I figured out how this can work.

Put the girl on her back 'tits up' and hang her head upside down over the edge of a bed or something. If the dude can spread his legs far apart enough she can probably wear a big hat.

Also other hatted blow jobs might be cool, top hat is obvious but how about that beanie/crown thing that Jughead wears?

I have seen baseball cap.

Military gear would be awesome, like one of those tooth brush crested war helms.

Cowboy 50,000,000 gallon hat.

Wizard hat.

Point being, as usual, things must be made as awkward and stupid as possible.

Party hat.

Wigs do not count as hats.

One of those Australian cork hats that repel bugs would be fucking amazing.

Hey ladies! Put your blow job hats on.

Visors count, like those old timey accountants wear in movies.

Head bands do not.

Pots and pans count.

A indian feather head dress would be perfect.

Bandana is not hat.

I actually own one of those horse riding jockey helmet things. That would rule as a blow job hat.

Silly hats + blow jobs + whores = satisfying.

Does this count?

Thanks Chuck. I appreciate it. Can you tell me where you found that?

That's Gen Padova from my Cum Catchers review. They all start out like that.

I'm checking Gag Factor 21 now, I think the dyke Rick Masters Gag Factored had a baseball hat on backwards.

GF21 review. She looses the hat when she goes tits up, but she has it on when she pukes all over his nuts.

Hey, another GF started with a chick in a fire fighter's hat, Dirty Harry was doing her....stay tuned

Thanks!

I really want to see a super awkward blow job. Thus the sombrero.

EDIT: In "Rocco never dies" there is a girl who wears a baseball cap. They censored it on the box cover because she was wearing a "Planet Hollywood" hat. I assume Rocco didn't have a licensing agreement.

your like a mad...hatter!

Look for a review of Gag Factor 20, including this Aaliyah Jolie scene, soon!

this freshjive ad with raylene was put to good use back in 10th grade.

Does the Sombero theme come with a Dirty Sanchez ending?

juan could only hope.