Working Late Again free porn video

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Phil Cooper was just about up to date with his work now but the prospect of fucking office cleaner Ruby Butcher up the arse meant that he was in no hurry to leave as most of his work colleagues left for the weekend, with it being Friday. He did not get paid overtime, except in exceptional circumstances, so the fact that he was hanging around in the office was not costing his employer anything extra and as he lived alone there was no hurry to get home either.

After Phil had fucked her to orgasm and had, as requested, pulled out before cumming and had also fingered her arse crack and arse hole to induce a second orgasm Ruby had told him that he could cum in her arse the next time that they got together.

The very attractive black woman was almost twice Phil's age, with her being fifty-four, but she was thrilled to have the sexual attentions of a much younger man and in fact, she was thrilled to have sexual attention at all as you was getting next to none at home.

Ruby had not had a cock up her arse for a number of years although at one time her husband Errol quite often inserted his penis there so as she approached the office block at almost eight o'clock she had slightly mixed feelings about taking Phil's sizeable prick in there but a promise was a promise.

She was back to the tight jeans that she had worn when she and Phil first set eyes on each other two nights previously and she wondered whether to bother about wearing any knickers but decided that they might be a good idea for after the event. She was not wearing a bra although it was her rear end that was likely to be getting most of the attention.


On her arrival in the office, the two of them met in a long lingering kiss and Phil put his hands to her substantial backside and squeezed her buttocks.

"I had better get the office cleaned, that is what I am paid for," she said as they broke from their clinch somewhat reluctantly.

There was much giggling as she did her work because from time to time Phil would run his hands over her bent over arse or stand in front of her caressing his own cock over his trousers. Eventually, the work was done so now it was time for play.

It was not long before they were both naked and they were standing with Phil fingering her wet cunt as she stroked his erect penis.

"I have not had a cock in my arse for a long time so it might take a bit of effort," she warned.

"How do you want to do it, bent over or what?" asked Phil.

"Sometimes with my husband, he would sit down and I would lower myself onto him, we could try that," she suggested.

"That sounds fine to me," said Phil who's penis was rigid although it seemed like they were debating something other than a sexual act.

"I have some lube," said Ruby who took a tube from her belongings and started to rub some lubrication around her anus.

She bent over and suggested that Phil apply some more and as he started to she purred because his fingering of her arse crack and arse hole the previous evening had made her cum for a second time.

With her arse hole well-lubed, Phil also lubed his cock  before sitting on his chair and Ruby backed herself towards him before having her large buttocks just above his stiff prick. With Phil holding the base of his cock she gently got her anus against the tip of it before oh so slowly lowering herself and gradually taking him just inside. 

She continued to lower herself and bit her lip as he was taken further and further into her arse before she slowly started to ride his cock. 

"Oh fuck, it is so big," she said as she moved up and down and then increasing her pace once her body got used to having a throbbing penis deep inside her backside.

Phil had only fucked a woman in the arse once before and that was done doggy style but the thrill of having his cock wanked by Ruby's arse was amazing.

"Hell Ruby, this is sensational," he said.

Ruby was getting close to cumming as she continued to move up and down and she panted, "Let's finish it from behind, stand when I do and stay in me,"

Phil did not protest and they delicately moved together until Ruby was bent over the desk but their change of position took Phil's penis deeper into her arse.

"Oh shit," she groaned as she got used to the new sensation of him being further in.

"Fuck me hard now," she ordered and Phil looked down to see his cock appearing from and disappearing into the woman's arse.

He did indeed fuck hard and she wailed, "Yes, yes oh fucking yes," as she came and that seemed to be enough to suck his spunk out and he exclaimed, "Oh fuck, here I cum," as his semen spurted into her arse.

"Yes, fill my arse with your cum," she breathed, still in the throes of her own orgasm.

Phil did fill her arse with his cum and some of it was running out when he finally stopped shooting.

"That was a great arse fucking honey," laughed the still panting and bent over Ruby.

