The boxes Steve took the box down from the shelf. It was wrapped in white tissue paper, tied with a pink bow, and was labelled #1. Five identical boxes remained on the shelf, numbered #2-#6. He held the box in his hand, sighing deeply. Shelly had smiled as she placed all the boxes on the shelf, nearly two months ago on new years day. "Each of these boxes is an orgasm for you, my sweet little sissy. If it ever gets too hard for you, knowing I am out with my boyfriend, while you are at home, locked in your little cock cage, all you have to do is open the first box," she had said, beaming at him. "That's it?" he replied. "i just open the box and i get to cum?" "Sweetie," she replied, her voice dropping a bit, as if talking to a simpleton, "No. Of course that is 'Not It.' It won't be easy on you, and these are the only six boxes you get this year." She had gone on to explain, that each box contained a padlock, a task, a key, and a tenga egg. She explained to him that a tenga egg was a single-use masturbation sleeve. He was to complete the task, unlock, and then use the tenga egg to masturbate. Upon completion, he was to use the new padlock to lock up, and dispose of the old lock and the used tenga egg. The temptation was great to tear open the first box the very next day, after all, at that point he had been locked in the cage for well over a month. Ever since Shelly had started dating her boyfriend in mid-summer, unlocking her husband Steve from his chastity device and letting him cum had been low priority. But he waited. Steve knew that he had to make the boxes last. He had six chances to be unlocked, and he knew Shelly was going to hold him to only those six times firmly. When it had all started, he figured it was going to go only the way he wanted it to go. His life would be exactly like all the fantasies he had built up throughout the years. In every relationship he had since he was about 20 years old, Steve had tried to hint that he wanted to be dominated, but until Shelly it had never happened. He suspected that some of his exes had gotten his hints, and wanted nothing to do with a man who wanted to be submissive. He had done the same with Shelly, dropping overt hints all the time that he thought sent the right signals, but after two years of dating, and then two years of marriage, nothing had come of it. His fantasies remained just that: Fantasies. Jerk-off material. Late-night internet sessions. It had all changed after that fateful new years eve, over two years ago. Shelly and Steve had attended a New Years Eve party at a friends house. The party went late, and was pretty raucous, as per usual. Shelly had lost the rock-paper-scissors contest at the start of the evening, and thus was the designated driver for the evening. Steve took full advantage of the fact that he didn't have to drive, and helped himself to drink after drink. When it came titme to leave, Shelly practically had to drag him out the door. On the car ride home, Shelly was pretty amused with Steve's antics, singing along to the radio, holding his head out the window, yelling "happy new years" anytime he saw someone on the street. They pulled into their alley, and into their garage. Steve stumbled inside, first, with Shelly not to far behind. Shelly dumped her purse and keys on the counter, and grabbed her cellphone charging cord with one hand, while digging in her purse for her phone with the other. "Oh shit!" she exclaimed, "I left my cell phone at Greg and Laura's house! Try to keep yourself together and still be awake when I come home, drunky boy!" "Aye-Aye Captain!" said Steve, clumsily saluting her as she left. Steve was determined to stay awake, because all the drinks had made him not only drunk, but more than a little bit horny. He went upstairs to their bedroom, and lit a few candles. He turned on some music, turned off the overhead light, and folded back the sheets. He stripped naked, and then went into the master bathroom to put his clothes in the hamper and get his robe. It drove Shelly crazy when he just threw his clothes on the floor, she was very particular about laundry. He opened the hamper, and paused. There, on top of all the other clothes, was a pair of Shelly's underwear. Not just any pair, his favorite pair. He was a little disappointed because that meant his favorite pair wasn't on her body right now! He picked them up off the pile as he threw in his clothes. He was hard as a rock already, just thinking about what the night had in store, and the scent of her sex wafted over him as he brought the emerald green silky and sheer panties up to his face. He glanced in the mirror and saw himself holding the panties to his face. "Why the hell not?" he said, smiling. One of his many fantasies involved Shelly "making" him wear women's clothes, which of course, he would do in a heartbeat, and he would not really need to be forced to do so. He tossed