Helping Sis Pick a Dress - Cover

Helping Sis Pick a Dress

Copyright© 2020 by Lubrican

Chapter 3

Coming of Age Sex Story: Chapter 3 - 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  

This time I didn’t try to avoid Mom when she got home from class. I hugged her and asked her how it went. She was taking algebra, because she hadn’t taken it in high school. I’d already had it, so I helped her with her homework when she got stuck. She was pretty smart, though, so I didn’t have to help very often. Usually she just had me check her work. I told her Cathy was out with Bruce and she asked me what kind of boy he was.

“Harmless,” I said.

“You’re not just telling me that to ease my mind, are you?” she asked.

“If I knew she was going out with a wolf I’d talk to him first,” I said.

“Really?”

“It won’t happen very often. You won’t let her go out with juniors or seniors. They’re the only ones she’d really need to worry about.”

“Like you?” Mom arched one eyebrow.

“I’m one of the good guys,” I said.

“I hope so, Bobby,” she said. “I hope you treat girls with respect.”

“Of course,” I said.

“And you never do anything against their will, right?”

“Mom, come on. If I did that, they wouldn’t go out with me again.”

“I know boys have urges, Bobby, especially when they get to your age.”

I almost asked her if she was going to have the same talk with me that she had with Cathy, but then she’d know that I knew about her talk with Cathy, and I was pretty sure Cathy didn’t want that.

“I’m handling my urges just fine,” I said.

“Good. A lot of parents think masturbation is wrong, but not your father and me,” she said.

You could have knocked me over with a feather! My mother ... my plain, old, forty-something-year-old mother ... had just said she didn’t mind if I jacked off!

“Uh ... thanks?” I croaked.

“Now I’m all embarrassed,” she said. “Go away and let me get these dishes done.”

I knew she was flustered. She was referring to the dishes from the supper Cathy and I had eaten. Dishes was one of our chores, and we usually got yelled at if the kitchen wasn’t spotless when she got home. The dishes had been abandoned so I could get naked with my sister.

I didn’t tell Mom that, of course.


I didn’t “wait up” for Cathy with Mom. Instead, I lay on my bed and read. I actually fell asleep, and was jolted out of that by my sister’s sharp fingernail in my ribs.

“Get up. Come to my room,” she whispered.

I stumbled after her, a little groggy. She was still dressed in the outfit I hadn’t chosen for her. It was more conservative than the one she’d worn to feel sexy in with Dennis. It was what I’d call a summer dress, with two inch wide straps over the shoulders and no cleavage at all. It was flowered. She had on sandals.

“How do I look?” she asked, once her door was closed.

“You look good,” I said.

“Thank you,” she replied.

“Mom was probably happier with that,” I offered.

“She was. Now, I want you to just look at me.”

She struck, a somewhat awkward pose, awkward because it was a pose, and then twirled slowly. She smoothed the dress over her hips and arched her chest.

“What are you doing?” I asked.

“Do I look sexy?”

“I already told you, you look sexy,” I said.

“Are you hard?”

I wasn’t. She’d just wakened me. My brain still wanted to be asleep. I looked down.

“Can’t you tell?” I asked, looking at the front of my briefs.

“Why aren’t you hard?” she complained.

“Give me a second,” I said. “I don’t spring to full hard-on every time you walk into the room.”

“Don’t be mean to me,” she said.

“Look,” I said. “It’s late. Just tell me what you want.”

“I want you to be hard,” she said.

“If you take off that dress I’ll be hard,” I said.

“So this dress isn’t sexy,” she said.

“Sit down,” I said.

I pointed at her bed and she perched on the edge. I sat beside her.

“Okay, here’s how this sexy clothing business works,” I said. “The girl gets dressed in something sexy, which makes the man want to take it off of her. The sexier the clothing, the less time she wears it. That’s if the guy has his way. So, when I look at you in that dress, what I think of is that it’s covering up what I know is a killer great body and since I wish I could see it, I want you to take the dress off. Does that make sense?”

“Then it doesn’t matter what I wear,” she complained.

“In one sense, that’s true,” I admitted.

“Then what’s the point in spending all that money if you only get to wear it ten minutes?”

“Five minutes,” I said, but I grinned. Before she could complain again, I went on. “A sexy outfit gets the guy going. And since you have to date lots of different guys, it also makes lots of different guys want to take you out. So that kind of sexy clothing you get to wear for a long time. It’s the sexy lingerie you only get to show him for five minutes.”

“I don’t have any sexy lingerie,” she said. “I don’t have anybody to show it to, so I don’t spend money on it.”

“Sure you do,” I said. “Your baby dolls are gorgeous. They make me want to get you naked the minute I see you in them.”

