When I was lucky enough to find a melding of the two, I would blast my biggest loads from masturbating. I hated wanting something so specific that I thought I would never find in real life. There I was celebrating alone at this club I'd never been to. There were trannies, drag queens, and gay guys everywhere. There I was drinking alcohol and trying to enjoy music that was too loud for my tastes. I turned and caught eyes with a beautiful crossdresser. She was like something out of a dream. I wondered how long she'd been coming here, I wondered what her name was, I wondered what her cock looked like... Ha, I wondered everything and was so afraid to even smile at her. She sat beside me and I offered to buy her a drink because what's the point of drinking liquid courage if you're going to waste it? Surprisingly she asked for some fruity concoction that only a girl would order. I, as a man's man, was drinking straight vodka and chasing with beers. I complimented her on how she. “Oh yes I’m so ready Miss Caroline. I want your cock in me, I want your spunk. I need it now.” With that, she pulled on a condom probed at my ass with her very erect cock. She teased around my anus, putting the tip into my ass gently, then withdrawing it. “Well here it is then bitch.” With that, she slowly inserted her cock. The was some pain to start, but once she had got the head in, that subsided. “Oh that’s a beautifully tight hole Candy.” She probed deeper. I trembled waiting for the intrusion of her cock. The pain became excruciating for a moment. She had to probe three or four times, then she was completely inside me. She stopped at that point to enable me to recover. My breath was coming a short gasps, a combination of pain, extreme pleasure and achievement that I had taken her whole length inside me. Once Caroline was happy that I was now comfortable she started to rhythmically fuck me. Oh my god the sensations that I was experiencing were like nothing before. She soon began.
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