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Preppy - Blog Posts

3 months ago

IM GONNA RUN MYSELF OVER WITH A CEMENT MIXER TRUCK


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7 years ago
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone
My Wife’s Fantasy Becomes Reality This Weekend.  Though She Has Been With Many College Guys, And Gone

My wife’s fantasy becomes reality this weekend.  Though she has been with many college guys, and gone on overnights, she is now at 54 going for her first full sleepover weekend, and it’s this weekend... Halloween weekend!

She had a hot intern this past summer, and during his last week, she tried dropping signals to him, and took him out to lunch and gave him her personal cell number, saying to call or text any time.  We invited him over after his last day but he couldn’t make it.  Now they’ve been sexting like crazy; she wants his young college cock and he wants to undress his hot businesswoman boss.  So this weekend, she’s heading up to Pitt to bed a senior.

Friday, she’ll head into work in her dark pants suit with white Brooks Brothers french cuff blouse, and her new PItt cufflinks.  She’ll duck out early for the four hour drive up.  Saturday, she has football tickets, but nobody’s going to be surprised if they don’t leave his apartment.  She’s going to wear the Pitt tie and the cardigan with another white blouse, khakis and boots.  Last night, she had me go buy the big box of Magnum condoms and put them in the cardigan pockets.  He’ll wear the mostly yellow tie.  Sunday, she’s got a brunch reservation, which they probably won’t make.  They’ll definitely be hungry, but they’ll also probably sleep through it after coupling late into the night.  When she does finally get up, though, she’ll wear her preppy “P” sweater from Hillflint with the bottom left tie, over a yellow shirt, jeans, and boots.  There should be afternoon sex followed by a pretty late departure, with lots of coffee on the four hour drive back home.


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4 months ago

Matt's transformation into servitude and obedience

Matt's Transformation Into Servitude And Obedience

Matt was just like every other lad his age, just finished uni and trying to find their way in the world. However, Matt was different, he believed he was bound to be stuck in his council estate all his life with zero purpose. He would roam the streets at night with his mates getting in people's faces and stealing from corner shops. That was until Matt met someone, someone that would change his life forever...

Matt's Transformation Into Servitude And Obedience

James has been a hard working business man for many years and travels around looking for new recruits for his company and tonight he has stumbled across Matt's council estate. James loved places like this, they always had the best men for him to take, or recruit as he liked to call it.

Matt spotted him at the local corner shop and walked up to him trying to intimidate him.

"Oi mate! What you doin around this part of town?!"

"Just doing a little research young man" Replied James as he eyed Matt up and down.

"Well go and do your research somewhere else or something bad might happen to you!" Matt yelled as he clenched his fisted hidden under his massive hoodie.

"I think I'm done here now anyways, I've got all that I need for now" James gave Matt his number and told him to call whenever he needed a little money, which for Matt was all the time.

Matt's Transformation Into Servitude And Obedience

Matt was scrolling mindlessly through his phone one day and was thinking about James. James had been on Matt's mind for the last couple weeks ever since they briefly met. But today, Matt decided to give in and call the number he was given...

"Hello?? Is anyone there?"

"Aha, I knew you'd call Matt, are you ready to join us, to join me and become a better you?"

"I thought you were just recruiting for a job or something mate?"

"Precisely Matt, good boy on remembering who I was, but it was probably pretty hard for you to forget wasn't it? Just come over to this location and we'll get you all sorted and ready for you new job"

Matt heard the phone line die before he could say anything else. He was scared but he knew what he had to do. He packed a bag with all the shit from his room he could find and set out to the address James had given him. He didn't know why but he could feel his life was about to change.

Matt arrived at the location James had given him. It was a sleek, modern building tucked away in an industrial part of town, far removed from the gritty council estate he called home. His heart raced, palms sweaty. As he walked through the large glass doors, he was greeted by an imposing figure who led him down a long corridor. It felt like entering a different world, one that Matt couldn’t even begin to understand.

Finally, they reached a large office where James was waiting behind a polished desk, his sharp suit and confident smile as poised as ever.

"You're here," James said, rising from his seat. "I knew you would be. Have a seat, Matt."

Matt hesitated, still unsure of what exactly he was stepping into. He sat down across from James, trying to hide his nervousness behind a cocky smirk.

"What's all this about, mate? You said something about a job, but this doesn’t feel like a job interview." Matt leaned back in his chair, arms crossed.

James chuckled, a smooth, almost predatory sound. "No, it’s not exactly what you’re used to. But it’s a job that will change everything for you. If you want it, that is."

Matt's eyes flickered with curiosity, but a small voice in the back of his mind whispered doubts. "Change everything? How exactly?"

James took a step forward, his demeanor shifting, more commanding now. "You’re a man of potential, Matt. But all that potential is wasted where you are—wasting away in that estate, living paycheck to paycheck, being nothing more than a product of your environment. But I can give you more than that. I can offer you something... greater."

Matt swallowed hard, his heart pounding in his chest. He wasn’t sure whether he was excited or terrified, but the thought of something more, something beyond his limited world, was too tempting to resist.

"I don’t get it," Matt muttered. "You just show up, give me your number, and now you’re telling me you can change my life?"

Matt stood up and tried to leave but he couldn't, there were a group of men, all dressed in fancy suits that were blocking all the entrances.

