An adult stories – Cummimg for Art by Anygood,Anygood ‘Greg will do it,’ said Pauline.
‘What’s she volunteering me for now?’ thought Greg after overhearing his grandmother on the telephone.
He didn’t have to wait long for an answer. Pauline came into the living room with a grin on her face. She was a fantastic grandmother who’d always been there for Greg. His parents both worked long hours and he’d spent much of his childhood at his grandmother’s house.
Now aged 20 and bouncing between dead end jobs, he still liked to visit her as often as possible. There was just one draw back. Pauline was always putting Greg forward to do odd jobs or run errands for her friends.
‘Greg,’ said Pauline, ‘You remember my girl Eileen?’
Greg sighed. He certainly remembered Eileen. He’d done lots of what his grandmother called ‘little jobs’ for the 57-year-old divorcee. The trouble was she was very attentive whenever he went over to her house.
She’d follow him about as he completed the tasks she needed doing. Whether it was painting a fence, fixing a window or mowing the lawn, Eileen was always right there chatting away and trying her best to flirt with him.
It was funny at first when Eileen remarked how handsome Greg was and he’d been flattered. But when she started wearing low cut shirts and ‘accidentally’ brushing up against his ass as she squeezed past him in her hallway, it had become a bit too much.
‘Yes gran,’ said Greg, ‘I recall Eileen. What’s she want me to do this time?’
‘Don’t be like that,’ replied Pauline, ‘you know she’s one of my best friends and she’s a lovely woman. She’s always asking about you and she insists on paying you to do little jobs for her that I know you’d do for free anyway.’
Greg wasn’t so sure he’d do any work for free but he humoured his grandmother and nodded with a smile.
‘Anyway she’s got into art,’ continued Pauline, ‘you know how she gets with her fads and obsessions. Well the latest one is painting or drawing or such like. She’s been taking classes and now she’s joined a group. They take it in turns to host. It’s her turn tonight and she needs help setting up so I said you’d go over and do any heavy lifting she needed.’
Greg sighed again. ‘Ok,’ he said, ‘when?’
‘The class starts in two hours so you’d better head to hers now,’ replied Pauline, ‘it’s not like you’re busy. You’re just playing video games and eating all my snacks.’
Greg knew it was no use complaining plus he had no plans for the rest of the day and could use the money so he stood up, gave his grandmother a quick kiss on the cheek and set off to walk the half a mile to Eileen’s house.
When he arrived he was greeted with the usual cheery welcome which of course included a huge hug that lingered far too long.
Eileen ushered him into the big room at the back of her house and instructed him on the furniture she needed moving. As expected she hung about to watch as he worked chattering away.
Greg wasn’t really listening but just nodded and made the occasional noise to appear to be politely taking in what she was saying.
‘Oh that’s great Greg,’ said Eileen clapping her hands gleefully, ‘I knew I could count on you. Thanks. Linda had her dog there last week but this will be much better. I’ll be the talk of the group.’
‘Hey, what, err sorry Eileen I was distracted, what did you say?’ said Greg, slightly concerned he appeared to have unwittingly agreed to yet another task.
Eileen smiled. ‘You said you’d do a bit of modelling for my art group,’ she said, ‘oh it’ll be fantastic.’
‘Shit!’ said Greg, ‘sorry for cussing Eileen. I’m sorry. I’m no model. I wasn’t thinking. Count me out.’
Eileen’s beaming smile vanished. ‘Oh Greg,’ she said, ‘please do it. This is my first time hosting the group and I’m still trying to fit in. I can’t have them painting a bowl of fruit. It’ll be fun I promise and I’ll pay you $200. It’s only for a couple of hours. Please!’
Greg felt sorry for Eileen and the idea of $200 was certainly appealing. ‘Oh ok,’ he said, ‘what do I have to do?’
Eileen’s grin was firmly back on her face. She clutched Greg in a massive hug. ‘Thanks Greg,’ she said, ‘it’s simple really. You just strip down to your boxers and do a few poses while we paint you.’
Greg wasn’t sure about the dress code but he figured it was no different to going to the beach so he nodded and said: ‘Sounds ok.’
Eileen clapped her hands once more and gave him another hug before heading out of the room to organise the snacks for the art group meeting while her young helper and soon to be model finished arranging the furniture.
About 15 minutes later Eileen returned. She handed Greg a bottle of water and gave him the run down of the plans for the night.
