Stephanie’s First Time

Disclaimer: All events in this story took place with people above the age of 18.

*****

It was a Tuesday morning and I had begun my usual routine. I woke up, put on some girly clothes, watched porn, and started masturbating. When I get aroused enough, I would grab my lube and dildo and I would start fucking myself until I cum. It was mostly satisfying, but this time it wasn’t really doing it for me. The excitement had finally run dry and I needed something more.

I had had the same feeling many times, and each time I did the same thing. I put up a posting on craigslist that read “Crossdresser in search of an experienced man for her first time”. It always got a response or two, but the people were either weird or I chickened out. This time was different though. It may have been that I was ready, or it may have been how Paul responded, but either way, it worked.

His response was as follows:

“Hi! My name is Paul and I would like to ask you a few questions if that’s okay? I was wondering first what your name is? I don’t mean your birth name, but your girl name. I see no point in calling you anything else, as I believe that is truly who you are on the inside. I would also like to know what you are looking for exactly. Do you just want sex, an ongoing thing, a relationship? Next, I just would like to know some basic information. How old are you? How long have you been dressing? Height? Weight? I’m 43 years old, 6’2″, 190 pounds. I have a 7-inch penis. Thanks for your time.”

His tone was different than anyone before and it made me feel comfortable. I responded and told him that my name was Stephanie. I was 21 years old, 5’7″, 125 pounds. I told him I was just looking to see where things would go. He responded quickly and asked if I would like to come over. I could bring everything that I need to dress, and that he would even do my makeup as he had practice doing it while he was in acting. He stated that there was no pressure. I decided to meet him.

Nervously I gathered all of my things Ümraniye Olgun Escort so I could head over to Paul’s house. I decided to go overdressed, as all I was doing was getting into my car, driving, and getting out of my car. When I arrived, Paul was waiting at the door to let me in.

“Hello, Stephanie!” He said enthusiastically.

‘Hi, Paul” I responded. He could sense some nerves in my voice and he gave me a big hug once I got up his steps.

“Don’t be nervous” He said. “You look beautiful”.

“Thank you” I replied.

“So let’s get started with your makeup” he continued. Paul brought me into his master bedroom where there was a large makeup station. He explained that he used to help with the makeup on the sets of the projects he was working on and that he would have me dolled up in no time. He was not lying. After a short while, he was done with me. I could not believe the results. I truly looked like a girl, and a pretty one. He had even replaced my wig with a better one that he had. I was unrecognizable. What I looked like as a boy was gone. I was a girl.

The rest of my appearance was perfect for the occasion. I was wearing a black skirt and a white blouse over a fishnet body stocking with breast forms in. My blonde wig and makeup complemented the outfit beautifully. As I looked in the mirror I knew it; I was about to get fucked. I was undoubtedly horny and Paul could tell.

“So should we move this over to the bed?” Paul asked.

“Yes. How would you like me on the bed?” I replied. I felt so sexy that my feminine and submissive nature took over. All I wanted to do was please the man who helped make me who I was right at that moment.

“Face down. Ass up.” He replied. He struck a tone that oppositely matched mine. The friendly and approachable Paul that I had come to know over the past few hours was gone, and the dominant Paul that was going to take my anal virginity was there.

I went over to the bed as instructed and got down with my ass in the Ümraniye Sarışın Escort air. Paul told me I was a good girl as he walked over. He lifted up my skirt. “It’s time for you to learn your place, Stephanie,” he said with a dark tone as he swung his palm onto my ass for the first spank.

He continued the spanking for about five minutes; alternating cheeks and talking dirty. I was so turned on, but I wasn’t hard. My cock was dangling and dripping with precum. “That cock of yours is now a clitty. Do you understand slut?” He asked, spanking me even harder than before.

“Yes sir,” I replied instinctively.

“Good girl. Now stand up.” He demanded. I did as I was told and stood up. Paul grabbed me by the ass and leaned in and started to kiss me. We made out passionately for a couple minutes until he pulled away and started to push my head down, putting me on my knees. “Undo my belt.” He demanded. I said “yes sir” and complied. He didn’t have to say anything else. I undid his belt, unbuttoned his pants, and pulled them down, revealing his nice hard 7-inch cock. “You know what good sluts do.” He stated, and I started to take his cock into my mouth.

It was wonderful how it slid in and out. I had practiced on my dildos in the past but this feeling was different. It was real and I was enjoying every moment of it. Paul could tell I was enjoying it as he kept encouraging me further; telling me to take it deeper. I complied and eventually had his cock all the way down my throat as he held my head in place. “That’s a good little slut,” Paul said as he released me. He demanded that I remove my skirt and blouse and get on the bed with my ass up as before. I, as I did before, did what I was told and assumed my position.

Paul then began to lube up my ass. He applied a generous amount and began to finger me. The feeling was wonderful coming from a real man and I started lean back against his fingers. “Eager are we Stephanie?” Paul stated.

“Yes sir” I replied.

“If you want Ümraniye Şişman Escort it you have to say so,” He said.

“I want it!” I replied confidently.

“Want what?” Paul teased on.

“I want your big cock to fuck my tight ass!” I said wantonly in the girliest voice I could muster. Paul needed no more than that as he pressed his 7-inch cock into my tight ass hole. The pain mixed with pleasure felt amazing as he slowly started in and out. I moaned and groaned as he picked up the pace, fucking me from behind. As he could tell that any pain I had was now turned to pleasure, he spanked my ass hard. “You like that cock baby?” He asked rhetorically.

“Yes sir I love that cock. Fuck me harder!” I replied. That was all Paul needed to start fucking me the way he really wanted to. Long and hard. He was punishing my ass, and I had never felt more like a girl in my life. I was incredibly turned on and Paul could tell. He reached around and grabbed my clitty and started stroking me. He was talking dirtier than ever at this point too. Calling me a slut, bitch, whore, and every humiliating word in the book. It only turned me on more and I came from all of the excitement. As I came he said “good girl”. It all felt amazing, but he wasn’t done. How could he be? He was still inside of me pumping his cock in and out. It didn’t take long for my arousal to start to build again, but it was his turn now. I had been taken care of.

Paul continued to fuck me and I continued to be a grateful slut. He put me in all kinds of positions Missionary, sideways, cowgirl, reverse cowgirl. At one point he had even picked me up and was fucking me standing. It was incredibly hot and more than I could handle as I moaned uncontrollably to my first fucking. When Paul was finally ready, he barked at me. “On your knees whore!” I obeyed and got on my knees. Paul started stroking his cock and a few seconds later he shot a large warm load all over my face. It was amazing and felt like it would never stop. When he finished, he said “good slut”, gestured for me to lay on the bed, and told me to eat as much of the cum off my face as I could.

I laid there in fatigue and pleasure. There was no going back now and I knew it. 20 minutes later Paul came back into the room. “On your knees.” He said. Round 2 and my life as a sissy girl had begun.