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First time sex with a man!

How my first time anal started and happened.
So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person.
At the time I was under the influence and I sent him this message.
"I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my cum/cumming in my mouth all dressed up frequently, so that I will be familiar when someone cums in my mouth; maybe when you cum in my mouth? Or even better how about you cum in my mouth after you fuck my tight little sissy ass? How does that sound? I know you want it. Humiliate me and take away any manhood I have left by putting your hard cock in my ass! I am a sissy and a sissy should have no manhood. But to lose it they need a strong, real man to put their cock in her asspussy. At this point there is almost no man left in this sissy! To strip them of their last manhood they need to be degraded fully by having a man's sperm released into their mouth."

The next day I reread the message and was embarrassed beyond belief that I had sent it! To make it worse we had an ongoing dialogue that night that I didn't remember. Apparently, I had arranged a meeting for us in one week!

I was thinking I need to cancel this, but inside I knew this is what I wanted. I was just too scared to make an initiative, until my true feelings came out when I was drunk. So I decided you have to try anal some time.

I arrived at his place. I was very nervous, my legs were trembling greatly. He invited me into his house and showed me to the bathroom where I could get ready. There was some lingerie laid out for me. A black see through babydoll accompanied by a lace bra and G-string. I smiled and closed the door. I was breathing hard my hands were shaky, and I was just a nervous wreck! It took me about thirty minutes to put all of the accessories, clothes, and make-up on. I felt bad for taking so long but the nerves were getting to me! I stood at the door for about two minutes before finally opening it.

As I turned the corner I saw the look on his face. It was a look of pure sexual arousal and I could tell he was going to be all over me. I tried to strut sexily towards him, but I feel as if I probably butchered it. The G-string was very small, especially with me being fully erected. I finally reached him and he was eyeing me up and down and stopped at my crotch.

He said, "Well it looks like someone is turned on."

I glanced up at him, smiled, and replied , "Sorry."

It was the first thing that came to mind, again I was nervous as hell! He told me don't be sorry and smiled and leaned in grabbing my crotch with his big hands and kissing me. I was not too into the kissing and pulled away. My first thought was I don't want to make him feel like I'm not aroused, so my first instinct was to turn around and bend over. It worked amazingly as he grabbed my hips and began grinding his hard cock on my ass. He pulled down his pants and put the tip of his cock pushing against the G-string right on my asshole. This turned me on so much and I began grinding on his cock, and this is where I knew I made the right choice and wanted to be taken by a man.

I turned around with my precum soaked panties and said, "Let's go to the bedroom and you can fuck me."

We made our way to the bedroom the whole time him groping my ass. 

He pushed me on the bed and said "Suck my cock, sissy."

This was the first time I have ever seen a cock in real life and it was right in front of my face. I saw his precum oozing out of the tip of his cock and I hesitated and just sat there because I was so nervous.

He then said, "I said suck my cock, sissy," and pushed it into my mouth and began face fucking me.

He grabbed the back of my head and was fucking my mouth like a pussy. This was my first time sucking a cock and I was gagging and gasping, but he kept on fucking my mouth. He pulled my head off of his cock and I was breathing hard, spit dripping from my mouth, my eyes a bit watery, and he said good sissy and laid me on my back. He kneeled to the side of me and told me to suck his cock and I eagerly did.

He then pulled my cock out of the g-string and said, "What a cute, small cock you have," and began stroking it.

I guess my cock sucking skills weren't up to par and he used his other hand to face fuck me again. I was gagging the whole time, but my body was in pure excatasy, and he knew that. After he fucked my mouth for awhile he pulled out and I laid there breathing very fast and stroking myself, he knew that I wanted it in my ass.

He told me get to the edge of the bed, get on all fours, and show him my tight virgin ass. Just to be clear I had not done anal play in over a month so I was really tight! He pulled my g-string to the side, licked his finger and shoved it in my ass. He began finger fucking me, he started going faster as he heard me moan.

He said, "I can tell you like it bitch by the precum dripping from your small, sissy cock."

I replied, "Mmm, yes please fuck me." 

He pulled my g-string to the side rubbed some lube in my ass and spit into it. He put on a condom and I felt the head of his cock up against my ass. I couldnt believe it, I was about to take another man's cock in my ass. There was no going back once my ass was fucked, I knew I was going to be a sissy. I could feel the pressure of him trying to push his cock in my tight ass and it didn't seem like it was fitting.

I said, "Maybe you can put more lube and stretch it out more with your fingers."

He simply replied "No," and grabbed my hips and thrust hard into my ass.

I whelped when this happened, there was intense pain in my ass and he asked if it hurt. I told him it did, and he said it will get better and began thrusting in and out. His dominance over me made me feel helpless and very submissive which was an extreme turn on. This mindset really helped because I believe pain is a mental thing as well. It worked, after awhile the pain turned to pleasure.

I began saying things like, "Is that as hard as you can fuck me? Fuck me faster, and I thought you were going to show me what a real man is." 

The last line must have clicked to him because he had a serious response. As soon as I said that he pushed all his weight on me, collapsing my knees; I was laid flat on my stomach unable to move. His cock was going deeper than before in this position.
He told me, "Shut up sissy and take my cock. A real man fucks bitches, you are sissy who just takes cock." He then whispered in my ear , "I'm going to make you my bitch."

He pulled out of my ass ripping the condom off and shoved his cock into my mouth. He face fucked me again and said "You're gonna take my cum in your mouth just like you wanted."

I realized in the email I'd sent that I said I was eating my own cum, but I was kind of lieing. I never had cum in my mouth before. I was unsure about taking a load in my mouth, so I suggested that he cum on my ass. He looked at me and shook his head and continued to fuck my face. I thought, well I have no choice, I guess I'm getting a load in my mouth. I began to move my head up and down on his cock because I was gaging so much when he was face fucking me. I was only going half way down his cock because I didn't like the feeling of gagging very much. He didn't tell me when he was going to cum, instead he shoved my head all the way down his cock and came in the back of my throat. I could feel his cock pulsating as the cum was released into my mouth. I tried to pull back but he held me there until he was done cumming. He pulled out and I was coughing on his cum, I even felt some in my nose. I was breathless and exhausted and fell to the bed. I laid there with my cock fully erect, asshole stretched and opened, and cum dripping out of my mouth.

At this moment, I knew in my mind I was a sissy.

Just an FYI, this is a true story and the cover image is what I was actually wearing during my encounter.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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