I struggled to hide my frustration with myself as I declined Jessica’s invitation to stay the night. I wanted to, very badly—maybe to wake her up in the morning with my mouth—but I knew she had work in the morning. I didn’t want to impose on her, nor did I want to risk blurring the lines. While Jessica might not know it, she was my client. I had to maintain a measure of distance.

How could I have failed to make her orgasm? Clearly, I hadn’t worked her up enough or been patient enough. Of course, there are psychological aspects to an orgasm as well, but if Jessica had suffered any trauma in her past, she hadn’t brought it up, and it didn’t show in her behavior.

I couldn’t rule out the possibility of a psychological block, however, so I resolved to try again soon and to get to know her better in the process. That way, I could figure out what was causing my failure—my first failure, ever.

I’d never failed with a client before. I had a spotless record. Of course, I had once been a teenager, fumbling and unsure, but by the time I’d started this business, I had known what I was doing and not one of my clients had ever gone away unfulfilled. I wasn’t going to let Jessica be the first.

The plan had been to just be an amazing one-night stand, to give Jessica the night of her life so that she would then be open and freer with dating and could find a good person, settle down, all of that. But I couldn’t just walk away now. I had to finish what I’d started and complete what I had set out to do. I had to.

Mary had only paid for the one night, but I didn’t mind. I wasn’t going to charge her more, not when she had the wedding to pay for and worry over. I would just keep seeing Jessica off the clock. I’d take on a few other clients for the days when I wasn’t seeing her, but for now, my main focus would be Jessica.

I was going to give her the orgasm of her life, dammit.

I called her the next afternoon at work.

“I was hoping that you’d be free for dinner this Friday night?”

I could hear Jessica’s smile in her voice.

“That would be great.”

“I’ll pick you up at six, then.”

At dinner, I planned on learning more about her and hopefully discovering why she hadn’t ever orgasmed. I had to be careful, of course. I didn’t want her to think that I was upset or offended, and I wasn’t supposed to know that she hadn’t orgasmed ever.

If I was too invasive with my questions, she would shut down. It was a more delicate approach than what I was used to. My clients were usually open and honest, and if they were shy at first, it was easy to get them relaxed with a few jokes and some foreplay. But my clients knew what they were in for with me, and Jessica wasn’t. I had to tread carefully.

The thing was, Jessica was really good at sex. She knew what she was doing. The blowjob, and the way she had hooked her ankles over her head like that—it had taken everything in me not to come on the spot when she had pulled that little trick out of the hat. So, it wasn’t that she was ashamed of sex or afraid of it. What was holding her back?

Our dinner went well, and I managed to get a lot out of her. More than I had expected, actually. It buoyed my spirits. If Jessica was this open on our first official date, maybe this wouldn’t take as long as I thought.

I picked a little Italian place that I had never gone to before, but looked good and was near the neighborhood where Jessica lived. I didn’t want to take her to any of my usual haunts, just in case someone who knew me came up and mentioned my profession. I didn’t think that it would happen, since my clients liked to be as discreet as I was, for obvious reasons, but you never know. Luck wasn’t always on my side.

But it was with me when it came to Jessica that night. For one thing, she looked stunning, wearing a slinky deep blue dress just a few shades darker than her eyes, making them shine all the brighter. Her hair was curled and half pulled back, with a clip securing it in place. And, she was wearing these black strappy heels that I would have really liked to see her wearing while she wasn’t wearing anything else—just Jessica’s tan, toned skin and those heels.

I tried to remind myself that Jessica was a client. That meant that no feelings should get involved, and the key to that was compartmentalization. I knew I shouldn’t fantasize about her, and should only get sexual with her when the occasion called for it. Additionally, I knew I should always be thinking about her needs first.

When you’re having sex just to have sex, it’s about the other person’s pleasure and your own in equal measure. But this was about helping Jessica have her first orgasm. My own needs didn’t come into it—or so I tried to tell myself—but it was rather hard to compartmentalize when Jessica looked like she’d sprung right out of my fantasies.

She was the image of the perfect woman, if I’d ever taken the time to figure out what my perfect woman would look like.

At first, I kept things light, away from relationships and sex. Then, when we got to talking about college again, I steered things towards relationships—still leaving the sex part out of it.

“So, Mary and the others were all real party animals?” I asked, hoping that I didn’t sound too much like a therapist.

I liked to think I was charming, but I could slip into this ‘therapist mode’ sometimes with clients when I was trying to figure them out. I wanted to avoid that with Jessica, especially since she didn’t know who I really was.

It was ironic that I was using my real, legal name—the one that I never used with my clients—and my real name was becoming my pseudonym, my cover for my profession and what my goal was with Jessica.

“Yeah,” Jessica replied.

“But you weren’t.”

“Not really. Don’t get me wrong, I love a good party, but I prefer it when I know most of the people there or I can find a place to sit and observe everyone. I just like people watching. You can’t really do that at a club.”

“Fair enough. But what about guys? I’ve found clubs are a good place to pick people up.”

Jessica laughed.

“Maybe if I was like Mary, I would have cared about that, but it’s hard enough for me when I’m getting it on with someone I know and trust. Having sex with a stranger didn’t appeal to me because sex is already so hit and miss.”

“Well, I hope Tuesday night was more of a hit,” I said, winking at her.

Jessica blushed, something I loved and wanted to get her to do more of. She looked lovely when she blushed—it showed a softer side of her, one that I think she tried to keep hidden beneath her somewhat aloof manner. If she would just show that softer side of her, she’d have men falling all over her.

