“I’ll tell you,” she said. “Eventually you’ll learn how to read it yourself, but for now, just listen and do what you’re told.”
So he did, slowing down a bit, getting in a rhythm, only speeding up when she told him to, eventually slipping another finger in at her request, following her every direction as accurately as he could, from depth to speed to positioning to what to do with his mouth, his tongue, his other hand.
Tommy was surprised to find that her enjoyment was getting him off. The more she got into it the more he did too, and it didn’t take long before his cock was rock-hard once again, without her so much as touching it.
“See,” she said, reaching down and giving Tommy’s cock a couple of strokes with her hand while he continued banging her. “I told you I’d take care of that part, didn’t I?”
Tommy nodded, too busy to talk.
“Now let’s see you put it to good use again,” she said. She pulled his hand out of her pussy, stuck his index finger in her mouth, licked it clean, and popped it back out of her mouth. “Do you think—” She popped his middle finger in her mouth and gave it the same treatment. “You can—” She paused in order to lick his ring finger clean too. “Do that?”
Tommy swallowed hard and again nodded. He knew that eventually he’d have to get over the embarrassment of talking during sex but for now he was going to stick with what was comfortable.
She slid up and away from him. Still on her back, she spread her legs and beckoned him over. “Then come over here and stick that giant cock inside me.”
Tommy didn’t need to be told twice. He practically jumped atop her, so anxious was he to fuck her pussy again. Grabbing his cock in his hand he slid it inside her and started to move quickly against her.
“Ah, ah, ah,” she said, her hand on his chest to halt his progress. “Slowly, just like with your fingers. Take your time. There’s no need to rush. It’s not a race.”
He started to apologize again but she cut him off by covering his mouth with her hand.
“I told you before, no apologies. You don’t have anything to be sorry about. This is a learning process. Nobody gets it right the first time. Okay?”
Tommy nodded.
“I want to hear you say it,” she said. “I want to be sure you understand.”
“Okay,” he said quickly, wanting to get it over with. His cock felt like it was going to burst through his skin. “I understand.”
“Slowly,” she said, drawing the word out.
Tommy dropped his gaze for a moment. With his cock still inside her, he took a deep breath to gather himself, then looked back up at her gorgeous face. “Okay,” he said, far more calmly this time. “I understand.”
“Then prove it,” she said.
He leaned in and starting kissing her. While moving his lower half very slowly inside her, Tommy explored her mouth with his tongue.
As she returned his kiss Tommy found himself moving slightly more quickly, still taking his time as much as possible, but unable to completely contain his excitement.
“That’s it,” she said, pulling her mouth off of his. They were face-to-face, their noses practically touching. “There you go. Right there, baby. Right there.”
Her encouragement didn’t help him stay calm. In fact it got him more excited, causing him to move faster against her. Which he was starting to think was her purpose all along, as the more quickly he moved against her the more she talked, which just got him going even faster, to which she replied by talking even more. She had to know what she was doing to him.
“Give it to me,” she said, her voice louder now, more intense, pushing him further and faster with every word. “Fuck me with the big cock of yours. That’s right. Like you mean it. Yes! Yes! Yes!”
Tommy was giving it to her with everything he had now, his cock slamming into her pussy with every bit of force he could muster.
“God-dammit!” she screamed, losing herself for the first time. “That feels so fucking good! Fuck, fuck, fuck! I’m gonna fucking cum, don’t stop, don’t stop, don’t fucking stop!”
He couldn’t stop, not now. It felt too damn good to even think about slowing down, let alone stopping. And her being so into it just turned him on even further. Right about now Tommy was a speeding train that had lost all its brakes. There was only one thing that could end his ride. The end of the line.
They got there at almost exactly the same time, her body shaking and shimmying beneath him just as he tensed up in anticipation of finishing up for good. Her gyrations put him over the edge, causing him to shoot his seed inside her without the usual extended moment of anticipation before release.
“Not bad,” she said between large gulps of air after they’d stopped moving against each other. “Not bad at all.”
Smiling, Tommy climbed off of her and dropped onto the covers next to her. He was proud of himself. He wasn’t sure exactly why, but he felt good nonetheless. Far different than the guilt he usually felt after orgasm.
She turned on her side and looked over at him. “You did good, kid. Surprisingly good, actually.”
“Thanks,” he said, feeling his face growing red. He was never very good at taking compliments.
“So what do you say? Should we try this again tomorrow. Say, around noon?”
“I can probably do that,” he said. “But I need to know one thing before I commit to anything.”
“Just one?”
“For now.”
“Then fire away,” she said.
“What’s your name?”
She looked at him and smiled. “Hayley.”
Tommy nodded approvingly. The name fit her perfectly. “Pleased to meet you, Hayley. I’m Tommy.”
“I know,” Hayley said.
“You do?”
“Of course,” she said. “Do you think I’d just bring home a stranger to fuck?”
“Well, I . . .” Tommy stammered.
