Thoroughly Modern Milton

I read somewhere that a stiff dick has no conscience. Being a woman in my 40's, I have witnessed many things in my life, not the least of which have been what men will do if they think they might get laid. Having been seduced out of my clothes and into their beds, I learned after they got what they wanted, it was, "you still here?" I have done the walk of shame many times. Too many times.

I knew deep within it was my fault. I was a romantic; looking for Mr. Right and finding only Mr. Right Now. D'Andre promised me the sun and moon. His love making skills were second to none and he swept me off my feet and into a Las Vegas marriage. I was happy to pick up the tabs for our marriage, subsequent honeymoon, and most everything else. I wasn't rich, not like Bezos or other Tech giants but I was comfortable. My parents left me a bit of cash and lots of stocks and bonds all of which allowed me to live comfortably without the stress of the work-a-day individual.

I had an inkling that my husband was spreading his big black cock around. It hurt me but I resolved to keep our marriage afloat. D would promise it would never happen again. And yet it continued. I didn't know whether he thought I was an idiot or he was that stupid. Lipstick on his collars, the diminishing scent of perfume on him when he'd come home late from work. It hurt. It made me resentful. I thought nothing he could do could be worse than cheating on me, but I was wrong.

Having tossed out my husband, I was looking for a man with whom I would exact my revenge.

To call what I wanted to do getting even would only be half right. Men have used me, abused me though not in a physical way. No, some have made promises they never intended to keep. And while I know it's my fault for being too trusting, my now ex-husband used my bank account to spend my money on his side-bitch. I had the checks on which he forged my name. I kept them with a plan to use them in the future.

So, if I seem bitter, it's because of men. Now I would turn the tables on some unsuspecting man. I'd find one who I would make into the perfect male. I planned to break his spirit and make him the perfect pussy.

I wasn't Milton's fault. What was about to happen to him was all my doing. I don't blame you if you hate me for it, but I had made up my mind to exact karma on some unsuspecting male.

I met Milton by chance. He was seated by himself at a restaurant during a lunch rush. When I looked around, his was the only table where there was any remaining seat. When I asked if I could join him, he blushed and stuttered "please do, ma'am."

Any attempts I made to start a dialogue was met with non-committal shyness. That told me that my lunch partner was inexperienced and uncomfortable in social situations with females.

It took a while but he finally told me his age, 23. He said he had an entry level job at some store. I forget, I wasn't all that interested in his particulars. I wanted to know him. I sensed there might be some potential in the young man.

As our time passed, my instincts were proven correct. He was a bit timid, lacked confidence, and could use some guidance. There seemed to be a plus side to this male. He was very polite.

In short order, I could see that Milton could be molded into something useful. On the outside he was pleasant looking. Blue eyes lit up when he showed his goofy smile. At 5' 8", he had a less than medium build. I thought that he was out of his element when in the company of a woman. Recently single again, I decided to make Milton my project.

His over-the-top politeness and the way he let me let lead the conversation told me that he had been primed to respond respectfully to women. He wasn't the usual dickhead that would ramble on about how great he is, how many women he'd conquered, his favorite sport teams. No, Milton sat and answered my questions with some prodding on my behalf, which, if he was being honest, told me more about him than I would learn if he just ran his mouth like so many men do.

I decided I'd push the envelope.

"Tell me about your childhood, Milton," I said. It was not a request but had the underlying manifestation of an order.

"My father split before I was born," he began. "I was raised by my mom, my grandmother, and an aunt."

"Uh huh. Go on. How was it being the only male in a female environment?"

I saw the look on his face as he recalled some uncomfortable history. "They were very strict with me," he said blushing at the memory. "Nana would punish me for the slightest infraction."

He had my interest. "How did she punish you?"

He was so cute when he could not make eye contact but looked at his hands folded in his lap. "Milton, I asked you a question. Rude boys get punished," I snapped at him hoping to get a reaction.

I knew I was moving fast. I didn't want to waste time on this male. He could leave now or stay. Look, if he just left, no harm, no foul. I'd lost nothing. But stay he did.

