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SataiRolePlayingGuy

Ashley x Maggie - Blooming Flowers

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SataiRolePlayingGuy

Aileen was back at the desk.  Quietly waiting for anything else to happen.  They were popular enough to have no danger of going out of business (especially with the help of several rather wealth and semi-frequent customers) but they did not have people lining up to come in either.  So her days tended to be rather slow.  The building itself was open 24 hours a day, but only because appointments could begin and end at any time.  The office had fairly standard office hours and it was rare for exceptions to be made on that.  So Aileen had her eight hours a day sitting at this desk, mostly silent, with customers trickling in with little pattern or warning.  At the moment she passed her time with the book of the girls.  Sure, she already lived with them, had seen many of them naked in person, even been in bed with some of them too.  But there was not a lot to do when there were no customers around.

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cutiepieyuki

Maggie shuffled in the door, looking for all the world like either a ruffian, or someone trying desperately not to be noticed and failing. Her rusty brown hair was pulled back in a ponytail, then stuff unceremoniously into a scally cap her father had left in her dorm, and a large black hoodie, which like all clothes forced her to chooe between fitting in the arm and around the chest, or around her chubby belly. Like every other time, she chose belly, erasing what little bust she had and giving her what the other girls called "boyfriend sweatshirt arms", due to the arms ending about half a foot past her wrist.

Taking a few deep, deep breaths, she worked up the courage to push open the doors. Behind the counter was  a beautiful grown woman, probably a clean foot taller than Maggie. I wonder if I'll get to sleep with her..., Maggie thought. She was everything Maggie wasn't: womanly, calm, composed, tall, staring right at her expectantly... shit shit shit say something "H-hi, I understand that, if someone wanted to, there were certain... Things that they could acquire here. S-services." She stammered out, feeling the taller woman's piercing gaze deep inside her soul.

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SataiRolePlayingGuy

Aileen casually looked the girl over.  Cute, young, there was admittedly some attraction, though she did not show it.  Girls were considerably rarer than men to come through these doors, especially as customers.  Past experience, 'company policy', and a little bit of genuine uncertainty, led Aileen to take a slightly different approach with a girl who happened to visit.  "Welcome.  Are you here to apply for a job, or set up an appointment with one of our girls?  If it is the later, just to be safe, I must point out we have no male employees, as much as some visiting girls might wish we did."  That was partially script, partially enjoying the girl's uneasiness.  She was expected to take a slightly different approach with all female visitors.  First confirming whether they were looking for a job or they were a customer, and if a customer, making sure they understood what was and especially was not available here.  Even after all of that, it was likely to be a little different, though it was much of the same questions she would ask a male customer.

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cutiepieyuki

Maggie squirmed under the intense attention directed at her. "E-employee? I'm kinda young for that, aren't I? I-i mean, not too young to be here, obviously!" she stammered and faked a deeper, more sultry voice than she naturally had about halfway though that sentence to try to fake being older. "I understand that I'll be matched with another woman. I-it's  a shame, but I'm sure it will do" she says, with the most obvious 'excited for my first lesbian experience' face  a girl could have, short of carrying a sign around. "Do I fill out a form, or pick from a book or do you line up all the girls and have me choose...." she rambles on, a bit lost.

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SataiRolePlayingGuy

Aileen thought about how bluntly to answer that, and decided to be completely honest as she would figured out soon enough.  She smiled at the fake attempt to sound older, amused by it or thinking she or the other employees would care.  "I can guess your age, at least close to it.  Most of us are are older, but we have some your age and even younger.  We tend to be...selective about younger employees and keep them the minority.  But there is not a strict minimum age.  If you wanted to work, I would not make the final decision on hiring you, but I would give you an application."

