A Little Roleplay Never Hurt Anybody ❤

’I should have gotten more info on what we’re doing. How am I supposed to roleplay if I don’t know what I’m doing? I’m not even sure how I’m supposed to roleplay. I guess I’ll just try and go with the flow?’ John pondered as he stood in the dark hallway.

He looked down at the case-like bag in his hands. Opening it, he found what he should have figured, since he’d held a case similar only days ago. A DSLR camera, one that seemed to be a more entry-level model than the ones Ashcroft used, despite that it was still a nice camera. He pulled the camera from the bag and put the strap over his neck.

’So I’m a cameraman? Is she going to be like an amateur model? Or someone I’ve convinced into a naughty photoshoot? Or is it a porn shoot? Maybe she’s paid for professional photos or something?’ John speculated while going through the camera settings. It seemed that the SD card was empty, not that he meant to snoop.

He hadn’t seen any lighting equipment, so he assumed that the only light would be from the one in the bedroom or the flash. John didn’t like the idea of using flash as he felt the lighting would be unnatural, so using his rough knowledge and a little search online he managed to set the aperture, shutter speed and ISO to hopefully give him the best pictures possible. Even if it wasn’t perfect, he should hopefully be able to quickly adjust the settings without taking the two out of their scene; of course, that was assuming John would actually be taking any pictures and not just using the camera as a prop.

After getting familiar with the camera a little and having a few more ideas about what they might be roleplaying, he turned and gently knocked on Diane’s bedroom door.

“One moment, I’m not decent,” Diane’s slightly muffled voice came from behind the door. Twenty seconds passed and John heard the lock engage and then disengage before the door opened.

Without a word, Diane turned and sashayed towards her bed. John looked her up and down and was quite happy with what he was seeing. The outfit had a formal cosy vibe; she wore a short beige single-button cardigan, a charcoal grey tennis skirt, and to finish it off a pair of knee-high wedge boots.

“I’m glad you were able to find my apartment easily enough, though I’m sorry that I had you visit me so late. I’ve been in meetings all day since I left our shoot this morning,” she said. She lifted her leg onto the bed, before pulling the zipper down, slow enough for John to hear as she unhooked each individual tooth. Once she’d pulled it off and tossed it, she pulled up her thick cotton socks, which matched the colour of her cardigan, to her lower thigh. “I only just finished the last meeting before you arrived.”

Quickly she discarded the second boot, ensuring to slow down when pulling up the sexy socks.

“So I think we should begin with some pictures in my office, if that’s okay with you?” Diane asked, taking a few steps towards the desk which was positioned around where John’s bed would be in his room.

“Oh, of course, and don’t worry about the time, it’s a pleasure to be your photographer,” John replied, turning the camera back on and following the sexy MILF.

Diane walked around her desk and turned on her laptop, as well as a desk lamp before sitting down in her office chair. “I’ll start with some basic poses, if that’s alright?” Diane asked.

John smiled and nodded. “That sounds great. Let’s start with you doing something on the laptop; you could go to any site but give a more focused expression,” John directed.

Smiling, Diane began typing. John took a picture, which caused her to pause. “Did you actually take a picture? Maybe you should turn the flash on? It’s a little dark over here even with the lamp and the main room light on,” Diane suggested.

John looked back at the image, and though it wasn’t perfect, the settings had made the image better. He made an adjustment before smiling and looking up. “No, the lighting is workable, that image came out pretty good, though you didn’t seem quite natural. Drop your shoulders, take a breath, then maybe take a look at your work emails?”

Diane looked at him, slightly surprised, but did as he asked. The picture looked much better and her genuine focus from seeing her inbox made for a good picture. “Okay, next how about you flip through some papers?”

After maybe a handful of poses over the course of a minute or two, Diane stopped the two of them. “I have an idea for some poses, if it would be okay with you?”

John smiled. “Of course, I’d be happy to see what you have in mind.”

Diane reached over her desk and pulled a pen from the mug used as a pencil pot, then she loosed the only button on her cardigan allowing it to open slightly. She bit the back of the pen while looking directly into John’s eyes with a smirk on her face and lust in her eyes.

John took a handful of pictures and Diane continued. She pulled the pen from her mouth and replaced it with a finger, biting, sucking and licking it sensually as her pen travelled down her body. She used it to pop the top button of the shirt beneath her cardigan, then the second.