His sudden intake of breath let me know I'd struck a chord. I knew instinctively that Milton had been trained by women to obey. That was something I needed for myself. Thus far, the men I have had the displeasure to be involved with had been the macho types. The kind that would care only for themselves when we had sex and everything else. They were like, wham, bam, thank you ma'am and then it was off to sleep or back to the TV..... or in D'Andre's case, back to one of his side-bitches.

"Nana would have me get her a switch, " Milton whispered as he recalled those events.

"And?" I prodded.

"Nana would have me pull my pants and underpants off and bend over the ottoman. Then she would chastise me for being late or impolite as she raised welts on my bare bottom."

"Impolite, Milton?" I questioned him.

"Yes ma'am. If my manners were slacking off, you know, if I forgot to say yes ma'am or yes Nana and just said yeah, she would correct my behavior with the switch she made me fetch for her. If my room was a mess, my bed unmade or I hadn't cleaned the house properly, mother or my aunt would use their hand on my bare bottom."

"And were your mother, grandmother, and Aunt there to watch whenever one of them punished you and saw your privates?"

He took a quick breath, "Yes ma'am. Most of he time."

The men I'd been with lacked the devotion to me that I craved. They lacked the ambition to be there for something other than their cock. This young man on the other hand had been trained to respect and defer to women, to put the needs of women ahead of his own. Milton had been taught that should his efforts fall short of the expected desires of the women in his life, corporal punishment would quickly and ensue.

"Milton, please tell me when you received your last bare-bottom spanking."

He blushed. Of course, he blushed. He was telling me his deepest, darkest secrets. Things he would never tell another male, he was unable to keep from me. I could hardly contain my excitement.

"Um, well, my last bare bottom spanking was the night before I turned 21, ma'am."

"Why was that your last?" I asked the blushing and very uncomfortable male.

"Please, ma'am, don't make me tell you that. Please," he whined.

Oh, he was going to tell me alright. We'd gotten this far. I'm going to have him cross the finish line whether he wanted to or not.

"Milton," I whispered.

"I got hard, ma'am," he said turning a deep crimson almost in tears.

"Shhh, baby boy. It's okay. I know you did. I just wanted you to be open and honest with me. I think it's a fine thing that you enjoyed your spankings."

"You, you do?"

"Ma'am," I corrected him.

"Sorry ma'am. You think it's not bad for me to enjoy, um..."

"Your bare-bottom spankings," I finished for him.

"Yes ma'am," he said looking down at his lap again.

"Are you hard now, Milton? Did telling me about your spankings make your dick get hard?"

He blushed and nodded, still looking down. I thought it was cute. This young man was vulnerable. It was a trait I wanted to use against him and for my own benefit.

"Now Milton, look at me."

He raised his eyes. "Yes ma'am?"

"I want the truth, young man. If you went home right now, would you beat off?"

He almost started crying. All he could do was nod, his face flush with shame.

"What if I told you it was okay that you got a boner remembering your spankings? What if I said that you could beat off, jack that little dick until it spit its salty tears? What if I said I want to watch you rubbing one out? Would you like that, Milton?"

Silence. Milton was swallowing, unable to respond.

"Milton. Would you please answer my question? Would you like it if I watched you tugging on your little pink dick?"

"Very much, ma'am," he managed to croak.

"Then you have two options young man. One; you can go home and jack that dick all by yourself."

I let him wait for few seconds before making his most treasured fantasy come true. "Or, Milton, I can take you to my home and watch you perform that nasty thing you're dying to do. Which is it?"

For many of you reading, that would be a rhetorical question. For young Milton, to be asked by a 40-year-old woman if he'd like to masturbate while she watched was what he wanted but was unable to put into words.

I knew I represented his mother, his grandmother, and aunt. I was nearly twice his age and authoritarian in dealing with him. It was something he missed and I felt something he craved.

"First, I want you to tell me this. Have you ever beat off in front of any of those women that raised you?"

"Oh, no ma'am. They all hated men and I was warned never to let them catch me of they'd cut it off."

"I'm sure they weren't serious about cutting your wee-wee off, Milton. Now come with me."

I paid on our way out and was pleased that the young man held the door for me without being told. He had such promise, promise I planned to exploit.

We arrived at my near-by flat. "Excuse me Milton. I'm going to get out of these clothes. Sit there," I directed him, pointing to a chair.

