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Carl & Gladys

Category: Mature
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I didn’t like Carl when I met him.

I liked him even less when I realized what he was up to.

The place was an upscale bar in a big city. It doesn’t really matter where. It could have been anywhere. It could have been in your hometown.

You know the kind of bar I’m talking about. Lots of wood, a friendly but quiet bartender, maybe a little jazz trio on some nights. It was the sort of watering hole businessmen and vacationers stop in after a day’s selling, conferences or touring. A nice place.

I liked staying here when I was in . . . oops, I almost told you where, but, like I said, it doesn’t matter. It could’ve been anywhere.

This time I was in town for a conference with some of my business associates but there were none at the bar this night.

There was only Carl.

He looked friendly enough but there was, I don’t know, a kind of harried appearance to him. Haggard. It could have been the look of someone who drank too much. It could have been the look of a man who sleeps but is never refreshed.

Carl was in his mid 60’s or so. Paunchy. Wheezy. If he didn’t smoke now, he almost certainly did once. And there was that uncomfortable pallor I mentioned earlier. Still, he brightened when he saw me. It was the smile of one of my salesmen who sees a potential customer walk in the door.

But I was feeling pretty good and decided to smile back. Sales were up. The conference was interesting and I didn’t feel like sipping my scotch alone. Carl beckoned to the bar stool next to him. He introduced himself and I shook his hand. A puny handshake. He was no salesman.

“Business?” he asked.

I nodded. “I’m here for a conference. I’ll be here another couple of days. How about you?”

“Oh, I’m retired,” Carl said as if he were a little ashamed of the fact. “Me and the wife are just taking in the sights.”

“Staying here?”

Carl chuckled. It was a loser’s laugh. It said: ‘I’m not worth enough to stay in a fine place like this.’ “No,” he said, “We’re staying at the Holiday Inn.”

I nodded, took a sip of my drink. “How come she’s not here?”

The little laugh again. “Oh, she’s around.”

He had lots of questions. Was I married? (Once). How old? (42) Job? (Sales manager). And once he actually had me stand up and get a snack tray from the other end of the bar. Strange because there were pretzels within easy reach but I did it anyway. Something weird was going on. Something funny. And I was curious to find out what it was.

And then Gladys came into the bar. Or, rather, she came from a corner of the bar. I hadn’t seen her there before. I started to think I was being “cased.” Interesting.

Gladys was also in her mid 60s and looked every year of it. She may have been older. She was only about 5-2 or 3 but must have weighed 160 or so. Hard to tell. Gray hair. Some styling but nothing special. Same for the dress. It was a simple sleeveless, one-piece green-patterned shift that couldn’t have been more shapeless.

But the thing that was most striking was Gladys herself. She looked shy. She looked frightened. She looked for all the world like someone who would rather be just about anywhere else. When I shook her hand, it was cold and clammy.

Not unattractive for an older woman, but Gladys was no looker. Carl ordered her a glass of white wine and she drank it slowly. She answered questions with just one or two words. She had two children, four grandchildren. She wouldn’t look me in the eye when she talked but I did my best to be polite and make her feel comfortable. I smiled a lot. She seemed to calm down some after a time.

Finally she stood up an excused herself but before she left she looked at Carl with that same fear and uneasiness and nodded slightly, then hurried off to the ladies’ room. Carl smiled widely.

“She likes you,” he said.

I was going to say ‘hard to tell’ but instead I said “I like her too.”

“Good,” he took a long drink, drained the glass actually, and slapped it down on the bar. I could now tell he must have been drinking for some time before I arrived as his words were a little slurred.

He spoke in a stage whisper. “Would you like to sleep with her?” Carl laughed and hiccupped at the same time. “Would you like to fuck her?”

So that was the game. Okay, I suspected something like this from the beginning. It had never happened to me before but one of my salesmen – he was actually here in the hotel – told me of an episode like this once except the players were far younger. Sport fucking, he called it. Hubby, wanting to fire up his sex life, gives his wife away to a stranger for the evening. My friend said it was the best sex he had in his whole life.

