Losing Bet

I want to tell you about something that happened last summer, the end of a period of significant change for me. About three years ago, on the advice of my wife and friends, I had quit my job and set myself up running a business consultancy specializing in optimizing distance working for companies and their staff. I like to say it was a prescient move on my part, but the truth is no one could have predicted how a global pandemic would change the way we all work. But, honestly, by May 2020, the phone was ringing off the hook, and I couldn't hire good people fast enough. I suppose this was the high-class problem, but it wasn't the only change.

During this period, my wife of 18 years and I concluded that our relationship had run its course as far as marriage goes. We still loved each other: indeed, we remain good friends now, but it became clear we were no longer in love with each other. Our physical relationship had all but dried up, and we both agreed it would be only a matter of time before either one of us ended up having an affair. I think we'd both separately come to the same conclusion some time ago, but neither of us mentioned anything for fear of hurting the other. Thus, when my ex finally told me she was thinking about a divorce, I laughed out of relief more than anything else. That night we discussed an open relationship, but sex wasn't the only issue, so I decided to move into the guest bedroom until we could sell the house.

One of the people I turned to was the only person I knew who had already gotten divorced, a friend from when I first moved to London some 20 years ago, Jen. She had split with her ex after he turned out to be a jealous, controlling arsehole. Hers was a bad breakup, so when my marriage ended Jenny was worried for me. Fortunately in our case however, the paperwork was the biggest thing I had to complain about.

Jen was lovely. I'd known her since my Camden days. My mates and I would hang out bumming a drink off anyone who would pay and skate the local spots badly. Jen had the dubious qualifications of being both interested in skaters and rich, as her dad ran a bunch of bars across London. He'd split up with her mum so lavished attention and a bank account on his only daughter, who in turn shared the love with her 'cool skater' mates. In truth, she wasn't the only rich kid slumming it with us. Back then, Camden was full of them, children of media types who made coin in the 90s. They had the money, and we were part of the alternative scene that made Camden cool. Unlike most rich kids however, the glamour of spending time with a bunch of dirty skate punks, never wore off for Jen. She stuck around long after most of those slumming it had gone off to something newer and cooler than us.

When we met, I was with the woman I would go on to marry. That cut out a lot of the flirting faff Jenny felt she should have to do with her male friends, and as a result, we developed a close and lasting friendship. She was one of a kind, and while no one could say she was stupid, she had a well-earned reputation for endearing ditziness. Jen could also be quite a flake at times, not turning up to things or disappearing early without warning or even saying goodbye, etc. Turns out underneath all the heart and caring, she had one hell of a social anxiety issue masked by drinking in her 20s. For a while, falling in love with her husband had helped replace that booze-fuelled confidence, but the anxiety came back with a bang after her divorce. She lost all self-confidence and was consistently dating some useless bloke as a crutch, eventually ditching them all for being too controlling.

The Irony of course was that she had nothing to be worried about. Standing a good 5'5 in trainers with long lithe legs and an athletic body that she simply didn't deserve given the amount of junk food she could put away and fact she never seemed to exercise. She was always complimented about her beaming smile that would light up a room and the brunette hair that had a ridiculous amount of body and bouncy curls. Even when I was married, I always thought of her as an absolute stunner, a storm in a D-cup if you will.

We had a joke between us that she was leaping from titanic to titanic, hoping one wouldn't sink. She was very much unlucky in love but, by her own admission, posed an easy target, 30 something daughter of a multi-millionaire with a taste for a bad boy. Probably not a great combination. Eventually, she was persuaded that perhaps what she needed was to be single for a while. Her dad was lovely as ever and offered to let her stay in one of his many flats, so naturally, she chose the penthouse with stunning views over North London. I didn't blame her. To be honest, who wouldn't if it was an option.

On the other hand, I did not have a benevolent millionaire dad with an excess of penthouses available, so I had decided that I should buy a reasonably sized two-bedroom flat in Clapham. Unfortunately, as much as the business had taken off, London housing prices are insane, and if I wanted to live anywhere reasonable, I would need to spend time fixing it up. But, of course, it wasn't an option for the first six months, so it wasn't until August that I managed to take a month away from the company and start work in my own place.

