Rachel's Dare Ch. 02: Bare in Boston

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Rachel gives me a re-match in our game of nude dares.
12.5k words
4.75
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Part 1 of the 2 part series

Updated 08/30/2017
Created 08/22/2014
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Note from the author: in "Rachel's Dare: A Walk in the Park", Rachel and I went for a walk in a park at 5:00am. It did not end well for me, with Rachel escaping the dare topless, while I was photographed naked. Needless to say, Rachel has a few ideas for a rematch.

*****

The cafe was full as I arrived. The threat of rain hung over the city, and the murkiness of the cloud-laden sky signalled a wet weekend may well be ahead. Despite all that, the promise of rain had not deterred a small army of officer and retail workers from retreating to the fleetingly-brief sanctuary known as Friday lunch.

I hoped Rachel was already here, otherwise we'd be in for the game of "hunt for a table" across the next six cafes, with no guarantee of emerging victorious.

As I stood in the door to the cafe, a woman at a near-by table gave me a sharp look, and without saying a word, gave me the hurry up to get inside and close the door. It was cold outside and she clearly didn't appreciate the draft that swept in with me.

Nodding my head in slight acknowledgement, I stepped forward and closed the door behind me. A waitress bustled over to me, menu in hand, with a slightly frazzled look on her face. I quickly held up a hand to delay her inevitable question, and cast my eyes around the packed room. Thankfully, Rachel was a hard woman to miss, and my search was rewarded within the space of a few seconds.

Rachel had a tendency to stand out in a crowd. Not through the use of extravagant or revealing clothing, it had to be said. As I spotted her sitting at an otherwise empty table, I noted that she wore a simple business blouse, with a couple of buttons modestly undone at the top. A smart, stylish, full-length rain coat was draped over another chair to the side of where she sat. Rachel was the kind of woman who'd look hot even in a rain coat, I thought idly to myself.

Still, all of that was hardly out of place or out of line with professional lady-like attire. As beautiful as she was, that wasn't what made Rachel such a find. It wasn't even her red hair that made Rachel so instantly recognisable, or the athletic physique that she'd maintained late into her thirties. No, there was something else that made Rachel stand out in the crowd. It was the way that she constantly seemed to have a faint, amused smile on her lips, and the way that risk and adventure seemed to dance in her eyes these days.

I pointed at Rachel and smiled at the waitress, who briefly acknowledged my gesture before heading off on her next task.

Walking through the crowd, the light drone of conversation drowned out my approach, so that I arrived at the table seemingly without Rachel having noticed.

"Hey." I said, by simple greeting, and collapsed into the chair opposite her. She'd had her head buried in the menu as I'd walked over. Looking up, she seemed surprised to see me, and momentarily opened her mouth. I looked at her, and as the seconds passed and she didn't say anything, a slightly puzzled expression crept on to her face.

"Umm... we were meeting for lunch?" I volunteered, as Rachel still seemed lost for words. Suddenly a light seemed to switch on in Rachel's eyes.

"Ohhh..." she said, finally, "Sorry, Peter! I almost didn't recognise you..." she paused again, and this time the corners of her mouth clearly twitched in what looked like a suppressed laugh, "... I guess I didn't recognise you, what with, you know, you actually having clothes on!"

Rachel lost the battle to suppress her laugh as she finished off her sentence, and the laughter almost drowned out the final few words. I rolled my eyes in silent protest at Rachel's obvious teasing, and she waved away my grumbles with a flick of her hand.

"Sorry," she continued, "I was sure I could get that out with a straight face." Rachel grinned and I just shook my head in mock sadness at her inability to properly deliver a decent teasing.

That only caused Rachel to laugh more though. She gave me a wink, whisked her phone out of her bag, and made a show of checking something on the screen. Holding it up in front of her, so she could see both me and the screen, she seemed to critically assess something, switching her eyes back between me and the screen several times. I rolled my eyes again. Clearly she was looking at the "evidence" of our walk yesterday morning. After a few moments of to'ing and fro'ing, Rachel seemed to visibly settle on a decision.

"Yes, now I've checked yesterday morning's photos again, I can definitely see a resemblance!"

I stuck my tongue out at her at that point, only causing her to laugh even more.

