Late Night Truth or Dare

Author's Note:

At its heart, this is a college harem series, but as it contains incest, it must be categorized accordingly.

This is the seventh chapter in the

Late Night Truth or Dare

Series. I do not recommend reading this as a stand-alone story as it will be missing much of the context and character development from the prior installments.

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Late Night Truth or Dare - Halloween

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The end of summer break meant the gang had to split up. Bobby returned to college, eager to finish his senior year, while Sarah, Ian, and the other girls set off to start their college experience, now more apprehensive than they'd been at the end of high school.

Jennifer was left at home, alone with her husband for the first time in eighteen years, a proposition she wasn't looking forward to. Maybe if he was the guy she wanted him to be, but as it was, she knew she would miss Ian, even if they'd only had a few short weeks together.

Toward the end of October, Bobby and his roommate John began to plan for their annual Halloween party. Each year they tried to go bigger and more outrageous, and with it being their last at school, they strived to host a party that would be talked about in school lore.

For Bobby, however, the party would not be complete unless it involved his sister and hopefully several of the other girls as well. He'd missed them since returning to school, more than he had let any of them know, and inviting them was on the top of his list, right above securing the kegs for the party.

*****

"Hey, Bobby, you got any girls to invite to our Halloween party? It's turning into a sausage fest," John asked as he leaned through Bobby's door.

"I got a few. But maybe we shouldn't invite so many guys? Parties are always more fun when you can actually move in the house," Bobby replied.

"If you say so. I prefer to crowd surf to the keg, but to each his own," John retorted. "What about those chicks you were hanging with over the summer?"

"My sister's friends?" Bobby asked.

"Yeah, those freshman sluts," John badgered Bobby. "I know they don't go here, but you think they'd make the drive? I've got a hankering for some teenage pussy."

Bobby rolled his eyes.

"Dude, you got to cut that shit out. Have some class from time to time," Bobby chastised John. "Even if they showed up, they're not going to fuck the likes of you."

"What? I'm not their type?" John asked. "Who is? You? What do you have that I don't?"

"Manners, muscles, brains," Bobby teased his roommate. "Oh, and a big fucking dick."

"Fuck you, man," John said as he shook his head and laughed. "I've got manners when I want," he finished with a smile.

"Let's hope you take a shower before the party this year. Maybe some girl will talk to you then," Bobby continued to lay it on.

"I would say you're one to talk, but the girls can't seem to get enough of you this year," John said suspiciously, "yet, you haven't fucked a one of them, have you? What happened? Did you go and fall in love with one of these hometown broads?"

"Something like that," Bobby replied.

*****

Bobby hesitated as he stared at his phone. It'd been two months since he last saw the girls, his mom, or Ian.

He'd kept in close contact with his sister Sarah, sharing erotic texts and nude photos almost daily, while Ashley, Dee, and Candace called him from time to time for phone sex.

He hadn't talked to Ian, but his mother constantly informed him what his half-brother was doing. It looked like he would make the baseball team. His grades were passable, and he looked as good as ever naked.

He didn't need to know that last one, but his mom liked to through it in to keep him humble.

As for his mom, Bobby had only had brief discussions about their encounter to end the summer, but from what he could tell, everyone was still happy and had no regrets. He wasn't sure what would happen when they got together over Winter Break, but he was looking forward to it.

Everything was going as well as could be expected.

Except for Bella. No one had heard from her since she left for college.

The girls were starting to worry that she'd freaked out about the events over the summer. Then again, she could just be distracted by the first few months of college... or a new guy.

Bobby had promised to invite them all to the Halloween party, but he was nervous to see them. Specifically, he was anxious to see them around other people -- ones that didn't know what had happened.

Unlocking his phone, he typed a group text.

Bobby:

Hey everyone. Me and my roommates' Halloween party is coming up. The theme this year is Slutty [Blank] Masquerade. Like, Slutty Nurse, Slutty Cat, Slutty School Girl ;) You're all invited if you can make it.

Sarah:

I've got just the outfit :)

Candace:

Me too!

Bobby:

I thought you two would like that.

Ashley:

I've got to go shopping.

Sarah:

You should match me and Candace. Bobby can be our hot teacher!

Bobby:

I'm in.

