Late Night Truth or Dare Ch. 01: Bobby

"Are we talking sucking dick or eating pussy?" Dee queried.

I was caught off guard by her frankness and use of crude terms. Not that I would have been any less surprised if she had said fellatio and cunnilingus. Additionally, I was disappointed in myself for not thinking about the options she set before me. I had self-centeredly thought of myself being serviced when asking the question, hoping to get a recommendation for later.

Now I was equally curious about who she thought would make the best carpet muncher.

"How about one for each?"

Dee did not have to look around the room or think about it. She knew the answer to both questions straight away. I'm not sure if this was from personal experience, hearsay, or a guess based on the size and shape of their tongues. No matter how she got to her conclusion, the answer came swiftly.

"Ashley sucks the best cock, and Sarah eats the best pussy."

My sister blushed next to me while Ashley smiled with pride, finally getting the recognition she had missed out on by not being named the biggest slut.

My sister, on the other hand, was embarrassed, and I couldn't tell if it was because she had been outed or if she was simply uncomfortable being connected to a lesbian activity. It didn't make a difference to me.

Part of me had always wished my sister was a lesbian so we could one day sit around and talk about which girls were hot, just like two brothers might do.

We moved on before I could think too deeply about my sister's reaction, or what Dee's answer meant.

It was Dee's turn to target someone, and she was resolved to get Bella involved in the game at last.

"Truth or dare?" Dee asked, staring down Bella like a lioness stalking her prey.

"Truth," Bella answered, with a quivering voice, unsure if it was the right choice.

"Did you wear such a sheer shirt because you wanted Bobby to see your nipples?"

This was actually an interesting question. A lot rode on Bella's answer, namely if I would continue to play the game.

I, and everyone else, looked on as Bella appeared startled by the question. She glanced down at her chest as if to check if her nipples were indeed visible, before looking around nervously. Her eyes quickly darted away after briefly locking on mine.

She was nervous about her answer.

I thought that I knew the truth, but I wouldn't guess how she would reply. Would she tell the truth, or would she lie?

"I had no idea Bobby was going to be here," Bella asserted before rambling out the rest of her answer. "I, uh, is it a crime to wear something like this to a sleepover now?"

"Of course not. Wear whatever you like. Hell, Dee looks like she's waiting for her boyfriend to come over and fuck her," I blurted out.

My joke did not get the reaction I was looking for. No one laughed, Dee shrunk, and everyone else seemed too scared to talk, either to chastise me or comfort Dee.

I figured she had worn the lingerie for the same unspoken reason that Ashley, Bella, and even Candace had worn their outfits. None of them were going to admit it, at least not in front of my sister or me, but they all knew the truth.

I thought I was lightening the mood, letting them relax about their clothing choices, but I'd hit too close to home and made the situation more awkward.

The next few rounds passed without much fanfare. The air was sucked out of the game, with the girls only tentatively sipping their drinks, seemingly hesitant to get drunk.

The only thing of note I can remember was that none of the girls were on birth control. This information came after rapid-fire cross-examinations of who had experienced unprotected sex. As it turned out, none of them had.

The lull confirmed there wasn't much hope for things to pick up, and my interest in forcing myself to stay awake quickly waned.

The extra alcohol was kicking in and was a convenient excuse for my behavior and a looming problem if I continued playing. The room subtly spun, more so when I closed my eyes, which was becoming increasingly prevalent as my fatigue grew.

As much as I wanted to stay and see things through, I did not want to embarrass myself by saying anything worse or, God forbid, passing out.

Plus, I doubted that anything risqué would happen, despite the promise from Ashley, while my sister was in the same room. Even if they wanted to, who was going to dare me to do anything intimate in front of Sarah? And would I even do it if asked?

"All right, girls, it's been enlightening, but I must go to bed before I pass out on poor Sarah here. That was one drink too many."

There was a chorus of mock boos as I stood, slowly making my way upstairs, careful not to make a fool of myself in front of my audience.

"Sleep tight, Bobby. I hope you dream of us, especially me," Ashley called out in a seductive voice, "although, it still won't be as good as if you stay."

