Challenge Accepted: Part 1 - A Simple Bet
"Huh, what did you say?" I inquire, adjusting my posture and anxiously wondering if I heard her correctly.
"Which one of us have you had a naughty dream about?" Bea teases, her arms crossed as she smirks. She can sense my discomfort, though I hope she can't tell I'm already beginning to respond physically. The game of truth or dare has already started to get quite risqué, but she's really taken it up a notch.
"Um, what do you mean by naughty dream?" I inquire, partially just to buy time and gather my thoughts.
Lucy clears her throat and removes her glasses, leaning forward to respond before the rules lawyer steps in.
"Well, any dream you've had about one of us that turned you on."
She bites her lip, observing my reaction. The quietest girl, yet she's chosen some interesting moments to interject during the game.
Jess interjects, "Exactly! It doesn't necessarily mean you've had sex. I've had plenty of dreams that included oral or just a good make-out session."
Finally, I decide to answer.
"...all three of you."
There's a heavy silence as my response sinks in. I'm uncertain where to look. I can see each girl is curious about which name I would choose, but they're all surprised by my response.
"Huh, so our little Tony's quite the player, huh?" Jess chuckles, breaking into a grin. She's sitting on the floor with her legs crossed, barely wearing clothes as she flatters her spectacular figure. The tallest and slimmest girl, she's not my roommate, so she can easily make me feel uncomfortable because I don't know her that well. But she makes it a hobby.
She exudes an arrogant confidence and pierces me with an intense stare. She's wearing make-up, because she was on a date prior to this. Her outfit presents an odd contrast, as she's wearing a borrowed shirt from Jess, which is stretched across Bea's larger chest, and hangs down just above her mid-thigh. She doesn't have anything on her lower half except her panties... hopefully.
This unexpected sleepover took place because Bea unexpectedly showed up at our doorstep, livid and crying due to a disastrous date with her long-term boyfriend. Rather than return home with him, she needed a place to stay and needed a distraction.
"So what kind of kinky dreams have you been having about me?" Bea asks with a grin, unconcerned by my answer. Instead, she seems anticipating making me uncomfortable.
"It's now Lucy's turn to face a truth," I stress, diverting the attention from me. I turn to look at Lucy finally, concerned she'll be shocked by my response. She's looking at me with intense concentration, examining me carefully. Lucy is a tall, chubby girl with ample hips. She's wearing a tank top and yoga pants, perfectly matching her exceptional curves. She's so precisely my type, I've had to avoid checking her out during our tour of the house initially. It was a struggle, but she's such a sweet, innocent girl I can't imagine her reacting negatively.
Me, Jess, and Lucy have shared a residence for six months now, and things have gone well. I've always tried to make them comfortable, conscious of the potential awkwardness of having a male roommate. But so far, it's gone smoothly, and we've grown closer. I've made sure not to be a creep or make any moves as a roommate.
Obviously, I've acknowledged Lucy and Jess's attractiveness. I'm not an exaggeration when I say I'm a slut. I'm drawn to most women because of their features. So many women have features I can't overlook. However, I've decided to remain silent about it, not wanting to make any of my friends feel like I was trying to get into their pants.
Except now, Bea has stirred the pot with her personal and probing questions. She seemed determined to make me the target for her frustration regarding her ex-boyfriend.
"Alright, I'll join in again," Lucy told me, sounding a bit apologetic as she gave me a look, "Time for truth or dare?"
"Dare me instead," I suggested, patting her arm, hoping my friendly gesture would help ease things between us.
"Lucy will be cautious too..." I heard Jess whisper, and Lucy looked over at her before fixing her gaze back on me.
Her cheeks were still slightly flushed as she declared, "I dare you to describe your dream about me in detail."
My mouth felt dry. While a part of me wanted to share my dream with her, I couldn't help noticing the other two girls seeming to be eager to hear what I had to say.
"Aren't... that sort of like a truth?" I asked hesitantly.
"Hmm, okay. I'll dare you to describe it while whispering directly into my ear. That way, only I hear it," she said before giving me a sharp look.
I weighed my options, considering whether to argue but then noticed the intensity in her eyes. She locked her gaze with mine, then walked around and perched on my lap. I felt her sitting down forcefully on my lap, causing her thighs to rub against my legs and her knees to press against the inside of mine. Despite the discomfort, I tried to shift so as not to embarrass us with my hardness. Lucy glanced at me briefly when our groins touched, then leaned forward and whispered in my ear, "Go on."
I contemplated whether to argue but instead, I told her about my dream.
It started with me awaking on the couch, groggy and half asleep. I stretched and proceeded to my room, only to hear a noise coming from hers. It sounded like she was in the midst of something arousing. I felt a strong urge to investigate, and knocked on the door.
