Undercover: The Adventures of a Real Life Gigolo

This was it. My Day of Reckoning. My first time of making a go of the escort work and I was damned sure it showed on my face. I bit my lip and forced myself to look up at my fellow travellers, like what I was about to do was the most normal thing in the world.

I realised I was staring straight at a woman. I’d been so caught up in my thoughts I hadn’t even registered her. I turned my head upwards to view the ad above her head. It told me which number to ring if I wanted to hire some air-con. I slipped a glance back at the girl. She was a couple of years older than me and was engrossed in her copy of Metro. She had dark eyes and smooth shoulder-length brunette hair with a fringe, and was better than average looking. An English rose.

You could, couldn’t you?

That was the crux of the matter. I slipped a glance at all of the women on the seats around me and weighed up whether I would shag them or not. And wondered whether any of them looked anything like Jenny.

The tube drew into Shepherd’s Bush and I got up. I swallowed back my nerves. I didn’t want to think too much about what I was about to do. I turned left out of the station until I reached Jenny’s street.

The further I followed the curve of Jenny’s road, the seedier the terraced houses became. Her address had all the hallmarks of a cheap multiple occupancy. An unkempt front garden that nobody took any responsibility for. Check. Tatty labels taped next to the doorbells. Yup. Makeshift curtains at some of the windows. You bet. Rob had so had the better deal.

This was my very last chance to split. I braced myself and pressed Jenny’s doorbell.

‘Luke?’ A tinny voice came through the intercom. ‘Come on up.’

I pushed open the front door, crossed the scuzzy hallway and mounted the stairs two steps at a time while being careful not to slip on the worn floral carpet.

Jenny was waiting on the first floor at the entrance to her flat. She was dressed in an oversized navy jumper turned back at the cuffs and a calf-length striped cotton skirt.

‘Gosh, you’re a good-looking young man,’ she blushed.

‘Better than Rob?’ I teased.

She looked down at her slippered feet. I cursed myself. Maybe she didn’t want to be reminded that she’d done this before and bottled out.

I was as much trying to relax myself as her. It wasn’t as if Jenny was ugly or anything. But she wore no makeup, and looked as if a harsh life had carved itself into her face. Her hair was short and black with white streaks and her colouring was mixed race, though I couldn’t for the life of me make out where she came from. Yeah, I could do her.

‘I liked how you sounded on the phone,’ she said.

‘What, startlingly handsome?’

What made things difficult was that she was closer to my mother’s age—she was in her forties or fifties, I couldn’t be sure which, and that was a whole new ball game altogether. That kind of business hadn’t been in either my or Mark’s head when we’d decided to get into this lark. We thought we’d be inundated with requests from hot young chicks, desperate for no-strings sex, or busy career women without the time for a relationship. I still hoped we would.

Jenny’s flat was sparsely furnished, aside from piles of unopened boxes. They were everywhere, and getting to the sofa in her living room was like wandering through a maze.

‘Would you like a cup of tea?’ she asked.

‘Yes please,’ I said, and stifled a laugh. Within a couple of days of getting here I’d realised that that was the Brits’ answer to anything.

She went out to the kitchen, and I sat down among the cushions on the seen-better-days sofa, stretched out my legs and tried to make myself at home and calm the rising sense of dread.

An ancient tabby cat appeared at my feet from behind a box tower and rubbed itself up against my ankles. It was followed by a younger one, which settled itself on the worn rug in the middle of the room and licked its paw, watching me as if it were sizing me up.

Jenny came back into the room. This was going to be tricky, I could see. It was one thing to talk about sex with my mates down the pub or kicking a ball around in the park. It was going to be quite another to switch my brain into a gear that could talk about such stuff with someone like her.

And then I remembered what I’d advised Rob. To ‘be every woman’s dream’. To do what he always did but just to be a bit more of a gent as he went about it. That wasn’t bad advice, even if I thought so myself. Mind you, it wasn’t as if he’d had the chance to test it out.

Jenny had two matching floral china mugs in her hands, and handed me one with a hesitant smile. She sat down a few inches from me.

‘Thank you. That’s a pair of handsome cats you’ve got there,’ I said.

‘Do you think so?’ she blushed, as if it was a long time since anyone had complimented her on anything.

We drank our tea for a few horribly silent moments, until I placed the mug down beside my feet and gently took Jenny’s hand in mine. She gave me a bashful smile, the lines around her eyes creasing a little, and funnily enough taking years off her. She reminded me of some scrubland creature you could only get up close to if you took it step by step, real quiet and slow.

No wonder Rob hadn’t even got to first base.

