Helping Sis Pick A Dress
Chapters : 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8
I read a story somewhere about a girl who asked her brother to help her choose a sexy dress to go out on a date
in. It didn't have any author name on it. This is my take on that plot idea.
I was playing a video game and had just died for probably the fifteenth time in a row when my sister called me into her
bedroom. I needed a break anyway, so I answered her bellow. I found her standing in front of the open walk-in closet looking
"What do you want?" I asked.
"I'm going out with Dennis Holly tonight. I want to
wear something sexy but I donít know what."
"You have a closet full of sexy clothes, Iíve seen you
wearing all kinds of hot stuff. So what do you want?" I repeated.
She looked up at me. "Help me, I can't decide what
looks good. You're a guy. What kind of outfit turns you on?"
"You do realize how weird this is," I said.
"What would your friends say if they found out you asked your brother what
She didn't rise to the bait.
"Come on, Bobby," she whined. "You've been
going on dates for years. You know how to do this. I don't."
She was right. I was seventeen and had been on a lot more
dates than her. She was fifteen years, six months old, which seemed like an
arbitrary age, except she'd gotten her first babysitting job, and that was when
she'd negotiated with our mother about getting a phone and being allowed to date. She had a nine
o'clock curfew and this was only her second date, and she was already thinking
about dressing sexy!
I stepped back from my sister and looked her up and down.
She stands about 5'6, comes in around 115 pounds. Her chest is much bigger than
any of her girlfriends, something that had embarrassed her until recently.
Until she was fifteen years, six months old, to be precise. For a girl not yet
sixteen, she was built. If I didn't know better I would have thought she was a
junior. She's got a pretty face when she isn't being a bitch, and her sandy
blond hair falls in easy curls to the middle of her back. She was wearing Daisy
Duke jeans shorts and a white halter tied at the waist so her midriff and belly
button were showing. She hated bras and halter tops were the only outfits she
was allowed to go braless in.
"Well," I said, "where is he taking you? You
should dress for the situation, right?"
"I don't know," she said.
"Wear what you have on, that's pretty hot."
"This is too casual. You know that. What girl have you
ever picked up who was dressed like this?"
"None, but if I had, it would have made my dick
She ignored my crude comment. "You have to tell me what
I should wear tonight, I'll try on some stuff and you be the judge. Remember,
it has to be sexy enough to get Dennis on his knees later. I want him to beg to
see my boobs."
"You're not showing some kid your tits," I
"They're my boobs," she said. "I can
show them to whoever I want to."
"If Dad finds out you're flashing your tits, your
dating days will come to a screeching halt," I said. "You're lucky he
lets you date at all."
"Who's going to tell him? You?"
"No," I said. "I wouldn't rat you out. But
why do you want to do sexy anyway? Dates are supposed to just be for fun."
"Feeling sexy is fun," she argued.
"C'mon, Bobby. You have to help me."
"Okay, I will, on one condition. You have to promise
your tits is all anybody will get to see."
"Why do you care?" she asked, her voice scornful.
"Because any guy who gets to see your pussy is going to
want to put his dick in it, and I don't need a pregnant sister," I said.
I was trying to shock her, but she just stared at me.
"If I didn't know better, I'd think you love me,"
she finally said.
There was more scorn in her voice, and the casual observer
might have winced, thinking she wasn't helping her cause. The truth was that we
were really quite close. When your father is a long haul trucker and your mom
works as a waitress and is going to night school, you sort of have to raise
yourselves, and it's a lot easier to do that as a team than separately. We
helped each other all the time, whether it was cooking, laundry, homework, or
just about anything else. The only reason I hadn't agreed to her request
immediately was because I wasn't crazy about her going on dates.† I knew
what I tried to get girls to do on dates and thinking about other guys doing
that to her made my stomach queasy.
The time for sibling rivalry was past. This was important.
She had no idea what lengths guys would go to, to get their dicks wet, and she
was a prime candidate for that pastime.
"I do love you," I said. "I know what
guys want, and if you get too sexy, they're going to try to take it. I don't
want that for you. I don't want you to get raped, or even scared."
"I get it," she said. "But I still want to
feel sexy. Please, help me pick something out."
I sat on the edge of her bed then relaxed back on a pillow.
