If you're obviously not a well endowed male...

you know what, there was this documentary made recently, two actually, one was called "the perfect vagina" the other was called " the perfect penis". I think that you two should watch those movies. I found em online at ninjavideo.net
guys always, usually due to new music and to porn and other media influences, believe their cocks should be comparable to an indian elephants. girls always seem to think that their breasts should be able to feed an african village. I mean the lists goes on about both sexes and what people feel they lack. but truth be told, the size of body parts, sexual organs included, all depend on the origin of your background and diet. ie, african, asian, etc.
if you wanna feel good tho during or after sex, just play with yourself and figure out what makes you orgasm and use his d*** to do it, he'll feel amazing that he is "man" enough to make you cum. also, when you're going down on him, deep-throat him and tell him how much you enjoy him and ask him as well. one of the disadvantages of being "too well endowed" is that you don't often get to enjoy that as much. that should make him feel happy with himself too. GOODLUCK!

Since I don't know any of you I guess I can say this much. My girlfriend has told me I'm the smallest of all the guys she's been with, however I'm at the point in my life where I don't care since it's not something I can fix and it's not a fault that I see in myself, that's how I was designed by God and that's how it's going to be. I'm a little over 6 inches at "full power". If my girlfriend told me I was large I'd probably think she's either bullsh*tting me or trying to make me feel better about myself. It'd be no different from me telling a girl in bed who clearly has a flat chest "I love your big breasts".

If you have to lie during intimacy to me that's bad already. I don't recommend telling your partner "I like how cute that little thing is" for the girls or "your mosquito boobs are so hawt" for the guys. Sex is all about flow and motion, you want to keep the momentum moving forward not backwards.

Penis size is pretty much the one thing that a man is terrified of finding isn't big enough. However it doesn't really matter what you say about it to him or about him as long as NOTHING referring to small is said. That will actually damage a guys sexuality. He will feel like he's a failure of a man. I knew someone at my school who turned GAY, because he was small (4 inch).

i have insecuritie, because I am only 5-6 inches and 4.5-5 inch girth, but the best way to let him know that he is big enough is to not hold back...in other words, scream if you wanna scream! it will make him feel a whole lot better when you actually scream!

In your situation you can definitely tell him he is big, because it's the truth for your case and it seems he may even be too big for you. It shouldn't hurt his dignity at all. He should be more focused on making sure there is a balance between the receiving of pleasure.

Now if you were in a situation with a guy who actually wasn't big enough for you then you could tell him w/e if it's part of the arousal talk but if he seriously asks you about his size you should be truthful. The guys shouldn't worry about something they can't change and it doesn't stop you from being creative to find ways to please their partner. In the worst case scenario, if the penis size is really a deal breaker for the girl and he'll have to find someone else who doesn't prioritize on size as much.

just show him you like it, and compliment it for its hardness, don't say its soo big if its a cocktail weenie, because he's painfully aware.

I don't think a guy really cares much about his size in this regard. It's like when guys settle into a relationship and start wearing wing-stained sweatpants around; after two years, he should be pretty comfortable with his size and how you handle it.

I think the issue for guys is when you've dated other guys and he's afraid you'll crave some previous boyfriend's better endowment in a fantasy. Ie: afraid you'll leave him.

When my girlfriend told me she came 85% of the time with me, I got the overall point of it, but was still a bit bummed. Male ego... in these cases it is at least applied to wanting your girl to be happy, although he needs to trust that you love him and want him because you love him.

Whilst I can't say I'm insecure, so don't really fit your criteria, I can say without doubt that all men like to be told they are "a big boy" not because they are necessarily but because we want to believe the girl feels we are the biggest and best **** ever (and a girl must feel we are a big boy otherwise don't bother saying it to us).

However, if a guy is truly minuscule in his dimensions, one would be better sticking with saying how satisfying his **** inside you. In this way, he will feel that only his **** could be this satisfying and make whatever mental association he is happy with in his head to meet this criteria.

