The Holiday Ch. 05

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We witness a solemn plugging and mum gets her reward.
4.7k words
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Part 5 of the 9 part series

Updated 09/13/2023
Created 07/22/2023
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I could hardly believe what was happening. I looked around the room and, yes, it was true. I was with three other women who were all naked and I was the only one clothed, if you can use that word to describe what I was wearing. If you can call the scantiest bikini imaginable as 'clothed'. If three tiny triangles covering my tits and my pussy could be classed as 'clothed'. In truth they barely covered anything. My tits were barely hidden, and my stiff nipples poked out through the thin fabric. The triangle between my legs squeezed between my lips pushing them apart and disappearing between them. But the other three were definitely naked apart from two of them that wore collars, and one of whom was my mum.

It wasn't that which was making me embarrassed. It was the fact that, in front of all three of them I was grinning broadly but at the same time tears were streaming down my face. The other two women were Audrey and her friend Jody, and I had only known them for a couple of hours, but I was overjoyed with happiness for them both as they hugged each other. It was crazy to become this emotional. I glanced down at mum who was kneeling on the floor gazing at the other two. I saw a tear slip down her cheek as well. We had just watched as Jody had accepted a collar from Audrey, a very significant moment. She had agreed to become Audrey's pet, just like mum was my pet. We both knew and appreciated how important that moment had been.

I subtly shifted my seat on the end of the bed and Audrey must have sensed it. I felt it was time for them to be alone. Audrey disentangled herself from their hug and sat up and turned to look at me. She reached out and softly wiped a tear from my cheek.

"I'm sorry, Audrey, but that was so beautiful."

"Oh Laura, thank you."

"It's just I think we should be going. I think you need some private time together. Perhaps we can get together tomorrow."

I started to rise but she put a hand on my arm, stopping me.

"I agree and thank you for being so thoughtful. But before you go there is one more thing you could help me with."

She reached sideways and picked up the bag from the shop where she had bought the collar and lead which now adorned Jody. I really must try harder to call her by her new name of 'pet whore' but it wasn't going to be easy. Audrey reached into the bag and came out holding a brand-new butt plug almost identical to the one that mum was wearing. The one I'd bought her as a present only this morning. The only difference was that while mum's ended in a ruby red jewel, the one that Audrey was holding was finished off with a jewel of emerald green. My eyes widened with joy. I glanced at mum, and she was grinning as well. Jody, or whore, was also smiling but her eyes were full of concern. She looked almost frightened, much as mum had when I had her fitted in the shop.

"I was wondering ... would you mind helping me fit this to whore? Neither of us have tried one of these before."

"This morning was our first time as well, but it didn't look that difficult. It just took determination and some lube."

"That's more or less what the woman in the shop told me, so I bought some lube as well."

"She tipped the bag over and a bottle of lube fell onto the bed.

"I think its best if Jody ... I'm so sorry ... if whore faces away from us with her head down and her bottom in the air. We'll be able to see what we're doing."

"Good idea. Whore, you heard what Miss Laura said. Get in position!"

Without a word, whore shuffled around, put her head on the floor and lifted her bottom. From our point of view, she looked gorgeous. Her pink and glistening lips peeking out from beyond her vulnerable looking pucker.

"Bitch," I told mum, "get over here and hold her cheeks apart."

She moved at once and did as she was told. Audrey picked up the lube and unscrewed the top. She let a stream pour out and then slide down the cleft over the offered anus. I quickly put a finger down to stop it running too far and started to work it in and around the sweet rosebud.

"The woman told me its best to loosen them up first."

"Yes, she mentioned that. Please, go ahead."

As Audrey poured more lube over the plug and then worked it around, making sure it was well covered, I started to press my finger into whore's very tight hole. She moaned under my pressure but gallantly did not flinch. As my finger slowly broke through, she started to take deep breaths through clenched teeth. I felt when her sphincter stopped resisting and my finger slipped easily in. I pushed far enough to get to my second knuckle and then stopped, allowing her to get used to it.

"Well done, whore, you didn't scream and howl like you usually do."

"It seemed to go in easily, do you use it often?"

"Certainly, regularly although I wouldn't say often."

"Enough to loosen her up."

"Time to try the real thing."

