Most Embarrassing Dares With Family?

[Truckernaut42]

What's the most embarrassing dare you've done with a family member

when I was 11 at a family gathering my cousin and I stumbled upon some diapers at our grandma's and he dared me to wear them and when Grandma came to check on us she caught me and made me wear nothing but the diaper at dinner which was humiliating

[TheoDares]

Human pup for like two hours

[Twins]

My mum walked in on my sister using my mouth as her toilet

[PlagueBringer]

The only thing I've done remotely involving family was masturbate while my mother was in the same room. She was occupied with the television and I was being commanded via skype. I didn't reach completion and it was very exciting being that risky, but I probably would not want to do that again.

[rhode64]

Originally Posted by Truckernaut42

What's the most embarrassing dare you've done with a family member

when I was 11 at a family gathering my cousin and I stumbled upon some diapers at our grandma's and he dared me to wear them and when Grandma came to check on us she caught me and made me wear nothing but the diaper at dinner which was humiliating

The only time I have done anything involving family was when my wifes mother came round and let herself in without knocking and I was sat in out living room naked and edging .I heard someone come in and went to investigate and ran into her naked and hard .Her face was a picture and my mrs and I had a good laugh over it when she left .

Before that my ex inlaws from my first marriage had seen their daughter and I naked fondling each other , and the 2 of us having sex a few times .

[lowlysub]

What's the most embarrassing dare you've done with a family member

Not much dare but here is my only 2 thoughts.

We went on a family florida vacation. I still wet the bed often. I successfully stayed dry that week. Once we got home I found a package of small size diapers (I was only one in family that size). I guessed my mom bought them just case for the trip. Over a few week period I stole them to wear. As for family member involvement my mom joked later on them disappearing.

I lost some stupid dare to my brother. I don't even remember what. We were home alone. He was 5 years older than me and much bigger/stronger than me. He walked away and soon called me to the living room. He was sitting on a char holding the family punishment paddle. I began yelling at him no, but he grabbed me and quickly I was nude over his knee. I dont remember how long but remember crying a lot. But then door opened and my mom came in. She say my butt and asked what happened. All my brother could say is just because. She yelled at least i have a reason for you. He quickly stripped also and was being paddled over my moms knee. She got his ass to same color as mine. Then she handed me the paddle to give a few. But I was weak so I know it did nothing except his pride.