I was raised with two sisters and a single parent. Mother not having much money raised me wearing my older sisters hand me downs but mostly I wore diapers and a camisoles. I was home schooled while my sisters went to public school. Mom always kept me dressed like a baby or a girl and I never had male clothes. When I was old enough Mom started training me to become how she put it, a desirable girl. After setting me down and explaining what all she was going to do to me, it made me cry. I was told all sissy boys go through this and I was no different. Crying is always one of the out comes when a sissy learns he is not a boy. I remember we discussed this on a Friday and the training would start after my sisters went to school on Monday. I had all weekend to come to grips with my faith but found myself crying most of the time.
When my sisters caught me crying they asked what was wrong, I would tell them nothing. They went and asked mom why I was crying and she came into my room with my sisters behind her. Mom asked, your crying young lady? Then my sister asked, why I was a crying young lady? Mom told them I was going to become a young lady soon and that is why I was crying. Both my sisters said they where young ladies and they did not cry. Mom said I had more adjustments to make before becoming a young lady. She told them my name was going to change and they where to call me Tammi from now on. She chased them out of my room and came to sit beside me on my bed. Being dressed in only cotton panties and t-shirt mom had me stand in front of her and lift my t-shirt. While standing there she hooked a finger in my panty hem and pulled it down. Looking at my penis she told me if I wanted, it could be removed permanently! Oh no I answered as I started to cry uncontrollably. Take your t-shirt off I was ordered. Once I managed to remove it I was asked If I was going to continue to cry? Not answering I was de-panted and told to lay on the bed.
Mom produces diapers and plastic pants, powdered my bottom then diapered me. Once she had my yellow plastic pants on she put a yellow camisole with lace on me. You will wear this from now on until you earn your panties back she told me. Then I was led by my hand to the living room where my sisters both laughed at me. Mom told them this was going to be my outfit from now on until I learned to be a lady. While the colors of my camisoles and plastic pants changed I was kept in diapers and camisole every day. When Monday came and my sisters left for school my pain started. I was stripped naked and told to bend over my bed, I knew something was up. Your going to start your training to become a young lady. I was given awash cloth to bite on if the pain was too much. I was told no yelling was allowed while in training. Mom spared my ass cheeks and smeared something in my butt crack and then worked something into my ass.
While doing this I was ordered to be still or it would hurt much more as I lay with something in my ass she talked to me in a soft voice. While working the item in and out of my ass telling me after a few times of this I will start to enjoy it. This lasted about a half hour then I was diapered again. Three hours later the scenario was repeated again. Over the next week this happened twice a day. Mom would tell me not to talk about my training with my sisters. This would result in harsher punishment such as an anal plug for a day. Not knowing what she meant I asked and she showed me a plug with a ring on the end and inserted it in me. I yelled so loud mom slapped my ass hard. I begged for her to stop but she kept pushing it in until it was seated all the way in. I was shaking from the pain as mom told me this would be the punishment for discussing my training. I continued to cry as she explain the punishment. While still in pain I was rolled over and my little penis was now rubbed a few times before getting stiff.
While mom stroked my penis, she continued to tell me never to touch my penis or play with myself unless I had her permission. If I did not obey I would be plugged for a day. I then had something squirt from my penis and was afraid I would get into trouble. That is alright I wanted to get that milk drained out of you she replied. For some time I was penetrated with what I found out was a dildo. The dildoing took place twice a day during the week and I was “Milked” as mom put it to get rid of my penis milk. I was told that the milk if left in me would make me boyish. I was still wearing diapers and a camisole until one day about six months in diapers. During this six month period I was introduced to another boy going through training also. Our moms decided it would be better if we trained together at the same time.
I remember when Diane came over with his mother he was dressed in a pretty lime green party dress with bows and ribbons and lots of lace. His hair was long and had ribbons and bows in it. I was ashamed that I was wearing diapers and a camisole. Our moms talks as if we where not present then introduced us to each other. Her sons or I mean daughters name was Diane and I was introduced as Tammi. Diane’s mother Miss Jones, asked why the diapers? Mom explained that I was crying when dressed like a girl knowing I was going to have lady training so she now keeps me in diapers until she decided different. Mom continued to tell her I was only being dildoed and milked twice a day as of now. Mom asked how far along was Diane on her training? Diane honey come here and take your dress off as her mom pulled it off over her head. Now standing in only her lingerie, pink panties with lace around all the openings, matching camisole top, and baby Jane shoes. I could see Diane’s little tent in her panties as she stood trying to cover it with her hands. Her mom was fixing her hair ribbons while talking. My Diane is plugged all day and kept in a penis ring for stimulation. Mom asked if Diane had any accidents with some thing called premature ejaculation? No she is milked three to four times a day Diane’s mother explained. How far along is Tammi?
Mom told her I had only just started my training being dildoed and milked twice a day. Diane was cowering close to her mother while trying to conceal her protruding penis. Come around here Dian she scolded her as she was pulled front and center. Stand still and remove your panties her mother commanded. Slowly pulling them down and stepping out of them Diane stood with a little cock ring and pink bow around her erect penis. Two little bells hung under her little ball sack. Why the bells mom asked Diane’s mother? So I know if Diane is playing with her self. Turn around Diane and bend over honey her mom ordered. Doing as told we could see Diane’s anal plug protruding from her ass. Her mom told mother to tug on it and check the tight fit of it. While doing so as she pulled and pushed it in several times asking Diane how it felt? I feel very full ma’am was her answer. Stand up and turn around and let misses Miller see your clitoris. I had never heard of the penis called a clitoris before. When Diane stood up and turned around I could tell she was embarrassed about her exposure. Mom asked how long does her clit stay erect? All day Miss Jones told mother.
