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Gambling Junket
11/08/2024
Still newlyweds at less than a year and we were talking to a family friend at a function, and he was telling us about always going to Vegas, Atlantic City and it was always comped!

We were in our early twenties and Jack was mid-fifties. She loved to hear his stories as she had wanted to go to a casino for a long time to play slots. This was when Biloxi was just getting going well and Jack told us that he could get a room and meals if we wanted to go. She was all for it.

He told us up front that he could not get two rooms so we would have to be good with sharing a room with him. She just wanted to go and said that would not be a problem. A five-hour trip for us so we headed down one Friday and was going to stay until Sunday. Got checked in and he was given a suite, and it was super nice with two queen beds.

She immediately wanted to go play and we went downstairs, and Jack went to play blackjack while I sat with her while she played slots. After about two hours of playing, she had lost all the money we had brought with us for her to play. We then met Jack to have dinner, and she was kind of quiet and Jack noticed and asked was she not having a good time.

She would not say much but after dinner when she excused herself, I told Jack the reason and that she already lost all the money she brought to play with. His response was oh that is not good so early into the weekend when we will be here all weekend. But without hesitation he said he could let us have some money, but she would have to make it last. When she came back to the table Jack handed her two hundred and said sweetie make this last.

She was happy again but close to midnight she was broke once again. Me and her had walked outside and she could not believe she had lost again. After a bit she asked did I think Jack would loan us some more money and I replied loaning it probably would not be an issue but paying him back would be. She was determined and said maybe I could make it worth his while. I knew exactly what she was referring to and told her as long as she made sure he knew it was not a loan.

We headed up to the room and was watching tv when Jack came in a little after us and was telling us he had a good night at the tables and looked at the wife and said did you have some luck sweetie, and she quietly said no she had lost what he loaned us. He quickly told her it was not a loan and that he wanted us to have a good time. We were laying on the bed, but she was still dressed in jeans and a blouse.

She said to me would I mind going and getting some ice and some coke and as I headed out, she whispered to me to take a little time to come back. I took about fifteen minutes and walked back to them sitting on each bed talking to each other and she was smiling again and showed me a handful of money and said Jack is helping me out again. She had her coke and then said she was going to get changed for bed and grabbed several things and went to the bathroom.

Stayed in there for a little while and then walked back in the room with a little black baby doll nighty set on. She kind of paraded around the room getting coke and looking out the window and Jack was able to see all of her. It was not getting close to three and Jack said he thought he would get ready for bed also and went in the bathroom and came out a few minutes later in just his white undershorts and got in his bed.

She waited a couple of minutes and then kissed me and whispered in my ear that she was going to get in bed with Jack. Lights were still on so she got up and walked over to Jacks bed and just said you want some company and he replied sure sweetie. She got in bed with him and he immediately put his arms around her and started messing with her. Lot of moving around and only minutes later she dropped his undershorts beside the bed followed very shortly by her little panties and nighty top.

She was on a mission to please him and was driving me crazy when she got up on her knees with her ass towards me and starred going down on him. It did not take long for Jack to work her into a sixty-nine position and had his arms on the inside of her thighs and was really working on her. After a while she slid off of him and then turned and straddled him. At one point she looked over at me and tried to smile but was biting her lip which she does when she is enjoying herself.

Jack eventually turned her over and got up between her legs and she immediately wrapped her legs around him and locked her ankles. My first thought was dam he has been going at it a lot longer than I do. I was watching her and know that look and that she came while he was fucking her. He continued before tensing up and kind of put his head back as he filled her. They laid there a minute before Jack got up and went in the bathroom. He came out a few minutes later saying he was going outside to have a cigarette.

He walked out the door and the first thing she said to me was oh wow he is good. he told me when I left, she thanked him for the money and asked could they maybe work something out for some more and Jack actually told her that was not necessary, but she told him she did not want it as a loan and wanted to make it worth his while, so Jack asked what she had in mind and she told him he could have her and he asked did she mean in a sexual way and she told him yes. He asked was I on board with that and she told him yes and that I had seen her with another guy before already.

When Jack came back in, she still had not gotten dressed and as I found out had no plans to. I kind of opened my eyes as some sun was shining in and I look over to see Jack fucking her again. They finished up and went and got in the shower together before getting dressed and us going to breakfast. She gamed on her earned money Saturday afternoon before we headed back to the room to get dressed for dinner with her fixing her hair and make-up naked in front of Jack.

He played blackjack and she played slots until about one am and we headed to the room, and she told Jack that she wanted a repeat of last night which he gave her. Nothing was ever mentioned on the trip home, she ended up winning money as did Jack. He did become a frequent visitor to out apartment until it just slowly fizzled out with him just coming around very once in a while before stopping completely.


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