Q: I’m 27 years old, and I’m training my body for anal sex with a partner. I wanted to practice with dildos or butt plugs first so I could move at my own speed and comfort level without the pressure of having someone else there. I have plenty of experience using sex toys for clitoral stimulation, but anything involving the bum is completely new territory for me. Do you have any tips for beginners when it comes to sex toys and anal prepping?
It sounds like you’re already in the right mind-set. When it comes to butt stuff, it’s all about moving at the speed your body determines. Although this can be said for all kinds of sex, including vaginal intercourse, the anal canal is significantly more delicate. Getting familiar with your own body before playing with a partner will only help make the partnered experiences easier to navigate. Deep awareness of your physical sensations and tension is key to preventing discomfort/injury and providing pleasure. And as a bonus, paying attention to the nuance of the sensations will probably make you more aware of your bodily sensations outside of butt play!
Before you consider purchasing an anal toy, it helps to start exploring with a well-lubricated finger. Using nitrile gloves can help reduce the discomfort of any rough edges on your fingers, and it also makes cleanup a breeze. Start out exclusively stimulating the external portions of your butt—the perineum, the outer area of the sphincter, whatever feels relaxing and yummy to you. Massaging the outside of your anus will help you become acquainted with how it tenses and relaxes. The anal opening has a ring of muscle in the sphincter that you can consciously relax or contract, but there is a second ring of muscle a centimeter or two past the opening that cannot be consciously relaxed. You’ve got to truly let go of any inner tension cords you’re unconsciously holding. In that way, anal play is a lot like meditation!Once your butt is relaxed, it will receive whatever you gently press up against it. Gentle pressure can help guide a finger, toy or phallus past the sphincter, but you never need to force or jam something up against your butt. Approaching the sphincter at a 90-degree angle generally doesn’t feel as gentle as approaching from the side and “tipping in.” Another benefit of starting out with fingers is that you can feel the biofeedback of how relaxed you are. Gentle circular or side-to-side, up-and-down motions can also help massage the sphincter into relaxation once you’re in up to your first knuckle. Past the sphincter, you have options! Fingering a butthole is very similar to fingering a vagina, just with a more delicate canal. You can move in and out, rock and swivel your fingers, or aim for prostate or indirect G-spot stimulation.
Once you’re acquainted with fingers, this playtime will inform what type of toy you’ll go for next. You can even measure the circumference of your preferred number of fingers, and compare that to the sex toy specs online to ensure you’re getting an appropriate size. The main difference between a plug and a dildo is that plugs are designed to go in and stay in, whereas a dildo is a more active toy. As long as it has a flared base or definite stopping place, such as a reinforced pull-ring that won’t get sucked up into your butt, it’s anal safe!
Plugs are great for getting more acquainted with the sensations of fullness. The slim neck toward the base of a plug allows the anus to close around it more comfortably so you can leave it in for longer-term wear. Dildos are generally going to provide sensations similar to anal sex with a penis simply because they don’t have a narrow area for your butthole to close around. There isn’t a specific size or amount of time for play that you should be aiming for; that will boil down to the subtle cues your body gives you as you explore.
Besides lube, patience and awareness, placing a towel or blanket underneath you will help you mentally relax. Poop is stored in the colon and doesn’t hang out in the rectum unless you’re about to have a bowel movement, but, given that the butt is indeed a poop chute, shit happens from time to time. Try not to worry about that aspect of anal play so much—worst-case scenario, you can wash the towel, shower and get back to it!
Finally, it’s important that whoever you are anal-prepping for is just as aware and educated on butt stuff as you are. No one wants their ass jackhammered immediately, like you see in porn. (Remember: Porn is fantasy and a performance.) Unfortunately, many givers of anal pleasure fail to pay attention to the cues of the receiver’s body, and anal fissures are not something you want to experience. Lube is mandatory, and it should be reapplied as much as needed. Starting on your back can help with relaxation, but some people find that sitting down on or backing onto a toy or phallus helps give them more control of depth. It sounds like you already have the right mind-set, so just enjoy the beauty of these new sensations without any self-imposed pressure to have it go down in a certain time frame—or at all! My butt is excited for your butt!Q: I’ve been dating the same man since high school. We’ve grown together in a lot of ways, but our bedroom routine hasn’t. I regularly use vibrators and dildos during self-pleasure, and if I felt comfortable using my sex toys with my partner it could help to add some variety to our intimacy. (He doesn’t know about my use of toys.) The thought of holding a vibe to my clit while he penetrates me sends me to a completely new level of arousal, but I don’t know how to broach the subject with him. How do I explain this to him without him thinking I’m judging his sexual prowess?
It can be hard to break any type of routine, not just sexual routines! Sometimes the anxiety leading up to a conversation about sexual needs is far more stressful than the conversation itself. It sounds like this aspect of your solo play is something you are excited to share with him, and I would let that feeling be the leading energy in the way you approach him.
