" Thanks, I guess." The grip on his cock had Kent building, building, until he began pumping cum up Penny's ass."Oh, fuck Penny. That feels so good." ... can feel it. Wow." Kent held himself in place letting her ass squeeze out the last drops, then he was gone and Penny felt empty. "OK, all homesty, I might do that again." Cool!" They took turns in the shower then dressed for the first time that day to walk into town. Unimpressed with the tourist shops they took the ferry back to the mainland.. But I didn't see a living soul, and I climbed into the wagon, unlocked the gate of Wimpy's cage, and slipped inside--nervous and excited as bell. I felt like a virgin bride on the way to the slaughter.I heard him sniff and stir as soon as I closed the gate. Then I just stood where I was and called softly to him. "Wimpy- Wimpy."I could hear him shuffling around and then he came lumbering over to me in the dim light. I began talking to him as I always did and held out my hand to him. He sniffed. So she suggested I dress in some of her clothes. I didn't want to disappoint her as she had been so kind to me so I agreed but it sounded fun as well. Everything worked out fine in the end although there were a few heart-stopping moments and my nerve nearly gave out a few times. The next day we were due to go shopping with Liz and somehow Rosy talked me into going out as Deedi again. Since Liz seemed to be happy with the idea that's what we did. The rest just seemed to follow naturally after. She told me tomake eye contact with every person looking at me. She explained that atthe motel I would not be able to hide from the staff, other maids orthe guests, and instead of hiding it, try to project as a woman. Shetold me that the next man that looks at me, I was to flirt.Shocked, I said no. She gave me a glare. She said that I needed toaccept the fact that I was a sissy and humiliation was a big part of myrole. She said that either I would flirt with a man driving by or wewould stop at.
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We just made it to the house just as the rain was starting to pour down by the bucketful. I thought this was a fitting end for our first “Date”. I
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