S.L - The Secret Courier

"Okay, this looks a lot more doable..." MJ said, examining the plug, while Erika returned the other sizes to the bag, not wanting the girl to dwell on the larger sized plugs in case they discouraged her.

"As well as wearing these butt plugs, I have this inflatable training device to help further train your anus to stretch, and another dildo just to help get your butt used to being full. But we won't be using them today or for the first week of our training probably..." the Italian woman showed the two dildos to the girl.

"Don't people use those as sex toys?" MJ asked, blushing at asking the question she obviously felt was a little inappropriate.

"Maybe... but people do a lot of strange things sexually... however we shall be using them as training devices, not toys."

"Of course... sorry." MJ mumbled, sheepishly.

"But now you've seen all that, let's get started with the training! You'll need to take off your skirt, tights, and underwear, and probably your blouse so it doesn't get in the way..." Erika said, wishing she had a reason to make the girl remove her bra too so she had her cute secretary fully naked but shrugged to herself, as after all, it was MJ's butt she was interested in, not her little breasts.

"What, here?" MJ said, looking surprised.

"Yes, we aren't going anywhere special to do this training..."

"Oh, I thought I would just take the plug home to use..."

"Yes, but I need to show you how to put it inside first, and how to also keep your anus nice and clean. Then you will take it home to practice further as homework." Erika explained patiently.

"Okay sure..." MJ said, and stood up to undress. She was glad the woman was giving her hands on tuition as, even with the smallest plug, she wasn't quite sure how she'd go about putting it up her butthole beyond just trying to shove it in, The petite girl was a little shy about stripping in front of her boss but obeyed the woman, unzipping her pencil skirt and stepping out of it before kicking off her high heels and pulling down her tights and panties then finally unbuttoning and pulling off her blouse. She stood in front of Erika, naked besides her bra, with her hand over her groin to modestly cover her pussy and little bush of black pubic hair.

"Now, bend over the sofa and show me your butthole so I can get a good look and make sure it definitely is suitable for carrying any sensitive documents..." Erika instructed, and MJ, with the redhead's directions, climbed onto the sofa, got on all fours then lowered her face to the cushioned seat so her butt stuck up in the air. She reached behind herself and grasped her bubble butt, spreading the cheeks apart so her boss got a good view of her asshole. She couldn't believe she was actually showing her boss her butthole, and thought how if someone saw them who wasn't aware of lawyers using secret couriers, they would probably draw the complete wrong conclusion of what they were up to!

Erika too couldn't quite believe the sight she was being treated to as she examined her secretary's tight puckered virgin butthole, which if things continued to plan, she would be training to stretch around plugs and dildos, hopefully gaping when they were removed to give her a view inside. She could also see the girl's pretty pussy with plump outer lips which looked enticing but she knew was out of scope of the scheme, but like the girl's breasts, she was perfectly happy to forget about it as long as she had MJ's asshole.

"I'm just going to take a picture so we can chart your progress..." Erika said, reaching for her phone and snapping a photograph of the girl's exposed butthole without waiting for MJ's permission, but knew her obedient secretary wouldn't object. "Now first things first, we need to ensure your butthole and the surrounding area is perfectly shaven... not that its hairy down there but I can spot a few little hairs we don't want getting in the way. Go and fill this bowl up with warm water..."

"Oh sorry..." MJ blushed, getting up and taking the plastic bowl that her boss handed her, embarrassed to have the woman point out the little black hairs around her asshole where she had never thought to shave before, though she kept around her pussy clean shaven and her little bush of pubic hair in a neat shape.

When she returned with the bowl of warm water, Erika got her to lay on her back on the sofa, and to spread her legs while pulling up her knees so her asshole was exposed again.

"Now, I can see you shave around your vulva so sure you will have no problem adding shaving your butthole to your routine, but I'll take you through it nevertheless. First get the area wet with warm water, to soften the skin and ensure its clean before we shave so you don't get any irritation from oily clogged pores." Erika said, dipping a cloth into the bowl and wiping it between the girl's bubble butt, making MJ gasp at the sensation of warm wetness caressing over her sensitive asshole and intergluteal cleft.

