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It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back....It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing her panties to work, painted my toenails, and she even did my make up. We did break up, but I still kept in touch with her. I did tell her about my plans for Halloween. Then I slowly started to ease it out. I could see that Fay was having to use some force to keep her in place. Slowly the bulbous part began to appear forcing her anus to expand. Then I let it sink back in. Again I pulled it out, a little further this time. When I let go it plopped back in of its own accord. On the next go I pulled until it reached the widest part and held it there, allowing her time to get used to the feel. I reached between her legs and began to caress her clit and she began. More

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