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shemale

“Are you a shemale?” the sweet, dim boy asked me as he sat down at the next table in my favorite coffee house.  Taking a sip from my still-hot triple-shot mocha, I theatrically licked the whipped cream from my upper lip as I put the cup down. 

“That’s ‘transgender woman,’ Honey,” I said wearily.  Red faced, he turned away in shame.  Damn – he looked so delicious, too.  But that offensive terminology is such a turn-off.  There was only one way to fix this situation for both of us. “Why don’t you finish that coffee and we can go for a walk?”  His ears perked up, and as tight as those skinnies were, I could see that his ears weren’t the only thing.  Gulping down our drinks, we were walking out of the place in under five minutes.

It was obvious he was embarrassed at saying something so offensive that he was afraid to speak at all, so I took his hand and squeezed it.  “Its OK, Baby. You just didn’t know.  Ask me anything you want to know.”  Most girls like me shy away from talking about our realities, but how will people know if we don’t choose to educate?

“I’m sorry I said ‘shemale’”, he said, a little louder now.

“I’ve never actually talked to a male-to-female before.  When did you decide to become one?”  Squeezing his hand hard enough that his legs seemed to buckle a bit while we walked, I just smiled and said, “Maybe we should hold off on the questions for now.”

Getting back to my place, I invited him to sit down while I made some coffee.  Setting our cups down on the coffee table, I took the spot next to him on the loveseat and lit a cigarette.  “OK, Honey.  First of all, I didn’t choose to be trans; I was born this way.”  He apologized again and was looking even more flustered than back at the coffee shop.

I usually don’t conduct my lessons in such a personal way, but this called for extreme measures.  Besides, he was rock hard and staring at the rising tent in my skirt.  Moving his hand up my leg, I said, “I’m a girl – a real girl, just like any other – except for one teensy detail.”  As I said, “teensy,” I pressed his palm against my dick.  Sweating nervously, he smiled.  “Teensy?”

And that, Loves, is how the boy who asked me if I was shemale ended up spending an otherwise unremarkable morning gagging through a highly informative lesson on gender nomenclature.  He was grateful to be educated, but there was no way he was prepared for lesson #2