Feminization Philosopher

I am super pleased to announce that I have finally had a full, anal only orgasm for the first time this past Thursday night, May 23rd, 2024. And it wasn’t just once, or even twice, but three in a row! I am extremely proud of the progress I’ve made in getting this far, and I’ve decided to write down everything that I did in an effort to educate other sissies/submissives in training on what worked best for me after a bit of further testing. I wouldn’t call this a be all, end all guide to sissygasms, but I’m sure that I can give you some advice that generally goes against some of the conventional wisdom of seen online. Do I have your attention yet? Let’s get started!

1. Precursor: Early Training and Mindset
2. Abstinence: Separation From the Old Ways
3. Submersion: Intense Hypnosis and Pleasure Association
4. Reform: Giving Up and Going “Pure Vanilla”
5. Surrender: Returning to Lock and Key
6. Finish: Final Thoughts (Skip to here for a summary/bullet notes)

1. Precursor: Early Training and Mindset

    This first section will be about how I first got into chastity and anal play, and how I gained the sensitivity necessary for the rest of the steps to work as they did. This can be done in a number of different ways, so you may find that you are able to go above and beyond what I did to get there. It includes helpful mindsets for getting started, content to help reinforce those mindsets, tips on choosing the right toys for you, and ways to increase your sensitivity. While this section has useful tips, but can be skipped if you’re experienced in anal play. Hypnosis is explained later in section 3, but it has better effects the more you listen to it, so include the first part of section 3 to your training below for maximum effect.

    I had been curious about anal play and chastity for a long time now, although only more recently has it become less of a fantasy and more of a reality. I had many periods in the past where I would put on a cage for a little while, try to play with my ass for a while, then get too pent up and quit before long. I believe my longest streak gone without cumming was just 2 weeks, and that was last year. In the first place, it was too much to ask someone who could masturbate every other hour of the day to hold back for so long. It was a multi step process to really get to the point where I would not only find chastity attractive, but come to crave it.

    Before anything else, you should find the right cage for you. Training without one is far more difficult, and the temptation to touch yourself could easily ruin days upon weeks of training. Choose a cage based on the dimensions of your penis when mostly flaccid, and look for options that come with multiple rings to try for the best fit. I made the mistake of buying my first cage based on my erect penis, and it was ridiculously oversized, but it did teach me one thing; Don’t wear a cage where need to get hard to completely fill. Your tip should comfortably rest at the end of the cage, and a ring that fits should feel tight but not restricting blood flow. I greatly prefer a cage with a fairly open top to wear full time since it makes going to the bathroom clean and simple, but see what you’re comfortable with and never forget to regularly wash yourself and the cage for good hygiene. 

    Once you have the right cage, the first big hurdle to overcome is idea that chastity cages are meant as a form of denial. I simply couldn’t hold back my rampant desires long enough to make more than a few days in the cage, and it was very difficult to make any form of real progress. It was then that I stumbled across Darkit, a content creator here on BDSMlr, who specializes in extremely positive chastity content. Their most recent content focuses on chastity maid play, but go a bit further back and you’ll find hundreds of captions to go through and see the mindset of a true chastity enjoyer. The correct view on chastity is that it isn’t a punishment you’re being subjected to, but a source of new pleasure you would have never found otherwise. There’s still plenty of value in submission and denial play, but that’s really only for experienced masochists with doms to control them, and doesn’t need to be set as the standard. It becomes far easier to lock yourself up for longer periods of time once you realize just how good the cage looks and feels.

    If you’re looking to adapt to the pleasures or anal play and chastity quickly, it’s most productive to start to focus on the pleasure of not cumming, or more specifically edging. At this point, I’m having difficulty discerning if I liked edging because of chastity play or the other way around, but realistically they go hand in hand. If you’re having a difficult time associating not cumming with more pleasure, then edging is a good start. Simply masturbate like you normally would, but slow down or stop entirely once you start to feel an orgasm approaching, staying on the “edge” of an orgasm. Be careful not to go far, as even after stopping you may still ejaculate. If you do have such a ruined orgasm, you won’t feel any pleasure from it, and can continue edging, although it will be more difficult to edge as your sensitivity will be increased. If you can begin to appreciate how much more pleasure you can get from masturbation that doesn’t end, you’ll begin to see the real appeal of chastity; it’s really just like edging, except the possibility of accidentally going over the edge and ruining it is zero. The sensations are remarkably similar, so you can train your brain to like the feeling of chastity in a more natural way before trying to delve deeper.

