What's "Up Chuck"?

If you missed part one, here is the link. Thanks to all of you for your comments on the first edition. Maybe I'll write more fiction in the future. Here is part two... The Nanny “So tell me what it is exactly that you’re looking for in a nanny.” Big tits and a tight pussy, I thought, but said instead, “Well obviously someone with experience with kids and as well as someone dedicated, who loves their job.” “I am the oldest of three kids and I was thirteen when my sisters were born, so I have practically raised them for years. Also I am a month away from graduation with a degree in early childhood education. I have been babysitting and watching children non stop since I was sixteen. I love kids Dave, and they usually love me.” I watched her as she continued to speak telling me her qualifications and experiences she has had with children but could hardly hear what she was saying. Instead I sat there smiling and nodding at all the right moments, but in my mind I was day dreaming of what she must look like without those clothes. The brief flashes I had been fortunate enough so far to see was just enough to get my fantasy juices flowing. ”So Dave, what do you think? I may only be twenty three, but I do have experience.” I watched as a drop of condensation from the bottom of her beer bottle dropped onto her breasts as she took another swig. Gravity pulled the small drop between the swell of her cleavage and below, beneath her blouse. “Yeah Ann, I would say you do. How about I show you the room I have for the nanny.” “Sounds great!” “Okay, after you.” I said standing and motioning in the direction of the foyer and stairs. I had recently had the fifth bedroom remodeled and decorated for the future nanny. It was tastefully done in pastels and I had added a whirlpool tub in the connecting private bath. Ann’s eyes widened when she saw the room and she crossed her arms tightly beneath her tits. “Oh wow, this is just beautiful!” She said. “I have never had a room so awesome. We never had much money growing up, and my dorm room at school is decorated circa 1970.” “Well, great. I am glad you love it. As you can smell the paint is fresh and I have had the bathroom remodeled too.” “What? I would have my own bathroom?” I pointed towards the closed door and she practically ran across the room to see it. “Oh my God! What a tub!” She giggled like a child and added, “It is big enough for two.” “Yes it is, but you should see the one in my bathroom downstairs, it’s twice this size.” She went back into the bedroom and turned her back to the bed then threw herself down across it. At first I was surprised at her forwardness at making herself so at home, but then all I could concentrate on was her body. She had her arms lifted above her head, stretched to the other side of the bed. Her huge bosom heaved with excitement. Her legs were slightly opened and her skirt had ridden up to within an inch of her crotch. I decided then and there that I was definitely hiring this young and beautiful girl and she would be able to name her price. I fought against my inhibitions and took a seat on the bed next to her out stretched legs. I suddenly had a tremendous urge to run either my hand or tongue, or both, up her leg from her ankle to her pussy. I wondered if all the excitement of the beautiful room had made her wet. God, how I wanted to find out. She sat up next to me on the bed and said. “Dave if you decide to hire me I promise you will not be making a mistake. I will do the best job possible for the boys and,” her eyes drifted down to my bulging crotch, “you.” She shifted herself closer to me on the bed and rested her hand on my thigh, halfway between my knee and package. “I really need this job and I really want to be a part of your family here.” I looked down at her hand laying gently on my leg and felt my cock continue to swell in my jeans. It was obvious to both of us that I was terribly turned on at that moment. There was no mistaking the outline of my hardened dick lying against my thigh, very close to her hand. She continued to look down at my cock for another moment, then looked up into my eyes and smiled. I cleared my throat and stood then said, “Ann, the job is yours. When can you start?” She jumped up from the bed, her tits bouncing and practically leaped into my arms giving me a hug. “Oh, thank you! I can start tomorrow if you’d like. I am so happy, I could just die!” She wrapped her arms further around me and rested her head on my shoulder. Wow, how good she felt. With those enormous boobs pressed into me I took my arms and wrapped them around her as well, placing one hand at her shoulders and the other at the small of her back. We stood like that for nearly a minute, just holding one another and celebrating both our good fortunes. In the weeks that followed everyone in the Martin household settled into routine. The boys simply loved Ann and she them. She took them to school, to their practices, and shopping and I was free to focus on work with very little interruption. Even though she wasn’t required to stay past six o’clock, unless I was out of town, she usually did. She loved her bedroom far too much to sleep anywhere else. We also got to know each other pretty well too. In the evenings, once the boys were in bed, we found that we enjoyed one another’s company and had much in common. To my dismay there were never any more sexual innuendos, but that was okay. She was my employee after all. I had to constantly remind myself, when ever I would see her walk around the house in her short shorts or just a long t-shirt, that I was paying her salary. It surely was hard, I can tell you. Everything was pretty much your typical “boss – employee” relationship till the night of June