On my last visit to Chicago, I had just two items on my agenda. The first was to see the jellyfish exhibit at the Shedd Aquarium, and the second was to watch my ex-girlfriend use a strap-on to have sex with an old man. The latter request came from my ex’s client, whom I’ll call James. My ex, whom I’ll call Vanessa, has been a professional dominant for years, though it was never something I’d witnessed, since by the time that stint picked up for her, she and I were both in love with other people. Like good lesbians, we remained close friends throughout the years, through different cities, lovers and occupations.
My relationship with Vanessa came at the tail end of a time in my life when sex felt more like theater, when I thought living meant merely saying yes to everything. I didn’t know anything about power or intimacy or trust, even though I played with these concepts continuously, recklessly, in private homes and sex clubs, with strangers I met online, and old friendships I needlessly complicated. Fear was something I thought I could talk myself out of, if only I had the right words. I knew so many words at that time, but I didn’t know what any of them really meant.
Despite the years we’d lived in other cities, Vanessa and I had always been perfectly candid with each other, especially the more she immersed herself in the sex worker realm, which was so foreign to me, and so alluring. I was still shocked nevertheless, when she asked if I would watch her dominate James while I was visiting Chicago.
“He wants to show off what a good submissive he is,” she said. “Plus, you’ll get free wine and sushi and dessert.”
Though I’d written about pegging dudes and orgies for various websites and publications, I considered myself fairly vanilla. I wondered if I’d be able to handle seeing Vanessa in Domme mode, if I’d be jealous or freaked out. I remembered a fetish night I wrote about years ago, which screened footage of a few Chicago Dommes grinding their heels into men’s testicles, and the thought of Vanessa partaking in such an act made me shudder. Regardless, it took me very little time to decide. I still knew how to say yes. I abide by the Writer’s Manifesto, after all: A good story is better than a good time.
After I relayed my consent to her, I followed up with a few blatantly novice questions. Should I dress up? Am I allowed to talk to him? Is he going to serve me too? The more I thought about it, the more I realized I didn’t know anything about Domme/sub etiquette. I half expected James to bow or curtsy upon meeting me, like I was some kind of British royal and not a 20-something in skinny jeans and a Jem & the Holograms T-shirt. Even though I was just a casual observer and not his Mistress, I didn’t know quite where I fit into their relationship.
When the day came, Vanessa picked me up and together we drove to an unassuming flat near Wicker Park. Once inside, the flat revealed a full-fledged, though modest, sex dungeon, with such accouterments as a medical examiner’s chair, a St. Andrew’s cross, a steel, human-size bird cage, and a wall of sex toys, ranging from innocent feathers to pinwheels and serious floggers. Since I have a kid-in-a-candy-store mentality, it was challenging not to pick up a bullwhip and start swinging. I also really wanted to test drive the bird cage. But, out of professional courtesy, and to retain an ounce of dignity, I merely allowed myself to touch some of the instruments before plopping down on the black leather couch while Vanessa changed into her Domme attire.
When she reappeared, she was wearing a revealing black lace slip dress, showing off her amazing legs, and simple black high heels. I tried to keep my gawking to a casual level. I had somehow forgotten how beautiful she was in the years we spent apart. We chatted as we waited for James to show up, and made fun of the dungeon’s CD selection.
“Portishead!” I nearly shrieked when “Dummy” came on the five-disc changer’s rotation. “I lost my virginity to this.”
“I’m not surprised,” she said. This was not, however, the soundtrack that James would lose his anal virginity to. Vanessa chose something moody and ethereal. Something I quickly forgot about as my tensions mounted.
The buzzer rang and Vanessa hopped off the couch to greet him. “Here we go,” she said, and smiled at me. I didn’t realize it until that moment, but I was grinning uncertainly.
“I’m nervous,” I said.
“Why?” she asked, not stopping her stride toward the door.
At the time I didn’t have an answer, but it probably had to do with a desire to please people. Even this strange man I didn’t know. This was clearly a fantasy for him, and I was a willing collaborator. I had a stake in his pleasure, even though it was minimal, and I wanted him to find the experience fulfilling. Transcendent even. Plus, I was not immune to the age-old female cliché of wanting to be seen as desirable. The thought that I could mess up somehow was fairly ridiculous. Like, what, would I fall off the couch? Set myself on fire? But still, my heart raced as Vanessa opened the door and natural light flooded the dimly lit dungeon ever briefly, then vanished.
