diggerman

Drag Queen Jessie's Pokemon Debauchery

Oh who could have seen this coming? I guess when you play with a Machoke's choker, it's only a matter of time before you want it to use strength on you.

Patreon Reward: Stuck in Horror Drag Sketch

Here we have a sketch reward featuring a small follow up to the Halloween drag comic I drew long ago, with the trapped rubber drag desperately yanking and pulling at their stuck rubber costume.

Patreon Pinup 4: Stupid Sexy James

Here we are with our fourth voted pinup a seductive drag queen James hitting on a rather aroused trainer just off screen~

Sissy Nikki

A long time ago, a friend and I thought about creating a "virtual" account of a sissy named Nikki. (S)he would be a joint account on Twitter, Insta, DA and such, posing as a professional sissy and such. Writing personal blogs, likes, flirting with people who interact with her, etc.It quickly...

Patreon Pinup 4 Sketch(es)

Hey folks, so this week Seductive Drag James in Latex Jessie uniform was chosen after a close vote. However, I'm having trouble deciding what that entails exactly. I even reached out to person who suggested it for clarification but have not heard back.So, since I have deadlines to reach, I'm...

Reupload: Horrifying Rubber Queen

This was one of my darker comics I drew for Halloween one year.A poor woman finds herself trapped and stuffed inside an unflattering rubber suit. Her struggles as the suit fills with goopy rubber get weaker as it quickly starts to harden. A flatulating device is inserted into her, stretching her wid...

Drag Queen Jessie and Ma-balls

Oh my, oh my, what has our naughty former Ash gotten himself into now~?

Pinup Poll 4

Okay, I've gotten your suggestions, quite a number of them this week, and have the possible ones down below for you to vote on.

COM: Hot MILF TG

A bit of a preview for a commission of an eager young man turning into a hot older milf woman.

Mrs. Mom Drag

A fun idea I read once involving a certain boy genius's mom (boy that doesn't narrow it down much does it?) turned into a fake boobed and butt drag queen.

Pinup Poll 4

Alright folks, welcome to a new month with me and I once again must thank your for your financial and creative support!That said, go ahead and drop your suggestion for this week's pinup in the comments below.

Reupload: Lewd Undies TF

And here we end the week of Ben with the first Ben TF sequence I drew long ago, and one of the first female to male transformations I've ever drawn.

Patreon Pinup 3: Lewd Rubber Drag Costume

It seems like some (un)lucky girl has gotten into a strange self-applying costume of a rather horny, inflatable drag queen!Sure she can still move around, as her new inflated appendages wobble and sway with every shift, but she'll have to play along and do as her new lewd voice box says if she w...

Bimbo Drag Slut

So while the personal cosplay may not be for everyone, I do feel the need to share at least this last piece which is an upgraded bimbo drag look complete with big fake bimbo lips!Ready to start my new online career, no? ;p

I'm Gwen, I swear! Sketches

I love the idea of girls turning into costumes of their former selves for their new male bodies, and Gwen/Ben is perfect fodder for that type of transformation.

More FemBen Sketches!

Patreon Pinup 3 Sketch

So here's the sketch of what I have so far of this week's pinup drawing.I'll be honest, I wasn't quite sure how to go about drawing a girl stuck in lewd rubber drag costume, but only because there are so many ways to draw it!In the end, I figured I'd tell a story in a way with a ...

COM: Hazbin Drags

Hey folks, today I'm bringing you a just completed drag pic featuring your favorite princess of Hell and her girlfriend now horny and playful drag queens inviting a third into the mix~Background is form the show and was included at the request of the commissioner.

Ben Princess and Gwen Fuze Sketch

Continuing the Ben sketch art, we have another princess Ben tf and Gwen turned into a certain rude and chubby guy.Hey, not all ideas and drawings can be winners. ^^;

Pinup Poll 3

Alright folks, let's get poll #3 rolling with this week's suggestions!

Ben TF Sketches

I don't remember what sparked this sort of tf, maybe because it's FtM, maybe it's he and his cousin are such easy transformation fodder, but either way, I had some moments of turning others into Ben clones.This time featuring sketches of a spoiled brat, a desert rose, and a princess.

Patreon Reward: Drag Nurse Joy

Another Patreon reward pinup today!It seems an adult Ash has really dived into growing his lewd drag costume collection is eager to show off his new latex Nurse Joy costume and look~!Sissy Drag Nurse Joy is will see you now~

Pinup Suggestion 3

Alright folks, last two weeks we've had drag queen Zelda and evil drag queen Link-rova. Let's see what we can suggest for this week's pinup in the comments below.

Reupload: Ben Gwen

Hey folks, I found that I had an unusual number of sketches and art centering on a certain Tennyson, so I figure this week will Ben week, though not exclusively.

Patreon Pinup 2: Evil Queen Link-rova

As per this week's voted poll, we have a drag queen Link, with a twist!After extensive torture, brainwashing, training, and a fabulous makeover, Link is now far more vocal as Drag Queen Twinrova! Tons of makeup/bodypaint and grey wig, he is now Ganon's right hand enforcer, concubine, and sub...

Evil Link Drag QueenRova

So there's some tweaks I'm open to, but I'm thinking an evil drag queen Link would love to dress up as the fabulous Twinrova while he dominates subjects and serves his king~

Drag Joy Sketch

New in the line drag Ash costumes comes everyone's favorite nurse! Look forward to see more soon.

Bimbo Drag Me Cosplay

You know how I often draw my drag queens with too much makeup and lighter than skin tone foundation? Well, one cant help but recreate things in the 3D space and thus my bimbo drag look comes to life.Fake boobs, fake blonde hair, and fake bimbo personality. Nearly the whole package!

Patreon Reward: Persona Sissy

Hey folks, today I'm bringing you one of the pinup rewards for a top tier supporter featuring a couple of Persona characters having a very erotic, but oddly drag time together~

Heather's Degradation Sketch

I mostly do FtM drag queen transformations but I do have a "regular" drag queen OC named Heather who is male through and through.Think of her as the Hyde to Metal's Jekyll. When my self insert needs to relax and unwind in the most degraded way possible, she comes out of the closet to go ...