I have a great looking lady working for me who just went through a bad divorce; she has seemed real down and has spent more time at work than normal. Being a caring boss who also finds this lady very hot, I decided she could use some excitement in her life. Since the divorce she has gone through the phases where she wanted to hide her body, since she felt no one would want to look at her to her current phase which is when you are built with 36D’s and a great ass you should show it off and see what happens. I really like this current phase let me tell you. In the office and traveling we started to play this game, (I dare you). At first it was simple things like trying a new drink or sometimes wearing a special low cut top, but lately it has turned into a much more fun game for me. Lynn is in her early 40’s but really only looks like 30’s. Since we work out of a small office operation and yes we travel quite a bit this game has gotten to be a lot of fun. The first dare that I gave her was to test to see how far she would go with this game. We were driving down the interstate and I dared her to strip and let me play with her as we passed trucks. She thought about it and agreed if I would agree to buy her some new sexy tops. Agreement was made and she removed her shoes and slacks leaving only a lace thong. Next she removed her knit top which contained her very nice breasts and hard nipples. She looked over at me and told me not to have an accident because she did not want to have to explain why she was in this state of un-dress. With that she pulled off her panties and reclined the seat back. I moved to the left lane and began to pass truck after truck, horns went off and she kept closing her eyes, I moved my hand over and rubbed her tits and then moved down and fingered her pussy, boy was she wet. Since we were in route to a hotel for the night I had her stay nude until we got to the hotel. That night we screwed for two hours as she was so excited about what she had done. The second dare turned out to be a bit more challenging since it involved actually letting someone touch her in an undressed state. It was about a week later; Lynn kept telling me about this cute guy (actually kid) who is with a courier service we use for shuttle between two offices in town. He is about 18 dark brown hair and perhaps 6 ft tall. He mows yards on the side so he is very tan and well built. Our office is actually in my home so there is a full bathroom right across the hall from Lynn’s office. So with this dare I was to stay in my office but not let the kid know I was there. She was going to leave a note on the door telling him to come on in and come to her office as he has done many times. On this day he was to arrive at 2 pm, which he did right on time, but when he came in Lynn was actually in the bathroom fully nude as she had just come out of the shower. All went as planned as he came in and came down the hall, but of course he stopped at the bathroom door and was very shocked to see Lynn naked. She played the part well as to be shocked to see he and then she attempted to wrap a towel around her, but with her build it was really not possible. He attempted to look away during this encounter but his eyes were fixed on her. She told him she was not expecting him so soon and she was very sorry to not be dressed when he came in. She told him she had just been to her lunch workout and wanted to shower before going back to work. She told him he would need to wait a minute until she could get the envelop that needed to be taken, then she said well what the hell you have seen it all, so follow me and I will get it for you. As she entered her office she let the towel slip exposing her breasts and while she was reaching for the envelope the towel fell to the floor. She attempted to cover herself but again he got a full view including her freshly shaved pussy. She apologized again but the kid by this time had a lump in his shorts that showed his intent interest. Lynn looked down and said, “My from the lump in your shorts, you must like what you see” the kid who had turned very red in the face said he really did. Lynn handed him the envelope and at the same time let the towel drop to the floor. She said would you like to rub lotion on my back since I cannot reach back there. He grabbed the lotion from the corner of her desk and as she turned around he rubbed and rubbed lotion on her back and butt, she told him he had great hands and asked if he would like to do her front. He was nodding as she turned around and let him rub her breasts , neck , arms and belly, then his hands moved down to her pussy and she kind of leaned back and spread her legs a bit to let him rub her smooth pussy. I knew she did not want to have sex with this kid, so when she reached down to give his lump in his shorts a rub; I called her phone, which was her cue to allow her to stop this dare if she wanted to. Lynn quickly grabbed her towel and told him he needed to go as her boss was due back any second. He leaned over and kissed her right tit and said he would be happy to rub her down any time. I think we both won on that dare! The final dare happened yesterday when we were staying in a hotel. This hotel had two towers but only one was completed the other was still being finished, which means workman working all night in most of the rooms facing our room. Since we were on the 5th floor I noticed that the painters were working in the room’s right across from ours but on the 6th floor. The towers were only