Tuesday morning I woke up later than normal. I walked through the house looking for anyone. By the pool scrolling her phone drinking coffee was my wife. She teased me for sleeping past eight a.m. I excused it by saying alcohol and up too late. The others went out for breakfast and tour along with getting supplies for the day and bringing in the new year on the boat. I asked why she did not go. She had done the tour before and wanted to be there when I got up.
Her reasoning for waiting became obvious. She and Tabitha had talked earlier. Tabitha gave a very detailed account of what transpired that night. After my wife telling me all of the discussion I was waiting for the hammer to drop. When I say detailed, Tabitha was very specific in her description of our position in the pool. She was very specific in her actions with describing how she would press my shaft into her slit and movements. Even the dunking she gave a listing of my hands and her tits. So I was waiting and had no excuses. In my mind I thought it was obvious to all that I found Tabitha very attractive and sexy. I was wrong.
After finishing, my wife started on how excited both Tabitha and her husband were on my new found friendship with her husband. I did not tell her that one conversation did not equal a friendship. I still did not know him so I kept quiet. She said that to get to this. She asked why I was so stand-offish with Tabitha and she thought I liked her. Confused I asked what she was talking about. This led to a very long analysis of Tabitha by my wife. The summary was as i understood it, Tabitha has a problem with insecurities and rejection going back to childhood. My wife said that Tabitha has never had a close girlfriend because of her personality and will reject others before they can reject her. That's a very short description of a very long explanation. I still did not get why I was having this conversation.
I explained that I really like Tabitha and love her free spirit of I don't care what people think. My wife said, but that's not true. Tabitha is really concerned what we think. She wants a close relationship with us and thought you were rejecting her last night. Now I was really confused. Now the kicker. Tabitha understood my statement of we were too close as a rejection. She saw my apology having my hand on her tit as a continuation of me rejecting her. After my wife's explanation I understood. I told my wife that in both cases we were alone in the pool and I was not comfortable without her being there.
My wife found this funny. She said, before the trip that Tabitha talked to her a lot about getting closer to me. They discussed boundaries that we had and they had. My wife had told her about my boss's applying sunscreen in detail. Tabitha loved the idea that I might do this. The summary of another long conversation was, my wife explaining that Tabitha is a hugging touching person in reality and wants me to be physically close to her. My wife essentially said, you know our boundaries you should enjoy this relationship as much as I do. At the end I agreed. I was excited at the possibilities and hesitant at the same time. My wife was happy with my agreeing to try.
If the others had been twenty minutes earlier they would have walked out back to a marathon sex session.
The boat was to be prepared by noon. My boss thought that was a good time for all to have the ability to recoup. Getting ready. The guys were outside talking. Tabithas husband was actually interacting in the conversation. The wives walked out in new bikinis. They were tiny leaving their asses on display. My wife and my boss's wife were barely able to cover the areolas with the tiny tops. They presented each of us with a bag telling us to change. All this was purchased by my boss on the earlier shopping trip. Turns out each wife chose a mankini for us. Tabithas husband's fit fine. My boss's was snug maybe a size too small. Mine must had been purchased from the toddlers section. Barely covered my ass crack and my dick and balls were stuffed in the front. Mine made a professional divers suit look massive. My soft dick was plainly visible by the imprint. I received a lot of teasing.
The most embarrassing and humiliating experience of my life was the walk from the parking lot to the marina and then past a large number of boats with people on them in boat slips to my boss's boat. It had to be almost at the end of the dock. I received a lot of looks, smiles, whistles, cat calls and sarcastic comments from men and women. The wives loved stopping and talking to ther boaters on the way. No sure if they were showing off their swimwear or for my benefit. Once on the boat my boss started a tour of the deck with me. The others went below to set up. We heard them laughing and getting loud as I toured the boat. When he took me below, all the wives were topless. They were celebrating with shots of a red liquor called fireball. I made a drink declining shots. After the tour my boss and I were on deck preparing to leave out.
A group of middle-aged people were getting on the boat in the slip beside us. Four men and two women. It was almost immediate, they saw my outfit and started whistles and laughing. One comment I remember was, I guess you are trying to set a new progressive trend in men's wear. I am not accustomed to embarrassment but I am now. When ready to cast off I thought I would give my wife a taste of this treatment. I called her up on deck to untie us. Out my topless wife walked. I did not get the response I wanted. She pranced and posed for them with each rope. She loved all the comments. Not sure the two women were very happy.
On the water going all three got naked. Had several boats blow horns and pass close. A few horns when at a long bridge. We stopped at my boss's favorite anchor spot. The girls were floating and drinking. We were sitting smoking drinking and talking except my boss was not drinking. Tabithas husband was a mess drunk. He was talking and slurring. He said, you will never guess what I did. He said, I was dared when we were at the marina to take an additional shot I could feel a tit. Two additional I could feel two. He took two shots and said he got to feel my wife's tit and my boss's wife. Laughing he added I got to play with my wife's with no shot. No too much longer he was throwing up off the side of the boat and sleeping below deck.
During our time there, the wives were pretty drunk. I had just maintained a sensible high drinking. Tabitha was getting more forward with each drink. Even my boss noticed. He said, you better be careful with that one she's got the hotts for you. I told him a little of what my wife told me essentially saying she's just trying too hard. I'll skip around during this time.
We were all floating and talking with drinks. For those unaware of a floating style. Take a life jacket and put it on like a diaper. It will hold you up freeing your hands for drinking and smoking. The water was I think around 76 degrees so not warm but OK.
