L: I’m 23, and I’ve never had sex. For a long time I felt like I was behind and really missing out, but more recently as I’ve learned more about anal only I’m actually glad that I didn’t have vaginal sex and lose my virginity with my pussy. I’ve been reading a lot, watching a lot of anal porn, and masturbating anally and I want to make my first time really special and train myself to be able to have double anal sex to lose my virginity and hopefully if it goes well, stay double anal only. I think it would be really fitting, not to mention exciting, to have saved myself for something special like this.

I’ve been wearing a butt plug most days, going bigger every month or so, and I’ve been masturbating with dildos a lot. I found I really like the feeling of a big stretch which is a good sign I suppose, and I’ve started using two dildos within a few minutes most sessions. Is there any advice you can give me to be ready to go straight to DAP the very first time without needing to warm up? And of course, how I can meet guys who are interested in DAP and who would be good to have sex with the first time?

I love your take on that, not missing out by not having sex, but saving yourself for the right thing. And I fully support and encourage your desire to go straight to double anal. You’re doing exactly the right things with your training and practice for it. Keep it up, work up to larger dildos until you’re at or exceeding average penis thickness every time you train, and start practicing trying to penetrate with both dildos together at the same time. You’ll get there, and once you can do that every day, you’re ready.

Finding two guys to lose your virginity to might be the harder thing, but it’s very doable. If you have two close male friends you could bring it up to them, or you could seek out people in a group sex lifestyle and see if anyone is interested. Men experienced with double anal would be best, but even just those who are open to or experienced with group sex could be quickly adapted to DAP. Just be clear you want it to be double anal only, no single anal, no vaginal, and set those ground rules immediately from the start.

Riley: I’ve been doing anal only for almost two years and recently started experimenting with double anal with my husband and his close friend. When it works, it’s absolutely incredible—stretching, overwhelming, intimate, and deeply fulfilling in a way I didn’t expect. But I’ve also had sessions where my body just wouldn’t take it, or I ended up too sore to keep up my plug routine afterward.

We really want DAP to be a regular part of our life. Not just an occasional treat, but a foundation. But I also don’t want to risk setbacks or burnout. Do you have any advice on how to build up the stamina and flexibility to make double anal sustainable, not just possible? I’m all in—I just want to do it smartly.

It’s amazing to hear how much DAP is already positively affecting you both emotionally and physically. It really is an amazing thing when it goes well. If you want to start doing it more regularly or even go double anal only, you’ve got to get to where it works easily all the time, not just sometimes.

Double anal demands more from your body than single anal, and it takes time to adapt to that, especially when you’re doing it regularly. You need to build up to where you can take two cocks at a moment’s notice with ease.

I suggest more regular plug wear in between sessions, especially focusing on larger plugs with thicker necks to keep your stretch active. Masturbate/train regularly with two dildos, or a large single dildo, so that you continue getting used to the more active penetration of two cocks in your ass together. When it’s just your boyfriend, you can use a dildo alongside his cock to stay warmed up for double anal.

After sessions, use aloe vera gel (make sure it’s pure aloe vera and not mixed with alcohol or other additives that may be harmful for anal use) on your anus and rectum to sooth it and help it recover.

Gradually increase the frequency and over the course of a month or two you should be where you can do double anal every time you have sex!

Joslynn: I’m a trans woman and for about 2 years I’ve been trying to find the limit my ass can be stretched, almost every day. I can see I’ve definitely progressed, but I want it even looser. How do all the porn stars have such blown out assholes and are able to take huge toys, literally, 2 feet deep in their asses? How are they able to be very rapidly fisted? I know part of it is a lot of practice, but there has to be something else, right? What am I missing?

Thanks for your question, Joslynn, and for sharing your goals. What you’re describing is something a lot of people who are deep into anal play wonder at some point: what does it really take to reach those advanced levels of stretch, depth, and responsiveness? You’re right that consistent practice is a big part of it, but there are definitely other elements that go into what you’re seeing in extreme anal performers.

First, body type and anatomy matter. Some porn performers simply have a more naturally relaxed pelvic floor or rectal elasticity, which gives them an easier time going deeper or looser. Hormonal status, body size, and even connective tissue flexibility can all influence this. That doesn’t mean it’s unattainable — just that some people may progress more quickly.

Second, many of the stars who can take massive toys or hands rapidly have put in years of very specific training. Daily or near-daily play helps, but longer-duration stretching sessions (think 30–60 minutes minimum daily with large plugs or toys, often multiple hours a day) are often a key factor. Many performers use incremental toy sizing systems, work up slowly over time, and frequently revisit sizes they’ve already mastered to maintain openness.

