Lovely Misadventures

My date with Cheerilee went swimmingly! She's so nice, and we talked for hours about engineering and popular mechanics. She's a real science wiz. She is a school teacher after all. She and I also know a lot about environmental science and marine biology, which we also could talk about for hours on end. Conversation flows so naturally between the two of us. Both of us are well aware of and don't give two shits about our six year age difference.

Though very minor and barely significant, there are a few cons to this one. She doesn't like it when I swear and I admit, I do it way too much. I also can't smoke around her and I'm going to find it safe to assume that she would be turned off if she knew how much I drink. She's the kind of girl I can wine and dine though, I know that much as she and I have made plans to see each other again over dinner at Snobby's Bistro. I like classy, upscale places like that and I think it'd be a good environment for the two of us to connect.

The day after the next was our next date at seven o'clock at the nice five star establishment. Sure, a bit overkill for a second date but I managed to talk her into it, which took almost no effort. I mean, we had such a great time the other day and you only live once. Well, right now, I'm putting on my favorite cravat and my best black collar in front of my bathroom mirror while I listen to to words of encouragement from my Princess friend.

"You know, Caddy, Shining and I have an open relationship if that means anything to you." Cadence said as I was only partially listening.

"Uh huh...Wait, what?"

"I said you look very handsome."

"Aww, thanks, Cadance."

"You bet. Now get on over to her place and you trot with her to that restaurant!"

I did just that. The night with Applejack was still lingering along with me as was the confidence brought on by our intimate encounter. Applejack may not have been the first mare I had sex with but she was the first one I had managed to get off. If I can make a mare cum, I can do it again. However, Cheerilee doesn't seem like the type to screw after the first or even second date. I've got a condom just in case but I don't expect to be getting intimate tonight.

She looked absolutely stunning in that dress that matched her eyes and I made it a point to let her know that. Even the trot to the restaurant was wonderful, we never paused our conversation or needed to take a moment to come up with something to say. No awkward silence, conversation just flowed perfectly. She mentioned that she'd love to get to know my nieces once they're old enough to start going to school. One of them just turned five and the other is three, so they will be starting school before too long.

We spent two hours at the bistro and only left because the place was closing for the night. I had to talk her into letting me pay the bill, as she wanted to go half on it. Call me an asshole or whatever but I guess I'm just a bit too traditional. Not sorry. I also held doors open for her and stuff. I know, how dare I, right? We ended up trotting around town and purposely took the long way back to her place. Neither of us wanted to but we had to bid each other goodnight but before we parted ways, I figured I'd try something new.

As we stood on her doorstep, I slowly inched my face towards hers and she responded by doing the same. We both then closed our eyes and pressed our lips together. It was unlike the kisses I shared with Applejack, this one was much more gentle and less sloppy. I had so little experience with kissing but I seemed to pull it off just fine. After planting a few more on each other, we gently broke off and stood there smiling at each other until she finally broke the semi awkward silence.

"Goodnight, Caddy." Cheerilee said, her green eyes looking into mine.

"Goodnight, Cheerilee." I said with a smile as I spread my wings and took to the air...nearly a week sooner than the doctor said I should even attempt.

As I struggled to fly myself back home, my wings burned like a motherfucker but I didn't care. Something else started burning and it wasn't my store. There was a fire in my chest and I fucking loved it. Cheerilee and I made plans to have a picnic in a nearby meadow in a couple days and both of us could hardly wait. Now, I could go home to cadence and tell her the good news. Though my body and wings are still a bit sore, I was feeling pretty damn good for the first time in years.

"I knew you two would hit it off, Caddy!" Cadence beamed as she and I both prepared to retire for the night. "I can see you two really flourishing as a couple!"

"I really like her Cadance!" I beamed. "I really owe it to you for setting us up!"

"Heheh, I am the Princess of Love after all!"

Cadence has been sleeping on my sofa for the past week now and I just didn't have the heart to make her sleep there any longer. Problem is, I can't sleep on it and give her my bed as my back and my wings are still sore so she convinced me that there was nothing wrong with the two of us sharing the bed. It's not like we're gonna do anything we shouldn't, we're just a couple of close friends sleeping together. I trust her when she says Shining Armor has no problem with it, she wouldn't lie to me. I really need to quit taking the few friends I have for granted.

The day Cheerilee and I planned our next date arrived and she and I, as well as Cadance were really looking forward to it. I packed up a cooler with our lunch which included potato salad, cucumber sandwiches, a vase full of daisies, some sodas and a bottle of wine that I've been saving for a quite some time. I met her at her house and we proceeded to have ourselves a nice trot over to where she and I planned to set up our picnic, which much to our relief, we found to be completely void of any other couple with the same idea. We had the whole meadow all to ourselves.

That meant we could do whatever we wanted with nopony trotting by and telling suggesting that we get a room. No, we didn't have sex on our picnic blanket, but we did make out and cuddle like crazy. I haven't felt this good in years. All my life, I'd been pushing others away and shying away from physical contact and now I know what I've been missing. I've never felt like such a fool before. Why have I been depriving myself of such wonderful things all these years?

