This is a story featuring Jessica, from The Tutor Gets Tutored, and Roisin, from The Desires of the Apprentice. It's meant to answer a few unanswered questions from that series, and perhaps if this story gets good commentary and feedback, I might continue it.

You don't need to have read any of my other work to enjoy this story

I took a swig of the cold brew as I walked through the bookstore, my mood dour. Another date, another swig and a miss, and another night of loneliness ahead of me. Apparently, being a broke, unemployed woman with a dual Economics and History degree wasn't a draw for little Miss Perfect Nails, and here I was, alone as usual. I gave a terse smile to one of the employees, a young man who I'd gone to high school with.

"Hey Jessica," he said, smiling at me. Joe was a gawky looking guy, but he'd always been nice to me, and I tried my best to put on a good mood. "Looking for anything in particular?"

"Thanks Joe, uh, nothing really specific," I said, pursing my lips. "Maybe some shitty smutty romance novel to get my mind off things."

He laughed, a sympathetic touch to his cheeks. "My girlfriend loves that shit. I could probably pull up a list. It's kind of funny though, I wouldn't have expected you to be into that kind of stuff. You were always so serious in high school."

Well, considering it had been months since I'd last had sex, and I was very rapidly approaching six months stuck at home with my parents since graduation, my seriousness had been replaced by an intense, aching need for distraction and pleasure. "Seriousness is overrated," I replied stiffly. "I think I found that out too late."

"Aw, but you went to Brown. I'm still finishing up at State," he said, shaking his head. "I wish I'd tried harder in high school like you did."

I snorted. "No, you don't, Joe. You would have hated Brown. It's full of nepo babies and douchebags." I took a quick hit off my vape. "And I mean, like, what good did it do me? I'm here, same as you, doing nothing."

He sniffed. "You can't do that in here."

"My bad." I put it back in my bag. "So... romance novels? Anything good come in lately?"

"Uhh..." He blushed. "You're like, into... girls, right?"

I rolled my eyes. "I've been out since I was fifteen, Joe, you don't need to ask. Yeah, I do, but I read straight romance sometimes too." I wasn't repulsed by heterosexual relations, and sometimes I found it fun to fantasize about it, but I'd never experienced any physical chemistry with a man.

"Well, it's not actually a romance novel, actually. It's a memoir by a journalist who was a member of a highly exclusive sex society of lesbians. I haven't read it..." His cheeks turned redder and he shuffled his feet awkwardly. "But it's gotten rave reviews."

"Really?" I said, my own cheeks coloring a bit. "That sounds ridiculous. How could it even be possible?"

He shrugged. "It's over in the memoirs section, tucked away at the back, top shelf. It's got a red spine. If you're interested. Or I could pull up one of the standard books."

I hesitated. This memoir sounded strange, fantastical. How could such a society exist? Even if it was fiction, I had to read it. "Get me that memoir."

He blushed deeper but didn't say anything as he retreated through the aisles. He returned with a red book in his hands, titled Desires of the Apprentice. "By Roisin McCormick," I read. I flipped open the book jacket and was surprised to see a photograph of her. She was a young woman, maybe in her late twenties, with burning red hair and pretty blue eyes, her pale skin heavily freckled. She was quite attractive, and quite accomplished.

She'd written for several sex and dating columns across numerous newspapers, and was currently a Senior Editor for a magazine called Sapphic Science. This book seemed legitimate indeed. I found I was excited to read it.

#

My excitement was warranted. Roisin McCormick was a tremendous writer. The story detailed her entrance into this strange Society, as an apprentice to the imposing, dominant Carmen. Roisin's lessons under Carmen were strange, complex, painful and highly erotic. She learned how to take and provide pleasure, and suffer pain in equal measures. I found myself reading the book into the late hours of the night, my hand between my legs, strumming my clit eagerly as Roisin described being tortured and tasted by the Mistresses of the Society, her body turned into a device for their pleasure.

When her training in the sexual arts was complete, Roisin set off on a journey of her own, to help Carmen rise to the top of the society. Here she was tested further, engaging in intense sessions of sadomasochistic pleasure, of anal adventures and learning to control her pleasure as well as she could deliver it with her gifted tongue.

