The Bet

** If you're want to catch up to speed, chapter 1 can be found here: https://www.literotica.com/s/the-bet-ch-01-15

I haven't made any plans for this at all, so please excuse any inconsistencies between Chapters. The writing of Chapter 3 has begun and continues apace - any suggestions welcome!

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Chapter 2 - Wednesday

Day Three of the Conference was even duller than the first two. A talk on 'The Effects of Brexit on the Office Stationary Industry', boiled down to one very simple answer: 'We Don't Know'. Before meeting Nancy, I had this talk marked down as the one that could explode into violence or, at the very least, mild excitement. A room full of testosterone-fuelled alpha male wannabes and a delicate subject like Brexit, Remainers mixed with Brexiteers? Surely a powder-keg of fisticuffs beckoned?

Yeah, I couldn't have been more wrong if I tried.

The guy delivering the speech was so nondescript and apologetic he defused any anger at all. He'd brought leaflets outlining the potential outcomes, the effects of Brexit on the stapler industry, higher import taxes on equipment which were so in-depth for any of fifteen outcomes, I didn't even have to make any notes. I switched off and reminisced about the night before - Nancy's soft, inviting pussy, her full buttocks, her smile, her sparkling eyes. A couple of times I had to adjust myself and reposition my paperwork to hide my memories.

We broke for a short recess at about 11 and I went for coffee. I needed something strong and black, added two sugars. I turned around and found Michelle standing beside me, helping herself to a herbal tea.

'Morning, Steve. Good night?' she asked. Her voice was pleasant and friendly, I sensed laughter wasn't too far behind it.

'It was, thanks,' I replied with all the innocence I could find. 'Yours?'

'Well, it took an unexpected turn, but I think everything worked out for the best.' She dropped her voice to a conspiratorial whisper. 'So who was she?'

'Who?'

She nudged me. 'Guys don't run naked round a hotel robbing champagne for other guys. There are two women here, me and Patricia. Patricia's in her sixties, so I hope you didn't go there. I was otherwise engaged, so... who was she?'

'Her name's Nancy. I met her in a pub.'

Michelle nodded. 'I thought it had to be an outsider. People in this company are...' she turned and looked at Phil, my erstwhile quizzing partner from Monday night. 'Most of them are fucking weird.'

'Phil? Nah, he's a nice guy.'

'Ever had him try to pull you?' she visibly shuddered. 'If you keep seeing this girl, don't introduce her to him. You'll never see her again.'

I laughed. 'You're going to have to tell me that story, you know.'

'Never. I don't want to think about it, ever again. So, are you seeing her again?'

'I hope so. She was sweet, funny. We connected.'

'Is she still here?'

'No idea,' I conceded. 'I left her in my room because I had to come to this.'

Michelle took my coffee from me. 'Go see her. I'll say you were for the whole session. Let's face it, you're not going to miss anything.'

On impulse, I kissed her on the cheek and ran out of the room. The lift was on its duty on another floor so I ran straight up the stairs, taking them two at a time. I got to my room, burst through the door.

It was empty. She'd showered, the steam was still lingering on the mirror. On the chest of drawers, I found a scrap of paper from the cheap notepad that came with the room, her phone number written on it. I added it to my phone and sat on the end of the bed, composing her a message.

Hey, it's Steve. Last night was amazing. See you later?

I sent it and headed back downstairs to the Brexit talk. As I slipped onto an empty chair on the back row, my phone vibrated with her reply.

Hey! Let me know when you're done and meet me in Liverpool One if you still want to take me shopping xx

The rest of the session stretched out like syrup from a spoon. By the time 3pm rolled around, I'd had enough of Brexit, staplers and given the choice of finding out more about online storage systems and their failsafe passwords or throwing myself from a window, I'd be looking for the nearest glass aperture.

Eventually, the final speaker wrapped up, one of the organisers thanked them for their presentation and invited each of us delegates to attend the evening's festivities, a blind charity auction. There was no chance I'd be attending. I sent Nancy a quick message to say I was done, she told me the location of a coffee shop in Liverpool One to meet her outside. I called a cab and was out of the hotel in less than twenty minutes.

She was beautiful in the daylight. She was wearing her hair up in a loose ponytail, blue jeans, her black puffa jacket and the same battered white trainers. I paid the cabbie and went to her. On the journey I'd began to persuade myself that she'd tell me last night was a mistake, that Luke was the guy she was meant to be with, that she never wanted to see me again.

