A little background:  

I am an early 50's hobbyist.  Been at the hobby almost 20 years.  Have also had various non-pro sexual relationships over the years with mistresses, sugarbabes, 2 marriages, and several girlfriends.  All the non-pro relationships eventually became condom-less sex.  All the provider experiences were safe sex at all times except oral.

I find myself not being excited about seeing providers any longer because of the need for condom use.  At my age, sensation is drastically cut with the condom even with proper inside lubrication and a larger size.  I've experimented with several brands/types/sizes, etc.

It's the age/condom combination that has become the problem.  When I was younger I had no problem with condoms but now it is a true deal breaker for me.

With condom-less sex I can stay hard and have 2 or 3 ejaculations through intercourse over the course of 3 hours (or longer).  With a condom I am finding that I have trouble having an orgasm even once.

I expect that I will hear the "female condom" advice and I will try that once I find a willing provider.  I have tried V, C, and L and those meds did help for a time.  I have used them for about 4 years but now find them less effective than they they were before.

I am considering the complete end of my hobby participation as a result of this issue but that doesn't make me smile.  I'm hoping to find a solution to my dilemma.

Is there anything that I haven't considered?  

I am assuming that it's fairly typical for men of my age to have this problem.  I am correct?  What have the others in this situation done to help with sensation when using a condom?

There's no need to orgasm with the cover on. I'm assuming you can still keep it up and have P/V intercourse? Enjoy what you can with the cover on and ask the ladies for some help finishing. A great BBBJCIM or a great hand job (highly underrated in my book) can lead to some mind blowing orgasms.

In addition, ED drugs can decrease sensitivity and make it harder to orgasm. If you don't need them to maintain an erection, don't use them.

A provider pointed me to a study which showed delayed O with ED meds.  I generally do take the minimum dose necessary.  V can be cut (warning it tastes like crap) as my MD directed me to.

I suggest you not be focused on multiple shots on goal...   I'm a one shot guy now due to a medical condition...  but that does not stop me, in fact I am a better lover now because I can focus more on my partner knowing I'll get mine on the last course.  Forget the Indy 500, it's about the journey & all the mountains & valleys we get to emjoy...

The most intense O I've ever had was a HJ, followed by a BBBJ/CIM with some porn style hand work.  

No, your experience is not typical of a man in his early 50's at all.

I'm going to be blunt, so if what I say upsets you, I'm sorry.

Regarding issues with erection, lose weight and see your doctor immediately. It is not at all typical for a man in his early 50's to be experience difficulty with erections, even with the help of ED medications.

Regarding loss of sensitivity, stop masturbating. I'm going to guess that you masturbate on a daily or near daily basis. All that masturbation desensitizes your cock, making it more difficult to achieve orgasm without direct stimulation. Cut back to once weekly, or even less frequently. You will be amazed at the increase in the power of your orgasm, as well as the increased sensitivity.

You're spot on about masterbation but why do you assume poster needs to "lose weight"? The majority of men over 50 experience such challenges because of poorer circulation, enlarged prostates, sex over 50 isn't as physical as much as "between the ears" & other reasons. I'm an in-shape 56 yo but have experienced the same symptoms. Doctors & my own research have educated me to how common this is so I go with the flow & enjoy the total experience, as another poster suggested.

Dear Sexy Man,

This is very common, and I can only imagine it is very frustrating.

If there are not too many overwhelming medical issues here is what I do:

I have made it a habit to use female condoms. Without fail and 100% of the time I get the same reaction from men who have never used one before....it feels like they are barebacking....they stay hard as a brick, and release a few times.

Used correctly and with enough lube, it is wonderful for me and them. Sometimes these are men who seriously are convinced they are having ED issues.

My advice to you is: do not masturbate for a few days before you see your lady of choice, watch your diet, book for multi hours, book a very skilled provider mature provider (not necessarily age mature, but mentally grown up, and informed) who uses female condoms and RELAX.

