The Waiter

Max Sebastian
Jul 31, 2019 · 11 min read
Image for post
Image for post

She said, ‘How about tonight?’


‘Sure. The waiter’s been flirty all night.’

‘Oh. Okay.’ My heart felt as though it was going to burst out of my chest.

My girlfriend, Lizzy, was always the more courageous of us, I think from the very beginning our relationship was one of those opposites attract type of deals. I grounded her. She challenged me.

I was also content for her to take the lead on sexual matters because she had had three boyfriends before me, whereas she was the first person I even kissed. She’d been sensitive and understanding when coaching me up as a complete novice, but every now and then our progress would take a real leap forward, as though she reached a limit to her patience, and just wanted to get me up to full speed.

Here was me thinking she was happy enough spending an afternoon lying in the middle of a nature reserve with me between her legs, faithfully lapping at her pussy, or bouncing around on her roommate’s bed, slamming herself down on my cock in clear contravention of the roommate’s code, or stealing her sister’s lingerie so she could tease me for once hitting on her sister before I imagined she would ever be interested in the likes of me. And really, she was already thinking about the next great turn-on, the next boundary we might push.

Tonight, we were eating in a quiet restaurant, for once, purposefully choosing somewhere obscure so that we could take a break from the relentless socializing of sophomore year. I thought we’d probably have a nice meal, get relatively inebriated and then go home and work it off between the sheets. But Lizzy was so much more creative than that.

‘Okay. We’ll ask for the check,’ she said, ducking down so her face was just inches from the starched white tablecloth, her voice conspiratorially low, ‘and then I’ll excuse myself to go to the restroom.’

‘Right,’ I said, trying not to be suffocated by the butterflies fluttering in my stomach.

‘And then I’ll ask him to show me where the restrooms are.’

I said, ‘You don’t think he’ll just point out the signs?’

She gave me the kind of mischievous smirk that instantly got me hard. ‘Not the way I’ll ask him.’

We’d come to a plateau in our relationship. It happened every now and then, it was no big deal. Usually, I didn’t even know we’d come to a plateau, as far as I was concerned, things were just settling a little, and I was getting used to the next step in our relationship. There was the one where our make-out sessions had gotten to the point where we were both stripped to the waist. There was the one where we’d finally gotten to touch each other intimately, but only ever did it with our hands. There was the time we did almost everything possible with each other, but I was still technically a virgin.

But Lizzy didn’t like to stick around for long in plateaus. Whenever I started to feel comfortable with where we’d gotten, she’d be there compelling us to go further — tearing off her jeans and her panties to stun me with her nudity, demanding I go down on her instead of simply sinking my digits inside her, asking me if she could fuck me, right then and there.

And tonight, she was pushing us into fulfilling secret fantasies.

‘It won’t take long,’ she said. ‘I bet he won’t last five minutes.’

I nodded. Took a huge deep breath. Couldn’t believe this was really happening. And yet, I was hard as a rock. And I loved how Lizzy looked with the flames of nervous excitement flickering in her devilish green eyes.

‘And then…’

‘And then you take me straight home. And I’ll let you do whatever you want with me.’


This all stemmed from what had happened a few nights earlier. While I had been lounging between her thighs, sucking on her delicious sex, she had gazed down at me and asked me what my secret fantasies were.

‘Secret fantasies?’ I was confused. My secret fantasies, such as they were, had involved actually getting to kiss a real woman, actually getting to see a real woman naked, actually getting to touch a woman’s bare breasts, and even perhaps, touch her between the legs. My fantasies had reached up to the point of longing to have actual sex. And every single one of them had been completely blown away by Lizzy.

‘Yeah, you know… sexual fantasies you’ve never told anyone about,’ she clarified.

I kissed her clit. ‘I always wanted to do this,’ I said, slipping my tongue into her slippery folds, lapping up her tangy nectar. ‘I always wanted to… sleep with somebody like you.’

‘That’s sweet,’ she said, stroking my hair, and I don’t think she was being patronizing. ‘But you never had any other fantasies? More… complex… than that?’

‘I don’t know. I’m not sure.’

I could see I frustrated her a little, though she was good at concealing it. I’d seen that in her before, during all those little moments where we’d reached another plateau. The last time had been when she asked me my thoughts on birth control, before she’d decided to go on the pill.

‘What’re your secret fantasies?’ I asked her, thinking it a fair question, considering what she’d asked me.

