Hard Cucking by a Stranger

First time author, I hope you enjoy!

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I travel for work often. And whenever I have time in a new place, I try to get acquainted with locals. I don’t love quick hookups, but being in town for just a couple of nights I usually need to limit the “get to know you phase” to a couple hours over drinks or dinner. 

When I walked into the hotel bar on a Monday night, James was already sitting at a high top. He wore a tailored light blue dress shirt and gray slacks, looking like any number of people enjoying a post-work drink.

It’s always hard to tell when a meetup will get interesting. Which is why I like to do my research in advance. I like the information asymmetry and ability to begin dominating  someone before they realize it. Anyone can choke a sub—and after holding my gaze for a second and greeting me with a warm hug, James knew he was going to let me do that to him tonight. 

What he didn’t know was that I relished treating him like prey and the game of manipulation more than just a quick fuck. I had done my homework before meeting him accordingly.

James was 33, just like I was. He was born in Florida but grew up in the suburbs of DC. He went to undergrad at Princeton and spent two years as an elementary school teacher for Teach for America in Chicago. He went to grad school after, earning an MBA from Harvard and turning a classmate into a husband.

McKinsey snatched him up out of Harvard and now he worked 80 hour weeks doing vague consulting on business efficiency. 

He and his husband met at a social mixer their first year at Harvard. They got engaged after graduation and married the following year. They bought a home here in LA. A mid century modern home that in most parts of the country would run 300-500k, but they paid 1.8 million for it in their trendy LA neighborhood according to Zillow. I figured James’ parents, both doctors, helped with the down payment from the subtext of his mom’s Facebook posts.

They often hosted dinner parties that looked like they turned into club nights and orgies semi regularly. 

In short, James was the exact kind of person I was looking for. Outwardly successful, sexually liberated, desperate for social approval. 

I smiled at James and asked if I could get him a drink from the bar. He requested a Manhattan and I told him I’d be back in a second.

I wouldn’t be drinking. I like being in control, setting the pace, and dictating the evening. It’s much easier to do that while staying clear minded. The trick of course was making James think I was drinking. The club soda with two limes would be good enough to do the trick.

I returned with the drinks. We had met on Grindr the day before. I was in this town often for work. We had exchanged a few messages and agreed to meet up here. 

I let him tell me about his time at Princeton and Harvard. It wasn’t really interesting to me. I knew he had gone to prep school and that both his parents were doctors. That he was smart, successful, and rich-ish wasn’t all that surprising. 

Him emphasizing these things was good to hear though. I liked to build up resentment and contempt for the boys I fucked. My therapist, as kink friendly as he was, often returned to this desire as something I should interrogate more. I would always tell him that there’s just something satisfying about being a little cruel and manipulative to people that really gets me going. 

I had to use the bathroom. As I got up, I noticed a fidgety gay nervously avoiding eye contact as I walked by. It took a moment to place him, but as I relieved myself in a urinal I realized it might be James’ husband, Timothy.

We hadn’t talked much about his husband. He wore a wedding ring, but hadn’t even told me the stupid origins story from a grad school social I’d found on their wedding announcement.

Timothy potentially being here made my pulse quicken. I took the long way back to my seat. Stopping at the far corner of a bar next to the man I thought was Timothy to grab James and I a couple waters. 

A quick glance at his ring revealed an identical engraving pattern to James’ and I was pretty sure I had the right guy.

Without looking at him, I said aloud “so how does this work for you guys? You watch him go on a date with another man sure, but is it because he’s cheating on you? Or you’re into getting cucked? Does he know you’re here?”

Timothy audibly gasped. 

I really was interested in what his response would be, but I also needed to get back to James. I took a spare hotel key out of my pocket and put it in front of him. 

“I don’t know what your arrangement with James is, but if it’s helpful you should wait for us in my hotel is in this building. Room number is on the key. If you do decide to join, you should know that you will be expected to sit quietly in the corner and not engage.” 

His eyes widened and he gave a slight nod. 

I hesitated with the waters in hand. 

“You know, it might be a nice gesture if you picked up the tab. That’s our waiter right there. Though of course you’ll need to do it without your husband realizing. That would ruin your little surprise, if that’s what you’re going for.”

I walked back to James. This was certainly a new one, but a very welcome development. 

