Sunday
I got my Sunday message from Sandy.
[Bob texted me while I was on my way over to his place to say his wife was home, so I'm going to go home]
Bah. I'd been looking forward to hearing about her getting fucked.
]When you get home, I want you to suck Billy off and have him shoot a point of view video of him cumming over your face. And how do I like my whores when they suck dick?[
[Naked, sir]
]Good girl[
True enough, about an hour and a half later I got a video in an email from her. It was looking down at her, kneeling and naked, in front of a fully dressed Billy. She reached up and unzipped his pants and pulled them down to past his hips. She fished around in his boxers and brought his dick out. She licked the shaft, holding his balls as she did so, then put the tip in her mouth. She then went to work sucking him off and after a surprisingly short amount of time he grabbed his dick and pulled it out of her mouth. She knelt there looking up at him as he jacked himself off over the lower half of her face. The final spurt landed on her knee and she looked down at it, then the recording stopped.
I wondered how the conversation about doing that had gone.
---
Monday
I had a quiet morning at work, and watched Sandy head out to Bob's office.
About fifteen minutes later I got a message from her.
[Bob was between meetings, so he just had me kneel down in front of his chair and suck him off]
She slunk back to her office and put her head down behind her monitor.
On her way out, Sandy came over and stopped at my desk. I was working, so the interruption annoyed me, but I looked up at her.
"Can I wear normal panties tomorrow, under the cheerleader skirt?" she asked me quietly.
"Why?"
"Because somebody might see under it - it's pretty short. I don't want anybody here seeing me in a sexy thong."
"I'll make you a deal," I said. "If you wear panties, you have to make sure that somebody here sees them, and text me about it. If you wear a thong, you don't have to show anybody. Your choice."
---
Tuesday
I got to the office on time. I said "hi" to Judy the receptionist in her cat costume.
Sandy was already there in her cheerleader outfit.
I dropped my bag on my desk and went into her office. I went to the side of her desk and looked down.
"Show me your panties," I said.
"Good morning to you too," she said, lifting the front of her skirt.
She was wearing normal, white panties.
"I look forward to hearing about your day," I told her.
"I notice you're not wearing a costume," she said.
"I'm an office drone," I said and headed to my desk.
Just before lunch time, I got a message from her. I hadn't even noticed her leave her office.
[I dropped my mug in the kitchen and Mike would have seen my panties when I bent down to pick it up]
Hmmm. I thought she could do better than that, so I texted her back.
]I want you to show your panties from the front[
A little after lunch, I got another message from her.
[Bob summoned me to his office. He lifted my skirt, then had me bend over his desk and pulled my panties down. He fucked me in the ass and I didn't cum. I dropped the condom in the ladies' room as you've told me to]
That wasn't going to count, and sure enough towards the end of the day, I got another message.
[I pretended to stumble and fall in front of Jim, and he got to see all of my panties]
That'll do, I figured.
---
Wednesday
I rolled into work on time and Sandy was already there. I went in and said "hi."
"Hi," she said.
"Have a good night of trick or treating?"
"We handed out a bowl of candy, yes," she said.
"In your cheerleader costume?"
"Yes," she said. "Billy really likes it. He made me take the panties off though."
"I bet you made some fathers' nights," I told her before heading back to my desk.
Towards the end of the day, Sandy was walking past my desk and stopped briefly.
"What should I bring to wear tonight?" she asked.
"Why not bring your cheerleader costume," I told her. "Seeing as it's almost Halloween."
She sulked off.
Later at home I hatched a plan for the evening. When Sandy got to the door, I invited her in, then watched her change into her cheerleader costume. Having changed into a sexy bra, rather than her sports bra, and the sweater, she took off her shorts and put the skirt on. She pulled a pair of normal white bikini panties out of her bag, but I shook my head.
"The thong'll be fine," I told her.
I took her hand and we headed for the door. We dropped her bag in her car, and I told her to lock it up. We'd be walking.
"Where are we going?" she asked.
"This way," I told her. "Not far."
I led her to a little dive bar a short walk from my place. It was off the main drag, and looked to have been converted from an old house, years ago.
"Now act normal and do as you're told or I'll leave you here," I told her, and she nodded, looking nervous.
Inside it was pretty dark. There were a bunch of old biker looking guys, and we smiled and nodded to each other, but their eyes were mostly on Sandy.
At the bar I waved to Red, the bartender, and ordered 2 bottles of Corona. Nick, one of the leaders of this band of misfits, came over and we bumped fists.
Nick and I go way back, and we've shared multiple adventures involving women over the years. He must have known Sandy was doing as she was told because there'd be no other reason why a younger woman would be with me, here, dressed like that.
"It's been a while," he said to me, but looked at her.
"Yeah," I said, "been busy. How's things?"
"Looking better," he said, almost licking his lips.
I got our bottles and handed one to Sandy. She took it, but didn't make a move towards drinking any.