One of the most important occurrences of my wife's trip was her interactions and conversations with my boss's wife when alone. I know I'm not getting the depth of their conversations exact and leaving off details. They spent a lot of time talking about themselves, husband's, married life to husband's that obsess about work, sex lives, their enjoyment of nudity and being exposed. During Thursday morning my boss's wife was explaining to her that she really appreciated us and especially my wife. She told her how much my boss looks forward to meeting me on trips now. My wife discovered that my boss tells her everything he and I talk about on our trips. How much he enjoys me relaying some of her activities. My wife told her the same about me hearing of her exploits.
In clearing the air to speak, this got both wives comfortable with each other because neither had anything to hide or be embarrassed about. His wife explained how much her husband wanted the same relationship we have with Xavier and his wife after hearing us talk about them and how close we are. This Thursdays morning visit gave both the opportunity to ask each other and discuss opinions and relationships. My boss's wife absolutely knows that the husband's are very loyal and trustworthy.
Enough of the rambling. Back to the hiking. When they were done and walking the path my boss's wife removed her top. She told mine that her husband love to walk this path with her topless. My wife played a little coy. She asked about getting in trouble. She told her that is not an issue in the two years she has done it. My wife kept her top on till they passed a couple. The man smiled and they both greeted them as they passed. She looked at my wife and said, see no issues here. She prompted her to remove hers. My wife did. They continued talking and siscussing. My wife said in the forty five minutes to a hour they walked they passed no less than twenty people, mostly men with an occasional couple. All either said nothing but smiled or greeted them with good morning. They put their tops on for the ride back.
She said they spent the morning, lunch and until around two in the afternoon topless at the pool continuing to ask each other questions and discuss. Around two my boss emerged and announced he was free the remainder of the week. He also told my wife I had done an excellent job in his absence and would be home on a late flight that night. Their Friday and Saturday plans was to go boating. After confirming my boss called the marina to have his boat ready for early Friday morning.
He took a picture of the wives topless in their sun chairs and text me. He text, great job with meeting, thank you, I'll now sign off and enjoy my comany. I did not get it till on the way to the airport later after dark. I responded, thanks and be careful, don't let them drink too much, my wife gets a little uninhibited when drunk, as you know. Sitting at the airport around nine thirty I get a response of two words, too late.
After ordering his boat. They sat around the pool talking. His wife took this opportunity to somewhat relay their previous discussions. My wife was surprised by my boss's responses. Her description was he responded with a gentle vulnerability. She loved the discussion and told me that he really bragged about me and how much he trusted and needed me. He thanked her several times for allowing him to have me. Until five she said they sat out moderately drinking. He took the ladies to another favorite restaurant and drove the jeep around touring his favorite spots. She said he requested that both ladies wear their tiny bikinis since the restaurant was outdoors. She did but wore a wrap to cover her exposed ass. Also he asked her not to have the top so tight. She argued that they were going to a restaurant and when not tight it will not keep her covered. For some reason his wife did not have the issue. She said it was because her tits sagged and my wife's were firm. She relented and had to adjust walking and riding in the jeep. She has had the top on around me and did not have the escape issues. She positioned the bottom of the cups and tied it loose on purpose to cause this effect. It works perfectly for bouncing boobs. She never told them.
Sitting at the outdoor table she said it was relatively empty with two or three tables. The bartender was their waiter and knew my boss and his wife. They introduced my wife. Not long my boss saw my wife checking her coverage. He said, you should just let it go. My wife said, ill need more drinks. His wife ordered her favorite. My wife said, it was strong and sweet. She told both that he should appreciate all the boob that's out on both us. My boss assured her he did because he never lingers like he's doing. Appetizers and several drinks later she said she was feeling the effects. Announcing a restroom break the ladies headed in. In the restroom getting ready to head back she looked in the mirror and a good portion of areola was exposed. Starting to adjust my boss's wife said, just leave it, there's no one here that will mind. She was referring to young people. My wife said it was mostly empty inside too and other than a few older men at the bar, was older couples.
She did adjust some but agreed not to touch it again. She did not think anyone noticed on the return to the outdoor table. Sitting looking down she said, the nipple was covered at the seam but areola was exposed. Her immediate thought was, if the top was floral rather than black it would not be so obvious. His wife told him that they made a deal, she said she would not adjust again. My boss loved it. When the bartender returned to take drink and food orders she said she knew exactly when he noticed. The top had very little lining and her nipples were hard and the one pushing at the seam was really trying to escape. He did a double take and smiled but took all orders from across her looking at her rather than moving around. He was very attentive his next few trips. Only one other table was outside after finishing the meal and she really needed to go to the restroom. She told them. His wife said, ill go too just to make sure you keep your challenge.
