Advice for a 40+ Year Old (Gay) Virgin

[AlexThompson]

I know this probably isn't the correct forum, but I need true sexperts, and you guys always have the best advice.  Simply put, I have spent my entire adult life without ever having penetrative sex with a man.  

I have had fun with lots of guys, including in Thailand, but never had the full experience.  I came of age during the AIDS era and have been gripped by fear ever since.  But now I'm willing to try, however I don't know where to begin.  To be honest, I don't even know if I'm a top or a bottom.  

My question is...how would YOU re-do losing your virginity?  Would you hold out for that special guy or would you go to an "expert"? 

[vinapu]

I don't think you want plan that,  try to find the guy you like and are comfortable with and let things take its course naturally. When you feel your blood it's at boiling point , you will know now it's time.

[spoon]

Beauty of hiring guys, u can dictate how u want your session to be. Since u didnt know if you are top or bot, and if u really want to start to try, i suggest for you to find a verse so u can try flip flop and see which u like better. 

Not sure about others, but for me, first time isnt always what you would cherish. In reality, sex gets better with practice lol

[ggobkk]

I'm sure there will be several opinions voiced and suggestions made.  Before they begin, I admire your honesty and openness.  I, too came of age as AIDS arrived and can understand the hesitation.

My own response is go to an "expert" and be as open with him as you are here.  I suspect you won't be the first and your expert will make it a valued learning...

[GoldMember]

I think you do need to plan how to do it. If you wouldn't need to plan for that it would have probably happened till now naturally in at least one out of many encounters you had with guys. But it seems that something is making things a bit harder for you regarding anal so in my opinion getting help on that is a preferable way of choice.  

I agree with @ggobkk that an expert will be beneficial for that manner. Not a regular bar boy but a highly rated guy from RentMen. These guys, if they are highly reviewed, have seen and done it all and you will be able to discuss everything with them freely. I would even start with a first encounter with non anal just to see if you get comfortable with the guy. I also agree with @spoon regarding that you should lower your expectations on enjoyment. It's a barrier that needs to be crossed and after crossed you might start enjoying that. 

If still in difficulty, and this subject is of importance to you, I would recommend seeking help with a sex therapist, preferably one with experience with gay men. If what you are experiencing is indeed Aidsophobia (which is not that rare with gay men), it can be sometimes related to hypochondria and/or some variation of OCD. A professional therapist would know how to make a better diagnosis and help you overcome the barrier with some guidance and support. 

On the other hand, you can decide that this subject is not that important to you and identify as Side: https://www.urbandictionary.com/define.php?term=Side. 

Good luck!

[spoon]

Ive read multiple experience sharing on utilizing of PreP and how it took away their fear of having sex due to Aids/HIV scare. Granted most of this story are either with HIV poz partner and/or those who bareback or lack adherence to regular condom use, there are some users who took it to reduce their own paranoia of the disease even when they religiously wear condoms. This is due to several incidents of condom slippage, breakage, under alcohol or drugs influence cases that makes using condom not their highest priority. Something to ponder as an added tool of HIV prevention. Of course this is totally an individual choice.

[zombie]

My advice: go to an expert. Find a popular bar and ask the ma ma san to recommend the best top or bottom available. of course you must use a condom.

[Moses]

Many-many years ago in Prague I took phone book in street phone booth and made choice from call boys adverts. When he arrived I told him what I'm virgin and need lesson "what and how". Then we spend 2 hours in explanations and practices. 

[Londoner]

Many gay men don't do anal sex. If you are enjoying your current practices, why is it so important to change? 

[spoon]

5 minutes ago, Londoner said:

Many gay men don't do anal sex. If you are enjoying your current practices, why is it so important to change? 

Maybe FOMO is in play? If u never try, ull never know

[AlexThompson]

Many thanks for your thoughtful responses, gents. I just assumed that anal sex is one of life’s great treasures that I’m missing out on, however I guess my follow-up question is...

Is anal sex so incredible that every gay man must experience it?  Is it something you could easily live without?

[Boy69]

At first anal first -as bottom- is very painful and unpleasant experience however after practicing it is incredible , others will be top only and some can be versatile.

Intercourse sex is great treasure you are missing I guess maybe you are hypochondriac and this is the main reason you are avoiding it on fear you'll be infected with HIV or other sex deseas ?

