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Nanny Susan invites all sissies to write to her with their problems, fears, and questions. 1. Dear Nanny Suzanne Recently my wife mommy gave me a pair of frilly panties for my sissy birthday. When I put them on I got so excited that I squirted and soiled my new panties. Mommy was furious. She says she will keep me in diapers until I learn not to soil my panties. I really hate diapers. How can I convince mommy that I'm a big girl enough to wear panties again? Dear diapers Sounds like somebody needs to learn to control himself. Ask your mommy if she will buy you a CB 600-chastity device, which will help keep your silly little naughty thing under control. You must be extra well behaved and not make any mistakes as long as you are in diapers. Perhaps after a time when mommy sees how good you are she will give you another chance. Good luck. 2. Dear Nanny Susan Whenever my friend Sissy Julian comes over he always makes a it point to show me the pretty bra he is wearing. Sissy Julian has boobs that's why he gets to wear a bra. He knows I don't have any boobs and don't wear a bra that's why he's always telling me about his bra. I know I'm supposed to like Sissy Julian and most of the time I do, but I hate being so flat-chested and not having any boobs and not being able to wear pretty bras like Sissy Julian. I asked my mommy and she says I'm too young to have boobs. Dear flat-chested Sissies develop at different rates and if your mommy says you are too young to have boobies, then you are too young because mommy is always right. Talk to your mommy about the situation. Tell her how you feel. Tell her about how Sissy Julian is always showing off his bra and how it makes you feel. Maybe your mommy will talk to his mommy. Good luck. Dear Nanny Susan Thank you so much for the wonderful advice. My Mommy talked to Sissy Julian's mommy and Sissy Julian got a good talking to and came over and apologized and we hugged and kissed and are friends again. Mommy says I'm still too young to have boobs but she promised to take me shopping for a training bra. I hope I can find a pretty one just like my good friend Sissy Julian has. I can't wait! 3. Dear Nanny Susan I feel so dumb. Many of my other Sissy friends are having periods and using tampons. And they're always talking about which tampon they are using and how it feels and discussing the various types. I don't know what they're talking about and when I ask them they just look at me and shake their heads and tell me I wouldn't understand. I asked my mommy but she says I'm too young to start having periods. I hate being left out. I feel like such a dumb bunny. Please help. Dear Dumb Bunny Having periods and starting to use tampons is a very important stage in the life of any Sissy. It's not nice that your friends leave you out of their discussions. If mommy thinks you are too young, then you are too young because mommy knows best. You might ask your mommy in your politest voice if she would please explain to you about tampons so you don't feel like such a dumb bunny. If mommy agrees well and good. If she declines you'll just have to wait until she decides you are old enough. 4. Dear Nanny Susan Mommy and I often go for a walk in the park. Recently I saw another mommy and sissy walking in the park. The Sissy smiled at me and blew me a kiss I think he likes me and I would like to know him better but I don't know what to do next. Please help. Dear Don't Know Maybe you can ask your mommy to talk to his mommy. Many mommies like their sissies to have other Sissy friends. Dear Nanny Susan Thank you for the wonderful advice. My mommy talked to the other Sissy's mommy and now I have a new Sissy friend. We hugged and kissed and played together. I'm so excited every time he comes over. 5. Dear Nanny Susan For the past several years I have been a good little girl for my wife mommy. Recently mommy met a man at work and started going out with this man. When he comes over to our house, mommy makes me stay in my room. I think they make love in mommy's bedroom. Now mommy has decided that she wants me to suck his cock. I want to be a good girl for mommy but I'm afraid. Please help. Dear Afraid Sucking cock is a big step for most sissies so it's to be natural to be afraid. Ask your mommy to buy you a dildo to practice sucking on. Ask your mommy to help you learn how to suck a dildo. After you've learned to suck a dildo properly, it won't be as scary when you suck a real cock. Ask your mommy if you can take it slow and easy, explain to her that you still want to be her good little girl. Good luck and don't forget to swallow. 