Im Running On Empty Ch 05

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 story follows "I'm Running on Empty Chapter Four."

This is the story of how I spent my time the first week of the month of April and what my penis was doing too.

Enjoy and thanks for the views and votes.

****

Before leaving the private dining room, I thanked Cindy our server; she kissed my cheek and whispered "Don't forget to text me!" as she handed me her business card.

In response I gave her a CYNSUITS business card and told her "Use the promotion code on the back and you'll get five swimsuits custom made for free. You'd look good in a black suit, or no suit at all."

Cindy laughed and smiled and then kissed me a second time on the cheek.

I smiled, happy to make her day, and wondered what she would look like topless around the pool or naked between my sheets.

She was an astute, pretty girl; I wondered if she was shaved or had a bush; did anal and if she had tattoos.

Maybe I'd find out the answers to these questions someday soon.

In the meantime, I was still on my business dinner with Lauren, although we had engaged in far more than just business over the last 90 minutes.

Lauren and I left the private dining room; next stop, her hotel room.

Lauren whispered to me "My God you cum a lot. I'm still dripping!"

I laughed, wondering if my seed had taken root inside of her. Probably not.

Or was I just marking my territory, even though it was just temporary?

All that shit was too deep for me - I just wanted to have sex with her.

Again -- this time horizontally.

I was already looking forward to Round Two.

My dick was sure ready. My dick was always ready.

Thanks to the blue wonder pill.

On the way out of the restaurant, Lauren and I stopped at a round table filled with eight women; all of them quite attractive.

She introduced me to them as her friends.

One of them was the brunette from the pool; we had not met yet but she stood up and shook my hand, introducing herself to me as Jessica. No doubt, all I could see was that she was a "10" and it was clear she liked me.

How did I know? Jessica wouldn't let go of my hand.

And the moment she did, it went to my upper arm.

She had pumped my hand the way I wanted to pump her: with a lot of energy and a smile.

I wondered what Lauren and she had spoken about after I left the pool area. Maybe I'd find out.

There was something sort of mysterious about her. It was intriguing.

Jessica wasn't wearing a ring.

Then they all stood up and one by one as I circled the table, I got a nice handshake and a business card.

It turns out that each of them worked for a different bank, doing real estate financing - hotels was one of their specialties.

They not only worked for different banks; they were geographically dispersed around the country.

Rather than try to remember their names, I asked them if they could just tell me where they lived and the answers came back Seattle, San Francisco, LA, Phoenix, Denver, Dallas, Houston, and St. Louis.

"These ladies are the ones you want to meet Jack" Lauren said to me in front of them. "They can do the deals you need to have done."

They were all in town for some sort of bankers convention.

Lauren told me later that she had picked up the tab for dinner as a way to thank them.

Looking at them, all of them very attractive women in their 30s and maybe early 40s, I could see why Lauren was so successful.

But I didn't know the half of it.

Lauren explained that these ladies worked against one another only on paper. In reality, they referred business to one another and helped each other succeed. As a result, they were all successful.

They made good money and wanted to make more, and Lauren had been able to get them all in (personally) on one hotel deal she did so they had some passive income but they wanted to invest more and they were hoping I would let them be part of my deals.

I asked the lady from Phoenix (Melinda) if she covered Santa Fe and she said she could. I gave her my card and said to her "Please text me your availability the next couple of days to go there and check out a couple of deals I have in mind."

She smiled and said she would let me know before midnight when she could be there.

Then I asked the lady based in Seattle (Lindsay) if she knew of the dealership I had recently bought.

When she said she did I told her I had several more lined up to purchase there, she asked me if she could meet with me before she left town to discuss the real estate part of the deal. I said yes and we set a time for the next day.

I handed out my business cards and promised to return their emails and text messages personally.

As we left the restaurant, and headed to the elevators, Lauren said to me as she took my arm, "Jack, they are all single, widowed or divorced and they will do anything to do a deal with you. Anything."

I nodded and took that into consideration but said nothing.

At first glance, I wouldn't hesitate to fuck any of them, given the opportunity.