My fears were put to bed as soon as she wrapped her arms around me, curling them behind my neck and kissing me. I slipped my arms around her waist before dropping one hand onto her butt and giving it a squeeze.

We broke away and stood, gazing at each other, holding hands.

'How was your conference?' she asked.

'Crap,' I replied. 'I'd much rather have been with you.'

She smiled. 'That's sweet.'

'Anyway,' I said. 'Shopping. You need a dress for tonight. Where's good to start?'

She shrugged. 'Dunno. I usually shop in Primark. I don't know anywhere posh that might sell the sort of thing you want.'

I spotted Marks & Spencers across the way. 'Let's start there.'

Usually, clothes shopping with women is my idea of hell. With Nancy, it was different. It was fun. We kissed, we held hands, we touched. I discovered more about her - she didn't like football, she liked pop music, wasn't keen on drinking too much, had four younger siblings. She found a black dress she liked in Selfridges then tried it and refused to show me. She wanted it to be a surprise.

I paid and then it was time to head back to the hotel. I needed to shower and get myself into smart clothes. I ordered a couple more cabs, one back to my hotel and one to take Nancy home. She gave me her address and I promised to pick her up at 6pm to collect her before heading into town.

Back at the hotel, I headed for reception, planning to ask the receptionist for a recommendation for a meal. As I arrived, I spotted Michelle and the night-porter whispering behind his desk. They saw me coming and broke apart, the night-porter switching his attention to me. Michelle smiled at me.

'Evening, Steve. Everything okay?' she asked.

'Yeah, it's grand. I was going to ask for any recommendations for a good restaurant in the city to head to?' I looked at the night-porter. His badge told me his name was Lincoln, he was a young, good-looking guy when seen in daylight. I knew he was blessed in the trouser department, which had to be why Michelle was down here, wearing a tight white shirt, a uplifting bra to emphasise her breasts and a promise she'd be leaving Liverpool in three days, no strings.

Lincoln nodded. 'I know just the place,' he said and told me about his favourite steakhouse.

I googled the place, it sounded perfect. I called and booked a table, then yet another cab. I loved how much cheaper they were in Liverpool than London, I was starting to become accustomed to being driven everywhere. As I got in the lift to go back to my room, Michelle slid in beside me.

'Hot date tonight?'

'Yeah, hopefully. What about you and that guy?'

She blushed. 'I told him you'd seen us.'

'Has he sent me to a shit restaurant now?'

'No, nothing like that.' She cocked her head and looked me up and down. 'Last night was the first time I've been watched. It was... nice.'

I had no idea how to respond other than to flush bright red, giggle nervously and pray for the lift to get to my floor. Thanking every deity I could think of, the doors opened and I dived off to my room to make myself look as irresistible as possible.

An hour later, I was in the cab to pick up Nancy, half-listening to the cabbie's inane chatter about his mother-in-law, butterflies in my stomach as I waited to see her. I caught the name of her street as we turned into it and then I saw her, waiting in front of a terraced house, bathed in orange streetlight. The house behind her looked rundown and dirty, the front garden overgrown and disorganised. All around us were signs of boredom and deprivation - graffitied walls, dogs barking, litter swirling in the light early evening breeze. Behind her, I could see a silhouette in the front window of what I assumed to be her house, joined a few seconds later by a smaller one.

Nancy spotted me in the back seat of the car and rushed over, waving goodbye to the silhouettes. The shorter one waved back, the taller one remained still. I caught side of another figure, skulking by the bushes a few doors away. As Nancy opened the cab door, the figure suddenly strode towards her and roughly took hold of her arm.

'Luke! I told you earlier, we're through. Now fuck off!' she said, fiercely.

I sprung from the taxi and stood beside her. Luke eyed me with anger bordering on hatred.

'You fucking cunt!' he spat at me. 'Me and Nancy was gonna get married until you fucking showed up. You made me look a cunt in front of the boys last night. If I see you again, I'm gonna fucking knife ya!'

'Listen, mate, I don't want any trouble. I didn't mean for any of this to happen, but if Nancy was really happy with you, she wouldn't have spent the night with me. I'm sorry things have ended for you, but you need to be a man and walk away.'

He took a step towards me, his chest puffing out. He made a gun gesture with his thumb and forefingers and pointed them at me. 'That'll be real next time.'

He walked away from us backwards, never taking his eyes from me. Nancy stood beside and took my hand.