6. Dear Nanny Susan My name is Mary Jane and I have been a good little girl for my wife mommy for some time now. We are both very happy. Now mommy has decided to introduce her little girl to her sister. She wants me to meet my new auntie. No one else knows that I am mommy's little girl and when I think about meeting my new auntie, I get so afraid I just want to run and hide. Dear Run and Hide Meeting new aunties can be very stressful for a Sissy, so it's natural to be afraid. Ask your mommy to help you practice greeting your new auntie so when you meet her you will make a good impression. Ask your mommy to pick out a pretty outfit for you to wear when you meet her. When you are wearing your prettiest outfit and using your best manners I am sure your new auntie will like you. Good luck. 7. Dear Nanny Susan Every time a bunch of my Sissy friends come over they always make fun of me because I have the smallest thing of all of them. It's barely 2 inches long. They all think they're so important and so much better than me because their things are three and 4 inches long. I hate being the shortest. Please help. Dear Shortest It's not very nice of your Sissy friends to make fun of you because your thing is the shortest. Ignore them and their rude comments and be the best Sissy you can be. Remember having a small thing means you have a smaller bulge in your panties and they will fit better for you. Tell your rude friends that you are a better Sissy than they are and your panties fit better because you are smaller. Good luck. 8. Dear Nanny Susan I am my wife's Sissy maid and when she has her ladies club over I serve them in my pretty French maid uniform. The reason I am writing to you is I have a problem. When I am bending over serving coffee or cookies, the ladies squeeze my bottom or rub my legs and it gets me very excited and I'm afraid I will have an accident. One time I got so nervous I almost spilled the coffee on one of my wife's lady friends. After they had gone my wife asked what the matter was. I explained to her how the ladies squeeze my bottom and rub my panties and stockings and how I was afraid I would have an accident. She said it was good for me to be nervous and that the ladies were free to rub my bottom or anywhere else they wanted to. But I'm still afraid I will have an accident in my panties and I know my wife would be very angry with me. Please help. Dear Sissy Maid Serving your wife's ladies club is a part of your Sissy duties and is normal for ladies to want to explore what a Sissy maid is wearing under her skirt. It's understandable that the Sissy would not want to spoil her panties. Ask your wife could you please have a CB 600 chastity device. Explain to her that this will help keep you from having an accident in your panties and will allow you to concentrate better on your serving duties while still allowing the ladies free rein for their exploration. 9. Dear Nanny Susan My friend Sissy Lenny comes over and we have a lot of fun playing dollies together. One day Sissy Lenny told me he was getting a new doll and he would bring it over the next time he came. But he didn't. When I asked him about it, he told me he had forgotten it at home. Now every time he comes over I ask him about his new dolly but he never brings it over. I told him I thought he didn't have a new dolly, but he said he did. I asked him where is it? And he said he left it at home. I said he didn't have a new Dolly and he said he did and next thing we were hitting each other and pulling each others hair and our mommies came into the room and spanked us both and made us apologize to each other. I still don't know whether or not Sissy Lenny has a new dolly. If he does why doesn't he bring it over? Doesn't he like me anymore? Please tell me what to do. Dear Dolly It's not nice of Sissy Lenny to not let you see his new dolly. It's hard to know the reason why. Maybe Sissy Lenny did not get a new dolly and he is telling you a fib in which case his mommy should spank him soundly. Maybe Lenny did get a new dolly and he doesn't want you to see it because he is afraid you might break it. Talk to your mommy and tell her what Lenny said maybe she will talk to Lenny's mommy. Dear Nanny Susan I did what you said. I talked to my mommy and told her what Lenny said. She talked to Lenny's mommy and it's true that he did get a new dolly. Mommy explained that Lenny does not want to bring his new dolly over because he is afraid it might get broken and he loves it very much. My mommy took me over to Lenny's house and I got to see his new dolly after I promised him I would not break it. In fact I did not even touch it. It is such a pretty dolly I can see why he loves it so much. The dolly has long blonde hair and is wearing a pretty dress with lots of ruffles and lace and the dolly is wearing Mary Jane shoes just like the ones that Lenny and I wear. I'm so so happy that Lenny got a new dolly and I'm