This story begins a little over a year ago. I had been married to the woman of my dreams for almost 25 years. I first met Linda in college during my senior year, while she was a junior. She had an amazing body and the most stunning face that I had ever seen. We began dating and the rest as they say is history. Linda was a very conservative girl, even being a virgin when we first met. Her very conservative nature continued through our first 15 years or so of marriage, which included giving birth to our four wonderful kids. Linda was always very conscious of what she wore to make sure she was not showing too much skin. When we were first married, I'll admit that I was fine with that when we were in public, as I did not want other guys seeing too much of her incredible body.
I'm not sure if it was my age, or maybe my own self-confidence, but by the time I reached my early thirties, the idea of other guys checking out my hot wife excited me. Over those next ten years, Linda was usually willing to go topless on a topless optional beach provided other women were also putting their breasts on display. Based on the reaction that Linda got when she saw other guys obviously checking out her perfect 35C breasts, her own self-confidence grew and she would wear much sexier tops provided we were not anywhere that someone we knew could see us. So, it was generally on the vacations for just the two of us that I was able to get her to show off her body more than her very conservative prim and proper upbringing would normally allow her to do.
Although we frequently fantasized about threesomes and would even occasionally role play them out, Linda always made it clear that she had no intention to ever let anyone else touch her. After trying to introduce several scenarios to her over those next few years, I had basically accepted the fact that no other guy would ever get to feel perfect breasts, not to mention getting to fuck her. I know that should be a good thing, but I still had that desire to at least see someone else feel up her flawless tits.
It was about this time that I saw an announcement on Playboy's website. It indicated that they were going to be doing a special section in their next few editions that paid tribute to America's hottest MILFs. For those of you that may not be into the acronyms, that stands for Moms I'd Like to Fuck. The announcement stated that they were going to select the top MILFs in the country based on age groups and area of the country. It provided a website that you could submit a picture and some basic information if you were interested in being considered. Without asking Linda, I submitted a picture of her laid out on our bed wearing only a sexy pair of pink panties.
Within a week, I received an email response indicating that they were interested in talking to her over the phone to validate some information, because she had made it through the first screening. That night, I told her what I had done and after at first being very upset with me, Linda softened up a bit, finding it very flattering that they were even interested in talking to her. So, although she told me that she had no intention to pose for Playboy, she said that she would at least call them to see what they had to say. When I arrived home from work a few days later, she indicated that she had spoken to them and was actually considering it, much to my amazement and delight. Imagine, my incredible looking wife showing off her incredible body in Playboy for millions of men to see around the world.
Linda shared that they were fine if she wanted to wear sexy panties for her spread, but would require her to show her face. They told her that she would be competing in the Southeast U.S. in the Over 45 category. Playboy would pay for the two of us to go to California for the photo shoot and give her $5,000 spending money while we were here. They indicated that they intended to bring out a total of 5 ladies per age group for each section in the country, and that the woman that they chose as sexiest MILF would also receive payment of $50,000. Linda's concern was the fact that people we know may see her spread, including our own children. Although I really wanted her to do it, I decided to let her talk through it and just be supportive of what she decides. About a week later, we were on a plane flying to sunny California for her photo shoot. I won't go into any details here, but it was an incredible trip and needless to say, Linda was selected as the Sexiest MILF in Southeast U.S. for the older than 45 category.
After the magazine came out, we were pleasantly surprised that the reaction that both of us received was very positive, complimenting Linda for doing such a great job of keeping in shape and having an incredible body. After a few months, the comments wore off and things seemed to be back to normal. After Linda purchased a new mini-van with her winnings, we had a little bit left, so we decided to take a short vacation with just the two of us. We decided that it would be fun to go to Disney World with just the two of us to let us do the things that we had always wanted to do there, but had not been able because we were always with our four kids.
