A number of years ago the wife and I were watching a special on HBO about hookers in NYC. I could tell my wife was getting pretty aroused and we wound up screwing like teenagers. I asked what turned her on so much about the program and she admitted to me that she had always fantasized about what it would be like to be a street hooker.
I suggested to her that if she was interested in finding out what it was like we could play out a fantasy of mine where she played the part of a hooker and I would pick her up and be her client. She thought a moment and then she said she didn't think she could ever do that.
A few weeks later we were coming back home from dinner at a friends and I purposely took a detour so we had to drive through the area where the hookers hang out. As we drove past a group of hookers I teased my wife that I could drop her off for a couple of hours. She was completely aware of what I was up too and didn't miss a beat with her come back saying she didn't have her working clothes on. We didn't really talk much after that but I noticed she was intently watching the women as we passed them. When we got home my wife was so aroused the we didn't even make it to the bedroom and ended up fucking in the middle of the family room floor, I was amazed at how wet she was. Afterward I told her that I didn't care if she ever lived out her fantasy but I really liked how horny it apparently made her when she thought about it. She giggled and said, "I'm glad you do...and by the way that will be $50.00." I just laughed at her and told her to put it on my tab. Over the next several months we started driving through the stroll area with some frequency and every time we did my wife would get extremely aroused. When we would get home we always played the hooker/john game and the sex was fantastic. It wasn't long before my wife and I would negotiate how much I would have to pay her to fuck me during the drive home.
On one or our little drives I suggested to her I could drop her off on a corner and then drive around the block and stop to pick her up like a real streetwalker. Unfortunately she said no. During the drive home that night she told me the reason she didn't want to take me up on dropping her off and then picking her up was because she was concerned someone might recognize her. She said the area was too well known and she didn't want to take that chance even though it excited her to think about it. Several weeks after that discussion I was driving back home from a business meeting in Chicago. Just north of St. Louis I ran into a traffic jam on the highway. It was about 9 p.m. so I figured there had been an accident. I got off of the highway thinking maybe I could go around the traffic. I wasn't real familiar with the area but was pretty sure I could figure a way around the traffic.
I was only a few blocks into my detour when I saw what I was pretty sure was a hooker walking down the street. A couple more blocks and I saw three women standing on a street corner, no question, they were hookers. I drove a few more blocks and it was obvious I was past the area they hang out. I turned around and drove through in the opposite direction just to be sure I wasn't mistaken. Sure enough, same women, this time one of them was talking to a guy pulled over to the side of the street. I began to wonder if perhaps this might be someplace my wife could/would finally live out her fantasy. I spent the rest of the 2 hour drive home thinking about telling my wife about what I had discovered and wondering how she would react to the information. I didn't get home until after 11 p.m. and the wife was already asleep when I arrived. I was disappointed but knew I would have to wait until the next day to share my discovery.
The next morning she wanted to know how my trip went and I told her about what I had found. I could tell she was interested but also very hesitant. I suggested to her that we take a road trip so she could check it out and perhaps. I told her even if she decided against it we could do some shopping, have dinner and spend the night in the St. Louis area. She quickly agreed to our sight seeing trip. We got to town about noon my wife insisted we go straight to the area and check it out. Given the time of day, even though it was Saturday, I didn't expect anything to be going on. I have to admit I was anxious to show it to her. When we drove through I realized the area looked a bit more rundown in the daytime than it did the night before. There were several bars and just after we passed through the area I had seen the hookers there were two little cheap looking motels. I turned around to go back through the area and asked my wife what she thought.
She didn't immediately answer me but as we drove down the street the car in front of us pulled over and a hooker got out of the car, apparently being dropped off by a customer. As we drove past her she waived at us and my wife told me she wanted to come back after dark to see what it was like then. We found a hotel and got a room for the night. My wife was pretty unusually and I thought perhaps she really didn't want to proceed any further with this whole thing. We had dinner in the hotel restaurant and then went into the bar and had a few drinks.
