This is the latest installment of a story about cross dressing and the changes in a relationship between a young man and woman at college. Bits are autobiographical, but not as much of it as I would like! If this is illegal where you live, don't read it. If this sort of thing offends you, don't read it. Please let me know if you like it, and where the story might go. I love feedback! This was going to be the final installment, but I got a bit carried away and so I guess there will be at least one more. Enjoy.
Story codes MF, CD, Feminisation
The light was gently filtering in through the curtains as Jack slowly drifted towards consciousness. For a moment or two of his half awake and half asleep state he was confused - something didn't quite feel right. He stirred in semi consciousness and his eyes shot open at the unfamiliar sensations that the movement caused. As he began to focus he saw not the ceiling of the bedroom that he shared with Sally, but rather that of the lounge. Ah yes he remembered - he was on the couch. That's why the bed feels funny. He had fallen asleep there last night after Sally had...no she hadn't really, had she?
He pulled back the duvet and looked down at his body. She had. Quickly it all came flooding back. Shaving his entire body at her insistence. The shopping expedition to Oxford Street, the women's underwear, being forced to cum in not one but two shops. Going home on the tube with his cum soaking into his underwear - well, the women's underwear that he had been forced to wear - and his jeans. Having fantastic sex with Sally when they got home and finding out that she had been and had all her pubic hair waxed off, much to his delight and her apparent arousal. Then Sally making him clean that lovely smooth and freshly waxed pussy afterwards, and the unfamiliar taste of his own cum mixed in with her juices. The but plug that Sally had inserted into his arse, something which he was pleased to note had gone, although he had no recollection of removing it, but whose presence he could still remember due to a dull ache from his sphincter.
The rest of the evidence was there though, all laid out before him on the couch. The white matching lingerie set that he was still wearing. The lace topped stockings with the stains around the lace borders from when he had been made to cum in his knickers by Sally in Topshop's changing room. Those same white lace and satin knickers with the clearly visible cum stain covering much of the front panel tented out by his usual early morning erection. The suspender belt with its straps feeding under the knickers to the stockings and finally the white lace bra, stuffed with a pair of his socks. The same socks he had put on only yesterday morning but which had spent most of the day on his chest. Finally he put his hand up to his face and could feel the dried remains of the cum that Sally had made him eat from her freshly fucked pussy. He had eaten his own cum from her pussy. She had made him - begged him to do it and to make her orgasm again. But eating his own cum? That was a first!
He smiled to himself and relaxed, allowing the duvet to slip to the ground beside the couch. It had been fun, but of course it wasn't the sort of thing that he intended to get up to on a regular basis. Even eating his own cum from Sally's now bald pussy had been exciting and new and he had secretly enjoyed it having often fantasised about doing something like that when they were fucking. The difference was that the fantasy always died off after he had ejaculated, and so he had never followed through on it before. Oh well, first time for everything, he told himself, smiling.
Jack's hands moved to his chest and cupped the fake sock breasts through the lacy material of the bra. He chuckled. It was as if he expected to be able to feel his touch as though the breasts were real and felt almost disappointed as a result. He really ought to snap out of this, he thought, but it was fun and no-one was getting hurt as a result, so what the hell! As long as no-one ever found out! His hands slid further down and reached the lace suspender belt which was now a little off centre. Jack slid his thumbs under the soft material and re-centred the belt. Next his hands slid lower still to the top of the white satin and lace knickers. He gently ran his fingertips across the front panel of the smooth garment, luxuriating in the sensations that his caused in his piss hard penis and smooth balls. He could feel the outline of the cum stain where it made the material a little bit stiffer than the rest. Finally his fingertips found the straps of his suspender belt and followed them down to the lace tops of the stockings. Jack closed his eyes and smiled. As his fingers retraced their steps to his rock hard cock and he began to gently rub it through the material, he heard Sally's light footsteps on the stairs. Quickly he snatched the duvet from the floor and covered himself up, suddenly extremely self conscious about what he was wearing and, even after everything that had happened the day before, embarrassed about looking like that in front of his girlfriend.
"Morning sweetie," she said cheerfully. "I thought you were going to sleep all day!"
"Hmm? What time is it? Jack asked.
"Nearly noon," she answered. "Yesterday must have really taken it out of you!"
"Yeah, I guess. I slept here all night?" he asked, indicating the couch.
"You certainly did. I was going to wake you up to get you to bed, but I couldn't. I managed to get the but plug out of your bum though," she giggled.
"Well, thanks for that, at least! Err, I really ought to get cleaned up and changed back into regular clothes."
"Well, you could certainly use a shower but I'm not sure about the regular clothes. Have you forgotten what day it is?"
