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Personal Stories, Advice, and Support 173 People

    I'M The Big Sister Part 13

    After eating we drove to a different shopping centre hoping to find some spring outfits for Beck and me to try on. We found a store that had rack after rack of spring dresses and my sister and I went nuts looking for something we liked. We each ended up with six outfits we...
    oldgrumpy oldgrumpy 51-55, M Apr 17, 2013

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    I'M The Big Sister Part 11

    I took off the skirt and top I was wearing so mom could help me on with the gown. She pulled half the tissues out of my bra saying that I didn’t need to be quite so big. She went back to her room for something she said I needed and came back with a strapless bra. “You can’t...
    oldgrumpy oldgrumpy 51-55, M 2 Responses Apr 10, 2013

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    Andrew To Andrea Part 4

    The dress made him feel very vulnerable and exposed; he tried to stay out as much of sight as possible just in case anyone should see him. Caroline took hold of his hand, this sisterly gesture had never happened before and normally he would have immediately pulled away. However...
    oldgrumpy oldgrumpy 51-55, M Mar 2, 2013

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    I'M The Big Sister Part 12

    Some of the outfits were for everyday wear and some were dressy but they were all so much more colorful than my regular clothes and there were so many different types of fabrics to choose from! Even if I decided to wear a plain outfit I could always wear pretty underwear under it...
    oldgrumpy oldgrumpy 51-55, M Apr 17, 2013

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    Model Part 16

    PART 16 Mom agreed and we hurried off to my room to get me ready for dad. Grandma had brought over a dark green velvet dress that I picked out for Christmas and I had a couple of slips and panties hidden in the back of my closet for wearing when dad wasn’t home. This was...
    oldgrumpy oldgrumpy 51-55, M 1 Response Nov 11, 2012

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    Mary Jane Sissygirl, Chapter 11

    Age 18 -- Reminiscing With Jamie The next really significant moment in my life came when my cousin Jamie turned 18. He was a month younger than me, so I was already 18 when he came by to visit me.  He was wearing white Nike "Cortez" sneakers with black "swooshes," white crew...
    OldRacer OldRacer 70+, M 1 Response Apr 3, 2013

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    Standing Up To Life Book 2 Ch 50 Pt 2

    Chapter 50 Part 2 The banter went back and forth for the better part of an hour - I was starving as went into my lunch hour. I don’t even know why they brought me into the room. What was the point anyway? Arguing about a settlement amount? What was it going to change...
    oldgrumpy oldgrumpy 51-55, M Jan 24, 2013

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    Scared

    Their I was alone and scared in a dark room. With nothing but a plasma sword, my high tech wrist communicator, my wits, and a light gun that shoots a beam of light brighter than ten suns yes I had the ability to control the element: fire, earth, water, air, metal, steam, ice...
    girlyboy2002 girlyboy2002 22-25 Jul 22, 2013

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    Model Part 10

    PART 10 Soon I was all set to see Grandma in a cute plaid dress like the girls wore to school, white knee socks, and shiny black shoes mom called ‘Mary Janes.’ Mom brushed my hair back into a ponytail and tied it with a ribbon that matched one of the colours in my dress. I...
    oldgrumpy oldgrumpy 51-55, M 1 Response Nov 8, 2012

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    Mary Jane Sissygirl, Chapter 9

    The Rest of The Week -- And The Next At eight years old, when I became Mary Jane Sissygirl, I was very girlish in appearance and rather small for my age. I was one of the shortest kids in my class at school, and I could fit into many of my six year old sister's clothes. But even...
    OldRacer OldRacer 70+, M 1 Response Apr 1, 2013

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    Fresh Start Ch5

    Josh arrived at the mud bath building at three. The sky was darkening on the horizon, and Josh wondered if they would get a storm. There was no sign of Lindsey, but he wasn't disheartened. He knew he'd see her at dinner. Liz had invited them over for a barbecue."Hey, Josh, over...
    Becnme Becnme 56-60, F 3 Responses Nov 4, 2012