glad he was not telling a fib because I do not want to see him get a spanking because we are friends. I told Lenny what a pretty dolly he had and thanked him for letting me see it and we hugged and kissed and mommy took me home and that was the end of an exciting day for me. 10. Dear Nanny Susan Mommy met a new mommy named Erica. Mommy Erica has a Sissy named Fred. Whenever I mommy Erica and Sissy Fred come over mommy tells me to play with Sissy Fred while she and mommy Erica talk in the kitchen. Sissy Fred makes me suck his Sissy thing and swallow his Sissy juices. I don't want to do it but he says if I don't he will tell our mommies that I said a bad word and was mean to him. He says if I ever tell anyone he will send his big sister over to spank me until my bottom is as red as can be. I tell him it's not right and that he should suck my thing once in a while, but he only laughs and asks if I want his big sister to come over and spank me. I don't know what to do please help. Dear don't know what to do Sounds like Sissy Fred needs a spanking. Tell your mommy what is going on and explain to her what Sissy Fred is telling you and asked her if she will talk to Sissy Fred's mommy. Dear Nanny Susan I did what you said. I told my mommy what Sissy Fred said and how he made me suck his thing every time he came over. My mommy told Sissy Fred's mommy and Sissy Fred got such a spanking that he was not able to sit down for a week. Sissy Fred's mommy made him come over and apologize to me and my mommy and made him suck my thing just as many times as he made me suck his. So at least we are even she also put Sissy Fred in a chastity device and told him he would be wearing it for a good long time. And threatened him with diapers if he ever misbehaves again. And I found out that Sissy Fred does not have a big sister and he was fibbing the whole time. After all that our mommies made us hug and kiss and now we play together nicely and I think we are going to be friends. 11. Dear Nanny Susan I have a problem. There is this friend of mine named Sissy Allen. Whenever Sissy Allen comes over he always says he is having his period and wants to borrow one of my tampons. I don't mind lending him one of my tampons now and then but I think every time is too much. I can't help but wondering if he is really having his period or if he is just saying that. What should I do? Dear wondering Mommies always tell Sissies when they are having their periods. But it seems strange that your little Sissy friend is always wanting to borrow a tampons. Explain the situation to your mommy and ask her to talk to Sissy Allen's mommy. Maybe Sissy Allen is really always having a period and needs a tampon. Dear Nanny Susan My mommy talked to Sissy Allen's mommy and found out that Sissy Allen is too young to have a period. Sissy Allen's mommy was very upset to find out that he had been borrowing tampons. She made Sissy Allen come over and apologize to me and my mommy and then she gave him a good spanking in front of both of us. Then Sissy Allen hugged and kissed me and told me how sorry he was and promised he would never borrow a tampon from me again. So at least now my tampons are safe. And Sissy Allen and I are friends again. 12. Dear Nanny Susan I am Bridget my wife's cuckold sissy maid. As Bridget I am kept in chastity and my wife makes me suck cocks of her lovers. But I am becoming worried, because whenever I see a man my eyes go immediately to his crotch, and I wonder how big his cock is and I wonder how it would feel in my mouth. I also wonder what his cum would taste like. I find I cannot help myself. I cannot stop thinking these thoughts. My worry is, am I becoming a slut? Dear Worried As a Sissy maid in chastity, the only relief you are getting is sucking your wife's lovers' cocks. So it is no wonder that you are obsessed with them. It is apparent that you are on the way to becoming a slut, and that is obviously what your wife wants to make of you. So do not worry, enjoy. I am confident your wife is pleased with your status and your performance. 13. Dear Nanny Susan My Name Is Millie. Even though I have boy parts, my mommy says I am a girl and makes me do girl things and wear girl clothes. Mommy is happy that I am her little girl and I am happy being her little girl. But lately I have been having a problem. There is this boy who lives across the street and he knows I have boy parts but he says it doesn't matter and he treats me as a girl whenever he comes over. He wanted to put his hand in my panties but I wouldn't let him. We kissed. It was kind of messy but I liked it. Now whenever he comes over we always kiss and hug, I won't let him go any further. Lately I have been noticing some of my panties are missing. I have many pretty panties and sometimes I cannot find