Dear Diary...
Sorry I haven't written in a while, but... For Luna's sake, where do I begin?

Just as Lyra suggested, I explained the situation to Doc and to Treehugger. They were both quite flattered to be objects of my desire (Doc more so, as Treehugger tends to be pretty chill about everything) and agreed to a staggered series of dates. Hearts and Hooves Day falls on Friday this year, so I started with Treehugger on Saturday night, followed by Doc on Sunday, then Treehugger, and so on. On Friday, I will present my decision.

So far... well... maybe I should just tell you what happened.

My first date with Treehugger went pretty well, and we had a lot of fun. It was a sunny day, so we decided to stop by the swimming hole... in February. Yeah, the water was frigid, but we both had a good laugh about it, then snuggled on the beach to warm up. The way she held me made me feel like I was the center of her world... I still blush thinking about it. She also taught me how yoga works, and it feels like it's gonna be a recurring thing between us.

Doc's date went great, too. He took me to a movie, a romantic comedy, and followed that up with bowling and dinner. A very traditional night out, I'll admit, but it was sweet, particularly when he'd try to be romantic but wasn't sure what to do. He thought he'd had this date all calculated and mathematically parsed out, but when he'd come across something unexpected, he'd get a little flustered. But he makes me laugh, and smile a heck of a lot. And even though we didn't do that great at bowling--the one time I trusted my eyes to aim for the pins on their own, the ball wound up outside--we had a marvelous time.

Now those are all well and good, but the second date with Treehugger… that's where things got interesting.

Early on the day afterwards, some hours before my second date with Doc, I stopped by Lyra and Bon Bon's house to say hello and let them know how things were going. We sat at the table and ate fresh candies that Bon Bon had prepared.

"So, how did yesterday's date go, Derpy?" asked Bon Bon.

"Tell me every detail!" Lyra added, leaning forward eagerly on her elbows.

I cleared my throat and laughed nervously. "Uh, well..." Shifting in my seat, I let my eyes wander about the room as my brain recalled the eventful evening.

"Things started off pretty calmly. I picked her up from the art studio and we grabbed dinner together, then went back to her place for some yoga..."

"This is a nice place you've got here, Treehugger." I said, taking in the room from multiple angles with my wonky eyes.

"Thanks." She said in her slow, ever-calm voice. "I try to keep it lookin' nice, but like, nopony ever comes over, aside from Fluttershy on occasion. You're the first pony in a while to come here--and, well, the first date I've ever brought back here."

"Oh. How nice!" I said with a smile. Suddenly, my eyes caught sight of a large mass of green on the opposite side of the house. "That is a lot of plants."

"Oh yeah, they're kinda like my housemates. We keep each other company."

I certainly knew what it was like to live alone.

"Each of 'em's got a name, too. That little palm is Sherrie, the cactus is Pete, and that rather dashing vine is Sir Tanglemore the Third."

"What about that one?" I said, gesturing to a particularly verdant plant growing from a pot on the floor.

"Oh, hehe. That's Mary Jane." Treehugger chuckled. "She helps me keep it real. So anyway, you ready to start today's lesson?"

I'd come to enjoy these yoga lessons: they're good for helping me limber up, especially since I often have back problems from carrying heavy packages. My 'instructor' introduced some new stretches that evening, and goodness, my wings felt so weightless, I felt like I could've crossed an ocean on them. By the time we finished our usual routine, the sun was setting.

With the cutest blush I've ever seen, Treehugger invited me upstairs to her balcony to watch the sunset. It was a nice little space, open to the cool night air, padded with pillows, decorated with flowers and incense burners. Much as we had on the beach, I leaned on her shoulder, wrapped in her forelegs as the princesses moved the heavens from the distant city of Canterlot.

"Thanks for coming to meet me at the studio." She said, nuzzling her cheek into my mane. "I've been having to work longer hours to make ends meet, and I appreciate the support."

"No problem at all." I said. "Do you enjoy doing that?"

