Prim And Proper Slut Needs More Cock

This story is a sequel to my tenth story published previously, about an acquaintance from my country club who had come over to "console" me after a breakup with a mutual friend. The first part is called "Prim and Proper Cock Whore".

This is the latest story in my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

Not everyone likes me or my stories. That's OK.

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Gabby, Part 2

Gabby was a friend from my country club who came over to my house one time under the guise of helping me get over a recent breakup with a mutual friend. Turns out, she was a closet big cock slut who had heard from my ex-girlfriend Susan that I had a big dick, so she came over the get a taste since her twenty years older husband did not, and struggled in the bedroom generally.

She had come over about four months prior, and I knew she'd be back.

Sure enough, as the weather started to warm up, I got a call from Gabby. I recognized the number, so I answered, "Hi Gabby, how's my favorite big cock slut?"

"Hello Philip," she answered. "I'm here at the club with Mr. Brown (the catering director of our club) going over some details of a new charity fundraising event that I am going to host. We are going over a list of potential sponsors, and your name came up as someone who might be a perfect sponsor."

It was funny to me to think that Mr. Brown was there in the room with her (thank God I wasn't on speaker!).

I played along.

"Sure, I'd be happy to discuss it with you. Why don't you come over tonight and try to convince me on just how big of a check I should write."

"Thank you, Philip," she answered. "yes, tonight would be splendid. I can meet you at approximately eight o'clock?"

"Not 'approximately'," I warned her. "Exactly eight o'clock. And I'll expect that you'll be wearing a light sundress with nothing on underneath it. I'm gonna rip that dress right off of you. And if I were you, I'd do some prep on your ass, because I plan on fucking that ass tonight. And it won't be gentle, it will be nice and rough, just like you like it."

"Wonderful," she answered, her breathing slightly heavier. "And yes, I believe that those arrangements can be made as well. Thank you for the splendid suggestion."

"One more thing," I said. "Try to keep up the formal, sophisticated lady routine as long as you can."

"Of course, Philip. It will be my pleasure to see you and make a pitch for this worthy cause."

"And it will be my pleasure to come on your face. See you in a few hours."

I laughed as I put the phone down. Fuckin' chicks are all the same.

At 8:00 on the nose, my bell rang. Gabby stood there in a yellow-ish sun dress, her big tits and nipples very evident through the thin material. I wore only a robe, naked underneath. I wouldn't be wearing it for long.

"C'mon in," I welcomed her. "I like that dress."

"Thank you. Your kindness is very much appreciated."

Good thing it was dark out, there was not much left to the imagination with nothing on underneath.

Gabby continued, "What a gorgeous robe! It fits you wonderfully. And this material is straight from heaven."

She was pouring it on a bit thick. But it was funny.

Gabby was holding a small tote bag, and a folder with some papers in it.

"Let's have this meeting down the hallway," I said as I guided her back toward my bedroom. "Would you like something to drink?"

"I'm fine at the moment Philip, but thank you," she answered. "I'm anxious to get to my presentation."

We entered my bedroom, and I walked over to the overstuffed chair that sat near my bed. I stripped off my robe, my cock already about three quarters hard, and turned to her. Gabby looked down at my dick and I could tell she was tempted to break character already, but she held it together.

"What a lovely penis. I do recall from our last meeting that you are quite well-endowed. Perhaps if necessary to close the deal on your sponsorship, I might partake again in the pleasures of your flesh."

I sat down with a laugh. I was enjoying this, and she was being such a good sport about it.

I stroked my cock and said, "OK, let's hear it."

Gabby spent the next five minutes very professionally explaining her new charity and the various levels of financial sponsorships that were available. I stroked my cock and watched her eyes dart back and forth from my dick to my eyes as she made her pitch to me.

It all sounded great, and I was happy to contribute at a high level, but we had to play our game first.

"This all sounds great Gabby, but I'm not sure it's right for me. Maybe I could be convinced to contribute at the lowest level if you get on your knees and suck on my cock for a bit."

"Of course, Philip. It's a bit unconventional to solicit donations this way, but I'm happy to go the extra mile to secure your support."

Gabby knelt before me and replaced my hand with hers. As she had before, Gabby made love to my cockhead, shaft and balls with her lips and tongue, expertly licking, kissing and lightly sucking me all over. It was heavenly.

