Dating Advice : Fourth Date

After her brother’s coaching, Helen is ready to go all the way.

On Thursday something happened that would change my life forever – I passed my driving test, first time! It was a real rite of passage because, as everyone knows, “a girl’s a woman when she gets a bra and a boy’s a man when he gets a car”.

I had some savings and a part time job, so I was hoping to find a cheap “motor” for myself, but Mum and Dad said they would buy me one as early 18th birthday present. I would just have pay for the tax and fuel – to help me get used to “adult responsibilities”.

So, my dad and I were huddled around our computer, looking for a car that was safe, reliable and within budget, when Helen returned home from her date. She gave me a secret smile and a “thumbs up” as she went up to her room – things had obviously gone well with Jason…

**************

We didn’t get the opportunity to chat until Saturday night, when our parents went to their friends” anniversary party and told us they wouldn’t be home before 11.30. Dad had left us money for a takeaway, so we enjoyed “a Chinese” and slobbed out on the sofa, to watch whatever trash was on the TV.

After a few minutes my sister curled up next to me and snuggled onto my side like a kitten
“Ro-o-ob?” she whined in a childish, singalong voice.

“Ye-e-es.” I replied sarcastically, wondering what she was after

“Can I ask you something?”

“You can always ask – I can’t promise to say “yes”.”

“Well, I had a nice time with Jason and I think I’m finly ready to “go all the way”.”

“Okay. Just as long as you’re sure and you both take care.”

“Yeah, but, there is one thing though…. Jason can be a bit… erm, rough.”

“You mean he hits you?
You don’t have to put up with that!
Do you need me to have a word with him?”

She giggled and squeezed closer to me, “No, don’t be silly!
I don’t mean that. He’s just a bit clumsy sometimes and I get scratched and bruised.”

“It’s probably his first time too. I guess he hasn’t been with many girls.”

“That’s just it.
He’s a nice guy, but he doesn’t really know how to handle a woman.”

“So…?”

She sighed – it was now or never.
“Look, it’s my first time and I’m a girl so l know it’s going to hurt and I’m a little bit scared. But, I’m sure it’s going to hurt less if it’s with someone that knows what he’s doing and not a nervous boy that’s making it up as he goes along.”

I pulled her close, “So what are you trying to say, love?”
I knew what she wanted, but needed her to say it.

“Will you do it?
Please?
I know people say we shouldn’t but, you’ve been so good to me already and I know you’ll take your time and keep me safe and be gentle with me.”

She stayed in my arms, silently, a little embarrassed, waiting for my reply after baring her soul, hoping I wouldn’t be angry.

I wasn’t surprised by her suggestion. It had been on my mind ever since I’d taught her how to do oral sex.
Like Helen, I knew people said it was wrong, so I’d been on-line to find out why.

There seemed to be two main reasons. Some people just thought all sex outside marriage was “wrong”, but I’d already been with three girls, so that wasn’t going to stop me getting it on with sister.

Lots of other people had another reason. These were the ones that made dark hints about the potential consequences for any babies born of such a union – two heads, brain damage – that sort of thing.
However it seemed to me that their problem wasn’t so much about the actual sex – they were just worried about the baby. So the answer to that was simple.

After careful consideration, I managed to convince myself that it would be okay to screw my sister, as long as we took precautions. After all, we were in a loving and committed relationship together, so it was perfectly natural.
Just like fucking any other girlfriend.

And I hated the thought of some desperate, clueless, young chancer ripping into my darling little sister, like he was opening a bag of crisps!
It would be
best if I took her instead.

“Are you sure?” I asked.

“Yes,” she breathed.

“Then….okay.”

“Thank you.”
She kissed me softly
“Can we do it tonight?”

We were both talking in whispers now.

“Okay, you go up to your room and I’ll get a wash. Text me when you’re ready. ”

“Okay,” and she was gone.

*******

Helen’s bedroom was typical of a girl on the cusp of womanhood.
Dolls in the window and teddies on the bed, but pop stars on the wall and makeup on dresser.
I was hovering outside in fresh boxer shorts and my silk dressing gown, awaiting the call to enter and to engage in the most adult of acts.