I admit the thought excited me when he told the story but I have this thing about fucking older women, about Gladys age, if the truth be told. It was just a fantasy though.

But now I was being offered my fantasy on a silver platter. I didn’t know what was sicker: me for wanting to do it or Carl for giving her up. I may have had lots of questions but one thing was clear: this was Carl’s idea, not Gladys’s. I didn’t want to look too eager.

“Don’t you think she’s a little old for me?”

“Old, schmold,” said the drunken Carl, and he pulled me close to him, like drunks do when they want to talk with you. “I haven’t had a piece of her in 8 years or so. Can’t get it up. It happens! It’ll happen to you.”

“That so?”

“Lissen, lissen,” he said. “Here’s the thing. She’s probably gonna be a little dry.” He slipped me a small box. “That’s KY Jelly. Use that.” He nodded.

Seems like the bastard thought of everything.

“Have you done this before?”

“Nope, never.”

“How’s Gladys feel about it?”

Carl waved the suggestion away. “Oh, she’ll do it, she’ll do it. ‘Cause I want her to.” He looked at me hard again. “So whaddya say?”

“And this is okay with her?”

“Sure, sure . . . but there’s one more thing. I wanna watch.”

A new, er, wrinkle. “I’m going to have a hard enough time getting it up for a grandma,” I lied, “let alone knowing my performance is being graded.”

Carl waved broadly again. “Don’t worry. I’ll be discreet. You won’t even know I’m there. So whaddya say?”

“My room?”

“Yeah, sure, anyplace,” he said, eager to get on with it. And then he leered, he really leered. It was ugly. “And no matter what happens, don’t stop. Do it good and let her go when YOU’RE finished.”

Like I said, Carl was a real piece of work. Take my old wife, rape her if you want to and throw us out the door when you’re finished. It was sick but, god help me, it turned me on. I nodded and told him to bring Gladys to my room in 15 minutes.

I got to the room, made a phone call, and poured myself a drink. I made another call and had room service bring up a bottle of wine like Gladys had been drinking. Fortunately, room service came quickly with the wine. Gladys came a few minutes later. But Carl wasn’t with her.

“Hi Gladys.” I smiled my very best sincere smile at the frightened old woman standing in the doorway. I decided it was a better-than-even chance that she would bolt down the hallway but she just looked over her shoulder once, then came into my room. I closed the door quietly but didn’t lock it.

Gladys looked around a little nervously and said with a surprisingly strong voice that “Carl will be coming up a little later.”

“Great,” I smiled trying to put her at ease. “We can talk for a while. I didn’t get a chance to chat with you much in the bar.”

I uncorked the wine and poured some into a glass which she took and sipped politely. She looked around the room and I looked over Gladys.

The long dress couldn’t hide the thick ankles. Like I said, she was no beauty. She had an ample ass and nice tits from what I could tell under the shift she was wearing but whatever charms she possessed were well hidden by her clothing.

“I’ve never done this before,” Gladys said, actually smiling a little.

“Me either,” I smiled back and touched her glass with mine.

“For Carl, sex was always more important that it was for me.” She took another long drink. I refilled her glass. “But for me it was just doing my duty. That’s what my mother called it. Doing my duty.”

Nice sentiment.

She continued. “But in the last ten years or so, Carl hasn’t been able to, you know, get hard.” She blushed a little. Cute.

“This is so difficult and I’m so embarrassed.”

I touched her bare arm for the first time to reassure her. “Please. Don’t be nervous. We’re just two new friends getting to know each other. Go on.”

She smiled again. Nice teeth. I wondered if they were hers. She flicked away some hair from her face and I could look up the armhole of her dress. Big heavy-duty white bra holding in their prize. I wondered how big the prize was.

“He’s been frustrated and I can understand that.” She took another drink. “Frankly, I was glad when he couldn’t . . . do it anymore. But he still wanted me to play with him until . . . he was satisfied.”

“Doing your duty,” I smiled.

This time Gladys laughed. Nice laugh, a little common, but nice. “He never was what I would call a considerate lover, even in his good days. Oh, I’ve read a little about it. Carl was more of a roll over, stick it in, fall off to sleep kind of man.”

