Innocence for Days

When I first established this blog, Daddy and I had intended to write it together. That hasn't happened (obviously!), partly because he's demurely insistent that he isn't a good writer, (though he absolutely is), and partly, I think, because he's come to think of this place as my own, a place where he can see some of what I think about this facet of our life.

Occasionally he'll ask me to write about a specific topic. Sometimes this is a simple request and sometimes it's more of an order. He made one such request some time ago -- a week? two? -- and I've been sitting on it ever since. I think I'm ready to address it now, though.

SO! Anal sex! Here we go.

Anal is something I think I've touched (heh) upon here but I'll review quickly. In the past, I've fucked nearly every biomale I've ever been with in the ass -- usually with my fingers or tongue, but occasionally with an appropriate toy or two. Now, it's not like I went into sex with guys thinking, "Gosh, I'm just waiting for the right moment to stick it in!" or anything, but as far as I'm concerned, there's not a lot I won't at least try if my partner wants it and gets pleasure from it. So by the time Daddy and I got together, I'd had quite a bit of experience as the penetrative partner in anal sex.

Receiving is a totally different story, though. I have always found it nearly intolerably painful. Even a single finger -- even a single SMALL finger -- caused me intense pain, no matter how much lube we threw at the problem. Not only that, but as far as I was concerned, I have a pussy and I'd far rather use that, thanks. But I gamely tried it time and time again, especially since I find the idea of having another orifice available for penetration quite hot.

Now, Daddy's past in terms of anal sex was somewhat similar in that he's fucked bioboys before -- even with a strapon, which is something I've not done -- but not as often, I think, as I have. Receptively he was even less experienced than me, however. His previous long-time partner found the idea disgusting and saw fit to mention that fact frequently and loudly. That contributed to his shame about That Area, to the point where he completely buried his real feelings on the matter. It wasn't until we'd become more comfortable with one another that he was able to admit that it's something he's always been interested in.

So with time I was able to discover that he enjoyed it when I took his clit in my mouth and gently penetrated him with a fingertip. I've worked up to an entire finger once or twice but this is something he can't take for long. We'll get there.

With that discovery came the discovery that he really, really wanted to fuck my ass. I wasn't sure how I felt about this. I was certainly willing to try, with the caveat that it wasn't likely to work, but hey, why not? So we did.

At first it hurt. He was gentle but I found anything other than simple massage to be painful, as I always had. I took to laying him on his back, laying my head on his ribcage and jerking him off or fucking him with one hand while he fingered my ass with the other. It gets him off beautifully and one night....it felt good. It felt REALLY good. It felt so good that I had what I can only assume was an orgasm -- it felt different from any kind of orgasm I've yet had but it felt GREAT and left me shaking so I don't know what else to call it.

I don't know if that night was a fluke, but we took full advantage of it. He flipped me onto my back and slipped a finger back into my ass, handing me a vibrator with the other. I turned it on as he penetrated my cunt with two fingers and roughly located my g-spot (which I love, love, love, oh god I love it so much) and placed it against my clit.

20 moments of bliss followed, my body so strung out with desire and arousal so acute it was nearly painful, and I came harder than I ever have before...so hard, in fact, that I ejaculated. That's a major first to me, and one we've been unable to recreate since (though we haven't done that exact thing since...perhaps that's a theory I'll need to test!) but as Daddy put it, one moment his hand in my cunt was slick and the next it was soaked. I'll report back on that for sure.

We haven't been able to repeat that experience (yet) but I hope to do it again because it was wonderful. Since then, it hasn't been as good and in fact, the other night it was downright painful. It's a difficult feeling to describe, especially since I get off on Daddy hurting me...just...not there. It's not the kind of pain I like at all. That's something we'll need to work on.

So we're making a lot of progress on the anal front. Having him inside me like that was actually quite moving for me, as that is the last of my "traditional" virginity. I often wish that he was the only person I was ever with at all, (though of course that would have its own challenges, I'm sure), so it makes me happy that he has that particular part of my sexual experience all to himself.

There are so many kinds of virginity, though, and in all ways that matter, he has mine. I say it all the time in these posts, but only because it's true: he's made everything new for me. I am the luckiest girl in the world.