Gabby paused after a few minutes, allowing my cock to throb in midair as she sat back on her haunches and said, "If you'd consider increasing to a bronze level, I would happily swallow your entire penis and accept a rigorous thrusting in and out of my esophageal canal."

With that, I grabbed her hair and pushed her head down into my lap. Gabby opened her mouth and engulfed my entire cock in one gulp, swallowing it to the root. I heard the head of my cock pass her gag point with a slight 'glug,' as it did so, and she held my cock in her throat for almost a full minute.

Finally, she started to pull her head back, and I went to town, grabbing her head and forcing my entire length in and out of her. It was a true face fucking, and Gabby took it like the big cock champ that she is.

I could've come, easily, but I had other ideas.

I pulled Gabby's head off of my dick, grabbing her hair and pulling her head back. She was out of breath, her lips swollen and her lipstick smeared from the blowjob that I had interrupted.

"Stand up," I ordered, and she complied.

"I'm thinking Silver level," I said as I grabbed her sundress around the collar and violently ripped it in half, right down the middle (probably a five-hundred-dollar dress, I thought). Gabby gasped as the material fell away, leaving her naked in front of me.

Gabby was ready to give up the facade, but she recovered.

"My goodness, well I guess I will have to fill out an expense report for the Foundation to cover the cost of that dress. I'm sure it will be covered as a marketing expense, since it increased your sponsorship level by a thousand dollars."

I pushed her perfect tits together and sucked on her pencil-eraser nipples, alternating between the two and biting down harder and harder with each switch. I then moved a hand between her legs, which she parted slightly, and found her soaking wet cunt.

I pulled back from her tits and looked up at her face. She was looking down at me lustfully, pleading with her eyes to penetrate her.

"Charity makes you wet, doesn't it slut?" I asked, then jammed two fingers into her up to the last knuckle.

"Oh God," she groaned, and her will was starting to break.

I could tell she was desperate to let loose with a string of profanities and dirty talk to match her arousal, but she held firm a bit longer.

I fingered her for a minute or two, tickling her clit with my thumb on occasion as my fingers pumped in and out of her wet hole.

"You have very talented fingers Philip. I recall your oral skills from our last meeting, and I must say that your fingers feel almost as good as your tongue did back then. Perhaps we can increase you to a Gold level, which is reserved only for those who love to perform oral sex on a woman from behind."

With that, Gabby turned around and bent over my bed, facing the full-length mirror on the other side of the bed. When she spied herself in the mirror, all resistance was lost, and she finally dropped the formal facade.

"Oh God," she gasped. "I love watching myself get fucked in the mirror! Eat my pussy and then stick that giant dick into me and fuck the shit out of me!!"

I knelt behind Gabby as she stuck her ass out at me, angling her hips upwards to open both her holes to me. I buried my nose in her ass and tongued her pussy from behind. I caught the faint smell of strawberry, then realized that Gabby had in fact prepared her ass for fucking tonight, having applied some strawberry flavored lube to her asshole.

Her pussy was delicious, as I remembered from several months ago. No doubt she had it professionally cared for weekly if not twice a week. Total heaven. I licked and sucked that wet pussy and those meaty pussy lips, driving my tongue up inside her as deep as it could go.

Gabby helped by lying on her torso and reaching back to spread her ass cheeks, allowing me even greater access to both her holes.

Ms. Sophisticated was gone, replaced by a trailer-trash talking whore.

"Yes, lick my pussy and asshole, you filthy pig. I spent the whole day with a butt plug in my ass just so you can fuck my ass without killing me, so finish licking me, then fuck my pussy and my ass."

I was more than ready, so I rose up and ran the head of my cock up and down her meaty lips, watched the head part the outer lips of her cunt, then grabbed Gabby by the hips and slammed myself home.

"Oh Jesus H. Christ!" she yelled as I reached full depth. "That fucking thing is God damn huge. Fuck me, don't stop, hard and rough please."

I pounded Gabby for all I was worth. I held her down and pushed her face into the bed, then wrapped her long black hair around my fist and pulled her head back.

She loved it all.

After a good ten minutes of pounding her, I yanked her hair until she was looking back at me, and said, "tell me what you really want."

