Helping Sis Pick a Dress - Cover

Helping Sis Pick a Dress

Copyright© 2020 by Lubrican

Chapter 6

Coming of Age Sex Story: Chapter 6 - 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  

I started hearing a lot more of Cathy whispering, “We’re pushing it, so pull out,” though I didn’t perceive it as her saying it “a lot more.” I’ll be honest, I never thought about her fertility. I always assumed that, if she let me go in her, she was safe. Cathy was just as addicted to sex as I was, though, and when given the choice between having oral sex, and having intercourse, she chose intercourse a lot of times she should have gone the other way. I’m not trying to make it sound like birth control is all the woman’s responsibility. We were adolescents, and adolescents use bad judgment a lot more often than we will later in life. That’s why we’re not allowed to vote until we’re eighteen. Most of us probably shouldn’t be allowed anywhere near a voting booth until we’re twenty-one, but that’s a different issue.

Anyway, one night, she whispered that I needed to pull out, so I did, and flopped onto my back, and her hand was right there to take care of me. She was an expert at jerking me off by now. Now, on this particular night, she had come to my room on her way to bed, which meant she said “Good night” to Mom and Dad, who happened to be home that night, and then, instead of going to her room, came to mine. She was dressed, of course, but it didn’t take long for her to get naked. We left the light off because you could see the bottom of my bedroom door from the dining room and either one of them might walk through the dining room on the way to the kitchen to get a snack or whatever.

So this should give you some idea of how rocky our sexual boat was. She didn’t even wait for them to go to bed, much less get to sleep, before she was naked with me on top of her, fucking her lustily. She knew I’d give her an orgasm before I came, and she would rather have that orgasm with my penis in her, than my tongue. So she got her penis-induced orgasm and then told me I had to pull out.

Then, because it was dark in my room, while she was jerking on my bone, and I came, she couldn’t see, and a blob of my cum plopped right into her open mouth. I didn’t know this, because I couldn’t see, either. All I knew was that her hand stopped, suddenly, and her grip on my cock hardened. She made a spitting sound at the same time she tried to whisper, “Shit!” Then she just kind of froze. Her hand disappeared from my penis, which was finished squirting by then, but she didn’t move. Using my keen senses, I deduced something was amiss.

“What’s wrong?” I whispered, thinking she might have heard something that led her to believe a parent was near. That will show you how stupid I was. I thought she might have heard a parent, and I was making noise that parent might hear.

“It got in my mouth,” she whispered back.

“What?”

“Some of your stuff got in my mouth.”

I had been trying to get her to leave her mouth on me when I came. She sucked my cock like she loved it, which was true. She did love having my penis in her mouth. What she was afraid of was having a bad reaction and ruining the moment. Plus, I had no bathroom in my bedroom, like she did. I had to use the bathroom in the hall, which Mom called the guest bathroom. Cathy, by virtue of being a girl, got the good bedroom, which had its own bathroom. Since we almost always engaged in oral sex in my room, if she stayed on, and then threw up, it would make a mess somewhere.

So she had never tasted my semen. Now it had gotten in her mouth, in the dark, when she wasn’t expecting it, and she’d had to deal with it. Happily, she didn’t throw up. If she’d done that, it probably would have been all over my stomach and my bed. And then I’d have thrown up, and for sure we’d have made enough noise to draw parental attention, and the world might have actually ended.

Instead, she decided it tasted weird, but not bad.

She did not tell me this.

“You okay?” I whispered.

“Yeah,” she replied. She got up. “I can’t see my clothes.”

“Want me to turn on a light?”

“No. They might see it. And it would ruin my night vision.”

I started to say, “You mean the night vision that isn’t working well enough right now for you to find your clothes?” but I bit my lip.

The next day we couldn’t talk about it, so I didn’t know until that night that she wanted to get more of my semen in her mouth to confirm that it was completely different (and less yucky) than she thought it would be.

On that night she did wait until our parents were in bed. She waited so long I thought she wasn’t coming, in fact. But she wanted to be able to have the light on, because she was planning on finishing with me in her mouth. Plus, she sat on the edge of my bed and talked about what she was going to do. She was still worried she’d toss, but not as much. She even brought her plastic trash can so that if she did throw up, she could take it back to her room on the run. She did not let me put it in her that night, but that made sense to me. She was leery already about getting my body fluids in her mouth. If she let me fuck her first, then her body fluids would be on it too when I pulled out. We didn’t talk about this, but I suspect that’s what she was thinking about. If I sucked her pussy, before I kissed her I wiped my mouth off on the sheets.

