Chicago Hotel Adventure

“You’re right,” Sylvia said nodding. “The truth is, I was really shy growing up. I used to wear glasses all the time, and I was a bit taller than the other girls, plus I read all the time.” She smiled. “I like to look nice, but that’s about all that’s changed about me. I’m not that out-going, but I know what I have to do to achieve what I want. Like playing the cello. It would be nice if someone would just give me first chair in the Boston Philharmonic, but I’ll have to work for it, and I want it.” She grabbed a cooled slice of pizza, her third. “Besides, you’re pretty quiet yourself. Quieter than me.”

Wes laughed. “Yeah, I know. I guess I’m just not as pretty as you are. But otherwise, I’m in the same boat. I went to school with a lot of non-farm kids, and they just weren’t very pleasant people. I was always physically fit, but I didn’t do much to show it. I had to kick a kid’s ass once, and that made my senior year of high school a lot easier, but it didn’t do me any favors when I got to college.”

“I’m surprised a pianist would punch a guy.”

Now it was Wes’s turn to be embarrassed. “Aw, I didn’t really punch him, just hit him in the gut a few times. I’m no tough guy.”

“Did you date much?” Sylvia asked.

And so the time had come to discuss past lovers. Wes had breeched this topic with only a handful of girls, but he knew that it changed the tone of any conversation. Talk of dating led to talk of physical experiences, of what the person was looking forward to or willing to do. Again, Wes reminded himself they were just talking and that it might never lead anywhere. This helped him to settle down inside. Above all, he wanted to come across as a gentleman and not a horn dog.

“Some,” Wes answered. “You?”

“Some.” They both laughed.

“Man, I dunno, I guess I didn’t date a LOT. I had one good girlfriend my junior year of high school. She had a beautiful dark complexion. We were really naïve.” Wes looked at Sylvia to see if she were about to speak, but her attention was rapt. Wes grinned shyly. “Geez, we were just kids. I hadn’t even done much kissing when I met her.”

“Was she a good kisser?”

“Yeah, eventually. We sort of taught each other to kiss. Hell,” Wes said with a shake of his head, “we taught each other to do a lot of stuff. Too much stuff.”

Sylvia smiled. “That’s sweet, I think.”

“Yeah, it was.”

“That’s how it was with me and my first boyfriend. We were sophomores. He didn’t know how to do anything at first. But eventually he knew how to do everything.”

“What kind of stuff?” Wes asked in a voice he hoped sounded even.

“I dunno,” Sylvia answered, pretending to be put out. “What kind of stuff did YOU do?”

“Well, everything.”

Sylvia sat on the bed with her arms wrapped around her knees, rocking back and forth just a little. “Yeah, me too.”

The movie on television had gotten to the point where Tom Cruise went into the bizarre castle place and walked around staring at people having sex as a church organ played somewhere. Wes and Sylvia watched quietly at scenes of couples having sex, two girls on one guy, a man licking a woman between her legs. Wes felt his heart pound so hard he feared it might explode.

“Are you a good kisser?” Sylvia asked without segue.

That caught Wes offguard in a big way. With no defenses of any kind, all he could say was, “Yes.”

“Wanna make out for a while?”

Wes licked his lips before he could stop himself. “Seriously?”

“I dunno,” Sylvia said with a half-grin. Her cheeks were flush even for her dark skin.

Wes did not wait for the girl to change his mind. He stood from his chair, which was only about half-a-foot from where Sylvia sat on the bed. Moving quickly to keep himself from shaking with nervousness, he leaned down and kissed her on the mouth, holding her smooth chin in one hand. She smelled even cleaner and more delightful than she had on the bus, and her breath smelled good too, although a little like pizza. Sylvia moved one hand up into Wes’s hair, which sent chill bumps across his arms. Her lips parted, and Wes sensed his tongue reaching for hers without his will to direct it. They kissed softly, moderately, breathing a little harder than they had before, although Wes still felt his heart thumping monstrously.

He didn’t know if he should sit down beside Sylvia or try something more forward. Then she pulled him down onto the bed so that they lay side-by-side. As they descended, Sylvia’s arms encircled Wes, and Wes also took her into his arms. Things were moving much faster than Wes expected. Sylvia moved her hands up and down Wes’s body in an intense meaningful way, giving him permission to caress her as well. Earlier in the semester, Wes had made out with a girl who didn’t really have anything better to do, and that hadn’t been intense at all. They’d ended up in this same position, but that girl seemed to be putting up with Wes’s advances rather than making her own. Sylvia, in comparison, was moving her legs up and down Wes’s denim jeans, kissing his neck, encouraging him to kiss hers. Wes forced himself to keep his hands above the waist and pressed against Sylvia’s back and ribs, waiting to explore further until she gave him some sign of permission.

