Merry May's Time With a Human
I ached as I finished my long shift of weather work. I’ve been pushing clouds all day and I haven’t even taken any break for the past twelve hours. Normally we aren’t supposed to do that but well, I need the bits so.
“Hey Merry!” I jumped off the cloud I was about to doze off on and peered over the edge. Ponyvilles resident human James, my best friend and my crush was waving at me and I yawned.
He was a tall slim man with brown hair, sea green eyes and was wearing a black hoodie, grey shirt, black jeans and boots that I secretly adored.
“Hey!” I called back as I pushed my cloud to the ground. “How’s it going?”
“Good. Wanna go get drinks?”
“I would but I’m exhausted. My wings and back hurts like crazy James,” I sighed as James rubbed his chin.
“Well, why don’t you come to my place?” James suggested as I instantly blushed. “I have more than enough room and can help you.”
“How so?” I asked curiously and tried to calm my blush down.
“Rub your wings and back like this,” James said as he reached out with a hand and rubbed the base of my wing as I tensed up and felt a shock of pleasure course through my body as he rubbed the base.
It felt so good and I felt the aching go away as I let out a low moan and closed my eyes slightly.
“You okay there?” James asked with a hint of concern in his voice and I opened my eyes. “You fell asleep for a few moments there. Wanna get going?”
“Mhh yeah,” I said as he lifted me up and I blushed again.
“W-what are you doing?” I asked and whispered. “There’s ponies watching!”
“Carrying you. Don’t lie, you enjoy it,” James snickered and brushed my ear as I sighed contently as he wrapped an arm around me.
“I do yeah,” I admitted sheepishly as I pushed down my feelings. There’s absolutely no way he would ever love me back. He’s a human stuck here forever and I’m a pony. As much as I want it to, it would never work out. “Let’s just hurry please I’m embarrassed.”
James offered no response, just chuckled as I nuzzled his neck. He must have came from sugarcube corner because he smelled like cherries.
In no time at all, we arrived at a large green house with a white roof that Applejack, Rainbow, Big Mac, Blossomforth and a few other pegasi I work with helped him build. Raindrops and Cloudkicker were both more than happy to help him.
He unlocked the door with one hand and me held in the another as he opened in and we walked inside. I’ve been inside here countless times and he always added more random decorations.
“Where’s that at?” I asked and pointed at a light house on a lake as James shut the door, smiling sadly.
“Lake Michigan. I was born on the coast of it. It was like my second home,” he stared at the painting sadly. Twilight had worked on getting his memories from home recreated in his house.
“It looks beautiful,” I mused as he nodded. “Maybe one day we can find a way to go there together if Princess Twilight can figure it out.”
“I’d like that a lot,” James sighed and shook his head before setting me down on a comically large couch. “Lay down how ever you want.”
I gave a nervous nod as I stretched my forelegs out followed by my hind legs as James rested his hands on my back and started to work my muscles.
“You’re very tense. Been flying a lot today?” James asked above my head as I nodded and moaned in pleasure as his hands worked the base of my wings and my wings stood up straight as I turned red.
His hands felt surprisingly well as he expertly worked my back and wings as I bit my lip.
“How did you get so good at this?” I moaned again as James smiled slightly.
“I don’t know. Does it feel good?” James asked and I snickered slightly.
“Beyond good,” I said as I felt much more relaxed and my back aching was gone. “Thanks, I feel much better. I lo- I appreciate you a lot.”
“Likewise,” James said as he picked me up and placed me on his lap, covering us up with a blanket so only my face was poking out. “Hi.”
“Hi.”
“You look adorable right now, I like your pink mane.”
“It’s plum colored,” I corrected instantly as James chuckled and scratched behind my ear. “Oh that’s the spot.”
“Glad to see you’re still part cat Merry,” James chuckled as he cuddled me. “What do you wanna do?”
“Make out?” I suggested with a playful grin. I didn’t think he even took me seriously until he pressed his lips to mine and my eyes shot open wide. “Mhmmmm.”