"Yes it was but I wish that I could make love to you in my bed," said Phil as he withdrew from her arse hole.

"I would love that too sweetie, but we can't," said the not very happily married Ruby although if she knew that her husband was fucking one of her friends she would probably not have been rejecting Phil's wish.

They cleaned up a bit and got dressed and Ruby was glad that she had decided to wear knickers because spunk was still likely to leak from her arse hole.

"I can't keep staying late at work or people will be wondering why," said Phil who had now got his work up to date.

"I know honey but it has been a great couple of days," replied Ruby.

"But I want to keep seeing you," said Phil plaintively.

"I would like that too but I don't see how we can," said Ruby, who really fancied this man twenty-six years younger than her.

They did exchange phone numbers and promised to stay in touch and hope that maybe they could get together again sometime.

They did send each other some very suggestive texts over the next week and Ruby was seriously tempted to take up Phil's offer of a night of lovemaking. She sort of convinced herself that she had not actually been unfaithful because the first time Phil had pulled out before spunking and the second time he had only cum in her arse so that didn't really count.

It was again Friday so it was a week since Phil and Ruby had seen each other and Ruby was in town. She saw one of her friends, Cheryl Morris, and had a lengthy chat with her.

A little later you saw another friend, Shannon Holford, "Hello Shannon, I have just had a chat with Cheryl and she seems very pleased with herself."

Shannon froze for a moment with her mind in turmoil, "Shit Ruby, you really don't know do you?"

"Know what, what are you talking about?" said a confused Ruby.

"I thought that you must have known," said Shannon, without answering the question.

"For fucks sake Shannon, what are you talking about, you are freaking me out?" said a flustered Ruby.

"Ruby, your Errol has been shagging Cheryl for months, we all thought that you knew," blurted Shannon.

It was now Ruby's turn to freeze, "No I didn't fucking know, why didn't someone tell me?" she said feeling let down by her husband, her now ex-friend and all of her other friends that knew.

Shannon and Ruby went for a coffee and, with Ruby occasionally sobbing, Shannon explained that it was common knowledge that Errol fucked Cheryl twice a week and Shannon was amazed that Ruby did not know.

"Twice a week he tells me that he goes to the pub to play cards and darts with his mates," said a bewildered Ruby.

By the time that she and Shannon had finished their chat, Ruby had come to terms with the fact that her husband was getting sex elsewhere and she was going to confront him about it that evening. She herself was not happy in the marriage but she was still hurt by her husband's actions.

She had cooled down a lot by the time that Errol got home from his work and she still had some time before she had to go to do her office cleaning, "I had a chat with Shannon Holford today," she said almost matter-of-factly.

"Oh, how is she?" asked Errol although he was not too bothered about the answer because he was not too fond of the woman.

"She is fine, I also chatted with Cheryl Morris," said Ruby, keeping calm.

This got Errol's attention and Ruby noticed that he momentarily looked a bit stunned, "Is she ok?" he asked trying to sound equally disinterested as he had about Shannon.

"You should know because you are fucking her," answered Ruby.

Errol did not attempt to deny it and although they had an argument, it did not get all that heated but Ruby ended it by saying, "I am going to work now but I might not be back home tonight."

"Where will you go?" asked Errol but he got so answer.

Ruby got to the office and before she started the cleaning she rang Phil's mobile.

"Hello Ruby, good to hear from you, how are you?" he asked.

"I am not too bad but you know what you said last week about what your wish was?" she asked.

"About making love to you in my bed you mean?" he asked hopefully.

"Yep, would you like to do it tonight?" she asked and felt a tingling in her cunt as she said the words.

"Fuck yes, but what has changed?" he joyfully asked.

"I will tell you later, I am in the office now but can be with you in an hour or so," she replied.

He had told her the name of the road that he lived in the previous week so only had to tell her the house number so in about an hours time Ruby Butcher was going to be going to Phil Cooper's house to make love.
 

