My eyes went wide as I entered Steven’s home. We stood in a large foyer as he took my coat from me and hung it up on a rack by the door. A short hallway led off the foyer to the main house, and after his coat was hung up next to mine, he gestured for me to go first. I walked down the hall which opened up onto a living room furnished with black leather and mahogany furniture. A fireplace sat at the back of the room, and there was already wood laid for a fire. I had vaguely noticed that the townhouse had four stories when we pulled up, and now, as I looked around, I knew the man had money.
Steven moved past me to light the wood in the fireplace, and then he stood next to it, his head down and his hands clasped behind his back.
“Nice place,” I said conversationally, but it was much more than nice. Wooden surfaces gleamed, stainless steel and glass fixtures shone, and the air was filled with a clean scent. The floor was covered in a gray slate tile with throw rugs strategically placed wherever they were needed.
“Thank you, ma’am.” He looked around, too. “This sub inherited it from his parents when they died. He grew up here.”
“Really? Must have been nice to grow up with money.”
He looked at me, a small frown on his face. “Sometimes, ma’am. Other times, not so much.”
“Why would you say that? With money, you never have to worry about where your next meal is coming from or if the bank will take your house next month.”
His frown deepened. “Is that what ma’am was used to?”
“Yes. when I was little,” I said, wandering toward him and trailing my hand over the marble mantle, “but not anymore. Now I’m comfortable enough.” Then I looked at him briefly before sitting down on the couch. “We need to talk, Steven.”
“Yes, ma’am,” he said, and he knelt at my feet facing me.
“What are you expecting to happen tonight?”
He cocked his head but kept his eyes on the floor. “Honestly, ma’am, this sub does not know.” His hands clenched into fists on his thighs. “This sub would like to give ma’am pleasure, though.”
I stretched out one foot and ran it over his crotch. “And would you like me to give you pleasure, boy?”
He caught his breath. “Only if ma’am desires to do so.”
“Hmm. We’ll see. A few things first, though. From now on, you are to refer to me as Mistress or Mistress Chiara. Understand, boy?”
“Yes, Mistress,” he said, and I could hear the smile in his voice.
“Second, you will stop referring to yourself as ‘this sub.’ It’s getting annoying.” He flinched, but I just continued. “You may refer to yourself in the first person in private. In the clubs, you will continue with ‘this sub,” however. Understand, boy?”
“Yes, Mistress Chiara.”
“Also, you have my permission to look at me and address me directly. Unless you are being punished, I want to see your eyes.”
He raised his head and stared at me. “Yes, Mistress,” he said softly.
“Now, tell me what your former mistresses did to you.”
His hands relaxed, and he laid them flat on his thighs as he answered, “I have had to wear cock cages and cock rings, Mistress. I have been flogged and whipped and caned and belted, but only the flogger was used during sex, Mistress. The rest were for punishment. I have endured CBT and orgasm denial and ruined orgasms, Mistress.”
“Ever been pegged? Fisted?”
“No, Mistress. Neither of those.”
He shrugged. “I suppose my former mistresses didn’t find them pleasurable or necessary, Mistress.”
“So, not because you set them as a hard limit?”
“Do you have a list of your limits, boy?”
“Yes, Mistress. In my study, Mistress.”
“Go get them. I want to read them.”
He jumped to his feet. “Yes, Mistress.” He ran off down a second hallway and returned moments later with a piece of paper. He knelt again and held it up to me. I ignored him as I got up to get my phone out of my coat and pulled up a copy of my limits on it. Then I took the paper and handed him my phone as I sat down again.
“Here are my limits, boy. Read them, and if you have any problems with them, we’ll talk about it.”
We both read for about fifteen minutes. I already knew some of his hard limits such as no public sex and only private humiliation, but others I was pleased to see were the same as mine. He wasn’t into scat or piss, he wasn’t comfortable with suspension, and he wasn’t into pain for its own sake. The idea of bodily excretions sickened me, I knew I wasn’t strong enough to safely suspend anyone, and I wasn’t a sadist in any sense of the term. I would punish him if he disobeyed, but, like Brenden, I hated to do it, especially something physical. I was much more into orgasm denial and chastity cages. A man who was denied the right to cum for a week was usually very obedient for a long time afterward. Under soft limits, he had listed pegging and anal fisting, wax play, and needle play among others. I wasn’t really into needles, but I would try the others with him. My last sub I had that I actually made physical contact with had loved getting fisted by me, and it hadn’t taken long for him to take my entire arm up his rectum. I looked up from the paper when I was done, and he was looking up at me.