She continued with "I get phone calls and emails from female bankers all over the country every week or so who want to be part of this group. I doubt if adding another eight or ten to this group will damage anything I have going on. So, if I go after more women, maybe you could interview them as part of my vetting process. I know that they would all enjoy meeting you and you'll want to do an in-depth in person interview, wouldn't you Jack? Just like the dinner we both enjoyed?"

I smiled in reply, thinking, and Lauren continued, "But before you even think about going to bed with any of them, and I already know you want to, I need a real good fucking from you tonight. A real good fucking."

"I won't disappoint you" I smiled.

"And I won't disappoint you either Jack. My goal is to please you. Tonight and always."

We got into the elevator and hit the button.

We kissed and my hands wandered down to her tight ass.

"You want to get fucked? Is that right little lady?"

She nodded and smiled and we kissed.

Our lips parted and I said to her in reply "You'll get that and a lot more" and as I pulled up her dress and then squeezed her butt cheeks, running my finger down her crack.

I felt her shiver.

Lauren knew exactly what was on my mind: fucking her ass.

"Will you be gentle Jack? It's been a long time since anyone was ... back there."

I nodded and smiled and we kissed again before heading to the room.

****

Lauren got the massage she asked for and I got what I wanted: my hands all over her body and my cock in her three holes.

She had arranged for a massage table to be delivered and set up in her suite in anticipation of me rubbing her nude flawless body from head to toe.

How did she know I would say yes?

Is Brent Kavanaugh on the Supreme Court? Is Maxine Waters nuts? Is Bill Clinton still chasing skirts?

Honestly, I actually gave Lauren a real, non sensual massage.

Well, at least at the beginning, starting with her neck and shoulders, then moving to her shoulder blades, her arms, hands, fingers.

I undressed her and she undressed me.

She looked at my semi and wanted to play.

Actually, she wanted her lips on my cock but I held off for now, kissing her deeply and then I lifted her up and put her, butt up, on the massage table, telling her "You can suck me later."

Lauren laughed and said "I like it, a man who takes charge!"

I rubbed her bare ass and she opened her thighs a bit, purring in response.

I worked my magic on her neck and shoulders.

I started out standing at the head of the table, working on her neck and shoulders.

Then I moved around on the sides of the table, pushing and pulling, the tension out of her back and down to her butt.

Lauren groaned and grimaced as I found and worked on the knots in her neck, shoulders and upper back.

Her neck cracked early on and it sounded like a rifle shot.

She had a lot of tension in her body.

I was fairly liberal with the lotion but there were a few times when I pushed on her semi-dry skin and she yelped.

Despite some pain, she had wandering hands, reaching out to touch me as I massaged her.

Even under normal circumstances I would have been turned on by massaging a nude lady of this caliber and I was; but her fondling; her playing with me, got me even harder.

(She loved playing with my balls. And I liked her touching them).

While I could say she wasn't taking the massage seriously, the truth was she was starved for physical attention; she wanted to touch and be touched.

We didn't talk much. I assumed that because I liked silence during my massages that Lauren did too.

She was pliable and easy to work with.

Using the lotion I worked on her back for quite sometime, as she had some knots that were actually pretty big.

Two, one on each side, were buried deep and that took some doing to rub those out.

But as I moved south, down her back, my long sweeps started to include her bare butt cheeks.

I didn't overtly grab or squeeze or fondle them, but using my hands I started sweeping the tension down her body.

My hands went down her from her shoulders down her back, to her butt.

As I did this, I made sure that there was plenty of lotion on my hands and I started to take some liberties with the crevices of her midsection.

I took my time on her lower back, giving the top half of her great ass a nice massage.

Her butt was amazingly firm and I broke the silence and asked her about it.

"Stairmaster Jack. Three hours a day. Everyday."

With that I smacked it and she laughed and she shook her butt at me saying "I guess that means you like it."

"I sure do" I replied, and then my hands pulled her lower cheeks apart, forcing her thighs to open wide.

Then I climbed on the table and sat on her lower thighs, and as I leaned forward to rub the top half of her ass from the south end, my erection found its way into her crack.

