Crime and Punishment

Crime and Punishment (apologies to Dostoevsky )

*

I am a single man, divorced twice and not about to get into that mess again. At forty-two I have some lady friends that are glad to drain my prostate occasionally.

Every Tuesday I have a cleaning woman come to my house. The cleaning service sent a new one a couple of months ago and she seems fine.

Her name is Gale, and she always wears tight jeans which show off her cute little butt. I have avoided coming on to her although I have thought about it.

A few times I 'accidentally' bumped into her as I walked by. I especially tried to brush up against her fantastic butt. She just smiled and I know she knew what I was doing. She knows her ass is fuck-bait.

This Tuesday there was an incident that you might enjoy hearing about.

Gale was working in my bedroom and I was in my office when I wanted to get some papers I had carelessly left in the bedroom.

I walked in just as Gale was putting my Rolex in her pocket.

"Gale, what the hell are you doing?"

She fumbled and stumbled and said, "Umm, nothing. Just cleaning."

"Cleaning my ass. You just pocketed my watch. I want it back."

She blushed beet red and took the watch out of her pocket and put it back on the dresser.

She couldn't look at me. She said, "I suppose I am fired."

"You should be. I should also call the police, and have you arrested."

Close to tears, she said, "Please don't do that. I am so sorry. I will do anything to make it up to you."

"Like what?" I said in a nasty way.

"I don't have any money I could give you. Maybe like cleaning your house for free. Or whatever else it would take."

She stood there in humiliation and shame. She is a cute young thing and as usual she was wearing tight jeans that showed a camel-toe in front and her tight sweet ass in back. My horny mind was working up a plan. I was imagining how her asshole would look (and feel. . . and taste)

"Honestly, I will come on my own time, on Saturday, and do the cleaning for free. For as long as you want."

I was hoping for something else. She is at my mercy so I will just say it.

"Here's the thing, Gale. Ever since I first saw you I have wanted to fuck you. That will satisfy me."

She acted shocked, but I was sure she was not too terribly shocked. She is in her twenties and she is very attractive, and I bet she has been fucked by lots of guys she just met in a bar or club and barely knows.

I let her suffer in silence to think about it.

"So, is this a form of punishment? If I endure it will you forget about the watch thing?"

"You might consider it a punishment. It might be pleasure. I hope you will not have to 'endure' it. Either way you would be off the hook."

I waited for her response.

"Gale, you are not naïve and innocent. You have been around. You don't have to be in love to have sex. I think you know what you need to do."

She avoided eye contact and nervously shrugged her shoulders.

She quietly said, "I guess so."

"All right then, take off your clothes and get on the bed."

She hesitated but then began to slowly undress, laying her clothes on the chair beside the bed. She got down to her bra and panties and stopped.

She looked like a lingerie model standing there in her underwear. My cock was growing hard. I wanted to take full advantage of the situation and fuck her up her sweet little ass.

"Those too, please."

She stripped them off and sat down on the edge of the bed with her legs tight together, trying to avoid exposing her crotch. Her trimmed pubic bush was all that I could see.

I undressed quickly, throwing my clothes on the floor. My cock was stiff as a board and swayed and bobbed as I moved close to her.

Her gaze was fixed on my hard-on which was about a foot away from her face.

Without taking her eyes off it, she softly said, "That's big."

I said, "It's going to feel good up your ass, isn't it?"

She flinched and recoiled at that.

She said, "Is that the punishment part of it? Do you have to hurt me?"

"It won't hurt that much. Maybe it will be uncomfortable at first. But you will get used to it. Lots of women love it."

"Think of it this way. If I press charges against you and you wind up in prison, there will be some lesbian guards. You know what they will do with a cute young thing like you? They will have you strip naked and back up to the bars and bend over. You will take a different guard's dildo up your ass every night."

Of course, I just made that up, but the idea of prison rape might make what I want seem much easier to her.

She stared at my cock which was staring back at her with its one malevolent eye.

After an awkward silence she whispered, "I don't think that will work."

I noticed that she had reached down and was rubbing her clit, with her legs now slightly apart. I also noticed that her pussy was open and wet. She might be apprehensive, but she was aroused.

