Glory Hole

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I almost groaned.

"Is she the one with that mark on her tits?"

"Yes, a birthmark."

"She is one of our best. I have had her a few times."

That made me wince, but I don't think he noticed.

"I will let you into a secret. If you want to get her going, ask her to pretend that you are her Son. She likes that."

As casually as I could manage, I said, "Thanks, I might just do that."

He then went off to serve another customer. Five minutes later I ordered another drink.

"So you don't want one of our other girls?"

I was undecided. Mother not being here had dulled the urge.

"Are there any you recommend?"

"I'm the wrong person to ask. I'm not very choosey, any hole will do, even Mary's."

He then laughed. I didn't join in, so I think he realised that I wasn't happy with what he had just said. He now looked embarrassed, and I thought he might even apologise, but he didn't, instead he bent his head towards me.

"Rose or Anne."

Then he looked around, to check that we couldn't be overheard, before saying.

"Rose, if you are a tit man. They are massive, with nipples you wouldn't believe. But don't bother fucking her, she has a big opening. I tried it, but my cock didn't touch the sides. She had to finish me off by hand."

Then he looked at me to check that I was taking it all in. I nodded.

"But if fisting is your thing."

I shook my head.

"Anne is our youngest, she is twenty five. I am not complaining, but I can't understand why she works here, it can't be for the money because we don't pay much. She is my favourite."

I could tell he was now thinking about her. From what he had said she sounded OK, but I wanted more details.

"What's special about her?"

"Tiny, with small tits, and the face of an angel. She is so small that when you fuck her it feels as if you cock is massive."

I thanked him, then I got back to my drink, and he got back to his bar work. Rose or Anne, or even one of the other two? I couldn't decide. I was even considering going home, but it had been three days since my balls had been drained, so I stayed.

I had decided on Anne, but she wasn't free, so I settled on Rose.

"What's your name big boy?"

"Simon, but how do you know I'm big?"

She then laughed. It was a full uninhibited one, and I could tell she didn't care if they could hear it in the next room.

"I always say that. It makes all the men feel good, even the ones who wished they had a few more inches."

That's something I have never wished for. Ten inches is enough for me, and for all the women I have been with.

"You are in for a treat. If you have ever seen a better pair of tits than mine, then I will give you your money back."

I had to laugh, this was included in the admission fee at the door, but my laughter was drowned out by hers. For now it was endearing, but I had the feeling that later on it would irritate me.

If I had paid her, I wouldn't be getting any money back. Her tits weren't just huge, they were firm as well, and they were topped by the thickest and longest nipples I had ever seen. Oscar had sung their praises, and rightly so. The two holes were big enough for most women, but not for her. She had pushed a lot into my room, but it looked as if there was still more on the other side.

For the next ten minutes I worshiped them. They had my full attention. I pinched and stretched her gorgeous nipples, then I sucked on them until my jaw ached. Oscar had said not to fuck her, but I was going to, if she would let me.

"Can I fuck you?"

"I thought you would never ask," then after she had finished laughing, she said, "But you need a big thick cock. I am not some teeny weeny size zero girl, who would struggle to take a little finger. I am a big woman, with a big pussy."

When I put my cock through the hole, it felt as if I was auditioning. I would only get to fuck her if she thought my cock was suitable. It's a long time, if ever, that I have been nervous about a woman seeing my cock for the first time.

I heard something, it sounded as if she was licking her lips.

"I like it, but I think my pussy will like it even better."

I waited for her to laugh, but thankfully this time she didn't. I was pleased I had passed the test, and I was now eager to start.

She didn't waste any time getting me inside her. As soon as my cock was at her opening, she had quickly pushed back, taking all of it in one go. Oscar was right, she was big, but there was some tightness there. Her cunt was definitely fuckable, but it required a long thick cock. One like mine.

"What's your name big boy?"

"Simon."

"OK Simon, this is what I want from you. You are going to fuck me hard. Nice long strokes using your full length. It's a long time since I have been fucked to a climax, but you are going to do it. I will be disappointed if you come before I do."

So no pressure.

I started slowly, but she immediately urged me to go quicker. After five minutes she was grunting at the end of each stroke.

