Happy Birthday Dear Sissy free porn video

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Happy Birthday Dear Sissy "My! What a good boy you are, Alan! It's so sweet of you to do the washing every day ? and I really do appreciate the sweet way you have folded all of my panties and other lingerie! Most boys wouldn't even touch them, let alone fold them so carefully!" She then tousled my soft curly blond hair and leaned over to give me a wet kiss. As she normally did it was a kiss on my lips. I had grown accustomed to her kissing me, and also to her wearing next to nothing when she changed after a long day at work. Today she was in a short silky gold robe with flowers. As she bent over her robe opened partly to reveal most of her breasts, which I thought were lovely. Her perfumed scent filled my nostrils. I blushed. "Thanks, Mommy." My blushing was partly because I happened to be wearing a pair of her freshly laundered panties under my cargo shorts. They were peach colored and were made of satin and had lace inserts dipping in to form a V over the crotch. They also had small white pearls sewn into the lace. I could feel my small cock getting hard in the panties. Mom and I had been alone since Daddy left a few years ago, and we were very close. Since Mommy put in such long hours at the mattress factory (she was the secretary to the owner ? Mr. Harris) I pitched in and helped doing many of the household chores. I didn't mind and I knew she appreciated what I did. A year ago she had shown me how to do laundry, and how to care for her soft delicate things. It was actually the favorite part of my chores. At first there were a few pairs of panties and bras in the wash, then slips, nighties and robes. They were so soft and pretty. After washing them for a few months I stood at the dryer removing her things and I wondered to myself why boy's underwear was so boring and scratchy. It didn't seem fair. I knew what I had to do. I took off my clothes right there in the laundry room and nervously went through the fresh wash. It was a load of entirely Mommy's things. I couldn't help myself. I took a pair of silky pale blue panties and slid them up my legs. They felt so wonderful when I pulled them into place ? the way they hugged my cheeks and boy parts. My cock got hard instantly. I then took a long white nightgown from the wash pile and slipped it on. It was like electricity. The silkiness felt so good against my body and especially my legs. I went to Mommy's room where she had a full length mirror and looked at my reflection. I looked rather pretty I thought, and twirled around, luxuriating in her things. Watching myself in the mirror I then lifted the nightgown to reveal my hard little cock in the silky blue panties. I rubbed myself and noticed a small wet spot. I pulled the front of the panties down and started stroking myself, watching my reflection. I was so hot! This was incredible! I clenched my cheeks still firmly embraced by the silkiness of the panties and shot at least four ropy strands of cum which hit the mirror. After I calmed down I took off the clothes. I threw the blue panties into the next load of wash, which consisted of my boy clothes. It was summer vacation, and since I was fourteen now I was allowed to stay home during the day by myself. I was under strict rules of course. No one was to be in the house when Mommy was at work, and I was restricted to the house, the yard, or to my neighbor's house, where my friend Katie lived. We had been pals since we were just little. I got into a routine. Usually Mommy would be gone in the morning before I got up. I slept until 9 or 9:30 and then would get up, wander into the kitchen in my boxers and make myself breakfast. I would clean up the kitchen, vacuum the living room and tidy up. I then moved to the bedrooms and gathered the wash. When I entered Mommy's room I would take her dirty things from her hamper, grab my own and take them to the laundry room. Since a week ago when I had tried on her panties and nightgown I had become a bit more bold. I would take off my boxers and put on her dirty lingerie. Her panties felt so nice and I somehow felt closer to her, knowing that her scent was upon them. I began to wear her panties longer and longer each day, putting off my second wash load when I knew I must wash the panties that we had now both worn. At first I found that wearing panties all day was very arousing, then they just became normal for me. I couldn't stand changing back into my boring cotton boxers or tight white briefs. I began spending more of my idle time in Mommy's room. I discovered her panty drawer and found so many pairs of beautiful panties ? some I had never seen before that were very exciting and sexy. Thongs, frilly lace panties, even some that felt like rubber or something. Emboldened I continued carefully checking her drawers. I found bras, stockings, slips, and nighties of course. Digging through one drawer I felt something odd at the back and when I pulled it out I found that it was a rubber replica of a large cock! I laughed but marveled at the size of it. Was that what a normal man's cock looked like? It was huge and three times the size of my own. Holding the huge rubber cock in my left hand I picked out a frill pair of white lace panties and slipped into them. My own cock was small as a thimble. I sat down on Mommy's bed, enjoying the feeling of the satin sheets and held the rubber cock between my legs, sticking it out where my own would be if it were hard. I stroked it a few times and pretended my own cock was that big. It would never fit in the panties, I thought. I placed the cock under my pantied bottom and had it stick between my legs. My own cock was now hard in the panties and was just dwarfed by the shaft next to it. I wondered if I'd ever be a real man. With my cock touching the rubber monster I stroked myself until I shot all over myself and it. Dressing in only Mommy's wash wasn't enough. I began waking, stripping and going into Mommy's room every morning to put on a pair of panties and a robe or nightie to do my housework. I wore them all day, unless I had to go outside, and even then I stayed in panties and maybe a camisole or bra under my boy's clothes. I took pride in my laundering, my cleaning abilities, and began trying to cook. Mommy was so pleased. "Alan, honey, what a good girl you are! Not only is the house all nice and clean but you've even made a meatloaf and baked some potatoes!" "Thanks, Mommy, but you said good girl!" "What's that honey?" "Nothing, Mommy." After dinner Mommy relaxed on the couch with her second cocktail. "Alan, would you do me a favor, honey?" "Of course, Mom. What?" "Please go up and start a bath for me ? and put some of my bath crystals in for me." I left the tub running and went to my room to play video games. After about forty-five minutes Mommy called to me from the bathroom. "Alan, honey, I need you!" Outside the door I asked her what she wanted. "I forgot