‘It was deadly. I slept with two sisters.’
‘Please tell me it wasn’t at the same time.’
‘God no, Phoebs. One after the other.’
‘Yes. That makes it much better. What about Sandra?’
‘You were right. She wouldn’t sleep with me on the first date, and it was a shite date anyway. All she did was talk about her bloody cat. Nice arse though.’
In return I told him about Stuart from work and for a second he seemed put out. Hardly fair given that he’s been off humping an entire family, but his response was, ‘I thought I was helping you out with this stuff. I thought we were doing another role play first.’
‘You were away with the incest twins; I couldn’t get hold of you. We’ll still do the role play – there’s no specific order to this, Oliver. Besides, this is about me becoming the master of my sexual universe. Be pleased for me!’
‘I know. I am! I was just looking forward to it, that’s all. Well, we’re doing it outside too. I’ll pick you up after work tomorrow.’
Wednesday April 6th
Oliver was waiting for me as arranged and I caught him getting a look at Stuart as he walked down the road. ‘I thought you didn’t like really short hair,’ he muttered.
We drove for about forty minutes and barely spoke for the entire journey. We eventually got off the motorway and headed up some dirty country lane leading to God knows where. Oliver stopped the car, checked his face in the mirror, got out and then walked round and opened my door. He was acting strangely, and I started to get a sinking feeling in my stomach, like he was about to kill me or something.
I started to speak but it’s hard to talk when someone has suddenly pressed their mouth firmly up against yours. I gave up and gave in.
We manoeuvred round to the front of the car and he pulled down my tights and underwear. I say ‘pulled’; it was more of a ripping action, which would have been sexier had I not been wearing industrial-strength pants and tights. With some help they were flung into a nearby hedge and I was flipped over and shagged on the bonnet of the car, quite dramatically. While it was obvious he wanted me, I could tell he was mostly trying to out-shag Stuart so he could then jump up and down in front of me shouting ‘I’M THE WINNER, I’M THE FUCKING WINNER!’ In the midst of it, as he was kissing my neck, he moved his mouth to my ear and said, ‘It’s never this good with anyone else, is it?’
I answered truthfully: ‘No. It isn’t.’
After we’d finished he kissed me and offered to help look for my pants. We found them but they had already been explored and conquered by some minibeasts so I gladly abandoned them. ‘You want to stay at mine tonight? I can take you home to get some new pants first.’
‘Nah, I have to get home. I want to do girlie things like paint my nails and cover my face in mud. Besides, I’m exhausted. This was fun though.’
So he drove me home, where I fell into bed, grinning to myself and feeling a tad tender. The sex-outside challenge has definitely been my favourite so far and was even better than I expected. I’m not sure if it was the danger element, Stuart’s lip biting or Oliver’s competitive shagging which thrilled me the most, but I intend to make this a regular event. I hope to God I don’t end up on some ‘Caught Shagging on CCTV’ website.
Thursday April 7th
‘Are you free tonight, Phoebe? Let me take you on a date.’
There are certain sentences you never want to hear your boss say, and that is one of them.
‘Hang on a second, Romeo! I made it clear that—’ but before I could finish my sentence more words flew out of that hole in his face.
‘Well, it’s not a proper date, obviously, but recently I’ve been struggling and I don’t know why. I’m getting really fed up, and you did promise you’d help me.’
‘You’re making me help you. This is feeling more and more like blackmail, Frank. But fine. We’ll go straight from work, separately. I’m not having Maureen in admin whip herself into a frenzy when she sees us leaving together. And you’re paying.’
I had arranged to meet Frank in a cosy Italian restaurant waaayyy across town. I was sitting at the bar waiting for him when Oliver called.
‘You want to grab something to eat? I’m starving and—’
‘Sorry, Oliver, I’m already out on a date. Well, a fake date. With Frank. I’ll explain later.’
This was met with a silence long enough to make me uncomfortable.
‘Come round later if you want. You can eat me!’ I quipped.
My attempt at a joke fell flat, as did Oliver’s tone.
