For the first time, Oliver looks slightly uncomfortable. “Um, I’m honestly not sure about those things. I’d be willing to try them, though. But would it be okay if I asked you to stop if it turns out I don’t like it?”
Rather than reply right away, I hold my hand out, palm up. He regards it for a moment, then slips his hand against mine. I close my fingers and caress his knuckles with my thumb. “Oliver, if we move forward with this weekend, you absolutelymusttell us to stop if you’re anything less than one hundred percent happy at any point. Is that understood?”
He considers me with wide eyes for a moment before nodding. “Yes, Master.”
“We will use a simple traffic light system,” I explain further. “Green means go, yellow is pause, and red is stop everything immediately. You will never,everbe punished for using your colors. In fact, I want to make clear how proud I am to hear your honest answer just now about the pain play. We have to be able to trust each other, Oliver, and that gives me a lot of faith in you.”
He smiles bashfully. “Thank you, Master,” he murmurs.
“Good boy.” I stroke his hand for a moment, giving him time to compose himself again. “I would be honored to experiment with the pleasure pain can bring for you. But if you’d rather, we can skip it entirely.”
He rocks from side to side, watching his hand in mine. “No, I think I’d like to try. That feels safe, knowing I can opt out at any time.”
“Exactly,” I agree. “You will always be safe with us, Oliver.”
“Thank you,” he says again, meeting my gaze. Those eyes. It’s not just their unusual color, but the sparkle behind them. I can’t wait to see what my Augie Pie makes of this young man, because I’m already smitten. “Is that everything?” he asks.
“Almost,” I say. “I have three more items to discuss. The first should be quite simple as we’ve partially covered it in our texts. But I want to confirm that you’re on PrEP?”
“Yes, Master,” he says eagerly, reaching into his bag. “I also swung by the clinic yesterday to get a quick turnaround checkup, and I can show you the results here—oh.” He goes pink and looks sheepish as he sees something on his phone screen. “Sorry, my best friend has messaged me three times to make sure I haven’t been murdered. She listens to too many true crime podcasts. Sorry, I…”
I gesture to the phone. “By all means, please reassure her. I like that you have people looking out for you.”
He smiles sweetly as he hastily types. “She’s the best. I wouldn’t have survived college without her. Okay, done! Right…oh, the test results.” He flicks between apps and then brings up a screen to show me. “All clear. So if you, um, wanted to…like you said…”
“I would very much like to negate the use of condoms this weekend, yes,” I reiterate. “I am all for safety. But they are hardly a culinary delight, which would dampen the mood I’m aiming to set for my husband’s birthday celebration. However, if this is going to be a problem for you?—”
“No,” he says quickly before shifting in his seat and looking contrite as he puts his phone back in the bag. “Sorry, Master. I didn’t mean to interrupt. But I’ve thought a lot about it since you already mentioned it. This is why I’m on PrEP. Usually, I put up with how condoms smell and feel, but if this is going to be a fantasy…” He sucks in a deeper breath and nods. “I don’t want to break the illusion by stopping to check for consent all the time, and I definitely don’t want to ruin the vibe worrying about anyone suiting up. I’m confident in the medication I’m on and, well, part of my fantasy is trusting you and your husband.” Hestraightens his back and looks me dead in the eyes. “Can I trust you, Master?”
“Yes, Oliver,” I say firmly, my gaze not wavering a millimeter. He might be shy and vanilla, but seeing this little burst of determination in asking for what he wants is extremely sexy to me. “That’s the most important factor in this entire arrangement. If we don’t have trust, it all falls apart. I would be bringing you into our home to please my husband, but I am a Dom. My priority is always on the safety, comfort, and enjoyment of my sub or subs. For this weekend, that would be both you and August, but I will pay particular attention to your needs as someone new on the kink scene as well as the boy serving his Daddy and his Master. I don’t want you to ever feel like you’re not being taken care of. No,” I amend, raising a finger at him. “Treasured. You will be treasured at all times. That includes your physical safety as well as mental well-being.”
I’m known for getting on my high horse with speeches like that. August enjoys teasing me about it. But I watch as Oliver nods, apparently absorbing everything I’ve said.
“Okay,” he says slowly but with conviction. “I like that. Thank you, Master, for respecting my wishes. So, we’re agreed? No condoms.”
“Agreed,” I tell him. He lets out a little breath and nods.
“Okay. What’s next?” He smiles and reaches for another cake. It pleases me greatly that he feels relaxed enough to keep eating. With a nod of my own, I consider that matter closed.
“The second is financial,” I continue to explain, genuinely unsure of how this point is going to be taken. “As my husband is nothing if not thorough, his food kink also includes being a sugar Daddy. He will want to buy his sweet treat presents, plural. He will also want to pay you for your time. Does that make you uncomfortable?”
Again, Oliver pauses. But I feel the weight of this one more. “Um, you don’t have to do that,” he says with a little frown. “I’d be doing this because I want to.”
“And my husband would be gifting you money because he wants to, as a way to spoil you,” I clarify. “He will know without doubt that you’d be joining us of your own free will. But it makes him feel good to share his wealth.” I flick my eyebrow at Oliver in a conspiratorial manner. “Did I mention that he’s filthy rich and literally earns more than we know what to do with? He gives away as much of it as he can to good causes, and you would be one of them.”
Oliver laughs hesitantly. “Um, well. Maybe? The gift thing sounds nice, maybe. But I might have to see how I feel about a bank transfer.” He wrinkles his nose. “If I’m being honest, I’m worried that might, um, cheapen the experience. I don’t know if it would leave me feeling kind of icky. Sorry.”
“No, Oliver,” I insist. “Thank you so much for telling me your true thoughts. That’s very important. I’ll be honest with you in return. I know this will be important to August. It will probably make him feel dejected if he can’t at least do something for you.” I take a moment to finish my tea as I think. Oliver waits patiently until an idea strikes me. “How about a compromise? If you genuinely don’t feel comfortable with a financial gift for yourself, would you be all right selecting a charity for my husband to donate to in your name?”
This adorable boy’s whole demeanor lights up like a Baked Alaska en flambé. “Oh, that’s a wonderful idea! Aren’t you smart? Yes, I’d be very happy with that, Master. Thank you.”
My heart flips in my chest. We’ve never had a sugar baby who didn’t happily accept everything August wanted to give them. And that’s the whole point, so nothing wrong there. But I knew this young man was special from the second I read his reply.I can’t deny how endearing Oliver’s humility is, and his casual praise toward me certainly strokes my outrageous ego.
It’s his kindness, though, that takes me a moment to recover from. He seems sincerely delighted at the notion of August gifting a check in his name. I’m curious what type of organization he might be drawn to. However, we can discuss that when—or if—it comes to it. I’m still hoping if he agrees to this arrangement, he might change his mind about my husband’s generosity.
“All right,” I concede. “We might need to revisit the specifics of this element again to make sure everyone is happy. But thank you for agreeing to an alternative option.”
He gives me half a shrug but the smile he tries to hide is bashful. “Thank you for offering one. Money can be a touchy subject for me.”