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His one transgression in his early teens was in the orphanage when he was found by a nurse hiding down in the basement when everyone else was out playing sport. He was dressed in a pair of snagged pantyhose and nylon panties he had found discarded in the female staff dressing room. He wore a sarong and a t-shirt with rolled up socks pushed under the t-shirt to imitate breasts. He's combed out his shoulder length hair and painted his lips with red crayon and lined his eyes with a fine tipped black marking pen. The nurse had berated him but kept the incident a secret.In university he shared a series of flats with other students and would dress up in his bedroom when no one was home; always with the door securely locked. He lost his virginity at eighteen to a female student and liked the sex enough to work his way though half a dozen girlfriends before he graduated. He never linked his crossdressing to sex and although he tried to influence to get his girlfriends to dress in a style. ” I heard Jack say.I turned around and saw a middle aged guy with a beard in the doorway with Jack. He smiled at me, then made his way over and took the buttplug out of my ass.Jack took a seat by his desk in the corner of his bedroom. The guy pulled down his jeans, revealing a huge cock. Not as big as Jack’s but still pretty impressive. He spat on his hand and rubbed his cock. Then he spat on my ass. Without any warning he shoved his cock in my pussy.I screamed in pain. He forced his cock deeper in my ass and began fucking me hard without mercy. I gasped and moaned as his thick cock filled me up. I look around and saw Jack filming everything, stroking his huge cock as he did it. The stranger grabbed my hair and fucked me violently. I was in a state of pleasure and pain. All I could feel was my ass getting ****d whilst the sound of the stranger’s moans filled the room. The stranger didn’t last too long until he pulled out and shot his warm cum over my ass. He spanked my ass, thanked.
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