Helping Sis Pick a Dress - Cover

Helping Sis Pick a Dress

Copyright© 2020 by Lubrican

Chapter 7

Coming of Age Sex Story: Chapter 7 - 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 thought about lying on my bed naked. I was pretty sure she wasn’t going to last long, trying to be mad at me. I mean if she really was serious about the baby thing (mind explodes with a silent pheow!) then there was no way she could resist me for any extended period of time. As for the baby thing (mind explodes again) I didn’t know what to think. Before she got the ring, while we had waited tensely for her friend to arrive and were worried she might be pregnant, I had thought about that a lot. My mind had played out various scenarios, most of which didn’t end happily. In fact, the only one that did end “happily” was the one where we ran away together and pretended to be married and she had the baby and we lived together after that. Of course, in that one, we never saw our parents or extended family again, so it wasn’t all that great an ending.

I was pretty sure she’d examined the options, too, and it was likely she’d run into all the same dead ends I had, so for her to say she wanted to get pregnant with my baby meant she was stressed out to the max. She’d always been emotional, which might be why she got emotional about me getting a boner for her way back, when all she wanted was for me to tell her what outfit looked hot for her dates. I knew she’d get over it, sooner or later. She wasn’t an idiot. She knew I couldn’t go fathering children on her willy nilly.

Anyway, I decided that if she came to my room and found me naked, she might think I had an overinflated sense of my worth, so I put on some shorts and a tank top. I was reading when she did, in fact, open my door and come in. I say I was reading, but I couldn’t concentrate on the book. I kept trying to figure out what was going through her mind. I mean how did she think getting pregnant would solve anything or make things better? She was complaining about me going away when all this came out, right? And if I got her pregnant, then I’d be going away for a lot longer than four years, and it wouldn’t be to college, right?

She had elected to get dressed, too, also in shorts. Her T shirt made it obvious she wasn’t wearing a bra. I loved it when her nipples imprinted on whatever top she was wearing. Our mother did not.

“Are you mad at me?” she asked, softly.

“I thought it was the other way around,” I said.

She came to the bed and sat on the edge.

“I just miss you,” she said.

“Cathy, I’m not even gone!” I groaned.

“I know that!” she snapped. “But you will be. And I’ll be miserable, and I know that, so I feel it already.”

“What do you want me to do?” I asked. “You want me to give up on college and stay here and get a job at Wendy’s?”

“No,” she replied, her voice surly.

“Well then, what?”

“If I knew that, I wouldn’t feel like this,” she groaned.

“I have an idea,” I said.

“What?”

“How about we don’t make a baby until at least after college,” I said.

She stared at me for so long that I started thinking I had screwed up somehow. I bet she just stared like that for two or three minutes. Finally she spoke.

“Are you saying that, after college, you would be willing to get me pregnant?”

I sensed danger, but I couldn’t identify it. It was like I was in the dark, and felt some malevolent entity out there that wanted to eat me, but I didn’t know which direction it was, or what it looked like, or how to protect myself.

“Maybe,” I said, trying to get more information.

She was just looking at me again.

“Can I ask a question?” I asked. She nodded so I went on. “Can you help me understand why you want me to get you pregnant?”

Because I love you, you dope!“ she said, instantly.

“I get that part,” I said. “And I love you, too. But how does having a baby help you to not miss me when I go to college?”

“I don’t know,” she said, slumping. “I guess I thought it would be like having a little piece of you with me, even though you were gone.”

“You know I can come home now and then,” I said. “It’s not like I’m joining the military and going on overseas tours for years at a time.”

“I know,” she moaned. “I just know I’m going to be miserable.” She looked at me intently. “But if I knew that, after we got through college, I could actually live with you, then having your baby then would make me very happy, Bobby, happy enough that I think I could stand you being away from me for one year of college.”

“Where did all this having my baby stuff come from?” I asked.

She leaned toward me.

“I just told you. It’s because I love you.” She sat back up. “I think I’ve wanted to have your baby since I was, like, thirteen.”

I was astonished.

“Thirteen?” My voice was weak.

“Yeah, about then,” she said. “I looked at all the brothers of my friends, and they were all dicks. But you were nice. And then I went to that stupid sleepover at Mandy’s and Crystal told me about how her brother had been fucking her for years and about how fantastic it was, and I got all confused about you. And then you got boners for me, and that made me feel even more confused, because I loved it and I knew I wasn’t supposed to love it, but Crystal loved it and she seemed completely normal, and she said she wanted to have David’s baby and that made me think about having your baby.”

She had to stop because she’d run out of breath. She took a deep one, but didn’t go on.

“I see,” I said, for lack of anything else to say.

“I think maybe that’s why I asked you to help me pick out a dress and got naked in front of you,” she said. “I didn’t think that back then, but now, I kind of think that’s what was going on.”

