I'm gonna answer your points one by one, these are all very simple problems that are easy to fix.
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-I have a....smaller size penis. My circumference is absolutely right on par, but my length is....eh. I'm not small, but im below average. I looked at a lifestyle condoms survey conducted by doctors on 400 male volunteers and the average was anywhere from 5.25-6.5, while I'm sitting at anywhere from 4.25-5 depending on how hard I am/how you measure it. This is probably the biggest insecurity I have about hooking up with girls. I feel like I'm limited to only a few positions and that they will compare me.
If you're insecure about your size, work on using your hands/mouth better. Although the size you are is big enough anyway dude, the G-spot is not that far in and it's just a classic case of "It's not the size that matters, but how you use it". 'Smaller' does not equate to 'too small' just don't worry about it.
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- My ex was the only girl I've ever made out with, and she sucked. She just let me kiss and bite her lower lip while she didn't really even kiss me "back". Now that I'm single I've hooked up with 2-3 girls and have noticed how absolutely horrible I am at kissing. I can kiss, but when a girl start kissing "back" I don't know how to "receive" it or make it "blend" in with my kisses that I'm giving. I've just feels sloppy and unorganized, not "fluid" motions. Does that make any sense?
My gf actually comments regularly about how good a kisser I am. The trick I use is to let them lead the kissing, dictate the pace etc, then if you want to be a bit more assertive just exert more pressure into it, pull them tight to you but let them continue dictating the pace and just match them blow for blow. If they aren't using much tongue, don't try forcing yours down there, if they are using a lot, just match them for it. Keep things simple.
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-I have only had sex about 15 times (with my ex) and I'm insecure that I am not good at it at all.
For this just get out of your head, I used to have this same insecurity but the key is (in my opinion) to open up the lines of communication and listen to what she's saying, if she says harder then you do it harder, if you are say fingering her and not getting much of a physical reaction, chances are what you're doing isn't working so change it up, if when you change it she lets loose a little moan or squeezes your hand if only for a second, continue doing what you've changed to for a little bit.
Biggest thing though is just get out of your head, don't think about it so much while you are doing it, just let things flow naturally but just keep 1 eye/ear open to anything you may need to change up.
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-I cum pretty quickly. Is it because I'm new to sex and still haven gotten "use" to the feeling? Like within 30 seconds-5 minutes and I'm done.My friend had the same problem. He said to just stop when you're about to cum, and keep doing it every time. After 5-10 minutes, you'll be able to hold back easily and he said he went for an hour! Do you think that will work? Or will it go away the more I have sex and get used to it?
Take your friends advice.