Scarleteen

hello, i identify as he/him but i am biologically female and i have been having issues with masturbating recently. as i deeply want to be penetrated i purchased a small dildo that is made for sex toy newbies. it is 15cm tall and about two fingers thick, a little more, with a slight curve and it mimicks a glans at the tip. but even that is too big, well the tip is too thick. it also has vibrating settings so it is not completely useless as i use it for clitoral stimulation.

the issue is in almost all of my fantasies i wish to be penetrated and i can feel myself get ready, i can easily push a finger in as i don't have problems self-lubricating (although i have lube just in case) but as i never had sex, i still have my hymen and about 4cm in i start feeling pain with the dildo, whatever the position i am in; although i noticed one that is less painful. i wish to know how to prepare myself so i can fully insert it with little to no pain? am i the type of person who has to feel pain during first penetration or is it possible to just prevent pain while breaking my hymen?

fyi: i am someone who is really into manicures and all and i like to grow my nails very long so i cannot use my fingers anymore.

Hi there.

So, the hymen isn't something that usually breaks at all, and it certainly isn't something that needs to be "broken." It also is something that gradually wears away over a lifetime with or without any kind of vaginal sex, so the idea that one person has a hymen different from someone else's because they haven't had that kind of sex when someone else have isn't realistic.

If you are having menstrual periods or have had them, then you know already that your hymen has openings in it, otherwise that flow wouldn't be able to come out. Now, it could be that the formation of your hymen now is such that it is making using fingers or toys inside your vagina more difficult, but since it's usually very flexible tissue, chances are good that's probably not the issue here. For more about the hymen, you can check this out: My Corona: The Anatomy Formerly Known as the Hymen & the Myths That Surround It

Too, no one "has to feel pain" with any kind of vaginal sex. I personally don't like or use the term penetration for a bunch of reasons, the biggest being that it tends to misrepresent the vagina as passive when it's not. I share that because when fingering, intercourse, or masturbation with toys hurts, it's usually because of reasons like someone not being turned on enough and feeling good enough for the vaginal canal to start doing what it usually does when this kind of stimulation is right, which is kind of pulling in (versus just sitting there while things are being pushed inside, if you follow me). Or, not using enough lubricant, or being too hasty when it comes to engaging the vagina because someone isn't turned on enough yet. Another biggie that often is the culprit for pain is expecting pain. So many people have been raised to believe that vaginal sex is or even should be painful, and that belief alone, and the fears and anxiety it tends to cause, can be why it hurts, all by itself.

So, for one, it may be that the dildo you have isn't right for you right now. Maybe what you need is something between the size of your two fingers and this dildo. Or, if it isn't curved, as your fingers often will be, maybe its the shape, not the size, that's the issue. Or not using enough lube, not being turned on enough, believing pain is expected or more.

I also strongly suggest rethinking "penetration," and the idea that you or someone else would be pushing things into the vagina. Try to think about it more like both a pull and a push happening at the same time, and where you want to go with the pull of the vagina -- and then slide whatever it is in a little -- rather than the push of whatever you're using. It's a thing that can take a little exploring and experimenting to feel, both in your vagina and with whatever you want inside of it, but it shouldn't take that long to feel out.

could it possibly be the angle then? because i have noticed that with different angles, the feelings would be different and more enjoyable. and i just realized that my dildo can actually be inserted from both sides (not as a double dildo more as a smaller tip on the other side) so i may try this and see how it goes.
i will try to relax as much as i can and try again with the smaller side but eventually search for a smaller sized toy as it tends to get frustrating.
but your advice is being really helpful, thinking of it in another way will definitely help!

It could absolutely also be the angle. A lot of times, people will go to go into the vagina like the canal is straight up or back. But it's actually curved, so kind of poking something straight in can tend to just push against the posterior wall of the vagina instead of sliding inside and upward, into the canal.