A Tryst With The Office Mature Ch 01

Note: This will be a longer story and is based on a true experience, only dramatised mildly to allow me to link into other potential stories. If you want a quick release, this likely isn't the story for you.

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The clock felt as if it slowed every time I looked at it.

My day was so dull, nothing was happening. Everyone seemed bored. I didn't want to be there. I was stuck in the humdrum of everyday life.

I needed adventure. I needed action. I needed something to distract me.

Suddenly, I was called into my boss's office, which made for a more interesting time; rather than clicking news links and pretending to be busy.

It was that time of the month, I had to do quarterly reviews with the staff. My manager, Iman, a goddess of Indian descent, smiled at me earlier that day as she delivered mine. Her smooth, dark, flawless skin, just radiated as she smiled at me. She wore a beautiful, yet professional scarf loaded with colour and wrapped it around her neck.

"It is quite chilly today, I have to admit.", I said gleefully, "that's a really nice scarf. The colours really suit you."

I caught her off-guard with the compliment.

"O-Oh, thank you. It was a birthday present from my daughters."

"How old are they?"

"13 and 15 this year."

"Oh wow, you don't look a day over, eh....", I thought about my response before responding jovially, and clearly sarcastically.

"28, that's right. Not a day over 28."

"Oh shush. That's no way to talk to your boss, but I am incredibly flattered."

Her smile lit up the room, and her amber eyes got my cock twitching. She was gorgeous. Her hair was jet black, long and silky. She was nicely dressed up, even if a little casual for the day, but you'd never go a day where you wouldn't see her in heels. She was wearing some dark green heels, with some bright denim jeans. Her blouse was a classy green to match her shoes. Then her scarf which draped beautifully over her shoulders, covering her kissable neck. I imagined removing it, and breathing on her sensitive neck, kissing lightly to get her juices flowing. I'd imagine her breathing more heavily as I approached and kissed her ear, just to send her senses wild. I imagined her soft, firm lips kissing me as our tongues danced. The image of her getting so warmed up that she would start to spread her legs so I could palm at her pussy. I'd had many quiet nights at home imagining her gorgeous amber eyes. Them looking up at me, or most specifically, seeing them glow after I'd mentally made her cum all over my face, her sweet nectar dripping from my tongue and chin. God, I was getting hard and having to re-adjust.

She must have been talking, and trying to grab my attention. I was lost, miles away.

"Are you even listening to me?" she asked.

"I'm so sorry. I was completely gone. Let's just say, I am absolutely floored by your eyes, Iman. They are so striking."

My throbbing cock made me get bold. Primal. I wasn't thinking about my environment. She started to blush. Her eyes fluttered like the one hundred butterflies in my stomach. Jesus Christ, why on earth did I say that to my boss? No doubt the conversation would change for the worst now. I'd be hauled into the HR offices, much to my delight with the lovely ladies there, but probably dragged over the coals.

Could this be viewed as some form of sexual harassment? After all, in this day and age you have to be careful. I glanced at the clock again, and time seemed to freeze, slower than before. The icy silence in the air done nothing but serve me to the proverbial wolves. I knew I would be reprimanded.

Iman's lips started to move. I braced for impact.

"I really don't think this kind of conversation would be viewed as appropriate by most-"

"I-I'm so sorry." I interrupted.

"You didn't let me finish..."

I shut up. Frozen in place. I got the sense she loved the slight control she had in that moment.

"Lucky for you, charming man, I am not most people. Oh, you've got me all flustered."

Iman shuffled around uncomfortably on her chair as I slowly came down from the tension I'd built up, assuming the worst. That really was close. I'd landed in hot water before just offering a genuine heartfelt compliment to a rather have-to-be offended lady in the sales department. All I had said was that she dressed really well and had a great figure. That was apparently not welcomed.

I used the opportunity to look down at the floor as Iman re-adjusted and watched her flick her beautiful bare foot in and out of her dark, green heel.

It was such an erotic sight. Moments like this are exactly what have made me develop some form of foot fetish. I just wanted to rub her feet, oil them up and slide my cock between them in a makeshift foot-job.

Fuck sake. I was working myself up again.