‘There’s only five of us in the group,’ she said, ‘they’re all lovely gals. We met at the class I started going to and the teacher suggested we form a group to help keep each other’s enthusiasm up.’
‘Sounds nice,’ said Greg.
‘Oh it is,’ Eileen replied, ‘we have a good old laugh and there’s a lot of chatting as well as the painting of course.’
‘Of course,’ said Greg. He was sure they’d be more gossiping than art going on but it seemed harmless enough.
‘So you go into the bathroom and slip out of these clothes,’ said Eileen clearly relishing the idea of seeing him down to his underwear, ‘the girls will be here soon then I’ll introduce you to them and we can get started.’
Greg took another swig from his water bottle then went to the bathroom. As he took off his clothes he felt nervous about standing in front of five women in just his boxer shorts. He was sure he looked ok but he certainly wasn’t a big body confident person nor was he used to being stared out while scantily clad.
He was growing increasingly apprehensive when there was a knock on the bathroom door. ‘Ready Greg?’ said Eileen.
Greg didn’t answer. He took a deep breath and opened the door. Eileen couldn’t contain her enthusiasm. She smiled and took a step back. Her eyes darted up and down the young man in front of her.
‘Well Greg,’ she said, ‘you’ve really filled out nicely. You were a scrawny kid when you first came over here with your gran but, well, you’re a real man now.’
This praise and her staring made Greg feel a mixture of discomfort and a bit of pride. It was nice to be complimented even if it was by a woman almost three times his age.
‘Shall we?’ said Eileen motioning to the door leading to the room where the art group was meeting.
Greg nodded and followed her. Inside the room there were four women all aged in their late 50s to early 60s sitting on stools behind easels. They’d been chatting but stopped at the sight of their model.
‘Oh wow,’ said one of the women as she peered over her glasses.
‘Everyone this is Greg,’ said Eileen, ‘he’s kindly agreed to be our muse for the night.’
‘Hello,’ said Greg, giving a sheepish wave to his attentive audience.
Pointing to each woman in turn Eileen said: ‘This is Gladys, Linda, Jane and Sarah.’
‘Pleased to meet you Greg,’ said Sarah.
‘You look lovely dear,’ said Gladys, who had been the woman in the glasses who’d remarked when he came into the room.
‘Ok,’ said Eileen, ‘Greg if you’d stand over there and take up a pose of some sort please.’
Greg shuffled into the spot she’d directed him to and awkwardly tried to stand how he thought a model might.
Eileen took her seat and the woman all began painting. After a minute or two there was some tutting and whispering that Greg couldn’t make out.
Gladys put down her paint brush and said: ‘Greg dear we’re not sure this is the right pose.’
‘To be honest I don’t know what I’m doing,’ replied Greg, ‘I especially don’t know what to do with my hands. I guess by my sides isn’t much use?’
Gladys smiled. ‘Quite,’ she said, ‘I have an idea. Maybe if you, well maybe if you slipped off your boxer shorts and used your hands to cover your modesty. That’d be something for them to do and it’d be a good pose. All for the sake of art of course.’
Greg’s heart began to beat fast. He wasn’t keen on the idea of standing naked in front of Eileen and four strangers. It’d been difficult enough to pose wearing his underwear.
‘I’m not sure’, he mumbled.
‘Oh come on now Greg,’ said Eileen. She stood up and walked over to him and whispered: ”y
You’re grandmother is a great friend of mine as you know and I thought we were friends too? Please don’t disappoint my guests. There’s nothing to be ashamed of and you’ll be covering up your you know what so what’s the harm? Please do it. I really want to impress Gladys and I’ll double what I’m paying you.’
Greg was conflicted. He didn’t want to upset Eileen or his grandmother and $400 would be a good pay off. Looking round the room he could see the four women sat eagerly awaiting his response. It was kind of exciting to be the center of attention and it was true he’d be covering up his dick.
‘Ok Eileen,’ he said, ‘but make it $500.’
‘Deal!’ she replied.
Eileen returned to her seat and Greg took a deep breath. He turned away from the woman and quickly removed his boxer shorts dropping them onto a chair a few feet away. With a gulp he turned back around. Both of his hands were firmly in front of his genitals and he was sure he was covered.
‘Excellent!’ said Gladys, ‘you look wonderful dear.’
