While we were driving, I suddenly thought of it! I bet my 30 points and challenged Jess to get off the car naked, flag a taxi down and take the taxi to the next street where I would be waiting for her with the car. She didn't even think about it and instantly refused, saying that it was too dangerous. I agreed but told her that she lost the bet anyway and she had to give me her shirt! Now I had the upper hand with 60 points.
It wasn't over though, I knew that she would definitely try to win back and give me something equally hard which I must do in order to win her! Sure enough, we drove for a while more and Jess stopped outside a 7-11 and wagered her remaining 40 points and dared me to go into the 7-11 naked!
I was shocked and didn't want to do it but that would leave Jess with 80 points and I couldn't allow that! So I bucked up my courage and stripped naked and stepped out of the car. I slowly walked up to the 7-11, the counter guy was reading a newspaper and he haven't seen and I hoped he would keep it that way as I reached out my hand to open the door.
Suddenly Jess shouted from behind for me to stop! She had come down from the car and was running towards me, her boobs bouncing vigorously as she was topless, though her nipples were covered by her nipple pasties. She scolded me for being mad and told me that I didn't have to complete the challenge after all as it was too risky.
I was so relieved and grateful to Jess but things had to be done and I insisted that I won the challenge and forced Jess to give up her points. While we were still outside the 7-11, she took off her skirt and her threw her nipple pasties on the floor, leaving both of us naked!
In the excitement of being nude, I suggested that we should go explore the hdb block that we were at in our current state! We went to park the car in the parking lot and chose the first block that was in front of us and waited for the lift.
When the lift came, both of us got in and we pressed for the top floor. When we reached, the door opened and I grabbed the car keys from Jess's hands, pushed her out with all my might and closed the door quickly! By the time Jess realised what was going on and turned back to stop the lift, the doors had closed fully and I was making my way down! It was really mean but at the time I only found it funny!
When I reached the ground floor, I went to the car, put on my clothes and drove off! I drove the car around the area for about ten minutes and parked it at another carpark which was about 10minutes walk away and walked back to the block!
When I reached the carpark, I wondered to myself where Jess could be. She had left her phone on the car so I couldn't contact her. What if she had been caught or raped while I left her alone! I expected her to be hiding behind a car at the carpark or something waiting for me return but when I checked the whole carpark she wasn't there!
I decided to go back to the block where we were and I took the lift all the way up and slowly made my way down via the stairs but she still wasn't there! Then I remembered that at the top floor the stairs continued leading up to the roof and I thought that she might be there! So I went there to check and there she was! She was leaning against the wall and she had put her knees up against her chest to cover herself and she was so confident that I would come back that had actually fell asleep! The audacity!
I decided to prank her while she was asleep. She had held her legs up and I spread them apart further, exposing her shaved vagina. She had leaned back quite abit and I was able to see her anus too! I took out two cigarettes from my bag ( I smoke at times, don't judge!) and put the first one into her pussy! She moaned lightly but remained asleep. I then put the second one into her asshole! This was a bit harder and required a little bit more nudging but I eventually managed to get it in! I then lighted up both cigarettes and it looked like there was smoke coming out of both her vagina and asshole! I had such a hard time controlling my laughter and I took out my phone to snap a few pictures.
I then took out my lipstick and drew a red moustache on Jess's face! It was so funny! I continued taking pictures until suddenly Jess woke up with a jolt! She cried out with pain and I realised that the cigarette in her pussy had almost burned out and it had burnt her! She quickly removed both cigarettes and when she realised I was there scolded me for leaving her behind!
I just kept laughing and told her to get moving back to the car. She was rubbing her vagina with her hand to ease the pain and she hadn't even noticed there was a huge red mustache on her face! We took the lift down and I told her that the car was a ten minute walk away! I was fully dressed and she was naked but she didn't really care, until we reached a point where we had to cross the road. It was a small road and there was no cars in sight so we quickly ran across!
We reached the hdb block opposite when we suddenly heard a lot of noise! Turns out there was this group of Malay guys sitting at the void deck and drinking! It was unthinkable what they would do to Jess if they saw her naked! So we had to take a detour round the block and when we turned a corner, we ran into a couple making out!
They noticed us and stared at us, or rather, stared at Jess who was naked from head to toe with a big red moustache drawn on her face! Jess didn't even scream or anything but just grabbed my hand and ran past them! Her boobs and butt cheeks were wobbling like crazy as she ran! We just kept running till we reached the carpark where the car was and we quickly went up.
Now we were on the car and safe, Jess said that she was really tired already and asked to go back so I drove us back as she fell asleep on the passenger seat still naked. I decided to play one last prank on her! I drove back to my house, removed every piece of clothing from the car and went upstairs, leaving Jess sleeping in the passenger seat naked with no clothes nearby! I left the window open of course so she would have air.