"Now, we will apply shaving cream to protect against rashes..." Erika explained, pulling a bottle out of her bag, and squirting some onto her palm which she had wettened in the bowl, then used her fingers to apply it around the girl's anus. She savoured her first touch of MJ's wrinkled butthole, unnecessarily rubbing it tenderly as she applied the cream over the few wispy black hairs surrounding it. The girl gasped a little at her boss' caressing touch between her buttocks, flustered but making no complaint as she understood she required a perfect clean shaven butthole for her role as a secret courier.

"Now with a safety razor..." Erika continued, fetching one from her bag. "You softly stroke between your buttocks..." The Italian woman demonstrated, gliding the blade over the girl's butthole, carefully removing all of the little hairs between the girl's buttocks.

"Perfect..." Erika said after she had finished her careful shaving, and wiped all the excess cream out from between the girl's buttocks. "Now I want you to ensure you keep down there as hairless as it is now. Do you think you can manage that?"

"Yes Ms Biancalana."

"Good girl, now we have another hygiene routine for you to learn before we can commence with the actual training... so go and replace this bowl with clean warm water please." Erika said, rinsing off the razor in the bowl, the water soapy with shaving cream with a few black hairs floating on surface, then passing it to the girl as she stood up.

When MJ returned, Erika had gotten the enema bulb out ready. "This is a tool to administer enemas to clean out the insides of your butthole. I want you to have an enema every day before you come into office as when you begin work as my secret courier, it shall be important you are ready to take deliveries whenever I require it, and I don't want my clients or myself being exposed to any mess from yourself. So, like with shaving, start doing this throughout your training so it becomes a habit. Don't worry, a plain water enema is fine to have every day, no need for you to take ones with saline as these are to help with constipation while this is just to cleanse you. Now bend over my desk so I can show you how to administer one..."

MJ nodded, nervously eyeing the bulb, but obediently bent over the desk, shuffling her feet wider apart so her asshole was easily accessible between her cute bubble butt.

"So you haven't ever had anything inserted into your butthole before?" Erika asked and MJ shook her head. "No matter, I shall just warm you up a little before inserting the nozzle. We shall be using plenty of lube in your training which helps things slip into your butthole as we don't want any friction causing you pain..."

Erika squirted some lube onto her hand, rubbing her palms together to warm it so it wouldn't feel too chill on the girl's sensitive butthole, then massaged a blob over her anus. MJ closed her eyes, glad she was turned away from her boss as she was ashamed to find she was finding the lubed fingers gently caressing her asshole a little pleasurable, which she felt was an inappropriate response to professional training.

"I'm just going to slip my little finger inside..." Erika warned the girl, before pressing her finger tenderly against the tight wrinkled butthole, and slowly easing it inside, telling the girl to relax as she could feel the sphincter tensing tightly around her little finger. With some deep breaths, MJ managed to relax enough to allow the finger to push a little further inside, and tried not to moan out loud when Erika began to slowly finger her tight hole. The girl couldn't believe how she ever would be able to take the big round container in her butthole if the woman's little finger felt so huge inside of her.

"Good girl, now I think you're ready for the nozzle of the enema bulb." Erika said, smirking to herself that she had actually had her finger up her naïve secretary's butthole. As instructed the girl had gone to the loo earlier in the afternoon so the redhead wasn't surprised that there wasn't any visible mess on her little finger. MJ was apprehensive about receiving her first enema, but felt a twinge of pride every time the woman called her a 'good girl' and encouraged herself by thinking that everything else they had done in the training so far had, though been unusual, gone fine.

Erika filled up the enema bulb from the bowl of fresh water, then applied more lube to the girl's butt, thinking a beginner like her couldn't have too much of it, and then carefully inserted the tip of the nozzle into the wrinkled hole, pushing it deeper inside until it was all the way in.

"I'm going to slowly squeeze the bulb so the water goes into your rectum... ready?"

MJ paused but nodded. "Yes Ms Biancalana."

Erika administered the enema slowly, pausing whenever the girl seemed to be struggling with the new sensation of having her rectum flushed with water. "Gosh, its feeling like far more water than that bulb looked like it'd hold..."

