Going Where No Man Has Gone Before Ch. 01

Late May

I suggest you please read and hopefully enjoy my story "I Rub an Asian MILF the Right Way" as a prelude to this story.

That is the story of how I met and bedded Akiko, a Japanese MILF who owned and operated a dry cleaners near my house.

Several weeks after Akiko got her first massage from me and we spent our first night together I took her to Las Vegas for a long weekend.

I had other women in my life and I will share their stories later but Akiko became my utility player, so to speak. When I had a gap in my schedule, I'd text her and ask her if she was available for dinner or if she wanted a massage. Akiko closed her store at 7pm weeknights and she could be at one of the hotels or at my house in less than half an hour. Ten minutes after that we'd be in the bathtub, the hot tub or I would have her nude on my massage table.

As for Lisa (see my story on becoming a Massage Instructor), I had calendared all of our weekends and Tuesday nights, so they were sacrosanct.

Monica, my Maid (read those stories too) had my mornings covered starting with her welcoming blow job and swallow and more sex during the day if I worked from home.

So, here it is late May and I was getting a lot of tight, wet and oh so willing pussy, plus blowjobs and anal sex too.

I ate a lot of pussy too, and was it ever appreciated by the ladies.

I would start with a nice massage and then on the flip, eat dessert and they loved it.

Taking those massage classes was the best thing I ever did.

As for Akiko, she never said no to anything I proposed or did sexually.

Each time we were together I took her in all of her holes.

Akiko understood my desires and fulfilled them, lovingly.

But it wasn't all her give and me take.

I sat down with her on several occasions and reviewed the financials books of her business and discussed marketing and profit strategies with her.

Like most retailers, she did not have an outreach strategy; she had a "if you open the doors, they will come" mindset.

It was sort of the Field of Dreams thing. Well, I've been to Dyersville, Iowa and not that many people show up, especially for the six months of the year the diamond is covered with snow.

From a business perspective, I knew that Akiko could survive, possibly, on that strategy, but she would never thrive with it.

I questioned her being open for so many hours and had her start tracking the revenue per hour to see if it made sense to open later or close earlier.

I asked, "Why open up at 7am if your first customer doesn't show up for two more hours?"

When she pushed back saying "I have a few customers that drop off stuff early on their way to work," I said "We can do a drop box just like the library does. You can text them pictures of their clothes showing them you received them."

I suggested that she consider leasing a clean, used van, slap a logo on it and do local pickup and delivery for corporate offices, reaching out to busy professionals and helping them by providing increased convenience.

She could also pick up and deliver to her customers, at a higher price.

I also suggested just doing the actual dry cleaning four days a week and not five, reducing utility and payroll costs.

Even though it would cost her a couple of points, I also convinced her to go to all credit card/debit card payments to avoid cash theft and to improve accounting efficiency.

We started scouting for a second location.

We also did a quick survey of prices and I recommended she raise prices.

The financial impact of these changes was huge.

What happened is her volume increased and so did her revenue and profits.

So much so that Akiko was able to hire a manager to work in and close the store on most Saturdays and Mondays.

This allowed Akiko to take some weekend trips with me, something she was never able to do before.

She'd been chained to the store for years, no wonder she never said no to any of my requests to meet up with her. I was a bright light for her.

We flew to Las Vegas one Friday night in May and stayed at a brand new hotel.

I picked it because it had an adult, European pool and I wanted to show Akiko off.

I know, shame on me for expanding her boundaries, geographical and sexual.

We were consulting adults and she had the power to say no or stop at anytime.

She never did, I think she enjoyed knowing that I would never hurt her or make her feel embarrassed or frightened.

Now, even though she used the word Master when she addressed me, she only did that when we were alone.

Other times she would call me Jack, or use a term of endearment like lover, sweetheart, sugar or honey.

When we had business discussions, she was the owner and I was her advisor; she often told me my ideas were full of shit (her exact language) or fucking stupid (also her exact language).

I never feared pushing her because I knew she could push back with the best of them.

So, what I would do is break the tension and we would make small bets on the outcome of my business ideas versus her status quo thinking.

