A Dare Worth Taking Ch. 2

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A coed's second game of Truth or Dare brings another first.
3.7k words
4.5
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Part 2 of the 2 part series

Updated 11/01/2022
Created 09/10/2002
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Near midterms, the student body gets a little stir crazy. Well, certainly the freshmen seemed to be anyway.

Jen was struggling in French but found the rest of her Humanities courses very easy. Philosophy was very stimulating, especially looking at her gorgeous professor each day, and she had two friends in Creative Writing. Veronica, her auburn-haired roommate, transferred into the class just before Drop/Add ended, and Brenda who was a really sweet girl from 2nd floor Holt.

Class time was practically the only time that they saw each other anymore, ever since Veronica started fucking her new boyfriend, Pete, on a more or less regular basis. Five or six nights a week, the studly Pete had Veronica at his apartment and the rest of the time she was filling Jen in on all the juicy, lurid details. Jen's room was never dull what with the constant traffic of girls from down the hall visiting, but sometimes Jen wished that she had Veronica's wild side, especially at night alone.

Brenda and Jen had begun to meet at the library and occasionally at the local deli after classes. Both were naturally introverted and each delighted to have found a kindred spirit. During their first party on campus, they had participated in an intimate game of Truth or Dare inwhich Brenda had secretly watched Jen have her first sexual experience. Jen didn't know if they had bonded so well because of this, or in spite of it. Either way, they never talked of it.

Jen's partner in that playful escapade was slowly becoming a bigger part of her life as well. She had spent nearly a month flirting with Andy whenever possible. They talked on the phone almost daily, met on weekends, and studied together whenever possible. She had even slept illegally in his dormroom one night when she stayed over a little past curfew, much to his roommate's displeasure.

Slowly they were starting to find places to sneak off together. Still, they hadn't gone all the way. She wasn't sure just why, maybe it was her promise to her mother many years back that she would wait for marriage. But she didn't seem to have the same hangup with oral sex; they'd even mutually masturbated once in her room. She still told herself, however, it was because he hadn't just come out and asked her for it. But boy, was she ready.

The Friday of her last midterm exam she actually hadn't seen Andy for three full days due to his Calculus and Chemistry exams. Such a typical scholarship student, she thought, even the possibility making out didn't keep him from cramming before a test. But she was planning on making up for it over the weekend. His uptight roommate was going home for that weekend and they would have his dorm to themselves. Hopefully, this was the time for him to make the move she had been fantasizing about.

Waiting for him to get out of class, Jen came back to her dorm to find a note that Veronica would be out all night. Changing into jeans, Jen heard a knock at the door and found Brenda at the doorway almost in tears.

"Oh no, don't tell me. Biology?"

"Yes, I... I think... I'm sure I blew it." Brenda sniffed and fought back a tear trying to smile. "I guess maybe I should throw myself at the mercy of my T.A."

Jen gave her hug and pulled her into the room. "No, no. You probably did fine. Wait and see if you failed first, before you agree to do him. There's always Finals to worry about."

They laughed and agreed to not mention school for the rest of the weekend. Brenda sat on the bed slowly recovering and helping Jen pick out tops for going out. Trying things on in front of her friend didn't make Jen uncomfortable at all, but when she removed her bra to try on a strapless silk blouse, Brenda seemed to get uncomfortable. She had occasionally looked that way around Andy too, Jen thought, but put the matter out of her mind when the phone rang.

"Hey cutie, how were your tests?"

"We've promised not to talk about those," Jen looked over at Brenda and smiled. "So I can't ask you either."

"Rough, but over. Who's we?"

"Brenda came over. She's fucking her Biology teacher next week and wanted to get some pointers." She stuck her tongue out at Brenda giggling on the bed.

"Lucky guy. She wanna go out with us tonight? My friend, Bob, you know, the baseball guy. He was thinking we could sneak into Herky Jerky's if we went early..."

"Bob, huh?" Jen didn't like Bob. He was a typical jock, which meant typical asshole to her. Still, he was hunky and Brenda needed a pickme up. "You're on, we'll meet you there at six."

Brenda pretended to protest, but soon they were down in her room picking out clothes and trying makeup combinations. Jen noticed that Brenda was modest when changing, but had several posters on her wall of seminude men. A closet sex fiend, she thought. They really were partners in crime.