Audrey had an almost evil grin as she held up the new plug, now shining with a good coating of lube. I slipped my finger in and out a few times before taking it out completely and passing possession to Audrey. I felt whore flinch and tremble with anticipation as the pointed end of the plug first touched her anus. Mum held her firmly as Audrey started to push, slowly but firmly. A few gasps and sounds of discomfort came from whore which Audrey ignored. I could see the muscles tense on her arm as she approached the widest point. Whore was giving up her anal virginity reluctantly. She started to make noises of pain and fight against mum's strong grip on her cheeks.

Then, we all breathed a sigh of relief as it disappeared, leaving just the jewel shining out like a green beacon. Mum released her hold and kissed her cheek before kneeling back. I made a swivelling motion to mum, and she got the idea immediately. She shuffled around so she was kneeling next to whore and bent over in the same way. Both their jewels were on display for us.

"Oh fuck, that is such a beautiful sight."

Both Audrey and I were smiling broadly, and I took her in my arms and hugged her.

"But ... I think it is time we left. I'm sure you two have lots to talk about."

"Thank you, Laura for such a great afternoon. I'm not sure how much talking we'll get done this evening but I'm sure we'll have some fun."

I picked up the loose end of mum's lead and smacked her lightly on one cheek with it.

"Come on, bitch, time to move. Let's leave them to enjoy each other."

I stood up and mum did so as well. I led her over to the door. As I opened it, I turned around. The new pet and owner were oblivious to us and totally absorbed with each other so I led mum out and closed the door as quietly as I could, we made no sound as we walked away through the soft sand.

When we got back to our cabin I sat on the edge of the bed and mum came and knelt in front of me in her formal pose, hands behind head and knees spread wide. I looked at her for a long time and she started to look worried. Had she upset me in some way, she wondered. Eventually I stood up and walked around the room.

"No need to worry, bitch, I could not be more pleased with your conduct this afternoon."

Her shoulders visibly sagged with relief.

"You have endured a great deal and done so bravely. You suffered under those nasty clamps. Did they hurt very much?"

"In truth, Miss Laura, yes, they did. Especially the one on my pussy. I was glad in a way that there was only one each."

"What do you mean 'in a way'?"

"Well, Miss although they hurt, I did find myself getting aroused. I'm not sure if it was despite or because of the pain, but I came to like them, Miss. I had to struggle not to cum, Miss."

"Curious. Perhaps I shall lend you to Miss Audrey for you to discover more."

"Whatever you may ask of me, Miss."

"But she will be busy now and I have other things to attend to. Your reward, to start with."

She perked up at once. At home I would occasionally reward her for tasks well done. I stooped and picked up the shopping bag from the shop where I had bought her plug and looked inside.

"I bought a couple of other things at the shop."

I pulled out, as if from the proverbial hat, the rabbit. Okay, not a real rabbit nor a real top hat but I tried to be as theatrical as possible. Her eyes went wide with delight. I placed it on the bed and reached into the bag again and came out with the strap-on. Her eyes went even wider, and she grinned.

"I know we already have a couple at home and that you like me using them on you, but I didn't bring one here with us. This new one will have to do for now. So, bitch, stand up and lie back on the bed. Then knees up and spread wide."

I knelt on the floor between her legs and looked up at her middle-aged pussy. It wasn't as neat and tidy as mine, but it had worn well. I looked at the items lying on the bed next to her. I reached across to them.

"Now, which of these will we try first ... this one, I think. You are going to love it I promise."

I held up the new rabbit vibrator. Looking closely, it looked a little soiled but I'm sure mum wouldn't mind that.

"I got the woman from the shop to try it out on me and, wow, did she make me cum. I'm surprised you didn't hear me even though you were tied up outside."

I held it to my nose and breathed in deeply. It still held a faint hint of my musky girl smell. I held it out to mum, and she lifted her head eagerly. She too savoured its scent and a look of puzzlement and disappointment showed on her face. Even now she couldn't help herself from acting like my mother, disapproving of the things I did. However, that thought quickly moved away and she eagerly opened her mouth and let her tongue appear, eager to taste the new toy. I let her take it into her mouth. As she did so I reached down and stroked her pussy lips. They were already soaking which I was not surprised about. When she had sucked at the rabbit for long enough, I pulled it away from her and knelt back. Experimentally I pushed some of the buttons on the panel. I set the main body vibrating at its lowest setting and then placed the very tip on mum's cunt. She jumped and then stifled a moan. I pushed a little further. Now she could feel its full size. She started to ooze even more juice and I kept pushing. She took it all gladly, moaning and groaning with pleasure. She was already almost there, and I hadn't even used the other options yet. I smacked her hard on the inside of her thigh and she yelped.

