All Three Holes

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Şub 15, 2022 // By:analsex // No Comment

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Katie was in the zone — that headspace during sex where all her stress and inhibitions had faded away and she just let herself be taken. The only thing she was conscious of was the growing warm feeling from her loins as a man pushed himself into her. The pleasure came in rhythmic waves, pushing her closer to losing her mind completely She was no longer worried about whether she should or not, only focused on the climax, maybe still minutes away, but still somehow inevitable. She was giving herself to a man who was confident, successful, rich and, somehow this made it hotter in a way she couldn’t explain, old enough to be her father. She had no doubt that her orgasm would be shattering and her moans started to take on a more insistent and encouraging tone.

Suddenly he pulled out of her and she suddenly returned to the real world for just a second, doubts rushing in. Why was she letting her boss’s boss fuck her unprotected less than a week after starting her intern position? That wasn’t the kind of girl she was. He’d called her in, asked a few questions about how she was settling in, then told her to lift up her skirt. She had. Why? He’d stood up from his big mahogany desk, walked round the other side and pulled down her tights and panties in one movement. As he reached between her legs, she was amazed to find she was fully wet. He didn’t seem to be. “Good girl,” was all he’d said as he bent her over the desk, unzipped and entered her.

Damn it! She didn’t want her brain to be turned back on. It had been so good. Why wasn’t he back inside her? Still bent over the desk, she looked around and saw him zip himself up, erection still clearly tenting his expensive suit.

“Mr Collins?” she asked.

“Get dressed,” he ordered. What the fuck, she thought, you have got to be kidding me, but she pulled up her panties and tights anyway.

He picked up the phone and dials a couple of digits — an internal number. “Hi Mandy, is Bill there…yes, I think you can interrupt them, this won’t be long…hey Bill. You want to pop by my office…It’ll be worth your while…The Marston client, bring him too, you must have been in negotiations all morning. Call it a break…okay great, see you in a second.” He put the phone down.

Katie found her face reddening. “I’ll just, err, go shall I?” she said. Damn, a twenty-first century girl should be laying into this cunt-tease for leaving her on the edge like that, but she found herself meek as a lamb. This man controlled billions of dollars, and the fates of whole conglomerates. She still could help but still want this lion to devour her whole.

“Stay please. Don’t talk.” He indicated a leather bound chair at the back of the room, next to the bookcase and far away from the desk. Katie obediently sat and started to nervously adjust her hair and clothes, trying to make herself look like less of a slut to anyone who came in. Of course, anyone who came in would know instantly what she had just been doing. How couldn’t they?

The intercom buzzed, and the secretary announced the visitors — Bill and Mr Sutcliff from the Marston account. There were the usual polite formalities. Mr Sutcliff (no, call me Peter) had met Mr Collins in the summer (yes, at the conference in Paris), but it had been a while, and, no, the deal wasn’t finalized yet, but was close. The pleasantries continued for a couple of minutes and none of them included so much as a glance in Katie’s direction from anyone. Finally, they reached a conclusion and Mr Collins clapped his hands together softly, as if to get down to business.

“So, Bill, I called you down here to ask you a question.”


“Which of our current admin staff has the tightest cunt?”

Bill gave a chuckle, but didn’t seem too surprised by the question. Katie, however, wanted to curl up and die. Bill thought for a second, “Well, if you hadn’t said current it’d be easy of course.”

“Of course, Mindy, but she left to join Goldstein’s last year. Lucky bastards. So, that’s why I’m asking. Who is it now?”

Bill shrugged. “Not much in it. Penelope’s the best overall package, but you couldn’t say she was all that tight. If we’re just talking about the cunt itself…Rebecca from IT, but she’s only any fun if both of you are drunk, as I think we all know.”

Mr Collins gestured in Katie’s direction. “I’d like to get your opinion on this young lady here. Intern from Leeds University, joined us last week. Be a darling would you sweetie, and bend yourself over for Bill, like you were for me just now. Peter, perhaps you’d like to contribute too.”

Katie couldn’t believe herself. She should walk out, of course she should. Slap his smug, sexist face and then sue the company for every penny. She didn’t. She hesitated.

“It’s okay. We’re all friends here. No need to be nervous.”

