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My stories are 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
I Take My MILF Lisa to Mexico
I’m Ambushed by a Very Hot MILF
For background, let me share the main characters in my stories:
I became a widower unexpectedly in January. I was lonely and in pain; I made an offer my maid Monica could not refuse. She stayed on as my maid and became my part time sexual playmate. (I Hire Monica the Maid; Monica’s First Day as My Maid; Monica the Maid’s Three Hole Day, I Massage Monica the Maid).
Coming out of my funk, I decided to learn how to give massages and I met Susan, a bathing suit model, who was my massage instructor, and we became friends. Between Susan and Monica I came up with some new business ideas (Hot and Sexy Business Opportunities).
I met Lisa, a divorcee, who was a student of Susan’s when I was a substitute instructor. We became lovers. (I Become a Therapeutic Instructor).
Lisa and I went to Las Vegas. (The Affair Continues in Las Vegas and That Was The Weekend That Was). I hired two ladies, Diana and Dana, to be with Lisa at the adult pool. Lisa arranged for my first threesome when we included her friend Michelle. (My Great Night in Vegas – not written as of this date).
After I met Lisa, and while I was casually dating her, I seduced Akiko, the lady who owned a local dry cleaners. I invited her over for a massage (I Rub an Asian MILF the Right Way). We traveled to Las Vegas (Going Where No Man Has Gone Before) where we met with Marie and Carmen.
The next day in Las Vegas (Cumming Where No Man Has Cum Before) I took Susan’s virginity and enjoyed sex with Dana. On Sunday and Monday in Las Vegas (Fun in Las Vegas with My MILFs) I had sex with Dana and Sandy (a hotel food and beverage employee).
I enjoyed my second threesome in LA with Eva. She was a manager at one of my client companies. (I’m Rewarded for a Job Well Done).
Leading up to the photo shoot for CYN Suits, I spent a week between LA and Las Vegas (That Was The Week That Was).
After the photo shoot, I had a lucrative business deal close. I made a lot of money that day and a friend of my late wife re-entered my life (I’m Ambushed by a Very Hot MILF).
My wife had been gone for almost seven months. In my very first story “I Hire Monica the Maid,” I explain how I work with attractive female employees of my clients.
In particular, there were three female employees that I had wanted to bed at one specific client, but I kept my pants on because I was married and after my wife’s passing, I achieved the ultimate rewards: money and pussy.
In my story I’m Rewarded for a Job Well Done” I took to bed one of the employees of the company (Eva) and this story continues after the deal closed.
In June, and into July, leading up to the sale of the company, I worked late with Cynthia twice and we enjoyed dinner together afterwards. She was the CFO.
As I have said before, my relationship with all employees, at every company I dealt with, was professional and above board.
Even though I was staying in a hotel near the client site, and we ate in the hotel restaurant, I did not do anything other than enjoy dinner and a glass of wine with Cynthia. Well, two glasses.
I made sure that we did not drink on an empty stomach.
Of the three ladies on the leadership team, I had spent the least amount of time with Cynthia.
She was also the youngest of the three, and with her education, background and level of thinking, I could see that she would be the choice, someday, to run either her current company or another one of similar size.
Cynthia had her BS in Accounting, had earned her CPA and had worked in a tax and audit firm for three years before joining her employer. The CPA firm had recommended her for the job as CFO.
She was reserved, most accountants are, but it was only by having dinner with her those two nights including wine that she let her hair down and opened up to me.
We talked about the company, and the deal, and what the future would bring for her, personally and professionally.
What was revealed to me was startling.
This young lady, aged 27, was very shy, had no real friends, and hadn’t been on a date in years.
Cynthia had gone to private girls schools through high school and went to a public university for her first year of college but she felt that it was too big and so she transferred to a private, mostly canlı bahis all female college where she did stellar in her classes and passed the CPA exam on her first attempt.
She joked that me asking her to dinner was the first date she had with a grown man since, well, it had been so long she couldn’t remember when. She shared that when she was at the public university she had a boyfriend for a few months but all he wanted to do was party and have sex and she dropped him when he wanted something she wouldn’t give him.
