Stretching Out Jenny

It's interesting how much our first sexual experiences shape us for life. George had his first experience at barely 18, and there were still traces left in his mind twenty years later.

Despite growing up poor, George clawed his way into finance. At 38 years old he made it to the top 1%. Look at him: steering his private yacht around, trophy wife hanging on his arm. That trophy wife's name is Jenny. She has short pale blond hair, perky bubble tits, shapely legs, and a perfect hourglass figure. At 5'6", she looks tiny beside her 6'2" husband. Her best feature is her facial structure, revealing her healthy Scandinavian genes. Trophy wives like that are one of the unofficial "bonuses" when you're a high-ranking portfolio manager at Silverman Slacks.

George's body was perfect, thanks to his private personal trainer and his fully-equipped home gym. Just a couple more "bonuses" when you trade stocks at that level. He and Jenny had enjoyed a healthy loving sex-life all ten years of their marriage.

But there was something missing. It took a decade before George could put his finger on it. It all relates back to that first experience George had, all those years ago.

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At 18, George had lost his virginity to the school slut. He never meant to do it. It was all the girl's initiative. George was drunk at a house party and she pushed him into a bedroom. Before George knew it, the school slut was on top of him, riding him with that gaping loose pussy. As school slut, she was so stretched out, it was an oceanic experience. The girl was no angel, but her pussy was ethereal.

Just imagine it: losing your cherry to a girl so loose you can barely even feel her.

George remembered it fondly. Reaching up to grab the slut's titties while she was bouncing up and down on him. She would thrust down with all her strength, like she was trying to crush George's pelvis. And yet, her pussy was so cavernous, the walls of her cunt only barely brushed her beau's raging hard penis. It felt so good and at the same time so frustrating!!! Soon George flipped the slut over and got on top so he could pound her endless pussy more vigorously.

"Yeah baby!" the school slut said. "Harder! Harder! You're so big! Stretch me out even more, baby!"

George was instinctively jackhammering, yet he could STILL barely feel her, that's how loose the fucking whore was. It took George twenty minutes to reach a climax, even though it was his first time. When he finally did climax, it was so amazing. The girl was such a nasty tramp, she even let George cum inside her. It was love at first fuck. George ended up dating that slut for three weeks. That's the longest she was ever exclusive with one guy. Of course it couldn't last: she was the school slut! But they were the happiest three weeks of George's life, endless hours exploring that bottomless pussy.

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George's trophy wife Jenny was the exact polar opposite of the school slut. Tight, tight, tiiiight!

Whenever George made love to Jenny, he would cum in two minutes. Her pussy was like a vice around his big white dick, squeezing it like a cobra. George would have to resort to pharmaceuticals in order to endure even ten minutes.

It's obvious now in retrospect, but it took forever for George to figure out what was missing. Finally at age 38 he realized what was lacking in his love life. He was missing that loose, gaping pussy he'd lost his virginity to!

The revelation came on the night of their tenth wedding anniversary. For the special occasion, George was determined to stay hard for fifteen whole minutes. He took a TRIPLE dose of pharmas. But still it was no good. His wife's pussy was so damn tight, George had his third orgasm at fourteen minutes. Pharma or no pharma, he couldn't go past three orgasms.

"Shhh, it's okay," said Jenny, stroking George's hair, comforting him. "It's okay honey. It's okay."

That's when George realized what the problem was. He didn't want that tight trophy wife pussy, he wanted that football-field school-slut pussy he had lost his V-card to.

Jenny was perfect in every single way except her over-tight pussy. She had perfect hair, perfect tits, a perfect ass, a perfect body in every way. Why did she have to be so damn tight!

Suddenly, George knew why his wife was so tight. It's because she had only ever slept with him! A dedicated gold-digger, Jenny diligently saved herself until she met the right man. That is, the man with the right credit card. She got all her previous boyfriends off with handjobs and blowjobs, and she gave George her hymen on the night of their wedding. She was so insanely tight that night, George could barely put the tip in.

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For a while, George was depressed. He contemplated visiting a prostitute, if he could find one with a real loose gash. But that would be cheating. No, George was stuck. Cruel fate, cruel destiny! His beloved school slut all those years ago had given George a hopeless loose pussy fetish. And now he was chained for life to the tightest ever trophy wife!

