tagTranssexuals & CrossdressersSister, Meet My Sissy

Sister, Meet My Sissy


George was mincing around the bedroom on his new high heels, almost moaning in joy as his big cock slid around in the inside of his panties. I could see the thick buttplug in his ass through the thin panty material and I smiled. George was a lovely sissy with almost feminine body type and features but with that delicious big cock. He'd taught me as much about how he wants to be a sissy as I taught him.

I was reclined on a divan in my bedroom, a lewd cock hanging from my strapon harness, playing with my nipples through my satin bustier and sliding my thigh-highs against each other. We had Britney Spears music playing (George's favorite) and I guess it was playing a little too loud.

I never heard Jackie calling or opening the front door downstairs. I never heard her coming up the stairs and it was only when she opened my bedroom door that I had any idea my sister had decided to make a surprise visit.

"Jane, are you having a party up here or...." Jackie's jaw dropped open as she saw George. George froze in all his sissy glory, only the heartbeat throb of his cock was moving back and forth. There was no way I could get out of the strapon harness fast so I just hustled Jackie out of the room and closed the door behind us.

"What are you doing here, Jackie?" I demanded, embarrassed and angry, mostly at myself. I forgot about the lewd cock hanging heavily in front of me. Jackie didn't miss it and stared at it even as she spoke.

"I... I thought I'd give you a little surprise, take you out clubbing," she said softly. She was dressed to kill in a tight lycra club dress, tights and high heels. "You haven't been getting out very much lately, though I guess I can see why now."

I wanted to make the cock go away, but again, it would have taken forever to get it off.

"Jackie, I think you should go."

Her eyes flashed and she grinned. "Let me watch!"

Oh god, no. Why had I ever let her watch me with Brad back in high school? She'd been fixated with watching people ever since.

She saw my reaction. "You let me watch or your little habits," punctuated by a flick on the end of my rubber cock, "will get a little more public."

"You wouldn't!"

"Try me," she said with a wicked smile.

We stared at each other as we'd done our whole lives, a showdown and this time I was going to lose. I must have stood there three minutes while she waited, but mostly I was trying to figure out what I was going to do when we went back in the room. She saw it.

"Just pretend I'm not there."

When we walked back in the room, George was laying out on the bed, still all dressed up, cock still hard and tenting his panties. He was blushing and anxious, looking quickly at us.

"Just ignore her," I said nonchalantly as Jackie perched in a chair in the corner. "Now, bitch, you've got work to do!" My firm voice snapped George's attention back to me.

I walked up to the edge of the bed and knelt on pillows that put my jutting rubber cock at just the right height. George slithered down the bed on his stomach and presented his mouth.

"Mmmm, you are a sissy slut," I began, trying to get back into my 'role' for our playtime. In the back of my head, I couldn't forget that my sister was staring at us and I felt deep down that it excited me.

"Do you want to suck my cock, sissy? Are you a little pussy cock-sucker?"

"Mmmm, yes, Mistress, I want to suck your cock. Fuck my mouth with your big cock..." moaned George. He seemed happy to perform for Jackie.

"Open your pretty painted lips, honey," I cooed, tapping his face with the end of my strapon cock. He opened his mouth wide and I began to tease his lips with the cum-hole tip of the dildo. "A little wider, you're going to take my cock down your throat, you slut..."

I almost forgot about our audience and grabbed my breasts, rubbing my nipples through the satin of my bustier. George was reaching his tongue out, lapping at the cock head. At last I shifted forward, pushing the cock into his mouth.

I didn't go deep at first, letting him suck and lick the head, but it wasn't long before my hand was on his head and I was fucking forward in a rhythm.

My head shot around when I heard Jackie moan. She had her club dress up around her waist and her hand inside her tiny thong. I could see she was stroking her clit fast as her eyes, big and wide, watched us.

And it got me very wet.

I pulled gently out of George's mouth. "Okay, bitch, time you open wide and let me get a nut off in you. Turn around!" I growled. George slid around in his lingerie until his ass was on the edge of the bed. I felt up the smooth shaved curves and gave his ass cheeks a slap.

"Beg for my cock, slut!"

"Please, Mistress, fuck my sissy-ass!" he begged with gusto. "I need your big cock in me to feel like the sissy-slut I really am. Take me hard!"

I squirted the lube all over my fingers and began to prep him. It took almost no time before one finger became two and two became three.

"Please, Mistress, please give me your cock, fuck my pathetic ass deep and hard, use this sissy like I deserve..."

With that, I pressed the head of the cock against his hole and after only a few seconds I watched the whole shaft disappear inside him. He moaned loudly followed a moment later by Jackie. She was cumming! We both stopped and watched my sister blurring her fingers over her pussy and whimpering as the pleasure overtook her.

After half a minute, she relaxed, lifted her fingers and sucked her own juices. Holding her legs lewdly open with only a drenched thong to cover her pussy, she smiled. "Go on..."

By this point, I needed to fuck my sissy bad. I grabbed his legs and began to piston in and out of his ass. I watched, enjoying the sight of my 'cock' disappearing and reappearing from his bottom. He squirmed in pleasure at the penetration, the stroking of the hard cock at just the right spots inside.

"Oh god yes fuck me fuck my sissy slut ass" he moaned and I complied with his wishes, slamming him until our sweaty flesh was slapping loud in the air. His cock was rock hard and slapping his belly with each thrust of mine. I looked around, realizing that I didn't have the glass near enough to grab.

Jackie saw me and stood up, her dress still hiked up around her belly. She walked over to where I was looking.

"The cum glass," I said hoarsely, my own pussy on fire as fucked him. He grabbed the big, heavy shotglass and walked over to where I was fucking the lingerie-wearing man. Without being told, she positioned it in front of his cock, ready to capture every last drop.

"Cum, bitch!" I barked and immediately his cock jumped, hard spurts of white cum hitting and splashing in the cum glass. I hadn't allowed George to masturbate for the last two weeks, so he had a lot of creamy cum. It made a thick layer on the bottom of the glass by the time he stopped pumping.

I didn't have to stop. Jackie took the glass and held it over George's lips. "Sissies suck cock and drink cum like the panty-sluts they are, don't they?" she asked him. He groaned in pleasure and nodded. She then dripped and poured the cum into his eager mouth, then let him lick the shotglass clean of the hot cum.

When he was done, I increased my thrusts and then ground myself against the base of the dildo as it lodged deep in his ass. It was all too much and I came hard, very hard. I sort of lost track of what I was doing and came to sitting on the floor by the bed. Jackie was looking at me, half-worried and half-amused.

"You always were a screamer," she said with a wicked smile. I realized that I had screamed as I'd orgasmed.

"But now it's my turn." She took the cock and harness off of me and put it on. She gave me a particularly lewd look when she pressed the base against her pussy, feeling my juices rubbing her.

"Now George, let's continue your sissy training... doggy style."

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