the panties on the tile, drunkenly tried to get a foot in, and finally managed to pull them up his legs. He looked in the mirror as he brought them slowly up over his erect penis, the small panties pressing it tight against his belly. He turned to look at his ass. "Looks good!" he exclaimed aloud. "Pretty hot if I do say so my damn self!" He began to sway his hips back and forth in time to the music wafting in from the bedroom, and rub his silken covered cock. He closed his eyes, and tilted his head back, imagining that he was being forced to dance like a stripper for a vinyl clad dominatrix, like the ones he saw on all the porn videos. "is that good mistress?" he cooed, and then answered himself back with a harsher voice, "that's looks good little sissy…keep dancing for me." "Yeah little sissy…Keep dancing for me" said Shelly, in a tone of voice he had never heard from her. Steve spun around to see her in the doorway. He opened his mouth to talk, but no words came out. "I decided I didn't really need to drive all the way back there and get my phone, and that I would have a better time coming home before you passed out, climbing on top of you and fucking you until you came. Then I would ride my vibrator until I did too. Looks like I may have to change those plans." Steve finally found words, and began "Shelly I…" "I believe I said you were to keep dancing for me" Shelly interrupted. "And bring your ass in here" she said, spinning on her heels and making a beeline for the drawer with her vibrator. She climbed on the bed and fired up the vibe, raising her skirt and rubbing the vibe up and down her panties. "like these panties too?" She asked Steve as he entered the room, awkwardly trying to dance, but finding it very difficult now. "Yeah, I uh, yeah I do." Steve weakly stammered. "Yes I do, Miss Shelly!" she yelled. "Yes I do, Miss Shelly," he replied dutifully. His mind was reeling. What the hell was going on here? Shelly had just jumped right into this role-play, like it was something they did all the time. Speaking of Shelly, she was ramping up fast, way faster than she usually did, towards what looked like it would be a very impressive orgasm. She ripped off her panties and threw them in his direction. "Stop dancing, and start licking!" she growled, grinding the tip of her vibrator right against her lit. Without thinking twice, Steve dove between her legs, and began to taste her. He could feel heat on his face, coming in waves. He wasn't down there for more than 30 seconds before she clamped her legs around his head, and began to cum, loudly. She shuddered for a bit, but never let up on the pressure of her thighs on his head. "you think I didn't know?" She asked. "the elastic on at least four pair on my panties has been shot in the past year" she growled, squeezing tighter. "On top of that, I noticed the browser history on our computer kept getting cleared, so I took the liberty of installing a keylogger. What strange searches you were doing…sissy, mistress, strap-on, chastity, cuckold…shall i go on?" Steve was held tight, his face pressed hard against her sex. "Well, that was the last time you will wear my panties, Mister. But not I think, the last time you will be wearing panties for me." She released her grip, and said "Again." Steve began to lick her in earnest, unable to believe what he had just heard. After she came a second time, she shoved his head away and said, "We'll talk more in the morning." He was still hard as a rock, but knew better than to ask if it was his turn. His mistress was ready for sleep, so he spooned her and within minutes she was asleep, but Steve was unable to sleep for a long time. Needless to say, Steve's life took dramatic turn the next day. He awoke before Shelly, and stumbled to the shower. The previous night seemed like a dream, and he had almost convinced himself that it was by the time he was cleaned and the fuzz of the hangover lifted. He got out of the shower and went to get dressed, finding Shelly had already gotten out of bed. He slid open his underwear drawer. It was empty. Confused, He put on the rest of his clothes and went downstairs. Shelly sat in their dinette, eating scrambled eggs and toast, drinking coffee and reading the paper. She picked up a section of the paper, revealing what was underneath it. He froze when he saw that sitting on the table were the emerald green panties. "Don't just stand there sissy, put on your panties. No sissy of mine is going to go out into the big bad world without underwear on." He stood there, dumbfounded. "Now!" she growled, and he quickly shed his pants and put on the panties. He went to put on his pants, and she said one word. "No." He stood there, in the kitchen of the house they shared, feeling his dick get hard in Shelly's panties. Now sober and in the light of day, he felt ridiculous. "I know I told you last night that you would never wear my