T-Girl’s First Time: Popping the Cherry on That Back Door Pussy

Every girl remembers the first time she lost her virginity. Even though I am not a traditional girl, I am no different. I was nervous too. Girls are worried about making a mess when they pop their cherry. No girl wants a guy to see all the blood that usually accompanies the first time, nor does she want to endure the pain that is rumored to come with losing one’s virginity. My traditional girlfriends talked about doing things to prep themselves for their first time. So when I was ready to pop my cherry, I tweaked some of the advice my girlfriends gave me to fit my unique situation.

I bought a big dildo and began using it on my ass so it would not be quite as tight. Every day for weeks I fucked my ass for hours with my special toy. I was afraid of shitting myself  when the guy I was seeing popped my cherry. I read about enemas, found a video online, and decided to make my own coffee bean enema. I was too embarrassed to go into a drugstore and buy a pre-made one.

The day before I planned on letting Ryan fuck me, I gave myself a homemade enema so my ass was cleaned out and I would have no embarrassing accidents to ruin the moment. I pretty much just drank water until I met him. After our date, I told him I was ready. He was not prepared. I had been stalling him for months. I told him I wanted him bareback in me. I mean, he didn’t know I could not get pregnant. We had to do it in his parents SUV in the back seat as we had no private place to go.

I was nervous for lots of reasons. Would it hurt? Would I make a mess? Would he realize I was not 100% female. I was in school still and only a few teachers and friends knew my secret. I fit in as a girl. Anything else I was a freak and I desperately wanted to fit in, but I could not avoid the first time forever. I had him take me from behind to hide my cock. It was dark. I had inserted all sorts of lube to make my ass feel like a wet pussy. It was his first time too so I figured he would have no baseline to judge.

It worked. He slid his hard cock in my back door pussy for the first time, popping my cherry. It felt so good. Better than I could have imagined. I don’t know if it was because I prepared myself for the first time, or that I was just meant to have cock in my pretty back door pussy, but I started fucking all the time. Soon my secret was out. But so many guys had fucked me and they didn’t want folks to know they had been with a T-girl so they kept their mouths shut. Now I don’t hide who I am. I am proud of my duality.  Proud of my big throbbing cock.

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