Matt's Transformation Into Servitude And Obedience

He was strapped into his chair and forced to stare at a spiral for hours on end. Matt could feel himself getting sleepier and sleepier but all he could think about was James. He couldn't remember where he even came from, what his past week looked like. All he could think about was James, and how he came here for a reason. To serve James and the company. When James came back into the room, he just looked at Matt and smiled. He knew it was complete so he took Matt down into the basement, into his special lair and gave him a change of clothes. James' employees have to be dressed properly of course, they must dress their part as they serve him.

Everything was now complete, Matt came out, dressed in his new uniform, and sat at James' knees as he knew that was where he belonged. He wasn't some council estate tough guy anymore, he was James' obedient servant day in and day out. He loved it so much he began to go out with James when he would recruit other men to his company. After all, it was the best feeling Matt had every felt in his life...

Matt's Transformation Into Servitude And Obedience

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1 year ago

Me fr

Me Fr

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2 years ago
Pretending To Be Preppy In The City Of Alts
Pretending To Be Preppy In The City Of Alts
Pretending To Be Preppy In The City Of Alts

pretending to be preppy in the city of alts


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3 months ago
Hope He Dies In That War (even Though It's Not Real)

Hope he dies in that war (even though it's not real)

@xkeehlx


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1 year ago

peek into my life 2

rehearsal is only in the afternoon today, meaning this morning i got to help my friend paint signs for the show! she is so good, literally an art master. i am hopeless but i helped paint the backs!! also got subway for lunch i love subway. we paint at a middle school because my company runs a theater program during the summer there, and their scene shop is so big :D the one at our home theater is TINY and you have to squeeze past the set pieces to get to the dressing rooms ugh. also the kids doing the program are so cute. i looked like a rat during middle school but they're very preppy now. lululemon, aviator nation, etc. i think its cute tho haha


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4 months ago

I FORGOR I DREW THAT 😭😭

@insane-dinosaur Made Som DISGUSTING Art Of Mee And Sahsa Nien. I Hate Sasha. I Am Hapily Married. I

@insane-dinosaur made som DISGUSTING art of mee and sahsa nien. I hate Sasha. I am hapily married. I dispise sassha. Adn now, for tihs, I dispite YOU. #cancelinsanedinosaur


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7 months ago

…don’t think I’m gonna forget about our affair, Scrimbus.

do you guiys liek sefora

Do You Guiys Liek Sefora

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1 year ago

I spent like 10 minutes on making it preppy

I Spent Like 10 Minutes On Making It Preppy
I Spent Like 10 Minutes On Making It Preppy

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1 year ago
Stop Why Does This Make Me Laugh- (credit To Og Creator)

stop why does this make me laugh- (credit to og creator)


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3 years ago

people are like ”you wouldnt survive in the past“ but i would. im irish-american and would leave a strange mark if a bit you. im the perfect candidate for a kennedy’s wife


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3 months ago
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,
Preppy Men Style In Versailles, Wearing Navyblue Sebago Classic Loafers, Long Burlington Argyle Socks,

preppy men style in Versailles, wearing navyblue Sebago classic loafers, long Burlington argyle socks, navyblue corduroy knickers (knickerbockers), Ralph Lauren blazer


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3 months ago
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,
Preppy Style, Winter In Versailles, Wearing Sebago Docksides Boat-shoes, Preppy Hackett Navy-blue Socks,

preppy style, winter in Versailles, wearing Sebago Docksides boat-shoes, preppy Hackett navy-blue socks, brown suede leather jacket, Vuarnet sunglasses


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4 months ago
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style
JM Weston Vintage Tassel Loafers, Bleu-Forêt Silk Dress Socks, Vicomte-A Wool Jacket, Preppy Style

JM Weston vintage tassel loafers, Bleu-Forêt silk dress socks, Vicomte-A wool jacket, preppy style


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4 months ago
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style
Versailles Walk In My Bass Burgundy Penny Loafers, Armani Dress Black Pattern Socks, Preppy Style

Versailles walk in my Bass burgundy penny loafers, Armani dress black pattern socks, preppy style


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4 months ago
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.
Journey To Paris, Wearing JM Weston Suede Loafers, Beige Sheer Nylon Socks, Preppy Casual Style.

Journey to Paris, wearing JM Weston suede loafers, beige sheer nylon socks, preppy casual style.


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4 months ago
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,
Hot Summer Days In Versailles, Wearing My Suede Preppy Rockport Loafers, Paul Smith Jeans, Striped Shirt,

Hot summer days in Versailles, wearing my suede preppy Rockport loafers, Paul Smith jeans, striped shirt, blue sheer tnt nylon socks


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1 year ago

Me, writing a very serious story about Batman's family.

Also me, adding a whole paragraph with Hal Jordan discovering that Batman's daughter (Female!Dick, and the only child of his the league knows about because he too was young and naive, once) is a cheerleader, cheer captain even, in which he talks about Bring It On and Mean girls and teenager dictators, while Batman broods (supposedly) because his daughter had the *audacity* to be preppy and "no daughter of mine will be preppy in this goth household, go change back from that cheer uniform, here is your everything-black and your white foundation sweetie."

archiveofourown.org
An Archive of Our Own, a project of the Organization for Transformative Works

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