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    Model Part 4

    PART 4 Mom took me into a room with lots of closets and told me to take off my shirt, pants, and socks while she looked for something. I didn’t understand why I needed to get undressed but I always listened to what mom told me so off went my clothes. A few seconds layer mom...
    oldgrumpy oldgrumpy 51-55, M 2 Responses Nov 5, 2012

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    Model Part 6

    PART 6 One afternoon the phone rang and I heard mom talking like she was very excited. She looked over at me and smiled and told the person on the phone that she’d call them back. She told me to go outside and play then called Grandma and started to talk to her. Before I went...
    oldgrumpy oldgrumpy 51-55, M 2 Responses Nov 6, 2012

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    The Perfect Baby's Breath.

    The story begins with the birth of a son to Mr.& Mrs. Marion Helms,The helms were married late in life after meeting in Denmark,some 4 years ago while Marion was was on a cruise on his lavish and very large yacht.Marion was 30 at the time and Murial was 28 It was a spring fling...
    shelle48 shelle48 61-65, F 2 Responses May 3, 2012

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    I'M The Big Sister Part 14

    Weeks went by and I never wore any girl’s clothes. It wasn’t easy, whenever I saw girls in my class all dressed up I thought about dressing up myself. Every time I saw my dress or skirt I thought about how much fun I had and how exciting it was when I wore them. I asked mom...
    oldgrumpy oldgrumpy 51-55, M 1 Response Apr 17, 2013

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    Model Part 12

    PART 12 I was starting to get tired of playing pretend after a couple of months. I couldn’t climb trees anymore or do most any of the other things that I liked to do because mom and grandma were afraid I’d get a mark somewhere that would show up on my pictures. They started...
    oldgrumpy oldgrumpy 51-55, M 3 Responses Nov 10, 2012

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    Once Upon A Changing Life...4

    For the next while, G made several trips into his mom's room...just to see what he could see- at least that was what he kept telling himself. Each time he would get a bit bolder and try on something different. But then he began to wonder if mom was on to him...afterall, it was...
    gellis gellis 56-60 May 1, 2013

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    Model Part 1

    MODEL Mom always thought I was good looking enough to be a model. She and dad were always arguing about it, he’d say that it was a waste of money and she’d tell him that he was blind! I can remember how she’d tell people that someday she was going to take me to a...
    oldgrumpy oldgrumpy 51-55, M Nov 4, 2012

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    Mary Jane Sissygirl, Chapter 10

    Childhood and Teen YearsThat's how it started. That's how I became Mary Jane Sissygirl.  The following Monday I started going to ballet classes with Caroline.  For ballet I wore plain white panties, a short sleeved pink leotard, lace-trimmed white cuffed anklet socks, and pink...
    OldRacer OldRacer 70+, M 1 Response Apr 2, 2013

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    Life Changes Part 14

    When Jessie got home, Angie was already there. She had told her mum what had happened at the pool."Jessie, though today might have been embarrassing, it should stop those idiots harassing you any more" said her mum."They know now you're real, just like them.""Thanks mum" Jessie...
    Becnme Becnme 56-60, F 4 Responses Aug 20, 2012

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    Once Upon A Changing Life...3

    The feelings that ran through G were-- there were no words at all...just the sensations that held a whole new world...he could see the shooting of white lines and sparks within the dark of his closed eyes...his body trembled and then stiffened as he exploded within himself- and...
    gellis gellis 56-60 Apr 25, 2013

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    Andrew To Andrea Part 3

    Caroline wasn’t able to see this little girl because her view was blocked by her mother who was standing in the doorway. If she had been able to see however, she would soon have realised that this pretty little ‘girl’ was none other than her brother Andrew wearing one of...
    oldgrumpy oldgrumpy 51-55, M Mar 1, 2013

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    Highlander Part 2

    My anger had adrenaline pumping through my body by the time I stepped off the elevator on the next stop to the top floor of the garage. It was only that surge of adrenaline that save me. Or did it? I sometimes wonder if I’d have been better off being killed. Oh, well, I...
    oldgrumpy oldgrumpy 51-55, M Mar 27, 2013