"Fuck my ass, please. Fuck my ass hard and rough and come deep inside me, please."

She didn't have to ask twice. I pulled my cock out of her pussy. It glistened with her pussy juice and was perfectly lubed. The lube and butt plug prep that Gabby has used earlier in the day was about to be put to the test.

I lined up the head with the entrance to her ass, and just as she felt it, Gabby forced her hips back, swallowing the head and the first third of my cock.

She screamed bloody murder, but did not try to escape. In fact, she looked back at me with fire in her eyes.

"More," she demanded, and we simultaneously pulled our bodies back, then pushed against each other. This time, about 80% of my dick reached into her inner bowels. Gabby's guttural scream filled my bedroom, but she wanted it all.

"Again," she cried. "All of it."

Once more we separated, just the head of my dick inside her ass. I grabbed her hips and pulled her back to me, my cock finally burying itself all the way inside her.

"Fuck me! Do it!"

I began a steady rhythm, sawing in and out of her ass, the pace and force increasing with each thrust.

Gabby loved it rough, so I pulled her head back by the roots of her hair with one hand, and began slapping her ass with the other. Each "smack" reverberated through my bedroom and elicited a yelp to escape her mouth.

After seven or eight spanks, Gabby muttered a throaty "more," so I upped the ante, letting go of her hair and really laying into her ass with both hands. The lighter skin of her ass cheeks began to turn red with my hand prints, then purple.

I gave up the spanking and wrapped my hands around her throat, then put my fingers in her mouth and "fish hooked" her, taunting her all the way.

"You are such a fuckin' slut," I scolded her. "Wouldn't all your hoidy toidy friends at the club with their thousand-dollar shoes love to see you now, bent over my bed, a big cock in your ass while you beg for more. They'd love to see what a cock-whore you are. Although they are probably the same way, aren't they?"

Gabby reached back to finger her cunt, then she grabbed my balls, and I responded by unleashing a load into her rectum as she bit down on my fingers that were still fish-hooking her.

"Ow, you fucking cunt," I yelled, removing my fingers and wrapping my hands around her throat again as I finished my orgasm. Gabby shook violently, another orgasm ripping through her.

I collapsed on top of her and we laid there, out of breath and sweating from the animalistic rough anal sex we just engaged in. Finally, I pulled off of her and fell back into my chair.

Gabby stood and faced me, then took two short steps toward me in my chair. She stood in front of me and pinched her big hard nipples, then leaned down and gave me a very sensuous kiss.

She stood back up and said, "I'm ready for that drink now. A Manhattan up would be great. I'm gonna jump in your shower. Why don't you give me about ten minutes and then join me."

Slipping on some gym shorts, I watched in admiration as her wide hips, round, red ass and long, shapely legs sauntered into my bathroom and closed the door, then I made my way out to my bar and mixed us each a drink; mine a bourbon on the rocks and hers a Manhattan, straight up.

I set the drinks on the nightstand in the bedroom, then opened the bathroom door. She was standing in my doorless, oversized walk-in shower. My timing was perfect as she had just begun soaping up her body, those luscious tits and pointy nipples being massaged with foamy soap bubbles from her body.

She spotted me and smiled, calling me forward with a hooked finger. I stepped in and helped her to massage her soapy tits, pinching those nipples that were sticking out like pencil erasers. Her hands were full of soap, and they went to my cock as she washed me thoroughly as well.

We turned to face the spray, and we watched as the water cascaded down her chest and the soapy white foam slid across her tits, down her stomach and legs to the shower floor. Very hot.

Gabby's hands continued to massage my cock, and whispered in my ear, "I can't believe this amazing cock and how it's always hard. I need you to fuck me again. Didn't you say something this morning about coming on my face?"

I smiled and said, "Oh yes, I'm not done with you by a long shot."

We kissed for a moment, then I moved my lips to her ears and whispered, "I won't be able to come again until I piss on you."

"Oh God," she groaned back in response.

I placed my hands on her shoulders and gently pushed her to the floor of the shower. She descended willingly and looked up at me expectantly. With my half-hard cock in one hand, I grabbed her by the roots of her hair and yanked her head back with my other hand.

"What a fuckin' slut you are," I snarled at her, then pointed my cock at her chest.

