tagTranssexuals & CrossdressersSissified by My Sister

Sissified by My Sister


I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me.

I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at her shoulders. Both very petite and feminine bodies. We both had fair skin and a blush was nearly always present. I feel like my sister Olivia and I have always had a strong bond.

It was a cold night in January. I was watching television and getting a little bit horny browsing porn on my iPod while the TV was running.

It was getting a little stormy and the TV cut off. The power must've gone out from the storm. I knew my sister was probably up even though it was 1 AM because she always watched TV until 2 in the morning most of the time, it helped her sleep. But since the power cut out she used to come into my room because she gets scared in the dark.

I continued to look at porn on my iPod, now no longer distracted from the TV. I looked at a wide range of porn, softly jerking my cock.

As soon as I started to speed up, I heard Olivia start to walk towards my room. I stuffed my dick into my pants and Olivia knocked on the door.

"Come in" I whispered and Olivia stepped into my bedroom.

"Hey, Dan, you're still awake?" my sister whispered.

"Yeah, you?" I said stupidly, panicking.

"Haha of course I am! You must be tired. Do you mind if I sleep in here? I cant sleep without the TV so I thought I'd keep you company" she said in the cutest damn voice. I couldn't resist.

"Yeah sure thing!" I sat up and hid my iPod.

"What have you been up to tonight?" she said

"Oh, ya know... just watching TV" I started getting nervous because she was climbing into my bed with me.

"Oh... okay, well I'm gonna try to get some shuteye. Goodnight brother!" she said with a wink.

"Hah, okay goodnight" I say

After a couple of minutes, I see her eyes are shut, I open up my iPod. I know it was probably a bad idea in hindsight, but I was just so horny. And having a girl in my bed didn't help, even if she was my sister.

I was looking at my iPod, stroking my cock, when I felt a presence over my shoulder. I turned over and I saw my sister staring at me. She looked a little scared. I say "Oh gosh I'm so sorry Olivia. I don't know what I was thinking!"

I would never forget what she said. "I think I know what you were thinking..."

It was then I would never forget what happened next. She suddenly looked at me with her beautiful blue eyes and kissed me on the lips. I didn't know what exactly to think. But my boner did, I felt so turned on I grabbed her intently and pressed my boner in between her legs.

Our tongues continued to dance together and I felt her hand brush my rock hard dick. Her soft hands fondled me. She pulled back and said "I've always wanted you, Dan"

She stopped and said "Wow... this isn't right. I'll be right back."

She ran out of my room and came back a few minutes later. She threw something under my bed and climbed back into the bed.

She said "sorry about that Daniel. I didn't mean to interrupt anything. So you were watching porn?"

"...y-y-yes" I studdered and she grabbed my iPod.

"You wanna keep watching? I'll watch it with you" She said, opening up the porn website I had up. "This isn't weird, is it?" she said.

"It is very weird." I said, she look mortified. "But I love it."

We watched a whole video together and softly stroked each other. We went from video to video slowly fondling each other.

Finally Olivia said "How about I pick the video?" she says.

"Sure thing, sis" I say. The words felt weird coming out of my mouth.

She clicked on the 'sissy' category of the porn site. She opened a video of a boy getting pounded by a dildo. A classic pegging video. At the time, I have never seen pegging. It was so strange to me. It turned me on. It turned Olivia on, too. I felt how wet she was. I knew she had a pegging fetish.

"You like this stuff?" I asked.

"Yeah.... ooohhh yeah!" Olivia whispered, fingering her pussy. "Do you wanna make me really happy? Reach under the bed."

Under the bed was exactly what I feared. It was a pleated red skirt and a red bra and panties and a blue tank top. She asked me to put it on and I complied.

I got to a mirror, and I gotta admit I looked really cute in it. The skirt and the tank top showed off my girlish figure just enough for it to trick me into thinking I was a girl when I looked in the mirror.

"Haha, you look like a dyke!" Olivia said. Seeing my short blonde hair in the mirror made me agree. I felt like a woman.

She kissed me gingerly and I loved feeling her long, wet tongue shoot down my throat. I wanted something more filling though. Never did I expect her to fulfill that wish.

She pulled a strapon from under my bed, a pink 6 inch dildo of hers she brought in with my clothes.

She slid the strapon on and she looked so sexy. Her short brown hair, her hips, her smile. It made me go crazy. I just wanted her to pin me to the wall and fuck me all night.

It was so strange to have a thought like that. I never saw myself in the dominated position, but I loved it. She guided me to her sexy strapon.

I started to suck on it and get it wet. I looked up at her lovingly and she looked so domineering. I wanted her to fuck me.

I turned around and she started to stroke my cock like she was milking me. She squeezed my balls and I felt so defenseless. I wanted her to just fuck me already.

"You ready for this, Dee?" Olivia lustfully groaned.

"Oh hehe, I like that name. Dee. Does it suit me? Am I a good girl?" I say.

She leans up next to me and whispers "No. You're a very naughty girl. And you need to be taught a lesson."

She slides my panties asides and guides the wet strapon into my ass. I've never had anything in my butt that wasn't supposed to be there. And I loved the feeling. It hurt a bit and I yelled out in pain. But it filled me up, I felt so sexy.

She grabbed me by the hips and thrust into my ass. "You like that?" she says.

"I LOVE THAT!" I grunt.

She keeps thrusting away at my ass and I start to see stars.

"You okay, Dee?" She says

"N-n-nauu-..." I moan, and I lose consciousness.

I blacked out with Olivia pounding me, it was so embarassing, but I guess it was to be expected. It was so much to take in, mentally and physically I just couldn't take it.

I woke up in the bed with her, her hands draped around my cock under my skirt. She had a smile on her face even though her eyes were clothes.

I hoped that one day very soon I can prove that I can take it from her.

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