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Its something I wanted, I was worried it would hurt too much but I knew I wanted to feel a man inside me, moreso cumming in me, I understood some guys wouldn’t want this but I joined to meet men that would take my transgender virginity and cum inside me at least for my first.
I had a few messages from guys, some saying they would fuck me silly and have me begging for more, but that wasn’t want I wanted, I needed a gentle man that would take his time and understand that whilst I’ve used toys (often) its not the same as a man behind you pushing his cock into your virgin ass..
I had a message from this guy called Iain, a nice guy and straight away we got on and it wasn’t long before we arranged a date and as he knew what I wanted I said we could meet round mine. I got dressed in sexy little summer dress and with makeup and making sure I was smooth all over I was ready for him.
My First
Iain was just what it said on the tin LOL…nice guy, gentle and after some small talk and drink we went into the bedroom as he knew what I wanted…We kissed, but I wanted Iain’s hard cock and pulling his trousers down my lips were quickly around his hard cock sucking and licking him..
I so desperately wanted him inside me and dropping my summer dress to the floor I was standing almost naked other than tiny panties. I turned towards a chair and pulling my panties to one side I gave him a dirty FUCK me look..
I pulled my ass cheeks apart and spreading my cheeks further exposing my anus as Iain comes towards me, standing in front me I suck his cock taking him fully to the back of my throat as he pulls away looking at my ass, he takes the lube and squeezes it on my anus and fingers..
He slips first one finger inside me working the lube then another as I try to relax feeling more cool gel go inside me, then I feel the head of his cock against my anus as he moves his cock around teasing my hole and ass circle around and around on my virgin hole.
TransWoman Virgin
I felt him starting to push in and my hole expanding, he felt a lot bigger than any of the toys and plugs I had been using but I’m sure that was just my imagination, but he kept moving, pushing into me slowly so I could adjust to his cock inside me.
At first it felt like he was going to rip me open and then he was fully inside with less pressure, and I could feel his cock pushing up into me. Iain held his cock still just letting me get used to it, then I started moving a little which was all the sign he needed and started pulling back, then forward.
He was getting faster and faster and now all the tight pain had gone and was loving the feeling of taking my first anal fucking and now all I wanted was his cum. Iain started to moan and quickened his speed pumping all the way in.
I could feel every bit of him inside me, almost like he was in my stomach, then with one thrust he started cumming deep inside me holding his cock deep in me. He pulled out and commented on my gaping and cum dripping from me and looking around at the mirror I was able to see a little and it looked so fucking sexy, I just wanted him back inside straight away pumping into me.
Iain was my first, was he, my best?. No, but he took things slowly and since then we’ve met again and its a lot more passionate plus the other males, although no more bareback thats just how I wanted my virginity taken