Fortified with liquid courage, he opened up to Jenny.

"Baby, I love you so much," he said, holding his wife against him on the sofa. The stereo was turned low, playing soul music.

"I love you too, George."

Jenny gave George's chest a little kiss.

"There's just one thing," said George. "I just wish your pussy was looser."

Jenny was understanding as George explained about the school slut. How that harlot took away his virginity. How she left him addicted to stretched-out pussy.

"Shhh, it's okay," said the trophy wife. She was stroking George's bicep. "I'm so glad you opened up and told me, darling. Don't worry. I won't judge you."

As a matter of fact, Jenny was relieved. She knew that with every rich sugar daddy, there's always some weird fetish after a long enough time together. She was glad her husband wasn't into something awkward, like ropes, or latex, or anything of that sort.

A loose pussy fetish isn't all that weird, in the big picture.

Jenny knew George was self-conscious about his fetish, and she was proud of him for opening up with her about it. She kissed her way down George's body, opening his robe to get at his sexy abs.

"I love you just the way you are," said Jenny. "You can admit absolutely anything to me."

She made her way down to George's lap, a trail of kisses leading to his big white dick. Then she started sucking him off, carefully keeping her mouth as wide open as possible, to make it a looser blowjob. She bobbed her pretty face up and down, jaws stretched so wide, George's dick would just barely brush against her inner cheek. She could tell that it was working! George's dick swelled up harder than she had ever felt it.

"Oh!" said Jenny, pulling away from the blowjob. "It looks like you like my loose blowjob, honey."

George was so excited from the loose blowjob, he just couldn't help himself. He pushed Jenny down on the sofa and mounted her pretty little body.

"Oh!" said Jenny. The trophy wife started mewling.

"Ugghhh!!!" said George. He was already cumming.

"Wow," said Jenny. "That loose blowjob must've got you excited. You came in like, two thrusts!"

Jenny was a perfect wife, and she never complained, no matter how quick her husband came. But after the excitement from the loose blowjob, George was more frustrated than ever.

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Jenny was at home all day while George was at Silverman trading clients' assets. She had plenty of time to think of ways to please her husband.

The first thing to try was lubricant. Jenny hummed as she clicked the shopping cart button. Soon, a dozen high-power sexual lubes would arrive from the nearest Amazon warehouse. Next, she looked up exercises housewives can perform to loosen their pussies. She was reading a forum on the subject, when she was interrupted by the doorbell.

James was George and Jenny's handyman. He came over almost every week to tune something up around the house. He was tall, he was black, and he was very very handy.

"Hi James," Jenny beamed at the contractor. "Thanks for coming. The washing machine is acting up."

Besides being handy, James was also flirty. Every time he came over, he would smooth-talk the housewife, tell her how pretty she was. He would also take every opportunity to touch her or cop a feel. James made absolutely no secret of the fact that he wanted to 'get to know Jenny better'. Jenny knew that James was on intimate terms with quite a few bored housewives in the neighborhood. That's just par for the course in a quiet suburb like Cherry Hills. Unlike those other housewives, Jenny was happy with her husband. She never took James's overtures seriously, even for an instant.

"None of that now!" said Jenny, slapping James's hand off her perfect ass. She was accompanying him to the laundry room.

"You know you want it, mama," said the handyman, unphased.

Jenny went back to the computer, a little annoyed by the contractor's forwardness.

But she also started thinking. What if she DID let some other guys 'get to know her better'? George DID want a looser-pussy wife, after all.

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The lube arrived and Jenny arranged a night of romance with George.

"How do I look?" she said, floating into the bedroom in lingerie.

"Damn, baby, you look perfect," said George.

Jenny floated to George and joined him on the bed. Ten years of marriage, and they still couldn't keep their hands off each other! Light petting turned into a hard makeout session. Jenny dived under the covers and started kissing George's shaft. George moaned when Jenny started giving him her loose-mouth blowjob.

Soon George was so excited his big white dick was straining.

"Honey, I have a treat for you," said Jenny, emerging from the covers.

