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Posts Tagged ‘crossdressing’

Last night my wanker played a major part in one of my dreams. We met in real life in a waterfront hotel room with furniture around the edges and a large amount of space in the middle. He was chuckling and delighted when I made him put on women’s clothes: shiny low-heeled patent pumps, almost-frumpy suiting (loose pencil skirts, blouses and polyester jackets) and wigs that all came from my own (imaginary) collection.

Crossdressing is not his thing, but he looked very cute, donning one outfit after another, handing money over to me with each costume change, and not at all as silly as I expected. I was surprised and excited both by how coyly he looked at me in his lady garb through the strands of fake hair hanging over his glasses AND by the stack of twenties growing fatter and fatter in my hand.

I walked across the room — quite a distance — to count the money with my back to him, looking over my shoulder to shoot smiles of encouragement at him. Just as I noticed with pleasure that he’d made a handwritten notation on each $20 bill — his name, the date, and a charming code indicating his humiliated status in relation to my status of financial and sexual dominance — the dangerous wharf gang boys were about to bust in to disrupt me taking control of two new modem/router combos I desperately needed for my networks. They intended to sell them on the black market. If they would rough me up for this pedestrian technology I knew they would rest this thick, hard wad of personalized cash from me in a second and I just couldn’t bear to part with it.

The hotel was located in the same building as a weird FedX/UPS warehouse. Before I knew it I was running through the warehouse between forklifts trying to sign shipping receipts and get my modem/router combos before the wharf gang boys did. I don’t know what happened to my money, but I think I saw my wanker walking away from me down a shady dirt road in a red skirt.

I’m guessing it was about $5,000 but I’m not sure since I’ve never held that many twenties in my hand before in my life and I couldn’t concentrate to finish counting them in my dream.