Prologue

Angelica looked through the yellow pages trying to find the number she needed.  As she flipped through the pages she was surprised to find just how many adult “novelty” shops there were in town, smiling as she was already thinking of ways to make use of that information.  Finally she found the one she was looking for and dialed.

       “Hi, I was hoping to talk to someone there willing to help me out with something I would like to try involving a friend of mine and a shopping trip to your store”  “Well, we are always happy to try and help out our customers, what can we help you with?”  Taking a breath Angelica gave a quick outline of her plan to send Anthony on a special shopping trip on his day off…

Chapter 1

Anthony woke to the sound of his alarm blaring loudly in his ear.  Angry at the intrusion into his dream and the fact that he was sure he hadn’t set his alarm for such an early time on his day off he reached over to slam the off button to find bright pink sticky note waiting for him.  “Hello, my little sissy slut, I know you planned on sleeping your day away today but I have some plans for you today so get your ass out of bed and read the note I have left for you on the dresser”

Immediately awake and interested, Anthony slid out of bed and walked naked (he always slept naked when he wasn’t told to sleep in his nightie or baby doll) over to the dresser to find a sealed envelope that smelled of Angelica’s perfume and had SISSY SLUT in large letters written on it.  Definitely interested in what his Mistress had planned for him, Anthony tore into the envelope to find a letter printed on bright pink stationary.  “Good morning my little sissy.  You had better be standing there naked as I have not told you to get dressed yet.  Before you do anything else I want you to take a picture of yourself right now and send it to me.  I had better get it before 9am or I will know you slept past the alarm I set and ignored my note.”  Quickly he looked for his cell phone and took a picture, sending it directly to Angelica, noting that his phone showed a time of 8:57.  She had only given him 5 minutes from the alarm to his time limit, it was a damn good thing he hadn’t hit the snooze or even gone to the bathroom before opening the letter.  He shuddered as he thought of what she might have planned if he had been late.

“I have planned out a special day for you that I know you will enjoy.  From now on follow every instruction in this note to the letter.  Do not read ahead as you go.  I have set it up so that even if you do read ahead, you will not know what lies ahead, but it will be much more fun for you if you only go step by step”.  With his cock hard as a rock and throbbing, he continued to read the note carefully.  “The first thing you will do is eat some breakfast; you will not have a chance to eat again for a few hours.  Stay naked, and don’t touch anything other than what is prepared in the fridge.  Leave the letter on the dresser so you aren’t tempted to read it as you eat.”

Putting down the letter Anthony walked through his apartment into his kitchen.  Immediately he realized how bright it was and understood why he had been instructed not to touch anything.  Every window blind in the apartment had been pulled completely open, giving him a full view of the outside world, and more importantly, giving the outside world a full view of his first floor apartment.  Feeling completely exposed Anthony was relieved to find that at least for now, nobody was outside as far as he could tell.  Quickly going to the fridge he opened it up to find a small bowl of cereal that had already been prepared.  Another small pink note was attached for him to read.  “By the time you read this I will have been gone for at least two hours.  I am sure your cornflakes will be just about ready for you.  Enjoy and remember, don’t touch anything else!”  Looking at the bowl filled with cereal that couldn’t even be considered soggy, Anthony picked it up and put it on the counter.   Without thinking, he opened the drawer to get himself a spoon.  He realized his mistake as soon as he felt the small piece of thread break and saw the big pink note waiting for him “BAD SISSY!!!!!!   I thought I was very clear about not touching anything!  This will be dealt with later…”  Looking at the broken thread his Mistress had secured to the drawer, Anthony knew there was no way he could replace it or hide the fact that he had opened the drawer.  Resigned to his fate, he took his bowl of mush to the table and looked at the chair.  This time, as his hand touched the chair he realized what he was doing and stopped.  Without moving anything he stopped and looked under the table and was rewarded by finding another note stuck to each chair and thin thread tied to each one.  Standing naked in his kitchen, with a bowl of the soggiest cornflakes he had ever seen, Anthony felt his cock once again throb to full hardness as he realized what his Mistress intended for him.  Placing the bowl in the floor in the middle of the kitchen floor, in full view of the kitchen window and Living room window, he knelt, naked in his hands and knees and began eating out of the bowl like a dog.

Chapter 2

After what seemed to take forever and involved soggy cereal going up his nose at one point and a scary moment with a small group of neighbors walking by his windows, Anthony finally finished his breakfast.  His tongue was tired, his knees hurt and he felt like he still had a cornflake in his nose, but his cock was still throbbing and had even started to leak a little pre-cum as he had eaten.  Standing, he put the bowl in the sink and hurried back to his dresser to see what else was in store for him.  “So did my little slut puppy enjoy his breakfast? I hope you followed your instructions for your sake.  I will know if you didn’t and you will be punished as I see fit.”  Remembering the broken thread, Anthony shivered at the thought of her finding it. 

“Time to get you cleaned up.  Open the top drawer in your dresser and follow the instructions.  You will find the key to the drawer on the picture shelf in the kitchen.”  A few weeks ago, Mistress Angelica had made Anthony install small hasps on each of the drawers of his dresser.  Using the hasps and small locks, she was able to take control of what clothing he was able to have access to and when.  Walking out to the kitchen again, Anthony had to stretch over the window being fully exposed to reach onto the high shelf; it actually took him a few moments of feeling around to find the key.  The whole time he could hear his neighbors talking nearby, but no one was in view of the window thankfully.

With the key he was able to unlock the drawer and opened it to find his pink instruction page and a large cloth bag.  “Before you get cleaned up on the outside you need to get cleaned up inside.  Prepare yourself an enema using the equipment I have provided.  You may read this entire instruction sheet to prepare it and to do it as I wish.  First take everything out of the bag.  Fill the enema bag with nice warm water and the solution provided, and then fill yourself.  You will give yourself a total of two, in order to make sure you are fully cleaned.  For the first one, allow the bag to empty and then you may relieve yourself.  After you have done that prepare a second one and just before you start the flow, push the start button on the timer I have provided, you will retain all of it until the timer goes off.” 

Anthony took the bag into the bathroom and emptied its contents on the counter.  He eyes grew wide as he saw that Mistress had dug out his large 2qt bag in place of his usual 1qt.  She had also replaced the usual small nozzle with a thick black inflatable butt plug designed for giving and retaining enemas.  On the new plug was another of those notes, this one said “I have already given it a few test pumps so you do not have to… I think 5 pumps will do for today.”  Checking the rest of the items he found that Mistress had been kind enough to include a small bottle of lube for the plug, two bottles of solution for the enemas, and the timer.  Looking at the timer, Anthony immediately noticed that the display had been covered with black tape, he had no idea how long it had been set for.

Working quickly, Anthony set everything up.  He empted a bottle of solution into the large 2qt bag and then filled it the rest of the way with warm water.  As it filled he realized just how heavy the bag felt and how much water it held.  Attaching the hose and nozzle he hung the bag un the shower and proceeded to lube up the ominous looking plug.  Slowly he inserted it into his tight ass and felt the wonderful fullness as his hole was stretched and filled.  Just as it felt like it was getting too big, it popped past the widest part and slipped nicely.  Taking the air pump he began to count.  On the first pump he was surprised at how much bigger it got.  By the third he was feeling incredibly full and wondered if he could handle all five.  Quickly he squeezed two more times and felt the plug expand inside him, stretching his tight hole and completely sealing it in.  With a low groan he sealed the valve on the plug and then opened the valve leading to the bag.  The warm water quickly flowed into him, making him shudder in pleasure.  The first few moments of the warm water filling him always felt so good.  As the water flowed, the pressure started to build inside him.  It didn’t take long before he got to his hands and knees, relieving some of the pressure brought on from standing.  As it continued Anthony got to the point he was quite used to after his normal 1qt.  But the water kept going.  As he filled more and more the cramps began and he could feel his guts clenching.  Before he realized it the water stopped flowing and the first one was done.  He released the air in the plug and quickly went to pull the plug out and relieve himself.

Once he had caught his breath he knew he needed to start the second one.  Again he prepared just as before and when he was ready he remembered the timer and hit start just before starting the flow.  This time the water seemed to flow even faster than before and the feeling was incredible.  It took a little longer for the cramps to start but when they did they hit hard and he let out a groan.  With no idea of how long the timer was set for, all he could do was wait.  As he waited, Anthony let his mind drift to what his Mistress might have in mind for him the rest of the day and as he thought about it, it kept him extremely excited and made the suffering inside him feel a little better.  He was even thankful for the new plug, with it expanded inside him like it was, he didn’t have to use any effort of his own to try and retain it, he couldn’t have relieved himself even if he wanted to with it in.  Finally as the cramps were about to drive him crazy the timer went off.  Anthony didn’t even turn off the timer as he ran to relieve himself.

Chapter 3

       Finished with his internal cleaning, Anthony went to the letter from his Mistress.  He found that the original one had ended and continued on in another letter that had been in the locked drawer.  So much for reading ahead, even if he tried he wouldn’t get very far with each new step being locked away.

       “Now that you are all cleaned out inside, go ahead and take a nice hot sissy bath.  Get yourself cleaned up and shaved nice and smooth.”  When his Mistress put him in sissy training, there were no basic showers anymore.   Sissies needed to take nice hot baths with oils and perfumes to keep their skin soft and smelling pretty.   Under the sink he found what had been left for him today.  A can of women’s shave cream, a new ladies razor and some very heavily scented perfume body wash and bath beads.  Drawing the bath, Anthony ran the water nice and hot and dropped in the beads and was happy to see that they were even the kind that foamed up letting him soak in a bubble bath.  Realizing that he was smiling at the thought if soaking in a hot perfumed bubble bath made Anthony think about just how much his Mistress’s sissy training was starting to take hold in him.