The group didn't get into Herky Jerky's, or O'Malley Pub, or even into The Beer Bucket. Neither Jen nor Brenda had ever seen a fake ID, and Andy's was so bad it was almost confiscated. Finally, they had to send Bob into Walgreens to buy them beer and some Coke for the rum back at the dormroom.

Bob and Brenda didn't hit it off but were sociable, especially when the girls beat the pants off of the guys in Quarters. It didn't help that the boys made side bets of shotgunning beers and soon were three sheets while the girls made fun of them. After two games of rum-n-coke trivial pursuit, won by the girls, and an uproarious game of Indian poker, won by the girls, Bob actually wandered off down the hall of Andy's dorm to find more beer. Still, neither Jen nor Brenda were disappointed that he didn't come back.

Andy was a hoot. He was slurring his words and beginning to look very droopy eyed. Jen leaned over to Brenda and whispered, "No sleep for two days" when he began humming Village People tunes. Before they knew it, the girls were alone playing cards, sipping on their drinks, with Andy passed out on the bed before them.

"Men. Can't hold their hooch," Brenda deadpanned.

"If I drank that much, I'd be dead. Question is, what do we do to him?" Jenny grinned and turned, looking at Andy lying on his back.

"What color nail polish do you think he likes?"

"You wouldn't..."

"Nope, but you could. And wouldn't even get in trouble. Let's just say I dare you." Brenda looked over at Andy, then back to Jen. She flipped her a bottle of Mayflower Rose from her bag.

After a rather delicate application of nail polish to his left hand without a hitch, Jen found it difficult to do the nails of his right without straddling her sleeping boyfriend. Several times his hand moved, including one big swipe above his lip and across his comforter. Stifling laughter, the girls delighted in the wide red swath drying over his upper lip as Jen finished the manicure. Crawling off him, she thought she felt the bulge in his jeans shift. Turning quickly to see if he was awake, she saw him lightly snoring and took her place next to Brenda in the floor.

Turning up the last of her drink, Brenda asked her if she wanted to play another game. Jen thought about it and then turned to face her friend.

"You dared me first so its your turn." She smiled in her most evil gaze. "Truth or Dare?"

Brenda smiled back. "I don't remember being very good at this game last time."

"Well, I was."

"I noticed."

"Well? C'mon, just between us."

After looking over at Andy and his lovely nails draped across his eyes, Brenda sighed. "I'm too scared of a dare, so gimme truth, or gimme death. Or something like that."

Jenny laughed. "I was hoping you'd say that, you know. I'm dying to know..." She paused a heartbeat.

"How much I saw of you and Andy?"

"Yes."

Pause. "I came up to see if anyone wanted to walk back to the dorm with me and almost walked into the room on you guys. At first, when I saw you, I thought you were wrestling or something and that you might be in trouble. But I couldn't move. Or speak. When you looked up, with that look... I knew I was watching something I shouldn't."

"I'm so sorry Brenda, we didn't think anyone was around. It was pretty dark in the room, wasn't it?"

"Not that dark."

"Did you stay... I mean... when did you..."

"Wait, no fair!" Brenda reanimated as if she had snapped out of a vision. "It's my turn now."

"Ok, but I'm not through with you yet, little missy."

"I'm so scared, really very, trembling." Her sarcastic look turned smug. "Truth or Dare?"

Jenny thought a moment and replied, "Truth."

"What was it like?" Brenda trying not to look overly interested but was failing miserably.

Jenny had never asked her friend if she was a virgin, but had just assumed it for some reason. Looking at her now, she tried to avoid sounding like the sex expert. But she understood. And she slowly began to describe what she had felt.

"It was incredible. I didn't intend to let it go so far. But, I don't know, the combination of the game and the video... Not to mention his gorgeous eyes. I really thought we would be secluded in the room. Everything he did to me was everything I had imagined. It was even better than masturbating the first time. And then, I saw you."

"Did that ruin it?"

"Not at all, I was so far gone. It was, like, I dunno, like showing off."

"Did it taste, you know, salty?"

"Yeah, a bit. I don't know if it was the amount of it or the sweat or what, but I can't describe the taste. It almost wasn't that noticeable. Taking the whole thing in your mouth was the harder part. The cock I mean." She giggled.

