Anal Sex -- I cannot make feel pleasurable

You match the criteria of "Twink" my favorite kind, and his too.

While society as a whole would scoff at you for trying to hook up with an older guy, that isn't important. If this is a sexual fetish of yours then go ahead and pursue it. You'll be making some older gay men VERY happy. This guy though I feel very strongly that you forget that you ever met him. There are LOTS of older men willing to have sex with younger boys. The only difference is that they care enough to wear condoms. AND YOU SHOULD TOO!!! Getting an STD now will give you nothing but regret, you will look back at losing your virginity and wish you had worn a condom or he had. I do all the time... Mind you it was a delicious experience, but the regret lingers and reminds me every time I look at my crotch...

Don't let your friend's actions determine your sex life. There are a lot of messed up people out there but there are also people who care very much for others like myself. If I had someone to call my own I would give him/her the world and I wouldn't look back. Your old friend probably looks back on his actions and feels guilt for it, now that he probably has some gay/bi/les friends, if not now he will in the future - or maybe he will never understand gays and that will be his loss.

Good luck with whatever you choose... I can only hope that you DON'T go through with what this man is proposing...

 

This may seem harsh, but I feel it's necessary.

COME ON!!! This guy is 22 years older than you, OLDER than your parents! I cannot believe you would even consider sex with him. He admits to being with 25 people, and you say he doesn't want to use a condom with you, so I'm assuming he didn't use a condom with them. So, that's 25 chances of him contracting an STD, and that's 25 chances too many.

DO NOT SEE HIM!

I seriously think he is a borderline predator, he met you online, he knows you're 17 and he insists on having unprotected sex with a minor? That show's you a lot about his morals. He doesn't care about you, you're a piece of ass to him, a young one at that. If I were you, I would go as far to report him to the local police. To be perfectly honest the whole age gap/unprotected sex/met online utterly disgusts me.

As for the bottom having a lesser chance of infection... FALSE. Especially if you're 'going all the way.' Think about it, he 'deposits' his potentially infected sperm into your VIRGIN anus, which has a greater chance to tear being a virgin. The greater chance of tearing, the greater chance that his infected juices gets into your blood stream.

Please do not let him take advantage of you, I promise you, you'll regret it.

 

Quite the opposite. This older guy, in my opinion, will not appreciate you or your emotions.

 

You asked for our advice now please listen to us! I'm really sorry it isn't the advice you were looking for but there are no ifs ands or buts about it!

 

Listen to what everyone here has already told you DO NOT SEE THIS GUY. He has no love and respect for you, he is just excited by the thought of screwing a young virgin.

As for anal sex feeling uncomfortable when you put your fingers in, this is quite normal because you are not in a highly excited state of mind for starters, you are contorting yourself in impossible positions in order to put your fingers in and also you need to get used to the feeling of something in your bottom before you start to move your fingers around.

There are some very good, small anal vibrators on the market, with plenty of lubrication you insert it in your anus already vibrating (for ease of turning the damn thing on) insert it very gently little by little and then lie back, relax and let the vibrations do their thing. I think you will find this VERY different from inserting your fingers. Often anal vibrators have a little bent bit at the end which vibrates on the prostate gland which is very pleasurable and will cancel out any discomfort of the anal muscle.

The more highly excited you are the more your brain releases endorphins, endorphins heighten pleasure and attenuate pain. If you are with a man who knows what he is doing and is there to give YOU pleasure (his will come another day if needs be) he will know how to get you into the right frame of mind, right state of excitation and only do what feels good to you (quite possibly stopping before he is finished in order not to hurt you) then you can always do other things.

A man who is only out for his own pleasure, like the older guy you have mentioned, will take his pleasure where he can and never mind the pain and discomfort for you and quite possibly ruin what should be a caring lovingin experience which will lead you to fully enjoying anal sex in the future. As for being excited by gay porn where the top is quite vigourous, you will just have to build up to this. As your muscles get used to being used in this way if will be much less painful (even enjoyable) and your partner can become more vigourous in his thrusting.

Just take things gently with a loving caring partner and see how things go just NOT with this guy! Don't rush into anything, find a guy you really like and who really likes you before jumping straight in to the anal penetration side of the relationship, there are lots of fun things to do before then which will lead you up to the stage where you are ready for penetration, and again your first time with a guy he doesn't have to penetrate you with his penis, just see how things go and play it by ear.