Mom then asked if Miss Jones would help her with me and bring me to stage Diane was. Sure Miss Jones replied lets take a look at Tammi’s clitoris. I was now shaking as mom helped me out of my plastic pants and diaper. I tried to cover my clit or penis with my hand and mom slapped it hard. I stood with and erection as Miss Jones looked on with a smile. Tammi, Miss Jones said you have a much larger clitoris than Diane does. Come here girl and let me look you over as mom pushed me to her, she reached out lifting my hands above my head. Reaching down she pulled on my erection asking when I was milked last? Then she stopped and noticed I was leaking milk from my clit. I am so sorry miss Jones for Tammie’s lack of control she has not hand any other stimulation other than her dildo. Then Miss Jones said Diane did the same but not as much.
Diane is training on fellatio with a penis plug and dildo. She has been eating her own clit milking’s for some time. She fought it at first but she learned it was the only way she would get to wear her pretty fillies if she obeyed. When she did not obey I had her clit tied for full stimulation and ass plugged only to keep her naked around the house day in and day out. I even kept her like that in front of company. When standing in front of my boyfriend Dale like that and he started to play with Diane’s little clit. She started doing as she was asked after that. Diane honey would you like to taste Tammi and relief her of her milk sweetie ? Diane’s mom asked her?
Diane turned red and looked down at my throbbing clit. Biting her bottom lip and looking at her mother, her mother nodded okay and she dropped to her knees and started sucking my penis. I unloaded in a few seconds spilling my milk into Diane’s mouth as she sucked greedily to get every drop. Good job Diane, her mom patted her head as she still knelt and licked my clitoris as it bobbed from the tung lashing she was giving it. My mother was very impressed at Diane’s eagerness to accept cock in her mouth and eat all the sperm.
Miss Jones then asked if I would like to lick Diane’s clitoris. With out thinking and as if in a trans I looked at Miss Jones and shook my head yes. Stand up Diane and let me remove your clit ring and bow so Tammi can suck on your little clit. Now do not squirt in Tammi’s mouth do you understand Diane her mom asked? Yes ma’am, Diane replied to her mother. I dropped and opened my mouth as Diane stuck her little clit in my mouth. Closing my lips around it and licking her clit head it was so soft and tender. I felt right doing what I was doing as our mothers looked on watching our expression. Miss Jones said I looked like a natural at clit nursing. Then she asked if I wanted to taste Diane’s milk? I started to whimpering and withdrew my mouth from Diane’s clit. Miss Jones said, oh no Tammi keep on sucking Diane’s little clitoris as she pushed the back of my head to Dian’s throbbing clit. I latched back on to Diane’s clit and continued to suck. Miss Jones told me not to stop until she tells me to or she would have to punish me.
Miss Jones pointed out to my mother how my clitoris has become erect again. That is normal for a girl to become aroused while clit nursing Tammi will become a natural. I can bring Diane by every day around ten in the morning and we can train the girls together. Mom was all for it and thought it was a great idea. I continued sucking as they talked over details. Miss Jones said she would not milk Diane in the morning but Tammi will need to suck her clity dry once we get here or Diane will ejaculate prematurely. Both moms agreed and I was asked to stop sucking Diane’s clit. Do you need to squirt Diane, her mother asked? Yes, please ma’am can I please squirt my milk? Her mom grabbed her coffee cup and finished drinking it down then held it up to Diane’s clit. Pulling the anal plug in and out three or four times as Diane squirted her milk into the cup. Here you go baby as she handed Diane the cup of clit milking’s. Diane took it without hesitation and drank what little spunk was in the cup. Thank you mommy, Diane said as she handed the cup back. Her mom asked if she had licked it clean and Diane took the cup back and licked every inch of the inside. Good girl Diane, her mother patted the bottom of her butt.
Put your panties on Diane and get dressed we will be back tomorrow at ten. While Diane dressed she smiled at me. Once her dress was fitted in place and straightened she came over and kissed me on my mouth and she hugged me. My clit was at attention as they headed out the door Miss Jones pointed out that my clit may need to be chastised until Tammi learns control like Diane has. We can talk more tomorrow when the girls are practicing on one another. Yes my mom said, she was looking forward to it. When the door closed mom turned to me and said. Once I learn to eat my own milking’s like Diane I could ask for pretty panties but until then I am stuck in diapers. I knew tomorrow I would be tasting my first clit milking. For some reason I was looking forward to being with Diane tomorrow.
My sisters where due home any time now and I was ordered not to talk about my training. The evening came and my sisters noticed I was happier than normal and asked why? I said no reason I was just happy but mom knew why I was happy and she just smiled and winked at me. My sisters called me sissy Tammi whenever using my girl name and mom told me to accept it since I was a sissy. When mom changed my diaper she asked if I enjoyed today with Diane. My clit became stiff as mom applied powder to it. Then pulling on it with two fingers she said you did like todays lesson didn’t you my little girl. I squirted all over when she said that. Oh you little rascal you and she wiped up my mess and re-powdered my clit and bottom. Pulling up my plastic pants she put me in bed and covered me up. Your going to have a big day tomorrow Tammi you better get your rest. Yes mommy, I did have a good day. I think I am going to like being a girl I told mom. I know you will baby, I know you will. Then can I wear pretty panties and dresses like Diane. Yes, you can have your pretty panties and dresses when you learn to eat your milking’s now go to sleep. I drifted off to sleep with an erection in my diapers thinking of tomorrows lessons.
Sissy Tammi Girl.
“CSM” Sissy Maker.