Hold Her Gently

by Bendy

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Rainbow Dash, Romance, Second Person, Comedy, Random, Sex, Human, Twilight Sparkle
Length: 3607

You just had 'sex' with Rainbow Dash... well sort of. However, Rainbow Dash now wants you to have 'sex' with Twilight to rid her of her virginity.

You just had 'sex' with Rainbow Dash... well sort of.

However, Rainbow Dash now wants you to have 'sex' with Twilight to rid her of her virginity.

A big thanks to Ravvij for helping me with editing to improve the story overall.

Published 2016-07-13 20:20:02 UTC
Last updated 2016-07-13 20:20:02 UTC

Holding Her Gently

“Awww yeah! I’m an alicorn now! Thanks Anon!” shouted the excited voice of Rainbow Dash, just after lifting her head off your softening member.

“You're... welcome... Rainbow Dash,” came your breathless voice.

All of a sudden, the alicorn mare lunged forward, pushing you over onto your back upon the bed, followed by pressing her soft lips against your own, along with wrapping her hooves around your neck and driving her long, thick tongue deep into your mouth.

For a moment, you had considered pushing her away, sickened by tasting trace amounts of your own seed within her muzzle.

However, when you saw how peaceful she looked with her eyes closed whilst kissing you, you decided against it and instead returned the kiss with gusto, along with placing your hands upon her rump, digging into the thin layer of soft fat with your fingers, before reaching the firm muscle beneath.

The mare atop you moaned aloud into your mouth when you began to dance your tongue alongside her’s, tenderly caressing and circling around her’s.

The mare giggled at the feeling of your front canine teeth as she rolled her tongue across the sharp surface.

Wanting to feel more flesh, you moved your hand between the featureless canyon of her backside, rubbing that area as if she had a vagina… or even an asshole for that matter, which none of her species had. While it got no reaction from her, you personally enjoyed doing that.

But, her whole body soon began to tremble erratically when you gave a gentle lick to a sensitive area under the bridge of her tongue, hitting the pony equivalent of a G-spot.

‘This universe is weird,’ came your thoughts.

From hearing the sound of a sad whine from her, you decided to stop teasing her and give her ‘love cuddles’ already.

So, with that you raised your hands upward onto the midsection of her back to get into the ‘cuddle position’.

Once there, you gave her a gentle squeeze, causing her to utter a loud, animalistic whinny into your mouth.

For the next several minutes, you two merely kissed and cuddled. To maintain the long kissing session, you breath through your nose, all the while Rainbow made a mix of both quiet horsey sounds and moans into your mouth.

On occasion, you gently licked that delicate spot you found under her tongue, enlisting loud horse sounds from her each time you did so.

However, when she tried to do the same to your tongue, the mare uttered sad whines from your lack of reaction.

In response, to hearing her so upset over not being able to return the pleasure the same way, you had reached your right hand behind her neck to tenderly rub the back of her ear, earning yourself a satisfying throaty moan from her.

A rather mean spirited giggle left you, when you felt her gently rub your right ear with a hoof in return.

Though, you soon regretted it, when she abruptly stopped kissing you, pulling back to stare at you with her eyes narrowed to slits.

“If you ever mock me again, I’ll bite your dick off next time I give you a blowjob,” she said in a quiet, menacing voice.

She maintained her angry look, until she saw the look of pure terror in your eyes. Subsequently, her look soon soften, eyeing you with concern.

“You took me literally, didn't you?” she awaited you to nod wordlessly in answer, before continuing. “Anon, you’re such a pussy sometimes,” she spoke softly, leaning forward to gently nuzzle the right side of your neck.

“I would never bite your dick off, Okay? Sometimes ponies say things when they are angry, but don’t actually mean it,” she spoke in a soothing, soft voice.

“Okay, Dashie, I trust you,” you spoke in a low voice.

“Good! Because I would terribly miss drinking your cum if you chickened-out from a blowjob,” she said sternly.

“I'll gladly put some cum inside you right now,” you said, pointing down at your recently re-hardened member.

The mare bit her lower lip nervously at your offer. “Sounds tempting, but I really want you to help out Twilight. She really needs love cuddles too.”

“I’m not sure if I should,” you replied nervously, shaking a little.

“Oh, don't be such a wuss!” she bellowed.

“I guess… you have a point. Let me just get my– ” as you spoke Rainbow Dash’s horn became surrounded in a rainbowish blur, before summoning a t-shirt and pants for you. “... clothes.”

“Let's go already!” she shouted.

With no further ado, both of you had sallied forth on your long and epic journey out of the bedroom into the hallway, followed by walking into another bedroom right across from your own bedroom.

Within this room, a purple unicorn was fast asleep in a small, single bed. A light blue blanket, decorated with several stars and half moons covered over her body.

