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Chapter 17
by
Nicegent42
What's next?
Chapter 16
A half hour after going to bed, Zeek was still softly weeping under the sheets when he heard a rapping at his chamber door.
“Please, just leave me alone, Liz. Let me sleep”, he begged after pulling the covers from over his head, not even realizing that he was still using his Ezme voice.
Despite Zeek’s pleas, the door still opened, though it was not his sister making an entrance.
“You sure you don’t have time for lil’ ol’ me, May-May?”.
“Oh, Thea, it’s you…”
Thea closed the door behind her and slinked towards the bed as Zeek peeled off the covers and swivelled round to switch on his bedside light. Thea sat next to him as he glumly slouched, small tears still eking their way out of his ducts, his nose gently sniffling.
“Hey, what’s wrong?”, Thea asked, feigning confusion and concern as she turned Zeek’s head to face her. “Why May-May, you’ve been crying! Aw, come here, baby-girl!”
Thea brought Zeek’s head to her shoulder/ bosom and let him weep for a while, one hand playing with his wig hair while the other softly held his hand. As she cradled the meek and helpless **** crossdresser, Thea could feel her juices flowing; there was nothing more arousing to her than a submissive; especially a submissive ‘gurl’ she’d feminised herself. And especially one looking so deliciously delectable in ‘her’ skimpy negligee.
Finally, Zeek’s tears petered off.
“There, there, it’s not all bad. You’ve been such a good girl, May-May. Remember that promise I made you?”.
“Promise?”
So traumatised was Zeek that he had forgotten all about Thea’s vow till she quickly gave him a peck on the cheek.
“Anything you do with your date, I’ll do with you.” Thea said, ending the sentence with a giggle.
Zeek’s eyes widened like saucers as he thought, ‘Ooooohh, that promise! How could I forget?!’
“Oh, yeah.”
Thea giggled, then ordered, “C’mere…”, pulling Zeek’s face towards her own and planting upon his lips a soft, languid kiss.
Instantly, Zeek melted into her embrace; it was nothing like the disgusting smooches Cal had given him. Zeek didn’t have to pretend to enjoy the attention, eagerly following Thea as she ended the kiss and began anew, following suit with each new technique Thea exhibited. She didn’t have to **** her way into Zeek’s mouth, but still she burst past his teeth like a band of marauders storming a castle, claiming the treasure inside that was Zeek’s own tongue.
As Thea gripped Zeek’s arms, she pulled him into a tight embrace, slipping her hands all over his back and sides, kneading his pert butt. Uncontrollably, Zeek moaned girlishly, making Thea giggle with glee between kisses.
Thea’s hand slipped between Zeek’s legs, parting them as it landed straight upon his panty-front, making the young crossdresser gasp.
Thea looked into Zeek’s eyes as her fingertips began to rub over the silky fabric, and she breathily declared, “You’re so beautiful, May before we move on I wanted to see if you would do something for me.”
Thea continued to dominate Zeek’s mouth as she rubbed over this underwear, feeling the less than large cock underneath rapidly spring to life and grow another 2 inches till it was at full mast. His unit hard enough, Thea disconnected her mouth from ‘Ezme’s’ and slipped her hand underneath the fabric, gently caressing and tugging at the uncircumcised yet clean shaft within. Zeek shuddered and gasped, never having felt another person’s hand on his member before.
“You like that, don’t you?”, Thea asked, her voice soft yet authoritarian.
“Oh yeah, I like that!”, Zeek laughed as he wheezed. “What do you want me to do?” he asked willing to do ant thing to keep her from stopping,
“And you like feeling pretty”.
“I… I guess?” he answered, wondering if this was what she wanted.
“That’s right, a pretty girl like you? You liked getting all dolled up, didn’t you”.
‘Oh. Yeah. This was the sort of stuff Thea said she was into when she first put makeup on me…’, Zeek thought despondently.
“What? No, I’m only dressed like this because my sister is blackmailing me. I’d never do this if I wasn’t being **** to”.
Suddenly, Thea’s hand stopped, and a disappointed frown appeared on her face.
