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It’s been a while since the last story by Mister S!
So here is a new hot short story!
As always, it’s so exciting to read something from Mister’s POV ;)
Enjoy gurls!

A Little Help For the First Time

by Mr. S

It’s so hard to meet a good sissy these days. Oh sure everyone wants to chat online about fantasies but to find one willing to do my online training and then even show up… Wow, that’s a real gem.

You arrive at my house as instructed and ring the bell. Almost immediately the door opens and you are greeted by a lady in a robe who beckons you in.

“You must be Sissy Lilly. You may call me Sissy Daisy.”

As your eyes adjust you get a better look at Daisy. Sure enough, this pretty girl is really a boy. She takes your coat and guides you to the back of the house into a spacious bathroom sparkling with white tile.

“Strip down and hop in,” she says as she gestures to the bathtub which is frothing with bubbles and flower petals. “Oh, don’t be shy. I’ve seen all the pictures you’ve sent to Sir.” With that encouragement you slowly strip naked and get into the tub. “Relax for a bit,” Daisy tells you as she scoops up your clothes and scampers out of the bathroom.

At first you panic as you’ve lost your clothing but you realize you wouldn’t catch her anyway. Instead you lie back and try to relax. It gets easier as the warm bath, bubbles, and delicate floral scent envelop your senses. The experience is very calming. Just as you’ve zoned out, Daisy returns and she kneels by the tub. She grabs a sponge and starts washing you down. It’s so relaxing as she gently cleans your body. Eventually she prompts you to stand and you do. She inspects you from head to toe.

“Oh, sweetie. You did a good job shaving. Sir will be so happy. Sit back down and soak and I’ll get your outfit together.” You relax in the tub and she scurries about getting everything together.

Eventually she directs you out of the tub and dries you with big fluffy warm towels. Once dry she helps you into a robe like hers and sits you by the mirror. From toe to head she grooms you. Starting with red nails and ending with a dark wig. She perfectly applies makeup and lipstick giving you dark eyes to match the wig and bright lips to match your nails.

At this point she helps you out of your robe. You’re a little shy still but finding it easier to be naked in front of her. She tosses the robe in a hamper and returns with a small box.

“You know about the chastity requirement, right?” She asks.

“Y-yes, he told me,” comes your slow, meek reply.

“Ever wear one of these before?” She follows up.

“No, no I haven’t,” you reply with nerves obvious in your voice.

“Well I think you’ll love it.” With that she kneels and slides the ring on immediately followed by the plastic tube which she wiggles on easily. Once the two are connected she threads the lock in place to hold it together.

“Where’s the key?” you ask.

“I don’t know. I’m sure he has it somewhere safe. Any pinching or tightness?” She rolls the cage around in her hands.

“No, not at all.”

“Good.” She rapidly clicks the lock shut. She rolls your encased package in her hands a bit more before returning to her feet. It’s oddly erotic letting her play with you while in chastity. She gets your outfit from the closet and returns.

“First things first.” She hands you a pair of panties and you step into them. They’re white, lacey, and most noticeably crotchless. As you pull them up your chastity cage flops out of them hiding nothing. As you tug them up you feel the delicate ruffles on the back. “Arms out.” Obediently you put your arms out and she threads a bra on you. It too is white and lacey. It’s a little tight and you stiffen your posture as Daisy slides behind you to fasten it. This done she hand you a skirt, a bright pink tartan skirt to put on. Pulling it up you realize it’s only about 4 inches long and won’t cover a thing. You do your best to position it on your hips but the comical shortness makes it useless. Daisy doesn’t skip a beat and fetches a pair of black four inch heels that she helps you into before popping back up.

“Well, what do you think?” she asks.

“I look ridiculous. I look like every teen boy’s fantasy of a schoolgirl.” You reply as you gaze into the mirror.

“I think you look sexy. And what better outfit for your first blowjob than a cute schoolgirl? Come with me.”

She leads you a few doors down the hall and into a large bedroom with a vaulted ceiling and Japanese inspired furniture. The bed sits low and the nightstands have bright potted orchids on them. It’s evidence of an analytical personality. You turn back to Daisy and stop in your tracks.

