A Gift for Alex

Alex almost tripped over the box as he stepped out to get the morning paper. It was a rainy Saturday morning, and he was trying to make a beeline for the spot where the Herald had landed earlier when the paperboy had missed his door by a good few feet. He tried to kick the box inside, but found it was extremely heavy. He decided to get the paper and then come back to push the box in. He ignored the box completely as he closed the door behind him, before any more rain could get in, and continued ignoring it as he went back to his kitchen to make breakfast. Try as he might though, just ignoring it didn’t mean he wasn’t curious, and by the time he had finished eating he was more than ready to open the box and see what was inside. He hadn’t ordered anything, but he had gotten a good enough look at the strange parcel to see that it was certainly addressed to him.
When he had gotten the box open, Alex was very surprised to find that inside was yet another box. Unlike the cardboard that surrounded it, this new box was wood and heavy. Strangely though, there was a modern looking keypad lock on the front. Try as he might, Alex couldn’t guess the combination, and all that the screen would display was “Check Your E-Mail”. Unsure as to what to do next, Alex decided to go with it, and checked his e-mail. Sure enough, amongst the spam there was a new notice from an address he didn’t recognize with the subject “A Gift for You”. The message itself was short; it only said to “Listen as you go to sleep each night”. Attached to the e-mail was a MP3 file. Alex downloaded it, but decided not to play it just yet. If he was supposed to listen to it as he fell asleep, that’s what he would do. He did notice that the file was long, really long, about 8 hours long.
The rest of the day was uneventful. Alex went shopping, stocked up on food for the week, little things he did every weekend. He wondered about the strange file, but never really thought too hard about it. He just assumed he would find out that night. By 10:00 that evening, Alex had decided that it was late enough to go to sleep, so he eagerly got into bed and turned on the audio file. A gentle voice started speaking to him, talking to him about relaxation and sleep. Alex had wanted to stay awake, to hear more of what was in the file, but it wasn’t long before he found himself just drifting off to sleep.
Alex awoke the next morning at 6:00. At first he turned over, deciding to go back to sleep, but found that he was completely rested. That was strange, he was never up this early on the weekends. He felt rested though, so he figured he should probably get up. He didn’t think about the box the entire day, in fact, he didn’t think about anything that had happened to him in the past 24 hours at all. He went about his normal business, acting as if nothing had happened. His week continued this way until Thursday night, when he received another e-mail, with the subject “Gift pt. 2”. The message contained several new audio files for download, as well as instructions to make sure all of them were recognized as one gapless album, and to put them all on an MP3 player, as well as a time on Friday night when he was to begin the album. Beneath this message, Alex found a 7-digit number and instructions to “use these”. Suddenly Alex remembered the box with the lock, and went to input the code. Sure enough, the number opened the box, but not in quite the way Alex was expecting. A small door opened on the side, revealing a tiny pair of wireless in-ear headphones. Trying them on, Alex found that they fit him perfectly, not falling out, and he couldn’t even tell he was wearing them. Alex immediately went back to his computer to download the new files and prepare them for Friday night. As had become his habit, at 10:00 exactly, Alex climbed into bed, and began the eight hour file he had received the week before, and as usual fell asleep within minutes.
Friday night came, and Alex was practically jumping with excitement about his new files. He had no idea what they were like, but assumed they were similar to the last one he had received. He sat and watched the clock, waiting for the 7:00 to roll around, and the second it did he pressed play.
The new file was different from the other one. It was the same voice speaking to him, but this time it referred to him by name. “Hello, Alex” it said, “I hope you’ve been enjoying the file you received last week, we certainly put a lot of effort into it. We would like to perform a little test this time, before getting started. When I finish this introduction, you may or may not hear a beeping sound. If you do, please pause the file, and request the B version of these files via e-mail, and continue enjoying the previous until we can send you the updated version. Please listen for the beep now.” At this point, a loud and rather unpleasant sound was indeed played through the new wireless headphones, and though Alex did not hear it. For the past week, he had been conditioned not to consciously hear this particular note at all, but rather to revert to an extremely relaxed state of suggestion.
