***All characters are over 18 and are fictional. Any resemblance to any real-life persons is purely coincidental.
...
Mike Billows entered the restaurant and looked around. It took him a moment to find, Jerry, the man he was looking for, in the crowd but found him sitting at a table in the corner. As he walked to him, Jerry stood up and they both cheerfully greeted each other and shook hands. He sat down and immediately the waitress came up to hand them menus and offered to tell them the days specials, but they both declined, only asking for coffee before she walked away.
"How have you been, Jerry?" Mike asked.
"Great," Jerry replied. "How about you?"
"Same," he replied.
"How's the realty business?"
"Great. We recently moved into a bigger office, hired three more realtors and got several more properties in our listings, we're really starting to grow," he said as he handed him a business card.
Jerry took the card and put it in his pocket.
"So why did you call me out of the blue all of a sudden? It's been about ten years since you last had to represent me."
"I'm going to right to the chase here. Remember after the last trial, you said that you owed me big?"
"Yes," Mike said, suddenly feeling nervous.
"I need to call in that favor now."
"Oh, I see."
"But don't worry, I'm not going to ask for anything bad, or would get you into any kind trouble," Jerry assured him. "But it is a big favor; it'll sound very strange but I think you're going to like what I'm going to ask you for."
Jerry was making Mike a little nervous. When your former lawyer who got you off some serious charges several years ago suddenly asks you for a favor, there's reason to be nervous. He had come a long way to change his life and didn't want to do anything to jeopardize it.
Up until about ten years ago, Mike, who used to go by a professional name, Hugo, was a male prostitute, or a gigolo some have called him. He preferred make escort because it sounded classier.
It started when he left home at 19 and had trouble making it his own. A friend he made at a night club he was working at convinced him to be a male stripper at a club he worked part time at. Mike gave it a try and found that he was a good performer and made a decent amount of money.
During that time, he had a lot of offers from his female patrons for his sexual services. He denied their requests at first but then he thought why not? Get paid to do the thing he loves to do with women. He eventually hooked up with an escort agency that gave him plenty of high-paying clients.
Several years later, the law eventually caught up to him. He was arrested for prostitution and for some drugs that he had on him at the time of his arrest. The number of drugs alone would've given him some serious prison time. The District Attorney tried to offer him a deal to wear a wire and spy on the escort agency that he worked for, in exchange for probation. The only problem was that the agency was tied to the Russian mob; not fully controlled by them, but associated enough with them that they were protected. Wearing a wire and testifying against them was like signing his own death warrant.
That's where Jerry came in. They knew each other from high school and coincidentally ran into each other on the street a few weeks before Mike was arrested. They caught up, Jerry telling him about graduating law school and getting a job with a decent mid-size firm.
Mike, of course, lied about his job, saying he was a telemarketer, which usually ended any further questions about his career. But when Mike called him after his arrest, he had to confess everything to him when asking for his help. A couple of weeks later, Jerry found some good technicalities in the police departments investigations and with their warrants and got Mike off those charges.
Mike didn't have a lot of money, wasting most of it on his extravagant lifestyle. Jerry was ok with it; he was just glad to have a story to tell his colleagues. Anytime a defender gets one over the D.A. it gets him some good respect among his peers. But Mike did promise that he was done with being an escort and said that he owed him no matter what it was.
Mike collected whatever money he had left, sold off anything he could for extra cash and left town to start a new life. He got a few real jobs, they didn't pay as well as being a high-priced male escort, but it was honest work. A few years later, a former girlfriend of his got him into real estate and got licensed as a realtor. A few years later, he was doing so well he went on his own and started his own realty business.
"After what you did for me, I wouldn't be here today," Mike said. "I'd either be in prison for refusing to wear a wire or dead for testifying. So, whatever you need, just say it."
"I need you to fuck my wife," Jerry blurted out.
Mike was stunned. He wasn't sure what he was expecting but he never would've expected that kind of request.
"What?" was all that Mike could say.
"I'll explain everything," Jerry replied.
Several ago Jerry got married to Vanessa, a very beautiful and sexually veracious woman. They enjoyed their sex lives with each other, as well as with other people. They especially liked going to sex clubs and have memberships to a few of the most prominent ones in the city.
They especially liked role playing, coming up with new scenarios to play out. One of Vanessa's favorite roles was to play a prostitute; Jerry would meet her in public places to pretend to be a man looking for a good time and pick her off the streets and take her to a hotel room, or some back alley.
Mike was impressed, he always wanted to meet a woman with that kind of sexual appetite. He met a few like that in his escort days, but never one he met on his own. Some of the women he meets were of course great, loved the sex he gave them, never asking how he is as good as he was.
Eventually, Vanessa had been wanting to actually play out her fantasies. She slept with a doctor who had to come over for a house visit. She once played a mugging victim to seduce a man who saved her thinking she was under attack, but it was actually Jerry. She even once slept with a cop to get off of a traffic ticket; that one took several tries before she kept breaking traffic laws and getting tickets to find the right cop who was willing to put his job on the line for a good time.
Those, plus others, were already too risky but Jerry played along because he enjoyed his wife's fantasies being played out, and she even helped him with a few of his own.
But one fantasy of hers has Jerry very worried about. Vanessa enjoyed playing a prostitute with Jerry, but she wanted to do it for real. She wanted to meet a guy in public, preferably on the street, and take her to a hotel or somewhere for sex. Some of her fantasies were already risky enough when it comes to sleeping with strangers, but Jerry felt that finding some random guy to pay her for sex was going too far because you never know who that stranger might be.
