Jessie was rocking back and forth and with each thrust the dildo felt like it would go in a bit more until I felt it break thru and slid in. Slowly sh...e started pumping my as with it and she began to increase the pass. Soon she was fucking my ass hard and I was telling her how good it felt. The door bell rang and I was wondering who could be at the door at 2 am. With me in a nighty Jessie told me she would check. A few minutes later she walked back into the bedroom with the clerk from the book. What do I do?" It won't be any different than when you and I and Scott got together, just more of it. We will go upstairs, you will get undressed and we will have sex. When I'm done Scott or someone else will take my place and so on until midnight or the guys have had enough, whichever comes first." You swear that no one but you and Scott will ever know who I am?" Promise." Okay then, let's get it over with."It pretty much went as Jerry had said it would go. He went first, was followed by Scott. My looks are good but not exceptionally but what is most important is that I am really shy around women. I can't talk to a beautiful girl or woman even I my friends dare me after a lot of alcohol. That's why it has been almost a year since I had some sort of sexual experience, I know its not that long but it's starting to make me very horny.I have always had a thing for older women. I just love the way they look like and the thought that they really know what to do with a guy just turns me more. The music drowned out most of their conversation although I saw Natalie glance speculatively at me several times as Sky presumably explained my desires. After nearly five minutes of whispered discussion Natalie looked up at me and said ' O. K. ' . I looked at Sky who nodded and said ' She can do it ' . There seemed to be nothing else to say, so I settled the bill and the three of us got into another taxi which took us back to my hotel.Chapter TwoThere is always an awkward moment when you.