Game Night for Alanna

You need to have read Making of a Cuckold Sissy for this story to make sense. That was written from Alanna's PoV; this is written third party, otherwise I'd need to chop and change PoV. Some parts are presented as though your author has done an interview with Alanna (with the full permission of Tony and Sarah of course), or with Sarah.

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This story is set a few months after the events in the previous story; Alanna, Sarah, and Tony have settled into their lives together. Tony still keeps his house, but spends most nights in Sarah and Alan's bed, while Alanna sleeps in the guest room, waiting to be called to come and help clean up Sarah after she and Tony have had sex. That is, of course, if she's not been told to stand there and watch, ready to start the cleanup process. Sometimes Tony will come through and wake Alanna up unexpectedly, so he can fuck her or have her suck him off; "Got to keep a sissy on her toes", to quote Tony. He's also been training her to deep throat him as that's a skill all sissy's should have in his view.

One change which needs to be noted is that not long after things had changed, Tony and Sarah had decided that while "miss" and "sir" was appropriate for guests, from then on Tony was to be referred to as "Master" and Sarah as "Mistress".

On this particular Friday, Alanna had slept through to her alarm going off. She got up, took off her nightie, had a pee and a wash, got dressed in her maid's uniform, and inserted her plug-of-the-day. Heading downstairs she laid everything out for breakfast for Alan and Sarah and waited for them to arrive.

They came down at 7:30AM as usual, but Sarah was acting a little excited. "Do we tell her the news now?" she said, as she came in the room.

"After breakfast," replied Tony. "Good morning, Alanna."

"Good morning, Master, good morning Mistress."

Breakfast was the usual routine; Alanna served juice and coffee and toast, while waiting for this news with some slight degree of trepidation.

"Now?" asked Sarah excitedly, as the last mouthful of coffee was drunk, before the cup had even hit the saucer.

Tony smiled indulgently, "all right then."

Sarah turned to Alanna.

"Alanna?"

"Yes Mistress?"

"You have some shopping to do, and some preparation too. Tomorrow night Tony is hosting a poker game for a few of his friends. 7 I think?" she asked Tony.

"8 if you include me. We'll need enough glasses, and snacks, and mixers, and I'll give you a list of the drink each person likes. Because it's the first time, I won't expect you to know them off by heart, but if this is a success we'll be making it a monthly thing and you'll need to be ready to provide any of them with whatever they normally drink, without having to be told."

Alanna nodded. "Yes Master. As soon as you give me the list I'll get started on the shopping. Will the usual online store suffice or do we need a special order?"

"The usual place will be fine. The list is printed out, and on your bedside table waiting for you. Clear up here then get on with the shopping. Oh, and the list also has the instructions on what we want you to wear for the event."

Alanna was excited, and nervous, about being seen by Tony's friends, some of whom she was worried would have known Alan. But she took comfort in her station in life as a sissy cuckold maid, and whilst having her own breakfast did the shopping as ordered, and then got on with her normal daily chores.

Saturday morning arrived, and Alanna dressed as she had been instructed, in her pink maids uniform, with matching frilly knickers, and her pink jewelled butt-plug, white suspenders and stockings, and white-with-diamante strappy heels. She'd also been told to wear basic make-up, which was a treat for her.

After breakfast the deliveries arrived. The online store that Alanna had shopped from always used the same delivery chap, and he was used to Alanna. Tony had taken him to one side the first time there had been a delivery, explained the situation, and given him a cash "donation to the Christmas fund" to keep him discrete.

"Good morning, Alanna," the driver said, as she opened the back door to him.

"Good morning, sir," she replied, bending down to lift the first load of carrier bags. Taking them into the kitchen she put them on the table and went back for the second load. One of the bottles had rolled out of the bag and into the hallway behind the door as the driver was putting them down, and so Alanna had to bend down to pick it up. Tony had taught her to bend from the waist wherever possible, as that gave the best view to those behind her, and she tried so hard to remember her training.

The driver therefore got an excellent view of her pink frilly knickers, atop her white suspenders, and wondered if he might want to renegotiate the "Christmas fund donation" to include some intimate time with Alanna. He resolved to talk to Tony about it the next time he saw him.