Without saying so Cynthia was telling me she was a virgin.
But she looked at me with a twinkle in her eyes and said to me “I took care of his needs in other ways.”
When she did this, she reached out and touched my arm and squeezed it.
By the time she started in on her second glass of wine, I learned even more about her.
The alcohol, of course, opened up her personality and she became a very good story teller and laughed a lot, and it got me laughing too.
There is no better way to get a woman interested in you than getting her laughing.
And, if they laugh at you, that’s okay too.
The conservative lady, who was always suitably dressed for her role as the Chief Financial Officer of the company, took off her suit coat, revealing a very nice set, accented by a starched white blouse. I already knew she had a great ass and set of legs from seeing her in the office.
As she talked, her eyes stayed on mine, and her pupils started to dilate, meaning her affection for me was strong and growing stronger.
Her hand remained on my arm, indicating to me that she wanted more from me; more physically.
But, as much as I wanted the opportunity, I had to beg off.
I did it at both dinners.
We talked about it, and I explained that my role as the facilitator of the selling process would be compromised if we took things to another level; if we got naked, if we had sex.
What I didn’t say was that I would be potentially liable for a sexual harassment lawsuit and the company would have a hostile work environment complaint if things went south while I was engaged by the company and fooling around with an employee of my client. I think Cynthia knew this intuitively but was so interested in me (or my dick) she was willing to look past it.
I did promise her that after the deal closed, after her financial future was secure, I would take her out on a real date.
And if that went well, we’d see about a second date.
Both times she reluctantly agreed and nodded at her understanding. And, she kissed me on the cheek as we parted.
I insisted that because she had two glasses of wine, she get a ride home.
I was tempted to drive her home but that might lead to a destination I didn’t want to go to just yet — her bedroom.
After making arrangements with the hotel bus shuttle driver to drop her off, make sure she was safely inside of her home I sent her packing.
I also arranged the driver to pick her up in the morning because her car was in the hotel lot.
We met for a quick breakfast the mornings after our dinners at my hotel.
So, with lovely Cynthia, I had the pot on simmer on the back burner for meals later on.
So, having kissed Catherine goodbye at The Westin, I headed home and got ready for my date with Cynthia.
I got my haircut, went and got a shave, and worked out a second time just to get the edge off.
As I have mentioned before, I didn’t like sleeping in my house so I made a reservation for dinner at the steakhouse in the same hotel where I had spent the night fucking Kayla and Eva (“I’m Rewarded for a Job Well Done”).
I made a reservation for a two bedroom suite in the hotel.
I knew that Cynthia was not much of a steak person and this place had a nice selection of both fish and chicken, a couple of pasta dishes and entrée sized salads.
Arriving at 4pm, I checked into my two bedroom suite. I emptied my suitcase, hung up my clothes and ordered champagne for the room.
I went back to the steakhouse and shook hands with the GM again. You may recall I met him in the story with Eva.
I tipped him heavily again in cash and asked him if he could put me back into that private booth where I had finger fucked Eva and Kayla and he said “Done!”
Kayla wasn’t working so he assigned another pretty waitress, Susana.
I tipped her $200 cash and said, “Be discrete and there will be more of this at the end of the evening.”
She smiled and thanked me. She said, “I think we both know Kayla. And she told me about your last dinner here.”
I said “It was a lot of fun but tonight it will just be my date and I.”
Back in my suite I took a short nap and shower before I changed clothes and met Cynthia at 7pm.
Cynthia met me in the bar with a kiss (!) on the side of my face with a twinkle in her eye. She stood close to me and she was constantly touching me as we enjoyed a split of champagne before we went to the booth.
She dressed in a little black dress with pearls and matching bahis siteleri earrings.
Her chest was impressive; this was one of the few times it wasn’t hidden by a coat or jacket.
I also noticed that she had on three inch heels which made her legs and ass standout nicely.
Cynthia had thin ankles, which was one of those things I like about women; it gave me a sense of the rest of their body.
