Lovely Misadventures

"I thought you were the Princess of Love, not cheap one night stands!" I barked as the mare herself fixed my collar before spritzing me with my favorite cologne.

"What's that supposed to mean?" She asked, slightly offended that I would dare imply that she was simply about to get me laid. "Hold still, I need to get this straight."

"Did you not see the look in her eye? Didn't you hear her say how she was gonna 'fucking pound the ever loving shit' out of me? I think it's pretty obvious that I'm not going over there to wine and dine with her."

"Okay, point taken, but given how high strung and pissed off you are, you could stand to have sex with a trusted friend.
Hey, don't button it up all the way, you'll look like a tight wad!"

"For the last fucking time, she's a business client of mine!"

"Well she's about to be a lot more than that soon. Now come on, we're gonna be late and I'm sure you don't wanna disappoint her."

After the incident at Sweet Apple Acres, Applejack talked me into meeting her back there after the workday was over. She and I agreed on seven o'clock so we could catch our breaths and get a chance to shower and clean ourselves up. I managed to get everything on my list done and out of the way with a little bit of help from Cadence, and within a few minutes from now, I'd be having sex for the first time in a very long time.

I've always ended up screwed over afterwards, which is why I gave up on it so long ago. I threw my virginity in the garbage when I was eighteen to some slut I met who kept promising me that we would become an item. After we fucked, I never heard from her again. Five years later, when I was twenty three, I started hanging out with this girl about my age. Single mom, wasn't really worried about that. Husband was in jail at the time. That didn't stop me either, the dude even thanked me for keeping her company when he got out. She kept telling me that she was leaving him but no such luck. I quit hearing from her pretty quick.

So that's me. Caddy Finz, the guy who was nothing more than a throbbing rod to a couple of sluts who wanted nothing to do with me afterwards. Fast forward to today, here I am flying back to Sweet Apple Acres with Cadence by my side to make sure I don't turn tail and run back home. I'm not gonna lie, I was nervous and, perhaps a little excited at the same time. Nervoucited, is what that insufferable Pinkie Pie calls it.

The closer we got to the orchard, the more nervous and anxious I became. Every possible bad scenario played through my mind. It's been years since I've done this and only twice in my life to boot. What if I'm no good? A mare wants a guy to get them off and both times, I sucked at it. I don't think I can go through with this! I can't do this! I just can't!

"Okay, Caddy, listen up!" Cadence spoke up as we grounded ourselves and trotted towards the farm house. "You've got this! You're a young buck in your prime! You're gonna go in there and satisfy a pent up farm girl and yourself! And after that, you'll have a new friend. Who knows? Maybe she'll love it so much, she'll want you to bang her more often. You could actually get yourself a steady stream of sex for the first time in your life!"

"I can't fucking believe I let you talk me into this."

"Okay look, I really don't want to be an enabler and support your concerning drinking habit but if it'll help you calm down, take this."

Before sending me to whore myself out, Cadence produced a bottle of whiskey into existence with her alicorn magic and proceeded to uncap it and shove it into my gob. With some much needed liquid encouragement sloshing down my gullet, I really did begin to feel much more relaxed. Wow, if this is the only thing that can calm me down, I really do have a problem. Fuck it, we can ignore it later. Right now, I've got some work to do. Who would have thought customer service could involve whipping out my dick?

"Alright, Cadence." I said as I puffed out and ruffled up the fluff on my chest. "I'm about to go make confidence my bitch."

"There you go! Here, one last thing. Take this condom. I've enchanted it so you'll be better able to get her off! I know you're a novice now, but she'll be begging for more later on! Now get in there!"

With a confident posture and some swag in my strut, I trotted over to the door and wasted no time giving it a firm knock. I didn't have to wait so much as ten seconds before I heard heavy set of hooves attached to some powerful legs thumping towards the door. She must be excited too but she's probably trying to hide it now because I know she's on the other side of the door but she's pausing. I couldn't hear anything beyond that but after about another thirty seconds, the door slowly creaked open.