The voice continued. “Hello Alex, this weekend we are going to try something different. We are going to help you build and discover a new personality within yourself.” Alex just stood and listened, completely relaxed, completely in trance. The voice guided him to the box, and gave him a new code to input. As he did, a new compartment opened, which revealed shaving equipment and nail polish. The voice told him to shave off all of his body hair beneath the neck, assuring him that the new headphones were completely waterproof so he could wear them in the shower. As Alex finished, the voice guided him through toweling off, and giving himself a French manicure and pedicure. Once he was done, the voice informed Alex that there were still things to do before going to bed, both of which involved opening the next compartment of the box. After inputting the new code, Alex obediently lifted a pair of silicone breasts out of the box, and went to the bathroom to put them on. They fit him perfectly, as if they were made just for him. “Look at them, see how they bounce and move with you. Feel their weight on your chest. You love it, don’t you?” the voice asked. He did love it, though he knew better than to actually respond. He wasn’t supposed to speak, so he wouldn’t. After putting on the breasts, Alex returned to the box once again, and removed his final item for the night, a corset. He stepped into the latest piece, and pulled it up to his waste. There were cups to support his new D-Cup breasts too. If he could truly think for himself, Alex might have realized that pulling the corset tight would be extremely difficult for one person, but the voice guided him to a hook in the wall meant for coats. How the voice knew the layout of his home, Alex neither knew nor particularly cared. He was instructed to place the laces on the back, already done up almost all the way, around the hook and tie them together to form a loop. He then leaned forward, allowing the laces to catch all of his weight and pulling the corset unimaginably tight. In this position, he reached back and closed a pair of clips near his shoulder blades, holding the strings in place, then he stood straight and removed the loop from the hook, untying his previous knot, and tying a new one in it’s place snugly across his back. He could barely breath, but was assured by the voice that he was just fine, in fact he was better than ever, since now he had breasts and an incredibly thin figure. He was also informed that it was now time to sleep.
As Alex walked to his bed, the voice congratulated him on his first day of progress, and somehow knew exactly how long it would take for him to lie down, because as soon as he did, a new file began to play, different from the old one, which put Alex to sleep within seconds. All night his mind was filled with dreams of obedience and the pleasure he derived from it. Dreams of his new breasts and figure, and what Saturday could possibly have in store.
When Alex awoke, precisely 8 hours later, it was again to the voice speaking in his ear. It was time to open more compartments of the box. When he reached into his wooden chest after inputting the latest code, Alex found a long black wig. He immediately returned to his bathroom mirror to put it on. He felt good doing it; he had looked so strange before, a woman’s figure and breasts, but such a man’s face. The wig didn’t solve all of the issues, but it certainly helped a lot. The next compartment did little to help this problem, but it quickly became one of Alex’s favorites. This compartment contained stockings; long, thigh high, white stockings. Alex felt them as he pulled them on, one at a time, felt them hug his legs, hiding all of the imperfections and drawing attention to his curves. The next compartment the voice guided him to was by far the largest in the entire box, and the reason soon became clear. It contained a full, frilly, black dress with white petticoats. There was a white apron under the dress, with a white maid’s cap under that. Alex’s dreams flashed before him, his joy from being told what to do and obeying, and knew that being a maid would bring him exactly these opportunities. He bent down to lift up the dress, and the voice began to guide him through putting on each part of his new uniform. The white was a sharp contrast to the black, drawing even more attention to his legs than before. The next compartment contained only a pair of black six-inch heels, which Alex put on immediately. They had black ribbons at the ankle that wound up and around his calves, tying into pretty bows just beneath the knees. It took some time for Alex to learn to walk in his new shoes, and he spent much of the next couple hours perfecting a sexy walk, which he could maintain without so much as a stumble. It was just a little past noon, but the voce informed Alex that there was only one more compartment to open that day. When he discovered what was inside, Alex’s face lit up with a smile. The day’s final compartment contained makeup of various shades and colors. He took it all to the bathroom mirror, and with the aide of the voice, covered his face in a thick layer of foundation and powder, giving himself a pale complexion, black mascara and liner, as well as slender black eyebrows, a generous amount of rouge, and bright red lipstick. It was perfect, Alex couldn’t ask for a better outfit. It was absolutely impossible to tell he was a man without lifting up his skirts.
