My first time
So I have always found myself attracted to cock, not necessarily to men, but cock. And I always thought to myself, "It sure would be awesome to be a woman". When I would watch porn I'd always fantasize about being the girl in the scene. Then I discovered trans porn, then sissy porn and was like "yep, one day I'm doing that".
Well, eventually that day came. I had posted an ad on Craigslist, back when they had personal ads, I had pics posted where I was wearing my mother's thong bikini lol, the whole nine yards. I got so many guys that responded, but one only lived like 10 miles away, he was 45 years old, and an absolute stud. For someone who wasn't attracted to men, I was attracted to him. So we set up a date for me to come to his house.
My little 18 year old self went out and bought Nair hair removal gel, a cheap little panty hose set, a little black thong, and I took a pair of my mom's high heels. Got all dolled up. Didn't have a wig but I had long, curly hair back then so it worked. And then I went to his house.
He let me in, and I was nervous as hell. I shed my protective layer of normal clothes and stood in front of his man dressed in probably the cheapest lingerie money could buy, and he absolutely adored me. He was touching me in ways that I had never been touched, kissing my neck, squeezing my nipples and ass. I, in that moment felt so loved and adored, it was honestly the best feeling I've ever had.
He led me to his bedroom, where he got undressed and I got my first look at another man's cock, already hard, and hard because of me. At that point I was completely immersed in the woman that I was pretending to be. All sense of my actual self was gone, this female character i was portraying took complete control. He sat at the edge of his bed and I crawled to him, got between his legs and just started sucking his cock like my life depended on it. Feeling him throb in my mouth and hearing him groan in pleasure because of me was the best feeling ever.
After about maybe five minutes of me sucking his cock he told me to lay on the bed and spread my legs, so I did. He started eating my ass, a sensation that I had never felt before, but I was lost in ecstasy. After he got my ass nice and warmed up, he lubed me up, then lubed his cock and boom, stuck it in me. At first it was extremely uncomfortable, but he grabbed my legs, but them over his shoulders and went nice and slow. Then he started sucking my toes while he fucked me, before I knew it my ass was just accepting his cock, I was moaning and just making the most girly noises ever. I was begging for his cock and his cum. He would lean down and kiss me, he told me how beautiful I was, all while just plowing my ass.
Then his paced quickened, I saw the look in his eyes change. He was about to cum. The primal look he gave me was the sexiest thing I've ever seen a man do. Then one big powerful thrust and I felt my hole get flooded with this man's cum. I never felt more alive and loved than I did in that moment. He leaned down and we kissed for a few minutes while his cock was still inside me. Then he pulled out. I felt so empty without him in me. But I also felt just so incredibly gorgeous. I was a woman in that whole period of time.
Me and him would have normal "play dates" for a bout a year after that, then sadly he moved away. I've had other encounters but none like the ones I had with him. Where I truly felt like a woman.
I know its a long post but I hope yall enjoy the read.