[EDIT: If you're looking for ACTUAL advice about how to break your hymen, read this post instead. The one on this page is more fanciful than helpful.]
EDIT 2: MYTHS! about the hymen – totally crucial to understanding your hymen.
So there was some confusion during my class tonight; we were talking about hymens and a couple students asked about, like, how big something needed to be to break a hymen, and I was all like, “Well, that depends how sharp it is.”
Because I have a habit of answering precisely the question that is asked, I had no clue (until a student generously came up to me after class and explained) that what they were actually asking was, “Suppose a woman has pain with penetration, due to her hymen, but there’s no one with a penis she’s interested in having break it. What’s a girl to do?”
OHH! Well heck, next time just say so! Didn’t I spend 10 minutes at the start of class explaining that this is a sex-positive safe space where no yucks are allowed and everything is okay? Look, all I want in life is to give people the sexual health information they want, so just ask!
Anyway, the answers to that question are:
(1) Very carefully
(2) With a little help from your friend(s) and
(3) Make a night of it.
There’ll be some pain – heck, the pain is the reason you’re doing this, right? And the key to managing that pain is to close the gate by overriding the pain signals with OTHER sensations. You know how when you stub your toe, you rub it? That’s closing the gate – overriding the throbbing sensation with the rubbing sensation.
With loads of sensation elsewhere – and I’m thinking a vibrator on the clit, another on the anus, breast stimulation, inner thigh stimulation, feet stimulation, lots of OTHER sensations – you can reduce the pain sensations.
So. Have a partner… or two… or three… or more, to help you out. Get warmed up, very aroused in whatever way works for you.
Because there’s no certain answer to the question, “How big and forceful must a penetrating object be to break the hymen?” I suggest fisting as the foolproof strategy. Fisting is a whole post in itself, but in brief, you begin with just one finger and gradually increase penetration until your whole hand is in the vagina.
Once you’re well-aroused, your partner (using plenty of lube) begins penetration with just one finger. Keeping a palm or a vibrator over the clit, maybe with pressure on the pubic bone, they maintain sensation elsewhere during the penetration. Go slow. Keep that degree of penetration until it’s comfortable.
Add a finger. Increase stimulation elsewhere – like add inner thigh stimulation to the clit stimulation. Keep that degree of penetration until it’s comfortable. Remember lube!
Add a finger and increase stimulation elsewhere. This will be your three longest fingers, which you should sandwich together, with your middle finger on top and your ring and index fingers touching at the tip. Penetration will thus be narrower at the top than at the base of your fingers.
Breasts and feet and lips are excellent targets of stimulation at this stage. (You begin to see why having multiple friends involved can be handy!) Keep that degree of penetration (plus additional stimulation) until it’s comfortable.
Add a finger, a pinky tucked up against the other fingers, and further increase stimulation elsewhere. Well-lubricated external anal stimulation in addition to clitoral, inner thigh, breast, feet, and lips, for example. Also fantasy and talk. Keep that degree of penetration until it’s comfortable, from the narrow tip of the middle finger down to the broad base of the fingers.
Now your partner tucks their thumb against their palm and penetrates past the last knuckle. Lots of other stimulation, closing the gate. Vibrators on clit, anus, and breasts, a mouth kissing your mouth, another mouth on your earlobe, another mouth sucking your toes (which will be curling by now).
And that, my friends, is how you break a hymen without a penis. Carefully, with a little help from your friends, and making a night of it.
Take lots of time and use lots of lube and make sure you maintain a high level of arousal with clitoral, breast, thigh, and other stimulation.
Let it be ritualistic and important, like a birthday. After all, for all that the hymen/virginity thing is bullshit, if you’re breaking your hymen in order to expand your sexual horizons, heck this is a moment!! Make it a night to remember.