Check... and Mate
by Ann Douglas
Copyright© 2026 by Ann Douglas
Erotica Sex Story: With rain ruining his weekend at Lake George, truck driver Mark accepts a chess challenge from rugged older technician Don. The game leads to candid conversation, a private wager and an invitation Mark cannot dismiss. By morning, he has explored a side of himself he had never been ready to acknowledge.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma Age Gap Consensual Gay Fiction Anal Sex Oral Sex .
Summer 1975
“Fuck, fuck, fuck,” Mark Palmieri said under his breath as the blond-haired twenty-three-year-old looked out the hotel lobby’s bay window, watching the downpour from the unexpected storm that had washed out his plans for the weekend. “I might as well be back home in Brooklyn.”
Twenty-four hours before, Mark had been standing in the office of Teresa Gennaro, the dispatch manager at Amalgamated Trucking. Prior to stepping into the forty-eight-year-old’s office, the rookie driver had been looking forward to his first weekend off in two months, but it had only taken seven words for any plans he might have had to evaporate like ice on a skillet.
“I need you to work this weekend,” Teresa said before Mark could even sit down in the chair in front of her desk.
A stern look filled the woman’s face as she waited a long moment to see if Mark cared to protest. When none was forthcoming, she motioned to the seat and, once he had sat down, began to explain why he would be doing so.
“Toby Tyler quit this morning,” she began, “and I’m sure you know what that means.”
Mark knew all too well, and with that realization he sank back in the chair and let out a low but noticeable groan. He’d started with Amalgamated eleven months ago, during which he’d only managed to take one step up the ladder of seniority — on which everything from assignments to vacation picks were based. The only name below him on the company roster had been Toby Tyler.
“Toby was supposed to make a run up to Clayton Springs this weekend,” Teresa said after she’d given Mark what she considered enough time to absorb his change of status, “and since all the more senior drivers already have prior assignments or weekend plans, you fall into the slot.”
‘Lucky me,’ Mark thought.
“You’ll be delivering exhibition material for an Industry Expo being held at the Mountainview,” the stocky brunette explained, “but don’t worry, all you have to do is show up on time. The people on site are responsible for unloading the display and then packing it back up for you to bring back on Sunday night.”
As she spoke, she handed Mark a brochure about the Mountainview, the back of which showed an address and local map. There was also a trip ticket attached that showed a more detailed map that outlined the route he would follow to get there. Flipping the pamphlet over, Mark took a more interested look at the photos of the lakefront beach and other amenities the resort offered, causing him to think this might not be so bad after all.
“Will I be staying at the Mountainview?” Mark asked.
“Not at what they charge for a night,” Teresa laughed. “No, you’ll be staying at a motel about a quarter mile down the road.”
“Oh, okay,” Mark responded, his tone showing his disappointment. Knowing how tight the company was with money, he could only imagine what kind of dump that might turn out to be.
“But nothing says you can’t hang around the hotel during the day and make use of the spaces open to the general public, which I’d like to point out include the beach,” Teresa stated, causing Mark to again look down at the long stretch of pristine sand bordering Lake George.
Mark again pictured himself sitting in one of the Adirondack chairs in the photo, soaking up the sun with a drink in his hand.
“You have to be there by seven,” Teresa said as she then handed him an envelope with expense money for fuel for the return trip and such, “which means that you need to leave the depot no later than three in the morning.”
“I’ll be there,” Mark promised as he checked the amount in the envelope and then signed the receipt that had come with it.
As he put the brochure and cash into his pocket, handing Teresa the receipt afterwards, Mark could well understand why no one with any seniority ever wanted to make this run. It would’ve been a lot easier to leave tonight and get there by midnight, but that would mean that the company would have to spring for another night of lodgings. And that wasn’t going to happen as long as old man Callahan owned the company. He ran the place by the motto — every nickel counted.
“Well, I guess that’s it, except to wish you a safe trip and have a little fun if you can,” Teresa concluded as she turned her attention to the papers on her desk.