Crawling in the water he laid back and enjoyed the feeling of the bath for a while before grabbing the new razor.   The shave cream felt good as he lathered it up and started with his armpits.  After making sure he was stubble free under his arms, he lathered up his legs and spent some time making sure that his legs were completely smooth.  When he had first started shaving his legs he had felt embarrassed by it, but over time he realized he liked the way they looked all smooth and there was no way he could deny how much he loved the feeling of his freshly shaved legs in a pair of stockings or even soft slacks.   Once his legs were done, Anthony carefully shaved the stubble that had grown around his cock and balls.  Again, he had to admit he loved the feeling and looks of being freshly shaven and clean there.  Shaving was getting to be such a pain though and he wondered just how serious his Mistress was about starting him on a laser hair removal program in the near future.

       Finally smooth from the neck down, Anthony climbed out of the bath and toweled off and finished off with a quick but thorough shave on his face, again wondering about the possibility of laser removal to make it so much easier…

Chapter 4

       Walking naked and smelling very pretty, Anthony found the latest note only to read that his next step was in drawer number two and that the key was in the planter on the back porch.  He had to read that a second time to make sure it was for real but there it was.  His back yard was small and well enclosed, but the planter was at least six steps out the door.  His cock betrayed him and sprang to attention at the thought of having to run outside naked to find the key.  Quickly before he had time to get nervous again, Anthony went though the apartment and out the sliding glass door in the back.  Without even looking around so as not to think about it, he walked straight to the planter and was relieved to find the key right on top and not hidden.  Grabbing the key he practically ran back inside shaking with the excitement.

       Unlocking the second drawer revealed a new note.  “Enjoy your little walk?  I wish I could have been there to see it.  Of course if I had been, I would have locked the door behind you and made you beg to get back in… Maybe I will plan that for next time.  For now it is time to start getting dressed.  In the bag here, you will find what you need to get started, you will notice it is a small bag, which is because there are no clothes yet, those will come later my little sissy slut.  For now, put on everything in the bag.  If you have to, you have permission to get some ice to help.”   Anthony nervously took hold of the bag.  The mention of the ice gave him a pretty good idea of what he was going to find and the sound of metal pieces clinking together confirmed his suspicions before he actually opened the bag.  He dumped the contents on the beg and began sorting them out, finding another note he set it aside for a moment as he looked at the items.   He found his Mistress had put together some interesting items for him to get started with.  A small black thong panty, a pair of silky smoke colored thigh high stockings, a black lacy garter belt to hold up the stockings.  He looked closer at the stockings and realized that they were not the kind that would stay up them selves, the garter belt was not just for show, it would actually be needed to hold up the sexy stockings.  A small butt plug was resting next to the garter belt along with a small bottle of lube.  A black lacy bra matching the thong and garter belt was next.  To fill the bra, Anthony saw that his Mistress had included his silicone breastforms as well. 

Finally, his eyes settled on the piece he had been expecting to find and the source of his nervousness and excitement.  At first glace it was nothing more than a small leather pouch and a long leather strap, but he knew that it was one of his Mistress’ more diabolical toys.   She had found it while causally looking through a catalogue filled with nothing but toys designed for locking up a slave’s cock and had decided to purchase it before she had even finished reading the description.    The “transvestite pouch” was a very simple but effective form of bondage and torture she had made sure to include as often as possible in Anthony’s training.   The pouch was just that, a small leather pouch with a buckle and strap on the open end.  The slave’s cock was stuffed inside the pouch and the strap was then buckled tightly behind the balls securing the pouch in place.  “Small” was an understatement, in order to fit in the pouch Anthony had to be completely soft and he literally had to be stuffed into the pouch, even then his cock and balls barely fit inside the bag.  Once in, the bag became an instant source of excitement and torment.  The feeling of tightness and just the fact that he was bound made him extremely excited, but that very same confinement allowed for absolutely no room for his soft cock to grow in any way.   Of course to ensure that the pouch stayed secure, there was a small shiny padlock that could be secured to the buckle making sure once it was on, it wasn’t coming off until Mistress wished it.  Many people would have felt that just having a slave’s cock squeezed and secured would be enough, but the clever device didn’t stop there.  Attached to the front of the pouch was a small D-ring that had a thin leather attached to that.  The strap had many uses of course.  The most obvious was as a leash that could be used to lead him around by his cock and balls, or simply locked to something else to hold him in place.  Looking at the strap Anthony could not help but remember just last weekend when he had been locked into the toy and the leash locked to a point on the wall, pulling it up very tightly.  He had begged his Mistress to lower it but she smiled and said, instead she would raise him higher.  The next thing he knew, he was wearing a pair of 9” ballet heels on his feet.  The heels made him stand on his toes taking the tension off his tortured cock, but after being left in that spot for two hours and unable to sit or even move more than a few inches, he had been almost ready to simply drop and see if a human could hang by his cock and balls just to take the weight off his tortured feet.  After the memory passes, Anthony saw that Mistress Angelica had of course included the additional strap that could be used with the pouch.  The leash was pulled up tight between the slave’s legs, pulling his encased cock back with it.  The thin strap was just long enough that it would pull back, split the slaves ass cheeks and reach the small of the back.  The second strap was then pulled through the loop at the end of the leash that was used as the handle.  Finally the second strap was pulled around the slave’s waist and secured, holding the leash pulled up tightly and therefore the slave’s leather bound cock and balls pulled back rather harshly as well.   The simple pieces of leather were extremely effective at both securing the slaves cock and balls, acting as a chastity device, and all with the addition of removing that annoying bump that all sissy boys have to deal with.

After being excited and hard all morning long, Anthony knew this was going to be very uncomfortable but he also knew he had no choice and loved the feeling of being so incredibly controlled.  He walked to the kitchen to get the ice and was not surprised to find that some crushed ice had already been prepared for him in the freezer.  His Mistress new him well and knew he would be in no condition to fit in the pouch without some help.  Lying on his bed, Anthony spread his legs quickly took a handful of ice to his throbbing cock.  The feeling was so intense that he gasped and shivered as soon as the ice touched.  He rubbed the ice all around, over his cock, his balls, even his thighs.  At first it seemed to have the wrong effect and he seemed to get harder and throb more.  Precum even began to leak out as he rubbed.   As the ice melted though it started to do what it was supposed to.  After grabbing another handful to replace the melted ice, Anthony noticed that his cock was indeed beginning to shrink.  Rubbing it around and holding the ice in place until it was almost too painful to stand, finally got his cock to shrivel up as small as it would get.  Working quickly, knowing that he would begin growing again almost immediately, he stuffed his shriveled cock into the pouch and pulled the strap tight.  Once he adjusted the buckle to the fit his Mistress had found to be just right (not too tight to cut circulation, but not too loose to allow escape) Anthony took the padlock and secured it to the buckle.   The next step was securing the other straps.  He put the belt through the leash and pulled them through his legs and was wrapping the belt around his waist when he realized he had almost made a huge mistake.   The butt plug had rolled under the bra and he had almost forgotten about it.  Thankful he had seen it in time, he lubed it up and slipped it into his tight asshole, enjoying the sensation of it sliding in and stretching and filling him.  Once the plug was in place, Anthony continued with the straps.  The way the thin strap was pulled up between his legs and between his ass cheeks, it ran right over the plug buried in his ass.  Once the straps were all pulled tight and secured, the plug would be held in place and locked in as well.  Making sure everything was adjusted as well as it could be, he buckled the belt in place and added the second padlock to the belt.  The feeling of his cock trying to grow at the sound of the click the lock made was almost too much and he had to concentrate hard to try to calm down so he could move around.  It was going to be a long wonderful day.

The transvestite pouch was followed by followed by black thong.  Next he put on the bra and inserted the breatforms to fill the cups.  The bra was only an “A” cup and not very large.  Anthony remembered how once upon a time he had fantasized about having large “D” cups and had been disappointed when Mistress had first bough him the smaller forms.   That had been when he had realized just what it meant to have them.  The breastforms gave him the feeling of weight on his chest and in the bra and filled the bra completely making it very firm.   Then Mistress had taken him out in public with it on under his shirt.  Even at an “A” cup there was no hiding them.  This was no thin lace bra that was hidden under a shirt that no one saw.  They were small, but very firm and very noticeable on his thin build.  The added weight to his chest ant the slight jiggle that movement caused made it impossible to try to forget or ignore that he was out in public with tits.   From then on, Anthony had been quite thankful that Angelica had chosen the smaller size, but after months of training and him growing more comfortable with wearing them in public, Mistress had started hinting that it might be time to try a “B” cup soon.

After the bra and panties, Anthony took hold of the silky stockings and slowly rolled them up his legs.  As he did so he had to admit to himself that this was one of his favorite feelings in the world.  He truly loved the feeling of the nice, tight, silky stockings caressing every inch if his freshly shaven and very sensitive legs.  He spent a few long moments just slowly working the stockings up so he would not put a run in then and to just enjoy the feeling.   The stockings were followed by the garter belt.  As he put it on he realized he had again made an error.  He quickly pulled down his panties and attached the garters to the stockings before pulling the panties back on.  His Mistress had always taught him that a true slut always wore the panties on top so they came off first and the stockings and garters could be left on.  