"No, I haven't forgotten/ It's Saturday. So what?"
"That's right. And the party is tonight silly, and we have to get you ready for it."
"Oh come on, it will take me 10 minutes to get ready for that. And anyway, I thought we were going to change when we get there."
"Yeah well I spoke to Lucy and it would be better if everyone turned up ready because there won't be enough space for anyone to get changed in. Anyway, I said that seeing as how they were going to so much effort, we would arrive ready to go. That's not a problem is it?"
"Errm, yeah, it is really. How the fuck am I supposed to get there in a dress and high heels?" Jack enquired.
"Oh, don't worry about that. By the time we set off it'll be getting dark and if anyone sees us we'll just look like a couple of girls on their way to a party."
"Hardly sweetie. Even if it is dark I don't think I'm going to fool anyone."
She laughed. "I think you might, actually, but I take your point. We could get a cab I suppose, but it isn't really far enough to make it worthwhile."
"Yeah plus the cab driver would likely pick us up again sometime so I'm not sure how that would help."
"Well, OK. The bus is clearly out then, so that just leaves walking. Don't worry, you'll be fine. I'll make sure you look the part and you can wear that black overcoat of mine. My mum bought it and she must think I'm about a foot taller and a ton heavi9er than I am because it's huge. It should fit you just fine, and it will go with the dress!"
"Great. I am going to get beaten up by some homophobic twat with a low hair line and an IQ about equal to his shoe size, and all because Lucy doesn't want us to change in her spare room."
"Don't worry, honey," said Sally with a grin. "I'll protect you from the locals yobs. Or are you afraid that you might lose your virtue?" There was a worrying glint in her eye. "Don't worry sweetie, all girls have to lose their virginity, and it only hurts the first time!"
"Yeah, very funny. You will recall that I am not in fact a girl, and I have no wish to lose my virginity."
"Not even to me?" She fluttered her eyelids.
"Well, maybe to you, but you would have to ask really nicely!" he replied, grinning.
"Well," she said with a Cheshire cat grin. "We'll just have to see about that I guess." And with that she slowly pulled the duvet away from him and towards the end of the couch revealing first the bra straps on his shoulders, then the delicate lace cups, then his smooth hairless stomach, followed by the lace suspender belt and the knickers and finally the tops of the stockings.
"Hmm," she purred. "You look a bit like a girl. Except that big lump in your knickers. That doesn't look very girly at all. Have you been playing with yourself honey?"
Jack reddened. Why was it that he kept allowing himself to be placed in situations where he ended up being embarrassed by her?
"I think you have, you naughty boy." She reached out with her hand and gently scrapped the nail of her index finger down the underside of his cock through the soft shininess of the white satin. "Were you wanking your cock in these satin knickers? They're not very clean are they? Did you have a little accident in them yesterday?"
As she spoke she wrapped her hand half way around Jack's cock, holding him through the shiny material. "Is that why they have this big stain on them? Did you cum in them? That's terrible," she cooed. "What could possibly have made you do such a thing?" She was stroking him through the material now, firmly but gently rubbing him through the already soiled underwear up and down the length of his shaft from his balls to the tip of his now throbbing cock.
Sally leaned a little closer and began to tease his balls through the material with the nails of her other hand. As she did so she began to rub her leg against the inside of his stocking clad thigh, adding yet another sensation to those already overloading him. Involuntarily he squirmed a little on the couch, but that just increased the sensations as the sating of the knickers caressed his buttocks and the silk-like stockings caressed his entire legs. Even the gentle tug of the suspender belt seemed suddenly too delicious to be resisted. Jack's back arched as Sally's nails alternately caressed the underside of his cock through the knickers and gently stroked his shaft. A groan escaped his lips and his back arched further.
"Oh sweetie, does that feel good?" she whispered.
"Yeah," Jack managed through the rising sensations, struggling to maintain control and so prolong the feeling but his rising orgasm was not to be denied and Jack began to cum with a load grunt, pumping load after load into the material of the knickers, soaking them, his own pubis and Sally's hand as the semen leaked through. She raised her hand to her mouth and sucked his cum from one finger, before putting a second finger in his mouth. Jack automatically sucked his own cum from the proffered digit. She withdrew her hand, and neither made any comment.
Jack slumped back down onto the couch, completely spent.
Sally leaned forward, the palm of her hand still wet with his ejaculation, and kissed him lightly on the lips.
"Feel better now sweetheart?" she asked.
"Definitely!" he replied with a smile. Sally sat up and surveyed her handiwork. The morning's cum stain had quickly grown past that left from the previous afternoon and it was clear that the whole front of the garment would be soaked very quickly.
