Emma's Initiation Ch. 02

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Emma and Ian live out more fantasies.
2.7k words
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Part 2 of the 3 part series

Updated 09/27/2022
Created 07/11/2010
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"Do you want me to pick you up from work tonight?" Ian asked Emma.

She had never officially moved into Ian's flat, but in the 3 months they had now known each other she had eventually started to stay there most nights. Ian seemed to encourage it, he liked her company and loved the sex they had. It was all going along nicely.

"Yeah, that would be good." She replied.

"I was thinking," Ian started tentatively, "I've always wanted to have sex with a prostitute but never had the balls to do it."

Emma said nothing, Ian wondered if he'd overstepped the Mark with this one.

"Look," He continued, "It's not a problem if you'd rather I didn't."

"No, it's fine." Emma replied. "We always said this would be an open arrangement didn't we?" She didn't seem to upset by this, but Ian wasn't sure.

"I know we said that," He went on, "But with you sort of moving in I wondered if that might change things."

"It doesn't have to," Emma said, "If you're happy with us both having other partners I'm still cool with it."

Ian felt a relief. If he had to admit it, he had really started to care for Emma and really didn't want to scare her off. But he also wanted to explore some alternative sexual experiences.

"I've only got one request," She continued, "Total honesty at all times. I lived a lie with Adam, having one night stands behind his back and whoring, and hated every second. Let's just agree to be straight with each other."

Ian agreed and kissed her lovingly on the forehead. He was delighted that his suggestion hadn't ruined things and went off to work with a spring in his step.

Ian had arranged to pick Emma up after her shift at the brothel. He would come in about an hour before she was due to finish and pay to have sex with the other girl working. Emma was working with Nicki that day, a pneumatic 25 year old blonde with false 40DD tits and a slim size 10 figure. She looked like a porn star and had a reputation for being absolutely filthy and really enjoying her job. She would be a perfect whore to fulfill Ian's fantasy.

Ian arrived at the flat at 11pm as arranged. The receptionist showed him into a waiting room and told him she would send Nicki in. He was trembling with anticipation by this stage.

When she walked in, he was amazed by how accurate Emma's description was. She looked like she would be up for anything.

"What can I do for you darling?" She said in her broad Essex accent.

"Do you do Anal or Rimming?" Ian replied. Nicki hadn't a clue who Ian was as they had decided to keep this their little secret.

"No problem luv," Nicki smiled. "That'll be £100 for half an hour, anything goes."

Ian happily agreed and handed over his cash. As Nicki showed him to the second bedroom, Emma appeared from the other with am embarrassed looking man in his mid 40s. The man looked at his shoes while Emma gave him a knowing smile.

Once inside, Ian took his clothes off and waited as instructed. He felt a mix of nerves am excitement, here he was paying to have Anal sex with a woman he'd only met 2 minutes ago!

"You look a bit nervous darling," Said Nicki when he arrived. By this time she was only wearing a bra, thong, suspenders and belt.

"I guess this is your first time paying then?" She continued.

"Is it that obvious?!" Ian responded?

"I'm afraid so darling!" She laughed, "Don't worry though, I'll soon get you relaxed."

Nicki tucked a condom into her stocking and joined Ian on the bed. She laid him back and stroked his rapidly growing erection. She then moved her head down and started to circle the tip of his cock with her tongue. She clearly knew how to please a man, going from deep long strokes to short then licking his shaft.

"You can come more than once if you want," She told him, "If you can manage it!" she laughed.

"I'll manage it, don't you worry!" Ian retorted.

"You can come anywhere on me, just not in my mouth." Nicki told him before continuing to suck his cock.

Ian lasted for a good 5 minutes before warning Nicki that he was going to come.

"I want to come over your tits." Ian told her. She got onto her knees while Ian stood in front of her.

He wanked himself off for another 30 seconds before aiming his hot spunk over her huge tits. Nicki cupped them and held them or him to aim at. As always it was a huge load, Nicki smiled when he ha finished and made her way over to the dresser to clean up.

As Ian laid back he could hear a groaning noise coming from the next room. He could hear Emma groaning loudly and telling a man to "lick her cunt". Ian had no doubt that this noise was for his benefit!

