The first time my wife Mistress Leanne dressed me up in sexy sissy lingerie for her lover to use I was very nervous but eventually I relaxed and enjoyed it very much! Made me feel so slutty and made me cum so much and so quickly!
Better yet would be to meet a woman like her but not be dating her. Just be her slave boy toy whenever she calls. She might live down the street from you and you get to talking one day. Next thing you know she has you over for drinks. Then before you know it your drunk and wearing her panties and stockings and taking her boyfriends big ol' dick in your ass for her entertainment.
I have jerked off to this video more times than i can count. I always try to time it to cum when she slips her hand around the bulls waist while kissing him. Its so fucking hot i can barely stand it.