This made it a game and we both loved to play it. I won a majority of our small bets.

Before we left for the airport to fly to Las Vegas I told Akiko "You will be nude or close to it the entire weekend. I won't let you get sunburned."

I did not provide details because she trusted me.

She kissed me and said, "If that will please you Master, I am happy to do it."

I told her "You have a great body and I want to show you off."

Akiko beamed at the compliment and kissed me again, deeply.

I was working to build her self confidence, as a business owner and as a woman.

While we were flying, Akiko turned to me and said, "Master, you seem more tired these days. Perhaps you should consider hiring a driver, a town car or a limo to take you to your client locations. That way you will not be so tired from driving and you will be able to use the car pool lane."

And, she whispered into my ear, "That means you will have more time and energy for me."

I thought what a great idea and told her so.

She smiled and said to me, "I care deeply for you and only want the very best for my Master."

We checked in to the hotel and got to our suite at 8pm and I ordered room service for the two of us.

She undressed herself and then undressed me, French kissing my soft cock before we climbed into the bathtub. We were still there when room service arrived.

I sent Akiko to the door nude except for earrings. She had pulled her hair up displaying her tender neck. She looked gorgeous.

The server did a great job setting the table and Akiko gave her a nice tip for her excellent service.

Before leaving the server popped the cork of a nice bottle of champagne.

A second bottle was chilling. Akiko ordered a third.

Akiko had always looked good but she had lost some weight around her middle likely because of the reduced stress of having better business results and having sex regularly. Her breasts had stayed the same size, large and inviting to the eye. And wonderful to touch, kiss, lick and suck.

She pretty much had an all over tan but I had encouraged her to cover her nipples and breasts with the white zinc cream lifeguards use while visiting my pool in order to create the illusion of faint tan lines which would draw more attention to her.

Her butt was still in the great ass category as far as I was concerned and I complimented her every time I saw it. I liked rubbing it and once in a while I spanked it, in fun of course.

Women strive for a great ass and when you see one, say something. Don't let the moment pass.

We ate lightly and quickly because I had several folks lined up to visit us that evening.

The first person to knock on the door was Susan, who had brought sample extreme bathing suits to show us. (Please read my story Hot and Sexy Business Opportunities for the background).

I had Susan in a room down the hall from us, on our floor. She was on a monthly retainer and was heading up the swimsuit project.

I wasn't too concerned about the bikini tops, because Akiko was going to be topless out by the pool, but I paid very close attention to the thongs.

We'd be there for two full days so I selected six of the tiniest ones, making sure they were comfortable on Akiko.

My plan was that Akiko would change thongs every two or three hours on Saturday and Sunday.

Akiko tried on the ones I selected and they all fit her well.

Susan, eager to get her hands on yet another of my ladies, worked to get the tiny suits on and off of Akiko between showings in the second bedroom of the suite.

There was champagne flowing and lots of laughter in the back bedroom, along with giggles.

Even though Susan had vowed to keep her champagne consumption to two flutes, I knew she drank more than that. Her commute home was about 25 steps, so I cut her some slack. It was good to see her having fun.

I asked Susan to "Please join us tomorrow morning at 8am for breakfast, and are you interested in spending the day with us by the pool? It's a top optional pool."

I also asked, "Do you have any additional suits for Akiko to try on?"

Susan was no stranger to nudity and jumped at the chance to be part of the weekend fun.

I was looking forward to seeing Susan topless. I'd seen the two pictures she sent to me teasing me but not the real thing.

I was hoping she could be with us on Sunday afternoon when the pool went nude. Susan had strawberry red hair and I couldn't wait to see what her bush looked like. That is, if she had one.

She was one fine looking lady. A swimsuit model. Gorgeous. I would fuck her in a heartbeat but I believed that she liked the ladies, if you know what I mean.

Right after Susan left, I asked Akiko, "What do you think of Susan?" They had not met previously.

Akiko's eyes got big and she smiled and shared with me that "Susan's hands were just like yours Master, all over my body. I like to be touched, you know that Master" as she kissed me.

I asked "Are you okay with that?"

