Beginning of April
It was now spring. I had buried my wife in January.
I was starting to get back into the swing of life.
There was a huge gap in my life and I missed my wife terribly, but life does go on, and so did I.
Monica, my maid, had been enrolled in massage school for a few weeks and she was going to start practicing on me.
Each day she was with me was a three hole day for her, starting with her giving me a nice blow job each morning.
Monica cleaned the house nude, did the towels and sheets, made the bed, cleaned the kitchen and bathrooms and fixed me breakfast and coffee and sometimes lunch and dinner.
She shared with me that the days she wasn't getting fucked by me she was masturbating several times to make up for the absence of my penis.
She also said she was getting more adventurous about trying new things in her ass.
I told her I would buy her some butt plugs to try. She wasn't sure she liked the idea but I said I want you to try them out.
I went online and bought her plugs, nipple clamps and Benwa balls.
I had previously mentioned that I told my pool guy, Bob, that I was letting him go and that I would have a business proposition for him.
I invited him over and we sat out by my new pool and talked business.
This was on a Tuesday afternoon at lunchtime, I timed it so that he finished his route so he wouldn't be rushed and also so that Monica was there.
The construction of the cottage was done with the outside and the guys were working inside so there weren't any distractions like pounding and sawing but I told them to disappear for three hours, paid, and gave them $100 to go have lunch. No drinking though. They left happy.
Monica prepared a lunch of soup and sandwiches.
I had her put on her smallest suit she owned to serve us.
I wanted Bob to see Monica in these tiny strips of cloth.
Her tits swayed, you could see her nipples through the material, her ass was separated by a tiny thong hidden between her cheeks, and her hairless pussy was evident with a camel toe.
She had her hair up wrapped in a matching bandana, showing her delicious neck.
Classy gold earrings hung from her earlobes.
She looked sexy as hell. I was proud to be fucking her.
When she finished serving us, I asked her to clean the pool like she had been doing.
Bob could not take his eyes off of Monica.
He asked me, is that swim suit legal?
I replied, probably not on a public beach but on private property, why wouldn't it be if the owner of the house was okay with it?
He looked at me and said where are you going with this?
I said Bob, you probably do okay cleaning pools, but you have the potential to make a shit load of money if we team up.
How would you feel about giving up the hassle of cleaning pools and spas and focus on expanding your business?
He looked at me and said what would it cost?
I told him, it won't cost you a dime. I will handle the finances and marketing and you handle the people, training and quality control.
We're going to change the business model and the pricing, and start recruiting pretty ladies like Monica to clean pools.
For their safety and to speed each cleaning along, we will team them up in pairs.
They'll show up wearing a suit like this, but with a large tee shirt covering to mid thigh.
When they get behind the fence, off comes the tee shirts.
Before they head out to the car, the shirts go back on again.
I smiled and said, if you're an old guy sitting around waiting for a pretty lady to clean your pool, the only thing that will make it better is if two pretty ladies show up to clean your pool, wearing suits like this one Monica has one.
To make this fair for you, I will guarantee your same take home pay that you're making right now, and will give you a raise in three months, six months, nine months and after a year. By then we should be in great shape and start taking out some profits.
Bob, if this works out, and I think it will; you are going to make a lot of money and have a very nice life once this gets going.
I want you to think about what we talked about, and I will have a proposal for you in a week.
Bob had heard me but his attention and his eyes were on Monica.
He was like an alcoholic, in a bar; they always have their eyes on their waitress.
He nodded. His eyes were still on Monica's fantastic ass.
I said Bob, the one thing you are going to have to remember is that you cannot go fishing off of the company pier, are you hearing me? You will need to keep your pants zipped up and no touching anything either.
He looked at me and said, I got that, Jack. I'm at the stage of my life where I am ready to make a lot of money. I can find pussy elsewhere.
With that Bob left and we agreed to meet in a week.
Monica finished cleaning the pool and she brought the dishes into the kitchen and then took me by the hand into the bedroom where she took off her swimsuit and then undressed me.
Going to her knees she French kissed my cock and gently pushed my legs apart so she could lick my balls.
I need to take care of you, Mr. Jack, you have to come again two more times today.
She licked my balls for a few minutes, getting them nice and stimulated.
She asked, did you like how I served you lunch and cleaned the pool in front of your guest?
Stupid me, I should have thanked her before she had to ask, shame on me.
I sat down in a chair and she crawled over.
I put my hands on her face and pulled her to kiss me. Yes she had penis breath but I didn't care.
I kissed her deeply and looked into her eyes and said, you were great, Monica, thank you for being such a good hostess, chef and pool cleaner today.
Monica beamed then she kissed the tip of my cock again and said, I will come and find you soon, Mr. Jack, once I watch my videos.
Please go do your work but don't work too hard.
That afternoon after she cleaned up, Monica watched her educational videos and masturbated while I outlined the new business that I would own and Bob would operate as a partner.
I bought the domain name, hot stuff pools, and called my trusty graphic designer and asked her to create a logo that would work for the white vans and tee shirts the girls would wear. I emailed my web guy and asked him to research websites, twitter, FB and Yelp accounts for the new company.
I emailed a franchise attorney my attorney had referred and asked him to meet with me and to advise me the amount he would need as a retainer for setting up a new franchise.
Monica came upstairs and said that I was working too hard and needed to take a break.
She stood behind me, her large breasts near my head and Monica started massaging my shoulders, it felt great.
She kissed my cheek and said, Mr. Jack, please come downstairs with me so I can relax you with a nice massage.
Taking me by the hand, I watched her very nice ass go down the stairs to the spare room with the massage table.
Monica had prepared the room well, and I kissed her again before I climbed up on the table.
She ran her hands over my ass and said, Mr. Jack, I want to start your massage by kissing your ass, because I know you like it.
Between the kisses and the small spanks and rubs she was giving me, I started to laugh; it felt good and was funny too.
Keeping her right hand on my ass, she bent down and kissed the top of my head saying, Mr. Jack, I will always kiss your ass because I love doing it.
You have always been so good to me - no one has ever been as kind to me as you, not even my husband, God rest his soul.
I said thank you Monica and she started in on my feet, my legs, and my thighs.
When she got to my thighs she started teasing me, specifically the inside of my thighs, higher up towards my crotch.
She knew exactly what she was doing, using lots of oil and soft strokes; she had me hard as Half Dome and my ass in the air as she played with my inner thighs, her hands brushing against my very tight ball sack.
When she finished with the left leg she moved to the right, with the same impact on the blood flowing to my penis.
She hadn't massaged my ass yet, only my feet, calves and thighs.
Monica gently rubbed my back, pushing me down to the table and said, Mr. Jack, please move over for me.
She climbed up on the table next to me and we started kissing.
She whispered to me, please climb on top of me, Mr. Jack, so I can kiss you when we make love, and I did.
Monica was sopping wet and horny as can be, I don't know how many times she'd rubbed herself to an orgasm watching the videos but it apparently was not enough.
As I entered her, she lifted her hips and reached out to me and said, I love your big beautiful cock, Mr. Jack, I love to suck it and to have you fuck me with it.
I began a slowly and steady thrusting into her and she held me tight and kissed me deeply, our eyes locked as we made love that warm afternoon.
She told me she got wet when she was cleaning the pool while Mr. Bob watched, she felt like she was on display, modeling her nude body in that tiny suit.
She shared that she liked showing her body off to men who appreciate her figure, especially to me.
