Guess where this is going? Just the tip, I promise.

Chapter 19: Butt Stuff

“Girls can wear jeans and cut their hair short

Wear shirts and boots 'cause it's okay to be a boy

But for a boy to look like a girl is degrading

'Cause you think that being a girl is degrading

But secretly you'd love to know what it's like wouldn't you

What it feels like for a girl”

--Madonna, “What it Feels Like for a Girl”

One thing I recommend to all men is to try being on the receiving end of butt stuff at least once. It doesn’t matter if you are completely heterosexual, get your girlfriend put a dildo up your butt.

The reason I say this isn’t because I’m suggesting that it’s going to feel all that good. It might, but whether it does or not isn’t the point. The point is to help discover, just maybe a little bit more, what sex feels like for a girl.

I lost my heterosexual virginity to a girl at the age of 15. Like most cases of losing one’s virginity, it wasn’t great. She was 14 and young enough to have an intact hymen, and most of our efforts were directed at clearing that away so that she could enjoy herself. After two tries, we did. She described it as being extremely painful, but then the pain completely went away, and after that she loved it.

We began having sex every single day, multiple times a day. Her mother was wise enough to immediately get her birth control. My parents were wise enough that when I told them to leave us alone, they did. We were such horny teenagers that at one point we had sex 18 times in a single afternoon, not counting oral.

The entire time I kept asking her the same question. What does it feel like? She took this as performance anxiety. She thought I meant, “Was I good?” “Did you come?” that sort of thing. That wasn’t what I meant.

What I meant was that I instinctively knew that what she was experiencing wasn’t what I was experiencing. I assumed the sensation at the clitoris, vulva, and mouth of the vagina was similar, but that seemed to me where the similarities end. I was literally inside her, pushing her internal organs around.

Compare that to my experience with sex. The underside glans of the penis are the primary erogenous zone, though they are of course buttressed by the rest of the apparatus. I control the pace, I control the depth, I control the force. None of that makes any difference to me except on a psychological level, mostly it just tingles pleasantly.

It makes a difference to her though. When you have someone inside you, you can feel your organs shift around. You feel an intense pressure. When they thrust and withdraw, you feel that pressure shift intensely. The sensation affects your entire body. You feel it in your stomach, you feel it in your throat, you feel it under your ears. There is a reason women scream and moan during sex, whereas men merely grunt.

I can’t even imagine what pregnant women experience. A little alien in there having a kick-boxing match with itself must be surreal.

The first time I learned this I was with a woman whom I was trying to get to let me fuck her in the butt. She was curious, but understandably a little shy about the idea. I didn’t blame her, I was also a little shy about the idea. While I’ve been with a couple of guys, I never did anal. In fact, I was never on the receiving end of anything. I’m more a pitcher than a catcher. Some people really, really like anal though.

That wasn’t the case with this woman. She liked to negotiate, so her gambit was that if I was going to fuck her up the butt, she was going to fuck me up the ass first.

I decided that was fair. She was the type of woman that liked to poop with the bathroom door open, talking to you the entire time. Anal sex wasn’t going to spoil her vanity, she just wanted to make sure it wasn’t going to hurt. This was during the phase of my life when I was dating models, and given how skinny she was, there was not much cushion for the pushin’ so I was sympathetic.

Also, given how slim she was, I wonder if her butt only ever had to deal with rabbit-sized poops. She certainly ate like a bunny. If she was used to turds the size of peanuts, it might be a problem.

Some people love anal, some do not. I’m in the “not” category, but I decided to let her try. She put a condom on her vibrator and stuck it up my butt. Supposedly, if you hit the prostate just right it’s supposed to feel really good. That wasn’t what she was doing.

Instead, I got all the pressure, all the organ shifting, but none of the pleasure. It did answer my question though, “how does it feel”. I just took the pleasure as read in a different textbook.

When it became time for us to switch roles, she completely chickened out. I got maybe an inch into her before she shut the whole thing down. I totally got played.

I didn’t get too bent out of shape though. Even though I was disappointed, she did answer that original question, at least a little. Since then I’ve done a ton of butt stuff. I’ve been in relationships with women who are really into that sort of thing. One ex loved for me to sit her on a bar stool, grab her hair, and pound her up the butt until I collapsed from exhaustion.

On one online date I went on I had a woman offer to let me fuck her up the butt on the side of the highway, simply because she hadn’t thought to bring a change of tampon. I declined, but only because I hadn’t thought to bring lube. I did bring condoms, I always do, but I didn’t expect anal on the second date.

I suppose it just goes to show how not scared of their sexuality people on dating sites are. They are on these sites to fuck. There is a stereotype that women always want relationships and men always want to play the field. If anything, I’m finding the opposite to be true. I usually walk into these dates open to a relationship, but generally the women I’m with just want to screw and move on. I’ve now officially gotten laid more often in a rusty old pickup truck than in any luxury car I’ve ever owned.