‘No, it’s fine. I’ll see you later.’
He hung up on me and I felt pissed off. What does he expect? That I’ll be there at his bloody beck and call? Then in lumbered Frank looking flustered and still wearing that stupid watch. We sat down at a table and the waitress brought over some menus. The date had officially begun.
‘Our soup tonight is minestrone. Can I get you some drinks?’
‘I’ll have a glass of dry white wine,’ Frank replied, taking off his suit jacket. ‘Large.’
‘Just make it a bottle,’ I added, watching him mentally undress the waitress. ‘We’ll need it.’
She walked away, completely unaware she’d just been added to Frank’s wank bank. A few minutes later she returned with the wine and took our orders – mushroom ravioli for me and some sort of fishy risotto for Frank. ‘So, did you get that half-page advert sold?’ Frank began, pouring himself some wine.
‘No work talk, Frank. It’s boring. Wow me with your chat.’
‘My chat?’
‘Your conversation, y’know, your witty repartee.’
Ten minutes later I knew exactly what the problem was, and when we’d finished eating I decided to nip it in the bud.
‘Frank, do you know that you’re the worst company on a date ever? And when I say “ever”, what I actually mean is “EVER!”’
He looked genuinely confused. ‘So far you’ve turned around twice mid-conversation to look at that waitress’s backside, you’ve poured yourself wine without offering me any, you’ve managed to turn two separate conversations into really dull anecdotes about buying expensive shit – speaking of which, your watch is idiotic—’
‘Jesus, Phoebe, you don’t have to be so blunt about it! I knew something like this would happen,’ he sniffed. ‘You see, Phoebe, there are two types of people in this world: people like you, and people like me.’
‘What “narcissist” and “blackmailed”? You might be right,’ I said, rolling my eyes. ‘And that very statement you’ve just made is the reason women would rather stay at home and self-harm than go out with you. Remember that.’
He wasn’t happy.
‘Look, you asked me to help you. Stop being such a big baby. I’m going to write all this down and email it to you in the morning. My advice is to STOP DATING until you’ve worked on this, but first step is to get rid of that bloody watch – it’s hideous.’
The one thing I didn’t mention was that, despite his lack of social skills, he smelled amazing, like vanilla, and it reminded me of cake and … STOP IT, Phoebe! Under no circumstances will you nibble your boss.
Friday April 8th
I got into the office bang on 9 a.m., caramel latte in hand, eyes shielded from the bright yellow cardigan Kelly was wearing. The very second I sat down my phone rang; it was Frank.
‘Good morning, Phoebe.’
‘Morning.’
‘Regarding last night, I would appreciate your feedback ASAP.’ He pronounced it Ay-sap. I couldn’t let him get away with that.
‘You do know that ASAP isn’t actually a word? You’re supposed to spell out each letter. It’s not like—’
‘Oh, stop being a smart-arse. And get on with it. And then get that half-page sold.’
He hung up and I opened my email and answered thirteen terribly unimportant messages before getting round to emailing him. When I did, I kept it short and sweet.
From: Phoebe Henderson
Subject: Further to our meeting
Frank,
Further to our meeting yesterday, here are some pointers I think would definitely help you with your problem:
1. Unless you are a rapper, stop wearing bling, you maniac.
2. Consider for a moment that there are many women in the world who do not give a fuck how much things cost or, indeed, how much you’ve paid for them.
3. If you must look at other women’s bottoms while on a date, learn how to be subtle for fuck’s sake.
4. When your date speaks, let her finish. It’s also helpful if your reply doesn’t start with ‘That’s the same as when I …’ because it isn’t anything like something you once did. No, don’t argue – it isn’t.
Work on this and we’ll try it again.
Saturday April 9th
Oliver called this evening, thankfully not in a huff, telling me he was going to Club Noir next Friday with a girl he works with called Simone. I didn’t even know he was into burlesque. He says even I’d find her hot, which brings to mind my next challenge: group sex or, more specifically, a threesome. But before I think of starting on this particular challenge, I’ll need to consider one question: do I fancy women? The only answer I’ve come up with so far is – I’m not sure.
