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    My first sexual encounter as a Sissy

    My sexual sissy encounters

    Part 1.

    The first time I met a man was some years ago now. We met online, the usual way. It was my first ever cock as i started my sissy lifestyle. He was a tall black man that was studying psychology at the time. So my first cock was indeed a BBC hehe. I wore a school uniform (pic below) for him, with hi heels, blonde wig, full make up, smooth all over and my sissy clit was caged. It was during the cold dark winter months. After making contact, we set up a meet. It was no bullshit just straight down to business, as it should be. So there I was on the night in full sissy attire, waiting in my bedroom with sheer excitement and full of nerves praying he wouldn't let me down. I had dimmed the lights and had an electric fire on to set the mood. I left my front door slightly open so he knew it was the right address. I had told him to come in, walk down the hall and enter the first door on the left. As I lay on the bed he came into the room and closed the door behind him. I was in awe just looking at him. My heart started beating so fast and my clitty started to swell a bit. He was so handsome and big. He then told me how cold it was outside and rubbed his hands together in front of the fire. We didn't chat much apart from a small introduction. He told me to stand up so he could get a good look at me and made me do a 360. He then took his big jacket off and pulled his Jean's down to his knees. At this point I was so excited I dropped to my knees and started sucking his cock. I didn't hesitate and the nerves had vanished. That feeling of actually having a man's cock in my mouth as I sucked him was something I couldn't describe. My first ever cock and it was a big black cock. Sucking and tasting him, I could feel his him grow inside my mouth. It was exhilarating. He put his hands on my head, guiding it back and forth. I remember smelling his manliness. At this point I was getting hard inside my cage, I could feel my sissy clit pointing upwards and leaking so much. As i continued to suck his cock I put my arms around him, laying my hands on his firm ass cheeks, caressing them and giving them a little squeeze. I wanted to embrace all of him and everything in that moment. I remember going to his balls and licking them and smelling them. As I stroked his cock I put his whole sack in my mouth and gently started to suck as I was looking up to him making eye contact. I thought to myself dam I'm pretty good at this and I'm more than just loving it. After a bit with him being fully erect he had me lay down in front of the fire, facing towards it, he took all his clothes off then lifted my mini skirt up and lubed up my sissy pussy which I had sitting on top of the bed with a few toys I had laid out just incase. He then took out a condom and put it on which I didn't even think about to be honest. I was just to excited, ready and waiting. He lay down behind me and made me lift my leg into the air. Slowly he started to work his big cock inside me as he was pressed up against my whole body. I remember the feeling of it sliding in. Like I said it was my first cock and it just felt unworldy. Nothing compared to a dildo. It was hard yet soft and it felt warm. I of course became fully erect in my cage, lying there thinking about the fact I have a man's cock inside my ass and I'm dressed up like a girl and behaving like one. I became instantly submissive and feminine. I noticed my voice changed and my moans lightened. It became extremely natural to behave in this way at that moment. I kept thinking to myself, I really am a submissive Sissy slut. It just felt so right. After he inserted his cock all the way inside me. He stopped and let it just stay in there. He then turned my face towards him and started kissing me, it felt very passionate and sensual. Slowly he began to pull out and then push forward with his hip. I began to feel every inch of his cock going in and out of me. He didnt rush, he took his time. After it was going in and out with ease he took my leg and kept it in the air, he had his other arm sort of under my neck with his hand on my throat. Not choking me but just holding me and he slowly fucked me for a while whilst looking at my face. Then of course, he began to pick up the pace. He was going a lot faster. I was letting out all kinds of feminine moans. I don't know why but I didnt realise just how attracted to his smell i would be. We had been in a few different positions through out the night. It was all very passionate. It wasn't rough fucking or him dominating me like a sissy. It felt like making love. At one point as we changed position I tried to take my skirt off for better access but he said "aww I like you with your little skirt on", so I of course kept it on. I remember one position where we were both sat on the floor with my legs wrapped around his waist and him deep inside me. We were humping and grinding, he wasn't fucking me, going in and out, almost just enjoying being inside me and looking at me. Knowing he was making me his sissy bitch. This felt really hot. It had my eyes rolling to the back of my head. I honestly couldn't believe it was all happening. It was the hottest thing I had done so far. A million times better than any experience I had with a female. Anyways after what felt like a very long sensual session of love making he lay down in front of my wardrobe mirrors and had me lay on top of him so you could see us both in full view. He shoved his cock balls deep inside me again. No thrusting, just pressed deep into my ass. He then asked me to suck his nipple and said each time I give your ass a little spank I want you to change nipple. This went on for what felt like about 10 minutes. He just lay there pressing against me and looking at us in the mirror as I alternated between each nipple at the command of a slap. I was surprised at how big his nipple's were. They became quite swollen after a while of me sucking on them. I knew he was just watching us in the mirror and in that position, honestly it felt out of this world. I became a proper submissive sissy at this point. I was there for his pleasure 100 percent. After that we got up and he bent me over the bed. He shoved his cock inside me in a sort of rougher fashion. He pushed my head down into the covers. Grabbed a hold of my hips quite tightly and began to seriously fuck me. He was pounding away, nothing like before. I was wriggling away, legs shaking, caged clitty flapping away. I knew at this point he was going to cum. I couldn't wait to finally feel a man cum inside me (even with a condom on) pounding my sissy ass I could hear him grunting and moaning. I knew it was any second now and then finally he let out a big manly moan. I felt his cock throbbing as he was squeezing out every last drop. The feeling was immense, i loved every second of it. This was the point for me where my fantasy finally became true in all its glory. I finally became a mans sissy bitch. I had a man have an orgasm while deep inside my body. It truly was mind bending but all in a good way. I didn't have an orgasm but this is okay for a caged sissy. I think I had leaked enough during the session. He then pulls out of my hole and asks where the toilet was. He was in the toilet for a bit but I think he was washing all the make up off that rubbed on to his face. He must have flushed the condom because i have no recollection of where it ended up. Anyways he came back into the room and we said a few words, it wasn't much. We then said our goodbyes and he let himself out. I was obviously in total ecstasy. I had a little drink after to calm myself down and I edged a bit more before finally undressing and going to bed with a swollen pussy and a huge smile on my face. I went through every detail in my mind before falling asleep.

    He went by the name King M.
    So thank you King M for making my first experience, one I'll never forget X

    I hope you enjoyed reading about my first sissy experience. Im going to write up the rest of my sexual encounters and show a picture of what I was wearing Stay tuned xoxo

     
      Posted on : Jan 9, 2024
     

     
    Add Comment
    scudtwo
    scudtwo's profile
    Comments: 5,212
    Commented on Jan 10, 2024
    Very hot! Nicely told.
     




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