A fantasy that’s about to become reality

I’d already had a few experiences with men as Julia, but I could count them on one hand, and none of them were comparable to what I’m about to tell you.

I was flirting with a guy, a little over forty, and we flirted by email and sometimes even over video chat. We got along well. He was always full of compliments, and you know how that makes us weak when we hear things like, “you’re beautiful, you’re sexy, you’re feminine.”

During one of our frequent Snapchat calls, he told me that the previous weekend he had hired a street worker to get off. I asked him a lot of questions to find out what it was like with a professional. To be honest, he confessed that it was really without feeling, and that it just came down to finding holes to empty himself into.

But the details he was telling me about the sex session in the hotel started to turn me on, and he sensed it. That night, he suggested we do a hot video session, and I accepted. During our session, we fantasized about what he would do to me and how he would do it if he had picked me up on the street, and I loved it. After he came on video, we talked, and I told him that I wanted to play that role for real. He was thrilled, of course. I specified that I didn’t want money and that I would prefer he meet me in a hotel room, not on the street. I also told him that I didn’t want to do anything without a condom. Of course, he was excited by the idea and told me, “You have to strike while the iron is hot.” He asked if I was free the next evening, which I was.

Not even 5 minutes later, he sent me the reservation confirmation for a room at a Formula 1 hotel located halfway between our respective homes.

That was it, he had paid for a room. I couldn’t back out now. So we said goodbye and arranged to meet at 9:00 p.m. the next day. He specified that I could go whenever I wanted, because the room was mine from noon until 10 a.m. the next day. I can’t even tell you how mixed my feelings were. Impatience, fear, and excitement all blended together at the thought of this first time.

I decided to pack my bag with the necessities and I took possession of the room around 3 p.m. Getting there early allowed me to take a good hot bath to relax and prepare.

I spent a long time in the bathroom. I had brought what I needed to make myself smooth and have skin like a woman’s. I took my time taking care of myself.

As for my outfit, he had asked that I only wear bottoms, a garter belt, and a bra, with my brown wig, of course. So the dressing session was pretty quick. He had asked me to have my rear end ready for use as soon as he arrived, so I put in a plug and a lot of lube.

I had brought a makeup bag and I started watching makeup tutorials to look like a porn star. After spending 30 minutes trying to get a porn star face, I looked more like a slut, a prostitute. To be honest, I’m not very good at it, but it would fit the context perfectly. I took out the plug that had dilated me well and made my tranny pussy an orifice ready for action.

The fear and excitement were building because his arrival time was approaching, but I didn’t want to chicken out.

The “client” uses my mouth

As planned, he sent me a text message to tell me he was in the hotel parking lot, and as we had agreed, I unlocked the door and got down on my knees near the bed. He finally arrived. He slammed the door shut, didn’t say a word, and came to stand at my level. He lowered his pants and his underwear and said, “Get to work, Julia, suck my dick.” It was the very first time I was meeting you, and it didn’t start with embraces and caresses, but that’s what we had planned.

I brought my tongue close and began to lick his balls and take them into my mouth to massage them. With my hands, I ran along his shaft to make it hard. It was warm and, most importantly, it was quite wide. He asked me to get him hard because he was waiting to be hard before he put it in my mouth. I felt it harden between my fingers and on my tongue. I loved it—being in my lingerie, on my knees, getting this man hard. From his jacket, he took out a condom which he gave me, telling me to put it on him and then suck him. I opened the package and slid this second skin of plastic onto his shaft, then I opened my mouth and he rammed it inside. I sucked his cock while kneading his big balls. His penis was the widest of all the ones I had used as a lollipop. His sighs showed that he liked it, so I continued with more vigor.

Then he put one foot on the bed and took my head firmly, and he started fucking my mouth. I didn’t have to make any movements, just stay still with my mouth open. He was pounding me, holding me with force, shoving it all the way in. He would pull out frequently to let me breathe before starting to pound my mouth again. It felt good to just let myself be used.

After about ten minutes, he pulled out, took off the condom, and told me to close my eyes and my mouth. I knew what he was going to do—he was going to spray me, and it would be my first facial. He started to grunt like a bear, and when he said, “Here, take this, you slut,” I felt thick squirts land on my forehead, on my cheeks, and my nose. It was very hot and very pleasant. I took a lot of pleasure in offering him my face so he could empty himself on it. I asked him with a mischievous look if he had liked it, he said yes, but that it wasn’t over. He took out another condom, put it on, and asked me to lie on my back on the bed, with my head hanging over the edge.

After my mouth, he takes my “pussy”!

He positioned himself above me and plunged his cock into my mouth again. He resumed the cadence and used my mouth and my throat like a cunt. He wasn’t holding back, but I liked it. I was in my lingerie, my face still covered in cum, having my jaw dismantled again. He was trying to get it deeper and deeper, which made me drool a lot. He was still hard. I felt that he was still taking up a lot of space in my oral cavity. He had been using my lips for at least 5 minutes when he told me, “Julia, I want your ass, your sissy pussy, get on all fours.”

I positioned myself as he asked, and he spread my thong before ramming his entire cock inside without any gentleness. Luckily, I had made myself “ready for use,” otherwise, it would have hurt. I felt his hands on my hips, holding me firmly, just as I felt his balls tampon my crotch. I heard the sound of his body slapping against my butt cheeks. I felt his shaft pounding at the bottom of my pussy. He was powerful, I loved it. He wasn’t paying attention to me; he was just fucking my ass, just as he had fucked my mouth. The cum on my face had dried, but the smell intoxicated me. I was in heaven. Fucking me like that, for so long, made an incredible pleasure rise within me. I wanted to cum, being fucked doggy style in that seedy hotel. And I came. For the first time, I came like a woman under the assaults of a hard column of flesh. I was moaning, I was squealing while some juice was evacuating from my boy’s cock.

I must have been making too much noise, because he put his hand over my mouth, and I continued to cum, but in silence. He didn’t stop; on the contrary, making me come had made him even more bestial. I was being anally sexed like never before, and my orgasm didn’t stop. I thought I would die of pleasure. After about ten minutes of making me moan with his cock deep inside me, he pulled out, took off his condom, and asked me to get on my knees again with my eyes closed, which I did. I heard the movements of him jerking off and waited to receive his cum. He again yelled, “Here, here, here, take that, you slut!” as he unloaded on my other cheek. He was still generous with his cream, and I felt several spurts crash on my sullied face. He asked me not to move. I heard him get dressed and leave.

When I opened my eyes, I was alone in my hotel room, my jaw sore, my little ass pretty wrecked, and my face covered in his cum. On one side of my face, it was dry, and on the other, it was still warm and dripping. I could no longer stand on my legs. I quickly wiped myself with the sheet and slipped into bed. The shower could wait until tomorrow. We hadn’t talked or kissed. I had just been fucked, and I was quite proud of myself. I was reminiscing about what he had done to me when I received a text from him that said, “You were perfect, I kiss you, next time we’ll make love.”