I've never seen Applejack like this before, and to see her with her hair down was actually kinda cute. Oh, fuck it, she was smoking hot. Any other time I've seen her, she was working or just getting done with her work but she clearly just finished brushing her coat moments ago. Her tail was no longer tied up with that red ribbon it usually has on it and that had obviously been brushed too.

The sweet smell of her perfume was enough to put me even more at ease, not only because of how spellbindingly fragrant it was, but the fact that she was wearing it meant that she wanted to impress me as much as I her. Maybe this wasn't such a bad idea after all. To see her and smell her like this made me see her in a whole new light. A whole other side of her that meant just like me, she too was a fellow equine with a life outside of work and bodily urges that she and I would soon fulfill. I think this could end up being the start of something wonderful, the more I look at her.

"Come on in." Applejack said softly, her intentions clear as day in her tone. "Glad ya showed up, hon."

"Heheh, why wouldn't I?" I asked, with confidence and poise as I trotted through the door. Hey, this ought to be easy! I just gotta use the same confidence I use when I'm here to sell!

"Ya know, Ah always thought you were an alright guy but Ah figured ya didn't wanna get involved with anypony outside yer job." She takes me by the hoof and leads me up the stairs. "I was mighty surprised when ya smacked mah flank earlier. Ain't gonna say Ah didn't like it. Boy howdy did that give me a rush."

"Hoho, if that was enough to give you a rush, then just wait until we get to your bedroom."

If I can just maintain this relaxed confidence, I think I can make this work. Applejack finally lead me to her room and pushed the door open and stepped in ahead of my, her tail raised high and proud, giving me a nice view of what I was about to get. Ooohohoho, fuck me, I'm about to get in on some of that flank. That firm, toned flank chiseled by years of hard, back breaking labor on the farm. I can already feel myself slipping out of my sheath.

It doesn't take much to get me started and get the blood flowing into my stallionhood. It was when she laid down on the bed and looked over at me like I was the tastiest apple pie she'd ever laid eyes on that my dick started to come out. I hesitated for a moment until she patted the bed next to herself that I strutted on over and laid down next to her. What she did next was something entirely new to me and though it was something very simple, I really enjoyed it.

As soon as I laid down on the bed next to Applejack, she just grabbed me by my shoulders and pulled me right up to her. It felt awkward at first and if anything, made me a bit anxious but as she and I looked at each other, our muzzles right up on each other's, I really began to assess my position. To feel the warmth of another body against mine felt incredible. It was something I've never felt before as both the other girls I got with just hopped out of bed and said "see ya" the second we were done.

This felt really nice. At this point, I don't care if we don't do anything more than cuddle like this, it was so nice. At first, it was making me nervous, but once I just kinda loosened up and got the feel for her body against mine, I felt so much more relaxed. Like she was supposed to be there and...being pushed away from me all of a sudden? What gives?

It wasn't she, nor I who was now pulling or rather pushing us apart as much as it was my own throbbing member coming between us and snaking its way upward as it became rock hard. She and I both let out a good, hearty laugh at the irony. Jeez, you'd think the last thing a part of my body that wants so badly to get inside this mare would want to increase the distance between us.

So here we are, just laying here. She can't seem to keep her eyes off my cock, which is kinda confusing. I'll let you on on a little secret. I'm not big, but I'm not tiny either. I am completely and totally, the very definition of the word average. Dicks like mine are a dime a dozen. It's nothing to brag about but at the same time, nothing to laugh at. It's nothing special but if I put it to good use, it'll get the job done.

She seems oddly impressed for some reason. Surely a strong farm gal like her would need some heavy duty equipment to satisfy her. Maybe that's why Cadance gave me this magically charged condom, she knows way too much about me. Oh shit, what am I doing just laying here thinking about shit!? I need to get this started and get my body moving before I put Applejack to sleep! Well, I can't just stick my dick in her without working up to it first. Our muzzles are together right now, perfect time to start kissing.

Out of nowhere, I just went for it. I went for broke and brought my lips to hers and in no time, our tongues were wrestling one another. This was also new to me, the other mares I was with just laid there while I sucked their face, didn't even so much as move their lips. It was like making out with a corpse back then and now, I had a girl who I'd spent time getting to know putting in the same effort that I was. She was obviously a lot better than me as I had little to no experience but I quickly got the hang of it.

