He still doesn’t know I watched that… but how can I tell him? Do I dare ask if he’ll let me join?

QUESTION:

I’ve got several roomies. One I have a special crush on. I found him online doing a great show in a jackoff chat room. He still doesn’t know I watched that… but how can I tell him? Do I dare ask if he’ll let me join in the show and do it with him on cam?

RESPONSE:

In this specific personal situation, I cannot tell you what to do. However, I can explore a bit of what might be going on to help you figure out your best approach. Clearly you find this roomie attractive. Apparently, you have not had any direct intimate experience with this man, at least not so far.

Your best approach is probably to create a conversational scenario of introducing the subject of masturbation, specifically, even if you have talked about it before. You can segue into the subject of chat room masturbation. If this doesn’t lead to your roomie offering more specific information, you might mention that you are thinking of doing a show in a chatroom yourself.

That might be a good idea! Watch Go ahead and plan to do such a chat room show, and approach it from your own angle. Maybe take the plunge and ask him if he’d like to watch your show. If he responds with any enthusiasm, you might propose he join you in your own show.

By this time, the situation ought to be clear enough to him, and he will probably have figured out that you saw him in the chat room. If he asks you, confess it fully, and put it in terms of great appreciation, how much you enjoyed seeing it. If the situation gets this far, either he might invite you, or you might ask him. Whether or not it’s on cam, it could be nice.

But prepare yourself. The worst he can say is “No,” and he may have his own reasons. He really needs no excuse. We all know there are still weird attitudes around masturbation. Also, there is a major difference for some guys between online behavior and in-person. To do a show together would require masturbating in the same space, at minimum. For some guys this would be a threshold they are not ready to cross.

On the other hand, he might find the whole thing just as exciting and enticing as you do! Start off your communications on a strategic tangent, to test the waters. Then sense when it’s hot enough to get down the business at hand, or “at hands,” (plural) if it works out well!

A note from The Batemaster: I’m honored that the guys at BateWorld have asked me to respond to some questions from male masturbators around the world every week.

Always check with your doctor about any issues you might be experiencing with your sexual organs. Prompt diagnosis and treatment are important. This article’s purpose is to inform and entertain readers and is not a substitute for medical advice or treatment.