As I turned into our driveway, I reflected on how in 90 minutes we had gone from a pleasant walk in the mall to the prospect of reengaging in some new sexual experiences.
Nothing else was said about our discussion for the next few days but I did notice that Kara had stepped up her pace of dieting and exercising. It took me digging through my old phone contacts to find the number for a fellow, Dirk, at the talent agency that had hooked Kara up with her previous modeling opportunities. We had talked on a few occasions in the past and he did remember me after I had mentioned I was Kara's husband. At first, he was excited and mentioned that they were always looking for attractive middle-aged models and he recalled how popular Kara was with the clients and customers. I hesitated, trying to find a delicate way to ask his advice. "Actually, Kara is interested in exploring something a little bit more risqué. We really enjoyed the attention she got, and she developed something of an exhibitionist streak." I paused.
After a few moments he responded. "I guess that doesn't surprise me completely as I had heard some stories. You know the kind of clientele our agency works with and obviously what happens after the assignment is over is up to the models and whoever they meet. But if you want to increase the opportunities there is something I might suggest. There's a website independently run that is something of a marketplace for models and customers some of whom are interested in, shall we say, more adult interactions. Most people remain anonymous, and all details are through mutual private communications. Potential clients post what they're looking for and the dates. Potential talent providers typically post some image images and generic descriptions of what kinds of events they might consider. Most discussions about compensation occur directly and are in cash. The opportunities range from seeking escorts to hiring extras for adult movies to ensuring there are some "amateurs" to compete in those naughty nighty and wet T-shirt contest that some bars host."
I responded, "Anything we do has to include me being present would that be a problem?"
"That might limit the opportunities, but I have seen posts where the talent indicates they bring their own security. I'll text you the website address and you can check it out."
"Thanks Dirk."
"Have fun and if you decide to use the site, don't mention Kara's age and include a picture in lingerie with a disguise or mask. I'm sure you will get some interest."
After the call my imagination was running wild. I wasn't sure if Kara would be interested. Let me say that differently, I knew she'd be interested, I just didn't know if she'd be willing to admit it or do anything about it.
Two nights later I was up till about 2:00 AM exploring the website. It was amazing, entertaining, and a little scary. There are some awful weird folks in this world. Some folks were looking for someone who looked like their ex-girlfriend or mother. A number of women seeking sugar daddies and the few fellas seeking sugar babies. Some photographers and artists, or at least people pretending to be that, seeking nude models. A catering company was seeking women to be topless servers and bartenders. One company was seeking 10 women to be topless wearing thongs in a pool for background in a video they were filming. Several adult entertainment places were seeking strippers or entertainer as they were called. There were some attractive women posting profiles and many not so much. It was clear Kara would compete well if she were interested.
There were several seeking entertainers for bachelor parties. You could tell most of these posters were novices and not sure what exactly they could say on a public website. A few caught my interest. One ad that particularly intrigued me was a fellow from a fraternity seeking women to participate in a fundraising event they were planning called "Naughty Games". They weren't particularly descriptive but did mention that it would be held off campus which seemed to be their way of saying that the planned activities wouldn't meet campus approval. I sent a note asking for more details. I followed up on a couple of bachelor parties and what appeared to be some guy trying to hire a woman to give his son some sexual experiences before heading off to college. My inquiries were rejected because I haven't posted a talent profile. It was time to talk to Kara.
Two days later that week I sat with Kara and shared with her the information about the website and my discussion with Dirk. She was apprehensive but curious and we spent well over an hour going through the site. I noted those opportunities that might be worth a follow up. My concerns that she wouldn't be willing to follow up were quickly dispensed as she mentioned she had an old wig and large sunglasses to use to remain anonymous in lieu of a mask for her profile picture. I quickly suggested my favorite lingerie ensemble to complete her outfit. Two days later we had the profile ready to submit. Fun Loving MILF; Age- just right; weight -- see pics; measurements -- see pics; Aspirations - Catch up on some things I missed while studying during college; Biggest concerns - safety, safety, safety; Conditions - will only consider opportunities in Central Florida and require my male security presence. We posted the profile and a link to a chat ap address and looked forward to seeing if we would get any reactions. We also reposted inquiries regarding the postings that seemed intriguing.
I noticed the Kara had evolved from the shy, coy and somewhat submissive participant in prior outings to being much more engaged and anxious. I began teasing her pretty aggressively, calling her a horny MILF anxious for young cock. She grinned a guilty grin and did not deny my accusation. Occasionally she expressed a concern that the younger guys on the web site might not be interested in her. As reactions to our profile posting came in, she was quickly relieved of those concerns. I was surprised at how much time Kara spent going over new postings and responding to flirtatious inquiries. I noticed she was particularly intrigued with events that involved a larger group of people. Her exhibitionist tendencies seemed to be a key motivation. But then again, a larger group would make my involvement a little easier to rationalize and less uncomfortable and would increase the chances of some chemistry between her and some guy.
