This is my first story.
I appreciate your comments.
All characters are over 18 years.
This is a work of fiction.
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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.
We arrived at the Principal's house 30 minutes early and I began setting up for my presentation. Tina and Mrs. Jones disappeared in the kitchen and worked together to finish up food and drink preparation. Mrs. Jones returned to the living room and approached me. She stepped a little closer than usual and handed me a glass of wine. "Thank you soooo much for agreeing to teach us again, Curt. You have no idea how much this means to us and to me personally. I can't wait to see what surprises you have for us this evening." She leaned in and gave me a little kiss on the cheek. I looked up and saw Tina from the doorway to the kitchen with a little smirk on her face. I stared at her with a "deer in the headlights" look and hoped she knew I hadn't initiated anything with the hostess.
Teachers and moms began arriving over the next thirty minutes. I recognized most of the teachers, but the mommies were new to me. I realized that I felt very close to the teachers who had taught my kids over the years. Katie, Maria, Jenny, Sue, Janet, and Marcie among others had played important roles in our lives over the years and now I only occasionally saw them in the grocery store or when I went to the school for a fire drill. It felt good to be surrounded by old friends and my new lady, Tina.
Eventually, Tina asked the women to sit down and invited me to the front of the room. They were all seated on a huge wrap-around sofa and assorted comfortable chairs forming a large horseshoe. I thanked them all for coming and began my instruction. From past experience, I knew that they had a short attention span so I was using a lot of hands-on skills and keeping the pace moving. I noticed that the wine was working and everyone was having a good time, but that included a lot of side conversations. I looked at Tina and indicated I could use some help focusing the crowd. As much as I tried, the volume continued to rise until no one could hear me talking about Airway, Breathing, Circulation...
Finally, Tina came to the front and said, "ladies, it looks like you're having trouble focusing. Let's take a break and refill our drinks". She then hugged me and said, "when they come back, I'm going to take your shirt off. That will help them focus on you. We might need to take off more later."
"Very funny" I replied. I was pretty sure she was joking, but not entirely.
As everyone came back into the living room and sat down. Tina came up behind me and quickly pulled open my pearl snap shirt. She then pulled it off me in a quick jerk and I stood there topless. I was shocked as the crowd of ladies shrieked and howled in disbelief. I shouldn't have been surprised, but I was. I'm in good shape and definitely an exhibitionist, but this was supposed to be an educational event for the school. Now, there I was shirtless. Then Tina said, "The next right answer gets his pants!"
I was really shocked. I looked at her pleadingly. She must have forgotten that I was wearing my girliest panties. She blew me a kiss and winked.
I decided that I needed to wrap this up or I was going to end up revealing my secrets to all of these important women in my life. I finished up the presentation, but unfortunately the last part was a trivia game based on what I taught. Tina came to the front and took the lead. "Ladies, here we go! The moment you've been waiting for: We're going to strip our teacher!"
I stared at her wide-eyed wondering if this had been part of the plan the whole time. I started overhearing parts of conversations among the teachers and mommies.
"Panties, sissy, girly". I heard all sorts of sexy conversations happening. I couldn't help but wonder what Tina had been telling the women about me all night. Mrs. Jones answered the first question correctly and practically ran to the front of the room.
"Tonight is your special night, baby", Tina whispered in my ear. I looked at her and shook my head "NO!" She giggled and said, "Oh my PantyBoy, all of these people get to see the real you. Now, let Katie Jones undress you, babe."
My cock began to tent in my jeans. I couldn't believe this was about to happen. They were about to see my panties. I was about to be stripped in a room full of women while wearing my prettiest sissy underthings.
Mrs. Jones dropped to her knees in front of me and reached for my belt and zipper. Tina was close to my ear and said, "Baby, they all know about you. I told them your secrets. They know you're wearing pretty panties and thigh highs and they want to see them. You're going to show them everything and be a good boy, right?"
I didn't know whether to laugh or cry. There I was, with my crush on her knees unbuttoning and unzipping my jeans with one of my dirtiest secrets about to be exposed to many of the women I most respected in the world. I considered running, but then realized that I wanted this. I needed this. I decided I was going to stay and be stripped and that I was going to do everything they asked of me. Tina was my Dom and everything would be ok.
Katie made quick work of my belt and began peeling my jeans down over my hips. Slowly, the lacy waistband of my panties came into view. The women were giggling and pointing, but also staring with eager anticipation. She continued to pull down until my hard cock came into view stretching tightly against the lacy crotch.
She stopped pulling with the belt resting just below my balls. I was in shock. This was both my worst nightmare and my dream come true. Tina's voice was ever-present in my ear "You're such a good PantyBoy, they love your cock in these panties, you look so sexy, they're going to love your ass in these, I know you're loving this attention, look in their eyes - they want you...Are you ready for some fun?"
My head was spinning as I stood in the front of the room with my pants pulled down and my pink panties on display. She stopped before my sexy thigh highs came into view, though. Tina thanked Katy for her handiwork and promised more skin to the next winner.
I was very distracted by the shouts coming from the audience like, "Hot panties Curt", "I have that same pair", "your cock looks great in those", "turn around and show us your ass!" I managed to ask a question and Maria, my daughter's former fifth grade teacher ran to the front. She giggled and whispered with Tina before standing behind me and grasping the sides of my jeans. I inhaled as she slid them down my legs, revealing my black thigh highs with a fishnet pattern and three inches of pretty elastic band stretched around my thighs. Nylons and panties make me feel so sexy, but right then, looking into the shocked eyes and open mouths of the ladies I felt very vulnerable. I suddenly felt like this was all a huge mistake.
I think Tina sensed the overwhelming emotion I was experiencing. She stepped in front of me and gave me a big hug. Then she began pulling me as we turned so I faced away from the audience. Of course, this gave the women a great view of my cute buns in those cheeky panties. Tina kissed me and said, "I know this is hard for you PantyBoy, but I'm very proud of you for sharing your sissy-side with these women. They will never forget tonight. You need to realize Curt, we are only getting started. Before the night is over, I'm going to show them everything... I'm going to take your mouth, your asshole...that's what you want. Right?"
As Tina whispered in my ear, Maria had been massaging my ass to the cheers from the crowd. She reached under the fabric, pulled them into a thong and kissed my buns. Needless to say she was enjoying herself. Meanwhile, my cock had softened a bit as I realized that Tina was going to change me tonight. I would never again be the strong, manly firefighter they all knew. I would forever be the sissy who stripped and let them fuck his holes and he loved it.
