Emmas Initiation Ch 01

This follows on from the Carly and Steve stories and is the 7th in this series.

*

"Bloody hell," Emma exclaimed to Carly, "That was Ian, he wants to meet me for a drink!"

The previous weekend they had met in a bar and ended up having a full blown orgy with 7 of them involved. Emma had given him her number but hadn't really expected him to call. After what they had all got up to that night she had assumed he was just being polite.

"Are you going to meet him?" Carly replied.

"Yeah, I am." Emma said.

"I don't blame you," Carly went on. "Just be straight with him about what you do from the start this time."

"I'm going to," Emma added, "I hope he's ok with it, he seems like a nice bloke."

"I can't see that he'd have a problem," said Carly, "He has watched you take it up the arse from 5 blokes in one night! I don't think he's expecting that you live like a Nun!"

Emma smiled, Carly had a point. Emma was still concerned though as there was still a stigma attached to her job. She was convinced that he wouldn't want to know her once he found out she was a prostitute.

Emma and Ian arranged to meet the following Thursday, she was a complete bundle of nerves by the time she was ready to leave. Emma wore a pair of black trousers and a tight red top that showed off her 38DD tits. She was a size 14 and a little bit bigger than she wanted to be but men always complemented her on her body. Her dark brown shoulder length hair and dark brown eyes were her best feature she thought, although most of her men would look a little lower! She kept the make-up to a minimum as well, she only overdid it these days when working for the maximum "Whore" effect.

Ian was already waiting or her a the bar when she arrived, he was taller than she remembered, about 6' 1", fairly slim with cropped hair. He immediately remembered why she fancied him and was hoping he felt the same.

"Hi," he said, giving her a kiss on the cheek. "You look lovely."

Emma blushed and gave him a smile. This was the first proper date she had been on for years. She had been with her estranged husband for 8 years in all, so she had only had the odd one night stand and clients in all this time.

They had a couple of drinks and chatted, just small talk at this stage. Neither had mentioned their previous night together.

"So what do you do for a living then?" Ian asked.

Emma had dreaded this bit but decided to take Carly's advise and tell him straight. She had no plans to quit her job, the money was too good, so he had to either accept it or forget her.

"I work in a massage parlour," she said, "Call me a whore, prostitute, hooker, whatever you like. I sell my body to men and make good money doing it."

Emma tried to sound as bold and brassy as she could even though she was shaking.

"I'm not surprised you make good money!" He smiled at her, "Not after what we got up to last weekend!"

Emma felt the relief, he didn't seem bothered at all.

"Does it not bother you?" Emma questioned.

"No." Ian said, "I wasn't expecting you to be the Virgin Mary after what we did that night!"

"Thank god for that!" Emma felt relaxed now this was all out in the open.

"Look, I'm not making any promises of anything serious but I like you." Ian continued. "Let's just see how things go, you might even be shocked by some of the things I get up to!"

Emma was intrigued by this comment, Ian clearly wasn't bothered about her past or job and sounded like he may have lived a bit himself.

After a couple more drinks the conversation turned more to sex.

"So how many clients do you see in a day then?" Ian asked.

"Usually between 6 and 10," Emma answered. "My record is 15 though!" She continued proudly.

"And what about at one go?" He asked.

"Carly, me and 2 other girls did a party once with 12 men, that was my most extreme job yet." She replied.

"How did you enjoy it?" He continued, clearly getting turned on by this talk.

"I had a great time," Emma said with a cheeky grin. She noticed he had a bulge in the front of his trousers now.

"Drink up," Ian ordered her, "We're leaving!"

Emma did as she was told, loving this good looking man taking the lead like this. Ian soon flagged down a taxi and gave him his address, his flat was about a 10 minute drive away.

As soon as the taxi pulled away they started kissing. Their hands started to wander over each other, the anticipation was building quickly. Emma could feel herself starting to get wet, while Ian's erection was now straining to get out.

Ian paid the taxi driver, giving him a sizeable tip, he didn't want to waste any time waiting for change. Once through the doorway into the flats, Ian pulled her close to him and kissed her again. He thrust his hand between her legs and started to rub her. He could feel the wetness through the material already.

"Shouldn't we actually get inside first?" Said Emma pulling away. "Anyone could come outside and see us!"

