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Diary Of A Playboy (18+) - Literature (4) - Nairaland

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Loving The Playboy (A Contemporary Romance Story) / Diary Of A Broke Playboy 2.0 / David.(A playboy's love story) (2) (3) (4)

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Re: Diary Of A Playboy (18+) by Landoffreedom: 12:54am On Dec 14, 2021
My sincere apologies for posting this in your thread. I need help with selecting 2 winners from a giveaway that I have going on here. I want unbiased and neutral voters to help me go through the plans each of these contestants (four of them) have on how they will utilize the fund. The best 2 plans will win the prize money of 50k each.

I created a thread for it here, I will appreciate all the vote I can get to select the eventual winners:

https://www.nairaland.com/6894416/should-win-50k-business-intervention#108478073
Re: Diary Of A Playboy (18+) by Awesome05: 8:28pm On Dec 18, 2021
Ride on
Re: Diary Of A Playboy (18+) by Ultimas: 3:39pm On Dec 21, 2021
Nancy shivered at my touch. "I don't understand it. Why can't I get you out of my head?"

"Probably for the same reason you're inside my head." And without thinking I leaned in and pressed my lips softly to hers. She gasped in surprise but a moment later Nancy flowed back into my kiss, her hands actually coming up and holding my face as she pressed forward, parting her lips to allow my tongue in as my heart leapt in absolute joy.

But as quickly as we started, Nancy pulled straight back shaking her head. "But I barely know you!"

"Then let's change that," I offered.

"But I can't. The whole situation is just too overwhelming for me. And you're cute and all, but... it's just so weird. The fact is, you're not just a cute guy I met in the elevator. you're New York's newest billionaire. And if I go out with you, paparazzi are going to be plastering photos of me in every trashy tabloid."

Once again I was holding Nancy's hands in my own. "Nancy, do you like me? Do you feel the same spark between us that I'm feeling?"

She looked at me. "Yes."

"Then what else matters?"

"I just don't know if I can handle all this." I could see the moisture in her honey brown eyes. "If you were just another guy, we could have had dinner last night and talked and who knows what might have happened? But then the Celebrity Sightings thing came on."

And I was reminded now of exactly why Nancy had gotten upset. I had just slept with Rosalinda. "In all fairness, Rosalinda has been my friendfor a long time. But there's no relationship there. And I had no idea I was going to meet you in the elevator that day. If we started something together, you and me... well, I'm not a cheater."

"And I think I realized that... It doesn't mean I'm happy about it. But it's not like I have any rights over you or anything. That's why I wanted to apologize. It's not very polite to kick someone out of your apartment." Nancy smiled for the first time.

"No it's not. But I understand. And apology accepted." My eyes sharpened as I looked right at Nancy. "Now, back to the matter at hand. I'm not much of a cook. So will you let me buy you dinner? Say, Friday?"

"A date?"

"Yeah, isn't that how this is usually supposed to go? We can start over fresh. I'm just a cute guy you met in the elevator."

"not that cute..." she teased.

"Hey, you just said I was cute!"

"you are, you are," she giggled. Oh, how I loved that giggle.

"Stop interrupting me." I exhaled and prepared myself. "I'm just a cute guy you met in the elevator. And you're just a very pretty young lady I want to get to know a little better. Come on, I'll take you to McDonald's!"

"Ooh, big fancy dinner from New York's newest billionaire!"

"nothing but the best for you. I can afford it."

Nancy laughed again and then leaned in and initiated the kiss this time, her lips soft and velvety against mine. She was just as sweet as I had wanted.

When she pulled back, I had to ask, "Is that a yes?"

"Yes, yes. Friday. Pick me up at eight."

THURSDAY

Helen came to the door at 9am promptly, with a guest. "Good morning, Mr. Robins."

I glared at her.

"Excuse me... Tade." A smile lit up her face as she called me by my first name. I think she rather enjoyed the little game.

"Better, Helen. How are you?"

"I'm good. It's a beautiful morning outside."

"I wouldn't know. It feels like I've been cooped up in here or in some other cold building every hour for the last week straight," I grumbled.

"Well, we'll get you outside soon enough." She then turned to her guest, a distinguished lady in her mid-fifties. "May I introduce our real estate agent."

Helen continued on, "The plan today is to tour some of these apartments you picked out yesterday. I've already set all the appointments. And..." she held up the paper bag with the Starbucks logo on the front and the three coffee cups in a carrier, "... I brought you breakfast."