my robe honey, the long pale green one with the orchids on it. You know the one. Please bring it to me." I did indeed know the one. I had worn it two days ago. I went to her room and found the robe in her closet. "Bring it in, dear." I opened the door to find her out of the bath and drying herself with her towel. As I entered she dropped her towel and appeared before me nude, her soft skin pink and blushed from the hot bath. I gulped but said nothing as she took the robe from me and put it on in front of me. She slipped into a pair of white slippers with fur trim and short heels. "Thanks, sweetie. My but that bath felt good! Well, I'm off to bed!" She leaned over and gave me a sweet goodnight kiss. I went to my room, stripped down to the pair of Mommy's panties I was wearing, climbed into bed and jacked myself off, thinking about her beautiful body and how sexy she looked in that robe and slippers. That night I slept in just her panties and had strange dreams about being a princess in a long formal dress. A handsome prince was holding my hand and when he leaned over to kiss my pretty lipsticked lips I awoke with a jump. I was hard as a rock in my panties. Half asleep I pulled the front of my panties down and stroked my cock until it erupted, catching most of it in my hand. I smelled my hand and wondered what it tasted like. For the first time I tasted cum. It was an odd taste, warm and smooth and rather salty, but not unpleasant. I wondered if this was how all guys tasted. I wiped up and went back to a deep sleep. The next day when I went into Mommy's room I found a pair of stockings attached to some type of strap. The strap part was jade green and was satin and lace. There was a pair of panties lying nearby which matched. The panties were thong styled and very sexy. Since I was already naked and ready to wear something pretty for the day I tried on the panties. They were really nice, but tight, with little room for my maleness, which was flattened in them. The thong part of the panties seemed to push and separate my cheeks. The stockings and the belt thing really intrigued me. I sat down and examined them. I undid the stockings from the holders and pulled them up my legs. Wow! What a feeling! I put the belt thing around my waist and found I could adjust the tightness of it. I then attached the stockings back to it, and adjusted the straps so they stayed up nice and tight. I was in a sensual state of heaven, and paraded around the room, admiring how nice my legs looked in the mirror. I felt the need for shoes, and found a pair of black heels in the closet that were a little big on me, but I loved the way they made me feel. Realizing I was nude from the waist up I went through Mommy's drawers until I found a cream colored camisole I had seen Mommy wear under a blazer. The silky fabric made my nipples hard when I moved around. I removed the shoes, figuring I would trip in them and hurt myself and spent the rest of the day in this wonderful outfit. I found even more exciting lingerie in Mommy's room over the next week or so ? a pink girdle and a black teddy, with snaps in the crotch (My! That was sweet to wear!), plus stockings that stayed up by themselves and a leather minidress. The night before my birthday Mommy came home after work and changed into a short red kimono with black stockings and black heels. She looked terrific. She made me dinner that night ? and with dinner she even let me have a glass of red wine with her. We laughed and had fun. I felt a little tipsy from the wine. We went into the living room and I found the coffee table piled high with presents, all wrapped in pretty pastel paper! "Who are these for, Mommy?" "Well they're for you, precious. I know your birthday is really tomorrow, but I wanted to surprise you and celebrate ? just us two!" I was really excited! She sat right next to me and handed me a box wrapped in yellow paper with a matching bow. "Open this one first!" I carefully undid the bow, and unwrapped the paper. Mommy smiled at the careful way I was unwrapping. I opened the box excitedly and realized it was clothes. I expected a T Shirt or something, and when I pushed aside the crinkly tissue I was shocked to see seven pairs of panties! They were all pastels, and silky and lacy. I looked up at Mommy with my mouth wide open. "Surprise!" "Mommy. What, Um, why?" was all I could stammer out. "Oh don't be so surprised you silly goose! I know you've been in my things for weeks! I thought it was time you had your own girly things, sweetheart!" "But Mom?" "Shhh, that's enough now sissy. I think it's wonderful that you like to wear pretty, sissy things! I know what my baby likes and needs! You've been leaving little stains on my clothes, and I can tell that you've been going through my drawers and wearing the clothes I've been leaving for you to find in my room. A woman knows when someone has been wearing her stockings, precious! Now I want you to strip down right this minute and try on your new clothes!" What could I say? It was true and she had caught me. I couldn't protest. I took off my shirt, and then lowered my jeans. "Just as I suspected! You look very cute in those pink panties, little girl! Turn around for me a few times and model them for me!" I slowly turned around a few times. "Oh, Alan! You are going to be such a pretty girl. And look how small your penis is in those panties! You barely have a lump that we have to worry about concealing!" I blushed. "Mommy! It's not always that small, you know!" "Oh, pardon me! Honey, I think your little cock is very sweet, but you have always been rather small "down there" you know. It's your father's fault, really. He was small too. It's part of the reason we had trouble you know. He could never please me properly and it really bothered him." With that comment she pulled my panties down and off me. I tried to cover my nakedness but she laughed. "Oh, honey, don't be so shy. I've seen your little cock and balls before. Put your hands down and let me see!" She took my cock into her fingers, and I felt myself getting hard. "Oh isn't that cute! Look how hard your little cockette is! Does it get any bigger, honey?" "Umm, no. That's about it, Mommy." "Well I think it's just the sweetest little thing. Do you know when you were just a baby I used to dress you in little girls clothes? I always wanted a sweet little girl, and I thought since your penis was so small and little that maybe you really should have been born a girl!" My cock softened and became very small as she continued. "Yes indeed, you used to be so small and sweet in the little pink and yellow dresses I put you in. Your father put a stop to it though ? at least he thought he did. Whenever you and I were alone you were always in a frilly dress or outfit. I used to call you Melissa, which is the name I would have called you had you been born a real girl. Even when you were a toddler you were in a pretty dress. When you became potty trained though I did