Jack looked down, seeing Sally's cum soaked knickers in his hand. His eyes focussed beyond them and saw the tops of his stockings. He looked at the school skirt pulled up around his waist and the lace boyshorts pulled over to one side to reveal his shaved and now wilting cock, dripping cum from its tip. His eyes followed his stocking clad legs to the heeled shoes on his feet and back to the wet crumpled garment in his hand. No way could he let her catch him with her cum soaked knickers like this. It would just confirm all the things that she had said about him over the past day or two. Quickly he stepped over to the laundry basket and buried the wet sticky mess that was Sally knickers somewhere near the bottom. It would dry before either one of them did the laundry next and she would never know.
He just had to pretend he hadn't been up to anything. To be caught like that while wearing his - or rather her - school uniform would be just - well, weird. He had to get his head back together. So much had happened in the past day that he could barely cope with. He had been shaved from neck to toes not once, but twice; forced to try on women's lingerie in a department store; masturbated by a complete stranger; made to try on and then wear a dress and women's shoes; masturbated again, this time into his underwear; made to eat his own cum out of Sally's now hairless pussy; and finally dressed as a schoolgirl and left alone in the house, at which point he promptly masturbated again! This had to stop. Whatever had come over Sally was great, but she had to recognise the lines that shouldn't be crossed. Not that he was entirely sure where those lines were and that confused him even more. He was straight. He had always been straight. And while he had always enjoyed playing with girls' knickers ever since he had borrowed a pair from his elder sister many years previously that didn't make him gay or a tranny. He had never wanted to dress up as a woman. It wasn't who he was and he took no pleasure from it. Except he did.
He tucked his genitals back into the boyshorts and let the navy blue pleated skirt fall back into place. Jack raised his eyes. There, gazing back at his from the mirror was, at least from the neck down, a young woman. It looked right and, although he didn't want to admit it to himself let alone to anyone else including Sally, it felt right too. more confused than ever, he turned away from the mirror and, skirt swirling around his stocking encased thighs as he moved, he got on with the chores that Sally had asked him to do.
After an hour or so Jack heard Sally's key in the lock. While she was away he had sorted the clean laundry and tidied the downstairs of their house and as he did so he had become more comfortable with the unfamiliar heels, modest though they were. Jack saw her look of approval as she glanced around the lounge.
"Thanks for doing all that clearing up. Did you have a nice time while I was away sweetheart?" she asked. "I hope you were a good boy and weren't playing with yourself while I was gone."
"Don't worry," he replied. "I haven't been playing with myself."
"Good, because we want you all full charged for later," she laughed. Clearly she was referring to after the party, but why did she keep bringing it up? Maybe the thought of dressing as a man and having him dressed as a woman was turning her on, Jack mused. If, then so much the better! When she got really turned on the sex was simply out of this world and if the price to be paid was a few hours in a dress with all his mates, then it was a price worth paying!
"OK," said Sally. "We had better get you ready."
"It's a bit early, don't you think? We're not supposed to be there until 7.30 and it's only 5 now."
"It will take you a little longer to get ready than usual, boyfriend!" she laughed. "Come on - upstairs."
Over the space of the next two hours more effort went into Jack's presentation than had gone in over the previous 20 years of his life combined. Sally led him into the bathroom and striped him slowly of the schoolgirl costume, and not without some secret regret on Jack's part as he was really starting to enjoy the sensation of the skirt, the stockings and the heels.
First to go were the shoes. Jack stepped down from the unaccustomed height he felt the muscles in his calves complain a bit as they were released from their unfamiliar pose. Next Jack felt Sally reach for the zip at the side of his pleated skirt. She smoothly ran the zip down and then deftly released the hook in the waistband and allowed the garment to drop to his feet. Jack studied the reflection in the mirror - the skirt pooled around his feet, stockings rising from the puddle of navy blue material and ending just beneath the white tails of the blouse. The blouse itself being held clear of his stomach by the swell of his stuffed bra that he was wearing beneath it, the straps just visible though the material.
Then Sally undid Jack's blouse, pushing it back from his shoulders and revealing his bra, suspender belt and panties. Jack drank in the intoxicating site and felt his cock begin to swell again.
