He is the son of an older couple that I know through work and we have known each other for a few years. I’ve asked him about girlfriends and relationships in the past and he always just dodged the questions. It finally came out that he had never been in a relationship so I invited him out for drinks with me and some other people we both know. When we were all going home offered him a bed at my place since he couldn’t drive home and a taxi would be expensive.
When we got back I offered him another drink and sat down right beside him. I brought up the no girlfriends thing, he was embarrassed and tried to explain. I told him to kiss me, after a few more prompts he did. We kissed for a while then I took him to bed and rode him.
It was awkward but he wasn’t too bad surprisingly. Obviously no experience but I’ve definitely had worse haha.