Correspondent: Several people, including existing partners, who wanted to know how my date with someone new had gone.
Date: A few weeks ago.
Content warnings: This letter is more explicit than the other NSFW ones have been. As you read, please keep in mind that I am a masochist and I actually enjoy this sort of thing, and that my date1 and I had previously established safewords.
For a lot of people, trust is passive. It shows up, unbidden, after enough time has passed without anything going dreadfully wrong.
That’s not the only way. You can decide to trust. You can give someone power, and then watch to see what they do with it. Maybe they’ll use that power to hurt you. Maybe they’ll take very good care of you.
Sometimes they do both at the same time.
It was our second date. I was euphoric after the first one. Our sexual chemistry, powerful from the start, had surged as we stoked it with dirty texting.
For our next date, I want you to choose a sexy outfit which is not trying to tease, or trying to emphasize some things and hide others, or trying to draw attention to the outfit itself. Rather, I want you to choose an outfit which sends a message: it should say that you are wearing any clothes, and therefore could have chosen to cover up, but you instead chose to expose yourself for my pleasure, holding nothing back. This is not an outfit to be torn off, because there is no need to tear it off - everything is visible, everything accessible, everything available to my control. The outfit is, metaphorically, the platter upon which you offer yourself up to be taken in your entirety.
I worry that I will cause a riot if I wear that in public and so when you first see me I might appear more demure -- but you’ll know that beneath the surface, I’m already yours, and you’ll prove it soon enough.
If you feel daring, I am particularly turned on by the prospect of you showing up wearing only a trenchcoat over such an outfit.
Some of the trench coats I’m finding online are nearly as scandalous as what they’re meant to hide. You’d probably like that too.
Not long before our date:
okay, so -- please imagine that I’m asking you this in a very subby way, looking up at you through my eyelashes -- may I please have some instructions? I need to pack very soon and there’s the MICRO trench coat which barely does its job but is very sexy or the NORMAL trench coat which I could actually wear outside of a strip club
[Location], 5 pm sharp at the front gate, micro trench coat, slutwear, and nothing else.
that’s terrifying
but I will do this
I’m good at managing anxiety. The key is to think about the scary future event exactly the right amount: enough to prepare for it, to make it go as well as it can, and no more than that. This is how I approached, say, childbirth. “Well, the baby’s going to come out, one way or another. I want to live through that once per baby, not a hundred times, so now that I’m prepared I will just stop thinking about it.”
This works very well for me. (It does not work for most other people. A few early therapy clients squinted and frowned at me when I suggested this, and I quickly learned to teach more accessible strategies instead.)
My brilliant technique utterly failed me in this case.
I could not stop thinking about this date. I thought about it in bed at night, in the morning when I woke up, and every time I took a break from work.
I reread his texts obsessively.
I visualized what could go wrong, out in the world in my micro trench coat. The chain of logic was always fuzzy, but it often ended with a stern police officer, or a judge for some reason, asking, “Ma’am, what happened to your clothes?”
This was ridiculous. I knew it was. But I’m the sort of person who has solutions and remedies for a couple dozen likely problems in my backpack. I believe in defense in depth. I plan ahead, and then I have layers of contingencies.
I do not go out with nothing. I’d be … defenseless.
Which I guess was the idea.
On the afternoon of the date, I put off preparing as long as I could, but finally I got dressed – sort of. I snapped a selfie in the bathroom mirror. I put my wallet, keys, and phone into the pockets of my coat.
Then I sat on the arm of my couch and tried to figure out exactly what time to call the Uber.
It wasn’t a long drive – less than ten minutes – and I very much did not want to arrive early. The idea of standing out on the street in my micro-coat, the wind tickling my bare labia in my crotchless panties, WAITING, was excruciating. I wanted to arrive exactly on time.
On the other hand, I knew that Uber was prone to being optimistic in its estimates. But how optimistic? I wasn’t sure. I’d never paid that much attention. I was always just early.
When the app predicted that I would arrive at 4:57pm, I poked the button, hoping I’d guessed correctly.
Then I sat and waited with growing horror as the app told me “Just one more minute! there are plenty of cars in your area! We’ll match you very soon!” and then finally said “Your car is eight minutes away!”
I was definitely going to be late. I just wasn’t sure how late.
I sat there, stewing in my own gastric and vaginal juices, not wanting to go down to the lobby of my building too early. The lobby is a high traffic area at that time of day, and I couldn’t even sit down without exposing myself.
When I finally took the elevator down, I could hear voices around the corner. It sounded like the building’s maintenance guy, Jesus, talking to another resident. I ducked into the mail room to hide. I was not ready to face Jesus.