I was thinking about how she had acted, back then.

“You seemed pretty disgusted, as I recall,” I said.

“That’s how I was supposed to feel,” she sighed. “Except Crystal wasn’t disgusted. And she seemed so normal!

“So this is all Crystal’s fault?”

“No.” She looked at me. “It’s your fault. If you hadn’t been such a good brother none of this would have happened.”

“If I had been a good brother I wouldn’t have gotten boners for you,” I said.

“I’m pretty sure I wanted you to get boners for me,” she argued.

“So this is all your fault?”

She ignored that.

“Do you love me?” she asked.

“Of course I do. You know that,” I replied.

“Well, then, we have to figure out a way to keep being happy, because I’m really happy right now, but I know if I don’t have you I won’t be happy.”

I thought for a minute.

“Okay,” I finally said. “Let’s look at this logically, instead of emotionally. Before all this happened, did you think it would happen?”

“Of course not,” she said.

“Okay, so you didn’t think this could happen, but then it did. And now you don’t think you’ll be happy when I go to college, but isn’t it possible that, just like you adapted to us being ... um ... closer than most siblings ... you might be able to adapt to me not being here all the time? I mean you will get to see me sometimes, and like I said, you could go to college at the same school, and we’d be together again. So maybe it won’t be as bad as you think it will.”

She rolled her eyes.

“I’m in love with you, you dope. Do you think I’ll just fall out of love? Do you think we’ll break up like you were some random boyfriend or something? And if you fall in love with some girl, do you think I’ll be all happy for you? Would you be happy if I decided I was going to let Jeff Hancock fuck me?”

I had to suppress the urge to kill Jeff Hancock, who she had gone out with a couple of times. After those dates she’d been extra horny and we’d made love with maybe a little extra passion.

“We can’t get married,” I said. “As much as I wish we could, you know we can’t do that. And if we live together and you start popping out babies, somebody’s going to notice that, especially Mom and Dad. So how do you figure to explain that?”

“I don’t know,” she groaned. “I just know what I want.”

“Well if you’re ever going to get what you want, then we need to be smart about it, and having a baby right now wouldn’t be the smartest thing you’ve ever done.”

“I know that, too,” she said. “I think I just panicked.”

“Okay,” I said.

She reached to run one finger down my chest.

“Can I go for a ride now on my stallion?”

“Can I check to make sure your ring is still in?” I teased.

She took off her T shirt and let me look at her breasts.

“I’d be unhappy if you didn’t,” she said.


Her emotional crisis passed, but another one exploded, and it almost ruined everything as much as her belly swelling would have.

Gina, under pressure from two cheerleaders, wrote a prescription for Oxycontin.

It was the star running back on the football team that handed the prescription to a pharmacist. He thought he was being clever by going to Granite Springs, where he thought nobody would know him. It was precisely because the pharmacist didn’t know him, and because it was a paper prescription, and because it was from a doctor in a different town that questions popped into the pharmacist’s mind.

So he called the doctor who had prescribed the opioid and asked him to confirm it.

To say the shit hit the fan is like saying shooting your foot with a nail gun hurts.

Long story short, there was a big investigation and Gina caved and confessed. They interviewed her and she admitted to everything. She named a few names, but because Cathy was her only real friend, she left us out of it. Of course the investigators looked at every prescription for birth control “Gina’s dad” had ever written, and started interviewing ‘co-conspirators’ for the legal proceedings to come.

And one day, an investigator showed up at the house to confirm that our parents knew about Cathy’s prescription for birth control.

Which, of course, they did not.

I was not privy to the conversations that took place between Cathy and our parents, but of course she told me about them.

She admitted that she was sexually active, but refused to say who with. My dad wasn’t impressed. His baby girl had been soiled and he wanted blood. The term “whore” was bandied about, until Mom yelled at him and reminded him that they’d had sex long before they got married.

He settled down, but then said that until she was eighteen, she had to obey his rules, and a new rule was that she was forbidden to date until she graduated and moved out on her own.

Mom, being less emotional about it, and remembering her own youth, took Cathy to our doctor (not Gina’s dad) and after a very thorough exam, he wrote her a legitimate prescription for the ring. I think Mom knew that once a girl is sexually active, she stays sexually active. There was a lot of unannounced checking up on Cathy, to make sure she was in her room and hadn’t sneaked out. Obviously, that put a big dent in our nighttime get-togethers.

A month later, Mom got Dad to relent, and she was allowed to date again ... as long as it was a double date, and I was the guy with the other date.

So for two months, every time Cathy went on a date, I was on the same date with another girl, chaperoning my sister.

We had fun, but not as much fun as if we’d been on dates by ourselves. It wasn’t great for the guy she was out with, or the girl I was out with, either.

