My first anal with a stranger

21.7.2019 22:06 anna_CD_

It was about end of May when I got the opportunity to have some me time. I knew that for some time so I started preparing in advance so I could have all my sexy things ready.

I chose to buy everything black.

Tights with a crotch opening for easier access to my pussy-ass, high heels, lacy panties, wig - everything.

My excitement was so big that I could feel myself shaking with the though of becoming a woman completely and enjoying myself.

And as the excitement grew I knew that, the big dildo I was using was not enough. I wanted something real. To feel a real cock, throbbing in between my hands and every single centimeter of it while it enters my ass. The thinking of this situation would make my small cock hard and my pussy-ass gape a little.

So I decided to join here, and started a few conversations and setup my first ever date.

I didn't have a place of my own to host and neither did he. So I rented an Airbnb for the evening.

I let him know what time to meet me and where and the time just flew by, while I was so anxious. On o e hand, cause I didn't know what or who to except since I only spoke to a stranger on the chat and on the other hand cause this would be my first time I'd be getting to feel a real cock.

And I was in for a surprise.

So after we set the time, I started to prepare myself very carefully. Had a long relaxing shower, cleaned myself and shaved perfectly for the date. I wanted to feel like a girl and my man to be pleased.

I started to get dressed. Put on my sexy underwear, tights, high heels, and short skirt he could lift and my wig. I was feeling very horny, just like a little slut.

I had told him that I wanted this date to be very specific and follow my instructions. In return, he could do anything to me. The instructions was that he'd ring the bell, and I would let him in. He'd find a few open doors and then reach my room.

In the room, I had switched off the lights. On the TV there was some porn playing. I was waiting on the couch doggy style moving my ass and legs in a provoking way but inside I was feeling anxious. I could hear him approaching the door.
He enters and greats politely then starts removing his clothes as I'd told him I'm advance. I wasn't talking at all, just sitting there waiting for him to do whatever he wants.

So he approached me from behind and started touching me. It was the first time a men was touching me. I felt like a whore. Exactly as I wanted and expected, a sissy slut.

He puts on a condom and I reach to feel his cock.

There's the surprise. His cock is HUGE. A BIG BIG COCK.

We never make eye contact, he comes on the couch from behind me while I'm doggy style and touches his big cock against my asshole. I spit on my hand and lubricate my sissy hole.

He started to slowly push his cock head inside but it was too big. After a few attempts, he's in. My sissy ass has a real cock inside for the first time, a huge cock and I just wanted him to fuck me in anyway, without stopping. I didn't say anything but I wanted to get fucked like a little whore. And so he did. But truth is it was a little uncomfortable as he was constantly trying to push all the way in, tearing my sissy ass. I could only feel pain, but as a good whore I decided to try and control it while he was enjoying fucking me. I wanted him to enjoy it.

I wish he'd cum inside me so I could feel his warm cum all inside my pussy-ass and then let it go out, and taste it.

After he came, he got dressed and left.
I sat there playing with my destroyed ass and I would become forever a sissy who would crave more cocks.

xxx :)

The stranger mentioned is somebody I met here. Would love to repeat this again. Hope to find more decent guys like. Text me :)

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That would be great time and energy moment for nastie thing.
Lovely story xx
what a great story! thank you for sharing! too bad there was no oral though...