Back in 1991 I had my only real life opportunity to be with a person who saw me as dreamt I could be.
Back then the internet was an infant and we had these online bulletin board systems to connect (BBS). I was the ultimate geek and spent time online in one which led to a real life encounter that was amazing.
I ended up meeting IRL with a systems operator (SYSOP) who supplied me with alcohol and he and his wife loaded up a computer sex board game. I want entranced and scared as encounters could happen with either gender even if you entered your orientation as straight.
While the game was interesting and resulted in my first time having intercourse with a woman on her period and only the second intercourse of my life at the time, it began a relationship with the SYSOPs wife that was amazing yet brief.
A few weeks later she left her husband for a weekend at friends house and invited me to join her as I had confided my desires to her in a moment of weakness.
Her friend was away and a bit larger. After I got the nerve, I joined her. She stripped, dressed me en femme, made me dance seductively for her and then seduce me as if I were a woman. She lived me and used a tiny vibrator on my rear before I could take no more and had incredible sex all night and all the next day. All that time I was dressed as a female but was always nervous.
It was an incredible weekend. A few weeks later she left her husband for two months and moved in with me and my brother. I gave her room and slept on the couch because my brother would not have tolerated a known relationship with a still married woman in our shared apartment.
In those two months she took me a long way. I experienced anal penetration with a dildo and learned how to pleasure a woman with a lot of coaching. I had long hair, which she had me wear in a banana clip whenever my brother wasn't home. I shaved my body had panties and lingerie to wear that she made me buy and always had painted toes and clear polish on my fingers.
Unfortunately I got scared. She made me an ultimatum to commit to her or she would go back to her husband. She preferred a feminine male by far and wanted me to be her woman. I was too afraid and that was the last time I had a chance to be with someone who could accept all of me.
Nowadays I want a pretty young man for myself on the side but can't find one. If you get your opportunity, don't wait - sometimes you only get the one!
Married but needing more wannabe CD who loves feminine MtF Trans non op and preop
