Separated, I Play Hard in MILF City

(I heard from my guards that several of the women orgasmed while being whipped).

Kelly came in seconds; the moment my middle finger hit her hard little bump.

She bucked on my hand for what I thought was a long time.

She told me later that she had come several times, and that was a first for her.

My right hand was wet; I pulled her hair back with my left hand, forcing her head up.

"Clean my hand slut" I ordered her and when she initially hesitated, I stepped back, grabbed the wooden paddle and gave her ten quick swats on her bare butt. Hard ones; my paddle had holes drilled in it to decrease air resistance.

At first she was surprised and then she started crying again, and even though she tried to move away from the source of the pain, she didn't get far before the hard wood found her bare butt none more times.

This time I approached her from the front, pulling her head back and forcing my still smelly wet hand into her mouth.

She had her eyes closed tight, thinking that if she didn't see it, well, maybe it was just a dream. Or a nightmare.

It seemed to take forever, and despite her wrinkled nose and some protesting groans, she did a credible cleaning job.

I am sure it was her first taste of pussy and I grinned knowing it would not be her last. I had plans for Kelly.

We didn't speak, she licked awkwardly like a sick cat and as I looked down on her, I realized I had a little female minx in front of me.

If she had been smart, and been in the know, she would have used this opportunity to please me and to tease me, licking and sucking on my fingers as if they were little cocks.

And what man doesn't want a wet female tongue licking his palm? That has to be one of the most erotic things on the planet.

But Kelly was too young to know better and so I would have to teach her.

She never did answer me how many lashes she wanted so when she finished, eyes still closed and still not looking me, I went back around her, picked up the paddle and smacked her bare butt rather hard with the paddle, giving her ten more very solid pats and leaving just her butt painted with a even, nice shade of dark pink.

When she had finished crying again I pulled up her panties and pants; put her in the back seat of the car, laying her on the seat so her hot pink ass could cool off, strapped her in and drove to a business I had been before.

That afternoon Kelly got her pussy waxed; her first time.

Another first was that she was nude for the first time in front of another woman who wasn't her mom or her doctor.

Kelly got over her shyness with a few quick swats on that young tight and now pink ass.

I noticed she had a couple of small tattoos on her and I told her they would be removed in the next couple of days.

Joy, the owner, greeted me with a kiss and a big hug. She did a nice job on Kelly, and at my request, had gone to the store and bought new clothes and a new suitcase for the trip Kelly was taking.

Post waxing session, that afternoon I had her fly to LA where I enrolled her in two week full blown etiquette class. It was a 24 hour a day boot camp which would morph her from young starving thief to a focused young confident woman who was very sorry about what she had done to me.

When she got out of the car, I handed her the ticket and said to her "I'll see you in two weeks. When you return I have plans for you."

Kelly got out of the car and asked "Why didn't you have me whipped like the others?"

Looking at her searching eyes I replied "You have potential. You disappointed me but I'll get you on the right track. If you disappoint me again, you'll get the whip."

She nodded and said "I won't let you down, sir" and walked into the terminal.

I wanted to see how she did before I promoted her to being my Personal Assistant.

I knew that Kelly had potential and I was going to bring it out of her.

One smack of the ass at a time.

****

As for the ten ladies, I put them in a five unit apartment complex in a shitty part of town. (Yes, I now officially a slum lord. Sue me.).

The building was behind tall walls and gated; barb wire topped the perimeter walls. Cameras were everywhere. My off duty female cops were always on the premises. I made sure they had a nice place to work.

That first night was rough for all the prisoners. They had to help each other out to recover from the whipping.

I had the guards take away all their clothes; we'd get them new ones when the time was right.

There was lots of lotion and tender rubbing that first night; still some tears and some anger too; talk about escaping from a few of them.

What they didn't know was that every room in the complex was covered by hidden cameras, sort of a "Big Brother meets Temptation Island" thing.

"Amateur lesbian" is a top search phrase for porn and I wanted to monetize this opportunity. These ladies were going to fuel my retirement plan. Or my next jet. Or my alimony and child support.

