Helping Sis Pick a Dress - Cover

Helping Sis Pick a Dress

Copyright© 2020 by Lubrican

Chapter 5

Coming of Age Sex Story: Chapter 5 - 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  

Having sex with my sister was oddly less rushed, or even maybe almost clinical, once my fear of embarrassment had passed, or been washed away by hormones or whatever. She rolled onto her back again, lifting her head and feeling around with her hands to make sure the towel was where she wanted it, and I got between thighs she spread apart for me. I stared at the mouth of her pussy, and learned something important. A menstruating vagina doesn’t look any different from one that isn’t menstruating. I’m sure that if I’d stared for hours, I’d have seen some evidence, but I didn’t stare for hours. While I was doing that, she bunched up a pillow and propped it under her head.

I bent over and put my hands beside her breasts, in her arm pits. My penis pointed at her face. She tried to reach, but my wrist was in the way and I had to lift one hand so she could get her arm inside it. I was too far down and she could only reach the tip with her fingers, so I moved up a little. She bent it down, aiming it somehow, and I watched at the tip slowly approached her puffy pussy lips. Then I watched as it nosed between those lips, pushing them aside like a running back might push aside two cheerleaders who were on the field for some reason and were in his way.

“Go slowly,” she said.

I thought she was worried it would hurt, but later she told me she just wanted to watch it go in her. We both did that, watching as it slowly disappeared inside her, like a hiker caught in quicksand.

Then there was nothing to see anymore, as my scraggly brown pubes meshed with her lustrous blond ones. Did I mention Cathy was blond? Her head hair was lighter than her pubic hair, but I think that was just because her head hair was exposed to a lot of sunlight.

Nobody was paying attention to pubic hair after that, though, because my pubic bone gently kissed hers, and since her clit was in the way, it got a little smooshed. She gave an audible sigh that even the village idiot would have known meant she was happy, and that tripped some instinct in me to press harder. I’m pretty sure I was only trying to get deeper in her, but all it actually did was crush her clit harder. Plus I moved upwards a little, which meant that my skin rubbed her clit while it was being crushed.

“Oh fuck yes,” she groaned.

And I spurted.

Just like that, with no warning of any kind, I lost it and my balls tried to climb out of their sack and shoot through my penis into her body.

“Nooo,” I whined. It couldn’t be over that fast! The world just wasn’t fair! I was being punished. I didn’t think about why the cosmos might be punishing me, but I knew it was.

Then, as Mother Nature encouraged me to seed my lover properly, she caused me to pull out a couple of inches and slam back in as my penis produced its second stream of ejaculate. That was followed by another little out and back in, and I realized I wasn’t getting soft. I was soft-er, but not soft. Not wanting to look a gift horse in the mouth, I started fucking her with short strokes. Her legs came up to wrap around me and I looked at her face. Her eyes were closed and she was biting her lip, grimacing like it hurt, but I knew it didn’t hurt.

I am convinced to this day that my premature ejaculation was responsible for the fact that I continued to make love with my sister, on a more or less regular basis for years, afterwards. That’s because, once I came (and didn’t go completely soft) I was clear-headed enough to pay attention to her, and try to manipulate things such that she would forgive me for popping off two seconds after I got in her.

In other words, I experimented with how to fuck a woman in ways that are intended to produce orgasms for her. I had heard the term “multiple orgasm” and knew it applied to the female, and not the male, so basically, I thought, “We’ll just see about that.”

I wiggled, and moved, and rubbed. I came out a lot, and came out a little. And, completely by accident, I learned that, if I went in deep and moved my lower body in big circles, it drove her bananas. I watched her have two orgasms that way before her hands came to my chest and pushed.

“I can’t breathe!” she gasped.

I stopped, but didn’t pull out of her. I didn’t know for sure, but I thought I was a little harder.

I didn’t ask her if she wanted me to stop. I just gave her time to catch her breath. I couldn’t quite reach her nipples with my mouth, unless I withdrew, and I didn’t want to withdraw. Then a radical, brilliant idea popped into my mind.

I talked to her about it.