'Don't worry about him. He likes to think he's a tough guy, but he's all talk.'

'That's the first time I've ever been threatened with a pretend gun before.' We got into the taxi and I gave the driver the restaurant to head to. 'So, were you engaged to him?'

'Fuck, no! You think I'd want to marry him? Hell, no!'

I laughed. 'Glad to hear that. How long were you together?'

'Six months. He started talking about marriage after about three weeks. It was kind of sweet. Look, forget about him. He'll find someone who's happy to be a wannabe gangster's girl and he'll move on. Let's have fun tonight. No more talk about Luke, okay?'

The taxi driver coughed in the front seat. 'Seriously mate, I wouldn't worry about that streak of piss. Looked like a decent wind would blow him over.'

***

We arrived at the restaurant and were escorted to our table by a purple-haired waitress with a tiny nose-stud. Nancy took her seat, and removed her coat.

She looked gorgeous. The dress she'd picked out earlier was a stunning black dress, with sequins that shimmered under the lights, held up by two thin straps over her shoulders and hinted very strongly she wasn't wearing a bra. It emphasised her curves and cut to mid-thigh, showing her legs off. She was finally wearing something other than trainers on her feet, pairing the outfit with a simple pair of black shoes. I swelled with pride when I realised other guys in the restaurant were checking her out.

I ordered a lager, she opted for a vodka and orange and we sat and stared at each other.

'You look sensational,' I told her.

She blushed. 'Thanks!' she mumbled, still not used to being complimented. She looked around the restaurant and I began to realise she was uncomfortable. I couldn't imagine she'd been in many places like this, no matter how beautiful she looked in that dress.

The waitress re-appeared with our drinks.

'To us!' I toasted and we clinked glasses. She smiled at me and my heart melted. She was gorgeous and stunning and lost and vulnerable all at the same time.

'How was your day?' I asked.

'It was... tough. I spoke to Luke, told him I'd spent the night with you. He didn't take it well and wanted to know how to find you to kick your head in. He's mostly talk, but he's angry. He might try something stupid.'

I shrugged. 'I'm only here for tonight and tomorrow night. Then I go back to London.'

The mention of my impending departure quietened us both for a few seconds. Then:

'Come with me. To London, I mean. I've got my own place, there's enough space for you. Sort you out with a job, maybe get you on your way to being a teacher. If you wanted.'

Nancy brightened at my suggestion. 'I don't know, what about my family? I don't know if mum could cope without me. She has depression. What if things didn't work out between us? I'd be stranded.'

She was being cautious. I liked that, it would have been easy to have been swept up in the moment and do something everyone regretted.

'Okay. Come down and stay with me. Come with me on Friday, head back on Monday. I'll pay for your tickets.' I took a deep breath. 'I think we could have something really special. I don't want this week to be the end of us.'

'Me neither.'

The waitress appeared with our food. Our eyes locked over the plates. I realised how pretty she was and how she didn't realise it. I could have swam in her chocolate eyes all night long. As I gazed at her, her foot began stroking my leg under the table. Just up and down on my calf and I had to fight the urge to reach under the table and caress her thighs.

We made small talk for the duration of the meal, I told a couple of stories from my university days. When she'd finished eating, she excused herself and went to the ladies. I watched her leave, the movement of her buttocks, sequins glittering with every step.

I glanced around the restaurant, taking even more pleasure in counting four guys watching her walk and four girlfriends glaring at them for doing so. She was gone for a few minutes, long enough for our plates to be cleared and a dessert menu left behind.

When Nancy had returned, she picked up the menu and glanced over it.

'There's nothing here I fancy,' she said. 'Is there anything else you'd like to eat tonight?'

I had no idea if she intended the double-intendre, but I wasn't going to let it slide.

'What I fancy eating isn't on the menu.'

She carefully laid her menu down on the table. 'Sounds nice. Is it the kind of dessert that needs extra cream?'

'Oh, I'd fill it with cream,' I replied. 'And second helpings. I'll definitely want second helpings.'

She gave me a wide-eyed, innocent look. 'It sounds delicious. Is it something you eat a lot?'

'Oh, I'd eat it every day.' I gave her what I hoped was a smouldering look. 'In fact, I'd eat it right now, if I could.'

She leaned back in her chair and stretched her arms above her. Her dress pulled taut around her breasts and it took all my willpower not to reach over and play with them.