To his surprise, the voice kept talking in Alex’s ears. Alex had no idea what more could happen that day, but he quickly found out. The voice guided him to his kitchen counter where he picked up his shopping list, and left the house for the store. On his way, Alex was the center of attention, everyone on the street stopped to watch this woman in a maid’s uniform walk by in her six-inch heels, a fact which didn’t change at the store itself. Alex walked confidently through the isles, picking up the foods he needed for the week, and taking them to the register. The girl working the checkout was young, younger than Alex, and she looked at him with pure amazement. Alex completed the transaction without saying a word, ensuring that his masculine voice wouldn’t give him away. That certainly wouldn’t do. As he loaded his groceries into the car, the voice instructed him to drop them off at home, then spend the day walking around public spaces, avoiding conversation, but inviting stares. He even was told to be a tad flirty, going so far as to kiss a man on the cheek for holding a door for him. A deep blush followed up the action on the man’s part, and a seductive smile from Alex, who left before the situation could progress any further. He was supposed to flirt, not start taking men home. By the end of the day, he had thoroughly enjoyed himself, having kissed two more men and three women, going so far as to make out with one each, and letting one man fondle his breasts. Once home, there was little to do beyond undress and head to bed, where the voice again lulled him to sleep faster than he ever managed on his own.
On Sunday morning, the voice woke Alex early, feeling perfectly rested as usual. It told him that there was only one more compartment in the box, and today Alex would get to explore it’s contents completely. First though, Alex had to dress. He wore the same thing as the day before, right down to his makeup. When he opened the final part of the box, a large layer at the very bottom, Alex found a large box of condoms, and several dildos of varying length and thickness. Following the directions of the voice, Alex laid on his back, covered his still exposed cock with a condom to avoid ruining his pretty dress, and started to tease his ass with a medium dildo. He never actually penetrated himself, only ever playing with his hole rather than going in. After nearly an hour of this, the voice instructed him to place one of the dildos on his floor, pointing up, and to squat over it. Having done this, Alex was now instructed to sit down. Having no choice, he obeyed, feeling the joy of obedience as well as the pleasure of the dildo entering his ass. He bobbed up and down a little, working his way down onto the hard object until the voice told him to stop and hold himself where he was. He was told to hold that position for half an hour, which he did, his ass almost completely filled with the dildo. Finally, the voice commanded him to fully sit, accepting the entire thing into his ass, at which point Alex had the largest orgasm he had ever experienced. Once it had finished, he was instructed to return to the box, for apparently there was more to this last compartment than he had thought. After removing the dildo from his anus, Alex walked over and reached back into the space, discovering a small box that he had missed before. The box contained anal plugs, which the voice said were to be worn as often as possible, in fact, all the time. Alex reached back to his ass, massaging the hole, and finally took a plug from the box and inserted it until it was clamped into place. The feeling was strange, but immensely pleasurable. Apparently though, there was one final item hidden within the box, beneath the bottom of this final compartment. Upon closer investigation, Alex found a thong built to hide his cock and hold the anal plug in place, even adding a little pressure to it. Once his outfit was completely assembled, the voice instructed him to suck on a dildo for an hour, then play with his ass again, and after that to remove his clothing, return it all to the box, which would remain unlocked, and to prepare for bed, at which point the file ended with the instructions to watch for new e-mails with activities Alex would be guided through each weekend. Alex couldn’t have been happier.