The First Twatsgiving

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Cross-dresser celebrates holiday with new family.
2.6k words
4.25
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My step-sister, Katie, wore nothing but a pink string bikini as she stepped out on the patio. She had long blonde hair, a doll face and a set of tits that would make Pamela Anderson weep. I watched from my bedroom window as Katie spread a towel across a reclining beach chair. She sat on the edge and spread suntan lotion on her long legs. When she finished, she laid back in the chair. Even with her hands over her head, her tits still looked enormous.

So, this was Thanksgiving in Florida: watching my 18-year-old step-sister sunbathe next to our pool. Katie was nice to look at, but I missed Ohio. I'd followed my father south a month earlier. He was a degenerate gambler who' finally had some luck and somehow convinced Katie's mom, Lisa, to marry him. She was the heir to a toothpaste fortune and a former fitness model. You might recognizer her. She used to make exercise videos. That was 20 years ago, but Lisa still has a smokin' body.

Yeah, pops had done pretty well for himself. After the wedding, I decided to tag along to enjoy the fruits of his labor. I dropped out of community college, packed a duffle bag and drove south. I'd been regretting it ever since. I absolutely couldn't stand my new step family.

While the rest of my real family was back up in Ohio watching football and eating turkey, I was down in Florida with Katie and Lisa, the two biggest cunts I'd ever met. Not even pops was there. He'd gone to Vegas for the week on what he called "business."

I watched Katie from my bedroom window. My cock began to rise in my shorts. I quietly began tweaking my nipples. As much as I hated her, I'd had a crush on Katie since the day we'd met and would've done anything to spend just one night in her bed. But she thought I was creep. I think she'd caught me staring at her tits a few too many times. And I think she was starting to figure out that I sometimes snuck into her lingerie drawer a borrowed a few items when she was out.

I'll tell you straight up: I'm a sick, twisted werido. My sex fantasies run to the extremes. I not only wanted to fuck my step-sister, I wanted to become her. To walk, talk, look, smell -- and even fuck -- like she did. And I wanted her to know about it. If I couldn't do it with Katie, I wanted to do it with her mother. They looked and talked almost alike, except they were 20 years apart.

But I didn't think it would ever happen. How would I even begin to broach the topic? I can see how the conversation would go: "Uh, yeah, I know I'm your step-brother, but would you mind if I dressed up in your bra and panties while you watched?" I figured she would surely tell my dad, who would undoubtedly kick me out of the house.

Katie sunbathed about 10 minutes before sweat started glistening on her chest. Through my binoculars, I watched a single drop slip from her neck to her left breast before disappearing into her swimming suit.

I couldn't stand it anymore. I ran down the hall to Katie's bedroom and went straight for her lingerie drawer. She kept everything neatly folded and scented with perfume. I picked out a corset and stripped off my jeans and T-shirt in her bedroom. My dick rose at the thought that she could've walked in at any momemnt.

The corset was a bitch to put on. There were a dozen hooks in the back. I didn't know what to do. I'd always worn bras, panties, dresses and bikinis. But rhe corset was something new. After struggling for 10 minutes, I finally figured out that I had to put on the corset backwards and then twist it around. It was worth the trouble. The garment squeezed my body in the exact right places, especially around the tits. I pulled all the flesh I could into the cups and almost filled them out.

Next, I put on thigh high stockings, hooking them to the corset's garter straps. This wasn't easy either, but I finally got it, even making sure the straps were even and straight. I finished off the outfit by slipping on a G-string over the garter straps. That's when I realized that the G-string usually goes on under the straps. But by this point, I figured, "fuck it," and left it alone.

I sat at a vanity table and used Katie's make-up to paint my face like a whore: heavy eyeliner and bright, red lipstick. When I stepped back to take a look at myself in the mirror, I saw like a pathetic, piece-of-shit cocksucker. What I needed was a good, hard, punishing ass-pounding. There was one place I knew where to find it.

The Internet.

I rushed back to my bedroom and turned on my computer. My plan was to go onto the site where local fags meet to arrange hook-ups and see if I could find a companion to sneak up to my room. But just as about to log on to the site, I felt the hairs on the back of my neck stand. Someone was in the room with me.

"Hello, faggot."

It was Lisa, my step-mother. She stood with her hands on her hips and her feet about shoulder-width apart. She wore a lacy, white bra and matching panties. She had a dime-size birth mark on her hip.

"Borrowing some of your sister's clothes?" Lisa asked.

