My first night with a man

My first night with a manThis is the true story of how I lost my virginity. It happened a few weeks ago.It was Wednesday morning and I was sitting in my car after having purchased a new bottle of nail polish at my local Walmart. I nervously hit submit on my phone, reserving a hotel room for later that day. I had made up my mind that it was time for me to truly live out my sissy girl fantasy to the fullest, and to me that meant being with a real man while I was as feminine as possible. I could hardly think of anything else that day, and mostly just counted down the minutes until it was time to leave and check in to my room for the night. I rented a room about a half hour from where I lived to hopefully avoid running into anyone I knew. I loaded up everything that I would be needing for the night and headed out, my mind racing as I drove down the highway. I again became nervous when it was time to check in as I figured the front desk worker would ask me why I was renting the room, but thankfully that wasn't the case, I'm sure she was used to one night rentals from locals. Soon after I was in my room with all my feminine attire and accessories splayed out onto one of the two beds. I had total privacy to get fully dressed and dolled up, getting as pretty as possible for what was to come. I had placed an ad on Craigslist a few days prior, hoping to find someone legit to use me like the sissy slut I know I am. It didn't take long as the first responder was the one I chose. He was tall, had jet black hair with a beard to match. I wanted a man who was totally masculine to offset my femininity. We emailed back and forth up until that night, and agreed to meet around ten at night. I had six hours to prepare and I used them all. First I stripped naked and went into the bathroom where I used nair on my legs and butt to really make them as smooth as possible for him. Once I was satisfied with how hairless I was it was time to get dressed. I locked myself into chastity to begin, not wanting to become erect at all while I was with him to add to the feminizing experience. Then I slipped on my purple nightie, followed by my wig. I looked myself over in the full length mirror adjacent to the beds before laying down on one of them to paint my finger and toe nails with the polish I had purchased that morning. Once I had finished with that it was time to apply my makeup. I took my time and applied foundation powder, blush, eyeshadow, mascara and lipstick. I admired myself in the mirror and took some pics while I waited for him to arrive. At this point it was about nine o'clock and I was starting to get nervous again, hoping he'd like what he saw. As I was taking deep breaths I heard a knock on the door leading outside and I got up, unlocked it, and slowly opened it to see him staring down at me.He came inside and shut the door behind him, leaving us alone in the room together. He hardly spoke but was quick to move close to me, pulling me into his body as he reached behind me and began squeezing and playing with my ultra smooth ass. He spread the cheeks and fingered me a little which caused me to moan very softly. Taking my hand in his, he guided it to his crotch where I felt his stiffening manhood under his pants which I prompltly began to caress. He then backed away from me and told me to get down on my knees which I did without much hesitation. He unzipped and then removed his pants and boxers, revealing his long cock which was semi hard, I began stroking it slowly for a few moments until he took his cock in his hand and put it between my lips. He was ready for me to suck it and I didn't disobey. I started to slowly lick and suck his hardening shaft, making sure to keep a good suction with my lips to really make it feel good for him. I could tell by his moans that I was doing a good job at that. A few more minutes on my knees and he was ready to move to the bed. He layed down and had me get on my hands and knees so that my butt was aimed at him and my head was in his crotch, I continued to give him oral as he squeezed and fingered me again. I felt like such a little slut, being used by a real man for his pleasure only. I sucked his cock until it was at full mast and then he was ready to use my other hole. He had me get in my hands and knees on top of the bed and then got behind me. At first it really hurt when he attempted to penetrate me and I had to pull away. He said he'd take it slow afterwards and began to penetrate me again. The pain subsided for the most part as he began rocking his hips back and forth until he was fully inside me. He picked up the pace and I could hear and feel the slapping of our skin as he began pounding me good and hard like the slut I was becoming. He fucked me in this position for awhile before having me stand up and bend over the bed. He stood up behind me and didn't take long before he was back inside me, pounding away at my gaping pussy. It still hurt some when he penetrated me fully as his cock was rather long. We continued for what seemed like hours as he would pick up the pace and then slow down or stop altogether so he'd last longer. After awhile he pulled out completely and layed back down on the bed before telling me to get down between his legs and suck him again. I didn't disappoint and began blowing him. He placed his hand on the back of my head and forced his cock down my throat until I was gagging. He fucked my mouth for a few more minutes until he was ready to get back inside my well used pussy. Again he told me to stand up and bend over the bed before he got behind me and re entered my wet hole. His legs were on the outside of mine, trapping me there and allowing him to pound me even harder. I was moaning like a whore as he fucked me deeply, completely flaccid inside my cage. It lasted another ten minutes at least until he finally came inside me. It felt very hot as he unloaded into me and he moaned in ecstasy. Once he pulled out I could feel his seed begin to drip out of my pussy and down both my legs. I had never felt so submissive, feminine and slutty before. Afterwards he cleaned himself off in the bathroom and we talked a little as he got dressed. He then said his farewells and took his leave. I stayed in the room for a little while longer, reflecting on my evening of sex with a man for the first time. I had never even been with a woman before so this was the first time I had sex with anyone. I only wish I didn't wait so long but I know it won't take nearly as long next time. I took a few more pics before getting undressed and removing all my makeup and nail polish. I then packed up all my things and left, my night of sissy bliss completed