## Preface

Ruined
Posted originally on the Archive of Our Own at http://archiveofourown.org/works/15370299.

Rating:
  Explicit
Archive Warning:
  No Archive Warnings Apply
Category:
  M/M
Fandom:
  Critical Role (Web Series)
Relationship:
  Mollymauk Tealeaf/Caleb Widogast
Characters:
  Mollymauk Tealeaf, Caleb Widogast
Additional Tags:
  Period Sex, Menstruation, Oral Sex, Trans Male Character, Established Relationship, Multiple Orgasms, Orgasms help with cramps ok
Language:
  English
Stats:
  Published: 2018-07-21 Words: 2,483 Chapters: 1/1

# Ruined

by keefling (orphan_account)

Summary

> Of course Molly could smell blood, that was his whole thing.

Notes

> Please be warned, this is about a trans male character who gets his period. There are descriptions of menstrual symptoms throughout.

> Caleb is a trans man in this fic and I use feminine-coded words to describe his genitals.

See the end of the work for more notes

## Ruined

Caleb was woken in the middle of the night by a deep ache in his abdomen. He had folded over on himself in his sleep, arms tucked between his chest and thighs and his forehead pressed to his knees. He felt the heat of Mollymauk against his back, but what was usually so consoling now filled him with dread. Even though Caleb had been suppressing his hormones for years, every so often he would menstruate. It had happened before when he had been more active or had eaten more, but in the disorienting darkness with what felt like knives twisting in his gut, the fates were the easiest to blame.

Caleb tried sitting up, lying on his back and on his other side, but he could find no comfortable position. His chest was sore, his stomach felt bloated, his groin ached and so did his thighs, all the way to his knees. When Caleb felt the tell-tale trickle of blood down his thigh, he slinked into the washroom, cursing as his suspicion was confirmed. Glaring at the dark red spot on his underwear, Caleb stuffed a cotton pad between his legs and shuffled back to bed. He climbed in carefully as not to disturb Molly, but his partner was already awake.

“Something wrong?” Molly asked, groggy.

“ N-nein, ” Caleb said, tugging the blankets up around his ears.

“Caleb? Please don’t lie to me. Are you alright, sweetheart?”

Caleb groaned. He opened his mouth and closed it. He did not want to lie, but he could absolutely not tell Molly about the root of his discomfort. What would Caleb even say? I’m bleeding from my pussy but don’t worry it’s normal and I promise I’m fine so go back to sleep?

Scheisse. Caleb buried his face in the pillow as if he could make himself go invisible.

“I normally wouldn’t press you, but I smell blood and I need to know you aren’t hurt,” Molly explained, gently.

Of course Molly could smell blood, that was his whole thing.

Caleb looked at Molly with pleading eyes.

“I am, ah….menstruating,” he said. The word felt harsh and ugly on his lips. His face burned and he felt tears prickle in the corners of his eyes. Molly had never seen him like this, and Caleb had hoped he never would have to.

“Oh, sweetheart,” Molly cooed, “That’s nothing to be ashamed of. It’s common for someone with your bits, isn’t it?”

“Not for me,” Caleb answered, “It should not be happening to me.”

“Is it painful?” Molly reached out and stroked Caleb’s hair. The contact was nice; something to focus on besides the cramps.

“ Ja, ja, very painful,” Caleb admitted, “I am sore all over.” He sucked in a breath through gritted teeth as he felt something seize up on his right side.

“Can I help? A cuddle? A massage? I heard that orgasms help with cramps. I could help you have one.”

“Mollymauk!” Caleb cried, blushing furiously, “You are horrible.”

Molly chuckled. “I’m sorry, dear, but my offer still stands if you change your mind.”

“Oh, gods, Molly,” Caleb groaned, smashing his face into the pillow, “You cannot touch me. I am….filthy.”

“Sweetheart, I’m no expert, but you aren’t contagious.”

“I know, I know, but it is disgusting, what my body is doing right now. I hate it. I hate it so much.”

“It’s just a bit of blood,” Molly argued, “I don’t mind, Caleb, I really don’t. It’s natural, and it’s definitely not disgusting.”

“Molly…” Caleb whimpered. He could not convince himself that his body was not home to some grotesque monster shredding his insides, but the reassurance sounded genuine on Molly’s lips.

“Caleb, my love, what do you need?” Molly spoke in a whisper, his voice so full of concern and adoration that Caleb felt like crying.

“Will you, ah, massage my chest?” Caleb’s voice shook as he spoke. “I know I have asked you not to, but this time, it’s….it’s sore and I think, maybe, that will help?”

“Of course, darling,” Molly said, sitting up, “Can you roll onto your back for me?”

Caleb’s stomach did not like being stretched out and it protested being pulled taut as he extended his legs. He put his hands on both sides of his chest, demonstrating to Molly where he wanted to be touched.