I wasn’t quite sure what the next move should be. But at least Jenny and I knew why I was in her home. And though I couldn’t quite see it now, clearly she had a thread of steel running somewhere through her to pick up the phone and make the call in the first place. And not just once. She knew what she wanted, even if the challenge remained for me to move on from the friendly small talk without scaring her off.

‘Shall we go to your bedroom?’ I all but whispered.

Jenny bit her lip and nodded and we rose to our feet together. Still holding her hand, I remained a step behind her and followed her around the wall of boxes into a room off the hallway.

It was a bedroom only in name. There were more boxes but not even a mattress. Just sheets and a duvet and matching pillows set out on the carpet in the corner of the room. In place of a wardrobe were a couple of open suitcases draped with her clothes.

Jenny must have sensed my disquiet, much as I fought to hide it.

‘It’s not as if I get much sleep anyhow. I work all hours.’

‘It’ll be fine, Jenny,’ I replied, and squeezed her hand as I stared down at her makeshift bed and wondered how we’d get from here to the actual sex. I chewed on the inside of my cheek, then took a deep breath and turned to face her.

‘Would you like to sit with me on your bed?’

She nodded and I made an ungainly move towards the duvet and trusted she’d follow my cue.

Head in the right direction and somehow we’ll get there.Surely.

We were sitting beside each other now. I threw her a tight-lipped smile as I gave her the once-over and worked out a plan of action. I didn’t say anything but reached out and took hold of the hem of Jenny’s jumper and raised it a couple of inches.

She looked back at me with her deep, dark eyes for a beat, then took the hint and stretched her arms behind her back and drew the jumper over her head. She shook it out, folded it and placed it on top of the pile of clothes in one of the suitcases. If we kept at this speed, the hour would be up before either of us got naked. Maybe that wasn’t the worst that could happen. For either of us.

Jenny ran her fingers through her hair. Removing the jumper had taken pounds off her. She wore a short-sleeved cream blouse. I still had my shirt on. Which meant that we were sort of on the same page.

‘I tell you what,’ I instructed as I reached for my own top button, ‘I’ll undo my shirt the same time as you undo yours. Okay?’

Jenny nodded in response but she still didn’t say anything. Her fingers fiddled with the little button at her throat and the cloth slowly parted. Her fingers dropped to the next in line but she kept her eyes from mine the whole time.

When she’d finished, her blouse was open and I could see her white bra beneath, but her head was still down and she was looking at her hands in her lap like she was ashamed.

I’d peeled my own shirt off without thinking. That’s just how it was back home. The climate made it easier to remove your clothes, not that you didn’t have to mind the sun. I’d been told about the Page 3 girls the Brits had in their papers before I came, but the people here didn’t seem like that at all. They wore layers because the weather changed so often. It had to be a really hot day by their standards for them to relax and strip down, and then it was like they did it with a real relief. Here with Jenny, I could see that it was vital that I respected a client and how comfortable or not she felt at every stage. The way to do that was to mirror her speed of undressing—though to take care to chivvy her along if I had to.

There was nothing I could do, it seemed, but spell out to Jenny what was needed and only hope that I didn’t scare her. I feared that if I went at her pace we’d never get anywhere. And the longer it took, the more gruelling it’d be for me too.

‘Jenny, slip off your skirt and underwear, will you, and while you’re doing that I’ll get myself ready.’

There. I’d said it. I’d made it clear what came next and there was no going back. I pulled off my jeans and my Calvins, and fished in a pocket for a condom. By the time I’d turned back towards her she was stretched out and waiting. She’d taken her blouse off but kept her bra on.

I realised I’d had nothing to worry about. Jenny wasn’t bad for her age, I could say that. She had the soft edges I’d expected, something to hold on to, which wasn’t the type of woman I was used to, but wasn’t something that repulsed me as I’d feared either. I was still going to have to give myself a helping hand though. She hadn’t stirred me that much.

Jenny’s eyes were fixed above my waistline all the while I nestled down beside her. I wrapped my arms around her and held her close for a few minutes to put her at her ease. One of her fingers drew a little nervous circle round and round on my chest.

‘I’m just going to protect myself,’ I whispered as I pulled myself gently away from her, ‘and then I’m going to make love to you.’

Just then I realised that the words I used and the way I spoke were as important as the sex act itself to Jenny. She was as nervous as hell and it was up to me to take account of that and make things good for her. But it wasn’t just about Jenny. Whatever happened after this, this was my first professional job. If I thought too much about that, I knew my performance would suffer—and Jenny’s enjoyment. Yet if I forgot I was providing a service, it wouldn’t be fair on her either. It was a fine line to walk. I fixed my mind back on my client. That was surely the key.

I took as much care as any guy can when he’s jutting into a woman. Jenny gasped and clung tight to me as my body lapped and battered against her then juddered to a halt.

