Right To A Bed

Two Weeks Earlier...

Tessa sat on her bedroom floor, wet hair wrapped in a towel, a bottle of water at her side, and a small book in her hand. "'Guys like a confident woman, taking control of a situation and not showing any fear can not only win you the attention of the man you're trying to impress, but also make you the center of whatever event you find yourself in.'" Tessa read aloud to herself, "I think I was doing that alright last time...I mean, I asked him out, I didn't freeze up or do something stupid like back at the pool..." The brunette cringed as she remembered the way she immediately started feeling Kenny's biceps moments into meeting for the first time. It was far from her finest hour, but she hadn't expected Juliet's cousin to look so...

Tessa shook her head and looked back down to her book, "'Confidence should also lead into the bedroom as well. Some guys like a girl to be more submissive or dominant, but regardless, being confident in both your body and yourself will lead to far better outcomes and memories. However, don't fall into the fallacy of overconfidence, pushing too far can very easily cause your target to run off before you can blink!'" Tessa chewed on her lip, unable to suppress a grin, "I don't think I was being over-confident, I tried to be fun but I also held back on the kiss...that I really frickin wanted too..."

Tessa let her head fall back, resting against her bed as she quickly fell into a daydream, thinking back to that moment at Kenny's car, but instead of turning her cheek this time she let his lips sail home. She could nearly feel the scruff on his face tickling hers and the taste of his lips, "If I can land it this time...if I can actually not put my own foot in my mouth long enough to get him somewhere, I can actually..." Tessa's body shuddered and she breathed out a heavy breath, "I'm sure he's done it lots of times by now, he could lead me through everything, and then I could finally know what it's like." Tessa shut her eyes contently, "Mhm, Ken, I can't wait for our date..."

This is going so fucking bad! Tessa internally screamed in a panic as she stared back at Kenny trying to not look as horrified as she felt. Did I say that?! Did I actually fucking tell him I was thinking dirty thoughts too?! I mean, I was...kinda? B-But that's not what I meant, I just don't want him to think I'm a prude, but what if he thinks I'm a slut now?! Oh God, I was supposed to be assertive, not a slut! Tessa felt her face becoming redder by the second. I only wanted to appeal to him, be bold, show myself off a little so he knew I was game, not -- Oh God, I made it so fucking awkward now! Shoot me! I have to try and fix this before he leaves!

Meanwhile, Kenny was doing his best to wrap his mind around the situation he found himself in. Tessa really just said she was thinking about dirty stuff too? Like, dirty sex stuff, right? That's what I meant, and she didn't skip a beat! Should I...do I ask her to come back to my place? No! No, I can't ask that, she'll -- It's already too awkward, I'll just make it worse! I should just pretend this didn't happen, we finish the date, I take her home, and then we can just forget about it all. I mean I totally put her on the spot, she must be sick of me now... Kenny finished with a low exhale. Maybe I should just ask if she wants to go home now...

"Hey!" Both teens said in the same moment, their eyes widened, "Sorry, you first!" They matched each other word for word once again. Tessa sank down in her seat, unable to look more mortified.

Kenny waited for a moment and Tessa did the same, making it clear he was to speak, "Sorry, I was just thinking..." The teen sighed and rubbed the back of his neck, "Want to just say forget the dinner and go now?"

Tessa's lips parted and a squeaking breath left, no words able to leave her mouth for a few seconds, but with a quick swallow she nodded quickly, "S-Sure, let's go now."

Kenny got up, leaving payment for the drinks on the table, and headed out with Tessa in tow. Okay, so this did not go anywhere near planned but that's alright. We can head back home, take a few days and then once things aren't so awkward, maybe we can try this again? I don't know, I just feel so fucking bad for doing this to her. Kenny thought as they reached the sidewalk, though, to Kenny's surprise, Tessa wrapped herself around his arm again, though she couldn't seem to find the courage to look him in the eye. "Um, want me to get a cab or something?"

"Huh? Oh no, it's not far from here," Tessa murmured back and she tentatively took lead, bringing Kenny up the road.