“Like that?” James asked with a warm smile as I turned red yet again and I hesitantly kissed him again. I didn’t really have any experience with kissing or any thing like relationships.
I felt his tongue press at my mouth and I hesitantly opened my mouth, feeling his tongue press against mine. His tongue was much less rough than mine and our tongues swirled together.
“I’m not entirely experienced at kissing,” James admitted after we separated with a thin strand of saliva connecting our mouths.
“Do you like me?” I whispered as my eyes flicked up to his.
“Of course. I don’t really know you felt but well, you were one of my first friends other than Twilight. You really defended me against some ponies who didn’t really like me or trust me. Namely Lily and Spoiled Rich,” James scoffed as I growled quietly. I had almost fought them both over him once.
“Yeah well now you know,” I rested a hoof on his couch nervously as he kissed my forehead.
“Wanna go again?” I asked sheepishly as he kissed me again and I felt his hand trail down my wing to my cutie mark and I sighed contently before jumping as he squeezed my flank. “Woah!”
“Did I fu-” James started nervously before I kissed him harder and lidded my eyes as he squeezed my flank again. He threw the blanket off us and he stood up as he started walking up his stairs and I inhaled nervously before kissing him again.
“Where we going?” I asked nervously as James kissed my neck gently.
“My room unless you don’t want to,” James answered as we stopped on the steps and I pushed down my fear.
“I want to,” I said nervously. “But uhm I’ve never had sex or anything so be gentle please.”
“I will,” James promised as he planted a soft kiss on my lips and I hummed happily as we walked into his room and Idyarwd around his large room as I laid on his large bed. Or well, large to me a small pony.
“Your bed is comfy,” I said as I purred and rolled around playfully on the soft sheets before stopping on my back.
“Thanks,” James smiled warmly at me as he climbed on top of the bed and I instinctively clenched my legs together and covered myself with a tail. “Merry May?”
“Y-yes?” I asked nervously as I stared into his bright green eyes.
“You’re a beautiful mare. You don’t have to be embarrassed around me and we don’t have to do this if you don’t want to,” James promised as he scratched my ear and I relaxed more as I moved my tail and slowly spread my legs as we both stared at my pussy as we both blushed.
“I trust you,” I said honestly as I felt a hand trace my lower lips and I inhaled sharply. “Oooh that feels weird but like a good kind. I’ve never had a hoof or well hands down there- OH!”
James rubbed me with a finger as I felt myself get wetter and I gasped a few times as pleasure jolted through me.
“Is that good?” James whispered in ear before nibbling my neck as I nodded rapidly as I grabbed onto his shoulder with a hoof and felt his finger push inside me and I yelped in surprise.
“Oh fuck,” I whispered and shuddered slightly as James continued slowly working his finger inside me. “It’s good. Really good Jamesy.”
“Obviously not if you’re still talking,” James commented mischievously as I felt him push a second finger inside me and I gave a grunt as I sighed happily. I had originally thought this would be way more painful than it actually was. Sure, there was some minor discomfort but not any real pain.
I felt my first orgasm of the night coming as I gasped loudly, arched my back and cried out loudly, splashing his fingers with my sticky mare cum.
“That was amazing,” I panted out and gave a tired smile at James as I stroked his side lovingly with a wing.
“I’m glad I could be entertaining,” James chuckled as I examined his boots.
“How do I get this damn boots off?” I asked as I fumbled with his boots and he pressed a hand on my side before untying them, tossing them lazily to a corner. “Oh and uhm what about those?”
I blushed and gestured at his pants as James turned red too before unbuttoning them and I couldn’t tear my eyes as he pulled his jeans off, pushing them on the floor and his underwear as he called it came next.
Humans wore too much clothing in my opinion I mused as I turned even redder and stared at his dick. I didn’t know anything about human dicks and I only know about stallion ones from health class but his was decent size to me at least.
