Banging the Boss ❤

John’s dick remained unmoving, caressed by the MILFs delicate folds. ’Fuck! Why would I have condoms? I didn’t expect this to happen, and I can’t exactly say, “don’t worry about condoms, I have a magic cock that lets me shoot blanks,” as if that could be believable even though it’s true…’ he thought in a slight panic.

“I would have just said that I’d get a Plan B or something tomorrow, but it’s a little risky…” Diane explained.

’Well, fuck, this sucks. I don’t really wanna lie and tell her I’ve gotten tested or something like that…’ John internalised.

Is it a lie, though? Do you think you aren’t constantly being tested for that kind of thing?

After a second John nodded. “I don’t have any condoms, unfortunately. I wasn’t expecting anything like this to happen… I know it’s just my word, but I get tested regularly,” he explained

Diane was quiet and John could feel her body twitching around his tip. “What if I was the one being a risk to you?” Diane asked.

“Uh... I… well… I think I’d trust you… but I wouldn’t want to do something you don’t want to, and I’d offer to go to the store… but I think they’d be closed by now,” John said, a little down trodden.

“I could maybe go down and get one from the drawer from the table at the top of the basement, but my… uhm, doorman might hear me…” she mumbled. John felt a tad confused then realised her ‘doorman’ was her son.

“We could do something else, there are other things we could do if you’d prefer,” John suggested. The gamer got quiet as he spoke his next words, “We could try… anal?”

Diane hummed as she mulled over her options. John tried to think of other suggestions but came up short, partly due to the eye contact he shared with the mature bombshell under him. His dick twitched as the blonde bit her lip.

“Whoa,” John exclaimed, catching himself on his elbows as he fell forwards; his dick pushed deep into the busty vixen, causing both to let out guttural moans. John’s stomach lurched and a pit of guilt formed. He tried to pull back but Diane’s leg was hooked around his back.

She leaned up and gave a sweet peck on his lips. “Mmmh… I hope I didn’t scare you there. I was… well, I wasn’t sure what to do, so I let my body decide and acted quickly before I could back out,” she breathed. “I can worry about dealing with whatever happens tomorrow on my way to work, but right now… I want you inside me… Fuck… It’s been way too long since I’ve felt this, toys just aren’t the same. I can feel every twitch, every throb… It feels amazing.”

A feeling of relief calmed John, but feeling the warmth of Diane and her pussy gently gripping his dick was divine. He leaned down and kissed the blonde enchantress, opening his mouth slightly and running his tongue across her lips. She eagerly responded in kind, wrapping an arm around his back and pulling him down onto her, sandwiching her boobs between them.

Diane’s leg fell from John’s back, allowing him to move, though he was content making out with the MILF while being snuggly as deep as he could be inside of her. She twitched and contracted around his dick. Diane became restless and began to gently move her hips as much as she was able.

John took that as his cue to take action. He moved his hips backwards earning a sigh of both disappointment and anticipation. Her loud moan of approval as he plunged back inside of her was only muffled slightly by the kiss they shared.

Diane was more than happy to move her hips in rhythm with John’s. There was a slight pause as John pulled back from the kiss. “Fuck, you feel amazing. Is this, like, all right for you?” he asked.

Diane let out a giggle. “It feels great for me too, everything I fantasised about at my desk and more. Would you mind if we flipped over so that you are on your back? I got a little ahead of myself and would like to taste that nice dick of yours again,” Diane propositioned.

John smiled and leaned down to kiss Diane again. He placed his hands firmly on her shoulders before rolling over and pulling Diane on top of him.

This time Diane was the one to cut the kiss short. “Woah, that was a fun ride,” she said giggling. “Now, I hope you don’t mind, but I’m going to taste my prize… I mean, give you your reward for such a good job.”

John felt as his dick was tugged downwards, Diane not bothering to pull him out of her and allowing her lowering body to do it for her. His cock rubbed up her body and between her chest, leaving a wet trail in its wake. Finally, his dick sprang upwards and hit his stomach with a loud wet slap.

She looked up at him with a sultry smile from between his legs. Taking hold of his twitching member, she leaned forwards and gave a series of pecks up the shaft and a longer one on the top. “It’s so bad I’m doing this. I can only imagine how HR would react if they found out I’d abused my power over you in order to get you into my apartment.”

Diane continued to kiss up and down his dick and smiled. “I have to admit, I had heard about your attraction to me only a week ago, but since then I haven’t been able to get you out of my head… This was an inevitability. One way or another, I was going to claim this gorgeous cock, and it was worth it.”

