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I had been introduced to pegging when I was in my senior year at high school by an older woman who happened to be our neighbor. She loved fucking me when I wore her sexy lingerie and acted like a slut. Almost every week I found myself on my knees or on my back taking her rubber cock. She loved playing the masculine role and many a time dressed up like a man as she fucked me. It turned me on so much to see the gender roles reversed like that. It made me feel vulnerable and submissive, just like a woman and I came hard every time.Alas, once I moved to college, it became increasingly difficult to find a girl who would share this fetish with me. I did have a few casual encounters with women I had met on the internet, but none of them ever dressed up in masculine clothing.As I reached the bar, a drag queen approached me and asked me what I would like to drink. I ordered a Manhattan and stood at the bar as I eyed the people inside, trying to see if there was someone who caught my eye.I. She squeals as I had to stretch her a bit further to get it In the top was tapered also so it was easy to get in. Ohhh she moaned from the cold steel. Her ass closed around it. I took a picture and showed her. Omg daddy my asshole is open. I’m gonna leak! I pulled her up to her feet. How’s it feel?Heavy she laughed. Walk around is it comfortable? Yes daddy Cum pouring out of her hole down her legs.This will stretch you to except my cock baby! Oh daddy thank you. And you can put stuff in me easy she giggled I gotta clean all that cum out, get on all fours! Yes daddy. I put the head of my cock and piss into her ass. So warm are you peeing in me? Yep! Ok daddy after I finish I pulled her up. Piss pours from her ass. Daddy I have to pee. Ok pee you don’t need permission. Her cock so tiny it runs down her balls and legs. A few days of wearing her plug and she could finally except my cock with out too much crying. 2 months later I could fuck her any time with little lube. 24 months later I.
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