Dear Abner - Ho for the Holidays
Posted: Mon Jan 01, 2024 2:14 pm
Dear Abner,
My family made it's money in real estate, but after I graduated from Wharton I used my families connections to start a hedge fund that has put me in the top .01%, even though I'm not even 30 yet. I have a fabulous condo overlooking Central Park, but I always come home to the family estate for the holidays.
When I came home for Thanksgiving, my stepmother Blake contacted me about an idea for a "really unique" Christmas present for my dad. One of the houses on the estate that the family frequently uses for our more debauched parties is, appropriately enough, actually designed to look like a Roman Villa. There is usually a statue of "The Greek Slave" in the alcove near the rear, but when my stepmother took me there I was surprised to see the "visual distraction" of the statue had been removed and a black marble pedestal had been placed on the landing.
Blake explained that her idea was to have me, my sister Brittany, and her pose for an oil painting of a Roman slave auction, with my idiot, ne'er do well younger brother Eric acting as the auctioneer. I should explain that my dad definitely has a "type", so Blake, Brittany, and I all look like sisters, especially since my stepmom is actually a year younger than me. As my dad is always cycling through slave girls during parties at the villa, and saying how he would fuck Brittany and I if we weren't his daughters, I knew that he would love the painting, and the chance to show off "his hot women" as he often referred to us.
"What will we be wearing in the painting?" I asked, sensing where this might be going.
"We'd be naked, of course," she said, smiling devilishly. "Except for our slave collars. Only a fool buys a slave slut with clothes on."
I actually blushed so red that my stepmother commented on it, and Helga, the fat maid who always seems to be around to listen in, remarked that my face looked like "a fat tomato." I objected, as I'm the head of a hedge fund, and the thought of posing naked, particularly in front of my step mom and lecherous brother, was quite humiliating. "I'll be naked too," she reminded me. "Plus we'll finally get to see which of us is the hottest."
I have to admit that idea intrigued me, for even though I compete on brains and not on beauty, my dad often comments on which one of us looks "the ripest" on any particular day. He usually chooses Brittany or my mom, because 'your glasses and business suits make you look like a guy." I know he's joking, but I'm very competitive, and I hate it when he says it. I was curious what his assessment might be if we were on equal, albeit bare, footing.
The truth be told, I also found it incredibly hot. Running a hedge fund, I have a million things to worry about and I'm very much in charge. I've often fantasized about what it would be like to be one of my dad's slave girls, naked and submissive and subject to the whip. I hope you don't think I'm weird, Abner, but I think a lot of girls feel that way, even if they won't admit it.
Bottom line is when my Dad flew to Atlanta we brought in the artist and he immediately started taking pictures and making sketches, some of which were quite explicit. Again, my face went tomato red. It got worse when we started posing together, and Blake, Brittany, and Eric (in a roman toga, cracking a long whip) saw me naked. Eric hates my guts, since he's older but I'm clearly the heir to dad's empire. Delighted to have the upper hand at last, he made no attempt to disguise where his eyes were focusing, and suggested several very lewd poses to the painter for me, so the audience could "see" the merchandise.
The artist, Pablo, worked hard and fast, and was always sketching and painting and taking pictures. Geez, he must have seen every inch of me. He encouraged Eric (who had been practicing with the whip) to crack the whip over my head, and "near her ass", because he liked the way it may my butt cheeks clench and unclench. At one point Eric, bastard that he is, suggested "her slave girl ass would look even hotter with a couple of stripes on it". Pablo and stepmom and Brittany (who by this time was very jealous of the attention I was receiving from Pablo, who was clearly arranging me as the centerpiece) quickly agreed. As a result I ended up with the whip cracking across my ass, and even between my cheeks, skinning my butthole. The pain was agonizing, and I howled, but (totally ensconced in my role) didn't break position. Pablo, fascinated, told Eric to do it again...
Brittany and Blake got very competitive, and soon they were juicing up to match me, which only made Eric hornier and the humiliation of it all the hotter. My Wharton degree melted away as I became tits and pussy, up for sale on the block.
The weird part is the more humiliating the poses and the more degrading Eric's treatment got, the wetter I got. The humiliation was a major turn on, and it amped up to an 11 when Helga decided to usher the staff into where we were posing in the guise of preparing for our annual New Year's even party. So every maid, butler, chauffeur, stableboy, groundskeeper, pasty chef, and handyman on staff got to watch bug eyed as I strutted my stuff buck naked on the block, with Eric cracking the whip while his boner tented the front of his toga. Some of the slave girls were brought in, ostensibly to clean, but as they were given togas and were naked they catcalled us, and teased us about what hot slave girls we were, and how "hot the whip marks look on your naughty slave girl bottom." Helga even had the pool guy and UPS guy come in for some fucking reason. Pablo didn't object, since "the more people watch them, the more they drip."
