Birth of a Sissy

At 18 I began to realize that I was curious about men.

I made a post on a personals website that I was looking for my first gay experience. I began flirting and sexting with men for the first time ever. I was in a small town and very nervous about meeting someone I might know.

After a couple of nights of emailing but getting no real results a got my first email from Levi. He told me that he lived in the next town over, he was 40 years old and could host in an hour. I told him it was my first time and I was a virgin. He told me we could take it slow. I decided I could no longer wonder and fought all my nerves and drove to his apartment.

When I got to his apartment I had to wait for him to let me inside. He showed up through the glass door. He was tall, at least 6'4", looked athletic and was wearing gym shorts and a T-shirt. He said nothing to me besides confirming my name and letting me inside. We rode up the elevator together to his floor in silence. I realized there was no going back after I followed him to his door.

The silence was broken as we got into his bedroom, he asked, "What do you want to try?"

"Sucking", I answered nervously. He pushed down on my shoulders and I got down on my knees. I couldn't believe I was about to do this. I was so nervous. I instinctively used my hand to start rubbing the front of his shorts. I could feel his semi erect cock and noticed I was harder than I've ever been before. He pulled his shorts down and there it was. It was beautiful. He was cut, had a nice trimmed bush and was big. It wasn't even fully erect and it was bigger than me. Letting my sissy urges take over I kissed his cock and began sucking.

After a minute or two of sucking he was fully hard and I realized he must be at least 8". I didn't know how to suck such a big cock. I could only get half of it in my mouth comfortably. I kissed the sides and licked it all the way down because he seemed to enjoy that. I could start to taste cum, and he said, "Is there anything else you wanted to try?"

Not thinking about how much larger he was than anything I've had and in a cock lust I confidently replied "Anal."

He helped me up and I stumbled out of my pants. My boxers were soaked with so much pre cum it looked like I had fully came inside them. He guided me onto his bed in a doggy style position. He grabbed some lube and put on a condom.

I felt the cold sting of the lube landing right on my hole. Then the sensation of his finger spreading it around. Then he told me to breath in and I felt something big and warm pushing right up against my hole. I knew it was his massive cock but until I could feel the impact of it on my virgin asshole I didn't realize just how big it was. He kept instructing me to breathe in and out and every time the pressure on my hole increased and then I felt it. A sharp pain throughout my body.

He was inside me. Not far yet. Maybe and inch. I tensed up from the pain and pushed him out. He slapped my ass and then I felt the pressure on my hole again, but this time the pressure subsided quick and he was inside me again. He worked his way in and out slowly. It was so painful. I was doubting my decision making. Here I was being sodomized by a man over twice my age and it was awful, I hate this and then... it felt amazing. He was even further in me and sliding in and out much faster and easier. I started to feel like I was melting around his cock and completely opening up.

He must have felt the change because he said, "You're a natural bottom". The compliment pushed me over the top and I came.

I was embarrassed and said, "sorry", but I also noticed when I looked there was blood by my cum. He could sense I was freaked out. He told me its normal the first time and he left to grab a towel. I didn't move an inch. He came back with a towel. Still hard, but no condom. My ass still up in the air like a dumb slut. He wiped around my ass and the bed. I was about to get up thinking this was over, but instead he slid right back into me. He was ramming his massive cock hard into my ass. He kept going hard until I submitted down to laying on my belly. He asked me if I liked it as he railed me deeper and deeper into the bed.

I mustered out a yes, and he said "good girl" and came inside my virgin sissy ass. I went home barely able to walk, bleeding and with cum running out my ass which now felt permanently gaped. This cemented my fate. This was the beginning of Lori Lux.