The girls giggled, clearly taking the outlandish statement as a form of teasing. Part of me hoped she meant what she was saying but it was better if she was messing with me, as then I wouldn't miss anything during the game, even if they did end up catching up to my drunkenness.

I was quickly out of my clothes and into bed, my earbuds blaring to drown out the chorus of giggles emanating from downstairs, and I was asleep within minutes.

*****

I can't remember exactly, but I was dreaming of Ashley when I was awakened. My blanket was ripped from my nude body, cold air spilled over me, and my testicles contracted at the base of my hard dick.

My uncertainty and shock grew when I felt two sleek legs push next to mine as someone straddled me. Leaning forward, they pressed my arms into the mattress, pinning me beneath them.

"Shhhh, don't say a word," the intruder whispered.

My door had been left ajar, allowing light from downstairs to seep in, although it was insufficient to illuminate the details of the figure on top of me.

I didn't struggle.

I didn't fear for my life and was more than a little turned on that one of the girls took the initiative to climb into bed with me.

The mystery girl lowered herself, her bare cunt pressing down on my cock. The heat and lubrication covered my rod as she slowly slid over me, teasing my head with her outer folds before moving towards my balls. I lifted my hips in time with her movements, trying to meet her. Trying to get my tip inside her.

Reaching down, she grabbed my cock, raising her hips, aligning my shaft with her slit. Without hesitation, she sank over me, engulfing my member in the warmth of her pussy.

Starting slow, she quickly upgraded the intensity, grinding on me, with her cunt gripping my cock as she guided it to her erotic points. Her hips swirled as she found her rhythm, and her hands released my arms as she leaned back.

I slid my newly free hands onto her thighs, caressing her smooth skin as I slid towards her hips. Her legs were toned, but so were all of the girls, but their size narrowed it down. Ashley and Dee had thick thighs, while Candace had skinny runner's quads.

This pair felt somewhere between, pointing towards Bella. She wouldn't have been my first guess, but it didn't come as a complete surprise based on how she acted earlier in the night.

I let one hand slide past her hips, trying to reach her breasts, but she declined to lean forward to meet my touch. She was focused on riding me and had slipped one hand between her legs to work her clit as she ground on top of me.

Her pussy was tight and felt amazing against my unprotected cock, but I was not on the brink of cumming. The alcohol had dulled my senses, and while I was eager to spill my seed, I was going to need more stimulation.

Bella, on the other hand, seemed to be immensely enjoying herself. Her breathing increased in volume and intensity as she picked up the pace, bouncing more than grinding, with her ass smacked against my thighs while impaling herself.

I could feel her cunt contract as she squealed in pleasure, not trying to hide our encounter from the other girls. She spasmed several times as she hunched forward, furiously rubbing her clit as she climaxed on top of me. Eventually, she collapsed forward, her sweaty breasts settled on my chest, and our bodies stuck together as she recovered.

My hands worked their way to her back, pulling her tight as I tried to thrust into her as she lay motionless. One hand found its way to her ass, cupping a cheek, squeezing her soft flesh.

Brushing her hair aside, I kissed the nape of her neck, working my way towards her mouth. Our lips met in a passionate kiss, with our tongues darting around each other. I was about to roll her onto her back to finish what she started when she broke from our kiss and slid forward, letting my cock flop against my stomach with a wet thwack.

Bella slipped down my body, stopping when my dick was between her breasts. They were not huge but were more than sufficient when she pushed them together and started to titty fuck my slick cock.

It had been a while since I titty fucked a girl, and I quickly wondered why. It felt amazing and dirty in ways that other sex acts didn't.

Bella was exemplary, obviously in good practice, and quickly had me approaching orgasm. As much as I wanted to cum inside her, I knew it was best this way, as she, like all the other girls, was not on birth control.

I had not objected when she was riding me, but now I had a suitable alternative and was not going to risk impregnating her, and my cum would look good smeared across her chest.

My breath quickened, and I started thrusting against her with the head of my cock popping from her boobs.

"Oh, God, yes. Keep that up. Make me cum all over your tits," I called into the darkness.

I shouldn't have warned her, as she abruptly stopped, letting my cock flop to my stomach once again.

