The day of the party finally arrived. The Smith's house was expecting guests to arrive from 6 pm. Everyone had their costumes ready. Matilda had arranged to come across at 2 pm to do Jessie's, Angela's and Jack's makeup. After she was finished Jack would be handed over to Jessie and Rebecca who were going to dress him.
Jack had a bad feeling about the evening. He just knew that Jessie had something else planned that would further humiliate him. There was just something in the way she had looked at him all week. She seemed so smug. However he had no choice but to wear the costume they had in mind for him. His Mum, Mrs Smith and Rebecca had all jumped on Jessie's bandwagon. It seemed the world had it in for him. If he backed out now he would forever be known as someone who whelched on a bet.
Jack hid in his room once he heard Mrs Smith arrive. She first worked on his mother then Jessie. His mother knocked on his door when her own make-up was complete. She instructed him to have a close shave.
It was nearly 3 O'clock by the time his Mother once more summoned him. This time it was to the kitchen where Mrs Smith had set herself up. Jessie was wearing a blonde wig and was heavily made up. Mrs Smith had done a good job. Jessie appeared to be middle aged.
Jack had to sit there as Mrs Smith worked on his face. They didn't allow him to look in a mirror. Not that he would have wanted to. The lipstick put on him was cherry flavored. His Mum, Rebecca and Jessie all hung around and watched Mrs Smith work. Lastly she fixed a net on his head and to that attached a blonde wig with pink and blue strands in it.
Mrs Smith packed up and departed. Rebecca and Jessie then got to work. By now both were already in their own costumes. Rebecca looked creepy in her black dress and gothic make-up.
Firstly he was given a ring by Jessie. She told him that he had to wear it. It seemed a strange thing to be the first request but he didn't argue. The ring wasn't particularly feminine. Jack was sure there were worse things in store for him. It fit him perfectly.
Whilst Mrs Smith was doing Jack's make-up the girls had laid out the rest of Jack's costume in his own bedroom. They had chosen that room as there were no mirrors. Neither girl wanted Jack to see his reflection until his cosume was complete. He was led back there and was astounded by the amount of feminine attire on the bed. 'Your kidding me aren't you?' was his comment to Rebecca on seeing all the undergarments. Rebecca just giggled in reply.
Firstly Jessie left the room while Rebecca helped Jack into the flesh coloured girdle his mother had supplied. This was designed to hide his bulge which would spoil the look the girls were hoping for. Rebecca also explained that it would also help to give him a feminine figure by enhancing his bum and giving him a waist. Jack didn't mind putting the girdle on as in the process of doing so Rebecca gently held his penis in place tucking it between his legs so that his groin appeared to be smooth. She was very gentle. The two had enjoyed intimacy together but Rebecca holding his penis was a novelty. Jack pulled up the girdle and Rebecca removed her hand. There were straps on the back of the girdle which Rebecca tightened making Jacks waist shrink. Rebecca was very satisfied with the result. She didn't have to tighten the corset much at all to give Jack a thin waist. The girdle must have had more padding in the bum than Rebecca had originally noticed as well. Jacks bum now appeared to be very well padded.
Jack noticed himself that his groin was suprisingly smooth. The garment had done a remarkably good job at hiding his bulge. Best of all it was painless. Jack found he could walk around without squeezing his balls. It was as if they were no longer there. Even his narrow waist didn't feel particulaly constricted.
With his groin no longer exposed Rebecca called Jessie back into the room. Jessie grinned with delight seeing what a good job the girdle had done then suggest the Jack needed to sit on the bed and put the flesh coloured pantyhose on. Rebecca once more helped Jack. The panty hose pulled right up to Jack's waist completely covering the girdle. Rebecca thought they did a remarkable job of hiding the hairs on Jack's legs. Jack's legs now appeared to be hairless and very feminine.
Next Jessie had Jack step into the lacy pink panties. They were a French knicker style. That had been Mrs Smith's choice. Jessie would have preferred Jack to be in a G-string so he didn't have a pantyline but it was no big deal.
Jessie sent Rebecca on an errand to borrow a fabric brush from her mother. This was an excuse to be alone with Jack. She didn't want Rebecca to witness Jack's breasts growing. Once they were alone Jessie clasped the pink bra around Jack's chest. She then pretended to stuff the bra. It was just pretend. Jack's bra was already filled by B-cup breasts. Jessie said 'These are gel implants. It will feel as though you have real breasts'. Before Jack could say anything she made him hold up his arms and put the pink full slip onto him. The slip had a high neckline.
As soon as the slip in place Jack's hands came up to feel the protusions from his chest. This was the moment of truth.
'Wow! These feel so real! If I didn't know better I'd say I had real breasts' Jessie noticed that Jack's voice sounded an octave higher.
'Try not to fondle yourself. It's unseemly. Probably best if you start now so you don't get into a habit'
Jack replied sarcastically 'Yes Principal Weems'
Jessie was already totally in her costume. She went with the theme. 'I'll give you detention if I catch you doing that again' For the rest of the dress up session even once Rebecca was back, Jessie only had to say 'Stop that!' whenever Jack went to feel himself. He would stop.