My First Time Being A Sissy

My family was gone for a day last week, so I decided to try some sissy stuff for the first time. I've only ever had girlfriends, and never actually had sex, but I jerk to gay porn a lot. As soon as they were gone, I closed all the windows and got completely naked. I walked around the house for a while, just fantasizing and swaying my hips like a sissy would. I then went to my parents room, and found my mom's sexiest see-through panties. She's in her late 40s and very curvy (she'll be the topic of a future post), didn't know she had anything so slutty. I slid the panties on, and then put on one of her bras. Her tits are amazing, 38DD so the bra didn't exactly fit, but I posed in the mirror and thought I looked quite sexy.
I decided that if I was going to look like a sissy, I should act like on too. So I found my dad's lube, and smeared it inside my asshole. I've put fingers in there in the shower, but never had any actual lube, so it immediately felt like heaven. I went and found a silicone spatual with a nice smooth handle, and put a towel on the floor. I took off the panties, and found some gay bottom cumming porn. Then, I lubed up the handle, and slowly penetrated my ass. It felt so good I immediately got hard, but then I tapped my prostate and oh god, it was bliss. I sped up my thrusts and watched my 7-inch erection shrink back to a flaccid 3, and start dripping precum. The sounds my ass made were so hot, as I violated my most hidden place. Unfortunately I didn't sissygasm, but I did eventually jerk with the spatula in my ass and came extremely hard. I'll have to try again sometime, maybe with a real cock!