You might also be seeing the effects of temporary gaping and preparation — often, stars warm up with trainers or hands well before filming. What you’re seeing on camera isn’t always just what their body can do “cold.” Some also use enemas or douches not just to clean but to soften and relax the lower rectum beforehand.

Lastly, don’t underestimate the mental side. A lot of what allows people to reach those extremes is a deep mental connection to submission, surrender, or accomplishment, and training your mind to associate big stretch with arousal, not fear.

You’re already doing a lot right. Keep listening to your body, celebrate your progress, and don’t rush pain or strain. Some of the deepest, most blown-out girls you see in porn got there over 5–10 years — and with plenty of trial and error. If you stay patient and intentional, you’ll keep making progress.

Anonymous: I have recently become curious about anal play and find that with a little stimulation my rectum produces enough mucus that I don’t need lube. I can use toys or just my fingers. It is really hard to find anyone talking about this on the web.

Everyone has natural anal lubrication to some extent, to help with digestion. The body produces anal mucous in response to stimulus. It’s often not enough for everyone to anally masturbate or have sex with, but as you train your anus to be more relaxed and elastic, it can be enough lube for some people, or your body may produce more in response over time. Some people even report developing a response to arousal where their anus begins lubricating similar to the vagina.

If it’s enough lubrication for you, great. If not, you might want to start out with a little bit of lube at first and then let your body’s natural lubrication take over, or supplement with more lube as you go larger in size if you find yourself feeling irritation from the more intense stimulation. Listen to your body and it will tell you if you need more lube than your body provides.

Saurav: Is it safe to have anal sex without condom if both partners are clean and monogamous. How much penis to enter the anus

It certainly is safe: if you’re comfortable having sex with each other without a condom from an STI standpoint, then you can safely have anal without a condom as well, because anal is natural birth control.

As to how deep to penetrate, that depends on the receptive partner and how comfortable they are. As deep as you both want to is fine, so long as it feels good. If going too deep becomes uncomfortable, then don’t go that deep for now, and revisit it later after more practice.

H Dean: For about the last 2 1/2 years my GF and I have been AO. An anal virgin prior to me introducing it to her, she requested we go AO within a week after her first anal orgasm – multiples, mind you. Over the last 2 1/2 years her ass has become quite receptive.

Now, my GF is a bit hesitant with the use of plugs. I introduced a Hush plug to her about a year and a half back. She said it was okay but tended to hurt after awhile. About 6 months ago I got a Square Pegg Medium sized egg plug. We started sporadic use of it shortly thereafter. Still she was hesitant.

It was on a warm day this summer I pushed a little and managed to get her to agree to using the plug. After installing it in her ass we left the house and went about our day. After returning to the house some five hours later I asked how her ass felt with the plug. Turns out she had actually forgotten it was in until certain movements reminded her of it.

Since that occasion we have used the plug only sporadically. Most recently I installed it after sex one night. It was in for about 8 hours while she slept and she didn’t seem to notice it.

So, why am I telling you this? Well, because I have discovered some very nice things about anal stretching:

First, once an ass is properly stretched entry is quite easy. Used to be that when my GF would get a little over exuberant and thrust her ass down on my cock so quickly it would cause pain from the sudden stretch. Since we have started plugging more frequently that no longer happens. In fact, if my cock is lubricated I can enter her in one quick thrust with zero pain.

Next, once stretched there the need for lube is lessened. For a long time we have only used saliva for lube. She would suck my cock and get it good and wet and then ease in. Now, she just rubs a little saliva on her ass and I can ease right in. The increased friction sends her over the top almost instantly and there is no pain.

Another benefit since using the square peg plug, so it seems, she has gained use of previously unused muscles. As most male anal enthusiasts know the sphincter tends to be the epicenter of sensation – it squeezes. Deep inside there tends to be far less constriction of your cock. However, at least after using this plug, her anal canal feels much like a sheath and I can feel far more sensation along the entire length of my cock.

Finally, while my GF was always quick to orgasm, she seems to orgasm more quickly and with greater intensity after making use of the plug.

In closing, and based recent experiences, I would highly recommend anal stretching for anyone who enjoys anal as we do. It’s proven quite beneficial.

