Lillian Teaches Me a Lesson

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."

"I'm ready to get fucked now. Since you just had to cum, Mr. Floppy there"--she pointed at my flaccid dick--"is not going to do me any good, so it's got to be the harness," she said. She held up my strap-on harness. I stepped into it and buckled it around my waist. A large dildo was already attached.

She had me lay back on the bench and then straddled me and slowly lowered herself onto the dildo. It was girthy and I watched to see whether it would fit. I had bought it with some doubt whether it would fit inside anyone. It did take some work. As she descended onto the tip, she gasped. She slowly moved up and down, moaning, mouth open. She sank further down and rested her knees on the bench. Her breasts bobbed and swayed as she impaled herself with more and more of the silicone cock. I watched Lillian rise up and sink down, up and down. My thoughts drifted... I imagined... what...

"Boy! Wake up!" Lillian said. I forced my eyes open once again. "Do you get the point yet, boy? After you cum, you aren't good for anything. You just get sleepy. I'm just going to try one more way to keep you awake. Take that dildo off." She detached the dildo from the harness and suction-cupped it to the wooden chest. "Maybe it'll work if the dildo's inside you. Hop on it."

I eyed the thing. It was huge. I didn't ever think it would fit inside me, but I knew I had to try. I spread it generously with lube, and then added more just inside my asshole for good measure. I straddled it and positioned my asshole over its tip. I wiggled to encourage it into the right spot, and lowered myself slowly. Pressure built up as I did, and then the tip popped in. I gasped and held still.

"Well, look at that!" exclaimed Lillian. "I want to get fucked and nothing, but when it's your pleasure it comes right up." I followed her gaze, down to where my dick had popped up into an erection. "Okay, mister, I want you to cum again, but this time just from the anal."

Even though I didn't think that would work, I didn't argue. I gingerly moved up and down on the dildo. My dick stuck straight out, bouncing with the right of me. Over a few minutes, I slowly eased more of the dildo into my ass. Something started to build up, for sure, but so slowly. Second orgasms take me a long time in any case and, in this particular case, I thought my knees might give out first.

After ten minutes or more of this, Lillian lost patience too. She squirted lube all over her hands, knelt down in front of me, and started rubbing my dick between both hands as I continued to fuck myself with the dildo. It felt amazing for the first few minutes, and then the lube started to get sticky. The extra friction, plus the anal stimulation, brought me closer to orgasm. It seemed like it took forever, but eventually I came, with a little scream. This time, there were only a few drops of cum, which landed on her face and chest. As she had me do to myself before, she kept going for a lot longer than I liked, and she had me keep going on the dildo, too. It even started to hurt after a minute.

She finally stopped. "Clean me up!" she said. I lifted myself off the dildo and grabbed a wipe. "No, lick it off," she told me. I licked the cum off her face, which had started to dry. I used the wipe to clean off myself and the dildo and the wooden chest.

As I cleaned, Lillian lectured me further about how selfish my orgasms make me. I sensed that we were almost done. As I finished up, she lay back on the padded bench and told me to eat her out to thank me for her lesson. I said, "Yes, of course, Miss. Thank you for showing me how my orgasms affect how I perform for you."

I leaned forward to Lillian's crotch and used my fingers to spread her lips. "Just a second, boy," she stopped me. "Hold me open just like that." Reaching her hand out next to the bench, she picked up a small cup. It was full of the cum from my first orgasm earlier. With one hand, she carefully positioned the cup above her pussy lips and slowly poured its contents. With her other hand, she swirled the cum into and around her pussy. "Now, lick me clean inside and out. And I want at least five more orgasms as you do it."

I've swallowed my own cum before, more than once, at her direction, but always when it was still warm, and always in one quick gulp. My own lips involuntarily puckered at the idea of licking it out, cold, one little bit at a time. I steeled myself and thought about how much I loved Lillian, and that let me get started. It got easier after she started responding to my tongue on her clit and around her pussy opening. I added my fingers a little while later, and it wasn't long before she was trilling to her fifth additional orgasm.

"Would you like more orgasms?" I asked her, as I always do.

"No, boy, that's good. Let's go to bed."

We wiped up a little more and moved to the bed. I thought over what she'd demonstrated to me tonight. I guess that it showed how much sense it made that, if I got to cum at all, it was always the last thing that we did.

I cuddled closer to Lillian and put my arms around her. "Miss?" I said. "May I sleep now?"

"Yes, boy."

I hesitated for a long time before I asked my next question. I hoped she could take a joke. But I couldn't resist. "Miss? When's the next time I get to masturbate?"

She gave a big sigh, but I could hear her trying to suppress a giggle as well.

And the next thing I remember is waking up the next morning.