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    Model Part 2

    PART 2 After that day mom kept looking at me kind of funny but wouldn’t tell me why. Finally, a couple of days later she said we had to go back to where they took my picture and talk to them. She ran her fingers through my hair which was longer than most boys and told me how...
    oldgrumpy oldgrumpy 51-55, M 1 Response Nov 4, 2012

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    Life Changes Part 11

    By the time they arrived home, Jessie had fallen asleep, exhausted by the mornings activities. They woke her gently, walked her up to bed and just took off the dress and shoes. She lay down and was asleep almost immediately. They realised that her stamina was still down.They...
    Becnme Becnme 56-60, F 2 Responses Jul 25, 2012

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    Once Upon A Changing Life...5

    G was sitting at his desk when the teacher called for order... "so...what shall we do with our 'spud' today!" There were the sugestions of 'walk around the school on his hands and knees!-- make him do doubble the homework!-- make him sing a song in front of the class!-- make...
    gellis gellis 56-60 May 1, 2013

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    Life Changes Part 2

    The force of the accident had sent the vehicles into a crazy dance across the intersection. It was miraculous that no other vehicles were involved, however the taxi was pushed into a power pole.  Police were on the scene seconds later having been in pursuit of the stolen sports...
    Becnme Becnme 56-60, F 2 Responses Jun 28, 2012

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    I'M The Big Sister Part 9

    Mom and Becky both thought I looked great in the skirt, it was short and my white stockings seemed to look really sharp with the red in the skirt. I found a spot where I’d be in the centre of several mirrors so I could see how I looked from the back. Just then a sales clerk...
    oldgrumpy oldgrumpy 51-55, M Apr 8, 2013

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    Andrew To Andrea Part 9

    He nodded and took the newly washed socks from his drawer while she swivelled around on the bed so that she was facing away from him. He then removed his school shoes and socks then proceeded to take off his grey trousers and underpants. They were quickly replaced by a pair of...
    oldgrumpy oldgrumpy 51-55, M Mar 6, 2013

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    Andrew To Andrea Part 1

    ANDREW TO ANDREA There are many stories about forced feminisation or petticoat punishment with quite a lot of these purporting to be true. Some of these are believable and some are partly so and some are all too obviously figments of the writers imagination. The following...
    oldgrumpy oldgrumpy 51-55, M 1 Response Feb 27, 2013

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    I'M The Big Sister Part 4

    Rich pulled on the top of his PJ’s and stood next to me in front of the mirror. “Isn’t it neat, we look like sister’s!” Wonderful, my brother and I are dressed up like a couple of sissies and he thinks it’s great. “We’re not sister’s remember! We’re boys, we...
    oldgrumpy oldgrumpy 51-55, M Mar 31, 2013

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    Mary Jane Sissygirl, Chapter 7

    Going To School As Mary Jane SissygirlI woke up the next morning wondering whether yesterday and Saturday had all been just a dream. But the silky feel of the panties and top of my pink baby-doll nightie against my skin convinced me it had been very real.  When I looked down, I...
    OldRacer OldRacer 70+, M 1 Response Mar 30, 2013

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    Model Part 15

    PART 15 I had a lot of pretending, mom calls it modelling now, to do and I didn’t have much time for my old friends. It didn’t matter too much though ever since mom stopped me from doing the things I used to do. Mom always told me that a model makes money with her face and...
    oldgrumpy oldgrumpy 51-55, M 1 Response Nov 11, 2012

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    Mary Jane Sissygirl, Chapter 4

    I Meet Some Neighbor BoysWhile my attention was focused on Karen, a group of three older boys from the neighborhood came up behind me. They had been out prowling around and had seen me talking to Karen and Bonnie.  Of course they could tell I was a sissygirl.Roland, the oldest...
    OldRacer OldRacer 70+, M 1 Response Mar 27, 2013

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    I'M The Big Sister Part 1

    I’M THE BIG SISTER Until a few months ago life was pretty boring for me. I was a twelve year old guy with a nine year old little brother. My brother was mom’s favorite from the day he was born and since dad died a couple of years ago he’s wormed his way even further...
    oldgrumpy oldgrumpy 51-55, M 3 Responses Mar 28, 2013