It was slightly impressive she guessed the process as well as she did and amusing how bad she was at lying ad hiding that another girl was exactly what she wanted.  Aileen closed the book she had been entertaining herself with and grabbed the other paper work.  "Follow me, there is a separate room for figuring that all out."  She led the girl into the side room and started putting the paperwork down on her chair.  Both the time options and the fetish list.  "Start with those."  She sat at the other chair and started going back through the book, this time sticking post it notes on various pages.  "Unfortunately, a girl does not have quite as much to choose from here as a guy does.  Some girls just don't want to do it with another girl.  Others will consider it but charge extra.  And some just don't care or will happily take a girl."  She left the girl to focus on the other paperwork as it would take a little while to go through the entire book and have it ready for her.  The pages already said what each girl thought about having other girls, but it was more efficient to mark the ones who were willing to do it.

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cutiepieyuki

Maggie flew through the first p-art of the forms, but as she got deeper, the questions got more and more personal and she got redder and redder in the face; soon, she was answering questions about her bust size, her preferred partner bust size, As she started imagining things, scenarios, partners, and the inevitable outcome, she felt her heart start racing, her face flush red, and her womanhood dampen. Great, now I'm the freak that gets turned on by the goddamn questionnaire. Maggie thought, taking a few breaths to calm herself, one of her small rituals she picked up from her mom. She held herself together long enough to finish the sheet, filling out "Whenever" for the time availability, and handed the two packets back to the attractive office lady.

Without the forms to distract her, however, her mind flipped through the scenarios again, and her heart, face, and pussy resumed their embarassing activity. She was suddenlly very glad for the thcikness of her sweatshirt, as well. Every time the lady looked up at her, Maggie blushed deeper, embarrassed by her immaturity.

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SataiRolePlayingGuy

Seeing her so flustered amused Aileen, though she wondered just how thoroughly the girl looked over the extensive fetish lists.  It might have been even worse if she noticed just how extreme it could get, things she might never have imagined she could or would do, stuff she might never do but still feel embarrassed to see the possibility and imagine it.  "As you can see, we allow almost anything you could possibly suggest.  With the right price there is almost nothing that cannot be experienced.  At least for boys.  It is slightly more limited for girls, though only in a few areas and you can still go rather extreme, to the point you can fulfill nearly any fantasy you want but at the same time almost no one is open minded to try everything."  She closed the book and slid it over to her.  It had many sticky notes in it, though a good chuck of the book lacked them as well.  "Those mark the girls who would be willing to take you.  You make the final choice as the customer, so take your time, though part of my job is to potentially make recommendations."  She sat back and let the girl begin looking.

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cutiepieyuki

Maggie flipped through the book pensively. She didn't want to make a mistake; this girl would be taking her virginity, after all. The variety of women, even just those willing to entertain other women, was impressive, and the variety of bodies was heartening to a young girl suffering from issues about her flabby belly and tiny chest. She pulled a pen and paper out of her hoodie and started writing down the page numbers of particularly attractive women, to her: soft bodies, large breasts, motherly-looking eyes. This continued in silence for a few minutes before Maggie turned the page and saw... HER. 'Ashley' was the name printed at the top of the page, and something about her made Maggie's heart skip. All she could do for several minutes was silently examine every inch of every photograph of the young girl. The soft, short brown hair, the buldge of her growing breasts, everything about her screamed perfect to Maggie. Tearing up her paper, she put the book down. "Her. I want her, whenever she's available." she said, firmly, to Aileen.

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SataiRolePlayingGuy

The customers were not supposed to tear the pages out, but the books were updated and reprinted often enough that it did not really matter.  Aileen was a little more distracted by seeing who was chosen.  "Pfft."  She (mostly) held back a laugh.  They were so suitable it was amazing.  More importantly, Aileen doubted the girl read much if anything about her and was more focused on the pictures.  Did she miss the rather important fact that that girl was a boy until rather recently?  "Excuse me.  Ashley is just...interesting and a better choice than I might have suggested after all."  She pulled out the papers, reviewing the price and checking for anything missing.  "You aren't picky about when, but how long do want her?  A few minutes, a few hours, a night, I assume you can not afford the several night option even if you had the time?"

