Bought By a Rich Man

Stacey wondered how it had come to this. There she was standing in an airport waiting at the busy gate to board a plane to Ibiza with her shorts down around her ankles. She could feel her face getting redder and redder as the giggles from the other passengers got louder and more noticeable. She had been told to wait a full 3 seconds before picking up her shorts to cover up her slightly flat and long chubby bottom. Her two friends Aimee and Rowan stood there equally embarrassed whilst snapping a few pictures of their friend for proof.

"At least that's £200." said Rowan.

"Yeah, this weekend better be worth it." Stacey sighed.

They had all been in a bar just last week for a girls night out. The conversation had eventually moved to how short Stacey and Rowan were on cash. Stacey needed money to pay rent after a flatmate had moved out and left her in the lurch with nowhere else to go. Rowan needed money for her upcoming wedding. Aimee was the only one who wasn't hard up for cash which meant most of the drinks were on her.

It was at the bar that they had bumped into Andrew, all three of them knew him from school. Stacey had dated him in the first year of high school. If you could call it dating at that age. They hadn't really been out on a proper date as they were only 11 or 12. Eventually Andrew had made fun of her flat ass and she'd very publically dumped him with a huge slap to the face outside of school in front of most of the year. Rowan hadn't really spoken to Andrew much during school except to make fun of him for wearing tighty whities in PE once. She'd noticed the VPL in his shorts. She playfully asked him next time he ran past her base in rounders. His embarrassed face said it all.

Aimee on the other hand new Andrew much better. He'd long had a crush on her and she regularly caught him staring as she bent over. Eventually one day he'd plucked up the courage and decided to cop a feel of the ass that he'd long admired. They'd been standing waiting for the teacher to unlock the classroom one day when decided to quickly grab then turn round to talk to his friends. His plan failed. Naturally Aimee wasn't happy, she immediately tapped him on the shoulder and kicked him hard in the balls. A few days later she caught him ogling her behind again. She turned round and whispered to him "Can you not get a real girlfriend you saddo? I bet the only reason you stare is because you're too small to get a girl. I should tell everyone". With that Aimee ruined his already uncool reputation at school. From then on he was known as 'little Andrew'.

Andrew had done quite well for himself after leaving school, he'd set up a successful business and sold it for millions. They got to chatting, Andrew told them about how he was back in town for his mum's birthday, and they all told him that they were out on a girls night out but that it hadn't turned into much as they were short on cash. It was at this point that Andrew saw an opportunity and with the drink flowing, he made his offer.

All three girls were about medium height, Stacey had green eyes and mousy brown hair. She was a bit curvy, some would say chubby with large 38DD breasts. Her ass was a bit long and flat but had some meat to it. Rowan was the largest of the three girls. Again mousy brown hair with luscious brown skin she had the big breasts and ass of a slightly larger girl. Think Rebel Wilson but maybe a little rounder. Aimee was the one Andrew had always fancied in school. Dark brown hair, bright blue eyes, 36D breasts and an ass to die for. She was slim but curvy in all the right places. Her ass was round and popped out from her back in all its glory.

"I could help you with your money situations..." He suggested. "...but not in like a conventional loan. You'd need to earn it."

The girls looked nervously at each other, knowing exactly what he meant.

"I'd love the money Andy, but there's no way I'm engaged." Rowan pushed.

"Listen, I'll give you £1000 each just to come out to Spain with me and stay at my place, it's then your choice to earn anything over that. I'll set a task list of things you can do to earn. After that it's up to you." Said Andrew.

Rowan looked confused. "So, like you'd just pay us £1000 to go on holiday for the weekend?"

"Yep." quipped Andrew.

"Deal!" all three said.

All three had arrived at the airport and just picked up their boarding passes when the text came through. "So, I'll have you picked you up from the airport. The first challenge is £200 to girl who lets the other two pull down her trousers at the boarding gate and then has pictures uploaded to Facebook by the other girls. You have to wait at least 3 seconds so that it's a good photo. One girl only".

Aimee laughed, "No chance, I don't need the money all that much. I knew he still wanted this ass!"

Rowan looked nervously at Stacey "I think that's too weird for me."

Stacey nervously replied "I think I'll do it. That's like half a months rent for me, I really need it. And at least it's nothing sexual."

"Seriously?! You better have some good underwear on." Teased Aimee.

Stacey was hoping the gate wouldn't be busy but when they got there it was full of groups all looking to party it up in Ibiza. Most of them were guys on 'lads holidays'.

"I can't do this. I didn't think it'd be this busy." Said Stacey. "There's loads of guys here. I've only got a black thong on. I'll be totally on display."

She text Andrew to say she was backing out. The reply made her heart sink. "Any backing out after agreeing will result in a £500 fine."

She showed the text to the other two. Rowan laughed. "Better do some quick squats to firm up that arse then!"

"Fine, let's get it over with..." sighed Stacey.

And that was that, Aimee gleefully pulled at her shorts. Her flabby ass wobbled slightly as the shorts came down while Rowan snapped away with her phone.

Hundreds of miles away in his luxurious modern villa in San Carlos, Ibiza. Andrew sat by the pool chuckling at the pictures appearing on Rowans Facebook page. "Looks like Stacey forget her shorts lmao!" Read the caption above to pictures of her embarrassed flabby rump.

