Chapter 2: Road Trip Hijinks 

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Lisa and I were getting ready for our road trip to my best friend's wedding. We had a six hour drive ahead of us and we planned on not stopping so we could get to the hotel as soon as possible. Unbeknownst to me, while I was downstairs packing our lunches, Lisa was up to something. She packed my suitcase and decided to only give me tighty whities and swapped my trunks for a neon bright pink speedo. She was always playing pranks and she knew this would be her best prank yet.

When I came back upstairs, I noticed she was acting weird, but I didn't pay too much thought to it. I grabbed our cases and carried them downstairs. I quickly put them in the car and went back to the house for Lisa and my backpack.

Lisa: Cole could you please wear those cute old shorts I love?

Cole: The old ratty pair with the hole?

Lisa: YES! that pair and wear those white briefs that I ripped.

Cole: Why? They are so ripped up, but I'll wear them only if you wear what I pick out for you.

Lisa: Deal!

We ran up stairs and Lisa stripped me out of my clothes. Her hands began to roam and she quickly found my cock and began to stroke it. I stood there and let her handle my body. The sensation was great and just before I was about to cum, she stopped and threw my clothes at me. She was such a tease and I loved it. I wasted no time and slipped on the torn undies and shorts. They did nothing to hide my boner as I tried positioned it upwards under my waistband.

Once I was dressed, I searched through our closet and found a black mini skirt, a matching crop top for her to wear. I opened our dresser and found her tiny pink thong and just knew she had to wear it. Once I had everything laid out for her, she stripped for me. Seeing her completely naked was always a joy. She gave me a little show and bent over for me as she took off her panties. I watched as her beautiful pussy came into view. She backed up and my face was immediately between her legs. I couldn't help but eat her pussy from the back and give her an orgasm.

Lisa: Baby, you keep that up and we will be late.

Cole: Sorry, I couldn't help myself! You're just way too hot.

Lisa: Well you better save some of that for later

Lisa slipped on the outfit and we headed off to the wedding. The drive started off very uneventful and average. It wasn't until we reached the halfway point that we needed to stop for gas. I pulled into a station and we both got out the car to stretch our legs. When we went inside of the gas station, I grabbed a couple of snacks and drinks. Lisa kept picking up more items and made me hold them. My hands were completely full by the time she was done. I stopped in front of the mini donuts when...

*SWOOSH*

Lisa had pantsed me! She immediately started laughing as my old tighty whities with the holes in them came in view for her and the attendant. The biker looking guy couldn't hold back his laughter at the sight of my exposed underwear. I turned two shades of red as I hobbled over to the counter to place the items in my hands down and pull my shorts up.

Attendant: Nice underwear, looks like you've worn those a lot.

Cole: * embarrassed laughter* what can I say, I like to be comfortable on long drives.

I quickly paid for the food and gas before rushing outside to finish pumping. I got in the car and plotted my payback on Lisa. She got in the car and I purposely dropped one of the snacks on the floor in front of her. As she bent down to pick it up, I grabbed her tiny thong and pulled it up her back. She let out the hottest moan as I pulled the thong over the headrest of the seat and locked it in place.

Lisa: Hey! Babe what was that for?

Cole: For being so naughty you have to stay in this until we get to the hotel. Now be a good girl and sit back.

As we continued our drive, the road was kind of bumpy and Lisa squeaked and moaned the entire time. Before long she couldn't take the wedgie any longer and pleaded with me to let her out. Of course I let her out, but only if she did something off of our kinky bucket list. She agreed and before I knew it, her head was in my lap and she had pulled my cock out of the holes in my underwear and shorts. She wasted no time in going down on my cock and giving me road head. The blow job was amazing and caused a couple truckers to honk their horns at us with a smile on their faces.

Just as we arrived in town, I finally blew my load after Lisa's constant edging. She swallowed every drop and fixed herself, but she left my cock hanging out of my shorts on the seat. When we arrived at the hotel, we got out of the car and I forgot to fix my shorts. Lisa noticed and had a big grin on her face as we walked into the lobby. I noticed everyone was staring at us, but didn't realize why.

Front desk clerk: Good day, how may I... Oh my sir!

Cole: What?

Front desk clerk: Umm your.. umm your member is umm showing.

Cole: My member?

I looked down and before my eyes it was the most embarrassing thing ever! My cock was hanging out of the hole in my shorts. Lisa laughed and drew the attention of guests nearby as they got an eye full of my goods. I quickly fixed the problem and hurried the clerk with our room information. When everything was clear, I embarrassingly walked to the elevator and quickly shut it.

Cole: Lisa! How could you?

Lisa: What? I wanted everyone to see what's mine forever.

Cole: Someone's being naughty again. That's it, give me your panties now.

Lisa: what why? Everyone can see us in this glass elevator.

Cole: You're being punished.

She finally slid her thong down and stepped out of them. She put them in my hand as I bent her over. Her entire ass and pussy was on display for anyone that looked up in the glass elevator. We had two floors to go, so I quickly gave her bubbly cheeks a spanking. I could see everyone looking at her as her ass became pink. When the elevator doors opened on our floor, a group of old ladies, who were waiting, caught us.

Old lady: Oh my, I remember when I was young. You two whippersnappers have fun.

Lisa was so embarrassed and we rushed to our room. The night wasn't eventful, but the next morning was shocking. I wanted to get a quick swim in before we had to head over to my friends house. So I looked through my suitcase and finally realized that Lisa had only packed me tighty whities and a neon pink speedo. I laughed to myself as I squeezed into the tiny speedo. The tiny suit left no imagination, anyone could see the outline of my cock. I didn't care too much and just went to the pool.

As I swam, Lisa came down to the pool area to watch me. I waved and continued my swim for another five minutes. That's when I started noticing people staring at me. I was getting slightly embarrassed of the tiny suit, so I decided to get out of the pool. That's when I discovered that my speedo was falling apart! Lisa had given me the dissolvable pair. Lisa and everyone laughed as my bare ass came into view. I tried to get my towel, but Lisa grabbed it. She ran and I was forced to run through the hotel naked to get back to my room.

I took the stairs and got back to our room first, so I hid behind the door. When she finally got back to the room, I surprised her and picked her up by her thong. I brought her over to the bed where I pantsed her and gave her a rough squeaky clean wedgie. I loved watching the tiny fabric of the thong glide between her pussy and made her moan. Before long she was soaking wet and the thong made sloshing sounds as I kept wedging her.

I laid her on the bed and turned her head towards me as she took my cock into her mouth. I slowly face fucked her while pulling her thong higher between her legs. The pace picked up and I was full on fucking her mouth as I ripped off her thong and dove into her soaking wet pussy. It didn't take long to give her one, two, three, four orgasms. She was shaking under me with pleasure as she deepthroated my cock. It wasn't long before I couldn't hold back anymore and pulled my cock out and painted her tits. We were both exhausted, but she got up and whipped herself clean before coming back.

Lisa: Alright, my turn! I need you to fuck me right now!

~ To be continued ~

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