what I thought was the responsible thing and dressed you as a boy full time. Now I see I was right all along. Well now sweetie let's have a look at your new pretty panties1" I nervously took the panties from the box one by one. They were very pretty. All in pastels, some had lace and little bows. "Precious, please put on the pink ones." I picked up the panties and stood to put them on. They were so pretty and feminine. Mommy explained they were full cut panties. They had lace around the waist and around the leg openings. There was a small white flower made out of little pearls right in front. They fit me perfectly! "There, that's better! Now you're in your own panties, darling. You look so sweet in them! Here ? open this present next!" I excitedly opened the next present wrapped in lilac colored floral paper. It had several bras inside. One was white and one was pink. "Put on your training bra now honey. Be a good girl!" I took the pink bra ? wanting to match my panties ? and put it around me. Mommy helped me to attach the strap. "Now darling you will have to learn how to attach this yourself. That is if you haven't already figured it out wearing mine. This bra fits you very nicely! This is what every young girl wears until her breasts develop!" The bra felt very nice and fit me well. The soft material felt so nice against my nipples, which I found were getting rather hard. Mommy then had me open a box with stockings, the strap thing (she said it was a garter belt), and several pairs of tights in pink and white. She had me put on the white garter belt and showed me how to put the straps under the front and back of my panties. She showed me how to scrunch up the new white stockings and to gently roll them up my legs until I fastened them to the garters. After my stockings were in place Mommy produced some thin short white socks with pink ruffles around the top. They were placed over the stockings, and carefully folded over so the lace was showing. Mommy called them anklets. The next present Mommy had me open was a big box. I opened it to find a Very full satin and lace slip. She called it a petticoat. "Here honey, let me help you. Oh, I'm so excited helping my little girl into her first petticoat! There! How does it feel?" "I love it Mommy!" "Oh good, darling. Now it's time for your shoes! She helped me to open a box containing a pair of shiny black shoes. "They are called Mary Janes, sweetie. Let me help you buckle them in!" The shoes fit perfectly, and I loved the way they looked. Just like a little girl would wear going to church or to a fancy party. I was so happy that I leaned over and gave Mommy a big kiss and a hug. "Thank you Mommy so much for understanding and making me feel so special!" "Oh, Darling. I am so happy to see you so pretty and contented, but you have a few more presents to open!" I opened a big box wrapped in pink paper with butterflies. It was a dress! The kind of dress a little girl would wear. I pulled it out and looked at it. It was a pink dress with what Mommy called a peter pan collar. The sleeves were short, puffy and lacy around the openings. The skirt was very full and had lace all around it. The front looked like it had a pale pink apron over the front which was also very frilly. Mommy told me to stand and she took the dress from me and lowered it over my head. I cannot express the excitement I felt as the dress fell over my body and she adjusted it over my full petticoat. She zipped it up the back and taking my hand we went to her bedroom ? to her dressing table. She sat me down at the table and pulled up a chair to sit next to me. Her robe fell open and I realized Mommy was naked underneath. I could see her breasts and between her legs. "Now, now sweetie. No peeking. We're all girls here tonight!" Mommy then used her makeup skills on me as I sat quietly before her. I felt her put blush on my face, eyeliner, mascara and lipstick. She told me to close my eyes and keep them closed. She returned a few minutes later and I felt her fussing about my head. She put a wig on me. Then using a brush she combed it out and sat there for a moment silently. "Come here, Melissa darling." I held her hand and walked a few feet, still keeping my eyes closed. "OK you may open them now!" I opened my eyes and was shocked at the reflection I saw in the mirror. I was dressed like the prettiest little girl! My hair was shoulder length and had blond curls. My makeup was very pretty, and my outfit was adorable. I felt so sweet, so feminine, so girlish. Mommy laughed. "I just knew you would be a pretty girl! I'm going to call you Melissa when you're dressed up honey ? I certainly can't call you Alan!" Mommy took me by the hand and we sat together on her bed. "Melissa honey, I've dressed you as a little girl for a reason. I know you will be fifteen tomorrow, but I feel you never had a chance to be a little girl like I wanted you to be. In order to be a good woman you need to first be a little girl, and learn the things girls need to know. I want to help you with that. Would you like that?" I thought for only a moment. "Yes, Mommy. Please make me your little girl. I want to learn. I'm happy when I'm dressed in girl's clothes." With that Mommy gave me a big hug and kiss. We spent the rest of the evening talking about being a girl and Mommy taught me how to sit like a young lady. When I went to the bathroom to pee, Mommy told me when I needed to tinkle I need to sit on the pottie like a girl. She even taught me how to curtsey! When it was time for bed it was time for more presents. I got my own pretty nighties. I put on a Barbie nightie in pink and climbed into bed after removing all of my makeup and hanging up my dress and putting my pretty things on the dresser. I slept like a baby. When I awoke the next morning I was wondering if last night was a dream, until I rubbed my eyes and noticed my surroundings. The morning wood I normally had quickly subsided and withered away as I discovered the changes around me. It was still my room, but different. The white walls no longer had the posters and things that were there yesterday. In their place were framed pictures of Victorian ladies in fancy dresses and parasols. The navy colored drapes that were here yesterday were now light pink and had ruffles. My blue bedspread was gone and I was covered in a pink one that matched the color of the drapes. Even the things on my dresser were gone. In their place were dolls and stuffed animals, and there were even a few stuffed animals on the bed. I found a soft cuddly teddy bear and a Raggedy Ann doll. Glancing around the room to my horror I noticed my TV and X Box were gone, along with the games. In their place was a Barbie playhouse, with dolls, clothes and all kinds of accessories. Even the lamp next to my bed was changed at it was a ballerina lamp with a ruffled pink shade. I was really awake now. I got up, took off the nightie I was in and went to my dresser to find something to wear. I had to