Private Lessons Ch. 09

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Lacey's week of anal experiences.
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Part 10 of the 15 part series

Updated 06/10/2023
Created 05/01/2021
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These next two chapters are going to be slightly different. Instead of linear progression, both will take place in the same span of time and overlap and you will need both of them for full context. You'll see what I mean when you read them.

After 2 weeks of sex-a-plenty between everyone's favorite girls, Headmistress' Classroom

Lacey fidgeted in her seat when Headmistress sat her and Shani down in front of her desk. Come oooonnn. What are we waiting for? Her cock throbbed and her pussy twitched in anticipation. Headmistress on the other hand simply sat at her desk with her hands folded, professional and still clothed. In fact they were all still clothed. A fact that made Lacey even more impatient.

"Lacey, calm down. We'll get to it in a minute." Headmistress shot Lacey a teacher-like look.

"But I want to get to it nooow!" Lacey shut up when she got an annoyed look from Headmistress. Not the 'I'm going to fuck you for that' annoyed, the 'guardian of a misbehaving child' annoyed.

"Thank you. Anyway. Girls, I have been thinking about something and I want your input on it."

"Our input? About what?" Shani took the lead. Lacey didn't dare open her mouth for fear of saying something that would get her in more trouble, so she was grateful.

"Girls, how would you feel about anal?"

"Yes!" Lacey's excitement boiled over and she stood from her seat. The quickness and volume of her answer startled the other two women. Of course, she was excited. Anal was quite possibly the only way Headmistress hadn't claimed her yet. She wanted to complete the set. She felt her ass tense and relax in anticipation.

Headmistress regained her composure. "That was to be expected. Shani, your thoughts?"

Shani hesitated. "I'm not against it..."

"Buuuuut?" Headmistress prodded.

"Won't it... you know. Hurt? Especially since you're so... you know." Lacey saw Headmistress' face get that smile she got when Shani acted shy. She also felt her face light up in similar fashion Now, without all the added subtext of their previous problems, she was free to truly enjoy watching interactions between the two.

"So what, Shani? You have to finish your sentences, otherwise I'll have to fill in the blanks. Let's see. What am I? Well, I'm not as in shape as you are. Could it perhaps be fat?"

"No!"

"OK. Well you are a big girl Shani. Could it perhaps be short?"

"No..."

"Hmm. Running out of things Shani. I hoped it wouldn't come down to this but it seems there's only one other descriptor." Lacey watched as Headmistress' grin grew wider. "Are you perhaps calling me old, Shani?"

"No! I was saying that you're... big."

Headmistress didn't let up. "That doesn't make sense, Shani. You are bigger and stronger than me."

Lacey watched as Shani hit her breaking point. "I'm talking about your cock!"

"Oh. Well that makes sense. Not to worry, Shani, I thought ahead." They both watched as she opened a drawer in her desk and brought out three items. One was a dildo of a decent size, then some sort of harness, and a large bottle of lube. "You see, Shani, I know just how big 'my cock' is. And I also know how much you two love it. But I do not want to hurt you two, so using these items, you two will prepare each other."

"That makes sense."

"That's not all, girls. I've decided to make this into a game of sorts. You have exams next week.'' At the mention of exams both girls just stared blankly at her. Neither of them had the typical worry of normal university students, for they always did well. "After tonight, I'll be suspending our meetings until after exams." She held up a hand to cut Lacey off before she could complain. Bullshit! "Before you two get mad, hear me out. Your grades are important and I don't want to be a distraction for you two. As well as... it's not all fun and games for me. During this week, you two will use these items to prepare each other. And I will abstain from any self pleasure. Whoever gets the better grade on my exam gets the first load of mine when we start again. Doesn't that sound nice? A little over a week's worth of hot, extra thick cum, right up your tight little asses?" If Lacey still wasn't so pissed about the paused sessions, she may have come in her skirt right then and there.

"It's obvious I'm going to win, so why bother?"

"Lacey, be nice. Shani's been working very hard and has seen major improvement. She might get you yet." As if. "And Shani, if you prepare properly, it won't hurt so much as just being slightly uncomfortable at first."

"OK, Professor." Shani looked up with her eyes wide, realizing her mistake.