“Orgasm?” I offered, curious, probing.

She bowed her head, didn’t look at me again. “I guess I’m one of those people who can’t have them. And now at my age, well . . . I can’t believe I’m talking like this.”

I took her drink and grabbed her hands in mine. “You’re a sweet lady. Why is he doing this?”

She shrugged. “He said he wants to watch me getting . . . being made love to.” Blushing. She looked at me again. “He can get satisfied that way, he says.”

“But why are you doing it? Walk away. I’ll understand.”

She patted my hand like she were MY grandmother. “That’s sweet of you but sooner or later, I’m going to have to do it and, well, you’re a nice young man. I owe it to him, I guess.”

I didn’t say what a bastard I thought he was on so many levels but I wanted to make this old woman happy or at least make this all as painless as possible.

“Where is he?” I asked, looking around.

“He said he’ll sneak in and hide. He’s funny that way. Don’t worry about it. Just leave the door open.” Gladys paused, looked down at her chest, then back at me. “Now what?” she said.

I stood up and she did the same. Years of obediently following her man were obvious. I held out my arms and she offered the same simple smile and came to me for a hug. I could feel her bulk and her warmth and her soft tummy beneath the shift. I pulled her tight to me, then looked down at her face and kissed her forehead.

“I’m so glad you’re a nice man,” she said.

If she had only known how my pulse was racing and my lust was rising like a brutal, ugly storm. I never realized until this moment how much I wanted her naked flesh against mine. Something about fucking this sweet, fat old woman sent me reeling but I forced myself to go slow.

I kissed her on the lips and she seemed a little surprised, then relented. Gladys was not participating but she was allowing. That would do for now. I flicked my tongue into her elderly mouth and found hers. It was still at first, even (if a tongue can be such a thing) surprised. Then her tongue found mine and she closed her eyes and even began to mew, her tongue gracefully gliding over mine as I pulled her body tight against me. I felt my cock tighten in my loins.

I sat down on the bed and she sat next to me, her face a little flushed now, looking embarrassed and then she surprised me by kissing me again. This time her tongue was doing all the work and her mouth was soft on my lips, her eyes closed. Breathing faster.

I found the zipper on the back of her shift and slowly moved it down her back to her waist. Gladys never missed a beat. She started kissing my neck and my chest while I ran my fingers over her smooth, chunky back down to her waist.

“Stand up, sweetheart,” I said and, obedient as always, she did so. The green shift fell in a heap at her feet. Her face was a little flushed but she was still clearly uncomfortable and crossed her arms over her chest.

I smiled again and she returned the smile, dropped her arms and placed them around my neck. She flattened those wonderful boobs locked in that great white brassiere against my chest and held her head to my chest. I felt down to the panties. Heavy duty also. White, old lady panties. Why did I expect anything else?

Looking her in the eyes, I kissed Gladys again on the mouth. Her crows feet danced as her eyes closed and our tongues played again. I let my hands run over the satiny panties and the huge ass, then I moved up and unhooked the bra and gently slid the straps from her shoulders while she was still kissing me. The bra fell to the floor.

Pushing her away, I had my first look at those great tits, much larger than I expected. Great silver dollar aureola and hardened nipples. They flopped down on her little tummy and just sang to be supported and sucked.

Grabbing one tit, I sucked greedily, snapped my tongue at the hard nipple and bit it gently. To my amazement, Gladys moaned and held my hungry mouth to her chest. I did the same thing to the other tit, bit harder this time and Gladys moaned even louder. She threw back her head.

“I’m so old,” she said. “And flabby. But, Atkins, you’re making me feel so good.”

I fell to my knees and kissed the great expanse of belly, pulling the elderly flesh into my mouth and grasping the fat butt cheeks with my hands.

What was that? A slight noise. I stood up, looked around and saw the closet door at the far end of the room close. Crazy Carl was here. Hiding. What an asshole. I was determined to pleasure his wife like never before.

“More,’ Gladys whispered.”