James was a mild-mannered gentleman, in his 50s or 60s, I’d guess, with short-cropped thinning gray hair, a tender disposition, and even gentler baby blue eyes. He could’ve been anyone’s father or grandfather, and maybe he was. I pushed that thought out of my mind, however. Even though both my grandfathers were dead, it did not comfort me to think about them ball-gagged or bound by a sex worker.
“Hello,” James said warmly, setting down many bags that contained gifts and food, to shake my hand. “It’s a pleasure to meet you.”
I’d assumed the scene would start right away, but they chatted for a few minutes idly, about the weather, parking tickets and such. While they talked, Vanessa asked him to rearrange pillows and furniture, in a firm yet egregious manner. Once she was satisfied with the room’s feng shui, she flatly intoned, “You may prepare yourself.” At that, James striped off his street clothes until he was wearing only a tiny, see-through, red lace thong. Vanessa smiled in delight.
“Wonderful,” she said. “Give us a twirl.” James spun around then looked at Vanessa admiringly.
“Very good,” she said. “Show us what you brought for us.”
At that, he got down on his knees, onto a pillow Vanessa thoughtfully placed before her, and carefully began to remove the contents from his bag. The first was a lace nightgown from Victoria’s Secret, elegantly wrapped, and a gift card, also boxed and wrapped impeccably. Vanessa praised his attention to detail, and choice of wrapping paper.
“Thank you,” he said. “I have a gift for Anna as well.” He pulled out a small orange box, which was wrapped so well it took me several minutes to open, which also contained a $50 gift card. Earlier that week, I had sent Vanessa a text, telling her to charge James an extra $10 and give that to me so I could call myself a “sex worker.” I was half joking, but James’ $50 gift did fill me with a curiosity I hadn’t ever admitted to myself. I wondered if I would be capable of dominating someone, if I could breach the boundary between sex journalism and sex work, or if I had already with interactions like this one.
Before I could really unpack these mental entanglements, James had removed several bottles of wine for us to choose from, narrating each one briefly on region, varietal and taste.
“This one is a sauvignon blanc from New Zealand,” he said. “I know you are fond of that region, which is why I chose it.”
What became immediately clear to me was that James knew Vanessa’s tastes and preferences far better than I did. I couldn’t even remember things as basic as her favorite color. I assuaged myself of this inkling of jealousy by noting that I knew her biblically, which was far superior than knowing her preferred wine region.
Vanessa poured us each a glass of sauvignon blanc. She then told James to take off her left high heel and give her a foot massage.
Aside from Vanessa’s occasional instruction and James’ intermittent toe sucking, the conversation that flowed easily between the three of us could have come from any benign dinner party. And not unlike my attendance at most dinner parties, I found my wine glass empty almost immediately. Vanessa barely sipped her wine at all. James refilled my glass, but only after asking Vanessa’s permission, and receiving her approval.
Since James and Vanessa’s relationship involved a clearly delineated power dynamic, it was difficult to not want to insert myself into it as well. I found myself mentally taking on kind of pseudo-Domme role, albeit a really polite one whose main role was to occupy couch space. “Why yes, James,” I said, my tone shifting to one of a more regal inflection. “I would love some more wine.”
The conversation remained light and G-rated, until Vanessa asked James to tell us how much he had learned from serving her in their two-year relationship, which had far surpassed the duration of my time with Vanessa. His face became boyish, animated. He was eager to share and please her, his face alighting each time he remembered something else.
“You may remove the right heel now,” she interrupted.
Once she was sufficiently satisfied by James’ foot worship, she allowed him to serve us dinner. He fed her sushi directly, with soy sauce and wasabi, according to her precise specifications, while I was thankfully allowed to feed my own face in peace. It was wonderful to be pampered, and again my mind wandered to the prospect of having my own submissive. I was raised working-class, and thoughts of servants or maids filled me with tremendous guilt. I cringe even when a waitress calls me “ma’am.” It felt wrong, to be given reverence when I didn’t deserve it. Yet having James serve me didn’t elicit such feelings. I delighted in them. Maybe because I knew it was temporary. That his subservience would end as soon as he left the dungeon for the far less controlled arena of the real world.
