(CW: CSA) Josh & Anna 47: Serial SM Commenter Anna Silent on Family Posts Lately. I Wonder Why?

[Mama Mia]

I know we keep talking about the “windowless warehouse” and how dismal it is — but somewhere a long time ago the Duggar’s did a post or a tour or something of it - and it’s somewhere around 1,500-2,000 +/- square feet of a larger warehouse /workshop that they’d already converted into a nice guest house. There’s a full kitchen, bathroom(s), bedrooms, living room etc… it is, or was, pretty low on windows, but seemed to have adequate exits. I know I’m biased from living in a stupidly overpriced area - but it’s hardly a hovel. And she has the advantage of lots of yard space. 

[SPHASH]

1 hour ago, OrchidBlossom said:

I just hear "Hi I'm Michelle and this is Jim Bob my wonderful husband and our children Josh, Jana, John David, Jill, Jessa, Jinger, Joseph, Josiah, Joyanna, Jeddidiah, Jeramiah, Jason, James, Justin, Jackson, Johannah, Jennifer, Jordyn and our latest precious addition, Josie" whenever I need to remember them. I hate it so much. I wonder where I can get a lobotomy.

You forgot "Josh, he married Anna.  And they had our first grandchildren Mackynzie, Michael, and Marcus."

[EmmieJ]

42 minutes ago, QuiverFullOfCondoms said:

Having money doesn’t necessarily translate into living lavishly. Living humble lives and being intentional about money is often what got people to become millionaires in the first place (Random but interesting study on millionaires). 
Now, did Josh make all that money on his own? Not a chance in hell. It’s probably Jim Blob laundering TLC money.

Did you think I was making a generalization?  I was talking specifically about one person, convicted piece of shit Josh Duggar.  

[neuroticcat]

8 hours ago, Antimony said:

If this story is true, I think the injury is kind of immaterial. They're paranoid at this point, right? Other insiders have suggested the Jim Bob loves to interpret things as "an attack" on the family. They're super concerned about "parental rights" and while it didn't make sense, they've even got the Defense lawyer pointing to Tor as a "privacy tool" for Josh. It all seems to come from one little seed of paranoia and persecution complex, so the injury could have been anything. It would make sense with all the paranoia. 

I'm not sure how a different ER helps you avoid doctors with sharp eyes who will, with any child with an injury, be a little bit more vigilant than they would be with an adult, but they also claim this flight was for paparazzi's reasons as well, so...maybe? Or maybe they didn't want to create too large of a medical record at one single ER. 

They claim this was immediately after InTouch released the report, so Josh would have been just let go from the FRC and may not have been working at the car lot yet. Poster mentions he (Josh and co.) drove around to houses to flip. I don't think the car lot was revived yet and he may not have been working at the time, officially, since he had just left the FRC.

Added Thought: Were I JB, I'd start being paranoid about God himself because it seems to me that every scandal Josh gets caught in is just pure bad luck for him. A data leak from Ashley Madison? It's not super likely. That isn't something you could guard against. An improper filing error leads to InTouch getting a police report that should have been sealed? What are the chances? The shit he downloads gets flagged by the government? He's not very good at hiding but even things that should have been hidden (credit card use at AM, police reports) he's got a bad string of luck with. 

I agree! But you’d think that a religious person who doesn’t believe in luck (don’t they make a thing about not saying good luck?), would, I don’t know, at least consider it a sign from God that their family is on the wrong path. 😅

[Bethella]

6 hours ago, Fjrocks said:

    Okay I am still back digging through 2015 ,  I want to see if the AMA timeline makes sense because it's compelling.   I am trying to figure out when Derick and Jill went to Central America.   I found a US mag article talking about how Derick and Jill came back for a visit and returned with Joy in tow in mid August.   I am trying to go back though and figure out when they first left. 

   I went back through the Dillard archives and.... I will be damned if I can find it in the Dillard archives because of thread drift.....    

   I give up fellow FJers, you win, I can't keep up with you all. 😆  Rufus help me.

 

6 hours ago, Snarkasarus Rex said:

They left when early July, when Izzy was about three months old.

https://people.com/celebrity/inside-jill-duggar-dillard-and-husband-dericks-life-in-el-salvador-photos/

 

6 hours ago, SassyPants said:

I believe they went to CA in late June or early July. I remember being shocked that they would take such a young baby out of the country, and was wondering if they would get him regular newborn care and immunizations while they were gone. The Dillards did seem to spend a great deal of time in the US though. I think the longest stretch in CA was when she was PG with Sam, so early 2017. 

