27M here, this is the latest meeting in my journey of exploration. As I have posted the background for this previously, but the short version is that with the help of a female friend (38F) I have been exploring sexual contact and fun with other men.
Recently my friend helped me convince my neighbor (18M) to join in some mutual masturbation which led to us rubbing our cocks together a little. After this experience I decided to invite my neighbor over again last night to go even further. My friend has been chatting with him constantly, and giving him encouragement to explore for himself as well.
The results were intense. We started out watching porn on my TV sitting on the couch. It was understandably a little awkward, but we were both hard soon, and both took our pants off and started masturbating. After a few minutes we stood up and started touching the tips of our cocks together, rubbing them gently. Then I aked if he wanted to use my fleshlight. We passed it back and forth, I made sure he was extremely turned on before asking him if he wanted to double penetrate the toy. I could see he was extremely nervous, but he nodded. He was sitting on the couch, and I told him to scoot to the edge and open his legs. I got on my knees between his legs and slowly started to insert myself into the toy, the underside of my shaft pressed tightly against his. We used lots of lube and before long the fleshlight was stuffed and our cocks were locked together.