I’m a 27 year old male (the receiver) my bf is 51 (the giver) But before I got with him, I slept with his dad!
His dad (now 72) , was at the time the manager of where my sister and grandma worked. He came out as gay in the early 00’s. He was a nice bloke and always got invited to family gatherings & parties. When I was 16 and thinking about coming out, I spoke to him – he was super cool and told me how to do it, where to seek support and what to expect from people.
When I was I signed up to the Grindr app for Gay hook ups. After about 6 weeks, a message popped up and it turns out to the dad. We got chatting and exchanged a few pictures etc, in the end I went to his – we had a few beers and I gave him a BJ and went home. After a few more meets I finally agreed to let him fuck me. Lots of lube, condom’s and a strict understanding that when I said it, he would pull out. This worked out well for a few times.
As things got more serious, we decided to both step up things. We both took STD tests and stopped using condom’s and he introduced me to light bondage, which I loved. The feeling of helplessness and the humiliation!
Again after a few sessions we switched stuff up again, he introduced some of his friends and a few toys and even did a few risky meets (one of which was me being fucked in the back of my sister’s wedding car by 2 of them about 45 minutes before my sister was due to get in it and cum going all over the rear seats!)
One sex tape even got “accidentally leaked” when he was sending it to his mates. It got uploaded to a Facebook group for a while. A video of me tied to all 4 corners of a bed whilst having a baseball bat shoved up my arse, me giving a few men BJ’s then sucking beer out of there assess – not my proudest moment.
However after about 6 years we decided to call it quits and move on, only for me to start dating his son – who I got introduced to at my sister’s wedding!
He knows about mine and his dad’s past and has seen the videos where his dad isn’t involved, we’ve even made some of my own. But now barely a time comes where we see his dad and I don’t get aroused and give him a cheeky BJ!
Source: reddit.com/r/gonewildstories/comments/ck7ya7/sex_and_the_boss_mm