Practice Date with Kim Ch. 02

Copyright ScottArroy December 14, 2021

https://www.literotica.com/s/practice-date-with-kim-2

This is a follow up to the first story I posted on Literotica. I was getting requests for a sequel so I hope this story will please my readers.

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My sister asked me to help out her best friend Kim. I have known Kim since she went to kindergarten. She is intelligent, kind and sexy. The only reason I had not pursued her was that she was my sister's best friend.

After twelve heartbreaks in eighteen months she lost all confidence and stopped going out retreating into her shell.

Kim was desperate to find out what she was doing wrong. Her CEO placed great esteem on relationships and Kim not being able to maintain one was seeing her being passed over for jobs at work.

Becky, my sister, promised Kim that a practice date with me would lead to a solution. I wasn't sure 'my treat them mean to keep them keen' approach would help but Becky made it clear I had no choice.

So yesterday I took Kim on a date. A practice date! After some prompting Kim wore a body hugging top that proudly displayed her J cups above her tight abs. Her jeans with laced sides showing quite a degree of hip and leg flesh, albeit unattainable. Perfect for a first date, hinting sexy but with clear boundaries.

The most outstanding thing I detected on that occasion was she undervalued herself. The second was she liked a drink knocking back ciders all night. The third and most interesting was that for a woman of strong integrity she certainly had submissive tendencies.

Kim was attentive and always made eye contact with me. At dinner I found myself enjoying Kim's company holding her hand without realizing it.

Kim was obviously enjoying my company sharing our dessert spoons. Willingly making out with me in public.

We lost track of time dancing into the early hours of today. When the so-called practice date should have ended Kim thanked me "for a wonderful night so far".

"So far?" I asked

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

"Are you sure Kim?" Becky's voice in my head saying 'don't you dare take advantage of my friend'.

Kim stood there with her chest pushed out. Her 34, 22, 28 never looked better.

"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!"

"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 up, 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 vigor. 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."

I was greeted by a huge smile, breasts standing proud with pointed square crimson nipples. Kim had her legs splayed out with a bushy black arrow pointing to her glistening also crimson labia.

"Oh my!" I didn't mean to utter anything but Kim was breathtaking.

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

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.

Kim may have been submissive on the date but she was an aggressive love maker. This was probably why the duds she had been dating didn't stay with her. Kim was too much for their fragile egos I suspected.

Kim was doing all the right things for me. I was hard as a rock or those rare nipples she was sporting. Her caressing was turning me on. I so wanted to plow this woman and retake control. I knew that to help Kim and more importantly keep Kim I needed to show her who the boss was.

I let her roll me onto my back. She smiled sensing victory as she climbed to a cowgirl position. As she lifted her arse with the intent of impaling herself I whacked that arse as hard as I could. She fell back down onto me short of her target.

Kim looked at me measuring my intent. Again she lifted her arse, her eyes affixed on my right hand. Whack! I landed another strike this time with my left hand. She lifted herself marginally from the pain and I lashed another stinging blow onto to left cheek. Immediately landing another on the right and then the left again.

I snatched her nipples and pulled her down onto my chest. Continuing to squeeze them when I could no longer stretch them.

I pashed her again with my soldier pushing into her belly button. I released her left nipple and commenced swatting then rubbing her left arse cheek repeating this until Kim groaned and released her private juices onto my thigh.

I rolled her over and inserted two fingers into her welcoming wet snatch. using my thumb to manipulate her clit. I worked an irregular pattern and soon she was panting into my mouth trying to enunciate "Dont stop!" and "Please dont stop!"

Her orgasm was fading when I curled my fingers and put the pressure of her own body weight on her g spot. Her eyes rolled back and her orgasm exploded at a new height as she uncontrollably spurted and spasmed.

No gentleman on this occasion I kept lifting her not relenting until after she passed out. I found my briefs and put them back on. Snuggling up to my sisters best friend.

I was shaken awake by Kim. "Alright Paul I need you to be a man of your word. You said in the morning, and that's now! If I want to do more we can."