"Doesn't that turn you on even more?" He asked.

"Well, yes, it feels great." She stuttered, "I just don't want you to get caught by your neighbours."

"Don't worry about that," he replied, placing her hand on his cock. "Look what you're doing to me!"

Emma hesitated for a moment then unzipped his trousers. If this was his little kink, the thrill of being caught, she'd be happy to go along with it. Emma freed Ian's thick 6" cock and dropped to her knees. She wasted no time swallowing as much of his length as she could. Being a bit scared of getting caught, Emma sucked his cock hard, wanking him fast at the same time.

Ian looked down, his face a picture of pure lust. He grabbed her hair pulling her towards him further. Emma normally hated this but was getting extremely turned on by the danger.

Ian then tensed up and without a sound, shot his hot come into Emma's mouth. Bolt after bolt of his seed poured into her mouth as she struggled not to spill any. Emma managed to swallow it down apart from a couple of jets that had ended up on her top.

"That was amazing!" Ian whispered to her, "Sorry I pulled your hair like that, I got carried away."

"That's ok," She replied, "I quite liked it! Now let's get inside so I can fuck you."

Once inside Ian's flat on the first floor they tore each others clothes off and kissed again. Both naked, Ian bent Emma over, with her leaning on a chair and started to lick her completely bald pussy. She gasped, feeling weak at the knees. Ian continued to eat her, making a filthy slurping noise as he did, he was clearly loving this. He then moved up and started to tongued Emma's arsehole. She let out a whimper before grinding her arse back into his face.

Ian stroked her clit as he tongued her anus, more juices were starting to flow from her moist slit as she started to come. Once her first orgasm subsided, Ian put 2 fingers inside her and started to rub her G-spot while continuing to rim her. This soon had her coming again, this time, for the first in her life she ejaculated. Not loads like she had once seen in a porn film but this was a definite first.

Emma collapsed onto the chair, exhausted. Ian joined her and held her in her post orgasmic glow. She felt a kind of connection with Ian, maybe she was reading too much into it but she felt something.

"You're the first man who's ever made me come like that!" She eventually said. "Where did you learn that little trick?!"

"I can't tell you that sort of secret yet!" Ian joked.

"I'm intrigued to hear about some of the stuff you're into." Emma said. "Tell me more."

Ian was quiet for a few moments then said, "Dogging. Have you ever tried that?"

"No," Emma replied, "I've tried most things once but never that."

"I was married until 3 years ago, my wife and I decided to give it a go." He continued, "We just went to watch others at first."

"Did you both enjoy it?" Emma asked

"I loved it, but Jo was a bit shocked by it all." He said, "It had been one thing talking about it but the reality was a bit too much."

Emma just sat and listened.

"We didn't go back for a couple of months so I suggested it again." Ian went on. "This time we discussed it properly, made up our mind that she would give me a blowjob while these men watched."

"Sounds like fun!" Emma said, "How did it go?"

"Great," He said. "We got to the car park and got ourselves together then flashed the interior light. That's the signal to let you know you want to be watched."

Emma again stayed quiet and listened.

"Jo took her top off and my pants down and started to suck me," Ian said, clearly enjoying reliving this story. "We soon had about half a dozen people crowded round. You guessed they were all men but you couldn't make any faces out, that added to the thrill."

Emma smiled and started to rub Ian's cock, he was starting to get hard again.

"I came in no time that night," Ian continued, "It was all too much,"

"I'm not surprised!" Emma replied, "Didn't Jo want any of the action?"

"Not that night," he said, "But she did eventually. We kind of built up to it until she ended up taking on anyone, she couldn't get enough."

"Did it not bother you, her fucking other men?" Emma asked.

"No, I enjoyed it." He smiled, "We both got a lot out of it."

"So how come you split?" she replied.

"We started to drift apart eventually," Ian answered, "Sex was the only thing we had in common in the end. She took a job in America in the end and we agreed to part."

"Shame." Emma sighed, "Not for me though! I want that cock of yours inside me!"

Ian picked her up and carried her to the bedroom, he was soon inside her making love to her rather than just raw lust. He came inside her before they fell asleep together.

Emma was up first in the morning and brought Ian a cup of coffee.

"Take me dogging." She said, out of the blue.