"I'll look past that for now. I've prepared a list of instructions to properly prepare. You can look at those later. For now," she stood from her desk, "let's give me something to get me through next week."

Lacey quickly put her chair aside and disrobed. Impatient, waiting to begin. When Headmistress and Shani were equally naked, and the mattress was set up, she approached Headmistress. "I want you inside me."

"Not yet, sweetie."

Lacey's impatience got the better of her again and she gripped Headmistress' arm. "Why not!?"

Headmistress just pushed her down onto the mattress. "Because I could go for a snack and I see the perfect little cream dispensary." Lacey could never stay mad at Headmistress for long. Especially when her lips closed around her shaft and her fingers entered her pussy.

Headmistress' classroom, several minutes later.

Lacey was trying her best to stay conscious after the way Headmistress just mauled her. The warmth Headmistress left inside her had spread throughout her body and made her feel so tired. She could hear the two of them talking about something but the words weren't quite reaching her. The gentle motions and rocking of the bed only served to tempt her to sleep. Wait... gentle? With those two?

Lacey mustered the energy it took to turn herself over and was rejuvenated by the sight before her.

Day 1 of exams Shani's room- Lacey

After a long day of exams and studying, Shani and Lacey retired to Shani's room for the night. After forty-five minutes of studying, they found themselves with nothing to do. Practice for Shani was suspended because of exams and so they had the whole night ahead of them. Lacey suggested they actually do something that girlfriends do, besides fuck. And so they ordered delivery and sat around all night watching movies, Lacey snuggled in Shani's arms. But as usual, eventually Lacey got the urge and she was stuck between ruining their fun and getting off.

She hesitantly spoke up. "Shani."

Her large girlfriend looked down at her from the movie. "Yeah?"

"This is fun, right?"

Shani gave her a big smile. "Of course. I'm glad you suggested we do this. I like just being here with you. It's different."

"OK."

The two of them went back to enjoying the movie, or at least Shani did. Lacey sat there uncomfortable. Why does she have to dress so light? Shani's loungewear was very simple. Short shorts and a t-shirt with nothing underneath. Lacey herself wasn't wearing much to begin with also. Normally she would have been wearing some cute pajamas or something but lately she's taken to wearing one of Shani's blouses and just her panties to bed. Usually it was the one she had worn that day as she liked how it smelled like her.

With both of their legs bare, Lacey had to feel the heat her girlfriend gave off as they cuddled. The thin shirts they both wore didn't exactly protect her upper half as well. Along with just the proximity to Shani, all of these things got her pretty worked up. But she didn't want to ruin the date.

After several minutes, Shani paused the movie. Before Lacey could react, Shani rolled them over so that was on top of her. Then she curled up, trapping Lacey beneath her and making Lacey rest in the fetal position, head against Shani's breast.

Despite watching her practice daily, Lacey forgets just how strong and big her girlfriend is because of always seeing her underneath and submitting to Headmistress or herself. The reminder of her strength and her subsequent show of that strength only made Lacey hornier. It was new and exciting to be pinned down by Shani. But now was not the time to get horny, no matter how good she smelled of how hot the situation was.

"What are you doin-nh- get off!"

"Not until you tell me what's wrong."

"Nothing."

"Wrong answer. You've barely watched the movie and you are acting weird and I'm not about to go through another situation where you hide your feelings. We've both seen where that leads. What's wrong, Lacey?"

Lacey felt guilty. Quietly she admitted. "I'm horny."

"And why is that something to be sad about?"

Lacey broke down. She started shooting out words at an alarming rate. "Because you were enjoying the movie and this is the first time we've ever just hung out and I didn't want to ruin it because of my dick and-" Shani shushed her.

"Calm down. Why would I get mad at you getting horny? You've fucked me most days since we've been together. If I had a problem with your sex drive I would have left a long time ago. Don't worry about stuff like that. It doesn't necessarily matter what I'm doing with you as long as I'm doing it with you. I love you Lacey."

Lacey was still feeling a bit guilty as she relaxed in the makeshift cocoon. "I love you too."

Shani unfolded herself and allowed Lacey her freedom. Lacey found herself missing being underneath the athlete. "Soooo. Do you wanna... try the ... other stuff out? We have to be ready by next week."

Lacey got a burst of excitement that she also felt guilty for having. "Yes."

