I was A Middle Aged Man Whore Part 1 - Sex Stories

I was A Middle Aged Man Whore Part 1

... bathroom , pulled up my zipper and headed back out to the living room. Trish was still sitting on the couch with her legs spread and one tossed over the arm of it and I could still see her pert nipples sticking through the silk of her shirt and the roundness of her gigantic tits . I sat back down on the chair across from her. She said "The next item on the agenda is to get you some nice clothes." I said "I am not a shopper or a G.Q. kind of a guy Trish , I wouldn't know what to buy and I don't have the money anyway." She said "Don't worry Matt , shopping is my department , all I need is your your waist size and your shirt size." I said "Fuck if I know Trish , my wife takes care of that shit." She said "Well , you look like a medium shirt , we will just have to measure your waist." She got up and walked out to the kitchen and started rustling around in one of the drawers by the sink. She came back a few minutes later , handed me another beer , and had one of those cloth tape measures in her hand. She was standing there with her pussy practically in my face and she said "Stand up , let's get a waist measurement." She reached down , threw her arms around my waist , and grabbed the tape measure with her free hand and pulled it tight around my waist . With the alcohol in my system , and the fact that I hadn't been laid in a long time , my cock began to stand at attention as her hands fondled with the tape measure at the front of my waist right above my cock. She looked down at ...

... the tape measure and said "I was almost right, a perfect thirty two inch waist." I said "That's nice to know." She dropped the tape measure onto the floor and placed her hand on my crotch and slowly began rubbing my cock . I flinched and pulled back a little bit and said "Wait a second!" She asked "You aren't honestly going to tell me to stop now are you?" Again I was tongue tied and sounded like a fool as I tried to form a complete sentence. The guilt of cheating on my pregnant wife was already starting to fuck with my mind but deep down I knew that I had to deal with it if I was ever going to make this work and get some money coming in. The sick irony of the situation was I had to fuck strange women and cheat on my wife if I was going to make money and take care of my wife, what a truly fucked up situation to be in to put it mildly. Trish stared into my eyes as she continued to massage my cock through my jeans. I could feel it swelling full from the shaft to the head as she reached up with her other hand and slowly started to undo the buttons on my shirt. She could sense that I was uncomfortable about it and said "Relax little man , just consider this a working interview." As she undid the last button on my shirt and peeled it to the sides , she brought both her hands up to my waist and slowly began to un-snap the button on my jeans. Her gigantic succulent tits were rubbing against my chest and I could actually feel the pressure of her huge nipples scr****g against my skin. I ...