"Don't go getting greedy and remember to ask me first."

"Sorry, Miss Laura."

Her voice was tiny, almost a whisper. I pulled the rabbit nearly out of her as a warning and then pushed it back in. this time far enough that the ears reached her clit. I pressed a button, hoping it was the one for the ears and thankfully I was right. Suddenly her whole body went stiff and her back arched alarmingly. I clicked the speed up to three and she went even stiffer.

"P ... please, Miss ..." she pleaded.

"Please what, bitch?"

"Please may I cum, Miss."

"Wait!"

I turned the intensity up a little more, but she was still only halfway. She started whimpering.

"Please ... please ...Please!"

I took pity on her.

"Cum for me bitch."

She bucked and her juices spluttered from around the rabbit, spraying everywhere. I got covered but I was beyond caring. Mum had collapsed back onto the bed and just lay in a heap, not moving. I knelt up to check on her, but she was breathing normally. She had just fainted. I carefully turned the rabbit down to its minimum but left it deep inside her, and then knelt back down. Suddenly I was starving, and I realised I hadn't eaten all day. Slowly I stood up and climbed over the insensible mum and reached for the phone. The same as always, a voice answered almost instantly.

"Yes, Miss, how may I help?"

"Do you do any take-aways?"

"Certainly, Miss, what sort of food do you require? We can do Chinese or Japanese or Italian or ...

I interrupted her list. Mmmm Italian, my favourite.

"Do you do pizza?"

"We certainly do, Miss."

"Can I order a large three cheese with extra anchovies, please."

"I will pass that order to our kitchen Miss. They usually take about ten to fifteen minutes. Cabin 36?"

"Yes please, and thanks."

The phone went silent. I lifted myself to climb off mum and realised she was back with the living. It must have been strange for her to come back with me lying on top of her, chatting on the phone. I kissed her on the cheek before rolling to one side and sitting up on the edge of the bed.

"I've ordered us pizza because I know you like it, and you must be as hungry as I am."

She tried to sit up, but I held her down. She had a look of horror on her face.

"But ... but we should get respectable, Miss."

"Don't be silly. They've all seen this sort of thing before, and they've seen you twice in situations just as bad."

To stop any more complaints, I reached out for the base of the rabbit and turned it up a couple of notches.

"Besides, you have at least five minutes to enjoy this lovely new toy."

I started sliding it in and out of her again, fucking her with long slow strokes. She was moaning loudly. I switched on the ears and her moans got even louder. I could tell from experience that she was about to cum again.

"Wait!"

My voice was severe and stern."

Please. Please, Miss Laura, please let me cum."

Just then came a knock at the door. I switched off the ears but left the main vibe continue as I called, "Come in."

I don't think mum even heard me as she continued to writhe. Luckily the pizza girl did hear me and opened the door. I instantly recognised the face and the almost invisible look of shock before her smile returned.

"Hello again. Its ... err ... Kyra?"

"Yes, Miss, I delivered sandwiches the other night."

"And now its pizza and you find us in an even more compromising position. What must you think of us? But come in and close the door. Not everyone is as accepting of us as you are, Kyra."

She came in, carefully carrying the pizza box. I pointed to a table as I continued to slide the vibe in and out of mum's leaking pussy. She was looking at me and frowning but making no attempt to stop me.

"Come and sit with us for a while, Kyra. Has your shift been busy tonight?"

"Tonight, has been quite quiet, Miss. May I ask if your friend is enjoying that?"

"This is her reward as she has behaved very well all day. I bought it one of the shops. Have you seen one before?"

"No, Miss, but it looks very complicated."

I took her hand and moved it to the base of the rabbit. She almost pulled away when she felt its vibrations. But I held her firmly, wrapping her fingers around the base along with mine. I continued my long deep strokes into mum's wet pussy.

"This button controls the speed and intensity of the vibrations and this one ... controls these ears."