He and Nicki chatted for a couple of minutes, laughing at the now even greater noise coming from next door. Nicki described Emma as a "right dirty cow!" in a jokey way. She told him he should pay her a visit some time too as she couldn't get enough. Ian just smiled and concentrated on his now growing erection, the sound and thought of Emma going at it with some stranger was getting him so horny.

Nicki got back down to sucking Ian's cock back to full hardness, before telling him to hold his legs back for her. First she licked his balls, gently sucking them into her mouth, then moved down his perineum towards his arse. She lubed it up by rolling her tongue around his rim before gently starting to probe him with her tongue.

Ian was loving it, this kind of treat was a rarity, and this time he didn't have to feel guilty for asking as he was a paying customer. Nicki hungrily lapped at his anus for a couple more minutes before warning him that they only had 10 minutes left.

"So you want to fuck my arse then do you?" She asked him while kneeling and spreading her cheeks.

Ian said nothing, grabbed her bum cheeks and buried his tongue into her tight hole. She screamed with delight and bucked her hips back onto his tongue. Ian worked her hole for a couple of minutes before applying the lube and condom Nicki had given him. He entered her tight bum hole with the tip of his thick cock, making Nicki let out a small cry of pain.

"Are you ok?" He asked her.

"I'm fine," She replied, "Just take it easy until I get used to you."

Ian edged his full length into her and started to fuck Nicki's arse slowly. She was incredibly tight and he was having to concentrate hard not to come straight away. He could also hear Emma screaming next door for her man to fuck her hard. After a couple of minutes he could hold back no more and buried his cock into Nicki's arsehole and came, filling the condom with another big load.

As he was getting dressed, he could hear Emma shouting at this man, telling him that she wanted his come all over her face. He smiled as he said goodbye to Nicki and made his way back to the car.

About 15 minutes later, Emma appeared and got into Ian's car.

"How was it then?" She asked him excitedly.

"She was great," he said, "And I could hear you through the walls which made it even better!"

"That was the idea!" She said with a wicked grin.

"And did he come over your face?" He asked.

"Yep!" She smiled. "He was one happy man!"

Emma spent the rest of the journey listening to all the gory details of Ian's session and also recounting the clients she had serviced that day. They really were getting on well, there's may not have been the most traditional kind of relationship but they were both really happy with it. Neither would admit it at this stage, but they both started to wonder if they were falling in love.

A couple of weeks later Emma and Ian went or a drink on a rare Friday night off for her. She wanted to tell Ian that he was in love with him, Carly, her best friend had told her just to go for it. Even if he hadn't have felt the same way, she was pretty sure it wouldn't ruin what they had. She really could tell him anything.

"I think I'm falling in love with you." She finally said I'm a quiet voice, almost like she hoped he wouldn't hear.

"Thank god you said that," Ian smiled. "I feel the same but I didn't have the nerve to tell you!"

Emma could sense a genuine relief in his voice, for the first time in years she felt totally happy and comfortable.

Later that night in bed, Emma brought up the topic of Dogging again. Ian had decided he wasn't going to push it and let Emma go at her own pace. He didn't want to force her away by pressuring her into it.

"Can we try dogging again soon?" She asked.

"Course we can!" He said gratefully, "Anytime you want."

"I really want to beat my record of 12 in a night!" She said with a wicked grin.

"Fucking hell! That'll take some doing!" Ian exclaimed.

"Would you mind? Hope you don't think I'm too much of a slut." She continued, looking a bit concerned she may have gone too far.

"Course I don't mind!" Ian said, giving her a reassuring squeeze. "It'll just take some organizing, that's all."

"I'll leave that in your capable hands then!"

Over the next week, Ian started to send out a few emails on dogging websites, he put out a date and a time and said that he was looking for a dozen or more men to satisfy his girlfriend. Within a couple of hours he had a couple of replies, he didn't tell Emma at this stage and continued searching.

Ian had made it clear that she wanted hard, anonymous sex with as many men as possible. The only rule was that condoms must be worn for sex, although they could come over her body if they wanted.

By the Friday of the next week, Ian had 10 replies. He knew a few more would be wandering by so sent an email telling them it was on.