That night, minus Kelly, I returned to the apartment, gathered the naked ladies and laid out the rules for the next five years of their lives.

I made it clear that if there was any issue with behavior, not getting along with others, or not working hard, they would all be subject to another whipping. They all assured me that they would do what they were told to do.

I told them they would be paid minimum wage as a salary, with plenty of opportunity for overtime. In addition, I would match their hourly rate for as many hours as they worked in a 401k, which meant they would be saving money from the very start.

Their first jobs were as nude maids and naked pool and spa cleaners. I teamed them up for safety. Horny homeowners, most of them retired old men, paid plenty for these ladies to visit. Once they proved themselves as revenue producers, I sent each of them to massage school and then graduated them to work at my newest company the health spa. More on that in a minute.

To their credit, all ten of them followed the rules and did their time without issue but it turned out that a couple of the ladies actually liked being whipped and asked me if I would "help them out."

Which is the subject for another story. Maybe.

Oh, and the subscriptions for the adult website generated a lot of cash. Actually, it was like printing money. Men and women like to watch lesbians

Even the straight ladies turned to pussy when they couldn't stand using their fingers anymore.

The sight of those women being whipped by naked whip masters was erotic as all get out.

I returned to my hotel, had a nice dinner with Joy, got her a little drunk and then I fucked her all night long

For an older, chunkier broad, she was pretty good in bed.

****

While my ten female parolees were tenderly applying lotion to one another that Sunday, I mentioned above that I that had taken Kelly to a place where she had been waxed.

I had been there once before, back in the first week of April before I flew to Santa Fe.

Catherine had set up that first appointment; she wanted my back, sack, crack and cock waxed.

I'll explain the reason for the torture soon.

Joy, the owner, took care of it and she did a great job.

Okay, it was somewhat painful but not as painful as it could have been.

It's essentially getting your pubic hair ripped out. One hair at a fucking time. Ouch!

Most of these folks wear gloves but Joy did her job with bare hands.

("The better to fondle you" she laughed but she wasn't kidding. She had very soft hands and they felt great on my nude body).

Without her saying so, I knew that she was more than impressed with the size of my cock, and she appeared to also appreciate the circumference and weight of my balls too.

At one point she shared with me that "By now all my male clients would have shot their wad" and then she looked at me with appreciation for my staying power.

Joy took her time and while she worked steadily, she took plenty of time to play with my cock, under the guise of checking it for errant hairs. Or that it was in the way of a spot she wanted to wax or rub.

The result was I was turned on, and it showed.

From time to time I leaked a little pre cum, which got Joy's attention.

A slight smile would appear on her face and I am sure she felt pretty good about herself as still being able to turn on a young, in shape male at her age.

She'd wipe it up with a soft cloth and say something under her breath like "This shouldn't go to waste" but she never used her fingers and cleaned my seed off them with her mouth.

Joy got turned on too. I could smell it.

Once the waxing was complete, and it wasn't always pain free in case you were wondering if it was something you wanted to have done, Joy took an extra special interest in my by now throbbing erection.

Now, she may have had a standard hand job in mind, but I wasn't having any of that.

Because once I got on the table, and Joy drew the shades to darken the room and keep the afternoon sun out, she closed the door, turned on some low soft music and came over to the table. Having removed her white, medical lab coat, she was barefoot and wearing only a thong.

"I like to be comfortable when I work" she giggled at me.

Joy seemed like a rather happy to go lucky lady; she wasn't a young lady anymore; she was middle aged and yet amazingly firm in all the right places.

Despite the pain she was giving me as she ripped my pubic hair out using some sort of silly putty, she allowed me, actually encouraged me, to allow my hands to rove.

And I did. Joy probably hadn't been pursued like this before; I am sure most of her clients were straight women.

So, having a good looking younger man taking liberty with your almost nude body was more than she could handle.

Pulling that thong out of her ass I reached between her thighs and soon brought her to two orgasms back to back with my fingers after making her semi-hairy pussy a sloshing wet mess.

Part of the seduction was that I sucked on her titties and we kissed a bit too. She loved the male attention.