According to my notes- they made three trips to Central America with significant time spent back in the US. 

Trip 1 July 2015-Aug 2015 (1 month)

Trip 2 Oct 2015-6 Aug 2016 (10 months)

Trip 3 16 Feb 2017-20 May 2017 (3 months)

They announced they weren’t going back on 9 Aug 2017. 

[EmCatlyn]

4 hours ago, nelliebelle1197 said:

Yeah but who is this person posting this?

I don’t know.  That is why I said it was speculation and gave the link so people can judge for themselves.  The guy included a bunch of links that seem to refer to various Josh and Anna financial transactions.

It seemed worth sharing because we have been so sure JB controlled all the money. Maybe he does, or maybe Josh has made some money on real estate.  The “one million dollars” seems an exaggeration, but with the booming real estate market, just selling one property could have paid for the lawyer.

[EmCatlyn]

4 hours ago, EmmieJ said:

I find the idea of Josh Duggar amassing a million dollars due to flipping homes in Arkansas pretty hard to believe.  Seriously, if he had that kind of cash, what's he doing living in a windowless converted garage/out building on his parents' property?  If flipping houses was so lucrative, why did he end up sitting in a tollbooth on a crappy used car lot every day?  

As I said, I think the $1M is an exaggeration, but the claim was not that he had “amassed $1M” but that the transactions liquidating his property came to almost $1M.  This could refer to the same properties being sold more than once in the entertaining LLC shell game the Duggars like to play.

The real point is that if some of the property that was in Josh’s name was really “liquidated” (and not just reshuffled to another Duggar), then that money would have probably gone to pay for the lawyers.  It’s an interesting possibility. 

  (As for the car lot, I could see Josh preferring to “work” there than to work from home. 😉)

[AprilQuilt]

Sounds like the bodyguard was with Josh and Anna's family for a brief and very stressful period, so I'd hesitate to extrapolate from his experiences what their usual family life and relationships were like.

If Anna wasn't very meek, good for her. She was in total crisis. I hope she yelled and threw things (at Josh). I imagine it's a struggle to parent how you'd want to through such an experience too. It's not like she's ever been given healthy coping strategies. I can see how in this state of panic she might have been very afraid that an injured child would provoke CPS investigation, and make the decision to get them treated out of state not knowing it would have no materially different outcome.

Ditto Michelle not being 'very motherly': towards whom? Towards Josh, her adult son who just lost them their TV show? We already know she wasn't very motherly in not protecting the daughters he'd abused, however loving her demeanour towards them. How she cared for her younger children in private we don't really know, and the bodyguard wouldn't have seen much of that anyway if he was placed with Josh's family*. I'm not convinced he'd have seen that much of Amy either - evidently at her wedding but again that is exceptional and hardly gives you a measure of a bride's personality.

On the other hand, if during those few months, knowing that he'd lost everything not only for his own young family but also the empire his parents had built up; knowing that he was being scrutinised; knowing that he required protection from the public because of what he'd done... if Josh Duggar was openly watching porn in his car in that situation, his complacency must have been off the chart. Had he stopped caring or did he never care in the first place?

 

*I don't mean any of this as a defence of the Duggars, by the way. I literally have no idea how Anna or Michelle come over in person, or how they parent. However, my gut feeling is that what the bodyguard saw was very likely not a representative sample and that he's massively overstating his insight.

[BernRul]

A lot of people talk about having sympathy for teen Josh, and while I do too to an extent ( his parents raised him in an abusive cult, he was pimped out for TV just like the others) we also need to consider the possibility that even if JB and Michelle did everything right, Josh could still end up watching CSAM as an adult. There is no known cure for pedophilia or effective treatment for sexual predators. Good parenting can't change that. Coupled with the fact that even mainstream American culture is very much drenched in rape culture and misogyny, there really is no reason to assume the Duggar parents could've changed Josh.  Their reaction was still horrendous, of course, and a big fuck you to their daughters. 

[nelliebelle1197]

5 hours ago, EmCatlyn said:

I don’t know.  That is why I said it was speculation and gave the link so people can judge for themselves.  The guy included a bunch of links that seem to refer to various Josh and Anna financial transactions.

It seemed worth sharing because we have been so sure JB controlled all the money. Maybe he does, or maybe Josh has made some money on real estate.  The “one million dollars” seems an exaggeration, but with the booming real estate market, just selling one property could have paid for the lawyer.