go find Mommy and get this straightened out. I opened my underwear drawer but there was nothing in it but panties, bras, stockings, garter belts and tights. In my shirt drawer I found a few pastel colored girl's shirts with lace and ruffles ? very feminine. In my pants drawer I only found a few short skirts and my petticoat. I looked in the closet. Not a male item to be found. Just dresses, blouses and things. All my male clothes were gone. Everything. Even my sneakers. I had to wear something. I put on a pair of the new panties Mommy had given me. They were yellow and had little embroidered daisies all over them, and white ruffles across the back. They really felt nice, but I couldn't think about that now. I pulled on a pink shirt that had the powder puff girls on it, and pulled a black skirt on. Entering the kitchen this Saturday morning I found Mommy in a black matching bra and panties set. "Good Morning, Melissa. How is my little girl this morning? You look so cute in your powder puff girl's outfit!" "Ummm, thanks Mommy. Where are my clothes?" "What do you mean, pumpkin? You're wearing your clothes!" "No, I mean my boys clothes!" "Oh, you won't be needing those for awhile sweetie. Have some cereal and then come to my room afterwards. I wolfed down my cereal wondering what on earth was happening and raced to Mommy's room to find her only in her panties. Her huge round breasts were right out in the open and kind of distracted me. "Come here, Melissa. Sit by me." I joined her on the edge of the bed. "Darling things will be different here from now on. I can't have a young man rifling through my things, wearing my clothes, playing with Mommy's dildo?yes, darling I know that you've been playing with that as well. What kind of young man would do this?" She put her finger on my lips to stop me from speaking. "The answer is no male would do such things. I decided that this birthday I would give you the gift of a lifetime ? to give you the opportunity to truly understand yourself and what you want out of life. I will not have you becoming a grown man and secretly dressing up, perhaps having sex with men on the side, hurting a woman you may love and possible destroying a family. No, I think this is better." I rolled my eyes. "Don't you roll your eyes at me young lady! Beginning today you are my daughter Melissa. You will only dress as a young lady. You will learn what is to be a girl, and by the end of the summer a young woman as well. All of your icky boy things have been removed from the house. Don't bother looking for them. But now I have some questions for you, and I want honest answers! "Have you had sex with a boy?" "No Mommy! Not with anyone!" I was mortified. "Have you kissed or been kissed by a boy or a girl?" "No Mommy, just by you." "That's very good Melissa. We're starting with a clean slate. Now I want you to join me in the bathroom." We entered the bathroom and at Mommy's direction I stripped. She looked my body over and gave me a plastic bottle and instructed me to rub the pink lotion over my entire body. As I finished it started to burn, especially in my pubic region. "I'm glad you're not very hairy yet, but we must remove all of that nasty male hair! You may take a nice shower now dear, and use this washcloth to scrub the gel from your skin." I jumped into the shower and rubbed vigorously. I could see the runoff in the tub was dark and my skin was smooth and pink. I stepped from the shower and Mommy handed me a nice fluffy pink towel. I dried myself and she had me apply a soothing lotion and then some baby powder to my body. I was smooth now, smooth and pink and I felt very vulnerable and not at all male. My little cock and balls had shriveled up and seemed to be retreating into my body. She then led me by the hand to my now feminized room. "Now Melissa, this is your birthday and I want you to dress in a very pretty outfit today. It's your birthday, honey, and I want it to be a special day for you. It may not be the type of birthday you were expecting, but I know deep inside you are enjoying this. Just let yourself go. I truly perceive you as a girl, and if you wish to become a boy again at the end of the summer then so be it. This is your chance to explore your true feelings. Now go and dress and I will help you with your makeup." I returned to my room and thought about what Mommy said. I had been thinking for some time what it would be like to dress like a girl all the time, and the clothes she bought me were beautiful. If I didn't like it I could go back, Mommy said so. I decided to give it a try. Picking out an outfit for the day was difficult. Hanging in the closet with the pink dress I had worm last night was a beautiful yellow dress. I decided I would wear it. I first put back on my yellow ruffled daisy panties, then my white garter belt and white stockings. The stockings felt wonderful on my now smooth legs. I put on the white training bra and enjoyed the way it felt against my chest. I put on the black Mary Janes and then slipped the yellow dress over my head. It was very pretty. It was cotton gingham, and had white trim and ruffles. With the petticoat it stood nearly straight out and I realized my panties were visible, but it was so pretty! I couldn't zip it so I went to find Mommy. "Mommy, can you zip up my dress?" Mommy was dressing in her room and was wearing a very pretty outfit. "Do you like my teddy, Melissa? Soon you will be a big girl and can wear sexy outfits like this too! They make men mad with desire and they will want to kiss you and make love to you! Since you're a sissy honey you probably don't understand how they would feel! Say! You look very pretty! Let's get your face done!" Before I could really think about her comment about me not having masculine desires she at me down at the dressing table and instead of just doing my makeup for me she instructed me as to how to apply the makeup myself. It was fun! With each step I felt more feminine and less and less like a boy. "Now Melissa I am going to use a curling iron to make your hair a little more girlish. I want you to let it grow this summer." When she was finished my hair, which was rather longish for a boy anyway, had soft blond curls. It was still short but with the makeup I did indeed look like a girl. "There. Look how pretty you are!" Looking in the mirror I saw a pretty girl looking back at me. It excited me so. I felt happy and content, happier than I had been in years. I helped Mommy finish dressing and watched as she applied her own makeup. She was so pretty, and really knew what she was doing. She put on a sheer white blouse over her red teddy and put on a short black skirt. She put on short black heels which matched her black stockings. We went downstairs and cleaned up a little. We had a nice lunch together and I tried to remember all she taught me about manners and how to sit and stand like a proper lady. She was pleased with my progress. We had just finished eating when the