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You Need Help: How Can I Make Penetration Less Painful?


A few years ago, I planned on having sex for the first time with my girlfriend, who was older and more experienced. For whatever reason, she either didn’t remember or didn’t respect how tight a first-timer can be. She didn’t use lube, toys, anything — she went straight into penetrative sex. Y’all, it HURT. I didn’t want to hurt her feelings, but ouch. The exact same thing happened the second time. In my defense I was A. totally inexperienced and B. convinced it was 100% my fault for not getting aroused enough. It made her insecure about her ability to have sex, and she eventually dumped me to sleep with other people.

So now I haven’t had sex in almost four years, and I’m genuinely worried about never being able to do anything besides top, which I do enjoy, but like, I would also like to be topped. I want to have sex, and I really don’t want to get dumped again. I’ve read all the guides for first timers and bought all of the recommended toys, but everything is still too big! And clit-stimulating toys, unfortunately, don’t do enough. I think I might actually need to have penetrative sex to orgasm. So y’all, how on earth can I make myself less tight down there for my next first time? What are some FIRST-first-time toys and tips for penetrative sex? Please help so that I can one day have fun strap-on times!


First, I just want to acknowledge that your “older and more experienced” ex-girlfriend’s approach to sex is not okay. Penetration can be painful for anyone — yes, even for veteran strap-on bottoms — when there’s zero foreplay and no lube involved, and communication is key. You didn’t speak up at the time because you “didn’t want to hurt her feelings,” but that doesn’t mean that the pain you experienced is your fault! It was your ex-girlfriend’s job to check in with you and show you that she values your pleasure. She didn’t do that, and now you associate sex with pain and shame. That sucks! And I’m so sorry this happened to you.

Before I get into how you can experience and enjoy penetration, I want you to think about why you want that. Do you enjoy penetrating yourself during masturbation? Do you fantasize about penetrative sex? Do you want to explore all of the sensations that your body has to offer? If this is something that you want for yourself, that’s great! But if the only reason you want to get railed is that you “really don’t want to get dumped again,” then pause your penetration efforts. Some peoples’ minds and bodies just don’t love penetration during sex, and that’s okay. There are so many other ways to enjoy sex, and you can have the experience of “getting topped” without any body parts or toys going anywhere near your holes. And there are plenty of people who will be totally down to fuck in this way! If you want to explore penetration, that has to be a choice you’re making for your own pleasure.

If you take the time to investigate these feelings and conclude that you actually don’t want to continue down the path of penetration experimentation, that’s great! Stop reading here. But if your hot bod is craving a pounding, read on.

From your question, I can’t tell if you’re talking about vaginal penetration or anal penetration, so I’ll touch on both. If you’re a life-long vulva-owner, here’s a fun way to think about your genitals: vaginas are “potential space.” This means that the elastic walls of the vagina stretch to accommodate what goes in (fingers, dildos, tampons, menstrual cups, a speculum, a partner’s genitals, etc.) and what goes out (all of the aforementioned things, plus whole entire babies). But vaginas might need a little coaxing to get there, and some just don’t stretch as much as others. If you’re not a life-long vulva-owner and you’ve had gender confirmation surgery, your vagina is not very elastic, so following your surgeon’s post-op instructions is super important for safe and enjoyable penetration.

Here’s the deal with anal penetration: if you relax and stretch your external sphincter (those are the muscles around your anal opening) and lube yourself up, you can welcome things in and send them out, but you can’t control your internal sphincter (this is the smooth muscle that’s deeper inside the booty), so comfortable anal sex requires consistent practice and a very slow pace.

Here are a few of the reasons why you might be experiencing pain during sex. This is by no means a comprehensive list, but it’s a place to start:

1. You don’t know how to communicate about the sensations you like.

You write that “clit-stimulating toys, unfortunately, don’t do enough” and that you “might need penetrative sex to orgasm.” I might be misunderstanding this part, but based on this information, it sounds like you know that you enjoy penetration (presumably during masturbation), but when you were having sex with your ex, your body was NOT happy. Before you dive into sex with a new partner, take some time to explore your own pleasure (and by that, I mean — masturbate more and focus on what you like). Once you really get to know the kind(s) of touch body digs, practice putting those techniques into words with a new partner and/or demonstrate — masturbating in front of someone can be incredibly hot.

