Helen knew what was coming even before Kim spoke.
Four days previously, Helen had told her best friend about her first painful anal experience, saying she had hated it. Deep down, Helen knew she was lying. Helen had loved it, though she denied it vehemently - even to herself. After much persuasion, Helen agreed to try again with Kim there for moral support.
Now, the formerly shy and nervous Kim was pressuring her.
"Get your arse fucked!" Kim ordered her. "I'm sure you'll love it the second time around."
Helen didn't dare tell her buxom Japanese friend about the previous day's aborted shopping trip that had filled her backside with cum. Again. And she had loved every filthy moment. She blushed guiltily, knowing she'd enthusiastically do it again.
"I guess," she replied lamely.
Kim laughed. "I know you; you'll just keep putting it off." She sighed, sounding exasperated. "But that won't do. You know I'm away from Friday; it must be before then."
Helen was still not used to this newly assertive girl, though Kim had never procrastinated like Helen did.
Helen knew few men; all of her three sexual experiences had been with complete strangers. "There isn't anyone to do it!"
Kim looked surprised. "I thought you said those rugby blokes from last time would?"
The time before last. Helen looked guiltily at her best friend. "I don't have numbers for them."
"There must be someone you like?"
Helen shook her head. "God, I can't imagine anyone from school. The story would spread like wildfire. I don't know anyone."
Kim shook her head. "I guess not." Kim laughed. "We'll have to hook you up with another stranger then."
Helen blushed scarlet once more. Not only had her riding instructor deflowered her on their first meeting, but her two subsequent anal experiences had been with utter strangers.
"I suppose so."
Kim laughed. "What's with you? I've never seen you blush before."
Helen grinned shamefacedly. "I seem to like strangers."
Kim looked determined. "That settles it, then. Two complete strangers, one each." Kim leered. "And both of them can bugger you senseless."
Helen felt her panties dampen. "I'd better enjoy it this time," she lied. "It can't be around here; everyone knows me," She giggled. "Let's go to London."
Kim frowned. "I don't want to trawl seedy clubs looking for skanky losers."
Helen shook her head. After his last trip to the city, her father had said disgustedly that all the posh hotels were full of high-class tarts.
"That's not what I meant. We'll check into a posh hotel, pretend to be hookers, and pick some randy businessmen up in the bar. Daddy says all the hotels are full of escorts."
Kim blushed, looking excited. "Oh, that sounds fantastic! And I've never been fucked by a stranger; it all sounds so exciting. Let's do it!"
Helen was suddenly afraid. She'd willingly submitted to being bum-fucked by complete strangers, but she had never deliberately planned it. Helen had loved both encounters, but the thought of actively seeking out strangers to invade her bottom was terrifying. She'd never even had the nerve to flirt with boys at school, let alone approach someone for sex.
"I can see you're nervous," Kim said. "Don't worry, I'll plan the whole thing."
Kim looked wistful. "I wish we could include your dad. I'd love him to fuck me again before I go away." She looked at Helen, grinning. "But with you there, that's impossible. So, I guess I'll have to settle for some random blokes, though I'll admit the idea of a stranger's dick inside me has me dripping wet!"
Kim was terrifyingly efficient. Soon, Helen had a hotel booking for the following day, rail tickets, and an email with the plan.
The plan became more complicated when her father suddenly announced he had a meeting in London and they might as well travel together.
Sure, it was convenient, but they couldn't discuss their plans on the train, and she feared she'd give them away.
From the moment she awoke the following day, Helen was torn. Half of her was terrified of approaching strange men, asking for her arse to be fucked. The other looked forward to the intense pleasure of a dick splitting her backside open.
The added worry that her father might work out their purpose meant that Helen was nervous and skittish until they got off the train at Finsbury Park, abandoning her father to his meeting.
Not that she need have worried he'd divine their erotic intent. Her father and Kim could hardly keep their eyes off each other, exchanging covert glances. It was sickening, really.
Twenty minutes by Tube and a short walk later, the girls arrived at their hotel. It was too early for check-in, so they dropped their bags at reception.
"Come on, let's go," Kim said excitedly. "If we are quick, we can be first in the queue at the Gallery."
Helen dreaded her best friend's enthusiasm for medieval art. She had endured many tedious afternoons listening to her friend. But Kim was her best friend, so thirty minutes later, they were in the queue for the National Gallery.
"Do we really have to do this?" Helen asked. "Daddy will never know if we skip it."
Kim laughed. "All part of our cover story. Anyway, I don't care. I love this shit."
