The Dare

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Tombstone makes-out with a random woman to win a bet.
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The guys—they dared me. And in my group that was a big deal. If you said no to a dare, the shit rained down on you for at least two months. One time our friend Brian came home to find goldfish swimming in the water bottles in his fridge after he said no to a dare. That was just the beginning for him. The next week he woke up without an eyebrow. Then came the worst of all. The other guys told the new girl he'd just started dating that he had herpes.

The poor girl bolted harder and faster than an unbroken mare. The sad thing about Brian's girl was that she was the first girl he'd actually liked in two years. And it was over in half a minute. Relationship ended. Dust.

Knowing my friends' habits made this particular dare even more frightening. They wanted me to make out with some random girl I'd never met—and I had to say yes without seeing a photo. They would give me an address. That's all. The question was—what was wrong with her?

Besides the obvious questions about whether or not I'd find her attractive, numerous questions bombarded me. Did she have uncontrollable acne? Halitosis? Or maybe she was just bitchy and the other guys wanted to get back at her for some perceived slight. Either way, I felt some fear and assumed the worst. Let's face it, bad breath sucks.

"Okay, I'll do it," I said. Last month I put Brian through the ringer and a bet, and I needed to maintain the upper hand. Really, I didn't have a choice. "So what are the parameters of the bet? What do I have to do to win?"

"You get to the house," Brian said, "you knock on the door. The moment she opens the door, you step inside and kiss her. No introductions. After the first kiss you can talk, but you can't leave until at least fifteen minutes of a make out session."

I watched the other guys carefully. Fifteen minutes didn't seem so bad. There had to be something more to it. Why would they dare me to do this? It was then I finally realized what a bunch of pricks my friends were.

Brian caught me looking at the other guys. "Look that's it," he said. "Fifteen minutes of make-out."

"Nothing else?" I asked. "Nothing beyond kissing? Anything like that?"

The guys shook their heads.

"I'll text you her address on the way out," Brian said. "You better get to it." He pulled out his phone.

I stood to leave, and the other guys and the other guys squealed at me with their high-pitched piggy voices, "She's expecting you, Tombstone! Make the little girl happy!"

I gave them the finger. Brian's text came before I even reached my car. Apparently the girl's name was Sybrina. She lived two towns over and I had twenty minutes to decide if I really had the balls to finish the dare or not. But in my heart I knew I wouldn't back down. Even so, it took me just over 23 minutes to leave the sports bar at 1:37 am in the morning and arrive at a brand spanking new house in a new subdivision at 2:01 am. I parked in the empty driveway. For minutes my knees shook in nervous anxiety.

I wondered what the worst that could happen was? No hygiene may have been the worst thing I thought of.

A couple of deep breaths later and I was knocking on the door. I waited, holding my breath. No one came. I did my duty, and I could leave. A part of me wanted to run like hell. Getting set up was never fun, and somehow, the entire bet felt like getting set up to the extreme.

Right before I turned away, I remembered how bad the guys retaliated after a failed bet, so I knocked again. I chose not to let the guys harass me for not doing my due diligence.

This time I heard footsteps. A shadow passed in front of the peep hole, and then the door swung open. Without thinking I stepped inside, caught a flash of black sweats and a black tank top in the low amber light, and leaned over to kiss the short girl who answered the door. The kiss lasted ten or twelve seconds, and my heartbeat at an accelerated pace the entire time. There was even a slight electric tingle.

Finally she broke away and I could see her dark features. Olive skin, brown eyes, black hair pinched into a ponytail.

"Wow, that was unexpected," she said. "But nice."

I took the rest of her in. A sort of plain woman stood in front of me, looking up at me with a quizzical look. The girl was thick, and I immediately knew I lucked out. One of the other guys, Dave, would say she was fat, but would have all fucked her in a second. But what did he know? He liked his girls built like boys. For me, her femininity shone through.