“Oh, that’s a shame”.
Thea retrieved her hand from Zeek’s panties, sighed and got up from the bed.
“Wait, why are you stopping?”, Zeek asked, needy desperation in his voice.
“I told you earlier how I like my girls, and boys, pretty. If you’re not going to play along so we can both have fun then there’s nothing for me here”.
Thea turned and walked towards the door, while Zeek quickly panicked.
‘SHIT-SHIT-SHIT-SHIT-SHIT-SHIT SHIIIIIITTTT!!! You were just about the finally score, you asshole! You already sucked your best friend’s dick, which your sister found out about; lying about liking being a girl or whatever for a while is nothing compared to that!’.
Thea’s hand was on the doorknob when Zeek shouted, “Wait! I was wrong! I do love being pretty and girly and stuff! I was just, errr… in denial!”.
Thea stopped moving, still facing the door as she asked, “So you really do enjoy being a girl, May?”.
“More… more than anything… You and… ugh, Liz… showed me what I had been hiding away from for so long…”.
Out of Zeek’s view, Thea grinned a nefarious grin. ‘Got er’.
“Oh. Well that’s good to hear. I’m so proud of you for coming to terms with who you really are, May-May”, Thea congratulated as she slinked back to the bed. “Get on up there and scooch back a little. I think we should put that new hair of yours into some rollers, don't you?”.
Zeek rushed to do as instructed, lying propped up on his elbows with his legs out-stretched. “So long as you don't leave.”
Thea climbed up onto the bed and onto all ours, stroking Zeek’s legs as she creeped up to his midsection.
What felt like an eternity later rollers now holding the glued on human hair in place Thea massaged the crossdressing boy's thigh, Her ordering him around, “Lift yourself up a lil’”, slowly slipping her hand into his panties, instantly seeing a tremor of pleasure run down through his body down to his knees. “Now, where were we?”.
Thea’s hand once again found Zeek’s turgid penis and began stroking, this time more firmly, peeling the foreskin back.
“You were saying?”, Thea led.
“Errrr I just love being a hot girl, making myself all pretty and stuff for you!”, Zeek squeaked out, melting at Thea’s touch.
“Mmm, and what do you love most about it?”, Thea asked, subtly increasing the intensity of her handjob.
“What I love most about it? Errr…all the attention I get! I love having everybody look at me and go, “Wow, she’s gorgeous! I wanna look just like her!”. When I was a guy, nobody ever paid attention to me…”.
‘Wow, getting candid here. Though this is a weakness that may prove useful to exploit later on’, Thea thought, Zeek’s impromptu confession betraying more of the fem-boy’s insecurities then he likely realised.
“Good girl. Let’s up the ante, shall we?”.
In a single swift motion, Thea bent over and swallowed the entirety of Zeek’s penis, making him yelp and draw breath. An expert at using her tongue, Thea went to town as she slurped and slathered over the phallus, and Zeek moaned, “Ooohhhh Oh God!” His own voice almost musical.
Thea withdrew her mouth and stroked, rubbing the head in the palm of her hand as she asked more questions. “And what specifically about getting dolled up makes you feel like you deserve all the attention?”
“I errr… like makeup! No, I love makeup!”.
As a reward, Thea sucked on him a little more, then asked, “And what things about makeup do you love the most?”.
“I oooh like the way ah ah eyeshadow and eyeliner and ahhh mascara make my eyes look big and eep pretty, especially when I ack, oh god that's good… have big fake eyelashes on that flutter and drive people wild! Ooohhh”.
“Fabulous! And anything else?”.
“I love how Eeekk! Creamy lipstick feels on my Mmmmmm my lips, and how it makes them hoooo ah yeah! Making them big and sexy and kissable! Oooh” he answered having a hard time holding back his own ejaculation. A part of his mind wondering if this is how he made Cal feel.
Thea’s mouth found Zeek’s cock again as Zeek held onto his bed for dear life, completely at his lifelong crush’s mercy. He was getting so close, and there was not anything he would not have said or done for Thea to keep up her attention, especially seeing as she was the first girl he’d ever done anything with.
