Pegging safely is important - if you are new please read FAQ before pegging.

Choosing the best materials for insertables is important. Different materials vary in durability, porousness, ease of cleaning, and reaction to lubrication. It is also important to know if you or your partner have any allergies to specific materials. In general, items made of silicone are better quality, simple to clean, and less likely to cause allergic reactions, however they must never be used with silicone lubricant. It is highly recommended not to use your vaginal toys for anal insertion, or anal toys for vaginal insertion. Even with care and precaution, anal bacteria can be transferred and even a small amount could have very negative consequences if introduced vaginally. If a vaginal toy is ever used anally, it should be used with a condom and then thoroughly cleaned, boiled, and disinfected afterwards. For toys used only anally, the higher the quality, the less necessary it should be to use a condom. If they are cleaned after every use, a condom is not strictly necessary, however you may choose to use them anyway if you wish. If used, make sure the lubricant is safe for the condom as well as the toy itself. If your man's anus is cleaned (see FAQ), you keep your toys separate and cleaned, allergies are avoided, and you have chosen the proper lubricant, you are ready to enjoy pegging safely and sanitarily.




Hands On
You don't need any toys to peg your man, all you need is your hand and a glove. Whether you are fingering him, fisting him, or going at his prostate, it is a powerful move to be physically inside your man and in direct control of stimulating him. Even when using toys, starting out with manual pegging using your fingers, above and beyond the application of lubricant to him is a good way to start the process of opening him up for toy penetration. Remember to make sure the glove material does not cause either of you allergies, and that you use lubricant that will not react negatively with the material of the gloves.






Fisting
An extention of fingering, but certainly not something to start off with. Fisting is powerful and symbolic method of pegging that requires a certain anal flexibility men new to pegging will not have. Once you have had some experience with pegging, and have stretched your man out to a more accessable size, you can deliver a sizeable pegging with only your hand. Remember to make sure the glove material does not cause either of you allergies, and that you use lubricant that will not react negatively with the material of the gloves.





Plug Up the Hole
Anal plugs are very useful for a variety of reasons. Plugs can be used to widen your man's passage, and to train him to be able to take your toys. Plugs can be used for inserting and leaving in, which you can require while your man does his work around the house, takes you out, gets sweet with you on the couch, is making love with you in bed, or at any other time or place where the experience will serve your domination and enjoyment. Plugs are also a great bridge between finger your man and pegging him with your strapon of hand tool, as they help to spread out and introduce lubricant, force his hole to relax, and stretch his hole in order to ease penetration with your main line implement. Also useful for many of these purposes are anal dilators, inflatable dildos, and smaller sized dildos. These can be used before pegging, or in situations independent of pegging to get him stretched out and ready for infiltration. You will enjoy far easier access to his rear, and this will greatly increase his enjoyment of pegging, as well as his ability to handle toys of different sizes, shapes, and surfaces. Plugs generally become more difficult to wear the longer they have been left in, as lubricant will dry up, so keep this in mind in situations where they are not being used as part of pegging. While some women train their men to wear plugs overnight and for long periods of time, your man will probably have a hard time falling or staying asleep plugged, unless he is quite used to the size, or until he has had enough experience to stay asleep with one in, so plugs are best left in for shorter periods of time, or parts of a day. When being used for pegging, these difficulties are not important, as plugs being slid in and out are very much the same as other toys in their use. Another type of plug toy is the prostate massager. Whether vibrating or the manual variety, prostate massagers are used like a plug, and inserted fully before being operated. While not all men will leak semen from the procedure, all men will experience an uncomfortable but strangely pleasurable feeling from them, and they can be left in during other play and even used to stretch for other pegging.






Insertables
Insertables, including plugs and prostate massagers, are anything that is safe and useful to peg your man with. Anal beads, glass wands, anal vibrators, and dildos of every kind can be used to peg your man by hand, allowing your a great deal of direct control over the angle, speed, and intensity of the pegging, in many cases even more than the strap-on harness itself. Some dildos can only be used for pegging in this way, but even dildos that can work with a harness can be used in this way. One benefit of this kind of pegging is that it allows for many different positions instead of just directly behind him, allowing for pegging while you are on top of him, he is over your knee, bound in different positions, with you along side him, or from any other position that gives you the access you need. You can also use slightly smaller insertables to prepare him for the slightly larger dildo you have strapped on.