panties again. So there you go. Those are my gift to you. Your first pair of sissy panties. They are all yours. Today at the mall you will outfit yourself properly. You are to buy ten pairs of panties, and and five camisoles. If the sales girl asks you who they are for, you must tell her that they are for you. The mall opens at ten, and I expect you back by 11:00." She picked up the paper and held it in front of her face. Steve glanced at the clock, and saw it was 9:45. From behind her paper Shelly added, "You may wear your pants to the mall." Steve nearly fell over putting on his pants as fast as he could, and running for the door. It was the weirdest drive of his life. His mind was reeling. On one hand, he couldn't believe he had been busted. On the other hand he couldn't believe his luck. After years of hinting to all his girlfriends, and secretly wearing their panties, he had fallen into exactly what he had dreamed about for years. Introspection time would have to wait though, he was short on time. He parked in the first spot he found, and pretty much ran into the mall, making a beeline for the lingerie store. He grabbed a handbasket, and started walking around the the store. At first, he was grabbing things as fast as they saw them, so he wouldn't have to interact without the sales girls, but then he started second guessing himself, and putting stuff back. He had no idea what he was doing. There were no other customers in the store. He saw the sales girls tittering to themselves behind the counter as they watched him. One of them came out from behind the counter and walked up to him. "Can I help you sir, you seem to be having trouble finding what you are looking for." she asked. Thank god, she hadn't asked who he was shopping for. If he played this right, he wouldn't have to admit to this young women what he was up to. "I think I am finding everything alright, I just want everything I buy to be perfect," Steve answered. The girl lock eyes with Steve "Who are you shopping for, sir, I can help you pick out something appropriate?" she beamed, flashing him a huge smile. Steve's head sank. "me." he said quietly. "I'm sorry sir? What was that?" Steve cleared his throat, "They are for me." he said, a little louder this time. "I see sir," she replied. "You must be the sissy that we were just phoned about. Ten pairs of panties, and five camisoles, correct?" she asked, with her smile never fading. "Er…Yes," Steve stammered. "Well, some of what you have picked will never work, sir. Sissies have to deal with a little bit of, how shall we say, cameltoe, in the crotch of their panties. You need panties that will cover your bits," Her eyes glinted as she pulled some of the slighter thongs he had selected out of his basket and put them back. The next thirty minutes seemed to be the longest of his life, as BOTH clerks walked around the store and talked to each other about styles and colors that were the best for a sissy. The amusement never left their eyes. When he had all he had been sent to buy, they asked him if he wanted to try anything on. "No! " Steve practically shouted as he handed them his credit card. "Very good sir, but you should know, Mistress Shelly was pretty adamant about you wearing one pair of panties and one cami out of the store…." Steve signed the slip and said "Fine, I will use the dressing room…Where is it?" The girls lead him back to the dressing rooms, tiny cubicles with curtains. One of the girls drew a curtain and waved him in. He turned once he was in, and noticed they were not moving. "Could I have a little privacy?" He asked. The youngest f the clerks face darkened. "Look here you little perv…the two of us have been real polite up until now, and helped you buy your dirty little panties. We wanna watch you put a pair on, and if you say a word, we will scream for mall security. " Steve didn't say a word, and tried to ignore their laughter as he quickly shed pants and panties and shirt, and struggled into the new panties and cami. He pulled his pants and shirt over everything and half ran out of the store hearing "have a nice day…." follow him out into the mall. Back in the car he breathed easier. It hadn't been so bad. If Shelly hadn't called ahead, he probably could have done that pretty smoothly, and without embarrassment. But it was over now, and he could go home. His phone let out a single beep, text message. It was Shelly. All that it said was an address, and the note, "ask for package for Stephanie." It seemed weird, but no weirder than anything else today. He texted back "Will do." and headed to the address she had sent. As the GPS gave him his final instruction to turn, Steve groaned. The address was the local "Sex Positive" sex toy store in town. It was actually a really nice place, in a nice part of town, not seedy, well lit, woman-owned. Steve was just afraid of what was in store for him inside. He parked