To my disappointment, however, the memoir ended rather abruptly. Roisin never did explain the end of her adventures with the sensual Latin goddess, Carmen, and instead said she could not reveal the end of her journey with the Society for privacy reasons. All the names in the story save her own were fake, but I couldn't get them out of my head. Did such a mysterious and sexually gifted society of lesbians exist? And if so, why was I masturbating in my bedroom at three in the morning, when there was a world of pleasure and exploration out there?

The vibrator buzzed as I groaned into my pillow, the book lying spread open face down on my nightstand. I soaked my pajamas as I climaxed, twitching and shaking and then decompressing, my spine uncurling with desperate relief. I pulled the vibrator from my nethers and sucked it clean, enjoying the taste of myself, before I put it back in my drawer. A gift from a former lover, an older woman who had educated me, much as Roisin had been by Carmen.

I lay back on my bed and vaped. Fuck, I was lonely. It seemed the loneliness would never end, and no amount of masturbating would take away the need to touch and feel and experience pleasure with another woman. I grabbed the book and flipped to the very last page, curious to read the afterword.

There wasn't one. It simply said the following:

Roisin is looking for women, early in their sexual journey (with women), to interview for her latest project. If you are interested in participating in an in-depth, hands on exploration of women's sexuality, please visit the website below, and submit your application. We are looking for women of all ages, sizes, and ethnicities.

I swallowed and put the book down. There was no way I was brave enough to do that.

#

The next day, after I'd masturbated for the second time, I decided I was ready to take a look at the application. It wasn't very complex, and the whole site looked very professional. It asked for my name, age, my sexual orientation, and my sexual history. It was not extremely detailed in its request for sexual history.

Please share the number of female sexual partners you have had, the age where you first had sexual relations with a woman, and whether you are in a sexual relationship currently. If you are in a sexual relationship, please identify your status (monogamous, polyamorous, etc.)

I'd only had sex with three women. I'd lost my virginity at twenty-one. I was very much not in a sexual relationship. That was easy to fill out, if embarrassing.

It also asked me for my ethnicity. I almost considered ignoring that, but relented and marked Asian and Latina.

The final request was to send a picture of myself. Nothing lewd, just a selfie. I spent about three hours agonizing over that. I took pictures over and over again, all over my parent's house, in the park, and in the bookstore where I bought the book.

In the end, I settled for a different photo. I took a selfie after I masturbated, my face flushed and glowing with the bliss that comes only after climax, my brown eyes sparkling, my blue-streaked black hair mussed up and loose on the pillow. It was just my face, but it was as close to sending a nude or sexy photo I had ever been. I couldn't stop my cheeks from burning after I hit send on the application.

Would she consider me newsworthy? I very much doubted it.

#

Two weeks later, I was sitting in my room with sweaty palms, waiting in the lobby of a teleconference hosted by Roisin. I couldn't believe it when I got the email, I nearly passed out when the video call was scheduled, and now I felt nauseous. How was I going to be able to talk about my sex life with this highly accomplished woman, who knew more about sex than I could ever dream of?

I was allowed into the meeting. I straightened my shoulders in the stiff, formal blouse I had put on, tucked into black, professional slacks. I didn't know why I had dressed for a business meeting, but it felt quite formal and important to impress Miss McCormick. My parents thought I was doing a job interview. I felt bad for lying to them, and knowing I would only disappoint them when I didn't "get the job" later, but it wasn't as though I could tell them I was talking to an investigative journalist about my sex life.

She popped onto camera, as lovely as her photograph in the book. She wore thick-framed glasses today and had her red hair up in a bun, which served to give her a cheerfully academic look. Her blue eyes sparkled as she raised her hand in salutation.

"Jessica Nakamura?" Roisin said, her voice lilting and musical, with a pronounced Irish accent. "I'm Roisin, it's very nice to meet you.

"Nice to meet you as well," I said, my throat dry.

"Thanks for agreeing to participate. Before we proceed, I'd like to let you know what this process entails." Her smile faded to a workman like firmness as she scanned the notes on her laptop. "This is an initial interview to decide if you are suitable for this project. If we find that you are, I shall conduct a more thorough interview in person." Her lips parted slightly. "The process is quite... intensive," she said. "There is absolutely nothing wrong with you if you don't wish to proceed."