She reached under the pillow and pulled out a special lube. 'Extra slippery,' the label said. It was a high grade lube, you were only supposed to use a drop. Jenny slathered George's whole dick with it. She climbed on top of her husband and lowered herself onto him.

"How does that feel honey?" said Jenny.

"Fuck," said George. "Baby, that feels so nice."

Jenny smiled and started sliding her pussy back and forward. George's dick felt so slippery inside her.

With the lubricant, George was able to last five whole minutes before losing it.

"Yeah? You like that, honey?" said Jenny, as she felt her husband's dick swelling up inside her. "Does your little wife's pussy feel nice and wet and slippery??"

George grunted and started thrusting faster, about to cum.

Suddenly, for just an instant, the image of their handyman James flashed in Jenny's mind. For less than a second, Jenny visualized the cute, fit, young, black handyman. Jenny had never slept with anyone but her husband, that's why her pussy was so tiiiight. A nice black handyman like James would do wonders to loosen her up a little.

As soon as the image appeared, it was gone, and George was cumming inside her. "Oh! Oh!" Jenny faked a little orgasm.

"I'm sorry I didn't last longer," said George. They were cuddling in the afterglow.

"It's okay, dear. It's not your fault your wife's pussy is so tight."

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Jenny started thinking more and more about sleeping around behind her husband's back. She didn't want to cheat on George, but she knew she couldn't satisfy him with her pussy as tight as it was.

It didn't help when James would come over to fix something and flirt or touch her while he was at it.

"Stop!" she said, slapping James's hand away when he grabbed her tit through her shirt one time. The young black contractor was visiting to replace the AC filters.

Despite slapping James's hand away, Jenny was excited by the attention. She couldn't help thinking how nicely James would stretch her pussy out and how much George would love that.

All these thoughts made Jenny feel guilty and ashamed of herself.

Gradually, these feelings of guilt and shame turned into feelings of anger against that filthy school slut. That no good whore took George's virginity all those years ago. It was HER fault Jenny's husband had a loose pussy fetish! Jenny burned up with resentment.

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"What's the matter, honey?" said George. Jenny was moping around, which was unusual.

"Nothing," said Jenny.

"Oh come on, I can tell there's something bothering you."

"No, really, it's nothing."

George did what he always did in this situation. He broke out a wine bottle.

Soon, the couple were cuddling on the couch. Jenny was tipsy.

"Now tell me what's bothering you," said George, gently rubbing Jenny's inner thigh.

"You wish I was like that school slut, don't you?" said Jenny. "The one with the loose pussy."

"Oh, baby, don't say that," said George. He gave Jenny a squeeze. "I love you just the way you are, Jenny."

"Do you wish I was a little bit sluttier in my past?"

"No!" said George.

"Even if it meant my pussy was looser?"

"Well..."

"Would you be happier if I let a bunch of guys stretch me out before I met you?" Jenny gave George a kiss on the neck, and then started nibbling his earlobe.

"I mean..."

"Would you love me more if my pussy was all worn out from a bunch of well-hung studs doing nasty things to me?"

"Honey..."

Jenny reached down and felt George's dick. It was hard like steel.

"What's this?" She pulled away so she could examine George's bulge.

"..." George felt ashamed of his hard-on.

"Do you get excited hearing me talk like that?"

Jenny started stroking George's bulge through his pajamas, letting him know she wasn't mad at him or angry.

"Do you get excited," she said, "thinking about your little wife getting all used up and stretched out by other guys before she met you?"

George's dick involuntarily twitched. Jenny gasped.

"You DO like it!" She gave her husband a curious look.

George shrugged helplessly.

Jenny got this naughty smile on her face. "So, my pervert husband gets excited when his little wife talks about her slutty past..." Never mind that Jenny had never slept with another man but George. Gears were turning in that pretty head of hers.

"Baby," George protested. But he couldn't control how hard his dick was. His penis was betraying him.

Jenny tugged George's pajama pants and boxers down. Her husband was at full mast.

"Darling, what if I was lying about being a virgin when we met," she said, sliding onto George's lap.

"Stop," said George, but didn't make a move to stop her.

Jenny started rubbing her pussy-lips up and down her husband's rock-hard white penis. "Would you be mad if I confessed something?" she said. "Before I met you I was actually with a lot of guys."

