A request for something she'd never do

• What's the most embarrassing thing you've ever done? Something you've never told anyone?
• I lost my virginity in senior year of college in a threesome with my roommate.

Tom's eyes went wide. He looked at Sandy's hands, but she definitely hadn't typed that. He looked at his computer, relieved to see that these messages still weren't showing up on it. "Um, Sandy? Let me have a look at your phone real quick."

"Okay." The shy young woman turned her phone around and showed him the screen. The slack app didn't show any messages between him and her today.

This made no sense. Someone else had to be writing these messages, but Sandy had done a couple of requests from messages she clearly hadn't seen. He had to test this, but he desperately hoped that he was right about nobody else at the company being able to see these messages.

• Tell me the story of how you lost your virginity, but do it out loud.
• Why?
• It's important to build trust with your mentor. This is a terrific trust building exercise.

Sandy cleared her throat. She adjusted her glasses and nervously asked, "Mr. Carlton? Can I tell you something?"

Holy crap! "Sure, Sandy, you can tell me anything."

"Well, I know you think I'm this perfect little goody-goody you can't relax around, but I'm really not. In fact I lost my virginity in a threesome!"

Tom tried not to freak out. "Oh? That's interesting. How old were you?"

She looked down. "Twenty-two."

"So, a year ago. How many times have you had sex since then?"

"Um, that was the last time."

"Oh, well, that's okay. Please continue." As he spoke, Tom wrote another message.

• This is incredibly hot.

Sandy blushed and looked at him with an intensity that he'd never seen in her before. "My roommate was this gorgeous girl named Rosa. She said I was too pent up, so she took me to a bar. We saw this really handsome guy, tall, beautiful smile, and the darkest skin I'd ever seen. He looked like a museum painting portraying strength. I was too nervous to approach him, so Rosa went with me. He was more interested in her than me, most guys are, but he didn't object when she asked if I could go with them back to his place."

• Show me some pictures and get more turned on as you tell the story. Be detailed.

Sandy bit her bottom lip as she flipped through her phone. "We didn't take any pictures that night, but here's what Rosa looks like."

She showed Tom a picture of herself side-hugging a hot Hispanic girl. Sandy hadn't exaggerated, the girl was hot as hell. Her thick lips looked like they were made for wrapping around a cock, and her eyes danced with mischief. As flat as Sandy was, Rosa had enough tits for both of them.

"You're noticing her breasts, right? The guy noticed them, too. I'm sorry, I don't remember his name."

"That's okay. Please continue."

Sandy was so worked up now, she was rubbing her thighs unconsciously. "Rosa kissed him as soon as we got into his apartment, but he quickly got her shirt off and laid with her on the couch so he could play with her breasts. She signaled for me to take off his pants, then waved at me not to freak out when I saw how big his dick was. I'd never even touched one before, but sucking it kinda felt good. I was soooo nervous! I don't think he noticed, he kept rubbing his face in her big breasts while he pushed my head down deeper on his cock. Oh my god, I can't believe I'm telling you this, Mr. Carlton!"

"No, this is good!" said Tom. "It shows that you have a lot of trust in your mentor. Please continue!"

Sandy blushed hard, still rubbing her inner thighs as she got more turned on. "He fucked Rosa on her back because he wanted to see her big breasts bounce. All three of us made out while he recovered, and he told us he was an engineering major. Isn't it weird that I remember that, but not his name? Then he fucked me doggy style. He said I had a cute ass and he liked looking at it. His dick was so big, I thought it would hurt, but it didn't. Rosa kissed me as he slid it in, and that kept me relaxed. God, she's so pretty! I really liked looking at her smiling at me as he plowed me from behind. It felt like it lasted forever. The guy was totally spent after that, but he did eat Rosa out while I massaged her back. I wanted to get his phone number, but Rosa said it was better if we didn't talk to him again, so we left after that."

"And that's how I lost my virginity."

Sandy was breathing hard and blushing like she'd just had sex. Listening to this story had also made Tom hard as hell. She glanced down at his crotch and noticed the obvious tent in his trousers, then turned away and hid her face.

"Thank you for sharing that with me, Sandy. It really shows that we have a trusting mentor/mentee relationship," Tom said as he typed another message.

• You should help me with this hardon. It's a good way to show that you're looking out for your boss and it's not really sexual harassment if you initiate it.

Sandy pulled her small hands away from her face and looked back at his crotch. She was breathing very hard as she said, "Mr. Carlton? Do you need some... um... help? I could... give you a handjob?"

Holy fucking shit! This really worked! Somehow these messages were going right into her brain. Tom tried to stay calm and professional as he said, "That's very thoughtful of you, Sandy. Go ahead, a handjob would be nice."

The cute young woman smiled and scooted her chair closer to his. She leaned forward and unzipped his pants, fumbling a little from doing this from an unfamiliar angle. She fished out his hard cock, which Tom knew probably wasn't as impressive as the cock of the stud she'd fucked in college, but it wasn't a bad size at all. Her little Asian hand went up and down it slowly as she smiled at him.

Fuck, this felt good! No woman had touched Tom's dick in three years. Even that had been boring missionary sex from a girlfriend his own age who barely liked him at the end of the relationship. Having a twenty-three year old so hot for him that her glasses were steaming up as she jerked him off felt incredible.

Just looking into her eyes was hot. There was a mix of admiration and lust that was getting him off as much as her hand. Hands, actually, since she'd just added the other hand to his pole. He couldn't get over the fact that he'd made it so this girl actually thought that jerking off a middle aged man was a good way to start her training as a junior editor. The look in her eyes was really hot, and feeling her little hands work his cock was amazing.

As he got closer to cumming, she moved her hands faster and faster, until-

"What the fuck are you doing?!"

It was Janeece, standing in the door of Tom's office, looking like she was about to **** him.