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My stories are in generally in chronological order. I encourage you to follow along and read these stories in this order as a prelude to this one:
I Hire Monica The Maid
Monica’s First Day as My Maid
Monica the Maid’s Three Hole Day
I Partner with Linda, A Salon Owner
I Massage Monica the Maid
Hot and Sexy Business Opportunities
I Become a Therapeutic Instructor
The Affair Continues in Las Vegas
I Rub an Asian MILF the Right Way
Going Where No Man Has Gone Before
Cumming Where No Man Has Cum Before
That Was The Weekend That Was
I’m Rewarded for a Job Well Done
Fun in Las Vegas with my MILFs
That Was The Week That Was
Now, this story, Sexy Swimsuit Photo Shoot
Then:
I Take My MILF Lisa to Mexico
I’m Ambushed by a Very Hot MILF
The CFO Gets Her Assets Worked Over
In Pursuit of a Very Hot MILF
The Second Time is Twice as Nice
Roadblocks Pursuing the Hot MILF
++++
Early June
Friday afternoon
The Bellagio Hotel, Las Vegas, Nevada
My cock was deep into her mouth, the tip just entering her throat, causing me to groan with extreme pleasure as my very sensitive little head found its way into the constricted passage.
Her nostrils flared seeking oxygen as my probing erection blocked air from reaching her lungs.
Her lips were stretched around the base of my erection, her nose nestled in my short pubic hair.
Her tongue caressed the bottom of my cock as she took me as deeply as she could.
I looked down at this gorgeous young lady, nude and on her knees, legs spread, sucking my cock.
She was Devine. Probably the finest piece of ass I’d ever had.
My right hand was on her head, guiding her efforts to pleasure me.
Our eyes connected; her eyes watered and I knew she was on the verge of gagging but she continued to hold my penis steady in her throat.
The movement of her tongue and the heat of her mouth felt heavenly on my throbbing love muscle.
She unexpectedly swallowed, tightening her throat around the tip of my cock and I moaned at the exquisite feeling.
Her watering eyes twinkled in response.
Then, she released her lips from my cock, pulled her head up and air once again entered her lungs.
She continued on, head bobbing, my cock being massaged by her mouth, tongue, lips and throat, over and over again, with only a single goal: providing maximum pleasure to me.
She was one of if not the very best at giving head I had ever experienced and what I liked about her was she was always seeking to improve her special oral skills.
Every time she blew me she got better and I benefited from her continuing education.
She loved pleasing me. And I loved her pleasuring me.
I had hired her six weeks previously.
I knew she was grateful for the job, the salary and the benefits, and the opportunity but this was not what I was expecting from an employee who wanted to thank me.
This wasn’t sexual harassment.
This was sexual heaven.
++++
I found her on a modeling website as I was looking for female companionship around an adult pool in Las Vegas. The search wasn’t for female companionship for me, it was for my new girlfriend Lisa.
It didn’t take much to sign her up for a cash assignment. There would be no pictures taken. There was no photographer. The task was to wear a skimpy bathing suit at the hotel pool; being topless was part of the assignment, and most importantly, be nice and friendly to Lisa.
If you read “I Become a Therapeutic Instructor” and you learn about Lisa.
I wanted Lisa to have a good time and talk to some ladies and since neither of us knew anyone in Las Vegas, this seemed like a nice way to make some friends.
Actually, I hired two ladies and let me tell you why. Women love to talk. Most guys talk, but not anywhere near as much as women do.
Women talk about anything and they do it forever. Guys talk about their jobs, their hobbies and sports. Oh, and women too. But women have little interest in hearing about work, men’s hobbies that they could care less about, or sports. So, hiring two nice looking ladies to be friendly and talkative with my girlfriend around the pool about the stuff they like conversing about was my way of setting up a fun time for Lisa.
I had never done anything like this before but it worked out well. For the two ladies I hired, it worked out very well. High hourly rate, paid in cash, be nice, talk, have a good time. Home in time for dinner and lunch included, whatever you want on the menu.
Her initial interview, if you could call it that, consisted of meeting me and her friend at the cabana poolside when the place opened. Read the story “The Affair Continues in Las Vegas” for some specifics.
When she took her bathing suit top off in the cabana with Lisa and the other girl, well, that sealed the deal for me.
