Thursday, February 16, 2012

Bottoming Success (NSFW)

All pics are from the-hairy-male.tumblr.com/.



Sorry for the lack of posting! I've been at my waterfront house where I've cancelled internet service for the winter.  It was an exciting and memorable Valentine's Day, that's for sure!   Spending about 14 hours in bed with a special guy was the sweetest, most intimate thing ever!  My first gay sleepover date!

It was the emotional connection was the most special thing and having enough of a shared history to know which sexual buttons will push your guy over the edge.  It was fantastic to wake up in the middle of the night to find your guy spooned up against you  with his arms around you.


I also bottomed properly for the first time, all the way this time.  My extreme level of relaxation helped, knowing that we had all the time in the world.  The glass of red wine I drank also played it's part.  However, this time was more successful than our last attempt largely due to my position.

Lying on my back with my ankles up around his shoulders was amazing .... who knew that this decrepit middle-aged fart could be so flexible?   I know  this will become my favourite position although I plan to experiment with the dozen or so different possibilities for anal sex.  It afforded me good fondling access to thighs and a furry torso and a clear view of his "O-face"... the best thing of all!


This was no slam-bam affair.  It was an extremely slow process and very gentle,  The pressure was fairly intense, but I was pain-free throughout.  It was a very special feeling to be "filled in" like that,  much like a woman might feel during heterosexual intercourse except much, much tighter.

There still wasn't much outright "pleasure" to be had for me this time;  I was losing my bottom virginity, after all.   But at one point, I wondered if his cock was pushing against my prostate, one of my G-spots.....  that had it's possibilities for pleasure, that's for sure.

It will take me quite a few more bottoming experiences for me to fully enjoy it, but I was enormously proud of myself for achieving this milestone.  After my first attempt,  I could very well have said, "Forget this idea!" so am very happy that I / we persisted.

I am finding this part of my journey all-consuming with respect to the time I'm spending on it.   Apart from the time we spend actually spend together, we do much texting, phoning and e-mailing throughout the day.

I am still getting plenty of messages and chats on pof.com and squirt.org, mainly from the 20-something flakes and 50+ dudes, many married and closeted but also from some experienced gay guys.   I have several 'irons in the fire' and at this point, do not feel the need to be exclusive although that may come soon.   However, my guy and I have agreed that we will not discuss any other guys who I may be hooking up with.  We did have these discussions at first but we found that opening that conversational can of worms did cause problems.

14 comments:

  1. So jealous that you found what seems like an amazing guy.

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  2. Glad to read that you had such a sweet Valentine's Day and I wish you many more.

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  3. WOW! Congratulations Buddy!I reckon you will never forget this valentine for the rest of your life and I'm very happy for you.When I do lose mine,I'll surely leave a comment (although it looks like it will take maximum 4 years ..lol)Happy Valentine's day from a friend who is feeling joy for you!Buddy one last thing if you dont mind do post a picture how this guy of yours look like,not a real picture of him,a picture of some other man that might look like him...so curious to see how he looks- James

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  4. Yay Buddy! I'm glad you passed another milestone on your 'coming out'. While I am very happy for you, I'm also quite envious. In the past we used to kid each other that we were both middle-aged bottom virgins. Now that you've graduated on to better things, I'm left all alone in the club :-(

    I noticed your absence from the internet over the last several days and suspected you were too busy with your intimate friend. I'm glad that turned out to be the case. You're a very special man and deserve all the happiness you can get.

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  5. :-) Congrats! I have to say you pick hot pics of men to post-- good taste in men! We have similar taste for sure!

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  6. I am so happy for you, and it obviously went very well with someone who took good care of you. From here on, it should get easier and you should begin to get that great prostate high. I wish I could do it in person, but consider yourself hugged for having aced one of the great landmark events in gay life.

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  7. anne marie in phillyFebruary 16, 2012 at 5:47 PM

    suh-WEET! my buddybear's cherry has been popped! smooches!

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  8. I am so happy for you. I must say, when you put your mind to something it gets done. Please write when you do get first Prostate orgasm. I know it will be amazing.

    So Cubby, when do you want me to come over. LOL

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  9. Thanks everyone! Yes, it was a very special evening and night in every way. I'm gradually making progress in adding to my sexual repertoire. I have much more to learn!

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  10. You sound relaxed and at ease - you've lost that hardness aspect of a virgin.

    Virgins are a tense lot; they look like an actress on stage imitating a cheap pain.

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  11. Wonderful news…as a newbie to the anal scene would you mind sharing how you prepared your ass for bottoming or should I write to you privately ???

    +++ Chip

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  12. Dr. Spo: you're too funny!

    Chip: I think I'll turn this topic into a post.

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  13. Yeah: I'm happy for you Buddy. enjoy life, and the beauty of sex with a man.

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