A Divorced Asian Earns Her Spanking

This is an adult sex story.

All the characters are of the age of consent or far over it!

Any children named or mentioned are not involved in anything sexual.

This is story number sixty six (66).

Please read my previous story for context.

For a complete list of my stories in numeric order, see my biography page.

Enjoy and thanks for the views and votes.

*******

Caroline Shen.

A very hot, very passionate lover.

She was also a needy lover.

And as it turns out, a very selfish one too.

I was going to work on that.

I was going to change that.

I was going to teach her to how to win a man over.

We fucked all night long ... after first gnawing on those tender nipples I pulled her scoop neck black dress over her head and reached for her tiny thong panties only to discover they were sopping wet.

I wasn't surprised at all --- when we were making out in the back of the limo headed to the hotel I could smell her feminine scent.

I knew she was hot and bothered and wet, and I was the cause of it.

But every time I moved my hand moved up her thigh to the Promised Land, Caroline stopped me with a laugh and whispered to me "Good things happen to boys that wait" which was a line right out of the movie "Terms of Endearment."

Anyway, once we got into the hotel I unzipped her little black dress while we were kissing and pulled helped her step out of it.

That left her with a shelf bra, her cocoa colored nipples erect and fully exposed and a tiny thong pair of panties that barely covered her snatch.

Silently, Caroline twirled around so I could see the whole package and I bit my lip as I took in that ass of hers.

The string of the thong was hidden between her muscled cheeks

Dropping to my knees, I slowly pulled those wet panties down her slender thighs only to find myself face to face with a bald Asian pussy in need of some oral attention.

I didn't delay.

Lifting her up, like I was some kind of caveman, I set her onto the bed and got undressed while she got comfortable and watched.

I was hard and she gasped at the sight of my throbbing manhood.

She giggled, putting her hand over her mouth in surprise and whispered "Jack, that thing is huge."

But her eyes belied any fear she had because she'd paid for this moment.

Climbing on the bed, my hard cock and tight ball sack swaying, I gently pushed her thighs apart, then I slowly started kissing her feet and sucking on her toes, one by one, which got Caroline laughing and hotter than ever.

Several times she reacted by kicking at me because my tonguing of her toes was so ticklish and pleasurable it was painful, but I grabbed her ankles and held them apart so I could monitor how her now steamy pussy was handling all this foreplay.

I was pleased to see that she was not only aroused with her lower lips engorged and she was slowly starting to rub and pull on her nipples as prelude to sex.

I imagined that she had played a lot with herself through the years and that masturbating with her fingers was her preferred way of getting off.

That was about to change.

I took my sweet time, and why not, I had all week, and as I slowly kissed my way down her calves and thighs to my prize, her hairless cunt, Caroline started playing with her tits and would have been playing with her pussy if I hadn't stopped her with a shake of my head.

"That's my pussy now sweetie and I'll be the one touching you there from now on."

At that she groaned, her hormones raging after so much foreplay and who knows how many months without suitable male attention.

But she kept her hands on her tits and actually spread her legs further apart in anticipation of my lips and tongue.

*******

Caroline had teased me at the restaurant about how good she was going to taste that night and in that she exceeded my expectations.

I ate her to multiple orgasms, perhaps the only time she'd been recently orally satisfied by a man.

Her pussy was small and tight; hairless and wet when I got up close to it.

Caroline could not spread her legs wide enough apart --- that was how hot she was for my tongue on her.

I didn't disappoint her.

Her fragrance was pungent, but that did not deter me; I was going to have her whatever the obstacles might be.

She was right, she tasted great.

Not sweet, not sour, but mellow, like an aged scotch or perhaps like a champagne with tiny bubbles.

I was looking forward to giving her a severe tongue lashing since that first day we met.

I loved how she responded to my efforts to pleasure her.

Moans, groans, whimpers, whispering, words of encouragement; nothing dirty but she certainly was appreciative.

I was appreciative of her being bald, waxed, clean, smooth and willing.

Given her healthy, thick dark hair, I could only wonder what kind of fur I would have had to lick through to get to her pussy if she hadn't been bare.

