Every Young Man's Dream Read online

  “Ever had your asshole licked?” she asked, her eyes looking up from the clipboard for a moment to read his expression.

  He shook his head again.

  “Given anal sex?”

  “No.”

  “Wanted to?”

  A pause, then Troy answered, “Yes.”

  Adriana wrote something down.

  “Received anal sex?”

  “No.”

  “Wanted to?”

  “Not particularly.”

  Again she paused, perhaps lending more credence to his not-so adamant denial than he’d meant to convey. But he didn’t have time to elaborate. Adriana was asking the questions more quickly now, rapid-fire style, which lessened Troy’s sense of embarrassment considerably despite the nature of the questions but didn’t leave any room for discussion.

  “Have you ever stuck your finger in someone’s asshole?” she asked.

  “No.”

  “Had someone stick their finger in your asshole?”

  “No.”

  “Does that make you uncomfortable to think about a girl playing with your asshole?”

  “A little bit.”

  “Why? Because it seems gay to you?”

  “Not really,” he said. “It’s just something that doesn’t seem like it would feel very good.”

  “I see,” Adriana said, writing this down. Then, looking up at him, she asked: “What if you were assured that it did. Would you be open to trying it then?”

  He shrugged. “Sure. I guess.”

  Adriana made another note on her clipboard.

  “Double-teamed a girl.”

  “No.”

  “Been with two or more girls at the same time.”

  “No.”

  “Have you ever peed on a girl?”

  “No.”

  “Wanted to?”

  Troy laughed softly and shook his head. “No.” He noticed Adriana was no longer even looking at her clipboard. Her eyes were locked onto his face.

  “Ever had your balls sucked on?”

  “Yes.”

  “Did you enjoy it?”

  “Yes. Very much.”

  “What about deepthroated?”

  “No.”

  “Wanted to?”

  “Yes.”

  “Have you ever tied a girl up?”

  “No.”

  “Wanted to?”

  “Yes.”

  “Been tied up?”

  “No.”

  “Wanted to?”

  A minor hesitation, then, “Yes.”

  “Interesting,” Adriana said. “Just a few more and we’ll be done. For now, at least.”

  Troy nodded in understanding.

  “Before yesterday, how many girls had you fucked?”

  “Seven.”

  “How many did you cum inside?”

  “Five.”

  “On their stomach or tits?”

  “Three.”

  “On their face?”

  “None.”

  “Did you want to?”

  “Yes.”

  “What about in their mouth?”

  “None.”

  “Did you want to?”

  “Yes.”

  “Did you titty-fuck any of them?”

  “No.”

  “Did you want to?”

  “A couple them, yes.”

  “Did any of them ever sit on your face?”

  “No.”

  “Did you want any of them to?”

  “It never crossed my mind.”

  “Is that something you’d object to?”

  Troy paused as he thought about it for a moment. “No.”

  “Did you ever get rough with any of them?”

  “No.”

  “Did you want to?”

  “Yes. With a couple of them.”

  “How many?”

  “Two. No, make that three.”

  “Did any of them ever get rough with you?”

  “No. But one liked to take charge.”

  “Did you like that?”

  “Yes. Sometimes, at least.”

  “Have you ever fucked a stranger?”

  “No.”

  “Have you ever wanted to?”

  “Yes.”

  “Well, that’s about it,” Adriana said, setting the clipboard and pen on her lap. “One last question and then we’re done.”

  “Okay.”

  “Was this awkward for you?”

  “A little at first. But by the end, no.”

  “That’s good to hear,” Adriana said. She set the clipboard on the stand next to her chair and started to take off the glasses.

  “Do you mind keeping those on?” Troy asked.

  “You like them that much, huh?”

  He nodded.

  “Do you want me to suck your cock with them on?”

  He nodded more vigorously.

  Adriana laughed. “Okay, but first you have to do something for me.”

  “Anything.”