about 25 feet apart with a small courtyard between the buildings. Upon arrival we conducted business and then went back to the room. I ask Lynn to put on a very sexy low cut short black dress that she had brought with her on the trip, but no underwear and hi heals. This dress was very low cut and her breast were very visible especially went she sat or moved. We when down and had dinner but left the drapes open to the courtyard, I also left the light on and tossed out on the bed some of Lynn’s sexy underwear for the guys across in the other building to get a view of. We had a great dinner with our waiter spending most of his time looking down Lynn’s dress whenever he was at our table. After a few drinks in the bar, I explained to Lynn what my plan was. She was really up for anything at that point because she was really getting into the role of being sexy. When we got into the elevator I put one hand in the top of her dress and played with her nipples and the other hand went straight to her pussy, with one rub I found her soaking wet. I knew at this point she would not turn back so when we got to the room I opened the door and turned the lights on and off a couple of time, just to get some attention. I let Lynn go into the room first and then I quickly ducked into the rest room which was just inside the door and back in the darker part of the room. My plan was to be able to watch what was going on in the room or rooms across the courtyard from that position. I had Lynn go into the room and stand in front of the mirror. It was only a matter of seconds until the painters who had already spotted her underwear on the bed gathered at the window. One was about 20 with a good build and no shirt on; the other was Mexican I think and perhaps about 30 years old. In about 30 seconds the lights went out in the main room they were painting but the bathroom light was still on letting me have a clear view of then in the window. I had Lynn go into to her act, she spent some time getting out of her dress and then rubbing her tits and legs with some lotion. She looked at the underwear on the bed and lay down on the bed with her legs spread toward the window. The guys at this point had a complete view of her on the bed. She reached down on the floor and got her pocked rocket and began to work it around her pussy. She was really getting into this she was pinching her nipples and rubbing her pussy to the point I thought she was going to explode. I had not figured out how this dare was going to end, should I come into the room, should she get up and come to the bathroom and just turn off the lights, I was really not sure, but then I noticed that there were a bunch of guys in the room watching, I would get the entire painting crew, but I noticed that the younger 20 year old was not in the window. I figured he must be jerking off somewhere or perhaps he had seen enough. Just then I heard footsteps outside our room and I could see from under the door someone was standing at our door. Not sure how this was going to play out I waited in the bathroom and then there was a small knock on the door, Lynn got up from the bed and came into the bathroom and said “what do I do”? I looked at her great looking body and said quietly, answer the door. She wrapped a towel around her but it really only covered her tits since hotel towels are not know for being large. She unlatched the door and turned out the lights in the room. When she opened the door, there stood the young painter, he smiled and told her she really should close her drapes, Lynn, as cool as possible, said did you not like what you saw. He turned a bit red and said, yes he really did. He then said that his buddies bet him 100 dollars that he would not come over and be able to get into the room. He said they also bet him 500 dollars that he be able to touch her tits and pussy. Lynn said, “wait a minute” and closed the door. She looked at me and said lets help this guy out. I said ok but he needs to know that I am here, so she opened the door and since the room was dark I told the guy to come in and said we will play along to let you get your money but you have to do exactly what I tell you. He was a bit shocked but agreed. Lynn turned the light back on and this shirtless young man came into the room and walked over to the bed. Lynn dropped the towel and walked over to the young man. She kissed him on the chest and with shaking hands undid his shorts and let them drop to the floor, she then slid his white underpants down and off exposing a nice 8 inch cock she took it in her hands and started rubbing it which it sprang to live from. He was all hands rubbing her tits and trying to finger her pussy. At that point I told him to move over to the window and close the drapes. Just as he was doing that Lynn took his entire cock into her mouth and sucked him. As the drapes closed he smiled and waved at his buddies. When the drapes were closed Lynn kissed his cock and stood up and looked at me. I had moved from the bathroom to the bedroom but was careful to not be seen by the observers. The young man thanked us for playing along and we thanked him for playing our game. As he was reaching for his underwear Lynn said, you know I would like one more taste of your cock. With that she took the full 8 inches and sucked him off. He blew a load that filled her mouth and then some. I know he wanted in the worst way the screw her but that fun was reserved for me after he departed.

We now play future dares so if you have an idea just let us know.