T'was the night of the summer solstice and my friend Timothy (although Everyone else calls him Tim) wanted to go out clubbing. The catch was though that he wanted me to dress up like I did quite often at home as a woman.
I am 21 year old Alexander Peter-James Matheson. Ever since I was a kid I liked to dress up as a girl, especially a young one, and when I talk about young I don't mean a 17/18 year old one. I mean as young as 5 and as old as 12. On occasion though I would invite someone over while I was dressed as a woman. That is how Timothy and I met face to face. Sometimes when my other friend Maria is over actually not sometimes really it's whenever she is over, I get dressed and treated like a baby girl. I have however worn diapers every day since the first time I was treated like a baby girl which was 2 years ago and I now have no control over my bladder and very little control over my bowels(enough to only go when I'm home) so basically i don't use the toilet.
I'm a very petite person as in I'm a hundred pounds soaking wet. I say I'm about five feet tall. I have long thin blonde hair with natural light brown streaks.
Timothy wanted me to do this because he hasn't been truly on a date with a girl in approximately 3 years (Although I tried to get him to be my boyfriend a few times while I was acting like a girl), so he wanted me to act as his girlfriend. I thought that it would be fun to do but was afraid of getting caught.
"Please do it Alex no one will catch you and you are a really convincing woman." he exclaimed. I did agree with him I made a very convincing woman. I thought about it for a minute and decided to do it.
He and I quickly walked up to my room. He helped me pick out a light blue dress that went down to my lower thigh. The skirt was about an inch thick in about 3 layers, but they were so close together that you couldn't tell the difference. Then I picked out a bra that an a-cup which meant it was really easy for me to wear.
"You can't have an A-cup bra on Alex, you need at least a B-cup on." Timothy explained. "But then I got to put on the silicone breasts." I replied "That's ok no one will know the difference" "How do you know?" "Because they look quite real to me." "Ok, than." I said finally letting in to it.
I grabbed a blue B-cup satin bra with a pink hearts and bright pink ribbon and the bottom of the cleavage part. Timothy had already gotten the breasts which he then helped me put on. Than finally I put my bra on and did it up.
Timothy than helped me up to my change table so I could get my diaper changed. He picked out a bright neon pink one that had princesses on it which was my favorite type and till this day still is. Those diapers I had specially made because of the simple fact that I don't work anymore so I live almost full time as a sissy baby when I'm not dressed as young girl. Either Timothy or Maria takes care of me.
When I turned nineteen two years and almost ten months ago I went in on a business venture with one of my cousins. The business became a complete success so my cousin offered me 2 million dollars about a year ago and a 10% stake of the profits for the rest of the life the business if I gave him my half of the shares. He knew that I liked to dress as a young girl and he also knew that I wanted to do it full time.
I said yes to sign over my half under those conditions, and under the condition that if for any reason at all he couldn't run it, I would be given Controlling interest so I could run it until he could run it again. He agreed and I get 10% of the profits every month which is usually 15 - 25 grand. So I basically get to do nothing and live a life of luxury.
Timothy quickly diapered me and then I did what I had to do with the little bit of control I have left. He then picked out a pair of blue silk frilly sissy panties that matches the bra and put a liner in it that I came up with. The liner basically allows me to wear panties and still be able to pee if I need to in the bathroom -which I always have to do when out-, without making a mess of my panties or making a mess of myself. I put the panties on and grabbed a pink petticoat and then put it on.
I grabbed the dress, pulled it up, and pulled the straps over my shoulders. I than went to my vanity and put on some light mascara and some light pink glossy lipstick. I was finally ready to go out clubbing.
The Night out on the town
We went to a nightclub downtown and arrived at ten so we ended up getting a meal together. He ordered for me and I ended up having a garden salad and Tim got a steak. We ate and talked having a good time. I had a glass of chardonnay and Tim had a beer.
When we finished Tim went to go pay the bill but he ended up not having enough.
"How about you convince the waiter to let us off with the rest of the bill" Tim whispered to me.
"How about you take me to the back room, you might like what you get?" I said to the waiter who I winked at.
"Alright my boss would be angry at me if I didn't do it if you're talking about what I think you're trying to say!" The waiter replied.
