Starting with an Anal Sex Virgin




This article focuses on physical techniques as well as general advice for the Top (the dominant/giver/penetrator) that are designed to open the ass of a Bottom (submissive/receiver) for the purpose of engaging in anal sex. As detailed as I have tried to be, it is not possible to cover every aspect of every persons personal responses. Conciser this advice as guidance for the wise and not rules for fools. This is all sound advice but be ready to vary things for an individual.

Before you get started with an Anal Sex Virgin


First and most important – Relax!


The very first piece of advice is to make sure the recipient is not harboring any anxiety. I am not just talking about anxiety about have anal sex, any residual stress from the day or anxiety with make things difficult.

The two primary sources of anxiety related directly to anal sex are the thought of it being messy and the expectation of pain. To avoid a mess and more importantly to give the bottom confidence that there will be no mess, starting with an enema is the solution for most. I have written several articles on the different kinds of enemas and on administering then but the start point is Eating and Enemas for Clean Anal Sex.

Next they need to associates any anal activity with sexual pleasure. I have written other articles on the psychology and physiology of enjoying anal and these aspects of anal sex should be understood first. This is less of a concern if the recipient is the initiator of anal sex. They already considering it as part of their sexual exploits.

Mixing Alcohol with Anal Sex


While there are a lot of ways to eliminate life’s anxieties, a simple solutions for many Bottoms is alcohol. This suggestion will raise Red Flags for some but there is nothing wrong with the Bottom being a bit tipsy to remove anxiety, remove psychological barriers and relax the muscles all at the same time. However, it is not good for the Top to be tipsy in any way, especially with an inexperienced Bottom. The Top needs to have their wits about them. I cover this in a lot more detail in mt article Alcohol and Anal Sex.

Warming Up for Anal Sex


It doesn’t matter if they are an anal sex virgin or not. If you want to get into an ass without causing pain, start with a warm up. Everyone knows you have to warm up or stretch your muscles before a workout. It is even more important for the anus.

It doesn’t matter if they are an anal sex virgin or not. If you want to get into an ass without causing pain, start with a warm up. Everyone knows you have to warm up or stretch your muscles before a workout. It is even more important for the anus.

A warm up for an experienced bottom might be as simple as getting them in the mood, but for the average newbie or the less experienced, it means physical stimulation and working/massaging the anus before stuffing a rod in it. If you ever take the time to watch “Behind the scenes” footage of an anal porn flick you will inevitably see the Bottoms wearing plugs and working their ass with dildos before a scene.

These warm up exercises are best done while you are sexually stimulating your partner in other ways, like cunnilingus/fellatio, genital massage, vibrators, etc. Aside from getting your partner in the mood and removing any background stress or anxiety, you are reinforcing the association of anal stimulation with sexual arousal, sexual activities and sexual pleasure.

Begin with just one finger


So you start with one finger, very slowly. This means just touching the anus and rubbing/massaging the outside with lots of lube. This doesn’t need to be the lube you are planning on using as your penetration product. In fact, it is a good idea to start with a general body massage that works up to including the anus.

When you feel that your partner is properly relaxed and ready to let you in it is time to switch to your chosen anal lube, if you have not been using it up till now. Don’t just start probing and pushing at the center of the anus. The technique is to place the pad of your finger over the rim and curl the tip of your finger towards the center. You will see what I mean when you try it. Slide your finger tip toward the center, gently pushing the lube inside.

When you just get the very tip of your finger in draw it back out again. Remember you are massaging the muscles, your are not have anal sex yet. Then work more lube under the pad of your finger and do it again, with each push slowly work the finger deeper.

You will certainly feel the sphincter muscle contract or spasm as you inch your way in. When you feel the spasm hold still for a moment. You want to maintain pressure on the sphincter, to help the muscles relax again, without any rubbing or pushing in and out. As the anus gets used to the feeling the spasm will pass and you can wriggle or push your finger in a bit further.

Pay special attention to any friction. The world is polarized on the subject of using gloves. Some demand them for cleanliness and because it is smoother than the skin on your fingers for the Bottom. For others gloves are a problem because the Top can’t feel as much.

If you feel the slightest resistance, if any contact between you finger and your partner’s anus is not totally slippery, I guaranty that it will be extremely uncomfortable and even painful for your anal virgin partner. Their anus is 100’s of times more sensitive than your finger. If you feel the slightest resistance then gently draw your finger back out and and work more lube in with the tip again.

When you finally get to the first knuckle you should feel the inner sphincter with the tip of your finger. Now you want to start slowly and gently wriggling your finger as you are moving it in and out to find the center and move through the inner sphincter.