I can appreciate a beautiful woman to the point of becoming quite taken with her, but I can’t say I’ve ever fantasized about ripping her clothes off in the way I’ve imagined doing to many, many, MANY men, from Jack White to Eddie Izzard and even those two blokes off MasterChef. I often wonder if they’d be as descriptive in bed as they are with their food … But I digress.
If I’m going to throw myself into this, surely it’d be better if there’s a chance I actually wanted to shag both parties? I remember when I was seventeen I kissed a girl. We were completely pissed and unfortunately the whole of my school found out, landing me with a ‘lesbo’ tag that I didn’t shake until years later. But there was part of me that secretly loved the fact that my sexuality was seen as ambiguous (mainly because I wanted to be Madonna) and that it pissed off the girls and intrigued the boys. What I do believe is that attraction is something you have no control over, and even though I class myself as straight, I’m open to the possibility that I could enjoy being with women too. If I was completely straight maybe I wouldn’t even entertain the idea. No! The point of these challenges is to do things the old me wouldn’t, regardless of how much they scare me. Am I just over-analysing everything? Sex is just sex … Right?
Monday April 11th
Frank called me into his office at lunchtime today. He wasn’t wearing his watch. Praise the lord.
‘So when can we schedule another date? It’s rather more urgent as I met a woman over the weekend and I like her. Vanessa. I mean, she’s only a checkout girl but—’
‘Christ, listen to yourself, Frank: “only a checkout girl” – who do you think you are?’
He looked embarrassed. ‘Well, I do like her and I don’t want to mess it up. Are you free tomorrow night?’
‘I don’t know, I—’
‘That’s settled then. Off you go.’
How did I get myself into this? I’m beginning to think getting fired would have been less hassle. Still, if I can help him impress Vanessa, he’ll get off my case so it’s worth it.
Tuesday April 12th
We’d arranged to go to an Indian restaurant tonight as Frank knows the owner and gets a mate’s discount. I met him by his car (hidden away in the underground car park) and stayed low in the seat until we’d left the city centre.
‘My God, Phoebe, are you that embarrassed to be seen with me?’
‘I told you, I refuse to be the subject of gossip at work. If anyone saw us together, I’d never hear the end of it.’
‘Well, I often drop Maureen from accounts home.’
‘I’ve never seen that happen.’
‘No, she lies down on the back seat until we get to the motorway.’ He chuckled quietly to himself.
‘Did you just make a joke? Fucking hell, maybe there’s hope for you yet! How long till we get there? I’m starving.’
Five minutes later we pulled into a side street and I saw the restaurant. Not much to look at from the outside, but inside it was warm, inviting and covered in colourful, modern Indian art. The aroma of cumin and saffron reminded me just how hungry I was.
‘Frank!’ came a voice from the other end of the room. ‘Glad to see you!’
A handsome Indian waiter appeared and man-hugged Frank. I was stunned that someone genuinely seemed happy to see Frank, let alone make physical contact with him.
He led us to our seats, where there was a bottle of wine waiting. ‘I’ll send someone over in a minute to take your order. Enjoy!’
Frank poured the wine (me first). It was clear he’d been doing his homework.
Astonishingly, I had dinner with a relaxed, bling-free version of Frank, who made jokes, complimented me on my green eyes (without being too cheesy) and personally went to fetch me some water when I ate some curry that made my face melt. After dinner I had to ask him how he’d done it. I mean, he was almost a normal human being.
‘When someone so brutally points out your shortcomings, it’s hard to ignore them, Phoebe. I don’t want to be on my own any more, simple as that. Being vulnerable isn’t something that comes naturally to me, but I’m trying.’
‘Don’t worry, you’ll be fine!’ And for the first time in the three years I’ve worked with Frank, I smiled at him. It must have been quite alarming.
Wednesday April 13th
I left work at half five today, and after standing at the taxi rank in the rain for fifteen minutes, I caught a cab to Oliver’s place. The rain was pissing down, my feet were killing me and I think I was probably more excited about getting my shoes off and lying in front of his fire than actually seeing him.
