A Different Sort of Mentorship (Jackie x Ashley)

[SataiRolePlayingGuy]

It was a little surprising, more applications were coming in and getting approved in a short time frame than usual.  The standard routine could only handle so much at a time, so a novel approach was being taken now.  Aileen was getting ready to help out one as another was set to arrive.  Improvising, and getting okay from above, she had asked for Ashley to come down.  The girl did not have a customer right now, and she seemed extra suited for this.

She came down looking irritated and ready for bed.  Wearing nothing but a semi-transparent pink nightgown that was not tight enough to be form fitting but tight enough to show what figure her still developing body had.  “What do want, Aileen?  I don’t want to sleep with you tonight.”  She had agreed to sleep with the futa sometimes, when she did not have a customer.  It was one way to help her get used taking cock in a fashion that appealed more to her.  Honestly, she did enjoy it, but Aileen had an ‘interesting’ personality, nosy, sometimes overbearing or a tease.  She was not really in the mood to deal with her right now.

”We have been getting lucky with the amount of fresh blood coming in lately.  Got two girls coming in tonight.  Unfortunately, I can’t cover both of them.  So we’re asking you to do my usual part with one of them.  Honestly, you were going to be her mentor anyway, so it isn’t that a big of a deal.  You just also get to show her around and tell her what’s its like to live here before doing the usual mentoring.  From the little I know about her, you two look like a good match.  You honestly could use some mentoring about being a girl anyways.”  Ashley shot her a dirty look but did not say anything.  She was sensitive about her gender and sexuality.  Biologically she was now a girl in every way, 100% functional with no visible hint she used to be a boy, but especially being the teenager she was, her thoughts and feelings were more confused.

Aileen just continued.  “Her name is Jackie, older for a brand new girl, 30.  But she’s got experience.  You just sit around here and wait for her to show up.  She should be here soon.  Let me know how things go between you two after you spend some tie together.”  Without waiting for a response she left the room to continue whatever she was doing in preparation for a different new girl.  Leaving Ashley to take a seat on one of the lobby chairs and wait.

[Hiddensub]

Looking up at the building Jackie took a steadying breath in before walking into the lobby. She tugged along a large suitcase and a backpack, all her belongings were there. This was the start of her new life, her ex had called her a whore several times at the end now she was just finally accepting it. Jackie had her long black hair tied in a pony tail wearing a white crop top and shorts, moving day required a more athletic look. 

Walking in she had a smile on her face looking around she noticed the young woman in the lobby. "Hello there, I'm Jackie." She introduced herself extending her hand to the young girl wearing a pink nightie, she looked so sweet. "I'm supposed to get started today, do you happen to know who I should report to?" Jackie asked with a relaxed tone to her voice as if this was completely normal to move into a whorehouse. 

[SataiRolePlayingGuy]

Ashley looked over the girl briefly, as she shook her hand, apparently not the sort who came here out of desperation.  She would not pry into that quite yet though, the time to share their reasons for showing up here among other secrets and get to know each other would be a little later.  "Ah, yeah, that would be me this time.  Sorry for not being dressed for it, I only just found out.  Normally the receptionist, Aileen, would do it but we got another new girl starting today and she is handling that one and asked me to take care of you."  She stood up, feeling a little awkward about being dressed like this.  "My name's Ashley.  My first job is to show you around, first to your room and other places in the building.  Give you a sense of what life is like here when you aren't working.  After that, I'm supposed to be you mentor, giving you an idea of what the work is like and answering any questions you have.  I was going to be doing the second part anyway it sounds like, which was why I was asked to both parts.  It will likely be at least a few days before you really start working."

She gestured for Jackie to follow her as she walked to the stairs.  "We will make a brief stop in your room first to drop of your things then roam around a little bit.  The room won't be much to look at.  Just a bed barely big enough for two and an empty cabinet to start with.  It is now your home and your workplace.  If you have any decorations among your stuff you can get them out and place them if you want.  Eventually you can and will want to add a little more furniture or stuff like that, but you will need to use your own money to do so."  She stopped at one of the doors, opened it and turned on the light.  "Here it is."  She waited in the door way to let the woman drop stuff off and doing any unpacking she wanted to do right away.  She also expected some sort of questions or conversations.

[Hiddensub]

Jackie smiled politely as Ashley introduced herself and oriented Jackie to the establishment. Jackie made sure to look around and try to commit the paths to her room to memory hut she knew she'd get lost once or twice. "It's nice to meet you Ashley." She said absentmindedly as they walked. When they finally made it to her room the older woman simply set down her bags. "This works for me, I'm sure I'll be able personalize it some in no time." She shrugged and silently stashed her bags beside the bed. 

