Jessica Line had just started as an administrative assistant at a large firm, she was 22 and fresh out of college. She was initially put in the secretary pool before being assigned to someone permanently. She was happy when she was given a permanent slot, but when the other secretaries heard who she got, she was informed of many rumors.
Alexandra Molly was an upper manager with a strange reputation, she never had the same assistant for more than a few months. At 30 years old, she was the youngest person in her position. She was stern and unapologetically authoritative. Almost all of the girls who worked under her had quit, and in there exit interview insisted they were doing so because something better came along, and not because their boss has treated them badly.
Jessica was a tough and mindful girl and had no intention of quitting the job she had just gotten. But at the same time she didn’t want to be bullied at work. She brought a special purse a friend gave her as a gift from a spy shop that had a little window in for your phone’s camera to secretly record. If she was going to be harassed she would tape it and either sue or leverage a better position with the company.
When she reported to Alexandra Molly’s office she was met by a beautiful woman in a fashionable business suit who was all smiles and friendly greetings. Jessica dropped her guard a bit, until she noticed a strange detail. Most assistant’s desks were located just outside their boss’ office in the hall, but Alexandra Molly had two desks in her large office; hers facing the door, and a second small one that ran perpendicular to hers and pushed against a wall. That did seem suspicious.
The first few days were pretty uneventful, Jessica learned a few of her new boss’ habits and how she liked to have things done. She made appointments and took messages, nothing out of the ordinary. Until Thursday came, and after lunch Jessica’s boss asked her to come over to her desk. Jessica got up and came over, her purse camera was rolling. “Yes, Ms. Molly?” She asked.
“I notice you seem to take a lot of bathroom breaks,” Alexandra started, “I understand you have to serve your physiological need, but I am worried it is leading to too much slacking off.” Jessica wasn’t sure what to say, admittedly when she went to the bathroom she would use it as an opportunity to send a quick text or chat with someone in the hall, but she couldn’t stop going to the bathroom. That’s when her boss offered a solution, “I’d like you to wear a diaper,” Alexandra said as if it was a perfectly reasonable request.
“Ms. Molly… I… I don’t know what to,” Jessica started to stammer, and then realized her phone was recording and the camera was angled right at her boss’ desk, this could be her big break. “Alright,” she agreed, “if that’s what you think is best.”
“Good girl,” Alexandra said pleasantly surprised, “hop up on my desk, bring your dress above your hips, and lay down long-ways on it with your feet up.”
Jessica couldn’t believe how bold her boss was but figured this would make great evidence for the HR rep so she complied fully. She hiked up her dress exposing her panties, and got on her boss’ desk laying down and resting her feet on the corners. She laid her hands across her stomach and looked like she was in a gynecologist’s chair waiting for the doctor.
Alexandra opened her large bottom desk drawer, Jessica couldn’t help but turn her head to look. Inside was a pack of diapers, some powders and ointments, and some other things she didn’t recognize. Alexandra stood between Jessica’s spread legs and closed them for a moment to slip the girl’s panties off before returning her feet to the corners, keeping her spread wide. “I’ll just hold onto these for you,” Alexandra said, dropping the panties into the drawer.
She took a baby wipe and ran it through Jessica’s vaginal lips, which made the girl buck her hips off the table and gasp. Alexandra placed a gentle hand on her waist lowering her back to the desktop, “It is okay, I am just making sure you’re clean.” Jessica swallowed hard and allowed her to continue, knowing it was all being filmed secretly for her gain. But her hands left their peacefully folded position and grasped the edges of the desk when her boss ran a fresh wipe through her ass crack and gently circled her anus.
After a sprinkling of powder, Jessica’s boss had her lift hips slightly as she slipped a diaper under her positioning it just above her ass. What was strange was that Jessica felt a strange sense of calm as Alexandra closed the diaper around her. When she finished and was told she could get up she even inadvertently blurted out, “Thank you Ms. Molly,” which made her boss just smile at her kindly.