I pulled the ears back and let them flick against mum's clit. She squirmed with pleasure that came from everywhere. I turned the vibe up to six and switched on the ears. Together Kyra and I continued to fuck her. Kyra's face was filled by a broad smile. This was an added bonus to her shift as far as she was concerned. I lifted my hand off hers and she continued to slide the rabbit in and out of mum without any urging from me. I slowly managed to wriggle backward and out from between them. Kyra immediately moved to fill my space.

"Just keep at it, Kyra, I'm just going to get a slice of that pizza. She can cum but only when you say she can. Do you want a slice of pizza, bitch?"

I got no reply as the ears once more made contact with mum's clit and she groaned loudly. I picked out a slice and went to sit back down on the bed. Kyra was now between mum and me and I watched them as I bit into the pizza. It was delicious, with all the usual herbs and the anchovies bringing that extra salty zing. I lay back and put my head close to mum. Her mouth was open, and she was panting. There were beads of sweat on her forehead. She looked at me with pleading eyes.

"Miss, please may I cum? Please, Miss?"

"You must ask Kyra. I've put her in charge for the moment."

"P ... p ... please, Miss Kyra, may I cum?

Kyra turned her head and looked at me with raised eyebrow and I nodded. I wish she had decided for herself, but I think mum had reached her limit. Perhaps another time I might take her further and deeper.

"Yes, err ... bitch, you may come."

I think mum's shrieks could have been heard on a nearby island or passing cruise ship. Her body bucked and writhed as her orgasm exploded. More of her cum squirted out and this time most landed on Kyra. I held my hand over the pizza to protect it. Slowly mum quietened down. She was still and I thought she might have gone to sleep but she stirred and made a little moan as Kyra slid the rabbit out of her. I took it off her and showed her how to switch it off. I had finished my slice of pizza, so I reached across both of them and fumbled for the strap-on. It was a puzzling mix of a large flesh-coloured dildo and a tangle of leather straps. I tried to disentangle them, but they made no sense. I looked at Kyra for help.

"Have you ever used one of these before, Kyra?"

"No, miss, but I've seen them in use a few times. A lot of guests bring them and use them on their friends. Guests always seem very careless when I knock on their door."

"I can make head nor tails of this one. I know where it's supposed to go but how ...?"

"If Miss could stand, I could try."

I stood up while Kyra examined the strap-on, turning it this way and that trying to work out how it all connected. Then she knelt on the floor in front of me and put one of the leather loops around my waist and fastened it. The base of the dildo hung in front of me just where my clit was. Two further straps went between my legs, one either side of my labia and between the cheeks of my bottom. At her request I turned my back to her. The two straps attached to buckles on the belt but spread apart which pulled my cheeks wide. With nothing more that the thin string of my bikini bottom to hide it this put my arse of full display. I hope Kyra admired it. I turned back around, and Kyra was indeed smiling. I looked down and the dildo was now standing out proudly as it was designed to do. it was also pressing into my clit, and I could imagine how that would feel as I thrust into mum's pussy.

"Down on the floor, bitch, and start getting this nice and wet. Unless you want it dry inside you."

Still slightly sore from her time with the rabbit mum struggled off the bed and knelt facing me. Her eyes widened but she quickly opened her mouth and let the dildo slide in. she started bobbing her head back and forth, coating it with her spit.

"I've never had a man inside me, but bitch has. What about you, Kyra? Have you had a man, or even one of these inside you?"

"Errr ... no, Miss. Neither."

"Do you want to try?"

"I ... I'm not sure if I should, Miss. The hotel might not allow ..."

"Forget the hotel. You're in my private cabin. Now, do you want to try?"

"If Miss would like me too."

"I would love to fuck your pretty pussy with this mighty dildo, you silly girl, Kyra. But I think you should help bitch get it all nice and slickly wet. I'm sure her pussy is good and wet but I'm not sure about yours. So, get to it."

Kyra immediately turned and put her face near mum's. She must have been listening as she took the dildo out of her mouth and pointed it towards Kyra who opened her mouth at once and let mum guide it in. She started to gag after just a few inches so mum was very gentle with her, never forcing it too far. When I thought they had had enough fun I told them both to turn and bend over the end of the bed. With both still on their knees I was presented with the nice picture of both their bottoms looking back at me. I reached over and pulled the strings that made the bows that held up Kyra's bikini bottoms and pulled them free.

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