Looking Ashley up and down she nodded "The nightgown suits you, you look sexy but sweet." She commented comfortable in paying a compliment to another girl. "I'm sure I'll have loads of questions" she chuckled a little before continuing "where's your room?" Jackie asked curious about her 'mentor' she seemed young but then again Jackie was only newly experienced herself with only a year under her belt in the outside world. At least here she wouldn't have to hide her sexual appetite.

 

[SataiRolePlayingGuy]

Ashley was silent for a second and blushing a little at the compliment.  After considering it for a moment she decided it was best to get the explanation over with quickly.  "Thanks.  Since we are going to be together for awhile there is something you should know about me.  This wasn't always me."  She said gesturing to her body.  "You would not believe it looking at me, but I used to be a boy.  That said, it eventually became clear to me that this is what I really wanted.  Well the body, not the job.  I was one of the first to go through a new procedure.  A gender change far more complete than the old way.  Full body adjustment, figure, voice, completely functional organs, everything that would physically make a girl a girl.  Could even have kids naturally if I want to someday.  Unfortunately it is a VERY expensive process.  That is why I am here.  They paid off my medical debt and put me under contract to pay off as much as can back to them.  I'm obligated to stay here in a way most girls aren't, though I have no desire to run away from it at this point."  She sighed softly, glad to have gotten it over with.  "Things like this."  She said, gently tugging at the nightgown.  "Sometimes I still feel confused, going a little extra feminine can help."

"I can show you my room as I you show around.  I'm not one of your neighbors, but I'm pretty close.  We will be sharing certain other rooms, we share a lot of things here.  I'm sure you are surprised about me, ask about me if you want.  I'm used to it.  I'm unique and there are almost no secrets between us who work here."  She waited to see if Jackie to follow her around some more or talk about her here.

[Hiddensub]

Jackie was a little shocked at her explanation, but that quickly subsided it did explain why a girl so young and pretty would be here. Jackie was old and chose this, to be essentially forced made her a little sad for the girl. But she wasn't angry about it so Jackie said nothing. "Well regardless you look beautiful and don't be so hard on yourself any change takes time to acclimate to." She shrugged and chuckled "at least that's what I'm telling myself with coming here." Smiling she scratched the back of her neck as she followed Ashley.

The older woman patted Ashley's shoulder gently "I leave myself in your capable hands lead the way Captain" she joked trying to get her to smile and laugh she looked adorable when she blushed and Jackie wondered if she could keep making her blush.

[SataiRolePlayingGuy]

Ashley had honestly gotten over much of the awkwardness of the change itself, though there was occasional confusion.  The work, she had more mixed feelings about, sometimes enjoyable sometimes not.  On the other hand almost none of the girls could say they never had a moment or customer they hated, most had varying degree of shame about the job and she was far from unique there.  She smiled a little awkwardly.  “I’m not so worried about my appearance.  Sure, I hope I develop more, but I’m still young and there’s still time for that.”  Honestly, she did have teenager insecurities at times, but that was mostly true.  This was where the change was most confusing.  It had some impact on her sexuality, but she still tended be closer to a boy, or perhaps a lesbian now, when it came to getting any sort of affectionate attention from other women.  She was starting to wondered if this woman shared Aileen’s personality in some ways.

She led Jackie on to the next step of the tour, passing several doors for the rooms of other girls before stopping.  “Here’s part of what I meant by sharing and lack of privacy between the girls.”  There was a small opening in the hall with a door on each side.  One had a traditional women’s bathroom sign on it, the other had sings of an old men’s room sign pulled off and replaced with one that just said ‘Showers’.  She opened that one while commenting on the other.  “Side effect of the building’s origins as an office building.  Nothing you haven’t seen before in the ladies room, just know you don’t get your own.”  As she opened the door the light automatically flicked on.  On one side there was a row of 10 or so shower heads, the other side had a pile of towels and wash cloths of various sizes.

”On the toilet, you at least have the stall wall and doors, as you would assume.  Here?  You take your shower at the same time as another girl, you both see everything.  You can probably guess, its an adjustment for everyone, but more so for me.  Towels are provided.  You bring your own soap, shampoo and anything else you want for the shower.  This isn’t the only shower room in the building, but you will be sharing it with everyone in this section, including me.  Sometimes you will be alone, sometimes not, we don’t set schedules for using it.”  She waited again to let Jackie look around, or ask about it if she wanted to.

[Hiddensub]

Jackie casually followed the younger girl noting that it was a little run down, but it wasn't like they could get city funding to pretty it up she supposed. Looking around she thought that maybe her first goal would be to help improve the conditions, if she was going to be a whore she'd at least work to make her environment better. 