Yeah, I actually thought that would remove both her scent and taste completely. And I had no idea that she’d tasted her own fingers after rubbing off, way back when she was twelve. I guess that’s not the kind of thing you tell your lover about.

Anyway, it was actually kind of anticlimactic. She jerked on me, and sucked the tip, and I told her I was going to cum, and she put her lips in the valley, right behind the head of my dick, and I shot off. Her eyes got big, and she blinked a lot as she sat up. I really only got two spurts in her mouth before she sat up. Her hands flapped a little bit, like chicken wings, but then she closed her eyes and swallowed and opened her mouth again and just breathed. Her eyes opened and she looked at me.

“It’s different,” she said.

“Different?”

“Than last night.”

“Okay,” I said.

“Better,” she said.

“That’s good, right?”

She looked at me and I could see the change in her eyes. They looked smoky, somehow, or maybe hungry.

“We won’t be making a mess on your stomach anymore,” she whispered.

Then she got naked and insisted I suck her pussy.


After that night, oral sex was better. Sort of.

I qualify that because we still didn’t communicate well enough to avoid some pitfalls.

For example, in the past, she’d let me go in her and then, when I pulled out, she jacked me off. That felt good, but not nearly as good as if I shot off inside her. Had I known she’d be willing to suck me off after I pulled out, I might not have pushed the envelope so much before pulling out. As a result, I got a lot of semen either in her, or on her pussy lips as I pulled out.

That made her unhappy. Worrying about whether her period will start (or not) is very different for the boy than it is for the girl. A boy might think about it for a few seconds, think, “I hope it happens,” and then go back to thinking about whatever. The girl, though, thinks about it all day, and about just how much her life could change (for the worse) if her friend doesn’t show up. And we were getting careless enough that she worried about that almost every month. It added to her PMS symptoms. Ironically enough, later in life, our mother would tell us that’s why she thought everything was normal between us. Once a month my sister screamed at me for little infractions. What Mom didn’t know was that, after screaming at me because I moved her books while she was doing homework, later that night she’d suck my dick and try to pull my balls out of my body through my dick.

It was nowhere near a love/hate relationship, but it got rough when she was worried her friend might skip out on her. It just goes to show you how helpless lovers can become. We knew when we shouldn’t engage in unsafe practices, but we couldn’t make ourselves abstain.

Don’t get me wrong. We tried. We went so far as to make a rule that one of us always had to be dressed when it was during the oral sex only time of the month. That was supposed to serve two purposes. First, I had been known to get stiff again quite quickly. That meant that, if she sucked me off, making me harmless, while I sucked her off, I got hard again. Then, more often than not, I got it in her and that usually led to getting sperm where she didn’t want it. If I sucked her off first, there I was, ready to rock and roll, while she was emotionally vulnerable and happy, and her pussy was all too eager to have something nice and hard and long stuffed in it. I was a fucking horn dog who always preferred to fuck her, as opposed to some other method of emptying my ball sack, so I was no help at all, when it came to avoiding unsafe sex.

If I had clothes on, however, and my unruly little friend was covered up, then it couldn’t get into mischief. And if she was dressed, then my stiff, eager little buddy couldn’t “accidentally” get in her while we kissed.

The other reason we made this rule was because, if oral sex was going on like that, and we got caught, it seemed more likely that our excuse for doing this would be believed. That excuse was that we were “learning how to do this to keep from being pressured into having intercourse on dates.”

If that’s not idiotic enough, did anybody notice that, under this system, only one half of the pair got satisfied?

See why we shouldn’t be able to vote?


How we managed to go the rest of the school year without getting Cathy pregnant will forever be a mystery. I had a lot of “accidents” and she didn’t seem to know how to say, “No, Bobby. Not right now. It’s too dangerous.”

If she stayed in her room, I snuck in there. I admit she did say, “Noooooo,” softly a whole bunch of times, but if I kept coming she made room for me on her bed. And she kissed me. And she let me finger her and suck her nipples. And if she didn’t stop kissing me and go down there to suck the firmness out of my banana, then eventually I’d roll on top of her and if she didn’t reach to guide me, I’d wiggle around until I felt heat around the tip of my prod, and then jerk forward.

These days, a lot of women would say I forced her, or intimidated her or some such thing, but that never happened. What happened was that her smart part told her to resist, and her lusty part wanted an orgasm. It was that simple.

