Twenty Cups Ch. 01

I nodded.

"Now watch," she said. She opened her lips like a huge yawn and drew the tip of my penis toward it. Suddenly, her lips drew back, unveiling two rows of white teeth. Mom very gently bit down on the tip. I caught a short breath.

She released me.

"Would you want to feel that, running up and down your erection, baby?"

I shook my head.

"No. Of course not," she murmured. "There's a right way and a wrong way for everything. Oral sex is no different."

I didn't say anything.

"Inexperienced couples don't know what the right way should be like, and sometimes they don't feel comfortable talking about such things. It can lead to real problems during intimacy."

I watched her face move even closer to my erection, and I felt her breath cascade over the tip. Her eyes rose and connected with mine.

"I...I'm going to put your penis in my mouth for a moment—just so you can learn, okay baby?"

I swallowed and nodded once.

She looked up and down the shaft, and then her mouth formed an enormous oval. I saw her fleshy pink tongue waiting inside. She drew my penis toward it and closed her eyes.

My jaw fell open.

Her soft lips took the entire tip in a wet embrace. Her tongue felt hot against it. Then, without a sound, I watched her lips unfurl and descend down the shaft, collecting another half inch and then clasping around it. Her lips opened and stretched again, and she gathered another half inch. And again. She gorged still more, and the tip of my penis pressed firmly against some smooth and slippery surface hidden in the back of her throat. Finally, with half of my penis in her mouth, Mom's lips began to lazily glide up and down, while her fat tongue nudged and dragged against the underside.

The warm sensation I had earlier felt was now gone. It was replaced by rippling heat, like being immersed in a bubbling jacuzzi, only this heat was under my skin, and it originated at the tip of my erection, where Mom's lips encased my penis, and spread from there to every limb.

When Mom's mouth opened, and my full erection reappeared, I blinked and swallowed. I drew long breaths. I had been laying down flat. Now, I was propped up on my elbows, looking down at her.

Her face was partially hidden by my penis when she asked, "Would you like to ejaculate in my mouth this time? To understand?"

I nodded.

"Saliva won't interfere with the results."

I nodded again.

"I'll have to be careful not to swallow any."

"Okay."

"And when you think it's over, I'm going to use my hand to get the last few drops into my mouth."

I nodded.

"Just hand me the cup when my mouth comes off your penis."

"Okay." I grabbed the jar and held it tightly.

"Don't worry, but try not to move too much. Relax and just let your semen fill my mouth, okay, baby?"

I nodded, and Mom pushed her tongue against the tip, and then closed her lips around it. Her head rose and fell, turning slightly so that I wasn't always looking at her bright red locks, but also seeing the side of her face sometimes—her cheek, her nose, her eyelashes, and her lips as they clutched and drew upon my penis.

I felt my chest rise and fall more rapidly. I squeezed my hands into fists on my stomach, still gripping the sample jar in one of them. When I grunted, Mom squeaked into my erection. Her head rose and fell, I grunted again, and she whimpered. I was ejaculating.

I grumbled like a bear while my the length of my penis rapidly squeezed. I felt the fluid pour forth from the tip in great bursts. Mom's lips clasped my penis just beneath the tip. I felt her fingers suddenly take hold of the base and knead up the shaft. The tip, still inside Mom's mouth, felt immersed in semen. Then, the throbbing eased.

Mom's fingers worked up the shaft caterpillar-like. When she reached the top, she started again, back at the base. Her head was completely still, but her hand worked feverishly to coax up any remaining fluids. I felt suction, as if the tip were suddenly tugged hard, and then Mom's hand let go.

She hummed, and I pushed the container into her empty hand. She took it. I felt her lips ease and let the tip of my penis slide free. Her head rose. She drew the cup toward her mouth and looked at me. Then, she opened her mouth. My semen poured from her lips into the container. A few final globs oozed out and hung on her lower lip. Mom spat them free, and then sat up on her heels.

I collapsed back on the bed and covered my face with my hands.

I felt Mom climb out of bed, and I heard her walk to my desk and screw the lid on the jar. I watched her come back beside me. "You did good, baby. I'll put this in the freezer, and then I need to get back to work."

I nodded. She reached out and took my hand. She squeezed it and then let it go. I listened to her leave my bedroom, closing the door behind her.

My bed had never felt so perfectly comfortable.

***

That night after dinner, Mom took me aside and told me that she was going to have Lia join us for the next morning's session.

"Why?"

