Young bellboy at Hotel Royale breaks into professional modelling with the help of a rich beautiful cuckoldrix and her feminizing, chastity belt training!
chapter 1 of Cupid in Chastity.
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Cupid in Chastity!
Chapter 1
TJ Ryder
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Timmy was thinking that whatever the upper class megababes want they always seem to get, one way or the other.
He thought it odd he would think that while taking a rare break from his work at Club Mandingo, but something about that cute interracial
couple on the beach triggered it.
Was it envy? he wondered! No yeah, but just, well, its just the way it is. Watching this gorgeous blonde fondling the huge black stud in his tiny lace thong out on the sand, and her in an ever smaller lace thong bikini, he allowed himself the luxury of watching interracial love without his hated chastity belt, knowing he had to keep his balls undrained until the weekend because he was on duty again and the guests,
especially the women, loved big blue balls on sissyboys wearing chastity belts. So instead of taking his break at the club he always walked down the beach a few hundred yards, past the private beach he worked as a poolboy and sissy maid, and in frontof the other beachfront hotels. There, he smiled, arranging his cock to straighten in his bathing suit, he could watch beautiful babes and black studs without a chastity belt or get in trouble.
While he couldn't take his cock out and spurt off afterwards, he could leisurely watch scenes like this as long as he wanted to without the constant interruptions a sissymaid always has on shift and even on the premises when he wasn't on shift.
There was something familiar about this blonde megababe, even though a majority of women he served at the club were blondes, either natural or dyed, making them more attractive they thought to the black studs they worshipped.
Even though his first view was her thong-covered bottom, and he groaned as she spread her thighs, revealing natural blonde hair around her tiny butt-floss thong. Mmmmm, he thought, I wish now she was a guest at the club. As they made out,he watched her move her small hand and fondle the huge lump in her buck's speedo, and her sweet lips press his, and then
her pink tongue dash into his huge lips. Was he imagining that her pussy was already wet?
AWmannnnn! he moaned, and then she turned and he saw her face! Beautiful as he expected, but not Mrs Cheltenham, the name he thought would go with the memory. That was the woman who recommended he work at the Mandingo whilehe worked a bellboy shift at another interracial hotel, the Royale!
Mrs Cheltenham, married young to an older oil tycoon, she was a regular visitor at the Royale where he carried her bags up, and she loved displaying herself to staff white boys. One day when she got in earlyand her buck hadn't arrived yet, and business was slow, she asked him to remain in her room while she waited. He hadn't been at the Royale all that long, figuring it was just a temporary job while his acting and modelling career took off, and it sort of did, in a way he never would have suspected.
"Your'e actually the right type, bellboy, for a new club my husband is starting up on the coast!"
fig 2
"Oh, thank you, Mrs. Cheltenham!" he smiled, aware this isn't idle talk from someone like this trophy wife!
"I did some modelling myself, you know, before I married
Sid!"
"I'm not surprised, madame!" He replied honestly.
"But this club wants boys who know how to treat the, shall we say, select clientelle, like the Royale services!"
"Oh," he said, uncertainly.
"Yes," she smiled, "open that small bag there and I have some press handouts about this new club! Plus last year's calendar. You know wer'e casting for a St Valentine's Day and it's an international chain of clubs?"
"Wow," he said, unzipping the expensive Italian leather suitcase, "that would be a lot of exposure!" As he took it out he saw a luxurious beach hotel called Club Mandingo! He swallowed as he noticed her smug little smile. Another interracial trystingspot for the rich and beautiful.
"Go ahead and take it with you, boy! If your'e interested I'll see you again later."
"Oh, thank you, Madame!"
The next night when he got home he came to the reluctant realization that as humiliating as some of these pictures were, any press was better than no press to an aspiring actor and model. These were centerfold layouts! And he had to admit he wasn't thestud male model type and opportunities like these were quite rare!
It was almost a week before he ran into Mrs Cheltenham again and that was taking another bellboy's shift, and to his relief she seemed to remember him. Still, riding up in the elevator, he had to make the first move.
"Um, madame, I, ah, would like to return this press release you lent to me!"
She was thinking of a giant black lover between her legs and paused, trying to put the face with the literature, and realized
this was the same bellboy!
"Oh, yes, Willie or something?"
Disheartened, he said, 'Timmy, madame! I appreciate your letting me have it!"
"Oh yes, that's right, your'e a model or actor?"
"Um, yes madame, you said we might talk if I was interested!"
"Mmmm, well, I have other things on my mind at the moment, boy! But, well, come into my room and we can chat for a bit before Tyrone gets here, he's always running late!"