I didn’t see any physical flaws, far from it.
She was gorgeous bahis firmaları and I found out later why she was a late starter with boys; she was so good looking she was never asked out. Her beauty intimidated the male species.
Over the course of the day I gave her additional favorable marks for being bold with Lisa, applying suntan oil to all the exposed parts of Lisa’s body, including her breasts (with special attention, of course, paid to Lisa’s sunburn prone nipples), kissing Lisa on the mouth and being upfront with me when we were alone by letting me know if I ever wanted someone else to spend time with, she would drop whatever she was doing, and wearing, to join me.
Part two of the interview took place later that same day when she and Lisa got better acquainted with one another. By that I mean, this young lady enjoyed eating Lisa’s pussy. Not just once, but repeatedly from the late afternoon into the evening up in our hotel suite. Lisa loved being licked, kissed and finger fucked by her. Lisa requested that I set up another session for the two of them to continue the, what will we call it? Conversation.
I agreed to set it up with my MILF Lisa on one condition. The condition being I be an active participant of the ahem; conversation.
Oh, and before I forget, this same young lady helped Lisa prepare her virgin ass for my throbbing erection by adding a lubed butt plug to Lisa’s ass to stretch her out a bit before I introduced my MLB baseball bat sized cock to Lisa’s tiny rosebud.
I’m kidding; it only feels like a baseball bat when it makes its way into a female ass.
It feels like a small redwood tree once its in all the way.
Part three took place in the same suite in the early evening hours when Lisa and the young lady in question undressed me and together, the young lady and I took a bath together. During this bath, she started out blowing me, with the goal to help me reduce my tension, but I removed her mouth from the redwood tree. First I made out with her, kissing her like she had never been kissed before and she melted, literally in my arms, surrendering to me on my kissing ability alone. (She was impressed by me physically too, including my dick).
I showed her I wanted to be with her alone and she said she wanted to be with me. After that I took over the situation by eating her to two orgasms, the first by a male mouth for her in months. The poor girl, as gorgeous as she was, was sex starved.
Part four of the interview consisted of me knocking lightly on her hotel room door at about 5:45 the next morning. I had just dropped a load of swimmers into Lisa, at Lisa’s request and told her I was off to the hotel gym for a morning workout. I had a workout alright.
I proceeded to pound this beautiful, firm, young, stacked and willing woman in all three of her holes while Lisa slept in upstairs. I ended her sexual drought.
What I learned later is that she had been saving herself for someone and had finally given in to her boyfriend in April and they promptly broke up. So, she was tight, and fresh and needed to be schooled in the sexual arts.
She opened her hotel door nude. Kissing me hello, she stripped me out of my gym clothes in a few seconds, all the while trying to kiss me. We kissed, and I fondled her. She had arranged for room service to deliver breakfast at 5:30. I didn’t ask how she dressed when she answered the door because I already knew. In addition to coffee, she had some English muffins, jam and jelly delivered.
As for the hot coffee blowjob, it was outstanding. She said she liked Orange Marmalade and that ended up spread all over my balls, which she licked off for her breakfast.
Rimming? No need to ask, I simply indicated with my hands for her to “Go lower.”
Her tongue was magical.
She got me hard with her lips, tongue, mouth and throat. She even nibbled my balls with her teeth. Her techniques were amazing and if I hadn’t just cum I would have spurted in just a couple of minutes, that is how good she was.
Her nude body was amazing. Just looking at her brought me to redwood status. Remember, I had just spent the previous afternoon around the adult pool with this young lady as she wore no top and the smallest amount of clothing I have ever seen covering, or attempting to cover, a fully shaved fresh young cunt.
The front of her swimsuit bottom was so small she was initially constantly trying to keep her pussy covered and sometimes the material gaped, which allowed me to see the whole enchilada. I mean taco. From my perspective, her pussy looked very edible. She caught me looking a few times and knew I was interested.
How could I not be interested? She was gorgeous.
Knowing I was looking, after a very short while, she gave up trying to move her swimsuit bottom around to cover up. if the material gaped, so be it. As for the thong, it was hidden in her crack, so at a distance, from the rear, she looked like she was naked.
