I'm Running on Empty

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 Five."

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

Enjoy and thanks for the views and votes.

++++

Hopefully you have read the preceding chapters of "Running on Empty" but if you haven't let me fill you in on me and how I got to this point in my life.

This is my fifty second story.

These stories cover my life from the day my first wife died in an automobile accident in January just about 15 months previously up to today. I was a business consultant and ended up being a business owner. And my business holdings, and real estate holdings, have expanded dramatically, since my wife died.

After my wife's funeral, I hired or rehired, Monica (the Maid) and then I repurposed her work efforts from just cleaning the house and doing the laundry to that plus cooking, running errands and having sex with me.

This is all in my first story, I Hire Monica the Maid.

She was a willing widow.

More than willing.

Open to almost anything.

What she wasn't open to, I converted her so that she was willing.

For starters, I converted her into a three hole input woman for my exclusive use.

That meant having lots of sex with her.

Soon after we started down the path of a healthy sexual relationship, anything went including me taking her anal virginity and eliminating any reluctance she had about eating pussy for my viewing pleasure and preparing the other woman for my cock.

I'd have sex with a woman and Monica the Maid would clean my cock with her tongue, mouth, and lips.

She was already an expert at deep throat and loved to swallow. I just had her practice on me. A lot.

So she could pleasure me even more, in other ways, I sent her to massage school.

I also hired a personal trainer and if I recall, a dietician so she would lose weight, look better and cook us healthier meals.

That affair, if you want to call it that, set the stage for a long period of nothing but hot sex and good times with at least forty women and more likely fifty ladies over the course of the next year and a quarter.

Each story that followed covered what was going on in my life, personally and in business, in mostly chronological order.

I had sex, great sex, a lot of sex, with a lot of different women.

None were married; I made damn sure I wasn't fucking any married women.

Probably the smartest thing I ever did was to learn how to give massages.

Notice I didn't say "professional massages" although I know how to do them.

It's just that giving sensual and sexual massages are just so much more fun.

And, let's be grown up about it: a naked female lying on a massage table with a male masseuse that they are attracted to, that they have been making out with, are going to end up with a cock in their mouth, pussy or ass, or at least two out of three orifices. If I had the time, I usually ended up in all three holes.

I also became wealthy as a result of hard work and being persistent. I was sorry that my first wife did not live long enough to see the day when I had made enough money so neither one of us would have to work another day if we so desired to retire.

Being wealthy didn't stop me from having sex and I did not flaunt my money to get women into bed. I didn't have to, because they liked me for whom I was.

About nine months after my wife died I married one of her friends, Catherine, a gorgeous French Canadian divorcee with two daughters. Catherine was pregnant in no time flat but she made it clear even before we got engaged that I could have sex with other women. In fact, she usually found the women for me to sleep with, and approved of them before she introduced them or put me in contact with them.

And, okay, I never planned to sleep with any of them, just to fuck them, but I did fall asleep a few times.

And life was good. Very good. Which brings me to this story.

****

This is the final chapter of the series "Running on Empty" of that first mind blowing week in April when my wife gave me the Mother of All Hall Passes, the one thing every married can only have wet dreams about.

(If you haven't seen the movie Hall Pass, you should).

Catherine, my pregnant wife, wanted me to enjoy one new "hole" each day of the month and I found out later she had arranged for me to meet a cadre of females on this trip.

All of the women were attractive, professional and way more than willing to have sex with me.

I didn't have to ask. Everyone of them invited me to fuck them.

They didn't say "Fuck me Jack" but they made it clear what they wanted.

Dick. Cock. Man Meat. That thing hanging between my legs.

It's hard to miss the signs when a woman is interested in you.

Now, they all wanted something from me (money, or a job, or to do some business or to buy their business) but setting that aside, the money was simply the door opening, the conversation starter, to get to know me so we could get naked together.

All were professionals on the outside but once they were undressed, or partially undressed, it got fun fast.

I wouldn't say that any of them went from professional to slut.

I would say that they went from professional to anything goes quickly.