doorbell rang. I looked at Mommy with terror. "Don't be so surprised, Melissa. We're having your birthday party!" I stood right where I was, frozen, as Mommy opened the door to my unexpected party guests. It was Grandpa, his wife Elaine, and her son Kenny. Grandpa had married Elaine a few years ago, and Elaine and her son moved in with Grandpa. My grandpa was well off, and Mommy always thought the Elaine, who could be really mean, was just after Grandpa for his money. Her son Kenny was 20 and lived with them while supposedly attending junior college. I had met him three or four times and thought he was kind of a burnout. Elaine burst into the room. "Oh, Sandy! She is absolutely precious! I love your outfit Melissa. You look so sweet! Come and give Elaine a hug and a kiss!" I shuddered but hugged her and kissed her cheek. She was just a little older than Mommy. Grandpa was not always "with it", I'm afraid and Mommy brought him right up to me. "Dad, this is your granddaughter Melissa!" He looked confused. "What? Where's Alan?" "Well Dad, this used to be Alan, but she's Melissa now. Isn't she pretty?" "Yeah, she's a peach ? but who is she?" Mommy was embarrassed and she and Elaine got Grandpa settled into a soft chair. Kenny slouched into the room. With a sly grin on his face he came up to me. "Hello, Melissa. It's nice to see you. You look very pretty!" I was mortified. Kenny was in a pair of jeans and a T shirt. His long dark brown hair half covered his face. While I looked at him he openly groped his cock through the jeans but only I saw it, and he smiled back at me, to let me know he caught me checking him out. "Melissa, go make Grandpa one of his cocktails, and get Elaine and I a glass of white wine. You may get you and Kenny each a soda." I went to the kitchen, rather nervous about my predicament. I felt very pretty and I must admit, very happy at the thought of being a girl for the entire summer, but I just wasn't prepared for guests. I wasn't so worried about Grandpa, he was a little out of it anyway, but Elaine was another story. She had always seemed rather mean to me and I wasn't sure what kind of grief she would give me. And then there was Kenny, who with his sly grin and grope was obviously enjoying what was happening. I just couldn't think about it, that's all ? I just had to carry on like everything was completely normal. I mixed Grandpa his brandy old fashioned, and poured two glasses of wine. For Kenny and myself I poured glasses of diet soda. I put them on a silver serving tray and carefully took the drinks to the living room. The thought occurred to me that I should be thankful I was in black Mary Janes, and not a pair of Mommy's high heels, as this task would have been nearly impossible. As I entered the room I found I was the subject of a conversation that had evidently been happening since my departure. "Well, Sandy", Elaine said, "I think it's terribly understanding of you to have your son dressing and living as a girl for the entire summer! What will happen then, I wonder?" "Well I don't know. I guess if Melissa wishes to be a permanent member of the family maybe we can ask Grandpa to pay for some surgery to make this change permanent!" Mommy, Elaine and especially Kenny all laughed heartily. Grandpa chuckled along as well. I nearly dropped my tray of drinks. "Thank you, Melissa! What a nice maid you would make! Hand a drink to each of your guests! And be a sweet girl, and curtsey to each of them." Will this embarrassment never end? I delivered the wine glasses to the ladies, and did a sweet curtsey. "Enjoy your drinks, ladies, and thank you for coming to my birthday party!" Elaine just laughed. "Oh, believe me, darling. I wouldn't have missed this party for the world! Let me see your pretty panties, Melissa!" I looked at Mommy. "Go ahead, pumpkin, lift up your skirts!" I lifted the hem of my pretty yellow dress and my petticoat to reveal my pretty yellow panties, trying to make sure that the men did not see my shame. "Oh, Sandy?I see that you bought a gaffe for our little girl to hide her boy parts! What a good idea! She is smooth and pretty as she can be!" "Well, actually Elaine, Melissa is not wearing a gaffe. You see she has always been rather physically undeveloped down there?it's something she inherited from her father." Elaine reached out to touch the front of my panties, while I obediently held them up. This was SO embarrassing! I felt Elaine's hand touching me, rubbing the front of my panties. Oh, God! "Oh yes, there?I feel something, something rather small! Melissa aren't you lucky not to have a normal sized boy's penis to get in the way of your femininity!" Kenny just laughed, and I dropped my dress and petticoat back down. I could feel how red my face was. "Now, now Melissa, don't you worry about that. You look very pretty!" Mommy tried to reassure me. Grandpa added his two cents worth. "Well I've always been hung like a horse! And young Kenny here ? I've seen his tallywacker and it's a good nine inches! A real trouser snake!" I had never been so embarrassed. Everyone in the room laughed. Mommy insisted that I sit next to her on the couch, and she tried to comfort me by holding my hand and rubbing my stocking clad leg. Kenny, sitting in a chair across the room just shifted in his seat and spread his legs to give me a better view, I guess. I could see the outline of his hard cock against the right inseam of his jeans. Our eyes locked until I diverted my attention. We chatted for a few more minutes and then Elaine left the room and re- entered with presents for me to open. Before she set them down before me on the coffee table Mommy whispered to me to close my legs and sit like a lady. I opened the first present, from Grandpa and Elaine. It was a large box, and wrapped very prettily in pink with a chiffon bow. Based on the wrapping job I just knew it was something very feminine. I opened the box to find an entire outfit ? one a school girl would wear! There was a short pleated red plaid skirt, a white silk long sleeved blouse in satin with a high collar, a matching plaid vest, and a black beret. It was really pretty, and there were oohs and aahs all around the room, even from Kenny, although I suspected his were an attempt to mock me. I also received several gifts from Grandpa and Elaine that consisted of panties, training bras, and garters and stockings. There were so many and so many pretty colors! My hands trembled a little as I examined the contents of the boxes. There was also a box containing back and white saddle shoes which Mommy said would compliment my schoolgirl outfit. I then unwrapped a small peach colored package. Elaine told me that it was from Kenny. I looked at him nervously and politely thanked him for the gift. From the way he was watching me I was relatively sure that he had no idea what was inside. It was a fine gold chain with a gold heart and earrings! The earrings were clip on, thank goodness and really very pretty. They dangled