Dark Fiction – A Dare with a Condom – Will She Win or Lose?

Her friend dared her to use the condom on a stranger – he was more than willing to help

“Mister, can I ask you something?” As the girl giggled, she glanced back to her friend, who was laughing as much as she was.

“Yeah, sure,” I replied as I glanced up from my paper. This business trip was dull enough, so I could do with some entertainment during lunch. And an attractive woman could always distract me.

“I was wondering…” She giggled too hard to be able to speak. Again she glanced back to her friend at the other table. “Could I come to your room and suck your dick?”

“What?” I asked amusedly. I mean, I wasn’t against the proposal, but I doubted I had heard it correctly.

She waved a condom in her hand. “My friend dared me to use this on a stranger, and I hoped you could help.”

I looked around the restaurant. I was the only male under the age of seventy, so I could see why she picked me.

“I’ll tell you what. I have my afternoon scheduled with meetings, but what if you come to my room tonight at, let’s say, eight? Then you have some time to reconsider, and I get a chance to prepare myself.”

She cocked her head to the right. “Okay, I could do that. What’s your room number?”

“471. And don’t feel obligated by your friend’s dare. I’m not forcing you. I won’t hold it against you if you change your mind.”

“I won’t. I’ll see you tonight.” She blew me a kiss as she returned to her friend.

She really was pretty. Barely legal, I guessed. The cogs in my head were turning. She wasn’t my usual type, but instead of doing the hunting, she basically threw herself in my arms. I could adapt. Now it was time to set things up.

I folded the paper and left the restaurant. The friend would never remember me well enough to give a plausible witness statement. Another thing that worked in my favour was that this old hotel didn’t have any fancy cameras. The camera installed in the early 90s could never be used to make a positive ID on anyone. And even though this was a business trip, I had used one of my alternate credit cards as a habit of force. The stars had aligned well for me. Now all I had to do was do what I liked to do best.

At eight o’clock sharp, there was a tapping on the door. I checked the spy-hole, but it was indeed Miss Giggly from that afternoon. I opened the door. “You made it.”

“Of course I did.” She held up the condom she had shown earlier. “It was a dare, after all. That shouldn’t be taken lightly.” She entered my room and looked around. “This isn’t a luxury penthouse.”

“My company isn’t that forthcoming.”

She giggled. “Aren’t they all?”

“Would you like a drink? Perhaps some Dutch courage?” I showed her my bottle of vodka.

“Sure.”

I poured her a glass, and she downed it in one gulp.

“So, what was your dare?” I asked.

She blinked and scrunched her face as the alcohol passed through her body. “My friend dared me to use this condom on a stranger.”

“Use it? But most condoms are used for intercourse, not blowjobs.”

Her eyes widened as she protectively crossed her arms. “I’m not sure I’m comfortable with that.”

“So, what is your suggestion?”

“I’ll blow you.”

“Okay, you ready for it?”

She nodded. I lowered my pants and boxers and took a seat in the armchair. I stroked myself slowly. “I suppose you do the condom?”

Again she nodded, though she was slightly hesitant this time. She took a deep breath, knelt down between my knees, unwrapped the condom and rolled it over my dick. It was nearly hard already but sprung to life at her touch.

She frowned but dutifully bent forward and took my glans in her mouth. She suckled a few times before releasing it and looked up at me. “You’re not a serial killer, are you?”

“Of course not,” I replied with a devious smile. “I’m just a horny dude looking to get his dick sucked.”

I grabbed her head and guided it back to my hard-on. She resumed her task and took me in deeper this time. I leaned back in the chair and enjoyed her ministrations. She was pretty good for her age.

While she was taking me nearly all in, her motions became slower.

“Are you okay?” I asked.

Her hand went to her forehead. “I don’t know, a bit dizzy.”

“The Dutch courage hit you too hard. Come, lie down for a moment.” I helped her onto the bed.

“Yes, thank you.” She smiled weakly at me. “Sorry I couldn’t finish the blowjob. Maybe in a bit when I feel better.”

“Don’t worry. Here, let me help you with your clothing. It looks a bit tight.” I undid the button of her jeans.

“What? No.” She rose up but fell back down immediately.

I grinned. “Still too dizzy, huh? Don’t bother; I know the way.” I took off her jeans and panties and positioned myself over her body. I spread her legs and fingered her. Despite her dazed state, she was already wet with arousal. I placed my dick at the entrance to her pussy and sunk it in. Her eyes widened in shock, but all she could do was try to push me away half-heartedly. I was happy to see the additive to my vodka was still potent.

I fucked her hard. The longer I lasted, the further she sunk away in oblivion. I enjoyed it. She was young and tight. If it hadn’t been for this dare, I never would have tried my luck with her.
I pounded her for a long time. I loved it when they were out. No protests, no demands; only my pleasure counted. I grabbed her boobs and twisted them, remembering how my previous lover had screamed when I did that. The memory sent me over the edge. I stayed on top of her until I had released all of my cum inside the condom.

It was time to end the show. I carried her into the bathroom placed her in the bathtub. I took my gun, put it against her temple and fired. Now she couldn’t accuse me of rape, nor could she identify me.

I packed my belongings and left. I had prepaid the room for the next six months, so either at that time or when the stench of her corpse would seep through the walls, would she be found. I’d be long gone from the state then, and there were no ties between her and me. I think it’s safe to say I won this dare.