I leaned in and inhaled the heady aroma. "Smells good."

A few minutes later, we'd finished our breakfast and I reclined into my couch while Helen sat next to me as our agent laid out some of the real estate dossiers. We then spent a short time laying out the itinerary we would have for visiting six apartments, the candidates for my future home.

But before we could get going, the door knocked.

Helen was immediately on to the door. Once opened, she offered her customary "Can I help you?"

"Who the hell are you?"

I knew the voice immediately, turning to see Rosalinda glaring up at Helen. It wasn't every day that a fashion model like Rosalinda met a woman taller than her.

"Rosalinda, that's not a very nice greeting," I admonished her.



Diary of a Playboy: https://okadabooks.com/book/about/diary-of-a-playguy/43624
Re: Diary Of A Playboy (18+) by FairCritic(m): 5:16pm On Dec 23, 2021
Nice update
Re: Diary Of A Playboy (18+) by Ultimas: 4:25pm On Dec 25, 2021
"Rosalinda, that's not a very nice greeting," I admonished her. I was surprised to find I was still a little wary of my longtime friend. After all, I STILL didn't know for certain whether or not she'd set me up for the paparazzi.

"Well you still haven't answered my question." Rosalinda cocked her head to the side and pouted while she put her fists against her hips. And I smiled; she looked so petulant and so pretty at the same time.

"Hello, I'm Miss Cooper," Helen offered, holding her hand out for a handshake. However, I could hear a little bit of an edge in Helen's tone, a sharp contrast to her gentle handling of Nancy's surprise yesterday. If Rosalinda was going to give her attitude, Helen wasn't the type to back down. "Mr. Kendall's law firm assigned me to Mr. Robins as his personal assistant. you're catching us just as we are leaving, Miss Brynn."

"Pleased to meet you." Rosalinda shook Helen's hand. "Just leaving? Where are you headed Tade? I thought we might be able to talk." And with that, Rosalinda gave me her best imitation of a helpless puppy dog.

I just started laughing. And just like that, I was prepared to give her the benefit of doubt. After all, she'd been my friendfor a long time, and friends don't mistrust each other. "About the whole Celebrity Sightings thing? Don't worry about it."

"Then why didn't you call me back?" Rosalinda came right up and hugged me.

"I'm sorry. My life's been a little crazy lately."

"I understand. A lot's happened to you." She leaned up and pecked me on the cheek. "you're forgiven."

And just like that, SHE was forgiving ME. How the hell did she manipulate me into that?

Our real estate agent interrupted the moment. "I apologize for intruding, but we do need to get going to our first appointment."

"Appointment?" Rosalinda looked at me.

"We're going apartment hunting. Time to find me some expensive, flashy new digs."

"Ooh! Sounds like fun! Can I come?" Rosalinda's puppy dog face was back.

Well, the face works. Especially on me. "Um, I suppose."

The agent helpfully added, "I'm sure the advice of your lady friendwill help you make your decision."

Rosalinda smiled brightly, already putting her shoes back on. "Let's go!"

And so we were off. For some reason, I had a feeling in the back of my head that having Rosalinda around for this house hunting trip was a ticking time bomb. And yet, the day went very, very well.

The apartments themselves were all fabulous, absolutely fabulous. Each of them had fantastic views and luxurious appointments. I really couldn't go wrong with any of them.

Rosalinda completely geeked out on all the expensive fixtures and rich textures. Before we were done with the first apartment, I realized a potential mistake in bringing her along. She would have her own opinions as to which place I should pick, and she might also be picturing herself as the "lady of the manor" as we toured each new home.

I had to admit, the thought didn't totally bother me. Rosalinda was gorgeous, smart, and had a great sense of humor. She could be a little self-centered, but what fashion model wasn't? She had her own social standing, her own experience interacting with New York's elite. And she was very, very good at cheering me up.

I found myself watching the raven-haired beauty as she gushed over some lavish drapery at the window. I had a magnificent view of Central Park through the huge windows behind her, and the whole picture was simply beautiful. Even Rosalinda's ears looked so cute with dangling earrings peeking out behind her short, sassy haircut.

Then Helen cleared her through behind me, shaking me out of my reverie and calling Rosalinda's attention over. My friendjust batted her eyes at me, brilliant blue staring right at me.

Then Helen directed, "We need to keep moving."

"I like her."

"Who?" I reached out and snagged another spider roll.