    Once you really start to see chastity as a source of pleasure, it becomes easier to keep training for longer periods of time, and start increasing your sensitivity. It’s best if you never touch yourself normally during this, as you are trying to focus on feeling new nerve endings. For this purpose, I was training my nipple sensitivity as well to use as a separate source of pleasure, but it’s more important to train the sensitivity of your prostate. To really boost your sensitivity, it’s best to continue masturbating until you begin to feel a little bit sore, and then continue for just another couple minutes softly. This will stimulate exposed nerves and boost your sensitivity if repeated regularly, but always make sure to give your body time to heal in between sessions. For soreness of the nipples or sphincter, Aquaphor works the best from what I’ve found. It heals the skin and makes it softer, so you don’t have to worry about the skin growing back thicker as you continue training.

    The best toy to use for this depends on your anatomy, so try a handful of different sized prostate massagers or plugs until you find one that feels really good. No matter what toy you end up preferring, make sure to actively train your prostate muscles to squeeze longer and harder (look up kegal exercises for more details). The massager was great for my training, as I lacked the physical strength and endurance necessary to bounce on a dildo for long periods of time. After a good deal of experimenting with different positions, I found the easiest and most pleasurable position for me was to push back against a wall and lean forward to a counter for support. When I say easiest, that’s because I would have needed to train many different muscles to pull off every other pose, but this way I only needed to train my back muscles to maintain a good arch and get the right angle on my P spot. It ended up working as 2 for 1 training, as building those muscles by walking around with my back arched naturally gave me a more feminine walk. Whatever method you use, consistency is key; you really want to be able to hit the same pleasureable spots every time. Using the same toy from the same position until you reach a high enough sensitivity is your first priority, but this is supposed to be fun! Feel free to mix it up a little if you’re craving something different.

    While it may be possible to slowly build up the resolve and willpower necessary to stay in chastity for longer periods of time, it isn’t a requirement. Even after the initial change in mindset, it was extremely difficult for me to get past a week without a full orgasm, and I would almost always unlock in a week or less. It took me a few years of infrequent anal masturbation to reach this point, however this just meant that I was training my sensitivity slower than a more dedicated person; With each session, my sensitivity was definitely increasing. All I needed was 1-2 sessions a day of masturbation with the right prostate massager and nipple play to hold back my desire to cum long enough to boost my sensitivity. Don’t aim to just masturbate since you’re horny, but try to keep going until you’re “satisfied”and no longer feel the need to continue, plus a little bit extra for good measure. These sessions will slowly increase in length as your training continues, so if you don’t have time for 2 sessions a day, make your one session at night to reduce the risk of morning wood.

    Sensitivity is the most important factor when aiming for an anal only orgasm. However, without the stamina (both sexual and physical) to masturbate for a long period of time, your chances of reaching an anal only orgasm are low. Before you get used to anal play, you run the risk of unwittingly expecting an orgasm after a certain point. Since playing with your prostate feels like edging, even if there’s 0 chance that you go over the edge during your training, reaching an orgasm is most likely so normal to you for sex that you’ll have a hard time drawing your mind away from that idea. All effort is good effort though, since it will ultimately boost your sensitivity bit by bit, even if you give in and masturbate normally. As long as you consistently build the connections with your pleasure receptors and become more tolerant to a higher degree of pleasure, you will consistently get closer to being able to cum just from fucking yourself in the ass.

    Repeat this training method, combined with the beginning of part 3 for best results, until you can train for hours on end without issue, and both lightly or vigorously touching your erogenous areas results in pleasure. Mentally, you should begin to see yourself as your effeminate and/or submissive goal. The thought of your training being cut short by the desire to cum will seem almost fearful, and you want to experience more pleasure that ever before to escape that possibility. If you think you’re ready, try the steps laid out below and see how it affects you, but read through the whole guide at least once at first to see the full picture.

2. Abstinence: Separation From the Old Ways

    Once you have enough sensitivity, you can begin to really focus your mind on that pleasure and move away from traditional masturbation. There were many times when I had simply swapped from masturbating normally to chastity play simply because I wanted to, but there was always this connection to the old ways that I couldn’t get around. It was then that I had a new idea; What if I simply refrained from masturbation completely for a while? 

