tagTranssexuals & CrossdressersMy Babysitter Ch. 03

My Babysitter Ch. 03


Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a woman. It doesn't matter to me, though, she's so perfect. From her juicy, pale ass to her soft, red lips.

Then I felt a touch that was so familiar but strangely different. The warm, friendly touch of my mother.

"How'd you sleep last night, my little guy?" My mom beamed.

"Mmmm good, still a little sore" I respond.

I turned to Annabelle and she opened her eyes and fixated them on me. She then gave me a sweet morning kiss.

"Good morning, you little slut." She said "Ya know you still have your mother's clothes on? You're so hot in those."

I blushed. "Oh gosh I forgot about these" The pink lace bra and the black lace panties were still on, my morning wood now poking out of them and out of my red pleated skirt, pressed against my white blouse.

"I see that cute little fella right there" Annabelle grinned, and rubbed her fingers across my dick.

After laying around in the bed a little, mom had to get up to go to work. Annabelle and I only had 5 more days to fool around, cause we cant do this kind of stuff when he gets back from Seattle on Sunday.

I was downstairs when Annabelle comes downstairs wearing a white tanktop and a red pair of shorts, her bulge prominent. She walked straight over to me and kissed me. Her lips were like soft and alluring. It turned me right the fuck on.

Annabelle stopped kissing me. "I got an idea actually. Lets look up a random porno and reenact it." She said with a smile.

"I dunno, what if they do something weird I'm not comfortable with?" I said

"Sam. What the hell are you not comfortable with?" She said, questioning me.

"I guess, lets do it." I say, unsure.

She opens up a porn site and searches "tranny + male" and clicks the random button. The video comes up and we both are watching intently.

The video starts with the boy tied up to a bed. At this point I know its gonna be bad.

Annabelle ties me down with some rope to my bed. I feel so restricted and vulnerable, my cock so exposed.

The video continued, the tranny walks up and shes wearing fishnet stockings, leather highheel boots, a yellow dress. Annabelle found a set of these clothes or the closest thing she could find in my mom's closet.

The tranny in the video begins to do some spanking, and I shook in my bed to try to get it. But I was secured too well. She slapped my legs and squeezed my balls tightly. They were so sensitive. I felt so susceptible and afraid.

The video then showed the tranny hop onto the man and rub him all over, Annabelle emulated this. She ran her tongue along his entire body and finally ended on his dick.

I felt so connected to the man in the video. It was like we were the same person.

Annabelle and the tranny begin to suck on mine and the man's dick, slow and really showy.

The video skipped to a scene where the guy is tied by his neck to the bed like a collar with the rope tying his hands behind his back too.

I was so horrified at this sight, even though I've taken it in the ass before. She tied me up and my ass just stuck in the air like a lone hill on the plains.

The video tranny started rubbing her fingers over the guy's ass and circled her fingers around his asshole. Annabelle repeated this and it turned me on like crazy. It kind of tickled. I tried to squirm but my hands were immobilized.

Annabelle and the video girl started slipping her dick into mine and the man's ass. I felt her little cock push into my ass.

She started fucking me harder, and I realize I've never had cum in my ass.

I tried not to worry about it and just enjoyed the ride.

She kept pounding relentlessly and finally she screamed "ooh baby I'm cumming!" and I felt the warm cum ooze into my ass. It felt amazing. I felt like a little slut. She leaned in and started licking the cum up out of my ass. It tickled and felt so wet.

We cleaned up and just enjoyed the rest of the evening together kissing and watching movies. Tuesday was almost over and the countdown to my dad being home was looming over our heads.

We went to sleep that night with cum still dripping out of my ass.

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by Anonymous

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by TWOSPERITS09/16/17

All three parts supper

I loved the story so far. Hope you have more.

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