It was a Friday night, and I was dressed to fuck. I wore a pink bra, matching panties and black high-heels. It didn't matter to me if someone pounded my ass or if I did the pounding. As long as my partner dressed up like a girl and held nothing back, I was down for anything.
I turned on the computer in my living room and checked my email to see if anyone had responded to my personal ad. The first two messages were from guys who "thought" they wanted to try cross-dressing. (They never do.) I deleted them and moved on.
The third message sounded promising:
"Loved your ad! I'm also into cross-dressing. Clean, non-smoking white guy in decent shape. 27 years old. Available Friday night. Email me after 7 if you want to play. P.S. You can call me Cindy."
I checked the clock on the wall. It was 7:02.
I hit reply and typed, "Horny as hell here. Wanna play?"
While waiting for an answer, I watched a slideshow of soft-core porn I had saved on my computer. Pictures of tits and asses wrapped in lingerie flashed across my screen. I folded my arms and tweaked my nipples. As the pressure built in my groin, I resolved to fuck someone that night, even if I had to get a hooker.
But that wasn't going to be necessary. Cindy replied quickly, just as a series of Jenna Jameson bikini shots began parading across the monitor.
"Come on over," Cindy wrote. "It's going to be a 3-some. I'm at 1021 Van Buren, Unit 2. Please be fully cross-dressed and ready to fuck. Need directions?"
Van Buren was on my sales route for work. I knew exactly where it was .I replied: "Don't need directions. See you in 30 minutes."
Within 25 minutes, I was cruising through dark suburban streets in my silver BMW. I wore a tight, black cocktail dress that showed off plenty of chest and thigh. My face was done up in heavy lipstick and eyeliner. I wore a pink "fuck me" wig that fell almost to my shoulders and then curled in toward my neck.
My heart thudded against my chest as I struggled to keep my car at the speed limit. The last thing I needed was an overzealous cop booking me on a one-way ticket to the county jail.
A million questions ran through my mind, but I kept coming back to one: Cindy said it was going to be a three-some-- who was the third?
The address Cindy gave me was a two-story town home in a swank neighborhood about a mile off the interstate. A light was on behind the curtains in Unit 2. I parked on the street, opened the car door and put my high heels on the concrete.
To my relief, no one was out on the street. I practiced walking like a woman on my way to a green front door with a gold lion's head knocker. I took a deep breath and told myself, "you're a fuck-toy whore -- act like it" and then rang the door bell.
Light footsteps rapidly approached the door. Someone on the other side paused to look through a peephole. And then the door swung open.
It wouldn't have taken anyone long to figure out that the person holding the door knob was a man trying to look like a woman. He wore a lacy, black corset with thigh-high stockings and panties that bulged with an obvious hard-on. The long black hair swept over his shoulder was no doubt a wig. Even the liberally applied make-up didn't do much to hide his gender.
"Hi, I'm Cindy," he said in a husky voice straining to be feminine. "You must be our date for the evening."
"I believe so," I said in an equally ridiculous voice.
Our eyes locked together. I held Cindy's gaze while stepping into the doorway. Cindy gave a sexy half a smile.
"I don't remember inviting you in," he said.
"Me neither," I said.
I leaned in to give him a slow, passionate kiss on his apple-red lips. My cock rubbed against his as we embraced. Cindy's lips melted into mine. I playfully flapped my tongue at them. He did the same to me. We might've fucked right there in the doorway, but a horn honked out on the street. Cindy jumped back. I looked over my shoulder. Whoever it was kept driving. The street was empty. Cindy giggled nervously. But not me. I was ready to get to business.
"Well," I said, "are you going to let me in, or do I have to fuck you right here with the door open."
Cindy straightened out quickly.
"You know," he said, "I don't think I've ever met anyone quite like you."
Cindy stepped aside and let me walk into the living room. It was lit with about a dozen candles and smelled of incense. A smooth techno beat played on a stereo. A coffee table was pushed into a corner. Four dimples in the rug told it usually sat in front of the black, leather couch.
I don't think anything could've prepared me for what was lying on that couch.
She was the sexiest woman I've ever seen. She had long, black hair, cantaloupe-size tits and slender legs. All she wore was a silky, blue bra and matching panties. She lay on her side with an elbow propping her up and one leg crossed over the other. The girl didn't say a word. The half-smile on her face did all the talking.
"This is my sister, Amanda," Cindy said. "She's going to help us fuck each other."
Amanda bit her pinky finger and giggled. It was the same sound her brother had made in the doorway.