When Wes kissed Sylvia’s ears, she began breathing hard through her nose, in and out and in and out. She dug her hands deeper into the muscles of Wes’s arms. Suddenly she threw her body on top of Wes’s, rolling him onto his back. She attacked his mouth with hers, methodically making love to his face. She was easily the finest kisser Wes had ever experienced.

Sylvia somehow kept her lower body from straddling Wes, which he knew would be the next step toward serious action. Instead, she slowed her kissing, transitioning from deep open mouth lashings to more tender lickings, and finally to gentle pecks on the closed mouth. Wes indulged in his fantasy of touching her beautiful curly hair, which fell around his face in long bouncy locks that smelled great. After a while Sylvia pulled away (Wes told himself she did so with effort), until she sat upright next to him, moving her palms flat against Wes’s chest in an absent-minded way. She looked dazed, her eyes open wide.

“Wow,” she said.

Wes could almost feel his teeth chattering. He clinched his jaw and said, “Yeah.”

Sylvia looked at Wes. “I’m glad we did that.” She was still breathing hard, and even though Wes returned Sylvia’s stare, his peripheral vision couldn’t block the image of her amazing breasts lifting and falling with her deep inhalations.

“So… I guess you want to finish the movie.”

Sylvia moved her head slowly from side to side. She turned the TV off and tossed the remote on the floor. The lamp beside them was the room’s only light now.

“Sooooo… wanna make out some more?”

“Yeah. I guess.” She sounded very nervous, and she did not move. When she smiled this time, she seemed like a different girl from the one Wes had passed in the halls of the Music department for two years. There was something intense and mature about that look in her eyes, but with an element of innocence that didn’t seem to fit with the rest. Not innocent, Wes realized, not innocent but basic, something fundamental. She looked hungry, nakedly hungry. Hungry for Wes, he understood with a start.

“Do you maybe want to…” Wes didn’t finish the thought.

Sylvia’s words were almost a whisper. “No one knows we’re here.”

“Yeah.” Wes was also whispering.

“And we’ll be here all night,” she said more confidently.

Wes sat up on the bed. He felt his mouth going dry. He asked, “How far do you want to go?”

Sylvia leaned forward just a fraction. “How far do YOU want to go?”

“I’d like to… make love to you,” Wes said.

“Have sex,” Sylvia confirmed. She was so quiet, he almost didn’t hear.

“Yeah,” Wes said. He had to keep himself from cheering.

“I don’t think we should limit it,” Sylvia said. She ran a finger along Wes’s chin.

Limit it? What could be further than fucking? Wes said, “Tell me what you’re thinking.”

“I don’t know,” she said, stalling. “It’s just… You’ve been so sweet, and I didn’t expect to be so attracted to you. Or to anyone. Not like this. I mean, Wes, you’re just really great. I guess I was thinking…” She was close enough to kiss. “I guess I’ve always wanted to really cut loose with a boy, and I’d like you to be the boy. The hotel room, the way I’m feeling – it’s all come together like this for a reason. I want to… you know, cut loose. I really want to.”

Wes took a long moment trying to find the right words. “Sylvia… girl, I agree. This feels right. I mean, if you want to just go for it and not have any limits, I’d love that.”

“What do you want to do to me?” Sylvia asked. She was almost panting.

Wes reached up and felt Sylvia’s breast through the t-shirt. Sylvia planted a hard kiss on Wes’s mouth and reached between his legs. Wes felt his penis grow even harder than it had been. Wes moved his kisses down to Sylvia’s neck – where she responded with violent passion each time – as he lifted her shirt up over her chest. His hands caressed her strong back as they made their way to her bra clasp. He fiddled with the hooks until they came undone and Wes could push her bra above her chest as well. Her tits were slightly bigger than medium size, fitting into each of Wes’s hands. He was surprised when Sylvia ripped off her own t-shirt and bra, leaving herself exposed in the lamplight.

“Want the light off?” Wes asked.

“Leave it on,” Sylvia muttered between kisses. She yanked Wes’s shirt out of his jeans and pulled it up hard and away from his body. They stood on their knees on the bed, naked chests pressed together, making out hard. Wes pushed Sylvia onto her back and moved down to kiss her breasts. Her nipple turned hard in his mouth, and she twisted beneath him. Still moving things along quickly, Wes kicked off his shoes and pulled at Sylvia’s shorts simultaneously, still lavishing her boobs with kisses and licks. He discovered that she didn’t have any underwear on, although with his attention on her torso, he couldn’t see anything down there. After just a few moments, she lay naked beneath him.

