Author's Notes:

Contains: talk of incest and acts of previous chapters, sexual confession to an authority figure, soaking a cushion with mare juice, and a secretly perverted Celestia

While I planned for 6 chapters, it seems the story behind all the clop demanded more room, so I think it's going to be 8-9 chapters. All things considered, this is the most tame chapter in regards to sex being present in every chapter. Yay for feels.

Next chapter will be Shining's side of the drama. That has a pretty impactful opening move...

Twilight Sparkle swallowed a lump in her throat. What she had been dreading had happened and there was no getting around it now. Something she never even imagined before the recent events of a few days ago with her brother now needed to be faced directly, though for better or worse was still undecided. She trembled on her cushion, trying to decide what she could say. The growing silence was awkward and oppressive as she stared at the floor.

“I-I… I’m…” Twilight began weakly before her subdued voice failed again, ears pressed back and thinking she probably looked as miserable as she felt.

Her eyes rose to meet those of the pony beside her again as her eyes grew teary, unable to stop the burning shame that left her face feeling like it was on fire. She saw the endless compassion in those eyes, the supportive kindness that said they’d always be there for her, no matter what. And it somehow felt both reassuring and damning at the same time.

“Twilight, I ask because you have been quite distracted for a few days now, and it is clearly something unexpected and substantial to occupy you this much. I know it is not your estrus, as you have always done so well in keeping it under control. Talk to me about what is weighing on you so. You know I will always listen, and I will offer honest advice, if I can.” Celestia said with a delicate sigh, tired of letting Twilight try to ignore whatever troubled her in silence.

“Princess, I…” Twilight tried again before her eyes closed and she sniffled, knowing she couldn’t run away or tell her mentor any lies. I know I’ll have to admit what Shiny and I did before this lesson ends. Please, please, please, Princess Celestia, don’t say I can’t be your student anymore because I fell in love with my brother on accident and ended up spending my entire day off in bed with him. We’re already prepared to walk away, no matter how badly we don’t want to.

Celestia’s voice took on the slightest bit more of an edge. “Twilight, we have reached a point where this is now, in part, a test of your trust in me. You need to talk to me. Whatever problem you are facing is impacting your studies quite substantially, and I won’t allow it to continue without some understanding. Even if you would prefer to keep it to yourself, you need to share at least a little of it so I know if this will continue to affect you to such a degree, and for how long it may do so.”

Twilight’s face still burned as hot tears began to fall, no longer able to keep them in. Every bit of her resolve was straining to keep herself from breaking down as she grit her teeth, forcing herself to at least give her beloved mentor a shaky nod in acquiescence as she gathered herself.

It was another long pause before she managed to speak. “I-I… A-a-a f-few months ago, I-I wanted to t-try getting some c-confidence and experience d-dealing with other ponies and i-intimacy. P-putting together a report for myself, I f-found the best option was…” Twilight paused again to take a calming breath, sniffling with the resignation slowly setting in once she started and an honest sadness in her tone. “Th-the… The best option seemed to be using the services of The Blind Date Company here in Canterlot. F-fully anonymous. No expectations or standing requirements. Near complete control of how meetings with another pony would proceed. Scheduled times and a surprisingly good system of selecting the kinds of ponies one meets with.”

While Twilight didn’t see it, Celestia allowed herself a tiny smile as she listened and her own thoughts ran. So my faithful student expresses that hidden daring streak I see deep down, and at Blind Date of all places? Someday, you will look back on this moment and laugh with me, my dear… Although, I really hope she never finds out I first met her father there, many years ago when he was a Private in my royal guard, and how I took him as my last long-time lover. That stallion was far too good with his dick. And it’s still funny how much Velvet blushed and squeaked when she thanked me for teaching future husband so many tricks. Hmm, now I have to wonder if Twilight squeals out her orgasms or tastes like her mother did during those threesomes we had before Night and Velvet felt it was time to marry and raise foals. Those are two questions I’ll likely never know answer to, now that I think of it. My little ponies have become so curiously prudish in the past century.

Unaware of her mentor’s mental memory monologue, Twilight continued in the same subdued tone, blushing to the tips of her ears. “I-I don’t know if you’re familiar with The Blind Date Company, Princess. D-do I need to explain more of what th-they do before I continue?”

Celestia gave a quiet, thoughtful hum, tempted to make Twilight actually explain the sexual liaison and fetish functions at Blind Date, but she didn’t want to overwhelm her. Celestia merely gave her a kind smile. “I am fully aware of them and the unique services they provide to my little ponies, Twilight. Please, continue.”

With another small, jerky nod, Twilight pressed on. “I-I found a n-nice sounding stallion’s profile, and we set up a first meeting and date. He turned out to be a unicorn.” Despite sensing she didn’t need to say it, the words spilled out almost of their own volition as her need to confess grew. “W-we had an… oral sex first date. H-he licked me and d-drank f-from me. Then I-I used m-my mouth in return, and s-s-swallowed h-his s-s-sexual fluids.”