'If you have a look, it's already warming up.' She winked at me. Slowly. Seductively.

'Oh, my...' I whispered before picking up a fork. 'Oh dear. I appear to have dropped my fork,' I said before tossing it to the floor. 'I must pick that up.'

I bent to look underneath the table. Nancy adjusted her dress slightly, tugging it up and discreetly opened her legs, giving me a full view of her shaven pussy. The line of hair I'd so enjoyed last night was gone, I could see her pink lips, the curl of her clitoris peeking out. If the tablecloth had been longer, I would have dived between her thighs, I really would. All I could do was look, admire and take my phone out of my pocket.

As I took my seat again, I hit the button to switch the video camera on and began to try and film her. With my other hand, I signalled to the waitress for the bill, and whispered there was a ten-pound tip for her if I could pay and be out the door in two minutes. Less than ninety seconds later, we were heading into the night.

What I wanted was beside the restaurant. A dark alley, looming shadows, no lights. I pulled her into the darkness with no apologies for the lack of romance. I needed her there, I needed her then. We dived between two bins, kissing passionately, feeding on one another. I pinned her against the wall and lifted her dress up as she fumbled to release me. A few seconds later, her legs were wrapped around my hips, her arms around my neck, my cock embedded in her.

The only sound was her breathing getting faster and faster as I ravaged her, again and again. She came silently, without warning, her pussy clenching around my shaft, her fingernails digging into the back of my neck. A woman orgasming always tips me over the edge and I grunted as I ejaculated, firing into her.

We remained still for a few minutes, holding each other and trying to get our breath back. Nancy lowered her legs to the ground and leaned against me for support.

'Fuck, I needed that!' I whispered, laughing.

'I love your cock,' she whispered back before kissing me again. 'Let's go before someone comes down here.'

'I've already come down here!'

She elbowed me. 'You know what I mean! Come on, let's get a drink and give you a rest. I'd like more dessert later, if that's okay?'

Shortly afterwards, we were in a pub, sitting opposite each other, holding hands over a small circular wooden table. I bought the drinks, lager for me, vodka and orange for her.

'What's the dirtiest thing you've ever done with a girl?' she asked. The bluntness of her question took me a little by surprise and I had to think for a second.

'I've watched someone giving a guy a blowjob,' I began, thinking back to the previous night and Michelle. 'One girl I had a one-nighter with at uni did ass-to-mouth, that was... odd.'

She screwed her face up. 'Shit, that's rank! Why would anyone want to...' she tailed off and shuddered.

'I saw her a couple of times after that, but never slept with her again. She was weird. Anyway, what about you? What's the dirtiest thing you've done?'

She thought for a few seconds. 'Not really had the chance to do anything crazy. Luke was always on at me to try anal, but I didn't want to. Not with him, anyway. And a threesome with this other girl he knew. He kept talking about her.'

'A threesome? Did you...?'

'No! The other girl, Lizzie? She's a right slag. I think he just wanted my permission to fuck her and see what she was like.'

'He sounds delightful, he really does. So all I have to do is not talk about anal and threesomes all the time, and you'll be happy?'

'I never said I wouldn't try things...'

'Can we go back to my hotel? Right now? I think I've rested enough...'

She picked up her glass and took a tiny sip of vodka. 'No. You can wait.'

To our left, another couple finished their drinks and headed off, vacating a booth with tall wooden panelling that offered privacy and long, cushioned seats. We grabbed our drinks and moved to the empty table before anyone else could get there.

I let Nancy in first, giving her butt a little pat as she climbed over the seat before sitting beside her. Rather than put her legs under the table, she turned longways and put with her legs over my legs with them slightly apart. I leaned forwards and turned slightly to block the view of anyone else, letting me look straight up her dress and giving me a grand view of the greatest sight on Earth. From our new vantage point, she could see the whole pub. I laid my hands on her calves and began to stroke her smooth legs. She leaned back in the corner and smiled dreamily at me. I began to let my hands explore her legs, over her knees and thighs, going a little higher each time.

My fingers brushed the bottom of her dress and then began to meander underneath the soft material. I tried to do it very discreetly, chatting away to her about anything and everything that came to mind, more stories from my university days, friends, my grandmother, all the while not looking at her. If anyone was listening, they'd have assumed I was the dullest date imaginable. After a few minutes, my entire hand had disappeared under her dress and my fingers flicked against the soft flesh of her pubis.