“Yes and no,” he said.
“I’m proud of your honesty. I’m sure it’s hard for you, being a man who’s used to being the dominant one.”
“I can do this.”
“So tell me. What is it that’s keeping this gorgeous cock so hard even though your face says that you’re a bit mortified? Are you humiliated being the only naked one in the room and with the window wide open?”
“Yes,” he whispered.
“You know, my gardener could come at any time and see you like this. Should I turn your ass to the window so he can really enjoy the show?”
“If you wish?” he ground out, trembling.
“What if he comes by as I have you bent over, fucking your tight ass mercilessly? Would you like that?”
“I’m not sure.”
I smiled, though he couldn’t see me. “I would make you face the window so you’d get to watch him watching you. You think edging delays orgasm? Imagine knowing that my gardener is watching you serve your master?”
“It would be an experience,” he said, and I laughed.
“You’re a good sport,” I said, slapping his other ass cheek and holding his privates tight so he couldn’t pull away. “They come on Mondays, so you’re safe.”
He let out an audible sigh of relief.
“I’m impressed that you’re willing to go that far to prove you can be submissive,” I continued. “You’re a bit stubborn.”
“I want you and this is what you want.”
“It is, but I think more than that, this is what you want. You’re just too ashamed to admit it.” Another two swats had him struggling, but he couldn’t move with my hand locked firmly around his cock and balls. When he arched his back again, I chuckled. “But you like that, huh?”
He nodded.
“I’m not really into hardcore spanking myself, but if you crave a trip over my knee, I’m happy to.” I sat down on the edge of the ottoman and he was over my lap so fast I felt myself getting excited. “Just a little taste,” I told him. “I have plans for you.”
“Yes, sir,” he said, his voice firm for the first time.
I pinned his legs between mine and he wrapped his arms around my ankle. The first swat landed across both cheeks and he moaned, holding his sweet ass higher in anticipation of the next. His excitement was arousing, and before I knew it, I had fallen into a rhythm and his ass was a deep pink and we were both breathing hard. When I let him up his cock was rock hard and a drop of moisture had escaped from the tip.
I eyed him sternly. “You don’t come until I say, understood?”
“Yes, sir.”
“Back on the ottoman,” I ordered and he scrambled into place.
This time, I didn’t have to adjust him, and his legs were far wider, his back arched almost painfully to present himself to me. I rubbed his reddened cheeks with a bit of lotion and he sighed, then I wiped it off and took the lube from the table nearby. “I’m going to start small,” I told him. “When you’re good at taking a plug, maybe I’ll have you wear one to work.”
His head snapped around and he looked shocked, but he quickly got back into position and I could see him trying to calm his excitement. I knew if I touched his cock he would explode, so I poured lube all over the purple plug and worked it into him as he struggled to relax.
“You are tight,” I admired when it was finally in. “How does that feel?”
“Huge,” he said with a shudder.
“Don’t you let yourself come. I can’t stress how disappointed I’ll be.”
“I understand,” he moaned. “I’m doing my best.”
“That’s all I ask.”
I stepped back and took in the sight of him. The temptation to take a picture for later was huge, but we hadn’t discussed it beforehand, and in his eagerness to please me, I was afraid he would say anything to make me happy.
So I stood there for quite some time just enjoying his beauty and how gracefully he’d crawled into the role of submissive. His cock strained and he flexed around the plug, the torture of his ebbing arousal too much for him. But he’d begged me to show him what I wanted from him, and I wasn’t going to let him down. Once I showed him how I liked to make love, he was going to be hooked.
He started squirming when his erection began to soften. I knew from experience that the plug would begin to feel much bigger and it was time to build him up again. When my hand wrapped around his shaft, he sighed, his body responding to me as if I’d spent months training him. “Whether you want to admit it or not, you’re a natural sub,” I told him.
I saw his shoulders tense and I knew I’d hit a nerve, but my touch soon distracted him and within minutes he was whimpering, begging for release. I chuckled. “Sweet Jeremy. We still have a long way to go if you’re going to prove yourself fit.”
Another whimper, then a heavy sigh when I removed the first plug and slathered the next size up with a different lube. This one warmed with friction, and I was looking forward to Jeremy attempting to keep himself from orgasming this time. Of course I would feign disappointment, but I was longing to see what his limit was, and how long he could hold off before he lost control.
The second plug went in so much easier, but Jeremy still squirmed against the stretching sensation. I watched him carefully and waited until he quieted, then I stroked him with one hand while twisting the plug in a circle with the other.
“That feels good,” he purred.
“The same rules apply,” I warned. “You don’t release until I say so.”
“Yes, sir.”
He was becoming bolder, and I could tell he was enjoying himself. His ass had faded to the softest shade of pink and my own cock jumped at the memory of him wriggling on my lap earlier. Maybe I just hadn’t spanked the right guy, I mused. It was so much more fun when they truly loved it.
I brought him to the brink three more times, each time he got close, I stopped and forced him to calm himself. The third plug was wider and a bit longer, and I delighted in the effort Jeremy gave letting it in. He moaned and wiggled, then his body relaxed and it slid in. This one had straps that went around his legs, locking it in place so it wouldn’t slip back out when he relaxed.
I went around to the front of the ottoman and sat on the edge, turned so I could look at him. “You’re amazing,” I told him, wiping a little bead of sweat that clung to his brow. “How are you?”
“I need to come,” he whimpered.
“I know.”
“I don’t think I can wait much longer.”
“You can and you will.”
“This is torture.”
“But you like it.”
“I do.”
Those were exactly the words I needed to hear.
17
Jeremy
When Brian had me climb onto the ottoman and had me there in front of the window talking about his gardener, it was all I could do to keep my cool. It was enough that I was naked, knees spread, cock and balls held tightly in his hand while he was fully dressed. I felt my cheeks burn and when he slapped my ass, it was a welcome distraction. I was into spanking. I just hadn’t shared that with him. It was the only time I’d ever wanted to switch before I’d met Brian.