"This is good, but you need to do better."

I felt as if I was failing. I was now determined to give her that climax that she had asked for, even if I didn't reach it, so I upped the pace.

"I like that, don't stop."

I didn't, but after doing it for another ten minutes, I was wishing that I could. She was getting to the boil, but I had no idea how much longer she would need before she actually reached it. I was a young fit man, but even so, there was a limit to how long I could fuck for without collapsing through exhaustion. Then a thought flashed through my mind, I might die. That made me smile, what would they put on the death certificate as the cause? Then I cleared my head, this was serious business, I needed to get back to work.

She was now being fucked harder than I had ever fucked anybody before. Her grunting had turned into loud moans, almost as loud as her laughter had been. They must be able to hear her in the next room.

It was brutal but it did the trick. As she climaxed she started to writhe, and her cunt contracted, squeezing my cock. That took me over the edge. More by luck than good judgment, we had both come together.

I quickly pulled out of her, but she didn't move until at least another minute, and then it was another few seconds before she spoke.

"Simon, you had better come back and see me again."

I didn't need to think about it. We had both enjoyed it, so why wouldn't I come back?

"I will," then I muttered under my breath, "But only when my Mother isn't here."

When I got back to the bar I could tell Oscar was eager to talk to me.

"You were a long time. Who did you see?"

"Rose."

"And was I right about those tits of hers?"

"Yes you were, they are magnificent."

"What about her..."

I didn't let him finish, "You were right about that as well. She had to finish me off by hand."

He was so pleased that I had confirmed his opinion of Rose, that he gave me a complimentary beer. I had been tempted to tell him that I had fucked her to a climax, but that might have got him wondering why he hadn't been able to do that. Not all men are lucky enough to have a cock the size of mine.

When I returned the following Wednesday, I knew that Mother was working. I had been trying all week to think of some way of asking her what day she was going out with her friends. She would be suspicious if I just asked without a good reason. On Tuesday morning, at breakfast, my problem was solved when Mother told my Sister that she was going out Wednesday night.

Rick was back, and there was no sign of Oscar.

"Hi Rick, nice holiday?"

He spent the next five minutes telling me about it, and I found out that Oscar was his Brother.

As I opened the door I was apprehensive, perhaps Mother was really out with her friends. I checked the doors, Rose, Mary, Vicky, and the last one, Lizzy. I punched the air with excitement. She was working, and she was free now.

"Hello, I am Simon. Do you remember me?"

"Of course I do, how could I forget my Son," then she giggled.

For a split second I thought she knew, but then I realised it was all part of the pretence.

"And I remember your cock. I would like some more of that," then she giggled again.

This time it had sounded more girly, as if she was much younger than she was. She might be forty three, but she could still get excited at the thought of a big cock. But not as excited as I was at the thought of fucking her again.

As I played with her nipples, I looked closely at the birthmark on her breast. My Father must have seen it so many times now, that I bet he hardly notices it, but I found it fascinating.

"I like your birthmark."

"Years ago I was thinking of having it removed, but my Husband talked me out of it. I am glad he did."

Then she giggled, and I wondered why.

"My Son Simon saw it when he was eighteen. It was by accident. I was leaning over and my dressing gown opened. He got a good look at my tits, and I could tell that he saw it."

I was nineteen, not eighteen. I even remember the day, it was a Tuesday.

"What I wanted to do was to let him suck on them, but I knew that was wrong."

I almost groaned, if I had known that at the time I might have reached out for them.

"Simon, please will you suck my tits."

"Yes Mummy."

I spent ten glorious minutes on them. Rose has a much better pair, but the fact that she was my Mother, made it far more exciting.

Now it was time for her cunt. This time she was so wet that she got three fingers straight away. She gave a deep moan of approval when they were fully in. Last time I had rubbed her clit with my thumb. I was going to do that again, but first I wanted to try something different. I rotated my fingers so that my thumb could explore her ring.

When I pushed the tip of it in, she purred.

"You naughty boy, putting your thumb into Mummy's bottom."

That sent a shiver of excitement down my spine. I suddenly realised, that my prim and proper Mother, who was a respected member of our community, was really a dirty bitch, who was up for anything.

