Glory Hole - Chris's Perfect Job

What do you do when you only have lemons? That's an easy question to answer. You make lemonade!

And that's what I did. But of course, we're not really talking about lemons, or any other type of fruit. It's about making the most of the talents that I have. And, unfortunately, I don't have many.

My name's Chris, and I'm twenty two years old. I like to think that I'm handsome, but nobody else has ever called me that, so I guess I'm not. However, I'm certainly not ugly. Regarding intelligence. Let's say average, and leave it at that. So what do I have going for me, what are my lemons? My family would say straight away, that it's my personality. I get on very well with people. The proof being, that I have lots of friends. However, my girlfriends would probably disagree, and put something else at the top of their list. The size of my cock. It's a real, 'Big swinging dick'.

What do you do when all you have going for you is a charming personality, and a very big cock? That's an easy question to answer. You work for Mrs. Templeton!

I met her a month ago, in a local bar. Despite her being at least twenty years older than me, I was instantly attracted to her. It wasn't just her beautiful face, or curvy body, that interested me. It was also her stylish clothes, and elegant demeanour. She was a classy lady. Two hours later, we were in bed together, and we weren't sleeping!

The sex was very good, and I wanted to see her again. But while giving me a nice smile, she said no. That surprised me. I'd made her come twice, and the second time, she'd actually screamed. So why was it a no? I was confused.

"Chris, I need to tell you something."

It didn't take her long, and when she'd finished, she asked me a question.

"So do you want to work for me?"

Without any hesitation, but with a big smile, I said yes.

"Good, but now that I'm your boss, you don't call me Anne. I'm Mrs. Templeton."

She had just given me my perfect job, so as far as I was concerned, I was happy to call her whatever she wanted.

It was late when I got home, but I called Andy. I wanted to tell him my good news. He must have still been up, because he answered on the second ring. I quickly told him.

"Is this a joke? If it is, it isn't very funny."

"No, all of it's true. Scout's honour."

"But you've never been in the Scouts."

I gave a deep sigh. This was hard work.

"Remember when we were five, and we made that pact. To be best friends forever."

"Are you sure it was with me?"

I just ignored him. It was, and he knew it.

"And we said we'd never lie to each other."

"OK, I believe you. But tell me it again."

I did, but this time, giving him more detail.

"So you didn't know when you were fucking her, that it was an audition? And she now wants to pay you to have sex with members of her club? It seems too good to be true."

"Correct, but she refers to it as, 'Providing the client with the service that they require'."

"And to do that, you put your cock through a hole in a wall."

"Mrs. Templeton calls it, 'A barrier that maintains anonymity'."

"You know what your job really is?"

I didn't, but I knew that he was going to tell me.

"You are fucking in a Glory Hole!"

He then laughed, and I had to join in. He had summed it up perfectly. Mrs. Templeton had shown me pictures of her establishment, and it was indeed classy. No expense had been spared on the fixtures and fittings. It catered for a very exclusive clientele, who paid a lot of money for their membership. However, when you stripped it down to its bare bones, it was exactly as Andy had said. I was going to be working in a Glory Hole.

A week before I was due to start, I went to the club. I had an appointment with Helen, the Manager.

She greeted me with, "We have a lot to do, so let's get on with it. Take your clothes off."

She was a formidable woman, both in looks and manner, so I did as I was told.

"Now stand in front of the screen. I'm going to take some pictures for our website. Don't worry, your face will be obscured."

When that was done, she took a good look at my cock.

"Ten inches?"

I nodded. That got a flicker of a smile from her, because she'd guessed correctly.

"It's too big for me, but we have some clients that prefer our men to have a large penis. And yours is definitely that." Then, after some thought, she added, "I'll put it down as eleven."

She must have seen the concern on my face, because she spoke again.

"Don't worry, they are not going to measure it."

When, after two hours, I left, I'd been given a tour of the club, and all the paperwork had been completed. I now had a pension, and medical insurance. I had a legitimate job, but one that I couldn't talk about in polite company!

On my first day, I was introduced to Simon.

"Hi Chris, I'm your mentor. That's a fancy way of saying that if you screw up, I get the blame."