and entered. instantly, Steve was greeted by a friendly looking woman. Can I help you?" She inquired. Steve mumbled " Package for Stephanie." "I'm sorry for that mix-up, Stephanie, Right away Miss." Miss? Steve thought about correcting her, but just decided it was better to pay and get out. The woman had other ideas. She handed him a wrapped parcel, and started talking to him about lubes, and making suggestions for what she thought was best for him. He agreed to whatever it was she was selling. He asked her what he owed, and she said, "The lady has taken care of it Stephanie, and the lube is my gift to you. Have a lovely day!" She winked as he gathered his parcel and left. He raced home, to find Shelly's car gone. He glanced at the clock, and saw that he was about five minutes late. He ran inside, to find a note on the island in the kitchen. My Dearest Sissy: As I told you last night, thanks to the computer I have known about your…tendencies for a while. It took me a long time to decide what to do, and I did plenty of research on my own in the meantime. All that was left was waiting for you to slip up, and boy, did you ever. Nice timing , though. Neither of us has work for a week after the holiday, and that gives me plenty of time to change some things around here. Please open the parcel you got at the toy store, and notice the contents. there should be three boxes, one says Stephanie (that's you) one says Shelly, and One says tonight. You may open your box now, leave mine alone, and open the tonight box tonight, say after dinner. Your box has some special presents for you to wear, one right after another, until just past dinnertime. The tonight box is a special something you are also going to wear, and I need you to put it on right away. I have gone away for a trip to the spa for some pampering, and will be back tomorrow morning. Love Always, Miss Shelly. Steve re-read the letter about four times, before scrambling to open the package. Inside the box labelled Stephanie were five butt plugs of similar shape, but gradually increasing in size. The biggest one was huge. Now he understood the shopkeep's insistence on the right kind of lube. He dropped his pants and panties, took out the smallest one, and smeared it with lube. Gingerly he pressed it to his ass. It took several tries, but he got it in, and shook with surprise when he got past the widest point and it seemed to suck itself into him, until the flange rested against his asshole. the afternoon was interesting, each plug was a little harder to manage. He didn't think he could manage the final one, but after a ton of lube, and a lot of in and out, he felt the now familiar rush, as he made it past the fat part, and felt it draw into his body. It was hard to concentrate on making dinner and eating, but he managed. After dinner he grabbed the box labeled tonight, and was uneasy. "How big is this plug going to be?" he thought. he shook it, and could here a solid rattle inside. Got to be another plug. Finally, he tore it open, and a smaller box tumbled out, labeled CB-6000. A chastity device. His hands shook. Yesterday, he had been living a normal life, albeit one with a lot of unfulfilled fantasies. Now, he was wearing women's underwear, had a giant plug up his ass, and was expected to lock away his cock. The box had already been opened. Inside were all the parts of the CB-6000, familiar to him from his time on the net. also was a note, handwritten by Shelly, who must have gone to the toy store while he was in the mall buying panties. there were only four words…. "Point Of No Return," written in her lovely script. Steve weighed his options carefully. He could say, "enough is enough, this game ends now." but then he might never get this chance again. He sighed heavily, there was no choice, really. Despite the whirlwind of the last 24 hours, he knew what he was going to do. He read the instructions that came with the CB-6000, and started to put it on. Ironically, he started to get hard, and it took him over an hour and some cold water to subside his erection enough to fit inside. He put the padlock on, and clicked the lock shut. His life would never be the same again. Sleeping that night was impossible. He tossed and turned, and felt agony, as his thoughts made him excited, and the cruel ring of the CB-6000 tried to tear his balls away from his body. He certainly had never realized what the reality of being chastised would truely be. Finally, sleep did come, fitful sleep, but sleep non-the-less. Steve woke up the next morning, groggy. Any thoughts that the previos day had been a dream left him as soon as he felt himself straining against the cage. He heard a door slam shut, and realized that Shelly had arrived home. She came into the room, as he was smoothing his hair and trying to adjust his panties. He started to speak to her, but she shushed him and said, "It's probably better