Chapter 2

“Sounds interesting,” Anna nodded.

“Which sort of mask would you prefer?”

“Anything that’ll cover my whole face. That’s for sure.”

“But how will you kiss?” CJ asked suggestively. “Or lick?”

Anna nervously clasped her hands on her lap. “I certainly don’t plan on doing any of that.”

“So you’re here purely as a voyeur?”

CJ removed her glasses to reveal her beautiful set of eyes. “Many women tell themselves that. But the deeper they get, the more they want to explore, until the exploration becomes everything to them. Do you catch my drift?”

“Yes, but it’s a little complicated for me.”

“Let me guess, you grew up in a strict religious family. Conservative values. Stern parents. You’ve always lived a sheltered life.”

“Am I that obvious?” Anna nearly blushed.

“Not too obvious. Profiling women is what I do. But more on that later. Right now we’re discussing you.”

“Okay. Honestly, I’m interested in watching, just from a curiosity standpoint.”

“Honesty is a good start. Now we’ll have to discuss the terms of your membership.”

“I’m on a budget, if that’s okay,” Anna replied, a little embarrassed by her financial restraints.

“That’s fine. Your friend Margery is a premium member and she’s helped you get a reduced rate. Here’s what we charge.”

CJ put her glasses back on and typed on the keyboard. Then she twirled the computer monitor around so that Anna could see the screen.

“Oh…” Anna nearly gasped, looking at the price.

“Most people have that reaction. Yet, no one seems to complain once their memberships begin.”

“Must be for good reason.”

“A great reason,” CJ agreed. “We provide unique experiences, training, and most importantly, safety.”

“That’s wonderful to hear.”

“It is. We do extensive background checks, health screenings, and we profile our members and tailor a program that suits them best.”

Anna nodded. “I can live with that.”

“Once that’s finished, we will conduct a more thorough examination of your mental state to create a clear profile. On another day, I will ask about your sexual history, your fantasies, thoughts, desires, and so forth. I can always tell if you’re being truthful or not. When the profile is complete, I will be able to place you in the right setting to fulfill your every need.”

Anna nodded, more slowly this time. “Okay, I can do that too.”

“If you consent, we can begin right away.”

A sliver of doubt crept inside Anna. Her conscience was berating her. But what the heck…you only live once…

“Sure, why not?” Anna replied.

CJ prepared an initial consent form for Anna to sign, who promptly signed it. Then another form asking for Anna’s personal details. Both women exchanged smiles and Anna was led to another room to begin a health inspection with a private medical professional.

Anna dressed in a more hip, and less teacherly attire the next day. She knew she’d be going back to the club to meet CJ again, so she didn’t want to look so rigid, wearing khaki pants and a small tshirt. At work though, she covered her small top with a loose fitting jacket.

When lunch time came, Anna made sure the classroom was cleaned and ready for the next period, while also waiting for Margery. They had already texted each other for lunch plans.

They went to a private area near the track and sat down on a bench with their lunches. Anna explained everything as they ate sandwiches. No detail was left unturned. All had been revealed, as Margery did her best to pry every little thought.

“You know, I feel the need to apologize,” Margery said when the story was finally over. “I feel as though I pressured you yesterday.”

Anna squinted. “These past 24 hours have been quite stressful. You could have saved me a lot of grief.”

“I’m sorry for dragging you into this. The truth is, I got a little carried away. You’re the only person I share these things with. It’s nice having someone to talk to talk to about this.”

“I’m only joking,” Anna smiled.

“Figures,” Margery smiled back, knowing something was up. “Do you think you’ll actually be able to go through with it?”

“I really don’t know. But frankly, I find this process to be fairly amusing. It’s certainly exciting.”

“Bad girl,” Margery said with a slight grin.

“You’re a terrible role model, as it turns out.”

“You’ll come to the dark side soon enough. When are you going back for the interview process?” Margery asked in a suggestive tone.

“Notice anything different about me?”

Margery looked a little more carefully, gave extra thought, and noticed that Anna was wearing more casual clothing, with slightly more attention towards her makeup and hair.

“Oh my,” Margery smiled. “Good luck with that. I hope you make the decision that’s best for you.”

“What do you think I should do?” Anna asked, her right eyebrow arched.

“That’s entirely up to you. But I want to see you at an event sometime. We could be– I don’t know –like partners there somehow.”

The bell rang, signaling that lunch was over and fifth period was about to start. There was sincerity in Margery’s voice and a look in her eyes, but they had to leave the conversation where it was.

After tossing their food wrappers in the trash, they thanked each other for the company, and went to teach their classes.

It was a small room in the club, which looked identical to a therapist’s office. Anna laid on a comfortable sofa, her head propped on a pillow as she stared at the ceiling. Her feet were bare and her toes pointed upwards.

CJ sat on an adjacent couch; a clipboard in one hand, a pen in the other, which had been tapping against her lips. She wore her thick framed glasses again as she looked at the potentially new client.

A series of questions had already been asked. Mostly basic questions at first, like Anna’s early life, her hobbies, her life goals, and other personnel topics. Then the questions became more personal, like Anna’s sexual history, the amount of times she masturbates per week, her sex drive, and things of that explicit nature.

“Tell me about one of your favorite fantasies,” CJ asked quizzingly. “Remember, this will always remain confidential.”

Anna continued laying there, eyes towards the ceiling. “I really like the idea of watching.”

“Lovers,” Anna replied without doubt. “I like watching passion. Real passion. I’ve never been interested in casual encounters or porn, where it’s just rough sex. I’m attracted to the real life intensity.”

