How To Please Your Women With Chastity

How To Please Your Women With Chastity

A close friend and ex-lover of mine recently shared his journey to becoming a better lover after reading the book She Comes First by Ian Kerner. I too listened to “the thinking man’s guide to pleasuring a woman” as an audio book and while I found a lot of the information useful, there were also times I had to refrain from screaming at the car stereo. At one point the author advises against face-sitting, one of my favourite activities from both perspectives, and my ensuing rage prompted this post. So from my perspective as an experienced Mistress, I share with you my take on cultivating female pleasure while ensuring your chastity device keeps you firmly on track.

Setting the mood

Even if your mind is constantly focused on your locked-up dick, don’t assume your Mistress feels the same. Work for her attention, let her know that you are capable of thinking about her needs and not just your own. Setting the mood for sex, pleasure or romance shouldn’t only start in the bedroom.

If your Mistress is anything like me, I guarantee the work you put in beforehand will pay off in intensifying her pleasure later.

  • Clean the house and groom yourself in preparation and remind yourself of your position in the dynamic. Consider what things she enjoys and plan your time together accordingly. 
  • Mood-setting activities I recommend include: watching a film (ideally sexual in content but don’t feel it needs to be explicit if that isn’t her thing), listening to a sex and/or kink podcast and using it as a starting point for discussing things she enjoys and fantasies about. 
  • Cook her favourite meal or treat her to dinner. Dress yourself up and encourage her to wear something she feels empowered in. Initiate sexual conversation throughout but ensure to focus your questions on her pleasure, not your own. 
  • Make eye contact whilst listening to her and engage in non-sexual touch such as a foot massage or gentle caressing of her delicate skin, particularly around her hands, arms, neck or back. 
  • Stroke her hair and give her a head massage whilst she tells you about her day. Being self-centred won’t win you any brownie points.
  • Run a bubble bath for her to enjoy and decorate the room with candles and plants. Make her a playlist to listen to while she soaks herself and prepare the bedroom for when she is done. 
  • Consider the atmosphere of the bedroom: room temperature, lighting and smell. Use an incense burner or scented candles if she enjoys them. A dimmable rock salt lamp or fairy lights can be a wonderful addition to set the tone. Brightly lit rooms can feel too clinical but total darkness will inhibit your ability to read her body language. An electric blanket underneath where she’ll lay will help keep her warm along with an additional throw if required. Pillows and cushions may seem unnecessary but ensuring you can get the best angles will make all the difference later so make sure you have a couple of extras to hand.
  • Don’t forget this is about her, not you. You aren’t looking for praise or reward but instead your focus is on being selfless and creating a relaxing environment for her. Removing any responsibilities and distractions frees up her mental and physical energy, allowing her mind and body to be filled purely with pleasure. These might not be the kind of things that get your dick instantly hard but lucky for you, your device won’t let that happen anyway.

Help her relax but don’t send her to sleep

When it’s time to start touching her body make sure you don’t get yourself worked up too soon. There’s a chance she may wish to use you later and it’s important for that to remain an option.

Indulge and relax her, remembering to keep it sensual. Now is not the time to work out her knots with a sports massage or provide a sleep-inducing aromatherapy session. Those times will come but today you are focusing on arousal and pleasure. Take your time to gradually and deliberately undress her and/or help her slip into something that makes her feel sexy. Now you can begin to erotically massage her body.

The ideal position to give a massage is standing at the side of your partner while she is lying down on her front, allowing easy access to her whole body. However, chances are you don’t own a professional massage table and it is therefore important to give some thought to how you position yourself. A bed can actually work very well for a more intimate massage session but you should remain aware of your own body as well as that of your partner. Straddling your Mistress will give you good access to her back and shoulders but unless you are skilled in holding your own weight, this can be a very uncomfortable position for the receiver. A better option is to kneel to one side of her and concentrate on the areas within your current reach, repositioning yourself as you move up and down her body. Consciously vary the amount of contact your body has with hers depending on which part of her you are focusing on and the pressure of your hands. For example, sweeping your fingertips softly over her lower back while holding your body away from hers slightly will encourage her to focus solely on the sensation of your fingers. Using your whole palms and forearms to press and knead between her shoulders while drawing your body close against her enables you to use your weight to deepen the massage.

I recommend starting at her feet. Position yourself at the end of the bed, massage her feet with gentle kisses and explore whether she enjoys her feet and toes being sucked or licked. Does she prefer a gentle pressure or something firmer? Depending on her sensitivity, a very light touch may prompt a ticklish sensation. Pay attention to how her body responds to this and vary the pressure accordingly. Encourage her to lay face down on the bed so you can begin to work up her legs. Take your time caressing the delicate skin between her thighs. Trace faint lines with your fingertips, hovering near to but not directly touching her vulva. Be lighter and more gentle than you think.

Move up to her back and shoulders. At this point, if you’ve done a good job, one of two things will happen: she’ll stop you right there and insist you begin to sexually pleasure her immediately (do not protest, she is in control) or she’ll start thinking about it and be a little disappointed that your touch has moved away.

