Orpheus Lulamoon: Diary of A Womanizer

It had been a few weeks since I started working as a teacher for Canterlot High. I enjoyed giving lectures and helping my students learn but as shameful as it is for me to admit, a part of me enjoyed the affairs I had with my students and co-workers more. Today after giving two classes in a row I had lunch with a cute male student named, Braeburn. After we enjoyed lunch I helped myself to 'desert'. A nice, tight bottom for me to worship and fuck to my heart's content and hid perfect lips upon my own after he gave me a wonderful blow job. It was during the blow job when Braeburn's cousin Big Mac entered. Braeburn stayed hidden under my desk as he swirled his tongue around my cock, "What can I do for you Macintosh?" I asked softly as I ran my fingers through Braeburn's beautiful blonde hair.

Big Mac was a tall good looking boy with short orange hair and beautiful green eyes. If I wasn't already being pleased by his cousin I would've taken the tall southern boy right then and there but good things come to those who wait, "Forgive me for intruding Mr. Lulamoon," Big Macsaid politely. It made my heart melt to see such a polite boy, "I have a favor to ask you."

"A favor?" I asked as Braeburn who had gotten jealous from me not paying him attention teasingly and gently bit my shaft. I kept the groan in as I forced the other boy to keep going before playing with his hair again. The other boy seemed pleased with my actions because he soon went back to being a good boy. Big Mac nodded before explaining that his sister and himself would be home alone at Sweet Apple Acres the next day to harvest the apples and they needed an extra pair of hands. Since the next day would be a Saturday they figured I wouldn't mind. They were both right, "I'll be there." I said softly. Big Mac seemed pleased and thanked me before taking his leave.

I pulled away from Braeburn and pulled him up by his hair earning a pleasurable moan from him, "You ever bite me again and daddy won't be pleased." I said licking his lips before deeply kissing him. His lips tasted of a mixture of myself and apples.

"I'm sorry daddy..." he moaned out as I began to bite at his neck earning more moans from the submissive boy. I soon got up and forced him to turn around before spanking him slightly. This caused him to moan again, his was already red from the ruler I used upon him. He was quite the masochist.

"Mmmm good boy," I said as I began sliding into his tight, little asshole for the second time. It seemed to get only tighter with my seed still inside it, "will you be helping your cousins tomorrow as well?" I asked as I took his hands within one of my own and kept them pin on his bare back as I fucked him more. He moaned like a little bitch as he answered my question with a nod.

"Mm, ah yes daddy!" He cried out as I spanked him for not answering me with his words. I love a boy who knows his place. Once we finished he had gotten dressed and took his leave but not before making out with me for a bit.

"I'll see you tomorrow cutie," I said to the boy before giving him another quick kiss. He nodded before moving out of the room. The day went by without any issues. I had a make out session with Fluttershy after school and made dinner plans with her on Sunday before checking in with Cheerilee who wanted me to come over to her place that evening. I accepted and told my sister's to have fun for the weekend with their friends while I spent the evening with my old flame.

The next day, I had gotten up bright and early showered and ate a quick breakfast with Cheerilee before heading off to Sweet Apple Acres, but not before giving Cheerilee a quick kiss.

I had soon arrived at Sweet Apple Acres where I was greeted by Big Mac and his sister Applejack, "Howdy Mr. Lulamoon." Applejack said shaking my hand. I smiled softly at her before wondering where I would be working. Big Mac lead me over to the south orchard and explained that I would be working with him.

"Ready to begin?" I asked the younger male. He responded with a simple 'yep' and before we knew it we were hard at work on collecting as many apples as possible. Big Mac and I worked for hours collecting apples sharing as few words as possible, I had never noticed how quiet he was until that day. The warm sun beat down on us as we worked quickly. I even had to remove my shirt just to keep cool. Occasionally I caught Big Mac checking out my muscles, I guess he was more alike with Braeburn after all.

"Lets take a break Mr. Lulamoon." Bug Mac said after awhile, I checked my watch noticing that we had been working for four whole hours, since it was now noon. I nodded and got down from my ladder noticing that Big Mac had set up a picnic. I couldn't help but smile at the fact that we were alone on his family's farm having a picnic and we were both shirtless. He knew what he was doing.

I sat down beside his and was surprised to see thst he wanted and feed me fruit. I've never had men offer to feed me fruit before, nor women come to think of it but I smiled all the same and took a bite of the apple slice he offered me, "Thanks." I said smiling to the younger male. He blushed slightly but smiled in return. I leaned over and while cupping his cheek lovingly gave him a soft kiss. He blushed more but returned the kiss as he wrapped his arms around me. I smiled into the kiss before looking around to see if we were alone, "Turn around." I said softly, I figured we had time for a quickie. Big Mac obeyed and turned around after undoing his belt with a knowing smirk on his face.

I smiled and undid his pants before pulling them and his boxers down to his knees before pulling mine down as well and sliding gently into him, "Oooh you're so big." He moaned out. I smiled at his moans before I began gently thrusting into him. He was actually fairly tight but not as tight as Braeburn. Once I let him get use to my thrusts began going harder and deeper. This made his moans become slightly louder, I soon picked up the pace of my thrusts as I squeezed his butt cheeks in my hands after giving them both a firm spank. This caused him to actually squeal before climaxing.

"You certainly didn't last long." I said softly as I stroked his hair. He tried apologizing but I missed him to silence him before thrusting some more, until I pulled out and moved over to Big Mac's face and ran my cock across his lips. He knew what I wanted instantly as he happily took my cock in his mouth with no protest. I smiled down at him as I played with his soft hair.

He looked up at me with innocent looking eyes as he sucked upon my cock, "You're so cute." I said teasingly as I spanked him again. He moaned more and began to bob his head up and down faster taking in all of my shaft. His mouth was magical, soon I too climaxed and I was proud to see him swallow everything before I kissed him again. We laid together for a bit afterwards before getting back to work, once we put our pants back on of course.

By dinner time we had finished with everything and I was about ready to leave when Applejack came to stop me, "Excuse me sir, but would you like to stay with us?" She asked. I was admittedly a tad confused by her offer but I was fine with it. Applejack blushed at me telling her my answer before heading back in and making sure that I noticed she wasn't wearing panties. She knew exactly what she was doing.