Danny pressed his lips together, breaking eye contact. I rested my hand on his knee, silently reassuring him that any answer he gave was the right one. At the same time, my chest tightened with fear that he was going to say I wasn’t giving him enough attention. He’d made clear his frustration with how slow things between us were progressing, and now I couldn’t help but think I should have paid more attention to his actions rather than doing what I thought was best for him.
“It’s okay, Danny. Anything you say stays in this room,” I promised him.
The corner of his mouth turned up in a slow smile. He traced my fingers and tipped his head to the side. This playful version of Danny was one who hadn’t come out often, but it was when he was his most beautiful. I wanted to do whatever was within my power to keep him in this zone. “It’s not that he doesn’t play with me, but sometimes I think he’s too careful, like he doesn’t trust that I’m not going to break. I’m not fragile, Doctor.”
“I see.” I scrubbed my stubbled cheek, trying to process his words. There was something freeing in our role play that allowed him to be brutally honest, even if that upset me for the pain I’d caused him. “And is that why you came on your own today? Are you hoping I’ll be able to help you convince him that you’re ready for this step?”
Danny nodded. “If you tell him it’s okay to be rough with me, he’ll believe you. He’s worried he’s going to hurt me, but it hurts even more when he’s always so careful.”
“There are several ways we can ensure you’re ready for more hardcore activities,” I explained as I lifted Danny’s shirt over his head and tossed it to the chair in the corner. My hand drifted down his torso, and I smiled when he visibly shivered. I leaned in close enough that I could feel his rapid exhalations against my neck. “You might have heard that I have some…unconventional techniques.”
“Wh-what type of techniques?” Danny stammered. “I’ll do anything, Doctor. He’s the best top I’ve ever had, and I want him to know I’m not worried about him being like the men I was with in the past.”
“Be careful what you offer, boy,” I warned him. He sucked in his stomach when I shoved my fingers behind the waistband of his shorts. “Will he understand that what we do in this office is purely professional? I don’t want you to go home and get in trouble with him for having a thorough examination.”
Danny shook his head. “I won’t get in trouble. Hopefully, he trusts that I would never have sex with someone else just to get off since he won’t fill me.”
“And is that what you need?” With one hand still teasing Danny’s hips, I pulled him upright so he stood before me. I quickly tugged on his shorts, allowing them to drop to the floor. Danny moved his hands to cover his erection. “You don’t need to hide that from me. Before we’re done, there won’t be any part of your body that I haven’t seen and touched. Now, hop back up on the table and lie back.”
I squeezed my balls, trying to relax a bit as I made notes on my tablet. Without turning back to him, I ran through a list of questions. With other boys, this was meant as a bit of a warm-up to help them sink into their role, but with Danny, it felt more like getting to the root of his feelings for me.
“You mentioned showing your partner your test results,” I said, trying to keep my tone cool and professional. “Does that mean you’re serious about him? I don’t get the impression you showed them as a courtesy even though you’re still wearing protection. Having sex without condoms is a big step. Are you aware of what that would mean?”
It wouldn’t do well for him to know how desperately I wanted to sink into his body and fill him. He didn’t need to know yet, how many times I’d considered what it would be like to plug him in the morning before I left for work and then add a second load when I got home but before he went to work for the night. I’d visit him at the bar, sitting on my stool, watching his discomfort every time the plug tapped against his prostate.
“Yes, Doctor,” Danny confirmed. “Some people might think I’m rushing things because my last relationship ended badly, but I don’t want there to be anyone but him. This is something I can give him that no one else has had.”
“That’s quite the gift.” I curled my fingers around the edge of the counter to keep from scooping him into my arms and telling him how deeply I’d fallen for him. “But this can’t be something you do for the other person, Danny. There’s no need to rush if you’re not ready to take that step for yourself.”
“But I am,” he insisted, then let out an impatient huff. “I’ve kissed the frogs. I am very well aware of the things Idon’twant, and he’s the opposite of all of those. Yes, I want to give him part of me that’s just his, but I also want to know what it’s like to feel him unload into me. And…other things, too, but you don’t need to hear about those.”
“Oh, I think you’re wrong about that.” I was definitely going to be dead before we left this room. My cock was throbbing and I was losing the ability to go slow. “As your doctor, it’s important that you don’t withhold any information from me. What else are you hoping he’ll do to you?”
The sound of the paper under Danny’s body crinkling as he squirmed filled the silence. I glanced over my shoulder to see him with a death grip on the bed and his hips flexing repeatedly. This was going to be fun.
“Tell me, Danny. If you want me to help you prove you’re ready for penetrative sex, you need to be mature enough to use your words,” I demanded, using the stern voice I knew turned him on. But maybe it would be even more fun for me to toy with his body as I guessed what he was too shy to say.
I pulled out the stirrups, lifting each of Danny’s feet into place. “Move so your butt is at the end of the table.”
The paper tore as he slid closer to the edge. I picked up a tube of thick lubricant, squirting a glob onto my fingers. He whimpered when I pulled his ass cheeks apart, pressing my fingertips against his entrance. “Do you want to have a sloppy hole for him? Is that why you want him to fill you?”
“P-part of it…Sir,” he admitted. His back arched off the table as the tip of my middle finger breached his entrance. “Oh fuck, I don’t think that’s supposed to feel good, doctor.”
“On the contrary, that’s exactly what we need today,” I corrected him. “I need to gauge your responsiveness so I can complete a report for you to take to your top. It’s going to include all the things you’re too nervous to say to him yourself.”
I pushed my finger deeper, massaging his taint with my thumb. “Now, tell me more about how you want him to use your hole. Is it just about feeling his cum leaking out, or is there something else that intrigues you?”
“All of…all of it, Doctor. There’s something about feeling full back there that turns me on. I…I want him to keep pushing his cum back inside, threatening to punish me if I can’t hold onto it.” His entire body flushed bright red with that admission. Precum leaked from his tip to his abs. His cock twitched, creating strings of the thick substance. “I want to wonder if someone’s going to catch us. I want to know he trusts me to tell him if he’s going too far past my limits. I don’t want him to be careful forever, Doc.”
I reached for the applicator, reassured he was going to love this part. He cried out when I pulled my fingers away. I pressed my clean hand to his stomach, gently rubbing as I soothed him. “Easy, Danny. We’re going to start the next part of the exam now. If you do well with this, there are a few other things we can try if you’re willing.”
“Yes, please.”
I chuckled, shaking my head. “I warned you about being too eager, boy. That’s a good way to get in over your head.”
“But you’re a doctor. I know you won’t do anything to hurt me.” Oh, my dear, sweet boy. I truly hoped he wasn’t this blindly trusting of doctors in real life. While most of them were nothing but professional, there were definitely some bad apples out there. I pressed the tip of the applicator against his entrance. “What’s that?”
“We need to get you fully lubed so I can see how tight your passage is,” I explained. “Sometimes, tops are worried about physically injuring their partners, so I like to give some assurances that there’s no risk. To do so, we need to test your elasticity.”