When Ashley showed her the lack of privacy with the showers Jackie frowned looking around noting that if she were to simply set up curtains it'd be just like her college dorm. "Just like college" she said rolling her eyes before smirking at Ashley. "Have the girls ever tried to set up a schedule? It might help." She asked curiously knowing full well that girl dorms could get crazy in usual environments when there was no privacy, she imagined it could be even more so here. "Is there any drama here with the girls I should avoid?" Jackie asked curiously 

 

[SataiRolePlayingGuy]

"...Just like college in more ways than you think, I imagine, or at least the stereotypical image of it.  Naturally, I have no first hand experience."  Ashley replied, while considering the questions.  "Jumping ahead to part of my mentoring, the idea is sooner or later you are going to be hired with another girl to share the same client or a pair comes in and they choose a pair of girls.  That being the case, you might as well get comfortable being casually naked around the other girls and letting them see everything.  The problem with setting up a schedule is a lot of times a girl wants to shower before and/or after an appointment.  Since you can't predict them too much ahead of time, a regular schedule is seen as too much trouble.  Most of us probably prefer it like this."

"As far as drama, we're human and living together, sooner or later you bound to get in a fight with one of them over something.  But, we look out for each other too.  If you are ever in real trouble, a customer breaking the rules, or something else, none of the girls will think twice about helping you, even if she slapped you and called you a bitch five minutes earlier..."  She paused, uncertain what sort of reaction she was going to get after the next thing she said.

"And we're a bunch of whores.  Just like college, many of the girls will get it on with each other when they don't have customers.  A few insist they are 100% straight and refuse to do it, but most do.  We have a few couples, though its usually for other reasons.  Some do it because they say it increases trust or the bond between them.  Some do it just because they are bored or horny.  You should expect at least your neighbors to show some curiosity towards you.  And at least 50-50 on anyone you are showering with."  She did of course leave her own personal thoughts or experiences on this unmentioned.  She wanted to give Jackie a more general picture, and suspected she would be prodded for her own details soon enough.

[Hiddensub]

Jackie nodded, it made sense. When Ashley mentioned being paired with a girl for a client she smirked and lightly nudged her shoulder to the younger girls "Hope it's you" she said with a wink. Looking around with her hands on her hips "Makes sense, we're all each other have now." She chuckled a little "Like a very strange family" She shrugged and tossed some hair over her shoulder.

Coming here hadn't been her first choice but the world out there rejected her and she suspected many other girls too. Thinking for a moment she curiously asked "What do we do to unwind around here, can't be sex all the time our clits would fall off." She chuckled a little at her off color joke hoping to put her young mentor at ease.

[SataiRolePlayingGuy]

Ashley still had no idea whether this woman was just teasing her, or had a genuine interest in her, or maybe both.  It was not surprising for a new girl and her mentor to get involved with each other and possibly quickly, but she was not going to rush faster than whatever pace Jackie might be setting it at, she felt she did not need to do anymore to encourage such an already enthusiastic woman.  “I suppose we would be an interesting pair.”  She mumbled shyly, not sure what would be going through the mind of a man who chose both of them as a pair and what sort of fetishes that would indulge.  She had nodded to the point of them being ‘family’ “Yes, as Aileen likes to say, we’re all a bunch of sisters in a way.”

Moving on to the question of non-sexual entertainment.  “You are somewhat limited in your own room.  It is where you sleep and work.  You can personalize it, make it feel more more like home, but you aren’t allowed to put something like say a TV or computer in there or appliances in general.  For stuff permanently plugged in you are generally limited to something like lamps or a fan or space heater.  For entertainment you could have something like a phone or tablet or a reasonably small book collection.“

”Outside of your room its sharing time again.  There is a single lunch room/cafeteria we all share for eating.  That’s the only place in the building with things like ovens, microwaves or toasters.  You could take small simple snacks back to your room, but anything more complicated, you are strongly encouraged to eat over there.  Then there’s the common room, the one place you find a TV in the building plus a number of chairs and tables, to just talk or just anything else you can think of.”

[Hiddensub]

Jackie smiled at her shyness, she hoped she wasn't making her uncomfortable with her forwardness but since losing her job and accepting the idea of being a whore Jackie threw herself head first into her sexuality not letting herself care anymore about hiding it. 

"That makes sense." She remarked and thought for a moment curious about her new little sister/mentor. "What do you like to do for fun?" She asked as she pulled her long black hair into a messy bun and moved to the sink to splash some cold water on her face and neck sighing with relief moving days were strenuous.

