Helping Sis Pick a Dress - Cover

Helping Sis Pick a Dress

Copyright© 2020 by Lubrican

Chapter 2

Coming of Age Sex Story: Chapter 2 - My sister asked me to help her pick out a dress to make her look sexy for her date. I told her she didn't need to BE sexy. She insisted. I told her she was already sexy. She still insisted. So I said I'd help her pick out a dress. I thought she'd change in the bathroom, but she changed right in front of me. Pretty soon there was incontrovertible proof that I thought she was already sexy. It was embarrassing. Then she wanted to SEE the proof and things just got weirder from there.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Incest   Brother   Sister   First   Pregnancy   Menstrual Play  

Cathy went on her date with Dennis. I didn’t get to see her before she left, so I didn’t know if she was sans bra or sans panties. All I could think about the whole time she was gone was what he was doing to her. Or what she was doing to him. Or what they were doing to each other. She got home at the stroke of 9 P.M., which was her curfew. Mom, who got back from her class after Cat left on her date, waited up for her, as usual. I was still too freaked out by Cat stripping in front of me, not to mention asking if she could touch my wang, to chance talking to Mom. She’d know something was up. I was sure of it. So I made sure I was reading with my headphones on when Mom opened my bedroom door and asked where Cathy was.

“Date,” I said, and looked right back at my book.

She was tired, as usual. She got something to eat and watched TV until Cathy got home. I took the headphones off and left my door open a crack so I’d hear when she got home. I snuck down the hall and eavesdropped.

“You wore that on a date?” Mom’s voice expressed displeasure.

“What’s wrong with this?” asked my sister, innocently.

“It’s a little brief, don’t you think?”

“It covers everything,” argued Cathy.

“That dress is designed to inflame a man,” said our mother. “Where did you get it?”

“It was on sale at Marshal’s. Isn’t it darling?”

“Cathy, you’re pushing your luck if you wear things like this on dates. And if your father saw that he’d have a heart attack.”

“Relax, Mom. I don’t go out with guys who have bad reputations.”

“Bad reputation or not, boys will think you’re easy if you wear things like that.”

“But I’m not easy, Mom. Just ask Dennis Holly. He might still be outside.”

“I’m not asking some boy how far you let him get,” growled Mom. “Don’t wear that dress on another date. In fact, don’t wear that dress again until you’re twenty.”

“Mom,” moaned Cathy, drawing it out. “That’s not fair.”

“What’s not fair is you teasing boys by showing them what you don’t plan to give them. That’s called being a cock tease, young lady. If I think you’re becoming a cock tease, I’m going to ban you from dating until you grow up some more.”

“Okay, okay. Ix-nay on the es-dray for now,” said Cathy, making her voice extra morose. “And I don’t tease my dates. I don’t even let them kiss me more than once. All we do is have fun.”

Then it turned into a hen party as my sister regaled our mother with how much fun it was to play miniature golf with Dennis Holly and some other kids they met up with. I wasn’t interested and went back to my room. Mom went to bed and I waited five minutes before I tapped softly on Cathy’s door. She opened it wearing half of her baby doll pajamas. Half was the bra and panties, without the jacket. This was something else she’d gotten with her allowance, supplemented by some babysitting money. It was made of ivory-colored silky-looking cloth, with some lace accents. You couldn’t see through it, like some of them I’d seen online, but it was still sexy as hell. Dad hadn’t seen that yet, either.

“What?” she asked.

I pushed my way in and closed the door.

“Did you show him your boobs?” I asked.

“None of your business,” she said.

“Come on,” I groaned. “Just tell me.”

“Why?”

“Because I want to know. That’s why,” I said.

Why do you want to know?” she asked, not budging an inch. “Is that part of your pervertedness? Do you wish you could spy on me?”

“If you don’t tell me, I’m going to tell Mom you’re a cock tease,” I said.

“You little sneak!” she hissed. “You did spy on me!”

“I heard you come in. I happened to be standing in the hallway. I can’t help it if you two talk loud enough for me to hear.”

“You are such a pervert,” she rasped.

“Said the girl who begged to touch her brother’s cock.”