As nice as her bottom was, her honey pot was better. When my thumb touched her clit she almost climaxed.

"Easy. Mummy is too excited."

For the next few minutes, I tried to be as gentle as possible, but even the lightest touch was making her squirm.

"I am going to have to fuck you."

That got a quick, "Yes," from her.

Her tits might not be as good as Rose's, but she had the better cunt. I was now deep up her, and it felt amazing.

"One day I might let my Son fuck me," then she moaned as I fucked her hard, before adding, "I hope he is as good as you."

That day had already passed, and I was now doing it again. I was tempted to tell her who I really was, but despite her admitting that she wanted to do it, that was no guarantee that she would actually agree to do it. It was best not to tell her. I was getting to fuck her, and she was none the wiser.

After only a few minutes I could tell she was ready to come. I had been hoping for at least ten minutes, fifteen would have been perfect. However, there was nothing I could do now except finish her off, and make sure it was a big one.

When she climaxed she was almost as loud as Rose had been. There was a lot of moaning and groaning from her, and some words that I couldn't make out. My orgasm was simpler. I just grunted once, then my cock twitched a few times until my balls were drained. I wasn't complaining, it's just that women do seem to have the better climax. Neither of us spoke until I was about to leave,

"Thanks Lizzy, that was really good."

"I enjoyed it as well. Simon..."

Then she stopped. My hand was on the door handle, and I was about to leave, but I waited. I knew she was going to say more.

"Tell me what you think of this," then I heard her take a deep breath before continuing with, "Next week I want you to come back. When you see me I will have my Daughter with me. Would you like both of us together?"

My head was now spinning.

I blurted out, "Your real Daughter?"

"Yes, but it's just for you. So don't tell Rick, or any of the others."

"Why?"

"She has a fantasy about fucking her Brother. This way she can do it without anybody getting hurt. So are you up for it?"

I nodded my head vigorously, then I realised I had to speak.

"Yes."

"Thank you. I was worried that you might not want to."

This was every schoolboy's wet dream, your Mother and Sister at the same time. There was no way I would not want to do it.

Back at the bar I drank two beers in quick succession. Ricky gave me a funny look, but he didn't say anything. This time Mother was back home before me, she must have left The Tavern shortly after I had left her room.

The next day we had breakfast together. Father had his nose in the newspaper, and we hardly got a word out of him. My Mother and Sister talked non-stop, and both of them appeared to be in a good mood. Had Chloe been told about what was going to happen next Wednesday? I would say yes.

For the next few days I found it a bit uncomfortable being around my Mother and Sister. I got an uneasy feeling that they both knew that I was the Simon that they would be seeing on Wednesday. But that was ridicules, there was no reason why that was the case.

I had managed to get myself so worked up, that I decided to ease the tension by visiting The Tavern Monday night after work. Before I had even managed to sit at the bar, Rick had got me my beer. I was now a regular, and I was been treated like one.

Rose was free, but I picked Anne. Oscar had rated her, so I was happy to try her out.

"I am Anne. You can do whatever you want with me."

I knew she was twenty five, because Oscar had told me, but she sounded as if she was a lot younger. It was exciting, but a bit creepy as well. If I hadn't known her age I would have walked out. Young yes, under age, definitely not. And it's always better to be safe than sorry.

When she pushed her tits through, I was surprised how small they were. They made my Mother's look huge. However they were nice and firm, and her nipples were pert. After a few minutes my cock was straining to get out. I had to briefly stop so that I could take my trousers and underwear off.

"Have you got your cock out?"

"Yes, and it's ready to fuck you."

She cooed with excitement, before saying, "I am only a little girl. Please be gentle with me."

As I put my cock into the hole, I waited for her response.

"Fuck me. That's a nice cock."

Yes, that's what I was intending to do. That's if the sight of it hadn't put her off.

"I need some extra lube for this."

I would have preferred it without, but she was the one to know if she needed it or not, so I kept quiet.

It was another minute before I felt her cunt lips touching the head of my cock. Then slowly, very slowly, she pushed back against me. She struggled with the first couple of inches, then she rested halfway, before continuing. It must have been uncomfortable, but she took it all.