As he left her office, Mark cursed the bad luck that had put him once more at the bottom of the totem pole. Even so, he couldn’t really get mad at Teresa. She’d gone out of her way the last few months to get him as many good runs as possible. The reason why she’d done so hadn’t exactly been innocent, however, because anyone who cared to notice could see that she had the hots for him. It was pretty much common knowledge that the very married mother of four liked to screw around with some of the drivers, and Mark was the latest target on her radar. So far, however, he’d managed to avoid her bed.
Stepping away from the window, Mark walked over by the front desk where a large, oversized board rested on a tripod display stand. On it was written the latest weather forecast. His heart dropped as he read that the rainstorm wasn’t expected to move out of the area until tomorrow afternoon, just a few hours before he was scheduled to start back home. As a result, all outdoor activities had been canceled, and Mark didn’t need to be reminded that most of the activities open to the public were held outside.
‘Well, at least I brought a book,’ Mark thought as, pulling the well-worn tome out of his back pocket, he headed toward the lounge in search of a comfortable chair.
After about forty minutes, he’d had enough of John Jakes’ The Rebels, the second book in his American Bicentennial Series. It wasn’t that he wasn’t enjoying it; he was, it was just that he had to be in the mood to read, and right now he wasn’t.
Looking around the room, he counted about a dozen guests, six of whom were sitting around a large round table with folders scattered across it. His guess was that they were here for the exposition. A few other chairs were occupied by individuals reading newspapers or other periodicals. Two were women, but of an age that made any thought of striking up anything more than a conversation rather doubtful.
‘Maybe I should head down to that motel the company made my reservation at,’ Mark thought as he got up from his chair. ‘There should be a television in my room, or at least I hope so.’
Rising from his chair, he started out of the lounge, only to pause when, out of the corner of his eye, he noticed another guest sitting by himself in the far corner. Gray-haired with a crew cut and a tightly trimmed beard, the man was wearing a light blue denim shirt and darker jeans, a sort of work uniform that made him look a bit out of place. Yet it wasn’t so much his appearance that caught Mark’s eye, but rather the portable chess set on the small rectangular table in front of him.
The seat on the opposite side of the table was empty, even though it looked like a game was in progress. Curious, Mark came up from behind him, stopping only a few feet away. After watching for about a minute, Mark realized the man wasn’t playing a game, at least not against a current opponent. What he was actually doing was working out a problem from some earlier contest. It had been a good number of years since Mark had played himself, but chess was a game that he really loved playing while growing up.
Intent on the problem, the man didn’t notice Mark, at least not until, after studying the board himself for a long minute, the younger man inadvertently expressed the move he would make, not realizing until the man reacted that he’d done so out loud.
Turning to the sound of Mark’s voice, the man displayed an expression of surprise. Not that he’d been interrupted, but that the suggested move was exactly the one he had decided was the one that should have been played in the original match.
“Do you play?” he asked.
“Not in a while,” Mark replied. “My uncle taught me when I was a kid, but nowadays it’s hard to find anyone to play with. The guys I work with are more into checkers or cards.”
“Well, if you’re not busy, would you like a game?” he then asked.
“You know, I think I would,” Mark smiled, thinking that was better than spending the afternoon cooped up in some dingy motel.
“Donald Harrington, my friends call me Don,” the other man said, extending his hand as he rose to his full height.
“Mark Palmieri,” the younger man said in return, reaching out with his hand as well. “Nice to meet you, Don.”
Handsome, with rugged good looks, Don was, Mark noted, a couple of inches taller than his own five seven. Weight-wise, he was about fifteen pounds heavier, with a frame that suggested he either worked out regularly or had a very physical job. Later, Mark would find out that both were true. Also, Mark initially thought Don was in his mid-forties and was surprised to learn he’d recently turned fifty-two.
Returning to his seat as Mark pulled out the empty chair on the other side of the table, Don quickly reset the chess board. Since the white field was already on the driver’s side, the first move was his.
“So, what brings you to the Mountainview, Mark?” Don asked as he made his counter-move.
As he studied the board, Mark shared his story, including how his vision of spending the weekend relaxing in the sun had been washed out by the storm.
“Ouch, that has to really hurt,” Don said as, after watching Mark’s opening move, he made one of his own.
