Twilight couldn't help stare. I mean come on now! She had read all kinds of medical books of anatomies of creatures and species across the world but none looked even remotely close to what was in front of her. "It's...safe to get a closer look right?" She asked cautiously, glancing up at her partner.

Chuckling deeply Jack nodded. "It has a few great reviews for it so don't worry about a thing." He teased lightly, chuckling once more with that easy smile of his. His legs swinging lightly in the pools water on either side of her.

She couldn't help watch as his penis bounced with his laughter. Licking her lips Twilight raised a finger and slowly ran it up the length of his shaft. The notepad scribbled further as she examined him. "Shape similar to average pony's but curved top instead of a flare." She said aloud, wrapping her fingers around the shaft. When he jolted at her touch she looked to him with nervous eyes.

"Don't worry, just know it's sensitive to stimulation even as light as grabbing it. Especially the head." He explained, smiling with a small blush of his own growing. He rested his hands behind him to support his weight.

Nodding and writing what he had told her down Twilight got closer to the object in her hands, her modest bust almost touching it. With a look of wonder she ran her fingers over his rod, taking minor enjoyment at it's twitching and Jack's little jolts and breathing. Leaning down she gave a small sniff, finding it rather enjoyable. "Ok...I'm going to l-lick it." She stuttered, opening her mouth to let her tongue out. With a slow motion she dragged it across the tip, finding the taste weird but not unenjoyable. With paced motion she wrapped her lips around the tip and jerked in drawn out motions. "Ok, the book said to swirl around the top especially." She thought to herself as she worked her tongue.

Jack for his part gave moans of encouragement, running a hand through her damp hair that hung around her shoulders. "You're doing great so far. Just make sure to watch any teeth ok. That's a generally frowned upon thing in this situation." He coached, scratching behind one of her ears as it flicked.

Growing bold and taking what she said in mind Twilight worked herself deeper down his shaft, her jaw holding itself wider so she wouldn't accidentally graze him with her teeth. Her hands shifted to explore the inside of his legs, running across his toned thighs and heavy sack. getting distracted from the sensations her hands felt she went too far and gagged from feeling him hit the back of her throat. Pulling back she began to cough roughly from the problem.

In one swift motion Jack pulled Twilight from the pool into his lap, rubbing her back to help with the coughing. "Easy. Easy. No need to push past what you can handle." He soothed, holding her tightly as she collected herself.

Embarrassed Twilight pulled herself from his grip. "I'm sorry. I'm sure you'd prefer one of the others more experienced in this sort of thing." She mumbled, looking away from the human. "I probably can't satisfy you as well as they can..." She added, moving to leave only to feel a tug at her hand. She looked back at the human only to have his lips connect with hers, her body being slowly pushed down by the larger figure. When they separated she stammered "W-wait, don't you want one Fluttershy or Spike to help with th- EEP!" She suddenly jolted as a pleasurably shock went through her body as a hand from Jack settled between her legs.

In a low rumble Jack looked up at her as he dragged a tongue across her ribs close to her breasts. "I don't remember asking them to join me here now do I?" He questioned, another hand working up to stroke her cheek. Shifting his body to settle between her legs Jack's voice still sat in a deep tone. "What I want is to experience a mixing of pleasure with Twilight Sparkle. Not Spike. Not Fluttershy. Not even the other princesses." He said, slipping a hand to gently massage her breasts while the other slipped a finger into her folds.

Twilight couldn't help arch her back as Jack took control of the situation. She could think to worry about satisfying him as he gripped her with his strong hands keeping any ability to leave locked away except for using magic.

And right now her mind was as far away from using magic as possible.

Her hands moved to his, making him squeeze or caress her hard. Her hips moved on their own as she ground into his hand. "Ahh, ahh, yes! I'm sorry for doubting. Please make me feel better." She moaned. Another finger slipped inside of her as his thumb found its place on her clit. "Ahhhhh!" She moaned loudly, an orgasm rocking through her body. Slumping on the ground she breathed heavily as he removed his hand. "I....I have never came that fast before." She breathed, her chest rising and falling quickly.

Jack leaned himself next to her, grabbing her hand comfortingly. "If that was too much and you feel too tired just say so ok?" He instructed, his other hand moving her mane out of her face.

"I think I can keep going." She said, gulping slightly as he shifted his form to above her. His hands wrapping around her thin legs. As she looked at him between her Twilight realized just how much larger this man was compared to her. If she didn't have her magic she knew she wouldn't be able to push him off if he was an assailant.

Angling himself at her entrance Jack slowly pressed his tip against it. Looking at the mare he gave a stern look. "Twilight, it's clear you are a virgin and this is a big step. I want to be absolutely sure you are ok with doing this as when I put it in there's no undoing what has happened." He warned, with a clear image of care for her.

Nodding her head as she threw the bad thought away she rested her head against the ground, looking up into the air. "I'm sure of it..." She said, reaching a hand out for one of his own. Finding it almost instantly.

With a breath Jack slowly began to push forward, taking his time to make things as comfortable as possible. He felt resistance, having to push slightly harder to get his penis inside her. He had almost gotten the tip fully in when he felt Twilight's hand squeeze extremely hard and shake almost violently. Immediately he stopped and pulled himself out. "Ok, we are done here." He commanded, standing up while waving a hand to pull two towels towards them.

"Wa-wait, why are we stopping?" Twilight questioned, looking at the man as he wrapped a towel around his waist.

Looking at her with a small grimace Jack pointed at her body. "We are stopping because of that." He simply stated.

Twilight looked down wondering what he was talking about only to see her body shaking uncontrollably. "Wahhh?" She mumbled to herself.

"you aren't actually ready for that next step." Jack explained, taking the second towel and gently placing it over her body, taking note of how she twitched at his touch. "Before you argue about how you want to continue, just know I will not try again no matter how much you ask." He added quickly after as she opened her mouth. "We will return to the others and enjoy the rest of the day with them.

She felt devastated. Not at Jack but at herself for not being ready after leading him up to this point. Her magic began to flare up as a teleport spell filled her head only to find it not working. Opening her eyes she found her had wrapped a hand around her horn, cutting the magic off. Tears welled up in her eyes. "I-I'm so sorry. I knew I couldn't match up with the others." She apologized.

She was cut off when Jack placed his lips once more over her own. Pulling away slowly he placed a finger over hers as an added piece. "For starters stop comparing yourself to others. I have grown to enjoy Twilight the book loving princess who leads the elements of harmony. Not Twilight who puts on acts to be like other mares." He lectured. "Secondly, It's important to not only trust your partner but also trust yourself. I know you care about me but you still have problems involving yourself when it comes to taking this next step. This could be a fear or just simple not feeling it yet." He continued, kissing the top of her head just under her horn. "I'm not stopping the whole adding you to my herd process. I'm just stopping us stepping over lines you aren't comfortable crossing yet. We can experiment and test things, ya know build you up to the point. At your pace." He finished.

Twilight's lip quivered as she sniffled. Leaning in to hug the human she let him carry her out of the pool back to the others. Before any could tease or ask how it went he gave a gentle shake of his head with a soft smile. Fluttershy and Spike along with Rarity and Ember caught on quickly, changing topics easily for the others to understand. They spent the rest of the day chatting and relaxing all while Jack never let go of Twilight's form in his arms.

Author's Note

Gotcha bitches! You were expecting the usual porn chapter but instead got loving two part in the future!