the ones I want to wear. I don't know where my panties are going, and mommy is starting to ask questions I don't know what to tell her. Please help. Dear Millie It is nice to hear that you have accepted your role as mommy's girl Millie. I think you are wise to not let the boy get into your panties. I am sorry to hear that you are missing panties. My suggestion is you talk to mommy and tell her you do not know where your panties are going. Perhaps your little boyfriend is taking them. Perhaps your mommy would ask his mommy. Good luck and I hope you find your missing panties. Dear Nanny Susan Thank you for your wonderful advice. Mommy talked to his mommy and you were right he has been stealing my panties. His mommy made him return all the panties he had taken and apologize. His mommy said she had punished him with a good spanking. He admitted he likes wearing panties and his mother promised me that from now on he would be wearing his own panties. She also said she has decided to make him into a girl because she has seen how well my mommy did with me. So it looks like we are going to be girlfriends, I'm so excited! I've never had a girlfriend before. I just know we are going to be good friends. 14. Dear Nanny Susan I am Jamie my mommy's sissy girl. My mommy spanks me every day even when I haven't done anything. I try so hard to be a good little girl and make mommy happy. I ask mommy what I have done wrong, she never answers me and I get a spanking anyway. Mommy says a spanking a day keeps the naughty away. I try to be the best little girl I can for mommy. I try to be clean, polite, obedient, and neat. I wish mommy did not spank me every day. I do not think it is fair of mommy spank me when I haven't done anything wrong. Please help me. Dear Jamie If mommy has her heart set on a daily spanking for you, there isn't much you can do about it. If you complain, your mommy may assume that you are being disobedient and spank you even harder. Nanny advises you to take your daily spanking like the good little Sissy you are and remember mommy loves you and mommy is always right. 15. Dear Nanny Susan I heard from my friend Sissy Alice that her mommy gives her an enema every day only her mommy calls it a douche. Sissy Alice says her mommy uses a big scary nozzle on a bag of warm soap and water. She inserts the nozzle in Alice's bottom and makes her keep it in until all the water has drained out of the bag. Sissy Alice says her tummy fills with warm water and she has to hold it in until mommy removes the nozzle and if she doesn't she will get punished. Sissy Alice says her mommy does it because she wants her little girl to be clean inside and outside. Now my mommy told me that she wants me to be clean inside just like my friend Sissy Alice. I'm afraid she will start giving me a douche every day just like Sissy Alice's mom does. The nozzle sounds so big and scary. I don't want mommy to put it in me. I'm afraid the water will be too hot and it might hurt me. When I think about that big nozzle I just want to throw up. Please help me. Dear Afraid It's very important for sissies to be clean inside as well as outside and I'm sure your mommy just wants to make you the best Sissy that you can be. Douching does sound scary especially the big nozzle, but I am sure your mommy will lubricate it well so it does not hurt you when it is inserted. Do not be afraid that the water will be too hot, I am sure your mommy would use nice warm water with just a touch of soap, in order to make your insides just as clean as they can possibly be. Douching is an important stage in your development as a Sissy and there's nothing to be feared. So be a good little girl for your mommy and remember mommy knows best. 16. Dear Nanny Susan, My friend Sissy Henrietta comes over every day and mommy makes me suck his thing because she says that sissy juice is good for me. At first I hated it and didn't want to do it,but after a while I started to like it and now I look forward to it every day. Sissy Henrietta's thing is 3 inches long and fits perfectly in my mouth. I love the way it gets excited and I love how excited Sissy Henrietta gets when I suck his thing and he squirts in my mouth. If I take his thing all the way in my mouth when he squirts it goes straight down and I can hardly taste his sissy juices. Mommy is happy because she says the Sissy juices are good for me. Sissy Henrietta is happy because he gets his thing sucked, and I am happy because it is so much fun for me to suck Henrietta's thing. But mommy says in a few days I will not be able to suck Henrietta anymore. When I told this to Henrietta he got upset and started to cry. Mommy came in to find out why Henrietta was crying and she explained that in a few days she wanted me to start sucking Sissy Roberto's