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Dating Advice: Second Date

1500 words | 3 |4.93

Helen is getting deeper into uncharted territory and needs her big brother’s help again.

I’d done all I could to help my sister prepare for her first date. Her best friend Fiona had helped too by making it a double date, so the two of them had set off together. Striding out in their cute summer dresses, to meet up with the boys at the cinema.

It was thoughtful of Fiona but it meant I didn’t get to meet Jason.
I wanted to do the “tough big brother thing” and make sure he didn’t dare do anything to hurt or upset my little sister. Maybe I’d see him next time and he’d better behave himself until then!

I popped into Helen’s room to check up on her that evening.

“Well, how did it go?”

“Oh, the film was great. We all had a good time, thanks.”

“You know that’s not what I meant.”

“If you’re asking about Jason, well that’s private, isn’t it?”

“Of course it is. I don’t want to know the details. I just want to be sure you’re okay.”
Actually, I would have liked to hear “the details”, but they were obviously “none of my business”.

“Well, it was pretty much like you said, but he didn’t go too far.”

“You’re okay then?”

“Yes. I liked it, okay!” she was a little embarrassed.
“If he asks me out again then I’ll probably say “yes””.

I kissed her goodnight, “I’m glad you had fun. If you need any more help, you know where to find me.”

“Thanks, you’re a good brother, even if you are a bit nosey!”

A few days later Helen was in my room again.

“I need some more help please.”


“Well Jason’s asked me on another date.”

“That’s good, isn’t it?”

“Yes, but he wants to go to a dance.”

“I thought you loved dancing.”

“I do, but I’ve never danced with a boy before.
What if he wants to slow dance?”

I tried not to laugh. “You always find something to worry about don’t you? Are you asking me to dance with you, as if you were my girlfriend?”

You can say no if it’s too weird, but I’d like to get used to it. I don’t want to panic and look like a silly little girl in front of everyone on the dancefloor.”

“Okay. I’ll show you, but just one dance.”

I selected a track on Spotify.
“My last girlfriend used to like this one, I explained, “It’s by a woman called Sade. It’s so old our grandparents probably danced to it, but it’s slow and sexy.”

I turned out the light and stood facing my sister.
“Okay. We’re just trying things out, so if you don’t like it we can stop, alright.”

She nodded.

“So, the girl reaches up and puts her arms around the boy’s neck.”

“Like this?”

“That’s right, you can get nice and close. And because hands are out of the way Jason can touch you anywhere that he wants to, so watch out!
But most boys would just put their hands around your waist like this. Okay?”

I pulled her close, pressing her tits into my chest and driving her crotch up against my thigh.
“Oooo. You’re holding me very tight.”

“That’s the idea, you act like you can’t keep your hands off eachother.
Now you look into each other’s eyes, as if you’re deeply on love and there’s nobody else in the world.”

“That feels funny.”

“Don’t worry, it’s just because I’m your brother.
It will feel nice when you do it for real. Now you start to sway and move with the music.”

“Aren’t we just walking around each other?”

“Yes, pretty much.
But you’re holding your “truelove” close, staring into his eyes and showing everybody how much you lovel him” I said soppily.

“You’re such a cynic!
Anyway is that all there is to it then?”

“Not quite, it also gives Jason a chance to feel you up. Don’t be surprised if he moves his hands down to your bum and strokes and squeezes it, like this.
You can just move his hand away if you don’t like it.”

“No it’s, mmmmm, quite nice and I ought to get used to it in case it’s something that Jason wants to do.”

“Oh, and of course, he’ll want to kiss you. Open mouthed remember?”

She did remember. She pulled my head down to hers and gave me a full blooded tongue kiss as I continued fondle her buttocks until the end of the song.

“Did you like that?”

“Oh yes. Very much. I don’t know what I was worried about. I do have one question though.”


“It’s a bit personal, but er. I felt something pressing into my belly while we were dancing.
That was your, er ..dick wasn’t it?”

I chuckled, “Yes, I’m sorry. I can’t deny it. You’re a sexy girl and that’s going to happen. You’re just going to have to get used to it, now you’re dating.”

“I thought it was.
It felt bigger than I expected.
I don’t know how big Jason’s is.”

“I should think not – you’ve only been on one date!
Anyway, is that all you need to know about dancing with boys?”

“Yes thanks, I’m looking forward to it now.”

“There is something else though,” she added nervously.

There was always something else.

“My tits!”


“He said he liked my tits when I let him touch them at the pictures.
I think he’ll want me to let him see them next time.”

“Well, I’ve told you, he can want all he likes.
It’s up to you whether he gets to see them or even touch them again.”

“I get that, but I don’t know whether I want to get them out for him or not.
The idea of it feels ever so sexy, but I’m not sure whether I’m brave enough. I might get embarrassed and chicken out and he might not even like them! No boy has ever seen them before and they aren’t the biggest ones in the world.”

“Are you telling me you want to practice that too? I don’t know about that.
I’m your brother, it’s not something I should be doing.”

“Awww please.
Just for a minute.
It would really help me out and you have already touched one – last time, remember?”

I sighed, closing my eyes and shaking my head. I couldn’t believe I was going to say this, “Okay then, go on.”

She hugged me and gave me a big kiss, “Thank you, thank you.”

“Yes, yes, but just for a minute and we’re keeping the light off.”


She pulled her tee shirt over her head and stood before me in her pretty pink bra.
She paused.
Maybe that was it, perhaps she had chickened out, after all.

No, she hadn’t. She bit her lip, unhooked her bra and threw it to the floor.

I thought she might cover herself with her arms, but instead, she put her hands behind her head and proudly pushed out her chest.

“What do you think?”

“They’re great.
Jason will love them”
I said simply.
And they were “great”. Helen was right, they weren’t “the biggest ones in the world” but they suited her perfectly; firm, perky, tennis ball sized, crowned by pointy brown nipples. Gorgeous.”

“Are you sure?” she asked, giggling and striking different poses to show then off.

“Yes, yes, I’m very sure. I think I’ve seen enough now.” I was getting a little flustered.
“How do you feel about showing them off? You thought you might get embarrassed.”

“No, it’s exciting. I like it.
Is that okay?”

“I’m sure it’s okay, it’s your body, after all, but that’s enough, for now.”

I wanted her to stop before we went any further, but she showed no sign that she ready to cover herself up.

“Don’t you think Jason will want to do more than just look at them?”

“He might but, like I say, it’s up to you.”

“If you were in Jason’s shoes and I was your girlfriend, you’d want to do more wouldn’t you?”

“Yes, I’d have my hands and my mouth all over them. But… hey… no, no we can’t do that…”

“Go on. Please.
I want to know what it feels like.

She cupped her tits, pushing them together, holding them up, offering them to me.
I couldn’t resist any longer. I dived in.

Kissing and licking her left breast, while my hand played with her right.

“Ooooh, that’s lovely.
You do look silly, though.
No don’t stop – don’t you dare stop!”

And I didn’t.
My hand continued to enjoy squeezing and caressing and my mouth sucked in as much tit as it could.

Sharon moaned in approval and positively purred when my teeth gave her a teasing nip.

“Ohmygod, ohmygod. Don’t stop. Suck the other one…..”


Helen was more than ready for her second date.
Jason was in for a treat.
Lucky bastard….

I’m pretty sure she’ll get a third date too…

👄This will be the best oral sex you have ever experienced.👅

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  • Reply Kevin ID:2px1ognpxvh

    Please keep going!!!!

    • Mr Rodd ID:1ah742a8hrd

      There will probably be two more chapters.
      Working on the third at the moment

  • Reply Kevin ID:1d1o1n82284r

    Omg more