I just have a hard time trusting Reddit “insiders”.  There is so much speculation and lack of discernment on those fundie snark subs over there.  That is what I like about our crew (h/t Sarah Maxwell).  We are a bunch of skeptics and much better seasoned and cautious in our fundie watching.  We have also exposed a lot of grifters, fake fundies and frauds so we know to question. I mean, look at that AMA.  FJers spotted the problems within a few minutes! 

[LilMissMetaphor]

Kind of surprised they didn't just name one of them Jiah and save the extra syllables.

[nelliebelle1197]

56 minutes ago, BernRul said:

A lot of people talk about having sympathy for teen Josh, and while I do too to an extent ( his parents raised him in an abusive cult, he was pimped out for TV just like the others) we also need to consider the possibility that even if JB and Michelle did everything right, Josh could still end up watching CSAM as an adult. There is no known cure for pedophilia or effective treatment for sexual predators. Good parenting can't change that. Coupled with the fact that even mainstream American culture is very much drenched in rape culture and misogyny, there really is no reason to assume the Duggar parents could've changed Josh.  Their reaction was still horrendous, of course, and a big fuck you to their daughters. 

I agree but…. big but. There equally is also no reason to think this was mostly nature and not  nurture. What did they do when their first born hit puberty and had questions? He was exposed to hypersexualized adults from birth in his hideous parents and constant breeding. Ugh, can you imagine what he HEARD in the small houses they had before TLC? He probably had the worst of Jesus training and at emotional abuse as a child since he was the oldest and they had more time to harm him. 
 

I don’t know - I guess I can just see the logical progression of child Josh through tween/teen Josh and think that this is quite frankly heavily  on his parents for not teaching him healthy attitudes towards sex and his body from day one.

[Expectopatronus]

1 hour ago, BernRul said:

A lot of people talk about having sympathy for teen Josh, and while I do too to an extent ( his parents raised him in an abusive cult, he was pimped out for TV just like the others) we also need to consider the possibility that even if JB and Michelle did everything right, Josh could still end up watching CSAM as an adult. There is no known cure for pedophilia or effective treatment for sexual predators. Good parenting can't change that. Coupled with the fact that even mainstream American culture is very much drenched in rape culture and misogyny, there really is no reason to assume the Duggar parents could've changed Josh.  Their reaction was still horrendous, of course, and a big fuck you to their daughters. 

There are some treatment programs with a pretty good success rate for preventing recidivism. The individual might still be attracted to children but no longer acts on those urges. For individuals who offend out of trauma rather than true sexual attraction to children, the success rates are also pretty good. I don’t remember the exact percentages off the top of my head but they were above 60%. 

[nelliebelle1197]

2 minutes ago, Expectopatronus said:

There are some treatment programs with a pretty good success rate for preventing recidivism. The individual might still be attracted to children but no longer acts on those urges. For individuals who offend out of trauma rather than true sexual attraction to children, the success rates are also pretty good. I don’t remember the exact percentages off the top of my head but they were above 60%. 

This is total speculation but I wonder if constantly being replaced by new babies children throughout his life impacted Josh in his desire to see children hurt. Heck, my Irish Catholic husband had six siblings and there were several miscarriages. His parents aren’t at all like the Duggars but his oldest brother has some serious insecurities and semi-jokes all the  time about how he is not the favorite - “Kevin is mom’s favorite”. “There is Peter, being mom’s favorite” etc. All the siblings have some of that. In fact, when my 1.8 pound baby came, a (lesbian!) friend of mine had a cousin  at the Vatican who got the baby on the pope’s prayer list because she knew how much it would mean to my inlaws, who are 24 hours away in New Zealand. I actually got a call from my BIL in Wales ribbing me about how I would now always be the favorite DIL! (the priests all over their Wellington suburbs apparently bragged about that for three years and we kept having to take her to meet priests on our annual trips!). 
 

Again, total speculation but it is just an odd thought.

[FusterCluck]

I haven’t read the AMA, so this is just my two cent speculation. Take accordingly. 
 

I am very close to someone under an NDA and their attorney has given them guidance on what they can and can’t say.  And just because you can talk, sometimes sharing everything isn’t safe. I mean, it’s also possible this bodyguard is inflating their own story, but I also have seen what fear an NDA can bring. Especially when the person holding the leash has more money. 