Chapter 5

       There were no games with the key for his next step.  It had fallen out of the transvestite pouch when he had moved it around just before putting it on.  Unlocking the drawer Anthony looked in to find this was the drawer with his outfit to wear.  The note waiting on top of the nicely folded clothing was a little more detailed than the last few.  “My little slutty sissy is almost done getting ready for today.  How are you feeling all stuffed in your tight pouch and tucked nicely?  I hope you remembered to put your plug in properly as well.  Well, while underneath you will definitely be the slutty sissy you are, on the outside I will keep you a little classier.  Finish dressing and getting ready and then you will leave to begin your errands.   I have left you a package in your mailbox that you will retrieve and open before you go.  It will have everything you need for the rest of the day.  Be sure you do not open anything within the package until you are allowed to do so, you will know when that time will be.  Your destination will be written on one of items, do not make any additional stops on your way, you are to go straight there and be there by 11:30am.”

       Looking at the clock Anthony saw that it was a little after 10:30, so his Mistress had guessed well at the time.  She definitely knew him well and had known just how long each step of his morning would take for him to complete.   Knowing that he was on a schedule now, made him hurry up just a little more since he wasn’t sure how far he would have to go once he left.

       Setting his outfit on the day he was rather pleased by the choice his Mistress had made for the day.  He found his black women’s slacks, a light pink blouse, a pair of black heels that looked to be about 3” tall with sexy ankle straps and open toes, and a large makeup bag.  The makeup bag had a small note telling him to be sure to put on everything properly.

       The pants went on first and he loved the way the material felt as it slid over his stocking clad legs.  They had looked long and hard to find a pair of pants that fit perfectly.  He was very proud of the fact that he fit into a size 4 almost perfectly, but length was always a problem for him.  This had been bough quite long and then hemmed so that they hung perfectly on his legs when wearing 3”inch heels, making his legs look much longer than they actually were.  The pants were made of a slightly stretch material as well and clung nicely to his ass and thighs.  Anthony had been working out long and hard to trim up his body and it was finally starting to pay off.  He was able to wear these tight pants and feel quite happy with the way they looked.  As he pulled up the pants he looked in the mirror and noticed that he could just barely see the outline of the garters underneath if someone knew what they were looking for.  His finished pulling them up and reached behind to zip them up, there was absolutely no mistaking these for boy pants in anyway.  He put on the blouse and buttoned it up, wondering how much longer it would take to get used to wearing women’s shirts with the buttons on the opposite side.  The blouse was a good fit just like the pants.  It was a light pink with a tapered fit so that it helped give the illusion of having more of an hourglass shape to him.  The blouse fit perfectly over his firm bra, emphasizing the small but extremely obvious tits that he now had.  The length was also just right, hanging just below the top of his pants.  Finally he slipped his heels on and buckled the straps in place.  He loved the way his legs looked in heels and the illusion the heels and pants gave of his long legs was something he always found himself staring at for a while.

       The makeup bag was last and he noticed it was heavier than he expected.  As he emptied it out on the counter he realized why.  Inside the bag his Mistress had included a few more surprises for him.  Besides the makeup there were two special leather straps with rings on them that he knew well, a long shiny chain, and 3 small padlocks.  He knew where each one went and proceeded to put them on.  The chain was what he would wear in place of a belt.  It slipped through the belt loops of his pants and  around his waist.  He had to admit it was a great idea his Mistress had found.  The chain looked like a great accessory  with most of his outfits and once locked around his waist, effectively kept him locked in whatever pants he was wearing, unable to take them off again without access to the key.   The other two straps were something he was rather proud of as he had made them himself.  Very simple design and very effective at what they did.  Small metal rings were attached to what looked like a short leather “T”.  First he slipped the metal rings over each of the the heels on his shoes, then he pulled the straps up and buckled them around his ankles and locked the straps in place.  The purpose was easy to see, with the straps in place, his Mistress was able to lock just about any pair of heels onto Anthony’s feet, with no way for him to take them off until she decided he was done wearing them.

       The final preparation was doing his makeup.  It had gotten to be second nature to him to apply his own make up these days.  He had been doing it for years now in secret and had lots of practice.  The colors that had been chosen for him were of course perfect for his outfit.  A foundation that matched his skin tone followed by black eyeliner and mascara.  His eye shadow was a light shade of purple that had been picked to go perfectly with his blouse, it had enough blue in it to bring out his blue eyes dramatically and enough red to make it compliment the blouse nicely.   Finally a light pink shade of lipstick that again complimented the blouse.   His makeup for the day was not exactly so subtle that someone wouldn’t notice, but he certainly didn’t look like  a painted whore as his Mistress sometimes liked him to be.

       Before heading out Anthony took a nice long look in the full length mirror in his room and felt his trapped cock try to grow as he took in the full effect.  He stood there in his pink blouse showing off some nice firm tits and feminine curves.  Long legs created by the nice stretch slacks and his 3”heels.  He couldn’t help to be aware of the fact that the pants and shoes were locked on and staying that way.  Underneath his outfit he was also fully aware of the sexy things underneath.  He could feel the plug deep in his ass locked away by the strap pulling his trapped and currently frustrated cock along with the stockings, garters and bra and panties he was wearing.   As he looked the overall image he could not help but notice one of the most important things his Mistress had done.  She had not given him a wig.  Without it, and with the still very male haircut that he had, he was very definitely not a woman, and he was not exactly a male, what he was, was a very obvious sissy getting ready to go out in public.

Chapter 6

       Anthony stepped out of the apartment, hoping that there would be no one out to see him and hearing each step in his heels sounding like a gunshot just begging people to look his way.  His mailbox was not too far away and he made it with no one noticing.  He did see a few people on the other side of the lot but he didn’t know them and at the distance he felt he was still safe.  Inside the mail box was a large envelope that told him to open immediately.  He looked in to find that Mistress Angelica had left him his car keys but she had taken his apartment key off.  He had expected to find his wallet, but she had replaced it with a small black ladies hand purse and he noticed that she had put a small seal through the clasp on it, reminding him he as not allowed to open anything but the large outer envelope.  He had no idea what she had out in the purse, but as she had clearly planned everything out very well, he trusted that it had all he needed.  Finally he looked at the sealed envelope that was inside the larger one.  Written on it he found “deliver this to a woman named Danielle at the adult novelty store we went to last weekend.  She is expecting you by 11:30.  You can be early but do not be late.  No parking behind the store either.”

       He turned from his mailbox to walk to where he normally parked his car and immediately noticed that is was not where it should have been.  Feeling his heart race he scanned the parking lot at finally saw it parked at the far end, as far away as possible.  Swallowing his rising panic he tried to walk as fast as he could towards it, wanting to run but knowing that if anyone saw him he would be noticed that much more if he wasn’t trying to be casual.  Behind him he heard one of his neighbors leave their apartment but with is back to them all he could do was hope they didn’t recognize him and notice the car he was getting into.  Finally getting to his car, with his hands shaking he unlocked it and climbed in.  As he started the car he found a final note from his Mistress stuck to his dashboard. “Hey slut, thanks for letting me borrow your car last night, hope you found it ok.  Have fun, and don’t forget the rules.”  For a moment he didn’t understand her mentioning his rules until he saw that the note had been covering the gas gauge.  Somehow last night she had managed to use up just about all of his gas and she was reminding him that he was supposed to go straight to his destination with no stops. 

       With no more time to delay, he pulled out of the parking lot and prepared himself as well as he could for what might lay ahead.

To be continued…..

 

Chapter 7

       The drive to the store was uneventful, but all the same it had been nerve racking to Anthony.  Until his Mistress had started making him go out in public dressed up, he had never left his house with more than panties hidden under his clothes.  And now here he was driving through the middle of town wearing nothing but women’s clothing, and extremely feminine clothing at that.  Even the act of driving was very difficult.  The plug in his ass kept wiggling with every movement, and the tight pouch with his scrunched up cock and balls continued to tease and torment him.  He had even almost gotten in a minor accident at a light when he had gotten his 3” heel hung up as he was stepping for the break.  Anthony could only imagine what it would have been like dealing with an accident dressed as he was.

       Finally he reached the adult toy store and pulled into the parking lot.  Remembering his instructions he found a spot in from of the store, unfortunately all the close ones were filled and he had to park much farther away than he wanted to.  He thought about waiting and hoping one would open up, but traffic had been bad and he only had a few minutes left before he was late.  He grabbed his keys, his purse and the envelope and took a few deep breaths and feeling his pulse pounding in his chest, throat and his cock, he stepped out of the car and walk as quickly as he could straight into the store.

       He had hoped that the store would be almost empty but he was no where near that lucky.  There were more people than he felt he had ever seen in the store at once browsing around.  Knowing that he couldn’t back out now even if he wanted to, he fought the urge to run out the door and instead walked towards the counter.  It felt like everyone was staring at him as his heels clacked on the tile floor and drew more attention to him.  Finally he reached the desk and counted three people standing in front of him.  As he stood there, a woman in front of him turned and looked him over, she did not even hide the fact that she was looking and checked him out from head to toe and back again, As she turned back around he could see she was chuckling lightly to herself.  Thankfully she didn’t say anything, but just at that moment from off to the side of him he heard a male asking his girlfriend “what the hell is that?” And could see him out of the corner of his eye pointing towards him.  Completely mortified, Anthony could do nothing but hang his head and feel his cheeks burn in embarrassment.   When the line moved forward he looked up towards the desk and saw the salesgirl looking at him, but she seemed to make a point of not saying anything or asking if he needed help since he obviously didn’t have anything to purchase yet. 

