The Annex Hotel

Fitz was having a great time with the three boys under his supervision. When elsewhere occupied, the three could be left in the darkroom. Today was one of those days. He was steward to a Master Winslow and his two "subs" 

The three boys needed no prodding to head to the dark room, the only admonishment from Fitz being to remember to keep douching.  

Room 336 was a large a suite able to accommodate up to eight guests. Being sent to steward Master Winslow was another babysitting job. This one Fitz wasn't so fond of doing. 

Dee and Freud were two barely legal twinks on contract to the master for the rest of the year. Fitz was charged with putting the young boys through their daily routines. This master was ruthless. 

"Alright Dee, you're first." Fitz held a twelve inch black dildo. 

Dee knelt before the steward, bent his head back and opened his mouth. Fitz so wanted to put his dick in this boy's mouth that his dick kept  twitching through the entire routine. 

"Fondle my junk while we do this"

The boys eyebrows shot up, not being allowed to speak with anyone but the master, the boys question was obvious. 

"Go for it, I'll let you  suck it after this. "

The boy complied as Fitz began feeding the dildo down the cute boys throat. 

Fierce, painful sounding gagging preceded an ocean of white spew. Unfazed, Fitz continued to fuck the boys throat. 

"The trick is to anticipate and make a conscious effort to relax, your throat muscles particularly. This will abate with daily gagging as will the vomiting....." 

The poor suffering boy was trying to sob along with the waterfall of tears he was producing but the throating precluded that. 

"Freud, suck your "brothers" dick, put a finger up his ass while you do that"

Freud, the other boy was equally wary of obeying the steward. A firm look from Fitz and Freud began licking Dee's chastity cage. 

These boys wore cages with a modicum of room for the erection of the penis. It still hurt like hell. 

A barb of metal, a feature of this style of cage, stuck about an inch into the boys dick slit. 

"Make a real effort Freud, I want this slave to give me a load through his cage . "

Dee was suffering. Two parts of his body were under attack. His dick felt Freud's tongue and began a painful journey to a determined painful not-quite-erection; his throat was being "sandpapered"; he couldn't concentrate on both. 

"Think about the load you're going shoot, Dee. And your prostate being tickled. You'll have a forbidden orgasm and no one in this room will tell daddy. It will be our secret, I'll even let you taste it" Fitz hadn't even slowed the constant fucking of this boys throat, the fantasy of replacing the dildo with his dick was being helped by the boy tentatively fondling his junk. "When we finish here I'll let you suck my dick if you want. You've got three things going on, the one capturing your full attention should be making my dick hard and making me feel your wish of having it in your throat."

Fitz strategy was working, the boys throat began to relax and accept the invasion. He still gagged, but not as hard and almost distractedly. Glancing at Freud and his tasks, Fitz saw Dee's dick try to engorge and fill the cage . Still painful but with the tortured pleasure Freud was inducing. Dee's prostate began to respond. 

The  confused boy began to choke, Fitz pushed Freud away and he removed the black dildo. 

"You did good, Dee. Tell me, does your master like you boys to suck his cock?"

Both boys nodded. 

"This training I know is hard, and it'll keep hurting until your body and mind  accept it as normal. " 

Fritz gave a warm smile, "Freud,  fuck him with one of those dildos" 

Both slaves responded with startled looks and raised eyebrows. 

"I want you both to cum this morning."

Freud took the training much worse. When the boy began thrashing, Fitz taped his arms, as uncomfortably as he could then moved him to a chair where the steward could sit on him while he completed his task. To his credit, Freud gagged constantly but only vomited once. 

"Ok boys, this calls for a break."

Two smiles greeted this statement along with grateful body language  

"For me anyway, you guys get on the floor and worship my  dick like it's your master's "

After an extended bathroom break and a snack from a charcuterie tray the boys obeyed their instructor.

