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This entry is different from the others i have posted. It is based on fantasies i have had around being caught being dressed when i was younger, developed while chatting here. The people in it are (mostly) real, but the events aren't. So much the worse for reality.
i was 15 when the idea of dressing up like a girl first crossed my mind. It was at my sister's school play; she was playing a fairy and i so wanted to put on one of the tight, feminine costumes. Just thinking about it made me hard, and it was not long before i tried it out, first putting on my mother's bra, panties, girdle and tights, and one of my sister's party dresses. i had a blinsong orgasm, and never looked back. As my sister grew up she wore sexier underwear, and i moved onto that. And my Mother's bikini.
My mother had a sister, Annie, who lived nearby. She was younger and although she was married to a nice man (who i think was having an affair with my mother) she was a bit of a nympho. She went for rough men, builders or plumbers who did work for her. A couple of times we visited her either just before or just after she was fucked by one of them, and even a virgin like me could sense (and smell) the sex in the air. She also wore sexier clothes than my mother, showing off her tits (even to me), with black lace undies which she left in her bathroom. i remember fingering the smooth material, sniffing the smell of her cunt mixed with the perfume she wore. One day i sat on the toilet in her house and could not resist sniffing at a pair of her lacy panties, rubbing them against my cock, putting them on..i was so busy i dodn'y notice her standing in the doorway, watching me with a wicked smile on her face..
i was so embarrassed. "They are nice, aren't they?" Annie said. "Why don't you keep them? Our little secret". i did, and wore them every night.
A fortnight later her husband and my mother went to a concert together, and Annie suggested that i spend the night at her house.
i cycled over. On my arrival, she asked me how i liked her panties. i blushed. "Did they make you feel sexy, little girl?"
"Y..yes" i stammered.
"Come upstairs" she ordered. i followed her to her bedroom, where she ordered me to strip, then showed me how to shave my body, She kept calling me a girl, which made my little cock hard.
"We girls are going to have a good time tonight" she said, laying out matching red satin bra, panties and suspender belt, all decorated with black lace. i put them on, marvelling at the way my maculinity disappeared as my cock disappeared into the panties, as my shape changed when she filled out the bra with stockings, helped me smooth the stockings up my own legs (the feeling almost made me cum then and there). Then she helped me into a tight, short red satin dress which clung to my body, leaving my shoulders bare. She put a shoulder length blode wig on my head, and made my face up.
The doorbell rang.
"Just in time". She let in a large, rough-looking man, the builder i had seen her flirting with. He looked at her hungrily. "Alan, this is Jessica, my..niece" my aunt said. "She's here to join our party".
Annie put a cushion on the floor. "Kneel here, Jessie". i obeyed. Alan came over and stood in front of me. i could see the erection in his trousers. Annie took my hand and ran it over his flies.
"Undo him, Jessie" as if in a dream i pulled down the zip. She moved my hand inside, and i could feel the heat and hardness of his cock. Annie freed it, and the huge thing sprang out, in front of my face. Annie took my hand and moved it along the cock. i could feel my own cock stiffen as i stroked. Alan sighed.
"Kiss it, Jessie" Annie said. i moved closer, and Annie pushed my head closer until i felt it against my lips. i gave the tip a kiss. Then he grasped my nose, and i opened my mouth involuntarily. He slipped his cock inside my mouth, them took my head a forced it down until i had it all in my mouth.
"Now suck, Jessie" Alice whsipered in my ear, and i did. Alan started to move my head up and down until i picked the rhythm up, feeling the hem of my dress ride up and down my stockinged legs. Feeling a mixture of shame..and excitement. Behind me Annie stripped down to her underwear, her hand buried in her cunt, watching me give her boyfriend a blowjib, dressed in a slutty short red dress.
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