“Bing!”
I had a text message.
Just two words – “I’m ready” – and a heart emoji.

I went into her room. She was lying on her bed, her hair down, her face made up and wearing a short, pink nightie.

“Is this right?” she asked, raising her knees and parting her thighs.

“Not yet, babe. Stand up.” I took her by gently by the hand.
“We have to get warmed up.
I need to get you nice and wet and you need to get me hard so everything will just slide in comfortably.”

She bit her lip, nervously.
“Okay.”

I wanted her to relax. I hugged her, “There’s no rush. Pick some music on. Let’s have a dance.”

She selected a favourite track and we danced. We danced slow, holding each other close, like I had taught her.
Kissing like the lovers we now were.
I ran my hands across her back and slipped them down to enjoy the feel of her silky nightgown riding over her smooth round butt cheeks.

“Untie my robe,” I whispered.

Helen, undid the loose knot and pushed the gown off my shoulders.
I took hold of her nightie drawing it up and off, over her head.

We continued our dance.
My arms around her naked waist and her arms around my neck, holding me as close, as close qa1can be. Bare chest to bare breast, completely comfortable with no awkwardness or embarrassment.

I slipped her knickers off scooped her up in my arms, carrying her to her bed.
I lay her on her back. Kissing her breasts and caressing her pussy.

Helen was still a little tense, but her heavy breathing and her moist pussy told me that her arousal was increasing.

I slipped one finger inside her… then another one. .. then moved a thumb to her clit.

Her moans and her body told me she was ready. Nevertheless, I went down licked her slit, just because I knew we both loved it and we might never get the opportunity again.

Then it was time…

I moved up Helen’s, still virgin, body until my cock was in position pointing at its intimate goal.

Helen gasped, as I invaded the first inch of her most personal space.
I paused, then gently pushed back and forth three times before reaching her barrier.

I had only ever taken one girl’s cherry before, so l was no expert, but I was going to do the best I could to avoid hurting my precious little sister any more than I had too.

I pulled back, asked her to raise her hips to meet me and thrust through, sharply.

“Owwww! Aaaah!”
She gave a cry of pain, but the carnal deed was done and she’d never have to go through that again.
I held my position, while my lover’s body adjusted to my presence in that previously untouched place.

“Are you okay.”

“Yeah.”

“Are you sure.”

“Yes. Fuck me big brother.”

She’d never used that word before, I wasn’t sure it suited her but, she had been doing a lot of things that she had never done before, during the last few weeks.

So I fucked her.
Slowly and gently, responding to her needs, but I fucked her, nevertheless.

Helen grew more excited as she was overtaken by myriad new sensations and emotions.
I held on, waiting for her to reach her peak. Eventually she was completely overcome, her body spasmed and her cunt muscles cramped onto my cock, triggering me join her in orgasm.

*******
We lay together in the afterglow.
Kissing and stroking blissfully, without the need for words.

Eventually, of course, someone had to speak.

“How do you feel?” I asked.

“Wooonderfullll. Thank you.
How are you?”

“I’m wonderful too.
You were great.
I meant how do feel…you know…. inside.”

“A bit sore, but it’s okay, I know you were as gentle as you could be.”

“Good.
Do you want to do it again.
You don’t have to, if you don’t want to.”

“Can we? Oh yes.”
She rolled onto her back again, expecting more “missionary”.

“No, let’s try something different, this time. You can go on top.”

“Can girls do that?”

I tried not to laugh at her, “Yes and it will be good because you’ll be able to decide how fast we go. How deep we go and you can stop me whenever you get uncomfortable.”

“Yeah, that sounds perfect.”

I explained how she could straddle me and a few minutes later she riding my cock with a huge grin on her face while I manhandled her hips, her slim waist and bouncing boobs.

I watched as more and more of my cock disappeared inside her until my horny, sexy sister was fully impaled, balls deep on my manhood.