“What are you gonna do?” Mark said with a shrug. “As they say, you can’t fight Mother Nature.”
Over the next few plays, Don shared that he was also here on business, his company having a contract to maintain the resort’s air conditioning system. The unit had been acting up of late, and in checking it out, he’d found a part that needed replacing. The problem was, it couldn’t be delivered until tomorrow. Fearful of having the system go down again on a busy weekend, the hotel manager had offered to put him up for the night, while still on the clock, so that he’d be available to try and fix any problem that might come up overnight.
“I didn’t have anything else planned for the weekend, so I figured, what not?” he concluded.
After about twenty minutes, each man had an almost equal number of captured pieces off to the side, showing that they were evenly matched. Halfway between that point, they’d been approached by a waitress who asked if they’d like something from the bar. Each ordered a beer, with Mark saying he’d pay for the first round. Then the game continued apace, with the younger man coming out the victor.
“I don’t think you’re as rusty as you thought,” Don smiled. “Another game?”
“I was about to ask the same,” Mark replied, sharing the smile.
This time the game went a little slower, each player taking more time to consider their next move. Spurred on by the beer, as well as a mutual enjoyment of the game, conversation became easier as well.
“Doesn’t your girlfriend mind you working all these weekends?” Don inquired in response to Mark having mentioned that he hadn’t had one off in two months.
“Don’t have a girlfriend,” Mark stated as he watched Don reach for one of his bishops.
“With all the time you spend at work, I’m not surprised,” Don said as he made his counter-move. “Still, all work and no play as they say ... a man has needs.”
“Oh, I didn’t say I didn’t play,” Mark clarified as he responded to Don’s action. “I just don’t always score.”
“I see,” Don observed as he studied the new configuration on the board.
“How about you?” Mark asked, having seen no ring on the other man’s finger.
“Are you asking if I have a girlfriend?” Don said.
Mark nodded his head.
“No, I don’t,” Don replied, pausing for a second and then adding, “but to be honest, women were never my thing.”
The answer seemed to confuse Mark for a second, enough that Don felt the need to clarify it.
“I prefer guys,” he simply said as he turned his attention back to the board.
“You’re gay?” Mark asked cautiously, the response not being one he expected.
“No, but my boyfriend is,” Don quipped, then added. “Sorry old joke, but yes, I’m gay — no boyfriend though.”
Then, as casually as if he’d simply said it was still raining, Don reached out and moved a rook.
“That doesn’t bother you, does it?” Don asked as he released the piece.
“No, of course not,” Mark said, a slight quiver in his tone.
“I’d understand if it did,” Don said as he looked up. “Some guys suddenly feel uncomfortable once I tell them, almost as if I was contagious or something.”
“That’s crazy,” Mark remarked.
“But unfortunately true,” Don pointed out.
As much as he might not want to admit it, Mark had a few friends that would’ve felt exactly that way. He hoped his expression didn’t reflect that.
“Well, I’m not like that,” he offered.
“I can see,” Don again smiled, indicating with his hand that it was Mark’s turn.
Again, Mark studied the board.
“It does make me wonder, though,” Don added, “if you have any friends that are gay?”
“Why would you think that?” Mark asked in turn, delaying his move.
“Your reaction,” Don replied, “or rather your lack of one. People with a gay friend or family member tend to see beyond stereotypes. At least enough not to make snap judgements.”
“No, I don’t know anyone who’s gay,” Mark said as he used his castle to take one of Don’s knights. “I just don’t define people by who they sleep with.”
“That’s a very liberal attitude,” Don noted as he quickly counter-moved, protecting his king. “It sort of makes me wonder who you like to sleep with.”
The question took Mark off guard for a second, just long enough for Don to take note of it.
“Are you asking if I like guys?” Mark asked.
“It’s just a question,” Don responded, “but not one you have any obligation to answer.”
“I’ve never slept with a guy,” Mark said without looking up from the board, making his facial expression difficult to see.
“That’s not really the question, at least not the one you presented,” Don pointed out, “but I can see that it’s not one you’re comfortable with, so why don’t we just forget I asked?”