I was midway through putting up the second coat of paint on the living room walls, now that the plaster finally cured when the phone rang. It was only 9:30 am on an otherwise ordinary Wednesday. Still, London was sweltering already and forecast to reach 30c. U.K. houses don't usually come with air conditioning, so I was more than a little sweaty already, even with the windows wide open.

"Hiya chump!" Jen opened with our traditional greeting to each other "What are you up to? I need you to come round and help me with something."

It genuinely didn't occur to her that I would likely be working or let alone with a client did it. She'd been accused in the past of trying to be some manic pixie dream girl by an ex of hers, but the truth was more mundane. Jen was an artist who had not been burdened the usual 9 to 5 routine since she left school. That and not being comfortable leaving the house half the time meant that such things as the regular weekday schedule didn't cross her mind.

"Hey, chump. I was busy painting, but yeah, sure, I could do with a break."

"Anything good? I'd love to see what you're working on."

"My living room Jen, I'm painting my living room, nothing glam."

"Oh yeah." There was a pause, and I could tell something was up. Her bubbles were less bubbly somehow.

"What is it hon, something up?"

"Hmm, do you mind coming round? I need help, but I don't want to say on the phone."

I tried to get the details out of her, but all she would say was she'd lost a bet. Intrigued, I jumped in the shower before grabbing what was left clean in the wardrobe and catching a tube across town to see what was up. When I got there around 11, Jen was already dressed to leave the flat. Like me, she's typically found kicking around in a pair of jeans, t-shirt, and trainers, so I forget she can scrub up. Jen was wearing a loose black silk camisole over an expensive but straightforward bra judging by the straps and a pair of loose culottes that came to her mid-calf. Gone were the usual vans; they too were replaced by a pair of strappy heeled sandals.

"Damn, girl!." I said when she greeted me at the door, "You've scrubbed up well. What's the occasion?"

She looked down at her outfit. "What this? Well, we're going shopping and not at the usual places you go."

"Shopping? Where? Wait, I get my suits from Tom Baker. They're nice suits."

"Yeah, but that's for work. You're normally a right scruffy bastard," she giggled, not being entirely serious. "How come you're better dressed than normal?"

"Combination of luck and social pressure."

We walked inside the spacious north London penthouse she 'looked after' for her dad. Jen looked at me, a little confused. I was in a smart-casual pair of chino shorts and a light blue linen shirt. Better dressed than usual, but as I said, it's what was left clean.

"What do you mean social pressure? Of all my friends, you give the least amount of fucks about anything when you're not at work and luck? I don't get it."

"Luck, I ran out of normal shorts because they're all covered in paint. Besides, I always feel underdressed when I come here. You live in a booji fucking penthouse overlooking London. I feel like I'm bringing down the property prices just by standing here."

"Ha, you got a point." Jen opened the fridge and poured me a glass of chilled fruit juice. "Still, this place is my dad's, not mine. I wouldn't be able to live here normally, but he loves me, you know?"

We looked out over central London, sipping our drinks and enjoying the view. I love having rich mates.

"So, what do you need me for? If you're going shopping, surely I can't be all that much help, and how does this involve losing a bet?"

Jen leaned on the balcony rail and told me how she was with Sam last night. The pair had spent the day sunbathing on the terrace and drinking, getting gently pissed. Sam ended up showing Jen an exhibitionist website where men published pictures of their wives and girlfriends in various stages of undress. In the members section things got even racier with pages of sucking and fucking there on the screen. All varieties were covered, men and women, women and women, group, gang, you name it. There were pages covering different fetishes and levels of activity. Some of the women wore masks or had their faces blurred, but some were utterly brazen and were perfectly recognisable even with a mouthful of some guys fat cock. Indeed, the reason behind Sam showing her was that she was one of the recognisable girlfriends in question, complete with a mouthful of cock. Jen thought Sam might have been trying to shock her but wasn't entirely sure.

