All of my stories are written for ladies, and reflect the fantasies they ask me to write for them, this is the first that is for a stranger, and it has been very erotic putting her desired story into words, I hope there will be more of Caroline's Adventures.
Caroline was in the office, it had been a long, hard few days, but the end was in sight the contract would be approved soon. She was keeping her head down today, yesterday when her boss had said he could not stay late because he was picking up his new Porsche, she had made a joke about it making up for his tiny penis. The whole office had laughed but he was not amused, and whispered to her that she would pay for that remark.
Caroline really did not understand that, she knew it was not near the mark, about 6 months ago when there was an attempted break in, she had responded to it as a key holder, as had he. He came running up the road in Grey sweats and t shirt, he said later that he had been at the gym when the alarm went off. However, when he ran up the road his big muscly body, which was normally hidden under a suit was clear for all to see, he was a massive man, with little or no fat. What really had got her attention though was his pants as he ran, there was what was obviously a massive cock swinging in those sweat pants, it was visible with every stride he took.
Caroline was a happily married women, and would never entertain the idea of cheating, but she had fantasied about that cock a few times since, his build didn't do any harm to those fantasies either, and the grey hair did suit him. She hoped her husband looked that good at 50 something.
Caroline was thinking about it again, when Jeff appeared at her desk.
'Nigel, wants you and I to assist with building the presentation tonight,' he said, '6pm his office.'
'No problem, will be there,' Caroline said, not happy at all, she had hoped to spend the evening with her husband. She picked up her phone and text him, 'Hi Honey, I have to work late, we have the presentation for procurement to finish today, will be a little late.' She liked 'little late' it covered a multitude for sins, from 30 minutes late home to 'a little late at night' for when she walked in at 11.
Jeff was hanging about, 'What Jeff?' she said with no patience in her voice.
Jeff looked at her for a minute then said, 'he really is not happy with you.'
'I know the penis joke yesterday went down badly,' she said, 'what's new, there are 4 or 5 of my jokes a week that piss him off, it will be fine.'
'If you say so,' Jeff said in a voice that suggested he knew it would not be.
'Fuck off Jeff, I have work to do,' she fired at him and returned her attention to contract she was going through.
She really hated Jeff, his nose was always up Nigel's arse, and although he was only a couple of years younger, and ridden on Nigel's coattails, he had never been as successful as he thought he should be. He flirted with her constantly, in the beginning she had played along, but he had become tiresome, and she normally ended most conversations with him now by telling him to fuck off.
At 5:50 she decided to go grab a cup of coffee and freshen up before the 6pm meeting, she walked into the kitchen area and put some water in the coffee machine, and left it to filter through while she went to the bathroom.
As she stood in the bathroom, she looked at herself in the mirror, she was not bad for 32, scratch that, she was fucking hot for 32. She puffed out her strawberry blonde hair trying to give it back some of the body it had in the morning after it was washed and dried. See looked herself up and down, she was not tall, but she was slim and there were no muffin tops, or bingo wings, she was a model of what a 32 year old body should look like. Then she got to her tits, she was not a small girl by a long stretch, her boobs were just about as big as they could be without looking odd on her body. She was very proud of them, they always got her attention, much to her husband's dismay.
When she thought she looked as good as she could this late in the working day, she wandered back out, the office was quiet almost everybody had gone home, and those that were left all looked to be packing up to go. She grabbed the coffee and walked past her desk to pick up her notepad and made her way to Nigel's office, Jeff was in there already, of course he was, worm.
The conversation they were having went quiet as she walked in, 'Don't stop on my account,' she said as she sat down in the chair in front of Nigel's desk.
'No, no, we had just finished that is all,' said Nigel, 'anyway, I hope we will be done in no more than 90 minutes, there are just a few things to get straight, something for you to take down, and hopefully things will come to a happy ending.'