“I want to suck your nipples some more, but I’d have to take it out to do that. Can I put it back in later?”

She nodded her head frantically.

“Promise?” I could be both brilliant and an idiot in the space of ten seconds.

She pushed on my shoulders and I slid out of her. My cock felt cold and lonely, all of a sudden.

I sucked, playing with the texture of her nipples, which were very firm. I don’t know if a shrink would say I missed my mother’s nipples, or what, but I really loved sucking Cathy’s. I always have, ever since then. Sometimes, if she’s sleepy, that’s all I do, real gently.

Her fingers played with my hair while I was doing this, and then her heels bounced against my butt, which was up in the air and I took that as a suggestion that I get back in her.

I was rock hard again and this time neither of us watched. She just reached, aimed and I sank home like I had been made to be there. She was really slippery and hot, which meant there wasn’t a lot of friction. I played with long strokes, but I had to hold myself up on stiff arms to do that and pretty soon my back complained. I lay down on her body, which felt like I was crushing her, but she lifted her head to kiss me, so I figured she’d tell me if it got to be too much.

With her breasts crushed against my chest, I could move a little, like they were tiny mattresses or something. What that did was move me in and out in her, but only a couple of inches. It just felt good. Nothing was urgent, on either her part or mine. We just enjoyed being in intimate contact like that.

“You want to cum again?” I finally whispered.

“Can I?” she asked.

I interpreted that as “May I?” when what she actually meant was, “Is it possible?”

I stiffened my arms, but left my loins crushed to hers, and started doing circles again. She was off to the races, and the noises she made spoke to my balls, which announced that, with a little more effort and time, they’d be willing to supply another dose of happy juice. It took longer, this time, maybe five or six minutes, long enough for me to begin to feel irritation where my pubes were being pressed into my tender skin down there. Then her hands gripped my hips and urged me to go faster. Those hand stayed there to guide me and she took deeper and deeper breaths until she got all tense and groaned like she was dying.

I wasn’t quite there, and I knew it would take too long to get me there, but I wanted to cum again, so I pulled out and did a one-arm pushup while I jacked on my cock. It felt sticky, but I didn’t care. With my hand on it, I was able to get there within thirty seconds, but about the time I spurted, my arm gave out and I fell back down on top of her. My cock spit aimlessly on her abdomen and made a mess, but her hands on my back, made it clear she didn’t care.


Sex can be messy business. It’s perhaps slightly more messy during menstruation, but if you get up and take a shower after sex anyway, there’s no difference if you do it after menstrual sex. That sticky sensation I felt was her blood. It turns out that menstrual blood is different from normal blood, due to its composition and its physical properties. I won’t go into what those properties are, because it makes some people uncomfortable. The point is that, from the male perspective, menstrual sex doesn’t feel any different than non menstrual sex. No difference at all. If you want the female perspective, talk to your own partner about it. The only thing that might be different is that you need to shower after menstrual sex. But then you should clean up after normal sex, too. It’s just good hygiene.

In our case, we took a shower together, got squeaky clean, and then I watched as she put a tampon in. Walls that would normally have been there had tumbled down and there was very little after that that was “private” between us. I’m sure it’s not like that with other people, but it was with us. Maybe the fact that we had lived together our entire lives had something to do with it. I don’t know.

I started getting supper ready while she washed the towel, which was all that needed washing. We were eating chicken nuggets and tater tots when the front door opened and our father stomped in.

“I’m home!” he yelled out. Cathy and I stared at each other and our eyes said it all. If he’d gotten home an hour earlier, Armageddon would have commenced.

His nose led him to the kitchen.

“We didn’t know you were coming,” said Cathy, as she hugged him.

“I got a load that let me stop by here on the way,” he said. “I texted your mother.”

“She didn’t tell us,” said Cathy. “You hungry? We ate it all, but we can make more.”

“What’s wrong with you?” asked our father, looking at me. “You look like you saw a ghost.”

I hadn’t seen a ghost. What I’d seen was in my imagination, and it was the man standing in front of us, on top of our mother, making Cathy and me. I’d never envisioned that before. My new status as ‘sexually active’ had changed my outlook on other things, and this was the first evidence of that. I pushed that out of my mind.