The car arrived. I darted outside and clambered into the Uber, carefully arranging scanty scraps of coat under my pussy. It felt impolite to leave the telltale stain of a scantily clad slut on the seat of his car.
The driver was very professional and did not ask if I was on an outcall.
I texted my date, my fingers shaking. Expert anxiety-manager, indeed.
Uber is saying 5:06pm. Anguish! I’m very sorry. I currently predict I will be appropriately contrite several times tonight.
6 minutes late, oh dear… keep an eye on that number, you’ll need to remember it later
Oh noooo
I clutched the phone in my hand and stared out the window, willing the lights to turn green, the traffic to move, the car to fall into a sinkhole to the center of the earth.
I arrived at 5:07pm. He was standing there, waiting, as I extracted myself from the car ass-first so as not to give the driver an eyeful. The car pulled away. My date grabbed me roughly by the lapels of the coat and he kissed me, hard. Normally I would want to melt into a kiss like that but this time it was just blocking the apology from falling out of my mouth.
“I’m so sorry I’m late!”
“You know what’s worse? You’re still not even at the front gate. Clock’s still ticking.”
I squeaked and tried to run for the gate. He held me for a few more seconds, waiting until his phone clicked over to the next minute. Only then did he relent, laughing, and let me in.
“Eight minutes,” he said.
I knew the site where we were meeting, and I had guessed in advance where he was going to take me. I had imagined we’d turn left, go between the buildings, go in and up and around…
But no, I was wrong. He steered me by the back of the neck toward a different building altogether.
“We’re going in there?”
“What, are you afraid someone might see you, walking right in the front door?”
I squeaked again. He laughed again.
What was I afraid of?
Mostly, I was afraid of other people seeing me at a disadvantage, shaking and vulnerable and naked – and worse, in a context where most people had on their cool, composed, and professional masks. Everyone else was there to work. I was there to – I didn’t even know, yet, I just knew it was going to be raw and animalistic and utterly out of place. It was private, I only wanted him to see, but he was marching me in the front door and I was letting him.
We went inside. He kept steering, up the stairs and around the corner. People saw us, but they didn’t really look. They were busy working, sitting on low couches. If they’d glanced up, they would have seen right up my scanty coat, to the tops of my stockings and beyond.
He opened a door into a tiny office. He drew me in, closed the door, pinned me to the wall, and kissed me roughly again.
“We’re going to fuck in here? There are people working right on the other side of that door!” I hissed.
He smirked. “You’re about to learn a secret.”
He popped open a hidden panel and revealed a ladder going up into the darkness, and then he gestured for me to go first.
Well, if the people on the couch could have seen up my coat, he was going to get an especially good look as I mounted the ladder ahead of him. As I climbed, slowly and awkwardly in my heels in the dark, he encouraged me by brushing his fingers under my coat.
At the top of the ladder I found…
A very unsexy attic. It had all the usual attic features: exposed joists and rafters, dark dingy corners, loads of sawdust. Was this where we were going? I clambered to the top and moved to the side to make room for him.
He called up. “Don’t step on the floor, it’s not meant for that, only stand on the joists.”
“I’m wearing stiletto heels!”
“Mmm. Sounds tricky. Don’t mess up.”
After dismounting the ladder he again took the lead. He offered me a hand, but I couldn’t afford to take it, I had to bear-crawl on all fours to keep my high heels on the narrow wooden joists. He shone a flashlight so I could see where I was going, or maybe just to enjoy the view of my trench coat failing at its only job.
He walked, I scrambled, and soon he pushed through a gap in a black fabric wall. I pushed through behind him, stood up, and blinked.
It was a dimly lit chamber with a proper floor, several couches around the edges, and a small stone coffee table in the center. There were fluffy rugs on the floor and blankets on the couches. I recognized his laptop and speakers set up in the corner. He likes to work to a soundtrack.
I only had a moment to take all that in before he pushed me up against a chimney and growled at me to take off my coat. I untied the wide belt, fumbled with the buttons until they gave way. I let the coat fall open, exposing the cupless bra, the crotchless panties, the garter belt. Little scraps of lace, covering nothing, exactly as ordered.
He released me. He slipped the coat off my shoulders and tossed it to the side.
“Turn around. Slowly.”
I did. He grunted appreciatively.
“Good girl. Well done with the assignment. The clothing part of the assignment, anyway.”
He shucked off his own jacket and shirt. I was too nervous to appreciate the view.
“Now go and lie down on the table, face up.”
The low table was about as long as I was tall. It fit me perfectly, my feet on the floor and my arms above my head. The surface of the table was cold against the bare skin of my back and my ass. Once I was in position, he bound my ankles to two of the table legs, and then bound my hands together and tied them to the table legs at the other end. I was stretched out, exposed.