Just make sure you don't bullsh*t him. Nothing more emasculating for a man than a woman lying about how much she's enjoying sex... we know (the guys who actually tune into their girl and have proper love making not just "sex")!There's no such thing as a fake orgasm to a properly loving couple, if you know your woman you know when she's cumming and when she ain't. So fake cumming is patronizing (though it works for men who treat sex as a sport).

There is no sense to LIE ! If you like it, It feels good, Your comfortable with it and like it tell him. You can help build his confidence by reassuring him he is pleasuring you ( if this is the case) and more than adequate.

its always nice to hear that its big and that you enjoy it from him. it will help to hear it from someone he cares about. make sure to do lots of foreplay and use some lube to help it get inside you if its sore.

LUBE LUBE LUBE... are you using LUBE?

I'd be less interested in what she's saying about my junk, than what the overall effect of my masculinity is on her. A little wiener can get big in due course -- it's really not too crucial in the long run.

A guy who's good in bed will not have these insecurities, because his girl--or more likely, girls--will be thrilled with whatever he has, and by the evidence of his eyes, he'll be doing fine. (Note: this is men who worry about penis size worry about exactly the wrong thing.)

So if he's a good lover, tell him. If he isn't, fix him.

Nobody likes to be patronized, if he is aware that he is under equipped for the job, then no amount of sweet talk or lies is going to change that. Penis size isn't everything, there are other things you could boost his ego with. Besides, last time I checked, vaginas ranged in size too if you want to make him feel better, maybe tell him you're just too big for him, not he's too small for you? O.o

Compliment him on his technique: it will sound much more credible (he knows his size!) and it is rewarding: a guy has to be more caring about the girl's feelings than about his to be a good lover.

Is the size of the tool an indication of the skill of the craftsman? Is a carpenter with a sledgehammer the best or even a good carpenter? I don't think so.

I would avoid saying it's big. Men are very logical. They aren't like women who if your friends say you don't look fat in those jeans we actually believe them. Even if we have a muffin top. He knows how big he is, that seems to be the problem.

When you see his penis, I would go with something like "God I am dying to have you in me right now".

Or the fact that you are saying it barely fits, I would tell him. It seems like you are pretty impressed by his size. So make it clear that it's more than enough. If when he is entering you, you are really feeling it, don't keep that to yourself, let that out. If you are raw from a particularly energetic time together, playfully let him know.

He wants to know that his penis effects you. Guys think "bigger is better". So they think the bigger the penis, the more satisfied a woman is going to be. If you are making it clear through moans and groans that his penis is affecting you, he won't be so focused that he isn't 9 inches. I don't mean fake at all! I just mean be vocal instead of keeping all those good feelings to yourself. He has dreamed forever that his penis would move a woman in an amazing way, so instead of being timid, show him that his dream is coming true cause his penis does move you.

Also, being very enthusiastic while giving a blowjob can help matters. If he sees that you adore his penis and can't wait to have it in your mouth, slowly all those locker room frustrations melt away. I mean you are dealing with years of him feeling like he isn't big enough. So saying once 'Oh your fine' isn't going to make it better. It's like him telling you once that you don't have big hips. Would that work? Or would it work if he was always kissing your hips, telling you how thin and nasty looking your friends were, always rubbing your hips and telling you how sexy they make you? It takes time to get over beliefs of being lesser in some way.

Also, I like talking about my friend whose husbands penis actually is 9 inches. I make it clear that she has really painful sex and it's just too much. And stuff like that. I just bring it up after I talk to my friend, not when we are in bed or anything. I can tell over time he really sees that I don't want that. I want him exactly how he is cause he pleases me.

I don't see how telling him something like "God you feel huge" could hurt. It's true and I think he'd like that.

If he knows it isn't big, then I would avoid telling him that it is. If he is asking you how it is in comparison to anything else you've had, certainly don't tell him it's the smallest (even if it is)- tell him that its about the same size as the others you've had. Definitely compliment him on the way he uses it. If you really enjoy something he does, brag about it in front of him and tell him that it drives you wild. Tell him how much better he is at doing something than anyone else. Size won't matter as long as he knows that what he's doing is satisfying you in every way possible.