Meeting My Probation Officer by Wilderness Cry

“And then the anal sex at the end?”

“But it would definitely be worth the wait to empty my balls right up inside your sexy little arse.”

She smiled again, looking totally unphased. “So, talk me through them then, one at a time. Tell me exactly how each one would happen… in detail.”

I stared at her blankly, suddenly realizing that this was the most bizarre situation I’d ever found myself in; I was in my first meeting with my Probation Officer, starting my sentence for a crime I hadn’t committed. She had the power to put me back in court to be re-sentenced – which would mean a worse punishment, like prison – and she was telling me to carry on talking pure filth to her.

I had to admit defeat; I was never going to be in control here, because I was in no position to refuse; and I couldn’t complain because she would obviously deny it and make something up to get me sent to prison.

Was that where this was going? Or was she just winding me up as revenge for what I had been stupid enough to say to her? I really did want to fuck her, anyway.

She was still looking at me, waiting patiently. “Well?” That killer smile, again.

I swallowed and took a deep breath. “Well, I guess…” I looked around the tiny room for inspiration. “I guess we’d have to do it at the table here. You would push your chair back and stand up. I would come round and lean against the edge of the table, facing you.”

My gaze dropped to her cleavage. Her blouse had enough buttons undone to just reveal the curves of her breasts as they disappeared from view; just enough to make me want to see more. I looked up at her again and she was still looking at me, smiling. She had watched me checking her out. I swallowed again and licked my lips. My throat was dry.

“I would take your blouse off, and then your bra, as you unzip my jeans. I would play with your tits as you start to wank me off. I would tell you when I was getting close, and you would sit down. You would wank me off faster, pointing my cock towards your tits so I couldn’t miss the target, and you’d just keep going until I spilled my nuts all over you.”

“I like the sound of that. What would happen at our next meeting?”

I paused and looked around again, the next idea quickly taking shape.

“We would start the same way,” I said. “Once you’ve got me hard, I would pull your skirt up round your waist, and you would sit on the edge of the table. I suppose you would already have taken your knickers off before I arrived. I’d start fingering you to make you wet, and you’d keep wanking me. Then you’d guide my cock into you and lie back on the table, so I could stroke your clit and make you cum while I fuck you. Then I’d bang you ‘til I shoot my load up you.”

I grinned at her, hoping she liked the sound of that, too. She did. “I’m glad I get the chance to cum, too. Good to know you’re not selfish. So, what’s next?”

I had to think quickly, because my next idea actually was pretty selfish. I added a bit in at the beginning.

“Err, exactly the same. I’d start by giving you a good fucking on your back, but then I’d pull out, kneel between your legs, and lick your quim until you cum. Then I would sit down, and you would kneel between my legs and gobble me until you’ve swallowed the lot. And the next time,” I quickly added, “we would do the same again, only you would pull away just in time for me to squirt my spunk all over your face. Then you would use the tip of my cock to wipe it all into your mouth and swallow it all down.”

“And finally?” she asked me.

“We would have to spend more time fucking and sucking while you got used to me fingering you up the arse, with lots of lubricant. I guess it would be easier for you to lay face down on the table for that. Then one day, I’d be fucking you from behind, and fingering your bum, and then I’d pull my finger out and put the tip of my cock just inside your hole instead. It would still be open a bit where I’d had my finger in you.

“Very slowly, and gently, I’d ease my cock all the way in. You would put your hand down between your legs, so you could frig yourself off, and I would roger you until I’ve emptied my balls in you. I don’t think it would take very long.”

We both smiled this time.

“Okay,” she said, writing something on the back of a business card, and sliding it across the table to me. “I just need your signature on the papers I filled out earlier, and you can go.”

I signed the papers without reading them, and I didn’t really listen as she explained what they were. I was still trying to get my head around our conversation.

“Your next appointment is at seven o’clock sharp tonight, at the address on that card. Don’t be late.”

I looked down at it. It was an official probation service business card with her name printed on it. I turned it over to see what she had written. It had to be her home address. I was shocked. “Oh, okay,” I said automatically. “I’ll be there.”

“You will if you know what’s good for you” she said, grinning at me. Then she got up and held the door open for me. It was time for me to go.

The address was an apartment in a tower block. It was in an okay part of town. I arrived a few minutes early, showered and shaved, and dressed in my best shirt and trousers. I had brushed my teeth several times and had on plenty of deodorant and after-shave. I wasn’t sure what to expect, but I wanted to be ready for it.

I hadn’t made any effort with my appearance for my earlier meeting. I guess I hadn’t been in a very co-operative state of mind. I’d worn scruffy jeans, yesterday’s t-shirt, and hadn’t bothered shaving. It was a pointless protest that I hadn’t really thought through.

But things had changed, and I wanted to make a good impression, although I must have done already, I supposed. Otherwise I wouldn’t have got this invite, would I? I don’t think I’m astonishingly good-looking, and my story-telling left a lot to be desired, so she was either a nymphomaniac, or the whole idea of me being obsessed with her body must have turned her on. Whatever; I was hoping for a good result.

If she was expecting me to take her out to dinner, I was hoping her tastes weren’t too expensive; I could do better than a Macdonald’s, but not by much without time to save up. Maybe she would go Dutch?

I paced up and down outside her door, trying to stay calm, until it was exactly seven. Then I rang the bell.

An instant later, she opened the door just wide enough to look through the gap and smiled when she saw it was me. She had to have been waiting just the other side of it. Stepping back, she held the door wide open. She was wearing a black see-through negligee and matching panties, and nothing else but that smile.

“Fuck me!” I gasped.

“Why else would you be here?” She grinned, and motioned with her head for me to go in.

She closed the front door and squeezed my bum as she brushed past me, wiggling along the passage. I followed her and found myself in her bedroom. She wasn’t going to waste any time.

I suddenly had an odd thought: was this an ‘appointment’? Did she have another one at eight? Was this the point when she gave me the price-list, with no option for me to refuse, on penalty of jail-time? That would be a clever little scam.

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