thing. Mommy said the Sissy Roberto measures 5 inches and it would be good for me to practice on his thing. She said that Henrietta can still come over and that Henrietta and I would still be friends and if I wanted to I could still suck Henrietta's thing once in a while but from now on Sissy Roberto would get most of my attention. I know Sissy Henrietta was disappointed and I am sure he thought I was a size queen but I have to do what mommy says. But I'm afraid. Will Roberto be too big for me, will Henrietta still like me? Will I like Roberto the way I like Henrietta? Dear Sissy Change is always scary but I am sure after a few days sucking Sissy Roberto will be just as much fun as it was sucking Sissy Henrietta. And I am sure 5 inches will not be too big for your Sissy mouth. Like your mommy said you can still see Henrietta from time to time I am sure in time you will come to love Roberto as much as you did Henrietta and two of you will be fast sissy friends. 17. Dear Nanny Susan My name is Emily and I am my wife mommy's sissy girl. I have a story to tell. One day I sneaked into mommy's bedroom to look around. Mommy doesn't let me in there without her permission, but I was so curious I just had to see what it was like. Mommy's bedroom was so interesting. It was filled with all her things and smelled so nice I couldn't resist going in. I was standing in mommy's bedroom when I opened up one of the drawers in her dresser and the drawer was full of her panties. Mommy had such nice panties I could not resist trying on one of mommy's panties. It felt so nice and my sissy thing get so excited that I accidentally squirted in mommy's panties. I was so horrified and scared of what I done that I put the panties back in the drawer as quick as I could and got out of mommy's bedroom and pretended nothing was wrong. But after a while mommy went into the bedroom and the most terrible thing happened she opened the drawer and found the panties. She called me into her bedroom and asked me if I had done this. I said I hadn't but mommy knew I was fibbing and I had to admit the truth. Mommy was so angry she took me over her knee and spanked my bare bottom right then and there. And then I had to stand in the corner with my panties down my dress up until mommy figured out what my punishment should be; she warned me not to touch my bottom or she would spank me some more. Finally mommy told me what my punishment would be. I had to wear diapers for a month and every time one of mommy's friends came over I had to tell her what I had done and ask her if she would spank me in order to help me become a better behaved little girl. Many of mommy's friends were ecstatic and eager to help so I spent a lot of time being spanked and standing in the corner. The embarrassing part was I had to thank them for my spankings and apologize to mommy every day. Finally at the end of the month mommy let me wear panties again and I was really glad about that and she gave me one final spanking and made me apologize again and the last part of my punishment is writing this letter to you. Nanny Susan says Let that be a lesson to all you sissies out there never lie to mommy, because mommy always knows best. 18. Dear Nanny Susan, My name is Sissy Jenny. I used to be a 16 year old boy named Johnny but I got in trouble and the judge gave me a choice of going to jail or becoming mommy's Sissy. I was very afraid of going to jail so I became mommy's Sissy. Even though I am 16 boy years old mommy says I am only 8 Sissy years old, so mommy dresses me like an eight year old girl. Mummy sends me out to play with the other little girls in the neighborhood and to make sure I do not get in trouble she locks my boy bits up and hides the key where I cannot find it. At first the neighborhood girls did not want to play with me and I did not want to play with them, but when mommy explained the situation to them and told them that they were in charge of me and that I had to do what they said or get a spanking, they changed their minds. Now they come for me every day. I have to play games with them, and pretend to be a happy little eight-year-old girl. Mommy dresses me in a sun dress and panties and puts frilly anklets and Mary Janes on my feet. I feel like such a Sissy especially since I am taller than all the other little girls and they really enjoy bossing me around. After a couple hours of play they bring me home and tell mommy that I misbehaved and that I deserve a spanking. They tell mommy that I was bad or that I pushed one of them or that I got my dress dirty. It really doesn't matter what they tell mommy because mommy always believes them. I try to tell mommy that they're always making stuff up but mommy always says I should not interrupt her and she always believes them anyway. Then