    Abstinence would be a great way to weaken the connections in my mind on what pleasure and regular masturbation feels like. Not only would it then be easier to focus my brain into fully adapting to this new form of pleasure, but it would also boost my sensitivity before I had even started training again. The only problem is you need to find a way to go days at a time without masturbating at all. While it isn’t necessarily easy, there are ways to greatly increase your chances of success.

    First, restrict yourself from internet and social media access filled with erotic content. The goal is to go as long as possible without masturbating, so there’s no good reason to make that more difficult by scrolling through Twitter and seeing porn. YouTube and Instagram are good choices for vanilla content streams, but it might be better just to make a new account on a site of your choice and then actively avoid any erotic content. To that extent, you should avoid doing anything you view as “erotic”. This includes wearing chastity, as the weight of wearing it may only serve as a constant reminder of what you’re trying to do. The ultimate goal is to forget all of that and simply enjoy life.

    To that extent, get out of the house and do things with friends and family as much as possible. It’s much easier to not think about masturbating when you aren’t constantly in a room where you’ve probably jerked it countless times. Habit is a fearful thing, and you may quickly find yourself bored and looking for a quick source of pleasure far more often than you may realize. If at all possible, go on a vacation or just visit some family for a week; just try to keep yourself busy during the day. Anything will do, so long as it isn’t too stressful and it uses enough energy to make you look forward to simply sleeping each night. 

    Once you’ve spent at least 5 days or more without masturbating, the feeling of ejaculation and penile stimulation will begin to fade in your mind. Your new goal from here will be to replace that old method of pleasure with the new, and deeply associate your ass as the proper sexual organ for you to use and abuse. 

3. Submersion: Intense Hypnosis and Pleasure Association

    Your goal is to experience a completely foreign form of orgasm that your brain isn’t accustomed to. Even if you have the sensitivity to do so, your frame of mind is equally important; you need to believe that this pleasure should be the way that you orgasm from. You are going need to completely re-wire your brain to a new source of pleasure and change how you think of both yourself and sex on a fundamental level. And what better way to do that than hypnosis and mind altering substances (alcohol, weed, etc.)

    Before I go into any further detail, I must be prudent and state that you need to clearly understand your limitations before beginning this process. It does you no good to get sick from drinking too much or getting so high you can’t do anything. If you are in a state where it’s legal, I would recommend buying some bud gummies (more specifically a hybrid or indica strain as they’re better for sleeping and I find also inducing a trance), but alcohol will also work. While you may believe you understand your tolerance levels in relation to alcohol, your tolerance to weed may be entirely different. Some people can eat 4 gummies (20 mg) at a time and still be highly functional, and others say 1 (5mg) is almost too much for them. Always try a small dose in the comfort of you home to test your tolerance level before proceeding.

    Once you have chosen your substance (in my case Camino gummies), it’s time to select a hypnosis of your choice. Hypnosis is a great way to relax your body and mind when you really get into it, and helps reinforce important ideas necessary to attain a submissive mindset. Try searching for keywords and erotic hypnosis scenarios you find the most appealing, and listen to a couple of videos or tracks sober until you find one you can agree with. Hypnosis isn’t some all powerful tool to change your mind; hypnosis cannot make you do something you don’t want to. If you enjoy most of what the hypnosis has to say except for a few key points you personally would never agree to (humiliation play, eating ass, body modification, etc.), you won’t be able to get fully absorbed in the fantasy. The right hypno for you should contain provocative ideas that arouse you, and nothing you feel so strongly against you resist the hypnosis. If the hypnosis you found is less than hour, find multiple tracks to listen to and set up a playlist. Ideally, you should be able to lay back and relax while listening to any hypnosis, with a vibrating toy or maybe even fucking machine to help associate these new ideas with pleasure.

    Now you’ll have every thing you need to begin your descent into a hypnotic trance. The trance itself will really only last as long as the hypnosis, and won’t have any lasting effects unless the listener is under extreme stress or emotional disorder. The only thing hypnosis can really make you do is think. With your mind working differently under the effect of your chosen substance, you will be forced to face all of these ideas of submission and anal pleasure in a new light. It will be helpful for your journey if you record all of your ideas after each session to see how your perspective is shifting, so you can listen to the hypnosis each time with a better understanding of the contents.