Greg shyly smiled and looked down to make sure nothing was showing that he didn’t want to be seen. The woman all returned to their painting and after a few minutes he relaxed and his nerves settled.
Standing there naked he began to daydream and consider what he’d spend his $500 on. This went on for a while when suddenly he became aware that the women were whispering to each other again.
‘What now?’ he thought to himself.
‘Erm Greg,’ said Eileen, ‘We’ve all about finished our first work and wondered if you’d mind changing poses?’
‘Ok. Like this?’ he replied moving his body to give a side profile.
‘That’s lovely dear,’ said Gladys, ‘but we were thinking, and only if you’re comfortable with the idea, but we were wondering if you’d mind moving your hands?’
‘You mean….’ Greg started to say but was cut off mid-sentence.
‘Yes dear,’ said Gladys, ‘we’d like to see your penis. Purely for the sake of art. You know, like Michelangelo’s David statue. It’s an artistic tradition.’
‘And you look magnificent,’ said Linda speaking to him for the first time all night.
‘I don’t think so,’ said Greg.
‘Oh come, come now dear,’ said Gladys once again peering over her glasses at him, ‘we’re all experienced ladies. We’ve seen these things before and like I said it’s just for art.’
‘I’ll double your pay!’ blurted out Eileen who was clearly very excited by the prospect of potentially seeing Greg’s cock.
‘Double the new amount?’ he replied, ‘so that’s $1,000?’
‘Yes!’ replied Eileen without hesitation.
That was a lot of money to Greg. He was still reluctant but now he was seriously considering doing it.
‘How about each of us give you 100 bucks on top of what Eileen is paying you?’ said Linda who was suddenly very talkative.
Without thinking Greg replied: ‘200 each plus Eileen’s 1,000 and I’ll do it.’
The woman glanced at each other and all nodded their agreement. ‘Ok Greg,’ said Gladys, ‘you got it. Now move those hands and let’s see that cock!’
Taken aback at this rather crude instruction, Greg briefly paused but then shrugged and removed one of his hands. His heartbeat was pounding in his chest. He was nervous but also excited. Looking down he could see the evidence of his excitement as his dick began to twitch and stiffen.
‘And the other one please dear,’ said Gladys impatiently.
Greg moved his second hand and, now freed, his dick sprung up and stiffened more as the five women all focused their gaze on it.
‘Oh that’s lovely,’ said Linda.
‘As I thought,’ chipped in Gladys, ‘you have a beautiful cock dear.’
‘You seem to be enjoying this Greg,’ said Sarah pointing her paintbrush at his ever swelling member.
‘Errrr,’ he mumbled.
‘Now girls we’re here for art remember?’ said Eileen, ‘let’s paint.’
The woman returned to their artwork but all seemed to be taking much longer looks up from their canvases than they had previously.
Greg stood there trying to calm his heart rate and his cock. But it was no good. Each time he thought he’d begun to get it to go down he caught the eye of one of his audience and up it went again. He could even feel a trickle of pre-cum.
‘Fuck,’ he muttered to himself under his breath quickly trying to wipe the tip of his dick hoping none of the women noticed the sticky liquid.
‘Oh Greg,’ said Gladys.
‘Of course she’d seen it with her eagle eyes,’ he thought to himself.
‘You seem a little excited dear,’ Gladys continued, ‘feel free to, how should I say, enjoy yourself. I’m sure I speak for all the girls when I say we don’t mind.’
The other women all quickly muttered their agreement but Greg wasn’t about to ‘enjoy himself’ or certainly not for free. Wait. What was he even thinking? No. There was no way he was going to do anything like that. This had already gone much further than he intended.
As if reading his mind, Eileen stood up, walked across to him and whispered: ‘$2,000 and you don’t have to cum.’
‘What?’ replied Greg.
‘I’ll give you $2,000 to stroke your cock a bit for us,’ she said softly, ‘just tug on it for a few minutes and get it as hard as you can without cummimg. That’s easy money for you and you’ve already gone this far. I’ll get them to pay more too. Forget art. This is the most excitement any of us have had in years. Please do it.’
‘If you get them to match you I’ll do it,’ he said scarcely believing what he was hearing himself say, ‘so that’s 4,000 in total and I’m not going to cum right?’
Eileen nodded and returned to her seat. The other women gathered around her and after a brief conversation it seemed they had an agreement.