That song by Cyndi Lauper that "girls just want to have fun" is still true, no matter how old the girl is.

And sex is fun.

Oral, vaginal, anal; they didn't care where I stuck my hard cock.

(There was some resistance (no pun) from a few on the ass fucking but I pushed past those objections quickly. And they soon enjoyed the experience so much that they asked me to do it again. And again, and again. You get the idea).

These ladies wanted my come, my baby batter, my man juice in them or on them.

While I deposited most of my loads internally, I also splashed a few faces, between some nice breasts, and on the backs and between butt cheeks of my partners.

Note to my readers: be careful not to splash on a woman's face after she's been professionally made up; they get really pissed off. And the anger doesn't go away.

Not on purpose but caught up in the moment, when I was coming a couple of times, I know I also ruined some expensive hairdos when my sauce blasted into their coiffed hair.

Some ladies were better at giving head than others, but let's be candid; the only bad blowjob you can have is when your cock is used as a teething ring by a woman who thinks a man likes his cock bitten. Not for me.

Some just suck on the tip because they believe that they have a gag reflex but I moved the reluctant female around the bed a bit to get them into an easier position to take a hard cock orally and my erection soon found its way into a warm and welcoming mouth and tight throat.

I encouraged the less skillful ones on with words of encouragement and instruction and the light use of my hands to guide. Oral feedback is best when receiving oral pleasures and I gave a lot of feedback.

Can every woman deep throat? I believe the answer is yes and I'll go to my grave turning tip suckers into sword swallowers.

They all swallowed cum; some gagging on my cock as I pushed into open mouths trying to get the head of my cock into their throat. Getting the sensitive tip into the top of a tight throat feels out of this world. Getting your cock down actually into a throat is beyond amazing.

Some, particularly the older ones (and there were a few more "older" ladies on this trip) gagged as my thick and salty cream entered their mouths ... to be swallowed.

I made it quite clear that spitting wasn't permitted.

As you shall read, one older lady tried to move her head away as I approached the point of no return to unload a good size deposit into her mouth.

But I held her head tight with both of my hands and used a firm voice when I said "Swallow. All of it."

I knew she didn't want to but when I did blast, there was some coughing, gagging and watering eyes.

Then I had her show me that she did what I commanded.

She opened her mouth and I found my load on her tongue.

"Swallow it now."

Her eyes locked on mine, her eyes watered as she choked it down.

She sort of smiled up at me in accomplishment looking for approval.

"Open up and run your tongue all around your mouth for me."

She did, swallowing a few more times, then opened up wide to show me her clean mouth.

My hands still holding her head I bent down and I French kissed her.

Yes, we were swapping some spermoza. So what, it was mine.

She was surprised and maybe a bit embarrassed but when our lips parted and we smiled at one another I told her "It's just sex and sometimes sex means breaking new ground." Then I complimented her on giving me a nice blowjob and told her she'd be practicing again soon, and yes, she would be swallowing.

The lady laughed in relief and then I told her to lick me to keep me hard and when she got me nice and ready, I fucked for a long time and she loved it, coming many times as I plowed her pussy.

Believe me, when it came to oral sex, I did not want to be a jerk about it, but if you want to do business with me, you swallow.

I also made it clear that I wanted pussy to mouth and ass to mouth. The younger ones were more willing but the older ones came around after some encouragement.

Encouragement defined as a firm hand holding their head so they had no choice but too swallow.

Most were very good in bed, demonstrating lots of enthusiasm. Generally, these ladies weren't afraid to try new positions. Those that weren't good in bed, meaning as responsive as I preferred, got spanked, hard, as I took them like a pony to improve their ... enthusiasm and performance.

They all had shoulder length or longer hair, which I pulled on as I rode them hard.

The spanking turned a lot of them on.

As I said before, women like to be dominated.

They want a man in charge, pushing them to do things in bed they wouldn't normally do.

Women talk about their exploits in bed and they aren't shy about sharing what they consider to be the most degenerate things they have done to their friends.

