Although she wasn't into having sex with woman anymore.Soon we were looking online for the right guy to have fun with. We found Alan who was coming to town on business the following week so after exchanging pics we agreed to meet him at his hotel lobby. We were both very nervous all that day. Jo dressed very provocatively in heavy makeup, a button down blouse with the top buttons undone, a short black skirt that allowed a view of the tops of her stockings and the bottom of her garter belt. She wore no panties so if she sat just right you could see her beautiful moist pussy. She'd dressed like this before and always give a good show to an unsuspecting waiter. What a turn on for all. She finished off her outfit with a pair of 4" come-fuck-me-heels. So, dressed to kill we went to the hotel lounge and waited for Alan. He arrived shortly after and we head up to his room. Jo, being nervous, wanted to get right to it. She unzipped and let her skirt fall to the floor. Alan's eyes lit up as. Maria said she was a woman trapped in a man's body wear as I was just a regular guy who liked to wear a dress on occasion.Some of the gals in the office even looked forward to giving Maria a wedding shower after she fully recovered from hir sex change operation. The irony here is I was the one who talked hir out of having the operation. And soon after that we broke up. Maria said s/he needed hir space to decide what s/he really wanted.That gave me a chance to play the victim card to the full. I even brought myself to tears. "I don't understand, why s/he changed hir mind," I'd sob."There, there, Lori," everyone would say, "These things just happen."Debbie was one of the ones who made made it allot better. The challenge was how to hide the fact that I would pop a woody every time Debbie gave me hug. That's the last thing I needed to show through a tight fitting dress when I was at work.Meanwhile it was now six weeks later. I knew if I ever had a shot at asking Debbie out it was.
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