On the other hand, I wondered what she would like on a nude beach or out by the pool with a full bush, that body and those tan lines.

With those thoughts running around my brain, and a shit eating grin on my face, I got down to the one thing I knew Caroline would appreciate: me eating her pussy.

After spending some time kissing and licking that extra sensitive fold between her womanhood and her thighs, she began to beg me to lick her, so much so that she brought both hands down off of her tits to hold my head down while she humped her way to heaven.

I had other ideas and a different timeline for allowing her to orgasm and forcefully took her hands and held them down with my own to let her know that for the next week, her orifices belonged to me. I'd let her know when she could cum.

Slowly, filled with purpose, I flattened my tongue, making the muscle hard, and proceeded to rim her tight little rosebud.

She gasped at the touch of the hard tip in her most intimate place.

I rimmed her well, because I wanted her to understand that her entire body was going to be my playground.

She kept gasping and began to lift her ass up to allow me better access, a clear signal to me she was enjoying my teasing.

Then, without warning, I pulled my tongue back out of her ass and licked in a single movement from her dainty rosebud up her slit to her little hard love bump.

Caroline groaned so loudly I thought they could hear her in downtown Phoenix.

I know she wanted me to continue but I stopped and looked up at her face and said "I licked it --- so it's mine now."

Her eyes were squeezed tight, her body had broken out in a sheen of light sweat and I knew that if she didn't come soon she would likely burst into tears ... that's how worked up she was.

But Caroline didn't answer, she just groaned at the loss of contact of my tongue on her pussy and she humped her hips a few times in an attempt to regain contact and friction.

Squeezing her hands that I was holding down, I repeated myself "I licked your pussy so now it's mine Caroline."

She finally got back to me with "Yes, Jack, my pussy is yours ... my pussy is just for you ... now please let me cum ... Pleassssse Jack let me cum baby ..."

I had barely started in again on my second lick from top to bottom when she started to shake and when I got to her proud hard clit, my tongue swirled and she screamed.

Caroline gushed, not exactly a tidal wave but enough so that my chin got soaked and so did the sheets beneath her humping, thrusting ass.

I let her hands go and they went straight to my head, directing me to keep on with my oral efforts.

She loved being eaten out.

I stuck my tongue out as far as I could and made into a hard flat surface to maximize her pleasure.

My right hand now free, I kept my tongue focused on her slit and her clit, rubbing it over and over with my human sandpaper, while my index finger on my right hand found its way into her slit in hot pursuit of her g spot.

My left hand snaked under her ass and quickly discovered her tight little rosebud that had been the starting point of her oral pleasures extravaganza.

I wasn't shy about probing her ass with my long middle finger and she initially protested and resisted the digital intrusion with a soft "no, no" but the pleasure she was having with my tongue and lips on her clit and my finger now playing the piano on the soft pad of her g spot, she relaxed somewhat, dropped her ass and opened up to my invasion.

My timetable was open as far as sticking my cock in her ass but I wanted her to know it was one of my objectives.

As in, I didn't want her to forget what I had added to her list.

Once my finger was in, well past the knuckle, I started to see saw my finger into her tight anal opening, getting her used to the feeling.

Her soft cries of "no, no" turned into "Yes ... Yes ... Yes" as I had two of her three holes busy on the highway to heaven.

My God her pussy was tight! So was her ass!

I tried to get a second finger inside of her cunt ... it took a long time to get wet enough for her up to accept it easily.

I realized that fucking her pussy was going to take some time ... I knew Caroline needed to be relaxed and there was no other way to do that then to have her cum, more than a few times and maybe, if things worked out, give her a massage in all the right places.

Then I could have her. My cock throbbed at the thought.

*******

I just focused initially on pleasing her with my mouth.

She was highly orgasmic orally and I used my fingers a time or two as well, just to vary things a bit.

Finally, after who knows how many orgasms, she pushed my head away, not forcefully, and said "Enough Jack, enough for now ..."

She rolled over in a fetal position and I snuggled up behind her, my hard cock finding its way into her butt crack. My hands snaked around her to hold her and I was careful not to touch her nipples because I knew that they would be very sensitive for at least a few minutes.