Oh, she lives on this end of town? Must be an apartment or something then? Kenny thought as he began to walk with the brunette. They made their way up the road for a few blocks, turned down the road, and went a few more before Tessa finally stopped. Her cheeks were positively glowing red and Kenny looked around in confusion, there was no apartment building, nor was there home, all that was in front of him was...the Mountain Lodge Hotel? "What are we doing -- You live in the hotel?"

"What? No? What are you talking about?" Tessa replied in confusion, her voice quivering with nerves,

Kenny's head tilted for a moment and like a lightbulb, he finally connected everything, "Oh shit..." He whispered under his breath, staring at the hotel with wide eyes, "T-Tess, when I said go earlier, I m-meant...Go home..."

"W-What?!" Tessa recoiled away from the teen. OH MY GOD! Tessa! What the fuck are you doing?! You brought him here to have sex and he wanted to take you home! Are you insane! You stupid, stupid girl! Oh God, how did I do something like this?! This is the stupidest thing I've ever fucking done in my life! Just kill me! Kill me now! He's going to think of me as the weird freaky slut girl instead of the confident one! I screwed up so bad! He'll never go out on another date with me! Tessa lifted her hands and pushed them through her hair, her mind racing with a million thoughts. Wait! Wait, I can fix this! Y-Yeah, I can fix this! Stick with what I learned! Be bold! Be confident! Take control! Take what you want!

"Tess," Kenny tentatively lifted a hand, "It's okay, it was a misunderstanding. I should have explained -- It's not your fault!" Kenny attempted to reassure the girl, though to his surprise she suddenly let out a scoffing laugh.

Forcing herself to stand tall, Tessa crossed her arms and looked Kenny dead in the eye, "We walked all the way here, we can get the room, and you want to leave?" She asked, her tone holding a bit of challenge, "What, are you too scared to do this?"

Kenny looked between the hotel and the brunette a few quick times, "Huh, What? Do you mean --"

Don't look scared! This is you being in control, he's the one who's scared right now, lead him through it! Tessa thought to herself, smirking as she looked Kenny up and down, "Look if you're scared because it's your first time or something, it's fine. I'll lead you through this, I promise, you'll like it." Kenny was nearly slack-jaw, only letting out broken breaths and the occasional start of a word that never made it to completion, "Seriously? Can you not handle this?" The brunette added on and finally, she saw a spark in Kenny's eye, and then it was as if something different suddenly took the wheel in his mind. Oh fuck...did I actually do it? Tessa's heart skipped a beat.

Kenny wet his lips and looked at the hotel, "Are you sure you want to do this?" He asked, his voice much calmer and more controlled than before, "I just don't want you to have any regrets,"

"Regrets," Tessa scoffed again, "I brought you here, remember? I'm not regretting a thing."

"Alright then," Kenny reached out and took Tessa's hand, "Then let's get a room," Tessa instantly gripped Kenny's hand and her heart started thumping harder than ever before. Holy shit! Holy shit! I did it! Holy fucking shit, this is happening! I'm gonna -- He's going to -- Oh my God! Tessa squealed in her head as she followed Kenny step for step into the hotel.

In mere minutes, the teens had paid for a room and gotten inside. Trying to continue her flow of confidence, Tessa locked the door and immediately went for her shirt before Kenny could say a word. She pulled it top off her body and tossed it aside before going for her pants. The brunette's body was a mess of nerves and excitement, but she did everything in her power to control her shaking hands, pushing her pants and skirt down to the floor. To her surprise, when she looked back up, she already found Kenny standing over her in just his briefs, drinking in the sight. Tessa let out a nervous squeak and Kenny crossed his arms with a smirk, "What? Feeling nervous all of a sudden?"

"N-No!" Tessa exclaimed, jumping right up and reaching back, unhooking her bra. However, as the fabric fell away, she immediately felt her confidence go with it. Pivoting her body, Tessa lifted her arm, covering her bare breasts from Kenny's eyes, "I just need...a...second," She softly replied until she was fully turned away and Kenny's arms slowly lowered. Okay, Tess, okay, calm down. You can do this, don't freeze. It's going to be okay. You. Can. Do. This. Don't lose it, stay in control, take the lead, you can do it...don't be obvious that this is your first time...

