Street vendors in Naples, Italy used to hawk them to American sailors for a buck when our ship pulled in back in 1971. “Hey Joe. Flying cock and balls?” They’re probably still selling them today. Some things never change. 
Here’s one I found through googling: http://www.liveauctioneers.com/item/23712550_wwii-silver-trench-art-key-chain-cock-and-balls
FWIW, the scientific term is “apotropaic”, Greek root, meaning “that which wards off evil spirits”. The Greeks also were lucky phallusmongers.
Good luck springing that one in conversation.
Ranger Jeff Respectfully, not a chance. My zeide Herman had plenty of pins with propellers on them. He also had a winged penis souvenir. There is zero chance it was anything but a winged penis.
Oh and since it is veterans day, I’d like to salute all the vets on the SDMB. Cause, freedom isn’t free.
I just was talking with my Grandma, who has 2 of these. 1 from her late husband, who was in the Army and my current Grandpa who is 96. The winged Penis was actually an award given from your commander to you for a job well done, so similar to being “coined” today. It was “from the head Prick of the regiment”. They would wear them on their collars or as a tie clip.
Now you know. I’ll try to get him to tell me more about it, but wanted to share what I had found out tonight, since there seems to be a lot of people looking for the information.
Welcome the SDMB, NrsSteph.
I am curious, what country’s army did your relatives serve in?
I remember the “hey, Joes” in Naples in 1972-73, and I clearly remember them being for sale. Never could bring myself to buy one
Perhaps a small penis got a hold of a red bull?
Simply_Cats, does it look like any of these?
My father was career Navy, and on one of his Mediterranean cruises he got a pendant like that. He said it was called the “flying cock and balls of Pompeii”.