It feels normal to me, in sexy situations, for my breasts and my pussy to be on display, but this was far worse. He had unfettered access to my neck, my underarms, my ribs. These are my tender spots, and I had no way to protect them. I was still cold, but I could no longer shiver, much, because I was locked in place. It was a relief, almost, to have all my agency finally stripped away. My decisions didn’t matter any more. It was all up to him now.
“Now… do you remember how late you were?” He had his phone out.
“Eight minutes. I’m so sorry.”
“Correct. You’re going to pay back those minutes now. This is an eight minute timer.”
He laid his phone on my torso, right below my breasts, and tapped the start button.
And then he raked his fingernails, hard, slowly, from my elbow to my waist on my right side. Every inch of the long raised line blossomed, sharply stinging, and then gave way to the more intense sensation of the next inch. I squeezed my eyes shut and softly wailed. He walked around and restored my body to symmetry, making a matching line on the other side.
It turns out there are over a hundred separately addressable areas of sensation on the neck and torso of an adult human female. My tormentor helped me identify them, one agonizing scratch, pinch, and bite at a time. As he worked me over, I tried to keep myself contained and under control. Not too loud. Not too messy. I wanted to take it, take all of the pain. It was only eight minutes. I can do a lot of things for eight minutes.
He raked my skin. I tried to focus on the music, but it was hard to follow the melody.
He dug his thumb hard into the nerve bundle at my groin. I tried to take a deep breath, but he interrupted it with a slap to my breast.
He twisted my nipples, hard. I tried to look up, into his eyes, but his head was backlit by the overhead lights, and he was only a silhouette. I couldn’t make eye contact, but I could still do my best to transmit subbiness and desperation and longing.
And then I stopped trying anything at all, and just let myself sob, still quiet, but no longer contained and controlled. I floated, at one with the pain, constantly reshaping myself to its contours every time it shocked me.
The timer went off, startling me. He silenced it.
“Already?” I laughed. I had just started to sink deeply into trance.
The table was no longer cold. My body heat had warmed it. A dozen minor physical insults buzzed at the edge of my awareness, but the endorphins must have kicked in, because I felt whole and alive and extremely aroused. I arched my back, stretched my legs slightly wider, nestled my face into my own arm, and smiled with satisfaction.
I was impatient with the restraints, not because they kept me from protecting myself, but because they kept me from wrapping myself around my torturer. I guess he was impatient too, because it wasn’t long before he untied me and I got the contact I craved.
He picked me up and laid me on a low cushioned bench, positioned so he could facefuck me and finger me at the same time. I gagged and sputtered and took him in again, while he laughed with pleasure at how sloppy I was getting. He praised me when I did well, when I took him more deeply.
He tied me again to the table and spent several minutes tracing patterns on my skin with a carving knife, never breaking the skin. Psychologically, I was prepared for this. I knew, at a gut level, that he would never damage me in any serious way – but I was surprised by how intense the physical sensation was, how sharp it felt, how much of the pain of cutting can happen while the skin is still intact. I quivered, trying not to wriggle so much he’d slip. I pictured the knife stuttering on my skin, digging in, the blood welling and then dripping darkly.
This time I did not make it eight minutes. I cried. I used my safeword. When he untied me I curled into his arms and buried my face in his neck and let him hold me and pet me until my heart finally slowed to a steady drumbeat again.
When I was calm, we wrestled and fucked and snuggled, until eventually we were hungry. It was time to go.
We snapped a very smug, beaming selfie together, and then we clambered back out of the attic. He carried my coat in his backpack so I could focus on traversing the joists in my lingerie and heels, a little more nimbly and recklessly this time. I felt lighter in my body than when we arrived. I think he probably enjoyed the view even more the second time, with no coat to hide my bruised and scratched body.
Before we emerged back into public view, he gave me a snuggie to put on. Once again, no one at the venue seemed to notice that I was wearing a snuggie, stockings, and heels. They were in a flow state with whatever they were working on, or they were too polite to stare. We’d managed a completely private date in a semi-public place.
As we walked to his car, I realized that I had no resources at all. My wallet, my keys, and my phone were all in the pockets of my coat, which was in his backpack. It felt good to be so unencumbered. Just me, mostly naked, with only a blanket to cover me. That was all I had to manage. The rest was up to him, and I was profoundly content.
I trusted him, and that was right.
He revealed later that night that he’d expected me to be late, because he guessed correctly that I would not dare to be early. It’s hard to time an Uber, after all.
My date was John Wentworth. If you are female and would enjoy dates like this, you can ask John out at: https://fetlife.com/johnswentworth. Logistically, dates will be easiest if you can meet him in the Bay Area, but feel free to apply from other locations; he sometimes travels.