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I have been thinking and fantasizing a ton lately about meeting a girl who gets turned on by sissyboys.. Ideally, this girl would really get off on taking a boy with feminine features, such as myself, and totally feminizing and emasculating him.. I want a girl who doesn't just tolerate it, but who gets really turned on by dominating, teasing, and humiliating a sissified male. She sits me in front of a mirror and give me a makeover, applying generous amounts of makeup.. She makes comments on how...

3 years ago
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BlankSlate The Teacher

Blank-Slate: The Teacher By: Paradox "I just don't get it, Lisa," John Wilkins said, sighing. "I try to be understanding of these kids, I try to give them every opportunity, but..." "John, listen," Lisa said. "You can't, like, blame yourself, y'know? Butch and Jimmy are, like, total meatheads. They don't care about learning and stuff." "Isn't it our job to make them care?" John asked. "In a perfect world," Lisa said. "Maybe I'm, like, a little biased though. Those two punks...

3 years ago
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A special box of chocolates brings more than one guy expected

Billy was ready for tonight. He had been ready for as long as he’d been going out with Leslie. He was sure tonight was the night that she was finally going to let him fuck her. And was he ever ready. Sure, she had given him a hand job here and there, and she had let him feel her up on countless occasions. But she hadn’t ever let him go all the way with him yet. For the first couple of months, he figured this was to be expected. They had both been raised in a Mid-Western town all...

2 years ago
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Chocolates for sale Part 3

Introduction: Becky comes back to sell more chocolates with her friend After lunch Becky and Nicole hopped on their bikes and cycled out to my place making plans as the came. If my wife came to the door they would try and sell her some chocolates and ask about chores in order to earn some spending money. Becky told Nicole not to let on that she had been there the evening before as she didnt know what I might have told my wife if anything. But how are we going to get Mr. Thomas to do anything...

2 years ago
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Working Late

I work for a small company and at about 7 o’clock one Thursday evening I was finishing a report that had a deadline for the next day. I was the only one left in the building but it meant I could finish my work without any interruptions. Needing a break I made my way downstairs to the water cooler. That is when I realised I wasn’t alone. My colleague Luke was there also getting water. I greeted him with a smile. He is my favourite colleague, my boyfriend and I sometimes get together socially...

3 years ago
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Working Late

My name is Tom; I've worked in an accounting office for the past twenty years. It has been a great place to work. One woman I have worked with over the past year is an absolute piece of ass. She is what everyone thinks of when they think of HOT. Young sweet ass and gorgeous tits she is definitely nice eye candy. Amber is 23 years old, and absolutely beautiful, she's about 5'5, 115 lbs. She always thought of me as just some nice older man. I always used to think that she'd freak out if she knew...

Straight Sex
1 year ago
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Working Late

I work for a small company and at about 7 o’clock one Thursday evening I was finishing a report that had a deadline for the next day. I was the only one left in the building but it meant I could finish my work without any interruptions. Needing a break I made my way downstairs to the water cooler. That is when I realised I wasn’t alone. My colleague Luke was there also getting water. I greeted him with a smile. He is my favourite colleague, my boyfriend and I sometimes get together socially...

Straight Sex
3 years ago
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  • 10
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Working Late

I was working late again, trying to get my proposal done before the midnight deadline. Just a few finishing touches and it would be complete and my cell phone rang. I knew without looking it would be my wife. She had been patient these last few weeks as I spent lots of extra hours at work, but I could tell from her attitude this morning she was looking forward to the end of it as much as I was. Hi honey, I said when I answered the phone. Hello, dear. Hows it going? she responded. I told her I...

2 years ago
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Collateral Damage A Halloween Story

= = = = = = = = = = = = = = = = = = = = WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain strong or even extreme sexual content. All people and events depicted are fictional and any resemblance to persons living or dead is purely coincidental. Actions, situations, and responses are fictional ONLY and should not be attempted in real life. If you are under the age or 18 or do not understand the difference between fantasy and reality or if you...