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cutiepieyuki

Maggie pulls a thick wad of bills out of her bag. It'd be enough to make anyone's heart skip a beat, at least until they realized it was mostly tens and ones. Still, it added up to a couple hundred dollars, and Maggie handed it to the leggy woman helping her. "How long will $400 get me? It's all my christmas and birthday money for the last year. I was saving up for a new trumpet, then the school bought me one, so I didn't really... S-sorry, I'm rambling..." Maggie blushed and averted her eyes, keenly aware of her own embarassment. "If it's not enough for a goodly portion of a night, I'll come up with the rest.

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SataiRolePlayingGuy

Aileen was not sure if she had ever seen someone this desperate to get laid, or at least not this obvious about it, and that was saying something working in a whorehouse.  This girl was crazy.  She wanted this that bad?  It might make it hard for her to become to be a more frequent customer, which was the goal with everyone.  But if this was what she wanted, that is what she would get.  "Oh that will get you one night all right."  She started looking back over the fetish list.  "If you want it that bad, is there anything else you want to add to this?  You could certainly afford to indulge yourself a bit if you want.  Think about it for a bit.  Once you are in her room, you only get what you paid for, the basic package includes quite a bit but is also missing a lot so be sure to request anything you can both want and afford."

 

OOC: I am being a little vague, because I don't exact prices in mind for this stuff, just a more vague general idea.  Just that that is more than enough for one night but perhaps still short of several nights.

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cutiepieyuki

Maggie gulped and blushed. Somehow she had never been as sure of anyhting as she was of this. "I-i'll take the change, then. I'll use it next time." Maggie looked at the woman with determination. Even she was surprised. She'd never felt this way before: her heart thumping, her mind racing, her mouth dry, but her determination sharp. All she knew was that she wanted that girl, and she wanted her as soon as she could get her.

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SataiRolePlayingGuy

Aileen pulled out the tablet and did a quick look over the calendars.  "Her night is completely open tonight."  Between the age and being gender bent, Ashley was quite a niche.  There was a small sub-section of customers who really liked her or girls like her but the majority would prioritize someone else.  She stood and took the money for the night.  "Wait here for a few minutes.  While she is open, I have to make sure she is ready for a surprise immediate appointment.  I will come back after I have checked and either escort you to her room, or schedule a later time if she is not prepared."  She walked out of the room and closed the door behind her.

Heading upstairs, she reached Ashley's room and knocked.  "We need to talk, Ashley!"  A moment later Ashley came to the door, wearing nothing except a pink sleeveless nightgown.  This was part of her thought process, think feminine, act feminine, dress feminine, partially because she just liked doing such things and partially because it helped her truly become a girl as she saw it.  She said nothing, waiting to see what Aileen wanted.  "Surprise!  A new customer wants you, for the night, and SHE wants you now."

Ashley looked skeptically at Aileen.  While she was willing to take female customers, she had none yet and had a preference for men.  More accurately she wanted to develop a preference for men.  It was natural for a girl to want men, to want them inside her.  There was nothing wrong with still liking women, but men should be the priority.  That was her belief.  “Was this your work, Matchmaker?”  She emphasized that last word, it might have been her job but it was also potentially interfering in the natural selection process and possibly sometimes preventing ideal pairings.

Aileen shook her head with a smile.  “Nope she picked you all on her own.  She wants you.  She wants you BAD.  She is here for a girl, though she is doing a cutely horrible job of hiding it.  She is also around your age and may have picked you for that reason.  It looked like she did not read the book at all though, and does not know what you are and why you are here.”  Another look from Ashley.  “You could have told her.  But I am sure you found it so amusing you hid it.”  She let out a sigh.  “Fine, I don’t get enough customers.  Send the girl up for the night.”  She closed the door to end the conversation.