"I think you had better get this lot off and in the wash, and while you are at it, you better get yourself in the bath!"
"Yeah, I guess you're right!" Jack laughed. "I hope cum washes out OK!"
"Trust me sweetie, it does. Otherwise I wouldn't have a thing to wear!"
Jack laughed once more. "I'll just have a quick shower though, I think."
"No, sweetie. You need a proper bath with lots of girlie products in it so that you look the part later."
"Whatever you say, darling!" Jack smiled.
"At last you understand!" she replied with a wink. Now get all that stuff off and I'll stick it in the machine.
Jack rose from the couch and set about removing the lingerie that he had now been wearing since the previous evening, and had cum in twice in addition to wearing it when fucking Sally the previous night. He reached behind him and felt for the clips for the bra but struggled to get the hooks undone.
"Having a little trouble there?" asked Sally from behind him. "You never usually have a problem getting bras undone!"
"Yeah, but they are usually on you, not on me."
She reached out and unclipped the bra and he shook it from his arms. "I might as well hang on to the socks 'cause I'll need them later, won't I?" he said.
"Oh, don't worry about that," Sally replied. "I'm sure we can come up with something better than a pair of socks if we think about it for a while."
Now free of the bra, Jack pushed the sodden knickers down to mid thigh. His now shrunken cock twitched as the air chilled its cum-coated surface. He pushed a little further and the soaked garment gathered in a pool around his feet. Finally, Jack reached behind him and, with a little difficulty, managed to undo the clips on the suspender belt. He unsnapped the straps from the stockings and rolled them down and so stood naked in the room.
Sally bent down and retrieved all the garments from the floor. "I'm going to wash this lot, so you go and run the bath. I'll be up in a minute," she said, turning towards the kitchen.
Jack climbed up the steep staircase naked, his still chubby cock swaying from side to side as he walked. As he entered the bathroom he caught sight of himself in the mirror and gave a start. It was not his usual image of himself. Other than his crotch being covered in rapidly drying cum, which was a bit unusual in itself, his body was completely devoid of hair for the first time since he was 12 and there were indentations in his skin as plain as day from bras, suspender belts and the tops of stockings. He paused, studying the image before him and turned around to see the continuation of the marks from the straps of the lingerie across his back. Finally, he turned away and began to run the bath.
As the steam began to billow up around him, Jack heard Sally come back into the bathroom. He turned towards her and saw that she was carrying a small plastic bottle. Sally removed the top and poured a generous measure into the hot water, immediately releasing an aroma of jasmine into the room. She picked up a second bottle and poured as smaller quantity of its milky content into the bath. Finally, she put down the second bottle and turned on the cold tap.
After a few minutes she stirred the now slightly cloudy water with her hand and professed herself satisfied with the temperature. "OK," she said. "In you get."
Jack stepped into the bath and sat down, enjoying the heat of the water and the aroma of the bath cream that Sally had added.
"What is this stuff that you've put in the water?" he asked.
"Oh, the jasmine thing is a sort of bath oil and the second one was is a moisturiser. They will make your skin lovely and soft, and you will smell good!" Sally sat down beside the bath.
"I thought you like the way I smell!"
"Of course I do, when you're being a man I love that masculine smell. But you need to smell like a girl today. I think you'll like it."
"I will like smelling like a girl?" Jack asked with a hint of incredulity in his voice. "Aren't you taking this a bit far honey? I mean it's only a party and I'm sure that no-one else will have gone to the lengths that we have. I mean, how many other guys will have had all their body hair shaved off?"
"Oh I'm sure all of them will have, but we'll see. Anyway, who cares what everyone else does. As long as we're going to do something, it's worth doing it right. And I think that you secretly don't object too much, do you?" She smiled at him and then leaned across and kissed him lightly on the cheek.
"Whatever makes you happy, sweetheart."
"I think it's not just me that's happy, is it? Go on - admit it"
"No, I mean it's OK and if you like it then I'm happy to do it, but it's not like it gets me off or anything," Jack admitted.
"Oh really?" she asked, archly. "Is that why you kept getting hard yesterday in the shops and everything? Because it was all for me?" As she spoke she leaned forward and gently grasped his soft penis in her small hand. She squeezed him ever so softly and he felt the first twitchings of his cock starting to stiffen. "I think that you enjoyed it a lot more than you make out, sweetheart. A lot more. But anyway, you're quite right. It is only for the bash at Lucy and Mark's place, so tomorrow it's back to boring old man underwear for you. After all, it's not as though you have a panty fetish is it?" she laughed. "OK," she said letting go of his now chubby cock. You have a soak for a few minutes to let all this stuff soak into your skin and I'll be back in a bit. I have to make a phone call. And no masturbating, OK?" And with that she turned and walked out of the bathroom, leaving Jack even more confused than ever.