Sitting back down Gladys said: ‘Ok Greg. Get to work. Tug that big cock for us ol’ grannies.’
She laughed as did the others. They’d all moved their easels out of the way to get a better view of the impending action.
Greg reached down with his left hand and gripped his penis. It was already pretty hard and he knew he’d have to be careful not to over excite himself and accidentally cum.
He started stroking up and down his shaft slowly. The women’s eyes were all laser focused on his cock and he had to admit that was making him hornier.
‘Play with your balls too Greg,’ said Linda.
He reached down with his right hand and cupped his testicles. Slowly he rubbed on his balls while continuing to stroke his shaft with his other hand gradually picking up the pace.
Linda stood up and walked across to him. She knelt down about two feet away, her glare never leaving his stiffening cock.
‘I’m just getting a closer look,’ she said gently, ‘you don’t mind do you sweetheart?’
Greg shook his head to signal he had no problem with her coming closer. This acted as a greenlight for the other four women who all moved in to get a much closer view of this young cock as it swelled with each of his tugs.
Several minutes passed by and Greg could feel he was getting close to ejaculating. He stroked his dick four or five more times then suddenly stopped. Releasing his grip on his penis it stood to attention with a long streak of gooey pre-cum hanging down off the tip.
He put both hands up above his head and looked at the women. Having started this entire night so shyly he was now feeling in control as they all stared up at him with looks of disappointment on their faces.
‘Well ladies,’ he said, ‘we agreed I didn’t have to cum so….’
‘But we hoped you would,’ said Eileen.
‘You can if you want to,’ added Linda.
‘Nah I’m good thanks,’ he replied trying to act cool but knowing he really wanted to blow his load, ‘I’ll finish off at home.’
‘Fuck that you will!’ shouted Gladys and without warning she grabbed his still rock hard cock tightly in her hand.
Greg was shocked. He was hoping to negotiate some extra money to cum for the women but now he was being groped. Before he could say anything Jane and Sarah had stood up and were clutching at his arms holding them behind his back.
They were strong for two older ladies and Greg struggled to get free. In the meantime Gladys was rapidly pumping his dick with her hand while Linda massaged his balls.
Greg could feel the cum building up and he no longer wanted to fight the women off. He just wanted to cum and badly. He relaxed his arms and stopped struggling.
Jane and Sarah released their hold on him and sat back down to get the best possible vantage point as Gladys went into overdrive roughly stroking, almost yanking, at his cock.
Linda was rubbing his balls furiously as if trying to drive as much cum up into his shaft as possible.
‘Cum for us Greg!’ yelled Gladys.
‘We want to see a big load please,’ said Linda.
The addition of the word please and the sweet way she spoke in contrast to Gladys’ barked demand made Greg smile and, as he edged closer and closer to ejaculation, he hoped he’d not disappoint Linda.
‘I’ll pay all the money if he cums on your face,’ said Gladys pointing at Eileen.
Greg was, not for the first time that night, shocked. He was even more surprised when Eileen nodded and knelt directly in front of him. But by this point he was way past making comments as he got to the precipice of ecstasy.
Linda let go of his balls as Gladys yanked harder than ever on his engorged shaft. After a couple of more tugs Greg felt the cum flood up into his cock.
Gladys pointed it towards the waiting Eileen and with two more pulls Greg’s dick exploded shooting out ream upon ream of cum.
The thick, white, sticky liquid smacked into Eileen’s face almost covering it from brow to chin. Greg thrust his hips forward as his cock pulsated trying to fire out as much cum as it could. Gladys continued to tug but with a bit less vigour as his climax receded. She squeezed his member hard a few times attempting to extract every last drop of liquid. Then she rubbed his dick on Eileen’s face.
‘Can I lick you clean please?’ said Linda meekly.
Greg was still coming down from his giddy orgasm but mouthed ‘sure’ silently. Linda gently took his still fairly rigid cock in her hand then placed it in her mouth.
There was something soothing about the feeling as Linda sucked slowly on his cock then removed it from her mouth and licked up and down until it was clean. It was certainly a welcome contrast to the rough, but admittedly pleasurable, tugging imparted by Gladys.
‘All clean Greg,’ said Linda with a coy smile, ‘thank you.’
Eileen had left the room presumably to clean off and Gladys, Sarah and Jane were back in their seats gossiping away. Linda stood up and joined them.
