Emily's Unconventional Aunt

It was the Thursday after Emily's cherry had been well and truly popped by her Aunt Shirley's good friend, Colonel Cartwright. And now here she was, less than a week later, her cunt barely recovered, sitting in the passenger seat of her aunt's Mercedes on the way to spend another afternoon with him. Only this time his good friend, Major Thornton would be there too.

Deep in thought, she watched the English countryside rolling past - green hedgerows, stone walls, and the occasional glimpse of old houses set back from the road.

"You're very quiet, dear," Aunt Shirley observed, one hand on the wheel, the other resting elegantly on the gear stick.

"I'm a bit nervous, Auntie," Emily replied honestly, her hands twisting in her lap.

"What are you nervous about sweetheart?" her aunt asked kindly.

"About what will happen this afternoon with Colonel Cartwright and his friend?" Emily said in a slightly high-pitched voice.

"You will be used in whatever way they see fit," her aunt replied matter-of-factly. "It's just how it is in the circle. You know that."

"Will they both fuck me?" Emily asked after a pause, her voice sounding slightly strangled.

"Probably, my dear. That is the purpose of your visit after all. It's all part of your training. No need to be nervous though, you managed the Colonel like a champion last week. Your virgin cunt was so willing, and stretched so beautifully - it was really quite remarkable. And two men is not much different from one, it's just more of the same," her aunt assured her.

Emily couldn't deny that her pussy was twitching at the memory. A 75-year-old gent taking her virginity on her Aunt Shirley's big bed while her aunt watched. Her entire body flushed with arousal as she remembered how it had felt and how hard she had come. And today, her little cunt was going to have another distinguished gent filling it. Her tummy fluttered with nervous anticipation.

"They will probably want to use your mouth as well as your cunny today," her aunt said, as if reading her thoughts.

"They'll put their penises in my mouth?" Emily said, her eyes widening in astonishment.

"Probably dear. Just like Dr. Dravnik did when he hypnotised you. You remember? It's perfectly natural."

Emily did remember. How could she forget lying on the doctor's couch last year just after her last session of hypnosis, her aunt holding her hand, while the doctor put his penis in her mouth.

"I felt like I was in a weird haze though Auntie, and I didn't really like it," Emily said choosing her words carefully.

She didn't want her aunt to think she was ungrateful. She knew that the hypnosis sessions were an important part of her preparation, and her aunt had been very generous, setting them up, and taking her to each one.

"Well, the hazy state you felt will have been due to the hypnosis, but having your mouth used for cock is something you will just have to get used to as you get older, baby girl," her aunt explained gently.

Emily recalled that the doctor's member had been so big it had touched the back of her throat and made her gag. And then there was the thick sticky semen that had spurted out of the slit at the end that she'd been made to swallow.

Auntie had explained to her at the time, that because she was now 18 and a big girl, it was all part of her preparation for being shared amongst her aunt's elite circle of friends. She explained that Dr. Dravnik was part of that circle, and that Emily must do as she was told whenever she was in the doctor's office.

They turned off the main road onto a private drive marked by stone pillars. The gravel drive stretched ahead, lined with ancient oak trees. After nearly a quarter of a mile, the Colonel's mansion came into view, and Emily gasped.

"Auntie, it's enormous!"

Her Aunt Shirley smiled. "Harry has old money, dear. Makes my house look like a cottage, doesn't it?"

They pulled up outside and Aunt Shirley leant over and gave her niece a kiss on the cheek.

"I'll collect you at six. That should give them plenty of time with you."

Emily looked at the house, then at her aunt, and then back at the house.

"Auntie, are you sure you can't stay? Just for a little while?"

"Don't be silly, Emily. Bridge starts at half past two and you know how Lady Henderson gets if anyone's late. Besides, you'll be absolutely fine."

"But Auntie..."

"Now Emily," her aunt said brusquely as she reached across and opened the passenger door. "No fussing, out you get."

Emily climbed out.

"And remember, dear," her aunt said through the open door, "you're a big girl now - no playing up."

"Yes, Auntie."

"Good girl." Aunt Shirley blew her a kiss and glanced at her watch. "Now I really must dash. You can tell me all about it later."