"Miss Cooper. Helen." Rosalinda had already put her chopsticks down, finished with her dinner. She ate like a bird. A very small bird.

"Hmm." I wasn't totally paying attention. We were sitting side-by-side at the bar of my favorite sushi place, OUTSIDE of my apartment, and I was going to enjoy this meal.

"She's calm, efficient, and of course very pretty. I'll bet she's a wildcat underneath that perfectly pressed business suit."



Diary: https://okadabooks.com/book/about/diary-of-a-playguy/43624
Re: Diary Of A Playboy (18+) by Zamar: 7:39am On Dec 27, 2021
Nice update.
Re: Diary Of A Playboy (18+) by Ultimas: 6:21pm On Dec 29, 2021
"Hmm." I wasn't totally paying attention. We were sitting side-by-side at the bar of my favorite sushi place, OUTSIDE of my apartment, and I was going to enjoy this meal.

"She's calm, efficient, and of course very pretty. I'll bet she's a wildcat underneath that perfectly pressed business suit."

"Hmm." I started trying to get the chef's attention and order some more sashimi. And they had this weird beef-wrapped asparagus thing I wanted to try.

"Those legs are just soooo long. Like, she would be a perfect model, except of course her tits are way too big. I mean, I'm already at the big endfor modeling. But maybe she could do Victoria's Secret or something. It's just so weird how she ended up a personal assistant instead."

I arched an eyebrow at her comments and offered my usual "Hmm" to let Rosalinda think I was listening, but satisfying my hunger was still the priority. I wolfed down two more pieces.

Rosalinda looked away across the bar, staring at nothing. "I guess I'd just love to get into her panties."

Okay, now I started choking. I was already quite buzzed from a couple bottles of sake and now the instant vision of Rosalinda and Helen twisting the sheets together caught me off guard.

Rosalinda just grinned and lightly patted my back as I fought back the tears in my eyes and caught my breath. "I haven't been with a woman in like, two years! And she is quite hot."

"Can we talk about something other than you seducing my assistant?"

"Fine, fine. Did you decide on one?"

I paused to pound back the rest of my sake and clear my throat out. "not yet. But I'm leaning towards the penthouse on 5th Avenue with the wide views of Central Park."

"Really? I would have thought you'd have gone for the corner place on Park Ave. It's certainly more luxurious and a lot bigger."

"Maybe, but (A) I don't need the room and (B) I figure I can always pay for more luxury. I can't buy a Central Park view like that over on Park Ave."

"So that's the one, huh?"

"I suppose so... Just think, in about a month you'll be visiting me in my luxurious penthouse!"

"Visiting?!" She slapped me on the arm. "Oh, no. you get a place that fancy and I'm moving in with you!"

I hesitated for a moment, not sure whether she was serious or not. "Oh, no you're not. I want the place all to myself!" I laughed, trying to make a joke out of it.

She caught my hesitation, and then leaned in close until her shoulder was pressed against mine and her dainty nose was just an inch away from my face. And in a quietly serious, husky voice, she offered, "Well, give a girl a chance to change your mind."

I had a hard time getting my key into the door lock, what with Rosalinda's tongue buried in the back of my throat. It was a kiss that could only be described as 'ferocious', and it also deprived me of my ability to see with any clarity.

By some miracle, I fitted the key and then we burst into my apartment. Rosalinda wasted no time, and once inside she physically slammed me against my own front door, pinning me in place as she sank to her knees and began opening up my jeans.

My eyes rolled into the back of my head as I sighed in resignation. I'd had the idea of winding up in my bed, but Rosalinda apparently wasn't going to wait that long.

But as my eyes rolled back down, in the corner of my eye, a red circle caught my attention. Perhaps my subconscious was looking for it; I don't know why else I would have noticed it. And as my eyes focused I saw the red circle was on my calendar, hanging on the wall next to me.

Tomorrow's date, Friday, had been highlighted, and in the middle of that circle was a simple word: Nancy.

almost immediately the sake fog clouding my brain lifted somewhat, and I half- crawled out of my own skin trying to get myself away from Rosalinda before she managed to slurp my erection into her mouth.

"What's wrong?" she quickly asked as I tried to hobble away, bare-butt naked with my jeans around my ankles.

"Oh, crap, Rosalinda. I shouldn't do this."

She didn't like the tone in my voice. "Why the Bleep not?"

I managed to get my jeans back up around my ass, sort-of. "I've got a date tomorrow. And I really like this one."