Several more moves followed with two more of Mark’s pieces leaving the board. He was considering a change in strategy when he unexpectedly returned to the question.
“I have sometimes been curious about other guys,” he said.
“Only curious?” Don inquired.
“Well, sometimes maybe more than curious,” the younger man admitted.
Even though he was sure there was a story behind Mark’s admission, Don didn’t press him to share it. If he wanted to do so, it would have to be of his own volition. After another exchange of pawns, he did just that.
It had been his seventh month on the job and he’d just finished a delivery of medical supplies to a storage facility up in the Bronx. Since it was his last run of the day, and traffic was already backed up on the Cross Bronx Expressway, Mark decided to get something to eat before heading back to Brooklyn. The delivery site was in an industrial area, with few places to eat, but he eventually found a small bar and grill just off the highway entrance.
Being only late afternoon, there were few customers in the bar as Mark took a seat at the end of the counter and ordered a burger plate and a small beer. So it surprised him greatly when, a short time later, a slim, short-haired forty-something gentleman slipped onto the stool next to him and started up a conversation. They’d only been chatting a few minutes when the man, who’d introduced himself as Sidney, unexpectedly said, “Do you know what goes good with a cold beer — a good blowjob?”
While it wasn’t a sentiment that Mark would disagree with, it wasn’t one he expected a stranger to say. He quickly glanced around to see if anyone else might have heard him — especially the bartender standing only a dozen feet away, cleaning a glass mug. If he had, Mark noted, it didn’t garner any reaction.
“I guess not,” Mark finally replied, then as a joke asked, “Know a good place to get one?”
Several times during his initial training, senior drivers had pointed out places where a guy could get his cock sucked, or, if he was really horny, his ashes hauled. They ranged from hole-in-the-wall whorehouses to diners where a waitress might offer something not on the menu. He’d had an encounter with one of the latter on his last day of training, a sort of graduation gift arranged by his instructor.
“Just down the hall,” Sidney replied with a cock of his head, much to Mark’s confusion.
Glancing in the direction the older man had indicated, Mark saw only the doors to the storage room, which had a lock on it, and the small bathroom. He’d made use of the second when he’d first arrived, noting that it held only a small sink and single toilet.
“I don’t understand,” Mark said.
Then it hit him. He’d noted the absence of any female customers when he’d first come in, but as that was pretty much the norm at most bars he’d been in, it hadn’t seemed unusual. When Sidney had first approached him, Mark thought the impeccably groomed man slightly effeminate, but didn’t want to make any assumptions on just that. Now he was reconsidering that choice.
“Are you interested?” Sidney asked as Mark turned his attention back to him.
Rather than reply, Mark instead surveyed the room, finding little to no interest in what might be happening down at the end of the bar. Then he again turned his head in the direction of the bathroom, thinking as he did that two men entering it together would clearly be using it for something other than its intended purpose.
“Oh, don’t worry about them,” Sidney assured them when he’d noticed Mark looking at the other customers. “They’re all regulars — they know the score.”
‘Is this a gay bar?’ Mark asked himself, again glancing around as if there would be a sign somewhere.
“So, what do you say?” Sidney asked. “I’m not looking for any reciprocation, if that’s what you’re worried about. I just like taking care of cute guys like you.”
“I have a girlfriend,” Mark lied.
“One that obviously doesn’t take care of you, because if she did, you’d have already told me no,” Sidney countered.
‘Why haven’t I already said no?’ Mark asked himself.
It wasn’t like he’d actively ever sought out a guy to suck his cock, but there had been a few times when he’d wondered what it might be like. Would a guy be better than a girl, since he knows what it felt like on the receiving end? If he did let Sidney blow him, who would ever know?
“You know, an hour from now, you’re going to be stuck in traffic on the Cross-Bronx, saying to yourself that you’d wish you had,” Sidney said as he began to slide off the stool, pausing for a few seconds to give Mark a last chance to consider the offer.
“You went into the bathroom with him, didn’t you?” Don asked, even though he already knew the answer.
Mark nodded his head, yes.
“And was it better than the girls you knew?” Don inquired.
