Like many women, thanks to what our society promotes as attractive, Lisa did not feel she was beautiful. I didn’t agree, and told her so, many, many times, but to no real change in her view of herself. I finally persuaded her to buy some sexy clothes and go out with me for a night on the town. I asked her to get a very short, skin tight skirt. Finally I asked her not to wear any underwear. She hesitated at this, but then finally agreed. The day of our celebration Lisa went shopping. She called me at work to tell me about her new dress. She seemed very excited about wearing it for me. She wasn’t sure, however, that she would feel comfortable in public wearing such a sexy outfit. I assured her that she would be a big hit with anyone who saw her. I don’t think I convinced her. The plan was to go out to dinner and then go dancing.

I couldn’t wait to see Lisa in her new outfit. She picked me up from work at 6:30. When I saw her I was stunned. She looked like one of those glamour models. She gave me a shy smile when I whistled at her. She said, “I can’t believe I’m actually wearing this.” I said, “You are the sexiest woman I have ever seen. Lisa was wearing a red dress that barely covered her privates. Her large breasts stretched the top to its limits. The dress was low cut with a full one third of her breasts exposed. I said, “I hope those shoulder straps are industrial strength.” Lisa giggled and said, “I hope so too.” I continued to stare at her as she drove out of the parking lot. I noticed two bumps in the front of Lisa’s dress. I was happy to see that she wasn’t wearing a bra. I glanced down at her legs and wondered if she was wearing panties. Lisa noticed my stare and confirmed, “No, I’m not wearing panties.” I asked her to prove it and she pulled her hem up slightly revealing her neatly trimmed bush. Lisa said, “I have to be very careful when I get out of the car or bend over.” I said, “I’ll bet.”

(…)
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