I nodded, feeling a little starstruck by her. Was this really the same woman who had been gagged and fucked in the ass every day, for weeks, during her rigorous training? Who had lapped at cunts while trussed and hung up for display at a sex party? She seemed so professional, so whip smart.

"Can I ask what's involved, or required of me?"

"Let's clear the qualifying phase first," Roisin said. Her tone was polite, friendly, but held a touch of authority. I felt myself immediately compelled to obey her. I could tell she would suffer no frivolity when it came to this process. "Tell me a bit about yourself, Jessica."

I smiled shyly and began to tell her. We discussed my studies, and my interests, and a bit about my family. She was patient and a good listener, better than any of the girls I'd gone out with recently. It was easy to talk to her, to open up about my feelings of failure as an unemployed, young person, and how I struggled with dating.

"It can be difficult," she said, nodding. She was only a few years older than me, but she seemed so much wiser. Probably because of her... experiences. "How did you come upon my memoir?"

"Uh, I was browsing at a bookstore, and my friend Joe who works there recommended it to me. He said it had rave reviews."

"Ah," Roisin said. "Did the contents make you uncomfortable?"

I blushed and shook my head. "No, I mean, I... I thought it was hot. And informative. I mean, I never knew there were so many techniques and ways to perform oral sex on a woman."

She smiled at me, and I thought I caught her glance traveling down my chest, briefly, before she composed herself and looked back up into the webcam.

"Carmen was a marvelous teacher. I was truly grateful to learn from her how to be a more passionate and versatile lover. Have you been fortunate enough to receive education on the sexual arts by a more experienced woman?"

"Yes," I replied, not missing the sexual tone of her question, the way her voice lilted. It felt a little surreal, like I was in the middle of a sexual encounter already. I could feel a flush spreading across my collar. "I slept with an older woman. Actually, I, ah... it started with me sleeping with her daughter. And she found out, and decided to take me under her wing." My cheeks flushed. "I learned a lot from her. But that was months ago. She's dating a man her own age now, and her daughter's gone to State." I felt the bitterness flood my voice. "I've been so alone. And frustrated."

Roisin's brow creased. "And how do you deal with this frustration, Jessica?"

"How?" I blinked and squirmed, looking down, trying not to reveal that I'd been masturbating like a fiend over the past week, fantasizing about her and the sex goddess that was Carmen.

"You said you've been lonely. Are you seeking out casual hookups or romantic relationships?"

"No, nothing like that," I replied, my face red. I knew I couldn't tell her, couldn't say what I'd been doing. "I'm, uh, taking some time. I don't know."

Roisin looked down at her screen. "Your profile states you've slept with three women. You've mentioned two. I'm assuming the other one was your first."

I swallowed and nodded, wondering how the conversation had gotten so intense, so quickly. I felt sweat trickling down my spine and wished I wasn't wearing a button down and slacks. This would have been a lot easier in my usual tank top and leggings. "Yes, she was, um. I had just turned twenty one."

"And why didn't it work?"

"I think she just wasn't intense enough for me," I said, twisting a lock of my blue hair between my fingers, the color fading as the bleach washed out. "After my experiences with the older woman... I think I need something more kinky in my life." My cheeks burned, but it felt good to vocalize such things.

Roisin raised an eyebrow. "Is that why you like reading about Carmen teaching me how to be an apprentice and submitting to her?" Her lips curled into a smirk. "I suppose you're wet right now, aren't you?"

"A bit, yeah," I stammered, swallowing and rubbing my neck, embarrassed.

"Very interesting. You're quite the intriguing young woman, Jessica. I think you'd make a fine profile for the project."

My heart leapt. "Really?"

"Yes." Roisin's smile drifted back to stoic, business-like formality. "Now, would you please tell me about your masturbation habits?"

I shrieked a bit, my hands slapping over my mouth. "What... oh, I don't..."

"Jessica, we're discussing very intimate aspects of women's sexuality. The level of masturbatory frequency isn't going to embarrass me or surprise me." Roisin shifted, a flicker of something intense crossing her face. "Now, please answer the question."

"Um," I said.

"Are you having a hard time because you've been masturbating excessively? Because that's natural. Sometimes we just have urges and need to give our bodies relief. Or maybe you're shy?"

"I, well... I do touch myself often," I said. "At least every night."

"Every night. Mmmm." Roisin was smiling again, a knowing smile, and it made my pussy ache with need.