‘Errrr right,’ said Greg, ‘what now?’
‘I’ll write you a check dear,’ said Gladys, ‘sorry about that. You got an old gal rather excited there and I couldn’t help myself. I’ll make it $6,000. My husband has plenty of money and you’ve done more for me just now than he has in years!’
Without replying Greg picked up his boxer shorts and made towards the door.
‘How quickly can you go again?’ asked Jane.
‘You mean…’ said Greg.
‘I mean can you get hard again soon?’ said Jane, ‘I’d like a picture to remember this night when I’m, well you know, when I’m engaged in certain activities.’
‘Yeah that’d be great Greg,’ said Linda, ‘can you do it?’
‘I promise I won’t make you go all the way,’ said Gladys, ‘unless you want to that is.’
After the attention of Linda’s mouth and all this flattery, Greg could feel he was already getting hard. He threw down his boxer shorts and took hold of his dick.
‘Yessssss!’ yelped Linda as she rifled through her bag looking for her cellphone.
As Greg worked on restoring his erection ready for the impromptu photoshoot, Eileen walked back into the room with her face cleaned off and a new shirt on.
‘What’s going on?’ she asked.
‘Greg’s going to let us take pictures of him,’ replied Linda clutching her phone and grinning like the cat that got the cream.
‘It’s for the art,’ quipped Gladys, ‘oh and I meant it. I’ll pay the full amount we promised Greg. Did you enjoy his, erm, his product?’
Eileen didn’t reply. She was clearly embarrassed she’d agreed to be the target for her friend’s grandson’s cumshot but the twinkle in her eye suggested she would probably happily do it again.
Greg continued to stroke his cock all the while wondering if he dared to ask for more payment. He decided it was worth a go. After all only Gladys was actually shelling out any money.
‘So are you paying me for this?’ he asked bashfully, ‘I mean…’
‘How much and what do we get for it?’ interjected Gladys who he later discovered was the wife of a man who’d founded a chain of restaurants.
‘I thought you wanted to take a picture of my, my private parts?’ he answered.
‘Linda does and yeah I do too but can we get more?’ she said.
‘Like what?’ Greg said.
‘Hmmmm,’ Gladys said tapping her finger against her lips in thought, ‘you’re a young guy and clearly you’re able to reload so to speak pretty quickly. How about multiple pictures, we all get to touch it this time and you cum again for us?’
‘How much?’ said Greg surprising himself with his responses.
‘I’ll pay another $2,000 if the others will each chip in $500. That’ll give you 10,000 bucks for the night and I think you’ve enjoyed your work too,’ said Gladys with a smirk.
Greg was still stroking his cock now almost absent-mindedly. That was a huge amount of money to him but he could tell from the eager look on the women’s faces that he could probably push it a little further.
‘Ok,’ he said picking up the pace of his tugging, ‘Take as many pictures as you like but none with my face visible.’
‘No problem,’ said Gladys.
‘And,’ continued Greg, ‘you can all take it in turns stroking my, my privates. Plus I’ll cum for you again but I want $4,000 more from you Gladys and $1,000 each from the rest of you.’
The woman formed a loose huddle and quickly discussed the situation. Greg slowed his stroking not wanting to ruin the potential lucrative deal by blowing his load for free.
‘Ok,’ said Gladys, ‘we agree but we want to touch all of your body not just your cock and we want to decide where, when and how you cum.’
‘Sounds reasonable,’ said Greg still not quite believing he was standing naked in front of five women tugging on his dick negotiating such a deal for more money than he’d ever had in his life.
‘But,’ he continued, ‘no putting anything up my ass and I want Linda to suck me.’
Linda beamed with delight. ‘Deal!’ she shrieked, jumping from foot to foot in excitement.
‘Sure,’ added Gladys, ‘but remember we tell you when, where and how to cum or it’s all off?’
‘No problem,’ replied Greg.
With that the women gathered around Greg. Eileen immediately grabbed his erect cock and gleefully stroked it up and down.
‘You’ve no idea how often I’ve thought of doing this,’ she said.
Greg lifted his arms above his head allowing the women to paw at his naked body. They rubbed his legs, chest, stomach and butt. Eventually, rather reluctantly, Eileen relinquished her grasp on his dick and Sarah took over on tugging duties.
Jane took her turn with his member and Greg could feel he wasn’t far away from cummimg but he remembered the terms of the deal and did all he could to distract himself.
