Sissy Bottom Stories

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Sissy Bottom Stories
Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
Since childhood, I was always fascinated by women’s clothing. I used to secretly put on my step mother’s dress s and liked feeling pretty and girly. I tried to stop those urges but it only grew bigger.
As time went by, I started to sneak into my step mother’s room more often. I tried on her outfits, her makeup and shoes. So, every time I was going to be alone in the house, I would simply dress up. I started to buy outfits, lingerie, hair wigs from online stores and kept everything hidden in my closet.
One day my whole family was going on a trip to one of our relatives. I somehow managed to stay behind, saying I have a few tasks to finish. It was a great opportunity to take the whole house to myself. So my parents left and I was so excited to get dressed. I really wanted to wear a full make-up from head to toe and spend as much time as a girl.



I started getting ready without wasting time. I started with makeup, then undergarments and a pink bodycon dress that I recently brought in. I finished my transformation with a blonde wig, pantyhose and high heels. It was surprising to see my reflection in the mirror as a girl. I thought I looked cute.
After I was ready, I walked around the house in my new outfit. It felt really great. I took so many photos and videos that I did not understand how time passed. My parents were only coming back the next day, so I still had time to spend as a girl.
I had been out to the backyard several times dressed before, but it was only for a short time.
I walked into my backyard, feeling a little nervous if my neighbors saw it. So I looked around until I was comfortable. After confirming, I set up the camera and started shooting.



I noticed there was a boy looking after me from the neighbor’s house. I didn’t know how long he stayed there. I immediately panicked. My heartbeat got faster and faster. But I still tried not to overreact. I simply and slowly entered the house.
I was terrified that my cross-dressing secret would be exposed and my family would find out.
Soon the boy rang the bell and entered the house and kissed me. I was now a boy’s girlfriend.
Awesome story. I actually kind of liked that you ended the story with saying that you’d become his girlfriend and let the reader’s imagination fill in the rest of the story after you two disappear behind the closed door to experience intimacy in private. Loved it!
I loved it when he kissed me. It opened up a new world for me. Not only was I dressed as a girl, but now I was loved by a sweet little boy. Oh, what I could do for him! Mmmmmmm . . . . . .
Miss Roxanne Lanyon
I hope you DID do it for him. And he do it to you… Uh, for you.
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Topic: A Naughty Little Boy (Read 26784 times)




Bertha


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« on: July 11, 2016, 12:02:25 PM »
This is not a story totally written by myself. I had the original stored for many years on a memory stick and about eighteen months ago I re-wrote it to my own personal taste. The original author was, (I think), Richard Parker and it was in M/m format. I posted my version to my blog and it was well received, so in the absence of my writing any new material I present it here for consideration. I will of course remove it if there are any objections. Thanks B. Philip was standing in the corner of his room sobbing quietly. His hands were on the back of his head, around his ankles were a puddled pair of pyjama bottoms; Philips pale blue, striped winceyette pyjamas. His bottom stung and was red from the spanking he had just received from auntie Agnes. Philip had been a very naughty boy and auntie had soundly smacked his little bottom until Philip was a very sorry boy indeed. Auntie Agnes had marched into his bedroom. Philip had to be up early as Auntie was going to take him shopping for new clothes. In her opinion, Philips shorts were not short enough. Philip was outraged, he hadn't worn any shorts with an inside leg of more than two inches since he became his aunt's little boy and here she was saying his shorts were too long. Philip had disagreed, rather too vehemently, hence the over the knee nursery style spanking he had just received. Auntie had pulled Philip out of bed, lifting him up by the scruff of his pyjama jacket and marched him over to the chair behind Philip's school desk. She sat herself down and draped the by now sobbing Philip over her upraised knee. She spanked Philip's bottom repeatedly for almost three minutes as Philip had howled and begged auntie to stop, promising of course, to be his aunt's little angel. Agnes Ashburnum placed him in the corner, hands on head, and busily began