and had little hearts at the end. Elaine piped up, "Aren't they darling, Melissa! How sweet, your first girly gift from a young man! Put them on, dear!" I did as she suggested and really liked the feeling of wearing jewelry. "Thank you, Kenny. I like your gift very much!" "Melissa, honey, I want you to go to everyone individually and thank them for making this such a wonderful birthday for you with a sweet little kiss!" "Yes, Mommy." I kissed Elaine first, smelling her heavy perfume. Then I went over to Grandpa. He made me sit on his lap and hive him a hug and a kiss. When I did so his hand went under my skirt and I felt his hand gently pat my pantied bottom. I leaned over to give Kenny a kiss, and that was the most humiliating thing of all. He didn't really react though, thank goodness. "Now Melissa, would you and Elaine join me in my room, while the men enjoy their drinks?" I followed Mommy and Elaine to her room and she closed the door and proceeded to begin undressing. "Melissa, I have something to tell you. For a few months now I have been seeing my boss, Mr. Harris. I truly enjoy his company, and he's taking me out tonight! Elaine ? since you, Dad and Kenny are staying the night would you mind keeping an eye on Melissa, here?" "Why not at all, Sandy! I'm so excited for you! Tell me all about him!" As Mommy began redressing, slipping into a short black dress that was rather tight she answered Elaine's question. "Well, Bob is really a very nice man, rather forceful. He's very handsome, strong and masculine. He has the most amazing hairy chest, and girls! What a cock!" I rolled my eyes. Now, now Melissa. Just wait until you experience lovemaking with your first young man ? these things matter! A woman doesn't want to be with a thin, smooth feminine sissy with a tiny manhood! She wants a real man! A man to kiss her passionately, and fill her with his manhood. Now, Melissa I want you to be a good girl for Elaine tonight and do as she says." "Yes, Mommy." I left the room and went to the bathroom. I made sure to check my makeup and combed my wig to make sure I still looked pretty. As I looked into the mirror I was so pleased at my reflection. I left the room and stopped outside Mommy's room to accidentally overhear Mommy and Elaine talking. "You're very tolerant, Sandy, letting your son prance around like a schoolgirl!" "Well, what can I do Elaine? He's been wearing my things for months! And he's always been a momma's boy. He has even been playing with my dildo, which was safely hidden in my dresser drawer!" "Do you mean he's gay?" "Well, I certainly think so, but it's more than that really. His lack of male friends, his willingness to perform household duties, and his feminine nature can't be overlooked. And then there's the matter of his penis!" "What do you mean?" "Well Dan and I were both alarmed about how small he is down there. We thought he would outgrow it but it's just never happened. You know his father was never very big in that department, but I'm afraid my son will never be able to please a real woman in a manly way. I've wondered if his maleness was some kind of mistake of nature, a mistake that I am forced to see about correcting. This summer should help bring the matter to a head, so to speak, before he is humiliated with a girl and crushed. I do so love Melissa, and want to protect her and be happy." "Well, you can count on your father and me to support you both." "Thank you, Elaine. Now I must hurry to be ready for my date. I am so looking forward to a sleepover and a night of passion with that man!" I quietly went downstairs, trying to erase what I had heard. Was I really a girl, deep inside, and a mistake of nature? Mommy's date, Mr. Harris stopped by to pick her up, and Mommy paraded me out to meet him. "Hello, Mr. Harris" "Well, this must be Melissa! I've heard all about you, princess! My, aren't you a pretty girl! Just like your Mama!" I blushed, and he and Mommy said their goodbyes and left for their date. Mommy seemed very excited. I was really happy for her. Mr. Harris was a very handsome older man ? in his late 40's I thought. He was well dressed and looked like he worked out. After they left things quieted down. I helped Elaine prepare dinner for us. It was fun to help her and she showed me a few cooking tips. We were just a couple of girls preparing a meal for the guys, who were watching a baseball game. She was very nice to me, and with each passing minute I felt more and more at ease in my new role as a girl. It was a very pleasant dinner with Grandpa, Elaine and Kenny. Afterwards Elaine and Grandpa retired to the living room with a drink to relax. Kenny and I were told to go downstairs to the basement rec room and watch a movie. I went downstairs with Kenny and was a little nervous, I must admit, to being alone with him. He was nice though, and even brought down soft drinks for us. We looked at the movies we had in the house and agreed to watch an action flick that he hadn't seen but I did. I wasn't really that interested in it, but Kenny was and I was trying to be nice. We sat down and put the movie on, turning down the lights. "It's really warm down here. Aren't you warm, Melissa?" "No, I'm O.K." "Do you mind if I made myself more comfortable?" "No, Kenny" Kenny's idea of being more comfortable meant he was stripping down to his boxers. They were plaid Abercrombies. I never really noticed it before but Kenny had a nice chest, and was pretty muscular. He sat down on the couch again, but this time a little closer to me. He sensed my nervousness. "Man, you are really uptight! Let's see if I can help with that!" Kenny leaned over, fumbled in his pants, and pulled out a joint and a lighter. He lit it and took a drag, then handed it to me. "Come on, relax a little. This will take the edge off. You've had a crazy day!" "No, I've never done that before! What if Grandpa or Elaine comes down here?" "Don't worry about it. Here!" He handed me the joint and I nervously inhaled. After what I had been through today what difference did it make? Kenny laughed as I coughed and taught me how to inhale, hold it, and then expel the smoke. By the time the joint was done I felt a little strange. I was relaxed, and just leaned back on the couch and mellowed out. "See, I told you that you needed this! Just relax, baby." Kenny sat back on the couch, and sitting a little closer, put his arm around my shoulder. I didn't really mind at this point. We continued to watch the movie, and I found myself really enjoying it, though I'd seen it a few times. Kenny seemed to enjoy it too, and I looked over at him. He really was kind of handsome, in a ruddy kind of way. He sat there with his legs spread comfortably, and I noticed him grope himself a few times. "Melissa, have you ever kissed a boy?" "No, Kenny, never! I really don't know how!" "Well, you're pretty and I like you a lot, I always have. Can I kiss you?" "I don't know, Kenny?" "Oh. Come on, please? If you don't like it