"Turn around," she told him.
Jack turned away from her, still watching his reflection in the mirror. Jack felt her hands unclasp the bra and push the straps off his shoulders. Looking at this reflection, Jack could see the marks of the bra straps in his skin. He swallowed. There was something peculiarly feminine about those marks and while he knew he should be uncomfortable with seeing them on his own body he was not. It felt weird seeing them, but it didn't feel alien looking at them and Jack knew somewhere that it should have done. He felt her hands go to the clasp at the back of his suspender belt and, with a surprising spark of sadness, felt the tension release as she unclipped the back and push the belt with the stockings still attached down his legs.
Sally made him take yet another bath, although he protected that he was perfectly clean enough already, having had one only a couple of hours previously, but she was adamant. She carefully washed and conditioned his hair, checked to make sure that there was no razor stubble anywhere on his smooth body and then bade him knell in the bath on all fours.
"What for?" he asked.
"Come on, honey, do as you're told."
Jack complied although as he did so a part of him was asking why he was being so obedient and almost as soon as he was in the required position he felt her fingers around his anus again.
"What are you doing?" he repeated.
"I want you to be completely clean, so you are going to have a douche."
"A douche. It's what washing inside is called. Lots of girls do it, particularly in America. But of course we'll have to do it to your bum"
"Well, I've never heard of it, it sounds pretty weird and neither one of us is American, so what say we give that a miss? And besides, I don't want you to wash inside my bum."
"No, I really want to do this honey," she replied. "I really want it to be perfect so that everyone sees that we made the most effort and got the best results."
"But how the hell is anyone going to see inside my bum?"
"No-one will. But I'll know and every time I look at you tonight I will know that there was one bit we didn't do and that will spoil it for me. Please?"
Jack was sunk. He couldn't refuse her anything and this was just a product of her perfectionist nature. Besides, what was this compared to all the other stuff that he and let her get away with? Thank God this was the day of the party and that it would all be over tomorrow.
"Oh, OK. If you insist. Are you going to try and shove a flannel up my arse?" he said, hoping that that was not actually the plan.
"No, silly, just this."
Jack craned his neck around and saw what she was holding. It seemed to be a rubber ball quite a bit bigger than a tennis ball with a white plastic tube sticking out of it.
"What the fuck is that?"
"It's for washing out inside your body. I've filled it with warm water and now I'm going to wash inside you, and then you can squirt the water into the loo."
"Yeah, sounds great!"
"You don't mind, do you? I mean, I just want to get this absolutely perfect. I'm sorry sweetie."
"No, it's OK. I don't mind. Do whatever you want darling," Jack replied, turning away to face the taps and thus missing her little smile of triumph.
"Thank you. I'll just put some lube on you so nothing hurts."
"Thoughtful of you!"
"I think of everything!" she replied.
Jack heard the sound of the pump dispenser being pressed and then felt the coldness of the lubricant dripping onto his exposed hole. He started as he felt her finger push into the fluid and then circle his arsehole several times while he braced himself for what he knew was coming.
He felt her finger stop circling and the pressure on his hole increase.
"Relax, honey." He heard her whisper.
As he tried to comply Jack felt her finger suddenly gain entry and felt her rotate it within him, spreading the lube around as she did so. Then the invader was gone and there was an ominous silence when the only sound that Jack could hear was the beating of his own heart. After a few seconds he felt something else against his hole. It was hard and, although not sharp, it clearly had angles and edges. Again he felt the resistance of his hole give way but this time the invader was thinner and harder. He felt it move slowly inside his body until he could feel the body of the red bulb pressing warmly against the cheeks of his behind. At least she warmed the water, he thought. Then she squeezed.
Jack gave a small yelp as he felt his bowel fill with something. He couldn't feel the warmth but the increase in pressure was quite another thing. He could feel that clearly!
"Oh wow," he said in a state of shock.
"Feel good?" Sally asked.
"Err, it's hard to say. It doesn't feel bad I guess."
"Yeah, I know what you mean. I do this to myself when I'm planning to get you to fuck me up the bum so that your cock isn't really dirty afterwards. Of course, when it just happens or when you decide you want me in the bum then it just happens and you get a pooey dick!" They both laughed but then Jack gasped as she pulled the tube quite quickly out of him leaving a distended and full sensation that was quite new to him.