third. For the past two years the third of June has been a particularly hard day for me. It was my late wife and my anniversary date. In years past I usually found myself closed up in my office, with a bottle of wine and our wedding album. This year was no different. Without saying anything more than good night to my boys, I left them in Ann's care at the dinner table and took my newly opened bottle of wine and closed myself up in my office. I miss my wife very much. Time has made her death easier to deal with, but still there are moments when I have to struggle from breaking down. Special occasions like Mother’s Day, Christmas, her birth date, our anniversary and the anniversary of her death are very hard on me. I try to keep it together for my sons, but when I can’t I typically find myself in the privacy of my office. As I drank my wine I clicked through the many folders of digital pictures I have stored on my computer. Mary was such a beautiful woman, and did so much to make me happy in all aspects of my life. Especially when it came to matters of intimacy. It had been over two years now since I had last made love to a woman, and I missed it in the worse way. Sure I had had ample opportunities to quench my needs and desires, but I never could bring myself to do it. All the approaches made to me by women over the years have done nothing but remind me of what I could have had, if not for the tragic car accident. I suddenly noticed that an hour had passed and my bottle of wine was empty. This is silly, I thought. I am a grown man; I do not need to be sitting here crying like a four year old. Sometimes life sucks and you’re dealt a shitty hand. That’s what has happened to me and I just need to deal with it and get over it. I kept trying to mentally push away my sadness when there was a knock at the door. “Come in” I said, hurriedly wiping away my tears. Ann opened the door and walked in wearing, what appeared to be, nothing but one of my silk dress shirts and carrying a bottle of my favorite pinot grigio. “I thought you might need some more,” She said holding the bottle out to me. I tried to force a smile, but couldn’t help but notice her attire. She looked down at what she was wearing and let out a nervous laugh and said, “Oh, sorry. I was getting your things ready for the cleaners and couldn’t resist putting on one of your shirts. I love the way it feels and smells. You have some killer cologne. I’ll change out of it soon.” “No Ann, that’s quite alright. It looks good on you. My wife used to do the same thing.” That sudden memory hit me hard and I found myself again pushing back tears. Ann noticed and walked over next to me and took a seat on the edge of my desk. “Dave I am so sorry. John mentioned earlier that today would have been you guy’s anniversary. That’s why I thought you could use some more wine. Is there anything else I can do?” She reached out and put her hand on my shoulder as I sat there in my office chair, my back to her and my head in my hands. I couldn’t stop the inevitable, and the tears soon came. For a moment I sat there and silently cried while she continued to rub my shoulder and back. Once I felt like I had composed myself enough I turned my chair around to face her but was not expected to see the terrible look of sadness on her beautiful face. As I watched a single tear poured forth from her eye and traveled down her cheek. “I am acting like a baby. What an idiot.” I said. “No, you have every right to cry and be upset.” She reached out and put her hands over mine and pulled me in towards her. My office chair rolled easily across the hard wood floor and within a second I was sitting before her as she sat on my desk. Her bare knees there right in front of me. She never said a word and never took her sad eyes off of mine as she opened her legs and pulled me between them and closer to her. I leaned into her and she held me as I sat there between her legs with my face, wet with tears, pressed against her perfect breasts. “I just feel so alone.” I said turning my face from the valley of her cleavage. “It can be so hard on me.” “I can’t imagine what you must have gone through Dave, or what you continue to have to deal with. Memories can be so hard to bare. Tonight, if you’d like, you do not have to be alone. I am here for you in anyway you want.” I continued to sit there squeezed between her thighs and resting my head between her breasts with my arms around her waist. It took me a moment to realize what it was she had just said. Once I had, I lifted my head and looked into her eyes. “I want to kiss you.” I said, and she leaned down taking my head in both her hands and gently pressed her lips to mine. As she broke away I grabbed her and pulled her back in for more. I was hungry for her kisses and I soon had her pulled down off my desk, straddling my lap, sitting on me in my chair. Our kisses were passionate and our tongues were eager to explore the other’s mouth. I pulled her into me even tighter and could feel her firm tits pressing against my chest. My cock had hardened and was throbbing in my shorts and I couldn’t help but wonder if she had panties on under my dress shirt. Panties or no, I was sure she could feel me since she was sitting right on top of it. As we continued to kiss I moved my hands down her back and cupped her tight ass with both hands. She lifted herself up a little so I could pull the shirt tail free from where she sat upon it, and I reached under and quickly had bare flesh in my hands. Yep, no panties. As I kneaded her ass she moved her hips front to back in my lap riding the full length of my hard dick, with only the fabric of my tennis shorts and boxers between our two parts. God, it felt so good, but I wanted more. To be continued...