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This is a question Cross Dressing

The last time I wore a skirt was not as liberating or exciting as it could have been. I'd lost a drinking game and had been given the task of running from the bar, across the road and back again whilst wearing a friends clothes as a forfeit.

Easy, I thought. I hadn't reckoned on them getting every person in the pub to block my way back to the bar whilst I was outside. I had to FIGHT my way through. And I'm not much of a fighter.

Your own thoughts on cross dressing for fun, pleasure or profit are most welcome.

(, Thu 15 Mar 2007, 15:05)
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Themed Fancy Dress Party
I once got an invitation to a fancy dress party, where the theme was cross-dressing. I decided to be witty and only put one of my arms in the armhole of my shirt and act bitter for the whole night, so I didn't have to embarrass myself dressing up as a woman. Surprisingly, I was the only person there with this idea. Unlike this QOTW, where everyone's doing it.

However, I discovered something very exciting lurking at the party -- women in suits. They look so very proper, but you know they're well-and-truly gagging for it. In particular, there was this tall brunette dressed up as a policeman. Her hair looked quite abundant, tied in a well sized pony tail trailing down her slender back towards her shoulder blades, while her black-rimmed glasses sat pleasantly at the end of her nose just in front of a pair of pearly blue eyes. With the policeman's cap cocked playfully to the side on the top of her head, she already had my attention, and I felt my member begin his respect for her authority.

I couldn't take my eyes off of her, and before I knew it I was admiring her tall form. She wore a black jacket, hung loosely around her shoulders, over a gleaming white buttoned shirt that was obviously a bit too small for her. Her large, rounded breasts were pressing heavily on the silky fabric that, like me, looked ready to burst. They were also incredibly firm, as she was clearly wearing no bra and the superlative jubblies stood as proudly and pertly as a head choirboy.

The shirt was tucked into her belted, black trousers that were sitting at the top of her shapely waist, and they dangled comfortably around her long legs. I could just picture the exciting boxer shorts she would have on underneath, perhaps with a jokey picture on alluding to possession of a penis, while all along it not-so-secretly hides her glorious mound of pleasure. Just looking at her, I ached to know her. Somehow, after a good few cocktails and glasses of wine, we got chatting.

Her name was Lucy, and as she talked her nose wiggled in a surprisingly buoyant yet curiously attractive way, while her small, spongy tongue eased the syllables past her luscious red-lipsticked lips. Surprisingly, she liked my outfit, as it advertised my burly figure and she had no interest in chatting to a bunch of "ill-adjusted cross-dressing freaks". I took this as permission to compliment her on her outfit, and I did so commenting on how incredibly sexy she looked. All of a sudden, her demeanour changed, and she grasped me firmly at the scruff of my shirt in a mildly aggressive manner.

"How dare you talk to an officer of the law that way! You're going down,", she said. Then, with a sly wink, she promptly dragged me up the stairs to one of the vacant bedrooms, and threw me down on the bed. She took off her hat and dropped it carelessly onto the bedroom floor, before letting her hair down. The streaks of brown radiant hair dangled over her shoulders and back and she looked purely animal. She climbed on top of me, setting her legs around my waist where my engorged manhood was happily waiting beneath my jeans.

"You have the right to remain silent," she growled enticingly, "but there'll be no chance of that", and she let her jacket slide off her arms and around my ankles, then leant forward and pressed her body against my bare chest, and her erect nipples pressed delicately through her silk shirt into my skin. She kissed me passionately, and I tore her clothes off of her body, revealing her wonderful, white, siky skin and began to kiss it willingly. She took her trousers off, and I saw she was wearing a neat pink g-string, although not for long as I pryed it off with my teeth and pleasured her generously.

Her moans of delight reverberated about the bedroom, and I climbed on top of her. She grabbed me by the waist and swung me around onto the mattress and sat atop me again, eyes fierce like a lion. "I'm the ranking officer here," she commanded as she guided my twitching ardour inside her, "so do as I say. Don't stop until the bed breaks" and she started grinding away ferociously, grabbing her hair and leaning back at the same time, presenting the full shape of her voluptuous figure to me. What followed was the most mindblowing sex ever had, obeying her every desire as she dictated position after position until I exploded my burning ejaculate into her tight lips and collapsed onto the bed, sore with satisfaction.

She stood up and got dressed. She looked at me sternly, and uttered "If you tell anyone about this, I'll see that you get the chair" and walked out, leaving my ragged form tired and broken on the bed.

So, cross-dressing, I'm all for it.
(, Mon 19 Mar 2007, 16:19, Reply)

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