Glory Hole Ch. 03

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When I first saw her, I just knew that she was Anne. She was everything I had imagined, but better. She was tiny, five feet tall at the most, and with a slim figure. Rick had said she had the face of an angel, but that didn't do her justice. She wasn't just angelic, she was beautiful.

As I approached her she smiled.

"Hi Simon, do you like my outfit?" then she moved close to me, before saying, "I was thinking of wearing my school uniform, but I thought that this would be more appropriate."

I was expecting to hear her girly giggle, but here in the wine bar, I only got a cheeky smile. After looking her up and down, I just said, "Yes," and from the look on her face I could tell that she knew I was pleased with what she was wearing.

I am no fashion expert, but everything she had on was classy, and expensive. Then I noticed her watch, and unless it was a fake, it was worth more than my car.

We stayed for almost three hours, but we only had two drinks each. We were too busy talking. I wanted to go back to her place, but she said no, she had some work to complete for tomorrow. I didn't mind, I knew it was a genuine reason rather than a brush-off.

On my way home I was in a good mood, despite not being able to take her to bed. I had learnt a lot about her. Surprisingly, Anne was her real name, and yes she was actually twenty five. She came from a very rich family, and had been privately educated at a rather posh school. Working at The Tavern was purely for fun, her real job was something to do with finance. I wondered if her wealthy parents knew what she did in her spare time. This was definitely an unusual relationship. It had started with me fucking her anonymously, and now I was getting to know her. I had to smile, it was the wrong way round.

When I got home, my Sister was in the kitchen. Without saying anything, she pointed to the table, then she smiled. I shook my head, but I knew she was just teasing. Mother was in the living room, and Father was upstairs, so there was no way we could do anything, even if we had wanted to.

The next day I was half an hour late getting into work. When I saw Victoria coming towards my desk, I decided that I was going to blame it on the traffic, but really it was because I had just got up late.

"Simon, I hope you can stay late tonight?"

"Of course."

Then she left, and I was thankful that my flimsy excuse wasn't needed. But I had forgotten about the promise I had made yesterday. I was planning to call Anne, and arrange to meet her again, but that would now have to wait.

At five, people started to leave, but I kept on working, waiting for Victoria to come and get me. It was almost six before that happened.

"Sorry to keep you waiting. I had some other stuff to finish first."

When we got to her office, the table was covered with papers. She quickly tidied them up, then she went to her desk and got a large folder out of one of the drawers.

Holding it up, she said, "This is what we will be working on."

Thirty minutes after starting on it, I was beginning to think that this was the only reason she had asked me to work late. After another hour, I was convinced.

"Let's take a break."

I was the junior, so I went to get the coffees. When I got back, I was surprised to see that the blinds were now closed.

"This next part is confidential," then she paused, before adding, "We don't want anybody looking in."

I nodded, that sounded sensible. But when she locked the door, I thought that was overkill. However, when she then stood in front of me, and leant over the desk arranging papers, and at the same time wiggling her bottom, I knew that locking the door was necessary.

Sometimes you can get the wrong signals from a woman. You think she is coming onto you, but she isn't. In this case there was no mistaking what Victoria wanted from me, but I hesitated. I thought about Anne, then I thought about the men she would be seeing at The Tavern. If she could fuck other people, then I could as well.

When I put my hands on her bottom, she placed her top flat on the table, then she opened her legs. I quickly put a hand up her skirt, expecting to feel her knickers, but instead I touched her naked cunt. She had planned this, and she was ready. I think she was expecting me to just fuck her, but I now had plans of my own.

"Turn over."

"No."

"I am going to lick your cunt, then I am going to fuck you hard with my big cock."

She gasped, but I think it was because of what I had said, rather than because she was excited.

"Do it."

I had said it with authority, and it had worked. She was now getting up. As she positioned herself, I took my cock out. A few swift strokes with my own hand got it fully erect, and I made sure that she could see it. She was now looking at it, and I could see the apprehension on her face. I knew what she was thinking. Was it too big for her? Perhaps, but in a few minutes she would be begging me to fuck her with it.

I started by pushing my tongue into her opening, as far in as possible, then I sucked on her lips. They were not as big as my Sister's, but still a nice size. Then I went for her clit. I had always thought that her best feature was her long legs, but I had discovered a hidden gem. It was big, and it was getting bigger as I sucked on it.

"This is so good."

It was for me as well. Then I started flicking it with my tongue.

"But that is better."

Now that I had found what she liked, I kept on doing it. After another minute I noticed her breathing heavily, so I eased off. As I continued, I could tell that she was heading towards a climax, but this time more slowly. It took nearly twenty minutes before she was breathing heavily again, but this time I didn't just ease off, I stopped. It was time to fuck her.