She stared at me. Apparently I looked nervous, or tired from being nervous, because her head cocked to one side and I felt like I was under a microscope.

“So you really want to know whether I let him see my boobs,” she said.

“Yes,” I said, perhaps too eagerly.

“You’re jealous!” she squeaked.

“Not so loud!” I hushed.

“You are. You’re jealous of some boy groping my boobs.”

“He groped them?” I whined.

She grinned, and cupped her breasts, lifting them in their silky covering.

You groped them,” she said. “Like this.” She grabbed both breasts and squeezed them. “Remember?”

I groaned. She grinned harder.

“Relax. I decided he didn’t deserve to see them,” she said. “My perverted brother is the only boy who ever groped them.”

Apparently I was visibly relieved, because she laughed.

“I can’t believe you’re jealous.”

She’d been honest with me. She could have strung me along and tortured me, but she hadn’t. So I was honest with her, too. Well, mostly, anyway.

“I was worried about you,” I said. “Guys try stuff.”

“Dennis was a perfect gentleman tonight,” she said. “The only guy who was a danger to my virtue was you.”

“Me? All I did was demonstrate how if you didn’t cover things well enough, a guy could get to them.”

She stopped smiling.

“You fingered me, Bobby,” she said in a loud whisper.

“I touched you,” I said. “Only to show you I could, because you didn’t have on panties.”

“Well, nobody else touched me, because I was wearing panties tonight. And a bra, too. I told you all I wanted was to feel sexy. I’m not going to let some boy put his hands all over me. I told you I’m not ready to have sex. So you can quit worrying and stop being jealous.”

“Okay,” I said.

“Now, get out,” she said.

I left, but I still wasn’t happy. I didn’t examine that feeling then. I just felt like something was wrong.

Our rooms share a wall, and it happens that my bed is next to that wall, and so is hers, on the other side. So, when we’re sleeping, we’re only separated by maybe a foot. That wall isn’t insulated, and I always jerked off in the shower instead of my room, because I was afraid she’d hear me. So when I turned off my light and lay there, and then heard her moaning, I was pretty sure she wasn’t sick or in pain.

It went on, and I could tell she was trying to be quiet, but she wasn’t being quiet enough.

So I got out of bed and tiptoed to the door. I slid my bare feet along the wall, going down the hall, and made it to the front door without making too much noise. It will show you how freaked out I was, because all I had on was briefs. The grass was soft, and a little damp. We live on a corner, and there’s a street light on the corner and at the entrance to the alley behind the house, so three sides of the house were lit at night. I knew about my side, of course, because the corner light shined into my room at night. The alley light shone on her window. What I didn’t know was if Cathy had closed her blinds, like I did sometimes at night when it was too bright. I hadn’t looked at them while I was in her room.

So there I was, at ten-thirty at night, sneaking along the wall of my house, dressed in nothing more than my underwear. Anybody driving by could easily have seen me. I got to her window. I eased my eyes up.

Her blinds were open and the curtains were spread all the way apart. The street light wasn’t necessary. Her bedside light was on and I could see everything.

She wasn’t wearing her baby dolls anymore. She wasn’t wearing anything at all. Her legs were spread and her knees were up. Her hand was busy between her legs and it was just obvious she was masturbating. That’s why she kicked me out. She was horny from her date and wanted to Jill off.

I realized my cock was rock hard and I pushed the waistband of my shorts below my balls.

It takes girls a lot longer to get there, apparently. She’d been rubbing for at least five minutes before I got my eyes on her. I shot my wad on the side of the house within two more minutes and finally came to my senses, and she was still going. Imagining the cops finding me there, with me in my underwear and spooge all over the side of the house under her window, I freaked out and ran for the front door. My heart was going a hundred miles an hour when I slipped into my room.

And when the rushing in my ears finally calmed down, and I could hear again, she was still moaning.


The next day was Saturday, and I had two big lawns to mow. My dad taught me to let he customer set the price, instead of agreeing to it before hand. If they paid good, I went back and took care of their lawn again. If they were cheap, I mowed it once and never went back. I learned a long time ago that if you do all the edging, too, you get paid more, so I was gone all day. Mom didn’t have class that night, and supper seemed normal. Cathy didn’t look at me weird and all our discussion around the table was unremarkable. Mom had homework to do, so we couldn’t watch TV, but there wasn’t anything on anyway. I was reading The Silmarillion, by J.R.R. Tolkien and it had so much detail and names and all that in it that I had to pay close attention to it, so quiet was fine with me. Cathy stayed in her room and I could hear her talking on her phone to one of her friends.

