As I mentioned before, I wanted to be open-minded about my relationship with my girlfriend, so I didn't want to pressure her. I'm not really the dominant type, but as we talked over the internet, it seemed like that was what she expected of me. But, either she masterfully misled me, or, she was just very naive about sex. She told me she was a virgin, and, as it turns out, I don't think she was kidding! Basically, we were in this hotel room looking out on the most beautiful beach I've ever been to, Boracay beach, in the Philippines. We went back to the hotel room to have sex, and, as it turns out, she was tight as a drum. It was like trying to fuck a C-clamp. I bent my dick in half, and the reality set in.

 I asked:

"Sweetie... Did you use that vibrator I had you buy?" 

She replied, "No." 

I just sighed, and calculated my next moves. 

Now, I have gay friends who've been through a similar situation. Someone might acknowledge that they're gay or whatever, and want to be fucked in the ass. But, they weren't really realistic about it. My best friend is gay, and he had a terrible experience with a boyfriend of his when we lived in New York. His boyfriend was certainly attracted to him, but that doesn't mean anything about practical knowledge about sex. So, unfortunately for either of them, he was trying to have sex with his boyfriend, and his boyfriend was wincing and crying in pain, but insisting they continue. He'd never even fingered himself, I suppose.

C'mon, people. Be practical. Sex shouldn't be painful and bloody. (Although, I did fuck an ex when she had her period. It was weird, but, she seemed to like it. And, no pain! Just smelled metallic.)

Back on topic:  So, I figured that I had to carefully instruct her on every move before I had sex with her. Now, I've been playing with my ass since I figured out I could play with my dick. I was writing stories about raunchy anal sex when I was nine years old. Can someone be a pervert before they hit puberty? I dunno. But, this is all true. So, I thought back to how I got into it. Just sticking a finger up my ass while I jerked off felt great. So, I brought her soft, small toys, and nice lubricants. As it turns out, they don't really have much of those in the Philippines, so, I brought them from the U.S. 

It's been slow-going. Like I said, she was tight as a drum. Even last time I went to visit her, she was saying, "Yay, I can fit two fingers in now." I thought, "Terrific! We can have sex now!"

Then, I get there, and remember her fingers are half the size of mine. 

Oh, well.