Mom said, "Well, baby, I told Lia that it was for her edification. As you know, she hasn't any idea how this works. She's is nursing school, and it would help her to understand this process."

"I don't want her there, Mom. It's embarrassing."

"You have nothing to be embarrassed about. I, however, do."

I stared at her.

She sighed. "I should not have used my mouth to help you ejaculate. An observer might even say that I performed fellatio on you."

I shook my head.

"No, baby, it's true. I was trying to help you learn, and I may have gotten carried away." She sighed, again. "The important thing is that we got a good sperm sample from you."

"But, why is Lia..."

Mom interrupted me. "I didn't just invite her to see and learn. I also invited her so that I would not be tempted to intrude upon you again."

"But, you helped."

"That's very sweet of you, but this is my decision. Lia will sit in and learn; I will keep my hands to myself."

"Emma isn't coming, too, is she?"

"No, baby, Emma's going shopping for presents in the morning with some friends."

I sat silently.

"Okay?"

I nodded.

"Now, tomorrow I would like you to use lubrication."

I nodded.

"I picked up a pillow rest for the tablet today—like a triangle-shaped pad that will hold it up. You can use that for your sexy dancing videos."

I nodded.

"If you need help at the end with the jar, just let me know."

"Okay."

"All set, then?"

"Yeah," I said, and then a thought occurred to me. "Mom, with Lia in there, I might get nervous."

"Oh." She considered this, and then, finally, said, "Tell you what, I'll invite her in the room only after you have an erection."

It was decided.

***

The three of us walked upstairs toward my room. Both of them were wearing tight pants that highlighted their butts. Lia was behind me, and I nudged Mom. When I had her attention, I surreptitiously pointed my thumb back toward Lia, and kind of bugged my eyes, trying to remind Mom of what we'd discussed the night before.

She nodded.

At the door my bedroom, Mom stopped. "Lia, dear, will you please wait here. I'll call you in when he's ready."

"Mom, I'd just as soon not come in at all. This is weird."

"Not weird, educational. Wait here. I'm going to help him relax."

"But...!"

"I've made my decision. Now, please wait."

"Okay," she said.

Mom locked the door behind us.

I undressed and laid on the bed. Mom handed me everything. On my left, we set up the tablet on the new reading pad. I turned it on and opened youtube while Mom unscrewed the lid of the container and set it beside the tablet. Then, I took the lube from her and set it beside me on the right.

She said, "Put some on, please."

"After it gets hard."

She gave me a look.

"It's weird when I'm soft."

She considered this, and then nodded and went to the chair—there were now two of them in the room, next to each other about five feet from my bed, level with my head.

Satisfied, I opened a new video on youtube. This one featured a voluptuous model named Veronika Podkapova. The clip featured moments from what appeared to be photo shoots—several different ones—and it showcased her butt and her large breasts. What I liked about it were the close-ups of her face, showing her bright, eager brown eyes and her simple, beautiful smile.

I sensed Mom lean forward, maybe noticing the new model, and watch the video.

I rubbed my penis, but it was not working. I kept thinking about Lia, waiting outside the door.

After about three minutes, Mom said, "Use the lubricant."

I whispered, "Nervous, Mom. Lia."

Mom said, "Can't you find..."

I held my finger to my lips.

She whispered, "Can't you find a video that is more distracting? You may use hardcore porn. I won't mind."

"Video's fine."

"Try something else, baby."

"I can't," I whispered, pointing toward the door.

Mom rolled her eyes and sighed at the ceiling. Then, she looked at me like she had an idea. She rose and walked to me, kneeling beside the bed by my hip. She smiled. Her hands slid up her tummy and over her breasts. She looked down at them and squeezed them into her fingers. Her hands could not encompass them; they were too big.

She looked at me. "Does this help?"

I could not respond.

She did it again. I watched and felt my heart pump.

I said, "Will you touch your bottom?"

Her eyes widened for just a fraction of a second, and then she nodded. She stood and turned around. Mom's butt bulged out from her lower back toward me. Her hips curved toward her thighs. Light shined off her pants at the most prominent point on each round globe. A dark line ran horizontally across the bottom of her butt, where the two plump cheeks perched on the top of her thighs. Gravity, the passage of time, and some added weight made her butt more full and feminine.

Mom's hands glided along the outer curve of her thighs and hips up to her waist. She moved her butt from side to side as her hands slid back down. She put her palms against each hefty cheek and squeezed. I saw how soft the flesh of her bottom was in the way her fingers sunk into voluptuous buns. Her fingers clutched her skin through her tight pants, pulling the halves apart, and then squeezing them together.