She removed the cardigan completely and John could see how thin the fabric of her shirt was when he noticed the dark outline of her bra. John raised an eyebrow, seeing the dark shape of her bra reach just under her ribs.

Diane cleared her throat, causing John to quickly look up. “It’s not quite professional to ogle your subject is it?” she teased.

John felt his cheeks heating up. “Sorry, I couldn’t help it,” he admitted before snapping a few more pictures.

Diane smirked, and pushed the chair back away from the desk to turn towards John, opening her legs and showing off a pair of soft-looking black panties. Another few pictures were taken and Diane leaned forwards, reaching out tentatively to press her hand against the front of John’s trousers.

Diane’s face took on a more serious expression. “I have something to confess, I know a little about you, John. We have a mutual friend, which was why you sparked an interest,” Diane confessed.

John’s stomach lurched. ’Who is it? Is she June’s friend? No, June said I know her friend somehow… Is she the mother of someone I go or went to school with? Was it someone mundane? If so, who?’ John thought. He gave a nervous smile. “Oh? Really? Who would that be?”

“It might be a little unprofessional to give out information like that; the important thing is that they vouched for you which was why you were offered the chance to be one of our photographers. Not only that, but they told me you happened to be a fan… with a little crush,” Diane confessed.

John’s body untensed as a weight lifted from him. He laughed awkwardly and massaged the back of his neck. “Oh, well, I, uhm… I guess you caught me,” he said, letting out a surprised grunt as Diane’s hand pressed against his crotch, slowly rubbing up and down.

“I know I shouldn’t do things like this. Not only am I in a position of power above you, but I’m much older than you… but I can’t deny that this is satisfying a few fantasies I’ve had over the years. I’d always wanted to do a naughty photoshoot but never wanted to let the images go public and never found someone I could do it with. I’ve touched myself at my office desk imagining myself having an intern pleasure me, and the thought of a younger man fawning over me gets my panties wet… So, John… would you like to indulge me? Would you allow me to reward you for a first day well done in an extremely unprofessional way?” Diane cooed.

John gulped and nodded, playing the part of the new employee, though the nerves were definitely genuine. “I, uhm, yes…”

Diane smiled and stood, keeping her palm pressed snuggly against John’s hardening erection. “Excuse me for a moment, then. I feel that I should change for our next set,” she purred, allowing her hand to slide across and away from John as she sauntered towards the bathroom. “Wait for me by the bed, won’t you?”

The door closed before John could answer. He followed halfway, standing by the bed. ’Should I take my clothes off? Or keep them on? What exactly are we going to do? More pictures? And how’s it going to transition into sex? Not that I’m rushing into it or anything…’

He wasn’t left pondering for long as the bathroom door opened once more. Diane stepped out wearing a comfortable-looking black robe, which ended just below her knee. She smiled at John as she closed the distance between them.

Her hand reached out and her thumb grazed John’s chin, before she leaned in and pressed her lips against his, but before he could reciprocate, she quickly pulled back. “Don’t worry, we can do that and much more, in time. Let’s start with a few more pictures first, though.”

John nodded and took a deep breath, catching the eucalyptus and citrus scent. “Okay, let’s start with you on the bed,” John said, trying to be more assertive.

Diane giggled, climbed onto the bed, and the two took several pictures in different poses, from relaxed shots of Diane sitting on the bed with a book, to an above shot of her spread out lying down, to her on her knees looking up at John. Everything was sexy but John would still call it modest; he hadn’t even gotten another panty shot or a good look at the bra she wore beneath the shirt that he’d barely been able to see.

She climbed off the bed and walked towards him. She put both hands on his chest and leaned against him. Forcing him to move the camera out of the way, she got close enough he could feel her breath. “Before we continue, I hope you wouldn’t mind taking off some layers? So that I’d feel more comfortable doing the same,” she asked, exaggerating her breathing.

John smiled and nodded. “How could I refuse a request like that? I wouldn’t want to damage my camera, though, so would you mind helping me?”

A sensual smile crept onto the MILF’s face. She popped the first button on his shirt, staring into his eyes as she did the second; this time she leaned in and planted a kiss on his chest where the button had been. She continued down, kissing further and further down; each kiss seemed to last a fraction of a second longer than the previous one and her eyes continued to be fixed to his. After the button just below his ribs, she climbed down onto her knees and continued.

