The pegging one
Strolling down the sidewalk, you keep an eye out for signs along the storefronts. Your friends suggested a cute maid cafe around here and you have some free time, why not check it out? Turning a corner, you see a girl in a maid dress standing in front of a store window and figure that must be the place. She has long black hair with bangs and a cheery smile, waving to you as you walk up. "Hello! Would you like to come in for some coffee and cake?" she greets you, pulling the door open. You thank her and step inside, taking in the sight of half a dozen maids running around with trays. One of them walks over and guides you to a table, pulling your chair out for you and handing you a menu. Hooking your bag over the end of the chair, you flip through the menu until someone comes up to take your order. The drinks here look fairly good, a lot of different types of coffee and tea, some shakes and smoothies too. The desserts look fairly generic though. Looking up, you notice something different about the maid walking up to take your order. They have short black hair and cute cat ears sitting atop their head, and what looks to be a tail poking out the back of their dress. They step up and pull out a notepad, ready to serve you.
"Good afternoon, miss, my name is Kenji and I'm delighted to serve you today" It's a boy! It's a boy in a maid's dress waiting on you! You bite your lip and smile, squirming slightly in your chair. When you heard about this place you thought it was just going to be a run of the mill cute maid cafe, but the crossdressing boy in front of you almost soaks your panties with his voice. With a trembling hand, you point out a drink and dessert on the menu and he jots it down. Watching him walk away, you can't stop staring at his rear even though it's covered by the skirt. Texting your friends frantically while the cafe prepares your order, you psyche yourself up in preparation of the next step. Kenji comes back with your tea and dessert, placing them gently in front of you, giving a bow.
"Would you like anything else, miss?" he asks politely, and you almost jump his bones on the spot.
"No, thank you. This is all for now" you stifle yourself, heartrate rising as you watch his ears wiggle. You're going to ruin this boy. It's happening.
Slowly sipping from your glass, you watch as most of the customers shuffle out after lunch. Once you're finished with your food, Kenji comes back over to collect your dishes.
"Excuse me, Kenji? Do you think you could show me to the washroom?" you ask, feigning shyness.
"Of course, miss. Just follow me" he replies, turning to lead you. You grab your bag from off the chair and follow him to a back room.
"It's just through here mis-" before he can finish, you push him through the door, following and locking it behind you.
"Wait, miss, I really can't do this, I could be fired!" Kenji protests, trying to make his way around you to the door. He hesitates as you pull off your shirt and fall to your knees, reaching up under his skirt to pull his undershorts down. Pushing him so he leans against the sink, you immediately take him into your mouth and wrap your arms around his waist.
"M-miss, please..." he stammers as you suck on him frantically, feeling him grow in your mouth as you swirl your tongue alone his head. He collapses back, propping himself up with his arms as you bob your head back and forth, feeling him hit the back of your throat as you take him deeper.
Releasing your arms from around his waist, you slip a hand into your pants and rub your clit as you deepthroat the catboy, causing him to groan out loud. Smiling to yourself, you swallow around him and work your tongue along the underside of his cock. Keeping yourself locked in place, you take your soaked fingers and move them to his ass, pressing the tip of one finger gently against the entrance. You can hear a bit of panic in his voice as he sways between ecstasy and fear, your expert tongue and lips winning out as you gently work your index finger in to the first knuckle. Putting a bit more pressure, you slide your finger in further as Kenji starts clenching tight around it, his cock twitching in your mouth as he does. Pulling off to suck on the head, you run your tongue slowly along the underside as he relaxes reluctantly, letting you slip your finger in and out completely. Finger fucking him steadily as he trembles under you, you force yourself to keep things slow. You let the head of his cock rest in your mouth as you curve your finger inside him, pressing lightly and a dollop of thin cum falls onto your tongue. You milk him slowly as he trembles, sucking lightly and swallowing every drop. A second finger finds its way inside him, and you twist them, cross them, making shapes insde his ring.
Satisfied that you've toyed with him enough, you kiss the tip of his cock and stand up, digging through your bag. Pulling out a large silicone dildo attached to a harness, you watch him stare as you fix it to your hips.
"N-no... I can't..." he whispers, backing against the wall. You tighten the straps and grin, reaching for a small bottle of lube and pouring a slow line along the length of your faux cock. Stroking it slowly, you stare into his eyes, making your way over to him. Without saying a word, you pin him against the wall and kiss him, hiking one of his legs up over your shoulder and lining up the head of your toy with his cute winking hole. Pressing your hips in lightly, you feel him fighting you. You keep prodding his hole methodically, your hand running across his chest to tweak his nipple lightly. Eventually he breaks, and his hole swallows the head of the strap-on as you drive in deeper to prevent him from breaking free. He's completely yours now, he can only shake and make cute noises as you stretch him open.
Kenji looks so cute, eyes closed, face contorted in a mixture of pleasure and pain. You lick up the side of his neck and bite lightly, your hand falling down to his half hard cock and giving it a playful squeeze. Your hips shift slowly, working the toy in deeper as you stroke him and you can feel his heartbeat quicken as you press against him. Rubbing your finger against the tip, you pull off a string of pre and rub it against his lips, slipping your finger into his mouth. Driving your hips in harder, you hear Kenji grunt softly. Angling the toy slightly, you watch as a mixture of cum and pre flow freely from his cock as you play with his prostate. Unable to take anymore, Kenji's legs give out and you lower him gently to the floor on his stomach.
"I'm not done with you yet" you whisper, pulling his skirt up and rubbing your toy between his cheeks. You hear him groan submissively as you lean over, working the strap-on back into him and laying on his back. Your hips move independently as you wrap your arms around him, pinning him in place.
Time passes, and you've plowed the shaking catboy in every position you can think of. He's thoroughly broken now, riding you absently, any resistance completely fucked out of him by your constant administration of prostate orgasms. You came a few times yourself from the friction of the toy and seeing Kenji shake and cum without anything coming out. He drops his hips onto yours, hugging you tight as he shudders, and you smile as you feel him cum again. You let him rest for a few minutes, gently pulling him off you, standing up as he kneels dejected on the floor. Washing the toy off thoroughly, you grab your phone and stand over him. Picking his face up by his chin, you slip the tip of the toy past his lips and snap a few photos. Fucking his face gently for good measure, you undo the straps of the toy and pull your shirt back over your head.
"This was fun, Kenji, I'll make sure to leave you a biiiiig tip" you giggle. "And I'll be back tomorrow to give you an even bigger one" Kenji just looks at you, giving you two peace signs as cute anime boys do, his yellow eyes faded.
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