Copyright (c) 2014 Corey Harper
A few of you have been hinting that you’d like to see a post about a proper way to have anal done to you. Some of the more experienced girls will already know most of this, and know what they need to work up to penetration in that most tender and vulnerable of areas, but for the rest of you, I offer this simple primer.
Be clear: I’m not a counselor, sex therapist, or porn star, These are just some things I’ve found that have worked for me. As the saying goes, your mileage may vary.
Safe sex should be a given. Wear a condom.
I’ll write this as if I’m tutoring guys, because as the possessors of the dick, they need to know how to control the damn thing and not freak little subbie out. Plus, I have one, so I’m familiar with its care and feeding. But if any of you experienced subs would like to write a post from the penetratee perspective, I’d appreciate it. Other than some basic experiments on myself to get an idea of what it would feel like for my girl, I’m a confirmed top; mine’s an exit, never an entrance.
Since many of you girls have already expressed an interest in this, I won’t go through the steps to get a girl curious about anal sex in the first place. We’ll jump right to prep and landing.
So she’s indicated in one or more ways that she wants you in her ass. Yay for you. If you’re a guy who has never fucked anal before, you are in for a mind-blowing experience. And if you have, you are in for a mind-blowing experience. But how to do it?
First, it ain’t a pussy. Seriously. It may look like another hole in your sweet baby girl, but it’s far more delicate than you think. And also not. Yeah, it’s a paradox; and if you haven’t already figured out that most things to do with girls are a paradox, I weep for you.
So. Not a pussy. Yes, it can take a pounding… eventually. But you have to work up to it.
Okay. Your girl has indicated she wants to take this next step. While there are several ways to prep and train her–including ever-larger buttplugs–I prefer the hands-on approach. Make that the flesh-on approach. But keep in mind that prepping her with tiny buttplugs and working up is another option.
The day of: I recommend eating lightly, and not going out for a big steak dinner or Mexican food right before. No matter how bad you want to plunge your cock into her there, keep in mind nature’s original intention for that particular passageway. And it wasn’t meant as a receptacle for your veiny dick, sport.
I won’t go into complex prep here–like enemas–as that is beyond the scope of this article. Seek professional medical assistance on that topic. Or at least read the label on the Fleet box.
So let’s assume she’s relatively “empty”. (But you should also be aware that it could still get a little messy, so I recommend keeping some tissues or other disposable wipes handy.)
Lube. Lube lube fucking lube. Can’t have too much, especially the first time. If you don’t already have a favorite, Astroglide is a good first-time choice. I’ll say more about lubes shortly.
Your girl needs to be relaxed. You are about to introduce her to something that could actually have some ramifications on your relationship, so don’t be an impatient dumbass. Take your time. Be more than patient with her. This is a BIG deal.
If the two of you drink, a little wine (NOT a lot; you want her conscious) and sensual music for awhile beforehand is a good start. Just sit with her and chat. You can do the chatting naked, in your bed, while you hold and caress her. Make her feel like she is the most important thing in the world to you. Because she is. Do NOT make her feel rushed. You know what you want to do to her. She knows what you want to do to her. You may know what it feels like to you, but she has no idea. And no doubt she’s been taught from birth that getting fucked in the ass is a Very Bad Thing to do. So take it slow; she’s dealing with a lot of emotions right now.
All right. The chatting and caressing is getting more sensual and suggestive. She’s relaxing, and maybe getting aroused. Now’s the time to jump on that and get her really hot.
Whatever she likes, give it to her. If she likes you to eat her pussy, do that. Get her to the point of coming, but DON’T let her come. She might get pissed at you, but hang tough, kiss and reassure her, and keep going.
Her pussy is now trickling like a happy little brook. Her nipples are so tight they could put an eye out. And she’s starting to rub up against you. It’s time.
My personal preference for the first time or three is for the two of you to lie on your sides on the bed. I prefer the left side. You are behind her, spooning her. She might start to hesitate here, because now it’s about to get real, but unless she really balks and calls a halt, keep going. (And if she does freak and call a halt, it’s up to you to determine if it’s a full-on “Red” moment, or if she is calling “Yellow” instead, and just needs more reassurance. Remember our discussion on safe words? You are using them for this, right?)
Got the Astroglide handy? And I’ll assume you bought the large size, and not the little one-use envelopes, because you are optimistic. In this first-time situation, you can’t use too much lube.
This next part may go against everything you think, as a Dom, but bear with me. The long-term rewards will blow your mind:
At this point, turn over control to her.
That’s right. For the next few minutes, your sub is in control. Why? Because she is about to do something that may terrify her, but she also wants to please you. Pressuring her at this delicate stage may get you the ass this one time, but cause you to lose it in the future. You can still guide her, but DON’T force her.
Give her the lube. Tell her to smear a lot of it on your (presumably hard and purpling) cock. Try not to come in her hand, no matter how good it feels, because trust me, there’s a much more fun place to put it.
Next, tell her to spread it on her asshole. And around her ass. Pretty much wherever it makes her feel more confident to put it. You want her to know that her opening is as greased as it can get.
Remember I said you can guide her, but leave final control of your weapon to her. Maybe down the road you can penetrate her like you are driving a railroad spike into a crosstie, but for now, she’s the boss.