And for the first time ever, she seemed wary of answering me. I wondered what she wanted to do that we were not already doing, that might make her want to be cautious. Was she wanting me to try anal sex with her? It wasn’t something that interested me, though I knew plenty of people apparently did it.

She pointed me to a website where I could answer a series of questions to determine what my secret fantasies were, and she would do the same, and the website would only reveal fantasies that we both shared. Okay. Interesting. The questions had started out with things like giving her a massage, taking erotic pictures of her, watch her masturbate. It moved on to things like shaving her pussy, wear sexy clothes or costumes for sex, come all over her face. There were questions about using sex toys, having sex in various places outside the bedroom and — sure enough — trying anal sex.

There were also questions about watching other people having sex, letting other people watch us have sex, engaging in a threesome, go to a strip club, take part in an orgy. Things that made me somewhat raise my eyebrows.

One question was about watching my partner have sex with another person.

‘What are you thinking about?’ she asked me, noticing me staring off into the distance while I contemplated that particular question. She had a smirk from suspicion that I was getting dirty ideas about what we might do with each other beyond conventional sex.

‘It’s a secret, isn’t it?’ I laughed. ‘Until we reveal what we both fantasize about?’

When it came time to reveal the fantasies we shared, it was a somewhat strange experience. I suspect my fantasies tended to include the softer, easier suggestions, which Lizzy might not have wanted to do because we either did them already, or she wanted to do things that were more extreme. But among the options that we did, apparently, both want to try, top of the list was ‘watch my partner have sex with someone else’. Or at least, that was what it was for me. For her, it was ‘have my partner watch me have sex with someone else’.


She was stunned. Actually, I felt mildly impressed with myself for making her react that way. You know — that someone like me could surprise, or even shock, someone like her. She was looking at me the way she had when I’d first made her come with my mouth.

‘Was that what you were thinking about when I asked you before?’ she asked me.

I had to sheepishly nod.

‘That’s really something you’d want to do?’

I thought about it seriously. Imagined what would happen. ‘I think… I might be a bit embarrassed… you know… being there when the other guy got naked…’

I flushed, but I was just being honest.

She didn’t tease me. She said, ‘But you wouldn’t be jealous? I mean, most guys would say they wouldn’t want someone else touching their woman…’

Okay, so now I felt a little embarrassed I’d apparently failed the guy test. But thinking about what she said… well, the truth was, I didn’t consider Lizzy to be my woman. I just happened to be with her. She’d had three boyfriends already, and I certainly didn’t imagine she’d stop at me. It was an incredible experience, being with her, sleeping with her. I just felt fortunate she was giving me this ride.

I wasn’t afraid of losing Lizzy, because I was kind of surprised she was sticking with me in the first place.

‘I think it would be fun… watching you,’ I said, thinking how much I might learn about this mysterious thing called sex by watching Lizzy doing it with someone who probably knew how to do it so much better than I did.

And she’d be naked, so that would be hot.

‘It doesn’t make you sick, thinking of me… with another guy?’

I shrugged. ‘You’ve already been with other guys.’

She grinned, even flushed. I think that was a first. ‘I suppose I have.’

Anyway, we talked about it. Or at least, she grilled me about why I might say I wanted to watch her with someone else, and why I might feel embarrassed about watching while another guy slept with her — which was basically because I was fairly sure the guy would laugh at me and ridicule me for being a complete dork.

‘What if you watched me fuck a complete dork?’ she asked me. Notice, she didn’t deny that I was a complete dork.

‘I suppose that might do the trick,’ I grinned.

‘I like fucking complete dorks,’ she grinned back. Well, that explained our particular relationship.

She also asked me, ‘What if I had sex with someone else… but you didn’t get to watch?’

I thought about that particular possibility. I figured the situation would have less risk of embarrassment if I didn’t watch her have sex with another guy. But it wouldn’t be as educational. At the same time, as I thought about her going off to fuck someone else… and then, presumably, she’d come back to me afterward… I’m not sure why, but for some reason it turned me on. And I looked at Lizzy, who was hardly a supermodel, but was definitely attractive, in a very down-to-earth kind of way, and I thought of her returning after a night spent in somebody else’s bed… and for some strange reason, she seemed more desirable in my eyes as a result.

‘I think it might still be… interesting… if you did that,’ I told her.