Suddenly Tessa felt Kenny's arms wrapping around her body and his chest pressing into her back. She let out a low gasp, immediately in love with the tickle of his scruff on her neck and the warm breath tickling her ear, "What are you thinking about so long over here? I thought you said you were going to be leading me through all this, right?"

"I w-was..." Tessa nodded, trembling as Kenny's right hand worked its way up until it was cupping one of her breasts and the left slid down towards her mound at a ginger pace, "I want to -- I needed to -- Haehh..." Tessa breathed out a moan, her whole body tingling from the sensation of Kenny's rougher, stronger hands massaging her most sensitive areas, "T-That's so different than when I do it..."

"Oh? You do this a lot?" Kenny teased, his left hand finally reaching her panties, and his two middle fingers began to slide up and down the length of her slit,

Tessa squeaked out another moan, and pressed her body into Kenny's, "N-Not like that -- In the shower I meant, o-obviously,"

'Yeah...obviously," Kenny hummed back, softly snickering along with it making Tessa blush even harder, "You're not very comfortable with this taking control thing, are you?" Tessa turned her head, giving Kenny a glare that told him everything he needed. He easily smiled at Tessa and with ease, pushed his hand right into her panties. Tessa let out a gasp and in the very next second, she found Kenny's lips pressed against hers.

The brunette immediately melted into the kiss and her body was all but limp against Kenny's body, using it for support as his fingers slid and teased her slickening slit. That feels good...really fucking good, so much better than when I do...my whole body feels tingly... Tessa thought, her body relaxing now and the pair reaching a natural flow with their kiss, their tongues starting to brush against one another before finally starting to dance. It's just like I thought...he's so good at this...mhm...his beard tickles. Tessa's kissing started to turn stronger. Fuck, his fingers are so fucking nice, it's making everything -- w-wait, they are really making me -- Tessa's eyes sprung open and she abruptly let out a shouting moan into Kenny's mouth as a sudden, and unexpected orgasm suddenly took hold. Her entire body tensed, her eyes squeezed shut again, her legs went to jelly, and a flow of her cum flowed onto Kenny's fingers until she finally gasped out, falling to her knees. "O-Oh my God..."

"Heh, sure you're alright? Do you want to slow down for a few minutes?" Kenny asked only for Tessa to look up, her crystal blue eyes swimming with lustful desire,

"I'm f-fine..." Tessa stammered back, letting out a few sharp breaths. Fuck, he's gonna know, I keep acting like some loser, be sexy! Be hot! Tessa calmed her breath, "No way I'd stop now, it's finally getting good," She confidently added while finally looking up, but her sly, teasing look shifted to one of awe and even a touch of fear as she now found Kenny standing before her, boxers off, and thick rod point right at her face, "Oh...my...God..."

"You alright?" Kenny asked once more, "Tess, we really can slow down a little,"

"I don't need to slow down!" Tessa barked back and abruptly grabbed Kenny's cock, pulling the teen even closer, "I am perfectly fine. You think this is the first time I've seen a big dick? I know what to do." Tessa huffed out a breath a sat up on her knees. She tucked her long black hair behind her ear and leaned in, opening her mouth far wider then needed. Blowjob, just suck on it, simple... The girl turned her head, still attempting to size up the best way to do this. Jesus, it'll barely fit! How is it supposed to fit inside me if I can't even get it in my mouth?!

"Tess..." The brunette flicked her eyes up and Kenny reached down, helping her to her feet, "It's your first time, isn't it?" Tessa's eyes sprung open, and her whole body started to heat up, her face immediately a bright red, "It's okay, you don't have to be embarrassed."

"H-How did you know?" Tessa squeaked back,

"Let's just say my first time was uh...a little similar," Kenny vaguely replied with a calming smile, "I was trying to do whatever I could to impress too. But you don't have to do that. We should both be relaxed." Tessa blew out a shaky breath and nodded in full agreement, "Good, so instead of trying to do everything you think you should be doing, you tell me what you want inside."

