Forced To Get Dumped

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A curious sissy forced into the life he really wants.
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James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way he could let that happen.

James looked down at his weekend's work. His slender body had been waxed head to toe, and tanned lightly. His finger and toenails were painted a bright hot pink, his hair tucked back under a flowing blonde wig. He layered his make up on thick and slutty, with lots of eyeshadow and red lipstick, as instructed.

Looking his body over for any flaws he might have missed, James sighed and went to his dresser. Every drawer was brimming with brand new clothes. Thongs, panties, hose, stockings and socks of all different colours filled the top drawer. Skirts, bikini bottoms and short-shorts filled the second. His closet, once full of comic books and baseball gear, was now stuffed with dresses and gowns, tutus and wigs, and more high heels than he could count. 'My college fund,' he thought ruefully.

All of it had been spend over the weekend, in the shopping spree his Mother had insisted on just hours after she'd caught him eyeing himself in her bedroom mirror, naked but for a pair of her silk stockings and black panties. He'd begged and cried, promised he'd just been curious, wanted to see what he'd look like. It was no good. His Mother simply snapped pictures of the sissy wretch with her cell phone and told him to put on some clothes.

"If you want to prance around in women's underwear then that's what you'll do, but you won't be doing it in mine," she yelled, watching him pull jeans over her lingerie, red faced. "You can pay me for those pair, they belong to you now." When she explained that they were going to the mall to buy a more complete wardrobe for her sissy daughter, James finally got his nerve.

"Okay! Mom! I get your point! It wasn't anything! I'm not gay, I don't want to wear women's clothes I was just-" She slapped him across the face hard.

"Listen here you little pansy. It's bad enough you have to ruin my favorite piece of nightwear, you are not going to give me sass as well! Do you want everyone at your school to know that you're a filthy pervert who plays with his own Mother's underwear?"

"NO!" He shouted, falling to his knees again. And so they'd spent the day at the mall, going from store to store, trying on endless shoes, blouses, dresses and corsets before ending the day with a mani-pedi/tanning session at the salon. The embarrassment was almost too much for James to bear, but it was better than what his Mother had threatened to do if he didn't cooperate.

That night, James had to tear down his room completely, getting rid of all his male clothes, video games, books and belongings. He put new pink barbie-themed sheets on his bed and was getting into his new purple footie pajamas when his Mother came in with a small plastic device in one hand and a key in the other.

"Not so fast, Jasmine. We need to put this on first." She said, pulling his soft, small dick into the plastic tube and fixing the plastic ring around his balls.

James tried to recoil. "What are you doing! And my name isn't Jasmine!"

"It is now, sissy. And this is your chastity cage. It's going to keep you chaste and honest tonight and every night from now on. I don't want you getting horny and erect, being surrounded by all your new girly possessions. You're my good little virgin girl and you don't need any more dirty perversions to reveal to your school cums do you?"

"No..." Jasmine whimpered, defeated.

Today would be the hardest he knew. Today was so unfair. But if he didn't do exactly as she had instructed, the entire college might find out about what his life at home was like now.

Pulling his skimpy pink thong over his tiny chastity cage, Jasmine remarked how feminine and girlish she actually did look, done up as she was. Maybe Kim wouldn't immediately hate and reject her, maybe she'd find her attractive in a new way. 'Unlikely,' he thought, pulling up his sheer stockings and hooking on the bra with realistic breast forms he'd had to buy with his college fund.

The maid uniform she was making him wear was outrageous. It didn't cover up anything, the apron left his fake breasts spilling out over top of it, and the skirt ended well above the half way mark of his exposed butt, allowing everyone to see his little thong and cock cage. The 6 inch pink heels were wobbly to walk in at first, but a few hundred laps around the pool had taught him how to strut in them properly, wiggling his butt to stabilize himself. His outfit was completed by a ridiculous tiara which was shaped in the word 'COCK' bordered by big red and pink hearts, and comically small pink duster that he had to hold between thumb and forefinger.