By the way, in their discussions my wife had told them of our challenges and her activities in some. My boss had already relayed those to his wife by our conversations but were now using it. My wife complained saying just walking inside will cause her nipple to escape. They joked with her. She asked his wife if she would just recover so nothing else escapes on the way in, that way I'm not adjusting and I won't touch it coming back. She declined. My boss then offered his assistance. My wife quickly agreed. She said he got up and reached across her running two finger under her cup across her nipple and others on top slowly pulling the cup across and covering making sure to keep two fingers on her nipple then released. My wife said, thanks and quickly headed to the restroom.
Looking in the mirror the cup had stayed pretty much in place. My wife returned with mostly covered. When done they were getting up to leave. She said my boss pulled her chair assisting her up. Once up he hugged her roughly. She asked what that was for. Smiling he was looking at her. She looked down. One nipple was completely out. The other was almost. She crossed her arms laughing saying not fair. He did the same to his wife. Nothing exposed. He reached and uncovered one and partially another. She did not even attempt to cover. He said, no covering. My wife said not part of the deal. They walked out with the bartender getting a good look at her tit. My wife kept hers covered.
Back at the house by the pool. The were drinking again but my wife said she slowed down a lot. Jokingly she accused my boss of taking advantage of a challenge. He agreed he did. By nine o'clock she estimated time, she and my boss's wife were naked in the pool. My boss stayed in his swimsuit. Only a few things occurred to this point. My boss's wife started trying to dunk her husband but unsuccessful had my wife assist. They did this three or four times and in the process she said her tits were grabbed several times each attempt along with his hands on her ass. She accused him each time of cheatting doing this. He just said two aginst one he had to have some advantages. They laughed. Later his wife went to bed.
My wife and my boss hung out together by the pool. They discussed his touching her to date and she wanted to hear his thoughts about it and what he thought his wife's thoughts. He essentially repeated his wife's responses and said he would not intentionally offend her or me. She was pleased with his responses. She said he was really similar to my dad except more forthcoming with his thoughts but just as protective. He brought up her masturbating pictures. She asked him what he does with her pictures. He took her to his office. He showed her that none were on his cell. He opened a safe and had a flash drive. Plugged it in his computer. She said, he had hundreds of pictures of his wife. Some with her giving him a blowjob. Some with his penis fully inserted and others in various places like beaches, boat, jeep, pool. Pretty much anywhere. He had all hers stored on his drive also.
She stopped on a selfie of his wife standing topless with him behind her her, had his hands on her tits in one and lifting pinching her nipples in another. She told him that she liked these most. He said they were two of his favorites. They went back to the pool talking. He was good and drunk later and asked if she would masturbate for him. She told him she was not in the mood. She said later they were talking about boating and she was tired coming off her drunk. She mentioned that she was about ready for bed. He offered to carry her again. She said he was definitely not in a condition to do that. She teased him saying you just want to touch my boob. She said he admitted he did. She told him between the restaurant touching her nipple and the countless times he grabbed her tits in the pool he should have had enough. He kept telling her that he was not too drunk.
She said in her half sober mind she was listening but knowing he was not capable. She said she was thinking how earlier his wife was encouraging her to let him carry her and how she was supportive of him grabbing tits in the pool. When he stopped, she asked, what if we do a selfie copying the one we just looked at of you and your wife. She caught him off guard by his expectation. She said, the one where you are behind her. She said he smiled big and responded, can I keep it. After seeing some of her close up pussy pictures he had she said, as long as no one sees it.
He came back with his phone handing it to her. Skipping additional discussion. She stood up. While looking for the camera he got behind her and ran his arms under hers placing a hand fully on each tit lifting and squeezing. He did it so quickly it startled her. Sill looking for the camera she said, I'm not ready yet. She was sure he was smiling, he said, I am. She said it took a good ten seconds to locate his phone and set for selfie. He was as she relayed gently squeezing and releasing her tits. Now posed. Looking in the camera he was smiling big but his hands covered her tits. She said after what was two purposefully failed attempts at trying to get his hands placed, he finally had fingers open with her hard nipples poking out between. She snapped the picture.
She said in all he was well over a minute playing on her tits. After both reviewing and approving the picture she said, time for bed. My drunk boss asked what about the second. My wife said, ones enough. He argued that he would have chosen the other. She relented taking his phone back. He immediately assumed his position with hands under her tits lifting with his thumb and forefinger squeezing her hard nipples. She said, of course he hands her a locked phone and took his time giving her the code saying he couldn't remember. A good fifteen seconds of nipple playing she was ready. She said not much longer and they both approved and went to bed.
My wife called and I was driving home from the airport. She gave me a full accounting of the trip since our last call. She was somewhat worried about my response to all the tit and nipple touching. I again relayed that if she was having fun she should have given him a full on masturbating show. She said that she thought that was too much. We mainly discussed all what she had learned from both. She definitely now sees him as some form of my dad. I again told her to have fun. I gave her a short version of my trip.
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