The woman had been rubbing and squeezing his body for several minutes. He felt Jane let go of his cock then a now familiar hand took it and began roughly yanking back and forth.
Greg looked down and saw Gladys tugging for all she was worth on his swollen cock. As previously it hurt a little but was still pleasurable. She looked up at him.
‘I’m going to make you cum,’ she said through gritted teeth.
Greg gripped his toes into the carpet and looked up at the ceiling. There was no way he was going to let $14,000 slip away. What was more he resented Gladys trying to get out of the deal especially after what she’d done earlier.
She tugged away on his dick almost violently and rubbed his balls but he held out even when she licked the tip of his cock unexpectedly.
Eventually Gladys admitted defeat and suddenly let go giving out an annoyed grunt as she did so. Linda moved in and took Greg’s cock in her hand gently.
He looked down as she slowly stroked it. Greg was a tad alarmed to see how red his penis had become but he guessed that was to be expected and Linda’s soft hands felt soothing as she moved them along his shaft.
‘I think we oughta get these pictures done girls,’ said Eileen, ‘I’m not sure how much longer he can keep this going.’
They all laughed and Linda let go off his cock. It felt strange not being held after so much attention but it remained rigid. The women all got their cellphones and started snapping away from every angle.
‘No face remember!’ Greg said.
‘Yeah, yeah we know,’ said Gladys, ‘now keep that big cock of yours hard for us. You’re not done yet.’
Greg didn’t reply to this barb but did give his member a few strokes just to keep it as stiff as he could while the women swarmed around him like bees round a honey pot.
Jane and Sarah both posed next to Greg’s dick pointing at it and smiling while Eileen couldn’t resist tugging it a bit more on the pretext of wanting it to look its best for her selfie alongside it.
Linda had a photograph taken kissing the end of his cock which made Greg’s entire body shiver with excitement much to her enjoyment.
‘$1,000 if I can slap it!’ barked Gladys.
‘What?’ said Greg.
‘I’ll give you 1,000 bucks if you let me slap your cock dear,’ she replied less aggressively, ‘one slap as hard as I like. Then I want a picture with it in my mouth. Fuck it. I’ll pay, or should I say my husband will pay, $5,000 to give your big dick a huge slap, have a picture with it in my mouth and another two minutes trying to make you cum. If you don’t then Linda can suck you like you wanted and then we’ll get to the last bit of our deal.’
Greg didn’t like the idea of his cock being slapped nor was he sure he could take two more minutes of Gladys’ tugging. He also wasn’t convinced he could trust her not to bite him when he was in her mouth but the money was getting really serious now.
‘Sure,’ he said, ‘my maths isn’t great but I reckon if you make it $6,000 then I’ll be on for a nice round $20,000 so if you’re up for that then I’m willing.’
‘Deal!’ snapped Gladys immediately.
She gripped Greg’s cock and began rhythmically stroking it with increasing pace. That soon turned into her more usual rapid tugging but try as she might she couldn’t make him cum.
‘Time’s up,’ said Linda, ‘let him go now Gladys.’
This was the most authoritative Linda had been all night and perhaps in surprise Gladys did as instructed. Greg’s dick was as hard as it could be at this point and Eileen and Jane both rushed in to snap selfies with it.
‘Step aside,’ said Gladys, ‘time for that thing to get a good ol’ slap!’
The women moved away and Greg braced himself. He closed his eyes and waited. Then crack, he felt Gladys’ hand impact sharply with his engorged penis sending it springing to one side then back.
‘Mother fucker!’ screamed Greg.
‘Ouch,’ said Jane, ‘that looked painful.’
‘That was the idea,’ said Gladys.
Greg’s cock was stinging from the slap and he hadn’t dared take a look at it but then he felt a warm, gentle sensation and glanced down to see Linda kissing his shaft.
She worked her way up and down it slowly and the pain gradually gave way to a much more pleasant feeling.
‘Ready?’ she questioned.
Greg nodded and she slid his cock into her mouth and began sucking on it while teasing the tip with her tongue,
It felt amazing. Greg thought she’d obviously perfected her technique over many years and he was now enjoying the benefit of experience.
He held onto Linda’s hair as she sucked faster and he really wanted to cum in her mouth but knew he mustn’t. All too soon she withdrew his cock and he felt the air hit it like a cold wind.
