It was 2004, I was 28, and everything was breaking my way.
I lived in a huge loft on the Bowery with a roommate I rarely saw. I had a job I liked, making decent money, a big group of friends, and a social life that routinely kept me out until five in the morning. I was dating a hot DJ, seeing another woman, and hooking up with other people in between. I knew bartenders, promoters, writers, weirdos. I could walk into a party and know half the room.
Basically, I had no reason whatsoever to leave New York. Then my hand was forced.
Earlier that year, my friend Peter asked me to help with a business he’d started. I’d been selling a similar product at another company and began advising him informally, for free. Pretty quickly, he started making actual money.
Then Sequoia Capital got interested.
This was Sequoia fucking Capital – one of Silicon Valley’s most prestigious venture-capital firms. They were prepared to put millions into my friend’s company, conditional on me joining the company, which meant moving to San Francisco.
It was certainly flattering. I still said no.
Like most successful founders, my friend wasn’t taking no for an answer.
This was the major leagues. Opportunities like this don’t come along twice. Fate was calling.
Eventually, I blinked.
But I was suspicious enough to have a lawyer put together what may have been the most lopsided employment contract in Silicon Valley history: moving expenses, a great salary and, if they fired me, something like a year and a half of severance. My lawyer deliberately made it ridiculous, assuming it would come back dripping with red ink.
To his shock and mine, Peter just signed it.
After a big goodbye party at my loft, I packed up my life, flew to Oakland and got in a cab. On the way into San Francisco, I saw a sign announcing the population of my adopted new home.
793,700.
Oh no.
Somehow I’d never bothered to find out that San Francisco proper had about a tenth the population of New York. I started doing the math in my head and started to worry that replicating my debauched New York existence in a much smaller city would be a tall order. My worries were well-founded.
In New York, I’d been out six nights a week, surrounded by beautiful, interesting party people. In San Francisco, I’d get invited to a house party every couple of weeks where forty dudes seemed to be forming a defensive perimeter around the one hot girl. If there was fun to be had in that city, at that time, I couldn’t find it.
Making things worse, my professional life and my love life seemed intrinsically linked.
I couldn’t close anything. I was feeling pretty down.
Then I met Lindsey…on Craigslist.
Craigslist in 2004 wasn’t merely where you sold your futon or found a roommate. Its personals section had become a place for people with extremely specific ideas about what they wanted from strangers. I’d just learned this from Peter.
One morning he’d come into the office* even more fidgety than usual. He kept adjusting and readjusting his package.
*This was the mostly empty Sequoia Capital office in Menlo Park where we shared space with three delusional nerds with a goofy-sounding startup called “YouTube”. Really.
“Everything okay down there?” I asked when his furtive movements became utterly distracting.
He explained that he’d seen a Craigslist ad in which a young woman set out the fantasy she wanted to realize. Quite simply, she wanted to fall asleep and wake up with a penis in her mouth. And because Peter was spending an inordinate amount of his free time scrolling these sorts of ads, that penis wound up being his.
This Craigslist thing was a massive revelation for me. Obviously I knew women had kinks and weirdly specific fantasies just like guys do. What I hadn’t considered was the logistical advantage they enjoyed in actually making them happen.
If I posted on Craigslist that I wanted to fall asleep and wake up with a strange woman’s ass as my pillow, I’d probably grow old and die waiting for a response. A woman posts the inverse and, within an hour, can take her pick of willing participants.
Peter was living proof.
As soon as I got back to my place that evening, I cracked open a beer and had myself a good old rummage in the “W4M” section. That’s when I came across Lindsey’s post in which she carefully described the itch she needed scratched.
Ostensibly, she would come to my apartment with a bag of sex toys. I would remain fully clothed. She would not touch me. I would use the toys on her. Then she would leave.
She emailed me some pictures. If they were really her, she was the kind of woman I hadn’t seen much of since arriving in San Francisco. She was gorgeous.
90 minutes later, she showed up at my apartment at the foot of the Mission.
Lindsey was a fucking dime. Even better than her pictures. And petite. Certainly not the kind of person you’d expect to see with a heavy, bulging, hockey bag hoisted over her shoulder. I took it from her and was surprised by the weight.
I could tell she was nervous, so we sat around talking, drinking beer, and laughing for a while.
The bag sat on the bed like a third person in the room.
After about forty minutes of pretty G-rated conversation, each of us furtively glancing at the bag, I finally addressed it.
“Well, that’s a pretty big bag you’ve got there.”
She nodded then slowly unzipped it and began taking inventory, laying each piece of artillery on the bed in the order in which she wanted it deployed.
There were little bullet-shaped vibrators. Chunkier ones. Smooth insertables, ribbed ones, and an enormous, veiny, powered dildo that looked less like a sex toy and more like a leg of lamb.
You have to remember, this was 2004 – years before sex toys came with discreet little USB charging cables. Some of these things ran on the sort of heavy disposable batteries you’d use to power a camping lantern. I twisted one of these bazookas the wrong way, and ejected a train of C batteries from the girthy shaft. They hit the floor in a quick succession of heavy thuds. Oops.
As she laid everything out, Lindsey explained what each one was for and what she liked done with it. I picked them up, inspected them, turned them on, listened to them buzz.
All while we were still basically having a polite conversation.
Except Lindsey was getting increasingly turned on. She started rubbing her thighs together like some horny grasshopper. At some point I looked down and realized a huge wet patch had spread across the crotch of her jeans in anticipation of what was about to happen.I guessed this was going as she’d hoped.
We reviewed the rules one last time. I stayed dressed. She wasn’t there to reciprocate. A deal was a deal.
Then we started working our way through the inventory.
The whole thing was surprisingly methodical at first. We’d try something small, then something more powerful. Something external, then one of the insertables. Sometimes two toys in combination. If something worked particularly well, that went back into the rotation.
And as the night wore on, the polite, slightly nervous woman who’d arrived carrying the hockey bag disappeared.
The toys got bigger. The vibrations got stronger. The pauses got shorter. Her orgasms seemed to build on one another, and every time I thought we’d reached the natural conclusion of the evening, she’d recover, look over at the remaining arsenal, and indicate that apparently we were not done.
Meanwhile, she was getting louder.
And louder.
By the end, after a couple of hours of steadily escalating battery-powered mayhem, Lindsey was screaming the fucking place down.
And then, just as advertised, she packed up her arsenal and left.
I never heard from her again.
As it turned out, Lindsey was the bright spot of my San Francisco adventure. The job I’d uprooted my life for quickly went to shit, and within a month or two I was heading back to New York.
But I wasn’t going back empty-handed.
They’d signed the contract.
So I returned to my enormous Bowery loft, my friends, my nightlife and the city I should never have left in the first place – with my severance money secured and one very strange, very loud memory of the Bay Area.
