My wife Ann and I had been friends with Tom and Lynn for about ten years now. I had known Tom from a previous job back several years ago and the two of us had been close friends ever since. Ann just loves Tom's wife Lynn, and the two of them stay in touch on a routine basis. Ann and Lynn are in their mid-fifties and they do a number of things together outside the home. When Ann heard that Lynn and her husband Tom had planned a cruise to the Caribbean it left Ann a bit jealous that she couldn't go.
I don't like to fly, and it made it almost nearly impossible that we would ever get the chance to enjoy a vacation like what Tom and Lynn were doing. I knew it had been a desire of Ann's for a very long time, and she knew deep down it probably was never going to happen.
Tom and his wife had planned out there cruise for this past August. As the days got closer I could see how excited they were. They hadn't been on a trip like this in years, and they planned on meeting up with another couple from out of town. It had been back in late July when their friend gave them some depressing news. He and his girlfriend had split leaving him with an extra ticket. With only a few weeks before the cruise there wasn't much time to find a replacement to go with him. It was then that Lynn brought up the idea of Ann going in place of his ex-girlfriend.
Mike had no problem with the idea as long as Ann would be okay with that idea. If you could see the excitement on Ann's face when Lynn ask if she like to go you knew there was no way she was going to turn down a chance like this. I am not an extremely insecure person by any means, and I had complete trust in Ann on handling things with Mike in a professional way. Mike was forty and had been divorced one time before.
He had been friends with Tom and his wife for years and I heard Tom mention his name in passing, but knew very little about him. The idea of Ann and him being locked in the same room at night was a bit concerning at first, and I even felt a bit of jealousy come over me, the thought of it also aroused me beyond belief. It only took me a few minutes to get past the idea of her sleeping in the same bed with him before I threw my support behind her on going. She may never get another chance to enjoy such an adventure, and I told her to have a good time without me.
Ann then gave me a big hug and told me how much she loved before letting Lynn and Tom know that she was going. They were schedule to be gone for more than a week, and Ann packed everything she could into one giant suitcase. She bought a new swimsuit just for the occasion along with a few other things, and I hadn't seen her this excited in a very long time.
We talked very little about Mike and the idea of her sharing a room with him as Ann had many other things to do before her excursion. In a way I don't neither of us had much too much to worry about as Ann was an adult and she can make her own decisions on how she wants to handle things.
When Ann left I gave her a big hug and gave her all the freedom she wanted. She once again told me how much she loved me, and she headed off to the airport with Lynn and Tom. The house seemed so quiet being that we were empty nesters, and it was now just down to myself and the dog. It had been later that night while in bed when I began to wonder how things were going.
I knew she had to bunk up with Mike, and even though he had been going through a nasty breakup it still didn't undermine the fact that he was man like all other men. I knew extremely little about him and I was left to waiting for her to return.
The next few days were extremely unsettling as the thought of Ann and Mike being together in such small quarters began to make me wonder. I had only received a few early texts from Ann telling me how great of a time she was having.
I figured with everything going on that she got so busy that she probably didn't have the time to send any others. She would be home soon enough so she probably figured she could tell me everything that was happening in person when she returns.
The week slowly passed and Ann returned home sporting a dark tan. Tom and his wife Lynn had just dropped Ann off when I began to notice something different about her. She had been acting a bit strange, and I asked her how things went on the trip and especially with Mike. Ann said she had a good time on the cruise, but when Mike's name had come up she tried to talk about other things.
I knew something wasn't right and later that night I asked her yet again about the two of them. She then confessed how she did something extremely wrong. It didn't really matter what she had done as far as I was concerned, and I told her that I will always be extremely supportive of her no matter what the circumstances were.
"You are going to be really mad at me with what I got to tell you," Ann replied.
Ann then went on to tell me how her and Mike had hit it off the second that they met. Mike was extremely nice and caring, and he even acted like a total gentleman around her. I began to wonder where the problem was and that was when Ann dropped a bombshell on me. She said that on the first two nights everything was okay. They shared the same bed together and Mike asked if it would be okay if he slept in just his briefs.
Ann told him that she had no problem with him just wearing his briefs to bed and that the two of them slept without incident. Then on night three is where things began to go array. They had been at a party on one of the decks with Tom and Lynn. They were having a great time and all four of them had been drinking moderately. Mike had a bit too much to drink as did my wife who rarely ever drinks.
It had been around eleven when they returned to their sleeping quarters together. Ann had already dressed for bed in a long tee-shirt over her panties. It was then that Mike asked if it would be okay if he slept with nothing on. Ann could hardly say no considering he had purchased the ticket and she was just along for the ride. She told him that would be okay as long as he goes to bed. They had a big day planned ahead of them and Ann just wanted to get some sleep.
Mike then removed everything he had on and began to trance around the room for a short time before finally retiring to bed. I asked Ann if she had glanced at him naked, and she readily admitted that she did. I now wanted to know more about him, and Ann told me that he was an attractive looking gentleman with an athletic physique. She then showed me a picture of him in his Speedo's by the pool and that was when I began to get a bit nervous.
Ann had already been in bed when Mike climbed in next to her. He told her how gratifying it is to be naked while sleeping, and he began to urge Ann to do the same. He had been getting a bit annoying at that point, and just to get him too finally shut up Ann appeased him by removing what clothing she had on. She then wrapped the covers tightly around her naked body to keep him from seeing or touching her.
Ann had been asleep no more than hour when she suddenly awoke to Mike spooning her in the bed. She said she laid there on her right side towards the wall as she felt his hand glide down across her naked body. His cock was fully engorged, and felt the head of his cock brush up against her ass a number of times. I told Ann at that point I needed to know everything that had happened, even the most delicate of details.
Ann continued and said he had the softest of touch, and that he ran his fingers from nearly her shoulders down across her hip, and along the rest of her leg. Ann felt a bit warm and fuzzy at that point. She knew he was crossing that line that had been establish from day one, but she didn't have enough courage to tell him to stop.
Mike then began to kiss her on the neck and the back of her shoulder. It sent a tingling sensation throughout Ann's lovely body as she felt a wave of arousal come over her. She didn't know if it had been the alcohol or just the fact that another man other than me had touched her in a sensitive way that made her so extremely aroused. Mike then turned Ann over towards him and began to tell her how sexy she was for being in her fifties.
Ann is still a very attractive looking woman who looks much younger that her actual age. Her body is extremely adorable and that most men would jump at the chance to be with her. Ann is nearly five foot five and around a hundred forty pounds or so, and I certainly could Mike's attraction for her. Mike apparently had a thing for women with big breasts and my wife's 38dd tits are quite special. This only added to Mike's excitement for Ann.
Mike continued to make out with Ann while caressing each of her lovely tits underneath the covers. He had one leg draped over her the top of her leg while his hard cock rested on her inner thigh. He slowly made his way on top of her as Ann did her best to keep her legs closed, but that all changed when she felt the head of his hard cock slowly penetrate in between them.
The head of his cock now touched up against her moist pussy and that was when she began to lose all control. She slowly began to open her legs as Mike took the opportunity to work a few inches of his cock in between the swollen lips of her pussy.