"Did I say that? It must have been the alcohol talking. You know Becky would be devastated if I took advantage of your innocence."

"You didn't drink any alcohol, mister! Does having your fingers inside me not count as taking advantage?"

I didn't respond so she continued her voice faltering slightly.

"What am I doing wrong Paul? Why don't guys want to have sex with me or stay with me for more than a month if they do?"

"I feel, to answer that, we may need a few more practice dates, Kim."

It was eight am and a text message beep sounded on Kim's phone.

'Let's go out for breakfast at Beachside Cafe. I'll pick you up in fifteen.'

"Becky will be here in fifteen minutes. I can't believe I'm saying this but you need to go."

"Ok!"

"So you're going to take me on a second practice date?"

"Kim, I feel I know what the problem is but I'd like to have at least three more practice dates."

"Three?" Kim looked very dejected.

"Please dont tell Becky I slept here last night."

"I'm hardly likely to tell your sister you didn't find me attractive enough to root."

"If you told her that, it would be a lie and we don't want you lying to your best friend. Do we?"

"You have to go!" We embraced and my morning wood turned from balsa to oak.

Kim didn't seem put off by morning breath as she played tonsil hockey in my mouth. I dashed out and drove off with only half my clothes in place.

Several hours later Kim called.

"Becky knows everything."

"She was outside when she sent that text message. She watched with great amusement as you left."

"Oh shit! Really?"

"I assured her you were a gentleman and she scoffed when I told her we didn't have sex."

"We sort of did though."

"Eventually she coaxed the full story out of me. I think she was proud that her brother didn't take advantage of me."

"I'll never hear the end of this."

"So when are we going on our next practice date?"

"Do you think we should, now that Becky knows?"

"It took some convincing for her to believe we didn't do the deed."

"I'm not sure I want my sister reading my report card on my sexual prowess."

"Did you ever play doctors and nurses with her?"

"You should know you were there! The three of us were always playing naked together when we were kids. It only stopped when your chest started to reshape."

"I think your sister is burning a candle for you."

"Don't be silly."

"She doesn't date any boys."

"Are you sure it's not you she is burning a candle for?"

"We have made out a few times over the years but its never been overtly sexual. More sister cuddling but I guess we have rubbed each other above our clothes but never to the point of an orgasm."

"What makes you think she has a thing for me?"

"She appeared to be vicariously invested in the retelling of what occurred and how I felt."

"How did you feel?"

"You're turning red so I gather you enjoyed it?"

"Yes!"

"All of it?"

"Yes."

"The denial?"

"Yes."

"The pain?"

"Yes."

"The orgasms?"

"Definitely yes."

"What are you doing tonight?"

"Hopefully going out with you."

"Alright I'll pick you up at seven again. I'll be keen to see what you choose to wear for a second practice date."

"Where will we be going?"

"How about the Comedy Club?"

"Oh that should be fun."

Kim wore a long sleeved bodycon black mini dress. The entire back was covered allowing a deep plunge through her cleavage exposing a third of her entire boobs. The lower part was stringed on the front quarter from the bottom of the dress to the waist on both legs. Curving inward following the natural curve of the body as the hip to waist measure reduced.

I slid my hands down her back as I pulled her in for a greeting kiss. Just above the waist I could feel a band that was aiding in supporting her J cups. The bra was otherwise undetectable. Kim either had a seamless g string or nothing. Four inch stilettos and her black hair up in a sloppy bun adding height. Her blue eye shadow and a gloss lipstick completed the alluring picture.

"Wow Kim you look sensational. No complaints about your second date attire. As it's a practise date. Plunge bra and g string?"

"I was hoping you may have thought I was going commando. Obviously not as seamless as I had hoped."

"No, the g string was a guess based on your personality."

"What, you think I wouldn't go knickerless for you?"

"On the third date perhaps. We both know I'm waking up in your bed tomorrow."

"Do we now?"

"Are you saying you don't want me to?"

"No, I thought it possible I'd be waking up in yours."

