tagTranssexuals & CrossdressersSissified by My Sister Ch. 02

Sissified by My Sister Ch. 02


Well about a week past, and my sister continued to come into my room to bury that hard strap-on into my ass. It started to become routine. Actually I was just thinking it was starting to hurt less when Olivia came up to me in private, and said "Ohh, my pretty little Dee-bear, my boyfriend is coming up for the end of winter break, just letting you know~"

And at that point I hadn't thought much of it. Later that night she did the usual. I started going to bed wearing the outfit that she lays out for me under the covers, and she sneaks into my room and "punishes me for being naughty." It's what I deserve for being such a sissy all my life.

The day her boyfriend Casey came over, I assumed we would stop doing stuff every night. But I was dead wrong.

I hopped into bed that night and I realized she left me a pair of striped blue and white panties, a light blue bra, a pleated black skirt, and a blue shirt. I reluctantly put them on and awaited the worst. I was so scared Casey would find out and beat me or her up!

After a couple of minutes of waiting, Olivia came in and said "Ohhh is my Dee bear all cute for me, yet?"

"y-y-yes.." I say, shakily. I don't know why exactly I was especially afraid this time, it must've been the thought of Casey bursting in.

Olivia steps in the room, black bra and panties with a garter belt, and a dark blue 7 inch strap-on. She has a devilish smile on her face.

"Liv, are you sure about this?" I mutter.

"Of course I'm sure! Now shut your little mouth! You have no right to question me, you little slut!" She barks back. "Now let me show you whos boss!"

She grabs my cock as hard as she can, and it seems like it gets hard as soon as she touches it. She starts giving me a handjob while she pulls a blindfold out from under the bed. She must have put it there when she put my clothes out.

She puts the blindfold over my eyes and everything is completely dark. I can't see through it at all.

She turns me over into doggystyle position on the floor and starts to rub her fingers along my asshole. "I have a special suprise for you tonight. But you're going to have to wait~" she says cheerily. I knew I was in for some shit.

She starts to slide her 7 inch strap-on in my ass and I clench and form a bit of a grip on the dildo. "Wow. I forgot how tight you are!" she says.

I feel her pull the strap-on out of my ass and then I hear her walk over to my face and I feel the heat of the strap-on after pumping my ass against my face.

I open my mouth and I feel it just slide in towards my throat.

I then feel the plastic dildo shove up my ass again. But its still in my mouth?!

I start to panic when I realize that the dildo in my mouth is actually Casey's rock hard cock.

"Haha, you just realized, didn't ya. Haha what a sissy." Casey said as he thrusts harder onto my face. "Oh... Dee, was it? Tell me if I hurt you. Hahaha"

Casey and Olivia were having the time of their lives on me. I felt so used. So slutty. I loved it!

Both of those rock hard cocks just pounding away at me, destroying my self-view. Turning me into a full sissy.

I think what turned me on the most was that it was Olivia doing all this to me. We used to always play pretend but of course it was never like this.

Casey pulled his cock out of my mouth, while Olivia followed suit. He pulled the blindfold off. Then something happened that I think even Olivia didn't expect.

Casey brought his face closer to mine, we both locked eyes. He wrapped his hand behind my head and kissed me. Right on the lips. At first I resisted, but I let up and began to slip my tongue into his mouth, and our tongues dance together. It was like no other kiss. It must be what girls feel like when they're kissed.

Olivia looked at Casey with a grin and she began kissed him, right after me. She looked at me and gave me a long kiss as well.

Casey brought his dick back up and Olivia started to suck it. She was amazingly good at it. It felt weird watching her suck dick after her being so dominate to me.

Even after all that happened I felt dirty watching my sister suck Casey's cock.

She sucked hard on his dick until finally he came in her mouth. She didn't swallow yet, though. She moved over to me and kissed me, swapping the cum into my mouth.

I've never had cum in my mouth. It felt so weird. It tasted warm, almost like mucus but slightly metallic.

"Now swallow the cum like a good sissy!" Olivia said, demanding satisfaction.

I smiled at both of them and thanked them for the good time. They both just laughed and Casey said "Maybe soon I can cum in your mouth, but I dunno... You may need to beg for it!" He laughed and left with my sister.

It was a strange night, and it all happened so fast. But I think it helped my sexuality a lot. Tonight taught me things about myself that I had not expected.

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byGreenGale© 10 comments/ 174430 views/ 40 favorites

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by Anonymous

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by cdCindy101/08/18

wonderful story

This story is so hot it made me cum hard into my hand -- and I ate it all up. I wish my sister (or even my wife) would sissify me, dress me up, fuck my man-pussy with a big strap-on and then have her boyfriendmore...

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by Anonymous08/31/17

Loved it!

I loved both parts of the story. I wish my sister would do the same with me.

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