You will feel the muscle spasm again as soon as you start reversing direction. When you feel the spasm, stop pulling out, just press gently on the anus and the spasm will pass. Remember you are massaging the muscles. Once your finger is out, gently start again, working your finger in a bit further. Make sure it is nice and slippery.

When you get up to the second knuckle, and beyond, the tip of your finger will enter the rectal cavity (rectum). You will feel there is quite a lot of space beyond the anus that opens towards the back bone. You can crook your finger a bit and have a feel around. It is good experience for the Bottom but be gentle, it will probably feel very weird to your partner and possibly very uncomfortable at first. Remember you want to keep the sexual excitement going.

The second step is Two Fingers


Once your partner can take one finger sliding all the way in to the third knuckle and out again, it is time to introduce the second finger. Work your fist finger in to the first knuckle and then start teasing/rubbing the outside edge of the anus with the tip of your second finger. You may well have to go even slower as you introduce your second finger. Very gently start pushing down with the finger tip that is inside to stretching the sphincter a little more. Start sliding your second finger along the back of the first. Remember to keep wriggling your fingers and follow the same process as before. Remember this is a massage session. If you feel any friction – work in more lube. If you feel the anus spasm – Freeze! If your do the massaging right the muscles will continue to relax and things start becoming easy.

As the anus relaxes further, gently straighten out your fingers so that they are sliding in and out side-by-side. This adds a bit more stretch. You will find that when they are in-line front to back it is easier. Slowly work your fingers so that they are side-by-side across the anus to slowly increase the stretch further.

When two fingers fit comfortably all the way in, it is easy to introduce the tip of the third finger. The the tips of three fingers is about the same distance around as the base of two fingers.

This will start to feel like a real stretch. Massage, relaxation and sexual arousal are the keys. The massaging of the muscles makes them release more and more but by now the skin might be getting tight. Nonetheless, you will still be able to slowly work the third finger into the anus as you did with the second. Same rules apply. The only question is how far can you go on the first try with three fingers?

The first orgasm with an Anal Sex Virgin


If you have been doing a good job with the sexual stimulation, by the time a third finger is introduced, your partner is likely to have their first orgasm. As an orgasm approaches the anus will start to clench and cause all sorts of anal spasms, during which you need to keep you fingers still but maintaining just a little pressure on the muscles.

After the peak of the orgasm the ass will completely relax. If you have been using the lube correctly, your fingers will slide all the way in, when the anus is not spasming. Now you must leave your fingers in while your partner is in that glowing phase. Just let your fingers hold the anus open. Wait until your partner starts to become conscious again.

At this point you will discover if you can continue or not. It all depends on your partner. People tend to be polarized into two groups at this point. If your partner can cope with it then you can move on. Either way, you might have to wait quite a while before they can tolerate any movement in their ass again. Just relax with them and with your fingers in their ass.

If your partner starts screaming “Stop… I’m done. Too sensitive!” then it is time to stop. If they are ready to continue then jump to the next step.

If it is time to stop then you job is to keep your partner calm and explain to them that they have to “push” your fingers out. Don’t just pull them out. You need to give you partner time to get control over their muscles again and “poo” your fingers out. This will feel much more natural/comfortable to them and will be much easier to cope with than having you just pulling out. As your fingers start to move the anus might clenching again. Freeze and tell them to concentrate and keep pushing. Later this practice will come in handy. When they are more experienced with have you pushing things in their ass they will actually be pushing out like this while things are being pushing in.

If they are too sensitive after an orgasm to continue then you have to respect that. You will have to wait for another occasion to go further. You will have to keep practicing with your partner till you can get at least three fingers full length in their ass without them having an orgasm. At that point you can continue with the program from here.

Moving beyond three fingers


So we are starting this step with at least three fingers buried deep in your relaxed but stimulated partner’s ass. Ever so slowly and gently start to wriggle and massage your fingers around on the inside. Your partner needs to get used to movement inside their rectum that is not the result of something telling them to go to the toilet. If they start complaining they need to go to the toilet, stop and relax and tell them to do the same. Reassure them it is just you in there. Now you appreciate the importance of the Bottom knowing there is no need to go to the toilet.

Now is the time to teach your partner to push you out while their anus is being probed. When they start pushing like they do when they poo, you will feel the anus completely relax and the muscles behind that, in the rectum closing to push your out. You should let your fingers be pushed out but not all the way. As you start to withdraw your fingers the your partner is likely to tense up and the anus will clench. Don’t let them. Tell your partner to relax and start pushing again. When you feel a spasm use gentle wriggling and even gently pushing back in is better than pulling out.