‘Right,’ said Gladys, ‘time for my picture then we’ll see you cum.’
She roughly grabbed his dick and shoved it into her mouth catching it against her teeth as it went in. Eileen snapped a photograph and, with one more nibble at his shaft, Gladys released him.
‘You’re lucky I didn’t bite that thing off,’ she said.
‘Really Gladys,’ said Eileen, ‘I don’t know what’s got into you.’
‘Sorry,’ said Gladys rather halfheartedly, ‘I guess I’m just projecting my frustrations with my husband onto this boy. Anyway it’s time for Greg to cum for us don’t ya think?’
The mood in the room lifted again and the women all signalled their agreement. Once more they gathered together this time to decide how and where they wanted him to ejaculate.
Greg stroked his cock slowly to keep it on the edge while he tried to hear what they were saying and hoped it wouldn’t be Gladys who picked what went on next.
Breaking away from their huddle, the women all looked pleased with their decision. Greg waited.
‘Well Greg,’ said Eileen, ‘we had a few ideas put forward. But we’ve decided to play a little game. Each of us will get a turn jerking you and the person who makes you cum won’t have to pay their share of your money.’
‘Unless it’s Gladys then she’ll just pay $1,000 less,’ said Jane, ‘don’t worry the others will make up the shortfall so you’ll still get your 20 grand.’
‘Fine by me,’ said Greg. He was pleased it was so simple and was determined it wouldn’t be Gladys who won.
‘So that’s the how,’ said Eileen, ‘and the when is obviously whenever you can’t hold on for any longer.’
‘Now for the where,’ said Gladys.
‘Yes,’ chipped in Sarah, ‘we’ve errrr, well we’ve decided to do it….’
‘Oh for fucks sake!’ snapped Gladys, ‘we’re going to make you cum in the front yard.’
‘What!’ yelped Greg, ‘no way. There’s loads of cars and people that go by out there even at this time of night. There’s a street light shining straight into the yard so I’ll be on full show. No way. I’m not doing that. Pick somewhere else.’
‘Then the whole deal’s off,’ said Gladys coolly, ‘say goodbye to $20,000.’
Greg was furious. This had been Gladys’ end game all along. She never wanted to pay all that money. He’d let them do all this and now he was getting nothing for it. No way.
‘Fuck it!’ he exclaimed, ‘let’s go. You want me to jizz in the front yard well that’s what you’ll get.’
The women all looked shocked, especially Gladys. ‘Are you sure you want to do this Greg?’ asked Linda, ‘I’ll pay my 1,000 bucks no matter what.’
‘Me too,’ said Eileen, ‘anyone could see you out there. Don’t take the chance.’
Sarah and Jane both agreed they’d still pay their share but Gladys wasn’t budging.
‘Cum in the front yard or I’m not paying a penny,’ she said.
‘Then lead the way,’ replied Greg determinedly.
Gladys laughed. The other women looked a bit concerned but also excited. For his part Greg was past caring now. He was making Gladys pay up no matter what.
The group made their way outside into the yard. There was only a chain link fence at the front so no privacy was provided and, as expected, the street lamps lit up the space brightly.
Greg stood there naked as cars whizzed by. He stroked his cock a few times hoping that would help him cum quicker and before anyone he knew saw him.
‘Right,’ said Eileen, ‘we drew lots and I’m going first. Five tugs each and if you don’t cum by the time we’ve all had a go we do it all again in reverse order ok?’
‘Whatever,’ Greg replied with a hint of resignation in his voice.
Eileen knelt down next to him and grabbed his dick. She put her other hand on his ass and began stroking his cock. The other women counted as she tugged.
‘One, two, three, four, five!’ they said in unison.
A man with a dog walked by just as Eileen was getting to her feet. He looked puzzled but carried on his way after a quick glance in their direction.
More cars went by as Jane grasped Greg’s member. She squeezed his balls as she tugged but he didn’t cum. The cold night air and the stop/start nature of the jerking was not helping nor was his eagerness to get it over with.
Linda was next but no joy and it was the same for Sarah. Then it was time for Gladys to have a go. She crouched behind him and reached between his legs taking hold of his dick and yanking it hard like someone trying to pull a tooth out. After four more similar tugs she stopped.
‘Well that’s round one,’ she said, ‘you’re going to be out here all night at this rate.’