She smirked and placed one hand on John’s upper thigh while the other vanished under her body. Her tongue extended, and she began meticulously licking the base of John’s shaft, completely cleaning off her juices. She continued up his dick, ensuring that only the saliva she used to clean him was left. His cock vibrated as she moaned almost constantly. John wasn’t sure whether it was because of what she was doing with his dick or what her hand was doing between her legs.

Just before reaching the tip of his dick, Diane stopped. “I know most of what I’m tasting is myself, but there’s something more to it. I won’t lie, I like how I taste, this is something else, though. It’s like your dick is completely changing the flavour, making it better. I could suck and lap at your cock all day,” she said before opening her mouth and engulfing the tip of John’s dick.

Both of them let out loud moans. John’s grew louder as the vibration of Diane’s vocalisations sent shockwaves through his cock. John wanted to keep staring into Diane’s deep blue eyes, but she seemed to be using her tongue in order to study every part of his glans, and the longer she spent, the heavier John’s head felt until he gave in and allowed his head to fall back onto the bed.

“Fuck,” John exhaled. He managed to lift his head to look down at Diane once more. “If you keep that up, I think I’m gonna end up cumming.”

She smiled and pulled away, licking the underside one last time. “Well, we can’t have that, can we? It would be a little disappointing if your reward were to come to an end this early,” she cooed.

Diane moved up John’s body, her boobs dragging across his skin. She bit her lip as she got further up, and then when she was face to face, she leaned down and kissed his lips. In a swift move, John rolled them both over so that he was on top once again, causing Diane to yelp and giggle in surprise.

He kissed the alluring blonde on the lips, then looked into her eyes. “You know, I’m starting to think that the private photoshoot was just an excuse to get me into bed. I also think this has less to do with rewarding me for a good job and everything to do with a touch-starved woman in power who craves sexual attention.” John leaned down and kissed Diane’s neck.

“That’s not-” The seasoned bombshell cut herself off with a moan as John’s hand cupped her right boob, and his fingers gently rolled over her nipple. He began kissing around her neck and collarbone while continuously toying with her hardened nub.

“It isn’t? If your only goal was to bring me pleasure, then you would have made me cum in your mouth, or even better, you wouldn’t have gotten off my dick after pulling me inside of you. You could argue that you just want to extend my reward or draw it out, so I could enjoy it longer, but you didn’t actually ask me what I wanted,” John teased as he began kissing her other breast, avoiding her nipple.

He paused and looked up at Diane who was now breathing much heavier and hanging on his every word. His hand left her tit and began tracing lines up and down her body. “I’ll make sure to fulfill all of your needs. I wouldn’t want my boss to think I’m not capable of satisfying everything and anything she might ask of me, would I?”

She opened her mouth to speak but only a gasp escaped as John’s lips closed around her nipple and his fingers pushed between her dripping lips. His probing fingers quickly found her clit and began gently circling it, mirroring the motions his tongue took around her nipple.

She twitched and shivered as she let out a loud breathy moan. John smiled and pulled his fingers from between the blonde vixen’s crotch. Looking up, he put his soaked fingers into her open mouth, and she immediately closed her lips around them, sucking and licking her juices from them as he continued to use his tongue on her nipple.

When John was happy that his fingers were clean, he pulled his hand free, allowing it to rub down her waist, then back up. He let her nipple go and she took a sharp inhale as he blew on it, sending a cold breeze over the tender flesh.

“F-fuck,” she heaved. “Oh! I, I don’t, I haven’t felt like this in years, taking care of myself,” she paused to moan, “taking care of myself is nowhere close to this.”

John smirked as he began kissing down her body, spending a little extra time appreciating her firm stomach then trailing down, planting kisses all around the neatly trimmed patch of hair above her crotch, before pulling back in order to reposition himself comfortably between her legs.

Diane breathed heavily, looking down at John between her legs with anticipation. Her eyes were locked onto his and John could see the slight hints of desperation as she waited. He smiled and leaned in, but then pulled back to look at her clit. The dark pink little button glistened, her wetness causing a sheen over it.

John smiled, and like her nipple, he gave it a gentle blow, causing her pussy to twitch. He watched with fascination as a trickle of creamy liquid rolled out from between her lips. Diane whimpered, which broke John out of his staring, and he leaned in, capturing the bead before it spread. In his pursuit his face was coated in a damp layer, he licked his lips and was happy to find that the mature woman’s flavour was pleasant. She wasn’t overly sweet, like some of the other girls he’d eaten out; it had a tangy, slightly sour, but in a nice way, taste, however there might have been a slightly sweet and metallic taste, though it was faint.

