Research. You should be doing a lot of research. however, based upon my own research, you being relaxed is key as if your nervous you will tighten up and that will make penetration harder and painful for you. You can achieve that by a sensual/erotic massage, some fingering etc. until you reach orgasm. When you do, if he is playing with your anus and penetrates it with a finger this could help not only intensify the orgasm but help ease you into anal sex in general. You can and should already be trying it out on your own, again with fingers or a small toy. This will help you get use to it and ensure that your the one in control instead of trusting him to know whether or not something is comfortable or not. Use lubricant (and it should go without saying that you should make sure you are clean (a water enema) and your bowls are empty (having gone to the bathroom within the last hour or so to be absolutely certain (your first experience should probably not end poorly so precautions are necessary))), a lot of lubricant is probably going to be needed until your comfortable enough to know how much you actually need (better to use to much then not enough). I've heard silicone based lubricants are best. As for positions, at first you should probably want to be in control so you on top would allow for that though its not going to go in as easily it does allow you to control depth and speed better. If your fine with trusting him, you lying on your belly would probably be best as doggystyle tightens the muscles and again, will make penetration difficult. As for the most pleasurable positions, honestly that would be, more then likely any position that causes the penis to point and apply pressure to, the front of your pelvis i. e. you lying down on your belly, cowgirl with you leaning back, you laying on your side while he is kneeling perpendicular to you etc. Though obviously those are subjective so you might enjoy other positions as well (those are just the positions that are going to most easily stimulate the vaginal wall and are aimed towards the g spot). Also have him research this as well as you don't want to rely on him doing this if he is not properly informed (he can't just jam it in, its not a vagina so that's going to more then likely hurt).
I am a gay man and an exclusive bottom who just loves getting fucked in the ass. If done right, anal sex does not really hurt at all, but can be a great source of pleasure for the person receiving it.
The key to success is physical and mental preparation. The physical part requires a clean hole and a lot of lubrication... To answer your question, water-based lubricants often work the best. As for the other questions, most of the time, I don't do enemas, I just make sure I have a complete bowel movement and a good shower before getting fucked. As you can guess, food that helps digestion will also work here to your benefit, like fibers, etc.
The mental part is about relaxing your body and your asshole. Once your hole relaxes, it can stretch beyond your wildest imagination to help take your man's cock into you...
A butt-plug may also help. This has been one of my biggest helpers to stretch my hole in order to be able to accommodate guys with really thick cocks. To that end, I'd recommend starting with a small enough plug that you can wear at the beginning. But, it should still be thick enough so you can feel the walls of your asshole stretching a little. After wearing that for a few days, you can gradually move to the next larger size, and then increase the size of the plug to really thick ones that you could not have accommodated at the beginning. This way, I've been able to enjoy really humongous cocks in my ass. I sure hope you will, as well!..
Please feel free to write back if you have any more questions. Good luck!..
lube and fingering your ass first
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There is proper way to do it, if you do it, it would be very easy. Relax, lube and practice is most, if you need step by step details you can pm me.
By practice you mean what exactly?
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Don't just try anal out of the blue. Train your ass first. Get a tapered butt plug the same thickness as your boyfriend and use it to gently dilate your ass. Here's the important part... do it while you masturbate because it associates the sensations with pleasure in your brain. Practice and train your ass while you masturbate until you're comfortable with the full plug inside you before trying the real thing. That will probably take a few weeks or more. Of, and use a good water based lube like Astroglide or this one...
Someone else mentioned silicone lubricants being best, but that's not true, especially for a newbie. They are not nearly as slick and slippery as good water based lubes. They last a little longer because they don't evaporate, but the water based ones still last a long time and are much more comfortable for the receiver than silicone lubes, which tend to feel a little "draggy".
I wouldn’t mind trying it on my girl but I think I’m too thick that it would hurt her more than give her pleasure but I’m perfectly fine with vaginal sex. 😊
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