"Was it hard the first time you...I mean, does it hurt inside you? To fuck?"

Jenny was surprised to hear her say that word. Maybe just in the way she said it. She hesitated and thought, "I'm torturing the poor girl." She squirmed a bit, and noticed just talking about it had made her very horny.

"Hey, it's not your turn to keep asking questions!" She tried to smile at Brenda but it was not returned. In fact, Brenda was staring at her, anticipating her reply. Jen looked over at the unmoving figure on the bed and said, "I've never done it. I'm curious about that myself."

"Never?"

"Well, no. It just hasn't felt right. What about you?"

Brenda didn't hesitate. "No, me either. My next door neighbor fingered me when I was twelve. It hurt like the devil, but I didn't make it stop. I can't imagine what it would be like to have more inside there."

"You don't use a tampon? Or masturbate?" Jenny was asking but knew what she meant.

"Yeah, but a tampon's not the same. And I... don't go inside it to cum."

Silence fell over them for a moment as they ignored each other's eyes. Jenny thought to herself how hot it was getting in the room. No, that's not right. How much she wanted to touch herself. Or better yet, wake up Andy and let him touch her. If she could only decide what to say to Brenda to get her to leave. Or maybe, she didn't have to.

"Ok, I get another one, cheater." Jenny looked at Brenda who was looking at Andy. When she turned to catch her eye, she smiled and nodded.

"Did you like watching us?"

Softly, Brenda replied, "Yes."

Jen looked over at Andy who had moved his arm slightly. "Well, I'm dying to wake that boy up and try again. Would you want to... again? I mean you don't have to. I didn't know, it's up to you." Jenny held her breath praying her friend would not look offended. Or say no.

Brenda said softly again, "I would love it. I've thought about it ever since that night." They looked at each other and smiled. Jenny wanted to hug her but Brenda started to stand up.

"Could I turn off the lights and see how dark it is?" she said, still whispering.

"Sure, there's a lot of window light actually."

Brenda moved behind the desk wall and the light coming from the other side of the room went out. Initially everything seemed black, but then Jenny could make out her friend sitting down on the other bed about six feet away without saying anything.

Well, this is it, thought Jen. She waited a moment to decide what to do, and then stood up. She suddenly wondered if that next door neighbor who had touched Brenda had been a boy? She had just assumed it. Before she knew what she was doing she stepped over to Brenda and brought her face down to her ear in the moonlit room. Just as she was about to speak, she noticed that her friend had her thin arm across her stomach and it disappeared into her open jeans. Even though she couldn't see her hand moving, she immediately couldn't think of what she had planned to say. It was the most erotic thing she'd ever seen.

Brenda couldn't help touching herself just thinking about watching Jen and Andy. She had just opened her jeans and slipped her hand inside her panties when Jen stood up and came toward her. She sat paralyzed, unsure if she had been caught yet. When Jen leaned down toward her, she thought for a moment she would feel a kiss. She closed her eyes and didn't move. Finally, she heard a whisper in her ear, "If he's asleep, you can help me. If you want." Then Jenny walked away, leaving Brenda to wonder what kind of help she had meant.

Jenny turned to face Andy and moved over to his bed. She wondered if he was even going to wake up, if his dick would even work in this state. Staring down at him, she decided to give Jen a show. She was turned on, and knowing that Jen would be watching her every move made her even hotter. She slipped her jeans down to reveal her narrow dark panties. She bent forward over Andy to take them off, knowing her ass was on display but would be lit from the side in the dark. Andy was not snoring now, in fact he was dead calm.

She knealt beside the bed by his legs and nimbly began to work on his pants. When she finally peeled them over his feet, she climbed onto the foot of his bed on the side opposite from Brenda. She looked over, but it was too dark to see more than a silhouette of a figure now reclining on the other twin bed. She eased herself up until her head was over Andy's boxers, which had been pulled down part of the way.

In the light it was difficult to tell for sure, but it looked like Andy's cock was rising out of the top of his boxers already. She reached over to feel the undersurface pointed at the ceiling and squinted. In fact, it was already as hard as steel and hovering over his abdomen. Her hand instinctively began to rub slowly back and forth over it; so much for worrying about how it would function.