I like this! I like it a lot! We both let out soft moans as we went from sweet, gentle kisses to full on make outs with our tongues flying all over the place. Now that I've got her attention up here, I'll try to get a hold of some down there. As I gradually moved downward and planted kisses on her cheeks, chin, and down to her neck, my free hoof made its way down to her marehood. Both our eyes were closed but I knew I reached my target when she suddenly broke the kiss and let out a gasp. Yes. I've got her right where I want her and she's loving every second of it.

I continued planting kisses on her neck as I rubbed her nether regions with my forehoof. I must have been doing a good job, as she no longer seemed able to focus on kissing me, her moaning and gasping growing louder and more passionate with every stroke of my hoof. Yes, she likes it. She's getting wet and she's wrapping her arms around me and pulling me even tighter against her body. As far as I'm concerned, a mare's vagina is like the perfect internal combustion engine; self lubricating, changes its own oil and I'm able to get her started with just one hoof. I know engines, I built my first one when I was six.

Speaking of lubrication, I think I've got her warmed up. Now it's time for me to get to work. Not only is my performance bound to play a factor in our relationship, it could affect my reputation in this little town. Ponies occasionally talk to each other for whatever reason. Okay, steady now. Just gonna use my wing to push myself up off of my side and on top of her while I keep kissing her neck. Oh, gotta get that condom ready, we're not doing anything without that. Now if I could jus-woah!

Without any warning, she just wrapped her forelegs around me, flipped me over and landed on top of me! Ohh, she must wanna play cowgirl. Hey, I'm not complaining, she can ride me all she wants. Okay, I'll let her grind on me for a bit and show her why ladies call me the land yacht...okay, they totally don't call me that but I can dream, alright? Now let's just get back to me and Applejack, I'm really digging that sexy look in her eyes and I want in on it. Before she goes any further though, better slip this rubber on and...there we go.

"Ah'm mighty glad ya came back tonight, Caddy." Applejack said, the tone in her voice making me harder still. "Ah always thought ya were a swell fella, 'n it really got me goin' when ya gave mah butt a swattin' earlier. Heheh...Ah've been thinkin' 'bout this allllll day."

"Keep talking, sweetheart, that drawl of yours is putting me in a mood like you wouldn't fucking believe." I cooed with the best sultry tone I could muster as Applejack positioned herself over me and slowly sunk down on my dick.

Ooh, she's a heavy one. Well, what the fuck'd I expect, she's all muscle. Not gonna lie, kinda turns me on. I mean, I guess we're kinda past the point of plain superficial arousal, she's grinding on my dick as I speak. Ooh, hot damn, she's tight! Again, the muscular physique probably has something to do with it. Ahh yeah, I'm liking this. I'm just gonna lay back, fold my arms behind my head and relax while this sexy thing rides me like the pony I am.

"Come on, hon, you're not gonna hurt me, I can take it." I purred as my new friend continued to fuck me and steadily pick up the pace.

Oh my god, I can't believe I'm really doing this! I haven't been laid in years and I have my dick inside a mare right fucking now! Yes! Ohhohohoho, thank you Cadance! Oh man, if you and Shining Armor had an open relationship I'd-ow! What the-ooh! Jeez, girl, ease up a bit!

"Yeahhh, keep it up, girl." I said, knowing that she was getting a bit rough for my light, pegasus frame.

Shit, she's making me her bitch right now! I didn't think she'd be to rough. Gahh, I gotta quit being a pussy. I'm not about to let her know that she's actually inflicting some mild pain on me right now. She's got her rock hard forehooves firmly pressed into my chest and the marks she's leaving will probably be permanent. No, I can't give in. I'm her big strong stud, I can't let her know that it hurts.

"Is that all you've got!?" I blurted out with a crooked, sideways smile. "Huh? Is that all you've got, girl!? Come on, put your back into it!"

I would end up regretting that, big time.