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spurgeonryan said:

A guy at my work (african american) has chicks with dicks and guys with boobs on his phone.

 

There are guys who like pegging and cuckholding.

 

If you are gay in this day and age, why hide it?

Pegging = guys who like B&D/S&M from a woman.  It's not an afinity for sex with other men.  It could have begun by a girlfriend fingering him while he ejactulated.

Cuckholding = A guy who lets his wife sleep around.  Often watching it.  It doesn't mean that they don't have sex.  His interest is in seeing his wife get used or pleasured.

An affinity for transgendered persons could be a number of different things, with homosexuality being the most likely reason.  However, for any of number of reasons he may not feel comfortable coming out.  Transgendered women ("chicks with dicks") are a way for him to experience one desire while keeping up appearences.

Why does it matter to you?