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First Time Anal while Crossdressing

"A true event"

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I wrote this about 20 years ago and thought it could do with a rewrite to add some missing details. I had to pick up my touring caravan from the site in the highlands after leaving it for my pal to use. I left work early and drove up. When I arrived I got the van ready and I also got changed into my fun clothes. Black stockings, suspenders, black lacy thong, lace bra, red blouse and black mini skirt (my sister in laws but that's another story!) I pulled on my trainers jeans and jacket and towed the van down to the town car park. I walked up to the toilet feeling great with my stockinged legs under my jeans. I went into the end cubicle and peeked through the spy hole. Imagine my delight when I see a lovely big cock hard and throbbing. As soon as I saw it I wanted it. This was going to be the day I lost my virginity. We exchanged peeks and passed notes under the cubicle. He would follow me to the car park, yes! I went in to the caravan and pulled the curtains shut, stripped off my street clothes and put on my heels. I opened the door and let him in. I was 40 and married he was 25 single and hung. I pulled him to me, we kissed I knelt down and let out his monster cock. I took him in my mouth but I really wanted him to fuck me. His cock wasnt that thick but boy was it long. I had only seen pics of monsters like this, made my little clitty look puny. I wanted him to fuck me so I stripped him of his clothes. I told him to lie down on the bed and I took down my thong lifted my mini skirt and straddled him. I reached under and positioned him at my tight hole. I had only had fingers up there before so I wasnt sure what to expect. I gently lowered onto him so I could control it. Fuck it hurt. He was 9 in but not too thick. At first I was hesitant, the pain was bad but I persevered as I really wanted it. I slowly lowered and lifted, eventually getting a rhythm going. After a while he began to get going and told me to get onto my hands and knees and took me doggy style. He was thrusting into me hard, calling me his bitch and holding my hips as he fucked me. He asked me for my slut name. I hadnt thought about it as although I had dressed since I was a teen I didnt go for wig and makeup. I thought of the first girls name I could and Eileen was it, I was wearing her mini skirt after all. I could feel him getting ready to cum and then he pulsed into me calling me Eileen, slut, whore, faggot, I loved it, I could feel him twitching in my man pussy. After a bit he pulled out, I could feel my ass squelch, I had finally done it, I'd been taken like a little whore and I loved it. I wanked my little clitty off as he got dressed watching me. He was dressed and had left as I came, remembering how it felt to be his bitch and then licked his juice from my fingers after I wiped my pussy clean. All true. Apart from being bareback, he wore a condom.
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Written by alwayshard

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