Dating Advice: First Date

It’s sister’s first date. What should she expect? Spoiler alert – This part sets up the story, she won’t be going all the way on her first date.

Knock knock. “Are you busy? Is it okay if I come in.”

“Yes, of course. Do you need help with your homework again?” Helen was three years younger than me and I knew she was struggling with her GCSE’s.

“No it’s not school.
Well it is school, but not work.
You see there’s this boy…”

“Oh, I see.” I turned off my TV and patted the bed inviting her to sit next to me.
“Come and tell your big brother all about it.”

“Well… his name’s Jason and he’s asked me out.”

“Erm, you’re a very pretty girl with a nice personality – I’m sure lots boys have asked you out.”

She shoved me, embarrassed. “A few have, but the boys in my class are all so immature.”

“But Jason’s different?”

“I think so and everyone else is doing it so it might be fun.”

“Doing what?”

“Dating, of course! What else would I mean.”

“Okay but you know you don’t have to do anything just because everybody else is.”

“I know. Now are you going to help me or not.”

“You haven’t told me what you need yet.”

“Well, you’ve been on lots of dates, right?”

I wasn’t quite the lothario she might think I was – like many 17 year old boys, I had occasionally, been guilty of exaggerating my success with the ladies, nevertheless I nodded,.
“Yes.”

“Well I haven’t been on any. I don’t know what to expect, or how I should behave. I’ll just make a fool of myself.”

“I’m sure that’s not true.
Where’s he going to take you?”

Helen took a deep breath., “He wants me to go to the cinema with him on Friday night.”

“Ooooh, smooching on the back row, l suppose?”

She shoved me again, “Don’t laugh at me. That’s just it. I’ve never “smooched” with anyone before. What will I do if he wants to kiss me or if he tries to… you know … touch me?”

“I’m sorry for laughing. I understand, it’s all new and a it’s little bit scary.
To be honest Helen, what you do really depends on whether you want this boy to kiss you or touch or… whatever.”

“Well…. I might want him to, but I’ve never been with a boy before. I don’t want to act like a little kid.”

“I’m not sure how I can help with that…”

“Could we practice?
I’m sure you’ve taken girls to the pictures before. Just pretend I’m one, so I’ll know what to expect and I have some idea of what I should do.”

I laughed at my sister again. “Okay, if you think that will help, but don’t expect any popcorn!”

I went to my DVD collection. “Let’s see, what do I have that you might like. Batman? Is that okay. Right I’ll put that on. Now turn the lights off so the room’s dark, like the cinema.”

“Oh yes, good idea,” said Helen, excitedly.

“Now we’re going to take our seats. Is Jason right handed or left handed?”

“I don’t know. Why?”

“Because he’ll want to put his arm around you.
Let’s say he’s right handed like me. He’ll sit you here, on his right.”

We sat on the edge of the bed and watched the film’s opening credits.

“Now, a few minutes after the film starts, he’ll probably do this.”
I stretched out my right arm and put it over her shoulders, resting his hand on her side.

She snuggled in against me.

“Now, you’ve snuggled next to him. That tells him you like having his arm around you, so now he’ll try to go further.
That’s how it works.
The boy can’t read your mind, he won”t know how far you want to go, but he wants to go as far as you will let him. He’s going to carry on, touching or stroking or squeezing or whatever, until you tell him to stop, or he loses his nerve.”

“I see, I hadn’t thought about it like that. So what might he do next.”

“I expect he’ll try to get a feel of your boobs.” I moved my right hand around her a little more, so I could reach the side of her breast.

Helen took a deep breath and bit her tongue.
“What should I do.”

“Well, if you like it or don’t mind, then you just carry on watching the film like it isn’t happening. He’ll probably get the message and go a bit further. If he does anything you don’t like, or you just think you’ve gone as far as you want to, then you tell him to stop.”

“Okay, well I don’t mind so far, so l’m just going to keep watching the film.”

“So he’ll probably try to do this.”
I slowly moved my hand further, cupping my sister’s boob for the first time. Surely she’d tell me to stop soon.

“Oooh no one’s ever done that before. It feels nice.”

“Thank you.
You feel nice too.”

