Moving East

I’m one of the boys; I’m one of them who live in my eastern English town of Witches’ Elbow. We’re all real tough nuts, living in the moment and ready for anything, be it a good tear up or a dirty woman in a back alleyway. Or sex with a man if the chance is there, coz I’m a six foot three transvestite originally called Harry who loves to wear women’s clothing.      

My mates’ cat call me Big Boy when we’re at work but out on the town in my gear my name is Gertrude. They’re a bunch of easterners who were suspicious of me at first; I soon won them over when I walked into work in one of my sister’s dresses sometime ago. A long flowing number made of silver silk, hugging my body in the right places leaving little to the imagination. I gave it my best, doing a slinky walk and showed a bit of my hairy unshaven leg. What a storm it created! “Do you like what you see ladies? I’m young free and single. Come and get me, do what you want to me,” I teased, tossing my purple wig and looking over their heads, being aloof.

“Oh my fucking Lord! Harry is a fucking bird! He’s dressed like a bint! I don’t believe it!” laughed Ian, my boss. His cigarette fell out of his mouth in amazement and shock.

“Well, well, what have we here then? A right sight for sore eyes,” chuckled Jon, the new teenage apprentice.

His gaze held me a little too long. Is he gay? I’d love to find out, I wondered. I pranced about the small tea room before we started work, with no cares in the world.

“You’re quite sexy for a bloke in a dress,” guffawed Liam, nudging Ian and laughing out loud like a man possessed.

“I see I’ve got your attention my comrades in arms. This dress belongs to my sister; she looks even hotter than me in it. But for now, you’ll have to make do with me. Am I enough for you? Please be kind to me,” I humbly said, looking down. I waited for their replies.

“A real beauty you are, a real beauty. Show us some more leg!” replied Jon, acting beyond his years, in the presence of older men.

“Just for you, my dear,” I commented, dancing over to Jon and fluttering my eyes at him. I lifted up my skirt and showed him some leg, a bit too much! I saw his eyes bulge like snooker balls. And another bulge appears in his jeans.

“I’d love it if both you and your sister were here,” shouted Ian, punching the air. “You look ravishingly sexy by the way. See you at my place at nine?” he added, grinning madly.

“Yes, I’ll join Liam and we can have three in a bed,” said Ian, nodding. “As I’m in charge of this work detail, I get to go first! Not bad for a northern monkey”, he added.

“Oh yes Ian, you can go first. The rest of you can fight it out, bitch to bitch on who gets me next!” I whispered. In one quick movement, I undid the clasp that held the dress up. It fell to the floor and I was totally naked, except for my size twelve steel tipped work boots! You should have seen my mates’ faces!