We both came once more.

“Fucking hell that was great!’ gasped my sweaty lover.

“You like being on top don’t you?”

“Yeah, I didn’t mind being underneath either though. It was nice with you in charge. I’m sure I’ll like it more next time, when I know what to expect and I don’t have to worry about getting hurt…”
“What was that?
Did you hear something.”

“Oh shit,” we heard a key unlocking the front door. Mum and Dad were home. “I’ll have to go.”
I gave her a kiss, but had to tear myself away.
“Love you.”

“Love you too, you’re a very special man. Thank you.”

I gathered my clothes and returned to my room, as quietly as I could.

It was nice of Helen to thank me, but there was no need. I had wanted to make love to her. And I didn’t think I was “special”, but what we had shared certainly was – it was very special.
It was such a shame that we would never be able to do it again.
She was my sister, after all.

***********

“You don’t think you’re going out dressed like that do you?”

“Awwww, Dad, it’s the summer, it’s a party. It’s going to be boiling. I can’t wear an overcoat can I.”

“I’m sorry lovey, your Dad’s right. It’s just not safe for a girl to walk across the park dressed so… attractively! On her own at night, these days.” Mum added.

Helen was going to a house party and naturally wanted to look her best. After all, she was planning to let her teenage boyfriend consummate their relationship and fuck her for the first time. I decided to help her out.

“Look, it’s a lovely evening and I fancy a walk anyway, so why don’t I walk Helen to Fiona’s house? Then she can look her best and I can keep her safe.
You did say Fiona’s dad is going to drive you the rest of the way, didn’t you?”

“Yes that’s right. And I’ll be ready for collection at midnight.”

“Eleven o’clock.” countered my dad.

“Eleven thirty?”

“Ok… yes.”

My sister and I set off toward the park. She took my hand, “Thanks for that. I didn’t want to get changed.”

“What do you mean. I just wanted to go for a walk.”

“No you didn’t!
You’re so good to me.”
She stretched up and gave me a peck on the cheek.

As we got closer to Fiona’s house I felt there was something I had to say.

“You know you look beautiful tonight, don’t you?
Jason won’t be able to believe his eyes”.

“Well I don’t know about that…”

I wasn’t finished, “You’ve grown into quite the young lady. Just make sure he treats you like one.
Don’t let him force you into anything and call me if you need to.
Oh and you might need these,” I handed her a pack of condoms.
“Just keep them in your bag. Don’t give them too him straight away – you’ll look like a right slapper.
Just keep them in reserve, ppin case he hasn’t got any. And if he won’t wear one, tell him to “fuck off”, I don’t care how cute he is!”

“Yes Dad.”

“No Helen, I’m serious.”

“Yes, Rob.
I promise
Thank you. I’m lucky to have a brother like you. You really are special.”

See met Fiona and I waved them off.
I walked home, mentally replaying everything that my sister and I had done together over the last few weeks.
The mere memory was enough to give me a raging hard on. It was sad to know that I had only been training her for her boyfriend and now our fun was over.
I knew it was wrong to feel this way, but I was jealous of Jason.

***********

I drove round to the party house at about 11.30. It took me a while to park as I had only got my car that afternoon. It was just a second hand Fiesta, but it was mine!

There were quite a few cars around the house and a knot of parents waiting for their offspring to emerge.
I decided to go straight in. I was young enough to look like one of guests and no one questioned my presence.

The music was loud and the air was thick with the smell of sweat, smoke, beer and maybe other substances.
The house was crowded. There were
teenagers chatting, arguing, dancing and snogging, as well as some who were just slumped in stupors having enjoyed themselves rather too much.

There was no sign of Helen but I spotted Fiona and beckoned her to me.

“Hiya Fi. Good party?”

“Yeah are you….”

We were interrupted when someone grabbed by the shoulder.

“Oy, lay off my girlfriend you fucker!”

The cause of the disturbance was shorter than me. A stocky, chippy sort of kid, who I assumed was a bit pissed.