Unaware of the thoughts in the driver's head, Alanna took in the rest of the delivery, stored everything away, and laid out the table for dinner, as part of her normal duties. People were due to start arriving around 8PM, so Sarah and Tony had told Alanna to have dinner ready a little early, which meant she had to rush a little, but meeting the requirements of her Master and Mistress was part of what she lived for, so she sort of enjoyed having to change her routine to please them.

Come 8PM, Alanna had every thing ready. The table was laid, with a drinks coaster and a table mat (for stacking chips on) at each chair and there was a comfy chair off to one side for Sarah to sit in and read or watch the game.

Alanna was waiting in the front hall when the doorbell rang. The first guest was here! She was so excited, but knew she had to control herself and make Master and Mistress proud of her.

She opened the door wide, to see a handsome chap in his late 40s standing there. She didn't recognise him, and so, as instructed, asked "May I help you?" in a warm friendly voice.

"Hi, you must be Alanna," he replied, "I'm Andy, not to be confused with Andrew who's also coming. Is everything ready?"

"Yes sir, if you'd like to come inside and let me take your coat," she offered, stepping back from the door.

He did so, shucking his coat and handing it to her. She turned and hung it on the coat rack, then pointed to the dining room door. "This way please sir, you're the first to arrive. Master and Mistress will be down shortly. May I get you a drink?"

"Scotch, rocks, please."

Alanna led Andy to the dining room, and turned to the drinks cabinet to make the requested drink.

"Any specific seating plan?" he asked.

"No sir, the only reserved seat is the one in the corner which is reserved for Mistress. Please, sit where you'd like."

Just then the door bell rang again. "Here's your drink sir, if you'll excuse me, I must answer that," she handed him the drink and headed back to the front door.

This time there were two people standing there. They introduced themselves as "Gavin" and "Terry". Alanna took their coats and drinks orders, showed them into the dining room, and started to produce the drinks.

While she was making Gavin and Terry's drinks Tony and Sarah came into the room. Tony was his usual dapper, casual, self, but Sarah... Sarah had really made an effort. Her make-up was flawless, almost invisible, accenting everything positive about her face, and her clothes made Alanna shiver. The dress Sarah was wearing was the one which she'd worn on the first night of their honeymoon, as they danced the night away in a Caribbean bar, before heading back to the hotel room and having the best sex they ever had. Things had gone downhill, sexually, since then, until Tony came into their lives, but that's a different story which hopefully you've read.

The three gentlemen already present jumped to their feet, and one by one shook Tony's hand, and hugged Sarah.

"The usual please Alanna," said Sarah.

"Yes Mistress. And for you Master?"

"The usual, thanks."

"I'm impressed," said Gavin, "she's so well trained. Did you send her away to some training course or other?"

Tony smiled, "she's totally self taught. We've filed off a couple of rough edges and taught her what we like, but what you is see pretty much her natural state. Turned out that all the time that Sarah was visiting me, Alan was studying to be Alanna. And Alanna is now our darling little sissy maid, happy to serve, in any way we wish."

Alanna blushed at the compliment, just as the door bell rang again. She took a few seconds longer to answer it this time, hoping that the blushing in her cheeks had faded.

Over the course of the next 15 minutes the remaining guests arrived, were greeted, had their coats taken, and drinks made. Alanna didn't recognise any of them as having known Alan, which made things a little easier for her as there was no past baggage to deal with.

"Well, the gang's all here," commented Tony. "Shall we get started? Gentlemen, take your places please. Does anyone need a top up? If so Alanna can provide."

Two of the guests wanted fresh drinks, so Alanna provided those while everyone was settling into place.

Tony looked around the guests. "As I mentioned when I invited you all, we'll need to finish at about 1AM, as Sarah and I have plans for tomorrow."

"The chips if you please Alanna," requested Tony, as part of her duties that afternoon had been to count out $2000 in chips for each of the guests and Tony, and put them in little trays, which she now distributed to the players.

As Alanna finished this, Tony nodded to Sarah, who opened the top drawer of the sideboard and produced three, still sealed, packs of cards, which she handed to Gavin. He selected one, and passed it to Steve, who inspected the seal and passed it to Terry. Terry broke the seal, and passed the pack to Andy, who removed the jokers and passed it to Tony, who had the dealer's button. The remaining two packs, along with the jokers, went back into the drawer.