The car pulled away over the gravel and Emily stood watching it disappear down the drive, feeling suddenly, acutely alone. She took a deep breath, walked to the front door and pulled the bell cord. It opened almost immediately to reveal a stern-looking woman - grey hair pulled back in a neat bun, sensible skirt and blouse. Mrs Winters, she presumed. The Colonel's housekeeper.

"Emily. Come in. The gentlemen are expecting you in the library."

Emily followed the woman through an entrance hall that made Aunt Shirley's country house look modest - marble floors, enormous oil paintings adorning the walls, a staircase that swept up in a grand curve.

"Through here." Mrs. Winters opened a door and stepped aside.

The library was magnificent, although it took a moment for Emily's eyes to adjust to the dimness. Heavy velvet curtains filtered the light to a deep red glow, and the vast floor-to-ceiling shelves of leather-bound books seemed to absorb what little light there was, giving the whole room a rich, shadowy quality. There was a stone fireplace, deep leather armchairs and dark panelled walls.

Emily was immediately aware of the two men as she entered. They were both standing. The Colonel she recognised as the man who had fucked her last week - and beside him stood another man she didn't know, but who she thought must be his friend, Major Thornton.

But there was some-one else too - a girl about her own age, on the floor on her knees, between the Major's legs, her head bobbing up and down, her long dark hair swaying in rhythm with the movement. As Emily's eyes got accustomed to the light, she realised with shock that the girl had the Major's cock in her mouth and was enthusiastically sucking it.

"Emily! There you are!" the Colonel crossed the room with a smile and took both her hands warmly. "Come in, come in! Now I would introduce you to my very good friend Geoffrey, but he's somewhat occupied right now with my granddaughter Naomi."

"Your granddaughter!" Emily exclaimed transfixed by the scene in front of her.

Despite her nerves she had to admit, the sight of the girl on the floor moaning around a mouthful of huge cock was already making her pussy throb. The girl was working the Major's penis so beautifully, moving her lips up and down the shaft in such a skilful way.

"Is she your granddaughter?" gasped Emily. "Oh wow, she looks so good at that."

"Yes, well she's a year older than you so she's had plenty of practice. You could learn a lot from her."

Just then, the Major let out a loud groan, and Emily watched mesmerised as his body tensed and he grabbed the back of the girl's head, pushing her mouth more deeply onto his cock. The girl made a choking sound as he thrust his hips forwards, holding her still, and then pumped his load into her mouth.

"Swallow it all, Naomi, there's a good girl," the Colonel called out, instructing his granddaughter from the sidelines.

He had put an arm around Emily's back and under her arm, and his hand was casually stroking her breast through her top, his fingers playing with her nipple, which was stiffening under his touch. Emily had barely noticed, she was so enthralled by the scene in front of her, but there was no denying the warm effect it had on her, and she instinctively relaxed and leant into the Colonel, allowing him to fondle her tit more easily.

When the Major had finished with the girl's mouth, he patted her head as if she was a favourite pet, and she leaned back on her ankles and wiped her mouth with the back of her hand.

"Marvellous, young lady," the Major said appreciatively, popped his softening member back in his trousers and zipped up his flies. "Just what I needed."

Emily watched transfixed as the girl stood up and, with a warm smile, approached them. She then stood on tiptoes in front of her grandad and opened her mouth. To Emily's amazement he slid his fingers in and circled them around, and Emily realised he was checking that she had swallowed all the Major's cum.

"Good girl, all gone," he said proudly.

The girl then then did a little pirouette in front of her grandad - smiling seductively at him as her tiny skirt swirled up slightly - to reveal the curve of her bare bottom.

"You little tease," the Colonel said grabbing her bottom playfully. "Wait til I get you into my bed later."

She laughed and turned to Emily.

"Hi, I'm Naomi - I've heard so much about you. We're going to have the best fun this afternoon - we'll be besties by tonight, like sisters." She flicked her long dark hair over her shoulders. "But first Grandaddy please can I show Emily the stables - you said she wanted to see the horses?"

"I suppose so," the Colonel replied, reluctantly. "But don't be too long girls, I have plans for you. Meet us in the billiard room in no more than ten minutes otherwise you'll be getting a thrashing."

"Thanks Grandaddy!" Emily exclaimed delightedly and taking Emily's hand, led her through the library to some tall glass doors.