I asked her what the atmosphere was like on the bus going back to the Marriott on Thursday night. Cynthia shared that people were in a very good mood and some of the folks stayed at the bar in the hotel until it closed.
I nodded, knowing full well who the characters were that would party like that.
“How about you , did you stay too?” I asked with a smile, know full well she wouldn’t have.
“Well, Jack, you will be very surprised – very surprised – to know that I did go into the Marriott bar and have one drink before I went home. I was a good girl.”
Then, she reached over and put her hand on her arm and leaned over to me and whispered “Tonight I’m going to be a bad girl with you Jack!” And with that, she kissed me on the mouth, our second kiss. In public no less! The barriers were falling.
She pulled her head back and whispered to me “I’ve wanted to do that for months, Jack Colton. Months! I’m going to make up for lost time with you tonight.”
Her eyes were sparkling and we kissed again, our tongues running into one another.
Her hands reached up to cup my face as we kissed again.
We were getting good at this and I noticed her nipples were hard. I was getting hard too.
I took her hand we went to the booth.
Susanna already had the champagne ready and she waited until we had a chance to sit down in the booth.
Cynthia was sitting on my right, next to me, close to me and when Susana approached the booth we were lip locked, tongues caressing each other and my hands were, well, where they shouldn’t have been in public.
I had my hands on Cynthia’s breasts. Even through her dress and her bra they felt great. Fantastic.
She was moaning into my mouth and her hands had pulled my head to hers. She wasn’t planning on letting me go anytime soon.
Susana had to wait until our lips parted and God bless her, she was patient and discrete.
She was also very thoughtful, and started out after saying smiling and saying hello to the both of us to ask “Are you here for dinner or should we send something up to your room?”
We all laughed and I said, “Please give us some time and then we’ll order dinner.”
Cynthia almost climbed on to my lap after that, but punctuating the kisses we each found something on the menu to have for dinner.
Between those long kisses, caresses under the table and sips of champagne, I got Cynthia purring.
Her face got flushed with the alcohol and the fondling.
I had her skirt up to her waist under the table but she refused to take her panties off and she wouldn’t let me take them off either.
I was able to determine she had a thong on when I slipped my hand under her backside and found a bare cheek.
I squeezed it and she laughed; she knew what was coming.
She said “I like that Jack, your hands on me.”
I kissed her and replied “When we get to the room how about I give you a massage?”
She laughed at that and said “If you’re asking if it’s okay for you to put your hands all over my body, the answer is yes!”
Cynthia was aroused and I could smell her.
She liked to laugh and the alcohol continued to loosen her up.
We were on to a second bottle of bubbly before dinner arrived.
We ate dinner and, she fed me part of her meal and I told her a few stories about my other clients that got her laughing.
As the laughter died down between us, she kissed me and said “Jack, I want to thank you for being my friend and my mentor and my confidant. I have a gift for you that I want to give you up in the room. Okay?”
Holding my hand we made our way upstairs to my suite.
We kissed waiting for the elevator, and in the elevator I unzipped her dress all the way down her back and reached in and started rubbing the top of her ass. I had my fingers under the top of her thong. Her ass felt good. Firm.
I got her shoes off too and we kissed again in the hallway.
When we got in the suite as the door closed, we kissed and then she gently pushed away and smiled at me and gave me a quick kiss.
“Make yourself comfortable Jack” Cynthia laughed as she headed to the bathroom.
I turned on some music, light jazz, and opened the champagne.
She opened the door to the bathroom.
“What do you think, Jack?” Cynthia asked, as she stood nude in the doorway.
Her blond hair was shoulder length, her breasts were larger than I had thought, firm and capped by pink small areoles and pencil size eraser nipples, which were erect.
Cynthia’s skin was smooth, and her bush was a lightly colored blonde, pretty full.
She had a nice thigh gap and her legs were smooth, sitting bahis şirketleri atop small ankles and small feet; her toenails matched her finger nails.
After taking this all in, my eyes found Cynthia’s and I simply said “You’re beautiful.”
Like in the movies, we both took a few steps forward to each other, and our bodies met and we kissed like long lost lovers.