Ashley:

Send me the link

Candace:

Ashley, your boobs will be ON DISPLAY in that outfit!

Ian:

Sounds like a hell of a party, but I've got other plans.

Sarah:

What could be better than this?

Ian:

Your mom :)

Bobby:

You're not wrong. Say hi for me.

Dee:

Say hi to Jennifer for me too ;) But I can't come. I've got a boyfriend. Sorry, Bobby. I've been meaning to tell you.

Bobby:

No worries, Dee. I'm happy for you. I hope he's a good guy. Will you bring him home for Christmas?

Dee:

That's the plan.

Bobby:

Has anyone heard from Bella?

Ashley:

Only a rumor that her family moved back to Mexico.

Sarah:

I hope everything is alright with her.

Bobby:

Me too. I'll send you all the deets for the party when we finalize them.

Sarah:

Don't tell anyone I'm your sister ;)

*****

Ian sat at his computer, still sweaty from his workout. He needed a shower but wanted to check his email while his roommate was still in class.

He found what he was hoping for -- a new message from Jennifer.

Hey, my sexy college stud. I've been thinking about you a lot, and I miss your cock, SO much. My husband hasn't fucked me since our last romp. I know you're probably happy about that, but I am dying to be fucked. Think you can help me out?

I've told him I have a conference over Halloween weekend and booked three nights in a hotel near your campus. Get your homework done because I don't plan on putting on any clothing the entire time I'm there ;)

xoxox

Jennifer

Attached to the email was a selfie taken from an outstretched arm above Jennifer's naked body. She was lying in a bed of white sheets, with the top sheet seductively wrapped around her legs and stomach.

Her large breasts were visible, only sagging slightly to the side, despite her breastfeeding two children and being in her forties.

Her free hand covered her pussy, but Ian saw two fingers inside her.

He never tired of the photos she sent him, especially ones of her playing with herself.

Ian dropped his shorts and quickly stroked his erect shaft, wanting to cum before his roommate got home.

*****

"I've got three girls coming from back home. Any luck balancing out the numbers on your end?" Bobby asked John.

"I threatened to revoke some invites if they didn't bring girls, so I think we'll be good," John said. "So, what are their names, and are they hot?"

"Ashley, Dee, and Sarah," Bobby responded, "and fuck yeah, they're hot. But like I keep telling you. They ain't going screw your dirty ass."

"Which one's yours? I'll keep my charms away from her," John joked.

"Sarah. Except, well, never mind," Bobby said, changing his mind about claiming all three girls.

If they wanted to sleep with other guys, he wouldn't stop them. Of course, he wanted to fuck all three, but that was a lot to ask at a party filled with plenty of other guys to distract them.

Although, if he did, he'd be a legend amongst his friends.

"How many people will be here?" Bobby asked.

"I know forty that said they'd show, so with walk-ins, it will probably be around sixty or so," John responded.

"That should be fun. As long as the cops don't show as well," Bobby said.

"I've talked with the neighbors, so we should be good. Just make sure to lock your room," John said, starting to laugh. "You wouldn't want anyone fucking in your bed again."

*****

Jennifer:

Hey sexy, I just checked in. My room is 609. Bring a change of clothes and a toothbrush. You won't need anything else ;)

Ian:

I'll be there in 30.

Jennifer:

I can't wait. I'll order room service for later.

Ian's phone dinged with another message, this time a photo.

Jennifer stood in her hotel room, already wearing a white robe. She had pulled the robe to one side, revealing one of her impressive breasts. Her nipple was red and swollen like she had been pinching it before she took the photo.

Ian's cock twitched.

No matter how many nudes Jennifer sent him, he didn't get used to them. Every new one brought excitement, and every time he thought about how lucky he was to be able to hook up with the woman of his dreams. If only they weren't separated by several hundred miles with him at college.

There was no separating them this weekend.

Ian arrived at the hotel, marveled at how nice it was, and picked up the keycard Jennifer had left for him at the front desk. She'd told him to come in when he arrived, with no need to knock.

Ian assumed she would be in the shower, or maybe the bath, but when he opened the door, he was disappointed.

Jennifer was asleep.

She looked sexy, curled up in her robe on top of the duvet, but it wasn't what Ian had hoped for.