This is the end of the part of section 3 to incorporate with section 1, the rest will detail my experiences and the build up to my sissy “awakening”.

    The hypnosis tracks I used most often were part of the “Bambi” series, a collection of hypnosis tracks centered around the idea of cultivating a brainless bimbo personality in the listener. The exact video was a 2 hour mash up of different audio clips to form one long trance experience, which I found myself hooked on after a long Sunday trip building up to the “Day 3” track. It cleverly uses suggestions to slowly open your mind to the ideas it provides, with triggers and phrases to reinforce multiple pleasurable sensations. There were further tracks in that series that go even further, but I only listened to 4 and 5 a handful of times after 3 since I didn’t enjoy the triggers for staying permanently in feminine attire and completely losing all sense as a mindless cock sucker. I was quite worried about it really was taking over my personality towards the very end of my training with how many times I’ve listened to it, but I’ve since found ways to ground myself. I had always remembered the contents and triggers of the hypnosis, and I still find the idea of it all erotic, I choose not to obey the triggers anymore. 

    Through a number of sessions taking 30mg and one 40mg session (which was really pushing my limits), I focused myself to forget about my current body as much as possible, and embrace a girly blonde bimbo mental state. From there, I began to tease my nipples and use a prostate massager to create a connection between this feminine persona and pleasure. Rather than listening to the track and mindlessly obeying, the last time I had listened I was so incredibly high that I used the hypnosis to dive deeply into my subconscious and make me accept my new sissy lifestyle. At the time, it felt like my hands and body were working on a higher level above the hypnosis to break down and rebuild my idea of pleasure. It was especially useful for finding the inherent appeal about a submissive mindset; obeying is pleasure. And not just in the most simplistic sense of “if I obey and keep going, I will feel more pleasure”, but rather that the act of obeying is pleasurable. The ideal submissive mindset is one that finds that all experiences are positive ones, so long as they are obeying what they were told. This new wave of experiences and emotions combine into a new submissive pleasure, one which greatly outweighs any potential discomfort avoided by not obeying. This pleasure is something you chose, something that you deserve for all of the dirty erotic things you’ve done to get here, and now, it’s something you crave. The realization that any discomfort created by not cumming normally is nothing more than another spice to add to the pleasure of the entire experience is the final hurdle to reaching that highest peak of pleasure. It’s definitely a tall order to ask for right away, especially considering how long it took me to finally understand it, but that’s what the next part is for. It’s time to understand what your life would become without this pleasure, to see if you now truly can’t live without it.

4. Reform: Giving Up and Going “Pure Vanilla”

    After my experience with getting unreasonably high and training myself to fully embrace submissive pleasures, I was initially worried that my mind might really give way to all of the body modification suggestions within the hypnosis and I would lose sight of myself, so I chose to completely distance myself from those ideas and “return to normal”. I went back to just penile stimulation, put away all of my assorted lingerie, cages, and toys, and tried to forget about the whole thing. While it was useful in pulling back from the troubling ideas in the hypnosis, all I ended up doing was proving that “normal” wasn’t good enough anymore.

    At first I went back to jerking off to my old straight porn again, and it did feel good for a while, but ultimately it felt like it was lacking something. I made it a point to not tease my nipples at all during this period, since I had made a strong association with playing with my nipples and prostate at the same time, and I didn’t want to break that association. My belief was that I could hold back those desires by not engaging in one or the other, and simply jerk off as many times as I needed to “recibrate” myself by to normal. However, ultimately that foolish idea backfired, and fully primed me to go deeper. All it took was one night of drinking to easily toss that entire vanilla bullshit in the trash, and gleefully lock myself back into chastity. Teasing my nipples had become such an important source of pleasure in my mind that I couldn’t go cold turkey for more than 2 weeks. In order to even make it that far, I had to constantly jerk off thinking about how hot it was that I was restricting myself from touching them, all the while slowly drifting back into consuming more sissy chastity porn. 