"Anyway, my handsome charmer, I was saying that I need you to finish off the last of the quarterly reviews by the end of the week. How many do you have left?"

"Oh, only three more. Thankfully the easy ones. I got the lower performers and difficult personalities out of the way first, so I could have an easy ride with the last ones."

Iman let a really sexy smirk shoot over her face as she repeated my words back to me.

"Well, don't we all like an easy ride every now and then?"

I laughed back at her suggestibility and gave her a lustful, wanton gaze.

Our eyes connected as her amber eyes filled my soul with fire. In absence of the real thing, I knew I would be going home and imagining her beautiful, mocha body sliding up and down my cock tonight. If I even made it home. I could disappear into one of the derelict meeting offices and relieve myself. If not, even to try and seduce her now. There was a lock on the door...

The tension could be cut with a knife and the moment was ruined by some professional, yet inconsiderate cock-blocker as her phone rang.

"I'll let you get back to work..." she offered as a consolation prize.

I left her office with a semi-hard cock, knowing that her eyes were feasting upon me as I stood up. After all, it must be tough, being a doting mother of two teens. Many office rumours suggested her husband travelled a lot. I could only bet she was gagging for some cock.

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I returned to my desk, still clock-watching. I was only an hour into my shift, so figured I would go and start some of the quarterly reviews. I needed to keep my mind off of my sultry boss, not least of all, I had some really good people to chat to. Adam was a guy slightly younger than me, 25 years old. He made it perfectly clear this job was a stop-gap for him before he went travelling. I'd save him to last as it would undoubtedly be the quickest.

There was Suzie, who was a few years older than me at 33. Very girl next door, only the party to a few of my at-home wanks, specifically the few photos on the internet from her Facebook page titled, 'My First Photo Shoot'.

She was a mother to three kids, to three different dads, so pretty easy going sexually. I could probably bend her over the board room table and take her, as we flirted for fun quite openly to the point she even gave me back rubs at my desk and brought me coffee. Pretty inappropriate, but equally quite exciting.

Finally, there was Dayna. She was 53, a mother of 4, all grown up. She was absolutely gorgeous. I found her mildly intimidating because she always carried herself so well. She was immaculate every day. Always dressed a cut about the others, blazers, blouses, skirts, or jeans and heels - much like Iman. I reckoned there was a little bit of womanly competition going on between them.

We had a small office just off from the main work floor that was coined the 'naughty room' by staff, as generally, that office was only used to reprimand people, or as a last resort. It was cold, empty and there was a situation a few years prior with a lustful IT specialist and my old boss who was fired for her interpretation of what the 'naughty room' was.

I started with Dayna. I was so sexually frustrated from my exchange with Iman, that I thought a meeting with Dayna would be a suitable alternative.

I called her into the room, and she brought her thermos flask of coffee with her, a notepad and pen. She was always so prepared. There was something quite sexy about her confidence and character. She walked with a straight back, took powerful strides.

I shut the door behind us and she sat down at the table. God, she was beautiful. She had a dimple on her left cheek as she smiled, full, white teeth and clearly looked after herself. How on earth was she 52? She had the face of a 30-year-old and the body of a 20-year-old. I knew her eldest son as well. He was in the same high school as me, a year below me. The subject of many teens fantasies.

"So, Dayna, how are you?"

Her smile immediately changed. There was a sadness in her eyes.

"I'm ok, thanks. You?"

We exchanged a few pleasantries and I sensed her distraction. She was so far from ok, but I felt I couldn't respond. We continued with her staff review, and I loaded on the compliments just to try and make her feel better.

"The thing is Dayna, anyone I ever talk to in our client base, they sing your praises. They want to talk to you. You conduct yourself impeccably, your work is flawless and it's a genuine pleasure to know you. Keep up the stunning work."

She started to tear up, "that's really so nice of you. Thank you!"

"I hope you don't mind me saying though, it's clear that something is on your mind. You don't need to answer, but is everything ok at home? New boyfriend still going strong?"

She burst out in tears to the point I lowered my voice to soften my tone.

"I'm sorry if I'm prying, but if it helps, you can talk to me. What is said in this room, stays in this room."