"What's that thing in my ass?" she laughed, knowing full well what it was and who caused it to be large and hard.

I was pretty turned on that late evening.

I wasn't dripping pre-cum just yet but I was headed that way.

"You know full well what it is young lady" I replied, as my hands separated her cheeks for the second time during her massage, allowing the cool air to find its way to her tight rosebud.

I was tempted to lick it just because I could -- but I held off.

I moved down to sitting on her calves, and I took my time on her lower butt, giving her great ass a nice massage.

I had further plans for her ass, but for the moment I got off of her calves then I spread the lotion on her lower legs, her feet and toes.

Her feet were sensitive and ticklish.

She started to laugh and kick at me as I worked the bottom of her feet, it sort of reminded me of a bucking bronco, but I prevailed, eventually.

I initially used lotion on her pedicured toes, then when I had finished the rest of her feet, ankles and calves, I returned to her toes and carefully wiped the lotion off of each toe.

I knew Lauren trusted me because she didn't ask what I was doing.

She was literally purring by now; stretched out completely nude on the table in front of me.

Carefully and slowly, I lifted each foot and sucked on each toe in turn.

She started laughing because it was so ticklish and she begged me to stop, even kicked at me a bit in a half hearted effort to get away but I held her tight and made her take the torture.

I really did go to town on those pretty little toes. And she loved it despite her protests to the contrary. But she was relieved when I stopped licking and sucking those digits.

She wanted me licking, kissing and sucking other things ...

Lauren had her hair done earlier that day so I didn't touch her head.

But I still had work to do on her thighs and her butt.

****

"So far, so good?" I asked Lauren.

"My God you're good Jack, this is the best massage I've ever had."

I walked up the left side of the table and gently rubbed her bare butt.

"Ready for the next phase?" I whispered into her ear and she whispered back "Yes."

I turned off all the lights in her suite, leaving only the music on.

The light from outside of the hotel lit the room just enough.

I started in on her thighs, running my hands from behind her knees up to her butt.

The second time my hands reached her ass I got the reaction I desired.

Lauren spread her thighs for me.

The third time my hands got to her ass, she lifted up her butt, allowing me access to the crevice between her thighs and her pussy.

I stopped for a second to apply more lotion to my hands and this time when I returned to her body my moist hands started in on her crack. I was going to give Lauren my Grand Canyon Massage.

Using both hands I spread her cheeks from the top down, and started massaging the walls of her canyon, from north to south, my strong thumbs rubbing places that had never been touched before.

It wasn't painful, it was just a different feeling, one that Lauren hadn't experienced before.

When I first started she sort of looked up and back at me like I was crazy but after just a minute of this she whispered a confession of sorts "That feels really good Jack."

After just another minute of my rubbing, slowly, but firmly, I leaned down to her head and said "I want you to reach back and pull your cheeks apart for me."

Lauren did what I asked without hesitation or pushback.

Her tiny rosebud was there for me to explore and after rubbing all around it, and even reaching below her to gently tease her bald pussy, just to let her know I hadn't forgotten about it, I carefully and slowly penetrated her ass with my middle finger.

I heard her inhale and felt her clench for just a second but I put my left hand on her lower back and said in a calm voice "breathe and relax" and she did.

Being persistent, it took just a minute and some patience before I was able to get my finger in past my knuckle and then all the way in.

Lauren was grunting and tensing a bit, and her bowels were trying to push my finger out of her most private place, but she didn't really resist.

In fact, she aiding and abetting me by holding her ass open for my finger to invade her.

It was soon time for a second finger and I knew this one would be a bit more difficult as it was going to stretch her a bit more.

I didn't announce what I was doing but I did reach under her with my left hand and found a bare pussy waiting to be rubbed.

Lauren made it easier for me by getting up on her knees, spreading those thighs, lifting that fantastic ass up, her head still down on the massage table.

My date, a power seeking NYC hot shot hotel broker was in the most submissive position a man could get a woman in minus ropes and handcuffs.

Lauren was at my mercy.