[vinapu]

24 minutes ago, AlexThompson said:

 

Is anal sex so incredible that every gay man must experience it?  Is it something you could easily live without?

considering tittle  of this thread answer to second question obviously is 'yes' but you need to answer this question : is   easy life worth living?

[spoon]

Its not just incredible, its addictive and as ubdoubtedly reported here and most of the gay forums elsewhere, even those in their 70s still actively seeking for it. Having said that, it is still not for everyone. Certainly straight guys went ok without ever having anal and pure top gay never experience bottoming, and pure bottom gay never top a guy. 

But like i said before u will never know how u feel about them until u try it. And at the risk of sounding like a broken record, with sex, specifically anal sex, especially bottoming, itll get better with practise.

[DrimVoiz]

As a versatile, you will not have the full sexual experience if you did not do anal sex, this is based on experience only and personal opinion only so I did not intend for an argument, okay?

When I visited BKK 4 the 1st time, I never, ever plan or even imagine 2 lose my virginity...until I met the go go boy from Dreamboys which I think got all I look 4 in a man...I even call him Mr. Perfect Guy...and I admit, the 1st time I really got hurt, he was only able to insert it, but on our 2nd encounter, WOW, he made me relax and we did it in a lot of sexual positions...I guess if u really like the boy and he is really your type, u don't mind the pain, but the pleasure after...now he becomes my regular and he always made my trip complete!!!

But of course I also enjoy twinks bcoz being a top is a bit easier than being a bottom, lol!!!

[anddy]

I agree with other's in saying never try never know..... 

To try to top should be pretty easy and straightforward. Bottoming is not so easy, and the key to bottoming IMO is:

1. you have to really want it (in that very moment, not just in general)

2. to relax there.

 

To get to the state of really wanting it probably takes two ingredients: the right guy and a high degree of horniness. Note: Horniness breeds desire, and desire kills anxiety. Which leads to the second point, to relax. Overcome your anxiety. If related to HIV, that should be easy as (i) there is no need to panic anymore anyway these days, (ii) use condom and (iii) consider Prep (in addition to (ii) of course). If anxiety is related to anticipated pain, there is no need at all for there to be any pain at all. Just learn to actively relax those muscles there. Train and practice with your fingers (increasing the number of fingers as you go), and probably with some, uhm, tools like a dildo (or a not too thick cucumber will do, too). Here @spoon's observation and advice is very true, practice helps. So practice by yourself, so you'll be prepared for the real practice with the real tools.

 

[spoon]

Btw, nobody mentioned about size here. For first time bottoming, u probably wont want those expert that have a huge endowment to begin with. And lube is very very important. Maybe u should get better quality lube to start with. Not to scare you or anything, but pain can happen, usually due to either not enough lube being used, or due to not relaxing the muscle. One more thing is position. My suggestion is maybe try to start with you on top so you have full control. Again, this is really personal preference kind of thing, so if it doesnt work, try different positions until u find one that is comfortable for both u and the your guy.

[lotus123]

13 hours ago, AlexThompson said:

Many thanks for your thoughtful responses, gents. I just assumed that anal sex is one of life’s great treasures that I’m missing out on, however I guess my follow-up question is...

Is anal sex so incredible that every gay man must experience it?  Is it something you could easily live without?

I would be very sad if for some reason I could never have anal sex again. 

[kokopelli]

14 hours ago, AlexThompson said:

Many thanks for your thoughtful responses, gents. I just assumed that anal sex is one of life’s great treasures that I’m missing out on, however I guess my follow-up question is...

Is anal sex so incredible that every gay man must experience it?  Is it something you could easily live without?

It is an honor that I dream not of.   Shakespeare

[GoldMember]

16 hours ago, AlexThompson said:

Is anal sex so incredible that every gay man must experience it?  Is it something you could easily live without?

I must say I do not agree with the majority's opinion here. Yes, for me anal sex is fun and sometimes a crucial part of intercourse. But I had a lot of very pleasurable and intense sexual encounters that did not involve anal sex. 

But that is just me, I know some people just don't like it or prefer to avoid it. And I know a lot of people that cannot imagine a sexual encounter without it. 

But all of this does not matter, neither my opinion nor others'. You are the sole person who can answer that question.  

[DivineMadman]

36 minutes ago, GoldMember said:

I must say I do not agree with the majority's opinion here. Yes, for me anal sex is fun and sometimes a crucial part of intercourse. But I had a lot of very pleasurable and intense sexual encounters that did not involve anal sex. 