Sam had always been one of Jenny's wilder friends, self-described as a slut with a near insatiable need for cock and pussy. She was fun in small doses as far as I was concerned, though she always struck me as someone trying too hard to be wild. That being said Sam was the first one to turn up whenever Jen was having a bad day, fight with a boyfriend, etc. and had to be physically held back from Jens ex-husband when she found out what he had done to her best friend. I might not be able to spend more than a night in Sam's company, but I both respected and loved the hell out of her commitment to my friend. She was good people.

Sam, it turned out, was particularly proud of this new outlet for her exhibitionism. After several more drinks, she had somehow suckered her mate into a. Jen declined to give me the details, assuring me that the nature was just simple drunken shenanigans and not important. What was important was that as she'd lost, Jen would now have to do a photoset with Sam behind the camera. Worse as Jen went double or quits and lost, she had to do two different shoots, and Sam would get to choose the themes!

Jen claimed she had only partially remembered it this morning, and it wasn't until Sam sent her a video from the night before agreeing to everything that it all came back. The rules were also set out in a WhatsApp chat message.

1. Jen would do two different photoshoots. The first would be themed Classy But Kinky and be in her lingerie, and the second would be looser and themed Slutty Bitch.

2. The shoots would be a week apart, starting with the first tonight.

3. The shoots will be revealing, with at minimum nipples showing on the first and more on the second. Both would be posted online.

4. Jen could remain anonymous if she chose though prizes would be awarded if she decided to show her face, at least on the private members' page.

Wow. This was exactly like Jen. She'd get drunk and agree to do all sorts of stuff with no intention of making good on the promise. It seems this time, though, she'd decided to go through with it or at least planned to. To illustrate what was expected, she even logged into the site and showed me one of the sets Sam had posted. I have to admit the thread started fairly tame with a masked woman in a dress showing a hint of lingerie. As we clicked through to the following pages, she began to show more and more. Finally, Sam's more confident ended up stark naked except for stockings, heels, and a smile. I made a note for later about the website's name for later perusal. I could see why Jen thought it might be fun, but she'd never shown any inclination towards exhibitionism before. Still, Jen was my friend, and while I may not always pay too much attention to it, she was also objectively hot. If she wanted to try flashing her tits to some strangers online, I wasn't going to stop her.

"So why exactly do you need me then?"

"Well, for one, I have no lingerie even vaguely appropriate for a photoshoot, let alone one called 'Classy but Kinky' and no idea where to start looking to get it."

"And two?"

"I have no fucking intention of going shopping for something like this alone." She looked at me expectantly. "Don't hold out on me, I know you've got a whole lingerie kink things going on and I know you spent a pretty penny on it back when you were married."

I said nothing

"Well, then where are we going?"

I had some thoughts. Well, of course, I did. She was right; I have a thing for girls in lingerie. Selfridges seemed like a good start. Money wasn't a huge issue for Jen, and the place had a bunch of brands. Everything else was variable after that, but I thought it was as good a place to start as any.

We grabbed a cab on her dads' account and headed into town.

Have I told you how much I love to have a minted mate? They make things so much easier.

When we got there, the fun began. We looked through a few brands mooching through the place, trying to get an idea of what worked and what didn't. Jen decided that she liked the look of stockings on Sam but hated the look of hold-ups, so that meant something with suspenders. Fortunately, that removed a bunch of brands for us and narrowed the field considerably.

Myla was our first stop, but Jen decided it was too girly after looking around. I thought Agent Provocateur would be a strong contender for a while, but nothing grabbed her eye, so we hung around the Bluebella stand checking bits out. Jen even tried some stuff on but came back unhappy with the look, so on we went. I was beginning to worry that we wouldn't find anything, and I would have to work harder in my role as a shopping guide.

That's when I had a thought; I'd discounted Bordello as being a little too racy, but perhaps that's what was needed. The moment Jen saw them, I knew we should have started here all along.

"Oh my god," she said, holding up a black bra comprised almost entirely of straps. "It's like a goth invented lingerie! Do you think I could pull this off?"

"I'm sure you could, though you'd have to put it on first."

"Very funny dickhead. Tell you what, you choose a set and I'll choose one if I like it? You never know, I might show it off to you."