“I’ve had my eye on you for a while, Tommy T. Carter. Quite a while, indeed. Of course, if I would have known how big that hand cannon you keep beneath your pants was, I would have manufactured our little collision quite a bit sooner.”
He tilted his head and eyed her carefully. “You planned this whole thing out?”
“More or less,” she said. “This morning was supposed to be the first of many accidental occurrences that would have inevitably led to the same situation that played out here today, but lucky for me things turned out differently than I had planned, so I sped up the process a bit.”
“How’d you know I go along with it?”
“Please,” she said with a smirk. “What young man wouldn’t take the opportunity I was affording him? Anyone you know?”
He had to admit, she had him there. “No, I guess not,” he said with a little chuckle.
“Of course they wouldn’t,” Hayley said. “Just as none would pass up the chance to continue the affair.”
“You’re that confident I’ll keep on coming over, huh?”
“Absolutely,” she said. “Especially once you’ve had a night to think about where we’re going to go from here.”
“You mean it gets better?”
“Well it sure as hell isn’t going to get worse. Not with what I’ve got planned.”
“And what is that, exactly?”
“You’ll just have to come back to find out,” Hayley said. “But let’s just say that today was just the tip of the iceberg. I’ve got a thousand little tricks I can teach you, if you’ll just give me the chance.”
“Like what?” he asked. “Just give me one example.”
Smiling, she leaned over and starting whispering in his ear. Just a couple sentences, but they were enough to make his cock stir around, even though they hadn’t been done for more than minute.
He laughed and shook his head. “Who in their right mind would pass up something like that?”
“Who indeed?” Hayley said.
“Certainly not me,” Tommy said.
“So I’ll
see you again tomorrow?”
“Do we have to wait that long?” he said, half-jokingly.
“Unfortunately I already have plans for the rest of the day,” she said. “Otherwise we could hang out and screw around until night fell. But as it is, I’m already running late, so I’m going to have to call an end to day one of your education.”
“That’s too bad.”
“Not necessarily,” Hayley said. “You can actually make it work to your advantage if you go home and do a little homework tonight.”
“What kind of homework?”
“Just a bit of studying.”
“What?”
“Positions. Things you’d like to do to me. Things you’d like me to do to you. Tomorrow we’re going to see how you react when you have control.”
Tommy’s face started to flush.
“But first you need to figure out how to get over your embarrassment,” she said. “Because I’m certainly not going to start mincing my words. If anything, I’m going to get more blatant, more bold as we go along. And I expect you to also. Do you think you can handle that?”
“I can sure try.”
“That’s not good enough,” Hayley said. “You need to figure it out. And right quick. Otherwise you might end up paying the price.”
“And what price is that?”
“You don’t want to know,” she said, flashing him an evil smile. “Of course, after you experience it, you might like it. After all, like I said earlier, it truly is impossible to know if you like something until you try it. And I seem to have a way of making people like it, no matter how much they think they won’t. I can make pretty much anything feel good.”
“I have no doubt about that,” Tommy said.
“All right, that’s enough chit-chat,” Hayley said, giving him a little peck on the cheek before climbing up and out of the bed. “I’ve got to get out of here. You can show yourself out I presume?”
“Not a problem.”
“And I’ll see you tomorrow?”
“I wouldn’t miss it for the world,” Tommy said.
“I knew you wouldn’t,” Hayley replied, looking over her shoulder and flashing him a smile as she made her way into the bathroom. “I’ll be expecting you around noon.”
“I’ll see you then,” he said, rolling out of bed himself. He made his way downstairs, gathered up his clothes, and put them on. With the sound of the shower filling the house he looked around one last time, laughed softly, then shook his head and made his way out the back door.
Tommy started jogging back towards his house, feeling a thousand things at once, and not one of them bad. He had a big smile on his face. For once he had homework that he was looking forward to doing. Life was good. And it was about to get even better. A whole lot better.
He couldn’t wait for day two.
#####
AGGRESSIVE & FILTHY: VOLUME 26
Well, so much for that.
The last time I wrote one of these confessions, I was coming off a particularly romantic session, so utterly unlike any of my previous nights with an escort that I swore them off and decided to make a run at a traditional relationship.
That was almost six months ago. Six months of confusion, emotional distress, arguments, disillusionment, and worst of all, boring sex.
So I gave up.
Last night, after contentious evening with my so-called girlfriend that ended with us broken up and me angry as hell, I made the call. I set up an evening with Bailey Mynx, a pornstar who escorts on the side. Although I’ve never been with her before, I feel like I know her well, having jerked off to way too many of her movies over the past few years.
Normally I don’t set up sessions with porn stars, mostly because they use their notoriety as an excuse to charge three times the average going rate. But I figured after taking so much time off in an attempt to go the legitimate route, I deserved to splurge. And so I did. Bailey is one of the most popular pornstars in the world, and from what I understand—not to mention what I’ve seen on screen—an incredible fuck.
