Lovely Misadventures

"That was the best fucking lay I've ever had." I said to Cadance as she pushed me out of the front entrance of the hospital in a wheelchair.

"I just find it funny that Applejack can now honestly say that she literally put a guy in a wheelchair." Cadance chuckled.

The doctor told me that I should be able to start trotting again in two days and flying within about a week. Even though she fucked me up pretty good, Applejack and I are cool. Better than we were before in fact. I definitely wanna fuck her again sometime but I think it's gonna be a while before I'm up for it again. Aside from my injuries, I'm feeling like a million bits simply because I got laid.

Am I taking time off work? Of course not! I mean, I'm taking the rest of the day off to get some rest because Cadance is going to physically make me and I can't fight her in this state. Come to think of it, she could kick my ass in her sleep. Nice to have her around to help me though. I don't deserve friends like her and Shining Armor.

"Caddy, now that we're back home, I wanted to talk to you about something." Cadance said as she pushed me through my front door.

"What's that?" I asked.

"I found another single mare that I think you could really hit it off with."

"Already? Don't you think I should take a break for a while after this?"

"You need more friends, Caddy. Besides, what you had with Applejack was casual sex. I'm talking about going on an actual date and getting to know somepony. Making a meaningful connection. Now that you've gotten some of your pent up, pissed off crap out of your system, you could stand to spend time with ponies and develop friendships. Maybe even more."

She just wasn't going to get off of this and as much as I don't like to admit it, she's right. Sure, I do feel better now that I got my dick wet, but I'm still no less an asshole than I was before. What do I have to lose? Who knows? Maybe I can bang this one too. Maybe I'll fall in love and it'll change my life. Not holding anything to that last one, but we'll see.

"Alright, Cadence." I sighed in defeat. "What's this girl like?"

"She's a cute one, Caddy, I think you'll like her."

"I like cute."

"She's smart, kind of a nerd."

"Twilight?"

"Heheheh, no Caddy, it isn't Twilight. This girl is thirty-three."

"A little older than me? Okay, nothing wrong with that. What else? What does she do?"

"She works with foals."

"Ah, somepony my nieces would get along with."

"Huh, I didn't think you liked kids for some reason."

I couldn't help but feel a bit insulted by that. Of course I like kids, my nieces are a very big, important part of my life and I'm proud to be heavily involved in raising them. Not to mention, I'm great with Flurry Heart whenever she's around. I get it, I'm a prick but I don't dislike foals. That's why I don't have any myself, I'd be a horrible father. Any youngsters that aren't mine should be considered lucky. It's not that I'd mistreat or resent my foals if I had any, I just know I'm not fit to nor do I have the time to raise any.

"Well, I can tell you that you were mistaken to think that." I said as a matter of factually as Cadance and I relaxed on the sofa with a beer. "I'm great with kids. You know Flurry Heart even calls me 'Uncle Caddy'. I can't believe you'd think that about me."

"You're right, my bad."

"M'kay. So, about this lady friend of ours..."

Three Days Later...

Turns out, I've met this girl before and I completely agree with Cadance, she's definitely a cute one. Cadence worked as the middle mare between us and set us up on a date in the park at four o'clock this afternoon. Just a casual meetup, I didn't have to wear my favorite cravat or anything fancy like that. All I had to do was work an opening shift at my store until half past three and trot on over to the park to see her. It worked out well for her too as she had just finished up at her own job for the day too. From having met her before, I know this young lady is really nice and could probably teach me a thing or two about not being a dick to others.

I was looking forward to this one. Only problem was that Cadance told me that this mare really doesn't like the smell of smoke so I made sure to go a few hours without a cigarette and chew a bunch of gum in between them. I made sure to only smoke outside too so I wouldn't stink like an ashtray. Well, I'm getting close to where we were supposed to meet up now and since I'm stone cold sober, I am a little bit nervous.

I find older mares a bit intimidating at times ever since I got into the retail biz since they're the worst complainers I've ever seen. I mean, this one's only six years older than me, it's not like I'm meeting up with some cougar who is completely indifferent to and never impressed by anything. Hell, even Rarity the owner of the local clothing boutique acts more like that and she's younger than I am. Anyway, this lady I'm about to go see is really sweet and bubbly so I think we'll hit it off just fine.

Oh, I see her now. She's over by the park's koi pond tossing food pellets in for the fish. I'll just slide up next to her and say hello. She's a maroon colored earth pony mare with a mane and tail of a couple different light shades of pink. She had a cutie mark of three cute little daisies with little faces on them. As I trotted closer with confidence in my posture and my stride, she turned turned her head around and looked over at me and her pretty green eyes met mine. What a pretty smile she has. All around good looking girl and I bet her personality is just as nice.

"Hi, Cheerilee!" I beamed as I trotted up and alongside my date.

"Hello there, Caddy!" She greeted with a diabetes inducing smile before hugging me all of a sudden.

Was I expecting a hug? No. Do I have a problem with it? Also no. That was actually kind of nice. It was like when Applejack pulled me in closer to her except a little less boner inducing. If things go well between us however, I certainly wouldn't mind getting intimate with this cutie.

"How are things going at the school?" I asked my date as she and I proceeded to trot down the path at the park.

"Oh, wonderful!" She replied. "I really enjoy what I do, I can't think of any other career I'd rather have!"

She's so bubbly and upbeat and the feeling is rubbing off on me! I like this girl and I'm really digging her vibes. We have a lot in common and I there's just something about smart girls that make me really want to be around them. When I was younger, the two sluts I got with were dumber than a box of rocks. I look back and feel glad that I never went anywhere with them, I can't stand stupid ponies. This one though; I've got a good feeling about her.