"Modelling? Yeah, it's alright. I've always been pretty, y'know, 'open' with my body. Not that I don't have a sense of modesty, it's just... like... this is me. This is natural. Why stigmatize it? That being said, having everypony's eyes on me is a bit of a thrill. I like the feeling of being exposed."

"Well I'm glad you enjoy your work, Treehugger."

"I know you do."

My face lit up red as I looked up into her gentle, knowing smile. "Wh-what?"

She gave a friendly giggle as I slid and fell into her lap. "I noticed how often you come to the painting classes when I model." She gently stroked the fur of my belly with a hoof. "Do you like looking at me?"

I gulped and gave a nervous, closed smile, my eyes fixed firmly on hers. She laughed and closed them, before half-opening them again sultrily.

"Hm... I'm very glad to hear that... because I like being looked at."

With her other hoof, she brushed aside some fur on her underbelly, revealing two--- well, I think you can guess. I shot up into a sitting position, covering my beet red face in my hooves. Treehugger immediately put a hoof on my shoulder to comfort me.

"Whoa, hey, I'm sorry! I didn't mean to startle you. Are you alright, Derpy?"

I nodded and gave a very quiet "yeah," turning to face her with an embarrassed red-cheeked smile. She smiled too, and took my hooves in hers.

"I'm so sorry. I should've made sure you were okay with that before..."

"Oh no! You're fine! I just, um... I've... tried to imagine what you were like for... a while..."

Treehugger blushed as brightly as I was, clearly flattered at my attraction to her.

"Well, hey, um... if you, like, uh... want to... do more... we can do as much or as little as you want..."

I gulped again. Was this really happening? The mare of my dreams showing the same desires I'd only dreamt of?

I nervously laughed. I wasn't sure how far I wanted this to go. I'd never even come close to any sort of intimacy before.

"Um... I-I g-guess, uh... would you p-please, um... k-kiss me?"

Treehugger smiled softly and planted one firmly on my lips. We held that kiss out for a good minute or more, feeling the textures of one another and tasting all we could. I had never kissed anypony with an open mouth before in my life, let alone with my tongue, but Treehugger clearly had. She guided me through this new, wonderful experience like fireflies in a dark forest, and stirred the heat of desire within me as I'd never felt before.

After we broke off our kiss, it was in this heat that I expressed a secret, forbidden desire I'd long held.

"Treehugger…" I said between shallow, panting breaths "I-I want you t-to pin me down..."

She gave a sultrier, more lustful smile as she lowered me onto my back, resting her warm belly on mine as she held me down, placing tender, passionate kisses on my mouth, face, and neck, earning little moans of pleasure from me. I held her in my forelegs at first as she worked; it was clear to me she'd done this before, possibly with other mares, as she knew just what to do to make me squirm. Just looking into her dusky, half-lidded gaze of desire and seeing her glistening mouth could've made me release then and there, but I wasn't quite ready yet. I wanted this tension to last as long as possible. It was time to up the excitement.

"Go lower..." I whispered.

Treehugger, tantalizingly slow and gentle, nuzzled her muzzle into my collarbone, then the fur of my underbelly, her soft, hot lips seeking out my two most sensitive bits hidden within... I think you can guess what. I bit my lip and began running my hooves up and down her torso, occasionally daring to pass them over her taut flanks.

She loosed her lips from around me, looking up with a guilty scarlet face. "You okay? You're shaking."

"Oh, I'm just... I'm finally touching Treehugger…"

"No..." she said in a playful whisper, locking eyes with me. She grabbed one of my hooves in hers, and moved it gently down her underside. I almost jumped when I felt said hoof touch something supple and wet.

She turned her chin up, looking down at me with domineering eyes.

"Now you're touching Treehugger."

She bit her lip hard and giggled from the back of her throat. Realizing where my hoof was being rubbed, my body started shaking even harder. I felt my thighs tense, and before I realized what had happened...

...I passed out.

"You did WHAT?!" Bon Bon nearly spat her drink across the room.

Lyra burst out laughing. "HAHAHAHA! She actually SAID that?! Hohoho, by Celestia, I thought I'D said some stupid things in the sack, but jeez! HAHAHA!"