When it comes to butt stuff, ‘go big or go home’ isn’t the best advice. Instead, it’s best to start with something small, like one of these butt plugs aimed at newbies

As a one-time sex toy retail worker, I often noticed that when customers came into my store looking shifty-eyed and incapable of expressing what they actually wanted to buy, they were usually looking for a butt plug. Sometimes, I’d lead them to the butt plug section unprompted, just to watch sweet relief bloom on their face as I showed them what they had wanted all along.

It makes sense that so many people are skittish about trying anal play. It’s still hugely taboo and shrouded in misconceptions — like that it “makes you gay” (nope), has to hurt (nope) or will automatically be messy (not necessarily). Given how intimidating anal penetration can be, both physically and psychologically, it’s usually best to start with something small — like a finger or a beginner-friendly butt plug.

Butt plugs are different from other anal toys in that they’re designed, more-or-less, to stay put inside you. You can thrust them in and out like a dildo or a set of anal beads, but staying still is what they were made to do, so they do it very well. This makes them a popular pick for combining with masturbation or sex — they can provide some passive prostate stimulation during a blow job, enhance the sensation of vaginal sex or amp up your pleasure when you’re touching yourself. They’re also the comfiest and most practical choice if you want some surreptitious anal sensations in public, like while on a dinner date with your partner.

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The deepest part of ourselves that we hold so much shame around, can unlock our nervous system, bring about deeper orgasms, and help release old stories that we have locked in our brains and body. The anus is connected to the root chakra, which responds to the coccygeal plexus of nerves. Anal can be a powerful way to explore these nerve responses, as well as the ideas of family patterning, feeling safe in our bodies, and primal responses. In tantra there is no abstraction. The physical body is the basis for consciousness. Anal sex requires deep, primal connection, communication and trust. Ass play, or “root chakra work” as I like to call it, can be extremely pleasurable, activating and healing.

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Anal Only April has now officially begun! Read through the earlier post for the full details, but in essence, it’s a challenge for you and any partners you may have to only have anal sex for the entire month, as an opportunity to explore the anal only lifestyle without a long-term up-front commitment.

If being anal only intrigues you, here’s your chance to try it for yourself. If you’re already anal only, take it as a month of celebration and as much anal sex, masturbation and butt plugging as you can manage, or an opportunity to explore a new twist on the anal only lifestyle that you’ve been fantasizing about or are curious to try. In the past, some long-term anal only women have made Anal Only April a “double anal only” month!

As always, if you plan to participate, let us know and share your experiences and questions throughout the month and beyond. After all, most people who try going anal only for a month or two at first find that they don’t ever want to go back to vaginal by the time their trial period is over!

Have you been curious about going anal only but haven’t had the push to actually try it for yourself? Well, now is the perfect opportunity. Anal Only April is one of several challenge months where we encourage people interested in the anal only lifestyle to make a month-long commitment and try out pure anal for themselves.

The rules of Anal Only April are simple: starting April 1st, whether on your own or with your significant other, stop all vaginal penetration for sex and masturbation, and replace it with anal instead.

Clitoral stimulation is optional. If you would like to go for a more advanced form of anal only, try doing it without touching your clit and only orgasming through anal. If you need your clit in order to enjoy anal, combine it with anal, but only rub your clit while also masturbating anally.

Oral sex is still allowed and encouraged, especially blowjobs and rimming. Cunnilingus is optional—some choose to exclude it, others still include it but don’t engage in any vaginal penetration as part of it.

Try your best to stick with anal only for the whole month—it’s a long enough period of time that while you might struggle a little bit with it at first, whether adjusting to the frequency of anal sex, or dealing with lingering cravings for vaginal sex or clitoral stimulation, by the end of a month most people figure out what being anal only is really like, and a majority of people who enjoyed their month trial either choose to stay anal only and not go back to vaginal, or return to it again later after a break.

If you’re already anal only, don’t worry—you can still enjoy Anal Only April yourself. Challenge yourself to have anal sex every day of the month, or to start wearing a butt plug or masturbate anally every day, or to experiment with clitoral denial and anal only orgasms if you aren’t already, or to start doing ass to mouth regularly, or to train your ass with bigger toys to be able to do anal fisting or double anal. The possibilities are endless for exploring new things as part of the anal only lifestyle. If you already enjoy double anal, consider trying making April a double anal only month—whether with two partners every time, or with a partner and a dildo, or two dildos.

Over the next week, get your plans in order, get your partner (if any) on board, and if you haven’t had anal sex yet or for a while, start working on training so that by the time Anal Only April begins, you’re ready to dive in!

If you decide to take part, let us know! Share your plans, ask any questions, and keep us updated as you start exploring the anal only lifestyle!