Start at her shoulders and give them plenty of attention before gradually making your way down her back towards her bum. At the shoulders you can be deep and firm in your touch as she’ll likely be holding a lot of tension there but become lighter and more delicate again as you move back down her body. Show her that you have range, that you have control over your actions. Be intentional.

Once you reach her lower back begin to kiss her gently at the part where her bum and back meet. Run your hands down her sides, coming to a halt when you firmly (but gently) grab her hips and use them to lower yourself down so that she can feel your breath, warm and needing against her lips.

Oral sex

In one slow but steady motion, run your tongue between her labia and gauge her level of arousal. Is her clit already swollen? How noticeably wet is she? Has her scent changed as her arousal levels build? Listen to her body and learn what it is that she wants and likes.

While this can be a very enjoyable position to receive oral sex, many women are more comfortable laid on their back. If this is the case for your woman, assist her in rolling over. Make sure she’s comfortable. Does she have enough pillows? Is she warm enough? Perhaps place a pillow under her lower back, angling her hips upwards allowing you better access to pleasure her and eliminating the need for her to support herself. Your woman is in control, remind her of that. If she’d rather straddle your face and have more power over her pleasure then enable that.

Take time to check in. Words can be sexy, silence can be daunting. Do what feels right in the moment and for her specifically, there is no formula to what each woman likes. If talking is her thing then ask her how she feels and if there’s anything she’d like. Is she happy for you to continue? Remind her that right now is all about her and that you’re excited to bring her pleasure and you want to be shown exactly how she likes it.

If she’s open to it, you can encourage her to demonstrate what she most enjoys with her hands and then replicate this with your own hands or tongue. Make sure to regularly assess whether her body language is relaxed and ask occasionally, but not too often, if you are doing it right. Is there anything you could do better? Ask what she’d like you to do. Listen and do as you are told.

By now your cock will undoubtedly be screaming for attention, tensing hard against its prison bars. All you want is to feel her touch, to be allowed inside her, to have something, anything. But now is not your time.

If she doesn’t enjoy, or doesn’t feel like, giving you direct orders then try some of these actions (laid on her back, hips angled slightly up is how I imagine her to be, but tailor the following to whatever is possible/pleasurable in her current orientation):

  • Run your tongue softly up each side of her outer labia, teasing her with just how close you are to her most sensitive areas.
  • Kiss her attentively. Kiss her labia. Kiss her pubic mound. Focus all your attention on showing just how ready you are to give her the best orgasms of her life.
  • Gently begin to run your tongue up each side of her clitoris, slowly forming circles around it but not yet making direct contact.

Check in, don’t get too carried away. Keep an eye on how her body responds to each of these gestures. Take more time over the things she visibly, audibly and palpably responds best to.

  • Once you feel her clit is swollen and ready for more direct touch, begin to part her labia minora with your tongue. Make repeated upward licks from the entrance of her vagina up to her clitoris. Start slowly with a wide flat tongue. Apply pressure and don’t be hesitant.
  • While everyone enjoys different sensations, wetter is often better. Make sure that there is plenty of lubrication either from her body or your saliva. Tilting your head slightly downwards during oral sex can help contribute to keeping things wet.
  • Try varying the way you use your tongue: explore the difference between using the centre of your tongue as it remains relaxed to tensing your muscles and using the tip more pointedly. Listen to her body. If she enjoyed talking then ask her how it feels and what she’d like you to do.
  • Once you’ve got her hips moving and her juices flowing, begin to introduce your hand. Nothing too intrusive. I know your cock is pulsating and pleading but you already know there is absolutely no way it’s getting a single ounce of attention tonight. Ignore it. Forget about it. I’m certain your pathetic dick is the last thing on her mind right now. 
  • Introduce just one finger at a time (your nails better be short and well-manicured!). Gently circle the entrance to her vagina with your finger, ensuring she is well-lubricated (if not, work harder! And also apply her favourite lubricant* - I’ll leave a note about this at the end). 
  • Once her body is asking for it (or, better yet, she verbally instructs you), slowly insert one finger, applying a steady amount of pressure along the front wall of her vagina (the surface closest to her stomach on the inside). You should still be maintaining contact with your tongue so now begin to use the strokes of your tongue in time with the movement of your finger. She’ll likely enjoy pressure against the part that feels ribbed (an area that feels similar to the texture of a walnut) but not too much poking or prodding. If you’re doing it right, this part of her may begin to swell slightly.
  • Move your finger in a consistent in-and-out motion though it's advisable not to completely remove your finger during this process. It can feel nice to completely detach from her on occasion but it can ruin the flow if you break contact with her body too often. If this is having the desired effect, try a ‘come hither’ motion by curling and uncurling the upper part of your finger against the front wall of her vagina.