With a hand resting each boys head, Fitz watched as his dick was licked, gently sucked, then his balls got similar treatment. Freud was adept at ball worship. His tongue made circles around each testicle before sucking it into his mouth where it received a thorough cleaning. The perineum was also licked. When the boy's tongue got dangerously close to Fitz asshole, a new plan began developing. 

Both balls were now in Freud's mouth, tongue barely able to move, the boy made Fitz's ballsack start a tingle in his crotch. Even his balls can stimulate his prostate. Hot damn!!

While Freud was employed, Dee was expertly exploring the firm dick's slit, then his tongue circled the head. At one point Fitz thought a vacuum cleaner had been hooked to his dick's head. Dee was bobbing up and down on Fitz stiffness while his "brother" kept popping testicles in and out of his mouth. 

"Freud, fuck my ass with your finger. "

Freud obeyed and licked his lips looking at Fitz 

"Don't worry, son, your tongue will get in there pretty soon". Freud's finger found new depth and connected with Fitz's prostate. 

The slaves took turns taking the dick to their throats. In a silent agreement they began deep theoating, taking Fitz's dick deep into their throats. 

"See, you two learn fast. Freud eat my ass. Dig that tongue into it. 

"When I cum I want both your mouths on the head of my dick. You boys are getting me close to that, so slow down. Just make love to my ass and junk for a while."

When Fitz saw he might be late for a second guest's request of his morning, he had both boys take turns jacking him until he brought their  mouths together to capture a quite pleasant orgasm's ejaculation. 

"Thanks boys, master will be back in a couple hours so get clean and I'll stash you away."With flavored water dripping from their asses the boys were locked in their cages. 

"See you boys tomorrow for a rerun "

Fitz rang the door bell of room 122; a smiling naked boy answered. 

"Hi Fitz, Ari already started with daddy "

"Let's see if we can catch up"

The boy, JJ, laid on a fucking table, his ankles secured in stirrups above. His asshole was leaking copious amounts of lube. The smile never left this boys face. 

Fitz sat on the provided stool and donned two elbow high blue surgical gloves. 

Starting with a finger, Fitz began to loosen JJ's hole. 

"Both daddy and Ari fucked me this morning, and I kept in a plug all night. I should be easily gaped"

Fitz replaced his single finger with three on the same hand and began pushing them in and out of this softly groaning young man. Fitz wasn't fond of hairy assholes but these two bears were,  he thought, super nice so they were the exception. 

JJ had blonde hair all over his body. His daddy has had him keep it that way since they got together. Ari had the task of bleaching his hair last week, a few black  hairs were threatening to undermine the perm. The steward got the boy so horny he began stroking himself. Eventually that turned into a heated jack off. JJ asked Ari if he could come in the stewards mouth so his dick head could be teased and sucked. Since the Hotel required all stewards to grant guest's wishes, Ari gladly obliged, after which he was asked to push the emission into his ass with his dick. Ari was requested then to deposit his own cum load to mix the two boys's semen together for the piggy daddy to suck out. 

Fitz took his time with JJ, he never wanted to shove his fist in until the boy was ready. A signal told Fitz it was time, and his fist cork-screwed into the already cum filled ass. Ten to fifteen minutes of fist fucking and JJ was ready to join his daddy. 

The Hotel handyman had constructed an apparatus which suspended JJ over is daddy. They were in the 69 position able to suck each other while the stewards continued fist fucking them both. The groans increased in volume and intensity. Both stewards's dicks were again hard as rocks, they were able to touch themselves but had to save the second cumming for the coup de gras. 

A few minutes in , "Baby, I want to cum. I promise to cum again later too" Daddy was ready. 

This encouraged JJ to double down on his  daddy's cock sucking and Fitz to position his fist just inside daddy's hole and corkscrew even faster. The older man was groaning louder though muffled by the boys dick in his mouth and his whole body shook. With a muffled "whoop" daddy shot cum into JJ's throat and mouth. JJ was ruthless with his after- cum torture, his daddy groaning in complaint. JJ licked and sucked  daddy's cock into softness. 