The coup de grace for her body, though, was her enormous rack. I made it a point not to stare at the cleavage at the top of her tank top.

"Do you want to come in?" she asked.

I nodded. We made it to the living room and onto a brown leather sofa. She brought me a glass of water and had one for herself.

"I can't believe I'm doing this," I said. "I've never been set up on a date, let alone a make-out session."

"Is that how they billed this to you?" Sybrina asked. "A make-out session? I just wanted someone to chill with and maybe watch a movie. Brian said they'd send someone by. Of course he said that I'd have to make-out for fifteen minutes for him to do it."

Her response told me a lot about how my friends operated. Maybe I didn't want to be their friends if they were going to coerce people into physical intimacy.

"He must have some kind of dirt on you," I said. "I mean, if he's going to con you into making out with perfect strangers."

Sybrina took a sip of water from her glass. I knew from the gesture that he did have some dirt on her and he wanted to make both of us squirm. It worked until I got here.

"That was an okay kiss, when you kissed me right there," she said. She was now smiling, her lips hidden partially by the water glass raised to her mouth.

I thought about it for a minute. It was an okay kiss, but then I thought about it even more.

"I didn't think you'd kiss me right away," she said.

The moment she said it, I had a realization.

"Wait, you kissed me," I said. Although the kiss took place moments before, in memory I thought she'd kissed me.

Her jaw dropped. "No you kissed me. But let's not argue about it. Do you want to go in the bedroom? It's more comfortable to watch a movie in there."

Brian had told her I'd really watch a movie with her. He was trying to set us up on like a real date. But he was making sure I'd have fun in some way no matter what. I had no problem with that. The only problem was that talking about having a pre-planned make-out session killed the mood. So once we reached the bedroom, I kicked off my shoes and got cozy on Sybrina's king sized bed. It faced the tv.

"I like Will Ferrell," she said. "Just found Step Brothers at WalMart for five bucks." She put the DVD on. I tossed my jacket onto a chair in the corner. Finally she sat down near me on the bed.

After ten minutes of the movie I was bored as hell. Will Ferrell was a douche, and so was that other dude who was playing his Step Brother. I felt a bit of relief when I saw Sybrina start kneading the back of her neck.

"Sit on the floor at the edge of the bed," I said. "I'll get that."

She sat cross legged on the floor. I positioned myself at the foot of the bed, and started with her shoulders, gently massaging the knots.

"Oh, that's so good," she said. "I don't know how that gets so tight."

Something in her voice, a slight hint of rawness, caught my attention down in my pants. The moment came back. I worked with a bit more zeal after that.

"You have good hands," she said.

My hands continued to work her neck, shoulders, and arms. Concentrating on the one or two soft moans she exhaled now and again kept my attention much more focused on her than the movie.

"Do you want me to work on you for a minute," she asked.

I only nodded. She stood and turned to face me. Before I could move to let her work on me, I pulled her close and kissed her for the second time. My lips found hers, and this time our tongues entwined. My hands roamed the small of her back. Because of her short height, with me sitting on the bed and her standing, we reached each other easily.

"That one was better than the last one," she said after breaking the kiss.

She stepped back for a moment, and from my vantage point, I could see a patch of bare skin peeking out between her waistline and her tank top. The shirt rode up just a tad. I wrapped my arms around her, pulled her close again, and kissed the bare skin.

"Oh!" she said a bit louder than before. I crept kisses up her stomach, pushing her tank top up until it bunched together near her breasts. "Oh, that's very nice."

I reached up and pulled the tank top over her head. Her enormous rack spilled out before me. She pulled my shirt off. Then, without waiting any longer, I swallowed as much of her left breast as possible. Her hard nipple fought to stand tall against my tongue pressing against it. Her fingers clutched my hair.

"This counts as making out, doesn't it?" she asked. Her words came out squeaky, like she was trying not to scream.

I mumbled something noncommittal. Between her nipple in my mouth, her hands tugging at my hair, it was hard to talk.

