Erotic Couplings

Daring Moments: Second Installment

Tony's roommates persist in challenging him with dares.

Spankmasters
May 27, 2024
10 min read
rough sexedgingdubious consenttease and denialAn Easy Dare Pt. 02masturbationexhibitionism
An Easy Dare Pt. 02
An Easy Dare Pt. 02

Daring Moments: Second Installment

As I drift off to sleep, vivid images fill my mind of Bea's supple body. My fingers trace her curves, soothing her with gentle strokes while her breath catches in her throat. It seems surreal that I could ever seduce her to this extent, even in my dreams.

If it weren't for her track record with men, I'd think she's been eagerly awaiting my touch. But she's never been one to demand attention and given her casual accord in the past, her passion now seems reckless.

Our encounter from last night comes to mind. With every agonizing minute, she rocked helplessly against me, impatient for the climax she so desperately sought. When compared to that neediness, she still wouldn't have fulfilled her own desires.

My eyes suddenly snap open, confirming my suspicion. It wasn't all a dream.

I cautiously withdraw my wet finger and listen for a reaction. Instead, the girl beside me gives a soft groan and her eyes remain closed. Unable to keep the jolt from my body, I marvel at the moisture I've left on her.

My thoughts wander to my dreams and how reality somehow blended into it. With a stunned expression, I try to piece together the moment I lost control.

Quickly, I slip out of bed and into a pair of shorts followed by a casual t-shirt. The bathroom should be a safe zone while I gather myself and prepare Lucy for my confession.

Ever since I met Lucy, our conversations have been limited to our shared interests. Without knowing more about her relationships, I steered clear of stepping into grey areas. But I couldn't deny the frequent times I admired her hair, her delicate face, and the way it framed her puffed cheeks. Deciding she needs to know about my attraction, I make my way to the kitchen.

Lucy's awkward and reserved demeanor hadn't given me a clue about her sexual prowess. Considering her slim frame, she must be wondering why she could turn me on. I can't suppress my admiration as I notice her embrace her figure in shorts and a strappy top. The uncharacteristic roominess of her clothing is probably an attempt to hide her clothesless body from previous nights. I glance at her bare chest and imagine how it must look to others, gentle, tempting, and feminine.

Upon spotting me, she greets me with a tight-lipped smile, acknowledging the awkwardness that hangs heavy. On a whim, I pour two cups of coffee.

"What happened last night?" she inquires, a slight suspicion in her tone. I stare at the unsettling combination of our dreams blurred in reality.

"Bea insisted on sharing a bed... when really, it would have been better if I slept on the couch," I force out, avoiding her eyes.

"Well, she must be possessive of you," she says with her polite, low voice. I can't hold back and confide in her.

"No, it's more... Nathan, I'm one of the better performers when it comes to this kind of stuff."

Fear trickles into Lucy's eyes and though she attempts a small laugh, her posture stiffens. "You gave in to her, right?" she questions, studying my expression.

"Not yet but..." I start before giving up. There's no use lying about my strong-willed opponent.

"Too bad," Lucy scoffs, tugging at her shorts. "You'll be put to the test again. She'll keep trying until you lose."

As she walks away, I can't control the tent in my pants. She seems to acknowledge her victory by checking me out. I drink my coffee as fast as possible and chase after her. Ultimately, Jess interrupts me in the hallway before I reveal too much.

"Hey there buddy, care to join me for round two?"

I stammered awkwardly, glancing at Jess who was standing there in just a towel, looking at me with a playful smile, "N-no I was, just... hanging out with Lucy."

"Aw, that's sweet. Come, let's hang out with me instead."

With a firm grip on my wrist, she ushered me toward her room. Despite her dainty frame, she was surprisingly strong - I knew this from her hockey practice over the years.

"So, what's up?" I asked, looking around her room as she dragged me in. She remained silent, causing me to feel uneasy. Especially when I realized, my pants were still way too bulky from the previous encounter.

She quickly shut the curtains and closed the door, turning on a lamp by her computer to illuminate her space. Facing the camera, she shrugged slightly before adjusting her webcam.

"Howdy guys, I just got out of the shower. But we've got a special guest today, maybe you can relate. Don't get too jealous of the view he's getting," she jested.

She dropped her towel aside, standing naked in front of me with her confident and toned physique. It wasn't the "type" I was usually drawn to, but her aura of self-assurance and way she filled the space had captivated me. She then straightened up, a betrayed look in her eyes, "So, care to enlighten the viewers why you're here?"