"Clench your bum hole," he heard her say. You need to make like your are stopping a really big poo until you get on the loo otherwise you will spray shitty water all over the wall. And if that happens, honey, YOU are clearing it up!"
Jack clenched for all he was worth.
"OK, stand up," she said. He stood awkwardly, struggling to gain his feet while still clenching like mad with his anus. He hobbled over to the loo and sat down with some relief, allowing nature to take its course.
"Better?" Sally laughed.
"Ha, ha," Jack replied. "Yeah, it's much better but I'm sure that wasn't really necessary!"
"Well, maybe, but there's no harm in it is there?"
"I guess not," Jack allowed.
Next came the hair. Sally carefully styled his long hair into a feminine style, mainly off the face but spilling down the right side of his face a little. Many unfamiliar hair products got their first outing on his head.
Then the makeup. Jack objected strongly to this particular humiliation, but Sally as ever managed to convince him that it really was necessary, that she wouldn't overdo it, and that if he truly loved her...
Helpless, he gave in.
She was true to her work. A light foundation layer, not too much colour on the cheeks, eye shadow that was tastefully understated and a modest shade of lipstick. He objected most to the mascara but even there he lost the argument.
Finally satisfied with the makeup, Sally turned her attention to the clothes. First of all came the stockings. Plain, but with delightful lacy tops. Sally supervised closely as Jack once again slid his feet and legs into the silky garment, enjoying the feel of the delicate nylon against his hairless skin. Sally then attached the black lace suspender belt around his slim waist and fastened it before attaching the clasps of the belt to the stockings. Next came the knickers. Sheer black with a delicate lace trim that matched the stockings themselves and the suspender belt. Finally she held out the bra to him and he treaded his arms into the holes. Sally stepped behind him and did up the clasp.
Familiar with the drill, Jack bent down to pick a pair of black socks up from the floor to serve as fake breasts, as he had yesterday.
"No, not those. Here," Sally said, handing him a box about six inches square and two deep. "These are much better."
"What are they?"
"They are your boobs darling," she replied as she opened the box. Inside Jack was astonished what were quite obviously two breasts. Flesh coloured with slightly darker nipples and made of some sort of silicone material.
"Where on earth did you get these?" Jack asked. "I didn't know you could buy tits!"
"Would you believe Amazon?" she replied with another laugh. "They're for women who want bigger tits without the surgery or for trannies. Here - feel them."
Jack took one of the breast shaped lumps in his hand. It was soft but had a well defined shape - just like the real thing. There firmness reminded him of Sally's own adorable little breasts.
"Do you like them?" she asked.
Jacked laughed. "Sure I do," he replied. "But don't you think this is taking it a bit far just for a party?"
"I thought we had agreed that if we were going to do this, we were going to do it right," said Sally.
Undoing a tube in the box she smeared a little of its content on the back of each of the breast forms and then slid each into its respective bra cup. A little adjustment and she declared herself happy with the look.
Last of all came the dress. A plain black cocktail dress which she fed over his head and pulled down, reaching behind him to pull up the zip, giving some final attention to the few hairs that the process had dislodged.
Finally the preening and pampering was complete and Sally declared herself satisfied with her work.
"Done!" she declared. "What do you think?"
She turned Jack back to face the mirror and for the first time he saw the whole picture. And it was quite a sight. What Jack knew was standing there-- shown there in the image was a perfectly natural heterosexual young man of 20. What he saw was a very attractive young woman of maybe slightly less than 20 in a flattering black cocktail dress with nylon encased legs, a pair of smart but not too dressy court shoes, a pendant and a shorter-than-average hairdo all kept in place with a decorative clip. The girl was well made up, had a great figure and, had Jack met her when he was single, he would definitely have tried to get into her knickers. Except his mind was telling him that it was him wearing the knickers.
"Well? What do you think?" Sally repeated.
"Err, yeah, not bad. Looks OK."
"Only OK? I think you're doing yourself down. You look great."
"Well, I look alright. Just look like a bloke in a dress!"
"Oh no, honey. You look much better than that."
"Yeah, I guess so."
