Practice Date with Kim

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A practice date with my sister's best friend.
1.7k words
4.18
53.8k
44

Part 1 of the 3 part series

Updated 06/10/2023
Created 07/29/2020
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Copyright ScottArroy August 01, 2020

https://www.literotica.com/s/practice-date-with-kim

This was my first story written on Literotica. It has been revised for improved reading.

My sister asked me to help out her best friend. Now I have known Kim since she went to kindergarten. She is intelligent, kind and sexy and if she wasn't my sisters bestie she would be on my radar. Kim for some reason doesn't so much like bad guys she just constantly falls into relationships with duds. After twelve heartbreaks in eighteen months she lost all confidence and stopped going out retreating into her shell.

Not that my track record was great either. Treat them mean to keep them keen probably best defines my behaviour. Don't get me wrong that wasn't a deliberate strategy, I just wasn't that into any of them.

I was however into completing university and my work placements. Always accepting any additional work irrespective of any impact that would have, to anyone I was dating.

Her CEO placed great esteem on relationships so Kim was desperate to find out what she was doing wrong.

Becky, my always scheming sister, had suggested and promised a practice date with me would provide her some insight.

So when I say I was asked perhaps it would have been more accurate to say my sister told me I needed to do this favour.

Becky made it very clear that nothing short of me being in a coma in an intensive care unit would suffice for a no show this Friday night.

At precisely six fiftynine I approached Kim's door to collect her for this date.

She answered the door with a hesitant but friendly smile.

That smile evaporated when I said "Surely you don't think you're going on a date with me dressed like that!"

"Don't I look alright?"

"It's smart casual and more than appropriate for a family barbeque but not for a date! If we were dating I'd expect you to be presenting some dazzle with a side split, cleavage or makeup something to make others notice you. For a first date I expect some effort! Show some sort of interest. I'm not asking for a statement piece but please show a little effort."

"I'm sorry Paul. I'll go and change. I won't be long." She let me in, then went into her room to change. Not ten minutes later returning sporting captivating eyes and a body hugging top and jeans with laced sides showing some unattainable flesh.

"Kim you are absolutely stunning. This is a good first date outfit. Hinting sexy but making it clear you're setting the boundaries."

"Thank you. Shall we go?"

"Kim what you should have said was ... Listen fella I'm not here to impress you or others! You're here to impress me! If you don't like who I am just turn around and walk away!"

"Oh!"

"Kim you are special; why don't you value yourself?"

"I do but perhaps I don't illustrate it."

"Let's go then. Your first outfit was nice for just hanging out but this one screams, adorable first date. While you shouldn't have had to change, I do appreciate the adjustments you've made."

She smiled warmly at that and we walked to the car where I opened the door for her. "You know if you just stand at the door for any guy that doesn't offer to open it for you, you'll send a very clear message not to underestimate you."

"Noted!" Again giving me her killer smile. Perhaps this practice date wouldn't be so bad.

We stopped at a bar for a few drinks. I drank Pepsi Max; Kim put away two ciders.

I hurried her to complete the second drink saying "We have a dinner reservation at eight fifteenth. I put my arm around her to walk her to the car and in guiding her into the car my hand ran up over her side boob. For a woman of strong integrity she certainly had submissive tendencies.

At dinner the conversation ran smoothly and I sat adjacent to her rather than across the table. Kim was attentive and always made eye contact with me. I noticed my eyes didn't go wandering either. Kim was onto her fourth cider and because I was driving I stayed with the no sugar cola option the restaurant served.

To my surprise Kim questioned or stated "You really take this practice dating seriously?"

"How so?" I innocently asked.

"Holding my hand!" Lifting it up as confirmation.

Now I hadn't realised I was holding her hand so quickly I recanted with "Ofcourse how else can I give feedback if we don't make it as real as possible!"

Desert came and Kim tasted the first morsel declaring it as "Delicious!"

Her second spoonful was thrust into my mouth and after a pause "It is, isn't it?"

"Yes it is! I sputtered.

I went to put a bite of mine into my mouth when Kim said "Surely dates who want a second date share their desert?"

I swallowed it.

"So you don't want a second date?" She flirtingly challenged offering a second taste of hers.

"We need to play this out for real and getting a second date has never been an issue for me."

"That could be part of the problem." I accepted her offer and presented some of mine so that we simultaneously ate from each other's spoon.

"If I dated guys like you instead of the losers I normally date perhaps there wouldn't be any problems."

