tagTranssexuals & CrossdressersJanie's Got a Dildo

Janie's Got a Dildo

byStephanieSeymour©

My stepsister, Janie, has huge, natural breasts. When she bends over, an impossibly deep abyss forms between them. The best part is that she knows how to carry her rack, showing them off without flaunting them. She buys bikinis a half size too small, so her tits look like they could spill out at any moment. She does something similar with dresses. The tight fabric gripping the top forms little waves of flesh, as if her nipples are trying to jump out the top to gasp for air.

For me, Janie's tits are the perfect size: huge. had But she's not some freak-of-nature, hefting around a pair of watermelons that could win a set of blue ribbons at the county fair. Her mounds are more like cantaloupes.

I once plucked one of her bras out of the dirty clothes. The tag said "36 DD." I put the lacy, purple fabric up to my nose and inhaled deeply. My cock rose as the scent of Janie's perfume filled me. I took the bra to my bedroom and strapped it across my chest. As the under-wire cups pressed into my flesh, I closed my eyes, licked my palm and stroked off. A porno movie starring Janie and me rolled behind my eyelids. I titty-fucked her in the fantasy until I came into my hand in real life. I dumped the load into my mouth while imaging what it would be like to watch Janie swallow my cum.

Never did I think my fantasy would ever come true. I mean, how do you make a pass at your own stepsister? I can see it now: "Uh, hi. I know we're technically related, but whaddaya say I titty-fuck ya until I cum on your face?" Yeah, I think that might make the next family Christmas party a little awkward.

A stunt like that could also get me kicked out of the house. My stepmother was just looking for a reason. I think she knew that I had a crush on Janie, who had just turned 18, making her legal. Plus, I was 24, jobless and still mooching off my parents. Dad, however, didn't have the heart to give the boot to his only son.

Before I go on, I should make something clear about Janie. If it weren't for my parents, I could've given two shits about offending her. Janie may have been hot, but she was a bitch. She tried several times to get me kicked out of the house. For example: When our parents went out of town for a week, she concocted this story about how I threw a huge house party. That was bullshit. A few of us -- 15 or 20 at the most -- met at our house before heading out to the clubs. That's it. Her lie didn't work. Dad totally sided with me. It was all about her wanting my bedroom, which was bigger than hers.

But the truth is, the more she pissed me off, the more I wanted to fuck her.

She must've felt the same way -- because I didn't have to make a pass at her. She came after me.

I was walking past her bedroom one summer afternoon when I heard her say, "C'mere bitch."

I stopped and doubled back.

"Excuse me?" I asked.

"I said come in here if you know what's good for ya," she said.

When I opened the door, Janie was leaning against a dresser. She wore a white, see-through bra and matching panties. Erect nipples pushed into the thin fabric. Her bush was shaved into a thin, Mohawk.

"Put your lips on my pussy," Janie said.

"Excuse me?" I asked again.

"You got a hearing problem or are you just stupid?" she asked. "Let me make it clear: you are going to suck my pussy or my mom will find out that you've been raiding her lingerie drawer."

"I don't know what you're talking about," I said.

I was lying but had to at least call her bluff. Truth be told, I'd been cross-dressing in my step-mom's lingerie for years. If Janie could prove it, I was fucked.

She pulled a lacy, black bra out of the top dresser drawer and flung it at me. I caught it with one hand and looked at it, trying to seem unimpressed.

"Exhibit one," she said.

"Never seen it," I said.

Again, it was a lie. It was my favorite bra. If I pushed all my flesh into it and bent over, it looked like I had real tits and cleavage.

"This proves nothing," I said.

Janie smile wryly.

"Exhibit two," she said.

Janie pushed play on a remote control. A small, pink television on her desk flickered to life. The camera angle encompassed the dresser and bed in my parents' room. A man entered the screen with his back to the camera. He opened the top drawer and plucked out some clothing. Casting aside his T-shirt and jeans, the stranger strapped on the bra and pulled up the panties. He finished the outfit with a pair of stockings and a garter belt.

"Now watch what this sick fuck does," Janie said. She had her arms folded and was smiling smugly.

The guy goes back into the drawer and pulls out an object about the size of a screwdriver and what appears to be a jar. As he kneels on the bed in a doggy-style position, he turns toward the camera. His face becomes plainly visible. Surprise, surprise. It's me with my face painted in my stepmother's makeup. By now it was obvious that I'd been caught on a hidden camera. Janie had probably tucked between some clothes on a chair in the corner of the room.

