Another school-day gone to waste, I thought as I walked home from school... finally. It was 4pm, and I've just got out of detention. My step mom was waiting outside, just putting out the cigarette she'd been smoking while she was waiting.

"Hey Harry, how was school?"
"It sucked... like always, but worse."
"What happened?"
"I got a detention for supposedly 'bullying' someone."
"Why?"
"Some cunt stole my bag. I had to tackle him and stand on his arm to get him to let go of it."
"That cunt should get the detention."
"I know."

We got home in about 15 minutes. I went to my room to do something while my step mom had taken a shower. I was just burning around time, like usual. It wasn't until I took a sip of the soda I hid in my bag that I suddenly realised I needed to go... bad.

I ran to the bathroom, where my step mom had taken her shower. That was the only bathroom in the house, and no I wasn't going to take a leak outside. Where was I to go? I knocked on the door, just to be curteous. After all, she was my step mom.

"Uh, Step Mom?"
"What?"
"I need to go. Can you let me through?"
"Sure."

Usually we'd have to wait till Mom was finished, even if we ended up pissing our pants because she took too long, but my step mom actually let me through. She didn't even worry that I left the door wide open. The question is: why?

"So why did you end up marrying Dad?"
"Well, he looked handsome, especially for someone his age."

No surprise. Dad was 36, but other people tended to think he was 28 or 29. Maybe it was the way he looked. My step mom was kind of stumped when she realized how old Dad really was... and even more stumped when she met me for the first time. She must've really wanted to marry me, and probably would've too if she'd met me earlier.

"You are old enough to have sex, right?"
"... yeah, why?"
"Alright, let's do it right here."
"But... you're my step mom."
"If I saw you earlier, I wouldn't be your step mom... I'd be your wife."
...
"Another thing, you're older than me."
"So, I'm 21, and you're what? 18? 17?"
"16."
"16, huh?"
"Yeah... 16."
"Oh, and don't even try to tell me that Dad will kill you if he saw us, he doesn't finish work until 8."
"What's the time now?"
"4:20."
...
"Well, you lose."
"But..."

I was too late. My step mom stepped out of the shower, fully naked. And she happened to be a shemale too. Wierd. But another thing come to mind that was more important than the realization that my step mom was a tranny: How the hell would Dad react if he were in my position? Go mental? Slap her? Kick her in the nuts? Grab a chainsaw and cut her dick off? Kill her?

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"So, how do I look?"
"You... look... hot..."
"Do I now? Can't wait to get laid now can you?"
"No... I... can't..."
"Good boy, now just do what you're told and you'll be just fine."

I really wanted to freak out. I wanted to run all the way to Dad's work place and tell him that my step mom is a shemale. Even if it meant that I got bolted on the head, twice. Once for telling him that his new wife is a shemale in front of his workmates and again for looking at her private parts (how the fuck else would I know?) But I just kept my cool. The last thing I wanted is for my step mom to hate me for running off after flashing her dick.

I looked at that huge piece of meat long enough. I opened my mouth, went right in, and bit down hard... I knew I did that wrong because my step mom screamed in pain.

"WHAT THE FUCK WAS THAT FOR!?"
"Shit... sorry."
"Next time, down bite."

The next time wasn't boding too well either. I was sucking way too slowly. My step mom wasn't getting any pleasure from it at all. I was going to fail at this rate, like everything except... nothing. Until she starting clicking her fingers, quickly and right up to my ear. I took the signal and bobbed faster up and faster down. I wasn't gagging anymore, maybe because I couldn't, until she finally climaxed. Her cum was so thick, I couldn't even swallow it properly.

Next she went behind me and started trying to penetrate my ass. She wasn't hard enough after that last time... which was good because I didn't want to feel that till the cows came home. My step mom had her ways though...

"Hey, why don't you suck on my boobs for a bit?"
"Why should I?"
"C'mon, you can't suck dick without sucking boobs. That'll make you gay."
"But..."
"You don't want people calling you Gay Harry, do you?"
"No..."
"Then start sucking."

I started to suck my step mom's breasts. I wasn't gagging this time, and I was actually enjoying it. So was my step mom, for obvious reasons. Her breast was pressed right up to my face, and she started giving signals that she was gonna cum... again.

Now with a rock-hard cock that was about to explode, my step mom started to ram my ass again. This time it went in. As she expected, I screamed like hell, but it wasn't over yet. She still had a fuckload of ejaculation to let loose, more than what she had when I stopped sucking her tits.

"You OK?"
"No."
"Don't worry about it, you'll get used to it."
"And why would I want to get used to it?"
"I'll be fucking you for a long time yet. Which reminds me, you haven't even shot since we started."
"Maybe because I had no choice?"
"Don't worry, you can titty fuck me after I get this dick out of your ass. How's that sound?"
"This better end fast..."

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My step mom moved that thing up and down, slowly. I didn't know how she could move it that slowly, but I didn't ask because that was a lot easier to bear. Deciding to get rid of all her cum now, she started upping the ante a bit. It didn't worry me any more because I didn't feel any more pain, only pleasure. It didn't last long though. She finally pulled her cock out of my ass. It now flopped like a fish in a barrell.

Now was my time to get even. With my step mom flat on the ground, and me on top of her stomach, I started to fuck those titties good. I never thought you could titty fuck a shemale... yet again no-one has even tried to. Don't know why. I was just glad it was over when I finally shot on my own step mom.

"That wasn't so bad, was it?"
"No, it wasn't."
"Good, I love you Harry."
"I love you too, Step Mom."
"Now don't tell anyone what happened here today, will you?"
"I won't..."

Now that's a promise I would keep because I never wanted anyone to know that

a) I had sex with my step mom
b) My step mom was a tranny
c) I had sex with a tranny

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wow great story... fun to read

Very wild story. Thanks for posting

Great story... loved the "Bottom" lines...

... Now that's a promise I would keep because I never wanted anyone to know that

a) I had sex with my step mom
b) My step mom was a tranny
c) I had sex with a tranny...

there was a moral to the story... is it...
"Don't ask don't tell"
"what happens at home stays at home"...
"don't let any know ... ya take it in the A$$...

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Its Time to throw out the Trash... and the Spam....

That pretty much sums it up

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That's probably happend to someone before which makes me think wtf why not me

good story. Thanks

I liked it and the family stuff kinda hot