    Looking back, I probably could have avoided this fate if I really wanted to. If I really hated the idea of becoming someone or something I couldn’t agree with, I could have gotten rid of all the sissy stuff I bought and completely distance myself from ever consuming that type of content ever again. In fact, I did do it before, roughly 4 years ago when I had first started getting into it. Purged all content saved, lock everything physical away, and grit my teeth while never teasing my nipples for well over a month. However, in the end, I came back looking for a higher source of pleasure, and have never fully escaped since. The hypnosis can’t really change your mind, it can only make you think; But the pleasure can be so captivating that it does change you, literally tempting you to open your mind and seek out more. Humans are incredibly resistant to pain, but remarkably weak to pleasure. Some part of you already likes the idea of being caged, teased, and potentially also feminized, so all it really takes is enough exposure and training to get to this point.

    If you’ve read this far, there’s a good chance you are stuck in this web of pleasure as well. You may be able to still back out, but it won’t be easy. Like any other addiction, you would probably have to fight for the rest of your life against it. As long as you are unable to completely reject the pleasures presented to you and the futures they lead towards, your submission is inevitable; It’s only a matter of time. It won’t happen in the short term, it will probably take years of exposure and casual masturbation like myself. But if you keep coming back, training again and again looking for this pleasure, eventually you’ll just accept that it’s better that jerking off, and you really don’t want to go back. If this thought scares you, then you should stop reading here, and get out while it’s still comparably easier. Otherwise, feel free to come with me down to the bottom of the rabbit hole, and find pleasures the likes of which no average male will likely ever reach.

5. Surrender: Returning to Lock and Key

    After having returned under lock and key for what may most likely be the last time, I noticed a considerable difference in attitude towards the experience. Before, I needed to constantly repress how horny I was, and couldn’t escape the idea that I wouldn’t be able to hold myself back from ruining an orgasm once I reached a certain limit. But now that I had this empty feeling in my mind from not staying on edge, I found that it only went away after 1-2 days of teasing and training. It was working, but I needed something more; I needed to hypnotize myself further.

    I wanted nothing to do with that hypnosis video I had listened to leading up to this, so instead I started micro dosing weed nearly every day and pivot towards self hypnosis. I had already laid the groundwork by building off of the hypnosis video, and I could easily enter a trance when high now. I didn’t want to actually undergo surgery and turn into a dumb blonde bimbo slut full time like the hypnosis suggests, but the appeal of chastity had grown so great that I wanted to foster the mindset I had started to create. So I cut back on the dosage of THC and tried my best to hone my mind on all the concepts and ideas of submission that I had built leading up to this point.

    I took one gummy eaten before bed, 24 hours after putting the cage on. Another gummy in the morning, once more the day after that, and another the following day (just 5mg each). Each time, I would focus on the pleasure, and continue to tease and train myself no matter what I was feeling. Whether I was alert, tired, focused, relaxed, satisfied, frustrated, riding on cloud nine, or feeling a strong urge to cum, I kept training. That pleasure could change whatever negative I might have been feeling into a positive, and every positive emotion into an even greater one. I was able to hypnotize myself to keep squeezing and pleasing myself for much longer than I ever had before, and it helped me overcome the greatest hurdle for continued chastity play; my desire to cum. It was in this state that for the first time, I had even begun to see my denial as a positive. The normally overwhelming feeling of horniness was now something I started to crave. I knew that I deserved this feeling, for I was below someone greater than myself, and they wanted me to experience this pleasure. Feeling horny is comparable to sitting in a sauna, with my experience allowing me how to last longer than ever before. What was once a scorching, unbearable heat, had become toasty to the touch, and I discovered that I could finally spend as long as I wanted basking in it.

    On the last day leading up to my anal only orgasm, I was sober the whole day. I simply spent my time teasing myself, but after nearly 4 days of intense stimulation, my nipples were starting to get a bit sore. I would then only lightly tease them to keep the strong connection, and focus more on anal play for the later half of the day. Towards the end of the day, I brought my favorite dildo to the bathroom to spent some quality time with it before my nightly shower like I had the other nights. I decided to wear an extra piece of lingerie tonight, which I hadn’t really done the days before. I looked at porn while riding the dildo attached to the wall, looking down at my shaved body in the lingerie. 