On Christmas Day the painting was finally revealed. The painting was hyper realistic, and you could see every hair and even the folds around Eric's tentpole toga. My stepmother Blake stood on the left stairs, her legs spread, licking her lips as she teased her nipples for the buyers, a pose that perfectly captured her personality. My sister Brittany was on the opposite stairs, squatting, leaning against the wall, legs spread as she played with herself, her spread, wet pussy and butthole on display as she worked herself to orgasm.
I was stage center, on all fours, leg spread, with a look of shock on my face as Eric cracked the little tails of the whip cracker against my asshole. My pussy was hot, spread, and literally gaping open. It was the most humiliating, degrading pose I could imagine, and my dad loved it, telling everyone that I was once again his favorite. He even gave me a new nickname, "Winky", suggested by Helga as she related the way my asshole 'winked' at the sound of every whip crack.
The staff loves my new nickname, and is always making sly references to my portrait, like leaving an extra cushion on my chair or hemorrhoid cream on top of a book I was reading or next to my dinner plate. They'll call me Winky, or say they didn't recognize me with my clothes on, or ask if I want to "spread out more", of if I'd like to swim in the nude (even with the pool boys gawking at me). I blush like crazy, but don't object, because it makes me wetter than the pool I'm swimming in.
My Dad LOVES his painting, and wants to display it in the alcove at the New Years Eve party. The idea gives me butterflies, as I know all of my families debauched friends are going to see me slave naked. It's unbelievably humiliating, as I think of all my dad's lecherous friends and all the bitchy girls I grew up with looking at me whipped and spread. It's incredibly hot and humiliating, if that makes sense? What really makes me nervous is Eric said he is going to wear his toga, and Helga has left the slave whip and the three collars on the black marble stage "for decoration", as she put it. I've objected to having the painting on display, but I've been ignored, and I am unsure of what to do. My real fear is that word will spread beyond the house, and I won't be able to run my hedge fund anymore if everyone in New York starts treating me like everyone at home is. How do I stop this train?
Winky
My family made it's money in real estate, but after I graduated from Wharton I used my families connections to start a hedge fund that has put me in the top .01%, even though I'm not even 30 yet. I have a fabulous condo overlooking Central Park, but I always come home to the family estate for the holidays.
When I came home for Thanksgiving, my stepmother Blake contacted me about an idea for a "really unique" Christmas present for my dad. One of the houses on the estate that the family frequently uses for our more debauched parties is, appropriately enough, actually designed to look like a Roman Villa. There is usually a statue of "The Greek Slave" in the alcove near the rear, but when my stepmother took me there I was surprised to see the "visual distraction" of the statue had been removed and a black marble pedestal had been placed on the landing.
Blake explained that her idea was to have me, my sister Brittany, and her pose for an oil painting of a Roman slave auction, with my idiot, ne'er do well younger brother Eric acting as the auctioneer. I should explain that my dad definitely has a "type", so Blake, Brittany, and I all look like sisters, especially since my stepmom is actually a year younger than me. As my dad is always cycling through slave girls during parties at the villa, and saying how he would fuck Brittany and I if we weren't his daughters, I knew that he would love the painting, and the chance to show off "his hot women" as he often referred to us.
"What will we be wearing in the painting?" I asked, sensing where this might be going.
"We'd be naked, of course," she said, smiling devilishly. "Except for our slave collars. Only a fool buys a slave slut with clothes on."
I actually blushed so red that my stepmother commented on it, and Helga, the fat maid who always seems to be around to listen in, remarked that my face looked like "a fat tomato." I objected, as I'm the head of a hedge fund, and the thought of posing naked, particularly in front of my step mom and lecherous brother, was quite humiliating. "I'll be naked too," she reminded me. "Plus we'll finally get to see which of us is the hottest."
I have to admit that idea intrigued me, for even though I compete on brains and not on beauty, my dad often comments on which one of us looks "the ripest" on any particular day. He usually chooses Brittany or my mom, because 'your glasses and business suits make you look like a guy." I know he's joking, but I'm very competitive, and I hate it when he says it. I was curious what his assessment might be if we were on equal, albeit bare, footing.