Interesting?’ she said, leaning forward to place her hands on the bulge in my pants. ‘Or are you saying it would actually turn you on?’

She was giving me that look again. That one where she was surprised and delighted at me. The one that explained why she was still my girlfriend.

‘I guess…’ I said, bashfully.

And so here we were a few days later, in a restaurant, and Lizzy was suggesting that she go into the restroom and take our alpha male waiter with her.


It would only be quick, that was her reasoning. And then we could go home and figure out if the thought of her having sex with somebody else really did turn me on. And if I didn’t feel comfortable with it… well, she’d had sex with other guys before me. Would it really be a problem to try to forget a five minute fumble with a random waiter as well?

‘Okay,’ I said, watching the fireworks going off in her eyes. ‘Go ahead.’



She was smiling like she’d just won the lottery. I thought, is it really such a big thing? You’ve had sex with other guys before. But she was my first sexual partner. I had nothing to compare anything with. Maybe when I’d had a lot more sex, I’d realize that it was a bigger deal, letting her have sex with someone else as well as me.

Anyway, where were we? Lizzy signaled to the waiter that we wanted the check. Then as I pulled out my card to pay it, she clearly excused herself to go to the restroom — and then asked our waiter, whose name badge and pre-meal introduction had informed us was called Nathan, to show her where the restroom was.

‘Uh… yeah, ma’am,’ he said, and then his eyes connected with hers. What did she do? It was some unseen body language, and yet he instantly changed course, and instead of simply pointing out the sign showing the way to the restrooms, said, ‘I’d be happy to show you.’

I watched her smile at him and run her eyes all over his tall, athletic frame, and then she scampered off toward the restroom as though she knew perfectly well where it was. Well, she did. Nathan stood there looking all confused, and then realized what was going on.

‘Can I get you anything else, sir?’ he said to me.

‘Uh… not right now,’ I said.

Then he was gone — walking surreptitiously toward the restrooms himself.


Was he really going in there with her? I sat at my table, stunned. Was he really going to become the fifth guy she’d had sex with? Five — that was a big number for me, at that time, since I was only on number one. But it as still a big deal to me, that she was going to up her experience of men by 20%.

I sat there, brooding over the check, as though trying to fairly split it between my girlfriend and myself, as though it was complicated. Really, I watched the clock. Five minutes. They must be really having sex in there, right? They wouldn’t be hiding away, doing small-talk. Or even foreplay. This was risky stuff — he probably had her up against the wall, or clutching the sink, while he thrust into her from behind.

I was so hard, thinking about it. Lizzy was really having sex with someone else. She was going to come back… and I would be able to tell she’d just had sex with someone else. And even just thinking about it, made me want to have sex with her all the more.

At the same time, as I sat there, I was feeling afraid. Unexpectedly, I did find myself frightened of the prospect of losing Lizzy. Of her deciding her waiter was better than me at sex, and that she would stick with him, instead of me. I was afraid that my great ride with her would be over.

Was that jealousy?

Oddly, it made me feel more like a normal guy. She’d said normal guys would be jealous, hadn’t she? I was normal. Sure, there was a strange, dark pleasure in sitting there knowing that my girlfriend was in the restroom, getting plowed by another guy. But I felt jealousy, so there wasn’t anything unusual or freakish about me. I was still just about a teenager, so I still felt that desperate need to conform, to be like everyone else, to not be a freak.

Ten minutes went by. Wow. What were they doing in there?

I felt the cold hand of fear close around my heart. Maybe I had lost her. Maybe she had sneaked out the back.

Oh God. There she was, walking back from the restroom, smiling at me as though she still loved me, as though she’d done nothing in there but freshen up and get into some long entangled conversation with another woman at the sinks about politics.

Was her hair a little more mussed up than it had been? Was there a slight glimmer of perspiration on her forehead, on her upper chest?

Had she really fucked a guy in the bathroom?

‘Hey honey, you ready to go?’ she asked, stepping to my side.

And I swear, I could smell sex on her. It was subtle, concealed by her perfume, but there was an unmistakable hint of muskiness, earthiness, about her. It provoked a kind of shiver of desire in me, made my pulse quicken, my manhood thicken to full hardness.

‘I’m ready,’ I said, casting a last glance at the bills I’d left on the check.

She leaned in to kiss my mouth, and the smell of sex strengthened. I shuddered. God. Lizzy had cheated on me?

I had never wanted her more.

[Image: LightField Studios]

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store