Three hours later, even Kim had had enough. After an extended trip to the gift shop, where Kim spent a fortune on books, they slumped in a nearby café sipping tea.
Most of the art had passed Helen by, but she smiled when she realised her butterflies had been banished for a while. Now they returned with a vengeance as she realised that soon she'd have to pick up a stranger and be paid for sex. But I'm not that kind of girl!
To distract herself, she asked, "Why aren't you doing History of Art like Jessica?"
Kim laughed. "Oh, I love the art, but that's too pretentious and all ego and opinion. History is far more satisfying. Evidence-based, if you like."
Ouch! Kim had skewered her own obsession with science. The girls argued frequently over the meaning and worth of evidence. If only science could quell her terror of a simple, if intimate, social interaction: you pay, you get to fuck my arse.
They returned to the hotel and checked in. The desk clerk gave them adjoining rooms and two keys each. Helen noticed him surreptitiously checking them out. The clerk's eyes widened when Kim inhaled deeply.
Their bags were dumped in Helen's room, leaving Kim's room anonymous for their planned escapade, with only some lube left by the bed. Satisfied they were ready, the girls went downstairs for food.
The butterflies in Helen's stomach meant she had no appetite. Scenarios rolled around her head repeatedly, but she couldn't see herself going through with any of her imagined approaches to strange men.
"Something light, I think." She grinned at Kim. "I don't want to be fucked on a full stomach," she said to cover her terror.
She knew all nervousness would vanish the moment she saw a rampant dick, but until then, she was resigned to the churning in her belly.
Helen picked at her meal until Kim suddenly said, "Leave that. It's time to look sexy but slutty."
They changed in Helen's room, as Kim's was empty. The two girls were naked when Kim brandished two butt plugs.
"Wear one of these. It will stretch your arse, ready for action."
Helen had never tried a butt plug. And although she'd gleefully submitted to dicks invading her arse, the idea of pushing a plug inside herself felt gross.
Her cheeks felt hot. "God, I can't! You'll have to help me."
Kim giggled. "Sure. Sit down on the bed."
Helen obeyed and watched her friend rub oil onto a silver butt plug. She craned her neck to watch when Kim approached, pressing the oily plug against her sphincter.
"Relax, or it will hurt."
Helen tried, but it was still painful as she watched her friend force the fat, silver plug into her tight, resisting ring. She gasped when the widest part slipped painfully inside, and her arse clenched around the narrower neck.
Kim smiled at her pained expression. "You'll soon get used to it."
Helen watched Kim grimace as she rammed the other plug into her own backside.
Kim smiled happily. "Come on, let's get dressed now."
Helen had picked out a figure-hugging dress. White and covered with tiny blue stars, it barely covered her bum and stopped at her armpits, showing off her big, perfect boobs. It was only held up by being tight at the waist. A decorative blue bow on a thin blue belt accentuated her narrow waist. The blue matched her eyes, and she wore her long blond hair loose, cascading down her back.
Underneath, Helen wore pretty, pink panties. Her legs were bare except for her white heels.
She checked herself out in the mirror and nodded. She thought the outfit screamed, "Available."
Kim's hair was in an elaborate confection, partly up, with a ponytail. She wore a killer little black dress that hugged her buxom figure, leaving little to the imagination. Like Helen's dress, it was scandalously short.
The black heels made her tiny friend seem taller, accentuating her shapely legs. Helen was envious of her sumptuous body.
Helen was still aware of the plug stretching her arse when they headed for the lifts, but, as Kim had promised, it no longer hurt and felt odd but pleasant.
"You look terrified," Kim said as they waited for the lift. She smiled. "Relax and enjoy yourself, and try to at least flirt a little."
When the lift pinged open, they descended to the ground floor and headed to the bar they had spotted earlier.
The girls sat at the bar on high stools. A barman came over and took their order, asking for ID. Helen grinned. His gaze never reached above chest height.
Helen watched the man pour the drinks. Kim was drinking Sauvignon, her favourite tipple. Helen was so nervous that she ordered a double G&T.
When the drinks arrived, the girls carefully arranged themselves, facing each other with a good view into the lounge bar. Helen felt self-conscious, imagining everyone knew she had a plug in her arse. People came and went, most staying for a single drink. A few prospects sat down, but the girls quickly dismissed them. Too ugly, too young, not rich enough. Finally, when they were on their second drink, Helen spotted two smartly dressed middle-aged men checking them out.
Remembering her friend's advice, Helen smiled at the men. She pulled her shoulders back, thrusting her chest out alluringly and nodded slightly to Kim, who inhaled deeply, careful to give the men a good view of her mammoth boobs.