True to her word, Sally was back 15 or so minutes later. "OK," she said. "That should be about it. Stand up for me sweetheart."
Jack rose, standing ankle deep in the milky bathwater, and noticing a certain softness to his skin that was unusual. Sally looked closely at his skin and ran the tips of her fingers across the newly bald area where, until the previous day, his pubic hair had been. "Hmm. You need a shave," she pronounced. "OK. Pass me the razor honey, and let's get you sorted out. You don't want to be going to the party all stubbly now, do you?" Her tone of voice indicated that it was not a question.
Sally reached for a bar of Dove and told Jack to raise his arms. She rubbed the Dove bar between her hands and then applied a generous measure of the soft lather to each of his underarms. Then, efficiently and effectively she shaved each underarm, working from the bottom up. Lathering her hands again, Sally applied the foam to Jacks nipples and removed the tiny amount of regrowth before repeating the operation on the line between his navel and his genitals, but stopping short of his pubis.
"Put your leg on the side of the bath," she ordered.
"Which one?"
"It really doesn't matter, silly. One at a time."
Jack raised his left foot and placed it on the rim of the bath, steadying himself against the wall as he did so. Sally lathered his leg from ankle to crotch with swift strokes of her soft hands, the backs of her fingers brushing against the tip of his cock as she did so. Working slowly and deliberately, Sally methodically removed any trace of hair from his leg, turning his this way and that to ensure that she got it all. Once she was satisfied with the left leg, Sally repeated the process with the right.
"OK," she said. "Turn around and bend over for me."
"What? What for?" asked Jack. Memories of the but plug had yet to fade completely.
"So that I can shave you bum of course. Hairy bums are gross on boys, but on girls that are just uber-gross!"
Still slightly nervous, Jack did as his was bidden and turned to face the tiles on the wall. He bent over. "Spread your legs for me honey," Sally told him. As he did so, Jack felt her hands applying the soft bubbles of the Dove bar to his buttocks, the cleft of his arse and finally around his anus. Sally was working much more slowly now than she had on his legs and seemingly taking a lot more time to ensure that the bubbles were evenly spread. Over and over again Jack felt Sally hands smooth their way across his flesh and her finger tips seemed to dwell on his anus more than was strictly necessary. He felt his cock start to swell again.
"I see you're enjoying it honey. Let me try this - you'll love it."
Jack felt one of Sally's bubbly fingers begin to press against his hole, sweeping round and round the wrinkled knot of flesh and pressing on its centre. Gradually she pressed more firmly with each pass until her finger suddenly broke through , entering his asshole to the first knuckle. Jack gasped, and Sally's finger stopped moving. "Everything OK?" she asked.
"Yeah I guess but I'm really not into this whole anal thing sweetie," Jack replied.
"You don't mind doing it to me though," she laughed in reply.
"I thought you liked it!"
"I absolutely love it, honey. That's why I want to do it to you too. You're going to love it once you relax and get over those silly homophobic hang-ups."
"I am not homophobic!" Jack replied, with as much authority as he could muster given that he was bent over in the bath and his girlfriend was fingering his bum.
"Sorry - I didn't really mean it like that. I know you aren't. I meant having hang ups about doing stuff that might be considered somehow homosexual and make you less manly, at least in your silly confused little mind! Just relax and enjoy," As she spoke, Jack felt the pressure on his anus increase as Sally pressed her finger in further and further until he could feel the rest of her and flat against his buttocks. He knew that she was inside him all the way.
The movement stopped. "There now," she said. "That's not so bad, is it?"
Jack didn't reply. It wasn't uncomfortable. In fact, it was quite pleasurable. Not so much that it would excite him, but a little.
"Yeah, it's OK." he allowed."
"How about this then?" Sally asked and as she spoke Jack felt her finger begin to move inside him in a circular pattern, rubbing against the front wall of his rectum. That brought a whole new burst of sensations and Jack was amazed to see that his cock was starting to swell again.
"I can see that little Jack likes it!" Sally quipped, using the pet name that the two of them sometimes referred to Jack's cock as. She continued to rub for a few seconds as Jack, eyes closed and head against the bathroom tiles, struggled to come to terms with the new sensations flooding his lower abdomen and as his cock continued to slowly inflate. Then, as suddenly as she had started, Sally stopped rubbing that particular spot within him and withdrew her finger from his body. He felt his anus almost snap shut as she did so.