if you don't talk right now." She had the 'Shelly' box, and opened it to reveal an enormous, L-shaped strap-on dildo, and a harness. She shed her clothes, and deftly put one side of the dildo in herself and secured it with the harness. There is no way to sugar-coat what happened over the next four hours. She fucked him repeatedly in the ass. At first it was uncomfortable, but by the end, he was grinding against the base, non-verbally begging for more. She called him a slut, over and over, declared his ass her personal property. He wanted to feel ashamed, but he couldn't. He was in heaven. His wife was in charge, and he was loving it. The rest of the vacation went much the same way. He spent hours between her legs, worshipping her sex, and more hours getting his ass pounded over and over. As she fucked him, she questioned him about the evolution of his kinky desires. But never one did she mention letting him out of the CB-6000. It would be weeks before that would happen, and even then, he was only allowed to cum by her manual stimulation, with his hands bound above his head. By the time the subject of her taking lovers came up, he could only nod and agree. Her logic was infallible. There was no reason she should have to suffer because she had married a sissy. Didn't he want her to be happy, more than anything else? The answer was yes. So, that is how Steve found himself about two years later standing in his kitchen, dressed in lingerie, wearing a chastity device, and holding the box that "promised" him freedom. He tore it open. As explained, a fresh padlock, a tenga egg tumbled out as he overturned the box onto the kitchen table, but no key. The only additional item was a note. On it was a phone number, and the words "you will tell her EVERYTHING, and you shall get the key." The number looked familiar, but he could not place it. He fretted for a while. Again, he knew what he would do, he would do as he was told, just like always. It just took a bit of courage. He found that courage in some white wine and grabbed his phone. He dialed the number, and was stunned at the voice that said "Hello?" His ex. The last one, the one before Shelly. It was all clear now what he was to do. Steve stammered "Hello Alice, it's me, Steve." Alice replied, "Hi Steve…Shelly told me you would call, but it seemed weird, and that was months ago. I had nearly forgotten." "Alice, I have something I need to get off my chest," Steve began, nervously. "Ohhhh-kay," Alice replied, sounding suspicious. "Yeah, so um, while we were dating I did some stuff." Steve said. "Go on," Replied Alice, clearly showing some interest in the conversation. "A couple of time…..A Couple of times….I may have worn your panties, and masturbated in them" Steve finished. A chorus of Hell No's, Oh my Gods, and What the Fucks poured from the phone. Finally Alice calmed a bit, and started to grill Steve. She wanted details, and he provided them as best he could remember. How many times he had done it, when he had done it, was that why he always did the laundry (yes), was that why he had always bought her nice lingerie (yes). she called him pervert, told him her Dad had been right about him, and generally made him feel about three inches tall. The funny thing was, as he revealed bit after bit, he felt better. This wasn't that hard, and getting it all off of his chest felt redemptive. and then, the line of questioning turned. "So she busted you, eh? That is what this is all about? What is this key business all about?" He had been told to tell her everything, and so he did. He told her about being locked, about being a sissy, a cuckold, and about taking it up the ass whenever Shelly wanted him. Alice was revolted. "You think I am keeping this to myself? Oh hell no! I am posting this shit on Facebook right now, EVERYONE is going to know what a perv you are, and what a little wimp." In a small voice, Steve asked about the key. "Oh right, the key, I almost forgot." Said Alice. She postured for a while about how she should't tell him, after all the gross things he had done to her underwear, but in the end, she relented, and told him it was in the breast pocket of his best suit. He had to admire the genius in that, a suit was a Mans outfit, and he was a shell of a man. He hung up the phone as Alice laughed, "Done, posted to Facebook and you are FINISHED! Go have your fun, you little perv, I hope it was worth it!" Steve unlocked himself, and cleaned up a bit. he opened the Tenga egg and squirted in the lube. As he entered it, he heard his phone begin to chime. By the time he came, his face streaked with tears, his phone was ringing off the hook. He silenced it and locked himself back up with the new lock. Somehow he knew that box number two was going to be even harder.
Thanks Strict Sir! I didn't see this when you posted it, but with the site design I was poking around old posts, and saw it today!