For a long time she didn't say anything and when her breathing got steady I assumed she had fallen asleep.

She surprised me when she said "Jack, I had no idea how much I missed having my pussy licked until tonight."

I kissed the side of her face and said "It was my pleasure."

Then she said, "I also had no idea how big your cock is. It's going to be a very tight fit."

Laughing in her bedroom voice, she said "They undersold you. The dildo I got from Tina was nowhere near your size."

I didn't know anything about a dildo so I just replied with "Let on your tummy and let me give you a massage."

Caroline complied, eager for my hands to be on her once again.

And she loved it when I sat just below her ass on her legs so that she could feel my cock in her crack.

She'd laugh nervously as my erection separated her cheeks when I lifted up to reach her shoulder blades but I swear I never had the tip of my penis near her rosebud.

I took care to wipe the lotion off my hands before rubbing her head and added extra lotion when I got to her butt.

I purposely avoided dwelling on her rosebud when I massaged her.

My fingers ran over it a time or two but I apologized when it happened and Caroline responded each time with a giggle.

By the time I got to her feet I thought she was asleep but instead she asked "So, how are we going to do this?"

I laughed and replied "One inch at a time" and she laughed as she rolled over on her back telling me "I need that monster inside of me Mister Colton. Now please."

*******

We fucked, oh how we fucked.

It took some doing, some time, some patience, some lube, despite Caroline's natural juices, but I finally got inside of her balls deep.

Given how much work it took to get all the way in, I was reluctant to pull out so I was careful when we changed positions.

I also found out she was a screamer, which was okay, I was just thankful that our suite was in an out of the way wing of the hotel and since our phone didn't ring with resort guests complaining, I just continued to pound her.

It was hard for me not to cum because she was so fucking hot, wet and tight but I managed to bring her off several times before finally depositing my third load as I took her on the bed from behind, pulling myself into her deepest recess in an attempt to get her pregnant at this first breeding session.

I stayed inside of her, our bodies heaving, until I had fully dripped all I had inside of her and then we both fell asleep, totally spent.

*******

Friday morning

I always wake up at 5:30am, no matter where I am or what time zone I am in.

As I opened my eyes, I wondered for a nano-second where the fuck I was ... and then it came back to me.

I turned my head to the left and saw a mass of shoulder length black hair on a pillow, and the full bare backside of a nude woman.

During the night she'd kicked the sheets off and was gently snoring; apparently she slept in the nude and without covers.

This woman had a great ass.

My cock, already hard from the need to pee, went to a new level of morning wood at the sight of it.

Who was this chick?

My brain was foggy ... then I remembered ... Caroline.

Scottsdale.

Her list.

Her amended list.

I smiled as I took it in, remembering how I slapped that ass while I was taking her from behind.

Caroline loved it when I took control, my hands holding her firm hips as I plowed that hot pussy and she liked the slaps too.

I took another look at her ass and I impulsively reached for it, slowly so as not to waken her, and using both hands I very gently pulled her taut cheeks apart.

No reaction. She didn't move a muscle, that's how out of it she was.

Deep in the recesses of my mind, as I slept, it somehow came to me that there was something interesting about her rosebud ...

Despite the fact that I had been nose to rosebud last night for a very long time, licking her to orgasm after orgasm, for the very first time this morning, in the dim morning light I noticed as I separated those cheeks that she'd had her asshole bleached.

You know, the darkened skin brushed with bleach and made to look brand new (!).

I smiled and thought about how reluctant Caroline was (or so it seemed at our dinner) for me to negotiate her giving up her virgin ass to fuck.

Now I realized she had it all planned out from the start.

She had her little surgery for me!

What a minx.

This lady was a schemer, a master negotiator; she wanted me to fuck her ass, she just didn't want to put it on her list.

She didn't just want me to impregnate her; she wanted the entire "boyfriend" experience for her money.

With these lewd thoughts running through my brain, I was tempted for a second to slip up beside her with my still solid erection and take advantage of the situation but I knew she needed her sleep.