Once the last button was undone, she tugged at the shirt while her kiss lingered, prompting John to pull it the rest of the way off himself. She smiled again, looking up at him. “Maybe you should get the camera ready for this next part,” she suggested.

John smiled, nodded and held the camera in a way to get a nice downwards shot. The first image was of her undoing the button on his trousers, then his zipper was slowly pulled down. In one motion she pulled both his underwear and his trousers down to the floor, allowing his dick to be freed of their slightly uncomfortable confines.

An image of Diane looking up at John’s dick a little wide-eyed followed. She stared for a moment or two, before reaching up and taking a gentle grasp on his cock. She stroked it a few times before leaning in. She closed her eyes and kissed the tip, then enveloped it, before backing away.

“I know that was a bit of a mean tease, but just a few more pictures and I’ll give you the reward you deserve,” Diane breathed, letting her hot breath pass over his cock.

John thought about giving her different directions but was curious what she might want him to take pictures of before they moved on.

She backed away, standing and climbing back onto the edge of the bed on her knees. She nodded towards the camera, allowing John to get it ready again. The belt of her robe was loosened, allowing the gown to part slightly.

John’s eyes widened as her generous exposed cleavage showed that she’d rid herself of her bra. His gaze dropped to her flat stomach; it wasn’t muscular but it was undeniable that she exercised which hadn’t been evident while she’d been clothed. A small neat patch of blonde hair peeked out from above her black panties.

The sight caused John’s dick to jump, which in turn earned a triumphant smirk from his mature subject. Enjoying taking pictures but wanting to move on, John took several more, and as he did, Diane turned to face away from him, flipping her robe up onto her back to expose her ass, and pressing her face into the sheets.

Slowly she peeled her panties down; a few visible strings of moisture clung before the distance was too great. Once they’d reached about mid-thigh, Diane flipped over, pointing her legs to the ceiling, and continued to pull the underwear down.

She bent both legs back down, planting her feet, and pulled one leg entirely out, leaving the black cloth around the other. Her free leg lifted straight up once again, while she spread her legs and lifted the other, allowing the fabric to dangle around her ankle.

“How about you come over here and we can get a few pictures with that nice dick of yours? Then maybe we can put the camera away until afterwards?” Diane suggested.

“That sounds like an amazing plan,” he said, kneeling on the bed and moving up towards Diane.

“Let’s get some of it between my tits and in my mouth, then you can move down to my thighs and… pussy,” Diane said, hesitating and blushing at the last word.

Moving up, Diane happily took John’s dick into her mouth again, her tongue lolling out in an exaggerated way while John snapped several pictures. Moving further down Diane enveloped John’s dick between her pillowy mounds; they were definitely bigger than Ellie’s. If he had to compare, he’d say they were about the size of Vanessa’s before he’d used Augment Body on them. She took pleasure in teasing his cock while he tried to focus on taking pictures.

“Give me the camera. I want you to push your dick between my thighs,” she ordered.

John shuffled down and could feel a nice amount of muscle in her thighs as his cock slid between them. Not only that, but the warmth he felt coming from her pussy as the underside of his cock rubbed against it made him twitch.

Diane obviously enjoyed the feeling too, made evident as she let out a shuddering groan.

After taking several pictures of John’s dick peeking at her from between her thighs, she opened her legs, handing the camera back to John, who took several pictures of his dick resting against her crotch.

She reached down and guided the tip of his dick towards her entrance. “I know you probably want to push forward but just one more picture and then I’ll reward you,” she said.

The picture was taken, and Diane took the camera from him, placing it on her nightstand. She opened the top drawer and her brow furrowed. “John… do you have a condom?” she asked.

Hey, I'd love to hear from you; whether it's a comment on the chapter, or in my branch discussion channel on The Gamer Discord, or a DM on either platform. As little as saying parts you liked in particular or things you might have liked differently, heck even just clicking the LIKE button at the bottom of the page helps me to see how well received the chapter is

For those of you who are willing and able to support me in a monetary capacity I have a coffee page, it allows for one-time tips, or you can become a member to gain access to my early chapters, as well as early looks at any art I commission.

Finally, I'd like to give a special thanks to my members.

Atreides
Thisisnotaname
Mekkosadx
Chiyo
Mouvar
Markas Lin
aBardNamedLily
Airda Notna
And the other members that prefer not to be named