Katie blushed, but stood up. She brushed past both men on her way to the front of the room, pulled her skirt up and her panties back down and bent over. What the hell, she suddenly thought, kurtköy escort if she was doing this, she should do it in style. She turned around and winked, “Gentlemen. I await your favourable evaluation.”

She faced forward again. She felt a man behind her, dropping his trousers, flesh started to probe her behind, pushing against her lips then suddenly he was inside her. Bill or Peter? She wasn’t sure.

“Hot damn,” he said. It was Peter then — clients first.

“What did I tell you?” said Mr Collins, “Isn’t the tightest little hole you’ve ever felt.”

Peter was moving back and forth. Not quite fucking, just testing her out. “That’s amazing. Bill, you’ve got to try this.” He pulled out and stepped aside.

Katie braced herself for another cock. Damn, she didn’t usually rack up three in even a year. As he entered, Bill immediately felt different. Larger. Much larger. She let out a gasp.

“Hot damn,” she moaned.

Mr Collins laughed. “See. You were in such a rush to leave, that you nearly missed out on Bill here. Always puts a smile on ladies faces, does Bill.”

“So we’re agreed then. Prime cunt. But what about the asshole.” For a just a second she felt his finger push insistently at her ring. She suddenly slammed her legs shut — with Bill’s cock still inside her, all this did was suddenly make her gasp.

“Bill, Bill, she’s still just an intern. Probably never had a man up there before. She still needs some training. Still, I know what your like. So, what do you say miss? Are you game, if Bill agrees to go gently on you?”

Katie nodded. How did you say no to these people? It seemed impossible somehow.

Mr Collins went round to the other side of his desk, to the intercom again. “Susan, could you join us please. Bring the lube and the party bag if you would.”

“I’ll be right with you, Mr Collins,” the intercom crackled.

Katie was mortified. It was one thing to be fucked by three different men — one completely crazy, unbelievable thing — but just one thing nonetheless. It was quite another to let another woman, a peer, see her in this position. Her reputation would be destroyed by the rumours.

She started to stand up, but Mr Collins was suddenly there behind her, stroking her hair. “It’s okay dear, don’t be nervous. We’re just going to have a bit of help to get you ready.”

Susan entered. Katie had seen her on the way in, but not really taken any notice of her. She was an attractive enough woman, though nearing thirty and just starting to put just a little bit of extra weight. She carried on old style doctor’s bag and a purple bottle.

Mr Collin’s smiled at her. “Susan, could you prepare Ms Lewis here for anal sex please. Take your time, she’s new and quite nervous.”

“Yes, Mr Collins.” She came over to the desk where Katie was still bent over. She put the doctor’s bag on the desk and pulled out a disposable plastic glove which she put on her right hand. It took her a moment to awkwardly straighten out the fingers. She poured a drop of lube onto her index finger, then gently spread it around with her thumb.

“Now, Susan, I’m just going to dilate you a little bit. The lube will be a little bit cold, but I just want you to relax and we’re going to take as long as we need to get you ready.”

The first touch of the finger on her hole was indeed cold. Susan moved it around her crack, spreading the lubricant gently around and above and below the hole.

“Whisky, gentleman?” Mr Collins went to the display cabinet behind his desk and pulled out a bottle and three glasses. “So, what’s the hold up on this deal? Government not playing ball?” The men retreated to the other side of the room, and started to talk shop.

“Ok, darling, I’m just going to stick a finger in, and start to work you loose.” Susan’s voice was calm and reassuring, but at the same time weirdly professional. She pulled the glove tight again and added just a little more lube to her finger. Twice she pushed gently, like pressing a button. The third time, the slid in just a millimetre. These were new sensations for Katie and she gave out the tiniest little yelp.

“Do you think we should offer the girl a drink?” Katie heard Bill muse from the back of the room. “Might help her relax a little?”

Susan was gentle moving her finger at this point, back and forward by mere millimetres, but also round and round, widening the hole.

“I wouldn’t,” Mr Collins replied “she probably has data entry or some such to do this afternoon and we wouldn’t want her getting it all wrong.”

“Good point, good point…mind if I have another? No you stay there, I’ll get it.”

On his way over to the desk, Bill stopped behind Katie for just a second, taking in the view. “Say, Michael. How about we go for a full three-holer? Been a while since we did that.” That was the first time Katie had heard Mr Collins first name.

“Hmm, yes. When was it. That conference in Tokyo. The little Vietnamese girl, wasn’t it.”

