Ok, I know this sounds weird, and maybe it shouldn't be in this section, but here goes...

I find that most of the time (like 75%), I can't penetrate. It like, skews off to the left or the right but not into the cave itself.

Or like, it goes down to the buttocks or something. I know the vagina is supposed to be a tight hole, but c'mon.

Is something wrong?

Here's some additional information

1. First girlfriend to go all the way with, so I'm inexperienced. I asked my friends about this though and no one seemed to ever have this problem.

2. I have my glasses/contacts off by the time I'm having sex because it's so late at night. But I swear even when I look, it doesn't increase my chances of hitting the spot.

3. I am Asian. Very Asian. I've measured myself at 3.25 inches. Don't laugh.
Is this affecting it? Making it difficult to get a good position?

I'm 20 and in college. Not sure if that helps but it sure as hell can't hurt.

Any opinions are appreciated.

Telling us your penis size wasnt necisary. Althought it could be the problem. I'm 16 and when i last measured mine it was 6 and a half inches, god i feel greatful :S

Of course it's necessary. If he didn't say his size - I would've asked, because that is a possible factor to the problem. However, YOUR penis size isn't necessary to share with the world.

are you sure you're as like, hard as you can be when you try to penetrate?

Is she wet enough? Is she relaxed, or nervous?

A good thing would be to finger her, but not just by clitoral stimulation, also with a finger or 2 in 'the right hole' (lol). This will stretch things up a little and will make you realise where exactly in her vagina you gotta put it in.

Maybe you just dont know how to find it? Ask her to help you, she's your girlfriend, it wont be weird. Put her hand on your penis and tell her to guide you in. Some girls are just very tight and if you ask her to help you (i've done this, even with SNL's) they will be helpful! Maybe your penis isnt that long, but width counts a lot in the first penetration.

If you run a finger over her asshole (OVER ) and then the next hole you find is the one you need!

Oh and also, good you mentioned your size, that IS very helpful in a thread like this.

Best advice I can give to you is: don't panic! Take it slow, calm down a bit and you will seem more like you know what to do. Make sure she is wet.. Like chillburg said, the right hole shouldn't be hard to find and there is nothing awkward about asking your girlfriend to "help".

Chillburg gave some good advice.

Yeah, sometimes when it's too dark/awkward position/intoxicated in the head I use my fingers to guide me in. Just rub her, find the spot, and guide your homing missile in.

Because you're small, you may need to make sure her legs are stretched out far - try and get them towards her head if you're going missionary rather than around your waist, this will let you get in easier. Doggy and some positions may be harder for you.

Don't be trying to charge in and joust her in the spot.

Just already be rubbing against her and slide it in with the use of your hands (or hers).

You will have problems once you're in as well because it will pop out if you're thrusting too much. If the problem is insistent you may want to focus more on different movements, such as rimming it, or going round in circles (many girls I've tried this on love it).

OK

You fucking moron, learn to measure correctly.

1. Take a soft cloth tape measure, the type you measure fabric with. Failing that, use a piece of string or anything else that's like a string. Dental Floss helps.

2. Do this on top of your penis. Not on the side, not under it, not around it. Do it along its top. Push one end of the string slightly into your pelvic bone. Not so hard that it draws blood, but nice and firmly. Take the other end and pull it up to the very tip of your penis. Measure the result. Make sure its accurate because even 0.5 inches matter since the average penis is only 4.5-6 inches long, depending on race.

There, you have your penis length.

That goes for all of you other PUAs.

_________________
Stormy: Being friendly to seek approval is needy. Being UNfriendly to "raise your value" is needy. Needy people depend on others' reactions.

AND FOR FUCKS SAKE, MAKE SURE YOU'RE AS HARD AS A ROCK!!!

_________________
Stormy: Being friendly to seek approval is needy. Being UNfriendly to "raise your value" is needy. Needy people depend on others' reactions.

OMG this has changed my entire outlook on life. After learning how to properly measure my penis size my inner game has jumped tremendously. I grew .5 inches by using this method, I can now tell girls with confidence knowing that Im not holding any inches back from her.

Thanks twn, I'm a changed man now.

_________________
Hobbit: Manwhore.inc: So good, it got FatalKill125 laid.
Co-Founder of Manwhore.inc

Although you are kinda small, keep in mind that it might not be entirely your fault for not being able to penetrate.

I believe one girl I'm kinda seeing currently has something called "vaginismus." It's a psychological condition where the girl subconsciously tightens her vaginal opening upon any attempt at penetration because she was raised to believe that sex is painful. It's a vicious cycle because it becomes even more painful when she tightens up!

There are also other various forms of dyspareunia (pain from sex) that many women (not all) frequently deal with. An ex-gf of mine had some form of dyspareunia, too. It took a while for us to start having good sex. I've also had a ONS with a woman who had been in a lesbian relationship for several years, and over time her vagina became accustomed to NOT being penetrated, so it hurt her when I tried.

I think that the most important thing to do in situations like this is to finger her while massaging her vagina in a way that slowly stretches her out. After a while, add another finger. Then another. Then, when you're both ready, pull the finger-cock switch.

first one finger, then another, and another, and another, then your fist

ROFL.

Ok so now to something more useful. The advice about starting with your fingers is right, and make sure to get her working on your 'junk' too so you stay nice n hard so when shes all ready you can enter easily, as has been said use your hand or hers to guide it and try a simple position like missionary, legs in the air would be good too as you could get deeper.

-SoZoS