"That's enough of that," Sally laughed. "We don't want you peeking too soon, do we? After all, you have a big night ahead of you?" She patted him on the bum. "Come on - turn around" she said.
"What do you mean, 'big night'?" asked Jack, a little confused. "don't think we'll be doing much shagging at the party somehow!"
"Ah, you never know, but I meant afterwards when we get home. You look quite hot in that dress and I might just decide to shag your brains out again. If you're a good boy. Or girl!" Sally giggled. "Kneel down for me."
Jack knelt down in the bath and watched as Sally once again lathered up her hands with the Dove bar. As her hands closed around his cock he shut his eyes and revelled in the sensations - Sally had always been good with her hands! He felt her rub the lather into his scrotum and pubis and opened his eyes as her hands left him. His cock was once again twitching. At Sally's request he rose and stood in the bath with his legs well apart. His six inch uncut cock was about half hard and describing a gentle curve from his body to point down at Sally's knees as she knelt before him and his balls hung low in their fleshy sack, having been thoroughly warmed by the bath water.
Sally picked up the razor and began to remove the suds and stubble in slow, deliberate strokes, careful not to work too quickly for fear of causing razor rash. She grasped his cock in one hand, pulling it this way and that to allow her to shave the base of Jack's pubis as well as the underside of his cock and his scrotum and as she did so he grew steadily harder until he reached full erection. Sally finished the shaving at the same time.
"OK," she said. "I think we are done." She lovingly stroked his cock backwards and forwards a few times, working his uncut foreskin up and down his glans. Then she leaned forward and took him into her warm wet mouth. For a few moments, Jack was in heaven. Already highly aroused by the manual stimulation and the shaving, this additional sensation was just heavenly but much to his distress, and just as he started to seriously enjoy it, she took him from her mouth. She kissed the tip of his cock once and said "Yuck. Tastes of Dove bar! Rinse yourself off honey."
Jack smiled at her as she screwed her face up in reaction to the taste of the Dove bar. "Good idea."
He turned the water back on and selected the shower attachment, stepping under the stream of warm water. Sally leaned over and pulled the plug out of the bath, and then turned away and picked up another bottle and a big white fluffy towel.
Jack switched off the shower and she handed the towel to him.
"Thanks. What's that?" he asked, indicating the bottle.
"Body moisturiser," replied Sally. "It will make your skin nice and soft. Smells pretty good too."
Sally watched as Jack dried himself then, without another word, she began to rub he moisturiser into his skin. She started with his neck and then, once again turning him this way and that worked her way methodically all over Jacks body, finishing with this genitals which received more than their fair share of attention and his bum which was once again penetrated by her finger.
"You're done. I've laid some clothes out on the bed, OK?"
"You've what? What are you, my mother?" Jack joked. "I'm sure that I can manage to get some clothes out of the drawer!"
"I'm sure you can, sweetie, but maybe not the ones I want you to wear." She kissed him lightly on the lips. "Now go and get dressed."
As Jack waked passed she smacked his bum, making him yelp. He quickly quit the bathroom and made his way down the landing to their bedroom, where he stopped dead just inside the door. Sally had said that she had laid clothes out for him, but all that was on the bed was a bra, a suspender belt, a pair of black stockings and the shoes that they had bought the previous day. That was some of the stuff for the party later on, but certainly not what he was going to wear for the rest of the day. After all, the party was still hours away.
"Where are these clothes then?" Jack shouted over his shoulder.
"On the bed, like I said sweetheart."
"Not so much, no."
Jack sensed Sally arriving by his side.
"Yup. There that are. That's what you need to wear sweetie."
"Look there's no point in getting dressed now. I can hardly sit around the house in a pair of stockings all afternoon!"
"Why ever not? Anyway, it's not the dressing up, it's the shoes. You need to practice with them, so you will have to put them on now and practice this afternoon."
"Sweetie, I do not need to practice wearing shoes. I have been wearing them for nearly 20 years now, and I've gotten really good at it!" Jack replied.
"So just how many pairs of heels have you worn?" asked Sally. "Honestly, it isn't as easy as you might think. I remember the first pair of heels that I got and I was tottering around on them for days."
"Yeah, maybe, but I'll just wear my jeans with them."
"No. You have to get used to it all. You need to practice wearing the shoes, but you also need to practice the rest of it. So as long as you are wearing the shoes, you can wear the rest. We don't want you falling over just because you've got that little heel on or are wearing a dress and breaking your ankle or something. Apart from anything else it would be tricky to explain in Casualty!" she laughed.