Sure enough, Kim's pornstar figure had the desired effect. One of the men stood and walked over.
The grey-haired man gestured toward the table where the men sat. "Care to join us for a drink?"
Kim beamed at the man. "Of course."
The girls walked over to the table. Helen tried to swing her hips sexily but thought she had failed. They sat in the low chairs, so Kim and Helen sat opposite each other, between the two men. Both men looked lean and fit. One was totally grey. The other had dark hair tinged with white at the temples.
The grey-haired man introduced himself first, "Hi, I'm William, but most people just call me Bill."
Helen was so nervous she cut across Kim.
"Kim," "Helen," they said simultaneously.
The other man laughed. "And I'm John. Pleased to meet you, ladies."
"What brings you two pretty young things to London?" Bill asked.
Kim laughed. "Oh, the usual. National Gallery this morning, shopping tomorrow." She leered at Bill's crotch. "Sex tonight."
Both men looked shocked. Helen was astounded her previously shy friend was so bold.
John tried to look innocent. "Waiting for your boyfriends?"
Helen giggled, too terrified to speak. Kim stretched languidly again, "In a manner of speaking." She scanned their groins again, which were tented by erections. "For a price, you two can be our boyfriends."
The two men paused, open-mouthed. Finally, Bill spoke, "What do you think, John? They are pretty enough."
John looked back and forth between Helen and Kim, his gaze fixed on their ample chests. "I do like big tits."
Finally, he grinned. "Let's show these young ladies a good time."
Brian popped a small pill and tossed the packet to John. "You might want this."
John read the label and nodded. He swallowed a pill, washed down with beer, leering openly at Kim's massive boobs. Brian grinned lewdly at Helen, his eyes fixed on her crotch, "We have to get our money's worth."
Helen zoned out as Kim chatted seriously with the two men, knowing her best friend was selling her body for intimate sexual services.
Finally, Kim was done. "So, two hours. Any hole bareback, both of you on both of us, repeatedly?"
The girls had decided in advance that this was what they'd allow, but Kim managed to weasel more cash for their services. Helen was astonished at the negotiated price.
The men looked at each other, grinning. "Don't move," Bill said, "we just need to get cash."
John laughed. "Don't worry, we won't abandon you." He looked at Bill. "You go first, then I'll go."
Bill stood and walked towards reception. Kim stood and sat on the arm of John's chair, pressed close against him.
Bill returned a few minutes later. He smiled, glancing at John, who had his arm around Kim, before looking at Helen. "I guess I get to screw you first."
Helen was too terrified to move. She spread her legs, exposing her pink panties. "Fine by me," she managed to whisper.
John disappeared towards the cash machine. When he returned, Kim passed him her room key and whispered the room number. "See you upstairs."
The girls downed their drinks and walked to the lifts. Kim opened her door with her second key.
They waited inside Kim's room for the two men. Helen fidgeted. "God, I'm terrified."
Kim looked her friend up and down. "Why? You've been fucked by strangers before."
It felt so different, deliberately and explicitly seeking them out. "I can't explain. It just feels scary." She paused. "And the money. It makes me feel ever so cheap."
The door beeped and clicked open, and the two men walked into the room.
Bill waved a thick wodge of notes, ostentatiously putting them on the bedside table. "It's all there."
It was a lot of cash! Suddenly, Helen didn't feel so cheap, though she was still ashamed she was selling herself.
When the door closed behind the two men, Kim grabbed John's belt and pulled the man towards her, feeling inside his trousers.
The moment had arrived. Helen knew she had sold her body for sex. I'm not that kind of girl! She froze.
Bill looked her up and down, licking his lips. He reached for the decorative bow on the front of her dress, "I want to unwrap my present."
His words and not wanting to ruin her dress snapped Helen out of her daze. She giggled and quickly turned her back on him. "Not like that; unzip me."
A strong hand groped her boobs. She felt Bill fumble for the zip, and his fingers ran down her back as it descended. The figure-hugging dress was now loose and open at the back. It slid untidily to the floor, leaving Helen wearing pink panties and white high heels. Bill's hot hands caressed her soft backside and then slid around her naked waist and up to tweak her puffy nipples.
Helen was still scared but aroused when she turned to face the man. Her hard nipples pressed against Bill's shirt, and she grinned shyly up at him.
"You've never done this before, have you?" Bill said, sensing her nervousness.
Helen shook her head. "We're only doing it so I can get my arse reamed."
Hands grasped her bum and pulled her cheeks apart. Bill leered. "We'll get around to that, I'm sure, won't we, John?"
John cackled lewdly. "I can hardly wait!"