“Really?”

“Sexy as all get-out,” I said.

“Stay there and close your eyes,” she said.

“Cathy,” I groaned.

“Just do it, Bobby,” she snapped.

So I sat there with my hands over my eyes while I listened to the rustle of clothing that meant she was getting undressed. I thought it was odd that, suddenly, she was shy, but I went with it. Maybe four or five minutes went by and then she said, “Okay, you can look.”

She had put on her baby dolls. This time she had the jacket on, but left the bra off.

“Is this sexy?” she asked.

I felt my bone stiffen and stood up. I pushed the waistband of my shorts below my balls and let her watch it go from a sagging, three/quarters hard-on to full anti-aircraft mode.

She seemed to float over to me and stood close enough that I could feel her body heat.

“Crystal said she loved learning to kiss with her brother.”

“You already know how to kiss,” I said.

“I got horny with Bruce tonight,” she said, leaning even closer.

“Did you let him do anything?” I rasped.

She shrugged off the jacket and took a mini step forward. I felt the tips of her breasts burn my skin.

“No. I saved it for you.”

My hands moved as if somebody else was controlling them. They slid up her sides and covered both her breasts. I could feel her hard nipples push into my palms. She closed her eyes and sighed.

“Mmmmm,” was all she said.

Part of my brain reminded me she’d referenced how much Crystal liked kissing her brother.

So I abandoned her breasts and slid my hands inside her panties to cup her firm butt while I kissed my sister.


You know that saying: Time flies when you’re having fun?

Well, not only does time fly when you’re having fun, your brain can go on “pause” while time is flying.

I have no idea how long it was between the first time our lips touched, to the moment when I regained consciousness. When I did regain consciousness, we were both stark naked, lying on her bed, and I was lying on top of her with the most delicious heat surrounding my penis that I’d ever felt. It took a few very jarring seconds for the realization to sink in that I was fucking my sister. It was unbelievable, because I couldn’t remember starting to fuck my sister. Then the next thing that registered was that my sister was not unhappy that I was doing this, because her arms were wrapped around me and her heels were firmly on the bed beside my hips and her hips were lurching upwards with more strength than I’d have thought she had in her.

She was making nonsense sounds, some gurgles and moans and just noises, that seemed to be in time with my thrusts. In the very few seconds before I was lost again, I was a little astonished that I knew how to do this, but my prick was slicing in and out of her like I’d done this a hundred times.

Then her voice stopped making nonsense sounds and she started panting, “Oh fuck, oh fuck, oh fuck, oh mommeeeeeee,” and it was just obvious she was cumming. I don’t know whether it was the knowledge that my cock was making her cum, or her fingernails puncturing my back, but one of the two flipped a switch in my balls and they upchucked. This might be the first time I had fucked, but I’d watched myself cum countless times, and my mind supplied images of milky white spurts exiting the tip of my penis, flooding her hot pussy. I did not feel shame. I did not feel remorse. I did not feel perverted.

What I felt was ... elated.

Later I would feel all those negative emotions, but at the moment I inseminated my little sister, nothing in the world could have felt better, or more right.

Cathy wasn’t nearly as ambivalent about things.

As we both collapsed, just breathing, her hands kept moving all over me. Maybe a minute later she started kissing whatever her lips could find to touch. Some of that remorse was starting to creep in, so I didn’t kiss her back until her hands came to grip my head and make me face her. She kissed me five or six times, and then breathed, “Thank you,” into my mouth.

By this time I was imagining millions of little sperm cells, all of which had my face, dolphin kicking their way into her uterus, sniffing for an egg. Just to show you how surreal this was, my imagination kept going until I saw one sperm cell sprout arms and a penis as it reached her egg. For some reason in my imagination, her egg looked like a baby blue Robin’s egg. Hands at the ends of the arms gripped the sides of the egg, and the penis fucked a hole right into the shell. My face, on that sperm cell, was grinning maniacally.

“How soon before you can go again?” whispered my sister. Her pussy suddenly squeezed, and my penis got pushed out of her. “Oooooo,” she complained.

“You’re insane,” I whispered.

“No I’m not,” she said.

“I just got you pregnant,” I moaned.

“No you didn’t,” she said.

That sperm cell in my imagination was now doing a victory dance, like it had just scored the game-winning touchdown.

“Yes I did,” I groaned.

“No ... you didn’t,” she said.

“How do you know?”

“Because I just started my period while we were doing that. I can tell.”

Have you ever seen one of those videos where a cat gets startled and jumps straight up in the air? I might have done that. I landed on my knees and looked down at my penis. It was tinted a little red, and my pubic hair was also wetly reddish.

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