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.

This is a really hot story, hope it true and I hope I run into you all somewhere. I can think of a couple of dares, perhaps strip naked and walk along the highway or perhaps get naked in a hotel elevator and then walk naked to your room. If someone see's you all the better.

After the hotel dare, we decided that two more dares would be fun, but these had to be special, something with some danger but not to the point of getting arrested or hurt. Back in the office one day I decided to ask Lynn what kind of fun dare she would like to do, you know just to get some input from her. She had always wanted to do a strip tease in from of strangers but not in like a bar. I thought about it for a few minutes and said hey, how out in from of a bunch of horny guys out in the woods? Lynn thought about it and said tell me more. I told her I would set up all up and all she had to do is perform when I told her too. The following weekend was a motorcycle rally at the local state park. This happens every year and for three days it’s kind of anything goes since really the only ones in the park are members of this group. Most are normal guys who just like to go wild for a weekend and most of the activities involve a lot of drinking and sex. Since I own an RV, I made a reservation in the camp ground that is right next to the area the bikers use for their rally. I took the RV out to the Park on Thursday so I could get a parking spot close to where the action was going to be but my good fortune shined as the first spot right next to where there big camp fire was going to be was open. Now the RV parking is about 50 feet away from the fire ring but it was close enough to allow us to be able to put on a really good show. The weather was very warm on Friday with a high in the high 80’s so when we arrived in the park most of the group had already arrived and were setting up. I had parked the RV so that are patio area was a clear view from the fire pit which was already being prepared for the first nights activities. There were about 20 big coolers already stacked around the fire pit stocked with various alcoholic brews. I had Lynn change into a micro bikini which was white in color, which set off her nice tanned body and her 36D, 26, 34 body. She had her hair at shoulder length and of course her public area completed shaved and smooth. Lynn when out and sat on the seat of the picnic table and she began to rub lotion on her body. This got the attention of every warm blooded male within 300 feet including the ones who had already begun celebrating around the un-light fire ring. Then Lynn spread a towel on top of the picnic table and laid down on the towel to work on her tan. It was not long before two of the guys called out to her to ask her if she wanted a cold beer. Lynn kind of pretended to be asleep but kind of jerked her head up when they hollered. She told them what she really wanted was some water to cool her off. One reached into a cooler and brought her over a bottle of ice cold water. His name was Jay. Jay started to hand the bottle of water; while he was undressing her with his eyes, but Lynn sat up and asked him to just pour it over her. Jay’s eyes got big and said sure, he took the cap off and began with her shoulders and then began to soak her breasts. What he had not counted on was the material of her bikini became transparent with the addition of the water and since it was ice cold her nipples reacted quickly to the cold water. Lynn’s nipples when they get excited grow too well over a ½ inch long. The thong bottom also became transparent showing Jay clearly that she had a clean shaved pussy. From inside the RV I could tell the effect of Lynn’s condition was having on Jay, since he had a tent in his shorts that showed his very hard erection. Jay told Lynn she had the body of a porn star and she should enter their wet tee shirt contest on Saturday night which was going to be held right here at the fire pit. Lynn took his hand and placed it on her now very cold wet chest and said do you think these would have a chance of winning? Jay smiled and told her, she had his vote. As it got darker, Lynn came back inside the RV and went to the bedroom to change, I told her to leave the window shade up as she changed clothes. She took the hint and did her strip tease show for about 20 guys who were now sitting at the camp fire ring and watching our RV. We had great sex that night getting very little sleep but it was I am sure entertaining for the troops at the fire pit who I am sure were watching the RV movement even though they had not seem me during the time at the camp. On Saturday morning Lynn had just pulled on a crop top tee shirt without a bra and a very short skirt with no panties when a knock came at the door. Lynn went to the door and opened it to find Jay and a guy named Rob standing there, as they looked up at Lynn standing three feet higher and inside the RV they had a plan view of her naked pussy. Jay stood for a moment and they told Lynn that the group would be having a cook out starting at 3 pm and they wanted to invite her to come over. They also told her that they had decided that at the wet tee shirt contest the winner would get $500. In cash and they hoped she would consider entering. Lynn thanked them and told them to expect her. Lynn and I talked about how to make this a fun but safe experience for her and agreed on a plan. About 3:30 pm Lynn put on a black thong, a very low cut black knit top and a pair of very small tight white shorts. Even I got a total hard on when I looked at her. She had a bit more makeup then normal and some great perfume. She walked out of the RV and went over to the fire pit which was now the gathering spot for over 100 guys and about 10 gals. They had pulled a trailer behind the fire pit and it was set up as a stage and the party had started with lots of food and lots and lots of flowing beer. Lynn walked around and talked and since there was music also danced with a lot of the guys including one guy named Rick who spent most of the dance rubbing his hands all over her tits and ass. As it got dark the bond fire lit the area so I could still see all the action and also making sure that things did not go too far. They announce the wet tee shirt contest and had the contestants go back behind the trailer and put on the tee shirts provided by the club. There were only four contestants for the contest, a slender girl about 20 with a nice body but small tits, a gal about 30 with a very nice body and blond hair, a lady about 25 a bit over weight with big tits and Lynn. The rules were simple; the girls could do anything to get the votes with the winner taking the prize. The girls were escorted onto the trailer/stage and the music began which was kind of a rap song. The contestants were shot with water and the shirts which were very thin to begin with became transparent. The crowd yelled and cheered but when the contest got going a bit more about the end of the first song, the blond elected to not remove the shirt, so she was voted out. The music started again and each girl got her tee shirt ripped off by one of the lucky guys who got to come up on stage to help. At the end of the second song, the slender gal with the small tits decided she would not let the guys take off her shorts, so she was voted out. This left only the 25 year old with the big tits and Lynn. As the third song began the guys removed each of the girl’s shorts leaving them wearing only panties which in Lynn’s case were a very small black thong. The announcer gave each contestant a change to quit but both said they were staying in the contest so as the forth song began the guys removed the panties and toss then to the guys in crowd. The girls were naked and dancing about this time several guys had worked their way up to the edge of the trailer and were attempting to finger the girls. The one other girl slapped the guy who had stuck his finger into her pussy and she stomped off the trailer into the arms of some guy, perhaps her boyfriend or husband. Lynn finished the dance and began to look at the RV for possible help. I stood ready to go to her aid but as the song was about to end and the guy on stage had finger her and them held up his finger after licking them. Lynn moved to the end of the trailer so as the song finished she could step down. As the song ended she bowed to the crowd and then ran over to the RV. I was surprised that none of the guys came after her, but they did not. In about 10 minutes there was a knock at the door and when Lynn opened the door there was Jay, he had a smile on his face and he handed her the prize of 500 dollars. Lynn smiled and told him thank you but she did not really want the money. Jay said, o no you won it and we want you to have it. After all we were really happy to be part of your dare! Lynn smile since she figured out that perhaps I had set up the whole thing for her. That night the RV really got rocking before we pulled out the next morning. O yes the second dare, she had to ride home in the co-pilots chair naked, giving anyone meeting us on the road a full view of her very happy body.