Sissygasm

You arrive at Megan's house the next day with a printed version of your embarrassing essay.

Her dad answers the door. "Oh, hey Aiken. Whatcha got there?" He grins.

You quickly yank the essay behind your back. "N-nothing! Just homework. Um, is Megan home, Mr. Brandt?"

He shrugs. "She'll be down in a minute. You know how women are." He leads you through their very nice house, inviting you to sit on their huge U-shaped sofa. "Been a while since I've seen you, Aiken. You look, uh, more... comfortable than last time."

You blush. The last time he had seen you, you'd been in a little black party dress. "Er, yes Sir..."

He chuckles when you call him Sir. "Well, guess it's none of my concern. I'm sure ol' Aiken knows what he's doing. Him and I have pretty similar views, after all. But if you ever need a little extra spending money - you know, for clothes and makeup and stuff - I can hook you up with a job."

"Oh, um... thanks. I'll keep that in mind." You shy away from his grin and turn a little to avoid his eyes.

"Of course, if you wanted to skip the job entirely, you could just model those cute clothes for me privately..."

What?! You look at him, a little stunned, trying to figure out how to respond. Luckily Megan comes down just in time.

"Daddy, stop teasing him. You know Aiken's a soft boi and gets flustered easily." She comes over and sits by you, pulling your head to her chest protectively. She's wearing leggings and a Sorority T-shirt, despite being a senior in highschool. You can smell her strawberry perfume as she tousles your hair. "Poor thing. Come on, let's go up to my room."

Mr. Brandt shrugs and waves as you ascend the stairs behind Megan. "Have fun you two. No need to keep the door open." You're sure you can feels his eyes following you as you ascend the stairs.

As soon as you're in Megan's room, you start looking for your key. You've been so pent up this weekend, you can't wait another minute.

"Looking for this, sissy?" Megan teases. She jangles something at her throat, and you realize she's attached your key to a little gold chain and is wearing it around her neck, letting it dangle in her cleavage.

You gasp out, seeing it there. "Yes! Please, Miss. Unlock me!"

She rolls her eyes. "Pathetic. You should be begging me to keep you locked up longer. It's for your own good, after all. That dicklet of yours is useless and just turns you into a horny perv. You'd be much better off trained to not get hard at all. Much more civil that way, don't you think?"

"I... um..." You aren't sure how to answer. You really, really want to be free of your chastity so you can unload the orgasm that's been building up for days.

She teases, pressing in on you and leaning down so you can see the key dangle just in front of you, along with her cleavage, a peek at her pink girly bra...

You wince a little and bite your lip. Your cock throbs and pulses against your cage.

"Hmm? What's that, sissy? Feeling a little uncomfortable all of a sudden? Go ahead, show me how much of a good boy you are, Aiken. Beg me to keep you caged longer. A whole month, maybe. Go on."

You squirm and suck in air through grit teeth. You lock eyes with the girl tormenting you and start to squeak and stammer, "I... P-please, Miss Megan..." but you can't do it. It's too much, too soon. "Please uncage me! I promise I'll be a good boy for you if you do!"

She stands up and sighs. "So disappointing. Alright, sissy. Pants down, on the bed and spread 'em."

You quickly comply and allow her to unlock the cage for you. You sigh with relief as it comes off, giving it a few strokes to rub off the feel of it being trapped for so long. It feels so soft and small right after coming out of the tight space.

"Ew! Don't do that in front of me, sissy! Bad boy! Put your pants on and thank me properly."

You follow her orders obediently and quickly, and thank her profusely.

"Better. Alright then, next order of business - I believe you have an essay for me?"

You produce the papers with a shaky hand - and she snatches them quickly away from you, reading greedily and giggling often.

"Oh wow, this is rich! 'I loved how cute and girly the sissy dicklets looked, especially when they had sissygasms. I wish my tiny sissy dick could drip like theirs...'" she reads out loud.

You wince and glance at the door, shivering with humiliation as you hear your own words read out loud.

"Shh! Your dad could hear. Come on, just read it later, it's embarrassing!"

Megan smirks and pulls the papers farther away from you. "It's your essay, sissy. You should be happy I'm reading it. Actually - why don't you read it for me? Out loud, standing in front of me like you're presenting to the class." She waves the papers in front of you. "You want to be a good boy for Miss, don't you?"

You grimace and take the papers. "Yes Miss..." and start reading. You know you can't say no. You were crushed under the power this cheerleader had over you, overwhelmed by the preppy popular girl.

You recite, "I enjoyed how delicate and feminine the sissies came. So different from a normal masculine orgasm, which is needlessly aggressive and messy. Rather, a sissygasm appears to be a simple, soft pleasure, derived more from the satisfaction of giving pleasure to the men fucking them, rather than from the stimulation itself..."

Your face burns as you read, hands shaking so you can hardly read the paper. But you keep going, knowing how wide Megan's grin is, how much she's loving this. You glance up and see that her phone is out, recording you.