She’s removed her robe and to your surprise is dressed exactly like you. The bra, skirt, and panties are identical. She’s even got a chastity cage on just like yours. The only difference between you is your long dark brunette hair and her light blonde bob.

“Just relax, I’m here to help,” she says as she moves toward you. She puts her hands on your face and pulls you in kissing you gently. You panic and turn causing your chastity cage to clack against hers. “See, we can’t get in real trouble. Why don’t you relax and play with me? Sir will be along shortly.”

With that she pulls you back to her and begins kissing you passionately. You melt and fall into her arms returning her lustful embrace. The kissing deepens and she pushes you back until you fall onto the bed. She quickly kneels between your legs, grabbing your chastity lock in one hand and petting your encased sissy clit with the other.

“Aren’t these just great? You get turned on and expand only to be squeezed back. Even the squeeze is erotic. In fact it feels like you’ve grown as much as it will allow. Is it squeezing?”

“Yes but it’s not bad. A dull ache. Somehow I’m more aware. More horny…”

“I know. It’s the best.” She drops the cage and climbs over you getting back to kissing.

You make out with her for quite a while. She’s a hell of a kisser and a real slut. She licks your neck, teases your ears, and repeatedly gives little tugs on your chastity cage. You melt into her and don’t even notice me walk in.

“Showtime,” calls Daisy as she turns to see me. She pulls back off of you and gently lifts your shoulder to torn you to the edge of the bed. Almost instinctively you sit up so your feet land on the floor and your knees are up high due to the short bed. As I walk to you with your head at the same level as my pants’ zipper the moment becomes surreal.

“Has she been a good girl?” I ask Daisy.

“Oh yes,” she replies, “Lilly here is a real slut. I love playing with her.” Turning to you she adds, “And you know what to do now.”

With shaky hands you undo my belt, unbutton my pants, and slowly draw my zipper down. My cock flops out and you briefly pause.

“You know what to do,” blurts Daisy, “give it some kisses.” Following her direction you lean in and start by kissing the tip. I reach out to Daisy’s face and she sucks the tip of my thumb into her mouth. What a whore. I love her.

My cock increasingly stiffens from your kisses and eventually you wrap your lips around it and suck it down. Long, slow slurpy sucks follow until I push your head back. I take two steps back and out of my pants which I kick to the side.

“Get off the bed and kneel,” I say. You slink forward obediently transfixed on my firm cock glistening with your saliva. “Is this what you want?” I ask.

“Yes – yes, sir,” you reply.

“Well then enjoy your first blowjob”

That is all the encouragement you need. Easing forward you once again take my dick in your mouth and begin to suck with a fervent desire. Jack hammering all the way down just as you practiced with dildos and sucking hard as you pull back up. You feel Daisy cuddle next to you putting just a little pressure on the back of your head with one hand and once again tugging on your chastity tube with the other.

“I think she’s really enjoying herself,” says Daisy who pushes your head to one side of me so she can lean in. Her lips and tongue slide up and down one side of my shaft with you on the other. At times you pause to kiss each other. It’s wonderful and playful. I can tell you are lost with the fireworks in your head.

Eventually Daisy pulls back and tells you, “Finish your job, sweetie.” You return to mouth humping my cock and you go for the gusto, bobbing up and down and twisting to get me off. Soon I’m ready and I gently push you into position as I hold your hand on my cock and help you jack me off on your face. I cum everywhere. Mostly in your mouth but streaks of my man goo coat your face.

As soon as I’ve shot my load, Daisy shoves your head back on my dick simultaneously coaxing the last dribble of semen out of me and forcing the relatively controlled dollop of cum on your tongue to slosh through your entire mouth. The spooge coats your mouth and throat causing you to choke a little which only forces some into your nasal passages. This is the cum anointment you wanted. Dizzy from horniness and sensually overwhelmed by jizz you’re lost.

Daisy pulls you back off my cock, sucks me a couple times to clean me and holds you. Gently she begins sucking and licking the spunk from your face only to redeposit in your mouth through a volley of cum filled kisses. You slowly come back to reality as she gives you a long cum flavored kiss and once again tugs at your chastity tube. As you regain your senses she pulls back from your quivering body.

“You did a great job, Lilly. Daddy, I like playing with her. Can we keep her?”

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