“Any questions, boy?”
“No, Mistress Chiara.”
“Give me my phone, boy.”
He held it out to me, and I set it on the small table by the couch along with the paper. Then I sat on the edge of the couch and said, “Come here, boy.” He shuffled toward me on his knees. I grabbed the strap of his harness that went around his neck and pulled him so that he was between my legs. “You said you wanted to pleasure me, boy?”
“Oh, yes, Mistress.”
“Let’s see what you can do, then. You are in control for now.”
He glanced up at me. “May I undress you, Mistress?”
I stared at him for a moment as I decided if I wanted to be bare before him, but there wasn’t really a question about it. I wanted to feel his hands on my skin, so I said, “You may, boy.”
“Thank you, Mistress,” he said, and I heard the smile again even though his head was down. He scooted back and prostrated himself on the floor, giving me a perfect view of his beautiful ass. He brought his mouth to my left foot and kissed the top of it softly as he undid the strap of my heel. He slid it off and then did the same to my right, again kissing it first. I sat as still as I could, but when he got back on his knees and slowly ran both hands up my left leg from my ankle to the top of my stocking, I couldn’t help groaning, and he grinned at me. I had expected callouses or at least rough skin on his hands, but they were soft, and he gently undid the garters from my stocking before reversing the path of his hands, taking the stocking with them. Then he took off my right stocking in the same way. What he did next had me holding my breath.
He slowly kissed and licked his way back up the inside of one leg while his hands caressed the other. When he made back to my thigh, he groaned softly as his tongue traced a path around the leg of the bustier. I wanted to hear what he was thinking, and, as I put my hands on his head, I breathed, “Talk dirty to me, boy. Tell me what you want to do to me.”
He looked up and grinned again, his brown eyes sparkling. “May I say anything, Mistress?”
“Yes, Mistress.” His sat up on his knees and was almost eye to eye with me as his cock settled between my thighs. His hands went to the laces of the bustier, and he slowly started to untie it. “I want to kiss you, Mistress Chiara. I want to kiss your mouth and your shoulders and your breasts and your hips and your cunt. I want to give you pleasure like you’ve never felt before. I want to slide my fingers into your beautiful body until you cum all over them. Then I want to suck them clean and do it again and again and again until you tell me to stop. I want to taste your body, Mistress. All of it.” His hands never stopped moving, and as he released the last lace, his hands moved to my shoulders, and he slowly lowered the straps which exposed my breasts to his gaze. As I pulled my arms out of the straps, he glanced down once, and then he said, “Please, Mistress Chiara, please let me kiss you.”
“Fuck, yes,” I breathed. My skin felt on fire everywhere his hands had touched, and I wanted more. He left his hands on my shoulders, leaned forward, and laid his lips on mine gently. My hands were still in his hair, and I fisted them tightly as he traced his tongue over my lips. I opened my mouth, and invited him in. He didn’t wait as his tongue immediately touched mine, but he kept the kiss short and moved his lips to my jaw and then to my ear.
“Getting bold again, boy?”
He chuckled. “Only because you told me to, Mistress,” he whispered in my ear before tracing my ear with his tongue. I groaned, and he sucked the lobe into his mouth. When he released it, he continued whispering to me. “Please, Mistress Chiara, let me fuck you later. I will show you such pleasure if you only let me fuck you.”
I didn’t say anything, and he trailed kisses down my neck to my shoulder. Only then did his hands move. As he kissed his way across my collarbones, his hands moved to my breasts, and he cupped them gently. Then he spoke against my skin. “Do you like it soft or rough, Mistress?”
“That depends, boy,” I breathed as his fingers drifted over the undersides of my breasts.
“On what, Mistress?” His thumbs found my nipples, and he ran circles around them as his kisses got closer to his hands.
“On my mood at the time.”
His tongue snaked out, and he lightly licked my nipple. I gasped and he did it again. “And your mood now, Mistress?”