She laughed. Greg was beginning to think she might be right. Just then a woman wearing a nurse’s uniform walked passed and looked straight into the yard.
‘What the?’ she exclaimed.
‘Just playing a game,’ said Eileen reassuringly, ‘birthday party stripper.’
‘Oh. Cool,’ said the woman, ‘I was on my way to work but, wow, can I watch?’
‘Sure thing,’ said Gladys without hesitation.
The woman giggled and entered the yard through the small gate. She was probably around 25 and quite attractive. She took a long stare at Greg’s cock and it twitched.
‘I think he likes me,’ she said with a chuckle.
Greg was way past embarrassment now and to be honest this new spectator had made him feel a bit hornier. Maybe it’d help get this over and done with, he thought.
‘Can I do a live stream?’ said the nurse.
‘Oh well, I don’t….’ began Eileen.
‘Go for it,’ said Greg, ‘just don’t show my face ok?’
‘Yeah no worries,’ replied the woman producing her cellphone from her pocket, ‘it’s ya big hard cock I’m more interested in. No offence.’
‘None taken,’ said Greg.
The woman began holding her phone up and, looking into it, said: ‘Hey guys. I was on my way to the late shift when I came across this fantastic specimen and I thought I’d share it with you. Enjoy!’
She turned to face Greg and walked towards him stopping about four feet away. Her phone was pointed right at his cock and it twitched again.
‘Yes this was going to help,’ he said to himself.
‘Ok,’ said Gladys, ’round two. Me to start I believe.’
With that she resumed her position behind Greg and grabbed his cock tighter than at any point previously. The nurse gasped and then giggled. She kept filming as Gladys stroked and the others counted.
After five there was still no cum and clearly annoyed Gladys let go of Greg’s dick and Sarah took her turn followed by Linda and then Jane.
Greg felt close to cummimg when Jane gave him her fifth and final tug but then she inevitably released and the feeling subsided. By the time Eileen had moved in and grasped him it was too late.
‘Round two over and we still have no winner,’ said Gladys.
‘Can I have a go?’ asked the nurse.
‘Sorry,’ said Gladys, ‘but it’s for a bet so not this time.’
‘Oh ok,’ said the woman, ‘shame. I’d love to get a hold of that thing.’
She giggled and Greg’s cock straightened with excitement. Perhaps seeing this and thinking it was her chance, Eileen rushed in and grabbed Greg’s member.
‘Round three!’ she proclaimed.
One stroke, two, three. Then Greg felt the cum rushing up into his shaft. He thrust out his hips and stared down at the nurse who was filming attentively. Eileen pulled hard on his cock and then at last it happened.
Cum shot from Greg’s dick like never in his life. He could feel the veins in his penis straining and pulsating as the liquid fired out narrowly missing the delighted nurse and landing on the concrete beside her.
Eileen kept stroking and Greg kept cummimg. Then as she slowed the pace then squeezed his shaft it was over.
The nurse turned her camera back around to face her. ‘Wow,’ she said to her online audience, ‘I certainly enjoyed that and I hope you did too.’
She shut off her camera and put her phone back in her pocket. ‘I’m going to be late for work but thanks for the show,’ she said, ‘what agency are you with? I’d like to book you for my friend’s birthday.’
‘He’s freelance,’ said Eileen, ‘drop in here sometime and I’ll give you his details if he’s available.’
‘Great,’ said the woman as she rushed out the yard.
Regaining his composure, Greg hurried inside followed by the five women who’s plaything he’d been for the last few hours.
He headed straight to the bathroom and got dressed. Each of the women, except Eileen, gave him a check before he made for the door to finally go home.
‘I hope you’re not angry at me Greg,’ said Eileen as she walked him to the exit.
Greg smiled. ‘Of course not,’ he said, ‘I made a shit load of money, got off twice and maybe found the career I’ve been looking for.’
Eileen was surprised but pleased with this response. She hugged him and said: ‘In that case perhaps we can do it again sometime?’
‘Sure,’ Greg responded, ‘but maybe invite that nurse instead of Gladys.’
Eileen laughed. ‘She’s the one with all the money though.’
Greg paused briefly. ‘True,’ he said, ‘ok. Let her come along with her checkbook but she’ll never make me cum!’
“I heard that,’ said Gladys who was standing a few feet away.
‘Just kidding Gladys,’ said Greg with a grin as he left the house, ‘it’s all for art you know dear!’