She pulled him up to kiss her mouth once again. Now he lay between her spread legs, nothing separating their bodies except his jeans. Wes held his body with his arms to keep his full weight from hurting her. He knew his muscular frame would seem heavy to her. They kissed slowly, lovingly. Wes opened his eyes for a brief instant and saw Sylvia’s open as well. He quickly closed his eyes, then opened them again to see if she was still looking. She was. They kissed, lips pressing, tongues teasing, looking into each other’s eyes. Wes pulled away, eyes still locked.

Sylvia said softly, “I’m almost sad we had to end our conversation. I haven’t been able to talk to anyone like that for a long time.” She moved her palms up to Wes’s shoulders. “I’m sort of afraid we won’t be able to talk after this.”

“So let’s keep talking,” Wes suggested. “Tell me what you’re feeling. Describe the experience.” With this, he leaned down and kissed her neck, licking her hard and hot.

“Oh god,” the girl moaned. “I like that, Wes, I really do. I… um… I love the way you kiss me. I like…” She moaned. “I like feeling your chest against mine. I like feeling all your flesh against me.”

“Tell me what I’m doing to you right now,” Wes said.

“You’re… oh… you’re kissing my neck… I like it… I can feel your tongue licking me. It turns me on so much. Now you’re… you’re kissing down along my collarbone to my chest. You’re moving your mouth all over my boobs. Yes, nibble my nipple, Wes. I want to feel your teeth.”

Wes sucked her nipple hard and pinched it lightly between his teeth. Sylvia hummed and moved her feet up and down Wes’s legs.

“Oh Wes… oh god… That feels so fucking good –”

Wes looked up. The word “fuck” had surprised him, and he saw in Sylvia’s eyes that she surprised herself when she said it.

“Was that okay?” she asked.

“Fuck yeah,” Wes responded. “I love to hear you talk dirty. Keep talking, sweetheart.”

“Fuck, Wes, oh fuck… You’re kissing my tummy, you’re kissing my tummy all over, all over… Now you… yuh… ah… you’re licking my inner thigh… It’s turning me on so much… ohhhhhhhh…”

The commentary came to an abrupt halt as Wes shoved his mouth into Sylvia’s pussy. He hadn’t gone this far with a girl in over a year, not since his freshman year. Sylvia’s genitals smelled strong and delicious, and he licked a visibly wet dollop into his mouth and down his throat. The lips outlined the hole to her vagina, and they were beginning to swell. She had shaved neatly around her lips and left only a small patch above the slit. Sylvia moaned deeply and lifted her crotch up, searching for Wes’s mouth again.

“Keep talking,” Wes said, then he glided his tongue up to her clitoris.

“I, I… oh… ah… oh, I… my pussy is so wet for you, Wes… I want you… AH… I want you to keep licking me so hard… right there, oh yes… just a little to the right… OH GOD, oh yeah, that’s so good… keep moving your tongue up and down like that… Oh yes, yes…”

Sylvia bucked her pussy against Wes as he rocked his tongue rapidly against the clit. He reached up and grabbed her tits as she grabbed his hair. Feeling his hair pulled made Wes lick harder.

“Ooooh, ohhhh, oh god, you’re making me cum… You’re making me… oh god… AHHHH, AHHHH…”

As the first orgasm washed over Sylvia, she clinched her jaw and grunted repeatedly like a woman in pain, shivering and rocking against Wes’s mouth. Finally she took a breath and spit out the words, “OH I’m cumming, OH I’m cumming, I’m cumming I’m cumming I’m cumming, OH my god…”

She pulled his face away from her pussy, apparently too sensitive to take any more for the moment. Instead, she pulled him up by the hair on top of her again. Sylvia looked hesitantly at Wes.

“I don’t want to turn you off if I get nasty,” she said.

Wes said, “I want you to be nasty. Whatever turns you on turns me on.”

“I want to taste myself on your mouth,” she said, pulling herself up to lick the juices and cream from Wes’s mouth, moaning softly as she licked. “If you cum on my face,” she said between licks, “would you lick your cum off my face?”

“I would,” Wes said.

Suddenly Sylvia pushed Wes off and stood up beside the bed. In the light of the lamp she looked like a goddess sent to punish Wes, a thing too beautiful to behold. Wes saw every curve, every rare freckle. The flesh around her pussy was still wet.

Sylvia reached out a hand, inviting Wes to join her. Wes stood, and they kissed standing up. He fondled her firm ass as she unbuttoned Wes’s pants.

“Now you tell me what I’m doing to you,” Sylvia said. She licked his neck hard like Wes knew she liked, and he knew why it turned her on so much.