"So? That's tomorrow. What does that have to do with tonight? Is she your girlfriend?"

"Well, no."

"How many dates have you been on with her?"

"Uh, well tomorrow will be our first."

"Oh, Come on. We've been through this before. When you've had a girlfriend, I've been good and stayed away. But this is different. you don't have a girlfriend. you're not even dating yet. And I'm fucking Hot!" Rosalinda was now the very picture of a pissed-off supermodel, standing with one hand on her hip while she fixed me with the evil-glare-of-certain-death-if-I-didn't-give-her-an-answer-she- liked.

I didn't really have an answer for that.

"Come on... it's only a Mouth Gig..." she cooed.

"Just a Mouth Gig?"

"I promise. Now please? I've got a craving for cum..." Rosalinda's puppy dog face was back. I never stood a chance.

Without me saying anything else, Rosalinda saw the change in my demeanor and she began stalking me once again.



Diary of a Playboy: https://okadabooks.com/book/about/diary-of-a-playguy/43624

1 Like

Re: Diary Of A Playboy (18+) by Graminyte9(m): 7:31pm On Dec 29, 2021
"Come on... it's only a Mouth Gig..." she cooed.

"Just a Mouth Gig?"

*it's the mouth gig for me grin grin*
Re: Diary Of A Playboy (18+) by Ultimas: 1:48pm On Jan 04, 2022
"Just a Mouth Gig?"

"I promise. Now please? I've got a craving for cum..." Rosalinda's puppy dog face was back. I never stood a chance.

Without me saying anything else, Rosalinda saw the change in my demeanor and she began stalking me once again.

I sagged back into my couch, acquiescent as Rosalinda pulled my jeans down once again.

My cock was only half-hard, but reacted somewhat as she blew a cool stream of air across its tip. But then Rosalinda leaned back and began to UnCloth herself. First to go was her blouse, and then she reached to the front clasp of her lacy bra. "I have to admit, I can't decide if I want to swallow every drop of your sperm, or if I want to feel its hot stickiness splash all over my big tits." Damn she was sexy as she pouted in mock indecision.

And without even touching me, she'd gotten my dick rock hard once again.

Rosalinda hovered over the waving endof my rod. She opened her mouth wide, carefully placing it around my cock without letting any part of it actually touch her. She exhaled then... hot, moist air surrounding my sensitive nerves and driving me absolutely crazy.

"You're teasing me," I complained.

"Yes, I am."

I had wanted to just lay back and let her have her way with me. I wasn't going to take an active role in my imagined infidelity to Nancy. It would be a very small moral victory, but one I wanted.

It was a victory I would not achieve. And with a pained roar I lashed out, seizing Rosalinda's head in my hands and forcibly shoving her onto me.

Rosalinda was able to open her mouth wide, and a second later Rosalinda's lips were pressed all the way up against my crotch, my cock a couple of inches into the tunnel of her throat.

"Stop teasing me." I released the tight grip holding her while leaving my hands on her head.

Rosalinda hummed as she pulled back, never quite pulling off and giving me a wide grin as her eyes flashed up to mine. And then she looked back down as she focused on pleasuring me.

At first, it was just her head bobbing up and down on me while I held the back of her head in my hands. I let my head roll back and groaned as I felt the warm, exciting sensations shooting up and down my shaft.

Rosalinda kept up a steady rhythm for the most part, but for a brief moment, she froze and moaned softly around my cock. Her shoulder twitched a little as I noticed that her right arm was moving, even as her head continued its up and down motion. I hadn't really been paying attention, but I now realized that Rosalinda was playing with herself while she blew me.

She had to pause a few more times as she brought herself to higher and higher levels of self-inflicted ecstasy, and at the climactic moment, she thrust her way all the way down to the base of my cock once again, deep threading me at the same time as she orgasmed.

I could feel the tremors shooting through her body all the way through her throat wrapped tightly around the head of my cock. It was an exquisite earthquake of vibration as she moaned, tears forming in the corners of her eyes as she rode out her climax with my cock filling her mouth.

Once that was done, Rosalinda sat back for a moment, catching her breath and wiping away the tears from her eyes. But then when she'd composed herself, she fixed me with a sharp look. "Time to finish you," she said. And then her hot mouth was on me once again.

