Secret Confessions of a Smart Girl

I have often thought about the fact that what I fantasize about, and what I actually enjoy, are two very different things. This came up earlier in the week, because of a discussion a friend was having about orgasming from penetration. Penetration is often a huge part of my fantasy life. Whether it’s dreaming about getting gang banged by lesbians with strap-ons, dual- or triple- penetration fiction, or straightforward romance novel “he’s so huge, will it really fit?” fucking, penetration is often a central feature of my imaginary sex life. In my head, being filled to overflowing, fucked for hours in every hole, and stretched to my limits is hot. In reality? I like penetration, I like it a lot, but I prefer fingers or a small toy to a big cock. I am not a size queen. My first lover was an extremely well endowed man, and while the rest of our sex life was incredibly hot, fucking him just hurt, and not in a good way. I’m a masochist, but that kind of pain felt like damage, rather than the white hot ecstasy of a singletail or blade. Despite knowing this, however, it’s still what I fantasize about. I think, to an extent, it’s what I’ve been conditioned to fantasize about, and thinking about it gets me off.

I do wonder, though, if it would be possible to take advantage of my masochism for a man to turn size to his advantage. Perhaps part of the problem is that neither my partners nor I had the goal of making sex hurt, and so the pain was an unfortunate side effect rather than an intended consequence. What if, instead, the setup was different? What if the goal was pain, rather than pleasure? I think it would be almost unspeakably hot for someone to force me open, to make their cock fit, to move and shift inside me until I am able to accommodate his pleasure, and then fuck me until I scream. I know a man who collects large dildos. On one hand, they scare me. On the other, the thought of him finding ways to get them inside, slowly working them in, inch by inch, not for my pleasure, but for his own satisfaction makes my nipples go hard and my heart rate quicken. Imagining the sensation of stretching, of pain, of being told that that solid hunk of silicone is going to go in even if it takes all night gets me writhing. But thats fantasy.

In reality, I don’t know. I prefer a lover who can fuck me without making me feel damaged. I would, however, like to experiment one day. I’d like to be tied, spread-eagled, to a bed while someone penetrates me with a toy that for pleasure’s sake is a bit too big. I’d like them to work it in, focused on their task, not because they think it’s going to give me an orgasm, but just to see if they can.