[HerNameIsBuffy]

11 hours ago, justmy2cents said:

So he knew he would likely be gone for a long time and he still spent a ton of money on a futile defense rather than leaving it for his wife who won’t work to take care of his children. Priorities. 

Take reports of wealth with a grain of salt unless you've seen the actual dollar figures.  JB has been putting properties into the kids names for ever and I'd doubt very much that he wasn't also on there are part of the LLC that they can't do anything with the properties without his approval.  

9 hours ago, AussieKrissy said:

I am pretty sure I remember it as him saying they took the child to a "friend" (who then treated them) out of state rather than the er 

I got the impression that the person they took them too would cover for them 

There are two doctors on the board of the Medic Corps scam and at least one lives in Texas, I can't recall if the other does as well.

[HerNameIsBuffy]

9 hours ago, QuiverFullOfCondoms said:

If she is indeed staying at the TTH, then my gut tells me she’s treated like all the other Js living there, receiving room and board. JB probably buys diapers and she’s on the family phone plan. She may get a little allowance here or there but I don’t think she gets direct deposits or has access to a bank account. JB is a cheapskate.

ETA: does Jim Blob now have temporary ownership of Anna now that her headship is in prison? Or does he remain her owner from behind bars? Obviously I’m not talking sexually, more in day to day life control.

I bet you're right about the money.  I think they probably treat her like a teenager living at home with her seven kids.  They pay for the basics and if she wants anything extra she has to ask.  I doubt very much Anna will be given discretionary funds.  If they do she would possibly be able to save up to visit her family or such, they will want to control her access to other people.  I expect every trip to the Kellers will be a gift from Lolli and Pop that she will gush over.  (Obviously speculation, but total control is JB/M's MO.

To your last point...At her wedding Pa Keller transferred authority to Josh so now that he is indisposed wouldn't she be rehomed back to her original owner?  All my dogs have been rescues so no personal experience, but I've read this is common for dog breeders - if you can't keep the dog you have to return it the breeder.  

I mean we know Anna isn't a pet, but I'm not sure they do.  If JB is now her headship can that at least be shameful for Pa Keller?  

1 hour ago, Expectopatronus said:

There are some treatment programs with a pretty good success rate for preventing recidivism. The individual might still be attracted to children but no longer acts on those urges. For individuals who offend out of trauma rather than true sexual attraction to children, the success rates are also pretty good. I don’t remember the exact percentages off the top of my head but they were above 60%. 

Are these offenders also sadists?  Sadistic predators are probably outliers of studies if not specifically included since their pathology is much more complicated than fighting attraction.

3 hours ago, AprilQuilt said:

If Anna wasn't very meek, good for her. She was in total crisis. I hope she yelled and threw things (at Josh). I imagine it's a struggle to parent how you'd want to through such an experience too. It's not like she's ever been given healthy coping strategies. I can see how in this state of panic she might have been very afraid that an injured child would provoke CPS investigation, and make the decision to get them treated out of state not knowing it would have no materially different outcome.

If she was assertive enough to get actively angry at him cheating then there is zero excuse for holding his hand during this trial unless she considers that worse than infidelity.  

And many of them do, and many of them can f themselves.

9 hours ago, Mama Mia said:

I know we keep talking about the “windowless warehouse” and how dismal it is — but somewhere a long time ago the Duggar’s did a post or a tour or something of it - and it’s somewhere around 1,500-2,000 +/- square feet of a larger warehouse /workshop that they’d already converted into a nice guest house. There’s a full kitchen, bathroom(s), bedrooms, living room etc… it is, or was, pretty low on windows, but seemed to have adequate exits. I know I’m biased from living in a stupidly overpriced area - but it’s hardly a hovel. And she has the advantage of lots of yard space. 

I saw clips of it on one of the shower episodes, maybe Abby's?  Yes, it's fitted as a living space but it's still no place to raise children.  Kids deserve a decent home.

Edited December 14, 2021 by HerNameIsBuffy

[AprilQuilt]

9 minutes ago, HerNameIsBuffy said:

To your last point...At her wedding Pa Keller transferred authority to Josh so now that he is indisposed wouldn't she be rehomed back to her original owner?  All my dogs have been rescues so no personal experience, but I've read this is common for dog breeders - if you can't keep the dog you have to return it the breeder.   