After only a few more minutes, Rosalinda's expertise had me whimpering in anticipation of what promised to be a very, very good orgasm. Her talented fingers came into the mix, nails of her left hand lightly scratching at my balls while she circled my pole with her right hand in a tight grip and stroked me.

"Bleep... Rosalinda..." I groaned.

She just looked up at me, so pretty, her eyes a royal blue that began its edging towards violet as she watched the rapturous expressions crossing my face. Her tongue swirled around the crown of my dick as she continued to pump me. She barely blinked even as my eyes fluttered as she pushed me to the edge of my orgasm.



diary of a playboy: https://okadabooks.com/book/about/diary-of-a-playguy/43624

1 Like

Re: Diary Of A Playboy (18+) by yungbanks(m): 2:37pm On Jan 05, 2022
Op why u just dey repeat the updates na
Re: Diary Of A Playboy (18+) by Saturn101: 8:50am On Feb 10, 2022
Waiting for more.
Re: Diary Of A Playboy (18+) by ThrillPlus: 7:27pm On Feb 22, 2022
kweensheba:
Ride on
Re: Diary Of A Playboy (18+) by Zamar: 7:14pm On Apr 26, 2022
Ride on.
Re: Diary Of A Playboy (18+) by Ultimas: 3:48pm On May 15, 2022
She just looked up at me, so pretty, her eyes a royal blue that began its edging towards violet as she watched the rapturous expressions crossing my face.

Her tongue swirled around the crown of my dick as she continued to pump me. She barely blinked even as my eyes fluttered as she pushed me to the edge of my orgasm.

My hips suddenly twitched and I was sure she could feel the tension in my balls, so Wumi backed off quickly and began stroking my cock with both hands as she aimed it right at her face.

My first shot drew a line straight from the bridge of her nose and down to her upper lip. The second spurted right into her mouth, which she closed and immediately began murmuring happily as she swallowed.

And without stopping the motion of her hands she pumped out the rest of my jizz onto her chest, where little puddles of my cum oozed down between her naked breasts.

I wanted to lay back and fall asleep in that moment, but the sight of Wumi covered in my cum held my attention on her even as the rest of my body sagged.

She smiled and used a finger to scoop up some of my cream, popping it into her mouth and sucking like a lollipop.

Still smiling, Wumi got up, completely topless. "I'll be right back," she husked as she grabbed her purse and her clothes and went into my bathroom.

We hadn't taken the time to slip off her shoes, so her heels clacked loudly on my wood floors with every step.

I fully expected Wumi to emerge fully clothed and ready to say goodbye. She'd gotten her own orgasm and she'd gotten her taste of cum. After all, she'd promised it would be just a Mouth Gig.

I should have known better.

Wumi came out almost completely nude. She was still wearing her jewelry and she was still wearing her heels. But that was it.

And so with an impish grin on her face, Wumi came right up to me and began pulling me off the couch.

"Wumi, you promised," I whimpered.

"Yeah, I lied." The phrase so casually fell from her lips, but then she was pulling off my shirt and pressing her hard nipples into my chest. Then she leaned in and whispered into my ear.

"Besides, for all you know this is your last night in this bed. We have to give it a warm sendoff." And then she licked my ear.

My knees were turning to jello, and yet they were still much stronger than my resolve. I managed to kick my shoes off, quickly followed by my jeans and then I was as naked as she was, except for her high heels. Those I wanted her to leave on.

I held Wumi's head in my hands as I kissed her, filling my nostrils with her spicy sweet scent. And for just a moment, we had a quiet peace. I was filled with all the desire and affection I had for this woman.

She was so sexy, so vibrant, so attractively self-confident. I knew I could be happy with this woman who had been such a dear friendfor four years, even if she was a little self-centered.


Diary of a Playboy: https://okadabooks.com/book/about/diary-of-a-playguy/43624
Re: Diary Of A Playboy (18+) by Awesome05: 4:04pm On May 17, 2022
Nice update.
Re: Diary Of A Playboy (18+) by BigBasher: 11:37am On May 22, 2022
Nice one.
Re: Diary Of A Playboy (18+) by Ultimas: 1:26pm On Jun 05, 2022
...
Re: Diary Of A Playboy (18+) by Ultimas: 11:53am On Jun 26, 2022
I held Wumi's head in my hands as I kissed her, filling my nostrils with her spicy sweet scent. And for just a moment, we had a quiet peace. I was filled with all the desire and affection I had for this woman.

She was so sexy, so vibrant, so attractively self-confident. I knew I could be happy with this woman who had been such a dear friendfor four years, even if she was a little self-centered.