I kneaded the right tit while sucking on the left. With my other hand I reached behind Gladys and placed my fingers between her legs and rested them on her panty-covered ass and cunt mound, flicking them like I was playing an arpeggio on the piano.

This 60+ year-old woman started pushing against my hand and I could feel the dampness in her crotch. This was one hot firecracker whose fuse, apparently, had never been lit.

“Take them off,” she breathed huskily. “Pull my pants off now, Atkins. Hurry.”

No need to tell me twice. I yanked on her panties and pulled them to the floor in one swoop. The hot aroma of aroused woman filled my nose as I gazed upon her thick bush and naked body. I turned her around, setting her on the bed and dove between her legs, lapping at her juices and flicking my tongue in her floppy, old cunt hole.

Gladys was moaning now, pushing herself against my tongue. When she bolted, I put a free hand under that huge ass and thought I was in heaven as my fingers probed her ass crack and her wet rectum.

Long pent up cunt juices flowed down her crack and I pushed one, then two fingers into her ass while eating her pussy with wild abandon.

“God, god, Atkins,” she said and pushed against my fingers in her ass while alternately bucking against my tongue in her cunt until she bucked harder and harder, then pushed herself against my fingers and shuddered like a great beast awakening, the first orgasm of her long life.

Gladys fell down on the bed and I took the opportunity to take off my clothes. I could just about hear the no-good Carl yanking at himself in the closet while I positioned Gladys for the kill.

She finally opened her eyes with the most beatific smile I had ever seen and one of the most lust-filled also. She was shameless now. Gladys saw my stiff dick and touched it gingerly at first, then nodded eagerly.

“God, that was great Atkins. I’ve never known . . .Can you do it again? Can you?”

I laughed at her enthusiasm. “I want to fuck your beautiful old cunt, Gladys. Can I do that?”

“Atkins, you can do whatever you want. Can you play with me like before She was breathing hard now, tits splayed out on either side of her great chest. I sucked one and she instantly started moaning again. “Yes, Atkins, fuck me. Do it now. Do it now.”

I worked my tool through the heavy bush defending her nether regions and found the yawning hole I had probed earlier with my tongue, now full of her juices. I slipped my prick into the aged pussy and there was just a moment’s resistance (no KY Jelly, thank you!) then blissful cunt flesh pressuring while I started pumping into that old body.

Grabbing a chunk of hair, I pulled her mouth to mine, mixing her cunt juices with her saliva while I fucked her, then reached behind with both hands to encircle the wonderful ass.

Fucking her hard now, Gladys’ moans rhythmic with my pumping, I slipped one finger, then two and finally three into her ass and pumped alternately with my dick, then my fingers until Gladys was moving back and forth rapidly and moaning in stacatto fashion.

A wild woman, she was tossing her head from side to side which was incredibly exciting, moaning and screaming “he’s fucking me, he’s fucking me!” over and over while I fingered her ass and ultimately pumped my jism into her cunt while pushing my fingers up her ass at the same time,

Gladys shivered with her second orgasm and as I pulled my fingers out, emited a little fuck fart and closed her eyes like she could now die a happy woman.

A knock at the door. I knew who it was. I looked back at Gladys, a little cum stream dripping out of her cunt and down her fat thighs. Pure contentment. I slipped on the hotel robe and went to the door.

It was Philippe.

I mentioned Philippe earlier. He’s the guy who had some experience with what he called “sport fucking” in uptown bars like this one. I had called him and suggested he stop by in a few minutes, unless he heard noise inside the room.

Now it was quiet, so he knocked. A good guy, Philippe.

He’s about 32, tall and slim and French, as you might have figured from his name. “Is it okay?” he asked. “Is it okay to come in?”

“Sure,” and I pointed over to Gladys on the bed, eyes still closed, floppy tits draped on either side of her chest, a big, soaking hairy bush peeking out from between her plump thighs.

Philippe smiled at me, then walked over to Gladys and kneeled down next to the bed. He started whispering something to her and Gladys opened her eyes, smiled widely at Philippe and then at me.

