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In the early 70s before strap on dildos, my girlfriend had a hung lady friend that was a sexy blond shemale. It was becoming popular for the girls in college to have their boyfriends fucked in the ass while they watched. I shuddered at the thought of taking cock up my ass, but my girlfriend convinced me that she would keep our secret behind closed doors. Her Friend was hot and after drinking a couple glasses of wine, she took me in the bedroom fucking my virgin ass for the first time with my girlfriend, witnessing and photographing the entire scene. To my girlfriend’s surprise, I actually liked taking it in the ass and actually ejaculated during the fuck. My girlfriend sucked her hard in invited her to fuck me on my back this time so she could sit on my face and get her pussy licked. Once I lost my anal Sherrie, my girlfriend insisted I bend over for other guys whenever she wanted to have a show.