I watch myself unscrew the jar of lube and grease up the vibrator. A low humming fills the room as I twist it on. I reach back and pull aside the panties. The sound becomes muffled as I slowly shove the dildo up my ass. It doesn't take long for me to flip over-- without pulling out the dildo -- and jack myself off, cumming into my hand. As I watched myself smear the cum over my face, I remembered why I did it. I'd seen a cumshot movie and wanted to know what it felt like.

Janie snapped off the video.

"You are a sick piece of shit," she said. "But that's OK because I'm going to use you like the miserable trash you are."

I was screwed. We both knew it.

"Fine," I said. "What do you want?"

"Like I said...lick my pussy," she said.

Janie slid her panties to the floor, spread her legs and leaned her ass against the ledge of the dresser. I dropped to my knees and sniffed her glistening clit. She smelled clean yet delightfully musty. I thrust my tongue at her pink flesh, batting playfully at the folds. Her salty juices melted into my tongue.

"Yeah, bitch," Janie moaned. "That's right."

I smashed my face into her crotch and shoved my tongue as far up her pussy as it could reach. Her legs trembled as my tongue wiggled. Then I moved to the clit and licked like a madman. This was when Janie lost her mind. She grabbed me by the back of the head and pushed my face into her cunt.

"Lick it, bitch!" she yelled.

Janie made no attempt to suppress her moans as I worked. All I could see was hairpie. Her perfume and musty love-scent filled my nostrils. It was exhilarating -- a feeling heightened by the real possibility that she might hurt me.

Janie yanked hard at my hair when she came. For a second, I thought she'd taken out a chunk. But she kept pulling, forcing my head back. Her thighs were soaked. She could barely stand, she was shaking so badly.

Janie gradually loosened the grip on my head as she regained her composure. After finally letting go completely, she threw back her head to take the long, brown hair out of her eyes.

"That was good," she said. "I needed that."

I stood up and moved toward the door.

"Not so fast," Janie said. "I'm not done with you yet."

She went back into the top dresser drawer and pulled out the panties, stockings and garter belt I'd been wearing on the video. She tossed them on the bed.

"Put it on," Janie said.

In the confusion, the bra had ended up on the floor. As I picked it up, I noticed Janie was taking a handheld video camera off of her bookshelf. She flipped open the viewer and trained the lens on me.

"Smile," she said, "you're on Candid Camera!"

"Whatever," I snarled.

I stripped naked, tossing my jeans, boxer shorts and REO Speedwagon T-shirt into a corner. Janie whistled mockingly at my naked body.

"Ooh, baby," she said.

It was obvious that the video camera was no prop. The red light was on. And Janie wouldn't take her eyes off the viewer.

I pulled the bra across my chest, hooking it in the front and then sliding it sideways until my tits were aligned with the cups. As I pulled the straps onto my shoulders, I began to feel like a woman. The bra put pressure on my tits in all the right places, like a pair of warm, friendly hands. I went for the panties next, but Janie stopped me.

"Do the garter and stockings first," she said. "I might need to pull off the panties in a hurry."

"Whatever," I said.

I rolled up the fishnet thigh-highs into little pouches and inserted my toes into the ends, then. carefully unfurled them up my leg one at a time. It was like putting a giant condoms on my legs. I was getting good at it, too. I didn't leave one run in the stockings.

The garter belt slid on with no problem, as I expected. The tough part was hooking the stockings to the straps. The hooks in back are especially tough. But I did it with little trouble, despite no help from Janie.

I finished the outfit by sliding the thong over the tops of the garter straps and stuffing my cock and balls into the small, silky triangle of fabric up front.

"You are very, very pretty," Janie said with as much sarcasm as she could muster. "Now do your make up."

I SAT on the pink, velvet stool Janie had in front of her makeup table. Janie followed me with the camera. My hand automatically went for the charcoal black eyeliner.

"Like a true whore," Janie said.

Ignoring her, I penciled on the makeup with the help of a mirror hanging above the table. Then I brushed on some light gray eyeshadow and lay on the mascara thickly. The lipstick I chose was fire-engine red. And because it was sitting there, I sprayed on some of Janie's perfume.

When I was done, I turned toward the camera, flipped open my arms and said, "Ta-da!"

Janie shook her head with a crooked smile on her face.

"You sexy, little whore," she said. "Go sit on the bed."

Janie set the camera on the dresser without turning it off. She adjusted it so the lens was pointed at me. The red light continued to glow.

