I find Jack a very smart and funny guy who has a great laugh. What I appreciated most about Jack was his brutal honesty and frankness during our conversation. It was fantastic talking to a guy exactly my age who is just starting to explore his sexual attraction to men; I feel we are kindred spirits. If Jack and I weren't separated by many hundreds of miles, I know we would be firm friends in real life.
This time, we spoke by means of Skype and were able to see each other. I saw Jack's torso from the chin down and Jack saw my mid-section, with me wearing my sexiest white bikini briefs. Sadly, we could only figure out how to record the audio of our conversation and not the video. Better luck next time!
This conversation is very long (15 minutes) and I cannot imagine anyone but the most devoted Buddy Bear and/or Explorer Jack fan who would be willing to listen to the whole thing. I've provided an index if you want to skip ahead to some of the juicier parts of our conversation:
Here is the youtube link to our conversation:
1:06 Jack discusses the differences between a 20 year old cock versus a 50 year old.
1:53 Buddy Bear talks about the best part of his hook-up with Hottie Nurse (hint: it wasn't the sex)
3:34 Jack talks about his sexual experiences with women.
6:03 Jack discusses his concerns about losing his bottom anal virginity
6:55 Buddy Bear discusses his underwear choices for our Skype chat
10:02 Buddy Bear and Jack discuss the joys of going "full frontal" on sexual webcam chats.
13:02 Buddy Bear discusses the hookup possibilities in his small town.
13:50 Jack expresses regret about not hooking up with men before the age of 47.
Hey all you experienced gay guys out there, do you have any advice for a couple of 49-year-old bottom anal virgins? We need help!