Credit: Amer Ghazzal/Alamy Stock Photo

Dangerous liaisons: A peep into the illicit world of adult dating sites

Sex has always been a big part of the internet, but as the Ashley Madison hack shows, it can be a risky business. We delve into an industry that offers everything from swinging to sugar daddies.

by Rachel Savage
Last Updated: 11 Mar 2016

From the very dawn of the world wide web, the internet has been used for sex - and not just the pornographic kind. Whether lusting after a one-night stand or looking for true love, it didn't take long for people to cotton onto the concept of going online to arrange offline liaisons.

But lately, with adultery-arranging site Ashley Madison hacked and 'swipe-right-to-like' app Tinder accused of commoditising dating, companies in the business of arranging encounters have been thrust, excuse the pun, into the spotlight. Is the industry facing a backlash of 12-inch proportions or merely ripples of discomfort from society getting used to more liberal ways of living?

It's mid-afternoon on a Friday and a dozen or so people are active on Heaven Social, the decidedly retro (think Facebook's first iteration) social network of Heaven Circle, a two-and-a-half-year-old company that throws 'elite' sex parties. A couple of chat boxes pop up.

'Hey there x/What are you doing in that pic? lol,' asks one half of a male-female couple. (Wearing a mask and brandishing a plastic sword as a fancy-dress assassin.) I explain I'm a journalist. They admit to being disappointed in their search for a bisexual woman to 'play with'. 'It's like picking a needle out of a haystack ... they may show some intention but it never leads to anything.'

Having an affair can put you in a precarious position (adultery street art by Banksy). Credit: Joshua Baker/Alamy Stock Photo

A man, who insists on Skyping to check I'm real, says he's had success arranging private offline encounters - and prefers Heaven to online competitors like FabSwingers and AdultFriendFinder. 'Everybody's a bit more refined, well educated, I guess,' he says.

For people into things that still aren't a topic of polite conversation, the internet is, unsurprisingly, brimming with possibilities. '(It's) played a huge part in the liberation of people of our generation,' says Heaven Circle co-founder Chris Reynolds Gordon. 'When you used to go to a club or a bar, no one had a badge saying that they were into certain things.'

So whether that's wife swapping or finding a wealthy man to fund you through university (more of which later), there will be a niche for you on the net. But how viable are these sites as businesses, particularly as many still look like they were created on GeoCities in the late 90s?

Reynolds Gordon, a champion middle-distance runner as a teenager, says emphatically that he runs the free site and its associated sex parties out of 'more of a love for it and (as) a hobby (rather) than a business'. (He refuses to divulge financials, or the details of a virtual reality camera he's spent three-and-a-half years fundraising for, which he claims will 'revolutionise the industry' when it's unveiled next year.)

There are fewer than 3,500 members on Heaven Social, around 15% of the people that have tried to sign up. That's partly down to an unashamedly prejudiced vetting process - photos have to show someone in 'good shape' and who claims to be under the age of 40. There's a quota for single men, to keep the male-female ratio in balance, and anyone who posts a 'dick pic' (ubiquitous in online dating, as any woman who has tried it will tell you) is deleted.

'If I was trying to monetise the site, I'd be taking every single guy that would want to send me money,' says Reynolds Gordon, who was once pictured with Russian secretary of state Pavel Borodin during a phase when he dabbled in diamond trading. Nonetheless, he admits the strategy helps sell tickets that cost from £50 to £150 for the parties he throws in LA, New York, Paris and London (a 1,200-strong event in Elephant & Castle in early September was billed as the biggest sex party the country had ever seen). Elitism is 'more valuable' he says, 'because people want to be part of that'.

Killing Kittens is also infamous for only accepting 'beautiful people' to its events. The company has gained widespread media coverage over its decade-long life, as founder Emma Sayle's charity dragon boat racing group The Sisterhood very briefly counted Kate Middleton as a member. It's only ramped up its online strategy recently - and, unlike its rival, uses a 'freemium' model where paid members of The Litterbox (a far slicker-looking network than Heaven Social) get to send direct messages, and other such perks.

Subscriptions, which cost from £10 a month for 'Silver' to £100 a month for 'Platinum', have grown to around 20% of its 45,000-strong user base since they were launched in April, Sayle says. The company's total monthly revenues, she says, have risen 250% in the last year to around £90,000. They're currently split 50/50 between the social network and the events, which range from £30 for a single girl to £450 for a couple's ticket, although online 'will take over offline in a couple of months'.

Dark pleasures: one of Killing Kittens’ 'elite' sex parties

Sayle says she has doubled her staff to six in the last three months and that the online growth 'has massively enabled us to launch internationally'. Outside the UK, Killing Kittens parties have been held in Sydney, Melbourne, LA and New York and others are lined up in the Gold Coast, Miami, Toronto, Hong Kong and Singapore.

Other 'swinging' sites target the masses. (Swingers Date Club) claims to be the largest, with more than three million members in 50 countries. Nonetheless, even with increasingly liberal attitudes to orgies and the like, it remains a relatively niche market.

Another business not yet deemed dinner party material is SeekingArrangement. Founded by self-confessed 'nerd' and MIT physics graduate Brandon Wade, the Las Vegas-based site allows 'sugar babies', predominantly young women, to find 'sugar daddies' or 'sugar mommies', who will spoil them financially and even fund them through college.