My hands roved down her bare back to her ass, which I cupped, pulling her into my newly created erection.
Cynthia moaned into my mouth and started to grind on me.
I let her, knowing how hot she was.
Meanwhile, I started playing with her ass, separating her cheeks and finding her rosebud, which I gently pushed on.
She groaned even stronger into my mouth, signaling her approval.
When our lips separated, her hands were cupping my face and mine were cupping her ass, we smiled at each other, nose to nose.
Cynthia said “I have a little secret I want to share with you Jack.”
She kissed me lightly.
I smiled and said “Okay, is this a secret I need to keep?”
I nodded and said “You know you can trust me.”
She smiled and gave me another quick kiss.
“I’m a virgin Jack, and I want to give my cherry to you tonight. To thank you. For everything you have done for me.”
I looked at her and smiled and said “Cynthia, I’m honored you want me to be your first.”
She kissed me lightly again.
She nodded and said “But, Jack, I’m no anal virgin Jack, I want you to start things out tonight by fucking me in my ass.”
I must have had a shocked look on my face, or at a minimum, one of surprise because Cynthia laughed and said to me “You remember I told you I took care of my boyfriend in college, right? Well, in addition to hand jobs and blow jobs, I let him fuck me in the ass. It’s how good Catholic girls like me keep a man interested while they keep their virginity intact.”
I smiled and nodded, and she continued “Not too long ago I helped Diana get prepared before you fucked her in the ass for the first time. Do you remember?”
I looked away for a minute, thinking. As my mind worked, slowly, I continued to hold Cynthia and rub her bare back and butt.
Cynthia had an outstanding young, firm body. I was as hard as I’ve ever been.
My eyes returned to her face and I kissed her and said “If I was a betting man, I would have lost the bet. You were the last one I would have thought of to teach Diana about that.”
She started laughing, “I come across as Miss Goody Two Shoes, Jack. But tonight I’m going to show you how much of a woman I am. Lets get started by getting you out of these clothes.”
Talking up a storm, the usually quiet and shy Cynthia undressed me, one piece of clothing at a time, being very considerate and hanging my clothes neatly in the closet.
With each garment she kissed me on the mouth and she knew I especially enjoyed it when my tee shirt came off and we stood bare chest to bare breast, her strong nipples and large breasts firm against me.
She brought her hands up to my head and pulled me down for a deep kiss and smiled, whispering to me “I like to have my nipples sucked and my breasts played with. Are you up for that Jack?”
I kissed her and said “Yes, I’m going to suck on your nipples until you push me away. But I only lick pussies; I don’t eat bushes so I think I might need to shave you. Are you okay with that?”
Her response was to groan into my mouth. I took it as permission to rid Cynthia of her pussy hair. In order to eat her better. And improve the fucking too, but that would only get better with every session we had together.
Our kiss continued for a long time and my hands roved to her front, slipping in between her thighs where I discovered a moist pussy. I rubbed my middle finger up and down her slit through the thick hair, and in response, Cynthia pulled me in even closer for our kiss.
My God she was so hot. Her young, firm body was incredible to touch and we were just getting started.
I made up my mind right then and there that I was going to cancel my date with Gloria for the next night (Sunday) and tell Dana not to show up at my house until Monday at noon (she was up in Las Vegas working on CYN Suits at the hotel pools).
As for Cynthia, I intended to keep her nude body in that suite with me until check out time on Monday morning.
We got sidetracked the closer she got me to being naked. It seemed like every piece of clothing started a whole new series of exploring of her body by me, delaying me getting naked but enhancing her pleasure as I touched Cynthia in places she never had been touched before.
When my briefs came down and my hard cock bounced out in front of Cynthia she looked at it and said “Jack, its huge!”
Most women would have reached out with their hands but Cynthia gave it a lick, generating a groan from me.
She smiled up at me and said in a very practical way, “This is going to be a very tight fit in me, but a very good one.”
I lifted her up and although she was tall, she was pretty light, I carried her to the bedroom. I pulled back the cover and the top sheet and laid her down on the bed. I climbed in beside her and naked, we started kissing and fondling each other.
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