"I want...I want..." Tessa swallowed hard, her bright blue eyes staring deeply into Kenny's, feeling a certain level of comfort from just how relaxed they were, "Kiss me. I want you to kiss me."

"Anything you want." Kenny murmured back while leaning in and with a little tilt of his head, his lips pressed against Tessa's. The brunette let out a low humming exhale, her hands tentatively worked their way around Kenny's back until she was now fully embracing him. Tessa stepped back and Kenny moved forward, the two tipped and fell onto the bed, their lips remaining interlocked and tongues swirling around one another.

Low moans escaped through the breaks of their kiss, and Tessa's hips lifted pressed against Kenny's hardened tool. The brown-haired teen could feel a warm, heavenly heat as she pressed against him and a sticky wet stream remained on his cock as she fell away. Tessa's breathing was turning heavier and huskier by the second, and finally she broke away from their kiss, "Please, just do it...I want you to do it, Kenny,"

"You sure?" Tessa rolled her lips in, swallowing nervously, but rapidly nodded her head. Kenny moved his hands down, gripping his cock with one and gently pulling Tessa's panties to the side. Tessa let out a small murmuring moan as she felt the fabric slide off her sensitive lips, Kenny's blew out a slow breath as he didn't really expect the girl to be as wet as she was. "F-Fuck me...please," Tessa begged one final time, just as Kenny's head came in contact with her lips.

Kenny let out a few panting breaths before he pushed his waist down, his cock pressing against Tessa's resistant hole. The girls face scrunched up, and her head tilted, the foreign feeling while odd and even a bit painful, wasn't fully unwelcome. Her body tensed as Kenny's throbbing head started to slip into her, Kenny let out a small grunt, and Tessa quickly reached up, gripping onto his forearm. "Y-You okay?" Kenny breathed out as he continued to push in, his body seemingly unable to stop from being enveloped by Tessa's tight heat,

"Wow," Tessa merely moaned back, her eyes closed and her mind clearly only focused on the feeling inside her pussy. Oh my fucking God, he's inside me, I'm...I'm not a virgin anymore...I didn't think it'd hurt so much but...Fuck, I want to feel more...I want so much more. Kenny could feel her slight tremble as he fed her his cock at a molasses pace, though each inch that entered sent shocked of pleasure through both their bodies. "J-Just give it, push in, push it all in," Tessa nearly growled as Kenny reached his halfway point.

The pair stared at one another for a long few seconds before Kenny's hands moved away from his cock and Tessa's panties. He fully bent over, resting his arms on either side of Tessa's head and with a fluid motion, pressed his hips down, sinking what was left into Tessa's fresh unused cunt. Tessa's eyes sprang open, her back arched, and her mouth fell open, yet no noise came out. Kenny froze in fear for a moment, merely waiting for Tessa to say or do something, he could feel the tenseness in her every muscle.

Then, to Kenny's relief, Tessa's body started to relax, and she exhaled a shaky but calming breath. "Are you okay? Tess, do you want me to stop?" Kenny instantly offered though he couldn't help but let out a groan as the brunette's pussy twitched and quivered, milking his shaft.

"N-No," Tessa denied, wrapping her arms around Kenny's neck, "Please don't stop, please fuck me, Kenny. Fuck me." She begged with a moaning whine, and the teen was all too happy to please. Starting with slow, but steady strokes, Kenny began to rock his hips, working just a bit of his dick out of Tessa before letting it slide back in. Each time he hilted in her the brunette let out a breathy moan and her arms squeezed him a little tighter. "Faster...go faster..."

"Okay, Tess," Kenny breathed back, rolling in his lower lips he bucked his hips with a bit sharper. This time the two could both hear the wet sucking squelch of his cock starting to piston in and out of the brunette.