  “You said you’ve eaten pussy a couple times before, right?”

  “Yeah.”

  “And that you thought you were pretty good at it.”

  “That’s what I was told.”

  “But more importantly, you enjoyed it, right?”

  “That’s right.”

  “Then come on over here and show me what you’ve got,” Adriana said, pulling the bottom half of her dress up over her waist and spreading her legs. She wasn’t wearing any panties. Her pussy was smooth, recently shaved. And glistening. Apparently the questions had excited her as much as they had excited Troy.

  He practically leapt off the couch and was on his knees in front of Adriana within seconds. He looked up at her expectantly, awaiting instructions.

  “This is all you,” Adriana said. “I’m not going to give you any direction. I want to see what kind of skills you have.”

  Troy nodded, then took a deep breath, grabbed ahold of her thighs, spread them slightly and pressed his face between her legs. He went to work on her shaved, incredibly smooth pussy, starting off slowly, licking the outside of her pussy lips, tasting her tangy sweetness on the tip of his tongue.

  He glanced up to see how she was reacting and saw her looking down at him, watching him carefully, a little smile perched on her lips. She definitely looked happy but not ecstatic, so he figured he needed to turn things up a notch bit. Returning his attention back to her pussy, he changed his approach.

  Troy stuck his tongue out and ran it up her pussy, starting at the bottom of her snatch and slowly moving it up to the top, lapping at it like a kitten drinking milk. Adriana started to moan softly so he increased his speed, licking more quickly now, his rigid tongue slipping deeper and deeper into her silky smooth insides with every pass.

  He ventured another glance up and saw that Adriana’s eyes were closed and her head turned slightly towards the ceiling. The look on her face plus the increased sounds of pleasure coming from her mouth excited Troy. He could feel his cock pressing painfully against his pants. He was enjoying this more than he’d ever thought possible.

  Adriana’s juices were gushing, drenching Troy’s face, inciting him further. Feeling adventurous, Troy grabbed Adriana’s legs, pushed them back further, giving him better access to her pussy. Then he took a deep breath and buried his head in between Adriana’s legs, smashing his face up against her flesh, forcing his tongue deeper inside her dripping wet pussy.

  Adriana let out an excited little yelp, followed by a deep, pleasurable groan. Troy shook his head back and forth quickly, further covering his face in her juices. He backed off for just a second to catch his breath.

  He looked up at Adriana and saw that she had pulled her dress down, exposing her glorious tits, and was groping them with both her hands. Happy and proud and excited all at the same time, he dove back between her legs once again.

  “Holy fuck,” Adriana moaned as Troy went back to work on her pussy, digging his tongue in as deep as he could get it.
“Right there, Troy. Right fucking there.”

  Adriana grabbed the back of Troy’s head with both hands and pulled him further up inside her, holding his face up against her flesh, her pussy opening up even more, allowing him deeper access to her insides.

  Troy breathed Adriana in, her wet, musky, tangy sweetness his only nourishment while she moved her body against his face, sliding her pussy up and down on his rigid tongue, riding his face, her legs quivering as she approached orgasm.

  And then she was there, her body tensing up for a moment before relaxing, an intense moan coming from her mouth as her pussy juices flowed out of her, soaking Troy even further.

  Adriana released his head, allowing him to breathe properly. He did so in gasping breaths, a big smile on his face while he looked up at Adriana, her nipples hard and her tits glistening with sweat as her chest heaved. Her hair was messed up and it hung down over her face, covering half of it. Her eyes were locked on his and her mouth was turned up in a satisfied smile.

  “Well, what did you think?” Troy asked, his own grin threatening to split his face in two.

  “I have to admit, I’m pleasantly surprised,” Adriana said. “You were pretty damn good down there. A hell of a lot better than most men. And even some women.”

  “Thanks,” Troy replied, starting to blush once again.

  Adriana laughed. “Still embarrassed, huh?”