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    Andrew To Andrea Part 5

    As the two left the room their mother called after them, “please try not to get dirty, we’ll probably be going out after lunch.” They walked out into the garden and Andrew overheard Gran talking to his mother. “You know he looks lovely in his dress you could take him for...
    oldgrumpy oldgrumpy 51-55, M Mar 3, 2013

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    I'M The Big Sister Part 2

    One day I came home to get my baseball glove and noticed some of mom’s underwear in the hallway near my room. When I opened the bedroom door I saw my little brother standing there in one of mom’s nightgowns trying to put lipstick on! Before I could say anything I heard mom...
    oldgrumpy oldgrumpy 51-55, M 2 Responses Mar 29, 2013

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    Mary Jane Sissygirl, Chapter 12 - Conclusion

    AdulthoodAfter Jamie left, I began reflecting on having to spend four more years bare legged in juvenile short dresses and Mary Jane shoes. Somehow I didn't mind.  In fact, I was kind of glad I'd have an excuse to spend another four years as a sissygirl.  Although if I want to...
    OldRacer OldRacer 70+, M 1 Response Apr 4, 2013

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    I'M The Big Sister Part 3

      “Isn’t this pretty?” He asked as he pulled out a blue party dress with long puffy sleeves. “I can’t wait to wear it, it’s so nice!” “I’m sure you’ll be the prettiest boy at the party in that!” I laughed, “Just make sure I’m not around when you wear it...
    oldgrumpy oldgrumpy 51-55, M Mar 30, 2013

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    Once Upon A Changing Life... A true story

    Once upon a time --- there was a young boy named 'G'...he was much like the other 10 year old boys of his time-- liked to ride his bike, go swimming in the lake or river, find frogs and snakes..just the things all the guys liked to do. But one of the best thing G liked was going...
    gellis gellis 56-60 Apr 24, 2013

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    I'M The Big Sister Part 8

    “What are you doing?” I gasped. Mom looked at me with an innocent expression. “You said it was okay.” “I thought you meant on you! I don’t want any of that stuff on me!” “Oh come on now, lots of girls your age wear cologne. It’s part of growing up.” “But I...
    oldgrumpy oldgrumpy 51-55, M Apr 5, 2013

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    Model Part 14

    PART 14 We all followed Mrs. Trippman out to the bathroom where the girls stood in a line by the girl’s bathroom and the boy’s did the same next to our bathroom. Before anyone could move though Mrs. Trippman walked up to me and asked me to follow her. I was horrified when I...
    oldgrumpy oldgrumpy 51-55, M 1 Response Nov 11, 2012

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    Mary Jane Sissygirl, Chapter 6

    Sunday: Church, the Park, and HomeThe next day was Sunday and I went to church with Jamie and Jodie and was introduced around as their cousin Mary Jane from out of town. Since everyone at church was used to seeing Jamie and Jodie in dresses and I was (allegedly) a Sissygirl...
    OldRacer OldRacer 70+, M 1 Response Mar 29, 2013

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    The Lonely Hero Who Gets Lucky-part 2

    The young man was walking across the bridge of the local park, the water below was very deep. He noticed nothing amiss, until he saw some odd shadow on the rail of the bridge some 200 feet away. he looked for a second, then got a chill as it moved in a way that made him start...
    amytheinvalid amytheinvalid 26-30, T 2 Responses Mar 15, 2013

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    Life Changes Part 15

    Time was passing and Jessie was growing up fast. Jessie's 12th birthday had come and gone and was now fast approaching 13. The topic among her friends was turning more and more to boys. While Jessie enjoyed the conversation, she was a little concerned that she started life as a...
    Becnme Becnme 56-60, F 2 Responses Aug 30, 2012

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    I'M The Big Sister Part 5

    I was about to pull down the front of my bottoms and panties when an odd thought popped into my mind. What the heck, I thought as I turned my back to the toilet. I pulled my bottoms and panties down to my knees then sat down like a girl. It was different looking down at my legs...
    oldgrumpy oldgrumpy 51-55, M 1 Response Apr 1, 2013

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