“You’re gorgeous you know that?” James asked as I nuzzled his cheek and he returned the gesture as I pushed him on his back. “What are you- woah.”
I tentatively flicked my tongue against his tip as James shuddered and I experimentally gave the shaft a lick up the side of it before stopping at the tip and going down the other side.
“W-wow,” James moaned repeatedly as I continued licking excitedly. I felt a haze of lust start to cloud my mind as I continued my eager licking before I took a risk and stopped at the tip, opening my mouth wider and slowly pushing my mouth down on his dick. “Merry, don’t hurt yourself-”
I continued trying to push my muzzle the rest of the way down his dick as tears welled up in the corners of my eyes. I gagged as I reached halfway before I was forced to pull my muzzle off his dick smd hid my face into his shirt.
“I’m sorry,” I muttered miserably and wiped my tears away. “I tried to make you feel good but failed.”
“You did good,” James reassured me and stroked my cheek. “I was more worried about you hurting yourself. I felt good don’t worry. Lay back and relax Merry.”
I gave a confused nod as I reluctantly got off his chest and laid on my back as I watched James climb between when my legs as my eyes widened and I realized what was about to happen.
“Be careful,” I whispered nervously as he nodded. “I’m scared.”
“I will,” James promised as I maintained eye contact with him. His green eyes were full of lust but more prevalent was a shocking amount of love as he kissed my forehead.
I let out a whimper as his tip brushed my lower lips and I grasped the edge of his bed.
Moments seemed to pass by and I internally knew words couldn’t recall either of us back at this point.
He pushed and I screamed as I felt him slowly sink inside me. It was painful, more painful than I expected and I continued to scream as he slowly sank deeper.
“Fuck!” I screamed in pain as James stopped and I hugged him. “Oh fuck my life. Let’s just sit here please while I get used to it.”
James started peppering my face with kisses as we sat in with him inside me as he wiped some tears off my face.
“I’m so scared,” I whimpered as James continued kissing my face.
“I know. It’s gonna be fine. You’re so beautiful and perfect,” James whispered back as I turned red at the compliments. I’m a sucker for compliments, especially from him.
“I’m ready,” I said confidently and James gave me a slow nod. I waited as he started pushing once again and I gave a loud cry. “Oh fuck!”
The pain slowly but surely disappeared and I soon focused on the pleasure coming from James slowly thrusting in and out of me. It was very pleasurable and I started gasping repeatedly as I pulled James close to me with a hoof and started making out with him.
James grunted into my kiss as I whined happily as wet slapping sounds echoed through his room as I thrust my hips back in time with his thrusts.
“Harder,” I whispered once we separated as James gave me a wary nod and I felt him pull back till only his tip was in me and I shrieked once he slammed even harder than before into me. “AAAAHHHH!”
I felt even more pleasure than before as James continued slamming away at me as I kept my loud screams and happily cries up, whinnying a few times as I faintly made out the neighbors turn on their lights.
“Inside or out?” James grunted as my tongue lolled out of my mouth and I started drooling on our pillow.
“I-inside!” I gasped out as i felt my walls get even tighter as I started cumming. “Oh yesssss.”
James growled as he held onto my shoulders and I felt a warm liquid squirt inside me and I sighed happily at the warm cum in me.
“I- holy fuck that was good,” James panted as he pulled out and collapsed next to me as a thin trail of cum leaked out of me. I was happy there was no blood like I heard happened to some mares. “I couldn’t have pulled out even if I wanted to, you’re super tight.”
I turned red as I curled up in a ball on his chest and James draped a blanket over us.
“I love you,” I whispered nervously as he gave me a loving look.
“I love you too,” James whispered as he hugged me and stroked my ears. “You’re the best partner I could have ever asked for.”
I sighed happily as I relaxed on my man’s chest and we fell asleep together in bed.
It felt nice to be loved in all honesty and especially by the one I’ve been chasing forever.
Author's Note
Be sure to tell me if you want me to do more collabs with TheKing2001!
