Expert: Chim Hedo - 1/22/2009

Question
When I first met my boyfriend he told me he had always fantasized about seeing me with another man but didn't believe that he would be able to handle seeing me with a man taking me on fully sexually,and the most he thinks he could handle would be to watch me be undressed by a man.
A month ago he wrote out a list of sexual activities I would be interested in. Some of them included but were not limited to: web cam with another couple, same room sex with a couple, buy a real-looking dildo and put on a show for him.
so far, I have only done the  dildo show for him. About the same time as the show, we began looking on craigslist for couples in New York(he suggested this as he said that way we wouldn't be pressured to meet with them...weird I know) to cam with. So we created an email together(so we could both see what was going on) and began searching. didn't find anyone that stood out/wasn't fake. Now, yesterday, he brought up to me that he had been emailing a couple in our city on his own email and said they were hot. He told me he would chicken out most likely, so I'm really confused about where he is going from this. If you could, please help me understand this situation from an outsider's perspective. I can't/don't have anyone to talk to about this

Answer
Hi Kristina!
 Let's try to understand this together.  Sounds to me like he would be game for a little sexual exploration, but is afraid to try.  You have really indicated your comfort level with any of it.  So you need to ask him the questions, and he needs to ask you the same.  What situations would make you comfortable, why, and uncomfortable and why?  What is the stability of your relationship?  I would also ask why he emailed another couple under his email, when you had an agreement to set up and email together to pursue it.  Secrets in the lifestyle is not a good way to start out.  You are confused about where he is going with this.  End the confusion.... ask him.  Rather than Craig's List, try out some Lifestyle websites.  Lots of answers are there, and may help you two to get the ball rolling and start communitcating.  Some sites will give you the opportunity to cam with other couples.  Start with that until you find your comfort level.  I can't stress it enough..... talk , talk ..... talk!!!
Good Luck,
Chim