She laughed and said, "Master, it was pleasing to the touch but not quite as nice as how you touch me. But if you weren't available I would certainly enjoy Susan's touch Master."

Food for thought, interesting things happen in Vegas.

As we were kissing, another woman knocked on the door.

Her name was Marie, and she was a seamstress who lived in Las Vegas. I say seamstress but she had a small clothing manufacturing company. But she needed more business (who doesn't) and I was thinking that I could either buy her out and let her run the place or buy the place and let her have a job there, and not run the place.

I had found her on the web, and I had met with her several times on my previous trips to Las Vegas when Lisa, Michelle, Diana, Kathy, Sonia, Susan, Monica, Kim and Dana were with me. (Those stories later).

I selected from the web site several sexy dress patterns for Akiko to wear when we were out to dinner.

Marie came by to measure Akiko and then would return sometime the next day around noon for a second fitting.

Marie was a short, older gal, I would say about 38.

She had a nice smile and was happy to see me not just because I was sending her business.

Marie liked me. More than she was displaying tonight.

A couple of times, when we met and none of the girls were around, she kissed me hello on the mouth. Her tongue found mine, briefly. She had plans to do more than business with me, and I was fine with that.

But since Akiko was present, and nude, we just shook hands.

Marie had a nice figure well hidden by her clothes.

My radar detected a nice rack, slight sag, big nipples, a slender ass and nice legs. A woman who has slender ankles usually has a nice figure and I was hopefully going to prove my theory with Marie.

I was hoping I would see her in fewer clothes at some point but so far it was all professional between us. Well, except for the kisses. And the hello and goodbye hugs when I could feel her nipples rubbing my chest.

She had lived in LA for years and was a graduate of FIDM, the fashion institute.

I asked Marie about wearing underwear under these new custom dresses and she opted to wait and see what they looked like on Akiko before making a recommendation.

Just then there was a knock at the door and room service arrived with the third bottle of bubbly.

I opened the door; a very attractive young woman came in. Akiko smiled at her and she said hello back. I signed the tab and she left us with a smile, looking back at the nude Akiko who was waving goodbye to her.

Marie was also no stranger to nudity and had her hands all over Akiko as much as Susan had. Akiko was getting worked up; I could see it in her puffy nipples. And her faced was getting flushed being exposed to yet another clothed woman.

I asked Marie if she would be finished with the dresses by lunchtime tomorrow and if so she could bring them to the pool, because I had booked a large air conditioned cabana. Akiko could try on the dresses there.

And, Marie was welcome to join our little party if she wanted.

Marie smiled and said "I'll think about it and let you know."

She also said "I will have samples of the first prototype of CYN Suits on Sunday morning; do you want to me to deliver them here?"

I looked at her and said, "Why don't we meet for breakfast downstairs? Would that work for you?"

She looked at me and smiled and said, "That will work Jack, is 8am good for you?"

I said "Yes it does and we can confirm tomorrow, okay?"

She nodded as she finished her flute of champagne and I refilled her glass.

I had previously sent her the measurements for Akiko, Susan and the other ladies in my life. Marie had also created a suit with elastic that would fit several sizes.

(CYN Suits was the name of my new Las Vegas clothing company, specializing in risqué pool wear. CYN is pronounced sin, as in Sin City, a nickname for Las Vegas, just like it is known as "Lost Wages." But in my mind, CYN was an acronym for Cover Your Nipples or Cover Your Nudity. We would barley covering anything. Each garment would have a diamond shaped tiny tag with CYN sewed into it).

I asked "Marie, you must have been intrigued by the new suit I sent to you to copy. Did you make one for yourself?"

She nodded as she sipped a flute of champagne, her beautiful green eyes smiling at me.

Akiko had slipped away for a minute and I leaned towards Marie and said whispered to her "I'd love to see you in it."

She laughed softly, a bedroom laugh, and replied back to me "Maybe you will Jack. Maybe you will."

I said, with a hopeful lit in my voice, "Soon?" and she replied, "I hope so Jack. But I don't want an audience. I'll wear it just for you and you alone."

I told her in a quiet voice, "I'll be back here at the hotel Wednesday by noon, and would that work for you? I'll want to discuss business with you after I see you in the swimsuit. I'll be traveling by myself."