Then he laughed, and I was happy to join in. Half an hour later, he was more than a mentor, he was a friend. And he had given me some good advice.

"It's all about their needs, and not yours, because it's them that are paying."

"Sometimes, the client will be difficult. Just take it on the chin. As far as Mrs. Templeton is concerned, the client is always right."

"Pace yourself. You can have up to three clients in an evening. Coming each time, is ambitious."

When it was time for my first client, he vigorously shook my hand, and then, as I was leaving, he shouted out, "Good luck."

As I walked towards the room, I remembered some more of his wise words. And I wished I hadn't.

"It happens to the best of us. Sometimes, no matter what you do, you'll find that you can't get it up. That's a problem, but you'll be OK, if you can manage to get them off by just using your fingers or tongue."

I was now worried. Was I going to get stage fright? This could be a disaster. My first time working for Mrs. Templeton, might be my last.

I was now in the room, waiting for the client. There was a discreet camera on the other side of the wall, and I was viewing the image on a small monitor. When the door opened, my anxiety increased, but when I saw her, I started to relax. She was an attractive woman, easy on the eye. Definitely fuckable. And surprisingly, not much older than me. Simon had told me that most of the women were at least mid-thirties, and that a client in their twenties was unusual.

"It's my birthday, so I'm here to celebrate it in the best way that I can, with a big cock deep up my little pussy."

Then she started to undress. So no introduction, and no small talk. She just wanted to get on with it.

It was over in only a few minutes. After undressing, she'd bent over, with her pussy against the hole. I had to push hard to enter her, but she managed to take most of my cock. Then she'd urged me to fuck her hard.

I was now back in the common room, telling Simon about it.

"It sounds like Melissa. Was she a redhead?"

I nodded.

"It must be her. She's not very talkative. It was only on my third time with her, that she told me her name. But don't worry, not all of them are like her."

He was trying to reassure me, but I was worried. I didn't expect to have a meaningful relationship with the women that I serviced, but I was hoping for at least some foreplay, before we fucked.

When I was called for my second client, Simon gave me the thumbs up, but all he got back from me, was a forced smile. If this wasn't any better than Melissa, then I would seriously think about quitting.

When I saw her, my heart sank. She was at least fifty, possibly older. My first client had been wearing stylish clothes, that showed off her body. This one was the complete opposite. Her clothes were baggy, and she'd made no attempt to coordinate them. Even to my untrained eye, it was obvious that her top and skirt didn't match. Had somebody else dressed her, possibly a child?

"I'm Alice, and I believe that you are Chris?"

She might not be my ideal client, but I should still do my best to give her a good time.

"Yes, and it's nice to meet you Alice. What can I do for you?"

"Lots of things," and then, after chuckling, she said, "And hopefully, all of them very rude."

I had to laugh. I was warming to her. This lady had a personality, and she was indeed a lady. Her posh voice had confirmed that.

"I'll do my best."

"Good, and I'll do my best to enjoy it. I'm told that you have a very big penis. My late Husband had nine inches. I hope you can match him."

Match him? I can beat him. Then before I could respond, she spoke again.

"I know that on the website you are eleven inches, but they always exaggerate."

"They do. But, hand on heart, I can confirm that it's really ten inches."

That made her squeal with delight. Then she started to undress.

"My Husband wasn't a nice person, and I don't miss him. But I do miss his big cock."

When she was naked, I took a good look at her body. Her breasts were a decent size, but they were sagging. However, I did like her prominent nipples. And, apart from one or two extra pounds around her waist, she was quite slim.

"So what do you think?"

That surprised me. The clients weren't supposed to know that they could be seen.

"It's OK. I know about the camera. I might be old, but I'm not stupid."

But what should I tell her? A younger woman would want me to tell her how gorgeous she was, but I instinctively knew that Alice would want me to tell it as it is. In her case, honesty was definitely the best policy.

"You look good for your age."

That made her smile.

"Now I think that it's time for you to play with my tits."

Everyone at the club calls it a Glory Hole, but really it's plural, because there's more than one hole. There's actually three. Two at the top for the woman's tits, and one at the bottom for the cock. And, to cater for all sizes of women and men, both rooms have an array of steps. I'm tall enough so that I don't have to stand on anything, but Alice will have to, so that she can push her tits through the top holes.