We had been there a couple of days and were at the Magic Kingdom when an opportunity presented itself to me. Linda was wearing a great looking pair of tight fitting terry cloth shorts that displayed her great legs and a sexy halter top that put some of her wonderful cleavage on display. We were waiting in the line for the Haunted Mansion when I noticed the couple right behind us. They were both in their early twenties and appeared very much in love. She was an attractive looking girl with long blonde hair, a beautiful face and nice long legs. The only problem for me was that she had no body. She was very thin, with no boobs or ass. Basically her body was straight down from head to toe with no curves. He looked like a guy who kept himself in good shape that had an attractive looking face with a short spiked hairdo. The other thing that I noticed about him is that he was really checking out my wife, especially her ass and tits.
I decided to tease him a bit and placed my hand on Linda's ass while we were standing in line, and think that I even caught him licking his lips a bit while checking out my hot wife. When the line began to move into the mansion, I made some eye contact with him and a hand gesture trying to suggest that when the lights dim on the first part of the attraction, that he could grab Linda's ass. I don't know if it was some kind of guy ESP or something, but he nodded his head and smiled after my attempt of giving him non-verbal permission to grab Linda's ass. When we moved into the stretching room, he positioned his girl friend to the side and slightly in front of Linda. I took a small step back from Linda in anticipation that he would slide over once the lights were dimmed. Sure enough, once it was nearly totally dark, he moved over and I could barely see him grab Linda's ass.
As the lights came back on, he quickly shifted over behind his girl friend and the proceeded through the open doors towards their doom buggy. My cock had actually gotten hard and I needed to shift my pants a bit as Linda and I followed the crowd. After we got off the attraction, Linda and I decided to have some lunch. While we were eating, Linda commented that she was pleasantly surprised to feel my hand slide up under her shirt to grab one of her breasts when it got dark, but she requested that I be more gentle with her nipples, because it hurt when I pinched it that hard. I apologized, acting as if was the guilty party, noticing that my cock was again hardening at the thought of this young stud not only grabbing Linda's ass, but getting a quick grab of one of her bare tits as well. I figured I'd never see him again, but would always remember the rush that it gave my cock.
A few hours later, as I was walking into one of the restrooms, he was about to come out. He stopped immediately and followed me back into the restroom and thanked me. He quickly introduced himself as Mike and asked if we intended to go to another one of the parks tomorrow. When I told him that we were actually just planning to relax at our resort's pool to get some sun, he asked if we were staying at one of the Disney hotels. When I told him we were and that it was actually the Boardwalk Villas, he said great since they can pool hop as members of Disney's time sharing program. I told him the time I expected to be out there and that I hoped to see him and his girl friend there.
The next day, Linda and I went to the pool as planned. I was sure to lead us to some chairs that had a few other open chairs around us and even placed our towels and Linda's cover-up over the chair next to us to ensure no one would grab it. Within a half hour, I saw Mike and his girl friend come into the pool area, so I casually removed the items from the chair next to me. Mike saw me and pointed at the open chairs next to Linda and I, and he and his girl friend made their way next to us. Mike sat to my immediate right with his girl friend on his other side. After they settled in, he and I made eye contact and he introduced himself and his girl friend Tina to Linda and I.
Mike and I proceeded to have some small talk and tried to include the girls as much as possible. Mike and Tina were young professionals recently out of college that lived in Fort Lauderdale. They were on vacation in Disney as an engagement present from her parents. Gradually, we came upon a few topics that Linda and Tina had in common, which resulted in Linda switching chairs with Mike, so the girls could be next to each other. Mike and I volunteered to go order some lunch and drinks. After we took the girls' orders, Mike and I made our way over to the pool grill. There was a pretty good size line, so it gave us a good opportunity to talk away from the girls. Mike again thanked me for allowing him to feel up Linda and said that she looked amazing in the bikini she was wearing.
He said that although he was totally in love with Tina, that her body lacked the sexy curves that Linda has, so he really appreciated the quick thrill of grabbing her. Mike indicated that he wished that he could do it again, but for an extended period of time. He apologized to me if he was out of line, but I told him I would love to see that happen as well. Over the next few hours, Mike and I used every opportunity that we were alone to discuss a plan on making both of our dreams a reality. By the time that the girls were done sunbathing, we had decided on the following plan.