I squared up to him.
“Actually I’m talking to my sister’s best friend and the lady has a name. It’s Fiona!”
I scowled down at him. I wasn’t there for a fight, but he was clearly a jerk and if he wanted a scrap, he was going to get one!

Fiona intervened, “This is Helen’s brother, Rob. He’s just here to pick her up.”

“Yeah if I can drag her away from her boyfriend. Do you know where she is?”

“She’s probably helping tidy up in the kitchen. She hasn’t got a boyfriend though.”

That was awkward. How could her best friend not know she had a boyfriend. Helen wouldn’t try to keep it secret would she?
I decided to play dumb. “Oh, I just assumed she must have – a pretty girl like her.”

“No, lots of boys have asked her, but she turns them all down.”

“Yeah, she always says she’s waiting for someone “special”,”the stocky kid interjected, assuming we were interested in his opinion.

Actuly it turned out that Fiona was very interested, “And how would you know what she says when turns a lad down? Have you asked her out?
You been hitting on my friend, haven’t you?”

“Well, I er, no. That’s not what er….”

“We’ll talk about this later.”
She turned her back on the boy.
“Let’s find your sister.”

We headed towards the kitchen.

“I’m sorry, I didn’t mean to cause you any trouble with your boyfriend.”

“It’s okay. He can be a right dick sometimes – it was nice to see you take him down a peg or two.”

“Yeah but if you need a ride home, I’ll be happy to drop you off.”

“I’ll be fine thanks.
I’ll walk back with Luke.
I know he asked Helen out, before we hooked up – she told me all about it.
I’m just winding him up.
It’s not just boys that can “treat ’em mean to keep ’em keen”.”

“Sounds like you can look after yourself.” I told her. ”
“Oh, by the way. Do you know anyone called Jason? There’s a dad outside looking for his son”
The question was a trick and it felt mean, but “on one hand”, if he was there, then I wanted to meet him, and “on the other hand”, I was starting to think that Helen might have made him up.
She had told me he was at her school, so if he was real, Fiona would know him too.

“Erm no, I don’t know a Jason,” she told me, “He’s probably upstairs with one of the girls; chucking up in the garden or asleep in the bath… Oh hi, Helen look who I’ve found!”

It took my sister a while to say all her goodbyes and hug all her friends.
We stepped out into the cool night air.

“Thanks for coming. I thought Dad was going to pick me up.”

“I told him I’d do it. He was ready for bed and, anyway I didn’t want him catching you doing anything you shouldn’t. ”

That made her giggle, “Thanks.”

“And I thought you might like to be first person to ride in my new car.” I pointed at it proudly.

“Oh, of course. I’d forgotten about that.”

We made ourselves comfortable and set off.

“Did you have a good time.”

“Yeah, it was alright, I suppose,” came the stereotype teenage response.

“Shame Jason couldn’t make it,” I ventured.

“Yeah, he’s not very well,” I was sure that was a white lie.

“I know, Fiona told me,” I answered, feeding her a lie of my own to see how she would react.

We travelled in silence for a few minutes.

“This isn’t the way home, Rob. Dad always goes through town?”

“He’s told me to stay off the busy roads till I get used to the car. It’ll take a bit longer this way but it’ll be safer.” That was just a ruse. I had a plan in mind.

“Right….. erm about Jason…”she continued.

“Yes.”

“I think I’m going to have to dump him.”

I knew this was another lie. It was her “exit strategy” and there was no need to embarrass her.
“Why?” I asked, “You seemed so keen on him last week.”

“I know but, like I say, he can be so immature sometimes.
I think I need a man that’s a bit older and knows how to treat a girl.
Someone special.
Maybe with their own car.”

I turned into a woodland car park and put my plan into operation.
I turned off the engine and looked directly at my sister.

“Tell me Helen. Have you ever fucked a man on the backseat of a second hand ford fiesta?”

She shook her head, “No Rob…. Well not yet away,” she added coquettishly.

“Would you like to?”

“Oooh yes please.”

We unfastened our seat belts…

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