She apologised for the unprofessionalism and I reassured her. I get very uncomfortable around an upset woman, a crying one even less so. In a bizarre look, her mature beauty was so alluring, that she even made crying look good.

"I need some overtime. I need the distraction, and the money.", she pleaded.

"Money is fine and well, but the distraction... are you in trouble? Are you safe?"

My mind went to the extremes, wondering if she was avoiding someone at home.

"Oh, it's nothing like that. I've just been so desperate for companionship that I'd stretched myself financially. I've fallen behind bills, I've got people knocking at the door saying they'll seize my assets. I'm stuck. I just don't know what to do."

"Do you mind me asking how much, is it a lot? Sometimes, just writing down your outgoings, and stripping back on luxuries, you can find you can save, and recover a little."

"It's why I stopped smoking. Saving a fortune already."

I awed at the fact she smoked, yet maintained such a healthy look and white teeth.

"I'm sorry, you don't need to hear about my woes. I've not told anyone. I didn't even tell Kevin, before we split up."

My mind went to a dark place, despite her vulnerability. I was in a mature mood given my interaction with Iman. I had to shake myself out of it.

"It's genuinely ok, Dayna. If I can help, I can. I don't know how much OT we have going, but whenever we need extra, I'll promise you that you'll be the first person I speak to."

"I just don't know what else to do. I feel embarrassed to even say it, but I secretly even did a little cam-girl work after Kevin left, even before he did. I just can't afford anything. I'm trying online dating too, to try and get some kind of connection."

My cock twitched. Dating, ok. Back up.... cam girl work? The thought of her gorgeous body on cam, paying her to do all the things I'd always dreamt of. Christ, I had to find her username... a fine way to treat myself.

We spoke, and continued to have a deep conversation about money, life and problems. I suggested she sell her house, and downsize as it could help clear everything and give her a clean slate. I even offered to loan her some money, knowing I could help. I didn't care much for money.

"I couldn't accept that."

"I have absolutely no problem doing it, that's why I offered. Dayna, you are a beautiful, mature and intelligent woman. I absolutely love the conversations we have, the friendship we've built over the years. I have absolutely no problem with cam-girls, or that lifestyle. Sex-work is pretty healthy. And it pays well."

She started to blush, as her eyes widened. Dayna probably hadn't realised she dropped that bombshell. I recognised the reaction and acknowledged it.

"I'm sorry to say it so openly. I promise you, what you told me stays with me. You're in a vulnerable place, and maybe you'll have a little more confidence now someone knows about it. It's not a secret now. It's certainly not a secret to be ashamed of. I'm not judging you."

I then felt fairly bold to confess too.

"In fact, I've used those services before. Even starred in a little video with my then partner."

Her demeanor changed.

"Now I am the one who should be apologising for being so open about it."

She dried some of her tears on the end of her sleeve, and I felt bad about not having any tissues or anything to offer as a gentleman. She then started to ask me about my experiences with cam-girls.

I told the truth. I said I had a partner who was making a lot of money on cam-work, and as they were exhausting themselves so much during the day, sexually, I participated on occasion. Particularly when people would pay to see my girlfriend getting fucked. It was quite a rush. I wasn't jealous, but I even subscribed to my girlfriend's camera. I thought it would also be quite sexy to get her worked up and then go and surprise her.

The relationship ended when she spent so much time on camera, and with certain 'whales' that she stopped investing in our relationship, even getting to know them far more deeply. When I spoke to her, and asked if we were ok, she said yes. But I knew. I knew we weren't.

So, I started a session with her on a new profile, and she told the user, me, that she was newly single and looking for a new sugar daddy.

I disconnected the call, then ended the relationship. She was always honest with punters about being in a relationship. So it's clear she was more concerned about the person who would be prepared to pay more for her time and fly her around the world. A shame, but I hold no hard feelings. I admired her making a living, even if it cost us our own relationship.

Dayna was transfixed. She listened intently and started to talk about how she had such a dry love-life as she raised the kids. It was missionary only, wham-bam style with no satisfaction. It served a purpose and that was to her then husband, who spent more time on the road as a trucker than anything.