“It was,” she assured me, “But when there’s no orgasm in sight, you tend to get pickier about who you sleep with, because they have to be really good to make up for it. Not that sex isn’t good without an orgasm. It is. But it means that there’s no rush to the finish line for me the way it seems to be for everyone else, so the entire experience has to be good. It can’t just be a mad dash; it has to be a marathon. And most people in clubs are sprinters.”

I laughed. I liked that metaphor. I was going to have to steal it to use with my clients.

“Good point, I can appreciate that.”

Then, I did a double-take, acting as though the rest of her sentence had just sunk in.

“Wait, did you say ‘when there’s no orgasm in sight’? What does that mean?” I added a self-deprecating grimace. “Sorry, I don’t mean to pry; it’s entirely up to you if you want to share or not.”

“No, you’re fine,” Jessica said, laying her hand over mine in reassurance. There was that sweetness again.

“Honestly, since we’re on the topic, thanks for Tuesday. You really paid attention to me and I appreciate that. It made the whole experience really nice for me.”

“Even though you didn’t…” I made a vague waving motion with my hand, trying to sound like a guy a bit out of his depth.

Jessica laughed, her gaze fond, like she thought I was a bit of a dork but she liked it.

“I’ve never had an orgasm,” she admitted.

“Never?”

She shook her head.

“Not even on your own?”

Jessica shook her head again.

“I’ve tried, but I just couldn’t get it. I felt weird doing it with my hand, and a vibrator was just…I don’t even know. It was all just so weird.”

“Maybe you’re not warmed up enough?” I suggested, even though I knew that probably wasn’t the case. “I know that can be a problem for a lot of women. Their partners don’t give them enough time.”

“My ex-boyfriend tried for two hours once,” she admitted. “That was right before we broke up.”

I frowned. Mary hadn’t mentioned this. I wished she had given me more details. But then, maybe Jessica hadn’t told Mary about any of this.

“He broke up with you because you couldn’t orgasm?”

“I think so,” Jessica admitted. “He said it was for a bunch of other reasons but I know that it bothered him that he’d never gotten me to come. Every man I’ve been with that I’ve told this to, they treat it like some kind of big challenge, something that will prove their manhood. I don’t mind—really I don’t. I mean, I do, because they’ve made me mind, but…it wasn’t like the sex wasn’t good. It’s not like I don’t get turned on. I wasn’t faking anything on Tuesday; I genuinely enjoyed everything that you were doing and it all felt good. It just didn’t build up into a climax, that’s all.”

“Were you—I mean—” I fumbled with the words deliberately, trying to sound out of my league. “I don’t know…maybe you’re more into women?”

Jessica laughed.

“Nope, I’m definitely just into men. Despite all of Jane’s efforts to try and match-make me with her lesbian friends while we were in college.”

I heaved a sigh of relief that was only partially faked.

“Well, I’m not saying this because I see you as just a challenge,” I told her. “But I would like to keep trying, if that’s okay. Because I think that you deserve to experience something like that. I mean, I enjoy it when I have it.”

Jessica laughed at that, as I’d hoped. I winked at her again and continued.

“So, I want you to experience that, too. But I’m not going to leave just because you haven’t done that. If you’re enjoying the rest of sex then that’s what’s important. It’s a marathon, and it’s about the buildup as well as the finish line.”

Jessica smiled at me, a bewildered look in her eyes, like nobody had ever said anything like that to her. I wanted to go back in time and punch the guy who’d left her because of something so ridiculous. Relationships were about more than just sex, and if that was the issue the guy was hung up on, clearly there were other things that he needed to be addressing.

But it wasn’t my place to say that, partially because I would risk giving myself away as someone who did this for a living.

When I had first started out, I’d figured that it would be easy—women weren’t taught to know their own bodies, and I would show them how it was done. But with it came the realization that sex and relationships were intertwined, and I often ended up helping my clients out with the latter as well as the former.

“Thank you,” Jessica said, and she sounded like she really meant it.

I turned my hand over so that I could squeeze hers, a comforting gesture. A smart, beautiful woman such as this shouldn’t have to walk through life feeling inadequate.

We went back to her place again that night. Having immediately torn off each other’s clothes, I went down on her, enjoying her cries and the way she clawed at the bedsheets. I didn’t want to rush her, so I spent my time teasing her. I gave her what she asked for, and then backed off into sucking kisses along the inside of her thighs and lapping up her juices while withdrawing my fingers from inside her and ignoring her clit.

By the end of it, Jessica was a trembling mess—which I could congratulate myself on—but she also hadn’t orgasmed. I had been certain that I was going to help her come that time, but despite pulling out every trick in the book, using both my mouth and my fingers, she hadn’t. She hadn’t even seemed to come close, instead coasting on this one plane of enjoyment that didn’t build beyond that.

I knew that feeling—it was the feeling of not too much pleasure and not too little, enough so that you could go at it for a long time but without the tell-tale buildup of the orgasm. It was enjoyable, and Jessica certainly seemed happy, but inside, I was incredibly frustrated. Twice now, I had failed to give a woman her first orgasm—my trademark, the reason for my business.

I couldn’t help but worry that this would continue and that I had somehow lost my touch. What if this was the start of a new trend? What if I was unable to continue as Dr. O?

Maybe this was a sign? After all, I hadn’t gone into medicine so that I could be the dirty secret, or secret weapon, for a bunch of high-class women. I’d gone into medicine to become an OB/GYN.

Perhaps it was time to go back to that and be a proper doctor again—but I wasn’t going to do it on a failure. If I was going to consider ending my career as Dr. O, then I was going to do it with my final triumph, not with my one failure.

Jessica was just a particularly difficult case. I would figure this out eventually. I had to.