[SataiRolePlayingGuy]

That was a good question, Ashley thought to herself.  “My life has honestly been crazy for quite awhile now.  First there was the process of making me a girl.  It was slow, and I was out for much of it, I couldn’t tell you a lot about what they did to make the process so complete.  Then there is whole learn how to live as girl, something I’m honestly still in the middle of.  Experiencing all the little things that are different.  I’m happy to be a girl, I truly wanted this, but its an adjustment.  Then, becoming a whore, as a 14 year old who just became a girl.  It wasn’t long ago I was in your place, but I had so much more to learn. I was a virgin as a boy, will never know first hand what sex is like for one now, but still learning to do it as a girl and doing it, with men and women was a whole nother thing.  It was a shock at first.  To put it short, I suppose what I do for fun is learn what it really means to be a girl, and doing ‘girly’ things, even if it isn’t all fun.  Maybe it will get boring or ordinary eventually, but it’s still fresh right now.”  Maybe it seemed a strange answer to a woman, but to her the whole process made everything that came with it worth it.  Going through it as a teenager might have even given her a special outlook on it someone older or younger would not have had.

[Hiddensub]

As Jackie patted away the excess water from her skin she looked over to the younger girl. Looking her up and down one would never guess that she was born that way. Looking back to the mirror she wondered if she would have had the courage to go through such a change as a teenager. Thinking on it for a moment "You're amazing, to go through something like that so young. I have to admire you." She said speaking in a softer voice "I can't imagine the adjustment you are going through, if I can help in anyway even to just take your mind off things for a moment let me know." She offered unsure of how she really could help but the older woman supposed just being supportive would be a good start. "Going through teenage years is already difficult but being a teenage prostitute on top of that must be ten times harder at least." Jackie said trying to empathize with her new 'little sister' 

With a smile she turned to lay a gentle hand on Ashley's shoulder "We're in this together right?" She asked bringing a certain warmth to her voice. While Jackie found herself as a prostitute, that didn't mean she changed who she was. It only meant that now she would get paid for sexual acts, not that she had to be rude or hate others. Going into this Jackie was determined to not let this change her kindness. "Are there any games you like to play? Chess?" She asked curiously wondering if she could find a fellow player here or if nothing else at least to teach the girls. 

[SataiRolePlayingGuy]

Ashley shrugged lightly.  “I guess.  But at the same time I tend to feel the same about the girls who came here out of desperation and need of money just to survive.  Yeah, what I did was a huge change, but it was for something I wanted and where the good outweighs the bad.  I never had to deal with what they did on a daily basis.”  Sure being a girl came with a few complications, biologically and socially, she did not previously have to deal with and sex, especially with men, was something she was still getting used to but most of the time she felt she had made the right choice and become who she really was.

She just nodded to the question of them being in it together.  She had no idea where all of this was going to go, as Jackie’s mentor, strange as that felt, it most likely would be different from her and the other girls, but she had no idea what that would mean in the longer term.  She was half this woman’s age, still growing up, and had only been a girl a little while,  It was strange to be looked up to.  “I tend to enjoy things that, though I’ve never been very good at them.”  The common room did include a small collection of things like that, decks of cards and some simpler/cheaper games.  “Of course anyone in the audience will likely insist it be a strip whatever game it is.”  In a place like this it was only natural someone decided the concept of ‘strip poker’ could be somehow twisted to apply to almost anything, it didn’t always happen, but you could expect the recommendation to be made.

[Hiddensub]

Jackie couldn't help but chuckle "Yeah I guess that makes sense" Looking at this younger girl she wondered if there were girls younger than her? Was she the oldest? Did that matter? Shaking her head the woman decided to let those thoughts silde, she would enjoy doing her job and doing it well she normally had a good work ethic but now that it would be mixed with something she enjoyed she was looking forward to it. 

Clapping her hands "Onward then to the common room Captain!" She said happily wondering if she'd be able to meet others. It made so much sense for the girls to have each others backs society wouldn't, so it was up to them. She hoped that would mean less drama - of course there would be some - but she hoped it wouldn't be as bad. 

[SataiRolePlayingGuy]

Ashley was not the youngest and Jackie was not the oldest, but most were in between, in the 18-23 or 24 age range.  Not having been asked, she did not think to mention that, though it was likely to come up at some point, or Jackie might see one of the younger girls, leading to the conversation.  Though something else did feel worth mentioning before leaving the shower.  "One other thing this room reminds me to say.  You will never see a man in here, the shower room that is, though we do have some men employed as security.  Those are the only men other than customers you are likely to see, unless one of the building owners makes a visit.  That said, you might see the occasional cock.  We have a few futanari working here.  Aileen is one of them, and a few of the whores are futa too.  Just something probably worth mentioning so you aren't too surprised when you eventually see one of them.  It can be rather surprising to see one for the first time."  Considering their rarity, it was likely Jackie had never actually seen one before, and they generally were not as open about what they were as they were here.

She turned to leave the shower room, if Jackie wanted to ask or talk anymore about that, they could on their way.  "Its likely to be pretty empty tonight.  Majority of the girls are likely to be in bed right now, some with a customer, some not.  Though it isn't impossible we might run into someone else tonight."  The hall was quiet other than their footsteps and occasional moan or pleasure drawn scream as they passed a room where a girl was currently working.  It would take a few minutes to reach their next stop.