Thoroughly Modern Milton

I'm not one to pace. As much as I wanted To rule Milton's world, there would always be another male like him. Males whose character is like Playdoh are a dime a dozen.

I sorted through my closet and selected my most matronly outfit. I wanted to appear as those women in his life whom Milton held in respect instead of some naked bimbo in some magazine he was used to beating off to.

My skirt buttoned up the front and was ankle length. To give my young male something to capture his imagination, I left it unbuttoned just up over my knees. I suspected that Milton, like so many others of his ilk was an up-skirt peeper. My blouse was long sleeved with high collar of ruffles. My shoes were 4" heels. And yes, I wore hose.

The knock was soft, barely audible. I ignored it. Seconds later, his knock was louder. Still, I waited. I wanted him to enjoy the excruciating moment hoping no one would see him in his naked state as he waited for me to allow him to gain entrance.

"30 seconds longer," I thought as I went to the door.

I wanted to have a little fun with my prey. I opened the door. "Yes?" I asked.

"Please ma'am, let me in."

"A naked male at my door? Why should I allow you into my home?"

"Please ma'am," he begged on the verge of tears.

"Will you behave?"

"Yes ma'am. I promise."

I secretly loved that his little willie was standing straight out from his groin. "Well, if you must," I said as I stood back and let him come in. The door was still open as he waited for me to tell him what next to do. "Place your clothing in that bag, Milton. Then, close the door and come to me." I turned away from him and walked to my chair.

I watched him neatly fold his clothes and carefully place them in the bag. Then he closed the door and came to me.

"Stop right there," I commanded him. "On your knees."

He knelt some 20 inches from my feet. Now to set the rules. "Milton, you must never try to hide your body from me. Open and spread your knees as wide a part as you can and place you hands on your thighs."

I smiled as he obeyed me. His eyes never left mine. His little dick never lost its hardness. I knew he hoped for another session like our last. That was not to be this evening. Leaving my submissive little pervert wanting would only serve to make him more pliable, more ready to please me.

I crossed my legs allowing my skirt to part. Seeing my stocking tops, Milton's eyes widened and his tiny boner jumped.

"Milton, were you looking up my skirt? Are you some pervert peeping up women's skirts?"

"Yes ma'am, I mean no ma'am. I mean I did but only because of where you have me. I couldn't help it and I am so sorry."

Fucking pitiful. "It's okay sweet boy. I bet you're curious about what women have under their clothes."

"Yes ma'am."

"But you've already seen my panties and more. That wasn't enough for you?"

Milton couldn't speak. I saw him screw his face up trying not to cry and I weakened for a moment. "It's okay, Milton. Never mind. We'll revisit that at a later time."

The look of relief that came over him was almost comical. Just as new as this was for the young man, it was also new to me. I was flying solo with no real flight plan. It occurred to me that I might be pushing too hard too quickly. I decided to change my approach.

"Come to me, Milton," I said pointing to a spot just in front of me.

He crawled!! Milton actually came to me on hands and knees. What a delightful young man. He deserved a reward.

"Milton, my feet are sore. Would you like to take my shoes off and rube them for me?"

"May I, ma'am? Please?"

I felt my heart softening for this tender male. "You may, Milton."

His hands felt wonderful on my stocking clad feet. While he rubbed one, I used my other foot to rube his little boner. The first touch almost made him double over. "Did I hurt you," I asked.

"No ma'am. I uh, it felt nice is all."

"Has no one ever touched you there?"

"No one, ma'am."

I pulled my foot out of his hands and presented him with the other. "You have nice hands Milton. I bet they feel wonderful on your dick."

He didn't answer but his blushing told me all I needed to know.

I'm going to send you home with an assignment, Milton. I'll write down a couple web sites that I want you to visit. I want you to look at the real men on those pages. I want you to look at the soft bois, like you, Milton who adore those real men. I want you to memorize everything you see. Will you do that for me?"

"Yes, ma'am."

That's my good boi," I smiled at him. I raised my skit up over my knees under Milton's watchful eyes. It was so cute that I pulled it up until the hem was at my stocking tops. "Milton, please rub my calves."

He was so eager and to be completely honest, his hands were making me horny. I saw his dick leaking precum. "Milton, remember what I said about your discharge soiling my floors and carpet?"

"I must not do that, ma'am."

"That right. But look at yourself. You're about to leak on my rug. Maybe we should do something about that."

"Please, ma'am. Whatever you tell me to do, I will."

"Whatever I want you to do? Did I hear you correctly, Milton?"

"Please, yes ma'am. I promise. I will do what you want me to do to keep me from messing up your carpet."

I pulled my skirt up to my waist. "Now Milton, remember your promise. It's too soon in our relationship for you to see my pussy. I want you to close your eyes and remove my panties, please."

His eyes were closed so tightly that he looked as though he was in pain. His hands trembled when he slid them up my thighs. He groped blindly feeling for the waistband of my panties. Finding it, he pulled them down with me raising my ass to assist him.

When he removed my panties, I put my skirt back over my knees. "You may open your eyes now, Milton."

The first thing he looked at was the panty in his hand. "Put them on, Milton."

"Ma'am?" He didn't understand.

"Put my panties on so your boner doesn't soil my carpet. Do it now before it's too late."

I thought it would be more difficult to convince my young man to wear panties. Not so Milton. He was quick to step into my panties and in doing so, without knowing it, Milton was also stepping into a new life.

You readers tell me. Should I continue with Part 2? Your comments will let me know.