Rainbow Dash wasted no time and began trotting over to the side of the bed, before gently shaking her awake.

"Twi… Twilight…?" Dashie sing-songed softly into the sleeping mare's ear.

“Mm, what?” the unicorn replied grumpily, her eyes fluttering open lazily. She rubbed them gently with her hoof before staring almost blankly at the intruders in her room.

Her eyes caught sight of the appendage on Dashie's head and they widened to comical size. She looked back and forth between Dashie and her horn, disbelief flooded over her like a bucket of cold water.

“Rainbow... you're an alicorn!?”

“Awesome, I know! But I’ve come here to get this nice guy to give you love cuddles.”

You rubbed the back of your neck, a nervous smile upon your face while Twilight stared at you with wide eyes.

“Anon, you will give me love cuddles?” she spoke softly, in nearly complete disbelief, and blushing profusely.

“Yep, that's right. I’m going to give you love cuddles,” you replied not sounding too sure, yourself.

Twilight climbed out from under her blanket and sat herself down at the side of her bed.

“I’m… not sure,” she spoke, tapping her hooves lightly together. “I-I'm not sure i-if I’m ready. I never had love cuddles before.”

“Come on, Twilight. He’s the best guy to lose your virginity to. He will give you the best love cuddles ever. Plus, he’s the only guy on this entire planet who actually has a penis!” Rainbow Dash stated in all the enthusiasm she could muster.

“A 'penis'? What's a 'penis'?” she turned to you, eyeing you curiously.

“It’s the thingy a human male uses to make a human female pregnant by cumming inside her vagina,” you explained proudly your expert knowledge of sex from years of experience.

“What's 'cum'? And what's a 'vagina'?” she asked, tilting her head to the side and perking her ears to hear whatever explanation you had.

“Well cum is– ”

“Cum is tasty creamy stuff that comes out of his penis when you suck on it for a bit,” Rainbow Dash interjected, smiling like a foal with an ice cream.

“Really? That sounds delicious,” she beamed happily, her eyes sparkling.

Rainbow Dash pointed to her horn. “His cum also gave me this!”

“Really? That’s amazing!” she shouted excitedly, jumping up onto her hooves.

“Uh girls, I’m right here,” you interrupted, feeling slightly annoyed and left out at the conversation.

“Oh… sorry, Anon,” Twilight said quietly, scratching the back of her neck nervously with a hoof. “You'll still give me love cuddles, won't you?” she said cautiously.

To answer her question you sat down upon the bed beside her and from there you gently took hold of her hoof and stared deeply into her large purple eyes.

“Of course I will give you love cuddles, Twilight.” you said sweetly.

“Will… will y-you be gentle... and p-patient?” she said, her body shaking. She rolled her hooves over each other as if to wring them.

“Yes, I will squeeze you very gently and be very patient,” you spoke softly, squeezing her hoof tenderly, stopping her nervous motions.

The unicorn uttered a happy sigh, her fears mostly allayed. She leaned her head onto your shoulder and her hot breath seeping through your shirt.

Rainbow Dash took this as her queue to leave. She backed out the door and quietly shut it with a barely noticeable click.

For a good while the two of you merely remained there, Twilight resting her head on your shoulder and you stroking her mane lightly.

After quite a bit of time had passed, you had decided to break the silence, “Twilight? You don't have to do this if you don't want to. I mean, you hardly even know me. I haven't been in Equestria for a week yet.”

Slowly, Twilight looked up to stare deeply into your smaller, human eyes. Her innocent gaze made your heart melt at the thought of just how trusting and cute she was.

“I trust you, Anon.” she spoke softly, leaning forward to gently press her lips against your own. The mare gasped at the feeling of your lips against her own.

Worried, regardless of how soft and cool her lips were, you pulled your head back, “Are you okay, Twilight?”

“Yes… I’m okay, it’s… it’s the cuddles that hurt, not the kisses,” came her near breathless voice.

After hearing that, you uttered a sigh of relief, the mare wasted no time in rejoining her lips with you, moaning in bliss at the feel of your lips against her’s.

For the next several minutes, the both of you just kissed. Not even tongue kissed, just the lips of both human and pony exchanging tender affection. You gently held her cheeks in your hands, stroking her velvety fur with your digits. Twilight did much the same as she pressed her hooves carefully over your shoulders and chest.

It seemed like forever when Twilight eventually parted lips with you, though you'd have been fine with more of forever kissing her.

“I’m… I’m… ready,” came her voice, low and nervous, and filled with heat.

Gently, you set her upon your lap and smiled at her. You leaned back slowly but kept your hands firmly on her sides.

"You can move whenever you're ready." you coaxed softly, lightly rubbing your thumbs against her fur.