    Within minutes, I felt this strange sensation in course through my body, and all my lower body muscles instinctively clenched hard around the dildo. I had felt this sensation before, but at first it felt like I was gagging on something, so I had stopped moving every time it had happened. I learned later that this action was extremely important, as not only did I need to squeeze my prostate with my pelvic muscles, but also use my gut muscles to push down the dildo into my prostate for more pressure. This time I obeyed my training, and continued to thrust despite the initial discomfort. Suddenly, I felt a spurt of jizz be literally squeezed out beneath me. I was in shock, I couldn’t believe I had actually done it. It was certainly an intense feeling, but I barely felt any of the pleasure I had heard of. But it was real, I scooped the dribble of my newly christened clitty onto my finger to taste it, and sure enough it was cum. Knowing that it was entirely possible to orgasm repeatedly this way, I continued pounding back on the dildo again. The second time was a bit more awkward, since I was focused on making sure I kept moving even as the sensation overwhelmed me, but I reached it again, and spurt much more than the first time. Finally, I tried for one last time to get there again, letting it build up a bit more slowly this time, and really squeezed as hard as I possibly could. I had done it a third time, but I couldn’t go any further. Not because I was too tired physically, but the experience took quite a lot out of me mentally. I pulled myself off from the wall, and saw the pool of cum that had collected at my feet. I had finally done it, and I was filled with a huge sense of accomplishment.

    In the days following, I proceeded to reach a pure anal orgasm at least once every night for the next 3 days after that. While I settled for just one the night immediately after the first due to injuring myself, I then followed it up with 2 straight nights of 4 in a row. I’m currently working on spreading out these milking sessions as doing every night seemed impractical, and I really wanted to build my affinity with denial. So far, I’ve only really had to suppress a few very mild headaches as I become fully adjusted to this new lifestyle, and keep myself satisfied with regular anal masturbation. I do have to make an effort to go to the bathroom before each fucking though, as I went straight into fucking the dildo one night without peeing first, and pissed like a bitch on my second orgasm. 

6. Finish: Final Thoughts

    In the end, the entire experience was nothing like I had imagined. I had expected for years that it would be my prostate massager that would do the trick since that felt the best, but all it took was fully adapting to my 10”dildo to completely overturn that belief. The sensation of the orgasm itself was not very pleasurable, but it was definitely intense and deeply satisfying. In the days after, I was able to reach that same state again and again each night. The build up to the orgasm has become far more pleasurable, and the satisfaction is slowly eroding my desire to cum normally at all.

    I had initially feared that despite all of my current efforts and progress, my desire to cum would eventually win over my desire to stay locked. But incredibly, I managed to achieve a full anal only orgasm in just 5 days of being locked, solving the issue before it got beyond my control. Even if the destination wasn’t this mind shattering orgasm that I had expected it to be, I believe that the value in making the achievement lies in the fact that I can now theoretically stay in chastity as long as I want. If I can always just release the pressure my sissy juices are creating, then the only limits are the ones I place myself. I am still adjusting to this new mindset, but staying in chastity has never been so easy. As long as the current trend continues, I believe these orgasms will continue to become more euphoric to reach and more fulfilling to complete, eventually eliminating my desire for a normal orgasm entirely. I am set to break my days locked in chastity record this Saturday night, June 1st, and definitely feel some cosmic irony on the record being broken on the first day of Pride month.

Here’s a summary of the most important things I’ve found through this experience:

• Sensitivity can be trained over a long period of time, and increasingly lengthy periods in chastity aren’t required 
• Chastity is an excellent way to literally and spiritually seal away the old self and focus on new pleasure
• Abstaining from any form of sexual activity before training can make separating from the normal forms of pleasure much easier 
• Repeated hypnosis during training is a great way to reach the right state mentally as well as physically, but know your limits and when to pull back
• At any point, you can return to vanilla masturbation and cut back on the concepts you find its all becoming too much (but you’ll likely be back eventually)
• If your mind and body are in sync, you can go beyond your maximum limit of pleasure and train far more effectively 
• Keep masturbating with your ass and continue to squeeze your prostate hard as often as you can, you can honestly never train enough
• All it really takes is the right circumstances for your opportunity to come along, your body will tell you when it’s ready; just don’t stop

    Thank you so much for reading, I hope this deep dive has given you some insight on surprising complex topic of fucking yourself in the ass. If you had any questions about something I talked about in this very long post, I’d be glad to talk more about it! If you have anything you’d like to add or simply feel inspired by some of the concepts above, I’d love to hear your thoughts. This has been Jasmine, and remember, chastity and anal play today keeps the post nut clarity away!