For the final time, Thea rose again to push Zeek further for her own pleasure. Unbeknownst to him, she’d been getting off herself, her free hand having travelled south to her gushing mound.
“So you like kissing. Do you like kissing boys?”.
“Yes! Yes I like kissing boys!”.
“And I bet there’s something else you like to do to boys with that mouth of yours? C’mon, what is it?”.
“I like.. I like…”.
“Yes?”.
“I like… sucking dick! I love dick!”.
“Good girl, May-May, good girl! And what about giving blowjobs do you like the most?”.
“Oh God, Oh God!”.
“C’mon, May-May, you can admit it! I love it so I want to hear you do too”.
“…CUM! I LOVE COCK BECAUSE OF CUM! I LOVE HOW IT TASTES, HOW IT’S ALL WARM AND GOOEY, HOW SEXY IT MAKES ME LOOK AND FEEL WHEN I’M COVERED IN IT AND A GUY WATCHES ME SWALLOW HIS LOAD! FUCK I LOVE CUM!!!”. Despite the volume of his words it had been a nightmare to be covered in the cum. Yet he had watched so many videos of girls getting their faces covered and imagined doing the same to his crush.
“I’m so proud of you for accepting that part of yourself, my beautiful little May-May! And speaking of cum, brace yourself…”
Thea really went to town on Zeek’s pelvis. She was licking, sucking, gagging, gargling, rubbing, spitting on, even nipping at his dick and balls while Zeek writhed in ecstasy.
‘Gotta give the gurl credit, she’s no quick shot!’Thea thought, having no idea of the effort he was putting in to hold back.
“Cum for me, baby! Be a good girl and cum for me!”Thea shouted, Zeek practically yelling as he approached the proverbial mountaintop.
“Oh Thea, I’m gonna, I’m gonna… Eeeeeee!”
Zeek let out a girlish scream as he finally blew his load right down Thea’s throat, her vacuum-suction mouth still wrapped tight around his now deflating pole, Thea simultaneously reaching her own orgasm from playing with her clit. Zeek continued to yelp as he emitted jizm, his cries dying down as he relaxed with the ebbing of his spurts, till he was a softly panting mess.
When he finally lay still, Thea crawled up to Zeek’s face, landing a kiss upon his lips. Zeek eagerly accepted, opening his mouth to receive her tongue but receiving a surprise present as well. His own semen filled his mouth, Thea’s tight pucker not letting any spunk escape from his mouth. With no other recourse, Zeek swallowed, downing as much of the cum as possible till Thea released him to splutter and cough.
Thea played with Zeek’s wig hair while he regained his composure, whispering, “Good girl, good girl. Who’s my sweet, sexy angel? You’re my hot little plaything now, aren’t you? My darling, submissive, beautiful girl-toy…”
After Zeek had recovered, Thea had him lie with his head in her lap and gave him a proposal as she continued to twirl his straight blonde manufactured locks around her fingers.
“So, May-May, I know you’ve only been with one boy. And how much you really adored that encounter. But from what Liz said, your date was the one responsible for putting that silly idea to ruin your lovable siblings hair in your head. If you come to think about it, all the strict rules and punishments that Liz has put on you have really been his fault. I wouldn’t blame you if you wanted to take out a little **** on him, my darling.”
“You’re not off the hook for hurting your sister, and won’t be for some time now I reckon, but if you want him to suffer as you’ve suffered… then you, me and Liz can ensure that he doesn’t get away without his own punishment. All you need to do is agree. So what do you say?”
All the agony, all the anguish, all the strife that Zeek had been through welled up inside him as he found somewhere to project his anger.
“Yes. Let’s get me a gal pal to play dress up with.”
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Locks for Love
Hair
Ezekiel is sick of hearing about how perfect his older sister is and plays a mean "prank on herby cutting her long hair, as punishment her has to learn how much effort goes into having long hair but soon as their father goes out of town thing get so uch more involved and worse for him.
Updated on Feb 12, 2026
by Nicegent42
Created on Dec 8, 2025
by Nicegent42
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