Crossdressing journey

I say buy it, wear it, enjoy it! I am older (70) and I know I would never pass for a woman. But that’s not what wearing lingerie is for me. I love the feeling of satin or nylon against my skin. It makes me feel feminine and submissive…I have never been with another man (married too long) . But my wife begrudgingly accepted my fetish and I am okay with that.
Like PinkOanties4me, At 69 and recently remarried, I have aged out as well, and purged everything for the last time, but I do have some fond memories, reflections and observations on my years as a closet bisexual crossdresser:

Prep time for dressing to host vs. dressing for self-pleasure varies by about an hour…
Your heart pounding when you first reveal yourself dressed to someone for the first time…
The secret satisfaction of seeing your partners arousal as he looks you up and down, from your wig to your boots….
Waterproof lipstick lasts longer, but it’s a turn on to see your lipstick on the cock you are pleasuring orally…
Pulling my wig into a ponytail to keep the hair out of my mouth when going down - and the “Oh crap!” moment when the guy you’re blowing inadvertently grabs your wig off your head…
Getting the cum stains out of that nice black turtleneck before they get crusty!
The fake eyelashes that end up down on your cheek during sex….
Thigh highs are the better choice than pantyhose if you are bottoming while dressed…
Reaching back to hold on to your 4” heels while performing a “hands free” blow job…
The cool breeze on your back side as the skirt gets flipped up and the panties come down…
Becoming so comfortable wearing heels that you forget you’re wearing them... until you take them off...
Although I have moved on from all of this, I still have years of memories and experiences to masturbate to when the mood hits me….! It was all a lot of fun, and I have no regrets!
 
Done it a little for another boy in school. I would also get dressed and go to this area at the city lake. Got braver and braver and would walk around. Nobody really seemed to notice. It felt great. After I got married my wife loved sex. We got to doing threesomes. One guy made me his sissy and I had to start wearing dresses. Wife loved the kink. We would go places on the weekend sometimes with me in a dress. We would go to Dallas or Tulsa to meet our guy with others and I would go dressed. He required it. We went to Dallas and I didn't take a single boy clothes. It was good for the mind though knowing I had no way out. I dressed as a girl a lot through my twenties and thirties. A few local people even knew about me.
 
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