A hands on kind of leader...

Wednesday October 28, 2020

Part 1 * Part 2

Jessica walked out of the arbitration meeting satisfied that she’d gotten exactly what her client wanted.  Well client was too formal of term really, girlfriend to be more accurate.  But to be completely accurate, ex-girlfriend.

Which was a little strange to be honest as when they’d gone in to the arbitration meeting they had definitely still been a couple.  By the end thought, well, both had agreed that they didn’t want to be in a relationship.  In fact, both of them had figured that their lesbian faze was pretty much over.

That was weird too, since Jessica had been a die hard lesbian since high school, but by the end of the arbitration session she had to admit that looking at Madison just didn’t do it for her any more.  Not to say that she wouldn’t have participated in a threesome with her, just as long as there was a nice hard dick involved as well.

Perhaps then it was for the best that the arbitrator had given her a pamphlet for one of the other companies that was run by the same people, The Perfect Match.  The literature seemed to be very high end and fancy, guaranteeing that users would find what  the perfect match for them.

She’d seen other internet dating sites, even used a couple of them, but they always failed to live up to their own hype.  But for some reason, this time, she felt like she had hope for it.


Jessica scrolled through the profiles and was impressed.  Impressed at least with the exclusivity of the site, she recognised some of the men on it as the most eligible bachelors in the city!

Something in the back of her mind nagged at her though, was she good enough for this kind of site?

She quickly took stock of herself, she wasn’t thin per say, having never lost those college 15 that she’d put on, but she wasn’t fat by any means either.  And her chest was alright, none of her previous girlfriends had complained about it at least.  But her style did leave a little bit to be desired she guessed.  Standing up she walked over to her closet full of power suites and professional attire and frowned a little bit.

Perhaps she could use some colour in her wardrobe that wasn’t black or grey or blue, but that was a minor thing really.

She walked back to her computer and continued browsing until a pop up appeared, “Hi, I’m Mindi, your personal VIP concierge!  Some of our members don’t make their profiles public and one of our VIP members has matched with you, if you’d like to see more about him, just click here to see his profile.”

She hesitated for a moment but eventually click on the link and a strange flash came over the screen for just a moment.


Jessica pumped her legs hard on the stationary bike as the sweet ran down the back of her neck.  She’d forgotten how hard it was to workout, she hadn’t done so since she was on the track team in high-school!

With a final push the count down timer finally came to an end and she let the spinning pedals slow down and take her legs up and down by themselves as she grabbed her towel and wiped the sweet from her face and back of her neck.

Looking around the gym of her condo building she saw a few other people there, but it was pretty late so they kept to themselves.  She’d never been here before a week ago, but since then she’d been in the gym three times.

Her mind flashed back to Jacob’s profile that she’d been invited to read, on of the many detailed items on his list of what he wanted in a woman was “Needs to spend time at the gym to keep herself in top form”.

It had been such a strange thing to read, but at the same time, so compelling.  Why wouldn’t a woman want to keep herself in top form?  It just made sense.  That’s when she realized that she hadn’t been doing that at all.  She’d been neglecting herself and that had to stop immediately.  She’d gone and bought some workout clothes the next day at lunch and headed to the gym that night.

Jessica stepped off the bike and took her towel back to her condo, satisfied that she’d soon be in top shape for sure.


Jessica looked at her closet and frowned.

Why did she have nothing to wear?

That wasn’t true, her closet was filled with the same business suits and professional attire it always was, but for some reason nothing seemed right.

She quickly walked over to her nightstand and picked up her phone, checking the time, and then dialing work.

“Hey, yeah, it’s Jessica. I’ve got a… personal… issue to take care of and need the day off. Yes, the Robinson account is fine, well on the way to a final settlement. Alright. Thanks.”

Jessica set her phone down and headed back to the closet, picking out the least objectionable outfit she could find before heading out the door with a slight spring in her step and a single thought repeating in her head.

“Needs to be fashionable but slutty at the same time, guys should always be wondering if she is wearing panties under her outfit”


Jessica looked down at her new tits and squealed out in joy as the doctor unwrapped them for the first time. She had known they were going to be great, after all she’d been fondling them for the last several days as she healed.

