Saturday, February 18, 2012

Prostate massage + hand job = cum


For Sean`s Dogably Pawfect Saturday, here is a cute guy - cute dog pic from cuteboyswithdogs.

The day after my bottoming success, I had coffee with with a 52 year old IT nerd who I`d chatted with on squirt.org.  Unlike all the closeted, married guys or twenty-something flakes I'd been chatting with, he was the first really experienced gay guy I`d met online. We arranged a  hookup for the next day.

As I drove to his house, I wondered, "Why am I doing this?"... but summoned up the courage to continue. I was on my quest for the Holy Grail... an experienced gay guy who knew his way around a man's body and could teach me a thing or two about gay sex.   Despite all my hookup success, I still hadn't cum in the presence of another man and I was deeply distressed about this.

http://gaymalelove.tumblr.com/



Bruce was very nice but not particularly attractive and, despite thirty minutes of passionate kissing and naked full body contact (two of my most favourite things!), my cock was a limp as yesterday's lettuce.  I just wasn't feeling it ... it was so mechanical!

He took his role as my mentor to gay sex very seriously and we discussed the possibilities to get me over my mental "not cumming" barrier.  We had a very long talk about my sexual history and I began to see what a sweet, compassionate man he really was.  He made me lock my eyes with his as we resumed our activities ... to deepen our emotional connection.  I found this very difficult to do.  Suddenly, our encounter "clicked"  and began to feel some passion in  our encounter.

I agreed to a prostate massage / hand job combo.  He inserted a well-lubed finger while doing a hand job with the other.  Such was his skill and gentleness that I had to ask him if he was at my prostate yet.  After some time, I felt shivers, then waves of trembling from my head to my toes with much involuntary writhing and moaning from me.  Fantastic!

Afterwards, he told me that I was "on the edge" for about two minutes and could feel my cock and prostate in spasms, ready to squirt.  Then, suddenly, everything stopped. I'd lost the edge. 

I finished myself off in about 20 seconds while he continued the prostate massage.  It was insanely intimate.   I'd had my first orgasm with another man.... a gusher!... incredibly intense.

He had a few very interesting observations about me:
1.  I needed an emotional attachment with a guy to have sex with him.  It was only after our intimate conversation that I truly began to 'get into' our encounter.

2.  He declared me a "true bottom" and said that he pushed his finger only half way in... and that during the prostate massage, I was rhythmically pushing my prostate onto his finger.  He said it was like my prostate was yearning for his touch.

3.  I craved and enjoyed kissing and full body cuddling, the closer and tighter the better.
http://gaymalelove.tumblr.com/


4.  He said of all the hundred or more guys he's been with, not one had his mind "shut down" his orgasm like mine did.   He said  (and I agreed with his insight) that I still must be carrying a great deal of guilt about having sex with men.  Although I was physically capable of having an orgasm, my mind was a barrier which was not allowing it to happen.

5.  He was certain that I had now overcome my mental barrier to gay sex... (I hope!)

Afterwards, I told him I'd feel selfish if I didn't reciprocate, so we agreed that I'd give him a hand job.   I decided not to do a prostate massage.... I'd had enough learning for one night! 

Much to my surprise, giving him a hand job was the hottest thing ever and I got rock hard again,  harder than ever, despite having just cum.  He held onto my cock while I jerked him off.   He provided much instruction as to what worked for him and with much moaning and writhing, he came. I felt like a sexual superstar!

I'm thinking that I will visit my new friend sometime soon for my next lesson at the Gay Sex University.

8 comments:

  1. Soon you will be an 'old pro' just like the rest of us.

    ReplyDelete
  2. Hey Buddy Bear. Great story and a great learning experience.

    A word of caution. This guy may be spot on, but he may also be full of shit! Don't take it as gospel. Everyone is different. Everyone responds to different things. Listen to your heart and then make your own decisions. The good thing is having some (safe) fun and discovering it all!

    ReplyDelete
    Replies
    1. Jack, don't worry, I very much know my own mind and I'm not easily swayed or lead. I`m pretty sure that I`ll end up being "versatile" and hope to enjoy being a top and bottom equally. As to his theory about my feelings of guilt, I have a sneaking suspicion that he may be correct.

      Delete
  3. Replies
    1. Thanks for commenting, but I don't know those symbols mean. Google tells me that it might be some letter in the Korean alphabet!

      Delete

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