Originally Posted by Esandes (Post 3531053)

This would also be a fun one to see if she would be willing to share it with him…

Originally Posted by toonzilla (Post 3531057)

Which one?

Originally Posted by toonzilla (Post 3531057)

I agree! See through but not extremely visible nipples. Not sure she would do that, though, at least right away. I’m trying not weigh in on what to send. Just letting Liv choose what she wants. 😜

Originally Posted by toonzilla (Post 3531296)

she said she was till waiting on a response but I'm sure she'll get one, and a positive one at that...

Originally Posted by toonzilla (Post 3531296)

Update: The insurance lawyer had to call Liv back to discuss business yesterday afternoon and after work talk brought up the pics again, repeating how impressed he was with her posing and how attractive she looked in them. He told her she missed her calling by not going into modelling. She just laughed and told him he was crazy. At that point, he mentioned again that she could feel free to send any more pics she wanted and that they wouldn't go any further than his eyes. I guess Liv thought it over and finally sent him these, showing quite a bit more than the others. When I talked to her last, she said she was till waiting on a response but I'm sure she'll get one, and a positive one at that...

Originally Posted by Esandes (Post 3531315)

I’m positive she will get an amazing response. I can’t imagine what’s going through his head. How hard he’s holding back asking for what he really wants! These pics are so enticing! I also wonder if she is thinking about which ones she will share next!

Originally Posted by toonzilla (Post 3531320)

I’ve been putting myself in his position too. Trying to figure what I’d do or say that wouldn’t be over the line. Though I’m sure I know what he WANTS to see, lol! Liv HAS been thinking about what to share next though because she’s been running stuff by me. I’ve been trying to leave it all up to her so I’m not giving her much input. Much to her chagrin.

Originally Posted by toonzilla (Post 3531492)

he found... her eyes to be beyond gorgeous

Originally Posted by toonzilla (Post 3531492)

What do you guys think she should do? Not just fantasy-wise but realistically.

Originally Posted by toonzilla (Post 3531492)

Update: Even though it’s a holiday here in the US, Liv got a response to her newest pics. Her lawyer friend texted her that he found her pics extremely sexy and her eyes to be beyond gorgeous. He said he knows it could be seen as inappropriate (and it definitely is, lol), but he was dying to see even more than what she was teasing him with. Liv told him she's not sure that would be a good idea considering their business relationship but she'd think about it. She asked me again what I thought she should do but I told her it was up to her, that she's the one that had to work with him. I think she said she needed to talk to him about another claim Monday so I guess we'll see what else happens...

I hate to post without a pic so here's one I think would be a good compromise for her to share. This or the one Esandes posted earlier, though his showed an obvious nipple. Not sure if she would ever consider showing her older pics to him either. I guess its all up in the air at this point. What do you guys think she should do? Not just fantasy-wise but realistically.

Originally Posted by y2kv2 (Post 3531500)

I could be wrong, but I do believe I've said that to you myself at least a couple times!

After almost 2 months of silence, gotta say it's great getting regular updates on Liv again, please keep it up :cool: Still holding out hope we'll get a video of her so we can hear her voice



*puts on serious hat* Ok, all fantasies and lust aside...

I'm a firm believer in the old adage "one should never fish off the company pier". All three of you have expressed concern over how "inappropriate" this is, and for good reason: because it IS inappropriate. Just based on what's happened so far, if the wrong people were to get wind of this, the least the two of them could expect is a stern talking-to from HR. The fact that the other guy is a lawyer, he ought to know better than any of the rest of us what the score is here, but I digress

There are ways to keep the enticement up & not alienate one another and not also risk anyone being sent to the unemployment line, but it involves strict discipline, "radio silence" (so to speak) and patience. Nobody can afford to have their feelings getting hurt, so everyone needs to be on the same page

1) Are their paychecks both signed by the same payroll office? Or are they on a "client/customer" basis? If they're on a "client/customer" basis, that's the easier of the two. Hate to say it, but in that instance, the best way forward is to stop now, wait until they no longer have business together anymore, then they can pick up where they left off, no harm no foul. If they're both employed by the same company, even if they're in different departments, the rules are vastly different and they need to seriously reconsider pursuing this any further until they're no longer working at the same place. Sorry

2) The manner in which photos and any written communiques have been shared, are these on company-issued phones or personal phones (that the company doesn't have access to & cannot demand be turned over)? On a similar note, are they engaging in these shenanigans using company email, or private email? Lastly, is any of this stuff being done on company computers? If it's personal phones & emails, that provides a little breathing room (albeit doesn't absolve the concerns of #1 above). If this stuff has been done on company electronic devices or using company email, she needs to approach him at his desk and watch him physically delete any and all communication between them of this nature. That means any photos she's sent (and any he may have sent her of himself), any texts/emails of a lascivious nature, all of it. Then she needs to do the same on her end and make sure he sees her doing it (that way he doesn't feel like she's having second thoughts, or worse, setting him up for a HR complaint; she's holding herself to the same standard she's holding him to, which will give him peace of mind). Then if they absolutely cannot hold off until the future, they need to establish a way to continue this stuff as far away from the prying eyes of their employer as possible (private email, personal/burner phones, etc), NEVER do anything on company electronics and never have any direct IRL contact with one another at the office unless it's strictly work-related. Like it was before this stuff all started. Be as flirty & sexy as they want when they're off the clock, keeping in mind the other concerns, but when they're on the clock or using company resources, needs to be 100% business.

