A
male
age
30-35,
anonymous
writes:*OP's own title*Hi.I got this fantastic boyfriend and we have been together for a little more than a year.He is very cute and is just perfect.But the problem I have is that we are talking about having sex for the first time. He is two years older than me and I am sorta the "girly" one of us. I have blown him and given him handjobs before but now WE want to make the next step. I am realy seccure with this but he is more experienced than I in gay-sex. I have only slept with girls before and this is completely new.I want to have sex with him but does it hurt badly to do it anal? We will use condom and maybe lube but still. I am quite worried that it will be painful and bleed.Thanks for any advice.
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female
reader, Miamine  +, writes (3 April 2010):
 Two finger if his dick is small.. lol
A
female
reader, Miamine +, writes (3 April 2010):
SLOW SLOW AND EASY.. ANAL TAKES A HELL OF A LOT OF TIME..
And we're talking hours not minutes, if you feel uncomfortable then stop, get him to try again with fingers then when you are comfortable, then you start trying again.
You need to be totally relaxed, he has to be slow, then you won't tear and theree will only be the first bit of pain and then you'll start enjoying yourself.. and yes, the fist pain is bad, that's why it needs so much preparation.. :)
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A
female
reader, Miamine +, writes (3 April 2010):
Your partner is a man, and your from Sweden, I'm happy to give you advice on anal.
First you must love and trust this man, trust and love is important for helping you to relax.
Second, alcohol or another stimulant will help.. get him to romance you and make you feel beautiful before you get into the bedroom.
He has to use a lot of lubrication, your hole is tight, lubrication will help it to open up.
He needs to also move slowly. First he needs to prepare you with his hands, this can take a long time. Once your able to accept three fingers easily with no pain, then your ready for a penis in that tight area.
The penis goes in, it will feel strange, once he starts to push it will feel unbearable. That's why you need to be in love and trust your man. If you trust him and want to be close to him you can bear the pain.
You push past the pain, and then then his in, kisses and cuddles will help you relax and reward you for being so kind and understanding.
One more push, he's in, and anal sex is started... enjoy.. yes it's painful, but when your in love and are loved you can bear the pain and move forward to pleasure..
TIME, TIME, BE GENTLE, TAKE TIME AND USE A LOT OF LUBRICATION.
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A
reader, anonymous, writes (3 April 2010): Yes, it will hurt. Hopefully it won't hurt much. Potentially, it could hurt like hell if not done properly.
But you have to start somewhere, and I think it's fantastic that you're going for it with your boyfriend: a guy you've already been with for a year, someone who cares about you, someone you can trust to be considerate and gentle with you. That's much better (and much safer) than heading out to a gay bar high on lust half-determined to give it up for the first sexy man you see, which is the way plenty of gay guys lose their virginity.
Obviously the two of you have talked this through, and you've decided that at this point in your life you definitely want to experience penetrative sexual intercourse. Of course you're dying to, of course you're excited about it. And of course you're also nervous and (having posted this question) well aware that it's likely to be painful to some degree. The first thing you need to do is buy a pack of condoms and a tube of lube.
This is going to be one of the biggest defining moments of yout life, and your first time should be special and as pleasurable as possible - this applies to everyone, but I think especially so for gay guys, because of the awkward fact that it IS going to hurt a bit.
So, I'm not saying you need a big candle-lit dinner, but you want it to be sweet, intimate and as nice as possible, so the setting is important. DON'T rush it. Slow and steady is needed here. Maybe have a glass of wine (don't overdo it!), take a shower together first, easy baby...You know, get yourself in the mood (you say you're the 'girly' one - maybe wear some sexy lingerie?) Spend lots of time on foreplay, oral etc. And don't go for the big one until you're 200% on fire with lust.
Your brain, heart and ass may be working in sync to some degree, your mind communicating its excitement to make you tingle down there, your ass expanding and contracting as if it knows what's about to happen - but even still, you will absolutely NEED lube. Lots and lots and lots of it. And also the condom. There will be a pretty overwhelming starburst of physical sensations and emotional/psychological feelings going on inside you, so all you can do is be prepared as best you can, physically, emotionally and psychologically.
Right, moment of truth: there are many positions, but for a starter, the best bet might be him sitting on the bed while you SLOWLY and GENTLY lower yourself onto him. You can go faster/harder as and when you feel more comfortable, but you need to go at your own pace, he can't just ram it straight in and thrust away. You need to TALK to him (ok, might be difficult, but you can moan). Let him know - with words or other vocal and facial expressions - what's going on with your body. You're likely to feel a definite but bearable level of discomfort - but if you feel PAIN, as in real hurt, STOP, pull back a little and adjust the angle. He needs to know if you're enjoying it and wanting more. You might cry a little. The response varies from one guy to another. Also, don't stay still: move up and down on his cock (not too fast though!)