Alanna was standing quietly in the corner of the room, eyes down, hands in front of her, paying enough attention to know when she was needed, but otherwise just behaving like a piece of furniture, which was what Master and Mistress liked.

Tony and the others had clearly talked about the evening beforehand; Tony said "as discussed, Texas Hold'Em, no limit. To keep things flowing, if anyone runs out of chips, we'll declare a winner and start again. All happy?"

Everyone indicated their agreement by nodding, saying "yes", or grunting.

"Cool, here we go then," commented Tony as he started to deal the first hand.

As the first few hands were played, it became clear that all the players were of pretty much the same skill level, which kept things exciting for them, as the luck of the cards became more important. Alanna had brought her list with her, and was keeping an eye on people's drinks, in some cases replacing them just as the last of the previous one was drunk. This got her more than one smile, and "thank you", which felt great, being appreciated by others.

After the first time someone ran out of chips (due to an ill-considered "all-in" by Gavin), there was a short break while Tony and Mike gathered up the chips and redistributed them. Alanna would have done this, but she was busy making drinks.

Once the chips were distributed, and everyone had a drink, Alanna noticed Tony glancing at Sarah with a questioning look and receiving a nod of agreement. Clearly something more was about to happen.

"Alanna, go into the study, and bring out the whiteboard that you'll find there. No peeking under the cover though."

"Yes, Master, no peeking," she replied, trying to keep the curiosity out of her voice. As she left the room, she heard one of the guests ask "What's this about Tony?" to which came the reply "Patience..." with the sound of a grin behind it.

Alanna brought the whiteboard through and set it up in a corner of the room. Lacking further instructions, she assumed her customary position beside the whiteboard. Tony got up, walked over, and stood next to her.

"Alanna, please remove the cover," he instructed. She did so, to reveal a table of the players' names (although not including Tony), and two columns, labelled "A" and "S". The names were written in Tony's handwriting.

"This is to add a little more spice to the game," he said, looking around the room. "Each time one of you wins a hand, you get to choose either Alanna or Sarah."

(Alanna, in conversation with the author): That phrase, "to choose either", that's when I realised that Master was going to share me, as he'd hinted he might do. My heart skipped a beat, I became nervous, excited, scared, and I'll admit turned on. For the first time since I'd become Alanna my little cock started to stir inside my cage. But I knew that part of me wasn't going to get any action, as Master had made that very clear when laying down the roles in the early days of my sissy-dom.

"What do you mean, choose? For what?" asked Terry.

"For having some sexy times with," replied Tony, causing a few raised eyebrows, and some chuckles. "It's optional, it's just another incentive to win a hand."

"There are some boundaries though," commented Sarah, putting down her book and unfolding her legs from where she'd been curled up on the chair. "Firstly, Alanna does not get her cock out. It stays in the cage. And because Alanna is mine and Tony's little sissy, we say what's acceptable and what's not as far as she is concerned."

There was some nodding around the table as people took this in.

"And Sarah has the say on what's acceptable to her," added Tony. This generated more nods and a couple of comments of "fair".

"Once you've picked one, you put a tick in the appropriate box, and you can't pick the same one twice. If the winner of a hand has already had both, then we'll decide who wins based on the cutting of the deck amongst the others. Oh, and if I win, you all get to cut the deck."

"Is everyone happy with this? We won't go ahead if not, but we can still have a fun poker evening. I know Sarah's OK with this, it was mostly her idea!"

(Alanna, in conversation with the author): My Mistress had come up with this idea? I was amazed, I was going to get cuckolded, and/or fucked, repeatedly, all evening!

"In the interests of fairness, and since she's had no warning, I'm going to break one of our normal policies and ask rather than tell," Tony continued. "Alanna, are you OK with this?"

(Alanna, in conversation with the author): I was shocked, Master was asking me? That was so lovely of him, he didn't need to do this, I'd have done whatever I was told. Once again, I was reminded why I was so happy with Master and Mistress.

Alanna looked up, saw Tony's face, saw the genuineness of the question, and replied "yes Master, I will be happy to serve your guests."

"You're such a good sissy Alanna, thank you," came the smiled reply.