Wes took a deep breath and searched for the words. “You’re unbuttoning my pants, Sylvia, and you’re pulling them down. I’m stepping out of them and you’re, well, you’re tossing them across the room like they offended you. Now you’re, uh, you’re kissing my stomach, tracing lines along my muscles, licking inside my belly button. You’re kissing the fabric of my underwear… Now you’re pulling my briefs down and… and my penis… my penis is sticking out. You’re licking your tongue up the shaft… and down the shaft… and back up again, and now you’re pulling off my shorts…”

Sylvia pushed Wes back against the bed, and he sat down. She started licking his cock again, and he couldn’t keep his hands out of that fabulous curly hair.

“I love to hear your sexy voice,” Sylvia said. “It’s the biggest turn-on I’ve ever had.”

“Oh Sylvia… you’re licking my penis again… you’re moving your hand up and down around it… I’m so hard, Sylvia, I’m so hard… I want to buck against your hand like I’m having sex with you… uh, uh, uh, oh man, ah, ah, ah… Now you’re… you’re moving… you’re, uh… you’re opening your mouth to take my cock inside your mouth… I can feel the roof of your mouth against the head of my… my cock… your hot tongue is wrapped all around my penis… and now you’re… GOD… you’re sucking me off…”

Sylvia reached under and grabbed Wes’s ass as she sucked. Wes pumped his member into her mouth like he was fucking her. Sylvia stopped sucking long enough to lick him, pump him with her fist, and say, “Don’t stop talking, Wes.”

Wes had to find the words to replace his moans and sighs. “Okay, okay… okay… my penis is so deep in your mouth… I feel my cock throbbing… I feel your lips glide down almost to my balls, slobbering all around the shaft, and love how wet your mouth is getting me, I like the feel of your hot saliva dripping from my balls… I like when the head hits the back of your throat… OH MAN…”

As Sylvia took Wes’s cock right back to her throat, Wes lost his vocabulary and simply thumped against her throat, feeling the even tighter caress of her tonsils around his head.

“Sylvia… Sylvia… It feels so good… It feels so good… I want to cum in your mouth and feel you swallow it all... is that okay, Sylvia? I don’t know if… ah, ah, ah… I don’t know if you want to swallow my…”

Sylvia looked up, cock still in mouth, and nodded. Her intent was clear.

“Oh Sylvia… I’m gonna cum… I’m gonna cum so hard… I’m gonna cum… OH MAN I’m cumming… Uh, uh, uh, uh…”

Wes grunted as the semen shot from his shaft, tightening his muscles all along his legs and stomach and even up to his shoulders. He leaned back and sent his seed into Sylvia’s mouth. She collected the cum in her mouth with the cock still inside. Wes felt burning fluid full and heavy all around. Then suddenly, as Sylvia swallowed, he felt an incredible pressure around his sensitive cock. He instinctively grabbed Sylvia by the ears to hold her steady, trying to reduce the shock to his system, as she sucked down what was left of the semen in his shaft. He felt so good he could hardly think. Finally he sank to his knees on the floor and held the girl in his arms, kissing her passionately.

When he recovered, he whispered in her ear, “I thought you wanted me to cum on your face.”

Sylvia whispered back, “We’ve got all night.” She moved her hand across Wes’s back and said, “I’m moving my hand across your back. I’m holding you as we stand up together.” They stood. Barefoot, Sylvia was only an inch shorter than Wes, who stood 5’11. “I’m looking at your face, thinking how much I appreciate you tonight and want to please you. I’m thinking about how turned on I am and how bad I want your cock in my pussy.”

Wes said, “I’m thinking about how beautiful you are and how regretful I am that I never said hello to you before. I’m scared this will be our last night together.”

“I’m thinking about how strong my feelings for you are and how desperately I want you to start dating me when we get back to school.”

Wes kissed Sylvia’s face. “I’m kissing your cheek,” he said. “I’m pulling you down to the bed… I’m rolling you onto your back. I’m looking at you, breathing hard, wanting you.”

“I’m touching your chest,” Sylvia said. “I’m opening my legs for you to enter me. I want you to fuck me so bad.” She closed her eyes. “I want you to fuck me, Wes, I want it so bad.”

Wes put his body into position above her. “I’m holding my cock, Sylvia. I’m aiming it at your pussy… I’m placing the head against your hole… I’m gliding the head into your… aaaaah… your wet… vagina…”

“Wes… oh my god… oh fuck… fuck fuck fuck… oh my god… you’re filling me up, boy… you’re filling me with your big cock… you’re fucking me so good, boy, you’re fucking my pussy so good…”

“Oh fuck Sylvia, I’m fucking you… oh my god this feels so good… your pussy feel like… oh, oh man…”

Wes buried his eight-inch cock as deep into Sylvia as it would go, pressing against her cervix. He didn’t move at all, but simply supported his body above hers. Sylvia twisted her head, moaning, then she opened her eyes and did not look away. The lamplight cast tiny shadows on her forehead where her curls fell.