John threw on his red leather jacket which was reserved for nights like this, nights on ol' reliable. Lenny would be waiting downstairs in the swanky lobby of the downtown Mariott, just as according to the plan, so all would be good to go. He patted his jeans pockets to ensure he had the room key and his wallet, then left the room, letting the door swing shut behind him.
In the first bar he tried, which was often the only one he needed to try, John ordered a cosmopolitan and sat at the bar, waiting to be approached. He'd learned a long time ago not to drink something too macho, as it usually meant he wouldn't be approached all night. The closeted guys he was after liked to be pretty certain he was a homo like them before striking up a conversation.
Tonight, John was aware that it didn't matter what the guy looked like or how old he was. The close shave last night had put him off actually doing anything with one of the marks for a long time. The slick lawyer mark last night had let slip right at the end of the con that John had blown him, and Lenny must've heard. He must've. But he hadn't said anything. Better to be safe than sorry though. The last thing John needed was his partner in crime asking questions about his sexuality. It'd taken him long enough to explain the concept of men liking men to Lenny when they'd first started running the con all those years ago. Plus, John wasn't even sure he could give Lenny an answer if he asked. John certainly didn't think he himself was gay, he just sometimes took it a bit further with the marks than was necessary.
John remembered the first time he'd gone further with a mark. They'd been running the con for a couple of years. That day they were in LA, and the mark was a little skinny guy in his mid thirties, worked as an architect or something and that day was particularly eager. They'd just got back to the hotel room, and the door was barely closed when the mark had pulled down his trousers to reveal a black thong, then bent over the bed with his ass in the air. John remembered he'd been especially horny that day, and looking at that skinny white shaved ass in a thong had made him hard. He'd needed no more invitation. He had pulled down his jeans and boxer shorts and rammed his full length straight up the mark's ass. He'd fucked him for a good ten minutes. He guessed the fact that he was shaved smooth and wearing a thong had helped. John seemed to remember thinking of his ex girlfriend Stacy the whole time, except the mark seemed to enjoy being fucked far more than she ever had. This had been the first time John had even considered a dude could jizz without even touching his dick, but this skinny guy had done. As soon as John himself had shot his load, the mark had cried out in ecstacy and dribbled what seemed like a pint of cum into a puddle on the bed, a puddle John had made sure to cover up before Lenny had burst in and the con had recommenced.
After this, John had scared himself a little, and it wasn't until the following year that he had sex with a man again. There'd been plenty of women in between of course. He was a good looking man and he could get women into bed quite easily. Despite this, he'd once bragged to a friend in Detroit who'd been in on the con that it was "a lot easier to bed a faggot". The second time he'd had sex with a man was after his girlfriend at the time, Sarah, had thrown him out after an argument about something or nothing. He remembered having looked forward to fucking her brains out all day, and had still been horny when she kicked him to the curb. He couldn't be bothered wooing a girl with expensive drinks and a night of small talk, so he'd paid a visit to a local gay bar and picked up a slim but athletic young man of around 25, with long-ish dirty blonde hair, whose name was Stevie. He and Stevie had talked for a short while, then gone into the toilets of the club where Stevie had dropped to his knees and sucked John's cock like a champ. To this day, John was sure he'd never had better head than that. The guy's nose had pressed into John's trimmed pubes and his stubbly chin had tickled his balls. It had been so good John had soaked the guy's throat in jizz within five minutes. It was at this point that John had begun to seriously consider that he might not be completely straight.
Tonight, John had been approached four times within fifteen minutes, but had turned down all the potential marks because none of them looked like they had any more than $150 in their bank accounts. It was a little later in the evening when a short balding man of around 50 carrying a brief case sat next to him at the bar and ordered a gin and tonic and whatever John was having. This was exactly the sort of mark he'd been looking for, especially since he was sure he'd seen him slip off a wedding ring before coming over.
After introductions (the mark's name was Frederick) and a little small talk, the man offered to take John to a hotel, to which John replied that he had a room already, and that he'd like Freddy - as he'd enticingly christened him - to accompany him. Freddy's eyes had lit up, and darted up and down John's body. As they left the bar, John noticed that the mark's eyes were transfixed on his ass. He had him in the bag. They walked through the cold streets, chatting about John's life, most of which he made up of course.