“Very good, they are healing nicely. Now as we discussed, they will settle a little, but with the high profile implants you requested, they will retain their projection well.”

“Thank you doctor, they look perfect!”

The doctor re-wrapped her bandages after removing the drains and gave her some more instructions. Including the fact that she could resume normal activity in another week if she was feeling up to it.

She could hardly contain her excitement as she left the office, it wouldn’t be long before she could stuff her new tits in to the many tight fitting dresses that she’d bought over the last few weeks and see just how slutty they looked now!

As she walked past the receptionist and towards her waiting Uber, she pushed her chest out and the image of Jacob’s profile popped in to her head.

“Big fake tits should never be hidden, everyone should know they are store bought”


Jessica stared at her computer monitor in horror, “Profile deleted.” was displayed after she’d clicked on Jacob’s bookmark.

She pushed her glasses up her nose and she clicked on the bookmark again and again. He couldn’t have left the service before she’d gotten a chance to message him could he?

She’d worked for weeks to be his perfect match and she was ready now to show him just how perfect she was!

She clicked the link again, the same message appearing again, but this time a pop up appeared as well, “Hi, I’m Mindi, your personal VIP concierge!  It looks like you’re trying to access a profile that had been deleted, can I help?”

“Oh, yes! I’m trying to message Jacob but I can’t seem to!”

“Oh, yes, I see here that he matched you six weeks ago. I’m afraid that he matched with someone else just yesterday and has closed his profile.”

“But… but…”

“I know honey, sometimes it happens. We’re very sorry, but perhaps I can make it up to you. I have a short term dating VIP match who I think you’d fit with perfectly. If you like I can send him over to your place in… twenty minutes? Here, this is his profile.”

Jessica was almost in a panic, but clicked on the link, taking her to Derek’s profile. The only detail in the profile sent a shiver down her spine right in to her pussy.

“Looking to slam my cock between two big fake tits and come on her face. Wearing glasses a bonus.”


Jessica sat on the edge of her bed, her tits on display as her glasses rested at the tip of her nose.

“So Derek… you want to fuck my tits an cum all over my face, is that right?” she said with a knowing smile as she pressed her tits together for a moment and then slide her glasses up to the bridge of her nose.

His smile was his only reply as he stepped over to her, slipped a finger between her tits, and pulled her dress down until her tits popped out of it.

“Do you like them? They’re new. You’re going to be the first man to fuck my new tits Derek.” she said as she pushed her chest out and then together with her hands. Her fingers wrapping around them and squeezing her nipples until they were hard.

Derek undid his pants and let them drop to the floor, Jessica spread her legs and moved forward pulling Derek in between her legs until she could get her tits around his hardening shaft.

“God Derek, I want you to fuck my big fake tits so badly. It’s been so long since I’ve had a real man, a man that would cum all over my face for me.”

She pumped up and down his shaft with her tits, the pleasure of it making her wetter and wetter. Finally, Derek pushed down on her sternum until she was flat on her back. He crawled up on top of her and she held her tits together for him as he slide his dick between the again.

He pumped harder and harder, “Yes Derek! Pump my big fake tits hard! Fuck them, fuck them, fuck them!!!” she cried out as she felt the first stream of cum hit her chin.

“Oh god! My face! My face!” she cried out as she titled her head down and the second stream hit her square in the glasses. By the time the fourth stream hit her, she was cumming hard.


Jessica scrolled away at the site, clicking on profiles and sending messages, but she wasn’t having much luck. Many had very specific requirements that she just wasn’t able to fill.. at least not yet. She already had an appointment at her hair salon on Friday to get her hair dyed blonde, but until then, she didn’t have a match.

Just as she was about to sign off, a pop up appeared, “Hi honey, it’s Mindi again! I have another short term dating VIP match who I think you’d fit with perfectly, do you want to look at his profile?”

Jessica smiled, she’d had a dozen short term matches over the two weeks since Jacob had deleted his profile and she’d been a perfect match for each and every one of them.

She click no the profile link as her pussy buzzed and she wondered how she was going to be fucked when he arrived.

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