I regularly dress up for my partner she loves me with painted toes, panties and a nighty....Tho i try to reaffirm my manhood and take control (we have a switch relationship) i always revert back to my sissy nature and jerk off to cuckold porn.
I painted my toes and removed some body hair the other day and she knew she was getting to be the boss for a few days, she made some comments about never seeing my porn so I saved some sissy and cuck caps and showed them too her.
She laid of some clothes, told me i was not to jerk off tomorrow and she went off to the bedroom to masturbate and go to relax (I often relax on the couch) I followed behind her a few minutes later to try and get my dick wet.
She allowed me to play with her tits while she masturbated and played with my cock when it amused her...after awhile i coaxed her into riding my face which lasted a good hour, where she wouldn't allow me to touch myself, she sucked and jerked but never enough to get me off.
Once she had enough she got off my face jerked my cock and made me tell her about other men fucking her, and isn't it cheating (that's always been her concern) I said its only cheating if i don't approve of it, and i went on to explain how she could make me watch, lick her clean, eat her while she is fucked.
she jerked me off until i came all over my chest and wiped her fingers of my face...i feel like she is about to take the next step very soon.
I sit here writing this hard as fuck in panties and a nightgown with pink toes and happy as fuck, here are a few of the caps/pics i showed her