All day his dick had been leaking in anticipation of renewing his fling with Jennifer. He'd imagined walking into her bedroom, tossing her naked body on the bed, and having his way with her, just as she liked it.

Instead, he stripped his clothes, donned the other robe, and lay on the bed behind Jennifer, carefully slipping his arm over her and snuggling against her as she continued to sleep. Soon Ian joined her.

He was exhausted from school and off-season workouts for the baseball team. He hadn't expected this much work from either, and having to cram to free up his weekend had put him over the limit.

If Jennifer had been awake, he would've found the energy, but given the opportunity, he slept like he needed to.

Knock, knock, knock!

the door sounded, startling the sleeping lovers awake.

"Room service," a female voice announced on the other side of the door.

"Coming," Jennifer responded, groggily climbing out of bed, leaving Ian lying where he was.

Ian closed his eyes and let his head fall back to the pillow as Jennifer dealt with the food.

Jennifer opened the door to see a petite young woman, probably a college student, standing behind the cart.

She was pretty but hadn't worn any make-up, and the bags under her eyes gave away her lack of sleep -- definitely a college student.

"Come in. You can set the food on the table," Jennifer said to the brunette. "Let me get you a tip."

"No need," the girl said, smiling and glancing at Ian. "That's tip enough."

Jennifer glanced at Ian, who appeared to be asleep again, and noticed his robe had fallen open and revealed his impressive dick. His impressive and erect dick.

Jennifer nodded as she held the door open for the girl.

"I hope you and your... " the girl paused.

"Friend," Jennifer filled in.

"Have a nice evening," the girl continued. "If you need anything else, you can reach me directly at this number," she continued, handing a business card to Jennifer. "My name's Colleen."

The door closed, and Jennifer stared at the card, not knowing what to think.

"Is the food here?" Ian asked, slowly waking from his much-needed rest.

"The food can wait," Jennifer said, dropping her robe and climbing onto the bed.

*****

Sarah:

Hey bro. We're running late and won't be there until around 10 pm.

Bobby:

No worries, the party won't heat up until around then, anyway. I can't wait to see you (and Ashley and Candace). I miss those schoolgirl costumes ;)

Sarah:

You've GOT to see Ashley. Her boobs are popping out all over the place. Not to mention her ass!!!! Want a pic?

Bobby:

No. Surprise me. I am sure all the guys will be drooling over the three of you.

Bobby put his phone back in his pocket and returned to work prepping for the party.

They had three kegs of cheap, light beer, several handles of bottom-shelf liquor, and an array of mixers. They'd ordered an ice luge, scheduled to arrive around nine, and John had borrowed a shot-ski from a frat-bro friend.

Beer pong and cornhole were in the backyard, and all the neighbors had been invited or bribed to keep them from calling the cops, not that they expected any problems as Halloween was the biggest party night of the semester and they were not the only party on the block.

Inside, someone had set up a stripper pole in the living room, not that anyone was expected to use it, as the crowds would be too dense, but it sent the message that this was a party where you could let your inhibitions down -- if the theme hadn't already made that clear.

Around eight, the early birds started arriving. They were mostly dudes looking to get wasted before the crowds slowed down access to the kegs.

Almost everyone that showed up had taken the slutty part of the theme to heart, with most of the guys going shirtless and many wearing Speedos or other tight clothing that showed off their probably stuffed bulges.

Around ten, the girls came flooding through the doors, packing the living room with more skin than a Las Vegas pool.

Everywhere Bobby looked, there were short skirts, bras, teddies, unitards, and even some pasties. The girls started dancing after a few drinks, and the guys followed soon after.

The music was loud, the temperature hot, and everyone was having a good time, except Bobby, who sat on the front porch waiting for his three

friends

to show up.

Around ten-thirty, he saw his sister's car drive past the house looking for parking. About five minutes later, the three girls came walking down the sidewalk. They burst into a run when they saw Bobby.

They all reached him at the same time, wrapping their arms around him in a group hug. Bobby tried to reciprocate, but his arms were pinned to his side by their ample amounts of exposed flesh.

Sarah kissed him, her mouth opening to his, as the over girls rubbed their bodies against his.

It felt good to make out with his sister in public for the first time. Finally freed from neighbors and acquaintances who knew their true relationship.

"Damn, you girls look

hot

," Bobby said, stressing the hot.