  “Not by what I did,” Troy said. “But hearing it come from your mouth. For some reason that still has a strange effect on me.”

  “Don’t fret it,” Adriana said. “I think it’s cute.”

  This just caused Troy to blush even more, which made Adriana laugh louder.

  “You did that on purpose, didn’t you?” Troy said.

  “What? Tried to embarrass you more?”

  He nodded.

  Adriana shrugged. Her smirk was predatory. “Maybe just a little. But enough talk. It’s time to repay your generosity.”

  She climbed out of the chair and helped Troy to his feet, then spun him around and dropped him down into the spot she’d just been in.

  With her skimpy little dress still bundled around her waist and the black-rimmed glasses still on her face, Adriana bent over, undid Troy’s belt, opened up his fly, and pulled his pants off, revealing his rock-hard cock.

  Adriana smiled. “Eating me out turned you on that much?”

  Troy nodded.

  She reached down and wrapped her hand around his cock. Laughing, she said, “It’s hard enough to hammer nails into a two-by-four.”

  “Yeah, but I don’t know for how long,” Troy said.

  “You’re that close to being done already?”

  Troy nodded sheepishly.

  “Wow, you really do enjoy eating pussy. I’ve never seen anything like it. At least, not from a man.”

  “Sorry about that.”

  “Don’t be sorry,” Adriana said. “Not at all. There’s absolutely nothing wrong with it.”

  “Okay,” Troy said. “If you say so.” But he didn’t sound like he believed her.

  “I’m serious,” Adriana said. “It’s a good thing. A very good thing. Trust me.”

  “I believe you.”

  With her hand still wrapped around his shaft, Adriana dropped down to her knees. Looking up at him from behind his cock, she said, “We’ll just take care of this real quick and then move on. We’ve got all day to play around.”

  And with that, Adriana took the tip of his cock in her mouth.

  Troy moaned and took in a sharp breath, then let it out slowly. It was all he could do to not cum right then and there.

  Adriana understood his situation and didn’t waste any time, her lips moving up and down on his cock in tandem with her hand, both working in unison, establishing a perfect rhythm, knowing that it was pointless trying to prolong things and just making it as pleasurable as possible for Troy in the short time he had before he shot his load.

  Moving quickly, Adriana was taking his cock halfway down before bouncing back up again, her hand following right behind her mouth, using the saliva she produced to jerk him off while she sucked his cock. Wet, slurping sounds filled the room as she moved faster and faster, taking him deeper and deeper in her mouth, maintaining eye contact the entire time, her eyes behind the glasses locked on his.

  Troy gripped the sides of the chair and held his breath, but it was no use. He was no longer able to prolong the inevitable. He muttered, “Shit, shit, shit,” and shifted in the chair so he was leaning forward just a bit, holding on as much as possible, trying to extract every last millisecond out of the experience before cumming.

  Even though he was right on the edge, Adriana didn’t slow down. She continued going after his cock with the same speed and intensity, even as his body tensed up in preparation of orgasm.

  “Holy shit,” Troy said, trying to give Adriana one last chance to get out of the way before he came.

  But Troy didn’t have to worry. Adriana knew exactly what she was doing. She kept on blowing him right up until the point where he started to cum, popping her mouth off his cock just as the first veins of white semen came shooting out of the tip of his cock.

  She continued jerking him off as he came, aiming his cock at her chest, taking Troy’s seed all over her tits as his body shuddered beneath her.

  Adriana jerked him off to completion, then slapped his cock against her tits a couple of times to make sure it was completely empty before letting go of it.

  Troy closed his eyes and shook his head quickly from side to side then took a deep breath before opening them again. Adriana was still sitting there on the floor, a big smile on her face, his semen snaking it’s way down her chest and towards her stomach, leaving little snail trails in their wake.