Sitting at her desk over the next hour was strange, she shifted her weight several times, constantly aware that she was in a diaper, with her panties across the room in her boss’ drawer. She looked over to Ms. Molly’s desk, who was busy at work, not in the least distracted by the events that just occurred, and unaware the incident had been filmed to be used against her.
The next hour was as bad as the first for her productivity, she had become physically comfortable with the diaper now, but that brought about psychological uncomfortableness. Did she enjoy being put in a diaper like that, did she enjoy wearing the diaper, did she enjoy the power her boss held over her. She imagined some insane scenario where somehow someone would come in and inspect the two women, she was wearing a diaper, but her boss kept her panties, she would look insane. This of course was a preposterous scenario, but her mind was clouded and confused. And then it came on her suddenly, she had to use the bathroom.
She eyed her purse, knowing the camera would still be running, the beauty of a new battery and a huge hard drive. She wasn’t sure if she has enough evidence to mount a case, or if she needed to keep going, or was it that she wanted to keep going. She wasn’t sure what to do, she thought about asking to use the bathroom, but then realized how that would make her look to her boss, she might be on to her. Jessica closed her eyes for moment, let out a small sigh and released her bladder into the waiting vessel. “Ms. Molly,” she spoke, “I need to be changed.”
Alexandra looked up from her desk, and again smiled her kind smile. Standing she gestured for Jessica to come over and lie on the desk once more. The girl got up and walked over, she couldn’t help but feel a flutter in her heart and she again lifted her dress to her stomach and laid down on the desk. The older woman undid the diaper, inspecting the it was only urine, she put it in a special opaque bag that sealed at the top, it concealed the contents of the bag as well as any smell.
When she brought a baby wipe to Jessica’s crotch, the girl seemed to push her hips out slightly, making more of herself available to it. This did not go unnoticed by either woman, as Alexandra took more care and more time to wipe the damp cloth through Jessica’s labia, before giving her ass the same treatment with a fresh wipe. After the powder, Jessica needed no instruction and was lifting her hips awaiting the diaper to be slid beneath her. A faint moan of relief escaped her lips as she was closed into her second diaper of the day. Again she thanked her boss when it was over.
Before she went back to her desk, Alexandra said to Jessica, “There now, isn’t that so much better than having to run off to the bathroom. You don’t even have to leave the office, and there are no distractions.” Jessica nodded in agreement, and hurried back to her desk.
The last two hours of the day passed by much quicker, as Jessica was able to concentrate on her work now much more comfortable in her diaper, still with the lingering thoughts of using the tape in the sexual harassment case of the century. When it was time to go home she approached Ms. Molly’s desk, “Um my…” she asked nervously, “my panties Ms. Molly?”
“Oh yes, of course,” she said, she opened her top drawer, unlocking it, making sure Jessica saw that she did in fact keep them under lock and key. She brought them out, and asked, “Do you just want them, or should I change you into them?”
Jessica thought for a moment, “a better case,” she lied to herself. “You can change me,” she said agreeably. And without any instruction pulled up her clothing, laying on the desk. This made Alexandra smile, knowing she had another one, another young girl under her control.
Alexandra undid the diaper, inspecting it was clean. She of course wouldn’t reuse it, but wouldn’t waste one of her scent sealing bags as they were expensive, she laid it to the side. She saw Jessica’s vagina was visibly wet, she didn’t want to over play her hand, but took a risk and ran her fingers through her slit without even the pretext of having a baby wipe. The girl gave a wordless shudder, and Alexandra slid her panties back on.
When Jessica stood up she eyed the diaper on the desk, “May I keep that Ms. Molly?” she asked. Physical evidence, she continued to lie to herself. She was kicking herself for not just taking her panties and walking, so she wouldn’t have to ask. This would have also saved her from showing her boss how turned on she was, but maybe she wanted her to know
Alexandra smiled at her subordinate, “of course,” she told Jessica, picking it up off the desk and handing it to her.
