Craig asks :

I'm currently in a relationship with a girl but we're different sizes; I'm 6'3 and she’s only about 5'4.
I'm rather well endowed and I'm worried about our first time together. I want it to be special for her and for her to enjoy it, but I'm afraid I may hurt her and ruin it.
Are there any suggestions about what things we can do, or positions we can take so that she enjoys it, too?

Tyler replies

It’s really sweet of you to be so concerned about your girlfriend’s comfort and potential pain - and that you want your first time together to be perfect.
Rest assured, height difference doesn’t bare any relation to how compatible you’ll be in the bedroom. Lots of ladies write in with concerns about being able to accommodate a large penis but the word on the street is that women’s vaginas are elastic, made to give birth, and that with the right amount of lubrication, no man’s penis would be too big.
Convey your concerns, make her realise you’re going to be understanding and careful - but maybe try to show her rather than tell her.
The last thing you want to do is to make her get a mental block, thinking about the size being a problem - it’s the only thing that is likely to create a problem getting in there.
It’s all about relaxing the muscles inside her, about getting her warm and wet before you enter her. Devote lots and lots of time to turning her on.

Lydia replies

If it’s your first time, and you want to be sure she’s comfortable, let her try a position that’s going to give her some control.
She may be happier to start with the missionary position because it’s where a lot of couples start, but only after at least half an hour of foreplay and getting her lubed up (talk about it first, discuss getting some lube - it’s playful, not problematic).
If she wants more control over how far inside her you go, and how it feels, she could go on top of you and you can help support her by holding her thighs.
She can play around by pushing the tip of your penis inside her first, and just building up to whatever feels comfortable.
If you get on with all of this okay, and want to try something from behind, again, you can just put the tip of your penis inside her and explore a bit - try spooning her from behind and play with her clitoris with one hand, while tickling the nape of her neck or playing gently with her hair with your other hand.
Just explore, and let her know she’s in control as much as she wants to be.