We use tools for nearly every aspect of daily life: eating, working, sleeping. We all have accoutrements that help us live our lives. Sure, we can eat all our meals with our bare hands, but forks, knives and chopsticks can help us enjoy our meals and eat more efficiently. No one has ever felt emasculated by the suggestion that they use a nail gun instead of a hammer to build a house or use a motorized lawn mower over a push mower! Vibrators and dildos are just like those types of tools—they just happen to fall into a more taboo arena. Sex toys, like tools, aren’t replacements for people. They are things people use! Vibrators can’t tell you they love you or embrace you, and humans can’t vibrate. Sure, humans have body parts that can penetrate and stimulate, but sometimes we get a hand cramp or we’re tired or not erect. Furthermore, the vast majority of people with vulvas need external stimulation or external paired with internal stimulation to achieve orgasm. Manual stimulation doesn’t do it for everyone, and vibrators help bridge the gap for a lot of people (myself included!). Although there are a lot of myths about vibrators out there, they ultimately make a lot of us very happy and help us have fulfilling sex lives.
If someone cares about us and our pleasure, they will support us doing what we need to do to experience that pleasure. I think if you share how much these toys/tools have helped you enjoy solo sex, it won’t come across as anything other than a desire to experience that with him. If he has questions or doesn’t know much about vibrators, education about sex toys will help him discard the myths we’ve all been taught from social discourse. Try not to assume that he will react a certain way or project an expected outcome onto the conversation. You might be very surprised; for all you know, he could be waiting for the right moment to suggest toys himself!
Vibrators and sex toys aside, it can be daunting to tell someone about any sex thing you’ve been keeping private, regardless of what it is. It always helps to be direct in your communication, and you’re always welcome to say something like, “I’m nervous to discuss this thing, and I’ve been having a hard time bringing this up.” If you know it’s not any statement on his sexual prowess, then there’s no need to even bring that up unless he expresses that fear. It’s not your job to coddle him and reassure him, either. You don’t need to make any apologies for the things you enjoy. You can point him in the direction of education and information on the wonderful world of toys, and he may need to do a bit of research on his own. That’s okay! Any relationship will have its moments of awkwardness and discomfort. Being able to communicate and grapple with those moments only makes partnership stronger!Q: My question relates to cuckqueaning, so brace yourself. I am in a monogamous BDSM relationship, and I am submissive. For a while, I have fantasized about the “cuckquean” phenomenon. Him being with other women while I’m forced to watch gets me off to the max. I have serious insecurity issues that are largely undealt with, stemming from adolescence. So it’s clear to me why feeling inadequate would actually be desirable, knowing how kink can work. I desperately want to explore this kink I’ve been suppressing, but it’s also the most terrifying thing in the world! I have already told him about it after much consternation, and he expressed interest and said we would take it slow. Do you have any advice on this tension people might have with their kink?
Absolutely! First off, congratulations for being so aware and identifying where these feelings may be coming from. You’re absolutely right that kink and BDSM can have funny ways of being connected to prior experiences, especially those from youth. It sounds like you have a supportive partner and have already had preliminary conversations surrounding what you want from the experience—not just what will excite you, but also the areas in which you are apprehensive. Solid foundation!
One major aspect of cuckqueaning/cuckolding that is in opposition to monogamy is the concept of “infidelity.” Googling these terms often turns up results with historical definitions that portray it as nonconsensual infidelity, with no acknowledgement of how it can be done consensually. Even if you know this is something you have enthusiastically chosen, the mainstream narrative around infidelity can creep back in and emotionally overpower you. It sounds like you’ve already identified the “what” and “why” of it all, and there are many options and exercises to consider to help you move forward. A good ol’ pros-and-cons list or cost-benefit analysis will help you determine whether the tension surrounding it is worth it for you. Nerves are bound to come up, but if the stress outweighs the enjoyment for you, now may not be the right time. You can always revisit the idea.
If you choose to go for it, identifying triggers of your insecurity will help minimize the potential for it to be a negative experience. Imagine the scenario in your head, and determine which moments spark that fear. Pause when you feel uncomfortable, and identify your emotions as well as your bodily feelings. Try to think beyond the sex acts, and picture what the moments or days after may feel like. What does the worst-case scenario look like? What does the best-case scenario look like? These questions can help you have better conversations with your partner and the person you invite to join in—because they are active participants too!
We are all afraid of loss, and we all experience jealousy and insecurity. Some of that is very rational, and sometimes those feelings are our trauma-brain shouting over our logic and intuition. It’s very likely that you will experience fleeting moments of insecurity even in a best-case scenario, so instead of trying to avoid those feelings altogether, you can plan ahead and create a toolkit for handling the various emotions that come up. It is no easy feat! Part of what makes kink so exciting is that we are playing with sensation and/or power exchange. There are many moving parts and variables that keep us on our toes, especially when a new person is brought into the mix. Ultimately, this is your desire, so whether you go for it or choose to keep it a fantasy, there is no rush. Meditate on it without overthinking, and communicate, communicate, communicate!