"So, why are we still talking about this?" asked Andrew, with a chuckle in his voice. Tony laughed and walked back to his seat. Alanna notice that there was no whiteboard marker on the board.

"Master?" she said.

"Yes Alanna?"

"Should I get a marker for your guests to tick the boxes?"

"Oh, good thought. Yes please."

Alanna left the room and headed to the study. Behind her she could hear the sounds of the cards being shuffled and some gentle banter. She picked up a pink and a red marker, it felt appropriate to have different colours for her and Mistress, and Mistress's lipstick was a bright red.

Returning to the dining room she put the markers on the whiteboard and looked around the table. Andrew and Rod both needed fresh drinks, so she quickly made those and delivered them. As she was standing between them, she felt a hand on her left leg, running up to the top of her stocking tops. She didn't dare react, but she found it exciting and thrilling.

The announcement seemed to have excited the guests as throughout the rest of the evening, every time she delivered drinks, she found she was getting groped, usually on her legs or knicker clad bum, but at least one person ran their fingers over her cage through her knickers.

The first hand under the new rules was won by Andy, who wasted no time in standing up, walking over to the board, and putting a big pink tick next to his name under "A".

"Alanna, I'd like you to suck my cock please," he said, as he walked back to his chair. Stopping next to it he dropped his trousers and undies and sat back down. Alanna quickly glanced at Tony for permission, he nodded.

Kneeling next to Andy, Alanna stroked his cock a couple of times, then placed her lips around it and slipped her mouth over the full length. She heard Andy moan gently, as she used every trick Tony had taught her, including taking Andy's cock right back into her throat. "Oh god, she's swallowed my cock, that's SO hot!"

She heard chairs scraping as people moved round to get a better look at her, on her knees, servicing one of Master's guests, his balls resting on her chin as she deepthroated him for several minutes, her months of practice and tuition with Master's cock standing her in good stead.

"I'm going to cum, oh god I'm going... I'm cumming" Andy moaned, as his seed shot down Alanna's throat, his cock pulsing in her mouth.

(Alanna, in conversation with the author): It was at this point that I felt like I was truly my Master's sissy cum slut. Pleasuring his guests, without any thought for myself, being used as a human cum dump. I will admit, I took pride in my skills, and maybe a sissy shouldn't have pride, but those skills had been given to me by Master for a reason, and if Master wanted to me to use them to pleasure his guests, then I was happy to do so to the best of my ability.

Alanna held Andy's cock deep in her throat until it stopped pulsing, then in one smooth move slipped it out of her throat and mouth, pausing to plant a little kiss on the tip before sitting back on her heels like she'd been taught.

Andy reached down, and offered her his hand, to help her stand up. She glanced at Tony, like she was supposed to, for permission. He nodded, so she took Andy's hand and stood up gracefully.

"I'd like to kiss you. Just once. To taste my cock on your mouth," Andy asked. Once again she glanced for permission, which was given. She leaned forward and let Andy kiss her, his tongue pressing between her lips just enough to get a taste, and then it was gone again. Alanna stood up straight and waited for her next instruction.

"Could I have a drink please Alanna," said Sarah, breaking the mood a little.

"Oh yes, me too," said Rod. "And me please," from Gavin.

Andy hadn't bothered to put his undies or trousers back on, but no one batted an eyelid. If Alanna had been able to think about it, the whole situation had clearly got a lot of history behind it. But she didn't care, she was happy serving and being used.

During the next hand, more drinks were needed, and Alanna found herself getting groped even more.

"My turn!" said Mike, as he won the next hand, "but I want to change the rules a little..."

Tony looked dubious, "in what way?"

"I want to save my turn, so that if I win again I can choose to have fun with both of them at the same time."

Sarah looked up from her book with a quizzical look, and said "what did you have in mind?"

"I'd like to have you sitting on my face, while Alanna deepthroats me like she did Andy."

Sarah and Tony made eye contact. Sarah nodded. Tony smiled "OK, we'll allow that change, but if we run out of time you've forfeit for this session."

"Alanna, if you'd put a question mark in the "A" column for Mike please. Next hand I guess then..."

The next hand started, there were more drinks, more caressing of Alanna, and then Tony won the hand.