tagTranssexuals & CrossdressersCum On My Step-Brother's Face!

Cum On My Step-Brother's Face!


My mouth went dry. My palms began to sweat. Each creak in the floor board seemed to rip through the entire neighborhood. The fear built so high, that I almost turned back.

But then I told myself, "It's cool. You're the only one home."

At least it seemed so at the time.

I pressed on toward my step-sister's lingerie drawer. Her bedroom lay silent, but it felt like the teddy bear on her neatly made bed was watching me. I turned it face down into her pillow.

I couldn't afford to get caught. How do you explain to your parents that you get off on dressing up in your step-sister's bras and panties? Somehow, I get the feeling they just wouldn't understand. And if they do, I don't want to know why.

When I finally opened Holly's drawer, I saw that I'd hit the mother lode. She had a wide selection of garments, all lace and silk folded into neat piles. A sheer pouch filled with potpourri and sealed with a pink bow sat in a corner of the drawer, filling the room with a sweet, sexy scent.

I stripped naked.

A framed picture of Holly sat on the dresser. She was laughing with her arms around two sorority sisters. My step-sister was stunning-- pretty enough to be in Victoria's Secret but sultry enough to be on the cover of Hustler. In the photo, she had on blonde hair with brown streaks draped over her shoulder. Huge tits bulged beneath her pink sweatshirt.

With her picture and lingerie spread in front of me, an absurd question popped into my mind: What would Holly want me to wear?

I had no reason to believe that Holly would ever go for something like that. But I snatched the fantasy and hung on to it. "What if she did get into it?" I asked myself.

I decided that she'd want me in a lacy black bra. It just so happened that she had one on top of the lingerie pile. I pressed the fabric to my nose and inhaled her perfume. She must not have washed it the last time she wore it.

The under wire cups dug into my chest as I clasped the bra behind my back and slid the straps onto my shoulders. Leaning over, I checked myself out in a mirror hung above Holly's makeup table. I had a nice set of tits for a guy. When I pulled more flesh into the cups, my breasts looked even bigger. Heck, I almost filled out the bra.

Holly had a matching black thong that I pulled on next. I always thought wearing a thong would be uncomfortable, like having a piece of dental floss up your ass. But it wasn't like that at all. The thin strip of fabric settled easily into my crack. It was always there without being bothersome, reminding me of my femininity. Up front, I had a little trouble fitting my cock and balls into the little triangle of sheer fabric. But I managed to get it done. I was determined.

Now it was time to dress up the legs. Sitting on the bed, I slid on a pair of thigh-high stockings, careful to make sure the seam went in the back. The garter belt that went with the stockings was a bitch to put on. There is an art to fastening the clasps, especially in the back. I admire anyone who can do it in less than five minutes.

When I finally had myself together, I checked the mirror again. Truth be told, I looked ridiculous. It would take a gallon of wax and a team of Swedish surgeons to make me pass for a woman. But I felt sexy. The outfit squeezed, caressed and hugged me in all the right places.

Holly's closet door was open. A black cocktail dress was right in front, separated from all the other clothes. Holly had worn it to a Christmas party and had looked amazing. I'd caught her boyfriend that night pulling her into a corner, kissing her hard and reaching under the dress to grab her ass.

"Fuck it," I whispered.

I yanked the dress off the hangar and slid it over my head. The wide scoop in front left plenty of chests exposed but enough fabric remained to cover the bra straps. It was a short dress. If it weren't for the panties forcing my cock upwards, it might have poked out of the bottom.

I sat at Holly's makeup table and made up my face as slutty as possible. Fire red lipstick. Heavy black eyeliner. Dark gray eye shadow. Then I draped a string of pearls around my neck and sprayed myself with perfume.

I blew myself a kiss in the mirror. I suddenly wanted very badly to be fucked, to be treated like the whore I'd become. My mind raced: Where could I find a quick lay? Then it hit me. I could have an escort service send over a call girl. But just before I turned around to look for a phone book a voice emerged from across the room, pimp-slapping me back into reality.

"Very cute," she said.

I recognized the voice immediately. It belonged the worst person possible in this situation.


I turned around. She had her elbow propped up on the door frame and her hips cocked to the side. A smile with an unmistakable message covered her face: "Gotcha!"

"Need to borrow a dress?" she asked.

I stammered, "I, uh, I guess--"

"Save it, fag boy," Holly snapped.

She stepped into the room and closed the door behind her. As much as she'd startled me, I couldn't help but notice how great Holly looked. She wore a pair of low rider jeans and a cut-off T-shirt. Everything from her hips to the area just below her tits was exposed. Holly had a flat, smooth stomach. The nipples poking into her shirt made it obvious she wasn't wearing a bra.

I watched her open a desk drawer and pull out a digital camera.

"What are you going to do with that?" I asked.

"Oh, nothing," Holly said.

She snapped off a couple of quick shots. I tried to turn and cover my face but I knew she got me.

"Unless you want those posted on MySpace, you'll do what I say," Holly said.

She had me. We both knew it.

"What do you want?" I asked. "Wash your car? Type your term paper?"

"It's not going to be that easy," Holly said. "You're going to debase yourself. You're going to act like the whore you are. You're going to suffer humiliation."

I didn't know what the hell she was talking about, so I said, "fine," because I didn't see any other options.

"You just sit there and look pretty," Holly said. "I need to make a couple of phone calls."

