I Could Really Use Some Extra Money (Part 1) - Sex Stories

I Could Really Use Some Extra Money (Part 1)

Boy, I could really use some extra money, I was thinking as I walked over to George’s for a Saturday visit. Maybe George would have some ideas. I arrived at George’s house. He greeted me once I was in the house with a kiss while he squeezed my ass cheeks. I loved the way he touched me. I’d known George for two years, since I’d started mowing his lawn. I lived with my Mom. She was a d***k and paid me no mind; I might as well have been living alone. But George had taken a keen interest in me from the beginning. We got some coffee and sat down to chat. After awhile, I brought up my money concern. “Well, I do know how you can make a few bucks, but it would be this evening and we’d have to pick up a few things… but no, it’s probably nothing you would care to do anyway.” “What?” I asked, leaning forward eagerly. “I’m having a little get-together this evening with five or six gentleman friends. We were going to play cards. But I have an idea for some entertainment for them. How’d you like to be a stripper?” “Wow,” was all I could say. I’d stripped for George alone, but in front of a bunch of his buddies? “Being dolled up and stripping for you was fantastic, I was going to suggest we do it again, but in front of a bunch of strange men, I just don’t know.” “OK, think it over, but quickly. We would have to go and buy you a few things to wear. I know just the place to go.” I started imagining doing this. It would be really naughty, but what a complete turn-on and adventure it would ...

... be. “OK, I’m in, but I’m gonna need a few drinks beforehand to give me courage!” “Great,” exclaimed George. “We’ll make a stop at the liquor store while we are out.” “Where are we going?” “Let’s get going and I’ll explain in the car.” We left and he explained that he knew a guy, an older drag queen, who had opened a store that catered to crossdressers and transsexuals. I blurted out, “I couldn’t. I’d be too embarrassed to shop. I feel nervous now just thinking about it. I don’t know…” “I have something for that,” said George, and he handed me a small gold pillbox. I opened it and saw some little round pills. “What are these?” I asked. “Valium,” replied George. “Take two now. The drive is an hour easily, and you should feel quite nice by that time.” I gulped down two of the pills and said, “Boy, I hope they work.” “They will,” said George. Gradually, as we continued on, the pills kicked in. We were almost there now, and I was feeling very relaxed. There wasn’t a tense muscle in my body. “Are we good to go now?” asked George. “I think I’ll be ok,” I replied. We pulled up in front of George’s friend’s shop and parked. In the window were mannequins dressed in sexy lingerie and elegant outfits. I started getting a hardon. We headed in and George introduced me to his friend, who used the name Nicole. George explained our mission and Nicole told me to look around and find what I’d need. First, I looked at all the panties, and settled on a pink pair with ruffles all around… very ...