just tell me and I'll stop." I turned to look at him and he held my face and kissed me. I melted under his lips. He pushed his tongue into my mouth and we kissed some more. It was very exciting. I just let it happen ? I went with it, and reached up with my hand to caress his long hair as he kissed me. "That's it, Melissa. You're so hot, I've wanted to kiss you all day. Do you know what kind of effect you've had one me today?" "Um, No, what do you mean?" "Look, baby!" He took my hand and put it down on his boxers. I could feel his hard cock straining against the cotton. My god, he was huge! I breathlessly initiated a kiss and placed my own tongue into his mouth this time, as he kept my hand on his hardening manhood. I was surprised at the effect I could have on a boy. Kenny then took his arm from around me and put it on my leg. He rubbed my leg and moved his hand up the inside of my thigh and under my dress. I had never been so excited. As we continued to kiss he pulled his boner out of his fly and out my hand around it. "This is the way a man feels, Melissa. Work your pretty hand up and down it. You know how, baby!" His hand worked its way up to my panties, and he put his hand inside them and gently rubbed my cockette and little balls. "You're so sweet, Melissa. You're all excited and hard for me. Let me help you!" Kenny pushed my skirt and petticoat up and started to stroke my little penis, which was dwarfed by his monster I was stroking. It didn't take long. With his tongue deep in my mouth I shot my sissy juice all over myself. Kenny took his sticky fingers and brought them up to my mouth, breaking our kiss. "Now lick my fingers clean, honey. There's a good girl!" I pulled my panties back up and lowered my skirts. Kenny kept my hand stroking him. "Now, baby - it's time for you to return the favor. A girl can't get a guy all worked up and then leave him like that! I resigned myself to jacking Kenny off, but that's not what he had in mind. "No, Melissa. That's sweet, but I can do that for myself. I want you to kiss and suck my cock!" "But, but?I've never done that before!" "Just kiss it then!" I looked at it and knew I wanted to. I leaned over and holding it in both my hands I kissed the very tip. It was sticky on the end but I kind of liked it. Kenny moaned and spread his legs further. It was so big! I then felt Kenny's hands on the back of my head. "Come on, Melissa, don't be a tease now. Lick it and suck on it!" With his reassuring, commanding voice and his strong hands on my head I took more into my mouth. I began going up and down on it with my mouth. It was so warm in my mouth ? so natural there. I would slowly suck it from the salty tip as far down as I could go ? only half way. There were veins in it that I could feel on my tongue as they ran over it. Kenny relaxed and spread his legs even further and released his hands from my head. He didn't really need to hold my head on his cock ? I wanted it there. "Oh yeah, baby. That's it. You really know how to suck a man's cock! How many cocks have you sucked Alan? I mean Melissa?" I stopped sucking and looked up at him. "None, Kenny?yours is the first!" "Well then you're a natural. I'm proud to be the first, and I just know you're going to suck a lot of dick in your life. You're a natural born cocksucker! Look at you - all dressed up real pretty on your knees with your lipsticked lips wrapped around my big cock! He continued talking as I sucked and slurped on his juicy cock. I found I had relaxed enough that I was taking more of it down my throat. I nearly had the entire cock down my throat. It was so delicious! "I've always known that someday you would have my cock in your mouth you know?I always figured you were a little faggot. You really do make a better girl than a boy!" "Hey! Watch your teeth!" "I'm gonna fill your mouth with big gobs of my cum, Melissa ? because that's what girls need ? to be down on their knees making a man feel good until he feeds them his spunk. That's it sissy Melissa in her pretty party dress ? make me cum!" His nasty talk made me voracious for him to cum. I wanted to drive him crazy with my mouth and drink his cum like a good girl should. I could feel his cock jumping in my mouth and it had swollen even bigger. He put his hands back on my head and began thrusting in and out. "Hang on Melissa. I'm gonna fuck your face now ? like your mouth was a pussy. Oh God, you are so hot and I've got a huge load for you. Be a good girl and swallow every drop!" I gagged a little as he thrust in and out of me. I was powerless to stop him from fucking my face and accepted my fate. I wanted him to come in my mouth ? I was desperate to taste his cum. I was so excited inside I was shaking, yet my little clitty was soft in my panties. I had never felt like this before. He shook and moaned and then went very stiff, holding my head firmly on his throbbing cock. I felt it spurt at least 5 or 6 times and I swallowed his hot cum as quickly as I could. It seemed like a reward to me, for doing such a good job of sucking his cock. When I had gotten every little spermie in my mouth and licked his cock and balls all nice and clean I looked up into his face. Kenny smiled at me and patted my head as if I were a child. "What an eager little cocksucker you are, Melissa! Did you enjoy sucking a man's cock?" "Yes Kenny, I did!" "Well now I want you to do something for me. Stand up here in front of me and take off your pretty panties." I lowered my panties, instinctively obeying him. I stepped out of them and felt my petticoat against my bottom and boy parts. "Now I want you to twirl for me ? very fast!" As I twirled my skirt and petticoat felt so nice rustling in the air and I could tell I was exposed underneath. Kenny had an evil grin on his face. "You sure do have a little cock, Melissa?it's more like a girl's clitty, isn't it?" "Umm, I don't know, Kenny I've never been with a girl before." "Well, my guess is since you're a little sissy with a tiny little dicky you never will. Girls like men to have a nice big cock to please them with. A cock like mine!" Kenny continued to casually grope his hardening cock as he spoke to me. "Now Melissa you have been a naughty girl and I want you to lay down over my lap!" I tried to think what I could have possibly done?.I had sucked Kenny as good as I could for my first time? I did as I was told and laid over his lap. He raised my skirt and petticoat up to reveal my naked bottom and I laid there nervously. Kenny took his hand and gently ran it over my bare bottom. "Your butt is so smooth and girlish, Melissa. It's so sweet and pink, but you disobeyed me and now you must receive your punishment. I was really scared. "But what did I do Kenny?" Out of nowhere I felt his hand hardly slap my left cheek as I jumped in shock and pain. "You bit my cock when you sucked it?and you didn't swallow all of my cum like I told you to! You have to learn to obey, Melissa!" His hand slapped down hard on my other cheek