Inside the luxurious suite that her older husband paid for, he dropped the suitcase on a divan and asked her if he wanted him to unpack it!
"Yes, go ahead, and lay out the green lace nightie for me, boy!"
He had only been at the Royale for a while, but he heard from the other bellboy of the games they played, and fact is, he was always fighting a hardon and wished many times he could bring refreshments up to the rooms like they did, but he only did luggageand other outside work so far. But at the moment he knew a Big Break might be waiting for him if he could get her to help him in his modelling work.
Holding up the tiny see through nightie, he swallowed, and gasped as he noticed she was peeling off her nylons. Taking the nightie, she smiled and said she would be right back!
He waited as he heard water running in the bathroom, wondering how long before that mammoth running back Tyrone appeared, and gaped as she strutted out, smiling at his reaction.
"Like it?"
"(Gasp!) wow!" was all he could lamely say, his throat tight.
"Well, anyway boy, you should be used to seeing white women like this at the Royale!"
"Oh, I only work the front so far, ma'am!"
'Then your'e priviledged," she said smugly! He nodded, blushing a little!
She giggled, "actors and models must not be shy, boy! You have to delve into the role completely! I learned that early!"
He nodded, it was true.
"So, what questions do you have about the Mandingo?"
"Um, you mentioned a job, and some calendar work?"
"Oh yes, but that's just because I see your face. Did you see the other sissyboys on the calendar?"
"Y-yes, b-but I'm not...!"
"You see, willie, you seem like a nice young man, but I want to get our new club on the map with a calendar spot. I can't spend the time on every aspiring out of work boy who isn't willing to do what it takes!"
"Y-yes ma'am, but I was trying to explain...!"
"Look, let me explain! Do you want a shot at it or not?"
"Yes ma'am!"
"Good, now strip!" He paused and she frowned.
'I have to see the whole package, boy, before I can begin to give advice!"
"Yes ma'am!" She sat on the edge of the bed as he blushed and slipped off his shoes. Soon his pale, slim and almost hairless body was naked, and he still had half an erection from her incredible body peeking through her peignoir.
"Hmmmmm, turn around, hands on your head? Do you photo well, Willie?"
'Yes ma'am, um, Timmy!"
"Whatever, spread your legs, and spread your cheeks! Hurry up!" She shocked him by slapping his bare butt cheek.
"Y-yes ma'am!"
"Hmmm, possibly! Go over there and get me a pad and pen and I'll make some notes!"
"First, if you photo test well, you might have a shot, that's the good news!"
"Oh, that would be great and...!"
"But that's just the raw physical side of it. You have much work to on your whole persona to fit in at the Club!"
"Y-yes madame, I'm willing to do the work!"
"I certainly hope so, because I would hate to be wasting my time with you, boy!"
"First, remove all hair, everywhere except your head, and let that grow out to shoulder length. And use a skin care product for smooth soft skin!"
"Yes ma'am, I do use a ...!"
"Your nipples should be an inch long! Don't you have a boyfriend?"
He gasped, trying to figure out how to answer that one.
"Your butt is good, but no more tanlines! Fortunately you have no beardline and your adams apple is not protuberant!" I noticed she was writing something down on hotel stationery.
"I made a list, boy, get them all done at once! I can't even send you up to the Club the way you are!"
"No ma'am, I mean, yes ma'am, I will!"
"And the real work is personality, boy! You have much to do! You would be wasting everyone's time and making me look bad if you passed the phototest and then failed the personality!"
'I want you to act like a perfect sissymaid. Maybe you should try a chastity belt for a while! Didn't I ask you about your
boyfriend?"
"I, madame, I uh, don't have a boyfriend!"
"Why not? A cute young slim whiteboy like you should have many big black studs!"
"B-but, I-I'm not, well, I have a girl friend?" he phrased it as more of a question than a statement! She laughed in amusement at that.
"Sounds like your'e not sure what you are, boy! That's good in a way for an actor, did you know that?" He replied no.
"Yes, for any role or any job, you must be whatever they need. And right now, the reason I hope I'm not wasting my time on you boy, is I want my club to have next year's Cupid for the Valentine'sDay calendar!"
"Yes ma'am!"
"Whoever gets the Cupid picture gets to travel all around the world visiting clubs, representing my club. And everywhere he goes he doesn't play Cupid. They want him to BE Cupid! You have to be able to slip into it like your most comfortable shoes!"
"Yes ma'am, I learned that in acting class!"
****************************************************
At break he groaned as he read her list, which conflicted with the imagined life of a high profile model travelling all over the world.
After his shift he went to this unique shop, mostly gay, he had to admit, that sold props and lotions and toys. The aging queen behind the counter was an old friend from acting class and smiled enviously at him, wishing he was still young andpretty.