I lay against her saying nothing for a couple of minutes and she stroked the back of my head.

‘This isn’t my first time, you know, Luke, though I’m somewhat out of practice,’ she said in a quiet but matter-of-fact voice.

That took me by surprise. It was as if the sex had broken her silence. I propped myself up on one arm to look at her lying there beside me.

‘Don’t diss yourself, Jenny. You were fine,’ I lied. She’d barely moved the whole way through, though it wasn’t as if I’d been expecting some sex-tiger anyhow.

‘I used to work in nightclubs, y’know. My boyfriend owned one and was a big promoter too. But that was a long time ago,’ she said with wistfulness. ‘It didn’t work out. And that was that. There’s been no one since.’

She made it sound so final. Which I suppose it was. Life had been hard.

‘But you’ve nothing to worry about, Jenny. You’re a lovely lady.’

I wasn’t lying this time. True, she needed more experience and a whole boost to her confidence, but she didn’t seem to have any edge to her. She was genuinely nice.

When Jenny spoke again, it was as if her mind was on another track and she sounded like she was somewhere else in her life.

‘And after him I fell ill, and by the time I was back on my feet, all my hours were taken up making ends meet. Still are. I haven’t had the time for anyone since.’

I sat up, my legs stretched out across the carpet.

‘So, it was quite something to call me and Rob out, then. You could have put the money towards a new bed.’

I regretted it as soon as I’d said it. Jenny looked at me, pained, and I wanted to swallow the words right back. Shit. It was none of my business. I’d stepped horribly out of line. But Jenny, to her credit, collected herself admirably.

‘I saw your advert, Luke,’ she said, stroking my arm with boldness, ‘and it reminded me of all I’d been missing. Not just the sex, but someone else’s touch and the tenderness. You’ve given me that this evening. It’s been lovely.’

‘My pleasure,’ I replied. And meant it. She hadn’t been what I’d been hoping for, but in a small way I felt proud. I’d helped out someone who obviously needed it.

We slipped off the duvet and got to our feet. I hugged her, and as I did I checked my watch. She had ten minutes left and I still had to get dressed.

‘I’m going to have to be leaving shortly,’ I said as I picked up my clothes.

‘I’d like to see you again, Luke. But not for sex or anything.’

I didn’t get it. Hadn’t she just told me that it was the tenderness she craved?

‘I’d like just to meet you for tea, and for us to talk, that’s all. Like I did with Rob? I’d pay you for your time. Isn’t that what escorting is about?’

‘Yes, but…’

Jenny held up her hand to stop me—‘Wait a minute’—quickly pulled her clothes back on and left the room. I got dressed. She returned a few minutes later with a wad of notes as I was buttoning up my shirt. She counted out the £150 onto a box lid and I scooped it up and folded it into my wallet. The easiest money I’d ever made.

I thought of how Rob had felt he’d won the jackpot. Which he had, for a mere chat over a coffee. Wasn’t what Jenny was now offering me the simplest part of this job? But it didn’t seem right.

‘I’d just like to see you for half an hour, before I go to work?’

‘Look, Jenny, I can’t have you pay for just that.’

‘But you’re not going to meet me for nothing, are you?’

She had a point. I was running a business, wasn’t I?

‘Well, no… But even so.’

Jenny took my wrist in her hand, and spoke without looking in my eyes.

‘I won’t hear another word, Luke. I’ll give you fifty pounds. How’s that?’

And then I got the message. She needed to pay something. She might have been hard-up but she had no need of my pity.

‘It’s a deal.’ And just like that I had my first repeat customer.

‘So, she was a right little goer, was she?’ leered Mark when I met him later in the local. He had just returned from the bar with our two pints. He set mine down in front of me and grabbed a chair, and I looked down into the mouth of the glass and the deep liquid. I lifted the beer to my lips and took a gulp. I didn’t know what to say. Because Jenny was outside what either of us had imagined, that was for sure.

‘Well?’

Mark wasn’t going to let up. He was facing me across the table, and this felt like an interview.

I set down my glass and flashed a ‘don’t go there’ glare.

‘Oh, come on, Luke. We’re in this together, aren’t we? You can tell me.’

I cradled my jaw in one hand, the other wrapped around my pint.

‘Look, the thing is, you weren’t there with me in the room, were you?’

‘Oh, if that was what she wanted, she only had to ask!’ he grinned, before knocking back more of his beer.

I shook my head at him and chuckled. For a second.

‘God, Mark. Be serious. It wasn’t like that. She wasn’t like that, y’know.’

There was a glint of anger in his eye.

‘What, suddenly you’re Mr Professional Escort all of a sudden? After one paid lay. Don’t make me laugh.’