"Shall we go and enjoy some comedy?" We walked out to the curb. Kim standing at the door of the car waiting for me to open it. I smiled and accommodated her desire. I wasn't disappointed when we arrived as she sat in the car waiting for me to open the door.

I ordered three ciders and a Pepsi Max. That should get us to the intermission break.

The first comedian started off saying, "it was my birthday last week. It was a shit day! My wife didn't wish me a happy birthday. My parents forgot and so did my kids. I went to work and none of my colleagues wished me a happy birthday. Except for my secretary who said, Happy birthday, boss! I felt so special even asking me to lunch. After work, she invited me to her apartment. Upon entering she said, 'Do you mind if I go into the bedroom for a minute?' "Okay," I said. She came out a few minutes later with a birthday cake, my wife, parents, kids, friends and work colleagues all yelling, SURPRISE! I was waiting on the sofa; naked. So my wife filed for divorse."

That had the crowd laughing. He continued on..

I thought my luck had changed earlier tonight after talking with that lovely asian lady there, pointing straight at Kim, in the theatrette. I asked how I could get to know more about her."

I froze.

"She replied Sex! Sex! Sex! Free sex tonight! Until her partner returned with those drinks they're now drinking clarified his friend meant 666-3629."

The crowd thought the story was hilarious. Fortunately so did Kim. Kim was Eurasian but it was hard to detect any asian in her appearance. Just minor details that enhanced her western look making her just that little bit more enticing.

"What about that?" the returning host MC said at the completion of his set. "Put your hands together one more time. There are certain tricks to communicating with your wife you fellas know that." signaling out a rowdy bunch. "I was having an affair with a beautiful lady who was my assistant at the time. Stunning! She looked just like this beautiful lady." Kim again being chosen for the story telling. "What's your name darling?"

Kim replied, "Kim".

Yes, same name, "That's not you is it Kim?" Holding his arm horizontally over his eyes pretending to cut out the glare.

"It is! But carry on telling the story." Kim won the audience support as laughter erupted.

The host continued, "Youre such a good sport and more."

More crowd laughter. "On this particular day we went at it a little too hard, didnt we?" Again looking at Kim.

"Exhausted, we fell asleep waking too late. As I dressed I had Kim go outside, thank you again darling, and rub my shoes through the grass and dirt. Even though she thought that was quite odd. When I got home you can imagine the interrogation. 'Where have you been?' demanded my wife'. Darling, I can't lie to you, I replied. I've been having an affair with my assistant. I fell asleep in her bed and didn't wake up until just now. My wife glanced down at my shoes and said, 'You liar!' You've been playing golf! Let me introduce the next artist..."

The second comedian finished with a question. Why is sex like math?

The MC returned asking, "Has anyone worked it out?" Of course there were a few audience responses, while funny none stole the punchline.

"You add a bed, subtract the clothes, divide the legs, and pray there's no multiplying."

The raucous night continued and two hours later we were buzzing with good cheer, about to depart the theater. Kim taking the opportunity to powder her nose.

"You'll never believe what's going on in there. Women of all ages removing their knickers. Look there's one there clutching hers. The best was that old lady in the plaid skirt, there. She went to exit the individual toilet then seeing the carryon retreated to the cubicle exiting shortly after boasting a hugh smile and her knickers visible in the top of her hand bag."

We headed back to the car. Arms wrapped around each other. Stopping occasionally making out in the darker, less lit locations.

I stopped at a pancake parlor purchasing a triple stack strawberry and ice cream to share.

We fed each other and chatted effortlessly. "Thank you for tonight Paul. My normal second date sees me in bed much earlier."

"We did speak about undervaluing yourself last time."

"Are you suggesting I should make you wait a few dates before I let you take me."

"No but you are within your rights to do so."

"I'm so wet! All this is talk of sex. You! Me! Last night. My knickers in my clutch purse. I really want to make love with you. Is that so wrong?"

"You know we are practise dating?"