I asked, "Haven't you done it that way before?"

"No. Can't you just do it the normal way? I am on birth control."

"I could but I really prefer the ancient original way of birth control. The way you are acting I think you want to try it that way too."

More awkward silence as she continued to stare at my stiff cock and masturbate. Some clear seminal fluid began to ooze out of me, and it formed a silvery thread hanging almost to the floor.

That did it. She caved in.

She reached over and smeared it all over the head and the shaft of my cock.

She said, "That will help. It's pretty slippery stuff."

Clearly she had decided to cooperate.

"Get up on the bed face down. Open your legs a little and spread your butt for me."

She replied, "Yes, sir" sarcastically.

She did as I asked, and I climbed on the bed and straddled her with my legs outside of hers.

Her asshole was a small light-brown hole right above her open wet pussy. She offered it to me by spreading her butt, following my instructions.

She had surrendered completely, and I could do whatever I wanted, so I pushed my middle finger up her asshole.

She squirmed and squealed but I relentlessly finger-fucked her virgin asshole.

She said, "I don't know if I am comfortable with that."

I pulled my finger out and said, "Let's find out if you are comfortable with the real thing."

I moved in close and put the tip of my cock on her tightly closed anus.

She felt the smooth head touch her tiny hole and she quivered with anticipation.

"Just relax and let it slide in."

"I don't know if it will even go in! I have never done this."

I began to push, applying more and more pressure. The tight ring of muscle at the entrance suddenly gave way and opened, and the head and another inch or so went into her.

She exclaimed "OW! It's too big!"

"Do you want me to stop?" I had no intention to.

"Yes. No. Maybe."

"Which is it? Make up your mind."

She thought for a moment and then said, "No. Don't stop. Just go slow."

I began to work it into her carefully, a fraction of an inch at a time.

Her virgin asshole stretched and accepted it provided I didn't push too hard.

When it was about half-way in she whispered, "Do you think it will go all the way in me?"

I think that was a rhetorical question, mostly intended to entice and encourage me. It worked.

"Yes. Just hold still and let it happen."

She murmured "OK" and surrendered to the inevitable.

As I pushed in a tiny bit at a time, she made a soft sound with each push, like "Oh . . . Oh . . . Oh."

I don't think it was pain, I think it was pleasure.

Slowly but surely my cock disappeared up her tight asshole. When the last inch slid in she grunted "Uhh!"

She held her breath for a few moments, and when she resumed breathing she was exhaling hard, like a woman in labor.

"Are you OK?"

"Yes. It's way up in my belly! I needed to catch my breath."

"How does it feel now?"

"It feels different this way. Like it's more way up inside me. Not like in my . . ."

How funny. She was too modest to say cunt, or vagina, or whatever, even though we were joined in the most intimate way possible.

"I know. Now I am going to finish in you. Do you want my cum in you?"

Her head was turned to the side and her eyes were closed.

Softly she replied, "Yes, please."

I began to hump her gently, in and out just a couple of inches because her virgin asshole was so tight. She let go of her butt and her hands fell to her side. My cock was now disappearing in her butt-crack.

After what seemed like an hour but was probably just ten minutes her breathing was hot and heavy. The room was filled with the musky fragrance of her wet cunt. It opened and closed from the pressure of each thrust.

The head of my cock was poking and prodding at her soft insides. The seminal fluid I produced was providing lubrication and I could give her longer strokes.

I sensed the finish line approaching and I said, "Do you want it all in one big squirt? Or four or five smaller spurts?"

I really can't control that, but I wanted her to think about it as if I could.

She answered eagerly, "Just pump it into me."

I pushed all the way in, with my balls flattened out against her butt-cheeks.

I made some animal sounds and my cock twitched and throbbed as the cum pumped through on the way into her belly.

She felt it gush forcefully into her and her eyes snapped open with surprise. As I continued to empty myself her surprise turned into intense pleasure. She murmured "Yes" with each spurt.

I reached around and touched her clit which was like touching the detonating trigger for explosives. She had a violent orgasm, almost throwing me off like a bucking bronco.