choosing the clothes her little boy was to wear on the way to the school outfitters. She was rather upset with her boy. How dare he complain or think he had the right to dictate what he was to wear, or how he was to be punished for that matter. Well, by the end of the afternoon, she knew a naughty little boy that would wear what he was given, and thank auntie for it, or he would again be a very sorry little boy indeed. Mrs Ashburnum began gathering the rather fine school uniform her boy would wear. She picked out a smart, little, white, short sleeved school shirt, a grey sleeveless jumper with red trim around the v-neck and the waist of the jumper, a pair or ankle length grey school socks with two thin red lines at the top. Mrs Ashburnum looked at the bottom of the wardrobe at the footwear section of her collection and picked out a pair of brown, t-bar sandals. She hadn't made her nineteen year old little boy wear sandals as infantile as this before, she was sure that Philip would make a fuss, well let the little scamp; he'll wear them with several hand prints to the backs of his legs if need be. She next searched through her vast school shorts section but couldn't find what she was looking for. Hmm … Just as well we are going to the outfitters. Can't have a little boy without pull-up school shorts. She found the next best thing, a pair of very brief, fully lined school shorts but which had an inside leg of only one inch. They were made of a flannel material, but not thick flannel. As they were second hand, and obviously, many a boy had been smacked in them, the material was quite thin. She chose a grey school blazer with red ribbon trim around the edge of the blazer and the lapels and a grey school cap with very short peak and also with red trim. Mrs Ashburnum called Laura and the maid promptly took the boy's clothes for the day and went to Philip's room and began running his bath. Philip, still sore from his bottom smacking, didn't want to be punished again, so meekly took hold of Laura's hand and was led to the bathroom, undressed and sat in the bath as if he really were a little boy. Philip just laid there soaking in the wonderful warmth of the water and bubbles. "Come along master Philip." said Laura "It's time for you to get dressed. Your aunt is going to buy you some nice new clothes today. Aren't you a lucky little boy? Laura grinned. Philip didn't feel very lucky at all. How many other nineteen year old boys were seen out in a short trousered sailor suit? He might be nineteen but when dressed up, he looked no more than ten or eleven. He was only five foot tall, had flawless smooth hairless skin, and was kept hairless from the neck down. He also had gorgeous straight blond hair with natural highlights that hung straight down in a little page boy hairstyle and had the most amazing blue green eyes, which could melt the heart of the strictest auntie. Philip got out of the bath and was enveloped in a big white fluffy towel by Laura who promptly dried the boy's flawless skin. As Laura was drying off the boys legs he noticed for the first time that Philip's legs now had a beautiful light tan while his bottom was a snowy white; or would have been if he hadn't been spanked by auntie that morning. Having dried Philip, Laura took the boy by the hand and took him to her bedroom where they both found the clothes for today laid out. Philip frowned and rolled his eyes as he saw the little prep school uniform. Philip stood while Laura began dressing the boy. She started with the short sleeved white shirt, then the little school ankle socks. Philip really frowned when he saw those, he much preferred to wear long socks with school uniform, he thought that little ankle socks, with or without the red trim made him look silly and even more childish than he usually did. Laura noted the boy begin to pout but said nothing, she next picked up the grey school shorts. Holding them up she noticed that these were shorter than the lad normally wore, the inside leg was only one inch. The thin flannel material was beautifully soft and had a white cotton lining. She held them open and Philip reluctantly stepped into them. Philip had to admit that they did feel very good, indeed, as Laura slowly pulled them up and tucked the white shirt in before fastening the shorts and pulling up the zip he felt himself shiver with excitement. "Turn around Master Philip, let me see how you look." Philip did as he was told, gently feeling his bottom through the thin flannel. Laura sat back on the bed and noted how well they marked the boy's bottom. As Philip was not allowed to wear underpants, the seam of the tiny school shorts disappeared up his bottom and the flannel clung to his bottom cheeks beautifully. Laura could just about notice a patch of now dark pink skin just showing below the