Jessica stuffed it in her purse and quickly departed the office, her face reddening. Once in the elevator alone, she reached in her purse, past the diaper and dislodged her phone. “Still recording,” she thought with relief, she caught the whole day on tape, and she headed home for the night.
At home Jessica sat in her bed watching the video on her phone. She watched herself being put into the first diaper, and then watched herself being changed into a fresh one, and then lastly having her panties put back on her. She rewound the video, and watched herself being changed out of the dirty diaper again, and then again, and then again. She felt a strange mix of emotion, it was degrading, it was humiliating, and yet she was so turned on.
Her resolve was gone, she hated herself for it, but she had to masturbate, and she had to masturbate to this video. She laid out a towel on her bed, Jessica was a squirter and a big one, and it was actually kind of embarrassing. She had only been with two guys and both were shocked when she came with them, and humiliated her, leaving disgusted and disgruntled. She thought she better warn the next guy, but that embarrassed her too much, and so there was no next guy.
She was smoothing out the towel, knowing it didn’t always catch it all when her mind went to the diaper in her purse. “It would restrain her squirt, even absorb it” she thought. She’d lose her ‘physical evidence’ but she was overcome and didn’t care. She retrieved it from her bag and frantically put it on, for some reason it felt good to be in it. She sat back down on her bed, feeling the diaper under her and pulled up the video again, slipping a hand into the diaper. It didn’t take long before she was screaming, hit by an orgasm, she could feel the splash of her ejaculate on her hand and then it was gone, the diaper worked. She slept like a baby that night.
The next day she arrived at work early and found Ms. Molly was already there hard at work. She passed her own desk, and walked right up to her bosses not even stopping to drop off her bag. “Do you want to put me in a diaper today Ms. Molly?” Jessica asked almost rhetorically.
“Do you want to be in a diaper today?” Alexandra asked back with the same rhetorical tone, looking up from her papers.
She had her, Jessica knew it, Alexandra knew it, there was nothing left but just to come out and say it. Jessica did just that, “Yes Ms. Molly, I want you to put me in a diaper.” Alexandra smiled, almost wickedly, clearing the papers from her desk as Jessica lifted her clothing, she made sure to wear a skirt today, and laid on the desk eager to feel her panties be slipped off.
“Grab the sides of the desks with your hands and keep them there until I say otherwise,” Alexandra commanded authoritatively. Jessica complied immediately, confused being the shift in tone, and slightly aroused. Alexandra slid her panties off and put them in her drawer. She stepped around the girl and reached into her bag pulling out her phone. She played with it for a moment as Jessica’s eyes took on a fearful stare. Alexandra nodded her head finding what she was looking for, Jessica could her the audio and knew her boss was watching yesterday’s events. The video stopped, Jessica heard a familiar whoosh, and then then a generic sound she wasn’t sure of and her boss tossed her phone in with her panties, locking the drawer, before saying, “I think it’s best I hold on to your phone while you’re at work from now on.” Jessica could only give a fearful nod in agreement, keeping her hands firm on the edge of the desk.
Alexandra, dropping all pretext, laid her hand on Jessica’s vagina, already moist. The younger woman had to grip the desk edge tightly to keep from moving her hands. Alexandra masturbated the girl gently as she spoke on, “I emailed the video to my private address and deleted it off your phone and from your outbox.” Jessica moaned low at hearing this, any leverage she had was gone. “You don’t get to where I am without learning all the little tricks, I knew you were filming me, that’s why I acted when I did. I knew you’d go along with it for the camera,” Alexandra spoke as she was increasing the pressure on her captive’s genitalia, intending to let her have an orgasm.