When she got in from work that night Ian had a big grin on his face.

"Hope you've got nothing planned for tomorrow night?" He asked her.

"Do you mean what I think you mean?!" She replied.

"I certainly do!" He continued with a happy smile. "I've got at least 10 lined up ready and I'm sure there will be a few more hanging around. You up for it?"

"Fucking right I am!" She squealed. "You are the best, you know that?!"

"I have been told that!" Ian said with a contented look.

The next day they talked about nothing else. Emma had the idea that she didn't want to see any of the men's faces. She wanted it to be completely anonymous. They agreed she would wear a blindfold and that Ian would video the whole thing for her to watch after.

They made their way to the arranged spot on that Saturday night. It was a remote car park at a country park on the edge of London. Pulling up and turning off the lights, the place looked deserted. Ian flashed the interior light to let any watcher know who they were.

"This is it then." Ian said to Emma, "You definitely still want to do this?"

"Yes, as long as you're still happy with it." She replied.

"Take your clothes off then." He instructed her. Emma did as she was told. Once naked and in the back seat, Ian tied the blindfold in place.

"If you want to stop, you just tell me." He told her. "I love you."

Her heart jumped like she was 17 again, "I love you too."

Ian got out of the car and Emma could hear him talking to some men. She couldn't work out how many were there but it sounded like a few. A couple of minutes later he came back to the car to see if she was ready.

"How many are there?" She asked.

"You'll see later on the video!" He replied

He guided Emma into place, with the car door open. She opened her legs wide and waited.

The first man was quickly into place, thrusting crudely into her. She let out a cry of pleasure and heard a small cheer, urging the man on. He must have lasted no more than 2 minutes before coming into the condom. Another cock was soon entering her. The man held her legs up and fucked her hard. He soon pulled out and a couple of seconds later Emma felt the familiar warm jets of spunk landing on first her tits, then her stomach and shaven pussy.

This routine was repeated for what felt like hours. Emma tried to keep count of how many cocks she she'd had but lost count after the 6th. She was also now awash with semen, her tits and stomach were covered in the stuff, a couple of stray jets had even landed on her face.

"Lads, I need to get up." Emma announced, "I need to change position."

Ian helped her up, her legs were wobbly but there was no way she was going to stop now. She knelt on the back seat and put her bum up in the air.

"Fuck me doggy style then!" She ordered them, "Keep the cocks coming."

With no second invitation needed she was quickly full again. The man grabbed her hips and fucked her hard. Her pussy was now starting to feel sore but the sheer lust of the night made her carry on. The man soon came over her back and arse, then another, then another. For at least another half am hour one after another of these men filled her then showered her with spunk.

Ian moved into place behind Emma and whispered in her ear. "I'm going to fuck your arse while they all watch."

Emma could barely speak by this time, she just nodded to tell him it was ok. Ian gently pressed the tip of his cock into her tight anus. He could feel her tense up but she soon opened up and welcomed his cock in.

Ian gradually built up his pace, fucking his beautiful girlfriends arse harder and harder. When he came he let out a huge moan and shot his load deep into Emma's arse. She slumped down into the backseat of the car, utterly exhausted.

Ian came and joined her and undid her blindfold. She had a drained but happy look on her face. She had an inquisitive look around but all of the men had dispersed. She could see a few cars leaving while the rest must have gone on foot.

They cleaned themselves up and made their way home. Emma was asleep before they were half way home, when back at their flat, Ian helped her into bed and left her to sleep.

The next morning Emma awoke cuddled up with Ian. She immediately felt sore, her legs, pussy, arms and back all ached.

"So how did you enjoy that then?" Ian asked her.

"It was fantastic," She replied, "It was all such a blur though, did you get it on video?"

"Every last bit!" He said, "Are you up for watching it yet?"

"Not yet, I think I need a few days to recover first!"

"Fair enough." Ian said, happy enough to leave that for another day.

Just tell me one thing," Emma said, "How many was it?"

"16" Ian replied

"16?" She exclaimed, "I suppose that explains why I'm so sore, I really lost count after a while"

They spent the rest of that Sunday lying around watching TV, life felt good again Emma thought, wonder where this will take me next...

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