I pulled my slacks off and tossed them and my blouse and bra in the hamper. Wearing only back panties under a thin white robe, I knew my prey would be able to see the outline of my contrasting panties through the gauzy material.

I caught him off guard when I asked him why he still have clothes on. "Do you often enjoy your disgusting habit while dressed?"

"Um, no ma'am. I just didn't think...."

"That's right, Milton. You didn't think," I snapped. "What's more, when you're with me, I don't want you to think. I want you only to obey me. Understood?"

It was a test. While most men would have hightailed it out of there, Milton apologized and said, "Yes ma'am."

"Remove your clothes, now."

I sat watching the young man shyly remove his clothes. He had his back to me. From my vantage, he had more of a slender build. Narrow shoulders, wide hips, bubble butt. From behind, naked, he might be mistaken for a female.

Now in T-shirt, tight white briefs, and socks, he pulled his shirt over his head and shook out his longish hair. "Underpants and socks, now Milton," I said with some authority, growing impatient. "Underpants first," I commanded my visitor. I knew he would have to bend over to take his socks off and I wanted him to show me that asshole. I was wondering if he could stand that humiliation.

I watched him step out of his tightie whities. When he bent over to remove his socks, I stopped him. "Stay just like that, Milton. Hold onto your ankles."

Doing as he was told; I joined the young man. I ran my hand over his back feeling him shiver and break out in goose bumps. I reared back and slapped his round bottom. "Ohhh," he moaned aloud.

"You like that, don't you, Milton?"

"Yes ma'am," he whispered, his whole body in full blush mode.

I felt his buttocks, "smooth, soft, nice ass, Milton."

Silence as I waited for a response. None was forthcoming.

"Milton?"

"Yes ma'am?"

"When a woman compliments you, isn't it rude of you for not thanking her?"

"I'm sorry, ma'am. This is so new to me." a short pause then he remembered. "Thank you, ma'am."

"It's a little late for that now. I think I shall punish you for your rudeness, Milton."

He was quiet as he contemplated this strange woman giving him that which he desired. "Ma'am. I deserve to be punished, ma'am."

"I didn't hear a please there, Milton."

"Please ma'am, I need to be punished," he said quickly.

"In time, Milton," I smiled to myself as I resumed caress his big ass. My index finger found his rose bud and prodded and poked just a little. Milton's reaction was to moan and begin to shake. "Oh, you like that. Has anyone ever put anything in your boi-pussy, Milton?"

"Excuse me, ma'am. I don't know what a boi-pussy is."

I gave his big bottom a swat, "This, Milton," and swatted it again. "This is your boi-pussy. You know what a woman's pussy is, right?"

"I do, ma'am."

"Boi-pussies are meant for the same thing, Milton; cocks. Boi-pussies are for those sweet bois who should be fucked rather than do the fucking themselves. So, how many times have men plowed your soft pussy? How many women have used a strap-on to make you their bitch?"

"None have. Not ever, ma'am."

"Never? No one. No woman, no man?"

"No ma'am. No one ever."

"Damn shame to waste this pretty pussy. I bet I could find a man, a real man, Milton who would love to take this fat boi-pussy and make it his. If you behave, young man and please me, we may make that happen."

When he shivered again, I began my assault on his bottom. My left arm encircled his waist. My right arm rose and fell again and again as Milton moaned, cried, and begged me to stop. I finally ended his first punishment when his bottom was fire engine red and hot to the touch.

I went back to my chair and sat. "You may stand up, Milton."

He stood straight, his back still to me. "Turn around and face me."

He hid his dick with both hands which I though absolutely childish and just wonderful. "You're hard, aren't you?"

He nodded, blushing even more red than his bottom.

"Show me. Put your hand at your sides, now Milton."

I almost laughed out loud when I saw his little dick, if one could call it that. "Cute little wee-wee, Milton. And no hair around the little thing. Touch yourself while I watch. Go on now, Milton. Beat off for me."

He looked down at his little boner and used his thumb and two fingers to gently jack himself off. I studied the victim of my harshness and noticed he had large areola and eraser-sized nipples. His slim waist flared out to those hips I'd noticed earlier. "I'm gonna rock his world". Milton may be a pathetic excuse for a man, but he has all the qualities to become an excellent sissy," I thought.