Without a word, Twilight lay herself down, slowly, atop you. From there, she tenderly placed her hooves on your shoulders, her blush ever present on her face which was now a mere inch from your own.

“Cuddle me,” she spoke sensually, leaning forward and kissing you.

You and Twilight exchanged a passionate kiss, to which she started by lightly pressing her tongue against your lips, asking, if not begging, timidly to gain entrance. You acquiesced and parted your lips for her. She slid her tongue in and, immediately, you could tell she didn't know where to start. You met her tongue with yours and guided her slowly.

She gradually became used to exploring your mouth, and especially your teeth. You reciprocated by pressing onto the places you'd found on Dashie, but were surprised when she didn't react the same way. Some exploration is in order. You searched for a short while and found not one but three spots that made her shudder. The strongest of which was on the roof of her mouth.

After quite a bit of time has passed, you carefully lifted your hands up, hovering them just above the midsection of her back.

She tentatively pulled her lips from yours, “I’m ready.”

With her consent given, even if it was a bit timid and scared, you proceeded to lightly touch her back, before taking the plunge.

With utmost gentleness, you began to squeeze her. The moment you did so, Twilight cried out in pain, she threw her head back and gritted her teeth before burying her face into your shoulder and her wails muffled by your mass and shirt.

“Are you okay, Twilight?” you spoke softly, immediately stopping your squeezes.

She did not speak, she only silently cried and sniffled into your shoulder, the sheer amount of her tears dripping down her cheeks was soaking your clothes.

“Shh,” you said softly, tenderly nuzzling her neck and lifting a hand to stroke her mane.

With utmost patience, you gently held the distraught mare in your arms, awaiting her to stop crying before you proceeded any further.

As if to reward you for your kindness, Twilight lifted her head, before leaning forward to rejoin lips with you, entering the both of you into a tender exchange of intimacy. You felt her lips quivering terribly against your own. Tears dripped down her cheeks onto your face, but you didn't mind. Clearly love cuddles really hurt a pony for the first time.

For the next several minutes, both of you merely kissed, slowly and gently. You were not going to risk squeezing her again when she's not ready. After quite a bit of time had passed, Twilight slowly parted lips with you.

“Anon, I need you to squeeze me and not stop, no matter how much it hurts me,” she spoke sternly, a spark of determination behind her gaze.

“You sure?”

“Yes,” she said firmly, while leaning forward to rest her head upon your shoulder. “I need you to cuddle me a little harder.”

Wow, she's being strong. you thought, admiring her resolve.

Reluctantly, almost guiltily, you squeezed the midsection of her barrel. Immediately, Twilight leaned forward and cried loudly into your shoulder.

Your heart sank and your chest felt constricted from hearing the pain she was in. Nonetheless you pressed on, despite the muffled screams on your shoulder.

‘How ponies lose their virginity is insane.’ you thought almost bitterly, and another thought came to mind, which made you appreciate her trust all that much more. ‘I imagine rape gets the death penalty, holy fuck.’ you cringed inwardly.

Over the course of several minutes, her cries and sobbing became quieter, soon becoming replaced with low moans and quiet horsey sounds.

Eventually, she slowly lifted her head to stare at you with her horribly bloodshot eyes.

“Thank you,” she simply said, in a soft, distant voice.

You leaned forward and left a soft kiss on her forehead.

Twilight stared back at you with her eyes literally sparkling in joy, before she leaned forward to enter another passionate kiss with you.

Once again, the tongues of both human and pony were joined together in tender affection, dancing with one another in a sensual exchange of love. Your hands gave her back a strong squeeze, earning you a deep, throaty moan from her and a nicker.

Breathing through your nose helped maintain the long kissing session you had with her, topped off with the loving squeezes you gave her every few seconds had made her metaphorically melt in your arms from sheer bliss.

Now, with the mare clearly enjoying herself a certain part of you began to rise at rapid speed, no longer feeling guilty about doing so.

In addition, considering that a very soft, quite a bit bigger, far more squishy backside than Rainbow Dash’s muscular backside, was resting oh-so gently against it, just barely out of reach within a thin layer of clothing stopping it from touching the soft fat of her rump.

Twilight's eyes widen in surprise, before she parted lips with you. She looked back to see what was poking her butt before turning back to you with a slightly annoyed frown.

“Anon, could you please stop poking me down there?”

You smiled sheepishly whilst lightly scratching your cheek with a finger. “Sorry, Twilight. My penis can't help itself.”

“Oh? Can I see your penis!” she asked in an imploring, happy tone.

A shudder coursed through your body. “I’m not sure. You have no experience, you could hurt me and– ”

Twilight must be an evil, cute demon, because she was now staring at you with quite possibly the most adorable, pleading, puppy dog look you have ever seen on a pony.

