Josh and sexuality is a prickly, uncomfortable topic that is simultaneously the lynchpin of KingCobraJFS' personality and something he continuously attempts to separate himself from.

Josh has a very particular type when it comes to women. Hot, of-age, biologically female, alive, non-related, consenting, and goth. Especially goth. What Josh determines as hot can be very arbitrary, as Josh thought THIS was attractive enough to smash. Much else of Josh's stipulations - Of-age, alive, non-related, consenting, etc., are self-explanatory. Curiously, despite specifying “biologically female” before, one of his favorite cam girls is Blaire White, a male-to-female transgender camgirl.

Josh seems to hold a love-hate relationship with women, both wanting to be with them but also holding numerous extremely sexist viewpoints similar in nature to involuntary celibate rhetoric, viewing them as the lesser gender.

Josh refers to his prolonged lack of sexual relations as his “Dry spell” - What he believes to be a cool gothic badboy way of not caring that he can't get a girlfriend.

Cobra met his first girlfriend, Stephanie, at Job Corps and started dating April 20, 2012. Unfortunately, most videos around the time of their relationship have been lost because of his YouTube account at the time “gothickingcobra52” being banned for nudity. He lost his virginity to Stephanie while at Job Corps in the bathroom, clocking in at a solid 2 minutes and 46 seconds. Cobra states he recorded the act on his iPod, but lost the video.

He has admitted several times to have cheated on Stephanie, and she in turn cheated on him. While Cobra has never went into much detail in his own videos, there are recorded Discord calls of him shedding more light to the subject, claiming that he and a friend were propositioned by a pregnant woman at a gas station to perform sexual acts with her, in return for a pack of smokes.

Stephanie on the other hand, cheated during their relationship because Cobra refused to have anal sex with her. She had a mutual friend who offered to give her the experience she was lacking from her current relationship. Cobra mentions that she “technically” cheated on him first, but the guy only fingered her so he never counted it as cheating, nor was he particularly bothered by it.

She ended up leaving him shortly after cheating on him “for real”, but it's debated as to why the two really broke up. It's no secret they both had their own instances of infidelity, but there are claims that Cobra threatened/joked that he would rape Stephanie to be “more kinky” in the bedroom - which might have prompted their quick breakup.

The two ended their relationship on July 4, 2014.

After his breakup with Stephanie, Cobra found himself in two different relationships, but for very short periods of time. Judy was a quick girlfriend during late 2014 - early 2015, and then he dated Ami sometime in the Spring of 2015 - but they broke up after a single day. There seems to be no proof of sexual relations with either of these women during this time, but it is assumed.

After ending his relationship(s) with Judy/Ami, Cobra now enters the official first dry spell. He went a year without sex, and was very frustrated by this. He was consistently rejected by females he showed interest in, and claimed to be asexual a few times.

In the Post-Wendy's saga, we have a more detailed look into the early years of Cobra in regard to his sex life - or lack thereof. He's sent a pocket pussy by a fan/troll on September 1, 2016. He did not mention the pocket pussy until a few days later on September 4, 2016, claiming he had no idea what it was and that he had not opened or used it. He seems to appreciate the gesture, and expresses how he's been a year without sex, but pretends to be disgusted by the idea of the sex toy he was sent and destroys it on camera.

November 9, 2017, Josh announced on Facebook that his dry spell had finally come to an end[5], but did not say what of-age chick he had been with. Naturally, he did not keep her name a secret very long. He had mistakenly wrote on the wall of his newly acquired female companion's Facebook page instead of messaging her, that he had made it home safely. It was now publicly known that Summer Moon-Roberts had ended the year long dry spell.

The two had a fairly short relationship, breaking up just a little over a month later on December 12, 2017. Summer claims her Facebook account was hacked by a troll, and the only photos of her child were deleted from her account. It's hard dating a YouTube celebrity, after all.

The start of the dry spell was marked by his relationship with Summer ending. The two were last together on December 11, 2017 and broke up the next day after pointing the blame to the trolls.

As a result of the breakup and general lack of ability to date women, Josh developed a concerning addiction to Chaturbate, and seems to have no issue exposing himself to anybody that presents themselves as an of-age fangirl. These trends would continue for next 7 years until the calamitous appearance of Jessica Anne "NakedAndLaughing" Boyle.

On February 9th 2024, Josh would go live on YouTube with the stream “Ended my Dry Spell TWU” where he would smugly grin and recount his sexual escapades alongside his at-the-time of-age goth girlfriend Jessica Boyle. The wrath of the bog hag would ensure that this relationship was short-lived, as Jessica would eventually lead to Josh's eviction from the Conquistador apartments. The BPD enchantress would continue to harass Josh on and off for several months until the disastrous Third Visit in August of 2024, where Josh attempted to commit suicide. Clearly, no of-age, consenting, biologically female, alive goth pussy was worth this headache.

With the departure of Jessica Boyle, Josh has once again regressed into his Second Dry Spell ways - Chaturbate, Gender Relations rants, and staying as far away from anyone he considers trolls as humanly possible. It is unknown if Josh will ever score again before his impeding demise.

Josh constantly reaffirms that he is straight, not gay. This has been a running gag in the Cobraverse since trolls began to use his address in Craigslist ads in meetups for gay men and Grindr dates, and Josh has had to leave a note on his door saying “I'm not gay, I'm straight” for most of his time in The Conquistador age.

The best way to describe Josh's relationship when it comes to men is in his relationship with Warlord: While it is clear that he is uncomfortable with an openly gay man who at least partially fancies him, he will still at least attempt to maintain a level of cordial, albeit distanced, relation with him.

Josh will routinely go through phases of being asexual in an attempt to cope with his extremely lonely lifestyle. These typically do not last long, and are often memory-holed once he sees an attractive female.

Josh has a long and storied past when it comes to sex toys. Josh has been sent sex dolls and fleshlights in the mail to assist with his dry spells, and will go through a fairly clean-cut cycle with these objects: Josh will get it, he will say he doesn't need them, he'll use them anyway, Josh gets disgusted with himself for using the toy, and he'll subsequently destroy it, sometimes in an especially ghastly manner.

After Josh's Xvideos account was discovered, Josh's taste in adult entertainment was exposed to the Cobraverse - Most of his interests revolve around lesbian porn, and any adult content that does not feature a penis in any way. Presumably, Josh is so straight that he refuses to even look at another man's reproductive organs, or he's associated looking at them with a certain traumatic experience.
Josh also seems to have a fart fetish, as during The Gothic Dee Feud a Trole would send Josh a video of a goth chick in spandex farting, to which Josh simply replied “Damn, that was kinda hot”.

Given the nature of many of his videos, including “the secret video” during The Gothickingcobra52 Saga where he would masturbate to completion before talking as he did in many other videos uploaded to more mainstream uploading services, Josh is something of an exhibitionist. This can be further exemplified by the fact that he let Jessica make a sex tape of the two of them.

Speaking of Jessica, it is at least alleged by her that Josh enjoys choking his partner during intimate relations, although this was said post-breakup, making it hard to discern if the statement is true or not. It does fall into fashion with many more claims Josh has made over the years, especially given the destruction of Fun Sized Felicia.

A few other minor fetishes seem to include black hair, fishnets, and cam models in general.