It happened during those 4 years that I was living in Alaska. Just like every 20 something year old guy I was in need of some money and willing to try just about anything to get it. One night I had a small get together with the usual crowd and a few new faces that my friend Kat brought along. We decided to play some cards and some drinking games. This is when the subject came up about making some extra money. One of the new faces in the crowd (Jeremy) told me about how an older couple hired him to take care of the wife. I asked him about the details of the job and about what exactly did he mean about "taking care of the wife".

He said "Take her out to eat, take her to the movies, bowling, drinking, you know...entertain her pretty much""

"That doesn't sound bad at all. Why would someone hire you to do that?" I ask, not sure if he was being truthful

"Well the old man is not exactly up to the challenge anymore...sort of speak" he said with a smirk on his face

"Man that sounds like something I can do. I would have to sacrafice some weekend days but I could use the extra cash" I said "How much do they pay you?"

"The old man pays me $300 a night, I get a little extra if the old lady recommends it" he said this with a devilish look on his face

"Man you have to see if you can hook me up with one of these couples"

With that said, the rest of the night went by pretty unevenful. A little bit of Poker, Spades, Beer Pong, and ended up getting laid by the usual girl.

Two weeks had passed and I had forgotten all about the conversation I had with Jeremy that night. That is until I received an email from him saying that there was a couple in their mid 60s that were looking for a young, fit, good looking guy to take care of the old lady. I don't mean to brag but I fit that discription perfectly. I'm 6 feet tall, 190LBS, Brown skin, light eyes, and I take care of myself physically. I work out 5 times a week and I run at least 4 times a week. Over the years I've adopted the nickname "Pretty Boy Sean" because of my looks. So needless to say I was very interested in this job. I replied to the email saying that I was more than interested and asked about the details. He told me that their names were John and Julia Dewitts and that they lived in a large house just outside of Anchorage. He told me that she looked pretty good for her age and that she was willing to pay up to $500 bucks a night for the right guy. I did not hesitate and took down their number and address and contacted the Dewitts right away. When I called Mrs. Dewitts picked up the phone and informed me that she would like to meet me for an interview later that evening. I hung up the phone, picked out one of my favorites outfits, got a haircut and got ready for the interview as if it was just another job interview. But little did I know what was about to happen.

I pulled up to the address provided to me by Jeremy and couldn't believe that I had the right address. The house looked like a house you would see on a post card with the words "Greetings from Alaska" written on it. It was by far the nicest house I had ever been to and from the looks of it they had plenty of help around the house. I pulled up and parked my Mustang GT right in front of the house and decided to call Jeremy to have him double check the address. But while I was doing that a young lady opened the front door and motioned for me to come inside. I did as I was told and entered the house. Once inside the young lady offered to take my jacket and that's when I noticed just how gorgeous the young lady was. She stood no taller than 5'5" around 100lbs, blond hair, green eyes, and the most perfect little body. I remember saying to myself that she couldn't be any older than 21

"come in, my mother is expecting you" she said pointing toward a bar located in the back of the room

"wow I gotta tell you, you are gorgeous" I told her completely forgetting why I was there in the first place

She smiled and said "Thanks, I'm sure my mother will like you. I've figured out her taste in men and you look just like the type. Please follow me, I'll lead you to her"

We navigated our way through the house and walked towards the back of the house where Mrs. Dewitts was waiting for me with a big smile on her face. She was not what I expected AT ALL. She was tall around 5'9", think in all the right places but far from fat, Blond hair, big beautiful tits, and a very nice ass. If I didn't know any better I would've guessed she was 50...maybe even younger. I walked towards her to introduce myself extending my right hand to shake hands with her but she pulled in close and gave me a hug and a peck on the cheek instead. While she held me close I could feel her breast pressing against my upper abs and I could tell that her breast were not natural. Once we broke from our hug she told her daughter that she could leave. At the point she began to study my body and face as if I was a car in a dealership. She circled around me a few times touching me all over. When she was done she sat down and told me what exactly she was looking for.

"I need you to take off your clothes" she said in a very commanding voice

"right here, right now" I said a little unsure

"Yes, if I'm going to hire you I need to know you have all of the right tools for the job" she said while sipping on her wine

I had nothing to lose and the idea of being naked in front of this hot lady didn't seemed to bother me at all. So I began to take off my clothes. I stripped down to my boxers and stood there in front of her not sure of what to do next.

"Go ahead, take them off" Mrs. Dewitts demmanded

"Okay, but I'm starting to get an erection...I can't help it" I informed her

"That's perfect, that's exactly what I need you to do" she said

So I proceeded to take off my boxers. As I did that my cock got hard instantly. My cock when fully erect is a good 8 inches (as you can see on my profile pictures) and pretty thick. At this point Mrs. Dewitts motioned me over closer to her. When I got close enough for her to touch me she reached behind my neck and pulled me closer. She whispered in my ear that she wants me to masturbate in front of her and that she wanted me to cum on her feet. I don't know why I agreed to do it but I started rubbing my cock and slidding my hands up and down my shaft. Mrs. Dewitts sat back and watched me jerk my cock with a smirk on her face while she drank her wine. It didn't take long for me to get that feeling you get in your belly right before your cock is about to explode. I informed Mrs. Dewitts that I was close to cumming. She just reached out her right foot and said "here's your cum rag". Without hesitating I grabbed her foot and watched as my thick white sperm flew out of my cock and onto Mrs. Dewitts foot. I came pretty hard, harder than usual and I remember thinking to myself "good timing for a squirting cumshot". Mrs. Dewitts was just looking at what was happening with a satisfied look on her face as she slowly made her way up to my face and eventually locking eyes with me.

"I think I'll be seeing a lot of you...."

"Sean, my name is Sean" I said looking at her with a smile on my face

"Yes, Sean. I'm going to go wash up. You can expect to hear from me soon, okay Sean? Right now you can get dressed and meet my daughter in the f****y room. She's take care of you for today's session. But before you leave Sean there is one rule. What I say goes, no what, and, if, or buts about it...understand?"

"yes Mrs. Dewitts. Thanks for the opportunity"

With that Mrs. Dewitts got up and walked out of the room. I put my clothes back on and made my way to the f****y room where the younger version of Mrs. Dewitts waited for me. She greeted me with a smile and handed me my jacket and an envolope. She informed me that they will be in touch and that she's looking forward to seeing me again. Once in my car I opened the envolope and found $500 bucks in it. I was shocked and very excited to say the least. That night I drove home and masturbated at least 3 more times thinking about Mrs. Dewitts and all of the things I wanted to do to her...

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Posted by Mzkitty
3 years ago    Views: 838
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3 years ago
great hot story part 2 ????
3 years ago
Can't wait for part II.