Not to be a jerk, because I loved Lisa, but even as she took off her bathing suit top the previous morning kaçak iddaa I imagined even then that this was a young lady I would like to spend the entire weekend with nude in a hotel room, or my backyard pool, hot tub and cottage. I wanted my hands on her, my mouth on her and my dick in her. I eye fucked her from the moment I saw her that Friday morning.
Back in her hotel room, My redwood tree turned into a Saturn Rocket Booster when her mouth, tongue and lips started in on my manhood.
Wide eyed at my size, she spread the Astroglide sauce on my large, angry penis. She looked up at me with those gorgeous eyes and said “I want you in all my holes. Would you mind starting in my ass because I want to get the painful part of your visit out of the way first.”
I smiled and kissed her and I replied “As you wish.” She simply said “Be gentle, Jack.”
I then took her anally, having liberally lubed her back package and primed it with first one, then two fingers before I successfully navigated past that tight ring with fierce resistance until I pushed my way in, half inch at a time, until I was balls deep, my ball sack wet from its interaction with her dripping pussy.
Her hands gripped the sheets and she buried her head into a pillow as she screamed at my penetration. She never asked me to stop, or slow down or pull out. I got in balls deep and had her breath through the pain.
As her hands lightened their grip on the sheets, I started pumping.
She told me later she had played with butt plugs and English cucumbers and I was officially the first in her ass. She was scared of my size but knew I was going to be gentle about it.
I had wanted access to her rosebud from the moment she turned to walk out of the cabana. It was all I could do not to grab her ass with both hands and squeeze it, fondle it, slap it, kiss it, lick it, spank it and rub suntan oil on it. As I sat in the cabana I watched her ass and dreamed of being in bed with her with my hard cock in her crack and my hands on both of her breasts, rubbing them for good luck and pulling on her nipples to wet her pussy so I could plunder it.
I didn’t cum in her ass, but I stayed erect and pumping in it long enough so that she could cum on her fingers, the fullness in her anal cavity aiding her pleasure. Or displeasure. She was relieved when I pulled my hard cock out of her ass. She literally breathed a sigh of relief.
She smiled at me as she collapsed on the bed, breathing loudly as her anal cavity emptied as I pulled out.
I slapped her on the ass and said “You haven’t felt the last of him.”
She laughed, and said “Not today, Jack, please. Give my ass a rest.”
I asked her to go get a washcloth and wipe me clean, and then with my hand on her head, had her check her work with her tongue and lips on my cock. I had her suck me hard again and it was all I could do not to come. She knew she was good at head and she smiled at me as I groaned when she teased me.
She wanted to ride me and so I laid back on the bed as she lowered herself on me. She was hungry to be kissed and so with those big puffy nipples and large breasts crushed into my chest, I rubbed her bare back and thighs and butt as we kissed and she rode up and down. When she sat up, my hands went straight to her tits where I tweaked and pulled on her nipples and rubbed her breasts. She came on my cock in this position, breaking into a sweat as she squirmed on my erection.
After she came she rolled off of me and I directed her mouth to my cock again, and without hesitation, she licked me to full hardness. If she minded tasting her own juices, she didn’t react.
She moved up to me on the bed and asked me if we could just kiss. Which we did, which led to more rubbing and kissing and licking and soon my hands were between her legs and I rubbed her to a nice quick orgasm with my thumb on her clit and two fingers slipping in and out of her very tight bare snatch.
After she came, I found myself licking that shaved pussy of hers. It didn’t take long to get her hot and bothered because I was the only man that had spent time between her thighs. Lisa had dined there the previous afternoon, but only for a single course.
She was so very grateful to me for eating her pussy. She was highly responsive to my tongue and my fingers.
Her hands held my head down as I licked her across the finish line, her pussy humping my tongue as I sanded her clit.
After licking her to two more orgasms, I climbed up on top of her and pounded her missionary until I unloaded into her welcoming tight hole. I laid on top her draining into her, then I rolled off and she grabbed me and pulled me into the shower.
I spent some time washing her while the water poured down on us.
I washed her hair, the way I had been taught by a hairdresser in my home town. (Gloria).
She groaned as a massaged her head, neck and shoulders.
With my hands on her breasts and my fingers pulling on her nipples I wondered how she would respond to nipple clamps.