Wade is well-versed in countering the inevitable argument that this is essentially escorting or prostitution. 'From a standpoint of a prostitute, a client is a client. There's no emotional connection, there's no chemistry,' he says. 'But I think a sugar baby on SeekingArrangement is looking for that special someone. She wants a wealthy boyfriend. Society has an issue bridging that gap ... even though in my mind it's actually a very clear line.'

Wade also has WhatsYourPrice (850,000 members), where men can buy dates with women; MissTravel (615,000), for 'generous' people to pay for holidays with 'attractive' partners; and OpenMinded (150,000), for people to meet others in non-monogamous relationships. SeekingArrangement, is the biggie, though: five million members, 30% outside the US, and available in nine different languages. It consequently pulls in 85-90% of Wade's annual revenues, which are forecast to grow from $25m-$30m this year to $50m in 2016.

But there is good reason to cast doubts on those kinds of numbers. Earlier this year, SeekingArrangement said US student members had increased 42% to 1.4 million in 2014. That would mean 6% of all America's 20.3 million college and university students were on the site. But the highest number of new sign-ups in the country was 425 from the University of Texas, which would still represent under 1% of its entire student body, according to number crunching by news site Jezebel.

It is possible that sugar daddies, who pay £35-£50 a month, are spoiled for choice and the ratio of men to women on Wade's flagship site is indeed one to five - the sugar babies are the ones with the financial incentive, after all. But he does admit there are 'escorts, prostitutes, people soliciting, people trying to hire models for their modelling agents, webcam girls trying to solicit clients to their webcam sites and Nigerians trying to scam lonely old women to part with their money,' on the site. He insists, though, that scammers and fake profiles only account for 5-10% of the total.

Those eyebrow-raisers won't surprise anyone who's been following the fallout from the Ashley Madison hack. Annalee Newitz, a journalist at Jezebel's sister site Gizmodo, analysed the roughly 37 million leaked user details from the affair-arranging site. And she estimated only around 12,000 of the 5.5 million female accounts belonged to actual, real-life women. You almost feel sorry for the millions of wannabe-adulterous men talking to fembots. Not so much for its now ex-CEO Noel Biderman nor its dead-in-the-water London IPO, which would have reportedly valued parent company Avid Life Media at $1bn.

Wade said in late August his sites' weekly revenues had fallen 15% since the Ashley Madison data was dumped online, as people stopped renewing memberships. It's not clear how many sugar daddies were also adulterous, but even a non-cheating, entirely consensual arrangement isn't yet socially acceptable on either side of the Atlantic. Swingers aren't too keen on revealing their identity either - online most seem to use pseudonyms and many only post body shots or blur out their faces.

Even at the vanilla end of the spectrum, online dating suffers accusations of commoditising relationships and women, who often suffer the aforementioned onslaught of douchebaggery and dick pics (the latter is also prevalent on gay app Grindr, although arguably more welcomed there). None is feeling the heat more than Tinder, which was recently the subject of a 5,000-word laceration in Vanity Fair that labelled the three-year-old app, which has more than 50 million users, as the cause of a 'dating apocalypse'.

Didier Rappaport, the 60-year-old French founder and CEO of Happn (like Tinder, but with a timeline of users you've been within 250m of, rather than being forced to choose instantly via swiping), is highly sensitive to such criticisms too.

'Technology is changing the world and it is true for the dating industry,' he says at the start of our conversation. He denies being 'a hook-up help', describing his app, which has notched up six million users since launching in March 2014, as trying 'to provide our users with an easy way to meet people around them.

'Roman Orgy' by Vasily Alexandrovich Kotarbinsky (1849-1921): there’s nothing new about sex parties. Credit: Heritage Image Partnership Ltd/Alamy Stock Photo

'Today, people first have sexual relations and maybe then they will find love. It's more a question of cultural change, social change, than technology will change the things,' he then argues.

Dr Bernie Hogan, a research fellow at Oxford University, sees a 'misdiagnosed backlash' that shouldn't just be aimed at Tinder. 'It's the creation of the social media self,' he says. 'We're not going to a bookclub to find somebody, we're not getting recommendations from our friends ... Online dating does create a shift towards individualism.'

It's surely a two-way thing. Online businesses are responding to more liberal, individualistic societies. Simultaneously, they enable and open people's eyes to things they wouldn't or couldn't have done otherwise, be it an orgy or a one-night stand.

Meanwhile, founders, wherever they are on the encounters spectrum, are cognisant of the need to get it right for women. Sayle markets herself as a woman running female-friendly sex parties and has introduced women-only talks and drinks events. Reynolds Gordon has his single men quota. And Rappaport insists they have designed Happn to make women feel 'secure' and 'comfortable'.

Wade, for his part, tells me more than half of a sample of female SeekingArrangement users described themselves as feminist - 'feminists who own their own body, sexuality and are extremely comfortable with using that to get whatever they want.' He continues, 'In a sense I feel the website actually empowers feminists.'

Sayle, who isn't interested in sex parties herself, is more blunt about her industry. 'It's much more socially acceptable for girls to go out and explore, but we're still not even anywhere near the level guys are. If they're single and shag around they're legends. If girls are single and shag around they're sluts,' she says matter-of-factly.

The online encounters industry is unlikely to achieve gender equality any time soon - there will be a surplus of horny, heterosexual men for the foreseeable future. But businesses with happy and unharassed straight and bisexual female users are surely more likely to be sustainable - especially as any hack would show more of said users are actually real. And it's not a stretch to think that the more female-friendly ones will be the first to pass that all-important dinner party test.

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