Oliver opened the door to a soggy wet shell of a woman who had a bottle of wine in one hand and her shoes in the other. Half an hour later I was showered, wearing his fluffy robe and lying in front of the fire listening to Regina Spektor. I want to marry his flat.
Like a vision of domesticity, Oliver sat across from me on his brown leather couch, reading a newspaper and sipping red wine. ‘Comfy?’ he asked, throwing a glance in my direction.
‘Very. This is perfect. Just ignore me if I start purring.’
He put his newspaper down. ‘That’s hot. I’m very glad you started these challenges – you’re a sexy bitch these days.’
‘Maybe I always was.’
‘Yeah, maybe I just didn’t notice. So what’s next on your list?’ He lay back on the couch and his T-shirt rode up a little, revealing his deliciously flat stomach.
‘You up for having a threesome?’
He nodded, eyes closed. The guy is so laid-back I sometimes want to poke him in the face to make sure he’s still alive.
‘Have you ever had a threesome?’
Again he nodded.
‘Oh, COME ON! Give me some feedback here! What was it like? Was it good?’
He glugged his wine, ‘It was OK. Bit of a let-down actually. It felt like someone was always waiting their turn, and unless everyone is totally into it, it’s rather pointless. I did get to shag two women though.’
‘Hang on, I’m confused. So if it wasn’t that great, why do it again with me?’
‘Didn’t you hear me? I get to shag two women.’ Fair enough.
He’s agreed to ‘look into it’, like some sort of sexual private investigator.
Friday April 15th
I didn’t get a chance to ponder my threesome for too long before I got the phone call.
‘Phoebs! Remember Simone? The girl from work? She’s agreed. The threesome. Are you up for it?’
‘What? Yes? NO! It’s one thirty in the morning, I’m in bed. I have big hair.’
‘Don’t bother getting dressed then. We’ll be there in half an hour.’
‘What? Now—’
But he’d hung up.
Yes, cool as a cucumber, Oliver had been to the burlesque night and somehow convinced his date to have a threesome. Just like that. Oh shit. I could have killed him, and did in fact plan his demise as I showered, brushed my teeth, hid my pyjamas and stuck some sexy undies on. What the hell was he thinking? And, more importantly, who the fuck was he bringing? If he brings a beast, they’re both leaving, but he won’t; she’ll be gorgeous and I’ll just be the third wheel. Why did I say yes? I still haven’t made up my mind about the whole ‘girl on girl’ dilemma, and now the decision has apparently been taken out of my hands. I would have liked to have at least had a peek at her first.
An hour later the doorbell rang and in came Oliver and Simone, looking very pleased with themselves and obviously tipsy from their night out. He was wearing a suit and tie and she was wearing a wiggle dress, complete with amazing red shoes I wanted to try on.
She wasn’t a beast thankfully: blonde hair, tiny compared to me, and pretty, like a little doll. He stood with his hands around her waist, nuzzling her neck, and I stood there not knowing where the hell to look. To say that the next few minutes were uncomfortable would be an understatement. I think I even offered them tea at one point, but when we finally made it into the bedroom the kissing started, which was a perfect excuse not to talk any more. Oliver seemed different somehow with Simone. He was very assertive, almost to the point of domineering, and she played along, doing exactly as she was told. I felt awkward. But, I thought, when in Rome …
Oliver and I kissed, Oliver then kissed Simone, and then he said to me sternly, ‘Kiss her.’ So we kissed, which I have to say was very, very nice. The whole thing was a blur after that. There was lots of touching and more kissing, hands were everywhere and I remember lots of questions firing in and out of my mind: would they prefer it if I wasn’t here? Does he prefer her body to mine? Should I have shaved it all off? As we all got completely naked, I forgot about my insecurities and actually started to enjoy it. Maybe I was into girls? Maybe this could be the start of something new? But as I went down on Simone my questions were answered with a resounding ‘NO!’ like a big, booming, Brian Blessed voice from above.
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