"Timmy, what brings you here?"
"Um, Bea, I got a chance at a gig, but I have to make some changes, and some of this I just don't know...!"
Bea took the list, and chuckled. "A girl's handwriting Timmy? Someone making you their sissygyrl?"
'It's a real gig, okay! How'm I going to do this?"
"How long do you have?"
"Um, yesterday?" Bea shook his head in amusement!
"At least two weeks for all of it. I can get the nipples done in a few days if you put these pumps and twisters on it. will be painful. Hair depilatories, no problem, tongue stud? Well, that will take a week to heal, ear piercings, a fewdays. Basic makeup kit. Lips and cheekbone padding! Mmmmm, you working the Royale and you don't know about this last one?"
"Geez, I keep telling people I just work the front!"
"Yeah well, you better start thinking about working the back if your'e serious about this! I can
give you a dildo set to get you started!"
"What?"
"And use lots of vaseline and do lots of stretching!"
"I didn't see that on the list!"
'You didn't want to, and better take animo acid cocktails from now on, and vegetarian diet, unless your'e getting oral protein shakes the old fashioned way!"
"C'mon, Bea, this is important!"
"If its really important you'll listen to me or your'e going to blow it!" Timmy was silent for a moment!
"Your'e going to have to change, Timmy, a lot! Are you ready to admit that?"
'That's kind of what she said!"
"The girl who made the list? She's right! Time for getting hired on your looks is over, boy! They want to
see performance!"
"Yes, but...!"
"Look, I'd give my balls for a shot like your'e getting now. And you don't have to become a t-gyrl, at least not
yet anyway!"
"B-but..."
"I'm going to put this order together and you think about whether your'e serious or not. And after a few days we'll talk bout step two, which isn't on the list, and we both know what that is, don't we Timmy?" Timmy pretended he didn't hear itand Bea smiled.
***********************************************
Mrs. Cheltenham smiled down at Timmy as he was on his knees in the bathroom trimming her bikini line.
"Very good, boy, you know I wouldn't be spending my time on you if I didn't think you had it in you to be a good sissymaid!"
"T-thank you ma'am!" He had stripped again on her orders to show his altered appearance, and now she was making him show his devotion to the role. He just wished he wasn'tdripping hard in front of her!
"Now, when I call for room service you will deliver it, and of course clean up for us!"
He moaned, his cock throbbing now!
"Yes ma'am!" his voice thick!
"Oh, and this is the new panties for maids at the Mandingo this year!" She reached into her purse and handed him a pair
of sheer pink bikini panties, cut for a males genitalia with little sacks for the balls.
"Oh, yes, so precious. I chose them myself for the staff. Do you like them, sissy? You must!(giggle) Your little dicklet
is getting stiff in them!"
"Y-yes, very nice, madame!"
*****************************************************
One of the things he did notice on his shift and even his daily life of going to grocery stores and commuting was as his appearance changed, he expected more of a change in response to it, but even with discreet eye shadow, fuller lips, tonguestud, and blatant flags like "Friends of the Black Experience!" pin on his lapel and Black Power decal on his shirt, the response from other people didn't really change until he changed things that others did not see!
When he began to enjoy wearing panties all the time, along with the buttplug, ball harness, chastity belt and nipple twisters that nobody could even see under his clothes; well then he began to get approving and interested looks from black men and white womenthat otherwise never noticed him!
Why, he wondered? Was it because he didn't notice those looks before? No, that couldn't be right. When he obediently lapped up Tyrone's cum and sperm-covered testicles the other day as he was still connected inside Mrs Cheltenham, he received an affectionate pat on the back of his head!
When Mrs Cheltenham humiliated and tested him more and more he knew he couldn't depend on her responses for a guage on his progress. But so far he still hadn't been granted the trip to Club Mandingo to photoshoot! And his social life!
Ah, that was another big change. A gorgeous temporary coed receptionist at the Royale that he had been flirting with for ome time, unsuccessfully, seemed to take more of an interest in him. The college freshman anthropology major was blonde with biggreen eyes and big firm breasts and so far hadn't taken the black-cock-only route that the staff working the Royale always seemed to go to since they were exposed to all the big black dick that New Orleans had to offer. But that ould be because she only worked mornings on weekends and didn't see what most of the staff did. The other thing was he began to read all the PR stuff that any representative of Mandingo had to know by rote.
All the afrocentric, black supremacy, Obeah and cuckold lifestyle, reciting the lines, practicing them, sometimes
with Mrs Cheltenham making him demonstrate. It was humiliating but also erotic and somehow in a deep way, satisfying!
***************************************
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