"It's so great having you here," Naomi was saying as they stepped outside into a beautiful garden. "I love sharing my grandaddy with other girls - it makes me so horny. And Grandaddy can come so much - so there's always plenty to go around - he is just the best. The Major is lovely too - his cock is massive and honestly Emily, he's a machine, he can produce so much cum. What you saw back there was just a warmup so don't worry there'll be lots more for you," she said smiling sweetly.

Emily nodded in bewilderment, feeling stupidly inexperienced and awkward.

As if reading her mind Naomi continued, "Grandaddy said you're fairly new to the circle. I know your auntie did your prep - I've heard about her, she's a bit of an icon, you're so lucky. I was prepped by Mummy - she's great but she's busy right now prepping my little sister Suki for her training - she's just turned 18, so I'm spending a lot of time at Grandaddy's. Not that I mind. It's great here."

Emily tried not to look shocked as they wandered through the lovely garden filled with butter-yellow daffodils and scarlet tulips. There were ancient rose bushes, just beginning to bud, and an apple tree near the centre of the lawn. Emily could hear the trill of a robin and the call of a wood pigeon. It was all quite surreal.

"I know you're still in training but will this be your first time with two men?" Naomi asked as they reached an old stone wall, its surface softened by moss and climbing ivy.

An arched gateway led them through to the other side, where a wooden stable was sat on the edge of a green paddock. Several horses were grazing nearby.

"Yes, I've only ever been with the Colonel, your grandad, before, and just the once," Emily replied.

She liked Naomi instinctively - there was a warmth and ease about her - and she could already feel the knot of nerves in her chest beginning to loosen. She gazed at the horses with delight. "Oh, they're beautiful!"

"Aren't they, perhaps we could go for a ride together one day," Naomi smiled, pulling a handful of grass and holding it out on her flat palm as a piebald trotted over, its breath warm and soft against her hand. "By the way - I love your skirt."

Emily glanced down and then laughed. They were dressed almost identically - tiny skirts that barely skimmed their bottoms, cropped tops that showed off their flat tummies, and white socks and plimsolls. The only difference was that Emily's skirt was white and Naomi's was dark blue.

"Oh thanks," Emily smiled. "My aunt chose it."

"Mummy chose mine but mine is like a schoolgirl's, whereas yours looks like you've just come out of church - you look so cute. Come on, we should get back - if we're late Grandaddy will have me over his knee in a flash!"

"Over his knee?" Emily repeated, somewhat surprised.

Naomi laughed, "Grandaddy is lovely, but he is a bit of a stickler for discipline. He loves giving my butt a good spanking."

"Oh gosh really," Emily felt her pussy contract - she rather liked the idea of being put over Naomi's granddaddy's knee and spanked. "Does he do that much?" she asked eagerly as they headed back to the house.

"A bit yes," Naomi replied. "He used to spank me a lot when I was younger when he couldn't fuck me. But now he can fuck me, not so much."

"How long have you been part of the circle?" Emily asked.

"I had the hypnosis when I was 18, finished the preparation not long after that, and then completed my training six months ago, so in total about two years now. They kind of fast-tracked me as I took to it so well. I've played with lots of the circle - so any questions just ask - I know it's a bit scary when you're just starting out. I'm still dying to meet your aunt though - she has an amazing reputation."

Emily felt a surge of jealousy that she tried to squash quickly. Naomi clearly enjoyed her grandad playing with other girls, and she realised that she might have to change her possessive attitude about her aunt if she wanted to stay friends with Naomi.

"Anyway," Naomi was saying "We are going to have so much fun this afternoon. You and me together with Grandaddy and the Major! I am so excited."

They were back at the mansion now, and as they crossed the garden Emily spotted Mrs Winters standing with her arms folded, her expression thunderously stern.

"Young ladies - you are wanted in the billiard room. Right away!" she called out, her voice clipped and sharp with disapproval.

Emily's heart leapt straight into her mouth. Mrs. Winters terrified her. But Naomi simply giggled, seemingly unconcerned, took Emily's hand and led her back inside, along a wood-panelled corridor where large oil portraits of ancestors loomed from the walls, their stern eyes following the girls as they made their way through the house.

The billiard room stopped Emily in her tracks. At its centre sat an enormous table covered in green baize, ornate brass light fixtures hanging low above it, casting a warm but somehow oppressive glow. The leather armchairs and sofas were dark and heavy against the walls, and there was a great stone fireplace at the far end.