Her head twisted toward me.

I nodded and whispered, "Beautiful, Mom. Show me?"

She turned away. Her thumbs slipped under the waistband at her hips. Her shoulders rose and fell, and then she pushed.

Milky white skin appeared like a sunrise against the black pants. If anything, as her butt unfurled to me, the curvature was enhanced. It was as if the tight pants didn't allow her bottom's true shape to show itself. It was more plump, more fleshy, more feminine. She stopped halfway down.

I reached out. When she felt my finger slip inside the waistband, she flinched. Yet, she allowed me to tug her pants over the outermost crest and down to the top of her thighs.

Her skin was flawless in color—no moles, no blemishes. Each cheek has a small patch of stretch marks running laterally away from the crack about halfway down. I lightly ran my fingers over each half. I pressed my hand against one cheek. It was silky smooth against the pads of my hand. I squeezed and kneaded. It was doughy. I drew the tip of my thumb gently up and down the crack. At the bottom, I cupped the flesh and squeezed it, tugging one side away from the other and briefly exposing her tiny, pink anus. I let go and the little hole vanished inside her flesh.

She pulled up her pants and turned around, looking at my penis. It was hard.

"Are you ready?"

"I think so."

She reached down and wrapped her fingers around it. She stroked it twice, and then let go. "You're ready, baby."

"Thank you, Mom."

She smiled. "I'm going to let Lia in. Just ignore us—pretend like were not even here." She walked toward the door, but stopped and turned back to me. "Use the lubricant."

I turned the video back on, and then opened the lid of the vaseline. I heard Lia walk in. She and Mom walked across the room to the chairs. I wiped the vaseline on my erection and spread it around with my fingers. I took it in my hand and made sure my hand was slippery.

"Is he normal-sized?" I heard Lia whisper.

"No, he's big."

"I thought so."

I began to masturbate, forgetting completely the instructions Mom had given me the day before.

I heard her clear her throat. "Massage it, baby. Like we talked about."

Lia asked, "Massage?"

"He shouldn't jerk or stroke too strongly. It can damage his penis."

"Oh."

They watched in silence for a bit, and then Lia asked Mom if she could see what I was watching.

"Sure. He won't mind."

I heard Lia pull her chair closer. Soon, she was right next to me, leaning over and watching Veronica smile and slowly undress. "This is different, Mom. This woman has really large breasts, like us."

Mom walked over and looked. "Yes, but is this tasteful, like the other ones he enjoys."

Veronica turned around, and her perfect, big bottom moved in circles for the camera.

Lia said, "Bottoms again."

"He really likes them," Mom said.

I glanced up at her. She smiled down at me.

I'd forgotten to use my technique again, and Mom said, "Stop, baby."

I did.

"Firm, but gentle grip. Massage up, and caress down, okay?"

I nodded.

I sensed Lia turn toward Mom. "How was that, Mom? Do what?"

"Massage up the erection, and caress down."

"Like this?" Lia asked. She raised her forearm and used her other hand to perform the act as described by Mom.

"That's close, Lia. Here." Mom took hold of Lia's arm and did it.

I wasn't watching my video any more.

"Try it on my arm," Mom suggested. She held out her arm, and Lia stroked and massaged it.

"Like that?"

"Yes. Good, Lia."

"But, forearms have a much different shape."

"And texture," Mom added. "It's very different with an erect penis."

Lia looked at me, and then at my erection.

"Lia," Mom began, "for educational purposes, do you want to try it on him?"

"I don't know, Mom. I think that crosses a line."

"Only if you want to Lia, and it does not cross any line. This is for your learning. There is a perfect subject in front of you."

Lia argued, "He doesn't want that."

Mom and I glanced at each other. She touched my shoulder. "Would you care?" she asked. "To help your sister?"

"Okay."

Lia glanced up at Mom. "Are you sure, Mom?"

"It's up to you, dear."

Lia slid from the chair and walked on her knees down to the level of my hips.

Mom cautioned, "That's vaseline, Lia, so your hands are going to get greasy."

"That's okay," she said. Her voice sounded airy and nervous.

Then, Mom added, "You may want to put some on your hands first, to make sure you're hands aren't too dry."

Lia took the container.

"Just get a little on your fingertips, and when you rub it on his penis, it will lubricate your hand."

"Okay." She swiped her fingers into the tub, and then closed the lid and set it on the floor. She reached for my erection with her hand and paused. "Do I just...I mean, should I..."

