Unexpected Dare

by Marcus
(Greenville, SC)

My wife and I have been married for 25 years and we have never done anything prior to what I am about to share with you. Have been on a weight loss journey and I have this pair of shorts that I have had for a very long time.

Those are the most comfortable piece of clothing I own. They are a part of me, yes they look like they have been thru a war, but they are comfy. They have become way too large for me and when I wear them I spend more time hiking them up to prevent them from just falling off.

My wife has been progressively getting more and more annoyed with them and has made many attempts to try and throw them away. To which I have rescued them from the trash more times than I can count.

So we made a deal. She will stop trying to throw them away and I can keep them BUT if I am wearing them out in public and they fall I am not allowed to retrieve them.

Where ever they may fall...will be their final resting place. So since I knew she was serious, I have made a point to just wear them around the house.

So one afternoon, I went down to the mailbox and ran into our neighbor Sandy. Sandy is 49 but looks like she is 30.A gorgeous woman. We have known her for as long as we have lived in this house but have never really hung out, done cookouts etc. Just a friendly neighbor.

So I am down at the mailbox chatting with Sandy about our other neighbor who is a constant source of drama. My wife came out to join us and the three of us were in the middle of a conversation when my wife took my phone and dropped that into my right side pocket which made my shorts drop like a sack of potatoes. Luckily I was able to catch them with my left hand. So my right side was sagging down from the weight of my phone which was exposing my right hip but my left hand was hanging on to the shorts so they would not fall.

Sandy stopped mid sentence and had a puzzled look on her face. I went to quickly grab my right side of my shorts and my wife scolded me and said UHUH...NO!!!

So my wife told me to put my right hand on my head and I did. Sandy then said ok, what is going on here. So my wife tells her everything about our shorts rule. So Sandy bust out laughing so hard she started snort laughing.

Sandy said well the good news is you do what you are told to. My wife said, "He better do what he is told." Now she was saying this in a joking manner. Sandy asked my wife "So, if I was to tell him to put his other hand on top of his head he will?" My wife looked at her and said: "Yes Mam."

Sandy looks at me and said, "Put your other hand on top of your head." I look back at my wife not sure what to think or do. My wife said "Do it."

So I did and my shorts fell all the way down. Sandy grabbed the bottom of my tee shirt and lifted it up to get a peek. Luckily for me, I was not going commando this day, as I normally do.

She said "Awe man, so close." My wife said "So close to what?" Sandy said with disappointment "I was hoping for a better show." With that my wife scanned the street back and forth like a pitcher in baseball looks back at Sandy and both smirk really big.

Before I knew what hit me Sandy looks at me and said "Lose your undies" I look at my wife and she said, "Lose em." I froze for a moment then I pulled my boxers right down to my ankles and stepped out of them.

I was starting to get excited because now I am standing down by my street wearing nothing but a tee shirt. I felt like Winnie The Pooh. We never discussed or did this kind of thing before so I was not sure what to do or feel. I was scared, nervous, and excited all at the same time if that makes sense.

Then she said "Yes this is much better, thank you." My wife said she was welcome. Sandy then said, "Hmmm, I am not digging the whole shirt thing."

Sandy took a step forward and grabbed the bottom of my shirt and pulled it off of me. Now I am completely nude and nowhere to hide.

Sandy laughed hysterically and I was still not sure how to react. I mean in 25 years I have only been with my wife and never in this situation. I was very embarrassed but very turned on.

To this day, I am not sure what the hell happened. All I know is that it was not planned but was so amazing. My wife and I talked about it and she said she did not know why it happened, but it did and she was glad it did and we left it at that.

Something that happened without reason, just living life. And I never felt more alive than I did that afternoon.