At the next conversational lull, I asked if we should head up to my room. I flagged down the waiter who said we were all set. 

James assumed I had charged it to my room, but I knew better. He made an effort to reach for his wallet but I waived him away with a smile.

We walked across the lobby and into the elevators. Having already aligned on broad strokes of a more dom/sub dynamic and him making it clear to me he’d be ready to submit but not bottom this first meeting, I nevertheless felt inclined to try and get more details on his interests.

I find it helpful to be direct. And of course consent forward. This situation was developing into a bit of a gray area as I thought there was a 50/50 chance his husband would be there. I wondered if James would have shot Timothy a text at some point telling him he’d be going home with his date. Matter of fact, I wonder if either would text the other and I hoped I’d find out at some point.

As soon as we entered my room, I pushed James up against the wall and started kissing him. I generally prefer a more subtle start, but I wanted to scan the room before we got in. 

Timothy was there, sitting in the office chair next to the room’s desk. It was all I could do not to laugh. 

Pulling my face away from his, I told James I had a surprise for him, and I hoped he would be okay with it. I emphasized that if he wasn’t into it, there was absolutely no pressure to stay.  His brow furrowed and he turned to face the room. He flinched in my arms and let out a yelp when he saw his husband. 

I calmly told James that I had found Timothy at the bar keeping an eye on us and that I thought he may enjoy a closer look. 

Timothy gave a pained smile as his eyes darted between his husband and me. “Don’t be mad, I knew you were getting drinks with a guy you met and I just wanted to see what your dates looked like.”

“Oh shit,” I said aloud, “Timothy, does James go on a lot of dates without you?”

Timothy nodded sheepishly. 

Barely able to hide my glee, I turned to James, “Why do you meet up with so many guys when you have a husband at home? Could it be that he’s not good enough for you?”

James getting into the spirit of things escalated far more than I expected. Sneering at his husband he said, “Timothy is a nice sofa. Comfortable and fine to sit on. But not really something you want to sleep on, and looks best by itself in a corner.”

Timothy looked down. It was clear I had stumbled into something I could work with here. It seemed like they had probably played with a similar dynamic at some point, though perhaps not quite as explicitly as they were now. I also wondered how much they had told each other about the night. Both before the date and via texts, how much of this was unfolding in real time and how much was pre planned?

I wanted to dominate James. He was handsome in a punchable face kind of way and fit in a Barry’s boot camp kind of way. One of those preppy nerds who came into his body in his late 20s and early 30s, but still liked to pay $40 a class to get yelled at by a gay who reminded him of his high school bullies, and now clearly enjoyed cruelly cucking his husband. 

But as I clocked immediately, as much as I wanted to fuck him, he wasn’t uniquely fuckable. I could have probably found a half dozen guys similar to him in that bar alone, let alone in the city. What was more unique was this situation. 

I had cucked guys before, but it had always been planned. Hot, but planned. This was a different thrill. And not being stressed about pushing too far and potentially having them leave my hotel, I decided to go for it.  

I picked up James who eagerly wrapped his legs around me with a moan. He was roughly my height and only slightly thinner than I was, but I was plenty strong to lift his lithe body.

I walked to the bed and gently laid him down on his back. Ignoring Timothy, I gave him gentle kisses and called him a beautiful boy. He whimpered excitedly, not sure what to make of what was a promised rough evening that had suddenly been crashed by his husband and was off to such a sweet start.

We made out for a bit before I told him it was time to begin. James took off my clothes and then his, before devouring my cock like a starving man. Looking across the room Timothy had at some point unzipped his pants and was stroking his cock. I shot daggers across the room at him. 

“Timothy, I don’t like to see useless dick when I’m fucking. I’m going to ask you to put that away for me and not to take it out again.”

Before he could protest, James interjected. “Tim, you need to listen to him, don’t fuck this up for me.”

With a nod he zipped his pants up. “Good job, little guy,” I said condescendingly to Timothy. “Why don’t you just pay attention to how your husband deserves to be treated and maybe I’ll give you something to do afterwards.”

Turning my attention to James who was giving a good, not great blow job I said, “Okay bud, we’re really going to get started now, are you ready?”

