Chicago Hotel Adventure Ch 05

Fifteen minutes after falling asleep, Wes sat up with a start. He really did need to let the trip organizers know he and Sylvia would be missing his airplane. He moved as silently as possible out of the huge bed he shared with Sylvia and tiptoed from the room, leaving her passed out after an especially intense sexual experience for which he was responsible. The gas logs in the fireplace hissed and glowed, warming the room that was chilled from the rain, now extending into its fifth hour of continuous downpour.

Wes flipped the light switch that turned on the living room fireplace, a much more colossal affair than the bedroom's. He crashed his naked body onto a sofa and grabbed the phone, punching the number for Roger's cell phone, which he had memorized. Roaming around a strange place nude made Wes feel both exposed and titillated at the same time. There was a feeling of power as he took advantage of the privacy afforded him in such a massive hotel suite, and he felt that power in a tactile way; he sensed the sofa texture under his buttocks and where his penis lay between his legs, sensed the heat from the fire on his legs and stomach, detected a draft from the air conditioner fluttering through his short hair.

Roger answered the phone. "Hello?"

"Hey, it's Wes."

"Wes! Oh my GOD! You are the coolest fucker on the planet."

"What?"

"Everyone's talking about you and Sylvia."

This could mean a number of things. "Like what?" Wes asked.

"'Like what?' You say it like you're surprised. I mean, all you did was lie about sharing a hotel room for three nights with the prettiest brunette on campus, disappear for half-a-day and almost miss the national finals for piano, which you ended up winning just before Sylvia won hers, and after that you both disappeared with your trophies and didn't tell anyone where you'd gone. Meanwhile there's a few HUNDRED students and professors waiting in the lobby of your hotel to find out where you are so we don't go to the airport and leave your asses stranded 800 miles from home. So, YEAH, you're the buzz."

Inexplicably, Wes grabbed a throw pillow and covered himself. Everybody was talking about him and Sylvia. The idea made his stomach rumble; not only had this week brought him the love of his life and the greatest sexual affair he'd ever imagined, it had probably also given him a raging ulcer. Only in moments like these – rare in his life, or anyone's – did he most deeply understand the extent of his social disorder. He wasn't just shy, he was debilitatingly shy. But... maybe, just maybe, with Sylvia by his side...

"We're not going back. Tell the professors we have airline tickets for tomorrow."

"They might throw you out of school, Wes."

"Bullcrap. We're money makers."

"I know. I'm just shittin' with ya. Hold on, your coach wants to talk to you."

"No!" Wes yelled. "I don't want to talk to anyone but you."

"I'm shittin' with ya again. You're both a pussy AND a dick. I love you."

"Roger, I should have kicked your ass."

"A, you can't, B, I know, and C, you love me, too."

"Stop saying that."

"I owe you one. Lunch was hot today. Faith and I got in that bathroom after you left."

"You're kidding."

"This time, no. In fact, a waiter figured out what we were doing in there and listened through the door. The horny toad had his ear pressed to the door when we opened it. It was hilarious. I threatened to kill the bastard, but my heart wasn't in it. I'd've done the same in his uncomfortable shoes."

"So you guys are better."

"Well, I thought about what you said. I was being an asshole, and I really like Faith, so I'm gonna tone my latent Rogerness down a notch."

"I'm glad to hear it."

"Oh shit. Your coach is walking this way. No joke. You sure you have a way back?"

"Yeah, I do."

"And you'll tell me everything when you get back?"

"Most of it."

"So how long are you staying? And where the hell are you guys anyway... No sir, it's my mom. She wants to know if I'm washing behind my ears. Wes, he's grabbing the phone. Run!!!"

"Wes? Is that you?" said a new voice. Roger had been telling the truth, and Wes now spoke with his piano coach, also the head of the instrumental music department. At first Wes thought about doing the responsible, adult thing and trying to explain his actions to the older man. But even as he debated what he'd say, his finger pushed the hang-up button. Then, dialtone. Hopefully the explanation he'd given Roger would suffice for the school chaperones. If not, well, he and his girlfriend could fly to Germany tonight.

The clock read fifteen 'til five in the afternoon. Wes watched the second hand on an antique clock for a full minute, enjoying the fireplace heat on his naked skin, feeling the stress drain. Certainly the posh hotel room had an inherent calming effect. (Could you call a dozen-room suite a hotel "room?") He thought he should go back to bed, but he just sat where he was, listening to the rain. Tiredness still held him in its grasp; sleep had been hard to come by all week, for one delightful reason or another.