"I- I... really loved how happy the sissies looked as they were being feminized and emasculated... it... it made my dicklet throb, and I fantasized about being them..."

By the time you finish the paper, your knees are shaking and you hold back sobs of embarrassment.

Megan sighs, satisfied as you scurry back to her bed and sit beside her.

"Good boy, Aiken! Very good boy. That was hilarious!"

You scowl and turn away, feeling some wetness tease the corners of your eyes. "Yes Miss."

"Aw," Aiken says pityingly. "Was that too much, sissy? Did Miss go a little too far and make you cry?"

You shake your head, holding it in with clenched jaw, gripping the bed sheets tight.

"There, there, come on, I'll make you feel better." She pulls your head over and clutches it to her chest. You can feel her breasts press against your cheek, the way her T-shirt slides against the silky fabric of her bra. She's so soft, but also warm and more comforting than you would have guessed. Her heart beat thuds dully through your skin and resonates across your body.

You close your eyes and breath in deeply, gulping down the tears that were threatening to burst from you. Your shaking ebbs and a calm washes over you.

"There you go, that's a good boy..." your Miss coos softly in your ear.

Then she adds with a slightly more flirty tone, "Would this help? Hmm?"

The next thing you know, her hand is slipping into your shorts, sliding over your smooth shaved skin above your pelvis, and to your cock.

Your breath catches when her soft fingers and palm slip around your genitals, cupping your cock and balls in one hand. She pets your hair and beings stroking, gently and slowly pulling her hand up and down to rub your sensitive area.

You release a shaky sigh and squirm a little. You've been so pent up, it feels amazing. The head cheerleader, Megan Brandt, was stroking you...

"Shh... don't move, sissy. Just relax. You're doing so good, hardly even getting hard at all. Good boy, Aiken. Just like that..." she whispers.

It's true - you weren't hard. After so long in the cage, your dicklet was still readjusting to its new freedom. You were semi at best, still floppy against her hand. But despite that, it felt incredible - better than masturbating normally did sometimes.

"Hmmmmhh..." your mouth opens on its own and a noise of pleasure comes out. A moan.

Aiken giggles, a twinkle of soft laughter that makes your heart flutter. "Does that feel good, sissy? I can tell you've been a little off, recently. Is this helping? I may be hard on you, but it's only because I want you to be the best sissy possible, 'kay?"

You nod. "Yes Miss... thank you..." and feel your body tense. Her painted nails brush the bottom of your balls and a wave of pleasure shoots up your cock.

"Hehe, did that feel good, sissy?" she does it again, tapping her nails over your balls then using her fingertips to massage them sensually.

You gasp and moan louder, your cock hardening and aching with a familiar deep pleasure. A building orgasm pulsing just on the edge of release.

Aiken slips her hand back, away from your dicklet just as you were getting close.

She leans your head back up and looks into your eyes. "Do you want to cum for me, sissy? You got hard again. Miss prefers you soft. You know that, right?"

You nod, answering both questions with a whimpering, ****, "Yes Miss... Yes... Please..."

She smiles and cocks her head like she were looking at a puppy that just did something very cute. "Aw, well... how could I say no to that face?"

She pulls her knees up and prepositions herself on the bed, sitting behind you and leaning your head back into the cradle of her arms, reaching over so she can continue rubbing with one hand.

"Relax, sissy... shh... good boy..." she whispers, brushing your thighs with her fingertips.

Your heartbeat slows and you relax, gulping. This new sensation is like being enveloped in a warm blanket with a mug of tea. It's relaxing and almost sleepy, but at the same time, unbelievably sexual. You want to please her, to hear her call you a good boy again. Every time she does your body tingle but in a way you've never experienced before. You didn't need to perform or stress over anything. You only needed to listen to her soft words and follow along, letting yourself get washed away in the gentle pleasure.

Her hand silently migrates to your balls, and you feel her fingers and palm work to stimulate them in soft circular presses.

You moan under your breath, a warm pulsing emanating through your erogenous zone.

Megan kisses your lips and slides her hand up your shaft, making you realize that you've gone slightly soft again. Then she returns it to your balls and whispers in your ear.

"Cum, sissy. Cum for Miss."

And you do.

You squeak and arch your back, feeling a sharp pleasurable tingle run up your legs and spine. Warm wet semen dribbles out of your tip and down your shaft, trailing over your balls and Megan's hand as she continues massaging. A few small spurts send little ropes onto your shorts and boxers around your knees, but for the most part, you only leak, not spray.

"Hehe, good boy! I think we can call that your first sissygasm, Aiken. Miss is very proud of you."

You catch your breath and sit up, gulping and blushing, but smile shyly.

"Thank you, M-miss... That felt... incredible."

She smiles back, strokes your hair with her clean hand for several minutes while you come down from your sissygasm. "Good, I'm glad. I was serious when I said I could tell that you've been in a rut lately. Once you get your little mess cleaned up, I think we should do something about it."

"Do something? Like what?"

She smiles, "I think it's time you go to school in girls' clothes."