"Yeah, good point," replied Mark, still not entirely convinced. He was pretty sure that walking in a pair of heels was not rocket science and that he could manage without having to parade around the house like that, but anything to avoid an argument, no matter how good natured it was, so with a sigh he picked up the shoes and slipped one of them on. In any case, pretty much anything would be worth it to avoid showing up in casualty dressed as a woman and with no body hair!
"You need to stockings too, sweetie," said Sally.
"No I don't," he replied. "It's fine like this."
"Honestly, you do. You need to practice how it feels to walk in the shoes with the stockings on. Trust me, it's different. Come on - stand up."
As he rose naked from the bed she placed the black sheer suspender belt around his waist and fastened the hooks.
"OK, you know how to do this now, and it's good practice, so you don't need my help," she said as she handed him the packet of black lace top stockings.
Jack ripped the packet open and extracted the first stocking, unwrapping it from the cardboard that had kept its shape in the packet. He held the first stocking up to the light and admired the delicate lace around the top. He had always admired women's clothing - not in some sort of perverted way, but rather almost an envy thing. There was just so much more variety. Take socks for example. Men wore socks. Women on the other hand had the choice between socks, stockings or tights. And even if Jack thought that tights were pretty horrible and should be banned, he still as a little envious of the options available. He became aware that he was standing staring at a stocking and shook himself out of his reverie.
"Dreaming honey?" Sally asked.
"Yeah. Sorry, miles away!" he replied.
"OK, do it like I showed you then."
Jack opened the top of the black lace topped stocking and put his flattened hand inside, as Sally had shown him. He gathered the material up his forearm as he worked his fingers down towards the toe. Reaching it, he gathered the material between his two thumbs and sat down on the bed ready to put the stocking on. Pointing his toes as he had been shown, he gently placed the first stocking over the end of his foot, enjoying the unfamiliar sensation of the soft material against his skin. He pulled the flimsy garment over the rest of his foot, making sure that the heel was straight and then drew the stocking over his lower leg, gradually releasing more material as he went. As he reached mid thigh he eased the stocking top backwards and forwards to make sure that it reached the whole distance and then adjusted it so that it sat straight and neat with three inches of up thigh between the lace of the stocking and his crotch. Jack repeated the process with the other leg and then, with some difficulty, attached the straps to the tops of the stockings. He straightened up and saw his reflection in the mirror. Added to the sensation of the silken stockings on his legs and the cinch of the suspender belt about his waist he began to feel himself beginning to become engorged once again and his cock twitched forward a little as it began to swell.
"God, sweetie, what are we going to do with you?" asked sally with mock exasperation in her voice. "You are insatiable aren't you? And you are really getting into this lingerie thing!"
"Sorry honey," mumbled Jack. "It's the stockings and everything - it just feels so good against my skin and I can't help it."
"I know, sweetie. It's all part of the fun of being a girl!" she laughed. "But you'll just have to learn some self control like the rest of us have to! And anyway, we need to save something for later," she said.
"What, you mean after the party?" Jack asked.
"Yes, of course. After the party. Now get some underwear on while you can still squeeze it into your pants!"
Jack laughed and turned away from the mirror. He walked over to the dresser and opened the top drawer and, reaching inside, he pulled out a pair of his customary pair of boxer shorts.
"No, not those," Sally said from behind him. "Put these on instead." He looked at what she was holding in her hand and saw a pair of black lace boyshorts that he hadn't seen before and boyshorts was not Sally's usual style.
"They're new," he said. "Are they yours?"
"Ours," she said with a smile. "Put them on. Your boxers would look silly with a suspender belt and stockings, and you need to get used to the sensation of wearing the whole outfit."
"Where did you get these?" Jack asked.
"Oh, I had to pop out this morning to pick a few things up and so I popped into the shopping centre and got some more underwear because you seemed to be getting it dirty as fast as I could get it cleaned, and mine won't fit you. At least, some of it won't. You've already tried on the rest of it! Anyway, I'm sure you will like it."
Jack took the black lace garment from her and bent down to step into it. As he pulled the boyshorts up his legs he felt the elastic of the material hug his thighs and then his genitals as he arranged them properly. He suddenly became acutely conscious of the lace as it sort of nipped at his penis, especially his foreskin, and his scrotum.
Sally handed him a matching bra. "This too," she said. Jack resignedly threaded the garment onto his arms and pulled the straps up to his shoulders. He felt Sally do up the clips and felt her fingers as she straightened the straps behind his back and on his shoulders. Sally turned him around and stuffed the cups with tissues taken from a box by the bed.
"Perfect," she said as she arranged his boobs. "I don't want you getting your dress messy, so I got something for you at the shops.