I wouldn't have minded just standing there, folding our naked bodies around each other and enjoying the simple pleasure of a kiss. But like usual, Wumi was in charge and she pulled me towards my bedroom.

The shades of my window were open, letting in the moonlight which cast the entire room in soft shadows. In this light, Wumi's clear eyes glowed a light grey, and her smile alone lit up this room.

She leaned back onto my bed and pulled me on top of her where we began to kiss slowly. So many of our encounters over the years had been rough and ready Bleep sessions. We were both terribly in a hurry and filled with lust for each other that we always ended up attacking each other in a frenzy.

But on a few occasions we simply made love. And it seemed like this was going to be one of them. Wumi hand was gently caressing my cock, and my fingers were not idle at her wet box either. Our tongues dipped and delved within each other's mouth while Wumi's other hand stroked along my spine.

I slid down her body until I came face to face with her steaming pussy. She'd shaven recently and the smooth skin glistened with her arousal. She spread her legs and hoisted her legs up into the air while my hands each gripped an asscheek. And now it was my turn to return the favor.

I strained to go slowly, softly. My tongue and my lips barely grazed against her sensitive skin, almost tickling Wumi. And I continued my gentle, agonizingly slow ministrations of orally worshipping at Wumi's altar of love. I felt like I could remain there forever, listening to her cute whimpers of pleasure.

But once Wumi started to get really turned on once again, she would have no slow worshipping going on in her temple. Wumi's whimpers turned into moans and then her hands were now on the back of MY head, pressing me deeper into her as I began to eat her out with more fervor. "Fuuuuck, Tade."

My hands circled around her ass and after inserting a finger deep into her sopping wet pussy, I pulled it out and pressed it against the tight muscle of Wumi's anus.



Playboy: https://okadabooks.com/book/about/diary-of-a-playguy/43624
Re: Diary Of A Playboy (18+) by YoungBruzzy(m): 10:07pm On Jun 27, 2022
Thanks for the update OP
I guess you are making a mistake with the names: You are now using Wumi Instead of Rosalinda. Please rectify that.

1 Like

Re: Diary Of A Playboy (18+) by BigBasher: 7:12pm On Jul 09, 2022
More...
Re: Diary Of A Playboy (18+) by Ultimas: 2:00pm On Oct 02, 2022
My hands circled around her ass and after inserting a finger deep into her sopping wet pussy, I pulled it out and pressed it against the tight muscle of Wumi's anus.

She shuddered in my grasp as my finger surprisingly slid in very easily. I'd gotten my finger wet, but not that wet. And I picked my head up in surprise.

"I lubed for you..." she giggled at the expression on my face.

My dick twitched violently on its own hearing those words, knowing instantly what it meant. Wumi wanted me to Bleep her ass tonight. And suddenly I had no more patience to continue going down on her.

Wumi didn't seem to mind, and in fact she whooped in glee as I suddenly pounced on top of her naked body and snatched up her feet in my hands. With her heels in my grip, I forced Wumi's knees back against her own shoulders until I'd damn near bent the girl in half. And then holding her legs wide in a big V, opening up her wet vagina, I aimed my cockhead and then pounded my way into the back of her womb in one ferocious thrust.

"FUUUUCK ME!" Wumi screamed. It was loud enough I'm sure the neighbors could hear. Of course, I was sure they'd heard us a number of times. And without letting go of her heels I jackhammered in and out of her rapidly.

It was apparently just what the doctor had ordered for Wumi. Less than a minute after my dick had entered her, Wumi was shrieking in the throes of her climax, the sound of her voice vibrating in response to the vibrations running up and down her body.

I wasn't about to let up on her either. Instead, I just kept fucking as hard and as fast as I could, my cock now swimming in a veritable sea of orgasmic fluid. And just when it seemed that Wumi's orgasm was waning, I pulled out, redirected, and then shoved my way into Wumi's asshole.

Wumi's shriek briefly went up an octave when the head of my cock penetrated her nether hole, but then her voice died out as she seemed to just run out of air. Her mouth was still open in a silent scream, tears in her eyes as she fought to breathe.

For my part, I was focused on driving my cock up her ass. Despite the heavy moisture coating my pole, and the lube inside her anal chute, I had a tough time forcing my way in. And as Wumi lit off into another orgasm, her muscles clamped down so tightly I thought she might actually squeeze my cock off in her ass.