Upon entering her room, I found her on her bed, wildly riding a pillow. Her top was off, and her hips were moving on the bedsheets. I was surprised, and hesitated before apologizing. However, she broke her grinding and apologized too, explaining that she just needed to reach her peak. Her hips continued to jerk uncontrollably as she spoke, and my body trembled with every spasm she caused.
I moved closer, wanting to help alleviate her discomfort. She dismissed my offer, but I ballsily persisted, kneeling by her side and asking if I could assist. Her initial response was to dismiss me, but my persistence must have convinced her.
She shook her head, saying something hasty like "You don't 'have' to," but I moved even closer, saying I really wanted to help. I repeated my insistence until she relented, allowing me to kneel by her side. My hips pushed against hers and my breaths quickened as I started to beg for permission to get closer. She responded by grabbing my hand and bringing it between her legs.
She hadn't spoken a word out loud, but she kept my hand there as I stretched my fingers to stimulate her. My fingers dipped between her folds, soaking up her juices from the pillow. The erotic aroma of her excitement filled the room, and I could feel the heat from her body.
I could sense how desperately eager she was to finish, but I didn't know how long she had been trying. I kept up my pleas, my lips pressing against her ears to encourage her. Eventually, she let go and let me take over, pulling my hand closer again. However, I moved to the side in order to kneel between her legs, kissing her inner thighs. I cleaned her up, licking up the remnants of her desire.
My hands were covered in her wetness, and I didn't want to just describe it, so I cleaned her up.
"...and then what?" Lucy questioned once I was done.
"Uhm, usually, that's when I end up waking up," I said, adjusting in my seat, still a bit uncomfortable and distracted by how quickly I had become aroused.
"Wait a minute!" Bea tosses a pillow at me. "So you're telling me you don't... you know? It's like she's upset that our fun has been cut short.
Jess grins impishly as Lucy inches her way off my lap.
"So," Jess says with a smirk, "Now that you've got a little bit of attention, how often do you think about that dream?"
"Well, er... it's not... it's true, isn't it?" I stumble.
Jess tilts her head, thinking. "Nah, if you want the truth, I've got something better for you."
My stomach feels a little heavy, but this is also turning me on. I don't want this teasing to end. Bea seems to feel the same as she gazes at my bulge.
Jess scoots behind Bea, playfully resting her chin on top of Bea's head. Seeing that Bea was about to make a comment, Jess cupped her chest, surprising Bea.
"Truth, if you could do anything you wanted to Bea's gorgeous body now, what would it be?" It makes Bea smile. She even reaches up to adjust her tank top, which raises the prominent cleavage even more.
"Interesting question," Bea says, winking, "I'd love to hear what you're thinking."
Lucy, a bit shocked, watches us closely. I felt guilty for what I'd been telling her, but her expression suggests something else.
"Don't forget, tell the truth," Jess adds casually. Her hand slowly travels up Bea's inner thighs. Bea opens her legs a bit, revealing more skin and more of her top.
"I'd want to eat her out," I say hurriedly. "To make her feel amazing."
Bea bursts out laughing. "Oh please! It sounds just like something a guy would say. It's as bad as 'you look so good without makeup.'" She makes a barfing noise.
"I really mean it!" I insist.
Jess giggles. "Hmm. If you're so desperate to prove this, let's make this a dare and it'll be easier to avoid if it's not true."
Bea nods in agreement. "We dare you to abstain from masturbating for a month. No dick for you, not even your own."
"I can do it," I agree without hesitation. I feel a strange sense of pride.
Bea adds mischievously, "If you agree, we can tease you, tempt you, and use you."
"I'll let you do whatever you want," I say hesitantly.
"Do the girls in this house get a say?" Lucy asks suddenly.
I frown, glancing at Lucy, surprised that she'd interject. "Don't leave me out. Just say 'the girls in this house'."
"Alright," Bea agrees.
"What about me?" I ask.
Bea shrugs casually. "Well, isn't this what you were asking for?"
I can't deny it...
Later that night, everyone heads off to prepare for bed. The topic of the dare isn't brought up again, but I still hold hopes that they were serious. But Bea is the most likely to flip the script. I'm on the small couch, trying to get comfortable when I hear a throat clear at the door.
I freeze instantly, thinking this could be Bea coming to collect on her threats. "What do you want Bea?" I ask cautiously, not daring to look at her.
She enters the room, dressed the same way as before except she's added a pair of sweatpants. "You don't need to sleep on this couch. You're too lanky. Go to your bed and get some proper sleep."