The Colonel and the Major were mid-game. They turned to look at the girls. Emily's feet stopped at the threshold, and she gripped the doorframe nervously.

"I have to go pee," Naomi said suddenly, and to Emily's horror she disappeared leaving Emily alone with the two men.

"Don't be long, you girls have work to do this afternoon," the Colonel called after her, putting his billiard cue down. "Now Emily, allow me to properly introduce my very good friend - Major Geoffrey Thornton. He has been looking forward to meeting you. Geoffrey, this is Emily, Shirley's niece."

Emily looked at the Major fully for the first time. He was striking in the way that older men sometimes are - thick silver hair swept back from his forehead and deep dark eyes that looked at Emily with a measured scrutiny. He was undeniably handsome, but the kind of handsome that didn't put you at ease. Naomi had called him lovely, and Emily supposed she could see why, but there was something behind his eyes that made her breath catch. She felt his gaze move over her steadily.

"Nice to meet you, Emily. You look very sweet and innocent, like you've just stepped out of a classroom," he said in a low tone.

"Now, behave yourself Geoffrey - she's nineteen, university student. But yes, she does have that innocent quality about her, doesn't she?" the Colonel's hand rested on Emily's shoulder. "And she was innocent, until last week, when I popped her cherry."

The two men laughed at the Colonel's joke and Emily smiled awkwardly, her face reddening. She wished Naomi would come back.

"Come here young lady. Let me have a proper look at you," the Major said gesturing to her.

Emily nervously walked over to him, and he immediately reached out and grabbed her bottom, pulled her against his body, and then slid his hands down and felt underneath her tiny skirt.

"No knickers!" The corners of his mouth twitched with delight, as he gave her bare cheeks a squeeze.

He then turned her slightly, lifted up the front of her skirt and slid his fingers along her hairless bare slit then pushed a finger inside her cunt. Emily whimpered and tensed.

"Just relax, it makes it all so much easier if you just let us do what we want," he murmured in her ear. "I don't want to force myself on you - but I will if I have to."

Just then, to Emily's huge relief, Naomi returned - she felt safer and more balanced, just by having her back in the room.

"Oooh look Grandaddy, Emily and the Major are getting very well acquainted," Naomi said excitedly, her eyes dancing at the sight of the Major with his fingers inserted in her new friend's pussy.

She snuggled up to the Colonel, who wrapped his arms around her as they watched the Major fingering Emily.

Emily whimpered softly as the Major's fingers pumped in and out of her wet cunt. Then, after a short while, when it looked as if Emily's legs might give way, the Colonel suggested it was time for the girls to get undressed, and the Major let go of her.

"But leave your socks and plimsolls on," the Colonel reminded them.

This was normal procedure in the circle; girls were expected to be fully naked except for socks and footwear, usually plimsolls. This was partly so their feet didn't get cold, but mostly it meant they could be transferred easily if someone wanted to move proceedings to a different location, such as a stable, a shed or an outbuilding. The other factor, of course, was that it made them look sweet and vulnerable.

Naomi moved over to Emily smiling excitedly. Up close Emily saw just how truly pretty she was with her full pink lips, dark brown eyes and mane of thick dark hair that reached to her bottom. With practised ease she took hold of Emily's top and pulled it off over her head and then reached around and unclipped her bra releasing Emily's breasts.

"Ooh they're so pretty!" she said cupping Emily's tits in her hands. "Mine are bigger but then you're younger than me so yours are probably still growing."

Naomi then removed the rest of Emily's clothes, just leaving her in her socks and plimsolls as instructed, and Emily stood, her arms folded across her chest shyly, as Naomi also undressed. The two men looked appreciatively at the two beauties in front of them, one with long blonde hair that swished around her waist, and the other with a dark mane reaching to her bottom.

"Grandaddy, can I just say something?" Naomi asked thoughtfully.

"Yes of course sweetheart, seeing as you've asked so nicely."

"I think we should give Emily one of your lollipops - it'll make her more relaxed."

"Excellent idea, angel. Naomi is right Emily, you're probably nervous without your aunt here and this being your first time with two men," the Colonel said kindly. "All perfectly understandable."

Naomi had crossed to a desk and returned with a large round lollipop - the old-fashioned kind, red and white swirls and handed it to her grandad.

"Here we are." The Colonel unwrapped it and held it to Emily's lips. "Open up. This will help settle your nerves."