CJ wrote some notes. “In these fantasies, do you ever join? Or are you purely a watcher?”

“I join sometimes. But sometimes it feels intrusive of me.”

“I like to fantasize about married couples,” Anna explained. “Like I would be in their home, their living room or bedroom. It’s a romantic setting. And I just stand there, peering at them while they make intimate love.”

“Do they know that you’re watching?”

“Why do they allow this?” CJ asked, writing more notes.

“They like being watched, I guess. It gets them off”

“Do you wish they’d invite you to join?”

Anna nervously twirled her fingers. “Sometimes I think about myself joining. But mainly I get off by watching.”

“Do you think of random couples? Or couples that you know?”

CJ jotted that down. “Interesting. Do you think this has anything to do with your religious upbringing? Do you feel that being a watcher helps take away the feeling of guilt?”

“That’s a fair assessment,” Anna admitted. “I went to Catholic school. I enjoyed it, but the nuns were often…cunts, for lack of a better word.”

“I hear that a lot. You have that air of purity about you.”

“Good thing, I hope.”

“A lot of people find that quality attractive, including myself.”

Anna clenched her hands. “You’re right, though. With my upbringing, I feel more at ease with voyeuristic fantasies. I feel like less of a sinner that way. Like the people I’m watching are the real sinners, and I’m still pure because I’m only watching them.”

“But you still have fantasies of yourself having sex, right?” CJ asked, jotting down more notes.

Anna paused and her toes curled, “Sometimes. Yes, I do. Once and awhile.”

“Any relevant lesbian experiences which you haven’t disclosed yet? Kissing, touching, rubbing, foreplay? Anything at all?”

“None whatsoever. I’m a virgin in that regard.”

“Tell me one of your favorite fantasies with another woman.”

Anna took a long silent breath. “I enjoy romantic, sensual fantasies. Like in a five-star hotel, or some place gorgeous and classy. Maybe candle lights for added effect. We’re dressed in expensive negligee and our hair and makeup are done like Hollywood actresses. Then we do things to each other.”

“What does the woman in your fantasy look like?”

“It doesn’t matter. It’s more about the sensations of it all.”

CJ quickly jotted more notes. “Tell me another favorite fantasy you have? Ever think about any of your colleagues? Is there another female teacher you’re attracted to? Maybe someone you’re close with?”

“Are you talking about Margery?” Anna smiled.

“Let’s start with that. Would you let Margery kiss you?”

“Well, she’s like an older sister to me, honestly. I consider her to be my mentor in teaching.”

“Answer the question,” CJ pushed.

“She’s pretty. Attractive. Yes, I would kiss her. Definitely, under the right circumstance.”

“Would you let Margery eat your pussy? Would you eat her pussy in return, if she asked nicely?”

Anna felt her pussy clench. “I guess…”

“What sex acts do you envision yourself doing to another woman? Any particular acts that really get you going? Massages? Kissing? Breast play? Do you imagine a lot of oral sex?”

Anna clenched harder. “It’ll start with a lot of slow kissing, we undress, then my breasts are fondled. My nipples are sensitive, I imagine them being sucked. Then we go to the bed and — you know — oral sex. A lot of it.”

“I can see your toes curling and your fingers fidgeting,” CJ pointed out.

“I’m sorry. Catholic school really did shape who I am.”

“You were taught that masturbation was bad, and sex is even worse. So just even sitting here makes you feel like a sinner in some way.”

“You read my mind,” Anna replied, amused.

“I went to Catholic school too. I know all the feelings of guilt and shame.”

“What changed? We’re worlds apart in our lifestyle choices.”

“I met a woman,” CJ said in a coy tone. “And she changed my life.”

“She must be beautiful, inside and out.”

“Yes. She also eats pussy like an angel.”

“I can assure you,” CJ said in a calming tone. “Your struggles are common among our members. I like the fact that you struggle with this. It makes it more fun to break down your barriers and expose the real you. The sexual, life-loving woman that exists inside you.”

“Sounds like a challenge.”

“Are you interested in that challenge? This is the part where we agree to the terms of your membership. I can understand if this isn’t for you. If you want to walk away, that’s understandable. This lifestyle isn’t for everyone.”

Anna gulped and mustered her confidence. “I’ve thought about this a lot since we last met, and I want to join.”

“Show me how you masturbate,” CJ said, putting the clipboard down. “Show me your courage and sexuality. Prove that you’re fit to be a member here.”

Anna gulped, then undid her pants. She kept her eyes on the ceiling. Once her pants were open, she slid her right hand underneath her panties. She closed her eyes and focused on her thoughts and fingers. She also heard something. She heard CJ in the background, beginning to masturbate as well, watching her…

Over a week had passed and Anna hadn’t heard anything. She had already been told that she’d be notified of the latest event which would be suitable for her introduction into the lifestyle, so she wasn’t totally surprised by the wait.

When school ended for the day, Anna did her normal clean up routine, then she went to her desk to get her belongings so she could go home. The classroom was empty, and suddenly Margery entered, carrying a medium sized brown box.

They made their usual small talk and banter, blowing off steam from the stresses of the day. Then Margery placed the box on Anna’s desk.

“I visited our mutual friend last night,” Margery said suggestively. “She asked me to give you this box.”

“What is it?” Anna asked, trying to figure out what was in the unmarked box.

“Your future, hopefully.”

“It’ll be okay,” Margery said to comfort. “You’re in good hands. You’re safe. Whatever they recommend for you, it’s for a reason. They’re experts at getting people started with the right scenario.”