2. You’re not using lube or you’re not using enough lube.

Friend, there is NOTHING wrong with using lube for vaginal sex, especially when you’re being penetrated with a sex toy. Using lube doesn’t mean you’re “not wet enough.” Lube makes penetration more comfortable so you can enjoy it for as long as your vagina desires. If you’ve had gender confirmation surgery, lube is even more important! And if you’re being anally penetrated, lube is absolutely essential — your butt doesn’t self-lubricate, so if you forgo lube in the back door, you could seriously hurt yourself. You can use water-based lube (my personal favorite is Sliquid Sassy) on everything from silicone toys to fingers or you can use a silicone lube (my personal favorite is Uberlube) for a slicker, longer-lasting option — just make sure that you’re not using silicone lube directly on a silicone toy, since this can degrade the material. If you really, really want to use silicone lube on a silicone toy, put a condom over the toy to protect it, but you’ll risk getting some lube on the base. Water-based lube on silicone toys is your safest and best option.

3. You’re not adequately aroused.

When you’re not turned on, your vagina and your butt will probably be hesitant to welcome guests. So when you’re moving towards a strap-on-athon, take some time to enjoy a little teasing and build-up before any penetration happens. Make out, grind against your partner’s thigh, use a vibrator against your clit or your anal opening, try some roleplay — and don’t let your partner put any body parts or toys inside you until your body is screaming for some thrusting.

4. You’re not in the right position.

Every hole is different and every dildo is different. If you don’t have the right match or the right angle, you’ll probably experience pain during sex. If you haven’t already, play around with different positions for penetration. The pain you’re experiencing could just be a dildo hitting your insides at the wrong angle. Try lying on your side, lying on your back with your knees up, bending over the edge of a bed or anything else that sounds comfortable and hot.

5. You’re using sex toys that are too girthy or the wrong shape.

Okay, I know you said you’ve tried multiple sex toys that are supposed to be for “beginners,” but dildos that are marketed as “beginner-friendly” aren’t always slim. And if you’ll allow me to twist an idiom, maybe your eyes are bigger than your openings? Before you shop for a new toy that’s as slim as you need it be, focus on penetrating yourself with your own fingers for a while if you can comfortably do so. Does one finger feel good? How about two? Maybe three? If you still want to shop for sex toys after appreciating the pleasure of your own digits, go to a brick and mortar sex toy store if you can. It’s much easier to identify which toys might work for you when you’re able to hold them in your hands and compare them to the girth of your own fingers. Opt for a smooth, firm toy without any bumps or ridges for easy insertion. Here are a few options: one of the smallest dildos I know of is the Silk Small ($32), which has a diameter of 0.8 inches. The Doc Johnson Slim Dildo ($34.99) and the Silk Medium ($42) both have a diameter of 1.1 inches.

6. You have internal scar tissue.

Some folks have vaginal scarring due to childbirth, surgery, or injury, and some folks have anal strictures due to surgery or inflammation. Scar tissue isn’t very stretchy, which makes penetration painful. If you think you might have vaginal scarring, talk to your surgeon or gynecologist — they can give you instructions on how to massage the scar tissue to create some more elasticity. If you think you might have an anal stricture, talk to your primary care physician or GI doctor.

7. You have tight pelvic floor muscles.

The “pelvic floor” is the hammock of muscles between the tailbone and the pubic bone. This muscle group supports the bladder, the bowel and the uterus in uterus-owners, and in some bodies, the pelvic floor can be very, very tight. This can happen for all kinds of reasons — maybe you have a history of holding in your pee or maybe you play high-impact sports. I have a tight pelvic floor because I have hypermobile joints, and my pelvic floor has to work extra hard to prevent my hips from popping out of their sockets. When my pelvic floor tightness was at its worst, I regularly used my fingers and a Njoy Pure wand ($110) for internal vaginal massage and I helped my muscles stretch and relax by using dilators, which are basically dildos in a range of sizes. You start with the smallest dilator, pop it in and hang out for a while while it gently stretches your vagina or your sphincters. Over time, you should be able to go up in size until you reach your desired girth. If you’re interested in trying vaginal dilators, talk to your gynecologist — they might be able to prescribe some — or you can pick up a set at your local sex toy store. There are lots of options out there, including the Wellness dilator set ($57.99), this silicone dilator and bullet vibrator set ($49.99) and the They-ology Wearable Anal Training Set ($79.99). And remember — if you’re using dilators or an “anal training” set in your backdoor, make sure those toys have a wide base! If you find that your pelvic floor is only tightening in response to vaginal penetration, you might have vaginismus, which causes involuntary muscle contractions in the vagina. If you think you might have vaginismus, talk to your gynecologist. They might recommend dilators, pelvic floor physical therapy, or something else.

8. You’re freaking out.

When you’re anxious and stressed, your muscles tense, and that includes your pelvic floor! Given your previous sexual experiences, you’re probably tensing up at the mere thought of penetration. If you think this might be happening, find some ways to prevent your mind from wandering to big, scary places during sex. Focus on your breathing. Play some music and focus on the melody or lyrics. Engage in dirty talk or verbal roleplay that will focus your thoughts on the hot, hot sex you’re having instead of your worries about painful penetration.

