AdultBaby Sissy Archives - Page 11 of 15

October 26, 2012

Published by Mommy Maddy at October 26, 2012

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A Good Cleaning

Do you what day it is? It’s the day that one of your “Uncles” comes over for a very special visit. Now don’t be like that, you know how much all your Uncles adore coming over and visiting with you. And you know how they like you cleaned up extra special for them. You need to be a good boy for Uncle, or he will be very cross with you, and punish you severely – you remember last time you were naughty and got punished, now don’t you? By that wide-eyed look of terror, I am gathering that you do. It hurt more then you possibly could have imagined, now didn’t it, so be a good boi and get you cleaning. Now hop up on the table, and let me insert the enema nozzle up that sissy hole of yours my dear. Uncle has made a special request this week. He wants you to hold your water until he arrives, and then see you empty your bowels into a double layered diaper in front of him. So after I make you take the two quarts, I am going to plug you up with an inflatable plug, diaper you up, and get you dressed exactly how Uncle like you – pink frilly dress, lace gloves, white anklet socks with Mary Janes. And you know how much he likes your pink lips gloss, don’t you! Yes my sweet little sissy boi, it will become uncomfortable, and more then just a little painful holding your water until Uncle gets here; but he wants to make sure you have a good cleaning, so if you feel the need to cry, you go right ahead and let those tears flow – Uncle likes to see you cry too, hehehe. Ready for your cleaning my diapered sissy? Lexus 1.888.430.2010

October 16, 2012

Published by Mommy Maddy at October 16, 2012

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Mommy’s Night Out

Oh don’t look like that you with that cute little sad face i know you want to go with mommy tonight but sweetie you can’t tonight i rarely leave you in the care of a sitter but i need some time out also.Look at it this way you will have such a wonderful time while mommy is out for a bit. The sitter will give you snacks and nice warm bath read you a cute bedtime story she might even play some games with you oh and guess what darling she loves changing diapers now see there i know you could smile big for mommy.You also know how much i love that adorable smile you always give me,Now do mommy a favor and make sure you make lots and lots messes for Josie heheh she loves those messy diapers.And especially sissy girl babies i have already told her where i keep those special mommy stockings i keep just for you at bedtime.Oh now one thing mommy forgot to tell you Josie might bring along some friends like AvA,,Samantha,Crissy,Gina,just never know who might show up with her might even be Minnie hehe just never know sweetie. Rebecca 1.888.430.2010

September 13, 2012

Published by Mommy Maddy at September 13, 2012

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Basement Sissy Baby

My best friend came over the other day upset and a bit lost – she wasn’t sure what to do with what she had discovered. You see, she had told me that she recently caught her husband being naughty in the basement and wearing girly clothes – I mean frilly little girly clothes, complete with ruffles and lace, right down to little white ankle socks and Mary Janes. I big smile came over my face; I told her I knew just what to do with her basement sissy. If he wants to be a naughty sissy baby, then I would be more then happy to help her train him up proper like. If her hubby wanted to be a naughty little sissy, then I would be pleased as bunch to give him exactly what he asked for – a classic case of “be careful what you wish for” if ever I’ve seen one. Well, I won’t go into details here (feel free to call me and ask for them though, hehe), but to make a long story short, his wife is now humiliating him under my teachings. I play with the sissy baby’s hair and make fun of her; I take her to the mall with me shopping to humiliate her; I make her dress up and suck her binkie when we are out; the list is quite extensive! It is so much fun training a new sissy baby. So tell me…are you a basement sissy baby in need of some of Mommy Lexus’ training? Dommy Mommy Lexus 1.888.430.2010