They all took my cock in the ass, despite some misgivings. Yes, there was some whimpering and a few tears, but I was gentle and was very liberal with my application of lube.

There were a few anal virgins and some who had sworn off getting a big dick in their ass because their prior experience wasn't particularly enjoyable but through persuasion and tenderness I converted the reluctant into the willing.

What made believers out of them?

First, I usually did my Grand Canyon Massage with each of them. They all loved my fingers around and in their bottom and they responded positively to the digital invasion.

Second, following the massage, my tongue made its way to their rosebud and many had never had this done to them before. They loved it, especially in combo with a finger fucking of their pussy.

Third, I took my time and used lots of lube as I expanded the hole as I went from using one finger to up to three.

The stretching was a bit more painful for some than others, but they liked the naughty play I was providing.

And, last, when I did do it, I took my time, usually a half inch at a time, and had them doing some serious breathing exercises as my hard pink baseball bat pushed in.

I was patient and kind, and made sure that each of my partners came with my hard cock buried deep between their cheeks.

How many holes did I have that first week in April?

I may have an answer at the end of the story.

I can say that I exceeded, greatly, Catherine's goal of one new hole a day.

I usually had that completed before breakfast.

****

The first week of April was the week my wife sent me out on a mission to plow new pussies, to penetrate virgin (and not so virgin) rosebuds, to be sucked to completion by beautiful smart women, all with her full permission.

My wife Catherine wasn't jealous; she knew I liked planting, depositing, and shooting my potent, baby-making man juice on and into attractive, intelligent, professional women.

Pussy, mouth or ass, it was all the same to me.

Oh, and condoms; those are for other guys to use.

I like having sex the natural way because it feels so fucking good.

I didn't want anything between my hard bare cock and bare pussy.

Catherine knew I hated sleeping alone so when we weren't together, she made suitable arrangements for me to have a sleeping buddy when I was away from home.

She didn't want me traveling; Catherine wanted me home, but if I did have to go, she wanted it first class in every regard for her husband.

Fly on the company jet.

Stay in nice hotels (the kind we were looking to buy).

Eat at nice restaurants (steak is good along with French champagne and Napa Cabernet).

Always a suite, never just a room: the more space to fuck in.

So, my sleeping buddies were hand picked.

Friends, I got some fine ass those nights.

Some very fine ass.

Like bucket list ass.

I've made no secret of my use of the wonder drug, Viagra.

With the women Catherine set me up with, I didn't need Viagra.

But I took it anyway, as erection insurance.

If nothing else, it got my hard again faster so I could continue my sexual extravaganza between the sheets.

That I got no sleep those nights was of no consequence to my wife, because she didn't have to pay the price of not getting any quality sleep and trying to function the next day as the top executive of an already large and rapidly growing business empire.

It was the allure of even more fresh pussy that got me through those days when I was literally "running on empty."

I should also mention that the "buddy system" wasn't foolproof.

Two of my sleeping buddies were pregnant (Janet The MILF) and Julie, my VP of Organizational Development.

I was surprised but shouldn't have been that this number would go up later as a result of this trip.

****

I was on the road and out of gas.

It was a Saturday morning, the end of the first week of April.

I knew my wife Catherine was frustrated with me, maybe even angry at me ,for not returning home to Los Angeles on Friday afternoon, as planned.

But we had an agreement that if there was bad weather I was to stay on the ground because she did not want me flying in tough conditions. (I wasn't thrilled about flying in turbulence either).

So, I had a choice: start driving west, on I-40 through the bad weather which was Plan B; or, stay were I was.

Plan B sucked. It would still take me at least 16 hours to get home, and that was driving nonstop in great weather and no construction, truck traffic or highway patrol officers to pull me over.

I opted to spend the night in Santa Fe and return home on Saturday after the storm front passed through.

I like to sleep in a warm hotel room. I sleep in the nude and don't want a lot of blankets on top of me. I keep my hotel rooms so warm I often sleep naked with nothing on top of me.