       Finally he reached the desk and the girl looked him over again smiling and asked if he needed help finding anything.  It took him two tries to get his voice to work but he managed to squeak out that he was supposed to ask for Danielle.  She nodded and said she figured he was the one that was supposed to stop by.   With that she picked up the phone and dialed a quick number.  To his horror, the phone was not a direct line but instead connected to the store speakers in the ceiling.  “Hey, Danni, yeah the guy, well I think he’s a guy, anyway the one you are waiting for is here. 

       Anthony wanted to crawl into a hole and disappear but instead the girl put down the phone and with a wicked glint in her eye told him that Danielle would be out soon and he could wait over by the side of the counter.  Of course after the announcement it seemed that if everyone hadn’t noticed him or looked at him yet, they made a point of walking by and looking at him now.  Some seemed shocked, others laughed and a couple people tried to act like they weren’t looking but found interesting things to look at that just happened to keep them where they could look over from time to time.

       Finally after what felt like hours but was only a few minutes, a rather attractive woman walked out of the back office and toward Anthony.  She looked him over as she walked but once she got there she gave him a full head to toe look and back again.  Before saying anything else, she simply told him to turn around so she could see him from that angle.  He turned for her, feeling both embarrassed by the inspection and excited by being on display.  “Well your friend wasn’t kidding when I talked to her last night, you are quite a piece of work aren’t you.  Well I am on break now so let’s see if this is actually going to be worth my personal time or just a waste of it.  What have you got for me” With that, Anthony handed over the large padded envelope and stood clutching his purse as she opened it and looked inside.

       Anthony watched her look inside the envelope for a couple of moments and then she told him to wait where he was standing.  She walked to the counter and he noticed that another salesgirl had joined the first one and they were both watching.  Danielle went to the desk and set the envelope down and pulled out a neatly typed letter.  But made a point of keeping the rest of the contents from his view.  She called the other two over and they all read the letter as he stood off to the side with no idea of what was in store for him.

Chapter 8

       “Thank you very much for helping me out with a little fun.  I do appreciate you offering to give up some of your break time during the day and I hope this will be fun for you or at the very least something a little different.  Right now he is probably looking like he is ready to run screaming as I am sure he is already feeling quite embarrassed.  Have no worries, he is not being forced to do this and in his own way he is enjoying this deeply.  Hopefully you will also enjoy and as I said last night, if you or anyone else is uncomfortable with this, any part of this, or if there are any issues at any time, I apologize and please feel free to send him on his way at any time.

For the most fun, please read this note step by step as you go unless you absolutely feel you need to know everything planned.  Also if you would please take his purse and hold on to it until he is done, there is a piece of red thread around the clasp the will let you know if he has opened it or not yet.  I hope to talk to you later about his day there and I hope to ask you if he opened it on his way there”

       At that point Danielle made the decision to stop reading but handed the letter over to the two girls.  “Go ahead and read it now and let me know if there will be a problem then feel free to watch of if you are not needed at the counter give me a hand.”  It only took a few moments for them to both read it, but both Anthony and Danielle could not help but notice as there were times that the girls laughed as the read something or made an exclamation and pointed at the letter or looked over at him as they read a part.  While they read, Danielle went to Anthony and demanded his purse from him.  He handed it over and she saw that the red thread was still intact.  As they handed the letter back to Danielle one of them looked in the envelope and said that it looked like everything was in there but they wished they could see what the other one was.  Both also agreed that everything would be interesting but not a problem and even suggested that all the options be included as well. 

       Danielle started where she had left off. “One of the things my little sissy slut is going to get is a new skirt.  I was in looking around a few days ago and found the perfect one.  The one you had on the display mannequin last Tuesday will work wonderfully.  If you don’t remember, it is the one that looks a little like a cheerleader skirt, but is all black leather and quite short.  Now here is where I need to ask a decision from you.  I would prefer that this be the first thing he has to do, because I want him to try it on (feel free to offer up a few of the wrong sizes first, preferably too small) and once he has the right size I want him to leave it on.  I do understand that this could cause problems if someone besides my sissy is uncomfortable with it (and if he is, too bad) so if it has to wait until he is almost finished that is ok, but I am sure you can see how much more fun it would be to do this first.  By the way, when it is time for him to try on the skirt, he is going to have a problem.  If you wish, please ask him to explain what it is, you will find the solution in the envelope and marked #1.  Oh and don’t worry about anything showing under the skirt, his man parts have been taken care of so make sure it is as short as possible.”  The last part made Danielle wonder about even more than the problem and solution they were going to find out about.

       “Before you get started I would also like to offer up that if at any time you wish to add something to all of this or make a change more to your liking please feel free.  Also please be aware, that I have previously priced everything out and have only given him enough money for the items I have chosen, another task he will have, and an extra $20 just in case.  If there is something you feel he just has to have that will fit in the extra $20, again feel free to add it.  And one final thing, inside the envelope you will also find a digital camera, please make use of it as you see fit, I definitely want a few of him in the skirts he tries on and any others that seem interesting, if you or your coworkers desire, I have no complaints if you also use your own cameras to take any pics for yourselves.”

       After reading, Danielle looked over to see the other sales girls, Stacy and Amanda, had already taken out their camera phones and had them on the counter as they were looking into the envelope and giggling to themselves.  She then looked over to Anthony who looked as though he was ready to cry as he stood there in his outfit with people walking by looking at him.  She saw no reason not to start in the order desired by Angelica so she called over to him.  “You! Get over here and let’s do this.”  She said it like she was very annoyed by the whole thing, but she had to admit this was going to be quite fun and definitely a different way to spend her break for a change.   “Follow me.”

       

Chapter 9

Anthony had been standing there ready to lose his mind.  He was so nervous and so humiliated by everything already and he knew it hadn’t even started yet.  He had seen the girls reading the letter and going through the envelope but he still had not been able to see inside it.  He had hoped he would be able to move around a little but when they done, Danielle had begun reading and he was still standing where she had left him.  Having to stand there seemed to make him even more obvious as now he wasn’t looking around or shopping, he was just standing by the counter not doing anything, which was causing him to be even more conspicuous.  The worst part was, through it all he couldn’t help but admit how excited it was making him.  The plug in his ass seemed to move and tease him with even the smallest movement.  The pouch was almost painful now as well, his poor cock was straining against it trying to expand, but it stood no chance against the leather.  He would have jumped out of his shoes if he hadn’t been locked into the when Danielle yelled at him.

       “Well let’s get started then, follow me.”  Anthony naturally walked behind her as she led him to the nearby clothing racks.  As he walked, he wasn’t sure but he thought he heard the sound of cameras being used but he didn’t dare look back to see.  When they stopped he noticed they were standing by a rack with many sexy pieces of leather outfits on it and his heart raced as he wondered what was going to be chosen for him. 

       Danielle knew exactly what skirt Angelica was talking about; she had dressed the mannequin herself and had even thought about getting one for her own small collection of leather clothing.  While she knew exactly where they skirts were and even had a pretty good idea of what size Anthony would need, she went to a different rack first.    As he stood there watching her, she made a point of pulling out different things;  A leather halter top, a leather bra, some latex pieces, finally a pair of tight leather pants that were obviously at least three sizes too small.  At the sound he made when she looked at the pants she briefly thought about having him try them on just see what would happen but decided not to this time (at that she realized she hoped there might be future times).  After a few moments of making him wait, she moved to the rack with the skirts.

       Anthony followed Danielle to the rack of various clothes and couldn’t help but stare at the things she pulled out.  Thee halter was incredibly sexy he thought and had to admit he was curious what it would look like.  The bra and latex items were also very sexy and he wondered just how large his collection of fetish clothing was going to end up.  Finally when he saw her looking at the pants she had pulled out he couldn’t help but let out an anguished “no way…” and a loud gulp.  He knew leather would stretch and mold itself to him and mold him to itself, but even if he could squeeze into them by some miracle, he wouldn’t be able to breath or move.  When she put them back he let out a sigh of relief and at the same time felt a twinge of disappointment. 

       As she looked at the skirts, Danielle knew it had been a very popular choice since they had gotten it in stock, but they had ordered plenty and she knew they had a few of each size.  Looking him over she felt he would most likely be a medium, possibly a large.  Knowing that, she still grabbed an extra-small and a small first for him to try on.  She didn’t say anything to Anthony and with the two skirts on her arm walked to the dressing room next to the sales counter.  When they got there, she handed him the extra-small.  “Get in there and try it on.”  Without thinking, Anthony took the skirt and went into the small dressing room and closed the curtain.  When he went to remove his pants he realized his problem.

       Danielle had stood waiting by the dressing room and Stacy and Amanda had managed to scoot much closer as well when they heard him call out.  “Um.. Miss Danielle, I can’t try this on right now.”  Intrigued, she called back, “What?  Why the hell not?” His answer came in a shaking voice that sounded on the verge of tears “I can’t take off my pants.”  You are in a dressing room, at least I didn’t make you do it out here in front of everyone” (this last made the other two salesgirls giggle at the possibility) “No, its not that I don’t want to, I really cant Ma’am.”  “Get out here and show me”

       With that Anthony walked out of the room practically shaking as he walked.  When he got to her he showed her his belt and the padlock keeping it, and his pants on.  Surprised but now understanding what was meant in the letter all three of the women laughed at his predicament as he stood there thoroughly humiliated.  Danielle reached for the envelope but was stopped by Stacy who already had a key in her hand with a tag showing #1 on it.  Taking the key She walked over to Anthony and reached for his padlock.  As she inserted the key there was no mistaking the sounds of cameras and even a flash this time.  The both looked over to see the girls; one had her camera phone and the other the digital camera left by Angelica.  “Now get your ass back in there and try on the skirt” Danielle walked back placing the key on the counter as he walked back into the room. 