He nodded with the head of my 8 inch dick in his mouth. He hadn’t been deep throating especially well so I decided to help him. In a flash, I wrapped my leg around his head and pushed. He was instantly pinned and struggled against the force of my vice grip. His legs flailed and he sputtered on my dick. I stared blankly at him, feeling a satisfaction that his next breath would happen only when I decided to give it to him. 

I held the pressure for a few seconds before releasing him from my dick. He coughed up spit with a dazed look in his eye. A lot of guys talk a big game, I prefer a matter of fact one. 

“Our interactions are about me.” I said evenly as he tried to catch his breath. “I am going to push both of you until we get somewhere interesting.”

I searched his face and found resolve, not panic.

“Resume” I pointed to my dick and James dove on it. This time I ran my hands through his hair lovingly while looking at Timothy. It felt like a good time to push us collectively further. 

“What would Mrs. Davis say?” I asked, referring to Timothy’s mother. The room suddenly got still. James froze momentarily until I hit the back of his head to get back to sucking my dick. Timothy’s eyes widened. 

I continued, “Sending her darling oldest son to St. Peters, probably inadvertently stirring the gay in him, coming to terms with and accepting him and his husband, only to watch his husband get face fucked by a stranger in an airport Hilton.”

Timothy’s pants tightened. I tried to imagine what each were thinking. James probably figured I knew Timothy from somewhere else. Timothy probably figured James had fed me information. In truth, I was racking my brain thinking about all the fun facts I had collected with the intention of love bombing James but now had a new application to use. 

I let my rhetorical question hang in the air for a moment and turned my focus back to James. He was doing a great job working the head and shaft with vigor. His coiffed hair had been sufficiently tousled and his eyes were red from my previous forceful actions. 

James flinched when I raised my hand. He was jumpy and I couldn’t blame him. I’d shown that I was willing to get rough with him and push limits. I told him to relax, I was just waiving his husband over. 

“Timothy I want you to watch this special moment closely. I’m going to cum down James’ throat in a moment here and he’s going to swallow every drop. Isn’t that right James?”

James’ eyes widened and he nodded as Timothy approached.

I hadn’t cum in a few days and I had a feeling James wouldn’t be able to swallow it all. 

I told James to get on his back and hang his head over the edge of the bed. I was going to get maximum leverage and throat fuck my cum into him. Timothy couldn’t look away, alternating locking eyes with me and watching James sputter on my dick. 

I was putting on a bit of a show. Cruelly keeping my dick in his windpipe just long enough for him to start flailing his legs and try to push me away before I would back off. 

After a couple minutes of this I knew James didn’t have much more left in him. I had broken him, deprived him from oxygen for several stretches over the 30 minute or so of blow job and throat fucking. His throat was just a plaything for me, I could tell he had gotten to a great sub space where my dick was the only thing he cared about pleasing. 

I locked eyes with Timothy and jammed my cock in James throat one last time. I held it there, unloading what felt like a massive load directly in his throat. I let out a gutteral grunt, having finally reached the satisfying climax I was so singularly seeking that evening. It was one of those soul leaving body orgasms that just feels like what men like me are put on Earth to have. 

James sputtered, pushing my cock away while cum was still ejaculating. It was a largely involuntary act I knew, a load like the one I shot must have felt like he was drowning. The last drips got on the carpet and James dry heaved some spit up as well onto the hotel carpet. I gently repositioned James’ head onto the bed and immediately began stroking his head gently. 

“You did so well beautiful, I’m so proud of you! I really pushed the issue some at the end and I thought you did an awesome job.” James beamed the most beautiful and content smile. 

I scooped him up and positioned his head on the pillows on the bed. I laid next to him, holding him tight and softly snuggling his body. I felt his heart still racing and knew the come down from a session like that would be meaningful. 

Narrowing my eyes I turned to Timothy. 

“Did you like the show, Timothy?”

His eyes widened at my acknowledgement of him and all he could do was nod vigorously. 

“Good boy. I’m sure you noticed your husband couldn’t quite swallow my load. I think it would be nice to the housekeeping team here if you cleaned up what he couldn’t swallow.”

Timothy nodded and retrieved a towel from the bathroom. He got on his knees to wipe up the mess while I held his husband now contentedly cooing and dozing in my arms. 

“Good job, Timothy. You can go home now. James will be back when he feels like it.”

Timothy opened his mouth to protest before catching the fire in my eyes. He exhaled and nodded, wordlessly leaving.