About me, I am a 46 year old trans Woman, just at the start of my gender journey. I've identified as bisexual since my late teens, and suppressed that for the last 25+ years as I am in a monogamous relationship. The lockdown gave me time to reflect on my life and face some truths about myself, which gave me the courage to come out as bisexual to my friends in spring of 2021, and as a Trans Woman in the winter of 2021. I am still happily married.
This story is about my first sexual experience with a man as I remember it.
The first time I had anal sex was with a man named Dan. I was bi curious at time, and we had flirted a little on those BBS sites and IRC CHAT that people hung out on in the early days of the internet. I was 20 at the time, and he was much older than me. He was experienced, with glasses, brown eyes, brown curly hair, goatee, about 5'8" maybe 180 pounds which gave him a cute little belly and soft brown chest hair.. He had a cute smile with a mischievous glint in his eyes when he did. We made plans for me to go to his house in the afternoon the next day while his kids would be at school. Back then, I was presenting as male, tall, about 6' and 190 pounds, with short dark brown hair. I was fairly skinny with a slightly wider than average cock. I remember being very eager for the next afternoon to come.
That morning, I prepped the best way I had been able to figure out how to do it. I had a large dildo, which was probably too large for me, and a butt-plug. I started by using the butt-plug on myself in the morning to loosen myself up a bit, and then graduated to the dildo once I felt relaxed enough. The dildo was just over 2 inches across at the head (circumcised) and was definitely a situation where it looked much smaller in the package. I've struggled to get it in me more than once, but once it's in it feels so good. It's so big, I can just barely wrap my thumb and index finger around it and have the finger tips touch. After I lubed it up, I squatted over the dildo with with the head resting against my asshole.
I gently began to sink myself onto the monster cock. Once I pushed through the tightness of having the glans of this massive silicone cock entering my tight hole, I was in heaven riding the veined shaft. The head was about a quarter inch larger than the shaft, which was great because I could pull it almost completely out of me but the head wouldn't pop out so I could go as fast or hard as I wanted. Every movement of my hips sent thrills through my body as the 9 inch long dildo pulled out and then was thrust home again. It didn't take me long to cum. Then I went and showered and cleaned up for Dan that afternoon. In hindsight. Dan turned out to be a thoughtful lover and I didn't need to warm up that much after all, but I enjoyed myself, so it was still time well spent.
I showed up at Dan's door exactly on time, showered, shaved, and ready to be fucked. I was in luck because Dan was a top, and I was curious most about being a bottom. After some small talk we went into Dan's room and the fun began.
Dan began by having me lie on the bed, then he undressed me. My cock by this point was already hard with excitement, and leaking precum. As he pulled my boxers down, and my cock stood at attention for him, he grasped it in his hand and gave it some gentle strokes, slowly rolling the foreskin back and forth. Then he leaned down and enveloped my cock in his hot, moist mouth. I am sure he was tasting my precum; he began to gently play with my balls in one hand, while he licked and sucked my cock almost until I came. Dan's head moved masterfully to let his tongue reach every part of my shaft. When he stopped, I let out a whimper, and then he smiled at me and said it was his turn.
