Advice for a first timer

Everyone is different! But I'm in my 60's, and it was only a few months ago that I was where you are. My avenue was cross dressing. Someone responded to an ad of mine, and i had him in my spare panties. I thought I was just looking to play dress up with someone....but his hard on stood out from the panties, and i was mesmerized, and hypnotically drawn to touching it! And it felt soooooo good in my hands, and later in my mouth! Soon I was wanting and doing it all, and once, gloriously, loved getting my ass filled with cock that squirted in me! Yes, I've fallen thru the mirror to Wonderland, and don't want to go back.

Some of these sissy hypno videos (pm me for a great list!), emphasize humiliation, which I don't go along with. I'm not less for liking to suck and fuck guys. I'm more! But one theme of these videos is something along the line, once you taste cum in your mouth, once you open up your ass, you'll never go back, and things will never be the same. That one's kinda true, at least for me.

Do what feels right! Try to recognize the societal puritanical pressure we all feel, to one degree or another, as the negative emotion it really is.

:kiss:
 
Be open to anything you're both comfortable with. You don't need to do it all in your first time.

This is a great opportunity. Don't let yourself be used, or forced into anything you don't want to do.
Take your time. There will be other opportunities, and other men.

Relax and enjoy. Tell him you're new at this, and let him be your 'coach'

I'm in my 60's, started sucking and having sex with men when I was in my teens. Among my few regrets is that I didn't suck a LOT more guys when I was younger.

Warning: Cock sucking can be addictive!
 
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Be open to anything you're both comfortable with. You don't need to do it all in your first time.

This is a great opportunity. Don't let yourself be used, or forced into anything you don't want to do.
Take your time. There will be other opportunities, and other men.

Relax and enjoy. Tell him you're new at this, and let him be your 'coach'

This is all great advice. I think the most important part is, don't do anything you don't want to do or don't feel comfortable doing.

You don't need to do it all the first time. My first time, all I did was jerk off with another guy while watching straight porn. It's ok to work up to more.

Honestly, think about your first experiences with a woman. Did you just jump into bed, make out, finger her, go down on her, play with her boobs, have vaginal and anal sex all in the first night? Or did it all happen gradually over time?
 
If you like his looks don't think just drop down and do what you know you want to do. You could watch some cock sucking videos and the hypnosis ones are great but when the time comes just do it. You need to suck him first before you cum because once you cum you will probably chicken out. Good cock sucking friend :kiss:
 
Like others say, do what you feel comfortable doing. Also, think about what you want to try - for example, if you notice men's asses, then do you want to top? If you're drawn to cocks, do you want to bottom or suck or both? Remember also that this being your first time, you don't really know what you enjoy and so on, so don't go in with too high expectations - just relax and enjoy.
 
Everyone is different! But I'm in my 60's, and it was only a few months ago that I was where you are. My avenue was cross dressing. Someone responded to an ad of mine, and i had him in my spare panties. I thought I was just looking to play dress up with someone....but his hard on stood out from the panties, and i was mesmerized, and hypnotically drawn to touching it! And it felt soooooo good in my hands, and later in my mouth! Soon I was wanting and doing it all, and once, gloriously, loved getting my ass filled with cock that squirted in me! Yes, I've fallen thru the mirror to Wonderland, and don't want to go back.

Some of these sissy hypno videos (pm me for a great list!), emphasize humiliation, which I don't go along with. I'm not less for liking to suck and fuck guys. I'm more! But one theme of these videos is something along the line, once you taste cum in your mouth, once you open up your ass, you'll never go back, and things will never be the same. That one's kinda true, at least for me.

Do what feels right! Try to recognize the societal puritanical pressure we all feel, to one degree or another, as the negative emotion it really is.

:kiss:
Y such good advice
 
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The more I think about your question, the more I think you should go for it.

There is so much more to gay sex than just getting naked with another man and sucking or fucking each other.

It's more than just skin to skin or mouth on cock. I learned so much about desire and about manhood, I feel it made me a more complete human. Now I look at straight people as sadly limited, knowing so little about sexuality.

There is something about knowing that another man desires you so much that he gets hard, tries to seduce you and get into your pants that is very flattering. But on the other hand, a hard man can be very insistent, a hard cock doesn't like to be denied it's relief. So I learned what I was putting my dates through for all those years.

Also, I learned it's OK to be attracted to another man. It's OK, and fun to play the masculine role with another man, letting him suck you and fucking his tight hairy ass, and to see how much he enjoys that. But you can also explore your feminine side by sucking him (SO satisying !) and let him take you up the ass. I was surprised that I really enjoyed the first time I felt a man's passion and manhood fully, by taking his cock up my ass. I was like now I knew what it was to both arouse, enjoy, and satisfy a man. And kissing a man is so different, and totally enjoyable.

Then afterwards you can like, trust and respect each other in a completely new way. And feel like more of a man, not less, since you've explored and experienced your manhood and his in a new way.

If you do this you'll probably never be the same. I often felt akward afterwards, and felt a lot of confusion and some shame. But I always, eventually, went back for more.

As I said earlier, my only lingering regret is that I didn't have a lot more sex with a lot more guys in more ways. I wish I'd gone to gay baths, and enjoyed gay orgies with three, four or more guys at once. I wish I'd sucked friends and roommates. I wish I'd become a regular at local gay bars and movie houses...the list goes on.

So 'Just do it' is my advice. But be prepared to be changed as a person by the experience. That change is called growth.

Two more thoughts: I never had a guy expect me to meet his emotional needs; to 'love' him like women often do.

Plus, I know that having had sex with men made me a better lover with women, because of the perspective I learned, about what it's like to be with a hot and horny man.
 
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The important thing is to relax and don't do anything you don't wanna do. If you wanna suck his cock just do it, it actually comes pretty naturally but watching porn does help learn a few extra things. If wanna learn those extra things from the best, don't watch gay or straight porn, watch TG porn. As far as anal goes, that's a comfort thing. You may not even do it your first time. Also try some frottage. If you don't know what that is, look it up. I guarantee you will both be extremely happy.
 
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