My First Encounter with a man who Loves Crossdressers

by Bill D (Spokane, WA)

Joe was on the back Pages. He said he likes men who dress up like girls. I've been dressing in secret for years. Beginning when I was 10 or so. Mom's girdles and bras were always my favorite. But then I began to wear my older sister's underwear as well. Now I'm older and have a pretty good inventory of sexy, girly clothes.

Even a couple of dresses. I've also collected some Halloween costumes. I have a maid's outfit and a sexy schoolgirl too. I've always dreamed of being manhandles when I'm dressed. And my fantasy finally was going to come true!

Joe told me to dress in the schoolgirl outfit and send him photos. I did my best adding knee high socks and cute little pink tennis shoes. He liked the pictures very much so he ordered me to drive right over to his apartment. He texted me his address and told me to not be late. I don't know why I liked him being so dominate and demanding. But I did. I followed his orders and rushed to the address. Inside the apartment he grabbed me, wrapping two leather handcuffs around my wrists. He began kissing me.

Kissing me a lot. I was getting really nervous being in a strange man's home, being groped, squeezed and kissed so roughly. I was alone and helpless. I was dizzy and afraid. The feeling of the handcuffs around my wrists was new, and scary. I told him I wanted to go. He told me I didn't. I agreed to stay. As he tightened the wrist cuffs and locked my hands behind my back, he told me I made the right decision.

He enjoyed taking many photos of me. I was posed in different stages of undress. Some showing my sexy black lace underwear peeking from under the schoolgirl blouse and skirt. He soon had me in a dog collar and ankle cuffs. The photos continued with me kneeling below him as he stuffed his cock in my mouth.

It was very humiliating and embarrassing being photographed and video taped sucking a man's cock. I was flushed red with embarrassment. After he blew his huge load in my mouth and all over my face, he dragged me into the bedroom where he had more bondage gear waiting.

In just my and bra and knee high socks, I was spread out face down on the bed with straps pulling my arms and legs out to the four corners of the bed. He used a washcloth to gag me then wrapped some tape around my face and head to hold it securely in. He said he didn't want to alarm the neighbors when he fucked me like a whore.

He squirted pink jelly lube all over my ass and poked 3 probing fingers in to get me ready. I was squirming and trying to cry out. But secretly, I loved it. He gave my ass a few good hard swats. I tried to scream but I only could muster a muffled "Mummph!" As he gave me one final spanking he slipped his cock between my wet, slippery cheeks and popped my tight little butt cherry.

His hands reached under me squeezing my 'tits'. He pinched my nipples hard as he slid in and out of my virgin hole. I felt just like a poor, helpless school girl on a very, very bad date. He whispered dirty things to me as he fucked away. I was his cock slut and bitch whore and that sort of thing.

He untied me and let me use his shower. But while I was in there he joined me, pushing me to my knees and throat fucking me again. This time he wanted my finger up his ass while I sucked. I pushed it all the way in, then he came like a freight train. He told me he would prefer to keep my chained and collared and have me there forever. But he said he didn't think I'd agree to all that. As I went out to my car I was thinking about it. Silly me!


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