Too anxious to truly sleep just yet, he decided to check out the rest of the penthouse. First he rummaged around in the study. It looked like a study from a real house and, in fact, reminded him of his friend Al's home back in Montana where Al's dad had a similar room. But all the drawers were empty, so there wasn't anything to find. He thought about turning on the computer, but the things bored him.

Beyond the study was a complete wall with a door, only the second full wall he'd seen. The door opened into a second bedroom, smaller than the first but still very luxurious, colored in reds and browns with scattered knick-knacks on tables and shelves, just like in a real house. He wandered around the room, not really looking for anything.

Lying on top of the bedspread, he turned on the TV, housed in a huge darkwood armoire. Even with 140 channels to choose from, he ran across eight different stations playing "Friends" reruns. Much more intriguing were the four channels of hardcore porn. A muscular fellow fucked a petite brunette on a bed while, inexplicably, another man fully clothes at in a chair and watched from the corner of the room, his head hanging in despair. What must the story be with these people? Flimsy, most likely.

"Sylvia's gonna love this," he muttered.

Wes turned down the volume and left the TV on. Feeling worn out both physically and mentally, he only wanted to crawl back in bed with Sylvia. A door in the opposite wall led to the penthouse's master bathroom.

"Whoa," Wes whispered.

Covered floor-to-ceiling in flawless marble, the room glowed peach and cream even without lights on. He saw a gigantic bathtub in the center of the room, with steps surrounding the basin. There were vanity desks on either side, and a shower encased in smoked-glass. Wes relished the sensation of being underwater, as the rain cascading the windows cast wide shadows across the room's floors, walls and mirrors.

Wes quietly opened the door and found his new girlfriend in her huge bed, pretty as a myth. He felt the strange compulsion to nibble her like a snack. He slipped under the covers. Sylvia stirred but did not open her eyes as Wes put his arms around her.

"Where'd you go?" she asked sleepily.

"To call Roger."

"Oh good."

"I've got a surprise for you."

Sylvia smiled. "Not now, you pervert."

"Later, sweetie. Go to sleep."

She drifted off, and Wes followed her. When he woke, the clock read 9:37 at night. Outside, the rain had not let up. Sylvia was missing from the bed. Feeling very refreshed from his four-hour nap, Wes stretched his tired muscles and crawled out of bed.

"Good evening," he said to his reflection in the mirror above. He threw off the covers and stared at his naked body on the ceiling. He looked fucking awesome, but why? Was it somehow caused by gravity pulling him back from the mirror? His muscles appeared firmer, more toned, and his face was just a touch more handsome. He also loved the look and feel of his hairless cock, plump even when flaccid, lying flat against his abdomen. For a moment he desired to touch his own body, but then decided he'd rather feel Sylvia's touch instead.

In the bathroom he found the second door slightly ajar; blue television light flickered beyond. Wes very quietly pulled open the door and looked in the room. He was not surprised by what he found. Sylvia, facing the TV, sat on the big king-sized bed, holding some kind of vibrator between her legs as she watched porn with the sound low but not off. She had no idea Wes stood watching her. On the screen, three girls lay in a circle, licking and fingering each other's pussies. None of the action was obscured; this channel was hardcore.

"Uh, uh, uh," Sylvia moaned quietly, methodically. Her hips circled against her hand as she fondled her breasts with the other, pinching her nipples. Only seconds had passed since Wes looked in the door, but already his cock was huge. He wanted to stroke it, but the magic of spying on Sylvia might be broken if she heard him, so he stood frozen, allowing his cock to throb as the blood crashed through his genital veins.

Instead of climaxing hard, Sylvia appeared to take herself to the edge of orgasm, then pull the vibrator away, letting her body wind away from the plateau, then move slowly back toward it. Wes had a hard time telling in the dark room, but she appeared to be holding a man's electric razor, the kind with three round blade heads, probably provided by the hotel. On the nightstand beside the bed, Wes saw the cover for the razor, which meant she'd removed the blades and was masturbating against some internal rotating piece.

"Uh, uh, uh," she continued to moan. Wes stared at the masturbating girl, racked with lust. Her tight stomach and straining thighs gyrated all around as she worked her poor wet pussy to a frenzy. TV light reflected off the soft, wet film on the inside of her thighs.

On the screen, a buff stud with a hard cock came waltzing into the scene. "Hey ladies," he said. Without ceremony, a redhead released herself from the sapphic group and stood on her knees. She licked the guy's truly impressive dick with her long, perfect tongue.