Marie smiled and said "That will work; I take Wednesday's and Thursday's off."

I had previously had Marie sign an NDA and I also warned her that these women didn't need to know about one another so she was to give the suits to me in person or send the suits to my house and I would give them out. That was why I wanted to meet her alone for breakfast.

I thanked her for coming and gave her a payment for the dresses, in cash.

Actually, I overpaid her, on purpose.

I very much appreciated Marie coming out on a Friday night for a client visit.

We shook hands and she left, saying "I'll see you around noon by the pool."

The last visitor on Friday night was a stylist.

I had asked Marie for a recommendation for someone to do Akiko's hair on Saturday morning before we went out to the pool and she put me in touch with Carmen.

Carmen, fortunately, was a traveling stylist and visited hotels regularly so dropping by the hotel was not an issue.

I was impressed that Carmen wasn't fazed by Akiko's nudity.

Akiko hit it off with her and we set an appointment for 10am in our suite.

I also overpaid Carmen in cash, thanking her for coming to see us.

I also invited her to join us by the pool, if not Saturday, perhaps Sunday.

When our last visitor hit the door, Akiko told me it was time for dessert.

Akiko undressed me, I had only been wearing a tee shirt and shorts, and she provided my cock with a French kiss and a lot more.

Since our first time together, Akiko had greatly improved her blow job skills.

I'm not saying I have a big dick, I think I would say I have an average one for a guy my size (6'1") but she could get it all down her throat once she got warmed up.

Without me having to do or say anything, Akiko had studied the art and science of giving head by reading watching videos and practicing on me.

Akiko liked to please me and she tried many things on my dick with her mouth, tongue, lips and throat.

I had mentioned to Akiko the first time we were together that if I wanted a hand job I could do it myself, and Akiko nodded in understanding so she learned to use other body parts for my enjoyment.

Once she got me rock hard, Akiko put a towel on a dining room table chair and had me sit down on it.

For dessert, she smeared warm fudge on her breasts and nipples, and straddling me, slid her hot wet pussy down on my hard cock and asked me to lick the fudge off of her.

While I was licking she was slowly riding up and down, shallow strokes, massaging my hardness.

When I was done licking and sucking, she kissed me and climbed off of me.

Then, she scooped up some fudge and spooned it on my erection and balls for her dessert.

I don't remember the seven stages of an erection but I was damn close to having a diamond cutter.

I came groaning into her warm mouth. My load was large but Akiko swallowed it all.

We finished the champagne, and took a quick shower together, getting the remaining fudge off of each other.

Smiling, Akiko dried me off and put me to bed.

She joined me after turning out the lights.

It was a long day, a long week for both of us, so I spooned her.

I got hard immediately and we began kissing. One thing leads to another and we basically fucked and napped all night long.

Akiko was worked up being touched by the ladies and I think she was extremely excited at the prospect of being seen nearly naked by strangers.

What I didn't tell her was that clothing was optional on Sundays after 3pm and she'd be nude for three or four hours that day. I don't think the other ladies knew that either.

I was excited at the vision of having four nearly naked women around me all day in a semi public place. And seeing a lot of semi nude women too.

For about two seconds I was concerned about my cum dripping into Akiko's thongs the next day and then came to a solution.

We were both excited at what the next day would bring.

So we made love that Friday night. I slipped into her, she was very wet but still oh so tight and I brought her to an orgasm, then I came deep in her pussy; she licked me back to strength and rode me to another orgasm, sucked me big again; I came deep in her taking her from behind. We fell asleep.

I woke to her sucking me and teasing my balls. Akiko whispered to me, Master, I need to come again.

I took her by the hand and we went into the living room, where the lights of Las Vegas lay blinking in front of us.

I entered her from behind, pounding her pussy until she collapsed in bliss.

I hadn't come yet so I said "It's your choice where you get my load, your mouth or your ass".

She smiled at me and without a word she took me by the hand, we went back into the bedroom and she laid face down on the bed, her ass in the air, and spread her cheeks using both hands.

I quickly probed her ass with first one, then a second finger, using some lube.