“That right. God aydıntepe escort that was one hell of a night. Peter, you would have loved it. Totally uninhibited. Come to think of it, was she a pro or was she part of the hotel staff?”

“I know we paid her like a pro in the end, but I think she was one of the waitresses.”

Katie wondered if she should ask what a three-holer was. The basics were kind of obvious, of course, but she wondered about the details. Would it be all three men each in a different hole all at once? Would it be each man trying out all three holes? She kept quiet. She’d moved far beyond any kind of informed consent. They would do to her what they would. Increasingly, she was sure she was going to love it.

“Okay, honey. So now I’m going to be going a bit deeper. Just the same finger.”

Then Susan’s voice dropped to a whisper. “I’m also going to be checking for cleanliness. Mr Parish is not going to be wearing any protection, so it’s important that we keep the passage unobstructed for him. Did you go to the loo this morning?”

Katie was incredibly grateful that she had. “Uh-hu,” she said.

“Okay. That’s good. There shouldn’t be too much, but just let me check.”

The finger went deep. With a couple of strokes, it was all the way in. Now Susan started to bend her finger, probing round the hole in all directions. She was methodical and precise, checking all the angles. Finally, she said, “I think you should be alright.” Katie wondered if that was it. If she was officially deemed ready.

Susan drew the finger out. She inspected the glove for a second. Katie wasn’t sure what if anything she’d seen, but she took it off, wrapped it in a tissues for a box on the desk, and threw it in the bin. She then put on another glove and lubed up again.

“Ok, you’re doing great. We’re going to go for two fingers now. It’s all about loosening you up as much as possible.”

Despite what she had said, for the first thirty seconds or so, it was still just the one finger. Then, as she withdrew one stroke, Katie felt the second finger start to press in on her ring. It didn’t go in at first and Susan didn’t force. With the rhythm unbroken, she kept moving the first finger back and forth and for six strokes didn’t increase the pressure on the second at all. On the seventh stroke, she pushed just a little bit harder and both fingers suddenly popped inside her. Katie let out a scream.

“God damn Susan. Don’t make her cum yet. That’s our job.”

“No, Mr Collins.” Susan said in a respectful voice. Katie didn’t need to look backwards to know she was smiling though. In any case, it was now clear to Katie that Susan was no longer just probing, or exploring or loosening, she was finger-fucking her.

“That feels….amazing!” Katie said. She blushed. “Does that make me a lesbian?”

Susan laughed. “No, not quite yet.” The way she said it suggested that if Mr Collins wanted Katie turned in that way, Susan would have a conversion process all ready to go.

And then, for the second time that day, Katie was back in her zone. There were no more residual worries about what she was doing or why she was agreeing to do it, just the touch of another human being. She wasn’t worried about it being her first time having anal sex. She wasn’t worried about it being her first time with a woman, or if it even counted as a first time. She was lost in sensations.

After some time, Katie had no idea how long, Susan pulled out again. “I know you were enjoying that, but we’re ready for stage three.” God, thought Katie, how many stages are there and how much more intense can they get?

Susan went back to the doctor’s bag, pulled out three objects and arranged them on the desk. They were butt plugs, in three different sizes. The first one looked small, not much wider than the two fingers she’d already taken. The second one looked, well, okay. Maybe she wouldn’t have thought so ten minutes ago, but it now looked manageable. She didn’t want to think about the third and largest one.

“Okay,” said Susan, “These should be clean, but you can never be too careful. I’m going to give these a thorough wipe over.”

Again, she reached into her back and pulled out two sets of wipes, wet and dry, and went to work on each one in turn. When she had finished with each, she struck it down with force on the glass of the desk so the suction pad on the bottom locked it in place. When she was satisfied, she went back to the bag and pulled out another two doctor’s gloves, this time one for each hand. She then put all the other items away, again very methodically and shut the doctor’s bag. She picked up the smallest one and started to lube it up thoroughly. When she was satisfied she moved behind Katie again. This time the object went in without any resistance at all. Katie felt her ring widen and then close again, the base of the plug remaining outside and locking it in place.

“Okay, we’re going to leave that in for a little while, before we move up to tuzla içmeler escort the next level. Mr Collins, we’ll still need a little time to be fully prepared, but, maybe, if you gentleman would like join us, we can make a start?”

The men put their whiskies down and rose from the side table.