I grabbed a set that seemed entirely made of straps and sheer fabric. Unfortunately, the suspender ended in thigh loops, but those could be replaced with stockings if desired. I handed them over for Jen to try, and while she went to the changing room, I headed off to find some seamed stockings to match. When I came back, Jen was at the counter. She turned and saw me while she was paying at the counter, and I could have sworn she looked a little disappointed.

"Where'd you get to? I looked for you when you came out, but you'd gone."

"I got you some of these to finish the look," I handed over several packets of stockings to her. "The seams will finish the look perfectly."

"But you don't know which set I got."

"Doesn't matter; you'll look stunning in whatever you choose."

She blushed; she actually blushed. "Do you really think so?"

I didn't answer, I just smiled and took my friend's arm, and together we walked off in search of the next bit of the outfit.

"Shoes. You need some shoes."

Jen took the lead, suddenly more confident. "I know exactly what I need and where to get them. I've always wanted an excuse to do this."

Jen positively pulled me along as she dragged me straight into the Christian Louboutin store.

"I've looked at these for ages, you know," she said, holding up a pair of black stiletto ankle boots with the obligatory red sole. "I just never had the outfit for them before."

"You? I never took you for a girl who wanted a pair of designer heels. Although, come to think of it, I've never seen you in a pair of heels. Can you even walk in them?"

"Oh yes, I have a bunch at home for going out with my dad. Whenever we go out for a meal, I need to dress up; they don't let you into his kind of places in a pair of trainers, you know." She hadn't even looked up from the objects of desire held in her hands. "I'm not always scruffy. Besides, I like heels, I love how my legs look in them, and I feel way more feminine in them."

"I'm sorry, I didn't mean to...."

"Don't be, just because you don't see everything about me. It's not your fault; you've only seen me one way; it's just I want to be sexy too sometimes."

"You don't have to tell me, you know. I have noticed. When I get home, I'm going to sign up to that site of Samantha's, so I get to see the results of today's efforts."

'Shit, why did I say that?' I thought. I just admitted I would perv on one of my oldest and closest friends parading around in her skimpiness. I mean, I wasn't lying; I was definitely going to perv on Jen when the pictures went up. But of course, I wasn't promising not to jerk off once or twice should then mood take me either, though I wouldn't tell her that. Fortunately for me, Jen didn't seem to have caught the last line as the girl arrived to help relieve Jen's credit card of the better part of a grand.

We headed out to grab lunch. Jen realized she hadn't eaten since last night and was starving, so we went to a little Vietnamese place she knew we could get a table. Seated in a secluded booth, we started chatting again. I had gotten the feeling that she was hiding something. What exactly went on last night regarding the bet.

"So, what was this bet then?" I asked once we'd been shown to our little booth and ordered. "I helped you today, so don't hold out on me."

"Nothing, it was just a silly thing."

"Bullshit." I laughed. "You are a great friend, but you suck at lying, honey."

There was that blush again. "I can't tell you. It's embarrassing."

"Do I need to ask Sam? I'm sure she'll tell me."

"Ugh, you're such a dickhead. Ok." She took a breath, steeling herself for what she was about to admit to me. "You know I said we were sunbathing and drinking yesterday when Sam showed me her pics on that website?"

I nodded.

"Well, after she'd showed me, I went to the loo. I honestly needed a piss, after all, that wine, but after I dabbed myself dry and, well, I was really wet. You know, between my legs."

I couldn't help but laugh. Sometimes she could be crude as any of our friends and swear like a sailor, but then sometimes, she could be so damn twee. So here she was telling me she'd got the massive horn looking at her friend's porn pics but couldn't say pussy.

"You mean to say your pussy was wet."

"Oh god, like you wouldn't believe. I don't know if it was the sun or the drink,"

"Or the porn," I interjected

"Or the porn." She agreed

"Definitely the porn."

"Probably." She grinned with a wicked sparkle in her eye. "But I couldn't help myself. I just had to finger myself."

Jen looked up, unsure if she'd said too much, but I was utterly enthralled and, to be honest, sporting a significant stiffening in my shorts. At that point, the waiter arrived with our orders, but as soon as he left, I had to know more