And then Cathy got the bright idea for us to go on double dates that were fake. In other words, we’d leave the house together to go on our double date, except that we just didn’t go pick up anybody else.

Finally, we had alone time again, together. Of course it was the middle of winter, so there were no blankets under the stars, where we could roll around and fuck each other senseless. There was a lot of oral sex, but we already knew that intercourse just didn’t work well in a car. At least not in our car.

It was April before she just couldn’t take it anymore and snuck into my room in the middle of the night.

We had to put a pillow over her face, because she started getting loud.


Graduation was emotional. I had spent so much time reminding Cathy that we had plenty of time before I left, that I sort of lost track of how quickly that time was passing. Plus everything was in turmoil because of the investigation. It had been a scandal all over town, because even though all the principals involved were juveniles, and their identities were shielded from the public, the rumor mill in town made sure that information got out. Naturally, any girl who got a birth control prescription from Gina was assumed to be a slut of the first magnitude, and that appellation got attached to some girls who, before this, were believed to be innocent, virgin angels. Like two daughters of ministers in town, for example.

So our routine had been thoroughly disrupted, so thoroughly that Cathy actually found out she could go without sex for quite a while. I, on the other hand, always had my ... hand. It wasn’t as good as a nice soak in Cathy’s hot pussy, but it got the job done. Cathy, at least for the first month or two, never knew when a parent would open the door without knocking and check on her.

Then, I think more from desperation than anything else, Cathy got a summer job. She worked at the city pool, checking people in and issuing baskets for them to put their clothes in and all that. It was a full time job. I worked part time for a construction company, cleaning up job sites, throwing the stuff I cleaned up into big dumpsters. I also unloaded lumber deliveries and that sort of thing. If the weather was good, I might work a twelve hour day. If the weather was bad, I stayed home.

I had applied to and was accepted by the college in our state that was called “The teacher’s college.” That’s because they specialized in turning out teachers. They had lots of other majors, of course, but because of Mr. Zalinski, our high school science teacher, who was the coolest guy I knew, I had decided I wanted to be a science teacher, too. I had decided I was going to major in secondary education.

So, in August, after a “last summer” that didn’t meet my expectations at all (and didn’t meet Cathy’s either), I went off to live in a dorm room and get on the path to my first career.

I got emails from Cathy daily. The first month it was almost always about how lonely she was, and how she cried sometimes at night. She didn’t say anything about dating, but I knew my dad, and I was pretty sure that, if I wasn’t there to chaperone her, Cathy wasn’t spending any time with boys away from school. When October rolled around her emails got less dark, and she started writing about what her friends were doing, and what was going on at school. She wanted to try out for a part in the musical that year, but Dad said no. He wasn’t letting her have that much freedom, where she might succumb to her base nature and let some boy fuck her. She mentioned several times that she was looking forward to seeing me at Thanksgiving. Meanwhile I paid attention in class and read all my assignments. I went to the student union pretty regularly, especially on weekends, and got fairly good at eight ball. I met some interesting girls, but it felt like cheating to think about going out with them, so I only talked to them, also mostly at the union. I also worked part time on work study for university services, which took care of the apartments they had for married and foreign students. I started in plumbing, which I thought would teach me something about plumbing, but it was almost all unplugging toilets, so I managed to get a transfer to the team that took out old carpeting and installed new.

Then Thanksgiving got there and I went home for the first time since I left home.

I got there on a Tuesday night, because I had to take a bus to get home. I didn’t have my own car. Luckily, Dad was home this year. There had been times in the past where he was too far away when the holiday got there to be able to come home. This year, though, he had four days off and picked me up at the bus station. He seemed normal. He asked me how school was and I said fine, and when I asked how everything at home was, he said fine, and it didn’t occur to me until much later that his reticence to talk might be rooted in the fact that he hadn’t gone to college and already thought of me as much more educated than he’d ever be. We got over that, eventually, but it made the ride home seem off somehow.

Cathy’s reception for me was strangely muted, especially since she had recently said in an email that she couldn’t wait for me to get home. She gave me a hug and a kiss on the side of the neck, and then said she had homework to do and disappeared. My room was unchanged, though Mom said something about turning it into a sewing room. What with her job and night classes, I wondered when she thought she’d have time to sew, but I knew she had a sewing machine and had repaired a lot of my clothes when I was younger, so I didn’t ask questions. Dad made it clear he expected me not to be like other kids my age, who hung around home for years after high school and “mooched off their parents,” as he put it.

It was actually kind of weird being home. I had nothing to do. A year before this, I would have had homework myself, or maybe gone to hang out with friends (or been in bed with Cathy) but now I felt like a visitor. So I sat down in front of the TV and watched a movie on Netflix. About halfway through it, Cathy plopped down beside me on the couch and asked me what I was watching. She sounded so much like a normal sister that I raised one eyebrow when I looked at her.

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