I got on the boat to refill and have a smoke, dry off and warm up in the sun. Sitting relaxed Tabitha got on to refill. She sat beside me and we were talking. I took this opportunity to tell her that I enjoyed spending time with her the night before. Her drunk expression changed to a big smile. She said, really, I though I was upsetting you. I told her not at all. She turned and laid down on my lap. She asked, do you like me. I said I absolutely do. She asked why. I could see the insecurities that my wife discussed. While telling her the truth why I like her I place my hand on her below her tits. I can not relay how distracted I was looking at her pale areolas and those hard nipples. Not to mention her light red pubic strip. I maintained focus and completed my response. I must have answered to her satisfaction. She followed with, do you find me attractive. I again answered honestly with, very attractive. She said, tell me why.
I proceeded to give her a mostly honest answer. I should have said that I was very attracted to her pale nipples and pale pussy and loved how her inner lips just peek out and the contrasting colors of pale white, to pink to dark pink of her pussy when spread. I mostly kept it generic but honest. Now she got to it. She asked why I placed my hand there rather than on her tit. I was not honest and said, no idea why I just did it. She asked, do you want to. I was not even close to as drunk as she was. Also, I recalled my wife telling me to tease her. I said, if you were not so drunk, I do not want you to sober up and be mad. Tabitha got a different look on her face. She said, I've been throwing myself at you trying to get a reaction sober and drunk. In the spirit of teasing I responded, so you do not care where I touch you, how I touch you or when. Laughing she said, no I do not. I really wanted to get my hand on that tit and nipple but instead I responded, so I can do this. I moved my hand to her pubic strip and was slowly rubbing. She smiled and said, you can do whatever you want. She opened her legs.
As I was just playing with her pubic strip I was questioning her about everything from her life to marriage to her friendship with my wife. The most I allowed myself to do was let my fingers slide over her mound and upper slit and lips. It took great restraint not to get to those inner lips and more. This lasted a good fifteen minutes. Very early into this I was getting erect. The tiny swimsuit was in no way going to contain my erection. I had to stop and release it out the top. So here's tabithas head and face in my laps and more than half my erection inches from her face. At some point I'm having a small leaking issue. She reached over wrapped her hand around my shaft and squeezed stroking up. This cause a small amount of precum to exit. She continues to the end cleaning my shaft and getting the additional on her hand in the process. She wiped her slightly wet hand on her side and continued talking. I had to tell her I need to get in the water to cool off. She sat up and stood. She hugged me, we got on our inverted life jackets and got in the water.
The second occurrence was my boss's wife and I were floating and talking holding the anchor rope. Of the three wives she was approaching being a drunk mess. She was struggling to hold the rope and talk. She backs into me asking to hold her steady. I had no second thoughts on this one. I ran my arm under her laying my forearm across her tit and my hand squarely on her other tit and nipple. Her response way, oh my. I'm holding her and said, it's the best way. She laughed responding its quite alright, your hand is warm. We are like this for some time and I took full advantage of this playing with her tit and nipple the entire time. My boss came to the front to check on us. He also laughed and said, I see you two are fine.
During this stop my wife and Tabitha would tease my boss sitting on his lap or hug him or my wife would stand tits pressed to his back as we talked. On the way back all but my boss and I were below to stay out of the wind and get dressed. My boss asked if I enjoyed my time with his wife. I said I did. He smiled and said it looked like you did. He asked if I went further. I said, I would have but if I had my hand between her legs she might have flipped upside down in the water. We both laughed. After some silence he said, you made her one happy woman doing that. I asked how's that. He said that she thought her age would be an issue. I assured him that is not the case.
Back at the marina. All the wives wanted to run to the house. My boss took them. Tabithas husband was up from his sleep and embarrassed. I told him it's happened to everyone at some point. He asked what he missed. I gave him a short version. After we were sitting quietly. I was thinking how to present to him I did a little playing with Tabitha. After a refill I did as he did. You will never guess what happened. His eyes got big and asked what. I told him that Tabitha was laying across my lap talking and I moved my hand to her pubic strip and my fingers were across her mound and upper slit and lips. His response was not what I expected. He asked, what did she say. I told him nothing she just kept talking. He laughed and said, that's Tabitha. He asked if I did anything else I told him no. He looked disappointed but I could have been mistaken. He then told me about their conversation about us in the pool. He added, Tabitha really wants your approval of her. I told him I already approve of her. He also went into explaining Tabitha and her insecurities. I explained that I do not require a physical relationship to be close to someone. He understood and said very plainly that Tabitha will not want sex but its OK to be physical with her. I found it so odd that my wife and Tabithas husband was giving me permission and even encouraging me.
When they returned I was allowed a tshirt and my normal swimsuit. My wife and I went for a walk. She loved the attention she got from others on the short walk. I told her about Tabitha. She already knew. I told her about my conversation with her husband. My wife was drunk but was not helpful when I asked why they were encouraging a physical relationship until she said. Her response was asking me what I tell her when she asked me if she could flash, be topless, be naked, sit in a lap or anything else. I thought about it. My response was and is always just have fun and be safe. She said, exactly, that I was overthinking everything. Just stop and have fun. She was correct. To defend myself I started telling her about my boss's wifes tit and nipple. She laughed and said that she told her at the house. I sarcastically said, I can not tell you anything first. Smiling she said, just remember that and have fun. We had roughly two plus hours till fireworks.
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