"She sure is a hottie, isn't she?" Cindy said.
"And barely legal, too," Cindy said. "Just turned 18 last week."
Amanda provocatively raised an eyebrow, while absently caressing her hip with the tips of her long, red fingernails. She had an evil spark in her eye, the kind that told me she'd be fun for a night but would cause a guy a lot of trouble over time. It didn't matter to me. I wasn't planning on sticking around after our sex-scapade anyway.
Cindy had his eyes locked on the muff that barely showed through his sister's panties. His cock throbbed with anticipation.
"So, you really fuck your own sister?" I asked.
"Yup," Cindy said. "Got a problem with that?"
"No," I said. "Kind of like it."
"Good," Cindy said. "Because she'll do whatever we want. She's really into cross-dressers."
"Does she talk?" I asked.
Cindy didn't have to answer. Amanda did.
"Why talk," she said, "when we can fuck?"
She sat up on the couch and arched her back. Amanda slid off her panties, revealing a thin, black bush. She used the thumb of her right hand and the forefinger of her left hand to pull the elastic taut. Amanda aimed for her brother and let go. Cindy let the panties hit him in the face and fall to the floor.
"Come on, big brother," Amanda said. "Let's show this he-chick how we do it in our family."
Amanda spread open her legs and leaned back on the couch. Cindy brushed by me and fell to his knees between his sister's knees. He gazed at the folds of skin between her thighs for a half of a beat before plunging in head first.
Cindy went straight for Amanda's clit, working it up and down. Amanda's jaw clenched. Her chest heaved.
"Lick it," she said through her teeth.
Cindy looked up and caught his sister's gaze. Their eyes locked together. They stated at each with burning intensity. Cindy kept lapping at his sister's clit like a kitten in front of a milk bowl. I just stood there and watched. I wouldn't have dreamed of doing anything to interfere with their moment.
Amanda broke off the gaze. She closed her eyes and put her head back while wrapping a hand around the back of her brother's head. Amanda pressed Cindy's head into her pussy. Cindy's tongue disappeared inside the creamy flesh.
Amanda grinded her hips against Cindy's face. She moaned softly. But not for long. She was soon filling the room with the sound of pleasure -- and she didn't care if the neighbors could hear or not. She worked her hips so violently, I thought Cindy would come up with a bloody nose.
But he didn't. Amanda let out a hair-raising shriek, and Cindy's head emerged from between his sister's thighs. His lipstick was smeared and his sister's love juices covered his chin, glistening in the candle light.
Cindy stood up. With his hard on straining against his panties, he locked his gaze on me. He looked crazy, like he were staring at me from somewhere far away.
"Fuck my sister," he said flatly.
"What?" I asked.
"You heard me!" he yelled. "Shove your cock inside my sister!"
Amanda lay limply on the couch, her eyes half closed and her thighs dripping with pussy juice. She didn't seem to care what happened to her.
I could see where this was going. Cindy wanted me to do more than just fuck Amanda. He was asking me to bang the shit out of her, to abuse her.
And I decided to oblige him. I let the anger well up inside me and then directed it all at the pathetic, little whore lying on the couch.
Cindy must've seen my face harden. He came over to me and hiked my dress around my waist. He had a stone grimace on his face. I could feel his breath on my lips as he grabbed my pink panties at the hip and tore them off my ass.
With my stiff cock leading the way, I stumbled over to Amanda. I grabbed her by the ankles and yanked her off the couch. She was coherent enough to realize what was happening and caught herself before banging her head on the floor. When I had her spread eagle on the white carpet, I positioned my meat rod at the precipice of her hot, wet snatch. Our eyes met. She smiled out of the corner of her mouth.
"Whattsa matter, bitch?" she asked. "Forget how to stick it in?"
I grabbed a handful of her long, black mane near the scalp and pulled hard. She shrieked. I rammed myself inside her. She shrieked even louder. Her brother loved it.
"Fuck yeah!" Cindy roared.
He pulled off his panties while I pounded Amanda's cunt as hard as I could. I gave her the cock with long, punishing, machine-like strokes.
Cindy kneeled next to his sister and poked his cock at her lips. Amanda opened up and tried to turn her head. I let go of her hair. It was Cindy's turn to take charge. He gripped the top of his sister's head and made his entire prick disappear down her gullet. He pulled most of the way out and then shoved it back in. And then repeated. His balls bounced off of her cheek.
Amanda seemed to love it. Cindy and I were giving it to her hard in two orifices, but she never flinched or gagged. She just let us use her body any way we pleased.