As soon as I'd opened up the holes, her tits were in my room. She was eager, and I liked that. And I was as well. Even though she didn't have a prime body, I knew that this was going to be good.

I was now enjoying her nipples. I was greedily sucking on one, and rolling the other one between a finger and thumb.

"You're a very naughty boy, playing with Mummy's tits."

I wasn't into Mother and Son roleplay, but if that was her thing, then I was happy to give her what she wanted.

"Yes Mummy, I am."

That got a loud gasp from her, that got even louder, when I sucked harder on her nipple.

Five minutes later, I wasn't playing with her tits, I was abusing them. However, she wasn't complaining that I was being too rough. She was even urging me to do more to them. But I knew, that as much as she was enjoying this, very soon, she would want her pussy to join in. And I was right.

"I need your fingers in my wet pussy."

As quickly as I could, I closed the top panels, and then I put my hand through the bottom hole.

"Do you want Mummy's pussy?"

"No, I want Mummy's cunt."

It was now against my hand, and I was pushing three fingers into it. She purred as they went in.

"Finger me, but don't touch my clit. When I'm ready for your cock, I'll let you know."

"Yes Mummy."

Hearing that, almost made her come.

For the next five minutes, my fingers moved inside her wet pussy. And now, she was making a lot of noise. She might not be ready to take it to the next level, but I certainly was. I was desperate to get my big cock deep up her pussy, and I wasn't prepared to wait any longer.

"Does Mummy want to be fucked?"

That got a loud gasp from her. I now knew that when she'd got her breath back, it would be a yes. However, she didn't speak, instead, she pulled on my hand. The meaning was obvious. Take your fingers out, and put your cock in.

When I pushed into her, she was pushing back. She was eager to be fucked. I had to smile. My first client was a lot younger than her, and she had a body that most women would envy, but Alice was exciting me more than she had.

I didn't stop, until I had no more to give her. I was now in her up to my balls.

"Fuck, I love having a big cock up my pussy."

She was going to say more, but she stopped when I started to fuck her.

I should have taken it easy, been gentle with her. But I didn't. I pounded her pussy continuously, giving her long hard strokes, until she reached it. It hadn't been subtle, but it had been effective.

I watched her as she dressed. She was smiling. I was pleased that I'd made her happy. As she was about to leave, she opened her handbag, and then she took out an envelope.

"A little something for you."

"Thank you, but it's not necessary."

"I insist. Frank was a bastard," then she chuckled, before adding, "But he was a very rich bastard."

When she put her hand through the hole, I took the envelope from her, and then I thanked her again.

"And, I'm going to make the most of his money, by buying all the cock that I want."

Then she laughed, and I joined in. She was definitely a character.

When I got back to the common room, I was eager to tell Simon about Alice, but he wasn't there. However, shortly after, he was back, and he knew who Alice was.

"She's a lovely lady. And she fucks better than most women who are half her age. Did she give you a tip?"

I nodded.

"Don't tell me how much, but I bet that it was generous?"

My big smile told him that it was.

"She's best friends with Mrs. Templeton. And apparently, she's as rich as Croesus."

"Wow, as rich as that!"

Then, to Simon's great amusement, I said, "But who the fuck is Croesus?"

While driving home, I thought about my time at the club. It had certainly been a mixed bag. The first client had been a disappointment, lasting less than ten minutes. Next was Alice, and that had been wonderful. And it had ended with a third client, Mary. All she'd wanted was to be fingered. I'd given her a nice climax, but my cock hadn't got any attention. It had left me frustrated. The first thing that I was going to do when I got home, was jerk off.

It was almost midnight when I got home, but Mother was still up.

"So how was it?"

"OK."

"As good as that?"

Then she laughed.

I'd told her that my new job was in a bar, on the other side of town. I didn't like lying to her, but telling your Mother that you work in a Glory Hole, isn't going to go down well, no matter how broad-minded she is.

"When I get some free time, I'll go there for a drink. It'll make a change, you serving me."