“Ah, capital” said Mr Collins. “Now how exactly are we going to do this? I think clothes fully off, as I said, the girl does need to get back to work later, and we don’t want to end up with a Clinton-style dress snafu, do we?”

“It’ll give us a proper look at that body as well. Yes, definitely clothes off.”

Katie wondered if she was going to be asked to do a strip-tease. Instead, Susan reached round from behind her and started to undo her blouse. When that was off, she snapped off the bra, then Katie pulled off her skirt, tights and panties. She stood there naked, apart from the end of the plug sticking out of her. Susan took the clothes, and matter-of-factly folded them and put them on a vacant chair.

The gentlemen were still fully dressed. They hadn’t discussed it, it seemed to be the done thing. All three had very clear erections sticking out of their expensive suits.

“Very nice, very nice” said Peter. “An intern’s what 22?”

“21” said Katie.

Peter hadn’t really been addressing Katie and he ignored her with his next comment as well. “Been a while since I went so young. Mature women have their charms, their skills, for sure, but there’s something about a young body…I don’t know…just, out of the box, so instantly amazing”. Katie wondered what Peter counted as ‘mature’. She wouldn’t have been at all surprised if he meant 25.

“Indeed. You know what though? If I’d been a bit more prepared, I’d have asked

Susan to shave her as well. Still I suppose we’ve already taken up enough of her time.” said Mr Collins. “So, three-holer then. Who’s doing what?”

“Well, Bill has dibs on the ass, that’s pretty clear.” said Peter “Say, do you mind if I avoid the oral. I like a good blow-job, but I don’t always cum from it.”

“Well, I don’t mind. I’ve enjoyed the cunt already enough today. I’ll take the mouth, if it’s not unseemly for the host to go first.”

“Not at all. By all means have at it.”

Mr Collins unzipped. Katie hadn’t really had a good look at his cock before, as he’d been taking her from behind. It was big, but she was also aware of how much older it was than her usual partners’. Again, she hesitated.

“Oh, Susan. Perhaps you could brief her on what’s expected. You see, young lady, there are certain conventions to these things.”

“Certainly, Mr Collins” said Susan. “So, Katie, it’s really very simple. Mr Collins is going to use and ejaculate in your mouth. Don’t think of it as a blow-job, per se, it’s will be more of a mouth fucking. What I mean is that you don’t need to demonstrate any special skills — no licking or teasing. Mr Collins will set the pace, just try to keep your mouth open, take as much as you can and try to keep your teeth away from his cock.”

Susan looked around for a second, found what she was looking for in the corner of the room and then brought it over — a small open waste paper basket with a black plastic bag in. “You’ll need to spit, so do it in here. Try to keep it off the carpet if at all possible. Now, this is very important, once Mr Collins ejaculates you are not to either spit or swallow his fluid. You should keep in in your mouth. Do you understand?”

“Right then. On your knees, girl,” Mr Collins ordered.

Katie obeyed. She bought her mouth close to his dick, opened wide and waited.

He put his hand around the back of her head and brought it in. “Close,” he said.

She sealed her lips around his dick, but otherwise didn’t move. He moved his hips backwards until his penis popped out.

“Again,” he said. They did exactly the same actions.

“Again.” This time, once her lips were sealed around him, instead of pulling out, he pushed forward, slowly but firmly. His dick moved past her throat and started to trigger her gag reflex. As she started to pull away, he put his other hand behind her head, keeping her in place. One second went by. Then two, then three, then four without release. By the fifth second, she spluttered and he suddenly released her. She reached over to the waste paper basket and spat out a huge trail salvia. Suddenly Susan was besides her.

“There, there dear. It just takes a bit of getting used to. Take a moment to get your breath back and then we’ll try again.”

Katie nodded, but then broke out into a fit of coughing. She could feel Mr Collins impatience, though he didn’t say anything.

“Ready to go again dear,” said Susan. Katie wasn’t, not really, but she nodded anyway.

It was exactly the same process. Twice he inserted and withdrew, and on the third time he pushed her head all the way down. This time she lasted ten seconds before coughing, but she also needed nearly twice as long to recover as well.

“Don’t choke her unconscious before we’ve all had a turn,” said Bill.

“Okay, okay,” said Mr Collins “I guess she’s not a natural deep-throater. We’ll have to work on that another day. All right, back in position girl. We’ll do this the easier way.”

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