"Don't worry, it's almost empty..." Erika said, squeezing the last of the water out of the bulb. "Now I'm going to pull out the nozzle but want you to make sure your squeeze your butthole so that none of that water comes out."

Erika carefully withdrew the nozzle, with MJ focusing on clenching her butthole as hard as she could, not wanting to embarrass herself by releasing the enema too soon, though her rectum felt full to bursting.

"Now hold the water for as long as you can to clean your lower intestines. As you practice at home, I expect you will learn to hold it for longer periods so perhaps you could begin by administering it, cleaning your teeth, then releasing it, and gradually add more of your bathroom routine in-between as you become able to hold it for longer... When you need to release, just squat over the bowl." Erika said, placing a second empty bowl on the wooden floor, moving the rug as she didn't want any accidents to happen on it though in a way thought she wouldn't mind a stain on it as a reminder of what she had tricked the dumb girl to do in her office.

MJ, with difficulty as she already felt cramps, straightened up. She wanted to just squat over the bowl and release straight away but didn't want to disappoint her boss by doing it too soon, as even though it was her first enema, she wanted to show she had the tenacity to hold it.

After about four minutes, MJ squatted over the bowl and released, feeling the water squirt out her butthole and tinkle in the bowl.

"Good girl, look at all the water you had in your rectum." Erika showed the girl the bowl of water, that was tinged slightly brown with a few flecks of fecal matter in. "Now we'll repeat until there is nothing but clear water coming out of you."

MJ couldn't help but groaning, not realising she would have to do the process multiple times, but didn't complain as she didn't want to sound like she was ungrateful for this important responsibility of delivering secret messages which her boss had trusted to delegate to her, and it was nice of the woman to provide the training personally as she felt she would of struggled to learn how to do all this by herself.

Besides she understood the importance of the enemas as it certainly would be embarrassing if she made a mess in Erika's, or anyone else's, office when collecting or delivering one of the messages. The girl bent over the desk again while Erika refilled the enema bulb from the bowl.

"Here, why don't you do this one yourself?" Erika passed the girl the enema bulb.

****

After MJ had clumsily self-administered her second enema, and filled the bowl on the floor up further with more water, this time perfectly transparent, Erika decided she was ready to begin her anal training.

"We'll start with this tiny plug." Erika said, fetching the pink silicone one that was 3.5 inches in circumference. "First we'll start nice and easy with just the little tip, until you become comfortable with relaxing your butt and pushing out. It may feel a little counter-intuitive but pushing out will help open your butthole up to be more receptive... I know the feeling might remind you of pooing but remember you have gone to the loo and cleansed yourself with enemas so nothing is going to come out."

Erika got the girl to lay back on the sofa again, spreading her legs and pulling up her knees, while she knelt on the floor ready with the butt plug and bottle of lube. "Take a few practice pumps of pushing out your butthole."

MJ obeyed, though, like her boss had said, it felt awfully like she was trying to force out a poop, and she heard her asshole make a wet squelchy sound. "Sorry!" MJ blushed, embarrassed at the fart noises her butthole had made right in front of her boss.

"Don't worry, that's okay, it's just some trapped air from your enemas, nothing to be ashamed of... now keep practicing pushing out your butthole like I told you." Erika said, enjoying hearing the noises coming out of the girl's cute anus.

After watching her secretary's pretty winking butthole while the girl practiced pushing out her anus, Erika introduced the tip of the butt plug, which she had liberally applied lube to, against her asshole. She tenderly rubbed it against the tight entrance before easing in the tip, gently fucking the girl's virgin hole with just the narrow tip of the toy. She held the tip of the plug inside the girl, getting her to breathe deeply until her anal sphincter muscles relaxed while stretched around the toy, before pulling it out to give the girl a little break.

"Not so bad is it? We'll go a little deeper this time." Erika said, pushing the plug back into the girl's asshole, this time a little further so it was stretched more to accommodate the increasing thickness of the toy. She gently fucked the girl then got her to hold it again, allowing her to grow accustomed to the stretch through deep breaths before pulling it out, allowing her a break, then reinserting deeper.