"You can swallow, baby". JJ did. 

"Thank you daddy. I love drinking your milk. I wish we could bottle it so I can have some anytime you're not home"

"A little extreme JJ. Now may I resume attempting to drain your juicy sweet dick?"

Daddy had poked two fingers into JJ's nearly prolapsed asshole. Though he didn't touch the boys prostate it appeared he didn't have to. It only took 60-90 seconds for JJ to eagerly fill his daddy's mouth with warm cum. 

The bears were hardly done. This session could go on for hours. 

JJ assumed a position up against the bed where he supported himself on his shoulders and his gaping asshole was pointed straight upward. 

Daddy emptied his mouth onto the bright red insides of his boy's rectum. 

Ari was first to add another load to the mixture, then Fitz. 

The stewards were finished with this scene, though Ari atayed with these bears, Fitz headed out. 

"Thanks Fitz, Ari, eat my loose ass for a while will you?" Daddy laid on the bed, his mouth prepared to indulge in the mixture of his boy's cum plus his own. 

"I'd love to, sir. May I finger your prostate?"

"Absolutely but not right away. See you next time Fitz."

"Looking forward, sir  

Fitz left to the gurgle of JJ's daddy sucking on the boy's hole. He knew JJ would be good for another orgasm, his daddy will love it. 

Fitz decided, the kinkier, piggier they were, the more he loves joining in. 

Fitz wasn't near done yet, being an extremely popular steward. His red hair and freckles; the sparse crop above his dick was also red. His talents were renowned in the steward bunkhouse. King of kink. 

Room 205's door hung open, the sounds from inside were readily identified by Fitz. Ralph and Carl were sharing a double headed dildo. Fitz's job is to fuck both men's mouths in rotation with the guests's room steward. These men didn't want any cum spilled in these session's except their own. The two stewards were welcome to step out on the room's small patio to satisfy their carnal needs. It wasn't unusual to see the two men shoving big dildos in each other's asses while two young twinks were on the patio fucking and jacking off. 

The double header was bigger the last time but the deal was that the stewards were to add their stiff dicks to the fucking. Though not allowed to cum, the boys stayed stationary inside and let the men continue fucking the big dildo. 

Raul was ready to cum, so the boys stepped outside to satisfy that urge. Fitz turned the brown skinned boy around and stuck a finger in his already wet asshole. 

"These guys both fuck you ?"

"Yeah. Only once each so far. You know how they like to edge themselves"

Raul shot a load into Fitz's mouth, then the red head dropped it all back into the Raul's  mouth. They went back to fucking  the men for another thirty minutes before Fitz was told he could go. 

Perfect timing. He had just received a  message to report to Lyric's office. 

This can't be good, the redhead thought. 

Lyric was always having his dick worshipped when Fitz went to his office but the sling was empty this time. 

"Hey Fitz I know you're busy today but I need you to finish with this kid and set him up in the bunkhouse."

A couple minutes later Fitz had issued the boy a cell phone to holster on his arm. Told him a few of the codes, but said most messages will be written out. 

"What's your name? I'm Fitz "

"Leif, but I'm mostly called Lee"

"Ok Lee, after the audition do you get an idea what will be required by you?"

"Yeah, I'm excited. Can't wait for my first assignment "

"Did Lyric give you any Viagra while you were there?"

"Viagra? What do I need that for?"

"Just as an example, I've had six assignments this morning. Two where I either just fucked or fucked and came. Right now I'm sure my balls are dry, but I need to finish my day. I take one pill in the morning, by 2pm I take another. The two usually keep me hard all day. You need to have a hard or semi-hard dick while here"

"No I haven't had any. "

"Plenty in the bunkhouse. We all make an effort to get along here. Trouble-makers are sent home."

"What did you do so far today, like with the hotel customers?"

"Call them guests not customers. I've fisted, fucked, sucked a lot, deep throated once, haven't been fucked enough though. But then who ever is?"