She whipped a phone out of her purse. In the first call, Holly said, "Yeah, hi, it's me. I was just wondering: Is Ted still bi?...Great, give me his number...Never mind, I'll tell you later. Bye."

In the next call, she said, "Hey, Ted, it's Holly. You interested in a quick hook-up with me and my step-brother?...Totally serious. He's a cross-dresser." A loud squawk ripped out of the phone. Holly smiled and pulled the phone away from her ear. "Great," she said. "Come on over. Just come up to my room."

Holly snapped shut the phone and smiled devilishly.

"Now the fun is really going to start," she said. "Let's start with a few poses for my photo album."

"What do you mean?" I asked.

Holly glowered at me, took two steps toward me and slapped me across the face.

"I ask the questions here," she said. "You get on that bed and pose like I'm a Playboy photographer."

I got in the doggy-style position on the bed and licked my lips. Holly snapped a shot.

"Good," she said. "Gimmie s'more."

I rolled onto my back and stuck my legs into the air like a chick begging for cock. The camera flashed. I started getting into it. I leaned over to give the camera some cleavage. Flash. Then I spun around and pulled up my skirt to show some ass. Flash.

"Stay right there," Holly said.

She rummaged through a drawer and came back with a long, slender, chrome dildo and a tube of lube. She set the lube aside and handed me the dildo.

"Wrap your lips around this," Holly said.

I did and the camera clicked.

Holly then set the camera on the desk and pointed the lens at me. She rushed over and stood in front of me. Holly undid the fly on her jeans and stuck the dildo through the hole, as if she had a hard cock pointed at my mouth.

"Suck it, bitch," she said.

I put my lips on the dildo just as the camera's timer expired. Flash.

"OK, enough of that," Holly said. "Time to get hardcore."

She got behind me with the dildo and the lube. Holly turned on the dildo. It hummed lowly, then she cranked it up to a whine. She gently set the dildo on my bung hole, outside the fabric of my thong. Blood rushed to my cock. I didn't think it could get any harder than it already was, but it did.

Holly pulled away the dildo and, with one hard yank, ripped apart the thong. She squirted some lube onto two fingertips and rubbed the dollop onto my corn hole. The cool gel made me break out in goose bumps. But that was nothing compared to what came next.

Holly set the dildo onto my asshole and just let it whine for about three seconds. Then she shoved it in but just a little.

"You like that, you fucking weirdo?" she asked.

"Yes," I grunted.

"I knew you would, faggot," she said.

With that, Holly gave me a full taste of the vibrating dildo. I don't think she shoved it in all the way in, but it was enough to make me grit my teeth and grunt again. Holly started working me -- slow and shallow at first, but steadily going harder and deeper. Each thrust took me into a higher plane of pleasure. Holly and her vibrator were reaching parts of me I didn't know existed. Cum began to leak from cock -- and Holly hadn't even touched it.

Without warning, Holly pulled out the vibrator. Breathless, I turned over to see what was wrong. A tall, frat-boy type with brown hair was standing in the doorway. It was Ted. I'd gotten so into my ass-reaming I didn't notice him come in.

"She's all ready for you," Holly said.

Ted looked at me like a tiger does its prey. Without a single word, he pulled off his shirt and jeans. He had ripped abs and a cock that went at least eight inches. Ted stepped to the edge of the bed and put his semi-hard dick in front of my face. I wrapped my lips around it.

My eyes locked onto his as I took his meat pole deep into my mouth. I felt him stiffen inside me. Ted tossed back his head and moaned softly. I was careful to give him nothing but lips and tongue. On each down stroke, I took more of his cock into my throat. He put his hand on the back of my head and made me take it all. The head of his dick poked my tonsils. But I took it astoundingly well. I didn't gag, just relaxed and let him do it.

Ted made me suck him faster. He began to shake. I thought, "This is it. He's going to cum." But then Holly screamed, "Fuck him in the ass!"

Ted pulled out. I got on all fours with my ass hanging over the edge of the bed. Ted gave me all eight inches at once. I thought the vibrator was nice. But it was nothing like having real human flesh pumping my ass.

Ted went hard and deep on every thrust. It was like having a pleasure button far up inside me. And Ted kept hitting it over and over. The tips of his fingers dug into my hips. I'd later find that he left small bruises. But I felt nothing but ecstasy at the time.

His thrusts got shorter and harder. Then he suddenly pulled out.

"Cum on my step-brother's face!" Holly screamed.

The second I flipped over, a torrent of jizz splashed across my face. Holly's camera flashed. Ted let it all out. Cum ran down my cheeks and chin. It felt like he'd dumped a gallon of it on me. I managed to open my eyes long enough to see Holly hand the camera to Ted and kneel next to the bed. She lapped the jizz off my face like a puppy.

Holly swallowed Ted's cum and then put her lips on my cock. I immediately burst. It was like the Hoover dam breaking. Holly couldn't take it all. Little streams ran down her cheeks. She held all she could in her mouth and then hovered above me. I opened wide and let her drool my own cum into my mouth.

I swallowed it.

Holly wiped her mouth with the back of her hand and looked coldly at me.

"If you want to keep those pictures off the Internet, you'll let Ted fuck you anytime he wants," she said. "You keep the dress and lingerie. Wear it for him, if he wants. Now get the fuck out."

I walked down the hall, feeling more humiliated and used than I ever had in my life.

And I couldn't wait for more.

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