George gasped and grabbed Jenny in an embrace, pulling her close against him. The side of his dick pushed hard against the lips of Jenny's super tight little pussy.

"Before I met you, honey, I was a nasty slut," Jenny said in a lewd voice. "I let guys do whatever they wanted."

George was so excited now he started thrusting his hips involuntarily, even though he wasn't inside Jenny yet.

"Honey, I took lots of big huge cocks in my naughty pussy..." Jenny was delighted at the effect her words were having. George looked like he was about to explode. Jenny leaned forward and gave her husband a french-kiss.

After the kiss, she pulled back. A strand of saliva still connected their lips. They were breathing hard.

"So many big huge cocks in my horny pussy..." Jenny said. "That's why my naughty cunt is so stretched out and so loose and so worn out..."

George lost it. He came harder than Jenny ever saw him cum before, even without any penetration. Jenny gasped as the cum shot as high as her chest, splattering her perfect tits.

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After that day, Jenny incorprated more and more roleplay into the bedroom. She would make up stories about slutty things in her past. George would get so excited he'd go absolutely crazy.

For example, Jenny would tell George about the time she slept with the whole college football team. "Most of them fucked me twice that day..." she said, matter-of-factly. She was on top, sliding her pussy back and forth on George's hard shaft, without inserting it. "One of them fucked me three times... honey are you mad those big mean football players ruined my pussy?? They left me permanently stretched out..."

George grunted and came all over everywhere.

Or another time: Jenny joined her husband in the shower.

She hugged George from behind and spoke in his ear. "Did I tell you about this time before I met you, in a shower just like this one? I was with this guy with the biggest cock, it was like, a baseball bat... he forced that thing inside me and I started cumming so hard on it... I could feel him thoroughly ruining my pussy, but it felt so good I couldn't stop him..."

Jenny grabbed George's dick and started rubbing beneath the showerhead.

"...Honey are you upset your wife was such a filthy tramp before you met her? Are you upset that big huge cock stretched your little wife's pussy out in the shower?"

George lost it and came in his wife's pretty little hand.

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The next time James, their black handyman, came over, Jenny was a better hostess. She didn't slap his hand away as fast whenever James touched her. She actually let him play with her breast a few seconds before faithfully resisting.

Jenny started calling James more often, inventing things for the contractor to work on. And she dressed more provocatively whenever he came over.

"Damn baby you're sexy," said James one time, on a visit supposedly to adjust picture frames.

He grabbed Jenny's ass with his big black hand. She was wearing denim short-shorts like she was begging to be fondled. The housewife wiggled her ass a little before pulling away and denying James.

At the door that day, Jenny let James give her a peck on the lips.

"Stop!" she said. But she clearly wasn't too upset.

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Jenny felt ashamed at how much she was letting James get away with. But she couldn't help it. All that pillow talk had awakened her inner slutwife. The sheer wrongness of what James did to her, only made it feel better. And the wrongest part of all was, James was black.

Jenny started slipping interracial elements into roleplay with George, at first subtly. She was testing the waters.

"Oh honey I was such a whore before I met you..."

She was on her back, and her husband was eating her tight little pussy.

"This one time I slept with two guys at the same time... they took turns on me... one of them was black... they stretched me out so much..."

George didn't seem upset by the new interracial twist. Jenny ratcheted it up.

They were in bed one night cuddling. Jenny started rubbing George's dick.

"Honey did I ever tell you about the biggest guy I was with, before I met you?" she said. "He was this big, tall bouncer at a stripclub. He was so fucking scary looking. He was BLACK, and he always had this furious look on his face. Honey, I went on a date with him and, I'm such a fucking nasty little slut... I let him FUCK me on that very first date."

George's dick swelled up like diamonds.

"Do you think it's true what they say, that first-date sex stretches a girl out more than any other kind of sex? Honey, his big BLACK cock was sooo huge. I thought he was gonna split me in half!"

George started humping his wife's hand.

"I didn't think I could even take that thing, it was so monstrous. When he pushed it inside me it tore my pussy to pieces. Honey, that thing was so massive, I could see the bulge of it in my tummy! I knew my poor cunt would never be the same again. I thought: My pussy's ruined for my future white husband!"