My second time was with an older crossdresser - I was staying at my parents' place in Bexley while they were away, and on the chatroom of TV Chix when a local popped up who I'd noticed before - as he was unable to accommodate, I'd never paid much attention other than perving over his pictures (great legs in nylon). He was looking, and I was in a rare position to accommodate, so made contact...

We spoke on the phone shortly afterward, and we both sounded nervous... we agreed on some things though. While I was also interested in, and indulged in, crossdressing, he made it clear that he only liked meeting with guys, and wanted to be the girl in the situation. There'd also be nothing anal on offer; that was all fine for me - I was still starting out, afterall.

He arrived looking like a normal guy in his fifties (which he was - I was still about 28 at this point), and hurredly retreated to a bedroom to get ready. I had a nervous wait for a few minutes while he transformed into a lovely looking MILF by the name of Gemma, wearing a short, tight black dress with black stockings and 4 inch heels, topped off with a brunette bob wig and well-applied make up. We sat together, not quite sure how to begin...

We talked for a while, as I recall, about how difficult it was to walk in her shoes, before my hand was guided onto her thighs and we began to kiss. This started escalating fast, and we were soon taking turns sucking each other, me naked once my robe had fallen away, and her with her dress hitched up and panties pulled aside. I came first, in her mouth - she told me afterwards that I was the first who had ever done that. I began to immediately feel that things were over for me, but didn't want to disappoint, but what had started as a desire to suck her and swallow her cum had scaled back to a hand job, leving her to cum all over my hands and her stomach. She was loud when she climaxed, and after she'd left, I noticed that the window had been open and was very hopeful that we hadn't been heard by the neighbours!

She left quickly after a quick change, and we parted on friendly terms, although never met again.