To Cum or not to Cum

All pics from http://guyscuddling.tumblr.com/. 

After our amazing coffee date, we have had three fantastic, lengthy intimate encounters.  These occurred in my home in the marital bed! (I still need to get my head around that one.)

The intimacy was incredible, both physical and emotional.  He is a bit older and more experienced, gentle, understanding, considerate, funny, charismatic, sexy as hell and has the libido of a man twenty-five years younger.  

He says I'm am amazing kisser and he certainly is as well!   He says I give the most amazing blowjobs .... fantastic ones!  (and just between us girls, I have to agree.  Damn, I'm good!!)   So what's the problem in this shangri-la of gay sex?   I haven't been able to cum while having sex with a man.  Not ever.

To put this in context, it is important that I describe my sexual history.  It would normally be embarrassing to reveal all these details, but, what the hell,  only two of my readers have ever met me  (Hello Cubby and Greg!), so here it goes....

I was an extreme late bloomer sexually;  I masturbated for the first time at 23 and lost my virginity to my future wife at 28, a few months before we married.  During the first year of marriage, my wife had sex 7 - 9 times per week and I loved it!.... absolutely wallowed in it.  This gradually dwindled down to no sex at all, due to the stress and exhaustion of having three children under the age of four.  The biggest reason for our sexless marriage was my emerging attraction to men although I didn't recognize it at the time.

However,  I've never had problems cumming with my wife or by myself during all those sexless years which followed.    My problem is:   I haven't figured out how to cum during man-sex.

During my previous two encounters with men, both attempted blowjobs but I didn't cum either time.  These would have been the first blowjobs I'd ever received, as my wife refused to attempt one.

This was understandable;  as a 48 year old gay virgin, I was exceedingly nervous with Hottie Nurse.  In any event, his blowjob technique would never have worked on me.  (a lollipop lick here, a cock head nibble there,  a tongue flick over my ball, all separated by long pauses.)

My second BJ encounter with Stoner  Dude, in a apartment reeking of cat pee, lasted all of 30 seconds.  His technique of gnawing on my cock head caused me to shout out in pain and sent my legs into spasms.

In one of our three encounters this week,  attention was paid to my cock head during the blowjob which became irritated and painful. When I wank off, I usually don't touch the cock head at all.  In the next encounter, my cock just became desensitized after several hours of heavy petting.  In both cases, I was nowhere near to cumming.

All the turmoil which going on in my mind is clearly not helping.  These include  an extremely serious crisis involving my wife (but having nothing to do with me), job demands, my medical concerns, financial worries, the on-going stress of constantly "showing" the house to sell and the newness of engaging in man-sex.

Throughout, my friend has has been kind, helpful and open to communication.    We decided that near the start of our next encounter, I should just wank off in my usual, no-fail manner, with him watching and assisting if possible.  Just before the very end, he might even take me into his mouth.    I'm hoping that this 'cumming success' will help me over this hurdle.

I described my problem while online chatting with a mid 40s guy staying at a local hotel.    He offered this comforting comment:
"I am familiar with not being able to come. I find that a challenge sometimes, but primarily with someone new.  I need to feel safe and comfortable with someone and sometimes that just doesn't happen up front ... especially if I hold off coming too soon and the "urgency" is gone. Anyway, I expect with all the things you have going on in your life that it's your head not letting you cum, not your privates. Things will settle for you and return to normal - stay positive."