Cheerilee and I started our date at two o'clock on this Sunday afternoon and completely lost track of time until the sun began to set at quarter to eight. We just couldn't get enough of each other, and just as we packed up our things and made our way back to her place, she let me know just how much more of me she would be hoping to get later on tonight.

"Caddy? Can you do me a huge favor?" Cheerilee asked, nearly sounding like she was about to beg.

"Anything for you, m'lady." I cooed.

"Will you meet me at my school in one hour? Please? There's something I've always wanted to try and you're the guy I want to try it with."

"Of course."

It's all in her tone and clear as day in her eyes. She wants me to rut her but why would she want to do it at her school?
Is that legal? Aw, who the hell am I kidding, I committed arson and got away with it, I think we'll be fine. Ooh, maybe she wants to try some kinda role play! Of course! She's the sexy teacher and I'll be the rowdy young stud stuck with her in detention! I love that idea! Ohhohoho, I'm gonna be bringing my swag in full swing tonight! Yes!

As far as I was concerned, our date wasn't over, not by a long shot. All we had to do was go home, get cleaned up, maybe put on some of my more, what Cadance calls, my more "sexy" cologne. Don't judge us, we're best friends, we can call each other that if we want!

Again, after some more encouragement, Cadance sent me on my way with a packet of rubbers, this time not magically charged. I should be able to pull this off without the extra help. They're ribbed anyway, she'll fucking love it. I made my way back to the school where the beautiful teacher would be waiting for me and hot damn am I anxious. I mean, I really don't have any idea what she had in mind. For all I know, she could have invited me to help clap the blackboard erasers.

Nahh! That's silly! What the hell kinda crack have I been smoking? No sense in making myself anxious about this, there's only one way to find out. Finally, I made it to the school to find a note taped to the door. It read "Caddy, it's unlocked, just come in." Oh, I'll come in something all right! I reached for the handle, pushed the door open and stepped inside. Everything was dark.

After a moment of stumbling around, my eyes adjusted to the darkness and I could make my way around just fine. Weird, where the hell's she at? Here I am just trotting back and forth through the hallway, looking around for my sweetheart. She's not in any of the bathrooms, the maintenance closet...how about I quit being a dumb ass and check the classroom then?

I trotted into the classroom which was as dark as the rest of the little school house. I went up to Cheerilee's desk and figured I'd take a seat while I waited for her wherever she was. To sit there and look at all those little desks facing towards me got me imagining what it would actually be like teaching foals. Sure, I like foals but I don't have the patience to be a teacher. Just when I started to think I'd be waiting for a while, all of a sudden, the light flipped on which immediately drew my attention to the doorway. Who I saw standing there was a real sight for sore eyes.

"Oh, Mister Finz." Cheerilee, sporting an incredibly sexy cheerleader outfit with a very short skirt whined, a cute little pout on her face. "The rest of the cheerleaders said that you were going to kick me off the squad."

Ooohohohohhh fuck yeah.

"Is it because my grades are bad?" She continued as she slowly trotted towards me with her tail high in the air. "There's got to be something I can do to stay on the team." She began to bat her eyelashes. "Whatever I can do to make some extra credit, please, just name it and I'll do it. Anything."

"Anything, you say?" I asked as I licked my lips, playing along with her little game.

"Oh yes, anything, sir."

If my dick was already getting hard, it was just about ready to explode when trotted past me and brushed her tail under my chin. Ohhh yeah, this bad girl's asking for it. This is going to be the most fun I've had in years.

"Well, little missy, your grades are pretty bad this month." I said with the most devious of smirks on my face. "You'll have to make up a lot of extra credit if you want to stay on the cheerleader squad."

"I'll do anything, Mister Finz!" Cheerilee whined as she trotted up to me in my seated position and sat herself down on my lap. "You've always been my favorite teacher, Mister Finz. I just know you'll help me with thi-mmmff!"

As the sexy little cheerleader sat on my lap, I pressed my lips against hers and buried my tongue in her throat. As both our tongues danced around one another, my stallionhood was now standing at full mast, she could poll dance on it in the position she was sitting in. The moans and squeaks coming from her as she wrapped her forelegs around me were adorasexy, if that's a word. Screw it, I'll make it a real word, I'm the teacher.

"Mmm-aah! M-Mister Finz! I've always had such a huge crush on you!"

"Oh, I know, Cheery." I cooed as I held her close. "I could read you like a book, you know." I quickly slipped my rubber on and I then placed my forehooves under her sweet ass and lifted her up over my desperate, twitching cock. "Now let's start making up that extra credit now, shall we?"

She was already wet so I had no trouble letting her down on my dick. The blush on her face is just about the cutest thing I've ever laid eyes on. That squeak she let out as she sunk down on me made me throb even more, in turn earning another squeak. It was the best viscous cycle I've ever found myself in and I don't think I'll ever want to get out.

"Mmm, this oughtta bring up your gpa, little missy."

"Ooohh yesss...Ohh Mister Finz, yes, rut meee." She moaned as l repeatedly lifted her up and let her down. "Y-yes! You're my favorite teacher, Mister Finz!"

Did I mention that I really like this girl?