#
My stomach is full of butterflies as I wait in my hotel room, working on my eighth beer of the evening. Normally, a session with an escort doesn’t make me nervous at all, but the six-month layoff combined with the fact that I was going to spend the evening with a pornstar instead of a normal escort had given me a good case of the nerves.
I’m reasonably certain it won’t affect my performance, but I’m sure it will mess with my personality a bit. Even with all the beers I’ve already finished, I’m still feeling a bit on the shy side. Although I doubt it will matter at all. Bailey is known for being a heavy talker, plus she’s undoubtedly used to being men who are a bit star-struck, so I’m sure she won’t care that I’m most likely going to keep my mouth closed all night.
There’s a knock on the door. I pound the last of my beer, take a deep breath, and head over towards it. After taking another deep breath, I open the door.
Standing there, in the flesh, is Bailey. I take her in with my eyes all at once, staring at her for what seems like an hour but is really only a second.
When I called I asked that she come over dressed normally instead of all decked out in a typical pornstar outfit and she’s obliged, wearing a pink and white striped short-sleeve sweater that exposes a little strip of tanned skin at the bottom of her washboard stomach, a pair of blue jeans and heeled sandals. Her long black hair covers half her gorgeous face and her makeup is relatively subtle, compared to some of the getups I’d seen her wearing in the movies.
Her big, blue eyes were ringed with just a little eyeliner, she has a stud in the side of her nose, and subtle lipstick that matches her sweater. Her tits are small and perky but her legs are long and toned. She’s a beauty to behold, one of the most fuckable girls I’ve laid my eyes on in some time.
My breath catches in my throat and my heart starts to pound. Not just because she’s so freaking hot (although she is) but because it’s actually happening. It’s amazing how much of a difference it makes when the girl standing out there waiting to come in and fuck me is a pornstar instead of a normal escort. It really shouldn’t matter, after all the principle is exactly the same, but it does. A lot.
“You must be TIM,” Bailey says, taking my shyness in stride, just as I figured she would.
I nod.
“Do you mind if I come in?”
“Of course not,” I manage to say. I stand aside and she walks by me. I peek at her ass as she walks by. It’s as tight as it always appears to be onscreen. I close the door and turn to face her.
She’s standing there, staring at me with an expectant look on her face. It takes me a moment but I eventually figure out what she wants. I dig into my pocket and pull out a wad of cash and hand it to her.
She gives me a little nod of thanks, then counts it and slips it into her purse. “You seem a little nervous,” she says. “Is this your first time doing something like this?”
“No,” I say. “But it’s been a while.”
“Just relax,” she says, dropping her purse on the coffee table. “I’ll take care of everything.”
She steps towards me and leans in and kisses me. I kiss her back, opening up my lips to accept her tongue. As we explore each other’s mouths, her hands drop down to my waist. She deftly undoes my belt and the top button of my pants, followed by the zipper.
As I take a deep breath to keep myself under control, she drops to her knees, pulling my pants and boxers down as she goes.
With my pants down around my ankles, I watch Bailey as she grabs a hold of my cock and holds it up against my stomach and runs her tongue lightly over my balls. Smiling, she looks up at me.
“You like that don’t you,” she says. “You like it when I lick your balls.”
I nod.
Smiling up at me, she goes back to work on my balls, taking them in her mouth and bouncing them around with her tongue while her hand moves up and down on my cock, gently jerking me off.
“You’ve got a very nice-looking cock,” she says. “Do you mind if I take it in my mouth?”
I shake my head.
“Yeah, I didn’t think you would,” she says.
Bailey opens her mouth and wraps her lips around the tip of my cock. With her hand gripping the base, she sucks on the head for a few seconds. She pulls her mouth off my cock, gathers up some saliva and spits on it. Her eyes still looking up at me, maintaining eye contact the entire time, she jerks me off, working the saliva in.
“Do you like how my lips feel around your cock?” she asks.
I nod again.
She laughs. “You don’t talk much do you?”
I shake my head.
Her mouth turns up in a little half-smile. “Feeling a little shy, are we?”
I nod.
“That’s okay,” she says, still working my cock with her hand. “I’m used to it. Besides, I’ll talk more than enough for the both of us. Unless you don’t like that sort of thing, of course.”
“No, I like it,” I say.
“Good,” Bailey says. “Because my mouth has a mind of it’s own.” She pops it open, her lips creating a big O. She slips my cock into her mouth, taking it almost all the way down before sliding it back out. “See what I mean,” she says once my cock is clear of her lips. “I just can’t seem to keep it closed.”
Smiling, I laugh softly and shake my head.
“Oh wow,” she says. “You do you have a personality after all.”
I raise my hand and bring my forefinger and thumb close together. “A little one,” I say.
Bailey laughs. “That’s okay,” she says. “The size of your personality isn’t what’s important right now. The size of your cock is. And it’s certainly not a little one.”
She takes my cock in her mouth again and starts bobbing her head forward and back, taking it three quarters of the way down every time, sucking me off at a good, solid, medium pace, her hand working in unison with her mouth.
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