‘No, listen. I didn’t mean that,’ I pleaded. ‘It was just… Jenny, she…’

‘Jenny,’ he sneered.

I ignored him. ‘Jenny is just someone who needed a bit of TLC.’

I spoke into my glass and heard my own voice grow quieter. I looked up at Mark and I could see he was listening.

‘And don’t we all,’ I sighed.

Jenny was hovering outside the Starbucks in Piccadilly. She hadn’t yet seen me approach. Her feet were turned slightly inward, and she was focused on the paving stones in front of them. One hand gripped the other against her thigh.

‘Jenny, it’s lovely to see you.’ I touched her shoulder and she turned towards me, a huge smile lighting up her face. I hugged her and felt her body relax against mine.

I ushered her into the café and went and ordered coffees for the two of us. She said nothing as I placed them on the table in front of us and sat myself down, but there was an expectant warmth across her face.

‘So, I didn’t put you off ever seeing me again, then?’ I smiled.

‘Oh, no, Luke.’

A tinge of pale pink washed across her face.

I flicked a look around the coffee shop and to the milling crowds in the street outside. We couldn’t have been more anonymous. I might even be mistaken for Jenny’s son.

‘So, do you have family in London?’ I asked.

She fiddled with the handle of her cup, and shook her head.

‘I’ve got a sister but I’ve lost touch with her. I’ve been trying to track her down.’

She changed the subject. ‘And you? That’s not an English accent.’

‘No.’

‘Well, it’s not as if you’ll ever be alone in the Big City. There are plenty of Australians here.’

‘Yeah,’ I grinned back.

God, had I found that out. When I was out with Mark and our mates it was sometimes hard to remember that we were anywhere else but back home.

I switched the focus back to her. I was on her time after all.

‘You said when we last met that you’d be off to work after this.’

She nodded. ‘Yes, just round the corner. I’m a cleaner at a number of the clubs round here,’ she explained. ‘I spruce them up before they open, and afterwards when everyone’s left.’

Grim, tough work.

‘You see a different side of the city, then.’

She cocked her head at me. The words hung in the air. She didn’t want to talk about work. This was her break.

‘Tell me about yourself, Jenny. Have you always lived in London?’

That was the cue for her life story. It poured out. How she’d never been quite good enough. The rest of her family were teachers but she’d gone into the clubbing scene. And how when that’d fizzled out she’d ended up cleaning other people’s clubs. She just wanted to talk. Just needed someone to listen.

Jenny’s time was up. But it was she who made the move to go. She was the one who was racing against the clock. I, on the other hand, had plenty of time to kill until my evening shift at the pub.

She gripped the table as if ready to stand up. And then slipped back down in her chair like she had just thought of something.

‘Luke, I’ve got to go to work. And we haven’t had much time together.’

‘It’s flown by, hasn’t it?’

She reached into her shoulder bag and pulled out a small roll of notes and gathered them in her hand and scrunched them into my own in the hope that no one would see. I pushed my clenched fist and its contents into the back pocket of my jeans.

‘I’d like to see you again, Luke.’

‘Would you like me to come to your flat again?’ I fished.

She looked at me and pursed her lips. ‘When I said I wanted to meet you for tea, I didn’t mean it to be a one-off. I’d like to see you again. To talk, I mean.’

‘You mean here again? Like today?’

She nodded. ‘On a weekly basis. Before work, like today.’

I let her see me weigh it up in my mind, like I was working out if I could fit her into my busy schedule.

Like hell I could.

But at the same time I couldn’t help thinking that Jenny wasn’t what I’d quite bargained for when I’d decided to offer sex for sale. She clearly needed someone to talk to. A listening ear, then, was going to be another vital organ in this game.

A Bit of Give and Take

The joy of sex is that it’s not just about your pleasure. Consider the other person in the relationship and the benefits will be felt by both of you. As an ordinary guy, I know what guys tend to want, but having made my living as an escort, I’ve learned what brings the most pleasure to women too. Follow the tips through Undercover and it’ll be win, win for everyone!

1. Introducing yourself

So, you see someone you like the look of across a crowded dance floor or bar.

 Smile, go and say ‘hello’, relax and be friendly.

 Focus on them, find something to compliment, flirt with your words, eyes and hands.

 Guys, don’t talk about the latest football scores, mistake joke-telling for a GSOH, or try too hard to impress with magic tricks and the like.

 Girls, retain some mystery. Hold back on the life story and any problems you have. Find a mutual interest but don’t fake it; he’ll see right through it and it’ll sound desperate.

 The sooner either of you gets to talk about sex, the more up for it you’ll sound. You’ll certainly grab his interest!

 And if you get the brush-off? Hold your head up high, put it down to experience—and their loss—take a deep breath and live to love another day.

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