Pranks around town

One day we had to take care of some errands around town. I wore a baggy shirt, sweatpants, and nothing else. It was my job to drive Mrs. Wilson and Kaylee to the store, but they took care of all the shopping.

We first headed to the grocery store. Since it was a week day, the stores were mostly empty with the exception of a few house wives. Kaylee had recently been taking to the habit of pranking me. This would usually involed stripping me in one way or another and yelling "Pranked!" It made me so happy that I wasn't needing to do anything to be humiliated.

When we got to the store I grabbed a cart and began down the first aisle. Mrs. Wilson had a long list of groceries and started looking through the different selections of fruits and vegetables. In this section there was only one other customer, a top heavy woman squatting down for the bottom shelf. She was wearing jeans and a button up shirt that was struggling to contain her large chest.

Kaylee pointed to the shelf above the woman and said, "Why don't you grab the apples at the top there? I want to get some good ones!" I had to reach on my tip toes to truly get them. I moved over in front of the woman and stretched to reach. My crotch was only a few inches from the woman's face when I heard Kaylee sneaking up behind me. She gripped my sweatpants and yanked them down to my ankles, exposing me soft floppy cock to the open air. She then looped her arms under mine to ensure I couldn't cover myself. "Pranked!"

The woman let out a gasp and my cock hovered in front of her face. "Kaylee!" I screamed. I wiggled my hips from side to side in an attempt to hide, but all this did was brush my cock against the womans face. Blood started to surge to my groin and I could feel myself getting hard."Oh my god this is so embarrassing! Im never going live this down!"

The woman blushed, "Oh dear, don't worry. I've seen it all, I have three sons that-" I cut her off by slipping my semi hard erection into her mouth. Her eyes widened as I did.

"Oops! Oh my god no!" I cried out. Kaylee began pushing my hips in and out, causing the woman to give me a blowjob. Regaining her respect, she pulled away, letting my cock drop out of her mouth, and stood up.

"You two are terrible! Putting up with her pranks must be awful!" The woman said with a wink, "I had best let you two go, no reason to keep humiliating this boy." She turned and began walking away.

Kaylee let go of my arms and gave me a sharp push toward the woman. I stepped out of my pooled pants and stumbled forward. As I fell I made sure to reach out and lock both hands into the woman's jean's waistband. Just as Kaylee had done to me, I pulled her pants down to her ankles. To my disappointment she was wearing panties. Simple pink cotton panties that gave full coverage. "Oh no!" I yelled.

She turned, giving us all a full view. For the first time Mrs. Wilson seemed to notice what was going on, "Sir! Just what do you think you are doing?"

The woman didn't even bother to cover up. "Oh it was an honest mistake, here let me help you up" she reached down and offered her hand. I took it and as I got up placed a foot on her jeans. As I did I slipped again, this time grabbing her shirt. I ripped it open from collar to waist, causing buttons to fly everywhere. Her enormous breast spilled into view. They were even bigger than Mrs. Wilson's! She had very small nipples that were already hard.

"Oh no I'm so sorry!" I said as I scrambled. My cock was completely at attention now. The woman's face remained calm, but I could see she was reaching her limits. Again, she didn't cover up her nudity.

"Ok, lets get you up very slowly!" Mrs. Wilson and the woman each helped me by grabbing an arm. It was hard not to stare at the woman's breasts as the swayed. I was shocked she hadn't worn a bra.

"Here let me get these," I said as I bent to pick up the buttons. I was now face to face with her waist and got a great view of her panties. Simple, yet sexy they covered all the important bits. I'm sure if she turned around her ass would be amazing. As i continue to collect buttons I noticed Kaylee sneaking around.

"Pranked!" She yelled as she yanked the poor woman's panties to the ground.

"Oh my lord!" She screamed as her pussy came into view. Completely shaved, I saw her exposure close up and person. This time her hands did try cover up but Kaylee did the same trick and pinned her arms.

"Kaylee stop!" I reached out to Kaylee, causing my body to press against the womans. Our sex's rubbed against each other giving a great sensation. Mrs. Wilson ran up to us to help the situation, but just ended up knocking us down. With a yelp, the three of us tumbled to the ground.

Kaylee was on bottom, the woman on top of her, and me on top. My cock was now firmly pressed against her, with the head at the entrance of her pussy. "What is going on?! I am naked in the middle of the store!" The woman screamed. She had finally lost it and wasn't giving us any more excuses.

"Hey! I was exposed first!" I said in feigned annoyance. I attempted to get up and instead fumbled by slipping on her discarded panties. This caused them to fling across the floor and also plunch my penis deep into her pussy. "Oh!" I let out a moan. Mrs. Wilson quickly picked up the discard panties and stuffed them into her purse.

"Sir get off of her!" She hooked her arms under my armpits and lifted me out. My cock popped out and stood erect as she helped me to my feet.

The woman stood up and grabbed her pants. Not even caring about the panties she put them on, pulled her ruined shirt closed and stormed past us. Kaylee laid there with the biggest grin on her face. Still bottomless, I reached out and helped Kaylee up. "You did perfect," she said as she pulled me into an embrace. My cock rubbed against her pants. She grabbed my ass in both hands and squeezed.

"Ok you two, we have some shopping to do!" Mrs. Wilson said as she handed me my pants. I slipped them back on, tucking my erection down a pant leg.

We continued on when I felt something in my pocket. I reached inside and noticed they were the woman's panties. When I looked up Mrs. Wilson was already making eye contact and gave me a wink.