It took me a few moments to recover, and then I collapsed on her. She mumbled,"Too heavy! I can't breathe."

I said, "Sorry," and pulled my still hard cock out of her asshole. I laid next to her and she kissed me like a lover, not like someone who has been coerced into taking it up the ass.

"I have never felt it like that. You put so much of your jizz in me."

I said, "I like the idea that it stays in you."

She thought for a moment and said, "I like that too."

She fondled my balls and stroked my cock which was half-hard.

"Most men go soft when they finish. Does yours always stay hard?" She gave it a gentle, affectionate squeeze.

I just smiled. She acted so reluctant at first, but she has handled cocks and played with ball-sacks before.

"Your balls are nice and big. Your cock is too. I love it."

We enjoyed the afterglow for a while and then she got up to get dressed.

She started to put her panties on, but I said, "Wait. Don't do that. Go commando. Leave them for me. Something to remember you by."

She smiled and tossed them to me. I caught them and put the crotch up to my face and took a big sniff.

"Thank you. I might jack off with them later."

With a look of dismay, she said, "No! Don't do that. Don't waste it. Save it for me."

"If I save it for a week it will be like giving you an enema."

She blushed and softly replied, "I might like that."

As she was pulling her jeans on she said, "Damn it! It's running down my leg. I'm sorry."

I said, "Let me help."

I got up and went to the nightstand drawer and retrieved a butt plug from my collection of toys.

She bent over and spread her ass and I inserted it. It went in easily past the thick end and her asshole closed around the thinner base.

"That will stop it. If you need to use the toilet just pull it out."

"I don't think I could have taken that before today."

"Your asshole has been stretched out and it will take a while for it to go back to normal."

She said, "I don't think it will ever be normal again." But she smiled as she said it. She must be thinking how easily a cock will go in next time.

We had a naked embrace and she kissed me as she played with my cock.

I went to the bathroom and moistened a washcloth with warm water.

Back at her side I said, "Let me clean you up a little."

I started down by her ankle and worked my way up cleaning up the cum. There was a large gob of it up on her inner thigh and I scooped it up with my fingers.

"Do you want to taste this?" as I offered it to her.

"No. Wait. . . Yes."

She sucked the creamy cum from my fingers and licked them clean.

"I have never felt this way about any man before. I would like to swallow a whole mouthful of that."

She pulled on her jeans over her naked butt and her pretty pussy with its little mustache. And then she put on her bra and top and slipped into her shoes.

I walked her to the door, and she said, "Are you going to contact the police about me?"

"No, I have my watch back and you did what I asked. I'm sorry if it seemed like punishment but I needed it that way."

We stood at the door for a while and she was reluctant to leave.

She was lost in thought for a minute, but then said, "I have to confess something. A couple of weeks ago I stole some cash from your wallet. I think I need to be punished for that, too. I need you to teach me another lesson."

I don't remember missing any cash, so I think she just made that up. If she wants to justify it that way instead of admitting she likes it I will play along.

"You have probably been a bad girl all of your life. I think you need frequent punishment, like once a week. I would be glad to provide that. Let's say every Tuesday after you are done cleaning."

"So, I still have to clean your house?"

"Sure. That's what I pay you for. I am not paying you for the sex. That's the punishment you deserve."

Like hell it is. She will enjoy every inch of it.

"Do we really have to wait until next week? I could come over after I finish work."

I replied, "Is tomorrow too soon? Will you be too sore and tender?"

"If I am you can give me that mouthful. I promise I will swallow every drop. I know you want it inside me."

She had a dreamy look in her eyes and she was aroused at the thought of a mouthful of my cum.

"Someday I would really like to have that special enema you mentioned. It would be difficult to wait a whole week but it would be worth it to feel a weeks worth of your semen pump into me. I would like you to give it to me so far in me that it wouldn't come gushing out like an enema. Maybe you would have to butt-plug me again."

"Gale, if your asshole is not too sore I will give you a preview of that tomorrow. I promise I wont jack off tonight or tomorrow. I will give you a 24 hour load."

I know I will enjoy disciplining her with my cock again. Maybe I will tie her face-down spread-eagled on the bed to reinforce the punishment.