Lillian was quiet during dinner. Sometimes she's quiet because she's upset with me, which made me nervous. After the meal, my anxiety grew when she took my hand and led me into the bedroom without a word. Then she told me to strip and lectured me a bit as I did. "You've been asking to masturbate too much lately. You know that I'm in charge of that. You gave it over to me and it's my choice when or if you do. And the hinting you've been doing lately is just as bad. I'm going to start marking your chances at masturbating on the calendar so that I don't hear from you so much about it. But those are plans, not promises, understand, and I can change them just as easily as I can set them."
Lillian wound down a bit. I sat, naked, on the wooden chest along one wall of the bedroom. I felt sad that I'd annoyed her so thoughtlessly. I didn't say anything, and in a moment she continued, "But, right now, I'm going to teach you a lesson about why I restrict your orgasms in the first place. Here, you'll need some lube." She thumbed open a bottle of silicone lube and squeezed a large dollop into my hand. I looked for a place to wipe off most of it but she shook her head and said, "No, you'll need all of that today," which left me confused.
"Start stroking," Lillian told me. "Get right up to the edge for me. Be quick about it." My dick was already half-hard from the scolding and it took only a few seconds to bring myself to full erection with my hand. In hardly more time, I was just short of orgasm, so I backed off, from hard and fast strokes, to light ones with a couple of fingers along the sensitive underside of my cock.
"Did I tell you to stop?" Lillian rebuked. "Keep it going fast. But don't cum." She loves to tell me this. It's impossible to stroke hard and fast for long without cumming. If I'm playing on my own--which is rare since Lillian normally supervises my masturbation--I have to slow down or stop frequently. It's a real dilemma to both keep going and not cum. She knows that and uses it against me regularly. In a few moments, I was trying to figure out how to look like I was stroking hard without actually doing it. That's impossible but it's always where my mind goes.
I approached the point of no return. "Miss! Miss! I...need...to stop...or I'm going to...CUM!" I blurted out. I stared at her, waiting for guidance. She looked back with amusement and handed me a little cup. This was clear enough, so I kept pumping and the first few spurts of semen landed in the cup.
I half-expected at this point to hear Lillian say, "STOP!" to ruin my orgasm and allow the rest of my load to dribble out slowly without experiencing the full sexual climax. I braced for it, but it didn't come. She allowed me to fully enjoy my orgasm. I leaned back against the wall as I luxuriated in the best cum I knew how to give myself. I squeezed the last few dribbles from the tip of my cock into the cup, and set it aside. I relaxed, released my dick, and closed my eyes in the beginning of my post-orgasmic blissful drowsy stupor.
Or so I intended. Instead, Lillian told me sharply, "No! Did I tell you to stop? Keep going, boy! Quick, just like I told you!" I resumed stroking. Soon, the extra rubbing on my supersensitive dick left me overstimulated. I squirmed and waved my legs around. My mouth opened and I moaned unintelligible syllables. I kept going for minutes at Lillian's direction, speeding up again when she noticed that I'd slowed down. The stimulation competed with my natural tendency to post-orgasmic drowsiness, like a furiously masturbating zombie.
After several minutes, even the constant stroking was no longer keeping me fully hard. When Lillian noticed that I was now stroking a flaccid cock, she motioned for me to stop. I let my eyes flutter closed for a moment and caught my breath. I was glad that Lillian had given me extra lube because, without it, I would have rubbed myself raw. I was too drowsy to risk closing my eyes for more than a moment, so I opened them again.
"Now it's my turn. Come over and get me started." Lillian had taken off her clothes sometime previously. Now she lay back on the padded bench set near the bed, her head on a cushion and her legs on either side. My dick hung limp, thoroughly spent, as I got out her wand. I connected the app and pressed the wand against her vulva. I started on the rising intensity patterns that I had figured out from trial and error, and I spoke to her with my loving and reassuring words. I knew that, together, these things would start getting her off within a few minutes.
And so they did. In less than five minutes, she announced her first orgasm with the fluttering trill that always accompanies them. I started in on the pattern that I knew from experience would get her off about every 2 minutes. After about 30 seconds on full blast, she started cumming with a little encouragement, and then after about another half a minute I backed off and gave her a break, and then slowly started building her up again. And then repeat for the next one. I was good at it, and I loved how she held back until I told her "Cum! Cum now!" I helped her through a second orgasm, then number three... four......... four...
"Hey!" Lillian said.
My head was down and my eyes were closed. I whipped my head up and opened my eyes and carried on. Had I nodded off for a moment? I hoped that it had only been a few seconds. Lillian was on her back, looking up, and I was at her feet, so maybe she didn't actually see my head sag. I focused on giving her as many orgasms as she wanted. What number were we on? When I thought I'd counted ten, I said, "That's ten, Miss! Do you want more?"
Lillian was quiet for a moment. Then, in a tone that suggested veiled frustration, she said, "Boy, you're showing exactly why I don't let you cum. It makes you sleepy, and right away. I am going to have to wake you up. Switch places with me. Face down." She got up, and I lay down on the bench, face down as she'd asked. I crossed my arms and put my head down and tried to keep my eyes open.
Behind me, Lillian picked something out of the toybox. A moment later, I heard a momentary whoosh, and then I screamed with pain and surprise. She had struck my ass with my meanest cane. I had always heard that impact hurt worse right after an orgasm, and this confirmed it. The lack of any warm-up, or any warning, didn't help either.
"Count! That's one!" Lillian said.
I repeated, "One!" She hit me again. "Ow! Two!" I said. "Three! Four!" She was hitting in the same place each time, across both cheeks, so each one got a little worse. On the bright side, it was waking me up.
Lillian went rapidly through ten strokes. Then she stopped. "Do you think you're awake enough now to pay attention to me?"
I nodded contritely. "Yes, Miss."