“Not really,” Mark admitted. “It wasn’t bad, but not any better either. The only thing that really set it apart was that he didn’t stop when I said I was about to come.”
“Ah, I take it that the girls you’ve known weren’t swallowers,” Don grinned.
Mark’s expression said that they weren’t.
“Did you reciprocate?” Don asked, adding that he knew that Sidney had said that wasn’t necessary, but sometimes a guy got caught up in the moment and...”
“I did think about it,” Mark admitted, “but before I could decide, someone was banging on the bathroom door. He said that he didn’t care what the two of us were doing, but could we hurry it up ‘cause he needed to take a piss.”
“I see,” Don said after making another move. “And that, I’m afraid, is checkmate.”
Mark looked at the board and, now seeing the opening that he missed in his distraction, he reached out and tipped his king.
“And much like the gentleman in your story, I have to take a piss,” Don said as he excused himself, “but if you want to go for the best of three, why don’t you set up the board and order another round while I’m gone? Tell the waitress I’ll settle up later.”
“Well, I guess it’s one more for all the marbles,” Don said as he returned from the bathroom and found the board reset and two new beers sitting off to its side.
As each had already played white in a game, Don took two different coloured pieces off the board and, after hiding them behind his back for a moment, presented both hands tightly closed around the rooks. Mark picked his left hand, which turned out to be black, so Don would go first.
“How about we make this a bit more interesting?” Don suggested before making his opening move.
“What do you have in mind?” Mark asked.
“A small wager, not much, just enough to make winning worthwhile,” Don replied.
“How much?” Mark inquired.
“Hmm, how about five bucks?” Don offered.
“That’s not much of a bet,” Mark noted.
“Well, the amount really doesn’t matter as much as the idea that you’re playing for something. I think doing so gives you more of an incentive to play your best,” Don said. “But if you think five isn’t interesting enough, we could always make it twenty.”
From the look on Mark’s face, Don saw that twenty was probably a bit more than the younger man could afford to lose. He immediately suggested that perhaps they didn’t need to play for money at all, at least not directly.
“How about the loser pays for the last two rounds?” the older man suggested.
“That sounds fair,” Mark replied, thinking that wouldn’t be much more than the original bet.
They hadn’t gotten too far into the final match before Mark’s remark about people playing better with something at stake proved true. Moves took even longer, with more concentrated deliberation between them. Somewhere around midpoint, Mark noticed that the new drinks had barely been touched, such was the intensity of their focus. Finally, there were only a few pieces left on the board, and, as Mark studied them, he had to admit that there was no chance of him winning. He could delay the outcome, but not change it.
“The game is yours,” he said, tipping over his king.
Pleased with himself, Don smiled.
“Having someone as good as you to play against was almost worth the price of losing,” Mark offered as, pulling out his wallet, he dropped a couple of bills on the tray the drinks had come on, telling the waitress to keep the change when she came over to pick it up. “I’ve missed playing more than I realized. Plus, the company was pretty good too.”
“You know, we could forget the bet and just split the bill,” Don suggested.
“Nah, a bet’s a bet,” Mark replied.
“I’d offer to go another round and give you a chance to win some of it back,” Don said after a brief consideration, “but I really need to head down to the basement and check on how that temp repair I made is holding up. Also, having skipped lunch, my stomach is reminding me I need to grab something to eat.”
For a moment, Mark thought, given how well they were getting along, that Don might ask him to have dinner with him. But that moment passed as the older man shifted his attention to packing up his chess kit. He briefly considered asking him, but knew that, even before paying off the bet, that would’ve been more than his wallet could handle.
“Well, it was really nice meeting you, Mark,” Don said as he extended his hand. “I enjoyed both the game and conversation.”
“I feel the same way,” Mark replied as he reached out as well.
After shaking hands, Don turned to leave, but then paused after only taking a few steps.
“You know, Mark, I was just thinking,” he said as he turned back and retraced his steps. “I should be back in my room by seven o’clock. If you happen to find yourself still here around that time, why don’t you stop by? I’ve had enough of chess for the day, but I’m sure we could find another way to keep ourselves entertained.”