If it's going well by this stage, congratulations you have lift-off! There's scope for both of you to rattle off mind-blowing multiple continuous orgasms. If you want to feel him deeper, he can maybe get deeper and better penetration of your prostate gland (a submissive male's pleasure centre, roughly analogous to the female clitoris) if you lie on your back with your knees raised, or on your side with your legs drawn up. These positions involve you surrendering control to a degree (maybe an added turn-on) so it's up to him how hard and fast he pumps you.
But, if it isn't working out, if it feels like it's killing you, just STOP, jump off, say 'sorry baby I can't', forget about it and maybe try some other time. He'll understand, and if he doesn't, he's not the man you should lose your L-plates to.
So, the day afterwards, you might feel 'that was wonderful and I want more' or you might feel 'that was a mess'. I wish you well and I think you'll be OK. I see two huge things in your favour: firstly, you're doing it with your boyfriend who you've been with for a long time.
Also, it sounds like you have no hang-ups or tormented feelings of guilt/shame about your sexual identity, you sound very happy with it. Wonderful. Most gay 16-17-year-olds are still fighting to deny their sexuality, a battle that can't be won and leads to lots of misery and soul-searching, and often makes 'the first time' more traumatic than it should be. You're past all that. You've crossed the blowjob hurdle (congratulations!) and didn't feel any reason to beat yourself up about it. Good lad.
Now for your next trick. I wish you every success. Take care, and have fun. Hope this helps.
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A
male
reader, AvgGuy1  +, writes (2 April 2010):
Yep... it'll hurt. It varies from one person to another. I find that initial penetration to be the hardest part... but... once I get someone in me... and I'm comfortable with it... it's WONDERFUL! As everyone else has pointed out. LUBE... and lots of it. Foreplay helps too!
Oh, and ALWAYS play SAFE (no glove, no love)!!!
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A
female
reader, Angzw  +, writes (1 April 2010):
Sorry to bring you down to earth for a moment son; but I have to bring up a crucial issue. Before you decide to take this next step I would advise you to go with your partner to get tested for HIV. There is a clinic in every county in Sweden offering this test. It is free and anonymous. You are actually asked to give a fake name when you get there. You say your partner is experienced so that means there may be a risk to you. You can't tell a person has HIV by looking at them; most infected people look perfectly healthy and strong. When HIV finally overcomes the immune system and the person develops AIDS, that's when they start to look ill and this can take as much as 20 years to happen. So dont judge by appearances; you really need to understand this as you navigate your way through your life as a gay man. The test is while you wait and takes about 10 minutes for results with another 20 minutes of counseling. Alternatively, every major city in Sweden has a Gayhälsan clinic and they can give you advice for free on any question you may have. Please do not neglect this step. Anal sex is more risky when it comes to STD's so EVERY time you have a new partner, start on a clean slate by getting a test then be faithful to each other. Good luck.
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A
reader, anonymous, writes (1 April 2010): IMO, it will be a bit uncomfortable, but need not be painful. Take your time, lots of finger play, stretching, I'd avoid toys as I find them too hard and that causes discomfort.
If you have pain, stop, breath, have him pull out a bit and lay still. In my experience once you get used to anal, it will be as natural as if you had girl parts...
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A
female
reader, WiseAngela23 +, writes (1 April 2010):
Heyy, no your not gonna bleed but it is going to be painful. It is painful for girls and guys. It will feel very good after a while but always go SLOW AND EASY at first!! ALWAYS!!! Make sure as he enters you tell him slow and easy.
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A
female
reader, Not My Name  +, writes (1 April 2010):
 You betcha it will!
I know my comment after doing that was that breaking my arm in three places had hurt less, ..and that was super slow, stopping at times, and with bucket loads of lube.
Don't let that deter you tho. I didn't and get mind blowing orgasms out of it, and for guys it should be even better, so worth persisting through the pain barrier imo.
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A
female
reader, RainStorm  +, writes (1 April 2010):
Yes it will be painful. Best way is to take it slowly, a finger, two fingers and so on. Use TONS of lube, it will hurt without it!!
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A
reader, anonymous, writes (1 April 2010): yes it will. Lube, lube, lube, lube, ....
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