sense all of a sudden. Julie had no idea that the "guy next door" and Stephanie were the same person.

I laughed off her question with the wave of the hand.

"Oh, don't be silly," I said. "You're not prying. It's just one of those complicated situations."

Julie rolled her eyes.

"Oh, I know all about complicated," she said.

"Honey," I said. "This is beyond anything you could imagine."

"All I know is he's cute, and you should stick with him if he's treating you right," Julie said.

"Don't really have a choice," I said.

Her eyes flashed to my tummy. While she will never admit it, I'm convinced Julie was checking to see if I was pregnant. I patted her knee.

"One day, we'll sit down and I'll tell you about the whole thing," I said. "But right now, I ought to go. You going to be OK?"

She forced a smile.

"I'm going to be just fine," she said.

Then she did the strangest thing. Julie gently placed a hand on my cheek and planted a kiss on my lips. She didn't slip me the tongue, but the kiss lingered just a second longer than a friendly peck would have.

"I like your perfume," she said. "It's sexy. I think he's really going to like it."

"Who's going to like it?" I asked.

"Whoever you're wearing it for," she said. "You are going out on a date, aren't you? That's why you're dressed all sexy, isn't it?"

I decided to test her.

"How do you know I'm wearing it for a him," I said. "Maybe it's for a her."

"Well, I'm positive someone is going to love it," Julie said.

My cock was swelling. I've been involved in some crazy shit, but this was a first. A jilted woman, who thought I was a woman, was hitting on me. I checked her out for the first time since sitting next to her. She was wearing a flimsy red dress with white polka dots that left ample cleavage bare. Folds of the dress hung loosely between her tanned, slightly parted legs.

I decided to make my move.

I put my hand on her knee and slid it up her thigh, stopping just short of her honeypot. I looked into her eyes. She fired back a gaze oozing with lust.

"You know, my plans aren't exactly written in stone tonight," I said. "Maybe you'd like to come to my place, and we could talk some more Have a girls' night, just you and me."

"That sounds nice," Julie said. "But how can we have a girls' night when he's there?"

Her head gestured toward my car.

"Oh, him," I said. "You don't have to worry about that. The house is empty. It'll be just us two."

"You sure?" she asked. "I've been sitting here since he got home from work, and I haven't seen him leave."

"Trust me," I said. "I know his every move, and we'd be the only ones home."

Julie shrugged.

"What the hell," she said. "You only live once."

I took her by the hand and led her across the lawn and up the path to the front door. I let her inside. Julie flung herself at me the second the door closed behind us. We pawed each other like beasts as our tongues darted in and out of each others' mouths. Her hands went from my neck to my ass, as I explored her hips, thighs and breasts.

My stiffening cock was threatening to slip out of the holster. I thought that if I could just get her into a dark room we could start to have some fun without her ever knowing about my eight-inch secret.

"Let's go to the bedroom," I said.

She was only too eager to follow.

The first thing Julie noticed was a shiny, gold vibrator on the nightstand next to my bed. It was narrow and about six-inches long, the perfect size for some anal action. A cross-dresser friend and I had been fucking each other with it just the night before. Julie picked up the dildo and waved it at me.

"Oh, you naughty girl," she said. "I've always wanted to try one of these."

She tossed me the dildo, and I caught it one-handed.

"Wow," she said. "You catch pretty good for a girl."

"You throw pretty good for a girl," I said.

"That's not all I do well," Julie said.

A come-hither smile spread over half her face as she pulled her dress over her head. She flung it at me. I let it hit me in the face and fall to the floor. Julie reached behind her back to unhook her lacy, white bra. A truly amazing set of all-natural knockers jiggled free.

Keeping my cock in place was getting tougher. It wanted nothing more than to be fully erect. Then it got damn near impossible when Julie bent over to slide her thong panties down to her ankles. She had an old-school bush-- big, full and black. I took a few seconds to appreciate her body. Every inch of her was perfect. For the first time, I noticed that she had amazing muscle tone. Her gym workouts must have been totally intense.

I couldn't take it anymore. Willie had to be free.

"Brace yourself, Julie," I said. "I need to show you something."

I slid off my miniskirt, then reached deep into my boy short panties. Julie's look of puzzlement turned quickly to astonishment when I whipped it out. My cock stood at attention as I slid the panties to my ankles. I bit my lip and carefully watched Julie's expression.

It wasn't good. She was getting angry.

"What!" she said. "Tell me this is a joke! Is that some kind of strap on or something?

"What you're looking at," I said, "is 100 percent the real thing."

"This can't be happening," Julie said. "You're a fucking guy?"

"I am," I said with a nod.

Julie's face was turning bright pink.

"Humiliated by two men in a single day," she said. "No! No fucking way!"

Julie lunged at me. I never had a chance. She instantly had me down on the bed. I tried to squirm away, but she overpowered me. Julie grabbed the vibrator. I heard her turn it on. With half her body holding me down, Julie reached over to the nightstand and snatched up a tube of KY Jelly. She forced it into my hand.

"Lube yourself up, bitch," she said.

"Fuck you," I said.

"You've got two choices," Julie said. "You can get fucked with grease or without."

