Welcome to Stretching September! This month, we’re putting a spotlight on the art of anal stretching, an essential part of the anal only journey. Whether you’re just starting out or have been enjoying anal for a while, Stretching September is about deepening your understanding and skill of this incredible practice.

If you’re new to the anal only lifestyle, Stretching September is the ideal time to start exploring the world of anal stretching. Start by using fingers or small toys and remember to take your time, using plenty of lube and going at a pace that feels comfortable. The aim is not to rush but to understand and respect your body’s limits while steadily progressing.

For those of you who are already familiar with anal stretching, this month is an opportunity to explore new challenges. Perhaps you could try a bigger plug or dildo, or push the duration of your stretching sessions. Always ensure that you’re warmed up properly and in a comfortable and relaxed state before attempting to stretch further.

For our advanced anal only enthusiasts, we’ve got the “Stretching Superstar” challenge. This is all about pushing your limits and reaching new milestones in anal stretching. Whether that means being able to take a larger toy, fist, or even double anal, we encourage you to safely and slowly progress throughout the month.

As always, safety and consent are the cornerstones of all our challenges. Use plenty of lubrication, listen to your body’s signals, and never push yourself too far, too fast. Stretching September is about celebrating the journey of anal stretching, not just the destination.

Ready to embark on Stretching September? Let us know your plans and share your progress with us!

Bob: Hi we’re a MF couple with myself a Bisexual Hetero Relationship and my gf is a Bisexual.

We have discussed my interest in being pegged and she’s happy to try it out, but she doesn’t know that I have been doing anal masturbation for a few years and able to fist myself or take big toys.

I know truthfulness / trust is important for a relationship but I’m anxious that she may freak out as she doesn’t do anal herself and more on the vanilla side to sex.

And so I was wondering if I should keep it all a secret and start small, so that we can both enjoy training my hole.

She already knows that you want to be pegged, so you could open up about the fact that you already play with your ass on your own and want to include her in it as well. You don’t need to say everything all at once or how experienced you are with anal play—not necessarily keeping it secret, just easing into it over time with her. If she wants to talk about it more and asks you, tell her, otherwise let her discover your interest in it gradually as you start exploring.

Or, if she proves very receptive to the idea and enjoys exploring it with you, open up more quickly about it and tell her all about your interests in anal play.

Loren: We have been doing double anal with hubby for many years but can’t do it all the time. Usually with his cock and a toy but twice with another man and many times with a trans woman which we both enjoy. This has led to anal fisting which puts me out of commission for at least a week. And of course we fuck the trans woman and the ass to mouth tasting each others ass on hubby’s cock is a huge turn on.

Is double anal all the time a goal for you, or do you prefer it as something occasional? With practice, I’m sure that you could make it a more regular thing if you wanted to.

As for fisting putting you out of commission for a week, it sounds like spending more time on warmup and gradually doing it more often until it doesn’t leave you sore or in need of recovery could be a good idea so you can enjoy it regularly without needing to take such a long break after.

Max & Nata: So, my wife and I are both 32, we’ve been married for 4 years, and about a year ago we have arrived to an unspoken arrangement that I only fist her pussy and I only fuck her ass (don’t know if this counts as anal only lol, but we’re both happy with that). She loves being fisted and says it’s the best thing ever – she also loves anal, and we do about 50/50 between these two (we also do oral, spanking etc., but we almost always finish with either anal or fisting, or both).

I’ve lately been trying to talk to her about anal fisting, as it’s something that is interesting to try – but she only said “maybe later” and was pretty elusive about it in general. I think it’s obvious that she’s a bit scared. She also says she doesn’t love fingers up her ass as much as she loves my dick and toys in there, because fingers don’t go as deep as she wants. She has some toys to use up her ass, and she uses buttplugs when I fist her — we recently bought another one that’s bigger than my penis in width.

The question is – should I be persistent with trying anal fisting, or maybe leave it as it is? Obviously I don’t want to do anything that she doesn’t want, but maybe there are some arguments I’m missing that can help convince her to try? Or maybe it’s I who’s missing something and should be happy with what I have?

Also, other thing with that is that she’s worried about is that if we do a lot of anal fisting, her ass can become stretched out and not as tight as it is now (her pussy being loose was one of the reasons we switched to anal only). To be completely honest, this concerns me a bit as well.

So, if you have any tips or comments, or experience to share about anal fisting, we’d be happy and grateful to hear it (she knows about this post and she will read the answer too). Maybe there’s a way we can work towards it without using fingers too much?

Thanks a lot for your blog and for the answer. Sorry if my English is a bit weird, not my primary language.