That Saturday morning my eyes adjusted to the morning darkness in my hotel bed in Santa Fe, New Mexico.

When I wake up I always know where I am and who is with me.

Meaning I don't get so trashed I can't remember whom (or is who?) I fucked or what I did the night before.

There was a pretty blonde in my bed; she was on her back, sheet down to her waist, snoring away.

She looked angelic; her straight hair was shoulder length; it framed her face and she was so naturally good looking I doubt she used much if any makeup.

It was a very nice view but it got better as my eyes wandered south.

Her bare breasts were large, firm; so firm I would have sworn they were man made but I knew differently.

Those magnificent mountains of flesh were capped by huge pink areoles, probably two inches across and rising out of the center were erect light pink nipples, along the lines of pencil erasers, maybe an inch high, waiting just for me.

To kiss, lick and suck. And if I wanted to, I could clamp them. Or motorboat them.

Just looking at those melons made me want to devour her and cover her bare fit body with bite marks and hickeys.

Her belly was flat, without the scars or stretch marks of pregnancy and childbirth and I was still a bit foggy so I couldn't remember exactly how much hair she had on her pussy.

Some, I thought, but it wasn't a thick, high plains bush.

Thank God I wouldn't need a pair of sheers to get to her love button or puffy slit.

I could just lick my way through her pussy hair.

As the fog in my head continued to clear I did remember that her bush was just a shade bit darker than the head on her hair or her eyebrows.

I smiled because I think she would have been even more of a knockout if she had a full, lush bush.

Or a bush that was nicely, strategically trimmed.

On a nude beach at the ocean or nude at the hotel pool in Las Vegas, she'd turn heads and silence the crowd just by her presence.

Her name was Lisa; she arrived at the hotel in the wee hours of Saturday morning after a long slow drive through West Texas dealing with lightening, thunderstorms and downpours.

****

I laid in the bed for a few minutes thinking back on the week.

The week started out on Monday morning with me dropping two loads at my house, one into the pregnant Janet (The MILF) and a second into the welcoming mouth of an also pregnant Julie before leaving for Palm Springs and then flying to Las Vegas where I went to get some work done.

I stopped in Palm Springs for a long overdue visit with my mother in law. Isabella was a temptress of the highest kind, a fifty two year old woman nude with a figure most 25 year old females would be jealous of, having me massage her, rub suntan oil on her, all the while she was teasing me, wanting me to cross the line and take her, fuck her, ride her like she wanted me to ride her since the moment we first met.

She'd always greet me with a kiss on the mouth, lips closed, but one of these times she'd want to French me. I just knew it and so did she. She was bidding her time.

But I didn't take the bait, I didn't cross the line. I was a good and faithful husband to my pregnant wife Catherine.

On the plane to Las Vegas the co-pilot Janey took pity on my condition ( a raging hard on) and gave me some relief with a world class blowjob that emptied my balls despite the fact that I had made two deposits already that morning.

I had a disciplinary session on an HR matter once I got to the hotel. It turned out my accounting clerk that we thought was embezzling was actually watching out for me because she identified internal theft that was taking place. Serious theft.

I won't go into the details now, but if you read the story you will enjoy, as I did, learning what a first class sword swallower Ziba was and that she liked, no, craved, anal sex. So, I fucked her in her ass without lube at her request and she loved every inch of my man pipe being in and moving in and out in her tunnel of dark love.

I also shaved her very hairy pussy; my reputation for being a good pussy shaver had preceded me.

That work behind me, I found my way to the adult pool where my pilot Pamela, co-pilot Janey and a former lover, Dana (Ziba's daughter), were sunning and getting in some rest and relaxation.

As I was massaging Pamela I noticed a very (VERY) attractive lady nearby. I nicknamed her The Blonde and she was exquisite in every way known to man.

As I left the pool to get to a business meeting up in my office, The Blonde, now topless, came up to me an introduced herself to me; we were having dinner together that night. Her name was Lauren. In the background was Jessica, a real estate attorney who I would meet a later in the evening.