3 years ago
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Collateral Ch 3

The day went by with Klaus seeing about his work, and Jake just observing from the corner he had been placed. Well, it was not exactly a corner, but it definitely felt like it. On the other hand, he was free to stare at the man, and that made up for everything.He had to admit he was pretty impressed. He heard Klaus talking on the phone in a language that he was almost certain it was French. The man seemed capable of switching between foreign languages without a problem, as he was talking to his...

4 years ago
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Collateral Damage

Tales of the Windy City Collateral Damage By The Professor Living in Chicago is not for the faint of heart. That was the first thought that ran through my head the blustery March morning my life began to change. I didn't know it was about to change, but maybe most of us aren't truly cognizant of that moment where everything either comes together or goes to hell. If we did, we'd do something about it before it got out of hand one way or the other. The sidewalks were still fairly...

3 years ago
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Pilates with a difference

Her heart began racing as soon as she heard his knock at the door. This was a gamble, but she had confidence in her observations."Come in," she replied. He'd been coming to her for a few weeks now, twice a week, to work on core strength. At first she thought she was just giving kinky meaning to otherwise normal things, but over time it had become very clear. The cane stripes, red and raised, poking out the bottom of his shorts as he exercised. The way his posture and performance improved when...

Femdom
1 year ago
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Pilates with a difference

Her heart began racing as soon as she heard his knock at the door. This was a gamble, but she had confidence in her observations."Come in," she replied. He'd been coming to her for a few weeks now, twice a week, to work on core strength. At first she thought she was just giving kinky meaning to otherwise normal things, but over time it had become very clear. The cane stripes, red and raised, poking out the bottom of his shorts as he exercised. The way his posture and performance improved when...

Femdom
2 years ago
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  • 18
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Special Pilates The Date

Hi, my name is Georgia. I read the story "Special Pilates" and recognized my life. To help all you readers appreciate the story more fully, I decided to continue the story with my own details about the first date with Sam. Watching Samantha walk up to my door took my breath away. Up until the video conversion, I did not ever imagine wanting someone who looked like Samantha. She was dressed in a sharp executive business suit, looking like a power player, going to a meeting or going out...

3 years ago
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Working late

"We have to get this project done tonight!" you say "It can't wait" we're at your desk looking at the figures, they don't look good, we're both frustrated and don't want to be here, it's late and the office is empty. I catch a glimpse of your breast through the buttons of your blouse. I look at your short pencil skirt riding high on your creamy thighs, my cock is getting hard and bulging in my trousers. You spot my gaze and although at first annoyed once you see my bulge you can't help but feel...

2 years ago
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working late

One night I was working a late shift at a truck stop I used to work at. There was a mature woman named, Katherine, cat for short. I was about to get off from work, then she asked for a ride home she told me she didn’t live to far the truck stop. So I agreed to take her home. She told me her son lived with her and might not be home yet and ask me to wait with her because she lived in the middle of nowhere I said fine. I got her home, and as she had said her son was not home yet so I walked her...

2 years ago
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Working late night at my office

That night I sat at my desk in the office.It was very late; but my Boss had asked me to complete my task before going home. I got up and went to the window.I stretched to relieve the cramp in my arms and shoulders.Then I sank back in the leather chair and wondered how I would spend the rest of the evening as my PC was closed down…I sighed, reaching for the small drawer at side of the big desk, searching for the small vibrator I always had hidden at the back. I withdrew that nice sex toy and...

2 years ago
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Life Is Like A Box Of Chocolates

"I am not going to sleep with you Mike so will you please get the fuck out of my office." Snapped Nicola. "I never asked you to." Protested Mike innocently. "I just thought maybe you would like go get a drink somewhere. We could talk about that promotion you are applying for." Nicola cursed her luck that her boss was such a jerk. She knew that a girl with her figure was always going to turn a man's head, but that still did not excuse a married older man offering her a promotion in...

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