Don’t let your finger be pushed all the way out at first. When your partner can push consistently and not clench, it is time to start working your fingers in and out further and further while they are pushing. Halt when you feel the anus clench and hold your fingers in position. Tell you partner to keep pushing and when the anus relaxes start pushing your fingers in and out again. Make sure the anus stays relaxed as you move to pulling your fingers all the way out and all the way back in again. Then it is simply a case of substituting whatever you want to push when your partner is comfortable pushing your fingers all the way out.

Proper lubrication before Anal penetration



Child’s medicine dosage syringe
Max Injector – Anal Lube Shooter

Before you start pounding away it is a good idea to inject lube inside the anus. You can actually buy lube shooters but an ordinary syringe will do.

If the bottom tightens up again, tell them to push while you press the head of your cock on their ass hole. Keep teasing their ass hole with your fingers if you must to open the anus for the cock.

Toys for Anal Sex Preparation


You may not get to where you want to be with fingers alone. You might need to employ an Adult Sex toy or two.

The best toy to open the ass of an Anal Virgin is  a smooth toy with a gentle taper like the Classic Chrome Vibe pictured. It is actually better not to start with a Butt Plug on an Anal virgin.

The sensation the first time the sphincter closes around the bulge in the plug is pretty intense and it is even more intense the first time you feel a pug being pulled out. Save that for other occasions.

Start with one finger following the process described above but instead of moving onto a second finger, start with the toy. After your partner can take the full length of the finger going in and out start inserting the toy. Some gentle vibrations really help the sphincters relax.

As before, it is better to put pressure towards the front or the back of the anus instead of pushing straight into the center. When you sense the muscles tightening around the toy stop trying to slide it in and just push gently against the resistance of the muscles and easy off. Keep pressing gently and easing off until the muscles relax again. But don’t just keep trying to push the toy all the way in. As the muscles relax you can go in just a little more and then withdraw the toy and start again. Each time you do this you will gain a little ground until you are sliding the toy in to its full width.

Max Beginners Anal Vibrator

Caution: the objective is not to get the full length of the toy inside your partner, just to get the anus to take the full width (depth and getting in deep is the subject for another article). The object of the exercise is to make sure that the muscles stay relaxed while the toy is moving in and out, so at some point you can take the toy out and can replace it with your cock (unless, of course, you don’t have one and you are working up to something else). Patient, you must be (bonus points for picking up on the pop culture reference) and If you get it right the sphincter can go literally from virgin to 1.5” or 2” in diameter (across) in the first session (10-15 mins should do it but there are no guaranties).

Anal Sex Virgin – Final pointers

If the ass is properly lubricated, there is still the possibility of pain of initial penetration which comes from the sphincter being shut tight. This is its natural state (no matter how relaxed we are, or feel, our ass remains shut tight for a reason). It is a regular misconception that your can penetrate an ass just as long as your partner is relaxing properly.

If you force any muscle when it is clenched you will strain it!

The sphincter usually only opens/relaxes to let something out and that is the opposite of what you are trying to achieve. Making sure the ass it clean and there are no accidents is another topic. So here are some techniques to help open the sphincter.

1. Have the bottom squat over you. Let them be in control of the initial penetration. Squatting, as discussed in other articles, will naturally stretch the whole (or hole lol) area but it also sends a familiar message to the sphincter which will make it relax. Also, when someone is a little anxious about the idea of pain, being in control can sort that out quickly.
2. Use the doggy position but pull the ass/hips right back towards you with the knees to the chest and the buttocks down on the heals. In yoga, this is call Child’s pose. As before this will stretch the anus naturally and help it open up.
3. Have your Bottom “bear down” (push out) while you are pushing in. This can be a tough ask for someone inexperienced (See – Exercising for anal). Of course, the rectum had better be empty when you practice unless you are into the brown stuff. This doesn’t mean the Bottom needs to have a high colonic first (Cleaning out is the subject of another post).
4. Putting a vibrator on (not in) the anus will loosen the muscles in a second. So use the vibrator as you start the penetration. Keep pressing the vibrator just above or below the anus while you first penetrate.

One final point on injecting lube into the anus. Even with your dick (or other object) well lubricated, you can still tear up the insides of the Bottom and you will not be able to feel it. Your Bottom will probably not be aware of any real hurt going on until it is too late. While injecting lube may not ultimately be necessary, you should consider it a must on the first occasion. If you tear up your Bottom’s insides on any occasion I guaranty it will probably be the last time you get inside that bottom.

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