One eyebrow arching in silent amusement, Celestia noticed Twilight’s scent in the air, already strong from her estrus, was quickly growing thick and heavy as the young mare was likely getting rather turned on from her memories. While she didn’t mind it, Celestia did have to giggle inside. Oh my, Twilight. This estrus cycle hit you extremely hard, didn’t it? You probably don’t even realize it is so obvious right now.

“The first meeting, we planned for no talking. The second time a few days later and it was the same plan, aside from getting to talk then. I came to find out he was fun to talk to. A couple times, we never even got to the oral sex, and just spent the whole session in conversation. I found out he…” Twilight paused, seeming to wilt a little. “He’s an officer in your royal guard, here at the castle. At first, I was infatuated with the idea of finding out who he was and teasing him whenever I could walk by. I knew I had a crush on him by that point.”

Celestia had already gleaned something had recently gone quite wrong for Twilight. Now it seemed apparent that it had something to do with this stallion she’d met. Depending on the rest of the tale, she might consider discussing things with young Cadence on how to improve matters, but that would take the rest of the tale first.

“A couple weeks ago when we met, I surprised him by letting him go inside my plot. I, I told him that I wasn’t ready for full intercourse just then, but knew I was going to enter my estrus cycle soon. H-he agreed to a Reveal Room with me and we planned our first time to be everything it possibly could be. We planned to take off the blindfolds just as we had our first orgasm during intercourse, and we’d just see how things went from there. I wasn’t really sure what I was feeling towards him at the time, just that the longer I went without knowing his face, his eyes, his smile, the more anxious to know him I became. He’d been so wonderful to me that I-I couldn’t stand not knowing, and maybe I rushed myself, I don’t know.”

Her face remained impassive as Celestia listened, but inside she tensed. While nothing specific had been said, her protective instincts flared. I may never be able to actually tell Twilight for decades, but she has become like a daughter to me. She hasn’t said anything to actually suggest as much, but if this stallion did her harm, I am probably the one pony alive that could track him down. My little ponies have long forgotten the reason why I was once known the world over as The Vengeful Sun and Ashmaker… With effort, Celestia prevented her magic from flaring alongside her urge to protect her foal, knowing Twilight would easily detect it, and she really didn’t need anything else to worry about.

Unaware of the internal reactions of her mentor, Twilight sniffled as she pressed on, her tail twitching a bit and she shifted on her cushion, painfully aware how much she was leaking her own arousal. “We… We met to do just that a few days ago. He was a perfect gentlestallion, as always. I-I had a standard suite of contraceptive spells cast by the Blind Date physician, so we didn’t have to worry about that. I even put a couple of sex spells on us to make it as amazing as possible. Everything was so perfect at first. His tenderness, how he felt inside me, the way he responded to my every need. Most mares dream of how perfect he made our first time together. The kisses he gave me, how he was the perfect length to get all the way inside and touch my cervix with the perfect level of pressure. It stayed perfect up until he started to flare inside me and we got ready for our first mutual orgasm as full lovers…”

Celestia felt a little confused as the story continued. If the stallion had treated her so well and she still had not shown the slightest hint of displeasure, then what was troubling her so?

Twilight took a shuddery breath and whimpered, feeling and hearing her marehood wink with a soft squelch, much to her shame. Her estrus had already begun to return in force, with no sign of slowing down, and was apparently making arousing memories far more effective at getting her riled up. The fact it was so powerful a moment was in no way helpful to keeping herself calm. The faint cool sensation around her haunches said she had best set the cushion she was using aside for cleaning when she got up. She burned with shame over it, despite knowing Celestia had more than once told her not to worry when it inevitably happened during her estrus.

After a moment to compose herself, she continued, fresh tears starting to fall. “W-we took off the blindfolds just before we went over the edge, our horns were touching so we could stare into each other’s eyes for our first release together. I-I couldn’t even finish telling him I loved him as I stared into his eyes for the first time, and I realized who he was.” Another sniffle. “I-I panicked. I tried to cast a half dozen spells at the same time and fizzled out pretty bad. Everything seemed to move in slow motion at that point. I felt my earlier spells activate to keep us locked together so he stayed locked fully inside when one or both of us would climax. I even distinctly felt his penis swell inside me and how his first pulse of semen raced down into my body. With the fizzle making me hypersensitive, it was like his semen was boiling hot as it squirted directly into my uterus, all while staring straight into his eyes. Because of one of my spells, my cervix was even held open and in the perfect place for him to send everything straight in. With another spell meant to keep all of his semen inside me, every little bit he released was kept where he sent it.”