Once I found her moist cunt, my left hand started to masturbate her with probing fingers and my right finger started to finger fuck her asshole.

I no time I could smell her the aroma of a very aroused pussy and I could feel the squishy sound of a pussy in heat as my fingers played.

Lauren started to move on my fingers, in search of another orgasm.

"Jack, don't stop ... don't stop ... please ..."

In the midst of her buildup I slowly inserted into her rosebud a second finger and she didn't say a word.

Not a gasp, not a "No" not a "Pull it out it hurts."

She was getting close to cumming on my left hand so I slowed down a bit, not stopping, just teasing her a bit, playing hide and seek with my fingers on and then off of her pussy which caused her to gasp out at "You bastard Jack ... let me come ... I need to come ... please Jack ..."

It was funny how -- she went from anger to begging in about 1.9 seconds!

The second the fingers on my left hand re-engaged her clit, she bucked on that hand with a "YYYYEEESSS" and I slipped three fingers into her asshole and began to vigorously fuck her bowels.

This time she noticed the stretching and the fullness in her ass which came out as a gasp but she said nothing because she was so interested in her own orgasm.

Nothing else really mattered.

With three fingers plowing her ass and my unrelenting teasing of her erect clit and her wet pussy lips, she was started to hump as if her orgasm was just a few short seconds away.

With my left hand, I pushed into her cunt with my middle finger hooking in search of her gspot.

Lauren spread her legs even wider to help me and while my thumb played with her clit, my middle finger found her soft pad and began playing the one note on the piano that was guaranteed to be number one in the jukebox.

Lauren first moaned then screamed as her body stiffened and then shook at the powerful tremors pulsating through her body as her climax hit.

It was all I could do to hang on as she bucked and gyrated on my fingers; she shaking went on for longer than any other woman I had been with, which was saying a lot.

Her pussy throbbed in pleasure and her rosebud pulsated as my finger fucking continued.

When her shaking had almost stopped I pulled my fingers out of her and she collapsed on the massage table.

Wanting to get in on the action, I quickly lubed up my very hard cock, climbed up on the table and prepared to mount the ass of a prone, nude Lauren.

I asked her as she was coming down from her orgasmic high "Do you want my cock in your ass?" and she whispered back "Yes, but be gentle, please."

When the tip of my cock touched her anus she flinched initially and then Lauren pushed back, actually seeking my cock.

I didn't delay; I pushed into her winking hole before it closed and even though she gasped as my trouser snake pushed into her, she didn't resist.

God bless Lauren, the next thing she did was reach back and pull her cheeks apart again to aid me.

Her ass was as advertised: tight, hot and wet, and in less than thirty seconds I was working on getting balls deep in probably the tightest hole I'd ever been in (minus the virgins of course).

Sinking into that world class, Stairmaster junkie ass was an E Ticket Ride.

I pushed in about three inches and as Lauren adjusted to the invasion I whispered to her "Do you like a cock in your ass?"

Softly, her head down, Lauren whispered "Yes."

I pushed in a bit more, and I heard a low moan.

Now I was six inches in.

Without prompting Janet whispered "I like your cock in my ass."

With that I pushed all the way in with a single thrust, going as deep as I could.

Lauren shook like a fish that had been speared but she responded by crying out "Don't stop. Please!"

I started to pump, slowly, slowly, picking up speed.

"That feels so fucking good."

For the next ten minutes I humped her tight ass, using some more lube and listening carefully for signs of any discomfort.

I don't know what Lauren's past history with butt sex was to that point, but even if she didn't enjoy it, well friends, she certainly got into it that night.

Was I gentle with her? Sure, she shed no tears but I was on a mission and I achieved it.

Lauren was so turned on she reached under herself to play with her pussy.

As I picked up speed, as my thrusting continued, pounding deeper and deeper into her ass, going into virgin territory, she began to say "Oh God, Oh God, OH GOD" as an anal orgasm neared.

She was no anal virgin.

Lauren knew every trick in the book when it came to ass fucking and as much as I wanted to last longer, I ended up making a very large deposit of baby batter into a deep corner in her dark rear cave a little sooner than I wanted to.