Bon Bon glared at her lover. "I happen to find those stupid things you say very sexy, Lyra." As the unicorn blushed, the Earth pony turned back and motioned for me to continue my story.

I woke up some time later, still on my back in the place I'd been pinned. I sat up and saw Treehugger laying on a pillow in the corner, flipping through a magazine.

"Oh, you're up!" She said, snapping to attention. "I'm sorry about that, I should've asked before I moved your hoof... I just got so wrapped in the heat of the moment, I had to..."

"It's fine, I-I understand." I scratched the back of my head. "D-Did you, um... did you...?"

She nodded. "Yeah, I did. Not long after you passed out, actually. I'm kind of quick on the draw. What about you?"

I looked down at the meeting of my thighs. You can probably imagine what I saw.

"Yeah, it appears so." I said, looking back up at her. "How was it?"

Treehugger blushed and looked away. "Amazing." She said under her breath. "Again, I'm sorry if I made you uncomfortable with that. I couldn't stop myself."

"It's fine, Treehugger. I'm glad you enjoyed it, too." I stood on shaky legs and mopped sweat from my brow. "Whew! Let me tell you, that's the fastest my heart has beat in years. I might have to find you this summer when my heat kicks in!"

Treehugger laughed heartily at that. "I wouldn't mind that." She said in a demure voice. She stood to give me a hug. "I hope that my actions this evening don't affect your Hearts and Hooves Day decision. I hadn't intended this as a trump card, I just..." she shrugged "...saw how you wanted me, and I wanted you to have me. I know all too well what it's like to pine over somepony for so long and never have a chance with them."

"Aw, you're okay, Treehugger. And don't worry, this won't affect my decision. It'll be our little secret."

She blushed as I kissed her hoof like a gentlecolt, then she brought me up for another kiss on the mouth. Afterwards, she sniffed the air; the scent of pheromones still hung heavy on it.

"Um, Derpy, you can, like, take a shower before you go if you want. I already washed up while you were sleeping..."

"Naw, it's fine." I said, swishing my tail and very likely scattering my pheromones across her bedroom. "I don't want to tempt either of us any more than we have already. If I fly high enough, I should be able to avoid anypony's prying noses."

And so, I left by wing into the night sky, flying uneasily in the high winds higher up. I could hardly believe the experience I'd just had. I wasn't sure how to feel about it, either. I had consented, yes, and I wanted it to happen, but part of me didn't feel... ready, I guess. Most of the flight, I was curiously regarding my left hoof and where it had been, as it still faintly smelled of her. I didn't tell Lyra and Bon Bon what I did with that hoof once I got home, but that's beside the point.

After I'd finished my tale, Bon Bon sat across from me deep in thought. Lyra was bringing over more refreshments.

"It's just that after all that, I'm not sure how to make Doc's date pop." I broke the silence. Bon Bon shook her head at me.

"Derpy," she began "you don't need to do anything intimate--or for that matter, anything extraordinary--to have a great date. Heck, the first two dates you've been on have been nothing but you hanging out with Treehugger and Doc."

"But you two started your scoodily-pooping after only a week and a half!"

Bon Bon reared up in great surprise, then shot a look of concern backwards at Lyra, who slowly backed out of the room.

"Yes, Lyra and I did jump each other's bones pretty quickly," Bon Bon said with a turn back to me "but that doesn't mean you have to feel rushed to. We're completely different ponies, don't compare yourself to us. Just be yourself, Derpy, take things at your own pace, and you'll be fine."

"Just like Treehugger." I added. "She lives in her own time zone. Though things sure seemed to move quickly last night."

"From the way you described it, what she said, how she acted, I think that was just her way of showing you love. I've heard things about her, and she seems like the type to believe in free love."

I blushed deeply. "It certainly felt like she'd done this before."

"You know, Derpy," Bon Bon gave a clever smile "I think I know of another couple in Ponyville who could give you some helpful advice."

Author's Note

Made you look!
Okay, but that's all, and I'm serious. I hope you enjoyed it, ~~you degenerates~~