Aileen came back down to retrieve the customer and opened the door to the room she had left her in.  “Good news.  Ashley is willing to take you tonight and I will escort you to her room.  Now let me just clarify how an all-night appointment works.  You get her for the entire night, do it as long as you want, until you get both tired.  You two will then sleep together.  We won’t force you to get up or leave at a specific time, but you will be expected to leave shortly after getting up, with just a little time to clean up and get dressed again.  After it is over, you can schedule a new appointment if you want to and can afford it, with either her or someone else.”

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cutiepieyuki

Maggie, who had been nervously fiddling with her hat while waiting, jumped up at the sound of Aileen's voice. She listened intently to the rules, not wanting to cause any trouble. Putting her hat on over her long hair, she nodded intently. "G-gotcha. I'll do my best to not cause you any trouble, ma'am." She said, gathering her things and following Aileen up and around the building to Ashley's room. Along the way, she couldn't help but admire the place; it was old, warm, and comfy, like a big old armchair. Looking around, she was so distracted she bumped into Aileen when she stopped in front of Ashley's room. "I-in here?" Maggie asks, putting her hand on the door. Taking a deep breath and screwing up her courage, she pushed it open.

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SataiRolePlayingGuy

Aileen had gone over a few more things as she led the girl to Ashley's room.  Her part in the process was over.  She would possibly see the girl again in the morning, if not, Ashley was probably going to tell her about it eventually.  As soon as Maggie was in the room, she closed the door and headed back towards the desk.  From here it on it would just be the two of them and Aileen would be back to waiting for other customers.

The room was fairly small.  Room sizes varied somewhat, but this one was small enough it was clearly a one person office in the past.  With its new purpose it had a bed on end that could fit two people, though somewhat cramped.  On the other side a dresser, small table with a small lamp on it, and a chair.  You were given a place to live while you worked here, but it was a rather simple living arrangement, and also your workplace.

Ashley was sitting on the bed slowly looking the girl up and down.  She was waiting to see what sort of approach and initiative the girl planned to take.  They were encouraged to be passive at the start unless their customer said or otherwise made it clear that they were supposed to make the first move.  The only thing she did was introduce herself.  "I'm Ashley, looks like we will be spending the night together.  I'm sure Aileen told you that, as the customer, you get to decide how this will go.  My job is to give you what you want and leave you satisfied when it is done."  This was a little awkward for her too in truth, she had occasional male customers, but this was also her first lesbian experience and she only had a very basic idea of how two girls did it.  She would have preferred to learn from someone more experienced, but at least this would be an interesting experience.

 

OOC: She would have repeated the stuff I had her tell Logan at the end of the last post in the Catina/Logan story, about initiative, expectations, or whether or not it would be just sex, all being things that were largely up to her, in at least close to the same wording.

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cutiepieyuki

Maggie looked around the room, her eyes flitting from object to object. Every time she looked at Ashley, here face went red and she found interest in a lamp, or the dresser, or the table. C'mon, do something, say something, you paid half a year's worth of pocket money to be here! "Hi. I-I'm Margeret. You can c-call me Maggie, everyone does..." She said, laughing nervously. God damn it god damn it stop being a shy little moron and talk! You literally paid this girl to do things to you, fucking speak! "S-sorry, I'm a bit... Bit nervous," she said, scratching her wrist. "I-i wasn't expecting anyone my age, let alone someone so... W-well, cute." Maggie admited, hopping up on the bed. Taking her hat off, she laid down. "I bet that seems silly to you, huh? Being so nervous. I bet you've been through this dozens of times." With her hat resting on her chest, still wearing her thick hoodie, Maggie had that super girly tomboy look some women spend ages trying to get.