       Anthony sat on the small bench feeling the pouch tighten more and the plug go deeper inside him as his cheeks felt like they were glowing from embarrassment after having to have someone unlock his pants so he could take them off.  He slipped the pants down his legs, revealing his garters and stocking and the fact that he seemed to have no cock with it tucked away and as he tried to remove his pants all the way, he really did almost start crying.  With his heels still locked on his feet, he couldn’t pull the pants over them. 

       Danielle had expected the first time, but was surprised to hear him calling out again.  “Miss Danielle, I am so sorry, but I still can’t take them off yet.”  Now truly curious as to what else there could be she told him to get his ass out to her and stop wasting her time.  After pulling his pants back up and zipping them, Anthony stepped back out of the room and stepped over to her.  “What the hell is it this time?”  Feeling very small, he explained that he could not get the pants over his shoes.  “What kind of idiot are you?  Just take them off” Now actually sniffling a little, he pulled up his pant leg to show her the strap and padlock keeping his shoe on.  As he pulled up the leg, the girls were all able to get a good look at his shoes and realized what the pants had been hiding, they were all pleasantly surprised to see the sexy 3” heels along with the stockings that had been hinted at as he had walked earlier.   Not even giggling anymore, but laughing outright Amanda grabbed the key and walked around the counter saying that she wanted to try.   She put the key in the lock and Anthony was very relieved to hear it click as the lock released but also wasn’t surprised to hear the cameras going off again as it happened.  Amanda even made a point of stroking his leg as she worked to unlock the second strap.   When she was done Anthony went back to the dressing room but as he did he made the mistake of looking up and was rewarded by seeing that almost everyone in the store had given up any pretense of shopping and everyone seemed to be watching him now.

       With the shoes unlocked he sat down again and removed them followed by the pants.  He looked at the skirt and found it had a waist just like his pants.  Above the pleated part of the skirt was a waistband that had a zipper in the back and belt loops all the way around.  As he pulled it up he wasn’t even half way before he knew there was no way it was going to fit.  Just as he realized it, he was startled by a knocking on the door.  “Any more problems in there, sissy?”   Knowing what was going to happen when he finally got to try the skirt on, Danielle had timed it just right to interrupt him.  “Um.. Yes Ma’am.  The skirt is too small and I can’t get it on.”  Guessing that the size hadn’t even been close and knowing that everyone in the store seemed to be watching (Danielle had been happy to find so far no one had stormed out or looked obviously disgusted with the show that was going on) she shoved her hand though the curtain with the small skirt and told him to give that one a try.

       Seeing the skirt handed to him, Anthony took it and quickly took off the first one to pull on the second one.  As he pulled it up he let his hopes climb that it might actually work.  As it got to his hips he began to worry but with some work he managed to finally work it over but to his disappointment, he was not able to do up the zipper in the back, it was still too small.  “Ma’am, I am sorry, but it is still a little too small.”  To his shock the curtain was pulled aside far enough for Danielle to look in.   She had again guessed correctly how the skirt would fit and knew he would at least be mostly covered with it on.  “Hmm yes, still not the right fit.  Stacy, please bring me the other skirts I have waiting on the counter for this sissy to try on.”  As they waited the few moments it took for Stacy to bring the skirt, Danielle stepped back from the curtain leaving it open just enough for Anthony to feel quite exposed (as it was, a woman standing at the right angle did in fact get a full view of him standing there).  When she arrived she had also brought the cameras and both she and Danielle took a couple more pictures of him standing there in his too small skirt.  Anthony also noticed the extra time they both took to take in a long look at the extent of his outfit now that the stockings and garters were no longer covered by the pants.

       After working the skirt down his legs and stepping out of it, Anthony was not surprised to find that he had only been handed the medium sized skirt.  He pulled it on, finding it much easier than the previous skirts and managed to zip it up.  With it on he looked at himself in the mirror.  While it could be zipped, the skirt was extremely short, standing still it barely came below his ass and he felt sure that if his cock hadn’t been locked up and pulled back, he would be visible from under the skirt.  Even the tops of his stockings and the tips of the garters were showing.  “Miss Danielle, I got it on, but I think it is still too small.”  This time it wasn’t just a little crack in the curtain, Danielle had thrown the curtain wide open, giving everyone a full view of him standing there.  If he could have gone through the back wall he would have but the best he could do was try to cower in the corner as he was stared at, again hearing the cameras and thinking he might have heard a few more coming from farther away…  Danielle looked him over. “Hmm, you might be right, that is a little short for any kind of decency.  Go ahead and try on the last size.”  With that Amanda handed him the last one and she took her chance to get a good look at him.  As with both girls, she giggled as she took in the view, but Anthony got the feeling from her that there was more than just amusement, she seemed to be enjoying the show on a much different level.

       Swapping out skirts went quickly and as he zipped up the final skirt he looked and was actually quite happy with the fit.  It hung comfortably at his waist and covered low enough that he didn’t feel like every step would be flashing the whole world.  He twirled once to see how it felt and couldn’t wait for his Mistress to see him in it and have him wear it for her.  Again the curtain was pulled open without even asking him.  “Yes, let me see.  Well, I do have to say that is a much better fit, definitely how that is supposed to look.” Anthony started to breath a sigh of relief and was about to step back in to put on his pants when his heart jumped to his throat and the pit of his stomach at the same time.  “Ok well get back in there and get the medium back on.  A slut like you shouldn’t be wearing skirts that fit right and are decent.  Oh and hold on a second.”  With that, Danielle reached in and grabbed his pants before walking back to the counter to wait for him.

       With no choice, Anthony went back into the dressing room and very nervously, realizing he pants were now in the hands of Danielle, put the short, medium skirt back on.  Knowing that she was waiting for him at the counter and he may or may not be returning to the dressing room, he also went ahead and slipped his heels back on before walking out.  He stepped out to hear snickering from the crowd watching, with everyone getting a full view if they hadn’t before.  As he walked, with his heels clicking and his skirt threatening to expose him to the world he could hear little bits of what was being said “what kind of guy would do that…”  “Oh my, heels and stocking too….” “What a whore…”  “Wow, I’m a girl and I wouldn’t be caught dead in a skirt like that…” and the one he barely heard that kept him from running out of the store “mmm that is kind of hot…”

       As he walked over the three girls took some more pictures and made a point of putting his pants down below the counter for safe keeping.   Amanda watched and also slid the envelope back over to Danielle.  When She looked at her with the question, Amanda just told her “You will see, read the next part”.  Danielle was quite happy she had chosen to have the girls pre-read the letter so they were able to be ready for everything and she was able to enjoy the fun of doing it as it happened.  Reading the letter she understood and took the envelope from Amanda.  She reached in and pulled out the belt and show straps she had put in the envelope to keep from losing them.  The letter had read “When he has the skirt on, make sure he puts everything back on that you helped him with.”   Anthony couldn’t help but notice as Danielle pulled out the metal chain and leather straps along with the padlocks.  “We wondered what she meant, until we found out exactly what problems he was going to have getting changed” This from Stacy as Danielle laid out the items on the counter.   Anthony knew what to do, even before he heard the “Put them on” from Danielle.

       Taking the chain he started to put it through the loops.  Amanda came around the counter and took the chain from him “I’ll help” she said.  With that she proceeded to move around him working the chain through all the belt loops of the skirt and got back around to the front.  Before she locked it she asked “So let me get this right” saying it loud enough for everyone watching to hear in case they didn’t see what was happening. “You can’t take this off without the key, and if you can’t take off the chain, you can’t take off the skirt.”  Feeling the humiliation and the excitement of his predicament so obviously explained, Anthony couldn’t do more than nod his head.  “What? I didn’t hear you.”  “Yes, that right” he answered, audibly this time.  “Try again sissy.”  This time Amanda added a little edge to her voice.  “Yes Ma’am, that is correct, I can’t take the belt or the skirt off without the key”.  That seemed to please Amanda and she smiled.  Still Smiling she pulled the chain snug around him and put the lock through the links, but just before she locked it closed, Anthony saw an evil twinkle in her eye as she readjusted the chain, going from snug to extremely tight before locking it closed.