Remember to listen. I know this may be a lot of information for you to digest all at once but, as the superior sex, us women have high expectations. If you want to prove yourself as the perfect chastity slave, you’ll need to pay close attention and work on this. If you want her to ever consider unlocking your cage again, you damn sure better let her know just how attentive you can be.

  • If her body feels ready (relaxed, well-lubricated and not too tight), explore how she likes the sensation of two fingers. Repeat the same action but this time giving her more girth. If she relaxes even more during the process, consider adding a third finger.
  • If your hands aren’t working for her or she simply feels you aren’t worthy of the pleasure, try with her favourite dildo(s) instead.
  • By now your tongue should be tiring - don’t you dare stop! Try other tongue gestures, picking one and sticking to it for at least ten repetitive movements at a consistent pace. Perhaps try very gently sucking her clitoris and flicking the tip of your tongue back and forth or side-to-side over her clit. Return to creating circular motions or varying the part of your tongue that’s in use. Explore different pressures, speeds, directions.

Keep up your energy and momentum and, if permitted, express how much you enjoy satisfying your goddess with the occasional moan or sigh of pleasure. Encourage her to orgasm and, if desired, repeat the above until she comes again (and again, and again…). Explore the use of a dildo to fuck her like you wish you could or a vibrator pressed gently against her clitoris and/or inserted. Ask her what pleases her and spend as long as it takes to ensure she is completely and utterly satisfied.


Should your Mistress desire a more penetrative experience, don’t be fooled into thinking there is any chance she’ll want your penis inside of her. You’ll remain locked in your cage throughout but there are other options for satisfying her. Strap-on sex is wonderful and can be enjoyed in many ways by all genders. In this case, you’ll be the one wearing the harness and providing your woman with the satisfaction that you could only dream of giving her with your own dick.

Be sure to choose a harness and dildo that works for you both and fits comfortably around your cage. This is a conversation best had prior to bedroom fun.

Make sure not to spend too much time away from your Mistress while you put on the harness. With a little practice, it’s possible to put on a harness one-handed so you can keep your other hand in contact with her, gently caressing her to keep the mood going. If this is impractical, you can either use two hands and make a show of it or give her a vibrator to enjoy herself while you fasten the harness in place.

Don’t be too eager. Return to stimulating her once more with your fingers and/or tongue to build anticipation. When she is well-lubricated and relaxed, hold the base of the dildo as you slide inside her. Use your hand to gauge the depth and don’t immediately thrust all the way in but take it slowly and gently. The more your goddess relaxes, the more pleasurable it’ll feel for her to be filled. Start slowly, with the addition of lubricant if required, gradually picking up the pace and finding a rhythm that works with her body.

Strap-on sex works in a variety of positions and, as most dildos are curved slightly upwards to imitate the shape of a penis, an added benefit is that the attachment can be adjusted or rotated in any direction (curved upwards, downwards or even to one side) depending on the angle of penetration and what feels good for her body.

No doubt by now your own penis will be straining and throbbing with jealousy in its cage, desperate to be the one inside her, begging for touch. But don’t let this distract you. You are a toy designed entirely for her pleasure, your own needs are not to be addressed.

Continue pleasuring your Mistress with the strap-on dildo and consider using a vibrator on her clitoris at the same time. Hands-free vibrators like the We-vibe can supply added pleasure both internally and externally as you penetrate her but be cautious not to get carried away using all the toys in the box. Sometimes simplicity is best and your hands should now be well-trained in massaging her clitoris to orgasm.

When your woman is fully satisfied, slowly withdraw the strap-on dildo and turn off any vibrators. Be gentle but precise with your touch; her body will be incredibly sensitive and you want her to remain in that orgasmic bliss for as long as possible.

Your cock will be disappointed. It desperately craved her attention, your attention, anyone’s attention and it got no more than the occasional sensation of the duvet fabric brushing past the outside of your cage. If your body was disobedient and leaked pre-cum during the experience, ensure it is cleaned up. Beg for your Mistress’s permission to lick it up and change the sheets if needed. Remember next time to be prepared with a towel underneath you to ensure she has no indication whatsoever of your pleasure - surely I don’t need to remind you again that this is not about you.

Lubricant - A liquid lifeline

*If you plan to use any kind of sex toys, it’s advisable to stick to water-based lube as silicone lubricants can interfere with silicone toys. If you accidentally destroy her favourite dildo you’ve got no chance of ever having your cock unlocked! No, that is not the way to get that outcome. Lubricant can be used during any kind of sex, including oral, however even the best brands won’t compare to her natural taste. Check in with her and, where appropriate, gently ask if she would like more lube. Just picking up the bottle can function as a more indirect way of posing the question, to which a simple nod or shake of her head will be sufficient indication of her preference.


1 thought on “How To Please Your Women With Chastity


Thank you so much I’m learning to understand why she ask me to wear a chastity I have not never thought about it like you have stated I guess I have always been thinking about my self so I better understand that I should wear a chastity for my girlfriend thank you to explain how I should consider her more

September 13, 2022 at 02:00am

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