This is the story of how many women in our small town learned my deepest and darkest secrets. Tina and I had been dating for about a year. She and I were both divorced and living separately each with our own two kids. Mine were in high school while hers were both in middle school. Our relationship had been an exciting mix of overnight trips, dinners, concerts, hikes... Occasionally she would indulge my kinky side and we would incorporate one or more of my fetishes into our sex. It was clear that she had a dominant streak in her, but mostly she was a very generous lover who kept me extremely satisfied.
One Friday after work, Tina said she had been at her daughters' school earlier that day and that the office clerk mentioned that I had done a First Aid presentation for teachers and PTA moms when my kids were enrolled there. Tina said she loved that and wondered if I would be willing to do it again. She even said she would "make it worth my while". I wasn't sure what that meant, but I had enjoyed being the only guy in a room full of women and told her I'd be happy to do it.
She jumped out of her chair with a squeal and gave me a big hug. "I can't wait to tell everyone you're coming back to teach them again!" It felt nice to make her happy, but I wasn't sure why she was so excited. I decided to just enjoy her happiness and started thinking about a lesson plan. She came back in a few minutes with two glasses of wine and said, "we need to think about where to do it and what you will wear". I told her that last time we did it in the teacher's lounge at school and that I didn't wear my work uniform because I was off duty.
She then said she wanted this time to be a little more fun so she would find a small banquet room in town so they could enjoy a drink or two while I taught them. I spent the rest of the weekend nodding along to all of her ideas. It was becoming clear that this was a big deal for her and that I would need to make my presentation a little more exciting than last time. Little did in know she had some ideas of her own.
Two days before the "big night", Tina informed me that she changed the venue to the Principal's house due to lack of a budget and need for comfort. She didn't know, but when my kids were at that school, I had a little crush on the principal, Mrs. Jones. It wasn't that she was super-cute, I just liked the image of an all-powerful woman in charge of the school. Tina also mentioned that I needed to "wear something cute" to keep their attention. I had no idea what that meant.
That Thursday night finally arrived and I had all of my props, CPR dummy, bandages etc all staged by the door. As we were getting dressed, Tina came up behind me and wrapped her arms around me. She thanked me again for agreeing to come to the meeting and again promised to "make it worth my while". Her hands slid down my chest, over my abs and down to my cock. She took it in her hands and began to slowly stroke me. I closed my eyes and sighed happily. She said, "I want you to feel sexy while all those women are staring at you, baby. Put on some cute, lacy pink panties for me, please? And some black thigh highs too. Please? Don't worry, no one will know." With her hands gliding over my cock and ass I was powerless to say "no". Plus, I was always excited when she "gave me permission" to wear my pretty things.
As I was stepping into my jeans, feeling the denim slide over my silky legs and up to my waist to hide my cute panties, Tina walked in. "It's too bad that I'm the only girl who will know how sexy you look under those jeans." I smiled and nodded. "Wouldn't it be fun if you could show off for them? Let them know the real you? Show them how sexy you look in a short skirt? Turn around and bend over for them? Admit your dirtiest secrets?"
She was driving me crazy and she knew it. My cock was as hard as a steel pipe, stretching my panties and becoming uncomfortable in my jeans. I hugged her and thanked her for that sexy imagery. It was always a gift when she indulged my "sissy side". The emergence of the feminine parts of me were recent, but very powerful. Those thoughts, the one's she detailed, were an escape for me and I was spending more time "experimenting" than ever before.
