That was until one day I got chatting via a gay dating website with Brian a 58yr old guy who as it turned out wanted to purely pleasure me, he wanted ...o be sucked and wanked but he did not want me to fuck him. This seemed reasonable to me, and after a few more chats we agreed to meet, we arranged for him to come to my place and fuck me there. It was during one of our chats that brian asked me something that no one else had ever asked before, he requested that I crossdress for him if would be. I looked at myself closer.The blouse left little to the imagination. He would easily be able to see the size of my chest. I purposely wore a conservative, full button down blouse during the first drawing session out of the embarrassment of drawing a nude man. I'm sure he was able to see that I had large breasts by the size of my large bulge, but he was not able to see the slightest hint of boob. This time was just the opposite. The blouse wasn't only small, but it was also well worn after too. "As you said please, how could I refuse your request," he replied withthe confidence well endowed men naturally had. "Pay attention to my ballstoo and make my cock rock hard because this time I am going to fuck youlike you've never been fucked before."I didn't fully remember the following thirty minutes. When he first drovehis cock in me I was hit with a rush that almost made me loseconsciousness and turned me into a writhing pleasure machine that meteach thrust of his with one of my own. I. Few people [statistically speaking] were still healthy at her age, let alone energetic and beautiful. She was one in a thousand. She was unique, fabulous, and funny. I enjoyed every moment with her, the old woman lit me up. At the same time, we both knew our relationship was hopeless.Even on the flight over, I wasn’t sure if I was doing the right thing. I had 3 months before school started again. Were we both being foolish, wasting our precious time? Ava needed a man who could be there for her.
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