The truth be told, I also found it incredibly hot. Running a hedge fund, I have a million things to worry about and I'm very much in charge. I've often fantasized about what it would be like to be one of my dad's slave girls, naked and submissive and subject to the whip. I hope you don't think I'm weird, Abner, but I think a lot of girls feel that way, even if they won't admit it.
Bottom line is when my Dad flew to Atlanta we brought in the artist and he immediately started taking pictures and making sketches, some of which were quite explicit. Again, my face went tomato red. It got worse when we started posing together, and Blake, Brittany, and Eric (in a roman toga, cracking a long whip) saw me naked. Eric hates my guts, since he's older but I'm clearly the heir to dad's empire. Delighted to have the upper hand at last, he made no attempt to disguise where his eyes were focusing, and suggested several very lewd poses to the painter for me, so the audience could "see" the merchandise.
The artist, Pablo, worked hard and fast, and was always sketching and painting and taking pictures. Geez, he must have seen every inch of me. He encouraged Eric (who had been practicing with the whip) to crack the whip over my head, and "near her ass", because he liked the way it may my butt cheeks clench and unclench. At one point Eric, bastard that he is, suggested "her slave girl ass would look even hotter with a couple of stripes on it". Pablo and stepmom and Brittany (who by this time was very jealous of the attention I was receiving from Pablo, who was clearly arranging me as the centerpiece) quickly agreed. As a result I ended up with the whip cracking across my ass, and even between my cheeks, skinning my butthole. The pain was agonizing, and I howled, but (totally ensconced in my role) didn't break position. Pablo, fascinated, told Eric to do it again...
Brittany and Blake got very competitive, and soon they were juicing up to match me, which only made Eric hornier and the humiliation of it all the hotter. My Wharton degree melted away as I became tits and pussy, up for sale on the block.
The weird part is the more humiliating the poses and the more degrading Eric's treatment got, the wetter I got. The humiliation was a major turn on, and it amped up to an 11 when Helga decided to usher the staff into where we were posing in the guise of preparing for our annual New Year's even party. So every maid, butler, chauffeur, stableboy, groundskeeper, pasty chef, and handyman on staff got to watch bug eyed as I strutted my stuff buck naked on the block, with Eric cracking the whip while his boner tented the front of his toga. Some of the slave girls were brought in, ostensibly to clean, but as they were given togas and were naked they catcalled us, and teased us about what hot slave girls we were, and how "hot the whip marks look on your naughty slave girl bottom." Helga even had the pool guy and UPS guy come in for some fucking reason. Pablo didn't object, since "the more people watch them, the more they drip."
On Christmas Day the painting was finally revealed. The painting was hyper realistic, and you could see every hair and even the folds around Eric's tentpole toga. My stepmother Blake stood on the left stairs, her legs spread, licking her lips as she teased her nipples for the buyers, a pose that perfectly captured her personality. My sister Brittany was on the opposite stairs, squatting, leaning against the wall, legs spread as she played with herself, her spread, wet pussy and butthole on display as she worked herself to orgasm.
I was stage center, on all fours, leg spread, with a look of shock on my face as Eric cracked the little tails of the whip cracker against my asshole. My pussy was hot, spread, and literally gaping open. It was the most humiliating, degrading pose I could imagine, and my dad loved it, telling everyone that I was once again his favorite. He even gave me a new nickname, "Winky", suggested by Helga as she related the way my asshole 'winked' at the sound of every whip crack.
The staff loves my new nickname, and is always making sly references to my portrait, like leaving an extra cushion on my chair or hemorrhoid cream on top of a book I was reading or next to my dinner plate. They'll call me Winky, or say they didn't recognize me with my clothes on, or ask if I want to "spread out more", of if I'd like to swim in the nude (even with the pool boys gawking at me). I blush like crazy, but don't object, because it makes me wetter than the pool I'm swimming in.
My Dad LOVES his painting, and wants to display it in the alcove at the New Years Eve party. The idea gives me butterflies, as I know all of my families debauched friends are going to see me slave naked. It's unbelievably humiliating, as I think of all my dad's lecherous friends and all the bitchy girls I grew up with looking at me whipped and spread. It's incredibly hot and humiliating, if that makes sense? What really makes me nervous is Eric said he is going to wear his toga, and Helga has left the slave whip and the three collars on the black marble stage "for decoration", as she put it. I've objected to having the painting on display, but I've been ignored, and I am unsure of what to do. My real fear is that word will spread beyond the house, and I won't be able to run my hedge fund anymore if everyone in New York starts treating me like everyone at home is. How do I stop this train?
Winky