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I'd been reposting images on tumblr for a little while. I used it mainly to keep track of dresses, art, captions, etc., that I liked/had found elsewhere on tumblr. What I didn't know was that my mom had found out about it. The first thing I knew was after I repost an image of a dress that had text "reblog if you'd wear this" over it. Image my shock when a couple of days later I get out of the shower to find the same dress on a hanger hooked over the wardrobe door in my bedroom. My mom walks in soon after me. "Well what do you think?" I'm stunned and have no idea how to answer. 'Surely she doesn't know,' I think to myself. "Who's that for?" I ask. "You," she confidently tells me in a tone that's clear she knows, "it's time you put your money where your mouth is." "What?!" I quick respond but as I'm about to continue she holds up her phone with my post on the screen. It's true, I did want to wear the dress but I definitely didn't want anyone to know nor did I want to wear it in front of anyone. The thought of being seen in a dress was mortifying on its own but this dress was very girly. It was a light yellow smocked dress covered with little teddy bears, a high waist, puffed short sleeves with ruffled cuffs, peter-pan collar and a skirt that would barely reach the top of my thighs. "You're wearing it," my mom tells me in a very stern voice, one that would make any son fearful. With that she walks behind me holding a bag. "Hold still," she says to me as she crouches down. She lifts my left foot, slides something underneath, and then my right foot to do the same. I'm dumbstruck looking at the dress. I'd fantasised about wearing a dress like that but I don't want it now that it's about to happen. I snapped back to reality as I feel my mom sliding something up my legs. I look down in time to see a pair of light yellow knickers, with frills round the waist and leg holes. She slides them up under my towel, and up to my waist. I can feel the elastic tight around my waist and legs. Before I can think of what on earth I'm supposed to do, she whips off my towel to leave me exposed in just a pair of little girls' knickers. Not even batting an eye lid, she goes to the dress and swiftly removes it from the hanger. "Please no," I beg as she comes towards me holding the dress up to place it over my head. I step back out of fear. "Listen little Miss," she quickly snaps in a strict voice, "you will be wearing this dress even if I have to spank you." I was shocked by her threat. Her tone alone was enough to halt me in my steps. I wouldn't have imaged she'd put me in a dress so I had no way of knowing if the spanking was an empty threat or not. As she lifts the opening of the dress up to my head, I automatically start placing my hands through the hand holes as if it was a t-shirt, but once it falls down into place I realise what I'd done. 'Is it too late now?' I think to myself. As I'm wondering if she really would spank me, my mom walks around me and starts buttoning up the back, ties off the ribbon that draw the waist in and then there's a click. "What was that?" I ask bemused. "I'm not having you back out of this so I ordered it with D-loops so it could be locked in place. Don't worry; you'll get the key at the end of the day." 'End of the day. I've got to spend all day in this,' I thought to myself. Next she takes a hairbrush from her bag, brushes what hair I've got before placing a yellow bow hairclip in it. My hair was only just long enough to secure the hairclip in place. Her final touches were a pair of white ankle socks that had a frilly hem at the top, and a pair of pale yellow court shoes. She has me spend the morning dressed like that, to the great amusement of my younger sister who'd not worn anything half as girly in years. "Come on, we're going out," my mom says popping her head round the door. I look over at my sister expecting my mom just meant her. Both of them look back at me. "You too missy," my mom proclaims staring straight at me. "What? I can't go out like this," I protest. "Oh darling, of course you can. You look adorable and those flats fight perfectly. You could walk for miles without them causing any issue," she tells me, clearly not about to let off on this unusual and uncalled for punishment. "Oh, can we walk mom?" my sister pipes up. All I can think is, 'What the fuck.' Her teasing me that morning was nothing compared to the horror of walking outside like this. Almost instantly my mom replied "Sure. It's nice outside; I see no need to take the car." It was a warm summer's day so no coat to hide what I was wearing either. "Where are we going?" I grumpily ask while trying to keep my head down as I walked. "First we need to stop by my sisters to get the key to your dress" she informs me. I find out she'd ordered everything to my aunt's house and "forgotten" to pick up the key. The walk to my aunts was torturous but nothing compared to seeing my cousin. She, unlike my sister, had not been told to not take pictures of me. My mom stepped in before they ended up on facebook but she didn't make her delete them. After that mom took us for lunch. Fleetingly, walking past people in the street was bad enough but now everyone around got a good look at me as we sat there for almost an hour. "You have been such a good girl today," she tells me in a motherly voice, "I'd like you to wear dresses more often." "No, please don't. I'll do anything," I protest. "I'm sure you will but I think this would be a good thing," she continues ignoring my pleads. "How about we get you something a little more age appropriate? Or should I order you more dresses like you're wearing?" she asks. It's not much of a choice but I don't want to keep wearing dresses that look like their designed for a girl more than 10 years younger than I am, so I reluctantly agree to shop for something more age appropriate. "Great. We'll go shopping after lunch for a completely new wardrobe." With that, our food arrives and I don't want to make a scene (or any more of a scene anyway). I look at my mom who's starting to dig into her lunch as if the conversation has concluded. I glance over at my sister who's finding the whole thing highly amusing. And that's how my journey into feminisation began...