“Over my shirt, please,” Caleb added.

“Alright,” Molly nodded, “Let me know if you want me to stop.”

“I will,” promised Caleb, “I trust you.”

Molly smoothed his palm over Caleb’s tender chest. He rubbed in slow circles, his eyes fixed on Caleb’s face for any sign of discomfort. Caleb’s eyes fluttered closed when Molly began to knead the flesh around his nipples, squeezing the soft tissue and rolling it between his fingers.

Caleb usually hated having his chest touched, so he was surprised by how much he was enjoying it now. Every inadvertent brush of Molly’s fingertips against his nipples shot a jolt of pleasure straight to his groin. Caleb's breath quickened and he caught himself moaning, realizing too late that Molly could hear him. Mortified, he grabbed one of Molly’s wrists.

“Stop,” Caleb said, “I’m sorry, please, it’s too much.”

Molly’s hands disappeared immediately. Caleb covered his chest with his own hands and could feel his heart racing.

“I’m fine, I am just very sore.”

“Did it help?” Molly asked.

“Uh, ja, a little bit,” Caleb said, shyly, “Actually, it was very nice. You can continue, if you don’t mind. A bit lower, on my stomach?”

“I don’t mind at all,” Molly answered. He began to rub Caleb’s belly and Caleb gasped as the fabric of his tunic moved over his sensitive skin. Caleb wordlessly pulled the hem up, exposing his belly for Molly to caress, skin to skin.

Caleb tried to relax, tried to let the tension out of his muscles, but the longer Molly touched him, the more restless he became. As Molly’s hands traveled lower, Caleb imagined those long fingers dipping between Caleb’s legs and stroking his throbbing clit. Gods, he wanted those fingers inside of him. He wanted to be touched and he felt ashamed. He knew Molly was down for almost anything, but this? Not this. This should not be happening and Caleb should not be craving sex. He was filthy and bloated and he could not ask Molly for help when he was unwilling to even touch himself.

Molly began squeezing the tender muscles of Caleb’s thighs with his strong hands. His fingers rubbed in circles and he dug the heels of his palms into the tissue, finding all the spots that were sore, making Caleb whimper in the back of his throat. He worked his up one leg and down the other until Caleb shivered and squeezed his legs together. Caleb felt wetness on his thighs when they touched, unsure if it was blood or pre-cum or more likely, a combination of both.

Caleb’s face burned as hot as the desire became between his legs. “Touch me,” he finally whispered, soft and desperate, like a prayer.

“Of course, my love,” Molly whispered back.

Caleb was grateful that Molly did not tease or question why. He simply hooked his fingers under Caleb’s waistband and tugged, and Caleb lifted his hips so Molly could undress him. Molly set Caleb’s underwear aside along with the blood-spotted cotton, seated himself between Caleb’s knees and continued massaging Caleb’s thighs until he reached Caleb’s pubic bone.

Caleb bit his lip to keep himself from whimpering. The thought of sex had repulsed him moments ago, but his body screamed for it like it never had before. The desire to be filled with anything was so great that Caleb could not think of a single reason to refuse it.

“Just fingers for now,” Caleb said.

“Whatever you want, Caleb, I’m yours.”

Caleb whined. Molly was too good to him, always. He should not be asking his partner to do something so dirty and shameful as to touch him while he was bleeding, but Molly did it anyway with no inhibitions.

They fell silent when Molly’s finger began to circle Caleb’s entrance. Caleb did not want to think about what exactly was lubricating Molly’s finger so well that it slid inside with no resistance. Molly turned his palm upwards and Caleb gasped sharply when Molly curled his finger into the spongy tissue near the opening. He took his time to explore inside Caleb’s pussy, massaging his inner walls with care. Caleb moaned in appreciation, pleased to find that it alleviated the ache that had settled deep inside.

Caleb stared at the ceiling and did not notice that Molly’s head had ducked between Caleb’s legs until he felt warm breath tickling his thighs. Molly’s lips suddenly wrapped around Caleb’s erect clit and Caleb bucked his hips before his brain could tell him not to. Molly bobbed his head, his lips moving up and down the length of Caleb’s clit and teasing the tip of the hard nub with both prongs of his forked tongue. Molly pulled off it with a soft pop and Caleb almost screamed when Molly licked a stripe up his dripping slit.

“Mmm, you taste good,” Molly growled, his exhale hot against Caleb’s pussy.

Caleb was unsure if he had heard Molly correctly, but he must have; Molly’s tongue parted Caleb’s lips and licked inside. Caleb arched up off the bed and cried out, “Mollymauk, fuck, Molly, what are you doing?”

Molly retracted his tongue and lifted his head, stilling the movement of his finger but not pulling it out. “Is this too much, sweetheart?”