hem of the shorts where Philip had been soundly hand smacked by auntie. Laura picked up the school tie and tied it in a Windsor knot, then came the v-neck sleeveless jumper and the blazer. Again, Laura noted how, with the blazer on, you couldn't see Philip's little shorts; Philip carried on pouting. Laura reached into the left hand pocket of Philip's blazer and pulled out the school cap and put it on the boy, making sure that some of the beautiful blond fringe showed below the peak of the cap, she thought it made Philip look like a mischievous little scamp. "Ah. We almost forgot your footwear, didn't we little boy, we can't have you going out in stockinged feet now can we?" Laura looked under the bed and almost giggled when she saw the childish, brown T-bar school sandals, she just knew that Philip wasn't going to like them; she was absolutely right. Philip took one look at the sissy little sandals and all he could do was flap his mouth open and closed like a goldfish out of water. " I can't, I won't wear those. " Philip almost screamed. "You will put these lovely sandals on right now you naughty boy. How dare you be so naughty when I'm trying to dress you? Your aunt will be told about your disobedient behaviour." Laura managed to force Philip's little right foot into the sandal and fasten it, when she tried to put the left sandal on Philip wailed and stamped on her hand. "That's it young man." Without another word she held the left sandal by the heel, took hold of Philip's left arm and began smacking the back of Philip's legs with the sandal. "You will wear SMACK, SMACK, whatever you are told, SMACK, SMACK. Six smacks landed from the sandal to his left leg, from the hem of his shorts to the back of his knees. Six perfectly marked, dark pink outlines on his leg. "Your aunt, SMACK, SMACK, has spent a lot of time and effort turning you from a tearaway teenager into a well behaved, polite little boy. You're not going to disappoint her or me with behaviour like that." Six more smacks of the sandal landed on his right leg. "Now little boy." asked Laura, holding onto Philip's arm, "do I need to give you a proper spanking over my knee before you do as you are told?" Philip didn't answer, he just wailed. He was smacked one more time on the left leg. "Well?" "No Miss Laura." "That's better." Finally, Philip was dressed in his very traditional, prep school uniform with little ankle socks and sandals and a blazer that covered his shorts, and what was worse, a stupid school cap. The slipper marks, showing clearly on the backs of his hairless legs, stung painfully. He went to rub and soothe them. "No, leave those marks alone, let them be a reminder of what happens to naughty little boys. "I'm so sorry Miss Laura." Philip sniffled, rubbing his eyes with his little balled up hands Laura sat the nineteen year old boy on her lap and stroked the inside of his thigh. "There, there little one, it's all over now." She said, gently kissing his smooth hairless cheek. "Just remember to be a good little boy and you won't have to be punished again." Laura took hold of Philip's hand and led him downstairs to the study. She knocked on the door and entered. Laura, instead of taking little Philip to stand in front of his aunt took him to the corner of the study and made him face the wall, hands on head. Mrs Ashburnum noted the back of the boy's legs. "Well, well Laura, I see you have had to impart a lesson to the little scamp." Philip was standing with his hands firmly clamped on his head, causing the bottom of his blazer to lift a few inches. Mrs Ashburnum could now see the hem of the tiny little shorts, but more importantly, see the bright pink thighs of her chastised little boy. "I'm dreadfully sorry Mistress, but your naughty little boy decided to throw a tantrum when he saw the sandals he was supposed to wear and well …" "Hmmm … don't worry Laura. From now on you will obviously have to take a more, shall we say, hands on approach in young Philips upbringing. You have my permission to administer smacked bottoms and legs at your own discretion." "As Mistress wishes," she turned and looked at the back of the boy's legs, bright and pink under the hem of his little shorts. They left Philip in the corner for half an hour; "Philip, come over here little boy." Philip turned around and saw his aunt sitting behind her huge, leather topped desk and Laura standing to her right. Philip walked slowly over and stood in front of the desk, eyes cast down, staring at his infantile school sandals; Goodness how he hated them. "I hope you've learnt your lesson little boy, I really don't want to have to punish you again today. "Sniff .., you wont auntie" replied Philip in a low voice. "We'll see." she said, then patted her lap. Philip smiled and ran over to auntie like an obedient puppy dog, who