When they arrived at the hotel, John gave Lenny the usual wink, and went upstairs with Freddy. Once in the room, as was usual if he didn't want any actual action with the mark, John said "you know, I might have to take a shower before we get down to anything"
"that's fine" replied Freddy, "maybe I could join you", he added with an effort at a seductive voice
"no, no, you just make yourself at home out here" John replied, "help yourself to the mini bar".
As usual, John made sure to take as much time as possible in the shower to give Lenny time to get up to the room. As he was turning the shower off, he heard the door burst open and Lenny launch into the usual garb. He tied a towel around himself and made his own entrance. He never quite knew what to expect at this point, but it was always pretty similar. Tonight, the mark had on more clothes than usual, as he had left his shirt on, but he had removed his pants and had laid face down on the bed, his short, hairy legs spread out, his back arched a little so that his chubby ass was in the air. John noticed the guy was very prepared. Much like last night's mark, Freddy had lubed up his hole. In addition, he noticed a litte gold bottle on the bed which he'd seen a few times before. Poppers.
"DREW HOW COULD YOU?" Lenny wailed, to which came the usual reply of "It's not what it looks like Baby honestly". The mark jumped to his feet, and hastily wrapped the bed sheet around his waist, his formidable boner making a tent over his crotch. The mark seemed stunned into silence as Lenny and John pretended to argue. It was when Lenny picked up Frederick's black leather wallet from the bedside table that he piped up. "Hey, that's mine." he said, nervously.
"I know it's yours" replied Lenny, opening it up. When he did, a gold wedding ring fell out on to the floor. Lenny picked it up and cried "As per usual Drew! He's married". At this point, the mark rushed forward and tried to grab the ring and Lenny threw it at his feet. John caught a flash of Freddy's pink, now redundantly lubed up asshole as he bent over to pick up the ring. At this point, Lenny picked up the breifcase from the floor and opened it, emptying it out on to the floor. He went straight for one of the many business cards that had fallen out, before noticing another object he'd liberated from the case.
Lying on the floor was a black, life like rubber dildo. John guessed that the mark had anticipated returning to his hotel room alone tonight, and fought hard to keep back a smirk. Soon though, he was fighting hard to keep back a semi, surprised to find the thought of middle-aged, chubby Fred drilling his hole with the black dick on the floor excited him. Fred was now an even deeper shade of red as he bundled his papers, pens, business cards and sex toy back into his brief case. As the plan dictated, Lenny read Freddy's name from the business card, "Frederick Lionel Smith from Albany, New York", and continued, "maybe I should give the numbers on this business card a call Frederick, I expect your wife would be interested to find out what you were up to here, and about what's in your brief case".
"please, no, she wouldn't understand". The usual begging commenced. The mark pulled his Ralph Lauren boxer shorts on as Lenny looked more defiant. "Maybe I'll go and make the call now in the lobby", he said calmly.
"Ok, look, I've got money. Please don't tell my wife, please" said Frederick. It was quite rare for the mark to make the first mention of money, and John saw Lenny's face change momentarily in surprise. "please" continued Frederick looking at John, "all I wanted was a quick bum, I had no idea you had a boyfriend, you didn't tell me."
"Look, Freddy, the best thing to do is give him the money. He won't let up, and he will tell your wife, he's done it before, seriously" said John, faking a panicked voice. As he did so, he held five fingers to his side, indicating that Lenny should ask for $5,000 instead of just one, since this mark seemed pretty rich. John had no idea if Lenny had noticed his signal or not.
"I can give you $1,000" the mark said.
"make it five and I won't call your wife" replied Lenny. John was relieved Lenny had seen his signal, even more so when the mark didn't put up much of a fight. He began to protest, then his face changed and he feebly said "OK, five it is."
When the mark returned, he handed Lenny the money in exchange for his business card and brief case and left the room chuntering. As Fred left, John's mind eagerly drifted back to the black dildo, and he wondered whether it would get used tonight after all. As they left the hotel room themselves, John struggled to hide the tent pitched in his pants.