I am in the predicament of wanting a man to hold me but suspecting that I have not yet mastered my ability to honor my boundaries. When I have asked men to just hold me, they never keep their word, and after becoming turned on from the contact, I lose the will to turn down their advances. These men have had partners, or condemned monogamous relationships, and so sex complicates things emotionally.

Also, all my sexually active life I have been dealing with what my gynecologist recently characterized as vaginismus. So even though I get turned on while cuddling, my vagina rejects a man’s penis. I have to do anal and/or oral, which increasingly fails to completely satisfy the man nor me. Afterward I tend to feel inadequate, used, and defective, especially if I don’t hear from the man again. Not to sound cliché’ but I need human contact! Masturbation doesn’t offer the comfort and security of relaxing in a man’s arms. Maybe I should just ask a female friend to hold me. But the same thing could happen with her. I am almost 23 years old. How do I learn to exercise self restraint, so this cycle will end?

I'm having trouble getting my penis into my girlfriend's vagina. There are some things that would probably be better put in point form, so here goes:

-I am average sized, leaning towards the shorter side of the spectrum
-I'm sure that we were ready - she was dripping wet down there
-I "think" she's really tight. For reference, one finger would get squeezed pretty tightly; two fingers would require a good deal of force to get in
-We've tried missionary, doggie, standing up from behind, and standing up face to face
-It's worked out twice in the missionary position but was really hard to accomplish; we don't seem to be able to get it to work again
-We 'do it' with the lights on

My question is, am I doing something wrong? She even tries to cram my penis inside using her hands but for some reason, it does not work - I just don't feel like there is an opening... We've tried several times and it is pretty frustrating...

-Ps. For the two times it went in, it did not feel as great as I was led to believe it would. I think I have more fun with a handjob - is this normal?