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Old 01-06-2016, 05:47 PM   #1
Truckernaut42
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Default Naked for pizza delivery dare

Went on vacation with some friends, sister, and one of her friends, ended up playing truth or dare when we got drunk and my sister dared me to order pizza and answer in my boxers (because her friend is into me and she wants me to be exposed for her friend) so I agreed. My friend added that if it was a girl delivering, I had to ask if she wanted me to drop my undies for her, and come back with the pizza nude, and if I accepted this part of the dare, everyone had to give me $25 as well as the pizza was free for me. I accepted because I've never ever seen a female delivery person. So we ordered and we got the call that the pizza was here. Our hotel was weird and you had to go up some stairs to unlock a door and let them in, meaning I had to walk through the hall in my boxers and up the stairs, which I did. I was getting hard as I walked up, which made me nervous because I really didn't want to have a boner for them.

I walked out the door barefoot and in my boxers only to discover that of all the times for it to be a woman, this time it was a woman. She seemed shocked and a little angry that I was barely dressed. It was very cold outside too so my feet were getting numb, but I explained the dare for her, and added that I had to get naked. I knew I would have to go through with it because my sister answered the phone and knew the delivery person was female.

She thought it was funny and accepted. I dropped my underwear right in front of her and my boner sprang right up and she just laughed. We made a bit of small talk while I paid for it and she quickly would look at my cock and back.

I went back downstairs completely nude and went back into the room. My sister's friend looked flushed. It was worth it for the money and really funny.
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Old 01-10-2016, 03:26 PM   #2
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Is there anymore to the story? If you don't mind me asking that is
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Old 01-11-2016, 06:17 PM   #3
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That sounds awesome, hope you get up to more things like this
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