"Do you think so? I have a string of exes that might disagree."

"Well I've known you most of my life. It might be more honest to say; I've never known a time in my life when you weren't in it. In all of that time you have always treated me with respect. I can only judge you with how you have been with me not on what has happened in other relationships."

I laughed but her words certainly left me warm.

We held hands walking to the car. At the traffic lights I commented, "Lucky this is not a real date as normally I kiss and molest my dates when waiting for the lights to change."

"I thought we were treating this as a real date!"

"Yes well.." The constant beep indicating the lights had changed saved the day. It was only two hundred and fifty feet to the next corner also with pedestrian lights.

We arrived at the lights and yes they were red. Kim turned to face me and I wished I'd had at least one of those ciders. I wrapped my hands around her clutching her rear cheeks and proceeded to kiss her. Kim offered no resistance. We made out till those annoying beeps sounded. I'd be lying if I said I didn't want to stay there.

We drove to the club this time walking arm in arm to the venue.

We danced for some time into the early hours of the next day and were stunned when the lights brightened and it was clear we were being encouraged to exit the building. Laughing we left not waiting for a traffic light excuse to embrace and pash. When we made it to her house she thanked me "for a wonderful night so far".

"So far?"

"Well you're supposed to be advising me on where I'm going wrong with my dating!"

"Are you sure Kim?"

"This might have started out as a practice date but if you weren't such a gentleman you would have noticed the wet stain in my jeans."

Now that remark had my eyes go straight to her crotch.

While my eyes were down there she continued. "I noticed you have wood, that you've been doing your upmost to hide. So I know your body is in sync with mine!"

I stood there hesitating, knowing this was my sister's best friend.

"If you want a chance at a second date buster you better get your tail and your other swinging bits in here right now. Do you really want to explain to Becky why you bailed on our date!"

I smiled, I couldn't recall a time when I'd been blackmailed before. I was considering the alcohol I'd plied her with. What effect dating Kim would have on Becky. Then I thought about Kim and about myself.

I knew I needed Kim and just perhaps she needed me.

"How would you feel if I stayed the night but we didn't act on any impulses we might have?"

"Will you sleep in my bed so we can at least snuggle?"

"Sure we can snuggle and when we wake if you want to do more we can and if you don't ... well that will be ok too."

"Deal! Now get your clothes off, 'cause no one wears clothes in my bed."

She stepped forward and started undoing my buttons pulling me into her house and kicking the door closed with vigour. My reluctance ceased and I had that top off promptly. Kim moved to my pants and had me unbuckled and dacked, pushing my bare bum onto a chair so my shoes and all could be easily removed.

Whilst discarding her top she screamed,

"Race you to the bed." Somehow managing to run in the three inch heels she was wearing.

I was into the game by this time and thought I'd be on her bed naked before her. I wasn't. My eyes encountered a face with a huge smile, breasts standing proud with pointed square nipples and legs splayed out with a bushy arrow pointing to a glistening labia.

"Oh my!" I didn't mean to utter.

"Come on Paul show me you can resist me!"

At that moment I wasn't quite so sure my gentlemanly intent would hold out. Kim was a goddess. Somehow I realised I'd always known that.

I jumped up onto the bed, my manhood landing just short of her homebase. Our mouths met and the pashing commenced when her giggling desisted. I knew I was a goner and this so called practice date was the best date I'd ever been on. I was pretty confident that might also be true for Kim.

I couldn't contain my smile when I realised this practice date was still ongoing.

Hey my name is Scott. Please let me know what you thought by comment and vote selection. If you liked it perhaps you follow me so you can read other stories. I wrote this on my phone so I'm still trying to work out how to best present.

All the best Scott.

Copyright ScottArroy August 01, 2020

https://www.literotica.com/s/practice-date-with-kim

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7 Comments
AnonymousAnonymousover 2 years ago

to a point its ok however whats beyond the point?

AnonymousAnonymousover 3 years ago
Good story!

Good story! Wish it went into details at the end!!!

AnonymousAnonymousover 3 years ago
First Story ?

I liked it, went a bit fast towards the end though, if you are going for a series then leave the reader hanging - make sure they read the next part !

AnonymousAnonymousover 3 years ago
Could have been better

This writer fixes comments

AnonymousAnonymousover 3 years ago
A good story but could have been better

The build up was good but the end was to rush you should have gone in to far greater detail on how you fuck her shooting your cum deep up inside her pussy

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