We got a weekly allowance and Cathy spent most of hers on clothes. I hadn't
paid any attention to that until now. Her closet was packed. Cathy flicked
hangers this way and that and pulled five things off the hangers and tossed
them to the bed. All together the five dresses looked like they might have been
made from enough material to maybe make a bed sheet. A single bed sheet. Maybe. Skimpy was the best word I could
think of for any of them and she hadn't even put them on, yet. I was expecting
her to hold the dresses up against her cute body and ask my opinion but once
she had her selections she said, "Okay, I'll try these on." She
glanced at her adjoining bathroom for a couple of seconds and I was thinking
she would go in there to change. After a short hesitation my sister surprised the
crap out of me by dropping her shorts and pulling off her halter. In seconds
she was standing unabashedly in front of me wearing just a blue lace thong.
While I stared at her firm, jutting tits with large pale brown areolas and fat
nipples my prick began to do what guys' pricks do when they see a hot chick.
She saw me looking.
"What are you staring at? You've seen me like this
before," she said.
"No, I have not," I sighed. "The last time I
saw you naked was when we still took baths together. Man, Cat, you should have
warned me. I'm pretty sure guys aren't supposed to think about their sisters
She snickered, "Don't tell me my brother is a pervert.
You're supposed to react to the clothes, not my boobs."
"What cave have you been living in? The clothes bring
attention to the body. When you're wearing something sexy, the guy imagines it
lying in a pile on the floor. He's thinking about what the clothing
While I talked, Cathy stretched her arms over her head and
slipped a yellow knit sheath down her arms and body. When her arms were
straight up, her boobs lifted, like they were shoulders shrugging. My mouth
watered. Once the dress covered her, she adjusted the waist, pulled at the hem
which was only a couple of inches below those panties, then spun to look over
her shoulder in the full-length mirror.
"Mmm, it makes my butt too big, don't you think?"
"No, but the color isn't right for your hair."
The yellow knit was quickly discarded. As she was stripping,
my cock grew even harder, it was beginning to get uncomfortable in my pants.
She put on a blue sequined outfit next. She owned a sequined dress! Who knew?
I'm sure my mom didn't. It was nice but too fancy and didnít show enough
cleavage. The blue garment joined the yellow in a heap. By the time she had put
on the third one, solicited my opinion, and then stripped free of it, my balls
were churning. It was a good thing our father had never seen these dresses.
He'd throw her in the basement and lock her up until she was twenty-five.
"This is making me uncomfortable," I said. I
didn't mean that I was uncomfortable on a cultural or moral basis. What guy
would turn down seeing a hot chick naked ... even if she was his own
sister. I meant I was physically uncomfortable because I had on tight
"So ... get comfortable," she said. Her attention
was on the next dress.
"In this case, getting comfortable would mean taking my
pants off, and if I do that, you're going to see just how sexy you already
are," I said.
"So you are a pervert," she said, merely
glancing my way.
"I'm a guy, and any guy would react this way to what
you're doing. That's what I'm trying to warn you about. Any guy who sees you
like this is going to want to try to fuck you."
"You haven't," she said, all sassy and
"Yet!" I said, trying to intimidate her.
"Show me what you got, big talker," she teased.
So I took off my jeans. I felt stupid in briefs and a shirt,
so I took the shirt off, too. The front of my Fruit of the Looms bulged
"Oh," she said. Her voice sounded a little faint
and she wasn't so cocky, now. I suppose, if you want to be all technical, I was
the cocky one. Or my cock was. My cock was definitely ... cocky.
I had to hand it to her. She was a trooper. She went on with the show like a veteran of Broadway.
Next she put on a white mini dress that was thin enough I
could see the blue color of her thong through it.
"If you wear that, you'll need flesh-colored
panties," I said.
She turned and looked at her butt in the mirror.
"You can see the lines," she pouted. "It
She bent over, reached under the skirt of the dress, and
took off her thong. Then she looked in the mirror again.
"That's better," she said.
"So now you want to go both braless and commando?"
"It looks better," she repeated.
"Yeah, and it's better for the guy, too. Now all he has
to do is slide his hand up your leg and he'll get a handful of hot pussy."
"Don't be so crude," she said. "I can keep my
legs closed. I'm not ready to have sex, Bobby. Ewww. I just want to feel
"And any guy who finds out you don't have panties on is
going to want to feel your moneymaker."
"Oh really? Well, maybe the guys I go out with will
have more class than you," she said.
Something sort of snapped in me. At least that's what I
think happened. I've thought about this many times since then and I'm sure
that, before this, I wouldn't have even thought about doing what I did.
