Madison Avenue Ch. 02

"Yes, sir. But not ... I mean ..." Her voice trailed off again as she stared wide-eyed at my cock as it bobbed slightly in the cool air of the room. "Not one like that."

"Am I deformed or something?" I asked with a chuckle.

"Not deformed, no. Just ... big ... and ... thick."

I laughed softly.

"Well, it's quite the debt your boyfriend owes."

"You're not fucking kidding," she blurted out, looking up at me, blushing an even brighter shade of red.

I smiled, stepping out of my jeans and boxers, kicking them to the side, and pulling my shirt up over my head, tossing it to the floor. She reached out tentatively, as though she were scared of my cock, and wrapped her fingers around the base, lifting it, looking it over, examining it.

"It doesn't bite, Madison."

She nodded and looked up at me, gulping, her eyes wide, scared, nervous.

"I'm not sure I can," she whispered, swallowing hard and looking back at my cock.

"Like I said, I won't force you."

She giggled. "No, I mean, I don't think I CAN. It's so big."

She was laying it on pretty thick. Like I said, I'm bigger than average, but I'm not exactly a tripod.

"Just do what you can, dear."

She nodded again and swallowed, licking her lips, taking a few deep breaths, generally acting like she was about to jump out of a plane for the first time. She moved her head forward slowly, taking a few unsteady, nervous licks at the head, tasting it, kissing it. It was almost too much, all of it, the roleplaying, the feeling of her warm, smooth tongue flicking over my cock, the sight of her kneeling before me. Somehow, I held on, closing my eyes and thinking of anything else.

I felt her lips stretch wide as she took the head into her mouth slowly, testing the waters with a toe, her tongue slipping rapidly back and forth across the underside of my shaft, teasing me as she started to get into it, taking a few inches into her mouth, sucking softly before stopping and pulling back, licking her lips and looking up at me.

"I can't believe I'm doing this," she said.

She didn't wait for a response, simply resuming her sucking, a few inches in and out of her mouth, lips gliding along the engorged, throbbing shaft, eyes closed. I watched closely, and when she opened her eyes and winked at me, my whole body shuddered. I reached down and pulled her away. As I've said, watching her is too much, it's too sexy, too incredibly sensual to withstand. She licked her lips again.

"More than just a blowjob is owed, I guess," she said, giggling, letting her character feel more comfortable.

I nodded. "As I said, Madison, it's a considerable sum of money."

She shrugged. "What then?"

"You asked me to promise to not do anything you didn't want to do, so I suppose I need to know what those things are."

"Can I stand?" she asked. I nodded and she rose to her feet, raking her breasts and hard nipples along my body as I helped her up. "Well, I was going to say, you know, no anal."

She paused, looking up into my eyes. Like I said, we'd experimented, but the word "anal" wasn't involved in our experimenting.

"But then I was thinking," she continued, "that like you said, my boyfriend offered my ass to save his ass."

"I wasn't talking specifically about your ass, Madison. I was being more general." Yes, I was offering her a way out. Roles or no roles, this was a young woman I loved. She needn't give me anything more than she was willing.

"I know that, Mr. Moretti," she said. "But fair is fair. And like I said, I happen to think I've got a great ass. My boyfriend never appreciated it properly. Someone ought to."

"And besides," I said, reaching up to tuck her hair behind her left ear, "this gives you a way to get back at him for the situation he put you in."

"Yes, sir, it certainly does that."

"Very well, then. I see no reason why we can't both get something out of this. Have you ever?" She shook her head, lowering her eyes again. "I'll be gentle then."

"Not too gentle," she said. "I want to remember this, remember why I left him."

"As you wish, Madison."

She stepped past me, her back to me as she faced the chair, reaching out for the glass of scotch I'd long since abandoned, downing it quickly.

"Still burns," she said with a shudder, setting the glass down and kneeling slowly in front of the big, leather chair, leaning forward and putting her arms on the seat as she rested on her knees. "You can fuck my ass now, Mr. Moretti."

I shook my head, turning to face her as she knelt submissively in front of me, looking back over her shoulder at me and nodding, her gaze soft as she looked into my eyes. I smiled, taking a step forward, reaching down to pull the thong down.

"Just pull it to the side, Mr. Moretti."

I nodded, kneeling down behind her and pulling the thin strip out from between the cheeks of her ass, pulling it to the side, and looking at her puckered asshole for the first time as something sexy, something desirable, and it was indeed that. I leaned forward and licked nervously, much as she had just done with my cock. Her body shivered.

"Oooh, you're nasty, Mr. Moretti. Lick my ass, get it nice and wet for your big cock to slide in." She giggled softly, wiggling her hips.

I did just that, lapping at the tight, little hole, getting it nice and wet with my spit. I'd never done that before, but I figured the wetter, the better. After I got it nice and wet, I licked my finger and pressed it against the entrance, wiggling the tip as her body fought against the intrusion before my finger popped in. It's a strange feeling, like a pussy, but tighter, warmer even, and without the natural lubrication. She moaned as my finger pushed in.

"I don't know how you're going to fit your big cock in, Mr. Moretti. Your finger feels so big in my little hole."

"We'll find a way, Madison," I said, twisting my finger and then adding another, an action greeted by another shiver, another throaty moan.

"Yes, sir. Yes we will."