Ah, but there's a flaw in your analogy. Responsible breeders do this. They care about their pups and where they end up. Irresponsible breeders stack their pups like cordwood, fail to adequately socialise them/educate them about the world, slack off on food and medical care, hand them over to new owners without adequately checking them out first, and absolutely do not want them back after all this, knowing full well that even if the pup did not leave their care with lifelong problems, it'll definitely have them now. I, ah, wonder what kind of dog breeders the Kellers are.

Edited December 14, 2021 by AprilQuilt

[backyard sylph]

1 hour ago, nelliebelle1197 said:

I agree but…. big but. There equally is also no reason to think this was mostly nature and not  nurture. What did they do when their first born hit puberty and had questions? He was exposed to hypersexualized adults from birth in his hideous parents and constant breeding. Ugh, can you imagine what he HEARD in the small houses they had before TLC? He probably had the worst of Jesus training and at emotional abuse as a child since he was the oldest and they had more time to harm him. 
 

I don’t know - I guess I can just see the logical progression of child Josh through tween/teen Josh and think that this is quite frankly heavily  on his parents for not teaching him healthy attitudes towards sex and his body from day one.

I tend to think nature is supported or weakened or strengthened by nurture. In that environment a person with natural proclivities toward harming children is to be pitied initially as it wasn't taken seriously or directed well in any sense, and as you say, he was exposed to just the sort of thing he ought not to have been exposed to. 

When we're adults and can choose paths for ourselves, the degree to which we feel pity for a person like that is certainly lessened. But I think I can still mourn for his messed-up youth while despising what he became, and although I never liked him from the moment I laid eyes on him, I can't hate him all that thoroughly because the amount of hate I'm capable of mustering is more directed toward his parents. The pity is for all the offspring they misguided and devalued in favor of their brand. 

[AprilQuilt]

18 minutes ago, HerNameIsBuffy said:

If she was assertive enough to get actively angry at him cheating then there is zero excuse for holding his hand during this trial unless she considers that worse than infidelity.  

Definitely not defending her, my best guess is she struggled to keep sweet for a bit and was surly/spicy before her "come to Jesus" moment re not making a something into a disaster, whatever it was she said.

She will have silently internalised every little bit of it, and this is probably why she was clinging to his hand outside court. All her pride and sense of self is wrapped up in trying to be a better wife, in smiling through betrayal after betrayal, cruelty after cruelty, outrage after outrage, and she will pursue this with grim determination whether he likes it or not, probably until one of them dies.

I'd love her to prove me wrong, but 🤷‍♀️

[käsekuchen]

1 hour ago, FusterCluck said:

I haven’t read the AMA, so this is just my two cent speculation. Take accordingly. 
 

I am very close to someone under an NDA and their attorney has given them guidance on what they can and can’t say.  And just because you can talk, sometimes sharing everything isn’t safe. I mean, it’s also possible this bodyguard is inflating their own story, but I also have seen what fear an NDA can bring. Especially when the person holding the leash has more money. 

He addressed questions about an NDA, there doesn't appear to be one:

Quote

Q: Thanks for doing this AMA! I’m curious though bc some of the Duggar’s have alluded to signing NDAs…did you have to sign one?

A: I’ve seen Amy post about NDA’s. We would not have signed the same one.

and

Quote

Q: How much do plan on profiting from your 15 minutes of fame and do you normally talk about your clients in this manner? Did you witness anything illegal? Did you cooperate with law enforcement? Did you ever bring anything up?

A: I dont talk about any of my other clients in this manner. But, none of my other clients are going to federal prison for csam. So I’m making an exception. Nobody wants to be famous for being the guy keeping Josh Duggar safe. I’d say infamous would be a more apt description. As for profit. I’m doing this for me. Everything else asked and answered.

Q: Does your NDA allow for such an exception?

A: I’m not bound by one.

IMO these are also good examples of how he leaves room for interpretation in his answers but I'm obviously not a native speaker

Also he's interested in getting a book deal:

Quote

Q: Hello, I’m a book editor who specializes in memoir, and I could help you put your book together and ready to shop to agents! I appreciate all of your thoughtful and direct answers here. This entire thread is fascinating.

A: I’d be interested in talking further. Message me.

 

[ILoveJellybeans]

10 hours ago, OrchidBlossom said:

Not blasting at all! But, I have to admit I take statements that Josh "confessed" with a big helping of salt. We know now based on Bobye's testimony that two of the girls physically fought back. We know one or two told their parents. I think "Josh confessed of his own volition because he felt so bad" is largely an invention of JB and Michelle to make him look less predatory. Perhaps there is a grain of truth, but ultimately we know now that he did this repeatedly and frequently, that two girls reported it to their parents themselves, and that there were physical altercations. That doesn't square with the idea that Josh knew it was wrong and genuinely wanted help.