Cindy's dispassionate face fucking didn't last long. After about a dozen long, slow strokes, he speeded up and then abruptly pulled out. His prick erupted all over his sister's face as I continued working her pussy. The first spurt hit her cheek. The second splattered across her forehead. Amanda had her eyes scrunched up by the time the third shot hit, but she kept her mouth open. An amazing amount of cum blasted across Amanda's face. I didn't know it was possible for one man to make such a mess. When Cindy was done, he flipped the last drop onto her nose, stood up and disappeared somewhere behind me.
I was close to dropping a load of my own. Amanda looked up at me with her cum-splattered face. About half of her brother's jizz pooled in her mouth. She held it there, half smiling, for me to see. I wanted to keep this sex adventure going, but it was tough to hold the cum in my loins. My pumps quickened. I felt like I had no choice but to let myself go.
I was wrong.
A pair of meaty hands grabbed me from behind and tore me off Amanda. I fell back on my ass. Cindy was standing above me with a chrome dildo smeared with something slick.
"Ok, bitch," Cindy said. "It's your turn. Bend over."
I got in the doggy style position and reached back to spread open my butt cheeks. My face was buried in the carpet. I heard Cindy kneel behind me and then a humming filled the room. There was no mistaking the sound -- the dildo was vibrating. Cindy gently inserted the tip into my bung hole. An amazing surge of sexual energy rippled through me. Pre-cum dripped off my cock.
"You like that bitch?" Cindy asked.
"Yeah," I said breathlessly.
He shoved the dildo deeper inside me. An involuntary grunt popped out of my mouth. Cindy gave me another inch of lubricated plastic. My cock felt ready to explode.
"More," I begged.
Cindy pushed the entire vibrating toy up inside me. He knew just how to fuck me. Cindy started with long slow, strokes and quickly built to an orgasmic fury. I'd been fucked with dildos before but never with such expertise. The last thrust was the best. Cindy shoved the vibrator as far as it would go and left it humming inside me for about 10 seconds. Then he took a full minute to pull it out of my hole. By the time he had the dildo out of my ass, I wanted to blow my load worse than ever.
But Cindy had other plans.
He tossed the dildo into a plastic bag and stood next to me. I rolled over and looked up at him. He was hard again. His cock -- at least eight inches -- bobbed invitingly. Cindy didn't have to tell me what to do. I got on my knees and wrapped my lips around the head. Cindy threw back his head and moaned as my lips slid down his pole. I opened my mouth and took the whole thing into my throat. I was careful to give him nothing but soft, wet flesh -- no teeth. Cindy didn't try to grab my head or shove himself inside me. He just let me suck him off in my own special way.
It didn't take long for Cindy's pre-cum to dribble across my tongue. Bu he wouldn't let himself blast in my mouth.
He pulled his fuck stick out of me and hurried over to his sister with his dick in his hand. She was lying right where we'd left her with cum still splattered across her face. Cindy kneeled next to her and aimed his cock at her face, just like before. I rushed over and did the same on the opposite side of her face. Amanda opened wide and squeezed her eyes shut. Cindy and I started stroking ourselves. I exploded a half second before him. The relief was immediate. My loins unleashed a gallon of cum.
Cindy and I covered Amanda in jizz from her forehead to her chin and left h a nice size pool in her open mouth.
"Clean it up," Cindy said, while flopping back on the couch.
Amanda had a dumb half-smile on her face, even with her mouth wide open and filled with two guys' jizz. Her eyes were closed.
I laid on top of her and thrust my still-stiff dick into her still-wet pussy. She inhaled sharply. I gave her a long, slow kiss, lapping the salty cum off her tongue. I pumped her slowly and gently while cleaning her right cheek and then the left. I licked the pools on her forehead and the little rivers that trickled down her neck. The cum slid down my throat like I was born to drink it. Just as I took the last drop off her chin, I shot my load into her pussy. Amanda accepted it with a gasp.
When I rolled off of Amanda, Cindy was already pulling his wig off his head.
"That was good," he said. "We'll have to do it again sometime."
"Yeah," I said.
"You know how to get a hold of us," he said.
Cindy didn't have to utter another word. The expression on his face said it all. He didn't want to make small talk anymore than I did. We were using each other for weird sex and that was it.
I pulled down my dress and hurried back to my car, leaving my torn panties and Amanda lying on the floor.
I don't know if Cindy and Amanda will ever want to fuck again. But if they do, I'll be ready for them.