Hard Labour
5 min

When daddy and son roleplay crosses the line (Part 1)

A hot, hung top deals with himself through sex

I often joke that sex work is like being a nurse, a small business owner and a therapist all in one. But while I have a basic knowledge in matters of health, financial management and psychology, I’m not an expert in any of those fields. I can take a pulse, administer first aid and talk someone down from a drug trip. But I also know when to call an ambulance, give the number to Hassle Free, or send something to my accountant, rather than dealing with it myself. Knowing the limit of your abilities is key in any profession. Sex work is no different.

Dan doesn’t give many specifics, except that he’s a top. Since 90 percent of my clients are bottoms, it’s a special treat to meet a guy who wants to fuck. When he opens the door I almost fall over. He’s a statuesque 50-something with salt and pepper hair and bulging pecs spilling out of his tank top. Often you have to work to find ways to be attracted to a client; his eyes, his smile, his nervous manner. But with Dan I know immediately that’s not going to be a problem.

He invites me in and offers me a beer, which I accept. His condo is small and jam-packed but well organized. A series of framed snapshots hang above the couch. The dining room table is covered in precisely organized stacks of paper work. Across from the leather sofa, a Mapplethorpe-esque black and white nude occupies most of the wall.

He offers me a joint from the pre-rolled stack and I spark it. The conversation is easy and flirty. He’s divorced with kids, but maintains a good relationship with his ex-wife. He has a boyfriend who lives out of town, but they normally connect every second weekend.

There’s a tiny part of me wondering why I’m here. This guy is stunning and should have no trouble getting laid. Why has he hired me? But then I remind myself of that thing I already know. People who purchase sex do so not because they can’t get laid any other way, but because they enjoy the transactional nature of it.

The THC is kicking in as he begins to run his hand down my chest. I turn to face him, straddling his legs as I kneel on the couch and press my lips to his. He immediately grabs my ass with the force of a top who knows what he’s doing. The make out session is brief, before he gives me a squeeze and gestures towards the bedroom.  

I often try to draw things out, making sure the client gets the full effect of his hour. But he doesn’t want to waste any time. He guides me to the bed, pulls my jeans and my underwear down in one motion, bending me over and burying his face in my ass. I melt into the mattress, my ass rising higher into the air and spreading apart.

He continues rimming me, gradually introducing a few fingers to ease me open. I haven’t even seen his cock, but as he presses into me, I can feel it’s huge. A shot of pain goes through me as he enters and my head snaps up with a breathless “No!” He keeps the tip pressed against the outside, massaging my hole as he speaks softly to me. “Don’t worry boy,” he says. “You can take it.”

He drops a bottle of poppers on the bed next to me and I take a generous haul. I’m not big on poppers during sex as they tend to kill my erection. But it’s clear he’s going to be the only one doing any fucking and I can tell my sphincter will need some artificial relaxation if I’m going to be able to take him.

As the amyl kicks in, I feel a warmth wash over me and all my muscles release slightly. His dick goes a little further in. It still hurts but I can feel I’m opening up so I’m no longer worried it’s impossible. Once he’s all the way inside, he begins slowly easing in and out, coaxing me to relax.

“Good boy,” he says. “Take that cock.”

Just because someone calls you “boy,” doesn’t immediately mean he wants you to call him “daddy”. Especially if you’re already into something heavy, you need to negotiate cautiously. Of course you’re trying to give the client exactly what he wants, including unlocking desires he’s not yet been able to access. At the same time, you want to avoid crossing any lines he doesn’t want crossed. In this situation, baby steps are the best way to get where you want to go.

“I want to be a good boy,” I say back. He grabs my hips tighter and thrusts into me.

“Good boy,” he says again louder.

The door seems to be open so I decide to step through it.

“I want to be a good boy. . .  for daddy,” I say.

He lets out a little growl and starts pumping faster in and out of my ass.

“Yes daddy. Fuck me!” I yell.

“Take daddy’s big cock,” he yells back. “Take it like a good boy.”

I’ve always had a rather ambivalent relationship to roleplay. It doesn’t especially turn me on but it also doesn’t turn me off. What does get me going, however, is seeing how turned on the other person gets when I’m willing to toss out a little canned dialogue, so I’m always willing to go for it.

We keep ping-ponging “daddy” and “boy” back and forth as he ups the force delivered to my ass. I feel the orgasm building inside me from the friction on my prostate and I shoot with a guttural moan, causing my ass to clench tighter around his dick. He grabs my hips hard, slamming into me and releasing a snarling growl as he cums.

He collapses on top of me, folding himself onto the bed, and bringing us into spoon position with his arms around my chest. His face presses into the nape of my neck and I can feel his breath. I glance at the clock next to the bed and we’ve only been at it for 30 minutes. Is he going to want another round? I could easily fall asleep in his arms. But I can feel his cock getting soft inside me and I want to be the one to grab the condom, in case it’s not squeaky-clean.

I gently extricate myself and head to the bathroom, pulling the condom off as I go. Not sure if we’re done, I skip showering, just wiping my ass with a handful of toilet paper while I piss. When I come back to the bedroom, he’s gone. I return to the living room to find him naked on the couch, puffing a fresh joint. I lie down, my head in his lap and he presses it to my mouth. In inhale hard and hold, letting the smoke slowly flow from my lips.

“That was great,” he says.

“Tell me about it, I haven’t been fucked like that in a long time.”

“And you’re okay . . .  with what we did? It doesn’t bother you?”

“Yeah. It was great,” I say, slightly confused and still fuzzy from the weed.

He looks down and smiles.

“That’s good,” he says. “My boyfriend won’t do that.”

I’m still momentarily perplexed but then it clicks. He’s talking about the daddy/boy banter . . .


Follow Devon on Twitter @devondelacroix)