mommy takes me over her knee, lifts my dress up and pulls my panties down and spanks me. The neighborhood girls all stand and watch and giggle. Sometimes mommy lets them spank me too. And then I have to apologize for misbehaving and I have to stand in the corner with my panties down, my dress up so everyone can see how red my bottom is. It's so embarrassing to be spanked with a bunch of little girls watching. I feel so humiliated at the way they laugh at me and tease me and I wish I could make it stop. I'm trying to become the good little sissy girl at mommy wants me to be because I do not want to go to jail. But I wish the neighborhood girls would stop telling fibs about me. It's bad enough having to dress in this sissy outfit which is suitable for a little girl half my size without having my bottom spanked so often. I wish it would stop. Please help me Nanny Susan. Dear Jenny, It sounds like the neighborhood girls are getting their revenge for all the bad things you did to them when you were a naughty boy. I'm sure you are not getting more than you deserve. Right now they are having fun bossing you around but soon they will get tired of it and leave you alone. So Nanny's advice is be patient little sissy. Who knows you may find yourself becoming friends with some of them. 19. Dear Nanny Susan, My mommy says that I will be starting my monthlies soon and that means I will start using tampons. My sissy friend Oliver says he heard that when I start my monthlies I will have to put a tampon in my bottom so my Sissy juices do not leak out. He says that tampons are 6 inches long and it hurts to put them in and they make you walk around bent over and you feel cramped all the time. Another sissy friend says that Oliver is all wrong and that tampons are used after your boyfriend has pumped his sissy juices into your bottom so that his juices do not leak out. I was so upset I asked my mommy if I could please not have my monthly flow, she said I was just being silly and a monthly flow was part of being a Sissy and there was nothing to be afraid of. But I'm still worried, is there really nothing to be afraid of? Please help. Dear afraid A Sissy's monthly flow is a very important stage in her development and tampons are an important part of that. What's your sissy friends have told you is all wrong and you should not listen to them. Your mommy is correct when she says that there is nothing to be afraid of, so listen to her and do as she says and you will be all right. Dear Nanny Susan When I was a boy I behaved very badly and mommy decided to make me a Sissy to improve my behavior. I resisted at first but now I have come to accept the fact that I am a Sissy. Here's the problem. The first time mommy put me to bed she put booties on my feet and mittens on my hands and put my nightie on me. Then she gave me a bottle and I fell asleep while sucking the bottle. The next morning I woke up and discovered I had wet the bed. I was so embarrassed. Ever since then mommy makes me wear a diaper to bed. She says I need the protection. I hate wearing diapers because I feel like such a baby. I am very glad I'm allowed to wear panties during the day. I begged mommy not to make me wear diapers to bed at night but she was adamant that I needed the protection. I continued to beg and finally she told me that if I could stay dry for three nights in a row she would consider leaving off the diapers. The problem is I can't do it. I try so hard. I go potty every night just before mommy puts my diaper on. I hold my Dolly and drink my milk from a bottle just like the good Sissy mommy wants me to be. But every morning I wake up my diaper is wet; it's so humiliating. I just can't seem to stay dry. I hate waking up wet every morning. What can I do? Dear Wet every morning Becoming a Sissy is often very stressful and it is perfectly understandable that you would suffer some loss of control. Once you get used to being a Sissy, Nanny is sure that your problem will go away. Just be patient and be the best little sissy you can. Good luck. Dear Nanny Susan, My name is Sissy Mandy and I have been my mommy's sissy girl for some time now. The problem is mommy only allows me to wear white panties. Many of my sissy friends are allowed to wear colored panties in pink and yellow and blue, or panties with frills or pretty patterns on them. I want to wear pretty panties too, but mommy won't allow it. She says I would just get them dirty and that I'm not responsible enough to take care of pretty panties. But I know I am. I know I am. I really really really want to wear pretty panties just like all my sissy friends. What can I do to change mommy's mind? Dear Panties It is understandable that a Sissy would like to wear colored panties just like all her friends. You need to convince your