"Of course," she continued, once she'd re-gathered a measure of self-control, "a woman can never be too careful in making sure who she's talking to is really who they say they are." Leaning in closer, and treating me to a gentle whiff of her perfume, Rachel whispered. "Perhaps you should take off that stuffy shirt, just so I can compare like with like."

Turning her phone around so that I could see what she'd been looking at, I was greeted with the sight of me - completely naked - standing by her car at the park, posing with my hands on my hips, and my chest and penis clearly on display.

"I was going to suggest," Rachel added, airily, "that you show me the full goods, but we should probably save something for the walk back to your office!" Rachel smirked at that, clearly very pleased with herself.

I coughed, gently pushed her phone away so that it lay - screen facing down - on the table, and delicately changed subjects.

"Sorry I'm late." I said, avoiding Rachel's stare, knowing without looking that her eyes were still filled with mirth at my "indiscreet" behaviour yesterday. "I've got a major work presentation after this, and wanted to make sure my slides were done."

Rachel tut-tutted at that, waggling a finger in my face. "Now, now, never tell a woman that she's playing second fiddle to a powerpoint presentation. She might start to think she's losing her appeal." Nonetheless, she put a hand up and attracted the attention of one of the waitresses. As the visibly harassed woman came over, Rachel whispered. "Well, since you're in such a desperate hurry, we should order now. Besides, we have much to discuss over lunch." She winked at that. As I remembered the outcome of the last time she'd had 'much to discuss with me', I went slightly red in the face.

I quickly scanned the menu as Rachel made her order, and eventually ended up having the same thing she was having anyway. As the waitress took away the menus and fought her way over to the kitchen, Rachel leaned back and gave me her equivalent of an innocent look.

"So... what are you up to this weekend?" Rachel asked, in an off-hand, casual manner, sipping some water from her glass as she finished.

My eyes narrowed as my suspicions grew. "Nothing much." I said. "I've got the presentation this afternoon, after that, not much until Monday afternoon." I sipped some of my own water. "I guess I'll watch the Bears/Patriots game on Sunday." Both Rachel and I were Bears fans. Recently, that had not been the most pleasant of experiences, although a couple of decent wins this season meant at least the Patriots match could be a close one.

"Good... good..." Rachel replied, nodding. "I'll probably watch the match too." She paused then, slightly longer than was natural. "I'll be in Boston though. Got a work conference Monday through Wednesday, so I'm heading up on Sunday. Guess I'll be in enemy territory." Rachel paused again. "You know what? You should come and join me.' she added, almost as an after-thought.

I was half way through another sip of water as she said that, and had to manfully try and cover up the fact that I'd almost sprayed the water everywhere. Looking at her intently, I tried to hazard a guess at exactly what she was implying. Seeing my look, Rachel grinned, and wagged another finger at me.


"Now, now." she said. "Separate rooms I'm afraid." She stopped, almost as if re-considering that. With a light shrug of the shoulders, she continued. "Well, for now at least." She treated me to another trademark wink with that line, and her eyes sparkled as she saw me look flustered and awkward.

"I have an idea though." Rachel said, carefully. I felt my blood pressure rise at that. Rachel's ideas now had a track record of ending in my nudity.

"Would I be right in thinking you'd be keen for a re-match after your... abject... total... humiliating... stark naked... widely circulated... " Rachel cast around for more adjectives, and then simply closed with "... defeat?"

I coughed at that, and kept my eyes down, half convinced that some of the people in the cafe had possibly seen the photos that had been shared online. While Rachel had let me cover my face for the online photos, every hour that passed made me more and more convinced that I was still recognisable.

"Well," Rachel said, "I think you're in luck... unlike yesterday.". Rachel's evil grin grew even larger at that. The beautiful red-head was clearly having the time of her life, and she even toyed with a button on her blouse just to further get my attention.

"So, how about you come up with me, and we have a little game of our own while the Bears are playing the Patriots. I've been told there's a good sports bar where we can watch the match."

"Sure." I replied, trying to sound calm and confident. "Maybe we can put a little something on the result of the match?"

Rachel nodded briefly in agreement. "You've read my mind, Pete." She held my gaze for a moment, and casually flicked open a button of her blouse, revealing the hint of a lacy white bra under the cream material of her work top. "In fact, why don't we make it that if the Bears win, you win, and if the Patriots win, then I win?"