This is why a lot of women, primarily teenagers, have undesired pregnancies.

And my role in all this?

Well, I was a male, and males everywhere, of all species, try to mate as often as they’re allowed to. Our lusty side wants to have orgasms, too.

At any rate, there were roughly five times that winter when neither of us felt frisky. Those were the times when she felt like her friend should have arrived already and was delayed for reasons unknown. Maybe her friend got stuck in traffic a lot. Or maybe she just didn’t have a handle on what time her friend had said he’d (she’d?) arrive. We didn’t know that the stress of worrying is sometimes enough to throw a cycle off for a few days.

And then she’d start, and suddenly it was worry-free and completely safe, and we made up for all the time we’d missed being worried. And a new twenty-eight days would start all over again.

Then, in early June, she went to her first slumber party of the summer and everything changed.

She had a friend named Gina, a kind of bookish, nerdy girl, who if you saw her in school didn’t look like the kind of girl all the popular girls would hang out with. And, for the most part, they didn’t ... in public. But outside of school she was highly sought after as a “friend”. Cathy was somewhat bookish herself. She got asked out by a lot of guys, but I think that was more because she was pretty and had big boobs, than because these guys all just craved being with her for the great conversation they expected to have. Most guys didn’t ask her out more than two or three times. She’d kiss them for hours and get them hard as rock, but that was all she ever let happen. She might not have any control when it came to me, but she had control in spades on dates.

Anyway, Cathy and Gina ate lunch together sometimes, and Gina invited her to a sleepover and promised it would be fun, so Cathy went. It turned out some of the popular girls were there, too, but it wasn’t to pursue friendships with either Cathy or Gina.

Gina’s dad was a doctor, and she had filched a couple of his prescription pads. Not only that, she was really good at forging her father’s signature.

For twenty bucks, you could get a prescription for anything you wanted except scheduled drugs. Those were too closely looked at.

But birth control? Have at it, sisters. She’d write those all night long.

Gina also knew a lot about the different kinds of birth control because her dad had all the literature. He had a pile of articles and pamphlets various pharma reps gave him, that gathered on a table, and which he read when he had a chance. Unknown to him, Gina read some of that stuff, too, and especially anything to do with birth control.

Which is why at this sleepover, when my sister indicated an interest in birth control, she came home with a prescription for the ring.

I didn’t know about the vast majority of birth control options for women. I knew about the pill, and condoms. And the rhythm method and withdrawal, of course. But I had no idea there were other things on the market. Cathy didn’t know, either, until Gina gave a mini seminar at her sleepover. Cathy said it was crazy. There they were, a bunch of teenage girls, sitting in a half circle, finding out there was a plastic coil-looking thing which, if implanted in a woman’s womb, not only kept her from getting pregnant, but in many cases it stopped her from having periods completely. And that lasted for up to five years! Of course none of the girls opted for that one. First off, a doctor had to put it in. Second, it cost like fifteen hundred bucks, or something like that.

What Cathy chose was the ring. I had never heard of this, either. It was exactly what its name implies; a flexible ring of rubbery material. This ring is impregnated with chemicals that are released into the body through the vaginal wall. It’s about two inches across and all you have to do is shove it up in the vagina and leave it there for three weeks.

Cathy was all excited when she got home and told me about all this, but there were a couple of things she was kind of vague on. The pharmacist who handed her the first set of them explained how to use it, which was good, because it wasn’t quite as “trouble free” as the company liked to say it was.

First off, it had to be inserted on either the day your period started, or the fifth day after your period started. There was a little dildo looking tool you used to push it up inside with. But there was more. If you inserted it at eight A.M. on a Monday, then you had to take it out at 8 A.M. three Mondays later. Not nine or ten o’clock, but right at eight. And not on Tuesday. Nope. If you started on a Monday, Monday was your day forever more. Once you removed it, you didn’t put a new one in for one week, during which you (probably) had a period. Using the scenario already established, if you did have a period, and it wasn’t finished by eight A.M. on the Monday after you took the last one out, then you put a new one in anyway.

We didn’t notice until after we had already violated this rule that, if you weren’t already on hormonal birth control when you started, you had to wait seven to ten days before having unprotected sex before the ring became effective. You were also supposed to check before and after intercourse to make sure it was still in there. The penis could drag it out under just the right (wrong?) conditions. I got pretty good at feeling for it before intercourse, but we never checked it afterwards. I mean wouldn’t it be obvious if a two inch ring of rubber was lying on the bed between her legs?

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