Hard to tell from the original police report as its so redacted, but I had always assumed that Josh telling his parents what he had done was prompted by one of his sisters telling their parents first, and that they had asked him about it.

Even before Bobye confirmed it had been going on for years, I assumed that the two times his parents found out what he was doing were just the tip of the iceberg, and that he only told the bare minimum that would sound sufficiently truthful to his parents if they asked the sisters what happened, and downplayed the amount of times he had actually done it. I think he only told them about times when a sister started to wake up and he thought he had gotten caught, or the two times we know of where the girls were awake (laundry room and storytime). I dont think he stopped for long between the time his parents first found out about it and the last time, I feel he was straight back to it once he thought he could get away with it.

I dont know why he told Bobye all the graphic details about the true extent of what he actually did. Was he asking for help then, because he knows he's just "Duggar kid #1" to his parents and they dont actually pay attention to him, but felt Bobye cared more and might listen? Is he a complete deviant and was trying to freak her out and wanted to see the look of horror on her face (my psychopath brother used to enjoy doing that, in fact he was apparently quite braggy when he was arrested and interviewed)

[QuiverFullOfCondoms]

38 minutes ago, ILoveJellybeans said:

I dont know why he told Bobye all the graphic details about the true extent of what he actually did. Was he asking for help then, because he knows he's just "Duggar kid #1" to his parents and they dont actually pay attention to him, but felt Bobye cared more and might listen? Is he a complete deviant and was trying to freak her out and wanted to see the look of horror on her face (my psychopath brother used to enjoy doing that, in fact he was apparently quite braggy when he was arrested and interviewed)

Spoiler

And did he tell Bobye the entire truth of what he did? How sure are we that he stopped at fondling

 

Edited December 14, 2021 by QuiverFullOfCondoms

[HerNameIsBuffy]

19 hours ago, SassyPants said:

A few things make me think question the BG’s authenticity: he was barely involved with the family, yet he defends Amy? Never mentioned Jana or some of the others at all, but supports Amy. Was Amy on the scene much in those short 2 months? Also, would he expose himself, professionally speaking, by speaking out on a forum? It wouldn’t be hard to figure who he might be from what he has reported. Can’t imagine a genuine person would risk doing that. Much of what was said seemed like someone saying what others might want to hear-

He said in the AMA he'd retired from that line of work.  He also said he was initially protecting Josh and then was moved to another family member when he couldn't stand working for Josh anymore.  It was clearly Jill as he told some anecdote about protecting her and Derek at their home.  Jill would have gone to Amy's wedding cameras or not.

My gut feeling is he probably worked for them in some capacity during that time but is adding fanfic for attention.  

[OrchidBlossom]

17 minutes ago, ILoveJellybeans said:

Hard to tell from the original police report as its so redacted, but I had always assumed that Josh telling his parents what he had done was prompted by one of his sisters telling their parents first, and that they had asked him about it.

Even before Bobye confirmed it had been going on for years, I assumed that the two times his parents found out what he was doing were just the tip of the iceberg, and that he only told the bare minimum that would sound sufficiently truthful to his parents if they asked the sisters what happened, and downplayed the amount of times he had actually done it. I think he only told them about times when a sister started to wake up and he thought he had gotten caught, or the two times we know of where the girls were awake (laundry room and storytime). I dont think he stopped for long between the time his parents first found out about it and the last time, I feel he was straight back to it once he thought he could get away with it.

I dont know why he told Bobye all the graphic details about the true extent of what he actually did. Was he asking for help then, because he knows he's just "Duggar kid #1" to his parents and they dont actually pay attention to him, but felt Bobye cared more and might listen? Is he a complete deviant and was trying to freak her out and wanted to see the look of horror on her face (my psychopath brother used to enjoy doing that, in fact he was apparently quite braggy when he was arrested and interviewed)

I have a guess that Josh talked to Bobye because he had been caught once (IMO when a sister told, not because he spontaneously wanted to do the right thing) and either knew that getting caught again was fast approaching or because he thought it would minimize the (already minimal) punishment if he 'confessed'. Knowing how close the families were at the time, and considering that the Holts had taken on a sort of oversight role for him for some reason, I think he thought it was the best avenue to avoid harsher consequences.

I do think there may have been an element of enjoying scaring or horrifying her though.