My stream blasted her first on the chin, then continued across her chest and tits. Gabby pushed her tits together, and I shot my piss into the crevice that was created, watching the salty fluid pool up in between her tanned breasts.

When I was spent, Gabby dropped her tits and the pool of urine flowed down her chest. I grabbed some soap and soaped her up again to clean the residue off of her, and her mouth went to my cock to suck me to full hardness once again.

I shut off the water and stepped out, grabbing a towel and handing it to Gabby, then grabbing one for myself. As she turned around and dried herself, I saw her still-inflamed ass cheeks from my earlier spanking. I had given her a pretty rough beating, and her ass was pretty sore looking.

Stepping up behind her, I ran my fingertips over her globes, then whispered, "Let's go sip our cocktails, then I'll rub some lotion on your sore ass."

Gabby gave me a knowing look, then sauntered back into my bedroom. She grabbed her drink and settled in on the bed with the towel wrapped around her. I joined her and we reclined back, quietly enjoying our beverages.

We finished our drinks almost simultaneously and set them down on our respective night stands. I then got up and grabbed some lotion from my dresser. Gabby saw me, and without being told, undid her towel and rolled over on her stomach, lying flat against the bed.

Applying some lotion to my hands, I rubbed them together to warm it up, then gently began rubbing the cream into the skin of her generous, round ass. I was careful because she looked sore, so my touch was light. Gabby quietly moaned in appreciation and enjoyment as I continued caring for her bruised flesh.

After five good minutes, my fingers slowly made their way into the crack of her ass. Gabby responded by raising her hips a bit and spreading her legs slightly, allowing me access to her recently abused asshole and now wet pussy. I bypassed her ass and found her wet cunt with my pinky, and ever so slowly began moving my finger back and forth. Gabby moaned louder and wiggled her hips in response.

I withdrew my hand and flipped Gabby over. Kneeling next to her as she lay flat on her back, I put more lotion on my hands and now began massaging the cream into those softball-sized tits and long pointy nipples. I would squeeze them together, then relax and focus on the nipples for a few seconds, repeating the pattern about a dozen times.

Gabby's eyes never left mine, until a drop of precum formed at the head of my cock as it hovered over her. Following her eyes, I noticed it as well, and Gabby groaned again as I scooped it up on my finger, then brought it to her mouth. She sucked the fluid off, then reached for my dick herself. She squeezed my shaft, causing another drop to form, which she scooped up and rubbed on her lips like lipstick.

Now it was me who groaned as I leaned down to kiss her and taste the sweet-salty fluid from her lips. Our kiss continued, and I laid down next to her as our tongues danced.

My hand slithered down between her legs, which she opened widely to allow me full access. I fingered her with first one, then two fingers, gently pumping them in and out of her wet hole. Gabby was thrusting her hips into the air, trying to get more and more of me inside of her.

After a few minutes of this, I removed my fingers and grabbed a fistful of her meaty labia. I broke our kiss and pulled my head back, our eyes locked as I squeezed my fist, the tender skin of her pussy lips being trapped between my fingers.

Gabby's eyes measured a mix of pain and arousal as I squeezed tighter and tighter. It must have hurt like hell, but pain was her thing, and she whispered, "please, more" as I continued to apply pressure.

Gabby's hands went to her tits and I neared the maximum amount of pressure I could apply. She pinched her nipples, then pulled my face toward her left tit. I bit down hard on her nipple as I squeezed her labia as hard as I could, and she exploded in a throaty orgasm.

"Oh fuck yes!!!" she screamed as her hips thrust into the air. I stayed latched onto her tit as she came down from her high, and I relaxed all pressure slowly from her nipple and pussy lips.

Gabby flopped back with a contented sigh, and I got the sense that she had had enough pain for the day.

With that in mind, I slowly made my way down between her legs, which she again opened welcomingly, and I was face to face with her abused pussy. I lovingly licked around the outer folds, then slowly worked around the inner folds and into her canal with my tongue, very gently.

Her pussy was on fire, hot from the abuse, and I remembered my drink on the nightstand.

I came out from between her legs for just a second, and stretched to reach for my glass, still full of ice. I took two cubes into my mouth as Gabby watched me, then her eyes got noticeably bigger as she realized the ramifications of what that meant for her.