“I’m just tired,” I said.

“Lazy, you mean,” he said, but he smiled. “It looks like you should have mowed the lawn days ago.”

“I’ve been mowing everybody else’s,” I defended.

There was more banter, and then talk as we caught up. He went to take a shower while Cathy heated up more chicken nuggets and tater tots. I opened a can of spinach, because I knew he liked that.

He ate and then took a nap until Mom got home. She was always tired, but having Dad there gave her a shot of energy. Cathy and I left them alone and an hour later we could hear them ‘catching up’ in the bedroom. It wasn’t loud. I’m quite sure we’d heard it in the past and ignored it, but now we knew what it meant.

“That was close,” said Cathy, now that we were alone and they were too busy to interrupt us.

“Too close,” I said.

She came up to me and pushed me against the wall, kissing me passionately. When she pulled back, her eyes were wide.

“Why does almost getting caught make me so horny?” she gasped.


So, let me recap. My sister asked me to help her be sexy for her dates. In the process she got naked for me as if it were normal to do that. I got a boner for her. When she found out about the boner, she wanted to see it. I groped her and fingered her pussy and we started kissing. I ended up on top of her, in her, spurting her full of incestuous brother goo. She liked that. Finally, when we almost got caught doing it again ... it made her horny!

Did you notice there how in the beginning there was one word emphasized, per sentence, and as things got farther and farther into this insane ... behavior ... more and more got emphasized, until whole sentences were in italics!

That’s what my life did. Everything was normal, and slowly, very slowly, things got more and more weird (emphasized) until my whole days were weird!

I didn’t know what to do. I mean for most seventeen-year-old guys, their day during a summer vacation involves goofing off (video games, comic books, etc), maybe doing some kind of chores, hanging out with friends, eating, and beating off. He might beat off twice in a day, if there’s some kind of special stimulus. So if you call beating off weird (emphasized) then maybe he’s weird ten minutes a day. It usually only takes three minutes, but you have to get ready, like picking out a magazine picture to stare at, or pull up some porn on the computer or whatever. It takes way longer to get ready than it does to jerk and shoot.

What most seventeen-year-old guys don’t do on a routine basis is see their hot sister naked and then fuck her.

In other words, this behavior isn’t routinely discussed in the locker room, where tips and advice about girls are routinely passed out.

Don’t get me wrong. I’m not trying to avoid responsibility for what happened. I admit I had a great time while I was rolling around on top of my sister. I came hard and I loved putting every single spurt deep in her belly. And I’d rather see her naked than any model in a magazine or porn site.

It was the afterwards part I had trouble dealing with. I think that’s because I actually knew what making love with Cathy was like. Before that happened, all I had was my imagination and some fantasies to dwell on. But now I knew what it was like and didn’t need my imagination cluttered up with that.

But what that did was leave my imagination with plenty of room to visualize all the things that could go wrong in this scenario. I don’t have to list them. I’m sure you can imagine them, too.

Basically, I was pretty much a wreck. It turns out that being pretty much a wreck affects your whole life. After almost getting caught by our dad, I went to my friend Peter’s house to hang out and maybe shoot some hoops. He was playing a video game, so I picked up the other controller and joined in. I got killed every thirty seconds because all I could think about was not talking to Peter about fucking my sister. I told him I didn’t feel good, and left and just walking down the street all I could think about was Cathy, with her friends, blabbing about this and that and her saying something like, “You should let your brother fuck you. I love it when Bobby sticks his cock in me!”

I knew she wouldn’t do that, but I felt like that woman in The Scarlet Letter, which they made us read in school last year. I didn’t have a big red A sewed to my shirt, but it felt like anybody who looked at me would know instantly that I was an incestuous pervert.

I was a complete wreck for a whole week ... but nobody called me out. Then another week went by and our secret was still a secret. Two weeks later mom started talking about school clothes for the coming school year and didn’t give any indication of any kind that she thought something was going on. Basically, it took a month for me to realize that, if we were careful about it, nobody was going to find out I was an incestuous pervert.

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