The first few inches went in easily. Good, she could take the width, but could she take the length? Yes, because I was now up to my balls in her.

"Are you OK?"

"I think so. You are twice the size of my husband."

"Do you want me to take it out?"

That got a quick, "No," then she followed it up with, "I want you to fuck me with it."

It's always best to give a woman what she wants, especially when she is your boss.

I started slowly, then I couldn't hold back. In less than a minute I was giving her long strokes, at times almost coming out of her cunt when I pulled back. She was doing well, considering that she was only used to five or six inches. She was taking it all, without complaining. This was a woman that needed a big cock.

All good things have to come to an end. I would have liked another five minutes, I would even have settled for two, but she was now climaxing. My boss, that was always under control, was letting herself go. The blinds might be closed, and the door locked, but if there was anybody outside they would be in no doubt about what was happening inside. As her orgasm faded she made less noise. Eventually she was silent, and that was when I flooded her cunt.

After leaving the room for a short while, she returned. Now she was composed, it was as if nothing had happened. It only took us another fifteen minutes to finish the work.

When I got home I called Anne. No, she wasn't free tomorrow, but then after some giggling, she said, meet me at that wine bar at seven. I was confused, it had been no, and now it was suddenly yes. What was going on? She wouldn't tell me, even when I begged her.

I got there twenty minutes early, but she was on time, almost to the second. I knew that because while I was waiting, I was constantly looking at my watch. I gave her a quick kiss on the cheek.

"What do you want to drink?"

She shook her head, then said, "We are not stopping. We are going to The Tavern, I am working."

Before I could say anything, she took hold of my hand, and started to walk out. I now understood. She wasn't free tonight, so if I wanted to see her, or rather fuck her, it would have to be where she worked.

When we got to The Tavern she surprised me again, because she took me to the back of it, to where the girls entered. As she unlocked the door, she put a finger to her lips. Inside was a corridor, with four doors leading off it. She went to the end one and then gently knocked on it. The door was quickly opened. She then went in, and I followed behind her.

"Simon this is Lizzy."

I don't know who was more surprised, me or Mother, but I was the first to recover.

"Hi."

I just got a nod from her. Anne must have noticed my discomfort, but she didn't say anything. She had probably put it down to the fact that Lizzy was naked.

Turning to me, Anne said, "I am working with Lizzy today. We thought you might be interested in joining us. And if you are a good boy, we might let you join in," then she looked at Mother, before adding, "She has told me all about you. And how she likes to pretend you are her Son."

Mother looked uncomfortable again, but she tried to hide it with a smile.

As we waited for the first visitor, I kept glancing over at Mother, trying to gauge how she was feeling, but it was impossible, I was getting nothing back from her.

After a few minutes, we heard the door opening.

"Hi I'm Lizzy. Who are you?"

"It's Albert," then he paused, before continuing with, "And I'm desperate to fuck you."

I watched as he did that. Anne didn't bother joining in, and Mother looked as if she was just going through the motions. However, when he had finished he sounded pleased.

After he had gone, I declared, "Another satisfied customer," and Anne laughed. Mother joined in, and she appeared to be in a better mood. He hadn't given her a climax, but I think she had still enjoyed it.

Shortly after, we had another one. It was George, apparently a regular with both the girls. When he found out that Anne was in with Lizzy, it made his day. He only had a small cock, barely five inches, but he knew how to use it, and he was enthusiastic. Anne got a climax, and Mother nearly did. I was impressed, especially when they told me that he was in his sixties.

Watching them at work was fascinating, but I wasn't getting any action.

"Next time can I join in?"

They looked at each other, then they both said, "Yes," at the same time. That made them laugh.

When they had finished, Anne said, "But don't make a sound. You are not supposed to be here."

I moved my fingers across my lips, to show them that my mouth was now zipped up. Anne thought that was funny, but Mother gave me a look that said, 'Stop being silly'.

When the next customer said his name, I had to put a hand over my mouth to stop myself from laughing. It was my mate Jim from work. He was also delighted to discover that Anne was with Lizzy.

The panels were now open, and both the girls had presented one of their tits to him. As he worked on them, I joined in. One hand went between my Mother's legs, and the other between my Girlfriend's. When I started fingering them they moaned. Jim must have thought it was because of what he was doing, but it was really my attention that was getting them excited.

I now had two fingers deep up both of them, but I was also trying to push another into Mother. I was finding it difficult to do, until she moved her bottom to make it easier for me. As I finger fucked them, the moaning increased. Surely Jim must suspect something? He may be doing a good job with their tits, but you only get the noises they were making, when a cunt is being serviced.