mommy that you are responsible enough to take good care of your panties. You need to be the best little sissy you can be. Show your mommy how responsible you are. Show her what a good sissy girl you are. Do your chores without complaining, help mommy whenever you can. Be extra good and point out to your mommy how well mannered and polite you are and tell her how hard you are trying to be a good little Sissy. Then ask her in your politest voice if she will please please let you wear colored panties. Ask her if she will let you wear a pair of pink panties for just one day so you can show her how responsible you are. If she agrees then you must show her how well you can take care of your panties. Do not soil or stain them. Show mommy how much you love them and how well you take care of them. Then ask mommy if you can wear your pretty pink panties one day a week. Perhaps mommy will agree and you could show her how responsible you are. If all goes well ask mommy please be allowed to wear pretty pink panties two days per week. When mommy sees that you know how to take care of your panties, she will probably eventually let you wear pretty panties every day of the week. Good luck and be extra good. Dear Nanny Susan, My name is Sissy Millicent and I'm 15 sissy years old. I don't know how old I am in boy years, but mommy says it's not important anyway since only sissy years matter. Mommy keeps my boy bits locked up, she says I don't need them anyway except to go to the bathroom. Sometimes my boy bits get all swollen up and they hurt, but mommy says to ignore them and the swelling will go down and it won't hurt anymore. Mommy unlocks my boy bits about once a week so they can be cleaned. If mommy finds any hairs there she pulls them out. Mommy says my boy bits should not have any hair on them. I'm not allowed to touch my boy bits when mommy is cleaning them and I have to stand with my hands behind my back so I won't touch them accidentally. Once when mommy was cleaning them I accidentally squirted and mommy was very angry and spanked me so hard I thought I wouldn't be able to sit down for a week. A lot of girls in the neighborhood are my friends and they all know about my special difference but they are my friends anyway. Mommy lets some of them come over and help her with my special cleaning. Not too long ago mommy started milking me. I am on my hands and knees with my panties down and mommy inserts this special thing in my bottom and when she finds just the right spot my sissy juices dribble out. Mommy catches them on a plate. After all the juices have dribbled out mommy makes me lick them up. She says that the juices are good for my complexion and that as a Sissy I have to be extra careful about my complexion. Sometimes she lets the neighborhood girls do the milking as well as cleaning. One time one of the girls was cleaning my thing and it accidentally squirted in her hand. I was horrified I thought she would be very angry but instead she just held up her hand and made me lick up my juices. If my thing gets hard or squirts, mommy says I am being rude. Mommy keeps my thing locked up so I won't be rude because nobody likes a rude sissy. I am always very embarrassed when mommy or one of the girls is cleaning my thing because I'm afraid it will get hard or squirt and I will get in trouble. Mommy says milking helps keep me from being rude. Recently I had another sissy birthday and among the presents I got was a dildo. It looked like my boy bits except it was a lot bigger. Mommy asked if I knew what to do with it and I said I did not. But one of the girls, her name is Sally, volunteered that she would teach me how to use it. Mommy said it was okay with her. Sally said there was no time like right now so she strapped on the dildo and made me lick the tip and the shaft to show how much I was enjoying it. Then they pulled my panties down and raised my skirt and made me bend over a foot stool. Sally knelt behind me and I could feel the tip of the dildo pushing against my bottom. Sally pushed hard and the dildo went into my bottom and all the girls clapped and cheered. I moaned because it hurt going in. It felt like I was being split in two and I was not conscious of anything else. Fortunately for me Sally left the dildo in place for a moment so I could get used to it. Then she slowly started moving it back and forth. With every thrust the girls watching cried boink. I don't know how many times I got boinked. The thrusting didn't hurt anymore and soon Sally withdrew entirely. All the girls watching clapped and cheered. I was so embarrassed about what I had experienced in their presence that I covered my face with my hands. I wanted to run and hide. But mommy made me put my hands down and thank Sally. The other girls wanted a turn, but mommy