The next week was like that, too, all just normal stuff. Cathy spent a lot of time with her friends at the city pool, and at the mall and so on. I met up with my friends and we shot hoops or whatever. Steve, one of my friends, kept trying to get a bunch of us to go Frisbee golfing with him. There was a new course set up in the park. But a single disc cost twenty bucks, and some of the people I saw playing had these little carts they pulled around that had eight or ten different discs in them. It was too rich for my blood.

And then it was Friday again, and Mom was gone again, and Cathy left a note on my pillow that said for me not to go anywhere between five and seven that night.

At five sharp she came home from wherever she’d been and made supper. While we were eating she said, “After supper I want you to help me pick out a dress for my date, tonight.”

I thought she was joking, or maybe pranking me, but she just waited. Finally, she said, “Well, will you?”

So, after we ate I followed her to her room and she did the look-through-her-closet-and-pick-three-dresses thing and, without a word, stripped naked in front of me.

She stood there, watching me watch her. She made no attempt to hide any part of her body.

“Am I pretty?” she asked, softly.

I finally stopped looking at her tits and pussy and looked at her face.

“You know you are,” I said. “Don’t fish for compliments.”

“I do not know I am,” she said. “I know some other girls who are pretty, but nobody tells me I’m pretty.”

“Yes,” I said, not wanting to have this argument. “You’re pretty. You’re better than pretty. You’re gorgeous.”

“Really?”

“Last week didn’t convince you?” I asked. “Remember how I perved out?”

“Are you perving out now?” she asked.

This was weird. It wasn’t just that she’d gotten naked in front of me. I mean that was weird, yes, but all this “Am I pretty?” stuff was even weirder. I mean what girl cares what her brother thinks about her? And the way she asked if I was perving out about her now sounded odd ... almost like she hoped I was.

“Bobby?”

I raised one finger to stop her, and just tried to think about things. I knew girls thought about their flaws a lot. Or what they perceived as their flaws. I knew girls were awful to each other, and that they talked about the flaws they perceived in other girls. If a guy treated me like I’d seen some teenage girls treating each other, I’d punch his lights out. So I came to the conclusion that this was all about self-confidence issues Cathy was having. She wanted some guy to get all horny for her and she was unsure enough about all this that if it was her brother who got that way, that was okay. It was at least a start, so to speak.

“Can I tell you something?” I asked.

Now she looked wary.

“Okay,” she said.

“You have a cute face. Your tits are to die for. You have a great ass, but most of all you have a great personality. You’re not as mean as a lot of girls. You’re funny, and interesting. You’re even pretty smart. It’s a great package, Cat, and a lot of guys wish they could unwrap it.”

“Have they said that to you?” she asked, her voice high.

“Of course not. They know I’d kill them if they did that.”

“So how do you know, then?”

“Cathy, I’m not an idiot, for one thing. I know lots of girls and what they’re like. And I know you, not to mention I got a boner for you last week. I’ve got another one now. I’m not supposed to get boners for you, but I can’t control them. Isn’t that proof enough?”

“You said you get them all the time,” she said. “Maybe you just get them and they’re not about me.”

“Trust me. I know the difference between a random stiffy and one caused by a girl I’m looking at or thinking about. You’ve caused several really good ones. Except, technically, they’re bad ones. Like the one I have right now.”

“Show me,” she said.

I didn’t drag it out this time. I just got naked with her and stood there with my anti-aircraft gun pointing at the sky. Don’t laugh. I guess guys just like to think of their penises as firearms of some sort. I know I love to shoot mine. Pun intended.

She stared at it a long time before she said anything.

“Bobby?”

“Yeah?”

“I thought I’d like it if Dennis got a boner for me. But I didn’t.”

“So he got one?”

“Yeah. He pushed it against me while we were making out.”

“And you didn’t like it?”

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