I also thought about a line of nipple kaçak bahis jewelry that she could model.
Why not? She had perfect tits and great skin. She’d look great on a website.
While we made out in the shower, I told her she had the tightest pussy I had ever been in.
She took that as a compliment and shared with me that she had waited a long time to give up her cherry.
She had given it up to her boyfriend, who dumped her once he got to be her first.
Which was fine with me, she was still tight as a virgin.
Needless to say, she did exceedingly well at my personal interview that morning in her hotel room.
I had other obligations that weekend, with Lisa, and that was all the time I could spend with Dana. I did do four things for her that were helpful.
The first was that I hired her full time and that I would send her the details when I got back to Los Angeles.
The second was that I would make any introductions on her behalf that I thought would be beneficial.
The third was that I would mentor her in business and life.
The fourth, and this surfaced a couple of weekends later, is that I would meet with her Senior Advisor to discuss with the professor that our CYN Suits video would be suitable and qualify as her Senior Project.
So, the next morning, just before leaving the hotel at 6am to drive back to LA, I texted Dana and told her that Lisa’s friend Michelle was asleep in the suite and I provided Michelle’s cell phone number so they could connect.
I thought it would be a nice introduction.
I found out later they connected and they enjoyed meeting, and eating, each other. All day Sunday and Monday too.
++++
I had arrived in Las Vegas on Friday afternoon, having flown in from Bob Hope Airport in Burbank.
I took a short limo ride to The Bellagio, where Dana was waiting for me in the lobby.
We went up to the suite, I undressed her, she undressed me, we took a quick shower together and then she put a towel down on one of the chairs in the living room and she proceeded to thank me for hiring her.
She liked having my cock in her mouth, the tip entering her throat, causing me to groan each time she bobbed and took me deep.
I liked watching her nostrils flare seeking oxygen as my cock went into her throat.
Her lips stretched to the base of my erection, her flat tongue caressing the bottom of my cock as she bobbed deeply on my cock.
My right hand was on her head, guiding her efforts to satisfy me.
She knew her task was to please me. To pleasure me. Nothing else.
Our eyes connected; her eyes watered and I knew she was on the verge of gagging each time she went deep but she continued to hold my penis firmly in her throat.
Her tongue and the heat of her mouth felt heavenly on my throbbing love muscle.
Her tongue played with my cock. It was indescribably amazing.
She continued on, head bobbing, my cock being massaged by her mouth, tongue, lips and throat, over and over again; I leaned my head back on the chair, closed my eyes and just enjoyed the what she was giving me.
Her hands found my tight balls and she began to tickle and massage them, which caused me to spread my legs to improve her access.
This was my Achilles heel; my balls. Once they start to be played with the countdown always started to an eruption.
My head came off the back of the chair and both of my hands found their way to her head.
She continued to bob, her eyes searching for mine, seeking approval for what she was doing.
I looked down and said to her three words: “Swallow every drop.”
Still bobbing, her eyes smiled as she knew her work was truly appreciated.
Very soon I felt the inevitable, the “it can’t be stopped I am going blast” feeling that every man knows and welcomes.
I groaned and spurted, holding Dana’s head down so my penis would not escape her throat.
In the past she might have gagged as the salty white fluid entered her oral orifice but not now.
It shot straight down her throat and she couldn’t taste a thing.
Holding her head to my body, my cock was massaged over and over again as Dana swallowed, those reflexes only improving my experience as I unloaded into her.
She waited until I lifted my hands and slowly backed off my cock, allowing it to plop out of her mouth.
Looking up at me, she licked the head, causing me to jerk back because the tip was so sensitive.
Smiling at me, she took me deep again, all the way down, as my slowly deflating cock drained into her.
Her eyes looked up at me for approval and I smiled and said to her “That was the best ever.”
She nodded and eyes closed, sucked me with a soft passion until I was back to normal.
Dana was sopping wet when she finished and I had her rub one out for me, which I videoed.
She liked being spread eagle on the bed, hands in her pussy, eyes closed, telling me how I was pleasuring her in this fantasy.
She got me hard and I took her the way she wanted me to, me on top, smothering her.
Dana spread her legs and guided my hard cock into her tight steaming wet cunt, wrapping her arms and legs around me as I pounded her with long hard strokes.
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