“Hey. Hey,” a voice said.

It was Carl, calling at me from the closet. If there was a more pathetic sight – Carl hiding in the closet after his reluctant wife was starting to come on to a second man after enthusiastically fucking the first – I don’t know what it is.

“Hey,” he said. “I’m ready to go. I didn’t say anything about somebody else.” He was still a little drunk.

I nodded. “Did you make a mess in my closet, Carl?” I knew he’d been jerking off. What a sick bastard. But Carl said nothing. He was losing interest in this game.

“Were you slamming the ham, Carl, while I was putting the meat to your fat old wife? I’ll bet you were.”

“We’re going to leave,” he said while starting to step from the closet. Gladys was sitting up now, unashamedly talking with Philippe who had a hand on her bare shoulder, talking with her.

I put a hand on Carl’s chest. There was no way he was going to walk through me. “I’m sorry, Carl,” I said, feigning a smile. “As I recall, your exact words were ‘do it good and let her go when YOU’RE finished.’ I’m pretty sure that’s what you said, Carl. But guess what?”

Carl just shook his head. He still didn’t get it. A bastard AND a moron.

“I’m not finished,” I looked over to Gladys and Philippe who were standing up, his hands on her fat waist, my cum still leaking down over her knee. “And I have house guests.”

With that, I pushed Carl into the closet, closed the door and took the desk chair to block it from being opened.

“Don’t worry, Carl,” I said. “I’ll let you know what’s going on. And don’t make a big mess in there. I wouldn’t want to explain it to the maid.”

Carl didn’t say anything. Either he was resigned to the situation or he really didn’t mind.

“Good news, Carl. Gladys has found a new friend.”

Philippe was kissing fat old Gladys while massaging her right nipple. Gladys had her arm around Philippe’s neck and with her other hand . . .

“Guess what, Carl,” I said through the door. “Your sweet Gladys is unzipping Philippe’s pants and pulling out . . . lord, what are you hiding in there, Philippe?”

Philippe turned briefly toward me with a big smile, then put his hands on his hips as Gladys pulled his pants down to reveal a huge cock. It wasn’t particularly thick but it must have been 9 or 10 inches. A less secure man than I would have been intimidated. Still, I thought Carl would like to know.

“Hey, Carl,” I said. “Have you ever fed Gladys 10 inches of meat?”

He groaned from inside the closet. This was fun.

“She seems to really enjoy this. I’m guessing she never saw anything like this before. She’s like a kid with a new toy, Carl.” Gladys was stroking Philippe’s long cock and it seemed to grow even longer.

“Your Gladys is licking Philippe’s massive dick, Carl. Oh, where’s a camera when you want one? This would make a great Christmas card photo for the grandkids.”

If Gladys heard any of this, she didn’t appear to care. She was wild-eyed with lust, her big tongue licking his scrotum and she even started biting at his pubic hair while pulling him to her face by cupping his ass.

“Get on the bed,” Gladys said. It was not a suggestion but I think Philippe would have gone along with it anyway. He was grinning from ear to ear. Still wearing his shirt, he laid down on the pillow, put his hands behind his head and Gladys crawled between his legs. Just Philippe, Gladys and a huge dick pole sticking up between them.

Gladys stayed kneeling in front of Philippe, bent over and started slurping his rigid cock like it was a really long, cream- filled popsicle.

This was a new view of Gladys. Her fat ass bobbing as she lapped up whatever Philippe was offering and a nice, soppy asshole looking at me eye-to-eye, so to speak.

I went over to my trouser pocket and took a box out.

“Good news, Carl,” I called back to him. “It looks like I WILL get to use that KY Jelly you gave me after all.” Gladys was slurping louder than ever, rubbing Philippe’s chest and taking – I couldn’t quite believe it – Philippe’s entire length in her greedy old mouth. I dropped my robe and was pleased to see that my Mr. Johnson was coming back to full attention.

“I’m ready for seconds, Carl. You know how it goes. It just takes a little time and inspiration to be able to go at it again . . oh, I forgot. You can’t get it up at all, can you Carl? Now that was just in bad taste, then.”