       She went to the counter to get the shoe straps, but this time Danielle stopped her and told her just to give Anthony the straps, not to help.  Amanda might be showing a little of a Dominant side to her, but Danielle was still in charge.  A little disappointed, she took the straps and locks to Anthony and handed them to him.  Danielle cheered her up by telling her, don’t worry, it will be worth it.  Anthony took the straps and looked around for a chair or place to sit so he could put them on.  Not seeing one he knelt where he was and started to put the first strap in place.  Before he even got started he was interrupted.  “Wrong!  A slut doesn’t kneel like that unless she is getting ready to take care of something else.  A sissy slut like you is going to stand with her legs straight and bending at the waist.”   Feeling his face burn with new levels of embarrassment, Anthony stood up and bent over as instructed, reaching down to fit the strap over his heel and his ankle.  At least Danielle didn’t say anything as he turned first to face away from the wall, this made it so he had to face the onlookers enjoying the show, but it kept his exposed panties and leather pouch out of their view when the skirt rode up as high as it could go.  He managed to quickly buckle the strap and lock it on but when he got ready to do the second one Danielle spoke again.  “This time, why don’t you face the dressing room.  I want to see what she meant by something.  Swallowing, he turned enough to face as instructed, knowing that this would have him facing directly away from Danielle and the two girls.  He could hear them as he tried to concentrate on the strap.  “Oh, nice panties. But where is his thing?  I know she said it was taken care of, but I don’t get it.”  This along with the sound once again of cameras being used 

       He finally managed to get the strap on and locked and stood up.  He was immediately told to get over and get behind the counter for a moment.  Danielle wanted him behind the counter just in case this was going to be pushing things a little too far, she didn’t want to run into problems with her customers.  She did notice a couple of them seemed to adjust their positions for a better view, but figured that if they wanted to see, they probably weren’t going to turn anyone in for anything either.    “Ok slut, show us what is going on down there.  Lift that skirt”.   Anthony did so, lifting his skirt, fully exposing his panties, the stockings and garters and his conspicuously flat crotch.  “now pull down your panties.”  He did, following his earlier instruction of bending at the waist with straight legs.  He was pleased to hear Amanda point out that he seemed to learn fast.  With the panties gone the girls were able to start getting an idea of what was going on.  Stacy was good enough to point out that he was all shaved and smooth.  Danielle then told him to turn around and bend over.   This was as exposed as he could get and he knew it put everything on display.  He heard the cameras again and this time there was no doubt that there were other ones being used on the other side of the counter as well.  With him bent over and his legs spread slightly his pouch was clearly seen with his bound up cock tight inside.  Danielle saw it and mentioned that they had to start stocking those for sale at the store.  One of them mentioned about ho no wonder he always looked so fidgety, it wasn’t just what was going on, that things must be horrible for him.  He did recognize Amanda’s voice as she started “It has him all locked away so well, and all out of the way and it looks so uncomfortable, I love it!.  Oh and look, he even has a plug up under that strap!  It even all locks on…”   As horribly humiliating as it all was, Anthony couldn’t help but admit this was one of the things he had dreamed of.  The girls weren’t just doing it because they had nothing else to do; They were all getting into it and enjoying it.  As much as he hated it, being examined, exposed, humiliated and teased, he knew that deep down he was loving every minute of it.

Chapter 10

       “Ok, we have seen enough, stand up but go ahead and leave those panties with Stacy so she can put them with your pants.  You won’t be needing them, that wonderful little pouch will be good enough under your skirt.

       Realizing that she might have a nice little protégé with Amanda, Danielle decided to see if the younger girl had figured out what she herself had noticed about Anthony’s current outfit.  “Amanda, you seemed to enjoy his little belt chain, what do you think of the straps on his ankles?”  Looking down, Amanda couldn’t help but go over them just as she had the belt before she tightened it.  Thinking of the belt she reached out and gave a little tug to it, realizing just how tight she had done it as she was rewarded by the slightest whimper from Anthony that caused her to feel a tingle deep between her legs.  “So the little metal ring slips around the heel on the shoe, and the leather strap pulls it up and locks it around your ankle.  Pretty good, it gives almost any pair of heels with a thin enough heel a sexy pair or ankle straps and it makes sure that you can't…. OH, I see now.  It’s not just the shoes you can't take off anymore is it.  You can't take off those stockings either.  And looking at those stockings… let me check something… (she reached out and slipped her finger inside the top of one of his stockings)  Yup, those aren’t stay ups; you have to wear the garter belt to keep them up.  How delightful, with those simple little straps you are stuck in the shoes, the stockings and the garter belt!  And we can't forget your little skirt here now either” As she said the last, she reached to grab his belt again and managed to grab the chain as well as the leather belt hidden underneath and gave it all a good tug, forcing the plug in his ass deeper and a painful pull to his cock and the belt at his waist.  The squeal he let out was music to Amanda’s ears.

       Anthony could hardly believe all that was happening to him.  He stood there dressed like a whore on display for everyone.  Most of his outfit was locked on with him unable to remove it.  And three women taking great pleasure in his humiliation, one of which was growing bolder by the minute as she seemed to enjoy it more and more.  As much as he tried to forget, he could not ignore the fact that he was not just on display for the salesgirls, there were at least 10 other people watching his get put through his humiliation.  Through it all his cock was in agony as it tried to expand inside the small pouch and he could feel the pre-cum that had been leaking out into the pouch for quite some time now.

       “Well let’s see what’s next then.” Danielle started to read the letter.  “The next thing he needs is a new butt plug.  If you haven’t seen it, he is currently wearing a small one right now, as with everything feel free to ask him about it.  He does own a medium sized one already, but what he needs is a medium sized one that vibrates.  I have seen the ones you have that are wireless and I think one of those will be perfect for him.  He will need some batteries for it as well.”

       Looking over at Anthony she smiled at him just before saying in a loud enough voice for all to hear “So the sissy slut has a plug in her ass today.  What size is it?”  Anthony knew they had already seen the base of it under the strap, but it was obvious that Danielle was just trying to make it known to anyone else watching.  “it’s a small Ma’am”  “Well it appears that Angelica would like to stretch you out a little more.  Let’s go get you a new one.”

       With that She walked out from the counter with Anthony following along, his heels clicking nicely as always.  They walked to the far corner, opposite where the skirts had been, to the wall with the many plugs and dildos on display.   Danielle began to look at them all very intently.  She grabbed one of the small ones and made a point of asking him if that was the size he had in right now.  When he said yes she muttered rather loudly “no, no, that will not do at all…”  As she went to put it up she missed the hanger and dropped the plug on the floor.  Without even looking she told him to pick it up which he did, again bending like he had been told, giving everyone a good flash.   Danielle took her time going through the large selection.  She would look at smaller ones, ones with tails attached, laughing and telling him how funny he would look with a pig tail coming out of his ass.  She lingered over the bigger ones that had ripples and bumps in them.  Every so often she would drop one and after the third time she didn’t even have to tell him to pick it up, he did it automatically.   After a little more looking around, and even sending a wave of terror through Anthony while looking at the extremely large ones that he felt would literally split him in half if they were used, she snapped her finger like she had just had an idea “I know, I have the perfect one.”  With that she walked over to a nearby strand that had the one Angelica had looked at.  It was the same size as the regular medium plugs, but it was a vibrator as well and the box said in big letters that it was wireless with a range of about 50 feet.  She took it and handed it to him.  Anthony’s mind raced immediately at the thought of the larger plug inside him and the obvious plans his Mistress might have with a wireless control for the vibration.  By the smile on her face, he could tell Danielle was having similar thoughts.

Chapter 11

Danielle had to admit she was having fun.  With more than a little anticipation, she led Anthony back to the counter to read the next part of the letter.   At the counter Stacy motioned to him to hand her the plug so she could put it with his things to be rung up later.  As he was about to, Amanda stopped him by saying she thought it would be better if he just held on to it for now, it would be more fun watching him carry it around for the rest of the trip.  So there he stood, dressed and locked up like he was, with a small butt plug already in his ass, and a larger one in his hand.   He didn’t think anyone has any unanswered questions about who it was for and where it would go.

“After the vibrating plug, my sissy needs a new magazine.  You carry issues of Forced-Femme and Enslaved sissy maid there.  He already has a growing collection of those magazines but when I was in, you had the latest copy (jun07) and he doesn’t have that yet.  If you are all out all ready, please feel free to choose any other magazine you think would be acceptable for him.”

Danielle simply turned and began walking to the magazine rack at the far corner of the store.  The rack was back closer to where the skirts had been and it was becoming obvious that Angelica had chosen the order of the tasks to have him walking all the way back and forth across the store with each one.   “Your Mistress feels you need a new issue of your favorite magazine.  Why don’t you go ahead and see if you can find one that you don’t already have.  Oh, and to keep it interesting why don’t you hand them to me one at a time until you find one you don’t have.”  Danielle had noticed Amanda at the magazine rack a few moments before while they had been finding the butt plug, she had a pretty good idea what she had done.

Anthony looked up, as always the magazines he was to get were on the very top shelf.  On a normal day he always felt exposed climbing on the bottom shelf and stretching to reach for the sissy magazines, but as with everything today, it was going to be a while new level this time.  He put his foot on the bottom shelf and reached up, he had to fully extend to reach the magazine and his skirt pulled up at least half way over his ass, fully exposing his stocking tops, garter belt and even his pouch to a few people.  He took down the first one, it was one he had bought two months ago, and handed it Danielle.  She smiled “Already have this one huh?  I guess a sissy slut like you loves reading about all these things, I bet you even like to look at the pictures.  What kind of guy likes to look at pictures of other guys dressed up like this?”  Anthony could only nod as his cheeks flushed from embarrassment.  There was no arguing, she was right.   He went through the process again, it was a different issue, but still one he had.  “Wow, you have this one too?  You really do get off on this stuff, maybe one day you will have a dream come true and be in one yourself, on display for everyone to read about”  On the third try it wasn’t even a sissy magazine, it was some gay porn about men being tied up by other men.  He handed Danielle the magazine and this time she didn’t really say anything, but thought about how just an hour ago she had made sure the rack was in order herself.  She had been right in guessing that Amanda had made sure this task was going to last a little longer.  

Finally after climbing up and down a total of seven times, Anthony found the new issue.  Somehow it had managed to be the last one in the stack.  Danielle looked over to Amanda and nodded her approval to the young sales girl.  Anthony didn’t even bother trying to adjust his skirt anymore, after going up and down so many times, he knew that everyone had already gotten a complete view of everything he had to show anyway. 