"Here," Mom said. She knelt beside Lia and guided her hand to the shaft. When she touched it, Lia said, "It's really warm." Mom led Lia's fingers up, down, and around my penis, spreading the vaseline all around. "Okay," Lia said. "I've got it."

She grabbed my penis gently and slid her hand along the length.

I snatched a breath.

Lia stopped.

Mom asked if her hand was lubricated enough.

Lia nodded. "Uh-huh."

"Then, dear, you may grasp it like we practiced earlier."

She did.

"Now, I think of it like milking a cow—which isn't something I've never done before, so it may not be the best metaphor, but it's how I think of it. I'm massaging the erection up to draw the milk—semen, pardon me, out. On the way down, I'm merely caressing it—giving a loving pet."

Lia's hand came alive on my penis. I felt her fingers undulate as they slid upwards, and then relax on the way down. I moaned, and my erection throbbed.

"Oh!" Lia cried, staring at me, wide eyed.

"What, dear?" Mom asked.

"It moved. I felt it squeeze."

"That's the muscle contracting—it's the same muscle that he uses to ejaculate."

"Is he starting to ejaculate?"

"No, not yet. It's a sign that you're doing it correctly," she explained. Then Mom looked at me and asked if I was comfortable. Lia stopped, waiting for my response.

"Yeah," I muttered.

"I'm doing it right?" Lia asked.

I nodded. I had to have looked like I was utterly at her command, a thing she could please or deny with a simple flick of her wrist.

"Oh, my gosh, this is so cool," she uttered, almost whispering. She gazed at her hand as it stroked. "Mom, should I use two hands?"

"On a penis like his, you can, but it isn't necessary. Besides, you'd need more lubricant for another hand. Best to stick with just the one, dear."

"Okay, how will I know when he's ready?"

"He should tell you, but if he doesn't, you can feel the muscle contract more regularly. You'll feel his penis grow larger..."

"Larger than this?" Lia interrupted.

"Yes. It will fill with even more blood, grow even more firm in your hand. His breathing may also be a clue. He may vocalize his readiness."

"Okay."

Mom watched Lia, and she seemed eager to say something else. Her hand was up by her face, and her index finger was tapping on her lower lip. Finally, she said, "I'm going to sit beside you Lia." She moved around Lia and sat on the bed near my knees. "One thing that may help tempt the semen out is to—very gently—massage his testicles, like this."

Mom reached between my legs and cupped my scrotum with her left hand. Then, she began rolling my balls across her fingers. I moaned.

"It's flexing again, Mom."

"Lia, when it's time, push his penis down to his tummy. I'll hold the cup. Try not to move left or right."

"You'll let me finish? I get to see it happen?"

"If you like, Lia."

She nodded.

Mom stood up, still playing with my testicles. She took the sample container and stood with one leg on both sides of Lia's kneeling body, straddling her.

The sensations on my penis and testicles were too strong. "Now, Lia."

"Okay." Lia lowered my erection to my belly, still stroking it. Mom held the cup over the tip with one hand, and continued massaging my scrotum with the other.

My body tensed. My heart thumped in my chest. My abdominals flexed and my head and chest rose off the bed. I grunted and pinched my eyes closed. I felt semen leaping out of me.

"Oh!" Lia yelled. "Oh, Mom! Look! I'm doing it!"

"Very good, dear. Keep going, even after he seems all through."

"I did it, Mom!"

"I know, Lia! Great job!"

The rush was ending for me, and I sagged onto the mattress with a long groan.

Mom let go of my testicles. "Lia, squeeze more firmly from the very bottom, close to his scrotum, and work your fingers up to the tip. Do that a few times."

"He's not done?"

"Not yet, we need to get the rest out of him."

Lia did as Mom asked, and her fingers worked a large drop from the tip of my penis. She said, "Oh, wow."

"See, Lia?"

After a few more tries with no result, Lia let me go. "Mom, can I see the sample?"

"Sure," Mom responded, handing Lia the container. "I'll fetch the lid."

On her knees beside me, I watched Lia inspect my sperm. She smelled it and tilted the cup around, watching it flow. She held the cup near her mouth, and she looked to me like she was at a bar, holding a shot of liquor.

Mom came back with the lid, took the jar, and sealed it shut. "Let's let your brother relax a bit and get cleaned up. This needs to go in the freezer." As the two left my room, I heard Mom ask if Lia had any questions.

I got up about ten minutes later and took a shower.