"You serious?" He said.

"Yeah," She said, "I want to try everything once!"

"You're on then," He said with a huge grin, "I'll check a couple of websites and find out where and when and let you know."

Emma left Ian with a lingering kiss and left for work. She had a spring in her step for the first time in a long while. Her shift was busy and flew by with Emma constantly checking her phone for Ian's call.

He finally rang her the following morning.

"I've found a meeting," He said excitedly, "It's short notice though, it's tonight."

"Bloody hell," That doesn't give me much time to get sorted!"

"You'll be a hit!" He laughed, "I'll pick you up at 8. Wear something sexy!"

Emma felt a mix of fear and excitement, and with Carly and Steve working she didn't even have a chance to tell anyone.

Emma did as Ian said and wore a pair of tight jeans with a low cut top showing off her tits. She had a push up black bra on and a tiny black matching thong. She felt sexy and couldn't wait for Ian to arrive.

Ian was right on time. Emma got in the car and gave Ian her best sexy look.

"Do I look ok?" She asked.

"Fucking gorgeous!" Ian answered. "They're going to love you!"

Ian said it would be about a half an hour drive.

"So have you got any limits tonight?" Ian asked her.

"No!" She smiled, "I never have!"

The chat was mainly small talk for the rest of the journey, the anticipation was building.

When they arrived they weren't alone. Another car was parked in a quiet corner. They had the internal light on and a small crowd of about 6 watching.

"Shall we just do it then?" Emma said. "I want to get started!"

Ian flashed the interior light as Emma took her top and jeans off. Ian took his trousers and pants off, his cock already semi erect. Emma was soon down to her thong and began sucking Ian's cock. Emma saw a face out of the corner of her eye, she couldn't make out the face properly, just like Ian had said but she knew they were being watched.

Emma and Ian climbed onto the back seat for some extra space and Emma got onto all fours to carry on giving Ian a blowjob. She made a point of thrusting her bum up in the air, loving the fact she was giving these strangers a good show.

"I'm coming." Ian said after a couple of minutes.

"Come in my mouth again baby," Emma told him.

Ian closed his eyes and felt his orgasm build. He let out am earthy groan as he shot his load into Emma's warm, welcoming mouth. Emma made a point of theatrically swallowing Ian's spunk so the watching crowd knew what she had done.

"Do you want to do anything with any of these men" Ian asked her.

"I want to be fucked." Emma stated, "But I don't want to see anyone's face."

"You kinky bitch!" Ian said. "I'm getting to really like you, you're up for anything!"

Emma smiled and took her thong off, she felt pleased with herself, maybe she'd finally met her match, a man who was game enough to try anything and not get jealous of her.

Ian wound down the window and explained what the score was. Emma couldn't really make out what they were saying but Ian was laying down the law telling them to respect Emma.

"There's 3 of them that want to join us," he said. "There are a couple more but they're just watching."

"Let's do it!" Emma said.

She got onto all fours and offered herself to the first taker outside the car. She felt a cock nudging her lips then entering her. She cried out as the full length entered her. His cock wasn't too big but certainly a decent size. The man held her hips and thrust hard, making Emma shout with pleasure.

Within a couple of minutes the man grunted and buried his cock in her up to the hilt. He withdrew and was quickly replaced by another man. Emma guessed he must have worn a condom as she couldn't feel the familiar trickle of semen out of her pussy.

The next man repeated almost exactly the first, roughly pumping his cock into her before shooting his come into a condom. The last man entered her with one swift thrust. His cock was huge. Emma loved the feeling of a big cock but didn't like it lasting too long as it made her sore. The man didn't last long, again spurting his load into his condom.

Without a word, they were gone. Emma laid back in the car was a satisfied look on her face.

"That was unbelievable!" She gasped. "I can't believe I've just been fucked by 3 men and I didn't even see their faces!"

"I knew you'd enjoy this!" Ian said with a triumphant look on his face.

"We need to do this again sometime soon." Emma told him.

"Don't worry, we will." He said. "Now are you coming back to mine for the night?!"

Emma smiled, knowing she didn't even need to answer that question. She felt a happiness inside that he hadn't felt for a long time. Maybe this was the start of a new chapter in her life, it could be quite an adventure.