Sylvia immediately pushed forward on the bed so she faced the TV doggy-style. Supporting herself with one arm, she reached underneath with the other and reapplied the buzzing appliance between her pussy lips, which Wes saw very clearly. "Ohhh, ohhh, ohhh," she moaned louder than before. She obviously saw something she liked.

"Hi," Wes said.

"EEEEEEEEEE!!" Sylvia screamed, jumping high off the bed, throwing her masturbator onto the floor. She sat like a cat, poised to strike, until she saw who had scared her. "Wes!!" She relaxed. "You fucking asshole! You scared the fucking shit out of me, you fucker."

"Shut up, you cock slut," Wes said as he pushed Sylvia down, laid on top of her and plunged his extra-hard cock inside her.

"I'll kill you... if you ever... uh... god fucking fuck yes... fucking FUCK me, Wes..." Sylvia pulled Wes down onto her body even as her neck twisted, trying to get a better view of the TV.

Wes rolled over so Sylvia sat on top, facing both him and the TV. "You're such a slutty pervert, Sylvia." He licked her neck muscles hard with his tongue, something he knew she liked very much.

Sylvia grabbed Wes's head by the hair and encouragingly pushed his face hard against her neck. "You'd know, you peeping tom. That's what you like, isn't it, to watch a girl masturbate watching three girls. That's what you like, isn't it, you fucker, you fucking pussy-licking boy whore."

Wes scooped Sylvia's perfect ass in his hands, deftly pulling her forward at the same time he opened her legs wider to allow more of his cock to drive inside her. Sylvia grabbed Wes by his pecs and ground her body down hard and fast into his, gliding her smooth pussy up and down the new, thick toy she'd found.

"I can't believe what a nympho you are," Wes taunted her.

Sylvia put her hand on Wes's face. "Shut your FUCKING HOLE," she said far too loudly. "Shut the fuck UP, you jesus christ cock-stroker. You like to masturbate while you think about me, don't you bitch? You want me to fuck you hard like this all the time, don't you bitch?"

Suddenly Sylvia pulled herself up off Wes's cock, yelling open-mouthed, and aimed her pussy at his chest. A huge gush of juice exploded from her cunt, a clear blast of pungent fluid that splashed heavily against Wes's chest and face. She moved her fingers to her clit and rubbed hard, coaxing a second and third gush out of her pussy. Sylvia shivered like a power tool as she sat hard on Wes's legs. Then she curled up against the big pillows, trying to put some distance between herself and the one responsible for her huge orgasm. Still, she had one eye open for the TV scene, where one girl rode the boy's cock, another sat on his face, and the third stupidly played with two sets of titties.

"My pussy is so raw," Sylvia said absent-mindedly.

"Let's give it a break," Wes said. Although his words had sounded sweet, he grabbed Sylvia's wrist and roughly moved her around the mattress until she sat above Wes once more; with his head on the pillows, his girl sat facing away from him, still watching TV.

Sylvia started breathing hard. "Tell me you're gonna do what I think you're gonna do," she said.

"I'm gonna do what you think I'm gonna do," Wes said. He reached between the girl's spread legs and dipped two fingers inside her magnificently damp pussy hole, down to the last knuckle, careful not to stretch her tender, hypersensitive muscles; even this simple act made her twitch with post-orgasmic shivers. After coating the digits with a thick, drippy layer of vaginal cream, Wes moved his fingers back to the hole between Sylvia's asschecks.

Sylvia relaxed her anus muscles as best she could, but there was simply no way to avoid stretching her as Wes's fingers worked their way in, pushing further, then pulling out a touch to keep the skin from stretching, then downward again, and so on until Wes felt his fingers buried deep inside Sylvia's burning rectum, the exceptionally tight walls squeezing deliciously around his appendages. Wes felt a sour-smelling trickle collect around his knuckles.

For a few long seconds, Wes fingered the girl's ass, gently worming around inside her. Sylvia's firm asschecks tensed again and again around Wes's hand; her back arched until her curly hair fell around Wes's face.

He removed the fingers easily, pushed out as they were by Sylvia's rectal muscles. Then, with his hands on the girl's hips, he directed her ass toward his dick head, with Sylvia reaching under to help aim the prick toward her tight hole. Wes's penis head grew warm simply from pressing between Sylvia's bottom cheeks, already wet with sweat. He eased his unlubed head inside the relaxed hole as gently as possible, which wasn't very gentle at all.