and I shrieked a little. He kept spanking me over and over ? first one cheek and then the other. After a few minutes I began to wiggle my legs and try to get free. Kenny just laughed and held me even tighter. The spanking continued as my bottom really began to hurt and I started to cry softly. There was nothing I could do. Kenny was a boy after all and very strong, and I couldn't stop him. "You have to watch your mouth when you suck a man, sweetheart?it hurts when you bite! I know you were enjoying yourself and you got a little carried away but a girl needs to learn to respect a man's cock and treat it like a precious gift! And to boot I told you to swallow all of my cum and I saw some leak out of the corner of your mouth! It's stained your party dress! How are you going to explain that?" Between my sobs I answered him. "I'm sorry Kenny, I didn't want to hurt you ? I wanted to make you feel good ? it's just that it's my first time! And I tried to take all of your cum but there was just too much for me all at once! I'm really sorry. I promise I'll do as you say!" "Well as long as you will be careful to listen to me and obey me we'll get along just fine. Just remember that I'm the man in this relationship and you're the girl and will do as you're told!" "Here honey, grab onto this for a bit." He guided my hand to his cock which was now rock hard again. He took his hands and gently rubbed my bottom. "Oh Melissa! Your ass is so hot all red like that! It feels so warm and smooth!" His rubbing felt very nice. I then felt a wet finger at my hole. I gasped in anticipation of what was to come. "You have such a nice little rosebud, baby. I'm gonna make you feel all better!" Kenny inserted his wet finger all the way inside me, and then moved it in and out. "Have you ever had a man fuck you? Melissa? Tell me the truth!" I hesitated. "No Kenny, but I put my Mommy's dildo in there a few times." "Well well?then I guess two fingers will feel pretty good then?" I felt a second finger inside me and he proceeded to finger fuck me as I laid there helplessly with a hand on his throbbing cock. "You have such a hot little cunt Melissa?so hot and ready for fucking!" "Get off my lap and lay down on the couch ? now!" I did as he said and he positioned me so that my ass was hanging over the edge. My legs were pulled up and my skirts were raised exposing my vulnerable hole. Kenny leaned over and put his mouth right up by my hole. "I've eaten pussy before Melissa and now I'm going to eat yours. Then I'm going to fuck it!" I gasped as he kissed all around my hole and then I felt the tip of his tongue at the opening. He put it inside me and proceeded to dart it in and out. "What a hot little pussy! Do you like that girl?" "Oh God yes Kenny?please don't stop!" He just laughed and stopped after a minute or so. Reaching into his jeans pocket lying on the floor by the couch he pulled out a tube and stood in front of me as I laid there spread out for his pleasure. "Be a good girl and put some lube on my cock so I can fuck you!" I took some of the clear jelly and put it all over the cock, making sure to cover it thoroughly. I knew I couldn't stop this from happening ? I didn't WANT to stop it from happening?and I wanted it to be as painless as possible. When his cock was fully lubed he put it against my hole, intently watching me. "I like you on your back like a girl! I want to watch your face as I push it inside you!" He leaned over and I grabbed onto his arms which were straddling me for support. His arms had such nice muscles! He pushed a little and the head went in. I gasped and shrieked a little. "Easy girl, just get used to it for a minute. You're a virgin after all!" I took some deep breaths and the pain subsided. He pushed in a little further. I arched my back and wrapped my legs around Kenny's back, which actually pulled him deeper inside me. Kenny smiled above me, watching me intently, and buried his cock all the way inside me. "There we go! You've got all of my cock inside your pussy now! You are so tight! I think you're the hottest fuck I've ever had!" Kenny began slowly pulling his cock almost out of me, and then thrusting all the way back in. Each time he did it I felt a chill, my nipples became harder, and I was panting. Nothing in my life before had ever compared with this! Having a man's hard cock inside me, helpless beneath him was just incredible! "Oh God Yes! Fuck Me Kenny! Fuck me hard! I want it Soooooo bad!" Kenny eagerly picked up his pace. He was an expert, mixing long deep strokes with short powerful jabs. He leaned over with his head close to my face and kissed me deeply and nuzzled my neck as he fucked me savagely. "Oh girl I am gonna give you a huge load of cum in your pussy ? you'll see?My cock feels so right in your snatch! I'd make a baby inside you if I could?I'll bet you'd like that, wouldn't you?" "Oh yes, Kenny?please don't stop!" "Sorry, baby but I'm gonna shoot. Hang on!" I held Kenny tightly as he grunted against me and with a massive shove that nearly made me pass out he leaned close to my ear. "Here it comes, Melissa?a big load of jiz for the birthday girl. Happy Birthday to you?.Happy Birthday to you?. As he finished softly singing the birthday song I felt him spurt inside me as I held him tightly. I had an overwhelming feeling of pleasure ? a girly cum if you will?my nipples were hard and I was tingly and short of breath. I didn't want this to end, and knew this was the first of many fuckings I would experience. As we both clamed down his cock softened and slipped from my dripping hole. I felt wonderful as he softly kissed me. It made me so happy to bring a man so much pleasure. The satisfaction I received, the awareness of who and what I really was and needed in life?it was the best birthday present I could ever receive.

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Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

3 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

3 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

4 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

2 years ago
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Happy Birthday to Me FEMDOM TRAINING

It was the early 90s; I was taking a full load in college and working full time. At nineteen I was making good money, going to school, and just married my high school sweetheart. I know it was too young, but it was 90's and I thought the only way out of my parent's house was to get married. We were married for a year now and, at twenty, we had a nice two bedroom, spacious, corner apartment on the second floor of an apartment duplex. My wife, Carol, was 5'4", 115lbs, short brown hair, blue eyes,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 49
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 44
  • 0

What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

3 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

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