picked him up and sat him on her knee. Philip liked it when she cuddled him. "Well young man, today we are going shopping for some new shorts and a few other thing for you.. Now, I warn you Philip, if you misbehave while we are shopping, I will have no hesitation in giving you a good smacking, in public wherever we are." Auntie had put on her stern face as she warned. "Then, upon our return home you will get a sound spanking and be put straight into your jimmy-jams and sent straight to bed without supper. Do you understand?" Mrs Ashburnum scolded firmly. "I'll be good auntie honest … cross my heart." "Well don't say I didn't warn you. Now please go to the car with Laura while I finish this letter." She stood Philip up and sent him off with a firm smack to the back of his shorts as he scurried away. Mrs Ashburnum smiled as she watched them leave with Laura tightly holding Philip's hand. It had hardly taken any time at all she mused. Oh of course she and Laura had easily overpowered such a small, weak willed man child. She remembered that first night how they had stripped him and lowered him into the bathtub. Yes, he had fought them but a few slaps to his legs had subdued him and he sat placidly but trembling as they washed him. His smooth, hairless body, no sign of facial hair whatsoever on the nineteen year old, and the strange timid voice should have been clue enough, but the tiny stump that was his pen-is explained why this nineteen year old was her perfect candidate. She put down her pen and began to think of the clothes she was going to buy her boy. He had plenty of school uniforms but realised that she didn't have a little Cub Scout uniform for the boy. Yes, we'll go to the school outfitters and kit him out as a little Cub Scout. He placed a call to the outfitters to let her friend know that they were on the way and also to find out if she had the shorts that she had spoken to him about a week earlier. Philip was going to be a very surprised little boy. Philip was very comfortable in his uniform, he no longer felt embarrassed at being seen in public wearing his school uniform, even with the tiny school shorts he noticed that people didn't really stare at him. He was happy skipping along by aunty's side as he held her hand. Looking at a mirrored shop front window he noticed how he looked just like a little boy with his auntie. He was learning that it was much better to behave and be the perfect little boy rather than be punished for disobedience. If he acted and behaved like a little boy no one gave him a second glance, save for people admiring his smart appearance. As they neared the outfitters, Mrs Ashburnum bent down slightly and wagging her finger in Philip's face reminded him to behave; in they walked. Philip had never been to a shop like this before, it smelled of wood polish and cloth, it was a very traditional shop with all manner of traditional boy's clothes, from play clothes to school uniforms and other uniforms beside. Philip held onto his aunt's hand as they walked up to a distinguished looking lady in a white blouse and grey pleated skirt; half moon reading glasses were perched at the end of her nose. "How wonderful to see you again Madam." She looked down at the boy who was trying to hide unsuccessfully behind Mrs Ashburnum. "This must be the delightful little boy of yours you were telling me about." She looked down at Philip and smiled, knowing full well that the boyish figure in front of her was in fact nineteen years old. She was struck by his shyness and noted the long expanse of bare thigh below his cute little school blazer. "Patricia, my dear lady, yes, this is my little scamp. He is actually a good boy most of the time, though he can be quite mischievous and naughty at times and requires a smacked bottom." Philip wanted the ground to swallow him up and blushed mightily. "Philip, don't forget your manners introduce yourself to the nice lady, you will address her as Miss Fortescue-Smythe." Philip, all the while looking at the floor, held out his hand. "Pleased to meet you Miss Fortescue-Smythe," he said in a whispered, embarrassed and remarkably childish voice. "What a sweet, well mannered little boy you have there Madam. It's hard to believe that he could ever be naughty or…..nineteen," she added. Mrs Ashburnum laughed, "I can guarantee you that he can be quite a mischievous nineteen year old. Still we will soon turn him into the perfectly behaved little boy he longs to be, with the help of Mr Paddle of course." Miss Fortescue-Smythe, her hands clasped together and her head tilted to one side, nodded attentively as Mrs Ashburnum continued. "Only today I have had to give his bottom a good spanking and Laura my maid, had to smack his legs for his misbehaviour." Mrs Ashb
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