"Another dress? Don't you think we are overdoing that?" asked Jack.
"Not quite," she replied. Jack watched as Sally picked up a carrier bag and delved inside. He was a little surprised when her hand reappeared holding a plain white shirt.
"A white shirt? I've got three of those in the cupboard! I thought you were going to have me dressed up like a cocktail waitress."
"No, honey, not a cocktail waitress. Put it on."
"Sure." Jack pulled the shirt on but was slowed a little when he discovered that the buttons were on the wrong side, so clearly it was a blouse and not a shirt. Once he had got the shirt on Sally's hand once again disappeared inside the bag and this time came our holding a blue pleated skirt which she handed to him. A school skirt. Sally wanted to dress him in a girl's school uniform.
"Sweetie, what is this? That's a girl's school uniform isn't it?" he asked, pretty pointlessly as it was plainly evident what it was.
"Well spotted! But not just any school uniform."
"What do you mean?" he asked.
"Don't you recognise it? Maybe this will help. Her hand went back inside the bag and came out holding, of all things, a photo album.
Jack was none the wiser until she opened the album to reveal the expected pictures, but it was the subject of the pictures that caught his attention. They were pictures of Sally at school. This was her school uniform. Well, not hers exactly, as no way would Jack, slightly built as he was, have fitted into Sally's size 8 uniform. But the same design - from her school.
Sally took the skirt back from Jack and held it open for him to step into. Pulling it up over his stockings to rest around his waist, she zipped up the skirt and fastened the catch at the top. Adjusting it to face the right way, she made sure that the blouse was properly tucked in and then stepped back to admire her handiwork.
"Oh, no," she muttered. "That won't do." Grasping Jack's arm she turned him around and a second or two later he felt the hairbrush from the dressing table begin to sweep through his long (or a guy, at least) hair. Sally methodically worked her way from one side of his head to the other, seeming to gather the hair behind his head as she went. Then he felt all the strands being gathered together.
"That's better. Look."
Jack looked at himself in the mirror and saw looking back at him a schoolgirl with her hair up and held in place with an elastic scrunchie. Beneath the hair a pristine white blouse covered what appeared to be a modest and yet not too modest pair of breasts, the straps of the bra just visible through the material of the blouse. Further down 'nylons' covered the legs that protruded from the hem of a modest pleated navy blue skirt and finally a pair of slightly-too-high-for-school shoes completed the ensemble.
"You make a pretty good schoolgirl."
Jack was speechless. She had gone too far this time. OK; there was a reason for the black dress - the party that night. But there was no reason for the schoolgirl costume.
"Yeah, this is too much sweetie," Jack protested. "I can't be dressing up like a little kid, even just around the house. It's not right.
"You're not dressed as a little kid, sweetie," Sally replied. That picture of me," - she indicated the one on the open page of the photo album - was taken the afternoon after my last A-Level paper. We were all 18. We all wore this all the way through school. And I'll show you the other reason why you're not dressed like a kid."
She turned Jack to face the mirror and stood behind him, lightly holding onto the sides of his skirt. Then, very very slowly, she began to raise the sides of his skirt from where it had come to rest, a couple of inches above the knee. As she raised the skirt a greater expanse of nylon came into view. Slowly the double thickness part - known to Jack only as the giggle band - was revealed. And then the clips of the suspender belt's straps. And then the straps themselves. And then the hem of the black lace boyshorts. As she continued to raise the skirt the full expanse of the lace garment was revealed with his shaved cock and balls clearly visible through the mesh of the lace.
Jack looked at the reflection, transfixed. Sally whispered in his ear "See sweetie? Little girls don't wear underwear like that. Only women do. Only the upper 6th. Little girls wear woolly tights and My Little Pony knickers. So don't worry about it." As she spoke he could only stare at the reflection. Although it troubled him deeply, the image was very arousing and he could feel his prick once again start to engorge. She moved her hand and squeezed his penis through the lace of the knickers.
"I think you like it, don't you?" she asked. It was again more of a statement than a question. "I know you've looked at my school photo album."
"What? No I haven't. I've never touched it!" Jack protested.
"Oh honey, I know you have. It's moved when I've been out. Just a little bit, but enough for me to notice. And I don't think that it's a coincidence that it now seems to fall open at that page of me dressed like this. There's no need to hide it from me. In fact I like it. Lucky for you it wasn't falling open at a page with someone else on it though!" she laughed as she gently rubbed his cock through the lace.