She found it hard to let go of my cock!

I could tell by the way she was standing, admiring the view that she didn't want the appointment to end.

When Joy finally announced she was done with her work, she teased me with some light stroking but I had had enough of that.

I needed relief and Joy knew it. And she wanted to give it.

But I had much more than a hand job in mind.

I'm sure she would have blown me as I lay on the table, but I wanted even more.

I sat up, took her by the hand and I sat down on a chair and gently, my hands on her shoulders, pushed her onto her knees, my hard and now hairless cock bobbing in front of her head, literally screaming for attention.

Oral attention.

"Suck" I commanded and she smiled and with a nod of agreement, complied with my request.

Joy was an accomplished cock sucker, of that there was no doubt.

She focused on the head, the sensitive tip; and my balls.

Okay, I love that.

But I wanted a complete blow job for the compensation of my pain, and gripping her head not with force but with direction, I brought her mouth further down my cock, sending a strong message to Joy that I wanted her to deep throat me.

"It's been awhile" she said, looking up at me "and you're the biggest I have ever seen" she smiled and I wasn't sure if she was lying to me or thinking I would go easier on her because of her flattery.

I knew she was capable; every woman is capable, physically.

But was she willing to go the distance, to make my day by taking me deep into her throat, swallowing my load as I came and making this the best afternoon I could possibly have?

It took just a few minutes with me making it clear what I wanted before Joy got it all the way down and I was lodged in her throat as she took me to the base, time after time.

Her eyes watered, she gagged but to her credit, she didn't stop bobbing and sucking and loving my cock as she demonstrated her rusty oral skills.

I noticed that her right hand had sneaked down between her legs and I could smell her female essence again as she played with her still wet pussy.

I didn't mind her doing that as long as she paid attention to her primary directive, sucking my cock and swallowing my load.

Trying to be a nice guy, I gave her a lot of compliments as she bobbed up and down on my penis.

I let Joy know in no uncertain terms that she was pleasing me and pleasuring me with the creative use of her mouth.

I was worked up, and I lasted longer than I thought I would. Joy was in her own little world, on her knees, sucking off a first time client. Her humming just added to my pleasure but I also knew she was happy.

When Joy sensed that I was going to blow, because my cock got harder, I held her head down and said again "You're going to swallow it all -- don't spill a drop ..." and then I came, hard, into her mouth with several large groans that could have been heard down on the street below.

Some snot (or was it my cum?) shot out of her nose as I emptied my army of swimmers into her mostly willing oral orifice.

Joy gagged and her eyes teared up again and I knew she wanted to pull off of me but I commanded her to "Swallow, baby, just swallow."

To her credit, she kept her mouth on my cock and worked her tongue like the accomplished cock sucker I knew she was until I was satisfied and finally pushed her mouth off of me.

Then I directed her to clean me.

My cock softened despite Joy's efforts to raise the dying piece of man meat.

I knew she wanted my hard cock inside of her. In her pussy; maybe in her ass.

It just wasn't going to happen on this visit.

I had Joy lick my balls for good measure.

She was good at it and I complimented her on her skills.

I held off pushing her head further south to lick my starfish.

That wasn't something she would do without a nudge but when she did it I bet it would be good.

Her post blow job work done, and done well, I bent down, pulled her head up to mine and we kissed.

My tongue went into her mouth and she responded back with a groan.

Joy liked kissing and it had probably been a long time since she had a man kiss her like I did.

Her knees were red from the carpet but she laughed as she got up.

I asked Joy if Catherine had paid for the service and she replied with a smile that she had.

Joy helped me get dressed, kissing me all over like we were lovers and we kissed goodbye but not before I left her $1000 for a tip.

"Any place, Jack, anytime" she smiled at me as I tweaked her still hard nipples.

She was very fuckable for a fifty year old.

Somehow I knew she was a three input woman and for me, all holes would be open for business.

I smiled in reply and said "I'll be sending business your way. See you soon."

****

The days went by rather quickly but I was lonely. I had sent Victoria to see family in Colorado.

In early June, things changed.