“ Nein, f-fuck, it’s just….keep going,” Caleb managed, “I cannot believe you are actually doing this, Mollymauk.” Yes, Caleb was bleeding freely from his pussy and Molly was clearly enjoying himself. This man is fucking insane, Caleb thought, but was grateful when Molly returned his attention to Caleb’s clit, sucking on it like it was a proper cock and humming while he did so.

It did not take long for the searing heat to rise in Caleb’s belly. When Molly added a second finger and curled them both inside, there was nothing Caleb could do to keep himself from coming. He clenched around Molly’s fingers and squeezed Molly’s head between his spasming thighs, gasping and sobbing and until his orgasm subsided.

“Don’t stop,” Caleb wheezed, his voice shaking, “Gods, keep fucking me.”

“Anything for you, love,” Molly said. He remove his fingers and just as quickly pressed his mouth flush against Caleb’s mound. Caleb felt that sinful tongue plunge deep inside him while Molly buried his nose in Caleb’s pubic hair.

“Molly!” Caleb cried, his hand flying down to fist itself in Molly’s hair. Caleb held Molly’s head in place while Molly thrusted his long tongue in and out like he had done with his fingers. It was hot and slick and Caleb could not tell what was saliva or blood or cum but it did not matter, Caleb’s body felt electric. His second orgasm came so quickly it caught Caleb off guard. He yelped in surprise and clamped down on Molly’s tongue that continued to fuck Caleb through his release.

“Keep doing that and I will come again,” warmed Caleb.

“You say that like it’s a threat,” Molly chuckled, “You are so beautiful when you come. I would never stop you.” His tail thrashed against the bed in excitement. He replaced his tongue with his fingers and fucked Caleb earnestly, staring at him through lust-clouded eyes.

Caleb wailed as each jab of Molly’s fingers against Caleb’s g-spot caused a jet of cum to squirt into Molly’s palm. Molly was grinning wildly, obviously pleased with himself. Caleb slung his free arm over his face and sobbed quietly into his sleeve.

“You’re so sensitive, Caleb,” purred Molly, “It’s never been easier to make you come. I didn’t even have to ask for it.” Molly kissed Caleb’s clit and flicked his tongue against it. “You’re my good boy, Caleb. You’re wonderful, sweetheart. Don’t ever let yourself think otherwise.”

Caleb gasped for breath as he came again, unable to tell where one orgasm ended and the next began. His hips quaked and his thighs convulsed. Even though it felt like his entire body would shake apart at any moment, Caleb knew that Molly, his sweet, gentle Mollymauk, would take care of him.

“One more time,” Molly said, slowing his hand and rubbing Caleb’s clit with his thumb. “Please, please, I know how much you love to make me beg.” Molly bit down on the inside of Caleb’s thigh, sucking the skin through his teeth, hard enough to bruise but not enough to bleed.

Caleb squeezed his eyes shut so hard that he saw bursts of pink and green behind his eyelids. He arched his back, lifted his ass off the bed and froze in that position as Molly drew one last orgasm out of him. When Caleb collapsed on the bed, he felt nothing but pleasant numbness from his core to his fingers and toes. The pain, along with his thoughts, disappeared in the height of euphoria. When he opened his eyes Molly was lying next to him with a big smile on his face.

Caleb could smell blood on Molly’s breath.

“I will punch you if you try and kiss me,” Caleb cautioned.

Molly smirked. “I wasn’t going to, but thank you for the warning.”

“Sorry, I just….gods, Molly, I cannot believe you did that.”

“You should know by now that I am full of surprises, dear. How are you feeling?” Molly propped his head up on one hand, gazing down at Caleb while Caleb caught his breath.

“Ah, much better, thank you,” Caleb answered, stretching his legs to make sure they still worked. The worst of the cramping was gone, although he still felt bloated and sore.

“It was my pleasure,” Molly said, pulling Caleb’s tunic down to cover his thighs.

Caleb sighed and let his eyes fall closed. He felt exhausted after the full-body workout Molly had put him through. The bed shifted and Molly disappeared, returning moments later with a warm, wet cloth. Seating himself on the edge of the bed, Molly thoroughly cleaned between Caleb’s legs, wiping down his thighs and pressing a single kiss to Caleb’s pubic bone when he was done.

“Sweetheart, would you like your pants back on?”

“The sheets are ruined, aren’t they?”

“Ah….whoops,” Molly said, glancing at the dark stain on white sheets, “That one’s on me, though.”

“Then no, fuck it,” Caleb murmured, “Come cuddle me, you vampire.”

Molly barked a laugh. He tossed the rag away and stretched out along Caleb’s side, stroking his hair as they quickly dozed off.

Tomorrow, they would skip town and never return. But for now, Caleb slept peacefully in his partner’s arms, amazed by the distance Molly would go to assure Caleb that he was loved.

## Afterword

End Notes

> This is all your fault, you know who you are. <3

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