  Troy watched as she rubbed his cum into her skin, all over her tits, on top of her nipples, which were still hard. He wasn’t exactly sure why but watching her play with his cum was strangely exciting, which made him realize that even though he’d just came a minute or so ago his dick was still sticking straight-up, as hard as it had been when they first started.

  Adriana noticed it too, nodding in the direction of his cock.

  “Does it always stay hard like that?”

  Troy shook his head. “It never has before.”

  “Do you think you can keep it up?”

  “I have no idea.”

  “Well, there’s only one way to find out,” Adriana said, climbing to her feet and then onto the chair.

  Before Troy realized what was happening, Adriana was straddling him, one leg on each side of his body, her knees and shins lying against the cushion, her ass pressing back against his cock as she sat on his lap.

  “I don’t think this is a good idea,” Troy said.

  “Why not?” she replied, lifting her body up and grabbing ahold of his cock. “Have you done something like this before?”

  “No, but—”

  “Then how do you know?” Adriana said as she pressed the tip of his cock against her pussy but didn’t slide it in. “It might be the best idea ever. Let’s find out.”

  And with that, Adriana dropped her body onto Troy’s, her pussy engulfing his cock as it slipped inside her.

  “Ho-ly fuck,” Troy said, drawing the words out between deep breaths.

  “It feels that good, huh?” Adriana said, smiling like a shark.

  Troy just nodded because he couldn’t talk.

  It was good, very good. But it was strange too. Different than anything he’d experienced before. Because it was so soon after he’d just finished, his cock was extremely sensitive, far more so than normal. So even though it was still hard it was also very tender.

  So far, Adriana was taking it slow and gentle, but even so, he was right on the edge between pleasure and pain. Every little movement made him wince just a bit, and when she bottomed out, her pussy pressing up against his balls, he had to bite his bottom lip to keep from crying out.

  Adriana saw his predicament and took it eas
y on Troy, staying on top of him with his cock all the way inside of her, not moving at all except to lean forward and stick her tongue in his mouth.

  Grateful for the temporary reprieve, Troy explored the inside of her mouth with his tongue, the pure bliss of making out with Adriana taking his mind off the precarious position his cock was in.

  Once he had himself back under control, he slid his hands under Adriana’s ass, spread her cheeks, and lifted up slightly, signaling to her that it was okay to start riding him again.

  She took his cue and ran with it, bouncing up and down on his cock; slowly at first but quickly picking up speed until she was riding him like a cowgirl, forcing his hands out from under her ass because she was hammering him so aggressively.

  Troy’s cock was as hard as ever, having not lost once iota of stiffness since they’d started. It was still more sensitive than usual, but not painfully so. His cock felt like it was on the verge of cumming, when the rest of his body was telling him he was still pretty far away from orgasm. It was strange, and different and wonderful. Yet another new experience brought to him by this gorgeous woman sitting atop him.

  His hands were getting lonely, so he slid them up her belly and slipped them under her tits, holding them in the palms of his hands. She leaned back, showing him the hollow of her neck and accentuating her tits by pushing them out even further.

  With his hands still groping her tits, Troy straightened his arms, forcing her back even more, changing the angle of his cock just a bit. He got his hips into the act, bouncing them up as she bottomed out on his cock, giving his cock deeper access to the inside of her.

  The low sounds of their grunts and hard breathing combined with the slapping of their bodies together and the sloshing of their juices to create a cacophony of sound that was music to Troy’s ears. A symphony of sex.

  Adriana grabbed his wrists and pulled them off her tits then leaned forward once again, even farther this time, pinning his wrists to the chair next to his head. Holding them in place, staring right down at him with an intense look, her body positioned so it seemed like she was hovering over him, Adriana slammed her body down on his, riding Troy’s cock from tip to base, picking up speed with every pass.

  Adriana was moving so aggressively against Troy now that she could no longer maintain her balance, so she released his wrists and transferred her hands to his chest, pressing down on him with her palms, giving herself more leverage as she pummeled him, impaling herself on his cock.