A Series Of Sissy Stories
By Amy Sadler © 2022
Book 1:
The Sissy Baby Trap
Dan MacDuff, was an 18 year old tough guy. Or more to the point, he acted as though he was. Though he never really had any muscles. How he managed to convince anyone that he was a tough guy, was anyone’s guess. Suffice as to say, that no one touched him, or made fun of him for that matter. He also attracted a lot of girls his age and some even older, but he never became their boyfriend. Why do that, when it was a whole lot more fun to have a different girl each and every single day. Dan was 5ft 4in tall of a very thin build, he had baby blue eyes and short black hair.
But there was one girl in particular Charlette Web, who did not only like this about him. She practically despised him and would not go out on a date with him whatsoever. However, she did not like his entire attitude, also the fact that he acted out to be a tough guy, but wasn’t, really infuriated her to her very core, that she simply had to do something about it. Charlette was 20 years old, she was 6ft tall of a very slender build, she had long blonde hair and cat green eyes.
So one day, when he made yet another attempt to go out on a date with her. She turned to him and said. “Well, actually. While I can’t exactly go out with you tonight. However, you can come over to my place. I have been asked to babysit for a friend of mine and the baby will be so quiet, that she won’t disturb us in anyway. So we could get up to.” Charlette suddenly paused for a moment and then continued to say to Dan. “Well, I will leave that part up to your imagination.” Said Charlette all demurely.
Dan had a huge big grin on his face. “Great. I mean I actually can imagine quite a lot.” Said Dan grinning form ear to ear. Charlette simply smiled at Dan and replied. “I’m sure you can. Soo it’s a date then?” She asked. “It sure is.” Said Dan with the biggest smile on his face. ‘I have finally gotten to here and wone here over. She’s going to be putty in my hands.’ Dan thought to himself. Little did he know what Charlette had planned for him. “Excellent.” Replied Charlette in a happy tone of voice and then added. “Come over to my place at eight PM. By the way, I live at number ten Holland Grove. Don’t be late.”
Said Charlette with a big smile on her face. “Don’t worry Babe. I won’t.” Replied Dan, who began to plan in his mind the things that he was going to do with Charlette, once he got to her place. So off he went, being very happy indeed. Dan lived in his own apartment and he was very proud of that fact. Charlotte lived in her very own apartment too, which was even better still. So Dan thought, he soon got ready to go out on his date and he was so looking to do a multitude of things with Charlette, once he reached her place.
It wasn’t a long walk and the apartment was a lovely detached house, it was white with an impressive red door with a gold plated door handle and a letter box. There was a doorbell at the side of the door. So Dan pressed the doorbell. A pretty little tune chimed and the door opened and there stood before Dan, was Charlette. She was dressed in a very sexy off the shoulder satin red dress, it was one of those bodice type ones that really accentuated her figure. On her feet, she had on a pair of red high heels, 5inches, that made her 5inches taller, but Dan really liked that fact.
In fact he was so turned on by her right now and he could feel his penis harden underneath his macho black colored briefs. He was wearing a white T-Shirt, since it was a lovely warm night. On it, was bold black lettering that read. ‘Macho Man Dan.’ He had on also a pair of blue Levi jeans and a pair of white socks and black trainers upon his feet. “Wow! You look real hot and sexy tonight Babe.” Said Dan, grinning from ear to ear. Charlette simply smiled and said. “Why thank you. Come on in and follow me.”
Dan gladly followed her through the front door, as Charlette closed it behind him and headed toward the staircase that was at the foot of the hallway. Charlette lead Dan right into her bedroom. Which surprisingly wasn’t at all girly. The wall paper was red with a gold band going along in the center, with furniture to match it. There was a bed with red satin sheets and matching pillow cases. ‘OMG! Her bedroom is just as sexy as what she is.” Remarked Dan in his mind. “Nice. Real nice.” Said Dan with a really big grin on his face.
“So, where is the baby?” Dan asked. “I’m looking right at her.” Charlette suddenly replied, which simply made no real sense, this caught Dan off-guard and confused him too. “Sorry, who did you say the baby was?” Asked Dan, scratching his head. “Why you are silly!” Said Charlette with a giggle and then all of a sudden, she pulled out some sort of a device that shot out wires at him, that attached themselves to his body. It was a stun gun of course and Dan immediately fell flat on the floor unconscious.
When Dan came to, he felt dizzy. He tried to talk, but to his dismay, his moth was gagged with a big pink dummy. There was a big mirror before him and he looked on in shock and horror. As he was sat on the floor, to what looked like to be the living room with a TV cabinet behind him. On his head was a pretty frilly pink baby bonnet. Over his body was a very pretty frilly pink baby dress.
Underneath that he had on a pair of pretty frilly pink panties, that was a diaper cover, that was over a ruffled butt pair of tights. As Charlette wanted his entire outfit to be as frilly as possible. On his feet was a pair of pink strappy shoes. Charlette stood behind the mirror with her stun gun ready to use, just in case he should try anything. She did think about tying up at first, but she suddenly changed her mind.
“I would not try anything stupid if I were you.” Said Charlette, warningly. “I have something for you to watch. So turn around slowly and face the TV.” Dan did as she had instructed him to do so. Charlette had a remote in her other hand, she pressed play, the TV came to life and a video played on the screen, showing Dan what had happened to him. After stunning him, she carried him over into the second bedroom, which turned out to be a nursery that was completely pink all over. Charlette then began to completely remove all of Dan’s clothes and then she began to put a diaper on him.
The very moment she begun to diaper him. His penis went rock hard, with Charlette giggling, as she proceeded to dress him in the outfit that he was now wearing. “You’re not so macho now are you?” Remarked Charlette with a big grin on her face. “You are certainly not macho at all. In fact you still have a hard on, even right now.” Said Charlette with a giggle, as she added. I have a very special camera that can see right through the diaper cover, the tights, the Princess plastic print panties and the diaper that you are wearing.”
Dan turned red with shame. “I had a feeling that your act of being macho to be false. In a way you should be grateful. And now you are and shall forever remain as my Sissy Baby Girl and your new name shall be Sissy Baby Jessica.” Said Charlette, grinning from ear to ear. Dan could do nothing but to simply accept his fate, or more to the point, his new role in life.
The End.