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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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Strip poker to poke her

It all started one fall afternoon. Joe and I were seventh graders, we had just started Junior High. Cindy was was in ninth grade and we all rode the same bus and lived in the same neighbor hood. As we all became friends while sitting aroung waiting for the bus that was always late, talking about anything and everything. Eventually the conversations turned to sex. Cindy talked as if she was very experienced in that area, and of course we talked as if we had been around the block once or twice....

First Time
2 years ago
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What I Saw

What I Saw.... My Fantasy As you lay on your couch, you can feel the warm leather plastered to your backside. There is a cool breeze coming through the door and windows. It is the last few days of September. The sensation of heat on your ass and legs while the cool breeze runs over your body is sending tingles down your inner thighs. You are sipping cabernet and the sweetness on your tongue from the heady cabernet is intoxicating. Candles are your only source of light. All these wonderful...

Masturbation
3 years ago
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Ambers Daddy and his need for me

Hill walking has always been something I have enjoyed since my p*****n years, in fact it is part of the Swedish lifestyle, skiing, swimming, to name a few others.One memorable moment was when I had a pee outdoors, again something that's very common and a great necessity, when the urge takes over.Most people, especially women, will nip behind a bush or disappear into the undergrowth, in case any males observing, take the wrong meaning of the girls intentions.I was out with my friends family in...

4 years ago
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BethChapter 48

August 17, 2017 Dear Ms. Diary, [Written August 21] I woke slowly to consciousness, a sister on either side of me. Certainly, neither girl was Rhee, whose breathing I could distinguish easily from years of experience sleeping with her. Since I also had fair experience with Heather as a bed partner, more so than either Liya or Gracey, I suspected that Heather was not one of my nearest neighbors. Last night came back to me, causing me to smile, although I had yet to open my eyes. Thoughts...

2 years ago
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Working It In

When the wife and I went out of town, we hired Tanya, the college girl from down the street who babysat our kids occasionally, to housesit and take care of our dog. Tanya was twenty, maybe twenty-one, and built, as they say, like a brick shithouse. She had long dirty, brown hair and firm full tits, with curves that made it very hard to look her in the eye for long. She was a wet dream, and she knew it. Every time she came over to our place to babysit, she was wearing clothes that managed to...

Anal
2 years ago
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Other Colors Ch 11

I ran. Honestly, I hadn’t intended on it. And yet at the earliest opportunity—as soon as I was dressed, and could put a closed door between us—I found myself clambering, almost methodically, out through the bathroom window, and down a cold, ivy-covered column into the snowy garden below. I ran by reflex. And looking back, it was just like me—the way my wheels worked. Like a Swiss watch. I didn’t go just because he broke me. I went because, afterward, he’d started to gather up the pieces....

4 years ago
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Boy wonder costume creates sticky situation

As the Halloween party that I had been invited to drew nearer, I was getting excited about creating my costume. I had always wanted to dress up like a superhero! The party was going to be a mix of men and women from the greater nyc area, most of whom I would probably never see again, as I was visiting my friend Todd. I had spent a fair amount on a Robin boy wonder outfit(red shirt, green speedo trunks, utility belt, cape,gloves, mask, and boots). The costume came without tights, so I went...

2 years ago
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What Do You Say to a Naked Niece Part Three

During our time apart, Emma texted me almost daily and was quite expansive in the topics she wanted to discuss. Everything from world events to homework to music and dating advice was fodder for conversation. The latter of which always gave me pause and even a touch of jealousy. I know she needed to lead a normal teenage girl’s life, and dating was a core requirement. And even though she assured me that her dates were just for fun and as a way to get out of the house, it was an uncomfortable...

3 years ago
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San Diego Summer 2

Like I said, things didn't get awkward between Kienan and me after our jerk off session in the van to get rid of the massive blue balls Cindy had given us. However, things did change. Things between Kienan and I became more relaxed or free spirited. It started with Kienan. One night I was in my bedroom watching TV before going to sleep. Kienan knocked on the door then entered my room. He was naked. His 8 inch cock was hanging between his legs. In a casual voice he asked to borrow some soap for...

Bisexual
4 years ago
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Hot Chocolate Ch020

Casey was sat cross-legged on his bed with his laptop open before him when he heard the familiar and teasing cadence of his sisters voice. Surprised by her presence he looked up from his laptop towards his open bedroom door, taking in the sight of his sister stood there, leaning casually on its frame, the hall's lights spilling into his room around her like an aura. She smirked as she held up her phone, wiggling it from side to side, showing him the most recent text message on display from...

4 years ago
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Mistake always happens

That evening I came from my office and found my sweet wife ready to go out for dinner. She said just the two of us…Anita had chosen a sexy short black dress, with black stockings and stilettos. She looked very classy and hot at the same time.I wanted to tear off her outfit and fuck her right there, but Ana convinced me we would have plenty time after dinner…Once we sat down at the restaurant, I asked if she was wearing any panties. Ana said no, she was not. My naughty wife gave me an evil grin,...

2 years ago
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Introductions

My sex life with my husband virtually ended when he had a serious car accident. For better for worse and all that, but I never expected that I'd have my last fuck in my early thirties. After I'd nursed him back to some sort of health he was very good in using his fingers and tongue to make me come, and I really appreciate the effort he puts into that, but I missed having a cock fuck me. One night after a few too many drinks, and he asked me if I was happy with our sex life, I admitted that I...

3 years ago
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Older man samples Lynn Chapter 2

This is a continuation of a husband sharing his wife. For context, Chapter 1 should be read first. There are references to incidents and characters from “The New Client Series.” Like the other stories I have written, it contains, wife infidelity, cuckolding, multiple partners, and voyeurism.  I appreciate your comments, suggestions and encouragement. The four of us walk down the driveway to the sidewalk. Lynn and Charles are walking next to one another. To the casual observer it would appear my...

Cuckold
2 years ago
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Miss Oh Loses Her Last Cherry

There can be absolutely no doubt that the seductive and submissive Miss Oh no longer possessed traditional openings in her luscious petite frame that had not been completely ravaged by multiple male admirers with juicy cocks that spread her open and sprinkled her with wet abandon for almost a full decade. She had been of the unfounded opinion that she had seen everything and done everything in the field of kinky relationships. She had been tutored diligently by her father, her uncle, her older...

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