Born Again Virgin? The Reason Why Penetration Hurts

So I always get a little raunchy in the middle of the month, close to when my period starts (where I happen to be my raunchiest, but I digress). It's been a while since I've touched myself, hell, even longer than since I've been with a man....almost four years, but I digress again...So I watched a little porn, trying to find the right one, because it's always the same and always so fake. I try to look for real couples who love each other and it's that tenderness and realness that gets me wet. I take my trusty pocket rocket and go at it. Stimulating my clit. But then, I got bored. It's happened before, where I will be masturbating and get this feeling of, "what now???". Like I said before, I haven't had sex in almost FOUR YEARS!! I'm freakin' 24 years old and I have the libido of one too. I'm sexually frustrated, like I've become a nun without anyone telling me.
So, why haven't I done the bump and grind for so long? I've been overweight since I was 8 years old, and I know that affects how men see me. But I did have a boyfriend when I was 20 that lasted 4 months, As for my second boyfriend, he turned out to be gay, and was embarrassed by my girly parts (he was also probably upset that my titties were bigger than his). The guy I dated 6 months after him was a total dick, and we only went on two dates. I dated another guy 8 months after him, and he wasn't interested in sex at all (probably because he wasn't attracted to me). He stopped calling and emailing me after 3 weeks of us going out. Don't judge me either! By that time I hadn't had sex in three years, sure I wanted to move fast, but I was so horny!
After another 6-7 months, I had enough and decided to find myself a 'friend with benefits' type of deal. I found him online, but he admitted straight to my face that I was too fat and that we would only be having sex, and that's it. I was so desperate that I agreed and we went back to his place. Well, guess what? The little fcker couldn't even stay hard for us to do anything! He also had this weird thing on his penis that looked like a balloon knot. I asked about it, and he said he had no idea what it was. Liar. I may be naive about sex and man parts, but I sure as hell know that if there is something on a man's penis, he will sure as hell will find out what it is. (It turned out to be phimosis, where the foreskin can't be retracted without surgery. Here's the wiki link: http://en.wikipedia.org/wiki/Phimosis. It took me ages to figure that out. Also, can you believe that he gave me sht about my weight when he had that nasty thing on his dick? It couldn't have been a piercing, which would have been awesome. But noooo, it had to be a freakin' balloon knot like a clown made a penis balloon and duct taped it to his groin.) Needless to say, we never saw each other again. By that time, I hadn't been penetrated, by myself or any other person, for 3 1/2 years.

  Fast forward to now, and I'm all hot and heavy, with a man nary in sight. I really wanted penetration, but I didn't have a dildo either. Then I remembered; I have a cucumber in my fridge! I warmed it in the microwave for 15 seconds until it was body temp and go back to my room. I turn on my video of choice and start up again. Except...I can't get it in. I stop everything and try again. Nothing. It wont go in. I get a mirror and look. My vadge is closed up, despite how turned on I am. I try to push harder. OW! That sucker isn't going in. It's not like the cucumber is big either, it's one of those english cucumber ones that are really narrow, maybe an inch in circumference. Putting it in felt like when I lost my virginity four years ago. Disappointed I continued with just my vibe and ended up throwing the cucumber away, unused.
  Now I know that I don't have an infection or an STD (no infection because I was just checked by my gyno, which was also quite painful, and she would have noticed something. STD because, well, not having sex is a great way to prevent STDs. Please note the sarcasm.)
 I do a bit of research online about it, and turns out, that if a woman doesn't have sex for a while, her vadge's walls close up like a virgins and when she has sex again, it's like the first time. Painful, but fortunately, without the tearing of a hymen and blood. So for now, I can either try again and be more forceful (ouch) or wait until I have a boyfriend who actually wants to have sex with me and he can give the old push and shove (still ouchy, but at least I can blame him. And slap him. Maybe cuff him to the bed...) Sigh.

Now I'm wondering, are there any other women who are also 'born again virgins'? Where you haven't had sex in a long time, because of differing circumstances, but with the same end result?