An After School Romance

Sweetie had no small reservations about putting the toy in such a sensitive spot. Even though a part of her was throbbing and wanted to go through with it, some sense of nervousness held her back. She had already exposed her most private organs to her teacher, and had them touched and caressed in ways that she never thought possible. It would only be right for her to return the sexual favor. But all the same, she had never actually been penetrated before. She had seen it on camera, but had never experienced it. So to say that the quivering she now experienced was from excitement would be more than mildly deceptive.

“I…I just don’t know,” she said.

Cheerilee noticed the worry painting her beloved’s face and turned to face her. “It’s okay, Sweetie Belle. All you have to do is just gently put it inside you, and then put the other end inside me. It’ll feel amazing, I promise!”

“But…doesn’t the first time…hurt?” Sweetie asked. She had seen a film once where the stallion took the mare’s virginity, and she couldn’t stomach the screaming. She knew that the rest of the experience was very pleasurable, but she didn’t like the idea of having to suffer in order to feel it. Her nerves became even more uncontrollable, and she felt tears begin brimming. She wanted so much to make Cheerilee happy, and she felt unable to do so.

Her marefriend saw the sadness evident in her face and pulled her into a gentle hug. She let Sweetie cry for a moment, before softly kissing her cheek. She slowly sat back, without releasing the nervous filly, and looked her in the eye. “Sweetie, baby, listen to me. I love you, no matter what. If you’re too nervous to go through with this, that’s fine. We can wait.”

“No,” Sweetie said as she pulled out of the hug, “I want this. But…I just don’t want the pain that goes with it.”

“I understand,” Cheerilee said compassionately, “because I remember when a stallion first slept with me. It hurt for a few seconds, but then the sheer ecstasy took over and I rode him to oblivion. There’s nothing wrong with a little pain to get to a lot of pleasure, darling. But, like I said, I’m willing to wait if you want to.”

Sweetie shook her small head. She knew that this would seal her love for her teacher forever, and she felt that she was only a few hoof steps away from it. She was just a little wary of taking them. But then Cheerilee, who had been backing her all along, suddenly threw her weight under the young pony, and she was able to face the prospect without fear. She felt all of her doubt wash away in the beautiful green eyes that cast their love down at her.

“Would you like some help?” Cheerilee asked.

Sweetie nodded, and her teacher maneuvered one end of the toy into an upright position. She then instructed her student, as gently as if she were teaching her a regular lesson, to squat her rump over the tip. Once this was done, she moved her hooves up over Sweetie’s flanks, and gently lowered her onto the plastic penis. Sweetie howled in agony as she felt it push ever deeper into her body, breaking her hymen and ensuring that her naiveté was destroyed forever. Her rump quivered as her vaginal muscles finally managed to take control of the toy, leaving one end poking outward.

Cheerilee narrowed her eyes and gently began to suck on the toy. To her delight, she found that Sweetie’s hold was ever so loose, and she began working the toy back and forth. Each new oral thrust elicited a deeper moan from the filly, and Cheerilee was happy to administer more. It wasn’t loose enough to where the toy tumbled out, but it was just so to where it could pleasure Sweetie. Soon enough, though, Cheerilee felt an urge bloom from her own flower, and she stopped her small blowjob. She bent upwards to kiss Sweetie, before turning around and asking her to proceed with the mounting.

Sweetie, having been exposed to this kind of thing via her sister’s secret stash, immediately clambered on top of her teacher. She attempted to move around so that her partner would be comfortable with the mating, but no matter what she tried, she’d always stick an errant hoof here or a misplaced joint there. She felt terrible, but her teacher gently encouraged her until she finally managed to find the right position. She lifted her rump, nodded at Cheerilee, and then pushed her way inside.

Cheerilee howled at the explosion of pleasure that laced her body. It ran its way up her spine and practically melted her mind. She knew that it was destiny for her and the beautiful filly to be together, and their first sexual session was fulfilling all of that. As Sweetie began slowly thrusting back and forth, the dark pink mare saw stars in front of her eyes. She hadn’t been with a filly since Smooth Swirl, and she had forgotten just how amazing they could be in bed. Sweetie’s muscles worked their way into a frenzy, and soon the two mares were moaning right alongside each other.

“Oh…oh…Cheerilee,” Sweetie groaned as she thrust, “this feels so good! I think it’s going deeper every time I pump!”

“It is, Sweetie,” Cheerilee panted, “that’s what makes it such a great toy! Oh! Oh! Oh! You’re pounding so deep! Come on, sweetheart! Come on, my love! Keep fucking me! Oh…yes! I needed this so badly!”

Their cries went unnoticed by the rest of Ponyville, which wandered by completely oblivious to the beautiful scene of love between a teacher and a student. Had they known, their reactions would have been mixed, as some ponies found that making love to foals was odd and weird, while others found that it was a beautiful way to show affection. Even Princess Celestia herself had an opinion, telling everypony that ponies had a choice in love, and some chose to love foals. Cheerilee was one of those ponies, even though the EEA had strict rules forbidding such interactions.

But those rules did not apply in this bedroom at this moment in time. The filly and the mare seemed frozen within some kind of self-contained continuum. It was a world where they were the only two ponies who existed, and their shared vaginal intercourse was the ultimate prize. They had exposed themselves to each other, body and soul, and they knew they could never recant their feelings. As Sweetie’s thrusts became harder, and their cries became louder, their love somehow grew.

“Oh! Cheerilee! I feel like I’m gonna explode all over this cock!” Sweetie cried.

“Yes! Fucking cum for me, baby!” Cheerilee howled back at her lover, “please, baby! Shoot your Celestia damned love juices all over that big toy! Oh, baby! OH! OH! OH! OH! FUCK! FUCK! FUCK! OH! YES! OH!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!”

“AHHHHHHHHHHHHHHHHHH!!!!!!!!!!!” Sweetie screamed.

Their conjoined orgasm was a magnificent thing to behold, and the two mares collapsed in exhaustion afterwards. Cheerilee managed, somehow, to pull down the covers and they cuddled underneath them. Their pants were rapid, and their sweat stained the sheets, but they were each incredibly satisfied. They knew that they would never betray the newfound love they felt, and their actions that evening had solidified it.

“Sweetie,” Cheerilee said as she buried her face in the filly’s shoulder, “you’re fantastic.”

“You’re not so bad, yourself,” Sweetie managed to get out as she instinctively ground her body against her teacher’s.

“Please, baby,” Cheerilee said, “stay with me forever. Be my mate, even in secret.”

“I will, my love,” Sweetie responded, kissing her teacher tenderly, “I promise I will.”