"Sometimes... lately, it's more often than that." I licked my lips and fumbled with the collar of my button down, loosening it and pulling at the collar to try to relieve the pressure building under the skin of my chest, a blush staining me from breast to cheek.

"When did that begin, Jessica?" Roisin was leaning in close. Her breasts looked larger in the screen, straining against the confines of her dress shirt, and her lips were moist and glistening. She looked hungry.

"I, uh, a few weeks ago. And it's gotten more frequent since I read your memoir." My thighs squeezed together as my core tightened, arousal shooting through me. I wished she was there in front of me. I didn't want to talk, didn't want to explain my sexual habits, I wanted her mouth between my thighs. I wanted her tongue.

"Oh, have you been touching yourself while thinking about me?"

"Y-yes. I have," I whispered.

"I see. So, what exactly have you been imagining? Describe the scenes. Paint the picture. What were you fantasizing about last night?"

I took a deep, shaking breath and closed my eyes, remembering the vivid, lewd details I had thought about last night. "I was thinking about the first time your Mistress fucked your ass."

"Oh. Yes, I remember that. It was a glorious day, being allowed to submit my ass to Carmen, her hands on my hips as she forced me to take that dildo deep."

"It sounded like the toy hurt," I murmured.

"It did. But Carmen helped me to accept the pain. It became a pleasurable thing."

I nodded. "I masturbated to that story, and the ones about you being tied up, and whipped, and all the other things. I couldn't get enough. My vibrator keeps running out of charge."

"Ah, so you use a vibrator?" Roisin studied me, eagerly, like a prized lab specimen under the microscope. "Perhaps I could advise you on your technique. How long do you take to climax?"

I hesitated and bit my lip. "It depends. Usually, um. About five minutes, maybe."

"Interesting." Roisin adjusted her glasses. "Would you like me to show you how to enjoy it more?"

My cheeks might have sizzled, they were so hot. "I... I uh..."

"Sit down in a comfortable spot and put your laptop where I can see your whole body."

Without thinking, without comprehending, I did as she said. I was mesmerized by her voice, her authoritative tone. I took my laptop and sat down on my bed, placing the laptop at the foot while I sat upon my pillows. "Is this good?"

"Very," she murmured, and her expression was suddenly sultry and hungry. "Take off that blouse."

Again, I obeyed. I was wearing a light pink bra beneath.

"Beautiful. Unfasten your slacks. Pull them off."

I kicked the black trousers down my legs. My panties matched my bra in color, simple but not ill-fitting as they had used to be. They were a gift from one of my ex-lovers.

"Lovely," Roisin said. "Now, take off your bra." I hesitantly reached behind my back. It was very out of character for me to do this - I'd never had webcam sex or even sent nudes to someone. But Roisin was irresistible, and I wanted to impress her. To please her. My hands fumbled behind me, and I freed the clasps, allowing the bra to drop from my chest.

Roisin inhaled sharply and I noticed cheeks flush, beautifully clashing with her freckles. "Your breasts are so gorgeous. God, look at those nipples."

I did, and I noticed they were erect, stiff and swollen. "Thank you," I breathed.

"Play with your nipples, first. Ease into it."

My hands shook a bit as I caressed the mounds of my breasts, before rubbing across the peaks, tweaking and gently twisting them. The pleasure was electric, shooting from the peaks to my aching center, and I moaned, closing my eyes briefly, imagining her lips and tongue there, on me, her teeth nibbling.

"Beautiful," Roisin repeated. "Don't stop."

"Mmm," I replied, panting a bit now. "Can't. Feels so good."

"Slip your hands beneath the waist of your panties, touch your lower lips. Feel the slick wetness between them."

I was surprised and impressed at her eloquence, her way of painting such erotic pictures for me. I was practically drooling, and the heat between my thighs had risen to an inferno. My fingers found themselves buried within my folds, exploring the slickness she mentioned. It was incredible, knowing I was this wet without a woman in the room.

"Take off your panties. I need to see your cunt."

No hesitation this time. I shucked my panties down, tossing them on the floor. My fingers returned, this time unhindered, stroking along the dripping flesh between my thighs. I watched Roisin's expression on the screen as she observed between my legs. She looked positively starving, and it thrilled me.