"I usually like the other breast better," she said.

"Don't worry, I always take care of any body part that has a friend equally well."

It only took another few minutes before I moved on. By that time Sybrina was talking to me. "Right, there baby. Oh you know how to use your tongue on a girl . . . oh! OH!"

Each sound motivated me to greater heights. I trapped her nipple to the roof of my mouth and rolled it around a bit. In my pants, my hard on remained trapped between my leg and my jeans. It begged for release.

For the most part I ignored it. My kisses traveled from her breasts to back down to her waistline, all the while her moans prodded me on. I hooked my fingers inside her waistline to pull her sweats down, but she stopped me.

"If those come off, we are going all the way. And we aren't going all the way till I know you better."

I didn't press that matter. Something inside me told me we'd be having sex soon enough.

"Okay."

My mouth returned to her tits. She surprised me before I got too far. She motioned for me to scoot up on the bed, which I did. "On your stomach," she said.

I got into position, and her cool hands massaged my back, like she initially asked to do. She started at my shoulders, worked her way to the shoulder blades, then the small of my back. At the lower back, she commanded me, "Turn over." I complied. I put my hands under my head, and the moment I got uncomfortable, she unbuckled my jeans and pulled them off, boxers and all, in one swift motion.

My cock jumped up, straight and tall, fluttering in the air conditioned room.

"That's nice," she said. She reached for my cock, and gave it a gentle tug. I closed my eyes, expecting her hands to work the same wonders they did on my back. Instead I got her mouth. Her tongue down one side of the shaft, then then other side.

"Damn, that's good," I grunted.

She spiraled her tongue around my head, once twice, then swallowed the entire thing. The sensation teased me so much I grabbed a pillow and moaned into it. She produced even more excitement when she cupped my balls in one hand. She gently squeezed and received one moan and two grunts. I lost track of how long she worked, but it was a nice long time before my feet began to kick involuntarily.

"You're going to cum on my terms," she said.

Usually I called the shots in bed, but her decision making turned my cock to stone, harder than I ever imagined. Sybrina reached for a bottle of massage oil on a dresser next to the bed. I hadn't seen it earlier, otherwise I would have used it on her.

She lay on her back and poured a ton of oil over her breasts and more in her hands. "Get over here," she said. The oil lubed my cock up nice and slick, and every stroke had me moaning. "Now I want you to cum on my chest, in my face, all over me. Slide that cock in between my breasts."

I straddled her, my balls growing unbelievably hot against her chest. She pushed her breasts together, enveloping my cock between them. With all the oil on her tits and my cock, I slid easily in and out, in and out. Each time I grunted, her breasts a nice substitute for her snatch.

"That's right, baby," she urged me on. "If it feels good, let me know with those grunts. I want it to feel good and I want your hot cum on my chest. Can you do that? Will you cum for me now?"

I thrust harder and my cock slipped out of her giant breasts. Her hand easily grabbed me and put be back inside after a stroke or three.

"Now put that big boy back in between these girls."

Again I thrust between her breasts and soon I was fighting it, trying to hold back. But between her expertise with her mouth, the oil, and her warm breasts, I couldn't resist much longer. A volcanic eruption of cum flew across the room. Some shot into her eyes, some across the bed and onto the dresser, some on her chest, and in other places. I grunted, my breath becoming heavy and ragged.

"Oh, that's the way," she said. "You're doing a great job. It feels so hot and warm on my skin. Just the way I like it."

Soon I was leaking the remnants from my cock's eye, and she grabbed it again and made sure the last of the cum ended up on her palm. One quick swipe and she swirled it around on her chest. I laughed, rolled off of her, and made myself comfortable.

"I'm not sure if that counts as making-out," I said, and we laughed.

"This is so hot, all this cum all over my chest. I'm so turned on right now."

