One Trick Penny – Chapter 5 - Sex Stories

One Trick Penny – Chapter 5

Tutorial Session It had been several weeks since I'd started turning tricks with my husband, but I was rapidly starting to run into a problem. While trying not to become repetitive, I had to admit I was out of kinky ideas. It wasn’t like I’d had much experience with fetishes and dominance before I got married; none really. Oral was as wild as I’d gotten. I was way past that now. Dave wasn’t much help. I was disappointed to learn that while he enjoyed our raunchy sex, he wasn’t all that inventive. The burden seemed to fall on me. Even his porno collection was relatively tame; a prospect most wives would be thrilled at, but in my case, I’d hit a dead end. I could only pose with my legs spread apart so much, before it became boring. I decided to try to find out how real life hookers kept their customers coming back. There was a hotel in the business district that had a reputation for being a place where women with tail for sale met with their money-tricks. The Aventeen was once a high end downtown hotel, but the surrounding neighborhood had gone into decline decades ago. The hotel never quite recovered as the surrounding area revived through gentrification, and thus it existed by providing a comfortable place for the higher-end prostitutes to ply their trade. Wednesday afternoon was the perfect day for my field trip to the Aventeen. Dave would be working late, and I heard the middle of the week was a hotbed of working girl activity. In my dressed down jeans, I sat in a quiet ...

... corner of the formerly eloquent bar, nursing a series of iced teas. The place was an oak paneled relic of times gone by. The heavily upholstered booths were dated and in need of restoration, but given the lack of big-spending crowds; the prospect was unlikely. I watched as women in tiny skirts and impractical heels sipped at Cosmopolitans until some man in a business suit sidled up next to them. Typically, they smiled, engaged in a brief conversation before disappearing from the bar for an hour and then returned alone for another Cosmo. Interesting at first but I soon realized it told me nothing about their techniques during that unseen hour. However, one woman in particular, caught my eye. She seemed somehow familiar. She was small, with dark hair cut into a bob style with bangs. She certainly didn’t look like what I’d consider to be hustler, yet she seemed to have the most activity of any of the other women present that day. At last, I realized, this was the same woman I’d seen in the adult toy store a few days before. I decided to approach her when there was a lull in her agenda. I ordered a Cosmo at the bar and carried it over to her table. “Hi, I’m Penny. I think you helped me a few days ago. The rental of the Sybian?” I realized how weird an opening line this was. She looked me over, without a word, as if evaluating my threat versus money making potential. “Would you mind if I sat and talked to you for a few minutes. I promise I won’t be a pest.” To my surprise, she ...