September 10, 2012

Published by Mommy Maddy at September 10, 2012

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Playing Dress-Up

I love playing dress-up with my sissy friends!! Daddy always spoils me so I have the prettiest dresses and shoes and makeup! The other day my sissy friend Owen begged me to come over to play dress up. I told him that of course he could come over and that I had a whole bunch of new dresses that he could try on. Annnnd I had just gotten a brand new strap on that I wanted to play with. Ten inches long, nice and thick, and a pretty pink glittery color! Owen came over and we went right up to my room and we opened the closet. Owen was so excited when he saw all my pretty girly dresses. He said it was too hard to pick one because there were too many and they were all too pretty. I flipped through them till I found the perfect one. Short and bright pink. I told Owen that it would fit him just right. Tight over his body and the ruffles underneath would make the dress stick out so his pretty panties would stick out. I gave him a pair of my white cotton panties with little flowers on them and helped him pull the dress on over his head. Owen twirled around in front of the mirror and giggled. “Want me to put some makeup on you?” I asked. Owen bounced up and down in excitement. After I put on my own pretty dress, sparkly silver with a bow around my waist, I sat Owen down and opened my makeup case. I brushed blush across his cheeks and sparkly eyeshadow over his lids. Made his eyelashes long and luscious with deep black mascara and smudged bright pink lipstick over his lips to match his dress. I finished him off with a sparkly lip gloss that made his lips shimmery and sexy! After I freshened up my makeup I let Owen kiss me so he could feel the way our lips slid against each other with the gloss! Soon I was putting on my new strap on and bending little sissy Owen over, pulling his panties down to get him ready to take my big toy! Wanna come play dress-up with me? I have sooo many cute and sexy dresses to try on, and lots and lots of toys to play with!! kissies, Cali 1.888.430.2010

September 8, 2012

Published by Mommy Maddy at September 8, 2012

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Sissy shopping with Mommy Josie

We have been training for weeks now. And now I think it is time for a special outing. This will be your first time in public since your transformation. It’s time to go sissy shopping with Mommy Josie. We have worked so hard for these past weeks now. Mommy has taken you through all the steps, bringing out your feminine side. We started with you as a sweet AB sissy girl and mommy took you through all the steps to becoming a young lady. And now it is time for your first training bra. Mommy is so proud. So go get ready like a good girl. I want you in your pre-teen sissy girl best today. All short skirts and tight tops with glossy pink lips. We will go to mommy’s favorite lingerie store and ask the sales lady to measure you so we can get the perfect fit. Awww, don’t be embarrassed sweetie, I know the sales lady is giggling but you will be so proud later when you model your new bra tonight for mommy’s friends. Your Nannies, Miss Scarlet and Miss Crissy are so excited to see you all grown up now. Maybe we can invite all the sitters too, I know they will just get a kick out of teasing you too. And now that you are such a big girl, you will have some shopping assignments to complete on your own. I know how much you love sissy shopping with Mommy Josie however, sissy young ladies like yourself must learn to do their own shopping as well and Mommy Josie is here to teach you just how to do that. All you have to do is pick up the phone and tell mommy you are ready for your very first Big Girl Sissy Assignment. Perhaps if you ask very nicely, mommy will come along and watch. But the rest is up to you… Mommy Josie 888~430~2010

August 19, 2012

Published by Mommy Maddy at August 19, 2012

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Training Sissies

I love ass training sissies. Although I have many in my care, I especially enjoy the ones I have from the very beginning. Being able to train them through from taking a finger, all the way to a 10 inch strap on is just so much fun. When a sissy comes to me they are usually very nervous. They know what they want but are sometimes embarrassed or ashamed to admit it. I take them in my care and treat them gently, knowing that I’ll have them begging for more soon enough. After I get them into matching panties and bra and a pretty dress, I get their training started. I always start them with a finger, usually holding them over my lap and slowly sliding down their panties so I can caress my sissy’s ass with one hand as I rub their hole with a lubed finger. I push my finger in slowly, massaging inside sissy to ease them open more. After a while I push in a second finger, then a third. By this point, my sissy is always moaning and rubbing against my lap. They rock their hips matching my thrusting fingers. From fingers we move on to various sized plugs. I love watching my sissies squirm as I maneuver the toys inside them, starting with the smallest. They of course learn to love each one and in fact crave more. Often my sissy will make a big creamy mess on my lap while I pump a toy inside them. And then in no time at all my sissy is ready to take my strap on like a good sissy should. When it’s sissy’s special first time I dress them in the prettiest dress I can find with a new panty and bra set. I let them suck my strap on first, taking it deep in their throat like a good sissy. She rubs her big sissy cock while she sucks me. Then I bend her over and pull her panties to the side, squeeze a glob of lube down her crack and rub it against her hole with my strap on. I have my sissy spread herself open for me so I can push the tip into her tight little hole. I can tell it’s hard for her to hold her cum as my strap on pushes further in. Slow steady pumps at first, turning into deeper harder thrusts, making my sissy moan wildly till her cock shoots a creamy thick load. Once my sissies are fully trained, their hunger for my strap on can never be satiated. If you’re ready to be a good little sissy, come to me and I’ll give you a training you’ll never forget. xoxo Samantha 1.888.430.2010