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Nic was 62 and very wealthy. He was handsome and had a nice muscled body. He loves young women. He has been dating the younger females since he was 30. He would keep them for a few months then buy them a very expensive gift and move on to another young lady. There was never a shortage of young girls for him. He liked them petite with big tits and a nice thick ass. Today he is picking up a young girl that he had fucked her mom many years ago when she was just 20. Her daughter is now 19 and wants...

3 years ago
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Like a Good Neighbor 2

A day after Jeff left for his latest business trip I looked up from my book to see Linda walking my way. As she reached my deck she pulled her shirt over her head exposing her now nude body. "Ted, we have all afternoon. I've never sunned in the nude, I thought that would be fun. I can get rid of these tan lines." "I kind of like your tan lines, but sure, let me pull over the other lounger and we can enjoy the sun together, but be careful of burning on the lighter parts." "OOh I was...

4 years ago
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Empty LandChapter 23

Withered leaves, stripped from the branches by stormy gusts, swirled along the ground. Naked branches bent and swayed. The wind shrieked and tore at the land with insane fury, then lashed the forest floor with sheets of driving rain. The sky was dark with tattered clouds, growing ever darker as the day drew to a close. "Got to keep going..." The lone traveller braced herself against the rough bole of an ancient tree as the wind tried to sweep her from her feet. "Got to find them... Find...

4 years ago
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Project

I was only fourteen when I became a high school junior. I had all the math and science credits I needed to graduate and if I took an English course in summer school, as I intended, would finish by August and could enter the university that had already offered me a full scholarship, a college freshman at fifteen. I had everything a kid my age needed except two, a driver’s license and pussy. I was a 100% virgin and most high school girls wouldn’t even look at me. I masturbated regularly and...

4 years ago
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Wrong NumberChapter 13

John was watching TV when I got back from my night out with Laura. I stopped in to say “Hi.” He asked how dinner went. “It was good. We had a good time.” As I looked at him, I pictured him with Laura. I said goodnight and went upstairs and took a shower. I could not get John and Laura out of my mind. Seeing Laura tonight and talking with her about her affair with my son had certainly been an experience. A very sexy experience. I could almost picture her naked with John’s cock in her hand. The...

4 years ago
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Sangeeta The Fucking Maid

Sangeeta was a sexy horny village-grown bitch. She used to work as a house-maid for Puneet, a friend of mine. She had got herself pregnant at the ripe old age of 18, and was sent to the city by her father for aborting, and a domestic help’s job to keep her away from her sexual linkups with village men. Puneet’s wife Pooja was a very pretty and sexy woman herself, and I suspected Pooja to have some inclination towards me. Being Puneet’s fast friend I did never want to take any leading action...