With those words, I couldn't leave it alone. I pulled her close and kissed her stomach in the same place I started near the waistline on her sweats. I was careful not to pull at them—if they came off, it would be her decision. Still, I kissed lower, and reached a hand up to her breasts. Finally, I slipped onto the floor, kneeling for a better position.

Her hands roamed through my hair.

"You're so good at this, and I'm so wet," she said. "Feel this."

She guided my hand between her legs, and I felt the fabric from her sweats soaked through with her juices. I pressed a finger to the edge of her pussy, eliciting another moan from her, and then she was pushing out of her sweats.

"I shouldn't be doing this, but you have me so turned on right now."

The minute her panties came off, I dove into her snatch, licking the skin near and around her pussy. She jerked this way and that, short squeals piercing the air. Finally, I took my tongue and slowly licked as much of her wetness as possible.

"Why are you teasing me so much?" she asked, her hands pushing me onto her pussy.

Her words sparked the heat and I lapped at her pussy lips. I took her clit in my mouth, sucked on it, trapped what I could of it to the roof. Down below my waist, my manhood jumped once, then twice in response to her cries.

My index finger came up and I inserted it deep inside her while I licked around it, or paid special attention to her clit.

"Right there, that's it. Right there," and then she was pushing my head down on her so tight I could barely breathe. She quivered once, twice, three times, and finally let go of me to grab a pillow and scream into it. The orgasm was so intense my cock sprang to attention.

After a moment she released the pillow to see me standing at the edge of her bed, my hard cock erect before her. I wanted to fuck her, to slip my cock inside her, but with her reservations decided to keep from trying. She would make that call. But when my gaze met hers again I saw the same coy smile she gave me earlier. The same one she gave me before we came to the bedroom.

"Oh my, is that for me?" she asked with a fake southern accent.

"He likes it when you scream," I said. "He'll stay energetic if you scream."

"If he's a good boy, he'll get what he wants."

She lifted her legs in the air, and spread them far, granting me easy access. I stepped forward and slapped the tip of my cock against her pussy, once, twice, three times. She exhaled, trying to get a handle on breathing. Then I slipped the head inside her—slowly.

It was my turn to grunt. Tingling sensations ran through my cock, and up my spine at her wetness. The sound of her labored breathing spurred me on. I slid my dick inside her.

Then out. No matter how good it felt, I needed leverage. I took both her ankles in my hands and used them as anchors. Her legs were spread wide in the air, and I propped them up to keep her from tiring. I was now thrusting slowly, but building up speed.

"You're so tight and wet. I can't remember getting any pussy this good for a long long time."

And with those words, I thrust once, nice and hard. Her eyes went big. She tried to mouth an "oh" but was shocked when I thrust hard again. She grabbed her pillow, and then I was thrusting as hard as I could. My balls smacked the underside of her pussy and soon I was grunting in time to her moans.

"It's your turn to cum when I say. Are you ready?"

I said it too late because she was in the middle of an orgasm when I began to ask. She shook and squirmed and thrashed and screamed into the pillow again, but I kept up with my thrusting, feeling an orgasm coming on soon.

I brought her legs together, clamping the ankles tight. This time I lifted her slightly so her ass was a bit off the mattress, and then I thrust as fast as I could. It took only seconds before I was ready to let go, a second orgasm built up inside me.

"If you're going to cum, do it on my chest!" she cried.

I almost didn't have enough time to pull out, but I did. She slid from the bed to her knees before me, and my load gushed onto her chest, once, twice, and just as the third spurt came, she swallowed my cock and I groaned long and hard. She swallowed the rest and licked me clean.

"Damn that was good!" I looked down at her, where she still licked my shaft and balls.

A minute later we were in bed together, cuddled up before the television and falling asleep.

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Tombstone82Tombstone82almost 7 years agoAuthor
Thanks

Thanks for the feedback. I appreciate it!

AnonymousAnonymousalmost 7 years ago
Ended too soon...

Good story, but what was the dirt they had on her? What was the reaction of the guys the next day? 4 stars - thx!

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