What that was, was that I got up and went behind her. I
reached around with my hands and cupped her titties. They were just as soft as
"What are you doing?" she gasped.
Before she could say anything, or do anything, I slid my
right hand down, under the skirt and up to her soft, blond pubes. I pushed my
middle finger between her labia, which were slippery, by the way, which meant
she was turned on, too. Then I diddled my sister's clitty, sawing my finger up
"Ohhhhh," she groaned.† Her hands came to resist,
and my head cleared. I let go of her. The hairs on the back of my neck were
standing up. I felt like running away, but I had too much pride or something. I
went and sat on the edge of the bed again. I talked before she could scream at
"You're too accessible," I said.† "You can't
just lay it all out there and expect the guys to keep their hands off. And when
a guy moves, it can be fast, faster than you can deflect."
That little blue thong was still in her hand. She threw it
I caught it. Do not ask me why, but I brought it to my nose.
Well, I suppose you don't need to ask me why. What I meant was that I
didn't do that on purpose.† It seemed I was doing a lot of things on impulse
Her eyes got even bigger and she stalked over and jerked her
"You smelled my panties, you lowlife perv."
"Sorry," I said, automatically. "But this
proves my point. I'm your brother, for pity's sake, and sexiness can
even get me going." I blinked. "I mean your sexiness."
"I know what you meant, you moron," she growled.
"You sniffed my panties, Bobby! I would never sniff your
"Apples and oranges," I croaked.
"It's not the same thing."
She stared at me. Her eyes dropped to my lap.
"Stand up," she ordered.
I expected her to say, "Now leave!" when I did, so
I stood. She didn't say that, though. Instead, she stared at the front of my
briefs, which were stretched way out.
"You have a boner," she said, needlessly.
"Uh ... yeah," I said. My tone of voice said,
"And I caused it," she said.
"That's what I've been trying to tell you. Dressing
sexy leads to this problem."
"Even if you're my brother," she said, pounding
another nail in my coffin.
"Guys are just built this way," I tried.
"This is what the Me, Too Movement is all about,
Bobby," she said.
"Maybe," I said. "My point is that if you
dress like that, it's going to get the guy going and even if he's a decent guy,
he can only take so much before he snaps. That's what just happened. I snapped.
I'm not proud of it. But it happened, and it can happen to the guys you go out
with, too. I'm not saying it's cool, or right, or acceptable or any of that.
I'm just saying you make it more likely if you dress like that. It's just nature.
It's how dudes are built."
"A guy should be able to control his urges," she
"I agree," I said. "But give a guy time to mature and develop some self control before you flash your naked pussy at him."
"I didn't flash anything at you," she said.
"You got behind me and molested me!"
I decided not to mention that she'd stripped almost naked in
front of me a couple of times and then took off her panties in front of me.
"Let me see it," she said.
"You heard me. I want to see how guys are built."
"That's not what I meant," I said.
She pulled off the mini dress and stood stark naked in front
of me. She put her hands on her hips. There was a scowl on her face, but even
this way she looked unbelievably sexy. I couldn't help but look down. My
fingers had felt sparse pubic hair while I molested her, and now my eyes
confirmed that, in the pubes department, she was only fifteen. She hadn't grown
a lot of it, and it did nothing whatsoever to hide fat, tasty-looking pussy
Another unsolicited behavior manifested itself. I licked my
lips. For a couple of years one of my fantasies had been to give a girl oral
sex. I actually wanted to do that more than get my dick in her. I mean oral sex
won't get a girl pregnant, and it can make her really happy, right? And maybe
she'll reciprocate. I mean surely a guy can live without intercourse, if he can
get regular blow jobs. Plus I just really thought a girl's pussy would taste
good. I mean it looks good, so it must taste good, too, right?
My eyes darted up to hers. I was sure she'd seen me licking
my lips, and I expected Mount Vesuvius to blow. She wasn't entirely clueless.
She looked shocked, or at least her eyes had gotten really big, but she didn't
scream at me.
"Show me," she said, softly. "C'mon, Bobby."
"This is crazy," I wheezed. "I'm just
supposed to be helping you pick a dress."
"And you are. You've definitely helped me. I know I
can't wear any of those." She pointed at the little pile of dresses on the
"I'm not supposed to show you my dick," I
"I'm naked," she pointed out, as if there
was any way in the world I could have missed that.