I got on the bed where Gladys and Philippe were happily engaged in good, old-fashioned fellatio and Gladys’ surprisingly supple old butt was bouncing around deliciously in front of me. I squeezed out some jelly and applied it to the sweet old ass I had finger fucked just a few minutes earlier.

Gladys jumped a little.

“It’s okay, sweetheart. Just relax and you’ll love it, believe me.”

Gladys nodded without ever dropping Philippe’s humongous pecker from her mouth. She was picking up speed and he was getting ready to go. I had to hurry.

I took my cock and slid it along Gladys’ ass crack while fingering her asshole. The KY jelly,my cum and her juices had slicked it up pretty well by now. I took my fingers out and slid in the head of my cock into her anus, past the sphincter. Some resistance . . .

“It’s okay, sweetheart,” I whispered. She really was a sweetheart. And a great fuck. I’ve got to fuck more old women.

She relaxed and I pushed it in. Heaven. Much tighter than her cunt but oh, so delicious. Gladys started moaning and, bless her heart, started pushing against me, forcing my dick even further into her elderly rectum. I started fingering her clit and held on for the ride. Gladys was bucking against me and onto Philippe’s cock, sweat rolling down her arms, tits beating like twin bells as I rammed it to her.

“I hope you can still hear me, Carl,” I called out while pumping Gladys’ fat ass. The sight of her tits flying and her fat ass pushing against me were incredibly exciting. I was probably breathing pretty hard but I wanted to keep Carl informed. “I’m fucking your sweet Gladys in the ass right now and let me tell you, she is one sweet ass fucker, Carl. You really should try it. I don’t think she’s done this before, Carl. Oh, that’s right. You can’t.”

I was going to cum soon. God, she felt great.. “Oh, Jesus!” Philippe was calling out. He ran his fingers through Gladys’ hair and held her head onto his cock. She was moaning, sucking, pumping back on me. I watched the entire length of my cock disappear in her welcoming asshole.

“She’s mine now, Carl. I’m taking our Gladys’ cherry out the ass.” It was boiling up in me, panting, hard to talk. “I say ‘ours,’ Carl, because I haven’t had her yet but . . . hang on . . Carl.”

Philippe screamed first and shot a load into and over Gladys while she kept sucking, licking and moaning louder herself, white cum dripping from her double chin, her lips.

I was next, blasting hot jism into Gladys’ eager anus and her head rose like she had been impaled, screaming “oh, God, oh god, oh god” with cum dripping onto her tits and I kept pumping into her sloppy asshole for what seemed like hours until, finally, blessedly, we fell in a heap, Philippe on the bottom, Gladys, then me, a panting, sweaty, cum-smeared mass of flesh.

My dick popped out with a little squish noise and when I gently slapped Gladys’ ass, she giggled. Yes, indeed, she had come a long way from the shy old Grandma I met in the hotel lounge earlier in the evening.

I got up, put on the robe again and leaned over to whisper to Gladys. “Thank you, my sweet, sweet Gladys. I love you, baby.”

She kissed my cheek and mouthed the words “I love you too.”

I let Carl out of the closet. From the smell of it, it seemed like he entertained himself pretty well during our adventure. He was sitting down so I crouched to talk with him.

“Carl, my friend. Gladys is mine now. Whenever I want her – and that will be pretty much anytime I get into town – she belongs to me. You can house her and feed her and be nice to her, but basically, she’s my fuck toy now and I’m hers. So, see? You got what you wanted.”

Carl couldn’t look at me.

“You’re a sorry piece of humanity, Carl but I want you to remember one thing: take care of my sweet little Gladys. Or else. Now you go back to wherever you came and we’re going to get cleaned up and take Gladys back to you when we – and she – are good and ready.”

I looked back at Gladys and Philippe starting to move on the bed now. “I wonder if Philippe can get that big pecker of his up her ass. That’s something I’d like to see.”

Carl moaned, deflated, defeated.

“Goodbye, Carl. And remember: be nice. This time I’ll be watching.”

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