"You've such a lovely pussy, Jessica," Roisin murmured, her voice hoarse, needy. "So smooth and soft. So deliciously pink. You've such a plump clit." Her teeth raked over her lower lip and then she spoke again. "Show me how you finger yourself. One at first, and then two."

I groaned. One of my fingers pressed against the tight, wet hole of my entrance. Slowly, teasingly, it entered me, and I let out a high-pitched whine. "Oh god, yes..."

"Look at me. Tell me how it feels," she whispered.

My brown eyes locked with her blue, and it was almost too much, the pleasure I felt and the lust in her gaze. I withdrew my finger, coated with my slick nectar, and rubbed it against the swollen hood of my clitoris, whimpering and arching. My voice trembled, barely coherent, as I whispered, "Feels amazing. It feels... it feels so good. And knowing you're watching, you're... god, I can't stop thinking about it."

"Stop," she said suddenly, and I froze, my middle finger a fraction of an inch from the apex of my clitoris. "Part your labia with your fingers." I pressed my fingers to the sides of my folds, and pried them apart. My former lover, Mrs. Slater, had also enjoyed doing this before eating me out. "Yes, I see. I understand the way your cunt works now," Roisin said, nodding knowingly. "Do as I say, and you will experience climax on an entirely different level."

My heart raced. Was such a thing possible? My hands moved, slowly, aching for more stimulation, and I spread my legs wider for her, trying to control my breath, trying to stay quiet, even though I longed to moan and shout and cry out her name.

She began to instruct me on the way to ease myself into a rhythm, pumping my fingers slowly inside, and out, with just the occasional brush of my thumb on my clitoris. At times she'd ask me to stroke up and down instead, and the new sensation of pressure against the bottom of my pelvis caused my head to swim and my stomach to churn.

"Don't come," she warned, her tone low and husky, and I was nearing my limits. "Wait until I say."

"I... I don't think I can, Roisin, I can't. Please..." My words trailed into a squeal as she smiled and leaned closer.

"Just a little longer, Jessica, and the orgasm will be even better, I promise. Now, keep fingering yourself, but try this instead. Trace small circles around your clitoral hood with the tips of your fingers, just enough to give it a small pinch."

"Nnnn, ooh fuck, fuck, fuck, shit..."

"Use your other hand on your tits," Roisin hissed.

My fingers moved on my right hand, my index and middle pressing into the sensitive, engorged skin of the hood, and my left went straight for my chest, my nipples pebble-like. I moaned, trying to muffle the sound by pressing my head into the wall, as my slutty legs writhed atop the pillows, my pussy leaking and squelching disgustingly. I'd never been so aroused, not in my entire life.

She tortured me for a half an hour, teaching me new tricks to stimulate my cunt and my nipples. But she refused to let me come. I rode the edge, whimpering with pain, frustration, and pleasure.

"You can do better, can't you?" Roisin said. "Let's see how long you last with your vibrator." I was nearly sobbing with need, but I found the vibrator in my bedside drawer and switched it on. "Good. Now, place it where it's supposed to be."

My face hot with shame, my eyes glistening with tears, I pressed the vibrator's rounded head to my clitoris, and immediately, a shudder ran through my whole body, the tension in my gut pulling tighter. The orgasm was right there, waiting. I'd been at the precipice for so long.

"Roisin," I panted.

"Yes?"

"P-please... may I..."

"Go ahead. Make that beautiful cunt of yours come for me, Jessica."

With a sigh of relief, a high pitched, wavering moan of bliss, I let go of everything. Every nerve, every muscle, tensed, and then released, as if they had been tied to the end of a bow, and I was the archer, releasing the string, loosing the arrow. The vibrator buzzed against my clitoris and the spasms took over, causing my whole body to shake and quiver as wave after wave of the most incredible climax of my life hit me like a brick, knocking the wind out of me and leaving me a trembling, drooling, shaking wreck of a girl.

I don't know how long the orgasm lasted. I just knew I didn't want it to stop.

It finally faded, and I gasped and pulled the vibrator off of me, tossing it aside, the sheets below me damp with my fluids. "Holy shit," I muttered, shaking my head. "What was... I don't..."

Roisin's face was as flushed as mine, her eyes beads of desire. "You're quite the incredible woman, Jessica. Would you like to do another interview with me?"

What answer could I give, but yes?