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I've been dry humping masturbating since I was a teen but I didn't start masturbating with my finger on my clit until a few weeks ago. I'm 29 and a virgin. I know, late start. I'm waiting until marriage or death, whichever comes first.
I've tried penetration with pens and small objects in the past but it doesn't do anything for me and actually is more weird (and a little uncomfortable) than anything else. I've attempted larger objects (still smaller than an average penis size) and it's just not enjoyable. It hurts, I feel like I'm doing it wrong and I always chicken out before anything is more than a few centimeters inside. I can get one finger in but two or more freaks me out. I would like to get over this so I'm asking for penetration ideas, nothing too big and not a dildo/vibrator. How should I do it? Positions? Anything you can advise me on really would be helpful. Should my vagina feel difficult to get into too? Nothing seems to glide smoothly in (even lubed up) which is why I think I'm doing something wrong. How many times am I going to need to masturbate with penetration before it feels good? I am assuming that I'm having orgasms when I dry hump or stimulate my clit but I'd like to have one with penetration too.

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I can't give you specific advice, being a guy, but I can say that a toy like a vibrator, which is designed to go into your vagina, would be more comfortable than a pen or other such object. They make small ones too. Also, at a certain age a boyfriend in wholly appropriate.

ec
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They have what is called a "silver bullet" that would be more you're in your ideal are. It's small, penetrates slightly, but vibrates. But..if you're wanting real penetration, you're gonna have to give in and buy a dildo or have sex.
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joely:  first relax and lay down on ur back get a tampon or ur finger and gently slide it into ur vag...nothing bad will happen it is very long and stretches get urself wet with lube or discharge and it willl be easier..start with a finger and work up to bigger things. i started w.my finger nd now can do penis and everything..it takes time but relax first
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