'Right, ok,' said Caroline, she was not sure what all that meant, Nigel didn't normally talk in riddles, but the 90 minutes bit was cool, not too late then.
'Before we start there is a couple of things,' Nigel continued,' he stood as he spoke, 'first off young Jeff here tells me that you are telling him to 'fuck off' on a far to regular basis, and that you seem to think being rude to him is acceptable.'
'Well he is an arse, and his flirting is creepy,' Caroline put in.
'None the less it is concerning,' Nigel was on a roll as he started to walk around his office, 'on Monday you made at least 3 jokes at my expense, and then yesterday,' he paused, and was almost around to where she was sitting.
'I know the Porsche joke,' she began.
'Was completely unacceptable,' Nigel bellowed, as he grabbed her arm and shoved her over the desk.
Caroline was shocked, she did not know how to react she was pinned to the desk, before she knew what was happening, Jeff was around Jeff's side of the desk had her arms, and was holding her down.
'What the hell do you think you are doing,' Caroline protested, still not sure.
'We are teaching you a lesson, young lady, you need to be taught some manners and to respect your elders,' Nigel said in a commanding voice.
The next thing her trousers and knickers were pulled down to her ankles, exposing her pert bottom, and more too. With one hand pushing her bottom into the desk to hold her in place, Nigel removed her shoes and then her clothes from her ankles.
'You can't do this,' she said, 'HR will be hearing from me,' she was fighting as best she could but they were too strong, her right leg was pulled to the side and cuffed to something, then the same with the left. She was spread eagle and naked, two minutes ago she was sitting down with coffee, what had happened. Before she had chance to protest again, and she thought of screaming for help, a ball was forced into her mouth and secured.
Nigel walked back around to his desk chair, and took her right arm from Jeff, he handcuffed this to the bottom draw of his desk on the right, then he took her left arm and did the same to left drawer, he sat back in his chair, and appeared to relax.
Jeff disappeared from her view, as Nigel said, 'Now that you are comfortable, and can't answer back, we can talk.'
Caroline fought the restraints but they were not going anywhere. She relaxed, whatever was happening, was happening, and there was nothing she could do about it now, but just wait until she was free, she thought.
'So you think that it is OK to belittle me to the rest of the staff, make fun, say things that I am sure you know not to be true. It's unacceptable, and then you made a big mistake yesterday. You think I have a small penis, you can see for yourself in a minute. Don't worry it's only small you will barely feel it,' Nigel laughed, an evil laugh.
'What is going to happen now, is simple. I am going to spank that bare, petite, beautiful bottom of yours, then Jeff here will follow that up with his spanking.'
Caroline did not think that was too bad, her husband spanked her, we was not really into it, and did it because she liked it, but she knew she could take a spanking.
Nigel must have picked up on her relaxing because his next utterance was, 'Don't get comfortable missy, that is to start, once your arse is so red you will not be able to sit down this week, I am going to show you how big my cock is, then for good measure Jeff gets a go too.'
Caroline tried to say around the gag, 'no you can't rape me,' but it just came out as suppressed noise, as she fought hard against the restraints.
'Don't worry you will be begging for it after the spanking,' Nigel laughed, at her futile efforts to escape, and with that he walked behind her.
She could not see him so had no idea what he was doing, then a slap landed on her left butt cheek, it was a hard slap, and his hand stayed there on her cheek. His hands were massive, he had basically cupped her cheek in his hand, and there was a sting running through her. Christ that was hard she thought as he raised his hand and slapped the right cheek.
After a moment, slaps started to come thick and fast to her left cheek, his hand swooped in an upward motion lifting her cheek from the slap then arcing around to slap again. After about the fourth of fifth one she could not suppress the yelps and they filtered out around the gag. When he stopped her cheek was on fire, 15 or so must have landed, but she was not sure. He moved around and started on the right cheek, using his left hand in the same motion, god it was painful.
