On Probation

My Name is Jack Jacobson. I was recently convicted of marijuana possession. Luckily, it was my first offense. I was put on probation and into a "diversionary program". One of the conditions of probation was that I refrain from using alcohol and marijuana, to that end I was to report for periodic drug tests. My probation officer's name was Jean Simmons.

So the fateful day came and I reported to the probation office. All I knew was what I thought was a "he" was named Jean Simmons. It was no big deal. I didn't want to go to jail so I had complied with the terms of my probation and would almost certainly test negative. Much to my surprise, Jean Simmons was a woman! Not only that but she was drop dead gorgeous. She must have been older than she looked because she looked 20 years old. I'm 25 years old by the way.

She was dressed like a classy slut with a too short black skirt, a black blazer and a thin white shirt. She must have been 6 feet tall in her heels. Maybe she was deliberately trying to create a sexually charged atmosphere because she had on slutty makeup, too much eye shadow and bright lipstick. Her blonde hair had some kind of shiny jell in it and it hung loosely to her shoulders.

After the introductions, we discussed my probation and basically she was against everything that is fun. She said she was a "hands on" probation officer. (which I thought meant she was going to ride me like a donkey to the full extent allowed by law, Just my luck.)

Then, she came straight to the point. "I need a urine test" and she handed me a cup. "Right this way", she said and we went down the hall to the bathroom. "Step right into that bathroom and we'll be done in a jiffy."

So I went through the bathroom door and as I shut the door, she blocked it with her foot and followed me in and said, "The urine test must be supervised"

I thought, this was just not right, what kind of fucking outfit were they running here. "I'm not going to pee in front of women. No way, I want to see your supervisor"

So we exited the john and went back into for her office, she paged the secretary and asked for the supervisor. After a few minutes, her supervisor showed up and turns out she's also an attractive woman. To make a short story shorter, she backed Miss Simmons up, the basic argument being "What if your probation officer were a man? We don't discrimination based upon a person's sex in this office."

"Then can I change to a male probation officer?" , I said, hopefully.

"Tell it to the judge, for now you're assigned to Miss Simmons." and off she went.

So we headed back to the bathroom where I said, "I just can't do it in front of a woman."

"We've already settled that, either you take this test or you're going to jail, now which is it going to be?"

"The urine test I guess"

Clearly annoyed, she said "Then get on with it, you wasting my time, I have other clients, you know, I've seen plenty of penises in this job and I'm sure your's is nothing special"

Quickly, she sat on the toilet seat and pulled me around to face her. She opened the button of my jeans and pulled down the zipper. I was too stunned to do or say anything. She grabbed the waistband of my jeans and pulled both my underwear and my jeans to my knees in one fell swoop!

Now I have a pretty big circumcised cock and it was rising fast since a hot female just pulled down my pants. Plus the proximity to her face, about eye level a just couple of feet away. She grabbed the cup out of my hands and grabbed my half mast penis and put the cup up there to catch the sample. "Now, Mr Jacobson, I need you to urinate, I can't do everything for you." She ordered.

But I had a full blown erection by then. All eight inches had pulled her hand up but she just changed to an upward grip and moved the cup up to meet it. She had a look of exasperation. "I don't have all day, get a move on"

I told her "Don't you know men can't piss when they have an erection?"

Still holding on to my hard cock, she said. "Why do you have an erection during a urine test? Can't you control yourself? Let's go, times a wasting"

"If you'd let go of my cock, maybe it would go down enough to piss" I said. "Why did you have to pull my pants down anyway, all you had to do is pull my penis out of the fly, or better yet, let me do it for christ's sake"

"Will that help get rid of your this erection?" She replied. So she grabbed my pants and started pulling them up.

"I can do it, I can do it" I said, but she just kept pulling them up anyway, then she buttoned the top button with my entire hard dick and my balls jutting obscenely out the fly and my boxers bunched up beneath my balls.

She resumed her grip and held the cup. "There, Is that better? now piss." No more "urinate" I guess. With even more handling of my cock I was more turned on than ever.

I said, "You've got to be kidding, I didn't mean my whole fucking cock sticking out the zipper, just a few inches, enough to reach the cup, that's how men piss."

"You are being very difficult Mr. Jacobson". Then she grabbed my cock and tried to stuff it back thru the zipper but it was harder than ever, so it bounced back and she kept pushing back - trying to do the impossible - stuff a rock hard cock back through a zipper. Her hand was rocking up and down she was like jacking me off.

"You'd better stop, Miss Simmons or I'm going to cu...." And I shot my load right in her face and hair, the biggest load I ever had, spurt after spurt. It seemed to last forever and she seemed to be pointing my cock in different directions to make sure her entire face and most of her hair where covered with jizz.

Finally she let go of my cock and said. "You goddamn mother fucking asshole, look what you've done, I should violate your ass right now for assaulting an officer of the court."

I was still in a daze. It took me a minute or two to recover, then I said, "I'm so sorry Miss Simmons, please don't violate me, I'm sure I can do it now if you'll just give me one more chance"

After a pause she said, "Okay, I'll give you just one more chance to meet the conditions of your probation and I suggest you take advantage of it."

Then, looking more like a bukkake porn star than a probation officer, she said, "Here, let me help you with that, Mr. Jacobson...