Strap-on Harness
Strap-on sex is a fun and popular method of pegging that allows a woman to use her body to penetrate her man. This method utilizes the intimacy and interconnection of traditional sex, is a powerful and invigorating experience for the woman, and an overwhelming and humbling experience for the man. It is also a psychologically devastating addition to chastity training, completing the reversal of traditional roles and making you the one who does the penetration in your relationship. In order to strap on your dildo, you will need a harness. while you can rig one up with rope or other materials, manufactures harnesses give greater stability, and allow different amounts of vaginal stimulation for you, depending on your preferences. Some harnesses are for specific sizes of dildos, while others have sized rings to accommodate different sized dildos, so make sure to get toys that are suitable for your harness. Some harnesses can only be worn over underwear or directly against your skin, while others will allow you to use them even when fully clothed. For women who like to peg in different ways at different times, having options is a good idea. Even dildos that are only one way can provide some or a great deal of sexual stimulation to the woman if the dildo is situated right, or if the harness has a built in vibrator or place for a vibrator to be attached.














Small and Thin Dildos
Smaller and thinner dildos are always an excellent way to start, particularly if you, or he, or both of you are new to pegging. Smaller dildos are suitable for pegging even the tightest of male bottoms, and allow you to explore speeds, methods of penetration, and your own stimulation with greater ease. Using a dildo too large for an unstretched hole will certainly not be at all enjoyable for him, and may even cause internal damage if it is far too large fro what he can handle. Even more experienced pegging may include smaller dildos, as they are a good way for earlier phases of a single pegging, and for loosening him up to prepare for larger implements. Depending on the particular dildo, a smaller dildo with different surfaces can be more stimulating to his hole than even a larger dildo that is smooth, so remember it isn't always size that matters as much as texture and the angle of the shaft of the dildo.











Smooth Dildos
Smooth dildos, no matter the size, are less abrasive to your man's hole, meaning they are usually far easier to take, as well as easier for you to move in and out as you please. Utilizing smooth dildos will allow you to advance your man to longer or thicker dildos faster for this same reason. Smoother dildos also mean that faster, more vigorous pegging, or longer, sustained pegging is much easier on the woman doing the pegging, allowing her to focus more on her own pleasure, and just what she is doing to her man.










Ridged Dildos
Just as with smooth dildos, ridged dildos have benefits of their own. Ridged dildos are the essential man trainer, guaranteed to overwhelm him. Since most of the nerves you will stimulate in him are right around his hole, the texture of the dildo is generally much more important than the length or even the size. Although it is usually best not to start him off with these, remember that your pegging will be more effective in training and humbling him if it is somewhat uncomfortable and difficult for him to handle. His discomfort is your ally, and his sacrifice and surrender in play is for your benefit, something he should be happy to provide, and if he isn't yet, this kind of pegging will help you teach him to be. As with all pegging, it is best to use plenty of lubricant, which will not diminish the experience, but will instead make it easier for you to work with, and allow him to focus on what is pleasurable and learning to enjoy this type of stimulation, especially in place of stimulation to his penis.










Double-sided Dildos
Double-sided dildos are a wonderful option to increase the sexual stimulation for you during pegging. Pegging is fun and an important part of his training even if you aren't getting any physical stimulation from it, but double-sided dildos give you the option of making pegging your route to pleasure when the time comes for it. Some women can derive so much more pleasure from pegging with double-sided dildos that they prefer it entirely to traditional PIV sex, a win-win-win for your chastity training of your man. Some double-sided dildos, can be used with or without a harness, some vibrate or allow vibrators to be used with them, while others are built right into the harness they come with. Adding your own sexual stimulation to pegging will encourage you to peg more often, which can only mean more fun, intimacy, and training for you and your man.