Brenda lay across the bed propped on her left elbow, hand still inside her panties. She could see surprisingly well, since the two bodies across the room were sidelit and directly under the window. She could see Andy's gorgeous cock already swollen and erect. She watched as Jenny ran her hand over it lovingly and then freed it from his boxers completely. Her friend's eyes glowed, her body looked amazing. It was not going to be long before she would cum, but she couldn't stop fingering herself.

Then suddenly Andy was awake. All in one motion he had reached up and grabbed Jenny, pulling her toward him and on top of him. She could see their figures together and then his hands slip inside her panties pushing them down. Brenda strained to see more but could only make out the line of her back and ass. She heard the faint smack of lips kissing and soon the figures were writhing together.

When Jen had pulled the front of his boxers down, she decided that she was going to try tonguing his erection before showing Brenda another blowjob. Just as she leaned forward to lick the tip of his cock, his hands swooped down and pulled her onto him. She was so surprised, she let out a gasp and almost pulled away. She peered at him, but was only met with a kiss. Slowly, she opened her mouth and let his tongue touch hers and explore. For a moment they kissed, oblivious to anything else.

Just as she became aware of his hands slipping her underwear down, he broke their kiss and began to kiss her neck in the most sensitive of spots. She could feel his hard rod underneath her, and she began to move it between them. Faintly, a voice whispered in her ear, "I know she's here."

Taken aback, she realized he'd been awake. For at least part of it. She kissed him, then whispered back, "Nevermind her, why don't you fuck me." She heard him sigh and soon her clothes were strewn around the bed.

Brenda watched as they stripped each other. They rarely seemed to break their kiss and when they did it was to whisper some imagined lusty comment to each other. She closed her eyes for a moment as the first signs of her impending orgasm began to build.

When she opened them, she startled, for now someone was rising near her, half standing beside Andy's bed. When she became oriented again, she saw that Jenny had one leg on the floor and both of them were on the edge of the bed nearest hers. Andy moved his hand to his mouth and then must have touched her between the legs because Jenny's buttocks squeezed and her head rolled back. In the shadows she saw Jenny holding his cock between her legs and then slowly sit down over it. She heard her gasp and then watched as the muscles of her thigh pushed forward to reposition for another try.

Jenny felt her slippery cunt squeeze over his fingers as he slowly inserted them into her the first time. As he fingerfucked her softly, though, she relaxed and she guided his throbbing glans up beneath his hand. When his fingers came out and reached down to the base of his cock, she felt an urge to refill herself with him. She sat down on him and almost had him inside, when it slipped and traveled back across her anus. She gasped and redirected her pelvis, intent now to have him inside her.

Brenda watched as they guided him again towards her pussy. Then suddenly her body slowly sank down onto his and she heard them both moan. Almost immediately, her fingers resuming their wonderful work in her panties, she felt a sense of relief and nearly release. She couldn't close her eyes, afraid she would miss some wonderful scene of passion.

She watched as his hands ran over both of her hips as they began to fuck slowly. She saw the bodies fall into a rhythm and move as one. Andy's mouth opened and encircled her nipples one at a time from below. She heard their soft moans and soon the smacking of wet flesh as they intensified their movements. Soon she saw him pull her around by the ass, Jenny now straddling him with her knees as she rocked back and forth on top of his cock.

As her own orgasm neared, Brenda could see his chiseled thighs lifting his cock into Jenny from below. His balls squeezed at the end of each thrust, and then the contoured shaft coming into view before disappearing again. His hands were spreading her ass cheeks slightly, revealing her asshole and pussy for the first time. She could see his cock moving in and out of her and saw her ass cheeks flinch with each stroke. As the thrusts became deeper, she saw his fingers spread her even further, one finger moving over her anus. Soon, their moans were constant and she couldn't hold off anymore. Brenda closed her eyes and came in quick and glorious spasms.

When she felt his fingertip touch her anus, Jenny knew she could not hold off any longer. He had begun to thrust forward into her as she rocked into him, grinding her clit into his pubic bone. As the sensations mounted, she arched her back, allowing more of her throbbing clit to rub against him as they fucked. With his lips around a hard nipple, she cried out and began to cum. Thrust after thrust she felt the waves crashing over her. Multiple orgasms electrified her body as she felt him tighten his grip on her ass and slip one fingertip into her asshole. He exploded inside of her, burying his face into her shoulder and her cascading hair. As his orgasm faded, her body wilted onto him.

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