When in doubt, cry about it (PG)
will Caleb's girl friend accept his weird disires
Posted on
Add A New Story
A long time ago a guy by the name of caleb went to a holloween party. Caleb is the kind of person that likes to stick out so he dicided to go to the party as a girl. At this party he fooled everybody that he was his girl friends cusin but she didnt have a costum. Caleb Loved this he enjoyed being in girl clothes infact he had planed this for months so he got a tan got thiner and shaved his legs and arms and barrowed some clothes from his cusin.

Chapter 1 -At the party

"oh my god caleb you look so adorible" said natalie (his girlfriend)
"ya i know"he sacasticly replied
they got into a car and went to the party(this is a middle school party so their al 14 and 15) when the got there everybody wanted to talk to him but he didnt have to voice for it so he claimed he was from switzerland and only spoke german but could write english so he wrote everything. lator this made sence cus the only two people in on it found him a swiss girl outfit for him. Well the party ended and everybody left but caleb didnt have a ride home so he regretfully changed his clothes and slept in natalie's gest bedroom
he had a weird dream about him being a baby again but his babysitter was natalie, his cusin, and becky(a friend of his girlfriend) and he was being dressed as a girl which he enjoyed but he also loved the diaper part of it too.
he woke to find himself wearing a miniskirt,babydoll tshirt and...A diaper, "how did this happen, he was freaken out this ment he was dressed in the middle of the night by a 14 year old girl and diapered at the same time, he got up an wraped himself in a blanket so no one would see and went to natalies room and woke her up. she burst out laughing and said "i guess you shouldnt have enjoyed the party to much"
"ya well how did this happen?!?!"
"well, theres thing you call your a heavy sleeper and my mom keeps big diapers for some reason and apparently knows how to change them"
"your not leaving this house until you say females are dominant and use the diaper"
" wo, wo , wo im not gonna use the diaper and i can leave any time i want just watch m.."
"realy so your gonna ride your bike the 6 miles wearing a miniskirt and a diaper sure go ahead"
"this is not fair this must be like sexual harassment or something...ok fine i will but its not coming easy your gonna have to wait"
"sure i can wait but to help you know female domanance we can either play dressup or tie you to my bed and wait your choice"
"ill go with dress up thank you very much the other one sounds perverted"
so the sissy boy went 2 steps without natalie makeing him crawl to her room and they got situated and plaied dress up for all of 2 hours caleb realy enjoying it. but with in minutes of the next event caleb had to go to the bathroom pee and poop...

Chapter 2-Going. going, FULL

Caleb kept trying to fight the erge to go but he couldnt and felt a warm sensation filling his diaper and a loud fart came out afterwards begining the poop stage. he quickly filled his diaper and he said "okay i did it can i go now?"
"no, you have to be\changed first"
"no, no thats were i draw the line your not changeing me"
"im not my mom is shell be home in an hour"
:...an hour i have to wait an hour, and what am i suposed to say he misses refeild i kind of had a diaper on and used it can you change me whats that going to sound like"
"what do you mean who do you think but diaper on you in the first place and plus she going to check you on her way in so dont even try to avoid her"
as an hour passed caleb sitting in the most girlish dress ever still wondering were she got waited an hour till they heared a door close and a yell"girly boy are you wet?!"
Caleb went up the stairs and looked at her she said "okay what do babies do they dont come up to you and ask for a change"
Caleb regretfully started crying natalie laughing her head off in the backround
"okay{she must have been muscular she picked him up}time for a change " she laid him down on the bed and changed him his face beet red the hole time"okay all set" she laid him down wearing an even bigger diaper thicker and bulkier"okay natalie can i leave now"
"what i did the things you asked why not"
"no you havent you have to express female dominence"
"ok what do you want me to do sit here and be a baby to you and your mom all day"
"ya that'll be good"
"no i was just kidding"
"to late already said"
Caleb realy wanted to go home and play some xbox live or something but instead was put in a playpin in the basement so natalie could watch him
"okay stay in here if you get out im putting these picture s on your mypace"
she quickly took pictures
"and no talking babies dont talk"
she stuck a oversized pacifier in his mouth and giggled and went back to her msn conversation..

To Be Continued.......
Last Post
3 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
great story, keep it going.

excellent story how come you still havent written the next part yet
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.