Vibrating Dildos
Vibrating dildos are an excellent choice for enhancing your pegging. They allow for greater amounts and styles of stimulation for you, while at the same time increasing the stimulation to his anus and prostate. No matter what level of size, length, thickness, and texture your man is able to take from you, a vibrating dildo of the same qualities will be that much more intense and dominating to him. Teaching your man to orgasm from pegging is also usually made easier by utilizing vibration. Even one-sided dildos worn over the clothes can give you stimulation during pegging with the addition of the vibration, meaning you can be enjoy greater physical pleasures while you are enjoying training your man.










Realistic Dildos
When choosing a dildo, style isn't the most important consideration, but with all the choices these days, you can get dildos that reflect you, you style, or how you are using them. Getting natural looking dildos isn't necessarily going to be your choice all the time, or ever, since they are no more or less effective than any other style. Besides simply choosing them for the look or style, a common reason for selecting realistic dildos is the psychological impact on your man's training. The reversal of roles is an important element of pegging, and its effect on your man's mind. The psychology of penis size, the manliness of erection and penetration, and the male egos relationship to his perception of his sexual prowess are deeply ingrained in the male mind. As much as possible, you want to use this 'against' your man for both your benefits, in as many aspects of life as possible, and none more so than in pegging. You now have the biggest and hardest cock in the relationship, so by this ancient 'logic' deep in the male mind, you are the 'man' in the relationship, and since you now are the one doing the penetration, you are the one in charge. Choosing a realistic looking dildo can reflect this arrangement, at most certainly amplifies the mental effect of all of this in your man's subconscious mind.

















Bigger Dildos
Once you have trained you man with fingers, plugs, and regular pegging, your man will be able to take bigger dildos for you. Choosing longer or thicker dildos from the start will almost certainly be uncomfortable and little fun for your man, so unless this is your explicit desire, it is best to ease him in and work him up to your more substantial implements. Once your man begins to learn to enjoy pegging, you will want to increase the challenge to his mind and body by using some larger dildos. Even if he is not getting to like it yet, once you have him properly stretched for your easier units, smaller sized dildos will be less difficult to handle, and therefore less effective in dominating him and advancing his over all mental training. While you certainly do want him to become used to pegging, and to learn to take pleasure in it, you never want him to become too comfortable, as taking the discomfort along with your pleasure is an essential part of the pegging experience. Longer or thicker dildos have a powerful psychological effect on your man, since penis size is very intimidating to a man whether he knows it or not. After taking larger girl cock from you, his level of submission to you in all aspects of life should only increase. Remember with longer dildos, proper lubricant and careful use is needed to avoid dangerous damage to his intestine, so as a rule, don't exceed 8 inches without care, knowledge, and experience.




















Huge Dildos
Don't ever use a very thick dildo on an anus that isn't trained and stretched to handle it. Very long dildos require serious preparation and safety. Dildos that are over 8 inches in length need to be eased in the further in you go, and need to be very well tubricated. Very long dildos cary increasing risk of damage to the intestine, which is a serious problem requiring emergency treatment. When it comes to pegging, bigger isn't necessarily better. How big and how long is too big? Only you can answer this question for you, however the majority of couples who peg never really venture into the realm of huge dildos. Most progress to the larger sizes that are at or just beyond the larger sizes of natural human penises. Adding further length or girth certainly adds more challenge, but will not necessarily enhance the experience for either partners. The only three reasons to opt for using huge dildos some or all of the time - one, you really enjoy making him take longer and thicker implements, two, he has learned to love your pegging so much and craves something even bigger than your biggest, or three, you decide you wish to make him for the accomplishments sake, to punish him when he enjoys more reasonable sizes, or just to make him do it for the sake of his training in submission. No matter why you choose a huge dildo, make sure it is not too much longer or thicker than what you are currently using, or he will need to be stretched out with larger plugs or dilators before it will be safe to proceed. For most who choose huge dildos, very long and smooth is the preferred choice, while only the most expert or sadistic pegging women will choose a huge dildo or ridiculous thickness and texture. For most women who peg, this kind of pegging is not necessary at all for their uses and interests.










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