Julie roughly stuck the humming dildo into my ass crack to show me she was serious. I uncapped the tube and squirted some lube onto my fingers.

"You know, I didn't have to show you my cock," I said, while reaching back to grease my bunghole. "I could've done all kinds of stuff to you, and you would've never known the difference."

"Feel lucky you didn't," Julie said. "If I'd have ever found out, I wouldn't just be fucking you with this dildo. I'd kill you."

Her tone left no doubt she meant it.

"OK," she said. "Enough lube. Get in the doggy-style position."

I obeyed.

It's a good thing I'm an experienced butt pirate because Julie didn't try to tease me with the fuck stick. She slammed the whole six inches inside me fast and hard. But six inches of plastic is nothing after you've taken 10 of flesh.

"You like that, slut?" Julie asked.

I turned my head to grin at her.

"Is that all you got?" I asked.

What Julie didn't know was that I prefer rough, angry sex to any other kind. My prick only got harder as she started pounding my ass with the dildo.

"You weirdo cunt!" Julie said. "You like to dress like a little bitch? Huh? Answer me!"

"Yes," I squeaked.

"You fucking call me ma'am!" she said.

"Yes, ma'am, I like to dress like a little bitch," I said.

The side of Julies fist slammed into my butt cheeks every time she shoved the dildo into my bung hole. Her speed was just as impressive. She kept the dildo going like a piston in a race car. I knew I was going to be sore the next morning, but I didn't care. I was totally getting off on it.

The nasty put-downs came at me just as fast.

"You fuckin' fairy!" she said. "You think you could fool me? Huh?"

"No ma'am," I said.

"Bullshit!" she said.

"OH GOD!" I yelled.

"What's the matter?" she asked. "Is it too much?"

"No ma'am," I said through gritted teeth.

"You like getting fucked, don't you?" she asked.

"Yes ma'am," I said.

"Look at this," she said. "You've got a little boner going. Isn't that nice?"

Julie shoved the vibrator deep inside me and left it there. I didn't dare move. She playfully slapped my cock and watched it swing.

"You get off on being treated like a whore," she said. "You fucking make me sick."

"Yes, ma'am," I said. "So sorry, ma'am."

"What?" she snapped. "You going to get cute with me now?"

Julie smacked my cheek. The sting hurt so good.

"Just for that you're going to eat my pussy," she said.

I was still in the doggy-style position with the vibrator humming in my ass. Julie got on her back in front of me with her legs spread and her glistening snatch inches from my face.

"Suck it, bitch," she said.

I had sucked a cock as recently as the night before, but it had been weeks since I'd eaten pussy. I inhaled deeply. Julie's snatch had that musty smell I loved so much. I started gently lapping the outer folds of her cunt with the tip of my tongue, but Julie wasn't having it. She grabbed the back of my head and smashed my face into her hairy wetness.

"Don't fuck with me, bitch," she said. "Eat my twat."

My tongue plunged inside her pussy. My nose was dug in that terrific bush of hers. It smelled like a rose garden. I started going crazy on her slit, licking her inside and out.

"That's it!" Julie said. "Suck that cunt! You know you like it!"

She started moaning. Her juices poured down my chin. Her pelvis bucked.

Then, without warning or explanation, Julie pushed my head away.

"Put your prick inside me!" she said.

Her pussy was so wet, my cock seemed to melt into her. The dildo began to slip out of my ass as I started thrusting. I had to concentrate hard to keep from cumming. I wanted to keep the experience going as long as possible.

I thought I was going to lose it when Julie snatched me by the throat. Her grip tightened. I could barely breathe.

"Don't you dare cum in my pussy," she said. "You wanna squirt, you do it on my tits. And then clean up the mess with your tongue."

When she released her grip, I gasped for air. The pressure in my loins became unbearable. I pulled out just barely on time.

The vibrator shot out of my ass as I sprayed my gunk all over Julie's chest. I came heavy. Streams of jizz dripped down both tits. She had splotches of my cream from her neck to her belly button.

"Now lick it up," Julie said.

I did it with a flourish, lapping up my own dick snot like a kitten drinking from a bowl of milk. I started with the big puddles between her titties and finished with the specks on her belly.

I flopped onto the bed next to her. She turned her head toward me. I turned my head toward her. We laughed our asses off.

"It felt good to be the dominant bitch," she said.

"I kind of liked being the submissive slut," I said.

"That works out nicely," she said.

We both sighed and started at the ceiling a while. Julie was first to break the silence.

"Tell me, what do you think of Roy?"

"I think he's an asshole for what he did to you," I said.

"But do you think he's hot?' she asked.

I pictured his big muscles.

"I'd fuck him," I said.

"Good," she said. "You're going to get your chance."

Julie had a sneaky smile on her face.

"What do you have in mind?" I asked.

"He has the hots for you," she said.

"Really?" I asked.

"Yeah," she said. "He made the same mistake I did. He thinks a hot chick is dating a guy who lives here. Can you imagine what his reaction would be if he found out he got his dick sucked by a guy?"

I snickered.

"He'd flip," I said.

"Exactly," she said. "So you'd help me set him up?"

"Honey," I said, "after a fucking like that, I'd do anything for you."

"Good," she said. "I haven't figured out how we're going to do it yet, but we're going to get him good."

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