"You shouldn't be," I said. "That isn't
"This is actually very helpful," she
argued. "I think I understand things better than I did. I mean I knew guys
get all horny and act goofy, but I didn't understand they get like ...
"This is normal," I whispered. I winced. "For
non-brothers, I mean."
"You said guys are guys," she reminded me. "I
get that this is weird, but it is helping. Now show me your penis,
Her use of the 'proper' word for it made things seem more
clinical. Or maybe I subconsciously wanted to show it to her. To a girl.
To any girl.
Very slowly, I hooked my thumbs into the waistband of my
shorts and started pushing down. I had to bend over, of course, but I was too
freaked out to stretch the waistband out, which mean that my dick bent
downwards and then flopped up once it was free. When my underwear was around my
ankles, I stood up. I was pretty sure I was going to be ordered to cover up
again, or get out, or something along those lines, and it would be easier if I
could just reach down and pull.
It was a pretty good stiffy, meaning that it was pointing up
at a twenty or thirty degree angle from my abdomen. It was at the perfect angle
to go in a woman, but when it was that hard it was difficult to beat off,
because I had to push it down. I use the word "difficult" loosely.
It's never all that hard to jerk off. I wanted to do that now, but controlled
"Wow," she whispered. "I didn't know."
"Didn't know what?" I croaked.
"It's big," she observed.
"Thank you," I said.
Her eyes came up to look at my face.
"Why would you say that?"
"Say what?" I felt like I was in a dream and
things were kind of misty.
"You thanked me for saying it was big. Didn't it just
grow that way?"
"I guess so," I said.
"You made it sound like you worked hard to get
it that big."
"Usually it's the other way around," I said.
"What?" Now she was the confused one.
"When it gets like this, I work hard to make it soft
again," I said. This conversation was so surreal I was beginning to be sure
I was dreaming.
"Oh," she said. "I get it."
Her hands came off her hips and she took a step towards me.†
As if I felt threatened, I tried to take a step back, and was instantly tripped
by my underwear. I lost my balance, flailed, tried to lift one foot, which just
stretched my shorts more, and went down in a heap. The bed broke my fall, but I
ended up on the floor.
She was over me in a second, asking me if I was okay and
trying to help me up. In the process one of her boobs appeared in front of my
face. One of those fat nipples was right there, an inch away, and whatever it
was that had hijacked my self-control slapped me on the ass. I forgot about trying
to salvage my dignity and leaned forward to capture that nipple between my
lips. I got in two little sucks before it was jerked out of my mouth and she
stopped trying to help me up.
"Bobby!" she squealed.
"Sorry! Sorry!" I gasped. "I didn't mean to do
"You can't accidentally suck a nipple!" she
barked. Her fingers came to massage the offended nipple, as if I'd bitten it or
"I'll just go," I said.
"You will not just go," she said. "Get
up off the floor."
I reached to untangle my feet, and took my briefs off. I got
up and, to my surprise, my cock was only half hard. Now, instead of pointing up
like an anti-aircraft gun, it sagged downwards at a forty-five degree angle,
more like the barrel of a tank. The foreskin was also covering more of the
head. This did not escape her attention.
"What happened?" she asked, peering at my manhood.
"I'm embarrassed," I said. "That affects
"Well make it get hard again," she said. "I
wasn't finished looking at it."
"I can't just make it get hard," I said. "It
doesn't work that way."
My sister might be young, but she's not stupid. She stood
back and moved her feet apart about a foot. She pinched the nipple I'd
"That felt really weird," she said. "When you
sucked, I mean. And before, when you put your finger here." She split her
fat pussy lips with one index finger. "That felt weird, too."
Presto, my erection was back.
"That's better," she said, abandoning both nipple
and pussy. "I'm starting to get the hang of this sexy thing."
"You don't need to get the hang of anything," I
said. "You're a natural."
"Aww, you're sweet," she said.
"No I am not sweet," I said. I gripped my cock.
"This is proof of that."
"Proof you're a pervert?" she teased.
"Yes," I said, perfectly willing to label myself
that way. I was, after all, wishing I could fuck my sister. "I'm definitely
a pervert, and the fact that you can turn your own brother into a
pervert should be warning enough that you can't mess around with this sexy
business on dates. Not until you're a lot older than you are."
"Lie down on the bed," she said, ignoring my sage
"I want to look at it," she said. Now she was the
one whose voice communicated, "Well, duh!"