“I squirt!” Jessica blurted out, ceasing her boss’ assault. Alexandra looked at her puzzled, as she disclosed fully, “I squirt when I come Ms. Molly, and it makes a horrible mess. I put on a diaper last night when I masturbated to the video,” her pussy had a spasm at her confession.
“My my,” Alexandra said intrigued, “you are an interesting one. It’s alright my little Jessie, you lack discipline, it’s a problem a lot of you young girls have, and I don’t blame you. You are just still in your anal retention stage,” she falsely referenced psychology to set up her next words, “and I have just the thing to help you with anal retention.” Alexandra went to a desk drawer and pulled out a small blue butt plug and tube of lube.
Lubing the toy generously she brought it to the girl’s anus, who clenched her teeth and grabbed the desk sides hard as it was pushed in, moaning in relief as the widest portion slipped past her asshole and it was able to shrink back down. Alexandra gave the base a little tap, with a pleasant, “There we go,” said. She put a diaper on Jessica, whose face took on its usual euphoria when it was fastened around her. Jessica bit her lip as her boss reached into the diaper and rubbed her clit, just like last night she was cumming in seconds, her squirt hit the diaper, and Alexandra had to stifle a laugh.
In her refractory state she was breathing heavy, her asshole involuntarily tightening around the butt plug’s base every so often. Alexandra took the diaper, soaked with squirt into one of her opaque bags and disposed of it. She used a baby wipe to clean Jessica’s pubic area, leaving the anal plug in and cleaning around it, she fastened a new diaper around her assistant, and moved away from her sitting in her chair.
Jessica stood up, regaining her composure as best she could, shifting her weight on her heels adjusting to the plug stretching her. “Come here Jessie,” Alexandra motioned for her to kneel on the floor between her legs. The girl did, and her boss slid her own panties off in front of Jessica. She too was wearing a skirt, Jessica didn’t notice until now as she hiked it up and showed off her pussy. Alexandra leaned forward and put her hand behind Jessica’s head saying, “I think you need a pacifier to suck on,” and pulled the girl forward having her mouth envelope her pussy.
Jessica had never performed cunnilingus before, but took to it like a fish to water. Happily licking away at her boss’ labia and sucking at her clit, she even complied when Alexandra pushed her head down further and had her eat out her asshole. Jessica’s own ass was adjusting nicely to the plug and she wiggled it in pleasure while she ate out her boss beneath her desk who was squeezing her head with her thighs. When she was happy with her secretary’s work Alexandra gently pushed her back, before she had her stand she used a fresh baby wipe around her mouth, and another on herself, before sliding her panties back on. She made of bit of a show if putting her underwear on, showing off to Jessica that she wore panties rather than a diaper, despite her ideas about them saving time.
She instructed Jessica back to her desk to begin her work, who did so dutifully. Jessica sat down gently, feeling the plug as she lowered herself. She worked hard, and only stopped to have her diaper changed, once before lunch and one after. Alexandra lingered with her baby wipes through Jessica’s vaginal lips, she tugged at the anal plug gently to ensure it was retaining well and tease Jessica in the process. At the end of the day, Alexandra took off Jessica’s diaper, unlocked her drawer and retrieved her phone and panties. She grasped the plug as she spoke, “each morning you come in a few minutes early to be changed into your first diaper, and have your plug inserted. I will hold your panties and phone in my desk until the end of the day, understood?” As she finished she withdrew the plug slowly.
“Yes Ms. Molly, I understand,” Jessica said back. Somehow the phrase ‘your plug’ stuck in her mind. When her boss slid her panties back on her she rose and gathered her things, her ass now adjusting to the absence of the plug. Before she left, Alexandra stopped her to say one last thing.
Her tone returning to stern as Alexandra instructed Jessica, “You are not to masturbate, have an orgasm, or wear diapers without my permission. And as of now, outside this office you don’t have my permission.” She did not ask if she understood, just made her statement. Jessica nodded with a familiar fear of her boss that made her respect her and submit to her so.