They let Jim and myself have almost ten minutes, then Mother put a stop to it.

"That was wonderful, but you now need to fuck Anne," then she giggled, before adding, "And after you can have me."

That got a loud, "Yes please," that made both the girls laugh. I almost joined in.

The panels were now closed, and Jim's cock was in the room. As I looked at it, Anne came over to me.

She whispered, "Hold his cock."

I shook my head.

"You don't have to do anything, just hold it."

Reluctantly I did, it was definitely a first for me.

"I love the feel of your big cock," then she looked at me, and grinned, before continuing with, "Would you like me to stroke it?"

I was now shaking my head again, this time vigorously.

"Yes", was Jim's quick response.

His cock was now getting long strokes, with a firm hand, but thankfully my Mother had taken over from me. She didn't do it for long, and when she stopped, it was Anne's turn. But this time she used her cunt.

When he was in her she gasped, then she said, in her girly voice, "You naughty man, fucking me while I am wearing my school uniform."

From the noise Jim then made, I think he almost climaxed. However, to me it was funny, because Anne wasn't in her uniform, she was naked.

He was now fucking her hard, and her little body shuddered every time he thrust into her. It was getting me excited just watching it, and Mother seemed to be enjoying it as well.

When I moved over to her, and whispered, "Bend over. I want to fuck my mummy's cunt," she turned to me and nodded.

She was now ready for me to enter her, but I pushed her top down to get it even lower. Then I parted her cheeks, before slowly pushing my full length into her. It was now a race to see who could give their partner a climax first. Jim had started before me, but Mother was so worked up, that it wouldn't surprise me if I won.

For the first few seconds, while I fucked her, I was listening to what the others were doing. Then I concentrated solely on my task, to give her a climax.

I don't know if it was because Anne was in the room, and I was trying to impress her, but I was like a wild animal. Mother had been fucked hard before, and some of those times had been by me, but this seemed to be on another level. Every stroke was long and hard, and as deep into her as possible. After only a couple of minutes, she was giving me all the signs that she was nearing her climax. Mine was near as well. It was only a few seconds after that, when she reached it. As her orgasm briefly tightened her cunt, it took me over the edge. As she slumped to the floor, she took me with her.

When I eventually pulled out of her, Anne was standing nearby. Looking at me she said, "Next time you fuck me, I want it like that."

I just nodded, then I remembered Jim.

"Has he gone?"

"Yes, one woman was enough for him. It's just as well, otherwise I would have had to stop you and Lizzy."

I doubted if that would have been possible, but I didn't tell her that.

After forty minutes without another customer, we called it a day. Anne went home on her own, but I shared a taxi with Mother. We didn't speak until we were in the house.

"Do you fancy a coffee?"

"Yes, and we need to talk."

She was right, we did. We waited until we were both seated at the kitchen table, coffee in hand, before speaking.

"It was a shock finding out that there is really only one Simon."

"Does it bother you?"

"Now that I am over the shock, no it doesn't."

Then she gave me a stern look, before saying, "But don't ever tell your Sister."

"Why?"

"What she likes about it is that she gets to have sex with you, without you knowing that she is your Sister. You knowing would make her feel guilty."

My face was now serious, but I desperately wanted to laugh, what she had said was almost word for word what my Sister had said about her.

However, somehow I managed to keep it in, while I solemnly said, "I understand."

"And if you are wondering what happens next?"

I certainly was.

"We carry on as normal."

This time I couldn't keep it in, but I did wait until she was out of the kitchen.

I was now laughing, almost uncontrollably. What we were doing could be called many things, but 'normal' was definitely not one of them!

--

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16 Comments
Sexy_Bear1Sexy_Bear1over 3 years ago

I love this series! I'm glad to see you've added to it since the last time I looked at it. I'm reading it again just because I liked it so much the first time.

AnonymousAnonymousover 3 years ago
What the hell happened

I mean at first she only had three kids, she even said it's a good thing we didn't have four. there was only John, Paul, and George. where the hell did simon and cloe come from.

DUBLXLDUBLXLalmost 4 years ago
Twists

Creative diversions, keep going, sounds like his new girl has plans for him.

animal99animal99about 4 years ago

I thought you'd be writing a typical "glory hole" story but I was impressed to find you didn't and instead gave me a wonderfully, creative story that made me laugh and turned me on, as well. I'm only on the 3rd installment but I am looking forward to reading future chapters! Thank you for not making it boring or full of cliches.

AnonymousAnonymousover 4 years ago

I loved the story. Well done. If you should decide to do another chapter, a wicked kink would be that Anne's mother was Victoria. Imagine Anne taking Simon home and Victoria's face when she sees him. You could even have him taking turns fucking each one.

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