"I used to have a pair of knickers like his and used to wear them under my school uniform sometimes. Only when I was feeling naughty though, because to be honest I found the constant stimulation from the lace to be a bit distracting. In fact, sometimes it got so bad that I had to go to the loo and take them off. But then having no knickers on at all was even more distracting. Usually I ended up in the loo having to Jill off. Would you have liked to watch that?" she asked, still stroking him through the lace knickers. "So I saw them in M&S and it brought all the memories back, so I thought I would buy a pair for you. In fact, I've bought two pairs. And two school uniforms. On each. Maybe we can play together sometime. Would you like that?"
Jack nodded, his mind now jammed with images of Sally masturbating in the school loo wearing what he was wearing now. With Sally's gentle massaging of his hard cock he was quickly approaching climax, but then, as suddenly as she had started to stroke him, she stopped.
"OK, sweetie I think that's enough for now. We don't want to go wasting anything now, do we?" she laughed. "I've got to pop out now to get some stuff for later. You be a good boy while I'm away, OK?"
"OK," he replied, frustrated and horny and wanting to cum.
"Now remember. The reason that you are dressed like that is because you are supposed to be getting used to wearing the heels, so you need to keep moving around while I'm out. Make yourself useful - you can put on the laundry and put the clean stuff away. Or tidy up, or something. Anything to keep practicing with the shoes."
And with that sally patted his cock through the lace panties and then let the skirt fall back into place.
"I won't be long," she said, kissing him on the cheek.
Jack was still gazing at the reflection in the mirror when he heard the front door close behind her. God, he was horny. He was desperate to cum and he had really thought that Sally was going to finish what she had begun but for some reason she didn't want him to. His hands found the material at the sides of his thighs and stroked it gently. He slowly turned this way and that, savouring the sensation of the skirt moving against his nylon encased legs. The sensation was out of this world. How did girls manage to get anything done when being constantly bombarded with sensations like that? How were they not masturbating 20 times a day?
Jack gently cupped his swollen cock through the skirt, feeling the little scratches of the lace against that most sensitive skin. He could feel that he had leaked pre-cum into the knickers and his cock was throbbing in his grip. He had to cum, there was no way he could stand this. If he came, he rationalised, then he would be able to get on with the shoe practicing and chores without the unbearable distraction. That would be the best thing, wouldn't it? Sally would never know about it. And anyway, it was his cock and if he decided to have a wank then it was his business.
As he turned away from the mirror his eye was caught by a crumpled white mass on the floor. Sally's knickers. The ones she had been wearing yesterday when she had been to have her beautiful pussy waxed and then taken him shopping. She had said last night that she had been really wet most of the day, and her pussy had certainly been soaking when they had started to fuck on the couch.
Jack bent to pick them up from the floor, his skirt caressing the backs of his thighs as he did so and doing nothing to add to his ability to control his arousal. As he rose he looked at the delicate little garment that had covered his beloved girlfriend's. They were a simple white plain pair of knickers, but there inside them was the evidence of Sally's arousal the previous day. Apart from the `usual' marks left by a healthy pussy, it was clear that she had soaked her way right through them at some point or other. He raised the knickers to his nose and inhaled the familiar and much loved bouquet, closing his eyes as he did so. Sally had been right when she confronted him the previous day. He did enjoy wearing her knickers, far too much in fact. But he also adored smelling them and even tasting them. He loved her aroma, and loved her taste even more and there was nothing better than tasting his beloved's knickers whilst masturbating himself. The added aroma seemed to make his orgasms much fiercer and longer lasting.
It was no good -- he had to. He simply couldn't help himself. Not caring that Sally had told him to behave himself, Jack lifted the hem of his skirt and, pulling the leg of the boyshorts to one side, began to masturbate his pulsating cock. Eyes close tight, he pushed the discarded knickers into his face, revelling in the smell of Sally's pussy and, opening his mouth, her delicate taste on his tongue. It was heaven. Nothing compared to Sally and to be here with her knickers and her smell was simply heavenly. As Jack felt his orgasm begin to mount somewhere in the base of his spine he took a final deep breath through the gusset of Sally's knickers and then wrapped the delicate cotton garment around the end of his cock. His orgasm broke over him and he could feel himself depositing squirt after squirt of hot cum into the knickers. He groaned involuntarily and collapsed to his knees.
As he opened his eyes he saw a figure in the mirror. It seemed to be a schoolgirl in her regulation uniform, but her skirt was hiked up around her waist and her lace boyshorts, perfectly framed between the tops of her stockings and the straps of the hidden suspender belt, were pulled aside to reveal, not the delicate pussy of a young woman, but rather the cum streaked shaved cock of a young man who was holding a pair of sum stained knickers to the end of his rapidly wilting cock. Jack smiled.