****

Her smiling big gorgeous blue eyes were locked on mine as my cock sank deeper and deeper, first past her lips and into her mouth and then into her slender throat.

I groaned loudly in exquisite pleasure as my sensitive tip bumped up against the tight walls of her tunnel.

Her lips were nearly stretched to the limit but she kept on task, her mouth wide open as she continued to lower her lips to the very base of my hard, wet, throbbing cock.

The wet skin made taking me easier.

Her lips and mouth provided an amazing feeling, almost indescribable in terms of pleasure, as she finally took me to the base without hesitation, coughing, gagging or her eyes watering.

I groaned as her lips fully encircled my very stiff love muscle and her eyes were now twinkling up at me as she wiggled her flat tongue on underside of my hardness.

I groaned again as waves of pleasure rippled through my body.

It was almost more than I could take.

If she kept this up I'd be blowing my load pretty damn quick.

Who taught her to do this? Unfucking believable.

She groaned as she pushed her head just fractions of an inch further, going as deep as she possibly could ...

God she loved to please me!

Without blinking or hesitation she began the slow up and down motion on my cock, pulling off my cock to the very tip which she teased with her lips and tongue, then going back all the way down to the base.

Slow and deep, just how I like it; knowing full well she was maximizing my pleasure and making me wait for the reward, she continued.

She was in no hurry. We had all night. Most of it anyway.

As she started her bobbing, her beautifully manicured fingernails skillfully started playing with and teasing my tight, all ready sperm filled sack.

I'd want; no need, relief soon.

She knew; somehow, she just knew that I loved to have my balls teased, touched and tickled while getting head.

In an ideal world, I'd have one warm wet female mouth on my cock, deep throating me while another female mouth, using her tongue, teeth, lips and fingernails would be working on my sack and crack, but for now, this one woman would be more than fine.

Her deep throating effort was always going to be a timed contest between how much pleasure she could give me and how long I could last before I exploded into her welcoming oral orifice, groaning loudly as my cock first stiffened then erupted into her tight throat until my balls were fully drained.

I yearned to come (what guy doesn't?) but I also wanted to hold off, to delay the inevitable pleasure I would certainly enjoy, so that when I did blast, I delivered a big salty creamy load to my lover, ropes of thick white protein, which she would greedily swallow with a smile.

Who was this Diva of Deepthroat? This Oracle of Oral? This Sultana of Swallow?

****

And so friends, the lady with the extraordinary oral skills was Natalie.

She was a beautiful woman: smart, educated; articulate; with a face you could just stare at all night long it was so captivating.

Natalie never wore anything but dresses, skirts and business suits and she had the legs and ass to pull it off.

No Hillary Clinton pantsuits for her.

Her voice was sultry, like Kathleen Turner the actress; her smile was big and natural like Jenny McCarthy and she had an impressive figure. Meaning big tits on a normal body type with a nice ass, great legs and slender ankles. She hid it well under the guise of professionalism but it didn't take me long to figure out there was a 9.86 body under those business suits she wore.

She loved to laugh, sing, and couldn't keep her hands off of me.

Trying to be professional in our dealings, I struggled to keep my hands to myself. But I did it.

During our business meetings she liked to sit next to me (right next to me!) and she was always touching my arm, or my hand, or my shoulder, touching me on the back, and those tits (OMG those tits) were usually crushed into my upper arm. On the Jack Colton tit size scale these were more than a handful. I must have aroused her; her nipples were firm when pressing into my arm. Not that I was complaining. Who would complain about any of this? (#NotMeToo!)

I could smell her faint but alluring "I want you to fuck me" fragrance and she had wisps of soft silky hair that brushed the side of my face. Lets just say the packaging was better than anything I had run across, and you know if you've read my stories, I've opened more packages in the last year and a half than 100 five year olds at Christmas.

Her sexy voice on the phone got me hard as I always drifted away to a vision of me ravishing her on the sofa in my office.

It never took me long to get hard when Natalie was near.

Sometimes I would get aroused just knowing I was going to see her.

In our business meetings, at any point we were so close we could kiss like it was the most natural thing to do on earth.