Dessert was just as impeccable as dinner. James really did have good taste. I suppose this shouldn’t have surprised me, as soliciting the services of a dominant is hardly cheap. He was clearly moneyed, and it showed in his pastry selections. Vanessa gave me first dibs on a raspberry cheesecake tart, and I tried not to wolf it down in one bite. I felt I had to maintain a sense of decorum, to compete with Vanessa’s calm assurance.
After dessert, James had one final gift. He placed it gingerly in her hands, like a baby. She unwrapped the tube-shaped package, revealing a small, but respectably sized purple dildo.
“It looked rather large to me in the store,” said James. “But once the attendants told me it was called The Mistress, I knew I had to buy it.”
“Very good,” said Vanessa. He’d been on his knees for at least an hour, but if he felt any discernible discomfort, it didn’t show at all.
She told him to drag a padded spanking bench over from the wall and to assume a position on all fours while she readied herself, donning a black leather harness, latex gloves, and placing a generous pump dispenser of lube by her side. I was giddy from the wine by this time, and looked down at James from my place on the couch, front row, center. He didn’t return my gaze for the first time that night, and seemed visibly apprehensive. You could tell this wasn’t an act he enjoyed. In fact, I found out later, he’d only done it one other time, a few months prior, also with Vanessa. He was doing it to please her. He’d do anything to please her, his look of intense concentration said.
His head remained rigid for the first few minutes, seemingly mired in anxiety, as she entered him. Her slow thrusts were accompanied by compliments of James’ performance, and his occasional strained whimpering for more lube.
“Good boy,” Vanessa said, encouraging him to obey her, to go deeper into the subservient headspace. His body began to soften.
At intervals, Vanessa would look over at me and smile this absolutely wicked smile, illuminating a sense of both mastery and farce. Can you believe I get paid to do this, the smile said, and with that she resumed her attention to James. I felt myself flush at the sound of her voice, which rarely rose above a whisper, and at the giving and the taking that was happening all at once.
The memory of my own past experiences wearing a strap-on with men arose, and I was dismayed to find myself getting turned on. My arousal caught me completely off-guard. Was it simple voyeurism, a man being exposed in this way in front of a stranger, that turned me on? Was it Vanessa, the hot nights we shared so long ago that were now only available to me in memory? But my thoughts couldn’t stray long before they were wrenched back to the scene unfolding in front of me.
She gripped his hips with both of her gloved hands, and he became less and less able to control his groans. I felt both amazed and overwhelmed at this subversiveness, something that rarely existed in my normal, day-to-day life. I cursed myself for drinking so much because now I had to pee, but not wanting to get up and miss anything, I endured the agony. I can’t believe this is happening, I kept repeating to myself.
And then, just as quickly as it began, it was over. The tension shifted as James cleaned up. He packed up his gifts for Vanessa to take home with her, the extra wine bottles, The Mistress, and the desserts that Vanessa’s girlfriend would happily eat when we arrived back at their apartment later to chat and finish off our night watching reruns of “Party Down,” like it was just another day. James removed his panties before changing into his street clothes, and placed them in a trash bag that he would carry out shortly. While doing so he told us a story about how he had once put the panties Vanessa made him wear in his pants pocket afterward and forgot about them, almost leading to an embarrassing situation in his presumably non-kinky life.
He gathered up the trash bags to take with him, and as he headed for the door, he left us with a bit of fatherly sentiment. “You girls be careful out there,” he said, as Vanessa shut and locked the door behind him.
When James left he took that whole reality with him. Vanessa and I didn’t discuss what had happened; we didn’t dissect or analyze anything. We simply went on enjoying each other’s company in the easy, platonic way we’d grown accustomed to. Watching James and Vanessa’s sweet, albeit atypical dance, reminded me of how far I’d come from those confused, exasperated attempts at sexual discovery in my youth.
I used to expect each new experience to transform me in some way, but they rarely did. Sex is an undoing, but it also abides by rules small and ordinary. You can’t experience intimacy without trust. You can’t know power until you’ve given it up completely to someone else. Living isn’t simply a matter of saying yes — it’s meaning it.