"Fuck, fuck, fuck, fuck, oh shit Kenny, just like that. Oh my god, that feels so fucking good." Tessa whispered before pressing her face into the teens shoulder. moaning out louder and longer with each passing second. Kenny let out a breaking moan of his own, increasing speed again as the heavenly feeling of her tight milking cunt started to slowly overtake him. "Yes, yes, yes, just like that, just like that. Fuck me, fuck me, Kenny!" Tessa encouraged with eager lifts of her hips.

Minutes past and the heat emanating from the teen's bodies was nearly burning, sweat was clinging to their flesh, and their hair was even starting to turn wet. Their husky breathing and wet slaps of their colliding hips filled the entire hotel room. "Oh fucking god, Tess," Kenny finally moaned out as he felt the girl lift and wrap her legs around his lower back,

"Oh god, Kenny, oh my god, don't stop, keep going! I'm close! I'm so close, please just a little more!" Tessa begged before squealing out as her first, and by far most intense orgasm overtook her. Kenny's squeezed his eyes shut and rammed himself into Tessa's cumming cunt, releasing his seed almost instantly. Tessa bit down on Kenny's shoulder and screamed out louder than ever before, her face becoming deep red as bolts of lightening were rocketing through her body head to toe. The feeling of cumming was one thing, but the sensation of Kenny's hot seed filling her insides was a complete other.

Kenny's eyes were seeing double as he continued to fire into Tessa's milking cunt, and he thought he might even pass out when Tessa's release finally passed and she went limp underneath him. "H-Holy fuck..." Kenny panted as he finished his fifth and final spurt, his intense orgasm finally passing as well. He swallowed hard and blinked a few times before feeling Tessa's leg slip off him and fall to the bed.

Rolling over the two sweaty teens began to gasp out heavily, staring up at the ceiling, "S-So that's what it's -- I never thought it'd be -- F-fucking wow..." Tessa stammered out as she draped her arm over her eyes, "I fucking loved that..."

"Me too," Kenny sighed in agreement before glancing over to the older girl, "I didn't hurt you?"

"A little at the start but fuck it was so worth it," Tessa breathed back, "That was better than I ever thought it was going to be," The brunette wet her lips and **** her body up, getting to her very wobbly legs. Kenny quickly sat up as well, "Whoa, okay, yeah that feels a little weird..." Tessa mumbled as she took a shaky step, "Sorry, I just want to shower, I feel really hot and sticky now."

"No problem," Kenny nodded back with a warm smile,

"Do you...want to join me?" Tessa added with a hopeful grin, "I don't think I could really go again right now, but uh, I don't know...I wouldn't mind the company with me..."

Kenny let out a breath laugh and swung his way out of bed, "Like I said, whatever you want. You deserve a special night," Tessa made no attempt to hide her blushing cheeks as Kenny made his way into the bathroom.

However as she took a few steps she heard Kenny's phone buzz on the armchair near the door. As Kenny started the shower, Tessa couldn't help but peak over at the device, seeing a text coming in from her sister.

• We're still on for tomorrow, right? Really want to make sure you'll be ready for the recruitment drive at the end of month! Plus, I was thinking of a few more exercises we could do after we close that you're gonna love. ;)

Tessa's eyes ever so slightly narrowed. I knew! I knew you were lying to me when you said Kenny was just a friend Mimi! Well, prepare for some competition! Kenny's way to awesome for me just to walk away because you've got a little crush and are back on the market! Hmph, bring it on, Mimi, bring it on. Tessa confidently decided before sauntering into the bathroom, putting an extra sway in her step.

"Hey!" Tessa exclaimed in a cheerful tone, and Kenny quickly glanced back, "I can definitely say once again I'd love to go on another date with you. What do you think about the end of the month? You know, after everyone heads off to BMU for college and you're tryouts for the academy are done?"

"Oh...uh...I -- Sure Tess, that sounds great," Kenny replied, putting on another smile, though he immediately felt his stomach twist into knots. Tessa didn't notice a thing, merely planting a quick peck on his lips and stepping into the shower. Oh Jesus Christ, what am I doing? I can't keep bouncing from girl to girl like this. I have to stop, I need to decide what the hell I'm actually gonna do here...