3) What's his relationship status? Does Liv know? That's kind of important. One of the tried & true rules of cheating is "tell as many lies to your s/o as you want, but for the love of god, do NOT lie to your side piece." It's one thing that Liv is married because, as her husband, you're "in the know" and don't have any issues with what's going on. If he's single, then it's all good. But if he's married or otherwise spoken for, unless the four of you are going out every other night as a group to play, like, pinochle or do karaoke, neither of the two of you have any idea what his s/o is liable to do if she (assuming female) were to find out what's going on. Hypothetical: say every reasonable precaution is taken, no issues at work, nothing. Then she finds his burner phone, or he leaves his computer on & she's able to access his email, and then finds out everything (or enough to confront him for further clarification). Who's to say that, in her very likely rage, she won't head straight to his job & inform them exactly what he's been up to and with whom? That would affect all 3 of you, but, as the victim (which is what she would be), it wouldn't affect her, at least in the same way. Worst case scenario: if she's married to him & doesn't work herself, with the way divorce laws are structured, she has every incentive in the world to report him, get both of them fired, file for divorce and then take half his shit for years upon years, and she can very easily do this with zero fucks given. Considering he's a lawyer, that's a pretty hefty paycheck for being the victim of infidelity; after all, a lot of guys with a lot less to lose than he has have gone under to a greater degree than that for a lot less. And that's not even factoring in the possibility that he may have kids. As complicated as this may be already, that would make it exponentially more complicated (and expensive for him).

Bottom line: if this hinky stuff between them is to be pursued, it's imperative his relationship status be fully disclosed to Liv, & if he is indeed spoken for, he's not the only one playing with fire; she is too. And by extension, so are you.

Just playing Devil's Advocate here.

Originally Posted by toonzilla (Post 3531636)

No new lawyer news but here’s a sexy sudsy Liv pic for your Saturday morning viewing pleasure…

Originally Posted by Esandes (Post 3531673)

So sexy! I love how she’s pushing her tits together. Thanks for sharing! Maybe one day she will be at the point of sharing pics like this with him.

Originally Posted by herbull (Post 3532013)

Liv looks so gorgeous. It would be great if the lawyer 'stumbled' across this site and these posts, and you/Liv could share posts with all of us including him.

Originally Posted by toonzilla (Post 3532014)

That would be awesome! Years ago, Liv might have even sent him this way but she’s gotten a lot more shy and protective of her pics since then. If the lawyer hadn’t taken an interest, I don’t think she’d even be sharing with him now.

Originally Posted by toonzilla (Post 3532329)

Hopefully, I’ll have new lawyer news soon but until then, here’s a sexy shot of Liv to start your week off right!

Originally Posted by toonzilla (Post 3532460)

Update: Liv and her lawyer friend talked again this morning. It was mainly about business but then it moved on to books as they found out through the course of the conversation that they were both avid readers. Liv remembered some pics we had taken that involved a book and told him she had the perfect photo to send him. He definitely got an eyeful with this one and responded to her text with “There’s a book in the pic?” I don’t blame him, her boob was just about ready to pop out!

Curious as to where you guys think this will go next. Still not sure she’ll send him nudes but man, she’s getting close to moving beyond teasing…

Originally Posted by Esandes (Post 3532518)

Wow we are really making headway! I love it. I hope she goes just a little farther with what she shares with him!

Ideally something like this would be a nice next step but hard to say if she would do it.

Originally Posted by toonzilla (Post 3532520)

I guess we'll find out together! Not sure if she'd do that or not. I'd be the first to know though because she wouldn't know how to crop it like that, lol, so she'd come to me! :D

Originally Posted by toonzilla (Post 3532729)

It’s Tits Out Tuesday! Enjoy Liv’s!

Originally Posted by herbull (Post 3532731)

Love Tits out Tuesday.

Also a fan of Wide open Wednesday :D

Originally Posted by Esandes (Post 3532825)

Just had some thoughts on what else Liv might want to share with her friend. Maybe something like this? Just some pictures that are suggestive and little teasing but kind of unclear as to what is actually occurring.

Originally Posted by toonzilla (Post 3532827)

Not sure she’d go that far but at this point I guess anything is possible! We can dream, can’t we!

Originally Posted by herbull (Post 3532731)

Love Tits out Tuesday.

Also a fan of Wide open Wednesday :D

Originally Posted by toonzilla (Post 3532961)

Update: Liv and her lawyer colleague talked again yesterday. First about work and then back to flirting/teasing. He reiterated how much he’s enjoying the pics Liv has been sharing and they discussed what’s attractive to him (and her as well, though sense of humor was number one for her). He told her he was a breast guy but since his ex had the boobs but not much of a backside, he was always appreciative of a good butt. Liv hinted that she had a pose he might like and sent him this one!

The lawyer replied back that he liked that one a lot and that Liv certainly was not lacking in the butt department! I approve of her choice of pics and agree with the lawyer! 😍

Originally Posted by Esandes (Post 3533057)

Very exciting. Thanks for the update. I love that this picture is more blatant than suggestive like the past few. It definitely sets a standard for what her friend might feel like he can ask for. It also opens the door for more pictures from this series to be shared. I love it, thank you!

Originally Posted by toonzilla (Post 3533058)

Yeah, this could go absolutely any direction at this point. I was a little surprised she sent this one but I guess you can see butts anywhere. They’re not as taboo as boobs or pussy.