I didn't know what else to do, and this crazy dream just
kept going on, so I lay on the bed, all the while thinking, 'She could look at
it with me standing.' My penis didn't quite lie down on my abdomen.
She came to the edge of the bed and bent over. I noticed the
shape of her breasts changed, but only a little. They'd felt soft in my hands,
but they were really firm. Her nipples were hard and I licked my lips again.
She didn't see that, though. Her attention was all on my cock.
"That skin on the tip. That's the foreskin,
right?" she asked.
"Yeah," I said.
"We talked about that in health class," she said.
"Somebody asked Miss Winston what it was for, but she said that wasn't
"Okay," I said. What else do you say in a
situation like that?
"So ... what's it for?"
"Um ... I guess I don't know," I said.
"What do you mean you don't know?"
"I mean I don't know what it's for," I said.
"How can you not know? You have it. You know what
everything else on your body is for. Why not that?"
"I don't know!" I complained. "It's just
there. It slides back and forth."
"What do you mean it slides back and forth? How?"
"I thought you said you talked about it in health
"It was mentioned. Miss Winston said some penises have
a foreskin, and others don't, because it's removed from some babies. That's all
"Well mine wasn't removed," I said. "That's
all I know."
"How could they remove that?" she asked,
leaning closer to my prick. "It looks like it's attached."
"It is attached."
"You said it slides back and forth. Make it do
"I have to ... um ... touch it to do that," I said.
"Then touch it," she said, somewhat impatiently.
So I gripped my cock and skinned the tip bare. She actually
backed up a foot.
"What? That's amazing! Do it again!"
"If I do, it will become beating off," I said.
"Okay. I'll watch."
"Cathy, this is already strange enough," I
groaned. "What happened to you?"
"I found out my brother gets boners for me," she
"A boner. One boner. This is the first
one," I said, trying to make me sound less perverted. "And you have
to admit you got naked in front of me, first."
"Okay, I admit I asked you for help, and that I changed
clothes in front of you. None of that means I want to have sex with my own
Her voice was triumphant, as if she had just unmasked the
arch villain in a movie. It had gotten a little louder at the end of her
pronouncement, but she wasn't screaming at me, or anything like that. It was
more like she'd just won the argument.
"It gets hard all the time," I said, lamely.
"Sometimes it even gets hard for no reason. So it doesn't mean I
want to have sex with you."
"Oh give me a break," she snorted. "You and
half the guys at school would love to get in my pussy. I'm not stupid."
"Now you give me a break," I said. "I
would never hurt you."
"I know that," she said, derisively. "At
least admit you want to climb between my silky, pale thighs and make naughty
"Why would you want me to say that?" I moaned.
"Come on, Cat. This is crazy!"
She stood up and grinned.
"It is crazy, isn't it. But it's also more fun
than I've had in I don't know when." She frowned. "So ... can I touch
"You want to touch my perverted penis?" I gaped.
"Well, I wasn't planning on touching Dennis Holly's.
Touching yours would be much safer."
"Cathy, you shouldn't be touching anybody's
pecker!" I said.
"You're not my mother," she said.
"I think it's interesting you brought her up," I
said. "Let's see. You want to touch a penis, and if a penis touches you ... in
the wrong place ... it can turn you into a mother. I think that's kind
of poetic. Not to mention that Mom would freak completely out if she found out
you were even thinking about playing with cocks, not to even suggest my
cock. And for sure let's not mention Dad." Our father was
conservative. He flatly forbade her to wear a bikini at the pool, for example.
She counted on her fingers.
"One, I'm not thinking about playing with cocks, plural.
I'm only thinking about touching one cock, yours. Two, of course Mom
knows I think about that stuff. We talk about it. And three, touching yours
with my finger will not get me pregnant. If you think that, then you're just an
idiot. And by the way, you did mention Dad."
"Wait. You and Mom talk about this?" I
pointed at my straining woody.
"Well, obviously not that one," she
replied. "When I got my period she talked to me about how I'd get curious
about boys and want to see things and touch things."
"And she said that was just peachy?" I asked,
"Of course not. She said I needed to wait to do all
that until I got married."
"So ... are you asking me to marry you?" I grinned.
I thought I had her on the ropes.
"You are an idiot," she snorted. "My
brother is a perverted idiot." She picked up a dress she hadn't tried on
yet. "I'll just wear this one. You can go, now."
Thirty seconds later I was standing outside her closed door,
holding my clothes in my hand.
The dream was over.
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