... I have found that, as Allure has alluded, female condoms are WAY better.

I HAVE met a provider who knows a few pretty good tricks for making a regular condom feel better than it would ordinarily. And in her case, it feels pretty close to bareback amazingly enough.

But overall, I think Allure is right. There are ladies out there who will use female condoms and these are definitely a great approach.

I'm not overweight at all.  I have a 33" waist and I work out 3 - 4 times per week with weights and on an elliptical trainer.  I'm in good physical shape.

I don't masturbate more than twice per week and I always keep hands off for 3 days before I know I will be with a provider.

The condom issue is fairly new for me.  I did not have the issue until about a year ago and nothing changed in my health or activity level.  I attribute it to age.

You say that it's not typical of a man in his early 50's but I have read otherwise in several place.

I think that you're just wrong.  (being blunt is not a way to respond when you don't know all the facts and you don't know the person to whom you are speaking.)

While not all of the advice given may apply to you, there is a lot of good suggestions here for the majority of hobbyists.  Age may affect libido and what we are used to experiencing, yet it should not affect how the condoms themselves feel. The issue is most likely (barring physical concerns) mental/emotional as you yourself state it was not an issue before, and that your other idulgences have usually become affairs with no party hat.

If PV ejaculation is the end all be all for you (which may be the sum of your issue) and none of the suggestions that come of this thread work for you, please do retirefrom hobbying and seek your condomless pleasures in other arenas... You are entitled to your preferences as long as you have a willing partner!

.02

I love to watch whoever I am with getting off on me physically. It's not as exciting watching it squirt into a condom as it is watching it cum all over my body! It's like an award for my performance and vice versa!

It ain't a myth. Men over 50 simply can't perform the same way as we did when we were young bucks. Life gets better & we can still have fun but - anecdotes aside - to expect an over 50 yo guy to defy nature is biologically & scientifically untenable.

Being height/weight proportionate and exercising reguarly are certainly important, but you are describing a persistent issue with blood flow. See your doctor. You can still suffer from heart disease even without the commonly accepted risk factors.

Why do you have to bring our date into this?

Yes! I love the female condom! It feels soooo fucking good when the lovely ladies use it!

I hate goddam condoms, but it's a necessary 'evil' in this sport.

But knowing I'm not wearing one? To me, it takes away a lot of the mental crap that goes thru my twisted skull!

Hey! I grew up in the 80's! WTF!!!

especially to be careful about possible heart disease even when exercising and physically fit. I had a good friend younger than you pass out while driving due to a heart condition. Look at Arthur Ashe...

Also, do not discount the problem between the ears. I went to the doc about problems with an SO, and he blithely diagnosed psychological issues. I was PISSED, and he was right.

I am overweight... pushing 50... and I can pull off 2-3 in an hour with the right gal.

Keep at it.

Yes....Stop masturbating. Sensitivity dramatically improves

You said, "With a condom I am finding that I have trouble having an orgasm even once."

Keep the condom on, just switch the hole.

a provider who uses them?  Not mentioned in their reviews.  Haven't seen it posted in websites.  Ladies don't want to discuss anything like this prior to a date (unless possibly a regular could get away with it).
I can see this guys point.  Last civvie date, no latex, no problem.  Throw a condom on there and It will not cum, if it stays hard for the whole game! Fortunately, many providers know this is common, and don't jump to some medical conclusions, or weight/height/BMI horsecrap like DR. SOF above.
There ya go, an Idea for the new and improved TER...a FCU (female condom user) registry!

OK, I am into my sixth decade, and the plumbing doesn't often work.

I haven't popped using a condom in years until I met someone who used the female condom, and then things changed.

But, life isn't over because you can't fuck. I actually prefer a great BBBJ anymore and damn if I haven't met a bunch of ladies who can make me come multiple times! And playing with a great lady still makes the hobby worthwhile.

"And playing with a great lady still makes the hobby worthwhile."

I second that!

Whether or not she uses female condoms, that is.