But once she relaxed again, I was able to glide forward, constant pressure pushing me in until my balls were trapped against her asscheeks.

We both paused to catch our breath, Wumi's body folded in half beneath me, blinking away the few drops of sweat coming off my forehead as she panted and laughed almost maniacally.

"Oh, that's so great, baby. But I wanted to change positions."

"Yeah?"

"Yeah, I want you to Bleep me like an animal."

"Well, I can't complain with that."

And so with the coordination borne only out of familiarity, I pulled out while Wumi spun herself around on my bed. I stood back, enjoying the momentary relief from the constriction of her ass on my cock, letting my orgasmic energy subside a little. With this little breather, I knew I'd be able to really ream out her ass for a good long while.
Re: Diary Of A Playboy (18+) by Awesome05: 4:50pm On Oct 03, 2022
Welcome back.
Re: Diary Of A Playboy (18+) by ThrillPlus: 1:15pm On Oct 06, 2022
Cool.
Re: Diary Of A Playboy (18+) by Ultimas: 8:49pm On Oct 08, 2022
With this little breather, I knew I'd be able to really ream out her ass for a good long while.

Wumi got into her position, facedown on my bed with her arms folded beneath her face. Her ass was sticking back at me, hanging off the edge of the bed with her high heels planted on the floor, forming an A-frame with her legs. Time for me to Bleep her like an animal.

Eagerly, I stepped between her legs, my hands spreading her asscheeks before me so I could see her distended hole. And then before she realized it, I'd shoved half my cock back into her ass.

"Fuuuuuck..." Wumi groaned.

And with a few extra shoves, I got myself fully seated, balls deep into her nether hole. The feminine ass in my hands was absolutely perfect. The hips flared prettily around perfectly-shaped tight globes. The skin was milky white and unblemished.

"God, Wumi, you are so fucking hot..." I groaned as my cock pistoned in and out of her ass. I really could stare at this sight all day.

That's when the pounding began.

I honestly lost track of how long I bleeped her. I can't even remember how many orgasms she had. It could have been five minutes or it could have been half an hour. I do know that the next morning my pelvic bone hurt like hell.

But that night, my eyes just rolled up in my head and I let myself lose control. I wasn't trying to last a long time. I wasn't trying to give Wumi pleasure. I just let the baser part of me give in to the lust and simply violate her ass. I bleeped and I thrust and I drooled and I bleeped some more. And when my conscious mind reasserted itself, I had Wumi's hips in a death grip, pinning her lighter body against me as I held myself as deep into her bowels as I could go. And I was cumming. Oh, was I cumming.

It didn't even feel like separate bursts. It felt more like I was pissing pure sperm into the darkest recesses of Wumi's anal cavity like a firehose. More and more fluid poured out of me, and when I thought I was done there was a bit more still coming out. My mind was in absolute bliss.

And when at last the flow stopped, I simply staggered back, my legs muscles suddenly locked into position and unable to move lest I inflict great pain on myself.

Wumi's feet had long lost their grip on the floor, and so she lay sprawled across my bed, a limp noodle absolutely destroyed by what we had done. Her asshole was stretched into a gaping ring, still not contracting and already dribbling rivers of cum out onto her thighs.

Both of us were gasping as if we'd forgotten to breathe during the whole ordeal. I was leaning against the wall, trying valiantly not to collapse onto the ground.

After a couple of minutes, Wumi groaned, "What the hell did you do to me?" Her voice was pained, but there was a smile on her face.

1 Like

Re: Diary Of A Playboy (18+) by BigBasher: 2:23pm On Oct 09, 2022
Nice update.

1 Like

Re: Diary Of A Playboy (18+) by Awesome05: 5:59am On Oct 12, 2022
Ride on.
Re: Diary Of A Playboy (18+) by BigBasher: 7:48pm On Oct 14, 2022
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Re: Diary Of A Playboy (18+) by Awesome05: 9:37am On Oct 17, 2022
Go on.
Re: Diary Of A Playboy (18+) by Saturn101: 7:30am On Oct 19, 2022
Go on.
Re: Diary Of A Playboy (18+) by ThrillPlus: 8:46pm On Oct 21, 2022
Next...
Re: Diary Of A Playboy (18+) by BigBasher: 7:19am On Oct 25, 2022
Go on.
Re: Diary Of A Playboy (18+) by ThrillPlus: 7:06am On Oct 27, 2022
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