Mark wasn’t sure what to say, but he doubted that another board game was what the older man had in mind.
“No pressure, of course, I just want you to know the option is there if you’re interested,” Don continued. “Oh, and it’s room 114 by the way.”
With that, he again turned and walked away.
Since he hadn’t had lunch either, Mark also decided to get something to eat. Only, in his case, he elected to go to the fried chicken place across the street rather than the hotel’s dining room. He could only imagine Teresa’s reaction if he submitted a bill for that, no matter how much she wanted to fuck him. As he ate, his mind kept going back and forth about the things he’d told Don and what the older man had replied in turn.
It was clear to him now that Don hadn’t asked him to dinner in order to give him time and space to consider his offer — and considering it, he was. Clayton Springs was five times the distance from home that the bar in the Bronx had been, and a private room was certainly better than a dingy bathroom. The question of whether this was something he really wanted to do, regardless of how many times he might have fantasized about it, was one he just couldn’t make up his mind about. Part of him said yes, but part also said he still wasn’t sure. He thought it significant, however, that there wasn’t a part of him that said — absolutely not.
By the time he’d finished his early dinner and walked back to the motel down the road, Mark had made up his mind to not make up his mind. Instead, he was going to just go with the flow and see where it led him. After all, if he had a chance of heart, he could simply turn around and leave — right?
Despite the motel’s limited amenities, Mark was able to take a long hot shower, followed by a close shave and a change of clothes. All he’d brought with him were fresh underwear and a second t-shirt, but at least he wasn’t still wearing what he’d worn on the long drive upstate.
The cheap digital watch on his wrist, his biggest indulgence since getting the job at Amalgamated, displayed seven twenty-two as Mark stood outside the door to room 114. It had said seven fifteen when he’d first arrived and had slowly advanced while he tried to come up with the nerve to knock. He finally found it, rapping his knuckles against the hard wood three times.
When no response came after what he thought was a reasonable wait, he knocked again, wondering if perhaps Don had gotten tied up with the air conditioning equipment. A thought, he admitted to himself, that brought some disappointment.
Mark was about to leave when he heard the sound of a security chain on the other side of the door being undone. Then the door swung open, revealing Don standing there wearing a short robe. Attire that, along with the wetness of his hair, showed that he had just gotten out of the shower.
“I thought that maybe I’d scared you off,” Don said in reference to Mark being almost a half hour late.
“No, not yet at least,” Mark quipped as he stepped into the room.
“Well, you’re here now, that’s what matters,” Don said as he closed the door behind Mark.
“When I didn’t get any answer,” Mark shared as Don turned back around to face him. “I figured that you’d gotten tied up with the air conditioning.”
“I almost did,” Don said as he gestured for Mark to have a seat on the edge of the bed. “That jury-rigging I did is still iffy at best. I wouldn’t be surprised if it crapped out before that replacement part gets here.”
“Shouldn’t you be down there watching it then?” Mark asked.
“Wouldn’t make a bit of difference if I was,” Don responded. “It’ll either last, or it won’t. If it’s the latter, they’ll page me.
“But the part is coming tomorrow, right?”
“Supposedly, it’s already on the way,” Don answered. “In fact, I put in a call to the distribution centre just before dinner to confirm it. I’m just waiting for a call back from the shipping manager.”
“Then maybe I should come back later...” Mark started to say, thinking that a phone call in the middle of ... whatever ... might be awkward.
“No need for that,” Don insisted. “He promised to get back to me by seven-thirty, so he should be calling any minute.”
As he listened, Mark found himself staring at Don’s attire, or more accurately, his lack of it. A loosely tied belt left the top open enough to reveal a hairy, well-developed chest, while short sleeves and a garment length that barely extended to his knees displayed arms and legs just as impressive.
“Would you like a drink while we wait?” Don asked.
“No, I’m good,” Mark replied, thinking that the beers earlier had been enough. He wanted to stay clear-headed.
“Okay, just let me know if you change your mind,” Don said as he stepped off to the right and picked up a small duffle bag sitting on the bottom of the bed, explaining that he always kept a change of clothes in his truck, never knowing when or where he might get stuck.
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