The two men laughed. "We've never picked up, err ... escorts before, so it's a first for us too," John said. "You two were so obviously gagging for it, and your friend was extremely persuasive. We thought she was a right pro, especially how she negotiated."
Helen looked at her friend. Kim was already naked, wearing just her black high heels. She was on her knees, undoing John's trousers. It was Helen's turn to laugh. "She's usually the shy one."
Helen slowly unbuttoned Bill's shirt and knelt, mirroring Kim's pose. Bill removed his shirt as she undid his trousers. Helen grinned when she heard gobbling next to her. A glance confirmed that Kim had John's dick deep down her throat. When she turned back, Bill was already out of his trousers. Helen massaged his Y-fronts, feeling his hard erection through the fabric. She was slightly disappointed. He wasn't small, but she had hoped for another monster.
Helen grinned up at him as she released his dick. Bill was circumcised, which she'd never seen before. Curious, she bent forward, and her tongue explored his glans. It felt rougher on her tongue and didn't have that shiny, wet look. I prefer uncircumcised. Knowing the man expected it, she took his rigid pole into her mouth, bobbing her head as her hand wanked his shaft.
"Enough," Bill ordered after a few moments. "I want to save my jizz for later."
Helen pulled back and smiled up at him with spit dripping off her chin.
Bill shook his head briefly. "You both look like bloody pornstars. Do you mind if I film you?"
Helen was excited by the idea. "Go right ahead."
She admired his firm bum as Bill walked over to where he had tossed his trousers. He bent over and pulled out a phone.
Helen stood up when Bill walked all around where Kim gobbled John's slimy dick, with his phone pointed at them and recording. "God, that looks so hot," he said when Kim's nose was pressed to John's groin.
Bill turned the camera on Helen. She thrust out her chest proudly. "Take off your knickers," he ordered.
Helen slowly pulled her pink panties down, leaving them around her knees, exposing the wispy, blonde fluff of her pussy. She stood still as Bill walked around her with the camera. "Gorgeous. I can't believe I'm about to fuck you."
She could hardly wait.
Behind her, he said, "Grab your ankles, girl."
Bill gasped. "Fabulous."
She felt a hand push against the butt plug embedded in her arse. A finger roughly probed her slit. "God, you're dripping wet."
Helen heard a groan next to her. "I'm coming," John said.
John's rigid cock was in Kim's mouth. "All over her face," Bill said.
Helen watched as John pulled out, and jizz immediately gushed from his cock, spraying sticky streams of cum all over Kim's pretty face and hair, missing her open mouth.
Bill laughed. "Perfect. Now let's fuck these whores."
A fresh wave of shame passed through Helen. I'm not like that. But it was true. They had sold themselves for sex.
"Get on the bed," John said. "Side-by-side in doggy position."
The girls obeyed. Helen stepped out of her panties and joined Kim on the bed. She pressed tightly against her friend. Kim turned her head towards her, and Helen briefly kissed Kim's cum covered lips, tasting salty spunk.
"I love the butt plugs," John said.
"Never fucked a girl with a plug in her arse," Bill said.
"Me neither."
The bed creaked when John climbed behind them. A finger probed Helen's wet minge, and she heard a sharp gasp from Kim.
Helen looked at her friend, who sighed contentedly as John penetrated her. "That feels wonderful."
John also sighed, "Your cunt is so small and tight. I don't want to hurt you."
Kim giggled. "You're stretching me wide open. Just pound me hard, please."
Bill moved slowly around the bed, still filming. After a moment, he tossed the phone onto the bed. "Fuck it. That'll do for now."
Moments later, the bed creaked again as Bill knelt behind Helen. Two fingers rubbed briefly up and down her slit. A cock nudged rudely at her entrance. She moaned when it thrust hard into her wet minge.
She felt every inch slide past the plug in her arse, stretching her pussy delightfully. Hands massaged her boobs before gliding down her smooth flanks to grab her waist.
Bill sighed. "So fucking tight."
Helen loved the excitement of another strange cock inside her. The sensations as Bill's dick slid in and out, pressing against the butt plug, were fantastic. Her excitement mounted as Bill increased the vigour of his thrusts, and she started panting softly.
Kim's hips rubbed against Helen as her friend was fucked hard alongside. Kim's loud moans told Helen that her friend was also aroused and nearing climax.
She breathed deeply and tried to hold back, wanting to come simultaneously with her bestie. That would be so fucking hot!
Bill grunted with effort as his dick slammed rapidly into Helen's tight minge. "Fucking incredible," Bill moaned. "So tight and wet."