Pretty Pony Pounding
The Japanese school girl uniform looked great on the effeminate equine. "Sammy? I'm not so sure about this anymore." His legs fidgeted and he stared at the ground. He looked amazing in skirts, of that he was sure. But what his friend had in store was different from what he usually liked.
"I promise you, it'll be fine. You'll love this. Now, lift up your skirt."
He timidly did as he was told, following what she said without question. Sammy enjoyed supporting the horse's crossdressing habits. He wasn't sure what it meant, if he wanted to be a girl or if he just liked the feel of pretty clotes. Sammy never judged, Sammy was supportive. But Sammy was so sure of what she wanted, and she knew Pepper looked cute enough to eat like that. So the mongoose convinced him to dress in their favorite outfit and to let her have her way with him.
Sammy was a sophomore in college whereas Pepper was weeks away from turning 18. She was his cool college friend. She'd stuck with him through all the rough years of school, helping him out of his depression, and showing him alternative lifestyles, trying to help him find his own path through life. She helped him buy all sorts of outfits and accessories, books and movies, all of which had to be kept at her apartment so his family wouldn't find them. She'd even helped him pick a new name. Charles just woundn't cut it anymore.
He couldn't remember how Sammy had managed to convince him. He'd merely expressed a curiosity about sex. In all her wisdom, she'd volunteered to take his virginity, having lost her own years ago. Now here they were in the bedroom of her apartment, reaching down to lift up the pleated skirt.
Lavender panties cradled his cock, soft like goose down. He blushed softly, turning his head away as Sammy knelt in front of him. Her fingertips lightly stroked him through the cotton. He jumped slightly, having never been touched there before. "Calm down," she cooed, pulling the undies halfway down his thighes. "This will feel really good, I promise." For someone so timid, he had a good 6 inches, flacid. She licked her lips, bending down and kissing the head. She ran her tongue along the entire shaft, wetting it. Pepper gasped and clenched the skirt tighter. It did feel good. His cock twitched and slowly began to grow. "There, see? I told you you'd love this." Her warm breaht excited him more. One hand grabbed hold of him firmly, stroking lightly. He choked on his words, clenching his stomach muscles.
She was just getting started as she stroked him, lowering her head more to lick at his sack. Pepper gasped loudly, precum already bubbling at the head. Not wanting to excite him too much too soon, Sammy merely ran her fingers up and down his shaft like feathers. Meanwhile, she flicked her tongue along his balls. She kissed and she suckled, almost getting them all in her mouth. Pepper's head lolled back, moaning pathetically, trying to keep his knees from buckling. He felt like water, loose and fluid. He managed to regain focus for a while once Sammy had stopped. The mongoose let him have a few breaths before plunging her mouth to his now foot long erection. She sucked hard on the head at first, the ceased and let her head sink. So many inches slid easily down her throat. He watched in amazement how deep she could go. Pepper was so lost he didn't notice her hand creep up behind him. They slid and sank into his unsuspecting tailhole. He clenched at first, scared. But some soft movement from her digits and he allowed her deeper inside. She looked up at him, eyes shining. "Is this what you want?" Her voice was so soft, he barely heard her. He nodded stupidly.
Sammy removed herself from him. She pulled those pretty panties all the way down before she stood up. Without anymore words, she led the pretty pony to her bed, instructing him to get on all fours. His tail flicked nervously and his cock dripped quietly onto his skirt and the sheets. Pepper heard his friend rummage through something. He heard plastic and rubber and something wet. He turned his head, watching her approach him with nothing below the waist but a bobbing strap-on. She climbed atop the bed, kneeling behind him. The mongoose lifted his skirt and brushed his tail aside, exposing his dappled behind. "Relax," she murmured as she inserted two fingers again. Now they felt slick and wet, making him feel so much better. Pepper moaned and tangled his fingers in the sheets. She turned them and smeared the wetness all along his quivering hole. Lifting herself and holding his thighs firmly, she eased the head of the rubber dildo inside. He panted, gasped, and held his breath, trying to quiet the pain. The strokes were slow and shallow, setting up a nice rhythm. Eventually, his body moved with hers, relaxing. She moved in deeper, moaning herself as a small dildo moved inside her as well.
Pepper spoke his first intelligent word as he felt her truly fuck him. "More." Sammy smiled and drove the rest of her faux dick deep inside. Again and again, she pounded him hard, receiving a cry in thanks. He thought he'd go crazy from such unbridled pleasure. "I'm cumming, I'm cumming!" he groaned, arching his back and readying himself. Sammy reached beneath him, clutching that aching hard cock. Orgasm ripped through him, splashing in white waves upon the bed. His friend milked every drop from him, feeling it pulse in her palm as load after load ejected. Slowing she removed herself, letting him cherish where she had occupied him. He lowered himself to the covers, sweat beading across his brow. Sammy removed the sex toy from herself and crawled in beside him, holding him close and stroking his mane. He looked up at her, seeing that familiar small smile. A blush crossed his cheeks. "Can...can we do that again?"
"Only if you promise to do my laundry when we're done."