She rose from the bed and scampered out of the room, leaving me and my swollen balls frustrated and confused.

I started to yell after her and beg her to return and finish me off, but I was rendered speechless when the silhouette of another girl replaced Bella in the door frame.

It was still too dark to make out specific features, but this girl was shorter and stockier, especially in the thighs and chest. Her breasts spilled beyond the sides of her rib cage, and her legs were built for power, not endurance.

It was either Ashley or Dee. Their bodies were too similar, and it was far too dark to differentiate the two. I didn't have much more hope of guessing which one it was once she climbed on top of me. They both professed to be sexually experienced and from what the other girls insinuated, good at what they did.

Just as Bella had done, the mystery girl straddled me, holding me in place with one hand as she guided me inside her with the other. I was still slick from Bella, and the new girl was soaking wet, making her efforts easygoing.

Quickly and quietly, I was buried inside her, with her ass sitting on my thighs. She paused a moment before she started to bounce, playing with herself as Bella had done.

Her insides felt slightly different. I had never had such a direct comparison, but I was amazed I could feel a difference at all.

Her ass had more cushion and provided more rebound when she rapidly speared herself. Her tits bounced more as well, and she quickly leaned forward to allow me to reach them, something Bella never did.

They felt firm and heavy in my hands as my fingers dug into her skin. I pinched her nipples between my thumb and index finger, and they responded by elongating, begging to be sucked. If only she would lean further forward.

She was in a hurry to cum, as Bella had been, but this time I was already worked up. It wouldn't be long before I shot my load, almost certainly before she was able to orgasm herself.

She didn't seem to notice and wasn't trying to prolong the experience, or maybe she didn't know how to go slower. It was all or nothing. Either she came, or I came.

Of course, I would be more than willing to finish her off if I was the first to explode, but I couldn't count on her doing the same. Not after Bella had abandoned me at the last second.

"I'm going to cum," I whispered as I clamped my hands down on her breasts.

I expected her to jump off me or slow her rhythm, but instead, she kept going, riding me like she was obligated to.

I grunted and pushed my hips into her as my cock jerked. Pump after pump of cum entered her, a massive load from being so worked up. I could feel it ooze out around my dick, mixing into her trimmed pubic hair as she continued riding me until my orgasm subsided.

She bent forward and kissed me. Not as deep and passionate as Bella, more of a disappointed hope of more to come. I tried to pull her tight, but she slipped out of my grasp and out of my bed.

"Don't go. I can help you finish."

My plea went unanswered as she cupped her hand to her leaking cunt and waddled out the door.

There was clearly something going on with the girls. Was this some sort of game? I had heard rumors of high school students playing sexual roulette but thought them baseless. I assumed it was nothing more than the rantings of scared Christian mothers who desired to portray the unholy as licentious sluts.

It was said that girls would take turns riding a boy, not using a condom, until either she came or he did. Each girl would get a turn, at least until the guy couldn't get it up anymore.

Could this be one of those games? Could Truth or Dare have morphed into them playing something so stupid yet so erotic?

My musings were cut short as another figure slipped through the door.

She looked taller and lankier than either of the first two. Her breasts were not visible in her silhouette until she turned sideways and revealed a perky set of small B-cups. Her long legs drew my attention as she strode across my room. This was the body of a runner. Her short, tight curly hair confirmed it to be Candace.

My cock was soft but not fully deflated, the circumstances keeping the blood flowing. I was coated in a mixture of cum and the first two girls' juices. A small pool of semen lay just above my pubic hair.

The new girl wasted no time licking her way up my shaft, tantalizing my tip, before slurping up the puddle of cum.

As if this was not enough to get me hard, she grabbed my cock by the base and guided me to her lips. Her tongue swirled about my still tender tip, almost too much to take as she licked the underside, her tongue flicking off the end of my shaft.

It was not an instant erection, but it was damn quick considering I had cum only moments before. I was no stranger to going two rounds, but usually, I took more time to recover.

Not tonight. Tonight was something special. Tonight was a once-in-a-lifetime opportunity, even if I had to tape a popsicle stick to my cock.

She clearly did not want to arouse me too much, opting to pop me from her mouth, still holding me in her hand, and positioning herself above me like the first two.

