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I'dnever have gone on my own.-After that evening I didn't see Tess for a week. Things were pretty muchnormal for me. I worked at home, usually wearing a short skirt and tighttop, changing only when I tidied the house. I didn't do anything aboutmy mayoral campaign and I had almost forgotten about it till Tess rangme Friday. I was tidying the house in my favorite maid's uniform."I've got some amazing news," she said. "A guy has promised me a hundredthousand dollars for your campaign..."My jaw dropped. Why would a complete stranger give me a hundred thousandbucks? I'd secretly hoped that Tess would end up raising only about 25bucks and the campaign would be off. But a hundred thousand? That'senough for a small campaign, leaflets, radio air time, TV commercials,... This was serious."He's a crossdresser and a multi-millionaire. He said he was only toohappy to contribute. I might be able to get some more out of him if Iask him nicely. I've got Felicity booking time on the radio and. " Ok, well we can make do I thought. I told her it would be OK, and then she blew my mind and said "We could try anal, although you are kind of big, I am willing to try." I almost shot off right then. She got some lube out of her bedside drawer and got into the doggy position. Her ass was incredible, and tight. I started just by lubing it with my index finger. Slowly working my finger n and letting her get used to it. Then I added another. Then three. She was responding well and even had a small orgasm as I finger her ass with one hand and played with her clit with the other. Finally it came time. I lubed up my cock and worked the head into her tight sphincter. I paused and then pulled out. I did it again and went in just a little deeper. She was grunting and I asked if she was OK, and she said yes, it felt weird but good. After what seemed like forever I had my balls resting on her pussy and my cock buried in her ass. I told her to set the pace and she did. She started slow but soon.
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