"Uhm, viewers?" I fazed, my mind (and other areas) preoccupied with her naked body. She climbed on my lap, positioning herself to cover me while her bare skin pressed against mine.

"The online audience," Jessica explained gleefully. "Don't fret, they won't see your face. Fans have been curious about your experience with Lucy last night."

"Uh, you mean the dare?" I stuttered, noticing her seemingly bored expression.

"Yes, that," she said, leaning into my neck and I leaned into the affectionate action, "but also, your adventures involving me."

She sauntered off my lap, kneeling back in front of her computer. Retrieving a vibrator from a drawer, she held it up for viewers to see before turning it on, "Feeling adventurous?"

She offered me her lap, saying, "I'll do my best to remain composed, but you'll have to tell enough of a story to bring yourself to climax."

I had to focus, pushing aside thoughts of my online audience. I relished the feel of her bare skin and could only guide my hands on her center, feeling her warm flesh on my palms.

I took a deep breath, picturing Jess seated in my lap, wearing her stylish red dress, her breasts invitingly out in front of my face, showing quite a lot between the gaps in the back and sides of her dress. Her thighs pressed against my hips.

Following her prompts in the dream, when she turned to be in my lap, her cleavage became a thing of desire, pushing her body into mine. "You say your date was dull, uninterested in you. Too bad. But you do ask for my compliments occasionally. You desire that, don't you?"

I obliged, saying her personality and appearance were gorgeous. But she didn't seem swayed, asking for more reassurance. As the story proceeded, I narrated her various tasks and turned her on, she began to hum and moan while grinding her pussy onto my erection.

In the dream, my focus faltered... [

"Must... tell... story..." I gasped, my hands on her stomach, avoiding her breast.

"If your story is compelling, I might reach climax," she said, turning to her computer, her body now sitting on top of my hands.

A buzz filled the room, indicating she'd turned on the vibrator. Her smile looked villainous while she played with it on her thigh, glanced at me and said, "Story time, babe."

I closed my eyes, just feeling her body against me, and my mind quickly conjured the scene. The room was hazy, as if I was trying not to think about who was watching us. Instead, I could only imagine Jess's skin as I caressed her stomach.

The dream began with me enjoying a film, while Jess came home in her date outfit. She was talking about her bad date, specific details to prod me. Jess demanded me to reassure her, using the phrases "good boy", "cute", "sexy" and "gorgeous."

By her constant prompting, I stressed how gushing compliments will make her more attractive. As I calmed, she turned around, straddling me completely. Her chest pushed against my face, the bra straps that showcased her ample cleavage.

I moaned into her chest as she sat upright, my lap suddenly pressed into her, and confessed, "You... said... good boy... I did."

She didn't react quite as I'd expected, acting slight offended, but her body responded with vehemently grinding on my lap. It was then I realized she found it sexy.

...how could I forget? The movement was intoxicating; she disappeared from my lap to retrieve the vibrator... halfway out the door, she smiled slyly.

"Go on, you can cum now."

Frantically holding her hips, the realization that she had full control, hit me like a ton of bricks. She'd be the one deciding my governance. I shuttered under the sensation.

I didn't even wear underwear. I couldn't stop whining. You scolded me, faking shock and embarrassment. As if you just realized the size of my erection when you scolded me.

I apologized but you said it's fine, you could find a way for me to make amends. As long as I begged correctly.

I didn't waste time, asking for your forgiveness and trying to hump you even as you pushed me back down. You soaked in my pleading before finally yielding.

Standing up, you told me I was pardoned. My tongue practically hung out of my mouth as I gaped at you... But you blew me a kiss.

You just thanked me and said you'd sleep better after that. I gawked in astonishment as you walked away to your room.

"Goodness, and that's it?" Jessica asked, her voice dripping with excitement despite being out of breath. One hand squeezed her thigh and brushed her fingers along her slit. She was more aroused by teasing than any direct contact. The vibrator was abandoned on the floor.

My other hand fumbled with her erect nipples, a touch she definitely loved as she rocked on me.

"Could I possibly be that cruel?" she asked, mock-dramatically, rubbing her pussy lips along my length through my clothes.

I could only grunt in response.