"Paul, I have feelings for you. I believe you have feelings for me. None of that means anything right now. We need to find out why I can't maintain a relationship. Please help me."

"We still have two more dates to work things out."

"So we're going to keep at it?"

"Yes."

"Are you going to wake up in my bed?

"Are you asking me to stay over again?"

"You know I am."

I opened the car door and Kim spread her legs as wide as she could lifting them to give me a direct line of sight to her slippery box.

"Just so you know. I never do that on a date. That was just for you."

"You used to do something similar when we were kids."

"Actually I think that was your sister."

"Well maybe you both did."

"I'm quite content being a ho for you."

I ran around the car and proceeded to sit.

"Oh my!" I've really got to stop expressing my voice in such situations.

Kim sat there with her dress hitched up fully exposing her snatch.

"I thought you might like to play as you drive me home."

I placed my hand into her lap tapping her cliterous, rimming her vulva and running my finger through her slit. I sucked my fingers tasting her juices before returning to the source for a second sample.

I held my finger up for her to do the same.

"Oh that is quite naughty." Kim said before sucking my finger clean.

I returned my fingers to the task required. Kim soon panting heavily, her juice flow increasing exponentially.

"I'm going to come, Paul. Keep doing that. Yes, just like that. Don't change anything!"

I didn't not until her orgasm kicked in. Then I pulled the car over sending several fingers down her private tube. A new wave of pleasure overcame her. I lowered my head onto her love box, kissing, licking and sucking it dry.

"Oh Paul, you do things to me that others have never. Thank you. I needed that release."

I drove on fending off Kims attempts to access my stick.

"Paul let me play, I promise not to be overt. I'll just keep you firm and if you're getting too stimulated I promise to back it off. No one wants a car accident."

I pulled over again. Kim fetched me out of my briefs and past the now open zip.

Kim's touch was soft and delicate. It was surprisingly wonderful. I had thought she would have me ready to explode and whilst that would be wonderful it would have been unwelcome.

Kim had me comfortably firm. Her soft caressing more in a style of seduction than sex. I don't think I'd ever been so happy in a woman's hand. No pressure, just light touching. Comforting and pleasant. Kim seemed to adore my extension as if this was the most unique or special thing she'd ever touched or at least that is how she made me feel.

We arrived at her house and I put things back together as best one can with a hard on.

"Can I offer you a drink? Tea, coffee, cider, beer, wine or spirit?"

"Yes please."

"I'm moving up to cocktails. Are you a bond fan?"

"Who isn't?"

"Do you recall the Vesper Martini from Casino Royale?"

"Only that there was one."

"Let's make them together. Can you fetch me a bottle of Gin, vodka and the Kina Lillet from under the bar there. I'll get some ice and two thin slices of lemon peel."

"Ok so put six measures of gin, two of vodka and one of Kina Lillet into the large shaker. Add the ice. Give it a good shake."

"I thought we were making this. I seem to be doing all the work."

"Oh no no no. See I've cut the lemon, secured the ice and for the finishing touch these chilled cocktail glasses." Reaching Into the bar refrigerator.

Kim added the lemon peel to each glass as I poured the icy drink into the glasses.

"May I?" leaning to clutch the bottom of her dress.

"Be my guest." I lifted it leaving her standing in her plunge bra.

May I?" Kim asked, starting to peel my tee over my head.

"Please do."

Kim attacked my Jeans unbuttoning and unzipping them. Pushing me once again into that chair to remove my shoes and attire.

My manhood at the ready.

"Will you undress me please?"

I found the three hooks at the front that gave the bra support. "Um how do I unleash this without hurting you?"

"I see." Once again taking over as I allowed those J cups their freedom. Her square nipples reflecting her level of excitement so firm and large.

We sat there naked drinking our Vesper Martinis.

"Would you like another before we head to the bedroom?"

"Why not!"

We made another round. Carrying the drinks to her bedroom.

I clutched her head peppering kisses to her face.

"Last night I set a stupid challenge asking you to resist me. Tonight I want you to make love with me as one might if we were going to spend the rest of our lives together."