"I'm sorry, I'm rambling..." Maggie said as she sat up and pulled Ashley closer to her. "I-i should take some inititive, for once in my life..." A sad smile, then a soft kiss. Nervous hands found Ashley's arms and pulled her closer as Maggie found some aggression in her tiny body, sliding her hands up and down Ashley's arms and shoulders, appreciating her soft, cool skin, the smoothness of it under her own delicate fingers. Soon, her hands slipped down Ashley's back and found the hem of her nightie. "M-may I?" Maggie asked, her hands groping Ashley's cute little butt.

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SataiRolePlayingGuy

Ashley started with correcting a few misconceptions.  “I’m a little young and new to have that much experience.  Also, we don’t get a lot of girls as customers.  I have done this with a few men before, but not girls.”  The biggest misconception was left unmentioned though.  Ashley was still considering how and if she wanted to clarify that.  She let herself be pulled over, with men she was used to them taking charge, but she had been unsure which of them going to take the lead.  She let Maggie control the pace, but gave her a little encouragement, kissing the side of her neck.  “Go ahead take it off.”  She answered while doing so and then lightly sucking her earlobe as she waited until the undressing forced her to take a break.

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cutiepieyuki

Maggie squirmed and let out the first of many moans tonight, discovering for the first time that her ears are very, very sensitive. She pulled the girl's sheer clothing off over her head, tossing it aside a bit carelessly as she deepened the kiss as it was rejoined. Maggie's hands roamed over the other girl's body; as curious as they were, though, the budding bisexual's hands soon ended up in predictable places, groping and teasing the gender bender's breasts, playing with soft flesh and stiffening nipples, trying to tease a moan out of the more experienced girl. "Well, then we're both on even footing, if you've never been with a girl... Let's take the chance to learn from each other!" She giggled cutely and hefted her own hands above her head, liek a child asking for their coat to be taken off.

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SataiRolePlayingGuy

It was a somewhat strange experience for Ashley.  As a boy-become-girl she was trying to get used to the idea of sex with men, to learn to desire them and what they did to her.  She had not lost her interest in girls though.  She did enjoy her experiences so far with men to a degree, but this was different.  Another girl was still capable of arousing her with more ease than a man.  Curiosity to experience lesbian sex was probably another factor.  Her body was much more sensitive to the touch, she was feeling a girl's arousal perhaps more strongly than she had before.  She let out a soft moan as her nipples proved much more sensitive than usual to the other girl's touch.  Teasing/encouraging her a little more, she rested her hand on Maggie's thigh and slightly rubbed it, getting intentionally close to her crotch without actually touching it.  A reminder of what they were working towards, though with the whole night available, there was no rush to get there.

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cutiepieyuki

Maggie moaned and spread her legs a bit as Ashley slid up her chubby thighs. She was lost in the mewling, moaning pleasure; she knew it would feel good, but somehow missed that it would feel THIS good. Maggie encouraged the girl's soft strokes as she placed her hand on top of the other girl's, leading it up her skirt to her rapidly-dampening panties. Maggie's face was bright red as she whimpered in need to the girl, her mouth finding the prostitute's nipple and sucking slowly. The girl was so soft, so smooth, so gentle... She had imagined sex as a rough, hard, mean thing, but this was like floating on pillows.

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SataiRolePlayingGuy

Ashely was capable of taking a more aggressive style, but this was part of the job, to figure out what the customer wanted and give it to him or her.  If this girl wanted a softer more affectionate approach, that was what she would give her.  She also found the novelty of it interesting and arousing, both the more ‘feminine’ approach and doing it as two girls.

Taking the hint for what she assumed it was, she reached further in, pulled down Maggie’s panties but left it to her to take them off.  Her finger went to work, rubbing the girls slit for a moment.  This was a part she was going to be mostly guessing on.  She had not spent a lot of time yet trying to pleasure herself, so she had a limited idea of what to try, but after a moment of rubbing, she pushed one finger in, keeping it in for now, but exploring and rubbing against various spots of her insides.  It was hard to keep the finger stead though it occasionally twitched and she moaned as the other girl sucked her breast.