Panting more as she struggled to control herself from grinding her own hoof against her marehood, she remembered exactly how it had felt as her brother had nearly broken her mind with the orgasm his turgid shaft had forcefully blasted into her deepest core. Twilight kept going. “I’ve never felt anything so powerful before. Before either of us was even halfway done with our orgasm, we were kissing and grinding against each other for more, completely unable to stop. Eventually, we just collapsed as the main part of it ended, but our shared orgasm kept going for several minutes, I think. I can’t really remember how much time it took, or how many times he squirted more of his semen inside whenever my body had another spasm and stimulated him again. All I really know is I couldn’t think about much of anything for a while as I was carried along for the ride.”

Twilight swallowed, her eyes having become a little wild and unfocused, though her tears started to pick back up again. “W-we basically woke back up from the extreme orgasm and found out my fizzle had d-damaged the spells. Most of them had remained triggered, rather than shutting off once their conditions were met. Our bodies were stuck together, so he couldn’t pull himself out. W-with the stamina and productivity spell I’d cast on him, he also quickly became fully aroused inside me again. We h-had a short conversation, and I knew there was nothing we could do until my magic started to function properly again. One way or another, he was going to ejaculate inside me multiple times before I even had a chance to fix the spells. I didn’t even know if the contraceptive spells were still functioning. With no other choices, I… I-I told him to make love to me. I completely gave in and realized just how much I loved him in that moment and I begged him to keep going. I told him how fertile and receptive I was, even outright begged him to breed me, even though we both worried whether or not I’d be pregnant by the time we were done. We that the choice to either keep still and we would both feel his arousal grow until my estrus stimulated him enough to release in me again, or we could make the most of it, and make love together for the same amount of time. The results would be the same, regardless of what we did.”

Celestia held her passive expression even as she wondered what the problem was. So far, apart from her recognizing the unidentified stallion and he was somehow a problem in some way, everything Twilight had been describing was all a fantasy come true for just about any pony alive. Getting to experience a first time mutual orgasm with a pony you loved, and while hit with hypersensitivity just before climax? It was difficult even for experienced lovers with practice at it, so Twilight would likely never fully repeat the event at the same level. Having done it a couple times herself, including with Night Light, Celestia discreetly added a little spell over her own marehood to prevent any hint of her own growing arousal from being revealed. Definitely using a dildo tonight. Poor Twilight. She’d completely lose it if she ever realizes just how casual I am about sex in private.

Twilight obviously knew who the stallion was, but Celestia would hold her tongue until the story was over. She could ask for his name later, if it went unsaid by the end, as Twilight clearly needed to let this out.

A shaky smile managed to form on Twilight’s face, even as her eyes were hazy and tearful. “W-we made love for over three hours. I don’t have any idea how long the fizzle really lasted because we were completely lost in each other until the room’s chime sounded and let us know the scheduled session was almost over. Fixing the spells was easy enough, and we separately went back to my apartment after we left. He got us some dinner and we spent the rest of the day and much of the night making love over and over. The whole time, every climax he gave me was kept inside me and I-I swelled up with it. By the time we were done, he had filled me with so much of his semen that I looked ready to have his foal.

“W-when we woke up together the next morning with him still inside me, I don’t think I’ll ever feel that level of total contentment again. It was just so perfect, aside from knowing it had to end. I-I checked the contraceptive spells and found the three protecting my uterus were still fine. The ones that failed led me to getting so turned on and having him climax inside me one last time. H-he actually managed to impregnate me at some point during the night, even though it wasn’t going to implant. I know it has since passed out of me, considering I’m experiencing my estrus again already.” She had to pause to whimper and sniffle, taking a slow breath to keep herself calm enough to continue. “W-we shared the most wonderful k-kiss before he cleaned up so he could leave. After a short talk to set up when we could talk things out when we weren’t overwhelmed with sex, he left. I-I… How could I meet him through Blind Date like that, and have it end up with him ending my estrus early by getting me pregnant? Why did I have to fall in love with my own brother? Why did my completely perfect stallion have to be Shining Armor?!”

As Twilight finished with a small wail and finally broke down completely, Celestia moved a wing over her and pressed Twilight against her side, holding Twilight’s head against the side of her neck as she curled around her sorrowful student. In one name, Celestia suddenly understood completely. And knowing the quality of character in said stallion, secretly already planned as next in line for her next Captain of the Guard, Celestia also knew how true Twilight’s predicament and feelings really were.

