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The Trip of a Lifetime | harolds | 4

 

"Since you seemed so interested in my suitcase, I'll show you what I like do with some of the toys," Cindy said, getting a devious look in her eyes.

"Great!" Dan replied immediately.

Cindy packed the toys back up and went into the bathroom. "You just wait here and I'll be right back." That devious look was still there. Suddenly, Dan wasn't quite sure what he'd gotten himself into. He heard the bathroom door click shut and the suitcase being opened.

Dan sat back on the bed, waiting for the beautiful dark-haired girl to come out. He couldn't believe what had happened in the last few minutes. He never expected to get a blowjob from a random stranger like that. Suddenly, he remembered the girls from the elevator. They were giving him some strange looks too. Do you think? Nah, they couldn't have had similar thoughts, could they? What if they did? What if everyone on this trip had only one thing in mind? The possibilities....

Dan's daydreaming was interrupted by the bathroom door swinging open. Dan's mouth fell open in shock at what he saw. Cindy was dressed in a black leather bra and fishnet stockings up to her thighs, but what really grabbed Dan's attention was the 7-inch black strap-on dildo she was wearing.

"Are you ready to pay your debt?" Cindy's tone made it clear that it wasn't really a question.

"Whoa, hold on a sec..." Dan's protest was interrupted by Cindy shoving him down onto the bed.

"Shut up!" Cindy barked. She climbed on top of Dan, dangling her strap-on cock in front of his face. "Suck it!" she ordered.

"What?!"

*THWAP* the head of the silicone cock his Dan square in the forehead. "I said, suck it. You will not make me repeat myself!"

Dan decided against arguing and hesitantly took the toy into his mouth. He had never imagined a cock feeling so big in his mouth, and he just had the tip in. Cindy began rocking back and forth, fucking Dan's mouth with her strap-on cock. She pushed it deeper into Dan's mouth, causing him to gag. As the toy popped out, Cindy pulled back.

"Very good, you're learning", she cooed. Glancing down at Dan's still exposed cock, Cindy laughed slightly as she noticed it starting to harden. "So, you seem to like that?" she reached down and began stroking his dick, causing it to spring to full attention. "Good. I like a man who can give and receive. Get up!" again, it was not a request.

Dan stood up slowly, unsure of what was to come next. Cindy spun him around and shoved him face down on the bed.

"Tell me Dan," Cindy asked as she grabbed a tube of lube. "Have you ever had your ass fucked before?"

"WHAT?? NO!!" Dan practically screamed.

"Mmmmm, a virgin! Nothing's better" Cindy giggled as she positioned herself behind Dan, running her strap-on up and down his ass crack. "Just relax. You might actually enjoy this." There was something in her tone that actually made Dan feel a little bit better.

Cindy continued lubing up her cock, making sure it was well-covered before spreading Dan's ass cheeks and positioning the head against Dan's asshole. "Deep breath" she instructed.

Dan inhaled deeply as he felt Cindy slide the toy up his virgin asshole. It was a strange feeling. Dan felt vulnerable but not violated. He knew his cock was rock hard, which puzzled him. Cindy began slowly at first, moving in and out ever so slightly, her hands running up and down his back, squeezing his buttocks.

Cindy pushed further, burying her strap-on deeper into Dan. Suddenly, Dan felt a wave of pleasure unlike anything he had felt before as the dildo slid in and out of his rectum.

"Hmmm, I think we hit the spot!" Cindy laughed. Pushing the dildo deeper again, Dan felt the shudder of pleasure again as the dildo, he now realized, brushed past his prostate. No longer concerned about the unusual situation, focused only on the pleasure Cindy was giving him, Dan began rocking in rhythm with Cindy's thrusts. He pushed himself up off the bed slightly with one hand, reaching down to stroke his cock with the other.

Cindy reached around and tickled Dan's balls with her hand before taking over the stroking of his cock. Dan kept his hand on hers to guide her as she fucked his ass and jacked him off at the same time.

Her thrusts were deep and fast now, in rhythm with the strokes on Dan's cock. He could feel the orgasm brewing within him. It was brewing deep within him, deeper than ever before.

Cindy, now thrusting with all her might, the full 7-inches buried into Dan's asshole, stroked his cock with equal fervor, teasing his balls with her other hand when suddenly Dan exploded. A hot stream of cum shot out of Dan with more force than he had ever seen before. The first spurt actually hit him on the chin before dropping to the mattress, the second shooting nearly as far.

Cindy slowed both her thrusting and stroking, gradually working Dan back down as the last spurts of semen shot out of him. Finally, she realeased his cock and pulled the dildo from Dan's ass. Free of any of her support, Dan collapsed onto the bed, landing in puddles of his own jizz.

Cindy flipped him over, kissing him deeply and licking the spunk off his chin.

"I'd say we're more than even now," she smiled at him.

Dan was too exhausted to say anything.

"I think my roommates would love to meet you," Cindy said. "Why don't you get cleaned up and come with me?"

 

What does Dan decide?


          Meet the Roommates

 
 
 

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