Caroline could not help it, this was the best spanking she had had in years, her pussy was tingling, she wanted to play with her clit but couldn't the pain in her bottom grew, but as it did, so did her desire for more, and her desire to cum. As Nigel finished on the right cheek, she felt so horny, she wanted more she could not deny it.
'Don't worry, that was only round one, 'Nigel said to her, it was like he could read her mind, 'Jeff is going to have a go now for a moment, then I will give you the final spanking.'
His hand had not moved away though, and he ran a finger down her pussy to her clit, it was soaking, and when he pressed her clit before removing his hand she shuddered with pleasure.
'See, you are loving it,' he said,' that pussy is dying for my cock.'
Jeff appeared in front of her with a riding crop, where the fuck had he got that she thought, as the evil smile on his face broke into a laugh.
'You took that well,' he said, 'this will really test you.'
She had never been hit with anything like that before and she was now really worried, that could really hurt.
The crop cut through the air with a whipping sound, and crashed into her arse in an explosion of pain, she screamed at the top of her lungs into the ball gag, while twisting this way and that in the restraints.
As soon as she stopped moving the whip cut through the air again and the other cheek exploded in the same agony at the first. She fought again to no avail and collapsed back onto the desk sobbing, she cried out into the gag with every slap of the crop, her whole arse from the tops of her legs to her back was on fire, and she could not shake the feeling that she liked this.
After a period of time that she could not determine Jeff stopped, she lay there humiliated, her bottom was the sorest it had ever been, she didn't even move as she heard the camera go, then Nigel appeared in front of her again, he showed her the pictures of her bottom on his phone, it was crimson, the photo had been taken so you could see it was her.
'I will finish your spanking in a moment, but if you don't moderate your behaviour and jokes, then this will happen again, do you understand?' he said.
Caroline, nodded, the thought of his big hands on her bottom again made her horny, despite the mess her arse was in, she wanted more. As best she could with being restrained, she straightened herself up and pushed her bottom out ready for its punishment.
The first slap landed and she collapsed back against the desk, with a sobbed yelp, her tender bottom might not be able to take this, but she wanted it. She pushed herself back up and her bottom out, the second one landed and she held her ground, the sting of pain went right through her and it made her clit tingle. The slaps came quicker, and she took them, the tingling and fire in her clit growing, she leant into the pain, as slaps came cheek after cheek, she wanted more, and more.
Nigel obviously knew, he kept up at a good pace, firing the pain through her, any touch to her clit now and she would cum, she needed to cum.
Caroline lost herself for a moment in the exquisite pain of her arse, as the slaps just kept coming, held as she was on the edge of an orgasm, she was brought crashing back to reality as Nigel ran two fingers between her pussy lips to her clit, he pressed hard.
Caroline felt all of her muscles tense at once, the orgasm exploded through her, is was like her whole body was her clit, twitching and shuddering, she had never experienced anything like this, she could feel Nigel squeezing and pressing her clit, and did not want him to stop, the electric shocks darting through her body that it caused were amazing. After what felt like a lifetime on a high, slumped against the desk, feeling dazed and slightly confused, what on earth had just happened to her? There were a couple of shakes as aftershocks run through her body.
When she finally focused on what was going on, Nigel was standing in front of her, undoing his suit trousers, they dropped to the ground, and his rock hard cock sprung out of his boxers. It was everything she had imagined from seeing it swing in his sweatpants, it was a good eight and half or maybe nine inches long, but that was not the most impressive thing about it, the girth, oh my god the girth, she had not seen a cock so fat before, even most porn didn't have cocks like that!
Nigel held it in his hand and moved it close to her face, it must be massive, because it did not look small in those huge hands of his.
'See this tiny cock that needs me to compensate so much for, as you suggested, it is going up you now, don't worry, I am sure it is so small you will not feel a thing,' there was an evil sound to Nigel's voice.
Caroline wanted cock, after that spanking, and that orgasm from god knows where she needed fucking, and did not care who, she just needed it.