I worked my fingers in and out, fascinated by the way it looked, by the way it felt. It was a completely foreign experience to me, as the whole roleplaying situation had been. I could feel the muscles starting to relax, her whole body starting to relax.

"I'm ready if you are, Mr. Moretti," Madison said, her voice low and steady. Scotch is a helluva relaxant, I guess.

"I'm certainly ready, Madison."

I rose up to my feet and crouched down, letting some spit drip down out of my mouth onto my cock. I rubbed it into the tip and then added a little more spit to her asshole, rubbing it in with the tip of my cock, before resting one hand on her lower back and holding on to the base of my shaft with the other.

"I'll go slow at first," I whispered, as much Christian as "Mr. Moretti."

Slowly and tenderly, I pressed the head against the entrance and really didn't believe there was any way it would fit. I could barely get the head in without pushing hard. God, I thought, this might be taking this game a little too far.

"Don't stop," she whispered as her body wriggled beneath me. "Don't you dare stop."

I pushed forward, pushing the head of my cock inside of her, along with the next inch or two of my shaft.

"Ohhhhhhhh, fuck!" she spat out. "So big, so fucking full. More, more."

Roles or not, at this point, Madison was in the driver's seat. I pushed forward, about half of my cock penetrating her tight ass, the muscles clenching tightly around my shaft.

"Give it to me, Mr. Moretti! Give me all of it."

I grunted, pushing forward again, inching my thick shaft into an entrance that clearly didn't share Madison's determination for me being there. But in the end, she won out over her body, and I rested there, my cock buried completely in her ass, my head swimming. I'd never felt anything remotely like that, though to this day I'm convinced that the idea was more satisfying, that her giving herself to me completely in such a way was more meaningful than the actual act was pleasurable.

Goosebumps rose up all over her bare back, and she lifted her head up, moaning.

"Jesus, Chr ... I mean, Jesus, Mr. Moretti," she growled passing over her mistake quickly. "That big cock is all the way in my ass, isn't it? My boyfriend's debt is paid, right?" Her breathing was heavy, and her fingertips dug into the leather of the chair.

"Not until I finish, Madison."

"Finish then, you son of a bitch! Take my ass!"

I growled, pulling my hips back and withdrawing my cock as she whimpered beneath me. Both of my hands were on her back now as I held her down against the chair, slowly sliding my cock back inside of her.

"Fuckin' loser ass boyfriend!" she yelled as I pushed back in. "Fuckin' asshole! Fuck my ass, Mr. Moretti, be the man he never was!"

I built up a steady rhythm, my hips smacking against her ass as I pumped my cock in and out of her ass, grunting and growling.

"You like it, though, don't you, Madison? Being a slut, paying off your boyfriend's debt with your ass?" I measured my words carefully, keeping my head, not wanting to hurt her, physically or otherwise.

"I do!" she yelled. "I love it!"

In and out I drove my cock, her asshole relaxing, taking what I could give it, though I admit I held back some, partly because of her, and partly because it was too much, such a new sensation, and I knew I wouldn't last long. And I didn't.

"I'm going to cum, Madison," I said through clenched teeth, my fingers digging into the skin of her lower back.

"Cum in my ass, Mr. Moretti! Cum in my slutty ass!"

I did just that, a knee-buckling, body shaking, almost hurtful orgasm. I came for what seemed like an eternity, cum spraying over and over from the tip of my cock, burning almost as it came out with such a fury deep inside of her ass.

It finally stopped, and my whole body was shaking as I felt myself start to soften, still inside of her. My eyes closed and opened, colors and shapes flashing in front of my eyes as I struggled to hold myself up, moving my hands from her back to the arms of the chair, knees against the chair as I fought to catch my breath. Cognitive again of her after a minute or two, I reached down, stroking her hair as she looked up at me over her shoulder, her eyes heavy.

"I came, too, Mr. Moretti. That was amazing."

I nodded, pulling my now soft cock from her ass and wrapping my arms around her, lifting her up as we both knelt on the floor.

"Are you okay, Madison?" I whispered, kissing her cheek.

"I'm great, Chris. Thanks for a great birthday."

*********

-December 18, 2006-

I was snapped from my daydream by the feeling of Damien's SUV coming to a stop. I blinked my eyes and looked around. The whole drive up to Cleveland had passed. We were parked close to the arena. Paul jumped out of the car, professing his love for the Cavs loudly to anyone within shouting distance. Damien turned off the ignition and looked back at me.

"You alright, bro?"

I nodded. "Nothing a Cavs game and a night on the town can't fix."

"You got that right." He smiled and nodded.

And yet as I climbed out of the car, I couldn't shake off the feeling that not only wasn't I alright, but I wouldn't be alright for some time. The visit with McAllister and Gutierrez had me shaken up, even if it didn't really mean anything. Why would the FBI care that I was back in town? My father was who he was, but I was never involved in anything he did in any way other than overlooking it. That didn't make me culpable. So why the concern? I had no rap sheet. Sure I had the connections to certain people, and I could get involved in something illegal if I wanted to, but that had always been the case, and I'd never taken the bait. Nothing had changed in my eyes, so why should it in theirs? Something didn't add up; none of the pieces fit comfortably.

Like I told them, I'd been in town for six months with no problems. What did they know that I didn't?

And then there was Madison.