Janie came over to the bed and looked down at me. Her tits were in my face.

"I am going to abuse the shit out of you," she said.

Janie pinched my nipples between her thumbs and forefingers, then rolled them. My cock became impossibly hard. I moaned unintentionally. My eyes closed. I floated into heaven.

Without warning, I felt the pressure come off my nipples. Janie had stopped tweaking them. But before I could open my eyes to see what was happening, her hand smacked across my cheek. Then the back side of her hand whipped my other cheek. My entire face stung.

"You piece of shit," Janie said. "Get on your hands and knees."

While I assumed the doggy-style position on the bed, I watched Janie go to the top dresser drawer. This time she took ou stepmother's chrome dildo and the jar of coconut-scented lube.

Setting aside the lube, Janie knelt in front of me on the bed. She held the dildo in front of her, as if it were cock.

"Suck it," she said.

I played along, wrapping my lips around the tip. Even though it was plastic, I treated the dildo like real flesh and blood. I was careful not to let my teeth touch it as Janie shoved it down my gullet. She face-fucked me like a man. I let her do it, opening my throat so she could go deeper. Our eyes locked together. She had a look of contempt painted across her face that could only come at the most pathetic of sights. At the moment, I was that sight.

Janie soon had enough of the simulated blow job. She pulled the dildo out of my mouth and moved behind me. I heard her unscrew the lube and slather a dollop across the fuck toy. She pulled the panties down past my thighs. The dildo hummed when she turned it on. It went a pitch higher as she switched it to full speed.

"Spread your cheeks," Janie said.

My face fell into a pillow as I reached back to open wide. Janie put the tip of the vibrator on the outside of my asshole and just held it there without sticking it in. Waves of pleasure rippled through my body.

"Ready to get fucked, bitch?" Janie asked.

I started to scream, "YES! FUCK ME!" But I swallowed the words because she immediately jammed the humming machine inside me. The waves of pleasure turned into a tsunami. Janie fucked me slowly at first but quickly built up speed. She was soon slamming my ass as fast and as hard as she could. I had to work hard to keep from cumming. The experience was so hot, I didn't want it to end. But I finally couldn't take it anymore. I was going to have to let go.

Just before I did, Janie pulled the dildo out of my butt. I spun around to see what was going on. Janie flung aside her bra and reached for the lube. She scooped out a handful and spread it across her chest, covering the area that formed her cleavage when she wore the right kind of dress. Janie laid down next to me and squeezed her tits together.

"Fuck 'em," she said.

I mounted her and slipped my cock into the cleavage. Each time I thrust forward, my dickhead peeked out the top of her tits, then retreated, like a turtle who kept checking to see if it were safe to come out of his shell. Janie stared revoltingly into my face, as if she'd never asked for any of this. The attitude made me push harder. But I couldn't fuck her tits for long. The jizz rose quickly through my loins. I held back as long as I could. But when I just couldn't any longer, my cock exploded.

Dick snot spewed across Janie's face. The first shot was like something out of a fire hose. Janie kept her mouth open for me. The second blast fell across her lips and tongue. Her face was streaked with my cum from forehead to chin by the time I finished.

"Now clean up your mess, motherfucker," Janie said.

Like a dog, I liked the my own jizz off of her face without leaving a drop. The goop was salty. I kept as much of it in my mouth as I could without swallowing.

"Give me a taste," Janie said.

She opened wide and I slowly drooled the jizz into her mouth. I watched her take it in. When the stream came to an end, she closed her lips and swallowed. She smiled sweetly.

Then her face hardened again. She pushed me off of her.

"Get the fuck out of here," Janie said.

I was stunned.

"You serious?" I asked.

"You're fucking right I'm serious," she said. "Get the fuck out until I'm ready to use you like a piece-of-shit cunt again. And, by the way, if you ever piss me off, both videos are going on the Internet."

What could I do? I just fucking left.

I went down the hall to the bathroom and cleaned up. Back in my bedroom, I changed back into my guy clothes and then headed for my parents' room to replace my step-mom's lingerie. Janie met me in the hallway. She stopped in front of me and gingerly put a hand on my cheek. A warm smile spread across her face. I thought she was going to apologize and tell me how much fun she had. Instead, she wound up and slapped me.

Hard.

"Cunt," she said.

Then she kept walking, as if nothing had happened.

So that's how it is with us now. Janie abuses me whenever she feels like it, and I take it.

But you know what?

I like it.

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