Mom's Friend Takes Control Pt. 04

Supervised Masturbation

As the week passed, there was no more mention of the underwear. I wore them each day feeling slightly embarrassed every time I put them, knowing that Sharon had chosen them and had inspected me wearing them.

But it wasn't just the underwear. All of the things happening since moving in with Sharon were starting to get inside my head. Other than one ruined and very embarrassing ejaculation, I had not cum in weeks. I couldn't remember the last time I had been so horny! Stroking my cock almost daily but never cumming had turned into a maddening series of teasing edges. The idea of Sharon asking me not to jerk off and then selecting undies for me was both humiliating and arousing.

And then there were the random comments from Sharon. Comments that hinted that she thought I was small down there and maybe pretty quick on the draw. Those were most embarrassing and, oddly, extremely arousing. Both of these things were kinda true, I guess. But I certainly didn't want Sharon to know!

To make matters worse, Sharon was often outside after work enjoying the sun in her bikini. Or coming out of her workout wearing those super-tight workout pants and a sports bra.

More and more, my fantasies were starting to be about Sharon! And this was a problem. Too many times when we were together I was struggling to hide my arousal. But she would catch me staring. Smile. And then continue as if nothing had been noticed.

By the time Friday night rolled around, I was horny as I had ever been in my life. Rule or no rule, I had to cum! When I went to my room that night. I got undressed, slipped into bed, and immediately grabbed my cock and started to stroke. It felt so good and it was apparent right away that this would only take a few seconds.

But suddenly I was overwhelmed with the sense that I was doing something wrong and stopped. What the hell? I was letting Sharon control my orgasms and this was crazy!

I grabbed my throbbing cock and started again...only to stop once more as I hit an agonizingly close edge.

I sat propped up against the pillows, my head back, eyes closed, trying to sort out exactly what was happening.

And then I heard the knock. And Sharon stepped into my room. I fumbled a bit to make sure my erection wasn't so obvious but I'm sure she saw.

She came in carrying a little bundle of things and wearing her sexy little pajamas. She loved little shorty pajamas with thin, spaghetti strap tops.

She came right over and sat down beside me.

"Eddie, I know this may seem embarrassing but I think the time has come to let you have a little orgasm. I've been watching you this week and I'm not sure you're gonna make it much longer without another accident if we don't release some of the pressure down there."

I just sat there stunned. Embarrassed. Staring.

"Let's get the sheet out of the way and get started," said Sharon, as she started to pull the sheet down. I grabbed at it frantically, trying to avoid being exposed.

"Come on now, Eddie. You know you need a little cummie and this is the proper way to have it. So let's get ready."

She pulled again and managed to get the sheet down to my ankles, exposing my naked, hard cock. I tried to cover myself with my hands. I felt so embarrassed. But my embarrassment only seemed to be making my cock harder.

Sharon reached for her little bundle of items and unfolded a white towel that she draped across my thighs. "This will be your 'sticky towel' that you can use for all your little releases. It will make cleaning up easier."

Then she reached back and picked up a bottle of lube.

"Hold out your hand."

I hesitated. I didn't want to lift a hand away from covering my cock.

Sharon just stared at me and stated in a very stern, no nonsense manner, "This is going to happen, Eddie, one way or another. And trust me, I think you would prefer this way. Now put out your hand."

I slowly lifted one hand and held it out to her.. She squirted a big glob of lube into my palm.

"Make a little fist, Eddie."

I squeezed my hand into a fist, making the lube squish all over.

"Now you go right ahead and jerk your little soldier the way you like. I'll just sit here till you're all done."

I just sat. Staring. The shock of this moment was almost too much. I made no move to touch myself.

"Go ahead. Don't be shy. I've seen plenty of boys rub their little penis. So go ahead." She reached and took my hand and moved it closer to my cock. "Go ahead now. Show me how you do it."

I slowly wrapped my fingers around my cock and began to stroke. It felt incredible, in spite of the awkwardness and embarrassment of the situation.

"That's it," Sharon whispered. "Nice and slow like that. We don't want it to end too quickly. Here, let me help you just a little"

With that, she grabbed the bottom of her pajama top and quickly pulled it up and over her head. Fuck! She was sitting right there naked from the waist up. And her tits were everything I had imagined. Full. Soft. Drooping just a bit but not much. And her nipples were a perfect shade of dark pink. And they were so erect!

I stared and immediately stroked faster. My breathing started to become rapid and gasping.

"Hmmm. I can see that inspired you. But not too fast. It will all be over in less than a minute."

I raised my other hand and reached out toward her naked tits, but Sharon took my hand and pushed it down. "You don't need to touch tonight. Maybe that can happen another time."

I blushed furiously. And stroked faster. She was just too sexy and her words were driving me crazy!

"Looks like you're almost there, Eddie. Before you cum, you should ask permission. That would be the proper thing to do."

I looked at her and gasped.

"Do what? I'm not asking permission! I'm a grown man!"

"That really doesn't matter. I'm in charge of this. And if you don't ask permission, we're stopping right now and you can wait another few weeks for your next chance to make a squirty."

I just stared in disbelief at what she was saying. "I can't hold back. I gotta cum!"

"You have to ask. Or else..."

"Oh fuck! Okay! Can I?"

She shook her head slowly. "That's not a proper way to ask, Eddie. How about a 'Ma'am' or 'Mommy' thrown in there to make it nicer."

"Oh shit," I gasped. I couldn't hold it any longer! "PLEASE, may I cum, Mommy?"

"Of course, Eddie, Spurt it all out. Show me what you've got for Mommy."

The orgasm slammed into my body. I nearly doubled up on the bed as I came harder than I've ever cum in my life. Squirt after squirt of cum shot out onto the towel and ran down my hand as I continued to stroke.

"That's it, baby, get all that nasty stuff out of there."

"Oh fuck!", I cried as I stroked out the last drops of cum. When I was done, my head flopped back onto the pillows as I just collapsed, gasping to catch my breath.

After a moment, I felt Sharon grab the towel and slowly start to clean me, wiping away the cum that had missed the towel. And then wiping off my cock. As she wiped, I started to get hard again.

"Oh Eddie, I do appreciate your eagerness, but you can calm down. Once is plenty for you."

I blushed again. It seemed like blushing was my new normal state of being.

"I hope you feel all better. Now, get some sleep and we'll have a nice weekend ahead of us."

Sharon stood up to leave, taking the sheet and pulling it back up over my exposed lower body. She gathered up the towel and the lube. And then picked up her pajama top.

"Here, you can sleep with this tonight. This will help you remember when you wake up so you don't think it was all a dream."

She leaned over and kissed me on the forehead, her full breasts hanging right in front of my face.

"Sleep well, Eddie. See you in the morning."

"Thanks. You too."

As she closed the door to my room, I pulled her pajama top up to my face and deeply inhaled her scent. With my voice muffled in the thin fabric, I whispered, "Good night, mommy."