He took me to the back, which ended up having a tiny room with a couch there. I'm guessing that people do things with waiters often. I kissed him on the lips while also touching his penis. We kept kissing, I than slipped my hand down his pants, with the other one I pulled his pants down. I pulled out his cock which ended up being seven inches, really skinny, blood red, and hard as a rock.
I knelt down than put his cock in my mouth and sucked it for about five minutes. He ended up having four orgasms, every time I swallowed all of his cum. Until the last time I pretended to swallow it but instead I kept it in my mouth. I kissed the waiter although this time I gave him tongue which also forced his cum into his mouth which he then swallowed.
He showed back out to Tim who had the remaining amount of the bill ready to pay him.
"You had the money on you?" I asked
"Yes but the waiter told me that he wanted you to give him a blow job and I wanted you do it as well!" he explained
I though WOW he just helped have the best sexual experience in my life. I thanked him for doing it and we than went dancing. Throughout the night I had at least ten men compliment my looks. Near one we decided to leave and head home. On the way out another man asked me if I wanted to go home with Him. I Told him no however.
We went out through the door. The man ended following us. We walked Faster but he broke into a run and grabbed on to me quickly. I thought this can't be happening again. I was going to be kidnapped again. Tim tried to stop him but the man hit him and knocked him out. He lifted me and put me in a booster seat in his car, and said well you sexy sissy baby were heading to my place now and you're going to be my slave.
We drove for what seem like an hour. He then gave me a pacifier that I back at him but he forced it in my mouth. That was the last thing I remember from the drive.
My Kidnapper's house
I woke up the next morning in a crib with my arms locked to the sides and my legs locked together which didn't really matter anyways. He had me in footie pajamas that also had hands but with no fingers. They must have had a slippery thing in them because even if I tried to do anything I couldn't hold on to anything.
The man came in to wake me up. He gave me a bottle that I began to drink. He then put a ribbon around it and tied the ribbon around my head. The bottle was filled with cum, piss, and a broken up piece of poop. I drank it and he said that's for giving me a hard time last night.
"As long as you be a good sissy baby and a good sissy slave I will give you a bottle of milk or just my cum." He explained
He let me out and changed me into a new onesie. I began to try to get him to change my diaper, but he told me that I will always stay in the same diaper until I go to bed the next night. He then took me downstairs and gave me a dollhouse and some dolls to play with.
Throughout the day he made suck his cock, clean his ass after he pooped, and then gave an hour in a normal age but, he put a 1ft chain around my leg connected to a pole preventing me from running. He silenced me by putting a pacifier in my mouth than wrapping a ribbon around my head that was connected to it.
At the end of the day he gave a bottle of his cum and Milk. The kidnapper than finally changed my diaper. He finally put down for bed locking my arms to the crib again. I fell asleep quickly.
When I woke up the next morning Tim and Maria were the ones to come in and wake me up. They told about how they paid the man to do kidnap me and do all those stuff to me.
The Choice
"Alex we want to ask you something we were watching everything through hidden cameras, and it seemed like you liked it quite a bit." Tim said
"I did like it a lot and that bottle that poop in it was it actually poop or not?" I replied
"No it was food coloring but you did clean out his bum for him."
"Yes, I did"
"Ok. Well anyways Maria and I would like to know if you would like him to stay at the house? And would you like to be locked up and not able to do anything? And also be a slave? if yes to all of these questions than you will be a permanent baby girl with the occasional 5-12 look and the occasional woman look, but the catch is you will be put on estrogen right away."
"Yes to all of those questions, I would love for that to happen." I replied without thinking.
"Ok well we are leaving soon so we must get a new diaper on you and put a new onesie on you."
"Why, can't I wear normal clothes?"
"Because you're being put into a car seat in Mike's car which I had specially made for you over the last few days. Oh and mike's car is in his garage so you will still be inside the house when your put in the car."
"Alright."
Tim and Maria got me dressed quickly I was put in my normal diapers and a pink princess onesie. They then put a pair of black tights on me so I would stay warm.
After I was ready they called out to mike and he came up and took me down to the car and strapped me in. He then gave me the same pacifier that he gave me when he first took me. He told me that it was a good three hour drive back to my house so I was going to sleep. I put the pacifier in and I was asleep in minutes.
To be continued