I'm a gay man, but I suppose my experiences can be translated into straight sex terms. I mean, I'm not going to do the translating. You can do that shit. I'm going to talk about my experiences. Maybe I'll use a few vague terms, though, so you won't have to switch pronouns in your head so much... assuming you're of the straight variety. Not that there's anything wrong with that. This post, though, will apply to gay and straight, alike.
I've been with a few anal virgins. I specify "anal virgins," rather than just saying "virgins," because so many guys will claim to be "virgins" when, in fact, they've had a number of cocks down their throat, or their cock has been down a number of throats, or their cock has even managed to work its way into another man's (or woman's) ass. So, for the sake of clarity, "anal virgin" means that this particular person has yet to take it in his, or her, backdoor. We're all clear on that?
Personally, I'm no expert on receiving anal. I've done it twice. It was an awful experience the first time, bordering on rape when the guy wouldn't slow down, nor stop when told to do so, and the second time, well, I was drunk, and it was just... meh. I might be an expert on giving anal, but they don't give a certificate for that sort of thing, and if they did, it would probably be covered in lube and other debris which I'd prefer to just keep my hands free from, if given the option. Also, that's not exactly the type of certificate you want hanging over the mantlepiece.
So, let's get down and dirty, shall we? I'll start by talking to the scared, soon-to-be bottom (receptive partner), who wants to know what he should do beforehand. Well, first of all, don't be scared. You're in more control than you think. If you change your mind and decide that you don't want to get fucked, then so be it. Any guy who can't handle that should be shown the door. And there might be times when you change your mind, for any number of reasons. Don't be afraid to do so. You don't owe anyone entry into your ass.
Second, that's the prep work. Anal is rarely going to be a spontaneous thing. When it is, expect that it might be messy. Messy isn't sexy, so, try to avoid that, if at all possible. Now, again, I'm not the expert, here, so I'll say what I've heard others say: Don't eat anything that's going to cause you to be gassy, or have the shits. No spicy foods. No tacos, or burritos, or anything of that nature. Try something high in fiber. A high-fiber diet is easier to digest and will go through your system more cleanly, shall we say. Next, you're going to need to take a poo... Do you like how I said "poo" instead of "shit," like I'm all classy, and shit? Damn right, I am! Anyways, yeah, take a shit. I read on some article, somewhere, that one guy likes to dig around in his ass with his fingers, afterward, to try and get all the little bits and pieces of shit out. The description, which I actually made sound more pleasant, was disturbingly disgusting, and hopefully wholly unnecessary. I think I would try just an anal rinse or douche. You can get one at your local adult store, you know, where they sell all the dildos, and stuff. You can also often get them at your local pharmacy. My guess is that they're cheaper at the pharmacy. Everything at the adult story is way more expensive than it needs to be. Anyways, hop in the shower and rinse yourself out with some warm water. Do it until you feel pretty confident you're clean back there. Also, don't forget to scrub your ass, itself, your crack, and around your hole, with some soapy water. Some guys and gals like to rim. Not me. Please don't ask me to rim.
Oh, by the way, this also works if you're a straight dude who is going to get pegged by your woman. So, go ahead and take notes for yourself, if you're a straight dude who is into that sort of thing.
You should also be aware of your body. This is kind of when the changing of your mind might occur. You might do all of this prep-work in the morning, or early afternoon, just in case you might get fucked, then, later in the evening, when things start to heat up and you're getting frisky with your partner, you might feel a rumble down there. If you feel like your bowels are full, or will soon be full, getting fucked in the ass will be both uncomfortable and messy. Fudge-packing is unpleasant for all parties. So, it is perfectly fine to say, "Not tonight." You might want to find some less than disgusting way to tell your partner that you have a round chambered*, so that he doesn't think that you're not interested, though.
*Round Chambered: Shit ready to evacuate the bowels. Defecation imminent.
I've fingered guys before and felt one up there and politely let them know that this was going on. Sometimes you can't do anything about it. Such is life. Be a grown up about it. Don't make it into a big deal. Do not freak out about it. Shit happens. Literally.
Okay, so, you're all prepped up. Your ass is pristine and sparkling. You're raring to go! Now what? Well, this part is for both you and the guy who is going to be going inside you. So, tell him to start reading over your shoulder at this point. I'll give him a minute to get here...
Is he here? Or she, if this is a pegging situation? Good.
Do not just jump into fucking. The ass is not a vagina. Hell, you can't even just jump into fucking a vagina. You have to take things slowly. Start out with all the foreplay that you like to do. I'm not going to tell you what to do. Do whatever gets you hot. The main goal, though, is to get the receptive partner ready for it. As he, or she, gets aroused, the anal sphincter muscles will loosen up a bit and allow for easier entry with less pain.
Oh, pain? Yeah, there's some pain. How much will depend on a few things: Your prep-work, foreplay, his size (length and girth), and your anatomy. All things being ideal, there will be minimal discomfort. Typically, any pain you experience will subside. If you're terribly worried about pain, consider how many people love getting fucked in the ass. Every one of them feels some amount of pain at first, but they put up with it for some reason, right?