My heart sank. She'd caught me. This was it. I'd be kicked out of the house for sure.

Towering over me, Lisa grabbed me by the chin. Her fingers pressed into my cheeks, forcing my lips to pucker.

"So, you want to be a little girl, is that it?" she said. "OK, I'll show you what it's like to be a little girl."

She shoved me hard. My neck snapped back.

"Get in my room now," she said.

I walked down the hallway with my head down. Just before making the turn into my parent's room, I figured out how Lisa had caught me. I'd left Katie's door open. Lisa must've walked by.

She followed me down the hall, yelling, "Dirk! Get up here! And bring my daughter!"

A deep, far-off voice replied, "Yes, ma'am!"

Dirk was a tall guy about my age who always seemed to be just hanging around the house. I was never sure what he did. Lisa told me he was a handyman, but he never seemed to fix anything. Turns out, he did much more than I ever imagined.

Dirk was Lisa's man-whore.

While we waited, Lisa sat next to me on the bed. She fixed me with a glare and grabbed my right tit. She squeezed and then did the same with the left. I moaned involuntarily. Lisa slapped me across the face. It stung.

"You think those are tits?" she said. "These are tits."

Lisa grabbed me by the back of the head and smashed my nose into her cleavage. My nostrils filled with the sweet scent of her perfume. I started to feel clausterphobic and tried to pull my head out. Lisa wouldn't let me.

Then I heard Dirk's voice.

"Uh, ma'am, we're here," he said.

When I looked up, Dirk and Katie were standing next to the bed. Katie, still in her bikini, was rolling her eyes.

"Oh boy, it looks like mom forgot to take her crazy pills again," she said. "What's it gonna be this time, mom? Want me to eat Dirk's ass while you fuck yourself with a dildo and anal beads?"

Lisa smiled.

"You know me well, daughter," she said. "But I was thinking of trying something a little different today. It seems your step-brother wants to be a little bitch."

I felt Dirk staring at me. A lump rose in his jeans. But he didn't move. He just stood at attention like Lisa's loyal servant.

Katie came over and sat on the bed. She planted a hot, wet kiss on my neck. I started breathing hard.

"Well, well," Katie said. "We've got another perv in the house."

Katie and her mother smiled at each other.

"Looks like we're gonna have some fun," Katie said.

Lisa nodded.

Then Katie slapped me across the cheek. The smack echoed through the room. Dirk winced.

"Let the games begin," Katie said with a giggle.

Lisa reached under the bed. Her hand emerged with a slim, silver dildo and a tube of lube.

"Bend over, bitch!" she said.

I thought she was talking to Katie, so I just sat there, totally freaked out by the whole scene. Then Ann corrected me. She grabbed me by the back of the neck and squeezed hard.

"That means you, cunt!" she said.

I got into the doggy-style position on top of the bedspread and waited for whatever was next. Anything could happen. It was turning out to be a very weird holiday.

"Grease that bitch up," Lisa said.

Lisa and my dad had a fancy bedroom set that included a mirror behind the bed. I could see everything that was happening behind me in the reflection. Kneeling on the bed, Katie moved into position behind me. She smacked my ass. Everyone but me got a chuckle out of it. Even Dirk snickered. I was too freaked out to laugh.

Katie slid the panties off my ass and down my legs. I had to lift my knees one at a time to help her get them off. Then Katie leaned over and stuck her tongue into the top of my ass crack. A tingle shot up my spine as she worked her tongue horizontially, then vertically, slowly making her way south. I knew where she was headed: the bunghole. My skin prickled with anticipation. Katie didn't play with my hole when she arrived. She spread open my cheeks with her fingertips and dove right it, as if she were trying to stick her tongue up my ass.

"Yeah," Lisa said. "Suck that he-cunt."

To that point, nothing in my life felt had ever felt so good. And it was about to get better.

"Lube, now," Lisa said.

Katie squirted some lube on her forefinger, then shoved it up my ass. She pumped a few times, then spread some lube on the dildo. When she twisted the bottome, the silver rod vibrated to life. Katie gently placed the tip of the fuckstick oton my asshole. I flinched. No one had ever shoved anything inside me before. Katie gently wiggled the dildo. My bunghole slowly loosened up. Sensing I was ready, Katie slipped the dildo inside me. My ass accepted it, as if I'd been waiting for it all my life.

"Looks like she likes," Lisa said. "Dirk, give her a little taste of salami."