said that was enough for today and they could have their turn tomorrow or the next day. Then mommy made me thank them for coming and kiss each of them on the cheek before they left to go home. Dear Millicent, What an exciting day you had. Thank you for sharing your experiences. Please write again in the future and let us know what else you are doing. Dear Nanny Susan One day when my friend Sissy Roger came over, we hugged and kissed as usual. I felt his panty bottom and he felt mine. Then when I felt the front of his panty I noticed something new. He lifted his skirt and pulled down his panty so I could see. There was a plastic cage around his boy bits and it was locked with a little padlock. I asked him what it was and he said it was his protection. He said his mommy made him play with the neighborhood girls and that the neighborhood girls were mean to him. They always rubbed the front of his panty so his thing would squirt in his panties and then they would take him home and show has mommy what he had done. Then his mommy would spank him in front of the girls something which the girls enjoyed very much. Sissy Roger said he always told his mommy that it was not his fault; that the girls held him down and rubbed his sissy thing to make him squirt but his mommy never believed him until one of the neighbors saw what was happening and told her. Sissy Roger's mommy put his sissy thing in the protection and since then Sissy Roger has not soiled his panties anymore and mommy has not had reason to spank him. Sissy Roger was very happy that he was not being spanked anymore and that his mommy knew he was telling the truth. I asked Sissy Roger if his protection hurt. He said it only hurts a little when his sissy thing is being rude. Sissy Roger said that when his sissy thing gets stiff and sticks out the front of his panties, according to his mommy he is being rude. Before his mommy used to spank him for being rude, but since he got his protection she doesn't need to anymore. So even though it hurts a little Sissy Roger says he is happy because his mommy is happy and he doesn't get spanked nearly as often anymore. Now my mommy is talking about putting me in protection and I am a little worried and afraid. I am afraid because my sissy thing is bigger than my friend Sissy Rogers and I do not think it would fit in a protection. My sissy thing really is bigger than Sissy Rogers, that is true, mommy spanks me if I don't tell the truth. What can I do? Dear worried and afraid Sissy Roger's mommy has found a clever way to help her sissy become the best little Sissy can be. As for you, there is nothing to worry about, because protections, in different sizes and I'm sure your mommy will find one that will fit you. Do write and let Nanny know how things work out. Dear Nanny Susan You are absolutely right. Mommy was able to find a protection to fit me and now I wear it all the time. It really helps me be a good little Sissy. When Sissy Roger and I have been extremely good our mommies decide that we can have a sleepover. Sissy Roger and I really enjoy our sleepovers. Our mommies release us from our protections. I like to wear my favorite nightie with marabou trim and Sissy Roger has one that is similar. We like to experiment with makeup and have fun painting our nails. Mommy always says Sissies should be pretty and we love being pretty. But the most fun we have is sucking each other's things. Mommy calls it sissy-nining. It is so exciting and Sissy Roger sucks my thing and I get so excited that I squirt in his mouth and he gets so excited that he squirts in my mouth. We are careful to swallow each each other's Sissy juices. We do not want to make a mess or do anything that would make our mommies angry because then they might not let us have another sleepover. After we have squirted and swallowed we fall asleep in each others arms. After a while we wake up and do it again. Sometimes we do it three or four times during the night. Sissy Roger and I often wake up sore the next morning, but we are happy and well drained sissies who just love our sissy lifestyle. Dear Nanny Susan My friend Sissy Kenny says that he is a better sissy than I am because his boy bits measure 4 inches and my boy bits measure only three. Is he right? Is he a better sissy? Dear Three inches Some mommies would say that the smaller the boy bits the better the Sissy because he has a smaller bulge in his panties. The fact is the size of a sissy's boy bits has nothing to do with how good a sissy he is. A good Sissy is obedient, he always does what mommy says, he is respectful and polite and cheerful. A good Sissy knows how to control himself so he does not embarrass himself or mommy. Nanny hopes that you will stop worrying about size and just be the best little Sissy you can be.