I hadn't said anymore about going back to the stroll area and decided that if she didn't bring it up I would just let it go. I was about to order another drink when my wife told me to go ahead and have one more but she didn't want one, in fact she was going back to the room to take a shower. I ordered another scotch and watched as she left the bar and headed for the elevator and hoped she was preparing for an adventure. I didn't rush finishing my drink, all in all, I headed back to the room about 25 minutes after she had left.
I wasn't really sure what to expect when I got to the room. I was hoping she had showered and put on a slutty outfit and was waiting to head back to the stroll. On the other hand I figured she could just as easily be in her pajamas and ready for bed. When I got back to the room the bathroom door was closed, I knocked and she said she would be out in a few minutes. I turned on the TV and was flipping through the channels when my wife walked out of the bathroom.
When I saw her I instantly knew what her plan was. She was wearing a truly slutty outfit. She had on a short flimsy white skirt, a red sheer blouse with a sheer black bra underneath and red hooker heels. Her skirt was flimsy enough that I could tell she was wearing a black thong under it. She hadn't stopped with just the clothing either. She was wearing really heavy slutty looking makeup and gaudy, large costume jewelry. Needless to say I was immediately hard. I got up to give her a hug and kiss but she pushed me away saying we needed to talk about what we are going to do. I sat back down on the chair and she sat on the bed facing me. She told me that after we got there she would decide if she wanted to get out of the car. She said that if she did get out she wanted me to understand what it was she wanted to do. She told me not to worry she didn't want to really turn tricks or anything but by the same token she hoped she would at least have someone, other than me, try to pick her up.
As she told me this I could tell she was not sure how I would react and I didn't make her wait long to find out. I told her that if she remembered our first drive through the hooker area at home I had offered to drop her off for a few hours, I explained to her I was not completely kidding and assured her I was okay with it. I asked her exactly what she had in mind for tonight and as she explained it to me I got so hard it actually hurt. It was at that point it finally hit me she might actually do this. We left the room and instead of using the elevator, she didn't want to be seen dressed the way she was in this hotel, we used the stairs, we only on the third floor so it wasn't a big deal. Our car was in the parking garage and it was now about 10 p.m. and no one was around. We headed for the stroll and the whole way there I could feel my heart pounding. As we reached the area it was apparent that it was much busier tonight than it had been the night before. While I didn't actually count how many working girls we there had to be 20 or more.
We drove the entire length of the area and I pulled into one of the cheap motels to turn around. I asked my wife what she thought and she said she couldn't wait for me to drop her off. I reached over to kiss her and she again pushed me away reminding me about what she had told me back in the room and telling me that I had to really pay for it tonight if I wanted her.
I drove back and turned down one of the side streets close to the middle of the area where the hookers were. I made a u-turn and pulled over to the curb several hundred feet from the intersection. My wife didn't hesitate at all, she opened the door and climbed out of the car and closed the car door behind her. As she walked away I couldn't really believe this was actually happening. I could clearly make out her silhouette through her sheer clothing from the street lights.
The sight of her walking away, her ass swaying as she walked made me lick my lips in anticipation of what was about to happen. My wife of 25 years still attractive at 48 years old. At 5'6" with a medium build except for her 40D breasts. Her stomach wasn't as flat as it was in her youth but her bubble but and fantastic legs more than made up for that. When she reached the corner she stopped for a second and then began walking up and down the sidewalk. Even from where I was I could see the outline of her bra through the sheer red blouse. The plan was that I would wait in the car as she strolled back and forth and that she would stay where I could see her. There were two reasons for this, first she said she would feel safer if she knew I could come to her rescue if something happened and second, I wanted to be able to see her if someone stopped. We had agreed that I would wait about 45 minutes before I drove to where she was and propositioned her like I was a john. There was a pretty steady stream of cars coming past where she was standing. It was pretty easy to tell which ones were there looking for dates even if they didn't pull over to the curb. At first my wife was just slowly walking back and froth, she would look at the cars as they drove past but didn't really make any gestures for them to pull over or anything like we had seen the real professionals do.