At the local farmers market

On one of Kaylee's days off I decided to take her to the local farmers market. Along the way she suggested a set of embarrassing challenges for me to preform throughout the day. "And if you complete everything, I'll let you expose me in front of everyone. Make it look like an accident of course, but you can strip me completely naked if you finish all of my challenges?"

This peaked my interest. Getting to embarrass both myself and Kaylee in one day was a dream. "But what if I lose your challenge?"

She gave me a wicked grin, "Well that just means I get to expose you to everyone instead!"

"Agreed!" I said at once.

For the rest of the ride she pondered different challenges and wrote them down on a piece of paper. She kept them hidden until we arrived. It was during a weekday so many of the fathers were at work and the children at school, leaving my favorite type of person: MILFs. When we pulled into a parking space I noticed the car next to us filled with four women. They were joking and laughing as they left their car. Kaylee handed me a short simple list:

1. Get a picture with a stranger in frame and your cock out

2. Put your underwear in someone's shopping basket and ask them for them back

3. Cum on someone without them noticing

I was grinning ear to ear. "I supposed I'll need to remove my underwear first if I want to have a shot at completing these." Kaylee nodded and made no effort to hide her gaze. I was wearing swear pants, a long sweatshirt, and tight briefs underneath. I slipped my thumbs into my waistband and lowered my pants and underwear to my ankles. As I was shifting around to get them over my shoes, Kaylee was given several glimpses of my cock. My sweatshirt zipped up in the front, but came down quick low. If I was standing up it ended just below my butt. I decided to leave my pants in the car and stuffed my underwear into a pocket.

As we go out of the car Kaylee ran up behind me and smacked me on the butt, "Daring today aren't we! No pants?"

I chuckled and said, "I'm covered! So long as there's no breeze!" I lifted up my sweatshirt in the front to flash her my cock as a little tease. She pretended to be shocked and covered her mouth.

We walked up behind the group of four women. They seemed to be a perfect target for my challenges. Their conversation broke off as they saw us approaching. The tallest of the women squinted at me and said, "Have I seen you somewhere before?" I felt a bit nervous. There were tons of places she may have seen me at this point. Each more embarrassing than the last.

"No I don't think-" I began before she cut me off.

"Yes! You were one of my old students back in middle school! My my how you've grown up!"

It suddenly came back to me, "Mrs. Peck? It is you!"

She was wearing a form fitting sweater than complimented her body well. She looked over at Kaylee, "Oh you would not believe this young man! Back in the day he used to get in so much trouble. I would catch him looking up my skirt from time to time and always had to give him a spanking, right in front of his classmates!"

Kaylee blushed, "Oh my! Well hey, why don't we get a picture of you too!" She was a genius!

Mrs. Peck looked excited, "Oh that's a great idea!"

I shuffled toward her and got into a pose next to her. This might be tricky since my back would be to Mrs. Peck's three friends. As I stood next to her she slid a hand around my waist, tugging me in close to her. I slowly pulled my sweatshirt up and bit by bit felt my exposure begin. My penis wasn't quite erect yet, so it flopped out along with my balls to the cold morning air. As I moved my sweatshirt I felt her hand on my waist touch bare skin. Luckily she didn't notice. I was hoping to hear something from Kaylee, but she seemed to be purposefully having trouble with the camera. "This darn thing! I can't seem to get it to work!" I was standing there flashing her and looking like a fool.

Mrs. Peck looked unbothered, "Oh don't worry, we're not going anywhere!" I would feel her hand squeeze my waist gently. Finally Kaylee seemed to fix it and snapped a few pictures.

"Oh these look great!" Kaylee said as she flipped through them. "Let's get a funny one! Mrs. Peck why don't you plant a big kiss on his cheek!"

Without hesitation she turned and grabbed my face. In shock I dropped my sweatshirt to again cover myself. She pulled my face to hers and kissed my on the lips with an exaugurated smooching sound. Kaylee giggled as she took several more shots. I embraced her in a hug and let my hands fall to her ass. "Oh it is GOOD to see you again." I said as I broke off.

Mrs. Peck walked over to Kaylee and said, "Here why don't you take my number and send those over to me!"

Kaylee grinned and said, "Can do! Why don't you give me your number and I'll send all the pictures we take today at the end of the farmers market." She gave me a wink as they exchanged information.