With his plug in one hand and his sissy magazine in another, they headed back to the counter ready for the next thing to do.

Chapter 12

       “The final thing to purchase today will be another anal toy.  My sissy needs to get one of those Aneros prostate massagers.  I have read about then and I am curious to see if it works.”

       Danielle had seen them too of course and had also wondered if they worked like the advertisements said.  The product claimed that by inserting it into a male’s ass, through the process of only clenching and unclenching the muscles down there, a male could achieve a hands free orgasm.  She thought it might even be interesting to see sometime.

       “Alright slut lets get the next thing.”  As with the rest of the items, Danielle simply walked off, not even looking back to see if Anthony followed.  Not that she had to look, the heels gave enough warning whenever he took a step.  Once again she did not begin by immediately looking at what was required.  It just happened that the same area that had the Aneros, also had a large selection of dildos and insertables.  After a moment of looking she began pulling things down and looking at them, Anthony thought his heart was going to stop when he saw her take down the very large one that was shaped like a fist.  He knew his Mistress had plans for anal training but he couldn’t even imagine that.  After teasing him for a little while going through the various items, she settled on the Aneros itself.  Picking it up she handed it to him and watched him struggle for a moment trying to hold on to all three items.  He dropped the first plug as he did so and was forced to bend over to pick it up.

       Taking it all back to the counter She allowed him to place the small collection near the cash register.    At that point Amanda caught Danielle’s attention.  “That letter said we could add something if we thought he needed it and it fit into the budget.  We think we found something to add.”  Curious, Danielle simply nodded her head and gave approval for whatever they had thought of.  Amanda quickly ran off and returned holding something making sure that Anthony could not see it.  She went to the far end of the counter and had Stacy bring her a pair of scissors.  At first it seemed she was just cutting off a tag, but then it was obvious that she was using the scissors to do more to it.  She struggled for a few minutes and then finally seemed happy with the results.  “Close your eyes!” she told Anthony and walked over to him. 

With his eyes closed he didn’t know what to expect until suddenly he felt her reaching around his throat and was placing what felt like a thin collar on him.  After she placed it around him he could feel her button two snaps on the back, by the second one he had relaxed, until on the heard one he heard a much more solid click.  Unable to see exactly what had been put on, he was very curious, but had no way to see.  Danielle looked at Amanda’s handy work and was pleased at the choice.   She had taken a simple snap on leather collar that normally secured with 3 small snaps at the back, and using the scissors, had pried off the last snap and punched a hole through both sides, allowing a small padlock to be put through securing it in place.  She had even chosen an appropriate collar as this one had the word “SLUT” very clearly visible across the front of it.

Chapter 13

       “That should almost finish my little sissy slut’s shopping experience.  I do have a couple more small tasks for him that he will find out about soon enough, one of which still involves you and your store, but I will leave that one as a surprise so he can get your full reaction, good or bad.  Also, as with this from the beginning, if it is not possible, just tell him so and he will have to accept that.  He may have access to his purse now to buy everything.  Inside the original envelope you will find another folded one with a key inside of it, please place his pants and the key from his chain and shoe straps inside after removing that key.  Don’t seal anything yet until he actually is about to walk out the store.”

       Standing there fidgeting as Danielle read the rest of the letter, Anthony found his hands feeling the collar at his neck and reaching back to confirm the padlock was in fact there.  He could also feel the letters on the front, but was not able to tell what they spelled.  He was still trying to figure it out as Danielle came walking toward him with is purse.  She handed it to him and told him he was allowed to open it now.  He took it and snapped it open breaking the thread that had been sealing it closed. 

       Inside he found his drivers license, cash, another note and his house key.  The note was slightly different in that it had writing on it, but it was also folded and taped closed.  He read the writing on the front.  Use the cash I have given you to purchase your items but before you leave, open this note the rest of the way and read that.

       Anthony stepped up to the counter and told the girls that he was ready to purchase everything.  Danielle looked at him and asked if there was going to be anything else.  “I don’t know, there is something on the inside of the note but I am not allowed to read it yet.  He watched as his pants were placed inside a larger envelope that had been inside the first one.  He had hoped they would hand everything, including the key to his skirt back to him, but he realized his Mistress had already thought of that.  As Amanda rang up everything he waited nervously wondering what was left for him to do.  Finally she gave him the total and he handed over the cash.    It was almost starting to feel like an anti-climatic ending as she handed him the store bag containing his new toys.  As she gave him the bag he broke the tape on the note and read the rest.

       “Unlike the letter She had with your tasks, Danielle does not know what this last one is any more than you do.   I didn’t check to see if it would be ok so you will have to tell me how it goes.  I want you to reach into the bag of things you just bought, and take out the vibrating plug.  Next, while displaying it in your hand, I want you to ask Danielle if you can use the changing room again and borrow a pair of scissors.  She seems smart and I am sure will immediately understand why you are asking, but if she asks you will explain to her that you have been told to try to go in there, use the scissors to open the packaging on the plug and then insert your new toy into your ass.  She has the key to your belt so that you will be able to do this, and just so you know, the key only works on the lock at the back for your strap, it wont work on the front to release your cock, so don’t even try.  She may not wish you to do this, or be allowed to let you, if that is the case you will explain to her that your Mistress understands and that you will need to borrow the key she has just found and ask that she holds onto your things for a moment while you go out to your car.  If you can not do it in the dressing room, you will take the key, leaving everything else with Danielle, and go out to your car and insert it there.  There is another note inside your glove box, if you go out to the car at this time, read it, if not, read it when you do get out there.  After inserting it, you may return to the store collect your things and leave.  Oh, and I believe the vibrator has batteries included and a small sample of lube, you have permission to use it.  If they are not included, ask to purchase what you need.”

       Anthony could not believe he was going to have to do this, right here in the store in front of everybody.  But after everything else, he was already totally humiliated and this next task was making him feel quite excited again.  He reached in and pulled out the vibrating plug  “Miss Danielle?”  She had started working on arranging some toys under the counter while he read and looked up, noticing the toy in his hand “Ma’am, may I borrow a pair of scissors and be allowed to use the dressing room again?”  Seeing the plug in his hand, it wasn’t too hard to figure out what his intentions were, but she asked anyway. “Why?”  With his face burning, Anthony explained what the note from his Mistress said and wanted to crawl into the deepest darkest hole he could find as he saw Stacy staring at him with her mouth open and Amanda laughing without even trying to hide it. 

       “Well it is against store policy, but after everything else today I don’t think it matters anymore.  I however can not let you borrow the scissors, they are very sharp and if you cut yourself I don’t want to get sued.  We will open it for you.”  With that she took the package from him and cut open the top.  Reaching in, she pulled out the plug and laid it clearly visible on the counter.  She then pulled out the Wireless controller and found the batteries taped to it.  She installed the batteries in both items but did not test it out.  She looked in and saw the lube that had indeed been included but made a point of dropping it back in after looking at it.  “I don’t want you making a mess with that, do it dry or if you have to use your own spit slut.”  With that she handed him the plug and told him to go.

       Shaking with embarrassment and humiliation, Anthony took it and after a couple steps remembered the key.  Danielle was already ahead of him and holding it up.  “Needing this slut?”  He accepted the key from her and walked to the dressing room.  Inside he placed the plug on the bench and lifted his skirt.  Fumbling around he managed to get the key in to the lock and undo the strap going between his ass cheeks.  With growing shame, he spread his legs and reached behind himself and pulled out the small plug that had been inside him most of the day.  As he pulled it out he couldn’t help but let out a small grunt which was immediately followed by the sound of giggling right outside the dressing room stall.  Realizing that the salesgirls were listening right outside didn’t help at all, especially knowing that he had to still fit the bigger one in.  He placed the tip against his sensitive hole and began to push.  There was still some lube coating him from the previous plug but as he pushed he found it was not going to be enough.  It had been a while since his Mistress had used anything other than the small plug and he was quite tight.  He pulled the plug out and with no other option, spit on it.  At the sound he once again heard the girls outside, and one of the, probably Amanda he correctly guessed, once again wet straight to full out laughter.  He managed to get it fully coated in his own spit to add to the small amount of lube.  Trying once again he felt it slip farther in and taking a deep breath he pushed as hard as he could and let out a very loud grunt followed by a moan as it popped inside him.  More laughter assailed him making his burn in shame.  With the plug nestled inside him, he pulled the strap that had been hanging between his lugs back to the belt and once again secured it in place. Locking the larger plug inside him.

       The second he pulled aside the curtain, the plug in his ass began to buzz and made him stop and catch his breath.  He should have realized that the girls were going to be testing it out, but his mind had not been thinking clearly for a while now.  He looked at the counter to see Danielle holding the controls in her hand.  He jumped again, but not from the plug.  Amanda called out from behind him “Looks like it works, he stopped walking really quick when you turned it on.”  Anthony began walking again as felt the vibration stop only to be surprised again as it was turned even higher than the first time.  It was left at that speed while he walked to the counter, right until he reached Danielle, who turned it off, then just as he took a breath, turned it on full.  They all laughed as he nearly tripped over his own feet.

       “So how does that feel slut?  Let me see your old one.”  Anthony held it up for her.  “Yes, that new one must be stretching you and filling you nicely.  How are those vibrations?”  She emphasized her question by sliding the control up and down making the vibration change inside him.  His voice quivered as he told her they were very intense and he could feel them over his entire body.  “Well, slut.  We have decided we have another task for you ourselves.  We want to find out how responsive this toy is and how good the range is.   First here are the levels on the control.  This is low”  He felt a mild tingle deep inside him.  “Medium” This was a much more noticeable feeling.  “And High”  This again sent the vibrations all through him, making his cock spasm in its tight leather prison.  “Now you are going to walk around the store, making sure you hit every aisle and corner while we randomly set the control.  When you feel it, you will call out its level.  When you get it right ten times, you will be able to stop.”