The three girls landed in Ibiza and were whisked away to the Andrews villa by limo. Aimee and Rowan tried to cheer Stacey up along the way. She felt better when she arrived at the villa. Andrew greeted them with cocktails and showed them round. There was an infinity pool over-looking the bay, a rooftop decked out with plush couches, inside an open plan area with a huge kitchen all stainless steel, a massive TV and more plush couches. The place was magnificent.

Once Andrew has shown them round he let them get changed into their bikinis and make their way to the pool to sunbath.

"So girls, time to read you the rules of the holiday." Andrew announced.

Rule 1: Each girl has to complete 1 task per day else the forfeit £500 prize money

Rule 2: There will be one mandatory task each night where all three girls participate

Rule 3: You are free to leave at any point but no money will be paid before the end of the holiday

"Wait, what!? You said we didn't have to do anything and you'd pay us £1000 each!" Rowan protested.

"Well I changed my mind, if you're not happy I can fly you back home tonight, but it means Stacey has just showed everyone her bum for free. You should see the comments it's getting!" Andrew smirked, knowing he had the girls' right where he wanted them.

"If you stay though you'll find that you'll earn quite a bit of money from the trip. Stacey, you could be living rent free. Rowan, your wedding could be paid off and Aimee, you could have some cash to go off travelling if you wanted."

The three girls looked at each other. Stacey knew she had to stay, there was no way she wanted to leave having bared her bum to everyone online. That picture was probably saved on all her friends' phones and laptops by now. After some deliberations, and pleading from Stacey, they decided to stay.

It was at this point that Andrew reminded the girls that both Rowan and Aimee hadn't had their humiliation for the day. He handed them a piece of paper and told them they had 2 minutes to decide who was doing which task.

The list read:

Option 1: You will be wearing an 6 inch butt plug for the next 24 hours - £800

Option 2: I will lie naked on by the pool while you lick my ass in front of the other girls until I've farted 3 time on you - £200

Option 3: You'll be wearing a babies nappy for the next 24 hours, the other girls will post a picture on Facebook of you sunbathing by the pool in the nappy - £500

Aimee quickly told Andrew she'd reluctantly take option 2. She didn't need the money as much and thought the others too humiliating. Rowan looked panicked. She didn't want people seeing her wearing a nappy so she was resigned to option 1.

With that Andrew gleefully fetched the huge butt plug. He handed it and a bottle of lube to Rowan.

"What, here? People on the boats could see me up here by the pool!?" protested Rowan.

"Yep, drop those bikini bottoms and sit on it. Aimee and Stacey can watch." he chuckled.

Rowan dropped her bottoms showing off her huge fat black ass. She bent over with her ass facing her three onlookers and lubed up her bottom. She kept reminding herself that she needed the money. "Glad it's not me, that things huge!" sniggered Aimee.

Rowan had just pierced the tip into her virgin ass. She gasped in shock before telling Aimee to shut up. She was feeling in pain and totally humiliated by the situation she found herself in. Out in public plugging up her ass in front of her two best friends. She continued slowly pushing the butt plug in. She got to about half way before she couldn't take anymore, gasping she said "I can't do it. It's too sore"

Andrew quickly reminded her of the penalties for backing out. Rowan continued to protest with 4" of the butt plug wedged painfully into her ass. Andrew offered to finish the job for her and push the rest in. Rowan agreed, simply to avoid losing money after going through all this pain. Andrew quickly applied more lube to the rest of the plug. Forcefully Andrew began to shove the plug quickly further up her ass. "Ahhhwww!" screamed Rowan. "STOP STOP STOP!" The plug had just reached its widest point.

"Omg my ass feels like it's going to split!" she screamed.

"You've reached the widest point, just a quick push and it's in place Rowan!" said Andrew.

"Come on Rowan, you can do it." Stacey urged. While slightly laughing at her friends' plight. She didn't feel so bad about having bared her bum to everyone now!

Without warning Andrew shoved the last bit of the plug in. "Awhhw!" Rowan squealed.

She fell to her hands and knees in pain, her huge round ass on display to the girls, the plug visible between her cheeks.

"That's a great sight Rowan, but pull your bikini bottoms up!" Joked Stacey.

"Shut up! You didn't have to shove a huge butt plug up your ass, this fucking hurts." Rowan retorted.

Andrew took down his boxer shorts and lay face down on a sunbed by the pool. "Your turn Aimee, get your face in between my ass and get licking!"

"Yeah, Aimee get your face in there and taste those farts!" Rowan teased.

Aimee slowly walked over, kneeled down and sunk her face in to his hairy ass cheeks. "Ew ew ew" she whispered to herself as she began to circle her tongue around his asshole.

"So Aimee, how's that taste?" Rowan joked.

It was at that moment that Andrew let the first one go "Bbbrrrrrrrrppp." Aimee winced as the fart hit the back of her throat.

She pulled back to get some air and let out a loud "eeeewwwww!!" Rowan and Stacey watched on giggling.

For the next twenty minutes Aimee licked away at his ass. Every so often Rowan would tease her and shove Aimee's face deeper into the hairy ass. Eventually Andrew relaxed and let out two loud farts in a row. Aimee jumped off humiliated. Her face smelly and her tongue sore.

Andrew jumped off the sun lounger, pulled up his boxer shorts and walked off back to the house. "I'll see you girls tonight at dinner for your mandatory challenge!"

As he walked off Aimee taunted Rowan for revenge. "How's that butt plug feel, it looks like you've crapped yourself in those bottoms, I might get some holiday snaps of you lying down later for Facebook!"

"Shut up Aimee, how'd that ass taste for you?" replied Rowan.

Too be continued...?