First of all, “anal only” means a variety of different things for a lot of different people, but the fundamental element is that you don’t have vaginal intercourse and have fully replaced it with anal. There are those who still use toys or other forms of vaginal penetration but who identify as anal only, so I think if being anal only is something that appeals to you, you can consider your arrangement to fit within that definition. I think there can be some additional benefits to going fully anal only for some people, and generally encourage at least trying that too, but everyone is different and different things work for different people.

As for wanting to try anal fisting, it sounds like she’s expressed some of her concerns already. Are those her only hesitations, or does she have others as well?

Not liking fingering as much as sex is not uncommon, but fisting is different from fingering and provides much more of a stretch and can go deeper as well, so I would encourage her to think of them as different things and not to write off anal fisting just because she doesn’t like fingers on their own as much. It’s an entirely different experience.

Fear of stretching and becoming loose is a common concern that isn’t that rooted in reality. Injury can cause muscles to become weaker, but “stretching” anal muscles is actually exercising them and frequent use can help them become stronger. What people equate with being loose is actually an increased elasticity that allows them to expand larger, but they still stay tight and closed when not in use. There may be short term looseness after for a few hours, but things tend to return to normal quickly. And even the increased elasticity is not something that happens overnight, so it’s something that you can start to explore and see how it progresses for the both of you. Chances are you’ll both find that it does not negatively affect your enjoyment of sex at all. Exercises like kegels can also help to further strengthen and “tighten” anal muscles.

But if she’s also just afraid of trying it, why not sit down and talk about it together and discuss her fears and concerns and whether she’s interested despite being afraid and what you can do to help relieve some of those fears. Remind her of how rewarding vaginal fisting ended up being for her and with the pleasure and intensity of anal how great it could end up being as well.

Good luck to the both of you!

Anonymous: I’m a self-described anal only slut and I just can’t ever seem to get enough of big things in my ass. I’ve been doing anal since I first started masturbating and knew right away I liked to put my finger in my butt more than my pussy, and pretty much have been anal only ever since, only trying it in my pussy a few times along the way, but otherwise it’s barely been used and I’m done trying, I just want it all in my ass all the time! I cum easily from anal and never have from my pussy.

I like using big toys, stretching my ass as much as I can and making it bigger until it gets easy and I go even bigger yet. I really like fucking guys one on one still too and it feels great but I’m compelled to stretch it more and more as well. I started doing double anal pretty often last year and that’s a lot of fun, both on my own with toys and with two guys at once. I think that’s my current favorite, but I’m getting into fisting now too and I’d like to start doing triple anal.

But how big should I go? Should I stop somewhere or just keep chasing my need to go bigger and bigger? I know how to be safe and not hurt myself and I always stop if something starts to hurt, I don’t want any long-term injuries or ill effects, and I don’t have any problems as a result of my passion even though I’ve been at it for years now. I saw you posted about some girls going double anal only and I’d like to try that at least for a while. I wear a 2″ plug every day and sometimes bigger, should I go larger with that?

Thanks for the message! Sounds like you have an awesome and healthy anal only sex life! While not everyone craves going to bigger and bigger sizes, there’s nothing at all wrong with that desire and I think it’s totally normal as you really get into anal and the anal only lifestyle, especially when combined with a slut lifestyle.

Go as big as you want and keep chasing that craving. As long as you play it safe, you aren’t going to hurt yourself or develop long-term issues. And don’t worry about getting “loose” either, assholes don’t really get loose, they just increase their upper size limit. And you can have a lot more fun with a well-trained, flexible asshole than an overly tight one! So definitely keep doing what you enjoy most.

Double anal is definitely becoming more popular lately. It’s been a popular porn genre for a while, but in recent years I’ve seen a huge uptick in real women starting to practice it, some occasionally, some regularly. I know several who have gone “double anal only”, as you mentioned, and who have made it their primary sexual activity, only having sex with two or more partners penetrating them anally at the same time. If that sounds appealing to you and you have the partners to make it work on a regular basis, it could definitely be something to explore. It’s a very fun idea for the right person.

There are a lot of large plugs out there. If you find your everyday plug really comfortable and not pushing your limits anymore, you might try going to a larger one as your primary one, which will help keep you relaxed open for bigger and better things.

Good luck, and let us know how things go. I’m sure you’re in for a very fun time going forward.

Still looking for a last-minute Valentine’s Day gift to give your boyfriend? If you aren’t already anal only together, why not go anal only for him? Whether it’s for the day, for a week, or for a month, tell him you want him to have anal sex with you as often as he wants without doing vaginal at all.

And if you are already anal only, this could be the opportunity to introduce something new, like clitoral denial, long-term butt plug wear, or working up to double anal, fisting or larger anal toy use into your routine.

And if by the end of your day, week, or month of anal only, you find that you really enjoyed it, just keep going with it! A trial period like this is a great way to discover that you actually prefer being anal only.