“Please Anon, let me see your penis. I promise, I’ll be very gentle,” she begged, in a low voice, pawing -or in this case hoofing- at your chest.

“I– I… I don't think-- “ you stopped speaking, your futile efforts to resist were soon broken when you saw her big purple eyes watering up a little at the possibility of you rejecting her while she looked at you as if she was staring into your very soul.

Thus, you uttered a sigh and said. “...of course you can, Twilight.”

A sudden squeal left her grinning a smile and she clapped her hooves together. She backed up and sat between your knees, waiting for you to remove your clothing.

As requested, you pulled down your pants to reveal your penis to the mare, which sprang forth from its cloth prison.

“Ooh... can I touch it?” she spoke, eyeing your member, her inquisitiveness clearly showing through like the bookworm she was. Even so, she was blushing furiously as she eyed the foreign appendage.

“Yes, but be very gentle,” you spoke nervously, shifting your weight from left to right.

The unicorn nodded, before bringing forth her right hoof to gently rub along your pole.

You gasped at the feeling of her soft hoof touching your member. Twilight giggled at your reaction, before she took hold of your member. She began to gently stroke her hoof up and down your spire, holding it with utmost care. You grunted softly and your whole body tensed. A worried expression washed over her face, but she continued to stroke you gently as you gave her no indication of wanting to stop. The soft fur of her fetlocks, like velvet, slid over your sensitive skin and pressed firmly against your engorged member.

Said worried look on Twilight’s face soon turned to a happy sigh at the sight of the blissful look upon your face.

“Well, somepony looks like they are enjoying themselves,” she giggled cutely, shooting you a half-grin.

“Sure am, your hooves feel really nice,” you replied, reaching your hands down to scratch behind her ear.

Twilight uttered a blissful sigh, leaning into your arm and gently licked you. The soft, wet muscle cutely poked out and back in again before leaving a slight cooling sensation on the spot she'd "kissed".

For a moment, she just stayed there with her head resting against your arm, before she bent forward to give the very tip of your cock a gentle lick. Your legs slightly jerked from the sudden contact.

Watching her contentedly, you notice a look cross her features. She looked as though she might be fighting with an idea– she suddenly leaned forward and quickly drove your cock deep into her muzzle, the tip hitting the back of her throat all at once. She moaned loudly as if she'd -well, technically she had- taken your entire length into herself in an attempt to get used to your size.

This caused your legs to jerk wildly and gasp at the sudden feeling of your cock in the warm, soft, wet confines of her mouth. The mare merely held your member in her mouth, not squeezing just looking up at you, concerned.

You placed your other hand on her mane and stroked it gently. She smiled accepting your reassurance, and you moved that hand to her other ear where you began to stroke her ears simultaneously.

The result was immediate as she closed her eyes and hummed approvingly, she began to squeeze and swallow vigorously upon your member, creating a wonderful tugging sensation.

Twilight giggled around her mouthful from hearing your moans of satisfaction.

Smiling, the mare slowly pulled back before dropping her head down, each time your cock hit the back of her throat she repeated the motion. Raising her head a little higher each time, she moaned all the while as your cock tickled a particular spot on the roof of her mouth.

'I guess it's different for every mare.' remembering Dashie's "g-spot".

Her slow bobbing was quite delightful. Her long, thick, and soft tongue felt absolutely amazing for your cock to gently roll back and forth against, whilst her head moved up and down over your dick.

At this point you were little more than a shivering wreck. Maybe it was magic, but pony blowjobs just seem to be awesome. Your hands merely held onto her mane, you couldn't concentrate on anything but the feeling while being sucked off.

“Twilight, I’m about… to cum,” came your voice, low and weak.

Twilight merely dropped her head down to the point that her lips were kissing your balls, before making a powerful swallowing motion.

… you only lasted about two seconds after that. Your legs gave a wild jerk, before going rigid and you unloaded into her loving muzzle.

Creamy stream, after creamy stream of your human spunk shot down her throat, the mare moaning loudly whilst her eyes shut tight, then opened wide and literally sparkled with joy.

The moment you gave her the last of your seed there was a blinding flash of light. When the light faded you noticed a pair of feathery wings upon her back.

Twilight squealed in delight around your softening member, before lifting her head off your cock.

“Thanks, Anon! Your cum is amazing!” she shouted excitedly.

Suddenly Rainbow Dash stormed in, “We got to get everypony to suck Anon’s dick. We need more alicorns!”

“Uhhhh, I’m not sure if that's a good idea,” Twilight replied in a worried tone.

“Meh, what’s the worst thing that can happen?” Rainbow said dismissively, waving her hoof nonchalantly.

The End