I didn't want to go against my own team, and the match previews were already beginning to talk up the Bears chances. I was a Chicago tragic, and I knew in my heart I wouldn't be able to cheer for the Patriots.

"Okay," I said, finally, "you're on." After all, I thought, it could hardly goes worse than our first daring adventure...

"Excellent." Rachel replied, very pleased with this turn of events. "We can discuss the specific rules and regulations of the re-match tomorrow, before we leave on Sunday."

Rachel moved some stuff around the table as the waitress returned with our lunches and wordlessly placed them in front of us. Satisfied that everything was as it should be, the waitress gave us both a smile and headed back to the next person in the long line of waiting customers.

Rachel smiled after her, waiting for the woman to be out of earshot. Once she was, my red-headed friend continued.

"Well, can I suggest you prepare for our rematch by purchasing a possible outfit that you might like to me wear at some point in the evening's festivities." Rachel took a bite out of her food, and looked at me intently. "Try to be imaginative, but don't spend too much money." Rachel took another bite and swallowed her food before clarifying her seeming concern for my bank balance. "After all, you won't be winning, so there'll strictly speaking be no need for the outfit." She flashed me her dazzling smile at that point. "Of course, I'll be buying something for you too."

As she leaned towards me again, permitting a second chance for me to be taken in by her perfume, she added. "Something that brings out your cheeks. You have nice cheeks."

I blushed at that, and was almost about to thank her for the compliment before she interrupted.

"Sorry, just to be clear, I hope you realised as I was talking about your ass cheeks."

I sighed at that, with Rachel visibly congratulating herself at her cleverness.

"Sure, sure." I replied, waving away Rachel's attempts to needle and tease me. "We'll see who's laughing after the game. You know what, I'm thinking the Patriot's season is about to come to a shuddering halt, and you know what's really, really strange?" I paused as she threw her hands apart in mock incomprehension at what I could possibly mean.

"I'm not even the least bit worried about that."

Fixing her with what I hoped came across as a more confident look than I actually felt, I finished up with "... strange, don't you think?"

Rachel laughed. Even I had to laugh at that, and we both grinned at each other as we made headway on our lunches.

As we worked our where through lunch, Rachel filled me in on the happenings of her day. For the time being at least, we put aside the matter of yesterday's walk, and Sunday's re-match, and we were just friends again. Perfectly normal, perfectly average friends, gossiping and chatting about the usual boring stuff. I asked how Rachel's kids were doing at University, and Rachel asked me if I'd seen the season premiere of 'Flash'. She knew I was a bit of a comic book geek at heart, and actually even managed to resist making a pun about my own flashing yesterday.

With the final mouthfuls finished though, Rachel dabbed her mouth with her napkin, and then gave me a serious look.

"Now," she said, "are you in the mood for a teaser for Sunday's escapades?"

I had no idea what she was talking about, but was nonetheless intrigued. I shrugged my shoulders, and gave a gesture for her to continue. Taking my cue, Rachel reached up one hand, and delicately took hold of another button on her blouse. As she did, her hand brushed the material, causing the blouse to open slightly and reveal even more of her white lacy bra.It was a simple seven button blouse, and she'd already had a perfectly modest two buttons undone when I'd joined her. With the removal of the third before the meals arrived, that only left her with four buttons left done up.

"I'll do a little dare with you." Rachel whispered, conspiratorially. "If you go into the men's toilets and remove your underwear, bring it back, and hand it over to me..." Rachel stopped talking, and played with the blouse button for a moment, almost but not quite undoing it.

"... Then this tiny, flimsy, little button, might just slip through it's button hole... " Rachel put her other hand to her mouth in an apparent look of horror. "... revealing even more of my sexy, lacy, practically see-through..." she was almost breathing her words at this point, the sexual tension rising with every syllable, "... brassiere. Oh dear! The scandal!"

Rachel looked at me with seemingly pleading eyes. "You won't do it will you?" she asked, sweetness and naivety dripping from her tongue. "You won't go and give me your big, manly underpants, and make little old me expose and flash..." she placed a hand across her forehead as if she was about to faint, "... my brassiere!"

I had to stop myself from openly applauding the acting, and I tried to spend a few moments trying to figure out what her game was. How exactly could this end up in my embarrassment? Admittedly, it was hard to focus on that with Rachel amping up the melodramatic over-acting with every passing second. This couldn't backfire on me, could it? Cautiously, I stood up, and nodded my head at the men's toilets.