Despite only working part time, she was a busy woman. Tennis, Golf, and charity work, took up a lot of her time. Hopefully, she would never go to, 'The Shamrock Bar'. But if she did, she wouldn't find me working there. I would be in the next building. And she would pass it without noticing it, because it looked like an office block. Part of it was, and the discreet entrance to Mrs. Templeton's club, was at the rear of the building.

I was now in bed, trying to get the climax, that I had been waiting all day for. As I stroked my cock, I thought about Alice. She was a perfect example of, 'Don't judge a book by its cover.' She was a passionate woman, eager for sex, but just by looking at her, you would never know that. Then I had a sudden thought, it was an epiphany, and it was about my Mother, who was almost as old as Alice. Since my Father died, just over three years ago, there had never been another man in her life. But did she want one? Underneath her calm exterior, was she longing for a man? Did she want a cock deep inside her pussy, and did she want it to be a big one? And with that image, of me fucking her, I climaxed.

The next day, I woke up with an erection. A very impressive one. When I started stroking it, I knew that it wouldn't take me long to come. Then I remembered last night, and my thoughts about my Mother, so I stopped. Some of my friends, especially my best friend Andy, talked about wanting to fuck their Mother. I never took part in it. Yes, my Mother was attractive, but I found it distasteful talking about her in that way. And now, I was as bad as them.

I was now in the kitchen, and Mother was making me breakfast. It had taken me the best part of fifteen minutes to get my cock under control. And then I had quickly showered, before going downstairs. But unfortunately, she was undoing all my good work.

It wasn't her fault. She was wearing what she always wears, and she was doing what she always does, but for some reason, she was exciting me. But why? Then I realized what it was. She reminded me of Alice, my second client at the club. And yesterday, I had fucked her to a big climax. If you were to dress Alice in the same smart clothes that Mother wears, and to change her hairstyle so that they matched, you could believe that they were Sisters.

A week later, I had got over it. I could now see my Mother, without thinking about Alice. That was a relief.

I was now on my fourth week at the club. I'd had a couple of awkward clients, but I was getting skilled at dealing with them. And the good experiences, were far outweighing the occasional bad ones. I was a young man, being paid to fuck. Life doesn't get any better than this!

But the following day, I did something that I shouldn't have. Something monumental. And I was now trying to come to terms with what I'd done.

At first, there was nothing unusual about that fateful day. In fact, it started well. Alice was my first client.

"I'm short of time, so it will have to be a quick one. I've got a meeting with Margaret, about a charity event. She means well, but she's always so miserable. In my opinion, she needs a good fucking, preferably by a big cock. That might even put a smile on her face."

Despite feeling sorry for Margaret, I had to laugh.

Ten minutes later, we'd finished. Alice had got what she wanted, a nice climax, and I had got a generous tip.

It was another hour, before I got my next client. And surprisingly, it was Alice again. So she wanted more. I was pleased to see that she'd smartened herself up. Had somebody had a word with her? Her clothes were more stylish, and they were coordinated. Then it hit me, like a bolt of lightning. My head was spinning. I didn't know what to do, or what to say. And it was now getting worse, because she was taking her clothes off.

"Do you like my bra and panties? I hope so, because I'm wearing them for you."

I should have looked away, and then I should have told her that I wasn't feeling well. That she should go. But I didn't. Instead, I stared at the monitor.

"I know that you can see me. Alice told me about the hidden camera. So do you like them?"

My mouth was dry, but somehow, I managed to get the words out.

"I like them. I like them a lot."

They were small, only just covering her private parts. They were what a woman wears for her lover. Yes, I did like them, but it was the body that was underneath them, that I liked even more. She was a desirable woman, and I wanted her, but there was a problem.

She was my Mother!

I could have stopped it, and I would have. If only she hadn't taken her bra off. That was a game changer.

"I've been told that I have nice tits, and that my nipples are perky. Would you like to suck on them?"

That got a quick yes from me, and it made her laugh.

"Someone is eager."

Yes, it was me. I got the top panels opened in record time, and then, as soon as her tits were through the holes, my mouth was on her nipple, and my fingers were on the other one.

As I feasted on her tits, I tried to ignore the fact that she was my Mother. But that was difficult, almost impossible. I was now feeling guilty, and I was also wrestling with my conscience. Should I stop, or should I continue?