Good luck

 

Where are you located you don't have to say town or city just like i can't imagine you can't meet someone around you somewhere to get the fullfillment of a first time instead of rushing into this with aolder guy.

 

You should listen to all the warnings.

It's clear to me that you want to have sex and this guy has shown you the interest that you're not getting from elsewhere - hence your attraction is blinding you to the obvious. In your haste to fulfill your desire, you're letting yourself "do it" with somebody who you shouldn't be doing it with!!

I can't believe you can't see that someone who won't use a condom doesn't give a f**k for your feelings. I believe he's using you and when he then dumps you, it's going to hurt you terribly. Forget this guy and take things easy. The right time, with the right person will come. Sorry to sound harsh but you wanted advice and you're getting similar advice from all of us of all ages. LISTEN TO US.

 

If you don't mind a female opinion . . .

First, I wouldn't see this guy. He doesn't want to use protection, has admitted to numerous sex partners. How do you know he hasn't lied about HIV status or that he's free of STD's? Even if you do see him, I would insist on you BOTH getting tested for STD's. I understand wanting to have sex, but at least be smart about it. Find someone who at least respects you enough to use a condom and be gentle with you. Find someone you aren't going to regret having your first time with, perhaps that you at least have feelings for.

Second, I don't think the age difference is a huge deal, IF he is truly interested in YOU and not just in getting some virgin ***. If he has real feelings for you, and he's interested in your opinions, dreams and thoughts, then it could be a good thing. If that's not the case, he only wants sex, and that's not a good thing.

Third, anal sex can be pleasurable, but you don't just shove anything up there. Try getting a small plug or dildo, if you can, something that has no chance of getting lost up there and take things SLOW, with lots of lube. That can at least get you used to the sensation, then you can try with someone who's going to RESPECT YOU.

Fourth, I have nothing against meeting people online, but not everyone is looking for a relationship. It doesn't sound like this guy is either. Is there no place else you could meet people, in person perhaps?

 

You def won't feel a difference as a bottom.
And yes, 20min of Nirvana aren't worth a whole life of illness.

 

That's exactly how I feel too. I would much rather have it in my mouth than up my ass.

NO!

No, it is easier to get an STD as a bottom. MUCH EASIER.

Exactly.

Me too

This is all true.

Exactly. He just wants to break a virgin. No matter what he may say now, he doesn't care for you. If he cared at all he would not be insisting on having sex without a condom.

I have seen this before, several times. Older guy comes on promising the world, makes you think this could be a real serious relationship, then has his way with you and you never hear from him again.

You have the hurt of being deceived and the fear of an STD or HIV. He lied about his intentions.... maybe he lied about his HIV status and previous partners too?

How do you know it's genuine? How do you know he hasn't had unsafe sex since then?

It takes up to 6 months for HIV to show on a test after it was contracted. How do you know he has had no sex with anyone in the last six months?

DO NOT SEE HIM!

 

I think so many have weighed in on the subject. Do no see this fellow and if and when you have sexual contact, do not do so without protection. People can say whatever but it does not make it so. Don't expose yourself to a lifetime of discomfort and sorrow for one night of possible pleasure.

 

yeah, again, DONT DO IT

 

22 years of possible STDS - as everyone has said, be careful...

 

This is a BAD,BAD,BAD ,BAD, BAD, BAD, BAD, BAD, IDEA.

Be Smart.The rest of your life with HIV is a long time.

 

considering your initial question was about the anal sex thing, I answered that.

With more information that you have provided, I think, if I were you, I would take heed of the warnings - DO NOT MEET THIS GUY! I think it's very apparent that he doesn't care for you, your personal and physical wellbeing, nor what impact this will have on you psychologically - as you said, it will be your first time. Do you really want it to be with a man, 22years your senior, who wants to have unprotected sex with you (risky!!!)?? I think we both know where the logical answer is there.

So, in a final bid to help you reassure yourself that this is definitely not the road you wanna take, DON'T DO IT! I WOULDN'T!

and yes... In reply to your other question - I am a gymnast! well.. past tense...hamsting and L5 injuries prevent me from competing, but i still train.

 

I'm glad you came to this conclusion. We will be glad to help you with any problems you may be having. From what I've seen this is a very non-judgmental place. If you share your experiences with us I'm sure it'll help with self-esteem. Getting things off your chest will make you feel better.

Good luck to you!