"I'll be right back." I said, meaningfully.

Rachel practically gasped at my "brazenness", and I heard her whisper - albeit through stifled laughter - "How could he take such advantage of me?!" as I left.

Within moments, I had returned to the table. It had to be said, the act of walking through the cafe with my underpants stuffed in a trouser pocket made me feel a lot more exposed than it should have done. Still, having successfully completed my part of the bargain, I discreetly handed over the requested item, and raised an eyebrow in expectation.

Rachel's sighed dramatically, and then - with clearly fake resignation - fumbled at the fourth of her seven buttons. The button undid easily, and the material of her blouse parted some more. Now, it wasn't just the faint hint of white, lacy bra that I could see. It was both cups, in both of their c-cup splendour. I leaned back in satisfaction.

"You know, I've got a pair of socks you could have." I offered. "All it would take is for to undo that fifth button." Rachel gasped again, and covered her mouth to stop a small shriek from emerging. Her eyes were full of adventure and mischief though, and she gave me a small wink, as the waitress returned to collect our plates. As the woman reached to take Rachel's, she caught a full look at Rachel's bra, and almost dropped the plates in surprise. Covering up her own embarrassment, the waitress mumbled something about paying at the counter, and hurried off.

Not for the first or last time today, Rachel laughed warmly at the reactions she was able to get from others.

"Okay hotshot," she said with a goofy smile, "how about you go pay for lunch. I need to go to the ladies. I'll walk you back to your office."

I smiled in return, and got up from the table. I realised that there was a slight bulge noticeable in my trousers. Rachel's antics were definitely warming me up. Focussing on the task at hand, I placed two hands loosely in front of me, and headed over to the front counter. It wasn't the smoothest of cover-ups, but everyone else was thankfully too preoccupied with their own business to notice me.

There was a small queue to pay, and I idly wondered what I'd get as way of a costume for Rachel. The woman would look good in practically anything. She'd definitely look good in practically nothing as well... Okay, that didn't help control the bulge in my trousers _at_all_.

Bringing my attention back to more immediate matters, I quickly settled the bill, and waited just inside the door for Rachel to show up. She did, after a few minutes, now safely wrapped up in her rain coat, her bag perched on one shoulder, ready to brave the weather outside.

It had managed to get even more windy and sullen while we'd been inside, but at least the rain wasn't pelting down just yet.

We walked back to my office, which by happy coincidence was only a few blocks over from Rachel's own work.

On the way back, Rachel asked what my presentation was about. She even managed to feign some modest interest while I rattled off something about a major project that we'd finally won a bid on, and that I now needed to present to the marketing team. After about five minutes of listening politely to me talk about the detailed intricacies of my job, Rachel's attention finally broke, and she patted me on the shoulder.

"Well," she said, "... good luck with ... whatever the hell that was all about."

I gave a short half-laugh. "Well perhaps you should come up and sit in on the presentation." I said. "I'm sure no-one would notice a plain, unassuming woman such as yourself, sitting in on one of my awesome presentations." That earned me a playful smack on the bottom, and a firm 'now don't be cheeky' look from Rachel.

As we reached my office tower, Rachel squinted up at the tower block.

"Have I ever even been to your offices?" She asked. I had to admit she hadn't.

"Well then," she said, simply, "lead the way. I'll at least come up the lift with you."

My office was on the tenth floor, and the trip up in the lift gave us the opportunity to arrange a time to talk on Saturday about the rules for Sunday.

As I stepped out of the lift. Rachel stayed behind, and gave me a short wave. "Well, talk to you tomorrow then, and good luck for that presentation." I smiled back. I'd thought ahead and brought the USB key with a copy of my presentation to lunch. All I had to do was head into the presentation room, and wow my audience.

As I turned to head off, Rachel called after me one last time. I turned around. The lift doors were still open, and Rachel was in the back of the lift car, positioned so that only I could see her.

Suddenly, with one slow yet sultry movement, she opened her rain coat with two hands. My mouth dropped open, as the coat pulled apart. My heart began to pound, and my eyes felt like they were about to fall out. Standing in front of me, rain coat now opened wide, a half-naked Rachel did a sexy little shimmy.