I turn to leave, desperate to hide my hard-on. "Only for tonight," I say sullenly.
Bea shakes her head. "Nope, not happening. Sleep in peace."
I go to the couch and leave her behind while I make my way to my room. As I slip under my covers, I inhale deeply, delighted by the scent of her shampoo on my pillows. I can't help but feel a bit sad that she didn't test me, or make me prove my claims about how long it takes me to achieve climax.
The truth is, I don't usually come quickly, even on my own. It takes a persistent girlfriend or a few hours of alone time. What really thrills me, though, is witnessing a woman's excitement and orgasms.
As I lay there, half in a daydream, reminiscing about the times Lucy used to tease me, I feel the door open. I listen as Bea drops her pants to the ground, revealing a small thong underneath.
With a sigh of frustration, she says to herself, "Someone fell asleep fast." She sheds her shirt and walks toward the bed. She doesn't notice that I'm fully awake until she climbs in beside me. Her giant breasts jiggle as she moves closer to straddle my body.
She brushes her chest against my face, and I can't allow her to see that I'm awake, so I keep my eyes half-closed. Her breath tickles my skin as she leans over me. When she pauses to take a deep breath, I hear her walk herself to the brink of orgasm, gasping softly as she strokes herself.
I can't hold back forever, though, so I open my eyes just enough to watch as her finger brushes against my bulge. I harden against the fabric of my boxers. She moans, grunting softly. She must think I'm asleep, and that's why she's unable to hide her own excitement.
I fold her underwear aside and free my erection. Her thong is the only thing left between us as she presses herself against me. She lets out an exasperated sigh, whispering, "What a waste." Regardless, I lean down to kiss her, pushing her head forcefully into my shoulder.
I feel her on top of me, but her control slips as she gets more aroused, causing the bed to shake against the wall. Riding my hips, she twists and arches her back.
"Oh, fuck, oh god... I, I,"
Smelling her anticipation, I grip her hips and flip her onto her stomach. My erection juts up against her ass, and I position myself to give her a tantalizing taste of myself. She squats on my stiff cock and pushes her ass back, eager for more.
"It's just part of your charm," she mumbles, dragging her breasts along my arm. I hold her down and enter her.
As I thrust into her, she begins to gasp and pant.
"Oh fuck," she mumbles after a while. "You can have your way with me," she says heedlessly. She attempts to return my thrusts, but quickly realizes that I'm in control.
Although it's not my usual style, I remain somewhat rough, pushing her timidly onto her back and rotating to hold her pinned beneath me. Her eyes go glassy as she cums a second time, her hips bucking uncontrollably against me.
I hold her down and begin to lick and kiss her stomach, my hand winding up between her legs to touch her. She's still rocking against me, desperate for more. I move my head lower, brushing past her clit with my lips before returning to her thigh.
Her hips help my quest, committing to the rhythm as she hovers over me. Excited, I reach up and secure her thighs. Unable to hold out any longer, she cries out with desire, rising to meet my touch.
I lean over her and circle her nipple with my tongue, then slide my hand between her legs, making sure to rub her clit just right. She gasps, rolling her head into the pillow as she climaxes, squirming and straining against me.
When she comes down from her high, I roll her onto her back and kiss her breasts while making her cum for a third time. I repeat the pattern, kissing her stomach and thighs, until I've made her a total of four orgasms.
Her legs trembling with pleasure, she begs me to stop teasing her. However, I still choose to focus on her excitement, kissing and nibbling until she loses herself in a fifth orgasm. Fearing that her body couldn't handle any more, I stop.
"This is what I've always wanted, do you believe me now?" I ask, watching her body quiver from the aftershocks.
"Jesus Christ--just fu--just fu--"
"You dared me! I'll give myself to you until you cum again."
"Didn't--didn't even finish," she stammered, panting.
"How many times can you do that?"
"I--Oh god, oh god," she moaned as I leaned down to kiss her.
Instead of describing the build-up, I went straight for it by pressing my tongue on her clit while holding her down. I made sure my entire mouth was wrapped around her and my tongue moved as fast as I could manage. She had another orgasm, causing juices to cover my chin before falling back on the bed. I licked my lips.
With a wink, I said, "Get ready for more," and kissed her stomach. I was pleased to see that she hadn't fainted yet.
However, she eventually drifted off into sleep, too exhausted to even lay back and let me continue pleasing her. So, I discreetly put my boxers back on but stayed close to her, still naked, sticky, and in an arousing condition.
Although I could easily take care of myself after a night like this, I chose not to. Instead, I just curled up close to her, letting her body settle back against mine and feeling my erection respond to her warmth.
There's still about a week left of the dares, and I don't want to let my housemates down.
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