       With no choice, and feeling like a slut on display (which of course he was), Anthony began to walk.  He had only taken a few steps when he felt the rather noticeable buzz.  Stopping in mid-step, he called out Medium, to the laughter of almost everyone watching.   Moving again walking away from the counter he was hit with a heavy jolt as he got near the wall.  “High” was his call this time.  Taking a few more steps, he felt a slight tickle, but wasn’t sure and then it stopped.  After a few more steps he felt the tickle again and called out “low?” with a question in his voice.  “Very good sissy. But you missed it before so now we aren’t sure if it is working, so we have to start all over again.”  His heart fluttered as he realized that this was not going to be easy at all, and the girls were going to be sure to drag it out.   Soon he had walked over every inch of the store calling out various settings and after a few false starts he was calling it right every time.  When he finally reached eight he thought they were going to finally let him finish but this time as he felt the tickle of a low setting and started to call it, the feeling increased, past medium, but then down again, and up again to high.  He was able to see the counter and saw Amanda with the control in her hand making the vibrator pulse deep in his ass.  “Hmm, seems like you missed that one, so guess we get to start over.”   They kept him at for about a half hour before finally letting him quit.  His feet were sore from the constant walking in the heels and his legs were even feeling the strain.  His ass was almost numb, especially after they had left it on high for about five minutes on number nine, pretending like they had forgotten to turn it off.

Chapter 14

Anthony made it back to the counter and the girls were finishing up putting everything back in his bags.   Danielle was holding the envelope with his pants and the keys to his belt and the new key to go along with his collar, he noticed she had not sealed it yet.  Amanda handed him his store bag and told him she was looking forward to his next visit.   Danielle came over and said that she would walk him to the door.  “I look forward to talking to Angelica later and thanking her for sharing you with us.  Who knows maybe we can work something out again, I have a thought for a living display mannequin for some items we have that just wont go on a plastic one quite right…”  She looked at him as she said that and noticed the wide eyed look on his face decided she would definitely bring that up later.  “Here are the rest of your things, good luck.”  With that she made a point of taking the control for his plug, sliding the lever all the way full, then dropped it in the envelop and sealed it up, out of his reach.  He almost dived in after it before she closed it, not knowing if he would be able to stand it buzzing away full strength for who knew how long.  She handed him the envelop with an glint in her eyes “Drive carefully”

       Anthony walked to his car in a daze.  He didn’t even notice the people outside staring at him as he went.  He climbed in and sat down, groaning as the plug was driven deeper than ever inside him, making his whole body shake.  It was almost too much, after everything he had just been through his body was on edge and the deep penetration with the heavy buzz brought him to right to the brink of orgasm.  But with his cock stuffed and locked away so uncomfortable there was no way he was going to be able to get the release.  Before he realized it he actually found himself grinding himself against the seat trying to work the plug inside him and get the friction on his leather bound cock between his legs.  It was no use, all it did was add to his frustration. 

       Almost in tears from deep need for relief and knowing it was only gong to get worse, Anthony started the car and was about to drive away, when somehow he managed to remember the note he was to find in the glovebox.  He opened it to find another small envelope.  When he looked in the envelope he found the note, accompanied by a tube of bright red lipstick and a lip pencil that more than a few shades darker than the lipstick.  He also saw two small business cards and once again his heart nearly jumped out of his chest when he saw what they were.  “Do you lips with what I have enclosed, and before you even think to question, yes I know exactly what the colors were I chose.   Don’t forget the lipgloss afterwards.  Once you are done, go back in the store and offer those cards to Danielle, she may keep one herself, and if she wishes, she may post one anywhere of her choosing.” 

       Pulling down the visor and using the mirror, Anthony started on his lips.  His Mistress had been working very hard teaching him about makeup and one thing she had always stressed was to make sure the lipliner always matched the lipstick, never more than a shade darker or lighter.  He filled in his lips with the pencil as he had learned, going just barely outside the line of his natural lips to help them look just a little fuller.  He followed it up with the lipstick, sticking to the natural shape of his lips.  After setting the lipstick he finished off with the lipgloss and was half horrified and half impressed with the final effect.  His lips now did look larger and almost pouty.  He was also very aware of where he had seen other lips painted like his with the obvious dark line penciled around his bright red lips, porn stars and whores.  “Cocksucker” was the only way to describe the effect.

       Taking deep breaths to calm himself, Anthony turned off the car and walked into the store again.   He had the feeling that everyone was talking about him (correctly so) as he walked in and they all immediately stopped and stared again.  Danielle was surprised to see him back and called out as he walked toward the counter “Well well, back already I didn’t thi…”  She stopped in mid-sentence as when she saw his adjusted make-up.  “Wow, what the hell does she have planned for you next… or maybe I should ask who does she have planned for you next.  Those are just begging to get smeared all over something!”  Amanda added in by pointing out that with that, he had definitely crossed the line from sissy slut to sissy whore.

       “Ma’am, I have been instructed to offer you these.  One is for you, one is your you to post at your discretion.”  Anthony couldn’t believe His Mistress was actually going to have him hand them out.  He had thought they had been done as a humiliating assignment a month ago, but nothing more.  Under her direction he had created his sissy calling card.  They were soft pink with roses on them.  On them in flowing script he had posted the name “Sissy toni”  along with the name it included his phone number, his e-mail address, an e-mail address Angelica used when she didn’t want her real one used and a link to a website she had told him to make a while back that had numerous pictures of him in all states of dress and undress as well as stories and blogs he had written.   On the back of the card was printed ‘Sissy boy, femme-slut for use.  All occasions; Parties, Maid service, conversation piece etc…”  “No charge, call or e-mail for scheduling”

       She looked it over and laughing showed it to Amanda who made it obvious that she would be making a copy of the card for herself.   

       Anthony quickly walked out of the store again trying not to think about the fact that he could hear Danielle telling everyone in the store that if they had liked what they had seen, they had some good news for them.

Chapter 15

               Driving away towards home and just wanted to lock himself in until his Mistress got home, Anthony got so distracted by the large buzzing plug and his deep frustration that he was quite surprised when the low gas light blinked on.  He had completely forgotten that Angelica had left him with very little gas for his trip.  Trying to figure out where to go, he realized that his options were limited and he only had two choices for stopping.  One was a small station that was never very busy, but also wasn’t in the best of conditions and was actually kind of skuzzy.  He really didn’t want to go there dressed as he was.  The other choice was a major station that was always quite busy right off the main street.   Thinking that he could pull into the larger station and simply try to blend in since no one ever really paid attention to each other anyway, Anthony went for the larger station.  As he pulled along side the pump, he realized the huge mistake he had just made and he didn’t have enough gas to go anywhere else.  Looking in his purse he realized Mistress Angelica had planned one more humiliating experience for him, the only thing in there was cash.  He was not going to be able to hop out and pay at the pump, hiding by his car.  He had even chosen a pump at the far end in hopes to be hidden more.  Now he was going to have to walk all the way across the station, go inside and pay in cash.

               Walking by people he kept his head down and at first he had been right in guessing that no one paid attention to others while filling up.  But then he heard the unmistakable sound of a guy noticing a short skirt.  A whistle followed by “Oh, damn look at that fine piece of…””Oh HELL NO!”  “What the hell is that shit?!”  With that, everyone in the station looked.  There was no hiding or blending in now.  Burning in absolute shame he literally ran into the station and threw down forty dollars saying it was for the pump he was parked at.  He ran out to find everyone pointing and laughing, some asked how much for a quick blow job behind the station while others called him a sick freak.  Through it all the plug in his ass kept buzzing away keeping him on the edge of orgasm, causing the humiliation and embarrassment to mix with the physical stimulus and work him farther and farther over the edge. 

               Somehow he managed to get to the pump and start fueling the car.  After only about five gallons he couldn’t stand it any more and pulled the hose out and jumped in the car and drove off, leaving quite a tip for a rather confused station attendant.

       

       

Chapter 16

               With tears in his eyes and his body trembling, Anthony found his way home and almost tripped as he went through the door.  “Well, it looks like you had quite a day”  He almost jumped out of his own skin at the surprise of his Mistress Waiting for him on the couch.  On the verge of collapse he dropped to his knees and crawled to her at the couch.

               She saw the condition he was in and was quite pleased.  He had told her about his fantasies involving scenarios similar to what she had put him through today but she had wanted to make it something he would not soon forget.   Seeing him still quivering at her feet she knew all the work she had put into the planning had been worth it.    “Stand up and let me see”  He crawled to his feet and she looked him over, noting the collar around his neck, making him turn around and then eventually bend over with his feet spread.  She reached out and lifted his short skirt the rest of the way over his hips and the lightly stroked the leather pouch between his legs.  She smiled as the sensation almost caused his legs to buckle and he had to catch himself.  As her fingers traveled over the pouch to where the plug was, she was surprised to feel the buzzing and gave it a little push just to hear him moan again.

               “Well I guess we are going to have to take care of all this aren’t we my little sissy slut?”  Whimpering, Anthony almost dropped to the floor at the thought of finally getting the relief he so badly needed “But first you are going to have to tell me all about your day in detail…”

END