But that is just me, I know some people just don't like it or prefer to avoid it. And I know a lot of people that cannot imagine a sexual encounter without it. 

But all of this does not matter, neither my opinion nor others'. You are the sole person who can answer that question.  

+1

[vinapu]

4 hours ago, GoldMember said:

I must say I do not agree with the majority's opinion here. Yes, for me anal sex is fun and sometimes a crucial part of intercourse. But I had a lot of very pleasurable and intense sexual encounters that did not involve anal sex. 

 

it never happened so far but I always say  that my  best encounter would be if I take guy just for hand holding session and on departure will ask him if he can come for the some in the afternoon. At end of day is whole guy who counts , not just his hole.

[DrimVoiz]

On 23 October 2019 at 11:10 PM, DrimVoiz said:

As a versatile, you will not have the full sexual experience if you did not do anal sex, this is based on experience only and personal opinion only so I did not intend for an argument, okay?

When I visited BKK 4 the 1st time, I never, ever plan or even imagine 2 lose my virginity...until I met the go go boy from Dreamboys which I think got all I look 4 in a man...I even call him Mr. Perfect Guy...and I admit, the 1st time I really got hurt, he was only able to insert it, but on our 2nd encounter, WOW, he made me relax and we did it in a lot of sexual positions...I guess if u really like the boy and he is really your type, u don't mind the pain, but the pleasure after...now he becomes my regular and he always made my trip complete!!!

But of course I also enjoy twinks bcoz being a top is a bit easier than being a bottom, lol!!!

Also, if I may add, aside from condom and lube which is a must-have, Mr. Sex God offer me a popper...and it made me relax and remove the pain since it will open-up your hole...ooopppsss, sorry, no offense meant...or was it bcoz Mr. Perfect Guy f*ck*d me the previous night?! Anyway, I'm still not that good at bottoming, haa haa!!!

[DrimVoiz]

16 hours ago, spoon said:

Btw, nobody mentioned about size here. For first time bottoming, u probably wont want those expert that have a huge endowment to begin with. And lube is very very important. Maybe u should get better quality lube to start with. Not to scare you or anything, but pain can happen, usually due to either not enough lube being used, or due to not relaxing the muscle. One more thing is position. My suggestion is maybe try to start with you on top so you have full control. Again, this is really personal preference kind of thing, so if it doesnt work, try different positions until u find one that is comfortable for both u and the your guy.

Also, just 2 share, based also on personal experience, my 1st time, Mr. Perfect Guy got a very gigantic m*nh**d but I was able 2 accomodate it fully, though he was not able 2 pump it since it really hurts 4 me, though he was able 2 do it on our 2nd time, but ur totally right, its safer and easier 2 do it when the size is not that huge.

On the position, it makes me wonder why I prefer missionary position which made me relax more, maybe bcoz I can see his face & muscles that it helps, idk, but I think that helps...I tried starting with me on top but the danger in there is u are always in the verge of quitting when pain strikes so I just let Mr. Perfect Guy do it slowly in missionary position, just sharing, I'm not opposing anything just 2 be clear.

[AlexThompson]

Thanks so much, @DrimVoiz and others for your continued insights.  I am definitely intrigued....

This past summer, I spent two weeks in Phuket.  I met a great 27 year-old local guy on Grindr on my first night and he slept over every night from that point on.  Handsome, fit, smart, big dick.  After a few days, I was surprised that he didn't initiate anal so i asked him about it and he said, "Oh, I just thought you weren't into that."  I was determined to prove him wrong, so I bought condoms and lube...

I was staying in a gorgeous, secluded house in the hills...it was pouring rain outside....the bed was amazing...we had been making out for hours...it was all so incredibly romantic.  I revealed the box of condoms and he looked surprised and then smiled.  He asked if I wanted to top or bottom, and I said bottom.  He slipped it on.  We were hot and ready  He made it to the entrance...

....and then I panicked and stopped.

Thankfully, it didn't matter to him and the rest of our time together was perfect.  But maybe I do have some regrets about not going for it? For me, it truly wasn't about the possibility of physical pain.  I think I just have this leftover fear from the 1980's.  So maybe therapy, PreP or a combination of the two?  And PRACTICE!  Definitely practice.