"Why aren't you getting changed?"
"Oh, my outfit's at Lucy's place. She hired them both from some fancy-dress shop so I'll just have to get changed once we get there. I'll just throw something on for now."
She opened a drawer and pulled out a pair of black stockings and a suspender belt. Jack watched as she stripped naked, revealing her gorgeous body to him. She ran the stockings up her legs and attached the clasps on the belt to the tops of the stockings. Then she stepped into a short denim skirt, pulled it up over her hips and zipped it up. Finally she pulled a cotton sweater over her naked breasts.
"Cool, I'm ready!"
"Minimalist dressing?" Jack joked.
"Absolutely!" she replied. "Less is more!"
"You forgot the knickers," he said.
"I thought I would go without. Would you like that?" As she spoke she stepped towards him and gently squeezed his cock though the dress and knickers.
"Come on, big boy. Time to go. We'll have to get some wine on the way over."
"What? I'm not going into a fucking supermarket dressed like this!"
"No, just the off licence up the road. Don't worry, he's short sighted -- you'll be fine."
They went downstairs and pulled on coats, collected keys and then headed for the door.
It was quite dark by the time that they left the house but the streetlights provided more than enough light for Jack's liking. Head down and coat pulled up to his ears, he locked the front door as fast as he could and all but bolted down the garden path and up the road towards the High Street, or at least as fast as the high heels would permit. Sally followed on and caught up with him as he rounded the corner at the end of the road and slowed down.
"Blimey, honey, you're in a bit of a hurry!" Sally said as they walked up the main street.
"Yeah, I don't want anyone I know to see me."
"Why would that be?" she asked. "I really don't think that anyone is going to recognise you dressed like that, especially under the street lights. You've got nothing to worry about sweetie!"
Jack gust grunted in reply. "Well let's not leave it to chance, huh?"
"Whatever you want sweetie. By the way, you looked pretty good rushing up the street like that. No-one would have guessed that it is only your second day in high heels -- not that those are that high! You just looked like a girl in a hurry."
"Thanks, I think!" he replied.
"I'm really proud of you sweetheart. Not every boy would have put up with this. I'm sure you'll be the best looking girl at the party!" she laughed. "How did it feel running like that?"
"Weird. Really weird. My feet couldn't cope with the heels, I could feel the dress around my legs and as for the boobs juggling around ..."
"Welcome to the fun world of being a girl honey!"
"Temporarily," he reminded her.
"Yes, just for a few hours. But I think you'll enjoy it!"
They walked along the streets of Victorian terraces arm in arm, Sally teasing him every step of the way about the big masculine man now wearing a dress and walking around in heels. After a few minutes they arrived at the off licence and Sally went in. For a second or two Jack considered waiting outside but changed his mind as he saw two teenaged boys coming towards him and running their eyes up and down his figure.
"Hi Sally," the owner called to her as Jack entered the shop. Typical, thought Jack to himself. He never says hello to me, the dirty old sod. "How are you?"
"Great thanks Tony," she replied. "Off to a party at a friend's house and just need a couple of bottles of the house plonk!"
"Girls' night out, huh?" he asked. "No Jack tonight?"
Well, at least he knows my name, thought Jack.
"Spot on. He's at home with some football match or other. Just us girls tonight," Sally laughed.
"Sounds like fun. And who is this picture of loveliness with you?"
"This is Julie and behave yourself you lecher - she's way too young for you!" Sally quipped.
"I'll be on my best behaviour!" Tony replied. "Hi, how are you Julie?"
Jack just smiled.
"Have we met before?" Tony asked. "You look really familiar."
Jack could feel the colour draining from his cheeks. This was it. He wasn't at all convincing and the guy from the local wine merchant was about to piece it all together.
"No surprise there - she's Jack's little sister." he heard Sally say. "Down to the big city!"
"Hi," he said again, holding out his hand. "Pleased to meet you."
Jack shook the proffered hand and managed a quiet "hi" in return, hoping that he managed to pitch his voice high enough to sound like a girl. He watched Sally pay for the wine and swap small talk with Tony. As he rang up the purchases Jack could see that Tony was repeatedly eyeing him up. Finally the transaction was complete and Sally picked up the bag from the counter.