Chapter 21 - My Pregnant Stepsister - NovelsTime

My Pregnant Stepsister

Chapter 21

Author: Burnedflame
updatedAt: 2025-09-09

CHAPTER 21: CHAPTER 21

"I’m sorry I didn’t show more faith in you today," I said.

"That wasn’t all your fault. My being secretive about my interview and then that airhead telling you I was with Steve. But for future reference, know that you can trust me," she said and then leaned across the table and kissed me.

A few days later, after our last exam, I came back home. I wish she lived close by; it would have been better. I didn’t come out until evening when my hard dick finally subsided.

It was time for dinner, but no one had called me to come eat. So I stood up, went to the kitchen, and saw nothing. Didn’t she cook, or what? I haven’t eaten since morning. I took two packs of instant noodles, cooked them, ate, and went back to sleep.

The next day, I woke up late. I stomped to my table and found a note—and it was addressed to me.

"Who might have dropped this?" I asked myself.

My door wasn’t locked last night, so someone could have intruded into my room while I was fast asleep.

I took it and opened it.

"Dear Joshua.

I know what you’re up to. If you don’t want your father to find out about your evil deeds, call me the moment you discover this note.

Maya."

I took my phone and dialed her number. She answered on the second ring.

She: Hello, she says in her gravelly voice, a dead ringer for Demi Moore.

Me: It’s me, I say. "I found your note."

She: Surprised?

Me: Very.

She: I thought you would be. Since you called, may I assume that you would like to keep our little secret from your father’s ears?"

Me: Yes.

She: "Then do exactly what I say."

Me: "Fine."

She: "Dress up in some of my clothes and makeup. Get as slutty as you can. I want to see you in lingerie and a dress. I’ve left a wig and size 12 high heels in my room for you. Wear those, too. Then drive to the Westin hotel in Longwood. It’s just off the Interstate at exit 21. Check into a suite and call me back with the room number. I hope you can do that."

Her demands walloped me like a baseball bat upside the head. I staggered backward and fell to the floor, slumping against my bed. My whole life flashed before my eyes. I saw everything being taken from me, just because of a fuck.

Me: I don’t think so. How can you demand that I should dress like a woman? This is evil.

She: "You better do it unless you want your father finding out about your little fetish."

Me: "Let’s settle this dispute once and for all. Let’s stop all this nonsense."

She: "Are you doing it or not?"

Me: "Why am I dressing like a woman for?"

She: "When you get here, you will find out."

Me: "It’s alright."

She: "Good. And one other thing. I want you dressed like a woman when you check into that suite. This isn’t my first stay at that hotel. I have friends there. If you’re wearing a T-shirt and jeans when you check in, I’ll find out and you will suffer the consequences."

Me: "This is fucking crazy."

She: "Yes. And if you don’t? You may as well pack your bags right now because your father will have you out of the house once he’s back. So, do we have a deal?"

Me: "As you wish."

She: "Good. I’ll expect to hear from you soon."

She hangs up, and the line goes dead.

I can hardly believe what’s just happened. My whole life has changed in one phone call. I feel used and abused, like a cheap prostitute. It begins to sink in that I’m going to have to go out in public in women’s clothes for the first time. I’m horrified. My heart is pumping like I’ve just drunk three pots of coffee.

I don’t think I’ve ever been so confused in my life.

Tell my dad about everything or do it? No. No. No. I can’t tell my dad.

I took my bath and went to her room and found some of her things laid on the bed. I locked the door.

As I stripped off my shorts, I began to absorb the depth of my stepmother’s sickness. Never before had she shown any signs of being a pervert. She’s always been a typical rich-bitch stepmom. She has always been a little bit of a flirt, but I never would have dreamed that she fooled around on my father.

It takes a special kind of weirdo to give the kind of orders she did. Almost as surprising was that line she gave me about having friends at the hotel. It’s as if she’s done this sort of thing before.

I took her bra and stretched it across my chest, putting the ball-like foam inside and fastening it behind my back. I put on the panties, arranging my cock so the underside presses against the lacy fabric. The panties are "boy shorts" that fully cover my ass and leave plenty of room for my balls.

I unrolled the stockings up my legs. I love how the tight fabric feels against my skin. With my cock hardening, I fastened the garter belt around my waist. Hooking the straps to the stockings takes some effort. Every time I think I’ve got a hook secured, it slips out of my masculine fingers.

I finally got the stockings hooked up and went into Maya’s closet to choose a dress. I quickly found a little, black cocktail dress that I pulled over my head. The stretchy material conformed to my body. I checked myself in the mirror on the closet door. After checking myself, I headed to the bathroom to do my makeup.

I painted my face as beautifully as I could with cherry-red lipstick, black eyeliner, gray eyeshadow, and mascara. Checking myself in the mirror, I saw that I wasn’t quite passable as a woman, but I was closer.

Only God knows what I am going there to do. I went back into the bedroom and searched the closet for the rest of the outfit Maya had directed me to wear. A box on the shelf above her blouses was labeled "wig/shoes." I took it down and set it on the bed to open it.

The wig fit snugly on my head. I suddenly had straight, black hair that fell just below my ears. The bottom edge was crisp and sharp like a broom. The bangs were just as dramatic, going straight across my forehead just above my eyebrows.

The shoes she had chosen for me were totally slutty. Shiny, black, six-inch heels. I slipped my feet into them and took a few tentative steps across the room. I felt the shoes forcing me to perk up my chest and ass. The line from that Shania Twain song flashed through my brain: "Man, I feel like a woman."

I took a cute, black purse and threw my wallet inside.

It was time to leave.

My Dad’s Lexus SUV was parked in the garage. I climbed in and cranked it up, thankful that the windows were tinted. At least I wouldn’t have to humiliate myself in front of my neighbors.

Longwood is usually about 45 minutes away. I’m careful to obey the speed limit. The last thing I need is a run-in with a cop. Once on the interstate, I found myself searching my iPod for Britney Spears, Madonna, and Lady Gaga. The drive flew by. When I hit the exit, I was tapping my foot to "Poker Face."

Not until I pulled into a parking spot did the full weight of what I’m about to do hit me. A chill was in the air as I opened the SUV door and swung my heels onto the pavement. I was shaking as I click-clacked on the concrete toward the entrance.

I was noticed for the first time by the bellhop, who couldn’t help but grin as he tipped his hat. I returned the gesture with a nervous smile of my own. The automatic doors slid open. The lobby’s heat enveloped me as I walked inside.

I was hoping to get to the front desk with as little attention as possible. But the floor was ceramic tile, and my heels must be made of some uniquely hard plastic because the clicking reverberated around the cavernous lobby. I felt like the whole world was watching as I approached the clerk behind the front desk.

He had his head down, and he was typing on a computer keyboard. He sensed my presence and greeted me without immediately looking up.

"Hello, ma’am, welcome to the Westin," he said.

The clerk looked up. His eyes popped.

"Er, I mean, sir," he said. "Terribly sorry—which do you prefer?"

I thought about this for a second.

"You can call me Stephanie," I said in my best female voice.

"Very good, Stephanie," the clerk says. "How may I help you?"

"I’d like a suite, please," I say.

"Yes, of course," he says.

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