Together they got out the stuff that Headmistress had given them and sat on the bed. Together, they read the little pamphlet she made for them. They each went to the bathroom and followed the instructions for properly cleaning themselves, and when they got back they set up the towels as instructed. And then they sat on the bed again and looked at each other.

Lacey started. "So um. Who goes first?"

"I was going to leave it up to you."

"But this is a big thing. I can't just decide all for myself. Besides, the guide says we should take turns."

"But we only have seven days. Someone is going to go more than the other." A pause between them.

"What if we both went today? The first step after cleaning is just fingering. It shouldn't take too long to do each other."

"That works, but who goes first?"

After going back and forth for a while with no clear answer the two of them decided to flip a coin. And it landed on Shani.

"I guess I should get comfortable then." Lacey had expected her to get on all fours over the towel but instead she laid flat on her stomach with the towel under her crotch. She looked over her shoulder. "I guess I'm uh, ready when you are."

Lacey sat down on her knees behind Shani and just stared at her ass, not sure where to begin. She loved Shani's ass. It was so big and round and brown and soft and firm. But she had never expected to go inside of it.

Slowly she reached out and just palmed a cheek, slowly rubbing it. Shani moaned into the pillow she placed by her head. The first step says that massaging it might make it looser. Lacey used her one hand to peel the cheek back as the other held the bottle of lube.

She just stared at it for a second. The dark little ring of wrinkles hidden deep within the cleft of Shani's cheeks. Lacey had never really thought about it much before, but in this moment she thought it looked beautiful. She must have stared for too long because Shani went, "is everything alright back there?"

"Yeah, everything's fine. Your asshole is very pretty." She saw and felt Shani's body tense at the compliment.

"Sh-shut up."

"No, I mean it." Lacey said that to reassure her girlfriend but after the words came out, she realized that she misunderstood. It wasn't that Shani didn't believe her; it was that the complement embarrassed her. Having that effect on Shani brought an air of familiarity back to the situation and she felt slightly more confident.

Shani just put her head back into the pillow and Lacey barely heard the "thank you" that she said.

"I'm going to start now." Shani just nodded. Lacey slowly took the bottle of lube and tilted it over her ass. She squeezed out a dollop that landed on Shani's ring. Shani's full body jumped as she let out a gasp. Lacey released her ass and dropped the bottle as she looked towards Shani's other end. "What's wrong!?"

"Nothing. The lube is cold." Oh. good. Lacey reopened Shani's ass and once again she was speechless. It looked good before but now that the hole was glistening and slimy, it looked almost alluring. Lacey caught herself licking her lips.

She went back to the pamphlet. First, try massaging it with a finger. Don't put any pressure, just touch it and play with it so they can get used to feeling something there and relax. This could also be used in conjunction with vaginal/penile stimulation to get them used to associating the feeling with pleasure.

Lacey took one of her fingers and slowly lowered it to Shani's asshole. When she touched it, Shani tensed again, but that was all. She never said how to massage it! Lacey didn't know what to do so she just traced slow circles around it, marveling at how it twitched and flexed against her finger. It's like it's winking at me. After a few minutes of the massage she recognized that Shani had been making noises. Those almost sound like moans.

She pushed slightly harder and Shani jumped again while letting out what was undeniably a moan. Lacey smiled. "Looks like we left out part of your name. You aren't just a slut, you're a butt slut." All Shani could do in response was moan into her pillow.

Lacey noticed a while later that there were slight movements to Shani's hips as she gave the massage. Upon closer inspection she looked past her hand, down to Shani's dripping pussy. She's grinding her clit on the towel. Lacey used her free hand to slap Shani's ass. Shani let out an unrestrained moan and shivered.

"Shame on you Shani! You have your smart, cute, loving girlfriend right here and you decide to hump a towel like someone first discovering masturbation. Is that towel better than me? Is that it?"

Shani whined. "Nooo. I'm sorry, your finger feels so good but it's not enough. I'm so close, I just need a little more. Please." Wait, did she just say she almost came from just my finger. She really is a butt slut. Headmistress is going to love this.