The three had made good on their promise to wear matching slutty schoolgirl outfits. Candace wore the red plaid she had modeled for Bobby in August, while his sister donned the gray and white version he'd bought her at the same time.

Both of their asses showed beneath the skirt, with Candace wearing a pair of red lace panties and his sister sporting a pair of plain white cotton undies.

Ashley was on another level. The outfit was designed for women with smaller assets than hers. It fit the slender frames of Candace and Sarah perfectly, but Ashley was spilling out of it in all the best possible ways.

Ashley had chosen to wear a thong, which showed off her entire ass, making it look like she was pantyless from the back. Up top, the tiny white collared shirt that tied across her breasts barely covered her nipples and allowed a significant view of her areolas. She'd had to tie it so tight that it dug into the flesh, causing her breasts to spill out in all directions.

To top it off, pinned between Ashley's compressed boobs was the little black tie that hung freely from Candace and Sarah's neck. She looked like she was getting titty fucked by a long and skinny black dick.

The three topped off their costumes with lace masks strapped tight against their faces.

"Look at you, sexy teacher-man," Sarah half-joked.

Bobby was wearing a tweed suit he'd bought from a thrift store, but he'd foregone a shirt underneath the jacket. His toned pecs and impressive abs were visible beneath the brown fabric.

"I better look sexy because this shit itches," Bobby laughed.

"Maybe we need to get you out of the jacket," Ashley suggested.

"Fuck, girls. I'm not sure I want to introduce you to anyone looking like this," Bobby said.

"What? You afraid we're going to hook up with someone else?" Sarah teased.

"No. I just don't want to waste time getting you to my bedroom," Bobby responded.

"There'll be plenty of time for that," Ashley smiled, "but first, I want to dance."

As they entered the house, the bass thumped in their chests, and the hems of the girls' skirts bounced with the beat.

"Oh my God, Ashley, look at your breasts," Candace screamed.

Ashley's boobs were vibrating to the music as well. Each pulse of bass sent shockwaves through the fleshy skin. Ashley played into this and started bouncing to the beat, accentuating the already visible movement of her tits.

Candace and Sarah quickly joined in with Ashley's bouncing. Their three skirts flew up every time they landed, ensuring everyone looking got a full view of their asses.

Sarah grabbed Bobby and pulled him into the middle of the action. He slowly found the rhythm and jumped with the girls. All four bounced off each other, their bodies colliding as their hands held them together.

The collisions extended beyond the four of them. The party was so packed that it was impossible to dance in the living room without bumping into other people, making it sexier for everyone.

The girls got plenty of stares but were not unique in how they dressed. There was plenty of skin showing from both the guys and girls of the party, leaving people with plenty to draw their attention.

Sarah turned her ass to her brother's crotch, grinding against him as his hand cupped her breasts.

Candace moved in front of Sarah and imitated what she was doing to Bobby. Her skirt rode up as she rubbed her butt against her friend. Sarah didn't limit her hands to Candace's breasts and slid one hand down the front of her skirt, reaching for the dampness that had already formed.

Ashley slid in behind Bobby, reaching her hands around to fondle his bare chest. She found the jacket cumbersome and quickly pulled it from his shoulders.

Tossing the jacket aside, she returned her hands to his front, with one grabbing his chest and the other reaching for the button of his pants. She quickly made it inside his trousers, reaching for his growing member, as the four truly danced like no one was watching.

"Holy shit, you didn't tell me there was a stripper pole," Ashley blurted out before she could pull Bobby's cock from his pants.

"Are you considering a new career?" Sarah joked.

"No, but I've been taking aerobic pole dancing classes at the rec center," Ashley responded, "it's a perk of going to a state school."

"All right, hotshot, show us some moves," Bobby dared her before clearing room around the pole.

Bobby leaned against the wall with Candace to one side and Sarah to his other. His arms reached around their petite frames with his hands full of A and B cups.

Bobby looked around the room as Ashley grasped the pole, slowly walking around it in preparation for her routine. His eyes caught John standing across the room with a slack jaw, unable to comprehend what he saw.

Bobby had told John he was fooling around with his

friend

Sarah but hadn't told him that it was much more than her. John was unprepared to see the three girls drape themselves over Bobby.