"Well, that's the end of our little session. I hope you enjoyed our little chat," she climbed off me, leaning on her desk as she giggled, "Oh, my goodness, you really did. That story was so enticing, but what a tease..."

I watched her as she pretended I wasn't there, but I felt how hot her thighs got, I know she enjoyed it.

"Please, Jess."

"Mmm, did you say something?" she taunted me, wanting more.

"Please, can I, can I take care of you."

"Oh don't be so selfish now. And strangely presumptuous too, what makes you so sure you can."

"Please." I stood up, reaching out to grip her left hip, "Please, I need... Need you."

"If you're so desperate, then you can certainly try, I suppose. But you'll only have ten minutes."

I immediately held her other hip in place and pushed the tip of my cock against her pussy, having already stripped naked when I stood up.

"Holy cow, you're full of surprises!" she teased me, even as she started breathing harder. I realized she hadn't expected me to go straight to pushing my cock inside. Not that she seemed worried as I slid further in and her head dropped. She was silent as I held her back against me.

"More, now," she ordered, barking out a command. I instead held myself inside, relishing the tight fit of her. I shifted my hips so I could press in at different angles, "Good dog, but I need you to pound me."

Instead of waiting, she pulled forward, I inhaled sharply as her pussy lips skimmed along my length. Instinctively, I followed her lead, pulling back. We both paused and I sensed as soon as she started to back into me, and I thrust forward.

"Yes, yes!" she growled. "Harder, deeper."

I was lost in the moment, so I didn't say I couldn't go deeper. And the next thrust proved me wrong anyway. I felt myself stretching, elongating into her tight grip as she moaned in delight. She didn't slow down at all, always reacting before me.

I felt the slap of my hips on her ass reverberate through me. The sound was my cue to pull back again, because no matter what I did, she kept reacting before me. She refused to slow down even as her breathing became ragged.

Braced against her desk, she rattled loudly each time I thrust inside her. She seemed to love it, making no effort to stop, even bumping into things accidentally.

But then, after one pull back, I felt her pull away completely. I stopped, watching her reaction as she turned to face me, and then grabbed my cock to jerk it.

"Against the wall, pin me down."

I swallowed, unsure if I could.

"Just hold me against it," she guided me to it, conspicuously choosing one with a selection of framed photos and prints adorning it. But it provided enough space for her body as she pulled me close and pressed my cock against hers.

"And my thighs can hold you inside me," she ordered, guiding me to her and the gap felt snug even now. I pushed myself all the way in, obeying her command.

"Good dog, who knew you were so compliant," she brushed her fingers through my hair, now letting me take the lead.

"You deserve a reward," she murmured, her eyes locked on mine, "What could you want more than having your way with me like this, hmmm..."

I was barely aware of anything as I fucked her again and again, relentlessly pushing my energy into making her moan my name as she came, enjoying my cock fully inside her.

"I've got an idea. Why don't I help you find a way to have rough sex with Lucy? You seem excited about the idea. I think you just need to understand she's already a wild one. You just might not know it because I'm near her room and hear her moans late at night. She sounds so desperate, even more than you do right now."

As I pound into Jess harder and harder, she keeps encouraging me. Her words make me even more eager. I can tell she's on the brink too. Her focus is getting harder to keep.

I pause inside her, pressing her tightly against me. Feeling how hard my cock is in her.

"You...you want me to-"

But I cut her off with a passionate kiss. One that leaves her lips wet and messy. I bite her lip and then say, "Cum on my cock Jess, get it wet. I'm going to fuck Lucy with it."

Her eyes lose focus as she hears my plan. And then, she bites her lip with a gasp, matching my own.

"Cum, Jess," I demand as I bite again. She gasps harder. I bite her again. Another hard order and she gasps more heavily. I do it one more time and she almost collapses, her lips trembling.

When I release her, she puts a hand on my chest firmly. She uses her other to close down her live stream.

She shakes her head, muttering a curse before saying, "Jesus Christ."

I look confused until she turns and sees the bites on her neck. She flushes over and says, "Oh, more than a little."

She takes a few quick glances in the mirror, examining the bite marks. Then she smiles, "You did really well."

Her clothes are nearly back on when she notices my awe her words bring. "You're not done yet, are you?"

I stare at her in confusion until she explains why she judged my strength. "You want to make Lucy groan like that, don't you?"

I nod dumbly.

"I'm trying to say," she says with a wide grin, "That you did great and you should try it out."

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