Erika repeated this methodology, thinking how though the existence of secret couriers was a lie, the training itself was at least genuine so MJ would certainly be gaining some new skills at the end of it. Eventually the girl, who couldn't suppress her moans from feeling the strange pleasure of having her butthole stimulated for the first time, managed to take the plug up to its thickest part. The Italian woman admired the girl's pretty anus stretched around the 3.5 inch circumference of the pink silicone plug, thinking how this was only the beginning and that she was sure she'd see the asshole stretch much more in the near future. She picked up her phone and took some photographs, again using the excuse that they were to track MJ's progress though really she just intended to use them to masturbate to later.

Erika felt the desire to slip her hand down the front of her grey suit trousers right there, but couldn't think of a way to justify it to the girl as somehow being part of the training. She found it funny how they both were clearly getting aroused by the anal training but neither of them could touch themselves...

"You've gotten used to the thickest part of the plug now, so ready to take it in fully?" Erika asked and MJ nodded. The redhead pushed the plug in deeper and found it was quickly sucked in by the ass, the girl's sphincter muscles tightening as the toy grew slimmer, ending wrapped around the little rod that connected the plug to its flared base.

"How does it feel?"

"Um.. kinda strange, I don't feel stretched now its inside me but it's a weird feeling of fullness... not bad." MJ said, shifting around a little on the sofa to feel the plug in her rectum.

"Stand up and walk around."

MJ obeyed, and Erika took pleasure in watching the girl walk around the room, the pink base of the butt plug visible between her cute bubble butt.

"Being a secret courier will be much like this, just that the container will be bigger than the butt plug you currently have in... can you feel it inside of you as you walk?"

"Yes kinda, or at least I can tell it's there but it's not too distracting... I kinda like it." MJ blushed and Erika grinned, pleased the girl was enjoying the sensation. She was doing it all for her own pleasure, but would like if the girl enjoyed the anal training too.

"Good, now get back on the sofa, maybe in the position you were in when you first showed me your butthole, and try pushing it in and out to practice a bit more stretching." Erika ordered, pulling over a chair so she could sit behind the girl and watch her fuck her tight asshole with the plug. MJ knelt on the sofa, putting her face down so her butt was stuck in the air, and reached back to take hold of the base of the plug, tentatively tugging on it to feel her ass stretch again, until she had warmed herself back up to pull it out halfway so her anus stretched around its bulbous middle, then got into a rhythm of pushing it in and out, again unable to stop herself moaning quietly in pleasure, blushing to herself in embarrassment at her unprofessional reaction but glad her watching boss didn't seem to care.

MJ was pleased with herself how well the training seemed to be going, and also was enjoying the care and attention her strict boss was giving her, as normally she found the Italian woman a bit cold and dismissive, never willing to devote much time in showing MJ things but for this secret courier training, the woman was attentive and mentoring. 'Obviously it must be very important...' MJ thought, feeling pride, and hoping she would be able to become a capable secret courier for her boss.

****

The training continued over the next month, with Erika pleased at her secretary's progress, having to admit that though the girl wasn't the cleverest, she was certainly a diligent and committed hard worker. Each morning MJ would arrive to the office plugged, showing Erika when she brought the woman her morning coffee, who would take some progress photographs of the girl's butthole, often easing the plug in and out to stretch the noirette, while also inspecting around her asshole to ensure there wasn't an unshaven hair. She was usually able to keep the plug inside of her a couple of hours before having to take it out with Erika encouraging her not to push herself any longer as she didn't want the girl getting an inflamed sphincter that would put a pause to the training. Before she went home, MJ would reinsert the butt plug, or one that was one size smaller than the one she had in the morning, and walked home with it inside of her to practice what it would feel like when she was couriering.

The girl worked her way up the sizes of butt plugs, and, alongside after work tuition, also practiced at home with the two different dildos Erika had given her. The Italian woman couldn't believe how many bottles of lube she was buying, but didn't mind the expense knowing it was going towards lubricating the girl's cute butt so it could stretch around bigger things.