That one time
Just every once in a while we have those moments we don't forget. The first time we tried something girly on, the first time we did something sexy with someone. My journey started a long time ago with curiosity and I have always hidden it. As I grew older and technology advanced I was able to meet other people who had experienced similar journeys as I have.
This story is about one of those times.
I am in my forties at this point and have been dressing secretly my whole life for the most part. I have never presented fem and am very masc in my day to day life. Facial hair, not fit, burly guy.
I had been married, have kids, but those urges have never gone away. I've always found the outlet online and in secret. 10 years ago I had started exploring, I just couldn't help it anymore. Going to ABS and theaters. Had given a few hand jobs and BJ's, but very rarely and it always left me feeling guilty and, to be honest, dirty.
Eventually my marriage fell apart, divorce happened, and ended up in an apartment of my own.
I had a friend I had made online, another crossdresser that had started a new life and started to transition. We have always kept in contact and she's still a friend. She was telling me about a guy she had met and she had some fun with. I told her, that I had never bottomed. She knew I had used a few toys on myself and had a few encounters, but she had assumed I had gone all the way already. She told me if I had the experience she had, I would absolutely love it, and if I had the chance, to do it. She was also the person who convinced me to stop doing all the risky things I was doing out of curiosity and frustration.
So I started on a mission. I joined a few groups and spoke to a few guys. Eventually I met a man I'll call the plumber. That's what he did for work, after all. We chatted over a few days and I learned he was in a sexless marriage and was looking for someone who could be discreet and give him some release. He had lots of anal experience but had never topped a guy and we thought it might be a good experience for both of us.
We decided on a morning before he went to work. I groomed myself, flushed myself, put on some panties and stockings, and waited. When the knock came my heart raced as I opened the door. I answered the door in a t-shirt, panties and stockings.
I barely spoke as I led him to my room and he swatted my ass before I turned around.
I sat in the edge of my bed and watched my hands shake as I unbuckled his belt and dropped his pants. His cock was semi hard, cut, and shaven. I took it in my hand and stroked it a little before leaning over and taking him in my mouth. This was all discussed beforehand so we didn't really need to speak. We were both worried about it being awkward.
He grew hard in my mouth and he pushed me away. This was more disappointing than I expected, I really do enjoy giving head, even if I knew why he did it. He had me get on my knees on the edge of the bed. I started taking deep breaths to relax myself as I heard the cap pop open on the lube. I was very surprised when the next thing I felt was his tongue around my opening. This was a first and it definitely made me gasp. I had to let out a slow breath and couldn't help but moan as I did.
The next sensation was very different. The head of his cock against me. I tensed a little no matter how hard I tried, but he eased in little by little, letting me breathe and adjust. It seemed like minutes passed until I felt his thighs on my ass and he was in me. His hands were all over my ass and thighs. He spanked me a few times as he waited for me to adjust.
When he started to move, the feeling was overwhelming. I had taken a toy that was bigger than him before, but it was so different...alive is the only word that comes to mind. My heart raced and I pushed back against him. He took this as encouragement and started to move faster, then harder. It took my breath away and gave me goosebumps all over. Then he cried out and buried his cock deep and I could feel him pulsing.
Then he was pulling out of me and it was over.
I stayed in my position and just tried to gather myself in. I was shaking all over and my heart was still pounding, my cock was completely soft, but dripping. I didn't want it to end but, at the same time, I couldn't believe it actually happened.
He excused himself to go clean up and I pulled my panties back on correctly and sat on my bed.
He asked if I was ok, I told him I was, but was a little overwhelmed, but in a good way. He smiled and said he was too.
Then it got awkward, didn't really know what to do next so I just sort of went to the door and asked if he had everything. He checked his pockets and nodded, then left.
We messaged a few more times, but he ended up reconciling with his wife and I've never seen him again.
Will be a moment that will always stand out