Dating can be a curious business for those over a certain age, that age being 50. After long term relationships are over, especially marriage, there is an urge to explore, to catch up on things missed, to indulge in things not available in the midst of an exclusive relationship.
When Barbara separated from her husband of decades, she had opportunities. That meant allowing herself to discover some passions. While her work and living situations weren't the best, she found a much younger man attracted to her and she loved it. Off and on, for a year, Barbara enjoyed this man for help at her business and for help with her sex drive. But it was too complicated because her business partner, a borderline personality type woman, was too envious of Barbara and basically drove the young man away.
Barbara had her own emotional issues, much of them tied to a time in her life when she was very overweight. During her marriage, she had decided to completely remake her body through diet, exercise, and the knife. It basically worked so that she emerged with a very feminine and alluring figure. It helped that she didn't have any children. It also helped that her business was thriving and she had time and money.
Her husband had made a choice to chase other women. When they visited the upscale nudist resort of which they were long-time members, he embarrassingly and drunkenly chased women while Barbara was left alone to subtly oogle the younger men that she never thought would be attracted to her. While not many to gaze upon, there were enough muscle-bound fellows to which Barbara mercilessly fantasized about. The fantasies were lurid and fiercely sexual. She wanted to be taken, dominated, and left panting and spent. She particularly fantasized about young men with bulky and built up muscles. Muscle Boys, she called them.
Through events related to the divorce process, Barbara found herself in south Florida living with her difficult business partner and her business partner's husband. The arrangement worked, after a fashion. As her business brought her around the country to various historical shows and festivals, she wasn't cooped up in the house. If Barbara wasn't traveling, she sent her business partner out to sell the merchandise. If all three were in the house, Barbara kept to herself in her own room so she responded to messages from her online dating profiles.
Those messages were many. One of Barbara's photos featured her wearing a tight cat suit costume. She had scads of costumes and sundry accessories. She liked events where she could both sell her custom jewelry and show off her newish figure. The cat suit did just that. Virtually all of the men mentioned that one photo and ignored the rest. After a few months of that, Barbara felt it tiresome. As she was actively seeking a cub for her cougardom, she did respond to messages from young men. Yet the few dates she arranged with younger men were oddly unsatisfying. Sure, such young men were capable of enthusiastic sex and Barbara found it fun. But still...
The other men she dated were definitely her age or above. She enjoyed their companionship but didn't like the fact that some were pushing 70 and had health issues. Such men made her feel too old and less vibrant sexually. Barbara was persistent. She did enjoy meeting new men. It was good for her feminine ego. It was also a chance for her to get out of the house and away from her business partner.
With so many incoming messages commenting on her cat suit costume in her online dating profile, it was a message that mentioned another of her photos that got her attention. The man who sent it had a rather goofy photo of him wearing a metal colander his head. His message included a comment on her rather creative headdress in one of her profile photos. His online profile words were well written. He was basically bald, middle age, and clearly not fat. He listed 5'11" as his height but Barbara knew that most men added at least an inch to their actual height. Regardless, if he was over 5'8" - her own height - he might be interesting for a date. Like her, he didn't have any children. She responded to his message.
His name was Justin and they were soon dating. It was a low velocity dating relationship. He worked a standard white collar, 9-to-5 job in Boca Raton and with Barbara's festival and show schedule, they didn't have much time together. Still, they saw each other when they could and soon established a comfortable and easy rapport after two or three months. They didn't live too far from each other when she was in town so dates and sleepovers were easy to arrange.
If discretion is the better part of valor, Barbara and Justin were well beyond valor and into military secret levels of discretion. Neither asked too many questions about their respective pasts, sexual or otherwise. Only cautiously did they reveal small parts of themselves and their histories. Based on hints and statements, Barbara learned that Justin once went to the same upscale nudist resort in central Florida where she and her husband were once members. She didn't ask for more details and he only said that he went with his last ex-wife and another couple for a weekend.
She did reveal that she enjoyed attending fetish events so she could show off her amazingly creative costumes but not necessarily indulge in any BDSM activities. Justin understood Barbara's need for attention and indulged her desire to attend those public fetish parties. She dressed in sexy and outrageous costumes and gave Justin some interesting outfits to wear.
They attended one large fetish party that advertised itself as "extreme" where public displays of sexuality were allowed, unlike the other fetish parties they attended. To their mutual disappointment, there was little action to observe. When she told Justin of her disappointment, he thought that this was a way of indirectly telling him that she probably has some voyeuristic tendencies with hopes that he would have a plan. But she was indulging him more than her preferences.
Justin did have a plan. He suggested going to an on-premise swingers club in Fort Lauderdale. It was a night when they were chatting online. When Barbara saw the text "we should go to a swingers club if we want to see more," she was not particularly surprised. Justin had described a previous job as the editor of an adult magazine and that involved doing research on adult activities in the city where he worked. He knew all about the fetish community, BDSM, and swinging.
By this time, Barbara had moved an hour and a half north of Fort Lauderdale so they chatted online quite a bit along with the occasional phone call. The distance between was not a big issue because she frequently drove down to stay with Justin and deal with her business inventory still in storage close to his apartment. While online, Barbara found an appropriate cocktail dress to wear and also some crotchless pantyhose. Justin ordered them online for her.
They made plans for a Saturday night a couple of weeks later when she wasn't working a fair. Like any couple in a dating situation, they communicated frequently and despite the distance, each felt a nice, secure warmth knowing they were together but not connected at the hip. On the scheduled Saturday, Barbara smiled when she knocked on the door. Justin's dog started barking loudly.
"Rex, get away from the door," she heard Justin shout. He opened the door and she stepped into his apartment. They kissed, the small dog trying to jump on her. Barbara was well pleased to be there. She had brought lots of stuff including some home-made food. After getting sorted and then relaxing with some wine, Justin got the dress for her to try on. It was a bit of a gamble ordering such a dress online. Right in the living room - the blinds were closed - she stripped down to her thong and pulled the dress down. The back was too low for a bra and the front was loose so that her ample breasts were covered only with the black fabric.
"We were lucky," she told Justin as she adjusted the front.