Dirk nodded solemnly and stripped off his clothes, starting with his shirt. It was obvious he spent a lot of time in the gym. Naked, Dirk kneeled on the bed in front of me with his stiff cock pointing straight at me.

While Katie worked my ass from behind, I let Dirk fill me from the other end. I opened my mouth and took in the head of his cock. Dirk let me set the pace, so I took it slow. After all, this was my first blow job. I moved my head back and forth, letting my tongue drag along the underside of Dirk's prick. He threw back his head and moaned.

"Look at this, Katie," Lisa said. "She's a fuckin' natural."

"I knew it," Katie said. "She even smells like a cocksucker."

She shoved the vibrator in especially hard. I emitted a muffled shriek.

The slow sucking didn't last for long. Dirk wanted more. He grabbed the sides of my head and repeatedly forced me to swallow his whole cock. Each time he shoved himself inside of me, I caught a noseful of pubic hair. He smelled like Brut.

A little pre-cum splashed on my tongue. Dirk's thrusts quickened. So did Katie's dildo strokes. I squeezed my eyes shut and waited for the nut to come gushing.

When Dirk jizzed, he didn't hold back. Cum flooded my mouth. Everytime I thought he was finished spurting, along came another shot. I couldn't hold it all. Jizz trickled out the corners of my mouth and down my chin.

Lisa flopped onto the bed next to me. Laying on her back, she said, "Give me a taste." She opened wide.

I let the jizz slowly dribble into her mouth. She refused to swallow any of it, allowing the juice to pool around her tongue. When every last drop had been transferred, Lisa sealed her mouth. Smirking, she looked at her daughter and patted the bed next to her. Katie gave the vibrator one last shove, leaving it deep inside me. She laid next to her mother and opened wide. I could hardly believe what came next: Lisa let Dirk's jizz trickle off her tongue into Katie's mouth. And, like her mother, Katie refused to swallow.

"Your turn," Lisa said to me.

She didn't have to say another word. Kneeling over Katie, I aimed my cock at her mouth and shot my wad. The first spurt missed, splattering across her cheek. But most of the rest hit the mark. As I came, my ass muscles squeezed the vibrator out of my body. It was a strange -- yet wonderful-- sensation. The dildo definitlely made me cum harder. By the time I was done, Katie's mouth was brimming with hot jizz. Dirk laughed. He had settled into a chair near the bed.

Lisa was smiling at me.

"You ever wonder what two guys' cum tastes like after it's been recycled through two mouths?" Lisa asked.

"Not until you brought it up," I said.

Lisa smiled, then fell onto her back with her mouth open. Katie dribbled the jizz cocktail into her mother's mouth. I knew I was batting clean up, so I got into position.

Lisa's face appeared over me. Her long, brown hair nearly touched my face. She looked down at me with her big, brown eyes and smiled for a long time with her lips bulging, reminding me the stream could be coming any time. Lisa finally let it go. But she wouldn't just let me have it. Oh, no, that would be too easy. Lisa released the jizz so it seemed to come at me in slow motion. I accepted the whole load into my mouth without swallowing, just like Lisa and Katie had done.

"You know what to do now," Lisa said.

I playfully flipped my tongue at her. A little jizz dribbled out of my mouth. Then I sealed shut and swallowed. It took two gulps, but the cum went down smoothly. Katie licked the wayward stream of jizz off my cheek.

I breathed hard. I thought it was all over.

But then Katie laid on her back and Lisa climbed on top of her in the 69 position. They ate each other's pussies with a shocking ferocity. I looked at Dirk. He shrugged as if to say, "Happens all the time." So, I settled in to another chair and watched. Lisa and Katie made each other cum hard. They moaned, shrieked and shivered in ecstasy.

When it was all over, Lisa rolled off of Katie. They lay next to each other breathing hard for a while but saying nothing. Finally, Lisa turned to Katie.

"Happy Twatsgiving!" she said.

"What do you think, mom," Katie said. "Should we make it a tradition."

Lisa smiled devilishly at me.

"Oh yeah," she said.

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3 Comments
pantyhosefunpantyhosefunover 2 years ago

Wish there was a Katie and Lisa in my life!

WannaBLucyWannaBLucyalmost 14 years ago
loved it

Great story any more???

AnonymousAnonymousalmost 17 years ago
Awesome!

Crossdressing, humiliation, and having women watch while sucking cock and swapping cum - what could be better?

I loved it! Please keep writing.

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