Author: datmythrowaway

Introducing the innocent girl to anal [m/f]

Over the last week or so I've had a great time writing about my time dating this sexually repressed woman and how insanely hot it was to break down her sexual barriers one by one. I'm sad to say I'm just about out of stories about her… but this final (or maybe penultimate) installment might be my favorite one yet. If you want to read the rest of the stories for some background, here they are:

Making her beg / Making her squirt / Eating her out

We'd been dating for ballpark five months, and the sex continued to be phenomenal. I kept pushing the boundaries, she kept resisting and eventually caving in. I came to realize that she loved the process of being corrupted as much as I loved being the corrupter– she was a sub to her core and came the hardest when she was being "forced" to do something that she felt was degrading or wrong. The hottest part was how she'd always end up begging for it– watching this nice Catholic girl implore me to choke her, to call her a whore, to make her squirt– those times remain some of the hottest memories of my life. Read more »

Eating out the innocent girl for the first time in her life [m/f]

I've written a few stories about a woman I dated a few years back– here's another favorite memory.

Like I've said before, Caitlin was very reserved and proper, with somewhat traditional, vanilla views on sex. On the other hand she was deliciously responsive, and when she got worked up there was nothing more fun than to see her inhibitions yield to her arousal.

We enjoyed a healthy sex life, but for the first few months she never, ever let me go down on her. "It's gross!" she'd say when I tried to eat a box lunch. Only once in those first two months, when we were both drunk, did she let me go down on her. I've seen Nina Hartley's video— if you haven't, this will change your girlfriend's life– so I had a solid grasp of the fundamentals. Ten seconds after sucking on her clit she came, violently. Fingers in my hair so hard she almost cut my scalp. She started breathing, fast, and muttering "whoa, whoa" under her breath. I smiled, looked up at her, wiped my mouth off, and went in for a passionate kiss. Read more »

Making the innocent girl squirt for the first time [m/f]

In my last post I wrote about the first time Caitlin and I hooked up. I went home the next morning (afternoon) after getting her off a bunch and not getting a ton back on my end besides some rubbing over the pants. PSA: women, unless maybe I'm wearing sweatpants that are drenched in lube, rubbing my dick through pants is like me trying to get you off with chopsticks. Not gonna happen. I can barely do pho for god's sake.

Anyway, time passes, we see each other a few more times, and things heat up. We start boning, and it's just straight fire. It's super easy to get her off, which of course makes me feel like a stud, and as I've alluded to before she has a wilder side that comes out when she's especially aroused.

It's one of the first nice days of spring, and we're at a roofdeck party at her college friend's house. Beer, burgers, views of the skyline, the whole deal. It starts to get dark and cold and we start to get drunk and horny. We see people migrating downstairs where it's warm, and I shoot her a look and snake my hand around her waist. Her panties were off and in a bunch next to the grill 60 seconds later, as I pushed her up against the railing and sunk two fingers into her soaked pussy. Read more »

Making the innocent girl beg for it [m/f]

Caitlin has the most amazing sexual tension of any women I've ever had the pleasure of fucking. By 'sexual tension' I don't mean two people looking at one another knowing the other wants to do the horizontal tango– although that was there as well. I mean the tension between her strict sense of propriety and her sexuality simmering under the surface waiting to be brought to a boil.

I'll start from the beginning. This will be a little long, so if you're a dirty scroller I suggest you jump ahead until you start seeing words like "pussy", "dripping", and "OMIGOD OMIGOD FUCK FUCK FUCK". Read more »