Kara was most interested in responding to the naughty games solicitation but that was scheduled for the weekend we were committed to taking our daughter to her summer camp counseling position. Both Kara and I spent some evening time looking through opportunities but hadn't made any commitments. Kara had been digging through her wardrobe to identify outfits she thought might be in keeping with the younger age group she was most interested in. While she looked great in the midriff bearing tank top and blue Jean cut offs with about 1/2-inch inseams, I encouraged her to differentiate herself and play the role of a hot MILF. Dress like a sexy confident woman, tight, short pencil skirts, satin or silk blouses, stockings, maybe a little black dress. With summer fast approaching and having been monitoring the website for three weeks Kara finally signed up to be a topless hostess for a company catering a 10th anniversary alumni reunion for a private boys' high school. We weren't quite sure what would come of this event, but they paid enough to cover our hotel room and travel costs, and it would be a good chance to get our feet wet so to speak. Plus, they were fine with my attendance if I helped out a bit and kept out of the ballroom. I was anxious to see how Kara would interact with the estimated 40 men in their late 20s scheduled to attend. Kara was to be one of 1/2 a dozen women they had hired for the event scheduled four weeks away.
We had no sooner got home from dropping our daughter off at camp than we got notified of a follow up inquiry from the folks planning the "naughty games" event. As it turned out, a heavy storm had caused them to cancel their original event date, and they were attempting to reschedule for the following Saturday afternoon and evening. The change in schedule had cost them several planned participants and they were anxious to secure other women to support their event. They included a detailed list of the kinds of things the participants would be involved in. They wanted six or eight women to compete in a mud wrestling competition where the men would bet on the winners. There would be a dunk tank where they would sell chances and we're looking for several women. They plan to have a body decorating contest where scantily clad women would be decorated with various foodstuffs and condiments in a competition. Finally, they were looking for women to be in a "touch box" a three-foot square plywood box with the top configured something like bondage stocks to hold the woman's head and hands and half a dozen 4 inch holes drilled in the box. Participants would pay to put on a glove and reach an arm in the box with the obvious intention of trying to fondle the woman inside.
I immediately nixed the mud fight as I didn't want to risk Kara getting injured. I left it to her to decide which of the other events she might want to commit to. I was certainly intrigued with the creativity of the organizers and anxious to see what might come of this. The event was organized by and targeted to college guys so they would be quite young. It wasn't quite clear how this might transition from a hot afternoon of sexual teasing to the prospect of more. Time would tell.
For some reason Kara found this event particularly interesting. She agreed to participate and expressed a willingness to work whatever events aside from wrestling where she might be needed. For the next few days, she was giddy with excitement. We arrange a hotel room nearby and planned our trip. I was intrigued at how obsessed she had become with wanting to display herself and spend several hours teasing young men. She wasn't offended by working only for tips since it was a charity event. She had sorted out two duffel bags full of outfits to wear for various events. I reminded her that she should differentiate herself from the young hotties and play the role of MILF. After all, she was almost old enough to be the mother of some of the men there and flirting with an older woman would certainly have some appeal to some of the men and their egos. We found out the young men, who had to register in advance to participate for the event, weren't just poor college kids as the registration fee was $200.00 with attendance capped at 100 men and the minimum age of 21 since liquor would be sold. The fee would raise a nice chunk for charity but for $200.00 the young man would expect to be well entertained. The event was scheduled from 4 to 9 pm on the ranch of a wealthy fraternity alumnus about 10 miles outside of Orlando.
We arrived about an hour before the scheduled start time. Kara met the organizer and the other women and interestingly I was put to work filling the dunk tank and setting up sun shades and chairs. There were eight women in total, several hired through the website but others who were girlfriends and sorority sisters who volunteered to help with the fundraiser. They were generally young and attractive.
When the event started there were about 75 men in attendance with others still arriving. The first scheduled activity was the dunk tank. The women were introduced to the men with of course made-up names and then the organizer indicated that six of the women would each spend 10 minutes in the dunk tank. But to select the order, he set out a shot of Brandy and a glass of beer In front of each woman telling them that the slowest one to finish chugging would go first with the following order based on their order of finishing. That of course got the crowd excited and cheering. Kara is a light wine drinker and showed her nervousness as the countdown for the competition began. Not only was Kara well older than the rest of the women, but her outfit was also distinctly different. All of the other women were wearing shorts, tennis shoes, and tank tops, a few with a bra and a few without. Kara was wearing a snug black short dress skirt, 3-inch heels, stockings, and a white silk blouse through which one could quite readily see a lacey pink bra.
Kara did fairly well, ending up with three women ahead of her in the dunk tank. The downside was that the 30-minute wait for her turn allowed time for the beer and Brandy to have its effect. The crowd had very much enjoyed the first three contestants, each of whom had been dunked several times with her skintight soaked clothes drawing cheers from the crowd. Kara giggled and squirmed as she made her way onto the dunk tank seat. I had snuck behind the tank and tightened the trip lever spring a few notches right before Kara took her seat. She was under the influence enough to begin aggressively teasing the young men as they prepared to throw at the target. Who would have thought my wife could have been a carnival barker in another life. Kara's distinct outfit had already drawn attention, and her teasing really ramped up the crowd. The first contestant was skunked completely. The next contestant was frustrated and embarrassed when he hit the target, but it failed to trip. Kara's teasing the "wimp" enraged him but to no avail. Finally, the 4th contestant hit the target hard enough to trip the dump seat. Kara, completely soaked climbing back up to the seat was a sight to behold. Her silk blouse was virtually sheer with the lacy pink bra highlighting her substantial bust line. The wet stockings glistened, and the tight black skirt dripped as it clung to her hips and ass. Her time on the hot seat was extended to please the crowd but they were only able to dunk her two more times before her time was up. With each dunking the crowd cheered as she climbed back out and took her seat on the dump chair. With each dunking another blouse button came undone. She had quickly become a crowd favorite.
