My First Time with a Man

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.

I got up as he laid down, and I began to undress him. I smiled as I pulled his underwear off and his cock was there for me. This was the first time I had a cock in my face. I smiled and then leaned down and repaid the favor to Dan, sucking his cock into my mouth, flicking the underside of the head with my tongue, I began to bob my head up and down slowly, listening to Dan moan as I sucked my first cock. I was incredibly turned on, it was so fucking hot to be sucking his dick. To this day, oral sex of any kind is my favorite kind of reciprocal sexual activity. I want to be used. I want a cock deep in my mouth, or a woman sitting on my face, grinding her pussy into my mouth. I could taste his precum, salty, like mine was (I had often tasted my precum and liked it a lot more than actual cum).

Dan was slowly bucking his hips as I sucked his cock, taking my time. He was gently fucking my face and I loved it. I kept trying to take his cock deep in my throat, but was not being too successful due to my gag reflex. The moaning and encouragement from Dan was exciting, I could look up while I sucked him off and could see the expression on his face. Then Dan warned me 'I am going to cum if you keep doing that'. Being the novice I was, and wanting to experience it all, I kept going until a fountain of salty cum exploded in my mouth, almost making me choke. I swallowed it all, and kept sucking and licking his cock until it started to shrink. After Dan had finished, I crawled up beside him and we cuddled for a bit before he told me that he 'wanted to fuck my ass'.

He had me slide down the bed so that my ass was almost off of the bed, then had me pull my legs up towards my chest, which exposed my virgin hole to him. He began with a generous drop of lube on my hole, and then began to work it in with a finger. It felt so amazing having someone else do that to me. He quickly moved on to 2 fingers. By this point, I was rock hard again when he moved into position and placed the head of his cock against my ass, then he gently began to push himself inside me.

'Oh YES!' I said as I gave myself to him. My legs supported by his shoulders, he pushed gently until all 6 inches of his cock were deep inside me and his balls touched my ass cheeks.

Dan moaned and said 'You are so tight!' This surprised me that I would be tight after riding the monster dildo a couple hours before, but I was happy to please him. Slowly at first, but gradually picking up speed, Dan proceeded to fuck my ass. Every in and out stroke of his cock into my ass was thrilling. My cock bounced around as he fucked me, God, it felt so good! I felt a little little tingle of electricity as he hit my g-spot again and again. Before I knew it, he had wrapped a hand around my cock and began to stroke it up and down as he plowed my ass with his member. I was so excited from the blow jobs earlier that I quickly began to shoot a cum all over my belly, time stopped as my whole body quivered with the best orgasm of my life. Not long after that, Dan grunted as he slammed his cock home in my ass and shot his load into the condom he had put on. I could feel his dick twitch inside me, using me, fulfilling my fantasy.

When he was done with me, we uncoupled. Wiping me down quickly with a towel, we laid in bed together and cuddled until shortly before his kids got home from school. I took a quick shower, and then left.

That would not be the last time I was with Dan, and he would also be another first for me near the end of our relationship, but that is another story.