A quick digression: I know the above to be true, because I had a sub I trained in the manner I describe, and at one point after a few sessions, she was happy to let me fuck her with no more lube than that coming from my cock. This does work. Down the road, you’ll be able to do some porn-movie type things, if you are just patient now.
Okay. You’re greased. She’s greased. You are so tumescent and throbbing you feel like you could kill with it. All you want is to ram it home, hear her scream, and blow your load into her ass.
Tough noogies. Wait.
Tell her to take hold of your cock. Nestle up against her ass, but DON’T give her any reason to feel you are going to suddenly plunge into her. I don’t mean you should lay there like a corpse, but for god’s sake be still and calm.
Now would be a good time to increase the caressing I assume you’ve been doing this whole time. Reach over and stroke her pussy the way she likes you to do. If she enjoys breast play, squeeze and knead her tits. And since you are reading this on this pervert site, she also presumably enjoys some pain, so pinch those nipples. Let her feel some pain. If she’s really into it, send those pain jolts from her boobies straight to her pussy. Amp it up for her.
This whole time she should have been holding your cock, her hand reaching behind her to grasp it. Maybe she’s holding you away from her ass, or maybe she’s gotten brave and split her ass cheeks with the head of little Dom. Either way, nestle closer to her, letting her know she can move forward.
But at her pace.
At this point she may be keen to put you in, or she may still need some coaxing. If she seems stuck, tell her to rub the head of your cock around her ass crack. Usually she will eventually begin to get more aroused, and will start to press the head of your veined beast against her asshole.
And it’s entirely possible she may get so excited that she tries to shove you in all at once. Don’t let her.
If she seems receptive at this point, tell her to SLOWLY press the head of your cock into her asshole. Her sphincter will likely resist instinctively. Make sure you are absolutely still; you want her to feel like she is totally in control of your rod at this point.
Okay, now we’re cooking. All that lube, all your caressing, all your murmured reassurances should be having the desired effect. Kiss her back, her neck. If she likes it, tug her hair a little. Maybe give her a gentle bite on her shoulder. Let her know you love her and are prepared to wait as long as it takes for her to relax.
Now ask her–ASK her–to press the head of your cock a little harder into her asshole. She doesn’t really know what to expect, and if she presses firmly enough, chances are your hardness combined with all that lube will make the head of your cock pop past the ring of her sphincter, and snap tight around your frenulum, just behind the coronal ridge.
Holy fucking crap! The feeling is indescribable. You want to pound. You want to come. As I said earlier, tough noogies. Wait. Be still. Don’t fucking move.
Because she might have stopped breathing at this point, at the foreign invader sticking in her ass. No matter how tight and glorious it feels to you, she is experiencing things you can’t imagine (unless you like being fucked in the ass as well).
Give the girl a minute to catch her breath and to process what’s going on up her bum. Trust me, the more patient you are with her now, the nastier the things she will be willing to do with/for you down the road. It’s a win-win, so cool your jets.
When you feel her start to relax, tell her you are going to push forward, but only a little. Promise her it’s only a little. Wait for her to agree.
Then do it, but keep your promise, and move it just a millimeter forward. Her sphincter will be adjusting like crazy at the different widths of your cock, so let her adjust.
When she does, tell her you are moving in a little more. By now, assuming she’s going to like anal at all, she will be starting to get past the initial shock, and things will be going on in her brain, and in her pussy. Very Good Things.
She may press back against you, urging you deeper. Making sure you are still over-lubed, press into her–slowly, this time, letting her feel every millimeter. (You can plunge in wholesale another time, once she’s acclimated to anal play.) She may stop breathing again, depending on how much of you there still is to go in.
Once in, stop moving. Yeah, I know that takes a lot of control. Look, you want to wreck that ass on a regular basis, or not? Just stay calm and wait her out.
Eventually she will want you to move. Now–finally–you can do what comes naturally to your rutting male brain. But start slow. Move in and out of her only a little. Then more. And still more. Finally you can pound her ass the way you’ve been wanting to.
Be prepared for some interesting reactions. This is something she’s never experienced, and it is not like a pussy fuck. She may get quite active. As in, tigress-ripping-the-throat-out-of-a-gazelle wild. It’s pretty cool.
She may try to climb up all over you, because the sensations she’s feeling are making her crazy. Hold her hips and control her movements enough that you don’t suddenly pop out of her, because that would be a Bad Thing at this point.
Try to hold onto your load long enough for her to get the full experience. She may want to go for hours, or she may get exhausted quickly from all the orgasming she’s experiencing. Either way, don’t push her. You’re getting what you want, and you’ll get it again.
Once you spurt your cum inside her, and she’s becoming desiccated from all her orgasms, it’s time to withdraw and give the girl a rest. Get those disposable wipes ready.
The dismount is something the two of you will have to work out–does she do better if you withdraw while still hard? Or does she respond more positively if you soften first? It will depend on her, so be guided by what she says she wants. It may take some trial and error, but oh happy day and lucky you.
Clean her up, and for crap’s sake don’t make any pea-brained comments about any mess you may encounter. If you aren’t willing to do this for her, then you shouldn’t be fucking her up the ass in the first place. A nice warm shower for the two of you at this point may be great aftercare, assuming she can actually stand on her wobbly legs. Wash her softly, tell her how good she was, how satisfied you are, and how much you love her.
And then start your evil brain thinking about the next time you get to destroy her ass.