Anonymous: I sent a message recently about wether or not I should lose my vaginal virginity to my boyfriend or not and in glad to say we talked and I haven’t! He is completely understanding and more than willing to stick to anal only. We have decided we want to be even more adventurous with our anal play. We already have his friends join us every now and again but i was wondering how to get even more adventurous? What do you recommend? Nothing is too crazy

I’m glad to hear that it worked out and that you were able to communicate your desires to him and he’s understanding that you want to stay an anal only vaginal virgin. That’s great. Communication is key, and is usually the most effective way of resolving such things and figuring out effective compromises. Keep it up!

As for being more adventurous, there are plenty of ways you could do that. Not knowing what you already do, there might be some overlap with existing activities for you, but I’ll list some ideas anyway. Not all may interest you, and while they’re listed in increasing order, they aren’t all necessarily dependent on previous ones.

• Experiment with clitoral denial and only orgasming from anal, which can have a similar amplification effect on arousal as edging and clitoral/vaginal orgasm denial does for a lot of women. If you like edging, you can actually do anal edging as well, which can be a lot of fun.
• Start incorporating regular ass to mouth into your routine. This pairs well with group sex with multiple men as they can take turns between your ass and your mouth.
• Start wearing a butt plug regularly and gradually training your ass for larger toys—plugs, beads, dildos, etc.
• After working up in size, try double anal. You can try this with toys first, then once you’re confident you’re ready, try it with your boyfriend and a friend of his.
• Anal fisting and large toy play can be a lot of fun once you’re ready for it.
• If you’re serious about remaining a vaginal virgin, you can help symbolize this with labia piercings that close off your pussy. This isn’t strictly necessary, of course, but some like the look and the symbolism of doing so. Plenty of women are anal only or vaginal virgins without doing this, though!

Hopefully those give you a few ideas and starting points to choose from. No doubt my followers can also reply and add some ideas of their own. Keep us updated with what you decide to do and how things progress for you! Enjoy!

Anonymous: My boyfriend and I have been anal only for 2 years now and things are great, but we are trying to find something to really test my anal limits. We’ve used toys like dildos, vibrators, etc.. But we are looking for something new. Are there any interactions you can think of that will take our anal sex to an extreme? We are very adventerous. 🙂

Congratulations on the two years anal only! There are all sorts of things you could try doing to push your anal limits and get deeper into the anal only lifestyle.

• If you use clitoral stimulation currently during masturbation or sex, you could work to stop that and focus on pure anal only and learn to orgasm from just anal (if you can’t already). Using numbing creams like Orajel can be a good part of this process as well, temporarily removing any sensations from your clit.
• You could start wearing a butt plug more often until you more or less always have one in whenever possible aside from when having sex, using the bathroom, or cleaning.
• You could buy larger dildos and plugs and continue pushing your size limits with them. Depth play can be fun in addition to increases in width.
• You could start working towards double anal, whether with a third partner if that’s something that interests the both of you, or with a dildo alongside your boyfriend.
• Similarly, you can start working towards anal fisting. The stretch can be similar to larger toys, but with the more intimate connection of your boyfriend’s hand inside you.
• Chastity piercings to close your pussy and anal only-themed tattoos can be more advanced ways of symbolizing your anal only status.

I’ll be interested to hear what you end up trying!

Anonymous: I just discovered the unique feeling of an asshole around my wrist, while my fingers were exploring the depths of the tube of lust, anal fisting is the ultimate hedonism my girlfriend told me when she finally could speak

Sounds like a good time for the both of you! Thanks for sharing.

Anonymous: I really love anal but my current daddy hates it. How can I make him fuck my ass? I’m dying to be fisted again. :'(

ditzystella: Truthfully? You’re with the wrong Daddy in my opinion if he “hates” it and you’re longing for it. So, maybe if you really want to be with him, get permission to use some toys on yourself? Are you cute? I can help! 🙂 haha

Actually I need help properly answering this, i’m not happy with my answer. @analsexonly can you please help here? Thank you!

Some people just don’t like certain sex acts and there isn’t much that’s going to change that for them, as much as we might wish there was. For example, I hate vaginal sex personally and have little to no interest in ever, ever doing it again. Nothing’s going to change my mind about that. It’s just who I am—I love anal and oral sex instead of vaginal.

However, not everyone is necessarily as set in stone about it as I am. You can talk with him and ask him what it is about anal that he doesn’t like. Is it actually the sex itself, or is it something else? Maybe he dislikes the need for prep with anal, or finds it limiting because you have to warm up to it first and he can’t go as hard or fast, or something of that nature. Some don’t like it because they feel the romance and spontaneity of sex may be reduced with something that requires more “work” before starting. These things can be mitigated if that’s his concern. Other people just don’t like the idea of it, find it gross, or don’t like how it feels. Some of those things have potential solutions, others may not. Everybody’s different, and if he’s set in his opposition to anal sex, you’ll have to decide how important it is for you to get it.