"Let me get used to it. It feels like you are splitting me in two. If it gets too much for me you might have to take it out."

I hoped it wouldn't come to that. Her tight little cunt was gripping my cock like a vice, and it felt good, but it would feel even better when I started fucking her.

"OK, but slowly."

We were now fucking, but almost in slow motion. After a couple of minutes, I speeded up. She didn't complain.

"Harder."

Good, she was now ready for a proper fuck. Surprisingly, she managed to keep going for another five minutes, the last two taking full strokes. When she climaxed, I only needed another stroke before I joined her. As her tiny cunt pulsed, it squeezed out all my seed.

Back at the bar Rick asked me who I had been with. I told him.

"What do you think about that voice of hers? Some customers think she puts it on, but it's her real voice."

I shook my head, "Yes, I can't believe she is twenty five."

"They have to be at least twenty one to work here. Don't worry, she is legal, but I must say I did check her passport very carefully when she first started."

It had been a good experience, but I was already thinking about Wednesday. I still couldn't believe that I would be seeing both of them together. I didn't talk much with my Father, but when I did it was mostly sport or politics. However, it looked as if my Mother and Sister talked about their sex lives, and what their fantasies were. It must be a woman thing, because I would curl up and die if my Father ever started telling me about what he did in bed.

I hadn't planned to go out Tuesday night, but Charlotte called. Her parents were away for the night so we had the house to ourselves, and she was obviously eager for me to join her. Ten minutes after I got there, we were in bed together. The sex was good, and she got the climax she wanted. I had one as well, but I would rather have saved it for tomorrow. I stayed the night, but I left early while she was still asleep. If I had waited until she woke she might have wanted to be fucked again. I might manage twice in one day, my Mother and Sister, but three times was too much.

I only worked a half-day. I had a dental check-up at two, and some jobs to do, so I took the afternoon off as holiday. I was back at home for five, and my Mother and Sister were there, but they were ready to go out.

"Where are you two lovely ladies going to?"

They shared a knowing look, then Mother said, "That would be telling," then they both giggled.

Then, with a more serious face, Mother said, "I am meeting up with my friends, and Chloe is coming with me."

She sounded convincing, and I wondered if that was what they were actually going to do. If that was the case, then I was in for a disappointing night. Ten minutes later they left, but I waited until six before I went out.

"It's nice to see you Simon, but twice in one week."

Rick was smiling, and I could tell there was no malice in his observation.

I shrugged my shoulders, before saying, "What can I say? I have a big appetite."

Then I heard him mutter under his breath, "And a big cock."

I pretended I hadn't heard him. The women must have been talking about me.

I didn't want to appear too eager, so I finished my drink before going into the back room. Lizzy's card was on the second door, but the sign was red. I would have to wait. I didn't like it, but there was nothing I could do about it.

"Let me guess, Lizzy is busy?"

I just nodded. Rick smiled, then he got me another drink. I waited another fifteen minutes before trying again. This time it was green.

"Hi, it's Simon."

"Hello Simon, I have been waiting for you. And so far tonight I have managed to please all the customers without fucking any of them. So you have a nice clean pussy to work with," then she giggled, and I heard another person join in.

"Is your Daughter there?"

"Yes I am, nice to meet you."

I could hear the excitement in her voice.

"Likewise."

I wasn't sure how this would work. I got the feeling we would make it up as we went along. It started with the two top holes being opened, then they were both filled with tit. The left with Mother's and the right with my Sister's.

I was like a kid in a candy store, where should I start?

"Suck me."

It was my Sister. As I did what she had asked, I also tweaked Mother's nipple. I then kept switching. Both tits were nice, but my Sister was only twenty, so hers was firmer.

"Do you like playing with your Mother and Sister?"

I mumbled, "Yes," and they both giggled.

"You are a naughty boy. What are you?"

I reluctantly raised my head from my Sister, so that I could speak.

"Mummy, I am very naughty."

One of them squealed with delight. It sounded like Chloe, but I couldn't be certain.

I then got back to work on their tits, but a couple of minutes later Mother spoke again.