"Fine. I'll be gracious this one time. Next time you cheat on me with an inanimate object though you're in trouble." Lacey reached her free hand down between Shani's legs while her finger continued its little loops. She stuck two of her fingers between the towel and Shani's pelvis and started playing with her clit directly. Lacey decided that she might be relaxed enough. Without her hand to pour lube, she leaned over and spit on Shani's asshole then gently applied pressure with her finger.

She expected it to take more than needed, but on the first sign of force her asshole eagerly opened and swallowed the digit. Shani's body reacted instantly and she let out a near shriek into the pillow. Wanting to heighten her girlfriend's pleasure, she started to gently move the finger in and out while scraping at the walls. Shani became the most vocal she'd ever seen.

"Yes! Yes-yes-yes-yes. Thank you, thank you thank youuuu. Don't stop. Please don't stop. Yesssssssss." On the last word, her voice transitioned into a drawn-out groan as she came. Lacey felt her finger get very snug as the ring and seemingly the canal itself clenched around it as Shani's body convulsed. Lacey was also made privy to the fact that they had set up the towel wrong, at least in Shani's case.

As Lacey kneeled and continued to finger her lover from both ends, she felt her arms, pelvis and even bits of her chest get splattered in Shani's juices. It came out with a force she didn't know it could have. So much for the towel. They had folded in half twice to fit under Shani for maximum absorption but if it had the force to soak Lacey, odds are most of it missed the towel completely.

When Shani's peak ended, she fully relaxed against the bed and Lacey's finger slipped out with zero resistance. The way Shani's body glistened with sweat and the soft rise and fall of her back reminded Lacey of Shani's workouts at practice. That must have taken a lot out of her.

Shani took a few minutes to reset while Lacey just stared at her ass. She really liked that. Is it really that good? When the bronze statue that Lacey called her girlfriend sat up, she decided to go directly to the source

"How was it?" Whatever Shani that had existed minutes prior was now gone and in her place was the normal, shy one. Shani picked up the pillow and put her face in it.

"Fine..."

Lacey tried to tug the pillow out of her hands, large smile on her face. "Just fine? That seemed more than 'fine' to me." After a few harder tugs Lacey huffed as Shani held the pillow close. "Shani, drop the pillow."

"No."

"If you don't drop it, I can't kiss you." She could see Shani wavering. "Also I'll tell headmistress you didn't listen to me and made me sad." That did the trick, as Shani dropped the pillow. Lacey promptly pushed Shani down and crawled atop her until they were face to face. She made good on her promise and kissed her blushing girlfriend. "See? Isn't this better?"

"Yes..."

Lacey took pity on her girlfriend. I'll get to the bottom of that later. "Good."

Day 4 Headmistress' office

Lacey was hopped up on excitement and horniness. She and Shani had made great progress in the past four days and she was eager to Show Headmistress their progress. Or to have her test it herself. Lacey thought slyly.

Full from her quick lunch, Lacey knocked on the door to the familiar office. "Come in." Lacey entered the office and saw Headmistress behind a pile of papers that she assumed were exams. When Headmistress looked up at Lacey, she kept the professor demeanor. "Good afternoon Lacey." She went back to grading.

"You look stressed." Lacey started walking around the desk.

"Yes, Lacey. Students have to take the exams and professors have to grade them. It's not fun for anyone. Now- what are you doing?" Lacey reached Headmistress' chair and took the pen out of her hand. Then she slid Headmistress' chair back far enough that she could stand between it and the desk. "Lacey please I have work to do-"

Lacey put a finger to Headmistress' lips as she climbed onto the chair to straddle her. "I think you could use a break." Lacey reached between them and started massaging Headmistress' bulge.

Lacey grinned harder at seeing Headmistress almost lose it immediately. She was rock hard in her skirt in seconds. She gritted her teeth and suppressed a moan while she reached down to stop Lacey's hand. "Lacey, I don't have time for this. And you know I have to wait until after exams."

Lacey put on a salacious tone. "Do you really? You could cum right now. I won't tell you if you don't." She could see Headmistress' face struggling with her suggestion. She's actually considering it.

Lacey would be lying if she said that she didn't hold a grudge for the last time she was here and got turned down. This was payback for then. As she should be. Like the first time She entered her office. In the palm of my hand.

In an act of pure force of will, Headmistress refused. "No. No I can't do that. I made a promise to both of you."

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