“Just keep doing what you’re doing, boy. I’ll tell you if it’s not enough.”
“Yes, Mistress,” he said, and then he sucked my breast into his mouth while gently taking my nipple between his teeth.
“Good boy,” I breathed as my back arched, putting my breasts closer to him. His only response was to worship them with his mouth and hands until I was panting. I knew if he kept it up, I’d cum just from what he was doing, and I so wanted to. It had been years since anyone had been able to make me climax just by playing with my breasts, but he was very talented. He seemed to sense that I was close to the peak because his tongue and teeth and hands worked together, alternating between the left and right, stimulating me until I cried out loudly as my first orgasm raced through me.
“Fuck, boy! Holy shit, yes!”
I felt him smile, and then he kept his hands on them, still tweaking my sensitive nipples, but he started kissing his way down my chest to my belly. His hands moved again when he reached the edge of the bustier, and then he lifted my ass from the couch and slid the fabric down my legs.
“So fucking beautiful,” he whispered against my pelvis, and his words caused my body to heat up. When the bustier was off, he dropped it next to him and trailed his tongue from my asshole, over my slit, and to my clit. He swirled his tongue around it, and I cried out. When he sucked it hard between his lips, I bucked my hips closer to his mouth, and he slid his hands under my ass. He kept his lips around my clit as his tongue worked it, and he quickly slid one finger into my wet cunt. “More, Mistress?”
“Yes, boy,” I groaned, and he slid another finger in.
“Fuck, yes, boy!”
“How many, Mistress? I don’t want to hurt you.”
“Just keep going, boy. I’ll stop you.”
“Yes, Mistress.” He sucked my clit into his mouth again and added a third finger to my cunt. That stretched me out deliciously, and I placed one hand on his shoulder. He got the hint and started fucking me with his fingers as he devoured my clit. Fuck, he knew what he was doing! Each time his fingers entered me, he rubbed one against my g-spot, and he did the same as he pulled them out. His tongue was masterfully stimulating my clit, and it didn’t take long before I felt my second orgasm approaching. My walls clenched around his fingers, but he never stopped moving them or his mouth.
“Fuck!” I screamed as my entire body stiffened with the force of my climax. My hand tightened even more in his hair, and when I finally relaxed, he sat up on his knees, pulled his fingers from me, and proceeded to lick them clean just as he said he would. Slowly and sensuously, he stuck one in his mouth, sucked on it briefly, and then pulled it out.
“You taste just as delicious as I had imagined, Mistress,” he whispered when he was done. “Again?”
“No, boy.” He frowned slightly but wisely kept his mouth shut. I hooked my finger under his neck strap and pulled him close to me. Then I reached down and undid the strap that went between his legs. His frown instantly changed to a smile, and he stared at me while I undid his harness. “I want to fuck you, boy.”
His smile turned into a grin. “Yes, Mistress. Thank you, Mistress.”
I released the last strap of his harness, and he let it drop to the floor behind him. Then I stood up and asked, “Where’s your bedroom, boy?”
He pointed down a third hallway. “Second room on the right, Mistress.”
“Do you have toys in there, boy?”
“Yes, Mistress. In the nightstand to the right of the bed, Mistress.”
“Meet me there in five minutes, boy.” I took one step in that direction and then stopped. “Don’t be late, boy, or I will punish you.”
I walked to his room, opened the door, and smiled. He had a four poster bed, and I could tell he had been restrained there before. Cuffs and straps were attached to each post, and I ran my fingers over them briefly before moving to the nightstand. I opened the top drawer and was pleased to see several dildos. I had no idea if he used them on himself or his former mistresses, but I was going to use them on him tonight. I then opened the bottom drawer and found a pink chastity cage, a flogger, and an adjustable cock and ball ring. I put the flogger and cock ring on the nightstand and chose four of the dildos he had. I put these next to the other items, lined up by size, along with a bottle of lube. The largest dildo was only about five inches long and about an inch and a half in diameter, but he said he hadn’t been pegged before, so I figured that would be enough for him for now. If he became my permanent sub, though, I would quickly train him to take much larger ones and make him wear them to work often. Then I sat on the bed to wait for him.