I hope this helps! Good luck on your penetration journey, and remember — you don’t have to have penetrative sex unless you want to.

You can chime in with your advice in the comments and submit your own questions any time.

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Ro White

Ro White is a Chicago-based writer and sex educator. Follow Ro on Twitter.

Ro has written 105 articles for us.


  1. also want to + patience & curiosity & exploration with lots of lube. i think the way my body is shaped is likely just not super common, and things that work for a lot of people don’t work for me. focusing on what listening to what my body is asking for, and reading a lot of sex positive articles (mostly here, thank you autostraddle!) about the vast diversity of what feels good for different people, has led me to things that do feel good, which don’t really line up a whole lot with what i read in advice columns or smut.

  2. Yeah, the first girlfriend did not treat you right.

    Personally I have developed tight pelvic floor muscles after abdominal surgery. Thing I learned it that if you do not use your (deep) abdominal muscles to keep you upright, you often compensate with the pelvic floor. And that is a very difficult pattern to break. What helps me most it to strengthen the deep abdominals for a stronger core (takes some of the work from the pelvic floor) and to stretch the hip flexors and rotations (laying down on the ground with the knees bent and the soles of your feet touching for the last one). This really deals with the whole area.

    I also invested in a wider bicyle saddle and that helped a lot.

    Not sure if this is the issue for OP, or if it’s one of the other causes, but I figured this might help some people here.

  3. (mostly for lifelong vagina-owners, but some info might be interesting for new owners or intersex people with individual genitalia)

    1. Locate the exact pain/tightness and what exactly causes it. That’s not as obvious at it seems.

    a. It could be a hymen situation, some sort of skin or cover or ring that partially closes your vagina some centimeters in. (And I’m really surprised that nobody mentioned that) That would be common if you haven’t had regular penetrative sex. In that case you should feel a narrower part that is not very thick, and behind that your vagina is wide again (when you are relaxed with yourself).
    For some people getting rid of that hymen can be painful and cause bleeding. You can consult a gynecologist to help with that if it’s too painful without anesthesia.
    Penetration might feel like getting stuck, and the pain would be a localised burning ring area.

    Note: In the rare case that the barrier is very thick and/or the opening is tiny (one small finger or less) i.e. the vagina is mostly closed, it might be a form of intersex. If possible, consult a gynecologist who is intersex-friendly.

    b. As someone mentioned, you could also have scar tissue, for example from a partially broken or torn hymen, or from other problems. In that case you would have localized pain in very specific areas when you touch or press them, like small wounds. Consult a gynecologist to find out details.

    c. If the painful/tight area is along the full length of the vagina, and the vagina cramps during penetration, it could be vaginismus, possibly with a more emotional background. You shouldn’t just try to “get over it” but rather find a self-loving approach possibly with a therapist or self help group.

    d. If the pain is along the full vagina or at the end, but only when you insert a finger or object, and the vagina feels very narrow and/or short, but at the same time soft and relaxed, your vagina might be naturally small. Check in with a gynecologist to make sure. In that case, you probably cannot be penetrated by larger sizes. Especially long toys can cause a numb, sickening pain at the end of the vagina when they hit the uterus. Adjust the toy size accordingly.

    2. Hardware: It’s not easy to find actual beginner dildos. But try something *really* tiny, like the Tantus Silk Small or smaller. There are anal toys and pegging dildos with a diameter of 2 cm or less. They come curved or straight, and are not very expensive, so you could get a couple and experiment. Gay sex shops often have a large variety and helpful assistants. Google for anal training, beginner, pegging..etc
    As mentioned in the article, there are dilator sets that are often advertised for women with vaginismus or trans women after surgery, that start with tiny (1.5cm diameter) dildos and go up 4 or 5 sizes.
    Try if you can use one of those small toys. They are mostly in silicone and can be warmed up and lubricated. Don’t feel that you need to “work you way up”. It’s fine if you find just one or two sizes that work.

    If you have physiological problems like scar tissue, the pain might be recurring. Don’t force it. Try to find the smallest toy and the best angle that works for you. Be extra careful and gentle. Imagine you are are your own girlfriend and she is in pain.
    It could take quite some time to find something that works for you. Be patient. Stay playful. Don’t force anything.

    When you have found a shape that works for you: some of these small toys can also be used in a strap on, esp. the dildos for pegging. Or try to find a toy with a similar diameter but longer. Experiment with the strap-on on your own. In case you can’t find anything fitting, there are “make your own silicone dildo” sets.

    When you introduce it to a partner, tell them not to move and do all the moving.
    After you make that work, go very slowly, with them moving, from there.

  4. Why would you want to have penetrative sex if you don’t enjoy it? It’s not mandatory for girl on girl sex. We don’t have to please someone with a penis. My orgasms come from my clit, not my vagina.

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