"FUCK!!!!" Sylvia shouted. It was loud, but not loud enough. "WES! WESLEY!! OH MY GOD!! FUUUUCK!! FUCK!!! GOD FUCK!!! AAAAH!!! EEEEEEEEEEEE!!!!" She screamed as fucking loud as she fucking could, gritting her teeth, pounding the mattress with her fists, once hitting Wes hard in the chest with her knuckles. Wes, juiced on adrenaline and libido, barely felt the blow as he concentrated on the task at hand. Slowly, slowly, he pushed his cock inside the constricting tunnel, working it in, working it out, working it in. When he was halfway in, he was already close to cumming because it felt so fucking good.

"Oh goddamn, Sylvia," Wes said, "you sexy bitch, you love getting fucked up your ass."

She gasped, breathed rapidly, trembled. "I do, I fucking do, Wesley, I love having my asshole filled with your big cock. Only you, Wes. Only your big thick cock. Oh FUCK."

Once Sylvia felt Wes's stomach against her ass, meaning the powerful membrane was completely buried inside her, she collapsed onto his tight body. The boy embraced her with his arms, wrapping them across her stomach and chest, relishing the feel of her hot flesh. On the television, the beefcake was emptying his load onto the blonde, while her friends rubbed the jizz into her tight tummy.

"That's so fucking hot," Sylvia said of the image.

Wes pumped her ass once, twice. Then he began to extract the tool, only to embed it once more, and this he did repeatedly.

"Ahhhhhhhh," Sylvia uttered softly, her head leaning back and mouth open wide. As Wes fucked her maliciously tight ass a little harder, she rode him gingerly, trying impressively to keep her anus relaxed but occasionally squeezing the boy's big penis with the force of scissors. Each time she clamped, Wes shouted "FUCK," and slammed up into the girl harder. When she could no longer take it, Sylvia moved a free hand between her legs and masturbated, dipping what looked like three fingers deep inside her sloppy pussy while she took it from behind.

Then they got loud.

"FUCK!!! SHIT!! YOU FUCK ME, WES, YOU FUCK ME!"

"GIRL, FUCK, I'M FUCKING YOUR ASS, FUCK! SHIT!"

"AHHHHH!!!!! AHHHHH!!! AHHHHHH!!!" Sylvia screamed as she had never screamed before, at least not since Wes had known her, a loud shrill that reverberated through the room, piercing, impossibly loud, in a perfect key of C three octaves up. And she hadn't even come yet; her hands were still beating the wet meat, smack smack smack smack smack, while the rest of Sylvia's body remained frozen in Wes's deathgrip.

When Wes came, his body shook violently, much harder than he could have imagined possible. The orgasm was an out of body experience for both of them. Tingling from head to toe, sloppy with sweat, Wes felt Sylvia's flesh along every inch of his body, and it created the odd sensation that his body was much shorter, impossibly small, focused like a bullet aimed at Sylvia. He believed his toes might be only inches from his face, because all his skin from one point to the other touched the girl and he felt every point. This was not a conscious idea; his brain was foggy from the explosive power of his orgasm.

Still acting on animal instinct, he threw Sylvia beside him on the bed and held her perfectly still, as a painfully powerful river of cum shot out his penis and crammed Sylvia's ass full of fluid. Sylvia had been close to her own orgasm when Wes yanked her down onto the mattress, and the physical jolt summoned her orgasm forth as though at a magician's command. She came like dynamite going off. No sooner did her cheek hit the bedspread than her voice, beyond her ability to control, belted out a shattering, staccato yell. "AY, AY, AY, AY, AY, AY, AY, AY, AY."

Mindlessly both her hands increased the pace of their rubbing, driving her powerful orgasm forward. Several long seconds passed as Wes suffered the girl's vibrations, his excruciatingly sensitive cock still inside her ever tightening asshole. Like a reluctant roller-coaster rider, Wes held on for all he was worth as Sylvia pounded herself with her hands. He looked over her shoulder and watched, knowing he could not afford to miss such a once-in-a-lifetime event, even though the sensitivity in his penis was becoming unbearable. Sylvia's legs flailed, her body bent over at the waist and flopped back against Wes then bent and flopped again. Her tits bounced hard in every direction, her hair flew all around. "UH, UH, UH," she continued to grunt, and still her hands rubbed hard.

Suddenly she stopped, seemingly lifeless to anyone looking on, except Wes held her and could tell every muscle in her body remained tight. She took short, sharp breaths through her thinly closed lips, and her back shivered almost imperceptibly. Sylvia kept her hands pressed firmly against her pussy, between her tightly closed legs.