Wednesday, December 21, 2011

Sexy Talk with Explorer Jack, Part 2
Yesterday, I had my second exciting conversation with that hookup-king, Explorer Jack.   I posted about that conversation here, but we removed the Youtube link after a couple of days.

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!


  1. The only way to know what you enjoy, sexually, is to explore it safely and sanely. IMHO, for your first time, if you are a bottom virgin, don't just bottom for any guy willing to top you (they will be plentiful); find someone you feel comfortable with, attracted to, who makes you want to explore what it would be like to have him inside you. Chat a bit, build some trust, explain your virginity and make sure they are willing to work with you and respect your directions. Before then, experiment with sex toys and stimulate yourself, anally, with fingers and toys to see if it feels good to you and induces a desire to feel more. Start with light anal play with another man: insertion of fingers during masturbation, oral sex, rimming, etc. Some may feel this overly cautious, but until/unless you know it's something you like doing and get pleasure out of,caution is the smarter way to go. The first time I bottomed, I was in highschool, he was straight, I was just a hole for him to put his dick in and it was awful and painful. Granted, we didn't know what we were doing, but hornyness, curiosity, and ignorance got the better of me and it left me with a revulsion for the act and a fear that I would have to "put up with it" in the future to have sex with men. Years later, I met a man who turned me on ferociously, knew my first experience and offered to take it slow. With him, I discovered the amazing experience bottoming could be for me and it became the center-stone of my sexual behavior throughout the remainder of my sexual relationships until I ultimately lost the ability with surgery that left me unable to be a receptive partner again. You may not enjoy bottoming, so don't feel bad if the experience isn't enjoyable for you, but odds are better that you may have a positive experience if you don't rush it, do it with someone you have some level of trust with and let it happen, slowly and easily and comfortably. And if you start to have doubts or get nervous, you may want to wait until a time, place or person helps relax you and puts you at ease. Good luck in your explorations.

  2. Thank you Sean, for taking the time to provide such excellent advice. It's much appreciated! Hugs.

  3. His advice is excellent, well worth following. Esp the trust aspect. Then the part of toys and playing is a very good thing. Even if you aren't destined to be a bottom, it can be fun and feel good.
    I really enjoyed your chat with Jack. One word for both of you, the anal region will stretch if done properly. My guess is you have passed things bigger than any cock you will receive. Personally, I never thought I would bottom either until the chance presented itself. I was lucky in that it was with someone I had been having sex with for a long time so we were comfortable each other. And I have to tell you, I think a prostate orgasm is amazing. The first time was almost funny. I didn't really know what was happening at first. I mean nothing was touching my cock and I was spurting. So, do what is comfortable and enjoy the journey.

  4. I'm 22 and virgin both cock and anal...i sincerely need a help as i have this doubt and its about sex and i cant ask my dad or my friend since im gay and still in the closet.....the question is do a bottom feels sensation or enjoy during anal sex?i'm asking this because i have read an article stating the bottom?reciever does not enjoy or have sensation during anal sex ..however i have also come across article who said the opposite...if any of you had bottomed before pls clear my doubt and I'm sure Buddy Bear will find it useful....and one more thing ,will the anal lose its control if you have lots of anal sex(like unable to contract or expand)....thank you for will be helpful for me and other guys.

  5. Man, do I have a LOT to say. But I will save it for a private email.

    @Anon: Yes, you do feel sensation during anal sex.

  6. Hey Anonymous: On anal sex, you would do well to read the advice of idleeyesandadory, skier and RG, above. If you e-mailed any of them privately, I'm sure they could provide more reassurance.

    Also, there are many websites which are devoted to the topic such as this one and this one. Keep in mind that all gay men do not do and enjoy anal sex .... do whatever is comfortable with as you progress, safely and with a partner you can trust.

  7. thank you buddy bear and other wo replied my questions....i read both the article you said and found it helpful...thanks again buddy bear i really appreciate it..and regarding the e-mailing RG,i dont know his e-mail address.if RG or anyone else willing to share their experience and friendship..i would be glad if they leave their e-mail address here...anyways thank you buddy bear again-James

  8. Anonymous, here is my permission for Buddy to give you my email address if you would like it.

  9. dear Buddy Bear,I have sent you a e-mail...thanks again and I'm glad for the friends i had made and will make through this blog.James


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