First experinented with frilly things as a child. I read somewhere that nearly all boys go through a crossdressing phase, which can last from 1 minute (trying on one female thing) to 3 weeks. A few stay with this 'hobby' for much longer.
This was an on/off thing until I started dating girls - was a late developer.
First sex at 21 was underwhelming. Female genitals could not grip as tightly as my fist.
Was very immature and kept breaking up with a wonderful girl, because making up was fun. I was an 8 year old pulling pigtails in the playground. I broke up once too often.
Was part of a loose group in my firsr job. Slept with a girl and she was pregnant. I'd assumed she was on the pill, but you HAVE TO ask.
We got married. For me, brought up Catholic, there was no alternative.
The marriage wasn't great. We didn't communicate well. She found comfort in another man's arms. I tried for 5 years to rescue our doomed marriage, but it ended.
I was alone and felt emasculated. My obsession with frilly things from years earlier returned. Online shopping and Internet chat arrived.
I posted some lingerie pics and was messaged by bullies, who demanded that I give up my life instantly and go fo live wirh them as their sissy slave!
Then I got chatting to a more patient man, who charmed me over a period of months.
I still saw actually meeting a man as completely out of the question.
But we did meet. Just two men, dressed as men. We went for long walks, only rarely mentioning my crossdressing.
He gave me something to wear on our next walk. A very nice bra and panty set. Seemed very expensive.
I wore just the panties. There was a flash of annoyance from him, but then charm again.
A few weeks later, we were in a park and he groped me, pulling at the bra and panties. He had bought me two more sets and I always wore one of the three.
Online he would get me to look at lingerie and other female clothing and tell him which I liked. He told me to buy some Black Opium perfume and always wear it when we met.
I blew him in a field some weeks later. Once you take a cock in your mouth, you are a cocksucker and can never undo that fact.
We had sex. It was my best sex ever.
He became very controlling. No more gifts, just instructions what to buy and when to wear it.
He asked me to blow his friend, with him watching and filming. I reluctantly did.
Then he gave me a speech about how I would become his prostitute and he would be my pimp.
That was to much. I ended it all. He went mad, saying that he would expose me.
He didn't. We have no contact.
Now just occasionally I meet with men or fellow sissies. COVID put a stop to that for a while.
location
Munich, Germany