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I sat with him and we had a few beers as he was nervous the entire time as to whether it would be worse if she stood him up or seen him and wasn't interested because she hadn't asked him for a pic nor did he send her one. Hours went by and it was already 1:30AM and still not a sign of her existance. He was beginning to fall asleep when I went into my bedroom and got into girl mode. I slid my feet into tight nylon knee highs and laced up my black heels. Denim skirt, pink designer panties and red lipstick. Blonde wig, heavy makeup and an all black t shirt. I remembered and made sure to shave close as possible the night before so I could ready myself quick as possible. My friend Matt was knocked out on the couch as I looked through the hallway touching myself. Oddly enough he's never had sex before and I've never had sex with a man. In a sense we would be taking each others virginity if I or him didn't completly freak each other out. As scared as I wanted to just go back into my room. “Wow,” June exclaimed, “has he done this before?”“Yes. I mean, no.”“Which is it? Yes or no? If I even think you’re lying to me, your spanking will be even more severe.”“Yes. Shep did lick me there once before.”“I thought so. Did you have an orgasm?”Gayle started sobbing again as she answered, “Yes, mistress. Please don’t think I wanted it to happen. I am so ashamed.”“Why? It happened. I’m pretty sure it happened more than once, didn’t it?”“Yes, mistress.”Are you embarrassed because I saw it?”“Yes, mistress.”“Don’t be. Relax and let it happen. Has Shep ever mounted you?”“Oh, God, no. He tried, but I wouldn’t let him.”“I told you that you would be humiliated. This is an example of how you will be humiliated, and I want to see how well you handle it. So far, you are doing good, so don’t screw it up. You will still have to be spanked for disobeying me, however.”“Yes, mistress. I know, and I’m sorry.”“Good. Now let Shep finish. I will let you prevent him from mounting you this time if he.
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