I watched him for maybe a minute. "Stop," I ordered sharply. "Look at me while you perform your nasty little habit. Keep your eyes on mine. I want to be what you see and who think of when you jerk off from now on."

"Yes ma'am," he had his sheepish silly grin on his cute face. He was clearly enjoying this training session but only because he didn't know he was being trained.

It took him nearly a minute before he was able to make eye contact with me but he managed to bring his eyes to meet mine. He was surprised at when he saw. My robe was opened now, my breasts available to his eyes, my hand in my panty caressing my pussy.

"You may begin again, Milton. Keep looking at me though."

He did look at me. His eyes were fixated on seeing me touch myself even if he couldn't see my pussy, he could imagine what it looked like.

"Have you ever seen a woman naked, Milton?"

He stopped playing with himself to answer my question. "Yes ma'am."

That surprised me. "Where, who?" I demanded.

"In a magazine, ma'am."

I smiled inwardly at that at the same time I berated him for looking at dirty pictures. "So, you're still a virgin then?"

"Yes, ma'am," he answered shyly.

"That's good. Maybe one day if you're good, maybe...." I left it there on purpose. I wanted him to have a goal, something to strive for but, and unknown to him, something he would never attain.

"Now finish what you've started but you better not get a drop of your disgusting discharge on my floor or furniture."

I watched fascinated by his stamina though I thought he might be holding back, pretending to jack off while staring at me rubbing my cunt. "Maybe this will help you," I said and pulled my panty aside letting him have a little peek at a real pussy.

I saw Milton shudder, his eyes rolled back, and his knees get weak as he groaned and used his left hand to catch his sperm. It was all so wonderful that I came with him.

As I gathered myself, I admired my gift from God who just stood there, his left hand under his now soft dick making sure not to let a last oozing drops soil my carpet.

I closed my robe and went to him. "Show me your hand."

Milton held his left hand up. There was a little puddle of his seed in it. Not much; but enough for me to test him once more. I dipped my finger in his hand and raised it to his lips. "Open."

He obeyed instantly. I put my finger in his mouth. "Suck it clean," I told him.

Now I shuddered as he complied and eagerly sucked on my coated finger."

We repeated that several times with me sawing in and out of his mouth. "That's my good boy," I complimented him. "Suck it like my finger is a cock. Nice boys like you should suck cocks, Milton."

His eyes shot open but he didn't stop sucking my finger.

I was so taken with my young man I wanted to reward him I opened my robe and smeared his sperm on my nipples. Then I put my hand behind his head and drew him to me. "Clean me, Milton."

He suckled my breasts like a hungry baby. It was beautiful. I wanted to own this young man with so much potential.

I sent him packing with his promise to return to me the next day after he left work.

I took a long relaxing bubble bath, with scented candles and a glass of red wine as I formulated a plan with which I could have Milton dependent on me and serving my every wish. And when he was totally in my grasp so to speak, I'd wreck his world.

I knew that the first thing I would do would be to remove what little manhood he may have from him. To do that, I would have to break him down, make him even less confident in himself than he already was. Then, when he was willing to do anything to stay in my good graces, I'll strip him of his pride and dignity.

I knew my plan would work. As soon as Milton followed me home and removed his clothes and performed for me earlier, I knew. Like all males and men, Milton thinks with his pecker. What his wee-wee wants comes first. I will make the needs of his wee-wee come second only to what I want, what I desire. My cute, little dicked Milton has no place in a world of real men and strong women in his current state. When I'm finished, he will know his place is to serve others.

I left a note on my door for Milton to read before knocking. If he reads it and complies, my work with the young male will be simply a matter of time. Should he read my note and not comply, I expect never to see him again.

"Milton," I wrote. "Before entering my domain, you must be ready to serve me as I see fit. To that end, I never want to see you in clothing again. That means you will disrobe outside my door before knocking. Once I permit you entry, you will bring your clothing inside where you'll find a bag just inside the door. Place your clothing in that bag and come to where I am seated. Should this simple act of your willingness to please me be too great for you, then you are dismissed and I wish not to have your acquaintance. In short, dear Milton, strip and knock or leave."

I placed that note in an envelope, taped it to my door with his name spelled out in bold print and waited.