As she held Twilight against her, sobbing against her neck as her coat was soaked with tears, Celestia let her mind drift. My dearest Twilight, I wish I could give you an easy answer this time. While incest in Equestria isn’t illegal, nor do we equines have to worry about almost any of the problems of some other races regarding inbreeding, the public opinion is very rigid and negative about it. How I wish I’d paid attention as views on it began to change two centuries ago. It will take me decades to undo, and I’ve been quietly working to correct the misunderstandings for several already when I finally noticed. If you perform as I have been preparing you for with the many great trials to come, and you save my beloved sister like I know you can, I know how much she will need my company. At least Luna will likely want to hide for a time, and nopony will know some of how I care for her. While we never desired each other for romantic love, Luna and I had a bond of deep intimacy I’d neglected to treasure and had ignored too long, like so many of my other great mistakes back then. Sisters-with-benefits, I think is the most apt term in this modern day. Hmm, maybe Equestria will see the Day or Night of the Trembling Heavens from one of us climaxing too hard and shaking our charge around in the sky again. It has been a long time, and we only ever seemed able to do it with each other… I sadly won’t even be able to tell Twilight I support her because of bucking politics, but at least I can easily continue to accept her without reservation. Still, if they’re found out and it becomes necessary, I will publically give her and her brother my support, and make any of the Nobles or general public back off, one way or another. Until then, I cannot otherwise get directly involved, if Twilight is to stay on her path to help save us all.

Minutes passed as Twilight slowly let her emotions out and was able to calm down. She had no idea how Celestia had taken her retelling of what happened, and gradually steeled herself for the worst. If she had to, she’d accept any rejection, or even loss of her apprenticeship, without complaint. She had messed up, plain and simple, and deserved whatever the Princess deemed appropriate punishment. All she’d do is beg that her brother be spared any hardship. His military career would never recover from a major strike against him. She’d take punishment for him, if it came down to it. Hopefully without him knowing.

Celestia let the faintest of smiles show as she looked down at Twilight, still being held snugly against her by a large white wing. “There now, my faithful student. Are you feeling a little better after telling me what has so troubled you?”

Twilight tried to scrub her face and clean off a bit of her tears so as to be more presentable, though she only succeeded in making herself look even more rumpled, unaware Celestia was secretly giggling at how adorable she now looked. Twilight let out a resigned sigh as she looked at the floor and prepared to face the music, as it were. “I do feel much better for being able to tell somepony. I’m sorry I messed up, Princess. I, I understand if you need to punish me for having sex with my brother. All I ask is if you feel the need to punish him in some way, that I be allowed to bear it in his place.”

After taking a moment to blink, Celestia actually did let out a small chuckle. “Oh come now, Twilight. I know you’re sharper than that. What law exactly would I apply in doing so?”

“It would… be…” Twilight had to blink as she paused, running various laws and statues through her head for anything relevant before she wilted a little. “There… aren’t any laws specifically saying incest is illegal? I’m not going to be punished or anything?”

“That is correct. While there are many misconceptions regarding it today, and public opinion of it is rather unpleasant, it was once an almost common practice amongst our smaller communities, and particularly around Equestria’s founding, when it was important to repopulate after losing so many to the ice. I am sure you can figure out the truth from fiction in this matter for the rest. So no, I have no reason to punish you, unless you really want me to. I’m sure I could come up with something.” Celestia said almost jovially.

Taking a very deep breath and letting it out, Twilight let herself relax a bit more than she was. “Thank you for saying so, Princess. Everypony seems so committed to it being deeply wrong, and I know if it got out that my brother and I had sex, that we’d probably receive a lot of anger over it.” She sniffed and leaned against Celestia’s warm side a little more, still being held by her mentor’s wing. “I… I love him so completely, Princess, but what do I do now…? I’m in such a publically-visible position as your student, and so is he with his position as a high ranking officer in the Guard.”

Even as she kept her expression neutral, Celestia made no move to release her wing embracing Twilight. As much as she wanted to tell her to follow her heart’s wish, she could say nothing to that effect. Twilight had to come to her own decisions for the larger plan to play out in their favor. It was of utmost importance that those choices, whether success or mistake, were Twilight’s own choices alone.

“I’m afraid I can’t tell you that, Twilight. It is your life to live, and I must remain neutral on this important moment in your life. All I can say is that I will never turn you away for anything, so long as you continue to live a good life. Just know that I trust your judgement when you have thought something through. Now, considering the situation, we can talk more on this or, if you’d like, we can simply chat and snuggle for the rest of our lesson time.”

Twilight nuzzled against her mentor a little more, not entirely satisfied, but at least feeling much better. And thanks to all her crying, a lot less aroused, if still feeling the slowly drying remains of her marehood getting completely soaked. A content smile appeared on her face, the moment once again reminded her of how she looked to Celestia like a second mother to her, but had never said a word about it because of their respective positions.

“You know, Princess, it’s been some time since we last could do it, and you just let me vent a lot of stress. Have any of the Nobles done anything particularly egregious lately you’d like to poke fun at? Maybe Blue Lord one-upped his own most inane proposal again?”

Celestia tittered, now free to give Twilight a gentle squeeze and happy to spend simple personal time with one she treasured so dearly. “Oh my, yes. The newest one was wanting to tax hoof-made potato corks he heard about from…”