Hard Labour
6 min

What a trick wants (Part 2)

Sometimes roleplay gets real

“You gonna be a good boy . . . for daddy?” I say.

A slight shiver runs through his body, like he’s seen a ghost.

“Yes, daddy,” he says.

“Get on your knees and show daddy that ass.”

He quickly obliges, contorting his bulky frame on the rickety mattress to flip himself over and present his backside. I run my hands up the outsides of his thighs to grasp his hips.

“Daddy thinks you’ve been a bad boy.”

“Sorry daddy. I tried to be good,” he says, his voice arching higher.

“Daddy knows you’ve been bad and you need to be punished.”

“No daddy, please! I’m sorry daddy!”

“Daddy’s gonna make you sorry,” I say. “Daddy caught you touching yourself and you need to be punished. Daddy wants you to be a good boy but you need to be taught a lesson.”

“I’m sorry, daddy,” he says, his whole body shaking.

I can’t see his face, but I know he’s got tears in his eyes, even before I deliver the first slap.

I’m going to pause for a minute to talk about the whole daddy/boy thing. For those who’ve never dipped their toe in the waters of kink, the idea of enacting parent/child incest as part of a sexual experience probably sounds deeply perverse, maybe indicative of mental illness, a history of abuse or the potential to be a sexual predator. But those who participate in role play regularly know it’s not strange or even particularly kinky. It’s Role-Play 101.

Most incest play has nothing to do with actual incest. It’s about exploring how power dynamics can heighten the charge of sexual activity. Getting your ass pounded brings about a specific set of physical sensations. But getting your ass pounded by someone who’s responsible for limiting your behaviour, caring for you, and the myriad other things parents are charged with doing, overlays a series of psychological sensations that heighten the physical experience in sometimes unimaginable ways. It’s like PNP, except the party’s all in your head.  

While my own excursions into role play were initially tentative, things went forward at lightning speed once one particular daddy unleashed that can of worms on me. It’s much less a part of my private sex life than it was at one point. But it’s particularly prevalent in sex work. Aside from wanting cum on their faces, it’s probably the most common thing people are looking for. However, as in Mike’s case, that doesn’t necessarily make it easy to ask.

As the flat of my hand meets his ass, he nearly crumbles to the bed, even though I’ve barely touched him.

“Say thank you to daddy,” I say.

His body is shaking but he manages to croak out a “Thank you, daddy,” before I deliver the next slap.

He’s ready for it the second time, letting his body relax to receive it. We continue to 10, and then I grasp his hips, and press my crotch into his ass

“Daddy’s gonna fuck your ass now, boy.”

“No daddy! Please!”

“No, you’re gonna be a good boy and take daddy’s cock all the way.”

I grab my lube from the pouch next to the massage oil, slather my fingers, and begin playing with his hole. He moans, arching his back to bring his ass toward me. I guess he does want daddy’s cock after all. My fingers slide in surprisingly easily. He may be new to role play, but he’s clearly no stranger to getting fucked. I roll on a condom and tease him with the tip of my dick.

“Daddy’s gonna fuck that ass now.”

“No daddy, please don’t fuck my pussy,” he cries.

Huh. Terminology change. Okay. Go with it.

“You want daddy to fuck your pussy . . . uh . . . little girl?”

“No daddy. Please. I’m just a little girl and my pussy’s so tight.”

Interesting. This is going somewhere unexpected. I wonder if he’s a cross-dresser who’s yet to discover his tendencies? Is it possible he’s trans? No, I think it’s just a fantasy. Daddy/boy I’ve done. But daddy/girl is totally new. Is it the same relationship? Do I have to play anything differently? He can’t seem to ask for what he wants, but that doesn’t mean he doesn’t know.

I press the tip of my cock against his hole.

“Be a good girl and take daddy’s cock in your pussy,” I say.

“Yes daddy. Whatever daddy wants,” he sobs.

My dick slides in as easily as my fingers and I begin pumping in and out. I get a lot of virgins or near-virgins, where you have to be so careful not to hurt them. He’s obviously not one of those, so I start really giving it, slamming into him, feeling my pubic bone collide with his ass. We continue our chatter, me saying how daddy wants to fuck his little girl, him begging me to stop.

I can feel him starting to pull away, and as I grip his hips, pulling him close, it occurs to me we haven’t set safe words. Normally the beginning of any SM scene means deciding on a protocol for adjusting or ending if necessary. But it all happened without any negotiation, so I have no idea whether his pleas are real or performative. Should I stop? Is he enjoying this? Am I hurting him?

I glance at the clock and there’s still more than an hour left in our session. Maybe it’s best to give him a break, I decide, and I should probably change the condom anyway. I pull out and deliver one final slap to his ass. He collapses in a heap on the bed.

“Daddy’s not done with you,” I say over my shoulder as I walk to the bathroom.

I slide the condom off, wrap it in some toilet paper and toss it in the trash. Standing at the sink washing my hands, I can still see him on the bed through the glass partition above the Jacuzzi. Even from a distance, I can see he’s shaking a little. I walk back to the bed and put my hand on his shoulder.

“Do you need a little break?” I ask.

He looks up at me. His face is beet red and streaked with tears.

“Actually,” he says. “I think I’m done. That got a little too real, if you know what I mean.”

I pull my underwear back on, head to the couch, and open another beer. He stays on the bed for a few minutes, but gradually pulls himself together and joins me. I’m rarely at a loss for words, but right now I have no idea what to say. I’ve clearly unlocked some past trauma. What’s the appropriate sex work protocol? Should I try to help him process? Am I qualified to do that? Is it going to last more than the hour we have left? If so, am I obligated to stay? Or should I just leave him to deal with this wound I’ve opened? Or do I help him find the appropriate professional to help, should he have the courage to do so, and absolve myself of any responsibility for follow-up?

If he’s thinking any of the same things, he’s certainly not sharing. Our conversation reverts to the same small talk from two hours ago, this time with him asking about good restaurants in town. My knowledge of French cuisine is limited, but I mention a few Thai places I like. This continues for another hour, and all the while I’m wondering whether he’s going to want to talk about what happened. He doesn’t, and we end the session in the same stiff formality we started with.

As the clock hits our appointed time, I let him know I should split and begin to pick up my clothes and sex supplies. At the door, he hands me a stack of American hundreds and offers a nervous hug before sending me on my way.

It’s after midnight, but I bike down to the river instead of heading home. Finding a bench, I light a cigarette and stare out at the water. This is the first time I’ve had someone cry during a role play and I’m not sure how to handle it. Did I cross an ethical line by not setting boundaries at the beginning? If this unexpected voyage of self-discovery takes him to a place he’s not ready for, how much responsibility do I bear? Should I have worked harder to figure out what he was looking for so I was prepared to take on the consequences of him getting it?

I’ve done plenty of role play since then. And now, when the tears come, I’m neither surprised nor unprepared. I play daddy most of the time, though occasionally I’m the boy, the teacher, the coach, or once in a while, the little girl. I understand opening these things up leaves people feeling exposed, possibly ashamed, and sometimes leaves them with some serious shit to deal with. I stick around until I feel like they’re okay and offer follow-up processing by phone if needed. As for Mike, I have no idea what the journey I started him on was or where it led him. But even though he couldn’t bring himself to tell me what wanted, I hope he got what he needed.

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