Nigel disappeared behind her and she felt pressure on her pussy lips, then the head was inside her, it was big, she relaxed into it, and he pushed. It slid up, she was not sure how much was in, but she knew it was not all of it, she felt so full already though, Nigel withdrew and thrust again, she grunted around the gag as more went in, again still not all of it.
Caroline, was in heaven the cock in her was the biggest she had ever had, and the burning of her arse cheeks really seemed to be driving her, she felt twinges in her clit again, as Nigel thrust in and out, he reached around and forced a hand under her his fingers pushing her clit again, but she was sure he still did not have his entire length in.
Jeff appeared at her side, he was filming on her phone, if she had been able to speak she would have said she wanted to see that cock going into her, she tried to indicate that, Jeff looked confused, but from behind her, Nigel said, 'If we remove it, will you be good?'
Nigel's said to Jeff, 'remove the gag, but if she is not good, and keeps her mouth shut she will regret it.'
Caroline had no intention of being anything other than compliant, and as soon as the gag was free, she said, 'make she you film the back, I want to see it going in all the way.'
Nigel laughed as he thrust, and she felt extra effort to force all of his cock into her, she grunted hard with every stroke, and Jeff disappeared from her view. The release of the gag, and the more forceful pounding, drove her closer to climax, she was going to cum again very shortly, and felt her pussy muscles tighten. The squeeze of her pussy obviously effected Nigel, the thrusts became harder still and in significant discomfort, she felt his legs hit her red sore arse, his cock was completely in, she released and said, 'oh god I'm cumming.'
That was it for Nigel his cock driven deep into her, exploded, she felt the cum spurting into her, as she climaxed again, it was more a normal experience not the explosion from before, but very satisfying.
As Nigel withdrew, she felt like she had lost something, she almost felt like she was empty without that huge cock in her. Nigel slumped down in the chair in front of her, his massive cock glistening with her pussy juice, she felt Jeff push into her, she could barely feel him, his cock must be tiny.
After four or five thrusts Jeff said, 'Fuck sake Nigel, your big cock has ruined her, I can't feel a thing.'
'Use her arse then,' Nigel said from the chair.
Jeff withdrew from her pussy, and she felt pressure on her arsehole, the only lube it had was the splash from Nigel fucking her, and whatever Jeff had on his cock from her pussy, and it was not comfortable as the head slipped in.
Caroline, squeaked and winced as Jeff pushed in more, but after about 6 thrusts he was in and pumping away, she grunted with each thrust, his average size cock felt good in her arse, there is no way Nigel's monster would fit.
Nigel stood and presented his still quite hard cock to her, 'Clean it,' he said.
She moved her head to his cock and started to lick her juice from it, taking the head into her mouth a few times, his cock twitched in her mouth several times, then he grabbed the back of her head and thrust it into her mouth, there was a couple of spasms that fired the last of his cum into the back of her throat making her gag.
The gag had caused her to clinch her arse, and squeeze Jeff's cock tight, he moaned, 'oh god that is good,' and she could tell he was close too.
Nigel was already putting his suit back on, but once he was dressed, he slipped his hand under again, and rubbed, her third orgasm started to build immediately, she loved Jeff's cock in her arse, and this was all she needed to push her over the top.
She again collapsed onto the desk, only vaguely aware of Jeff pumping his seed into her arse.
When she came back around, both her hands and legs had been released, and she was alone in the office, laying half naked over Nigel's desk. Her phone was on the desk beside her, she picked it up, there were a number of photos and a video on it, of the last hour or so.
Caroline called her husband and when he answered said, 'Hi Eamonn, I will be leaving in a minute, all done.'
'That's good,' came the reply.
'Yes, we really got into it quickly and Nigel was really happy with my efforts, gave me a big reward.'
'Brought you pizza again,' Eamonn laughed from the other end of the phone.
'Something like that,' Caroline replied, wondering how she was going to explain this when she got home.