Okay, Mr. Giver-of-the-cock, you're making out, exploring each other's bodies. Maybe you've done a little oral... or some rimming. While you're down there for the oral or the rimming is a good time to see how ready your bottom is for this adventure. If you're sucking his cock, or eating her out, discreetly put a little saliva on your fingers and start rubbing that asshole. Do not hack up a loogie. Do not make a production of spitting in your hand. Most people will find that repulsive. Personally, I'll give head and just try to make it a little extra slobbery (gross, I know) and get my hand up on his cock to get a little spit on my fingers, then move them down there. If your partner is a woman, do not go from rubbing her ass to rubbing her vulva in any way with that same hand. You'll cause a yeast infection. Just an FYI, there. So, you start rubbing the hole and eventually you'll start to feel it give a little bit. You'll be able to get your finger tips in a little, then you'll be able to go in a little more, and a little more. You may occasionally need to add a little more spit. Again, discreetly. Once you can easily get a finger in there, leave it in a bit, finger him, or her, for a little while. If it's a guy, you can feel his prostate by curling your finger just a little upwards, like you're telling someone to "come here," with your finger. It'll be a sort of hard bulb-like thing. Rub that and he'll love you.
While you have your finger in there, you'll be able to feel a little more confident that your bottom is clean, and the bottom can feel a little more confident that he won't feel much pain. You now pretty much have a green light.
This is when you hopefully already have lube, and condoms, if you plan to use them, handy. I recommend that a bottom's first time being anally fucked be face to face, if at all possible. The primary reason for this is that the top (the giver of the cock) will be able to read the bottom's face and know if he or she is in pain or not. The top is going to need to sheath up with his condom, assuming he's using one, and put some lube on both his cock, and around the receiver's asshole. It can also help to finger him a little bit more at this point as this will get a little lube up inside, and will aid in penetration.
It helps to raise the bottom's ass a bit when you go for entry. You can either put a pillow under his butt, with a towel over it, to keep it from getting messed up (sex isn't clean), or you can hook his legs over your elbows or shoulders, which will lift him up. Feel for his hole and line up and go in as slowly as you can. Sometimes aiming is tricky, and the bottom might have to help you out. Let him or her. When you enter, go slowly and carefully. Put just enough push in to get in a little ways and watch his face. He's going to look like he's in a little pain, but he should not look panicked. If he tells you to stop, stop. Typically that doesn't mean to pull out, but means don't move. Make sure you're clear on that with the bottom, though.
One of the advantages to the face to face position is that it frees up the bottom's hands so he can put them on the top's thighs and provide physical feedback. He can push to slow or stop you, or grab your legs to pull you in. So, if you're the bottom, utilize that method. It's rather helpful.
There are two sphincters in the ass. Well, technically, one is right there at the main entrance, and the other one is just a little ways in. That first one tends to be the easiest to get through. The second one will usually relax under pressure, but it will be a bit uncomfortable for the bottom. Once you've slowly entered... wait a moment. Just pause and let the bottom get used to this. At the moment, the sensation he feels is like he really has to take a shit. So, bear with him for a moment. He'll likely give you a nod when it's okay, or you can just take it upon yourself after a few minutes to slowly pull out just a tiny bit, and then back in. Again, slowly, slowly, slowly. No pounding. No thrusting. Not yet, anyways.
After a few moments, the bottom will feel more relaxed and really start to enjoy it. It will either just feel great, or it will be a mixture of pain and pleasure, which many people love. At this point, you can start to pick up the pace.
For the top, you'll want to mix up your routine a bit. You're not churning butter, here. You're not hammering a nail. You're fucking someone, and you want him to get off, hopefully, unless you're an asshole. But, if you were an asshole, you wouldn't be reading this. Anyways, change it up. Go from slow, to fast, to hard to gentle. Even change your angle of approach a little bit sometimes. The bottom can learn to control his anal muscles and tighten down on your cock. It's all part of the same muscles you used to stop pissing, mid-stream. Tighten that muscle, and it'll tighten around his cock.
A good bottom can coordinate things so that you both cum around the same time. Don't expect to be a good bottom. And don't expect to be able to do that every time. The trick, though, is that the bottom is feeling this amazing prostate massage, but will most likely not cum until he starts stroking his cock. Once he does, it won't take long before he cums. So, if he's good at reading facial cues, or his partner is pretty vocal, he may know when the top is about to cum, and can try to cum at the same time. Sometimes the bottom can cum first and keep getting fucked, but, I don't recommend it. If the bottom is a guy, he's pretty much lost interest once he's blown his load, so he's not going to enjoy having a cock in his ass for very long at that point.
If you're the bottom, try not to ask the top if he's about to cum. I don't know about everyone else, but with me, that puts too much pressure on me, and basically you've now prolonged it, or made it impossible for me to cum altogether.
So, I think that pretty much covers it. This was longer than I thought it would be. Leave your feedback below, if you have any other suggestions, of if you used any of my advice.