Before inviting his girlfriend Kim to come by, his Mother mused on what might be the most humiliating thing to have her walk in on him doing. She considered making her new maid rub her feet and massage them thoroughly. That would be cute for Kim to see - her loser boyfriend done up as a french maid rubbing his tired mum's feet like a good boy.

Or maybe it would be better for her to find him in his proper place in life - scrubbing the toilet on his knees. She'd certainly have him doing that quite a bit from now on. Whenever he didn't have more important chores to keep him busy he could always work on polishing that toilet.

She finally settled on having him kneel on his knees up in the living room where his new 10 inch black dildo was fixed to the wall. She set him to sucking and slurping at the new big black toy, not relenting until he could make the big realistic balls touch his chin while he deep throated. The vibrating butt plug in his ass only added to the discomfort and humiliation, and James - now Jasmine, had no choice but to suck and suck while fighting to urge to cry.

He heard the knock at the door and his heart sank. His Mother rushed over to answer and invited his girlfriend Kim inside graciously. When she saw James, dressed like someone's gay fantasy, furiously sucking a plastic dildo, her face turned shocked.

"James! What-What the fuck are you doing!"

With all his strength, James took the dick out of his mouth, thought of all his friends and future colleagues laughing at him and said the words that he'd been trained to say.

"Oooh, sorry honey! I forgot to tell you that on weekends I like to play dress up and suck-suck with my Mommy. I have all sorts of panties and pretty shoes and I've gotten really good at pleasuring men! I hope this doesn't change anything in our relationship."

Kim just stared at him blankly, with a mixed look of confusion, pity and disgust. "Well, alright," she said finally. "Maybe you should do that more from now on. Like, all the time. I don't think I'll be seeing you around. Um, bye."

And with that she all but ran out. James felt tears well up as spit dribbled down his chin. "Don't you worry about it," his Mother cooed. "Sissy faggots like you shouldn't be bothering nice young real girls like Kimberly! She needs a real man in her life at this age, and you're just a loser with a caged dick and drawer full of pantyhose. Now get back to your practice cock! You heard her- we've got a long week ahead of us!"

Kim quickly spread word of her ex's humiliating lifestyle to all his school friends. He's now gainfully employed as a gloryhole favorite in Bangkok.

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AnonymousAnonymousalmost 2 years ago

This isn’t even a story. It is barely a thought. Good thing you gave up trying to write.

AnonymousAnonymousabout 4 years ago
Really

pathetic fantasy

zazrix9zazrix9over 5 years ago
I'd like

to own her

GrrrreatImaginationGrrrreatImaginationalmost 6 years ago
Well...

Sorry about the length, I got caught up in the story's potential.

There is a really usable story-line buried in this story. Erotic stories often have tension between some or all characters, and you nailed that. Wow, Mom has some major control issues, eh? And James isn't that bright, so he'd be kinda easy for her to manipulate, over a week or a month, into that scene with the girlfriend. Instead, she just steamrolled him, with no one enjoying themselves (bummer).

Oh, btw, you have this in the wrong category. No big deal, just a pet peeve. I'd call it Non-Consent/Reluctance. Why? James never consents to any of it, because he's blackmailed (that's coercion). Maybe we could call it BDSM, but even in BDSM _somebody_ is enjoying. You could have called it TS/CD if you'd shown him actually enjoying himself. I know, I know, you had him modeling Mom's undies at the very beginning, but since he's never described getting off on... well, anything, that leaves N-C/R.

I hope you give this story-line another try. I don't really care what category. Take your time, though. Make Mom the controlling bitch you started with (good job on that), but have her stretch it out over more time, and hold the college fund hostage to get him to comply, only revealing at the end that the money's used up. And make sure either she or James or both of them are getting off on it (even secretly). I'm telling you, you've got the makings of a really good story here. I'm gonna go check out your other stories. Keep writing.

AnonymousAnonymousabout 7 years ago

Wow... harsh, but kinda hot!

:p

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