Transvestite swingers party: ‘We glam up and swing too – it’s perfect!’

With a make-up artist to transform men into glam ladies, plus a dungeon and five ‘playrooms,’ this is one transvestite swingers’ party guaranteed to go off with a bang

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by Mel Fallowfield |
Published on

Originally published 21 August 2012;

An industrial estate in a village on the outskirts of Shepperton, Surrey, seems an unlikely venue for a swingers’ party – let alone one for transvestites and their wives.

Transvestite swinger
Transvestite swinger

But, behind a nondescript brown door, there’s a new world to explore. Husbands, boyfriends, builders and accountants by day can don sexy dresses and receive a makeover, before relaxing in the candlelit bar or indulging in one of five 'playrooms' – including a 20-person orgy room and an eye-watering 'dungeon,' with whips.

The party – which takes place four times a month – is organised by 47-year-old former builder Jenni Sheridan – a transvestite whose real name is Simon. She set it up four years ago to combine her two loves – swinging and dressing up. She says: “It’s a safe place for transvestites to have fun – and, let’s face it, girls do want to have fun! I’ve been dressing up since I was seven, pinching my mum’s tights or pants. It still makes me laugh that, when I was 13, she asked if she could use some of my wardrobe space to hang her dresses. I kicked up a fuss, but I was thinking, ‘Hell, yes!’

'But, although I loved it, I felt alone – I’d drink with my builder mates every night to bury my desires. That was until I started looking on the internet 12 years ago and realised I was far from the only transvestite. I also loved swinging – I’ve never been the faithful type, so it made sense to combine my two loves.'

Jenni – who lives in Sunbury, Surrey, and dresses up as a woman five times a week – is helped behind the bar by her bisexual girlfriend Lou Wilson, 30. They’ve been together for two months.

Lou says: 'We met at the club when I was employed as a fire performer. We chatted all afternoon and I love the fact Jenni’s a transvestite. I find both Jenni and Simon sexy. We swing together, both wearing dresses!'

'Many transvestites take up to three hours to perfect their appearance'

The party – which is run by club Candygirls – costs £15 if you’re in a dress and £20 if you’re not, and kicks off at 9pm. But, before then, some guests start arriving to get their glad rags on – with the aid of beautician Busty, 25, whose job is helping to do their hair and make-up. This is at an extra cost, and many transvestites take up to three hours to perfect their appearance, donning sky-high stilettos, dresses and false lashes.

'I love working here,' says Busty, who’s single. 'I’m into swinging – I first went on my 16th birthday – and when I discovered this night, I thought it was a great idea. I love putting make-up on men and enjoy helping them out. Sometimes, they’re nervous if they haven’t been before.'

Roberta, 56, from Ashford, is having her nails done. She works in IT, has been married for 29 years and has been cross-dressing as a woman since she was eight. She insists her wife is accepting and sometimes joins her at the club – although she’s at home tonight.

She says: 'I’ll kiss and flirt with the other girls, but nothing more. I like the S&M "dungeon" room, which is equipped with manacles and special furniture – although my wife complains about the whip marks on my bottom!'

Cross-dressers Brandy, 60, a builder, and Donna, 37, who works in management and has been married three times – although she’s currently single – are among the first to arrive. They’re not a couple, but have known each other for 15 years. Brandy started out as an 'admirer' – someone who’s attracted to transvestites.

Transvestite swinger

Brandy says: 'When I was 25, I saw a drag act and I found the artists fascinating. Then, a few years ago, I realised I was missing out, so I started dressing up, too. I fancy women and men in dresses and I have a very supportive long-term girlfriend, who’s happy with me coming here and even having sex – she knows I’d never run off with a bloke in a frock!'

They’ve certainly both come with sex in mind – and even have condoms tucked into their garter belts. Donna says: 'Sometimes, I’ll have sex with different people – five or six times in a night.'

By 11pm, the party is hotting up – there are more than 100 people, ranging in age from their early 20s to over 70s and with jobs from ex-army officers to corporate financiers. 'Admirer' James, 26, who’s an accountant, says: 'I can’t explain my fixation and I’ve never told anyone. I’m 100 per cent straight and I don’t want to dress up, but I fancy transvestites and have slept with a few. I’m open to suggestions tonight.'

There are also a handful of married couples – one, who didn’t want to be identified, say: 'We like swinging, but we come here as much for the social occasion. There’s no pressure to do anything and, if we do swing with other couples, we stick together.'

In a 'playroom,' transvestites Yoko, 55, an engineer, Joanna, 66, who’s retired from her corporate finance job and 'admirer' Dave, 58, are having fun. It’s Dave’s first time and Yoko and Joanna are up for sex with an 'admirer.'

Meanwhile, in the 'dungeon,' there’s a huge Dodge Jeep for the 'dogging experience,' where people have sex in the car while others watch. One transvestite in laddered tights, who’s built like a rugby player, says: 'I was getting down to business when they strapped a naked woman to the Jeep – it was very distracting!'

An hour later, Yoko’s in the smoking area, where she lifts up her skirt for a spanking – three participants oblige, and there’s applause from others having a burger from the food stand.

At 4am, the party is still in full swing. All the 'playrooms' are occupied and there’s plenty of action in the 'dungeon.' Jenni says: 'Everyone is happy – they can let their hair down without any judgement. And they leave with a smile on their face.'

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