AnalCD25's blog Profile | Galleries | Favorites | Fanbase | Clubs | Comments | Blog My first Attempt at Being a Sissy During a phase in my life when I wanted to try absolutely everything—well past the age of 20, but standing 1.74 m tall and weighing 62 kg—I possessed the kind of proportions that were in demand. Consequently, I offered my services as a "sissy" on several occasions. That is how I ended up on my first date as a sissy with a 27-year-old bisexual guy in the Wedding district. He lived in a row house and, with his family away for the evening, he had the place entirely to himself. We arranged to meet late that night, at 11:00 PM, near the Gesundbrunnen S-Bahn station. I waited for his car at a nearby bus stop, illuminated only by the glow of the glass shelter. It was quite thrilling; every time a car approached, I wondered if it might be him. Then, he pulled up. I opened the door, and he gestured for me to get in without saying a word. During the drive, he asked me all sorts of questions. He seemed satisfied with my answers; he grinned and remarked that he liked me—he had always wanted someone like me all to himself. I was cautious with my responses, as I didn’t have much experience. He made it clear that his intention wasn’t just to treat me like dirt; he simply wanted to use me for his own pleasure—whatever that might ultimately entail. I suspect even he hadn’t fully worked out all the details himself. We arrived at his place, got out, and walked about 50 meters to the house. "Go ahead of me—it’s around the right side of the house," he said, pointing the way. Once we arrived, I stepped inside his home. He gestured toward a chair against the wall, telling me to put my things there. "Go ahead—start undressing slowly, down to your underwear—just enough so that you still look like a sissy." I stepped forward to the chair and took off my clothes, one item at a time. Meanwhile, he leaned against the window opposite me, watching. Once I was finished and standing there, he took two steps toward me and began to feel my body. He ran his hands along my arms and legs, then took my cock in his hand and explored it. "You like this, don't you?" I got an erection. Then, he gripped my buttocks with both hands, stroked them, and turned me around. "Raise your arms and clasp them behind your head." I did as he said. With visible pleasure, he began to run his hands over the side of my body, my back, my buttocks, and my legs—all from behind. I had a rock-hard erection by now. "Bend over a little." He held my neck with one hand while pushing me forward with the other. Then, using his feet, he nudged my legs further apart. He worked on my buttocks, traced the crack, and reached down to my scrotum—tugging on it firmly enough to make me groan. He then grabbed my entire package and gave it a few sharp, backward tugs. I let out a short yelp of surprise; he let out a brief laugh. That was the "greeting." He then gave me instructions on how I was expected to behave as a sissy. If I wanted to ask him something, I was to get down on my knees and keep my head bowed. Next, he sent me to the kitchen. Guided by his hand on my arm, I walked to the sink, where he positioned me just right. He explained that doing the dishes was part of my duties as a sissy. I had to run the water and wash the dishes in the sink, while he stood behind me. He then began to caress me from behind and reach between my legs. He grabbed my balls again and pulled me back a little by them, forcing me to spread my legs wider. Finding it amusing to assist, he pushed them even further apart—to the point where I could barely manage to stay standing. Then, he bent me forward to get a better view of my asshole. In this incredibly hot position, he leisurely fingered my hole, occasionally pressing against my hips and legs. As a result, my hard "lady-cock" rubbed against my pelvis. This went on for about 15 minutes. Just before I was about to climax, he stopped and asked for a coffee—instructing me to get one from the machine and bring it to him. Without another word, he disappeared into the next room. Once the coffee was ready, I brought it to him. He was sitting in an armchair in his living room, legs spread wide, wearing shorts and watching TV. I waited on my knees, holding the cup. He gestured toward a stool beside him and the carpet at his feet—he had beautiful feet. I set the cup down and sat on the carpet. "You’re a good boy," he said. I replied, "Thank you." After he’d had his coffee, he directed me into an all-fours position that offered a clear view of my backside. Slowly but firmly, he pulled me closer, inch by inch, while I braced myself against the floor with my hands. "Just let go," he said, "show me your...hole”, behave yourself. After all, I was positioned somewhat backwards, leaning over him. His hands guided my hips, just as they had in the kitchen, and his cock pressed against my rear opening. It hurt. He wanted to get inside. After another three or four minutes, I was seated on his cock—forced to ride him in that position. In the process, his cock kept brushing against my prostate. Naturally, that couldn't end well. I just barely managed to keep from ejaculating on his carpet, ending up on my own underwear instead. The pressure from my anal muscles brought him to his own climax. I realized then that he hadn't used a condom—but in that moment, I didn't care. Once his cock went limp inside me, he told me to get up, but to be careful so that nothing would leak out. He didn't feel like explaining to his wife where any stains on the carpet might have come from. He told me to get dressed immediately and leave, adding that I could take the bus to the station. It was an experience, I suppose—but it didn't leave me feeling entirely satisfied...     Posted on : Oct 26, 2026     Add Comment sissyonknees Comments: 52 Commented on Nov 11, 2026 Mmmm your Daddy knew how to train u perfectly to be his sissy bitch. Luv how he kept u in suspense with each order, making u hornier by the second as he spread your legs wider and wider. Your sissy ass pussy spread wide open as his property for his view and use...u rode him like the dirty sissy slut bitch he knew u were. So hot !