Alcohol does have a definite effect on sexual performance. From the Wikipedia link:
I personally have noticed that my orgasm while under the influence occurs roughly 2 to 5 times later than if I was not under the influence…sometimes it didn’t happen. But when I have not been drinking, I have no issues.
Experiment: Abstain from alcohol and masturbation for 1-2 weeks and then try again.
(time passes)
It’s been fifteen days now, and his girlfriend had to take a short trip out of town to care for an ill relative.
Suddenly, the neighbors hear, “LIKE A MOTHERFUCK!!!” bellowing from the bathroom.
I’ve had the same problem at times, and I’m younger and in better health than you. Alcohol is an absolute no-no for me before sex; it desensitizes my wedding tackle completely. Changing condom brands and styles also makes a difference, but I see that’s not part of your problem.
The one absolutely guaranteed method for being able to blow your load during sex is to starve the beast, as it were. How frequently do you masturbate?
Honestly, I usually go at it at least once a day. If I’m home alone on the weekends it can go as high as 5 -7 maybe.
I have been trying to not do it, but holy shit it isn’t easy. I mean I live alone and when I get bored, the porn just shows up on the computer monitor.
I truly do not know if I could go 2 weeks without doing that or not drinking (as suggested by a different poster). I can certainly give it a shot though.
I would urge the OP to make an appointment with a urologist and be quite frank about the problem. It may feel embarrassing, but he’s heard it before.
A half gallon of bourbon/scotch is about the equivalent of 40 standard drinks. Divide that by seven, and that’s 5 drinks a night. That’s way, way too much. If you are only getting a slight buzz, that is because your tolerance is so high. Seriously man, we are talking alcoholic territory here.
And Jerking it once a day and 5-7 on the weekends is a lot for a teenager, let alone a 37 year old man. Few people would be able to pull that off and have an orgasm during sex.
I disagree with Siam Sam here. You don’t need a urologist. There is an obvious cause to your problem. Stop drinking so much, and stop jerking it, and you will almost certainly solve the problem.
I only mentioned a doctor because the OP seems so worried about it. Sure, cutting the drink may work, but maybe it will take a doc to get him to believe that. Would be good to know there really isn’t any underlying causes other than that anyway.
I had the same problem when I was younger. I had intermittent problems with orgasming until I was in my 20s. It was probably a combination of new sensations, anxiety, intimacy issues, and other stuff. Condoms didn’t help things, nor did the huge though vague pressures of the possibility of getting the girl pregnant or getting AIDS (when I was coming of age, awareness was high, but facts about transmission and prevalence still very low).
In some ways it was a good thing. One of my girlfriends when I was about 19 or 20 told her roommate about my problem once. The roommate said, “Wait, he’s gone for five HOURS without coming!” and then slapped her boyfriend in the back of the head.
Also, some women took it as a challenge 
When I did finish, it was generally mind-blowing.
The bad things about it were chafing, eventual lack of natural lubrication, and cries for mercy (once you get past a certain point, going too long is just as unpleasant for women as dealing with a guy who’s too big) as well as severe blue balls on several occasions; which condition I can attest does exist and is extremely unpleasant.
My problem cleared up through experience, basically. I’ll bet that your problem is all the emotional baggage you’ve built up over the 10 years you waited for her. I daresay that there may also be trust and intimacy issues, depending on your relationship during that time and how she eventually became single. It will probably go away through time as you build your relationship.
In the meantime, don’t worry about it. Just have fun. Make the sex about contact, experimentation, and intimacy, and focus on an experiential mindset instead of a goal mindset. Sex is about the path as much as the destination. And as an added bonus, enjoying the little stops to “look at the flowers” or “try hopping on one leg” as you — ahem — walk the path leads to some almost transcendental orgasms when they do happen to occur.
Also, when you masturbate you can get an immense amount of pressure there that you won’t often get during normal sex. It could be that your body has gotten used to that amount of pressure before you orgasm and treats it as normal.
As was mentioned already by the “death grip” posts.
Is death grip the only (or even the foremost) reason why a frequent masturbator would have problems with orgasm during real sex? I would imagine it might cause a problem for getting it hard and ongoing, but lack of orgasm?
Couldnt it be related to you knowing your body far better than anyone else and knowing how to get the “most out of it”?
P.S: slight thread derail, does the amount of semen “in stock” plays a role in getting it hard (I dont mean no juice left, but low stocks)?
That’s probably it then. You’ve got to cut back, try every other day at first and then even less. 5-7 times on weekends? Why do you have a girlfriend? Cut that out.
Use a light touch and try to finish quickly rather than prolonging it. Practice doing it less and more quickly.
Eventually you can get to the point where you look and touch by yourself, but save the orgasms for the girlfriend.
5-7 times on weekends? Holy shit man! Try watching football!
And I just want to agree that this frequent amount of masturbating probably is the cause of your inability to come during sex, combined with the whiskey dick your operating with on a daily basis.
I seem to recall going cold turkey drinking wise can actually be a dangerous thing to do, so don’t do that without further research/medical advice. 5 or so drinks during the course of a day is a mild buzz. 5 drinks all in the evening after work is a bit more than a buzz IMO. Maybe just try cutting way down on the booze for one evening (in combination with not chicken chocking for a significant period of time). If that works, well, then look into how you can safely cut down on the booze.
Steady on, tiger. You only have to go like 3 days. Jerking-wise, that is.
There are so many things it could be on a spiritual level, from your former partners and fantasies to her’s and the interplay you and her may have had over the ten years.
Who is the one generally in control during sex, and who want’s to be.
You haven’t given a lot to go on but from this:
It appears like she has captivated you, which means taken captive, which does put you in a vulnerable spot, including any past fantasizing about her.
Again this is from very little to go on, but if it rings true, perhaps share this with her, if you think she could be of help releasing you (she may not be willing however).
Honestly, I have no idea what this means.
It isn’t you.
Well, let me ask you this: are you posting from a cage?
OK, fair enough, The simple way, is if she is willing, to act out fantasies and be open as to what you want, and explore deeper into them. In such sexual fantasies usually a power dynamic is present and pretty obvious.
The basic concept is the person in power, as part of the sexual play, release the other from the submissive position. Though that happens over time usually, not one episode. But it’s good in any such acting out that at the end the partner in power does release the other.
This may be either way, with you in power, or her.
An example, which may or may not be any help to you.
Lets say you had a fantasy of being tied up by her, in normal sex play, she might be the one who is on top, in fantasy play she might actually tie you up. (in this the power dynamic is much easier to see). This alone might help you get off. But also work into it her releasing you from the bondage as part of the play, which would helpfully release you again if she is willing.