Her dirty little secret. My weird little adventure.

Sometimes Aphrodite's gifts can be pretty interesting.

Last autumn, completely on a lark, I posted on Craigslist. I wrote seeking to exchange body massage and possible oral with a laid-back partner whose schedule was as crazy as my own. I wasn't really expecting a response. A long while later, I got a response from Stacy. We arranged to meet over coffee.

We never got to the coffee.

Stacy came to my place to see me three times during this past winter, and I quickly figured out that things were going to be a little weird. We would only meet when she contacted me first, and that could be on the spur of the moment. She didn't tell me her last name, or even her age, until our last meeting. She was very hush-hush about most of her life and world. Generally, I was encouraged to not call her, but textmessages and emails were fine. By our second meeting, I figured out that I was supposed to be her Dirty Little Secret. She agreed.

As it turned out, Stacy was a grad student with a very troubling life. She was living with the after-effects of beating a major illness. She lived with terribly ill parents, had a workday full of crisis and strain, and grad school. Stacy responded to my ad because she sought straightforward, no-strings-attached escape. She wanted to fuck, pure and simple.

At age 29, she was almost totally sexually inexperienced. She had never had an orgasm. I know she came close at least once when we were together, however. I would have enjoyed ushering her through that completely.

During our first time, she showed almost no interest in kissing. She enjoyed my oral, and I enjoyed the sweetness of her completely bare pussy. She eagerly sucked my cock, but her technique was mechanical and dispassionate with one very bizarre exception.

Apparently Stacy really wanted to learn how to deepthroat dick. However, her way of accustoming to the technique was by forcing herself to take as much as she could, reach the point of gagging, push a little further... and then suddenly leap off me and speed herself to a sink where she would spit and probably puke. And then she would come back for more. Over and over again.

Now, maybe with thanks to pornstars like Anastasia Blue and sites like Throat Gaggers, "forced blowjobs" seem to be a thing. (Shayne recently told me about an encounter she had with Don, a Top who did the whole fingers-in-mouth, gag-on-my-dick thing with her, and apparently she found it really hot.) Me, I appreciate how that kind of rough cocksucking fun could have a place in d/s play, but as far as being blown is concerned, the act of having one's cock sucked, the sensation isn't anything particularly special.

Give me wet, wanton slurping. Give me intense suction. Give me your moans and groans. Tell me how much you're liking it. Grasp my shaft and stroke me while you suck. Hold and caress my shaven, full balls. Caress my legs. Let me tap my cockhead on your face, making your face glow with your spit.

But have me actually try to gag you? Hrm. I'll experiment with Shayne (hear that, baby?) sometime. All in the interests of science, of course.

But when Stacy repeatedly forced herself and ran off to puke, it kept me from enjoying her sucking enough to cum. I just don't respond well to start-and-stop nonsense. Then she'd get frustrated because I hadn't filled her mouth with my load. I'd be frustrated too. This is all a big real shame, because she otherwise really enjoyed sucking my cock, and I love it when a woman really enjoys sucking my cock.

I gave Stacy her first anal fuck during our second time together. To my amazement, she took me in with much less preparation than I'm usually expecting to give an anal virgin, and she was both confused and thrilled that she liked it so much. Her ass was exquisite. She was full, very round, and while she was a little (and charmingly) self-conscious with how big it was, she was shaped in such a way that it was a beauty to behold. A real booty. Her anus was delightful to see: crinkled and pale, readily winking at the slightest touch. I'd really been looking forward to fucking her lovely ass again.

She opened up that she had rape and bondage fantasies. We touched on this during our last time together, with me hoisting her wrists far above her head in my grip as she stood against the wall, her toes barely on the floor.

"I've been watching you," I whispered huskily into her ear. "I see your comings and goings. And I know what you're really about. Everyone else thinks you're this prim and proper woman, this sweet grad student, the perfect daughter... but you and I know the truth about you... that you're really a dirty, whorish little slut who craves sucking thick cock and getting fucked in your tender little asshole. Isn't that right, you little skank?"

She would swoon and nod her head.

"I'm going to fuck you. There's nothing you can do about it. Do you fucking understand?"

She got very wet.

"You have only one decision to make, slut. Am I going to take you hard and rough, force you and leave you bruised and battered? Or are you going to be a good little cocksucker and yield to me? Either way, your fate is sealed: I will fuck you, no two ways about it. Or would you rather accept your fate and start sucking my dick like a good little whore?"

She dropped to her weak knees then and started sucking. But, again, something intangible was amiss.

I'd like to say that sex with Stacy was the hottest thing ever. It had all the hallmarks of a man's fantasy: a young, very attractive, very inexperienced but eager woman with a fantastic body seeking no-nonsense NSA sex. But the truth is: it was an effort, and sometimes my gentlemanly skills had to be called into play. Stacy approached sex like she had something to prove and had to do it this instant.

Maybe it would have been better if I were an uncaring, inconsiderate prick and just fucked her senseless without regard for her. Great fantasy and d/s play maybe, but you know, so sorry, just not my style.

I did everything I could to escort her through a rewarding experience, but somehow I just couldn't overcome the fact that her inexperience and lack of sensuality kept me from my orgasm. Part of the challenge was how our arrangement was so skewed, with me almost being expected to drop my world to be available for her, or how she always seemed to be in a huge hurry to fuck and leave. Positions happened staccato, rather than fluidly and with shared pleasure.

Sometimes sex with Stacy felt like what I'd imagine sex with a hooker would be like, dependent on my pleasure but also hurried and without sensuality, except that it was free.

In the end, the fact I hadn't had an orgasm with her distressed her so much that she would email me to cancel our occasional get-togethers. To her, that I hadn't cum indicated that something was wrong with her. In her mind, a man should be able to get it up and get it off in no time, no muss, no fuss.

Maybe when I was 18 that could happen, but that wasn't because I was more of a stud then than I might be one now. It's because I didn't know better, because I was less sophisticated about my sexuality, my cockwants, women's bodies.

While she definitely had some issues, I also think I could have nurtured her more, and certainly could have shown her more about what it takes for get a man to cum. (Like, stop hurrying. Like, have some fun yourself, dammit.) It's unfortunate because I had begun to plan something more no-holds-barred for her, but hey.

Sometimes I associate certain drinks with specific lovers. Shayne is dirty martinis and Wiser's whiskey. The Grrl was Frangelico. Diva was Bailey's. Stacy introduced me to frozen Limoncello, which I would later discover was even better with a fresh raspberry. It seems fitting to me that as I write this entry, I've taken the bottle of Lemoncello from my freezer and nursed it. I had saved it mostly for Stacy's visits, but now it's appropriate that as I conclude this, it, this post, and my fucking Stacy, is finished.