Gilligan's Island

[SuperSissy]

Stranded with Gilligan and the crew, who would you rather be? I'm more Mary Ann, I think. Approachable, plain and not too flashy, very easy and willing!

 

[Excitabletom]

If I'm going to cross dress, I want to be Ginger! All glam with fancy dresses and perfect make-up!

 

[TheF1x3r]

The guy who lives on the island watching all these pervs getting wild before telling them they're not actually stranded.

 

[SuperSissy]

Yeah, Mary Ann, wearing cute little sundresses, fresh and clean and acting all naive...

 

[ericrodman101]

Being Gilligan would be like being those young guys in porn who play it all naive when their teacher or stepmom comes onto them. And then they fuck like pistons with that dumb Gilligan look on their faces.

 

[SissySalina]

Always thought Mary Ann was the better looking of the 2.

 

[BlackSatinKnight]

Gilligan. During the day I’m clumsy and I ruin all the efforts to escape the island. At night, I’m in one of Ginger’s gowns on my knees in the hut blowing Skipper, the Professor, and Mr. Howell to completion every night.

 

[AllenJames]

I'm actually pretty sure that the Professor is bi - so I'm choosing him! And if a trunkload of sexy clothing lands on the island I'll really surprise the girls!

 

[SuperSissy]

Gilligan. During the day I’m clumsy and I ruin all the efforts to escape the island. At night, I’m in one of Ginger’s gowns on my knees in the hut blowing Skipper, the Professor, and Mr. Howell to completion every night.

Hmm, that sounds like a good plan, too!

 

[BiliBottoms]

Gilligan and being the Skipper's 'cabin boy'

 

[GentlemanJedi63]

I’d be Mary Ann! Of course, I’m still looking for the Lost Island of Gay Men Over 65 to be stranded on! Wouldn’t that be plain heaven? Sun, surf, and cock!

 

[GentlemanJedi63]

The more I think about it, I think I would throw Mary Ann and Ginger in a volcano, then I could wear Mary Ann’s little outfits and be the only girl for the men. Also, when the “headhunters” arrived, I’d meet them at the lagoon on my knees and mouth wide open. I could say that the headhunters “came and went.”

 

[ericrodman101]

The more I think about it, I think I would throw Mary Ann and Ginger in a volcano, then I could wear Mary Ann’s little outfits and be the only girl for the men. Also, when the “headhunters” arrived, I’d meet them at the lagoon on my knees and mouth wide open. I could say that the headhunters “came and went.”

One of the episodes has to be called 'Headhunters'. It's a great pun.