4 years ago
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Watching Anita again and again

Watching Ana again and againThat Saturday afternoon I was at my desk at home, when my loving Ana came back from the gym. She blew me a kiss from the door and said she was going to have a warm shower.One hour later I was surprised by not hearing my lovely wife doing anything around.I went worried and moved from my desk to check out inside home.Finally I found Ana in the garage… but she was not alone there.My sweet wife was fully naked there, bent over her car’s trunk, exposing her bare perfect...

2 years ago
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All The Kings Horses AdaptingChapter 2

"Is there one of the husbands who is the leader?" Julia asked. "My husband, Will," Val answered, and the others agreed. "Would you all give me permission to call Will and tell him that I am working with you. It would help me a lot if I could get a sense of what the men are feeling and thinking." "Oh, please, do that!" Val said quickly. The others added their encouragement. Fortunately, Will was able to free himself when his secretary told him that the call was from a doctor and it...

4 years ago
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Posing for Art Class Leads to Great Sex

Becky is 20 years old, lives across the street from us with her family and attends the local college. She is a very talented artist and a very attractive looking young lady. Last semester, she knocked on our door to ask to borrow something. Babs and I had just finished our workouts and were still in our sweaty exercise clothes. All I was wearing was a pair of shorts and Babs was wearing a sports bra and shorts. When I answered the door, Becky’s eyes instantly surveyed my sweaty torso and...

3 years ago
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The Officeplay

Your handle was officefuck69. This intrigued me. I checked the rest of your profile and thought you were worth sending a message to. 'Hi: Thanks for the flirt. I checked out your profile and you have my attention. What exactly are you looking for? Tell me a bit about yourself and feel free to ask me anything. I will answer any and all questions.' SEND I checked out a few web cams, read a few articles and was about to log off when I saw that I had a message. 'I'm looking for...

3 years ago
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My first lay was my friends mom

When I was 19, I was hanging out and sleeping over my friend's house fairly often. We were working on computers and trying to write a game and all sorts of other geeky stuff. During that time, I struck up a friendship with his mom as well. She was 43yo at the time, and very hot and young-minded for her age.There was one evening when my friend had left to go hang out with another friend, and I didn't want to go along, so I hung out with his mom and we just watched TV and talked. She asked me if...

2 years ago
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My First Sex

I’m 22 years old living in Chennai. I always feel like sniffing a girls armpit and pussy. But I didn’t get a chance. I’m so horny always. So I used to read iss stories and watch porn videos. Some times I used to check in locanto also. I’ll contact the girls on locanto but I never had a gut feeling to have sex with them. Recently I saw one ad in locanto. A Telugu girl posted an ad for fun. I responded to her add. She gave her email id and asked me to chat in Gmail. After seeing her email id, I...

4 years ago
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Me And My Girlfriend On Her Birthday

Hello friends my name is jay from Mumbai. Forgive me for my mistakes as this is my first story on iss. This is how I and my girlfriend finally had sex and that too for her birthday. For those who want hot action u may have to wait as this may be a lengthy story but if you don’t want to wait then you can change to another story. So beginning with the story – I and my gf were dating for 3 years and we only had oral sex till now. Last week was her birthday and I had to surprise her in a very...

1 year ago
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Night away in London

I was at the time working as a Director of a large company leading a regional team. As happened a few times each year the company was invited to a dinner in London and I was asked to attend on behalf of the CEO. I was booked into a hotel about half a mile from the dinner venue so dressed in my dinner suit I arrived at the required time and was greet by a team hosting the event. Having provided me with a glass of wine I was introduced to a lady called Wendy who told me she headed a division that...

Cheating Wifes
3 years ago
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Candy Ass

I adore her ass, and she knows it. Best of all, she revels in it. She's never afraid to show it to me, offer it to me, and let me lose myself in its warmth and softness while I seek the deeply erotic scents and tastes that lie between her ample cheeks. She knows, understands, and thrills to the power that her anus holds over me. It, in turn, is a zone of intense pleasure for her.She's a heavyset woman, about 5-foot-2 and 140 pounds with curly, reddish hair. Her ass is big and round, yet firm...

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