She was wet, very wet, and my head slid into her with ease. I, however, was not hard enough. When she let go and tried to sink onto me, I folded in half and popped from her.

Not discouraged, she grabbed me, gave me a few strokes, and pushed me inside once again. This time she held on as she slowly eased herself up and down. The tightness of her cunt gripped my head and coaxed my member to full strength.

Compared to her predecessors, Candace's ass was boney. It provided little cushion as she bounced on my lap. She quickly slipped a hand to her clit, rubbing fast and hard as she hunched forward, pushing her free hand into my chest.

She settled into a short, quick grinding motion, her fingers trapped between her clit and my pubic bone. The head of my cock was hitting the roof of her vagina, just shy of her cervix. Not the most stimulating position for me, but it worked for her.

I was still working my way into our session when her breathing quickened, and she lurched forward, pressing hard into my chest.

I slid one hand up to her small breasts, finding a nipple and tweaking it. My other hand gripped her petite ass, and my fingers slipped between her cheeks, stopping just shy of testing her anal limits.

I rolled her nipple one way, then the other. Her hips started to buck, and she slipped out a moan. She grew louder and louder until she was screaming into the darkness of my room, something between a wail of pleasure and a shriek of excitement. It started guttural and finished with a high-pitched exclamation, unlike anything I'd heard before.

Candace collapsed on top of me. Her mouth landed to the side of my head, her breath sounding in my ear. I gently kissed her shoulder as I ran my fingers over her back. She was not muscular or thick and barely had an ounce of fat on her.

My fingers ran along her spine and over her ribs. I thought about rolling her over and continuing to fuck her, as my cock was still hard inside her, but I knew she would be leaving soon.

"You've got an amazing cock, Bobby," Candace whispered as she wiggled her hips, "I want to feel you cum inside me."

"Rollover. I'm more than happy to fulfill your desire."

"I can't. It's against the rules. But I know where you live."

"Bella fucked me with her tits, leaving me primed for whoever came second. Maybe you can bend the rules just a little. Let me give you another orgasm."

"Bella exploited a loophole, and my tits aren't big enough, but I'll certainly take a rain check on that orgasm."

Candace kissed me on the cheek and rolled to the side, speeding out the door before I could persuade her to stay. As disappointed as I was, I knew that another girl would be coming soon.

Unfortunately, Candace had cum so quickly that it would take a lot of work for me to reach my second orgasm of the night. Hopefully, Ashley or Dee, whichever I had not experienced yet, wouldn't be so quick to cum.

In the brief interval between encounters, I reminded myself that none of these girls were on birth control. I had already shot my load into one of them and did not want to risk impregnating a second. It was not worth the danger.

I could always finish myself off, or maybe the final girl would take pity on me and suck me off. Either way, I vowed to keep my seed out of her uterus, no matter how much baseball I had to think about while she rode me.

My final partner of the night skipped into the room, clearly eager to get her chance. She bounded towards my bed, just as Ashley had bounced away from me earlier in the evening. Her breasts bobbed with her, circling with each hop. Now that they were free from the shirt, I could fully appreciate them, even if only in silhouette.

Unlike the first three girls, Ashley mounted me with her ass facing me, opting to ride me reverse cowgirl. She was just as wet as the others as she guided me inside, but her cunt did not feel as tight.

Not that she was loose, but the others had pussies that felt like showroom models. Ashley's had clearly been more than driven around the block. I could see why she had taken umbrage at not being named the biggest slut.

It still felt amazing to be inside her, like nesting my cock in a warm sheath specially designed for me. Every pussy was different, but they all felt custom-made when I was inside them.

Ashley used a circular motion as she rode me. Her hand occasionally brushed against my balls as she eagerly toiled away at her clit. I reached out and ran my hands along her back, scratching my nails across her bare skin.

Propped against my pillow, I could not connect with her breasts. I settled my hands on her hips, letting them move unassisted as I enjoyed the stimulation.

While Ashley seemed to be quickly approaching orgasm, I was not getting the friction I needed. I was staying hard and hitting the right spots for her, but I was safe from pumping her full of my baby-makers.