The nerd happily leaned back in, coating his face further as he pushed his tongue inside, earning a pleasured moan. He couldn’t blame her for cleaning his dick if this was the peculiar flavour she was savouring. His tongue retreated and he began kissing her clit, circling it with his tongue and occasionally sucking on it.

The room grew louder as Diane’s voice rose in both volume and pitch. At this point her legs were trembling and her pussy pulsated. John could tell that she was getting close so he stopped, and looked up as the toned vixen’s chest raised and fell rapidly. Her hands were balled up and gripping onto the sheets beneath her and her eyes told John what she wanted, but he remained motionless, watching with enjoyment as his dick throbbed from the sight.

Her body calmed down and she seemed about to say something when John pushed his tongue back into her. John worried for a moment that her son might hear and burst into the room. In fact, he worried for a moment that the neighbours might hear and call the police.

John moved back, sitting on his haunches and watching as the MILF almost writhed in pleasure and looked down at him with desperation in her eyes.

This time, Diane shakily **** herself up, flipping over and raising her ass into the air, while she hugged her pillow, face half buried in it. “I… P-please, I need you… I need it inside me, now!” she half demanded and half begged.

John shuffled behind her and admired her ass. It was a great shape and a little bigger than he might have expected. He fought the urge to give it a light slap and instead lined his dick up, and shuddered as he felt Diane’s body pulling him in, twitching around him. The sound of him sliding inside of her caused him to throb and twitch. Both of them let out moans, John’s was deeper and much quieter, while Diane's was loud and sounded as if she’d had an orgasm just from having his dick inside of her.

He planted his hands firmly on her hips and paused as she continued to spasm around him. Diane slammed herself backwards, her ass hitting him and sending a slight ripple across it, accompanied by a loud groan. John began to slowly pull out then thrust all the way back in with one strong motion, sending another shockwave across her ass.

Every time he slammed back into the mature enchantress, she cried out in pleasure. John slowed down and Diane’s vocalisations quietened; she looked at him confused. “What’s… wrong?” she groaned.

John pulled himself free, and Diane let out a disappointed sigh. He then laid next to her on the bed and looked at her, her face still half-buried into the pillow. “That was amazing, but I want you on top,” John said, breathing heavily.

Diane smiled and **** herself up onto her hands. She leaned over John and kissed him as she pulled her leg over to straddle his lower half. The gamer’s hand dropped down seeking Diane’s twitching pussy, and as he made contact, her breath hitched.

John was surprised when he felt a set of dainty fingers wrap around his cock, guiding him back into the toned enchantress. She unceremoniously sank down John’s full length, letting out another guttural sigh, and remained there while the two made out.

Pulling back and sitting up straight, she looked down at John with a lustful smile. “Sorry, I just… need a second to catch… my breath,” she heaved.

John was breathing almost as heavily and replied with a smile. He stared up at her chest and couldn’t help himself as he reached up to cup each one in his hand. Diane let out a quiet chuckle and leaned over him, placing a hand on either side of his head as she began to rock back and forth.

Not wanting to be a lazy lover, John slowly thrust upwards with some effort, matching the busty blonde's pace, and though she was slow, her body came down hard, sending static through John.

The sound of hard wet slapping and Diane’s loud moans and cries filled the room, with John’s groans seeming like barely a whisper. Diane’s nipples were taken between John’s thumb and fingers and he gently pinched and tweaked them while continuing to enjoy her bouncing boobs in his palm.

With the extra stimulation, Diane began rocking faster. “Hey... I’m… going to cum,” John said through pants. Diane didn’t stop and John’s hands dropped to her thighs. “Diane, I’m… nearly there.”

She looked down smiling. “I’m almost… there too, just a… little more,” she moaned.

Diane let out a loud long moan as she pushed her pelvis down on John, her insides clamping down on him as her entire body shivered and twitched. Her upper body fell down onto John who was unable to postpone his own orgasm. The MILF’s pussy contracted around him trying to pull him deeper as his cock spasmed and twitched as he began to cum.

Feeling his cum enter her, Diane let out a pleasured groan and pressed her lips against his. She giggled and rested her head against John’s shoulder. “You don’t mind if we just lay here for a while? I haven’t had that kind of exercise in a while, not to mention I was already kinda tired from working all day. Oh, and if you want to spend the night, that’s fine with me, though if you need a ride somewhere, we’ll be setting off a little early tomorrow,” Diane offered.

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