After all, we'd been up all night fucking.

I had dropped three loads into her pussy and it was sure fun doing it.

I was not going to get any more pussy at the moment, so, I quietly did my thing in the bathroom, and quickly dressed and headed out of the suite to the workout room.

I (we) were in the Presidential Suite at The Phoenician, an exclusive and swank golf and tennis resort just north of Camelback Road in Scottsdale, Arizona.

My buddies Tom, Paul and Dan were all flying in by lunchtime and a weekend of golf and baseball.

Caroline had made some other plans for us.

I had plans on my own, from the list I made up as I worked out.

Starting with getting a blowjob.

Her not even getting her mouth close to my cock last night was worthy of a nice spanking which I was going to love to deliver.

And for a woman who was so interested in eating pussy for me, it was kind of strange that last night she didn't want me to kiss her after I'd eaten her out.

Another reason to spank her.

And, to push her boundaries she was going to be a model in a photo shoot.

She wouldn't be the only model though.

Plus a few other things she hadn't put on her list but I would.

*******

After my workout I picked up two cups of coffee and the newspapers and headed back upstairs.

I was trying to be a nice guy bringing my lady of the moment some coffee.

Quietly entering the suite I checked on my hot Asian divorcee and found her still sleeping. It looked like she hadn't moved.

She was still snoring away. (So, she wasn't perfect after all).

Using my trusty iPad I started looking online for what I needed and found to my surprise an adult toy store located just a few miles away.

On a whim I called before they said they would be open and I reached the owner.

I placed my order with him, and told him I would be sending someone over to pick everything up.

He chuckled when I said I was paying him in cash, then he added "Just the kind of business I like to do."

I hung up the phone and asked that the valet come up to my room.

Getting back on the web I found another local shop.

I made my second call to a small women's bathing suit store also not too far away.

Using the measurements of Caroline's bra, panties and dress sizes, I ordered some sexy bathing suits off the rack.

I told the owner "I want the smallest pieces of cloth you have for the bottoms, and even smaller ones for the tops."

She came back at me with "The tops aren't elastic so if they don't fit ..." and I finished her statement with "Then she'll just have to go without won't she?"

She laughed and said "You are a very naughty boy" to which I replied "I sure am."

I told her someone would be over shortly to pick up the clothing; thanked her and disconnected.

There was a light tap on the door and I opened it to find a very nice young lady of about twenty five in a white polo shirt and tan shorts.

From what I could see she filled them both out very nicely and her skin was already bronze from the sun.

She greeted me with a smile and I handed her an envelope with $300 in cash.

On the envelope I had written the address of the adult store and my name; gave her $100 tip and told her to hold the package for me at the valet stand.

And I said "It's all hush-hush" and she nodded and said softly "I get it."

Then, while she waited I slipped more cash into a second envelope and wrote the name and address of the bathing suit store on it.

The valet nodded her head, smiling and said "Okay, two stops and leave it at valet for you."

I watched her walk down the hall to the elevator ... she had a nice ass and she knew I was looking.

My third call was to the General Manager of the hotel; I inquired if, for a fee, one of the smaller pools at the resort could accommodate topless bathing.

He hemmed and hawed, stating it wasn't their usual policy so I dangled a trip to Las Vegas or San Francisco on my personal jet and we cut a deal.

The pool I had my eye on was right below my suite and new signs ("Adults Only") were quietly put up within the hour.

I didn't have to make a fourth call; I emailed the women's tennis coach at Arizona State University for a favor.

Her name was Nikki. I knew her because she had called on me one day right after I took over the Scottsdale car dealership looking for a sponsor for the tennis team. I didn't have clean financials at that moment so I allowed her to use one of our loaners as part of the sponsorship package and then after 90 days I started sending money each month.

In return I asked for an email update from her each month and that she send along a status report on the progress of her players and prospects.

I also said that I knew nothing about the NCAA recruiting policies but if she needed help within the guidelines with that I could probably help there too. Meaning, buy dinners, use of a car for a visit, pay for hotel rooms, and so forth; all she had to do was let me know.