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cutiepieyuki

Maggie squirmed a bit, working her panties down her thick thighs and over her plentiful calves before kicking them across the room. Idly, she hoped that she would have a chance to get them back before anyone saw how tragically un-cute they were. The thought, however, was soon interrupted by Ashley wiggling her slender fingers inside Maggie's damp, virgin hole. Letting out a soft moan, Maggie thrust her chest forward. Reaching down, she yanked off her sweatshirt and blouse, before pulling the other young girl slowing into her developing chest, thrusting an aching, despreate nipple at her.

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SataiRolePlayingGuy

Ashley paused for a moment then pulled her fingers out.  "Let me indulge myself for a minute.  We can try other things afterwards if this does more for me than you.  We have all night after all."  She put her hands on Maggie's shoulders and gently but assertively pushed her on to her back.  She spread the other girl's legs and positioned herself between them.  At first she ground their crotches together but after a moment, began bouncing her's up and down.  The truth is she thought of herself as a girl but there was still some man inside her.  She was beginning to mock a man's thrusting, but without anything to thrust into the other girl.  And this was as close as they were going to get.  There was plenty of equipment available to the whores, including strap-ons, but those cost extra and were not going to be in use, for tonight at least.

She alternated the technique, mixing up the grinding with the mock thrusting.  Sometimes the thrusts were hard sometimes she kept their closer but did it faster.  Ashley decided to leave it a mystery why she was doing it for now.  The truth was to deal with some lingering impulses to fuck her like a man would, but for someone who was not familiar with her past, other motives would have seen more likely.  Maybe it was just a fetish of hers, or perhaps she was asserting herself as the more dominant partner.  She was used to being on the receiving end here, but having a girl awoke older desires in her, desires she wished to fulfill before trying other things.  With a man it might have been risky to escalate so quickly on an all night job, but it was not nearly as risky with two girls.

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cutiepieyuki

    Maggie blushed as the other girl pushed her knees apart with a gentle ease. She wasn't a prude, but her catholic upbringing was deep, and she whimpered as the prostitute grinded the crotches together. Little electric sparks snapped through her head as the two pussies rubbed against each other, only to be replaced with a thrusting that felt... weird, and silly, but fun, and the girl alternated between the two. The changing pace and tempo sent Maggie into a tizzy, her confused mind losing it's former cheeky confidence, reverting back to the mewling, needy little schoolgirl she was a few minutes ago, writhing and begging for more. INdeed, it wasn't long before Maggie was writhing on the edge of ecstasy, whimpering and moaning. "PLease, more... Harder, soething... I'm really close...." she begged, with sincere need.

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SataiRolePlayingGuy

Ashley had not expected that to actually be so effective.  For a brief moment she almost wished she was still a boy, or better to be like Aileen.  But she could only work with what she had.  It did feel good for her too, though she was not that far and she was not sure she could climax off something like this.  Not so quickly at least, though maybe she continued to do it long enough.  For her though this was mostly just to work off linger male impulses and instincts.  The fact that Maggie was enjoying it as much as she did was arousing.  She thought it was probably about time to really explain things to the other girl, what she was and why she did this.  She would do that in a moment though, after taking care of the girl's immediate need.

She pushed her upper body up to get a better angle.  "Cute.  This is the sort of thing you really want, isn't it?"  She asked, with a smile, finding it genuinely appealing rather than mocking her.  "Let's see if this is better enough for you to finish..."  She started grinding harder, continuing it for maybe ten to fifteen seconds, then doing the mock thrusting again, harder than before for a similar length of time before returning to the grinding and repeating the alternating pattern.  The mocking thrusting usually started with one or two slow thrusts and then going rather fast for a bit before returning to the grinding.  She was half improvising here, half doing what she thought she would if she was still a boy.  If she was still a boy, she likely would have came already or would have very soon.  But as a girl it was a more moderate pleasure, sometimes moaning and very briefly pausing, but not as close as Maggie was to orgasm.

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