She giggled.
“Is that it? I mean what else might Jason want to do?”

“It depends how brave he’s feeling. He might get over excited do this.” I gave her tit a sharp little squeeze, through her clothes.

“Ow!” she jumped.

“But I wouldn’t try that, because it’s embarrassing if the girl squeals, like that, and you might get thrown out.
So of he’s cool he’ll just rub your boob like this, or he might…. well no we don’t want to do that…”

“Go on, do it, it’s okay.”
She giggled and snuggled into me.
“It’s felt really nice so far.”

“Okay, but just a little bit more and you have to tell me to stop if you want me to.”
I hoped she’d stop me soon.

“Okay” she whispered.

I took another deep breath. “Because it’s dark at the pictures, he’ll think he can get away with a bit more than if you were in the park, or somewhere like that. So he might try to slide his hand under your top, like this and if you don’t stop him he’ll slowly work his way up until he’s touching your bra.”

“You mean touching my tits?”

“Yes.”
She’d made no effort to stop me so, sister or not, I touched one. It was soft and smooth – previously untouched by human hand.

She sighed.
She was liking this and seemed to want more.
I was supposed to be helping Helen find out how far she would let her boyfriend go and I hadn’t discovered her limit yet.
I have to admit, I was having fun, but that wasn’t the point. I was failing her.
I would have to try harder – whether I wanted to or not.
I decided to go a step further.

“He might even do this”

I pulled the bra down and gave her bare tit a good squeeze, rolling it in my hand, enjoying the feeling of her hard nipple. It felt so good – my little sister was growing into an attractive young woman, but it also felt so wrong – my little sister was, well, my little sister!

I was relieved to hear her say, “Oh, I wouldn’t want him to do that. Not in the cinema, with all those people around!”

“Then you need to learn how to tell him to stop.
I’ll show you how. Let’s try something different.”
I needed to leave my sister’s tits alone, before I went too far.

I put my hand on her knee.
“Does that feel nice?”

She gave a nervous giggle, “It’s okay.”

“Now, he’s going to slide his hand up your leg. You don’t want him to touch you right up there do you?”

“No, of course not!”

“So you need to tell him when to stop.”
I slid my hand a few inches under her skirt.

She pushed it away angrily, “Don’t you do that you dirty sod, who do you think I am!”

I pulled my hand right away.
“Well that would certainly stop him! But it would get you both thrown out of cinema and ruin any chance of another date.”

“Look, sometimes you might need to act like that. If you tell a boy to stop and he doesn’t or if he if tries to force you, then you should make a scene!
Yell at him. Slap him if you need to. He’s an arsehole and every girl in the room needs to know it!
But the first time, you can just ask nicely. The boy was trying to see how far he could go. You’ve told him so now he knows, he’ll probably respect it.
So be a lady about it, make a joke if you like. That way you’ll still be friends and the date can carry on, but on your terms.”

“Alright, that sounds sensible. Can we try again and I’ll try not to freak out.”

I was happy to try again.

I pushed my hand back up her skirt, she let me go further this time. Further than I thought a brother should go. I must have been close to the knicker line when she took hold of my arm.

“That’s enough, naughty boy.” she whispered as she pushed my hand back five or six inches.

“Perfect. No big fuss, ladylike, firm and a little bit bit saucy.”
“I think you’re ready for that date now.”

“I don’t think so. You haven’t shown me to kiss yet. I don’t think a normal brother and sister kiss will do, will it?”

“Ok. I’ll show you.
Just follow my lead and pull away when you want to stop.”

I put my hands on either side of her head and pulled her face to mine. Her lips were puckered at first, as if she was kissing her granddad, but she soon copied me, opening her mouth and kissing me like a lover.
We embraced tightly and tumbled back onto the bed, joined at the lip, our tongues in each other’s mouths and our hands all over eachother’s bodies.
I don’t know how many minutes we spent rolling around in eachother’s arms before we had to come up for air.

I was supposed to be in charge, so l tried to regain some composure and act as though I were simply giving my sister dating advice.

“Yes, that’s very good, Helen.
Maybe a little too strong for a first date, though.You don’t want to suffocate the poor boy, but I think you’ve got the general idea.”

More dating advice to come soon.

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