She said she found it liberating and had thought about escalating her sessions more, doing some filming.

I joked and said, "well, I have experience directing some of the films. Perhaps I could give you some pointers."

She smiled. We wound up the conversation with a few more pleasantries. I said I was getting my hair cut after work, and she offered to do it. She made more 'honest' money as she called it, cutting hair and using her beauty degree to work when she was on maternity years prior, so I took her up on the offer.

If not to spend time with a gorgeous woman, maybe... just maybe... I'd get her cam-girl username, or more.

Suddenly, I'd looked at the clock and three hours had passed. We stood up to leave the meeting room and I politely said to Dayna I would help her any way I can, and she could talk to me any time.

She kissed me on the cheek and gave me a hug, as she whispered, "thank you" in my tingling ears.

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Dayna has offered to come to my place around 20:00.

I used the time to tidy the place up, make it look slightly more respectable, not that I was a very messy person and showered, spruced up with some aftershave to smell nice. Perhaps stupid as she was cutting my hair, I'd likely have to shower again after.

The mind started reeling. I pictured her stood in front of me, her face up close as she observed my fringe and took gentle cuts from me. I imagine just leaning in, kissing her and then a hurried fuck on the chair where she pushed her panties to one side and hadn't even gotten naked.

I was rock hard. The meeting with Iman, then Dayna. I was itching to stroke myself. Itching to feel my cum jetting out of me as my head throbbed from a hard stroking technique.

Oh, she was online dating? I used it as an opportunity to peruse the categories on a few dating sites. There she was. 52, single, looking for companionship. Her username didn't match her actual name, which made sense, but sunkissed68 stuck with me.

Before long, I was typing it into various cam-girl sites, to no success. One final attempt on adultwork.com revealed a hit.

NO. FUCKING. WAY.

It was too much of a coincidence not to be her, but the profile wasn't very detailed. Her image was of a gorgeous breast and dark, hard, nipple. No face pictures. That was it, surely! Last online two days ago. Well, she wasn't exactly inactive. I created an account, added her to my favourites list and checked religiously, even though I knew she was coming to my house to cut my hair soon and probably wouldn't be on.

I checked her main social media account where we were connected and it was equally void of images, bar a few family photos. She was utterly gorgeous, and so were her daughters. Her son, pretty strapping too. Good genes ran in the family, clearly.

It was 19:40, and I couldn't fight the urge any more. I slowly lowered the zip on my trousers, fumbled with my cock and suddenly, the doorbell rang. She was a little early, clearly.

I opened the door and was utterly floored. She'd obviously made some effort, even for a simple and innocent trip. She'd curled her hair so her blonde locks bounced as she walked. Her dimple shown as she smiled. We made a few pleasantries and hugged at the door before I invited her in. The smell of her perfume made my heart skip a few beats. I was totally swept off my feet with the scent.

I asked what it was to offer a compliment but was so fixed on her gorgeous smile and dimple that it didn't register with me.

I took the bag from her hand, full of her hair equipment and just admired what she had on. She had some sexy heels on which revealed her French manicured toe-nails, an incredibly elegant look to match her hands. Her thin, beautiful hands so perfectly made up would be beautiful wrapped around me.

I shuddered at the possibility of undressing her. I knew I would have to ask about her cam-work at some point, but work up to it.

I gave her a brief tour of my home, and then she led me to the dining room, pulled out one of the dining chairs and ordered me to sit.

"Can I get you a drink first, at least Dayna?" I asked almost submissively.

"Later, let's get this mop of yours sorted first."

I complied. I have never been so unbelievably aroused throughout the whole endeavour. To have her touching my head, running her fingers through my hair and making those gentle cuts. It was sensual. I imagined her fingers running over my body, with me reciprocating over her gorgeous curves.

When she came round to my fringe, I was smitten. Her low cut top left enough to the imagination where it was sexy. And when she came up close to my face to observe her work, it was in close enough distance where it was almost tantric.

She asked me a few questions to break the tension and heavy breathing.

"So, what do you do when you aren't at the office, we haven't really engaged outside of it much, beyond work events", she asked me.

Her hands and fingers still running through my hair, sending shivers down my spine.