I'm a Man Now

"Come on, get on top of me, babe."

Climbing up over the couch, Anna didn't reply to him in words. She moved with action, straddling his lap once she had climbed up over the couch and then using both of her hands to hold up his swollen cock. She glared at him with her big blue eyes, dropping her lower lip to give him yet another view of hunger with her teeth gritted.

"Before I ride you, I've got something to ask."

"Shoot."

"Do you wanna cum inside of me? Cause I plan to ride you until I get to."

Matt shook his head.

"No, I want you to suck me off again. I've always dreamed of being able to cum on your face."

Anna giggled at him.

"Oh, you wanna blow your load all over me like in some porn video you might have watched?"

"Fuck yeah!"

His reply made her laugh again. Tightening the grip of her fingers around his cock, that dripping wet pussy hovered above it, just begging to take a downward thrust. Matt's face had lit up enthusiastically in glee, but she could read his mind easily. From the way he was handling her, it was apparent that he took inspiration from how his dirty mind developed through watching porn.

"Alright, I'll let you. I just hope you don't end up wasting your load inside of me when I cum."

That statement would be the true test for Matt, whether he knew it or not. Anna had experience handling men and knew that it would be a tough task at hand for a virgin not to hit his orgasm alongside hers when she had reached hers. Without saying anymore words, she slowly lowered herself down, filling her juicy cunt with his swollen rod. Letting out a soft moan, she looked at him while placing her hands up over his muscular shoulders.

"I'll go easy on you, nice and slow as I rock you."

In this position, Matt was given the full display of her perfect breasts up in his face. He reached his hands up, squeezing at them as Anna began to slowly roll her hips and thrust herself downward over his cock. Inch after inch pushed inside of her while she felt him playing with her boobs. Raising his head up further, he smashed it between her breasts, sucking and licking on them. Anna let out a moan and then moved her hands down to cup the back of his head, pushing him further into her breasts.

"Ohhhhh yeah, you love those tits. Give 'em some love, Matt!"

Moving her hands to her breasts, she squeezed them around his face while he was still slobbering over them. All while she worked her hips simultaneously to push herself up and down his cock. Eventually Matt moved his hands away from her lovely tits and roamed his palms over her smooth skin. Once he found her hips, he got a grip and then moved his face away from her tits. Leaning forward a bit on the couch, he began to buck his hips, throwing Anna off guard as she gasped and bounced atop of him.

"Oh, fuck!"

She wasn't expecting this from him, as she believed he would've allowed her to rock atop of him with ease, but Matt was clearly still in control. He simply allowed her to get on top, surprising her once again with his knowledge of sexual acts despite the lack of first hand experience. This boy was going to be a hell of a man with handling ladies and taming them, she thought to herself. It brought her a sense of pride deep down to know she was taking his virginity, being his first in what would likely be a long line of women in the future. Anna planted her hands back to grip on his shoulders as Matt's eyes were glued at watching her big tits bounce in front of his face.

"Ohhhhh, fuck! Yes!!"

Crying out to him, Anna's long brown hair swayed, getting in her face and causing her to use her right hand to shove it back. At this rate he was bound to make her cum soon, but would he be able to hold back his own orgasm? That question still lingered. Her fingernails dug down into his skin, causing slight stinging pain. Matt gritted his teeth momentarily, letting out a grunt as he was still pumping his hips to drive that cock into her pussy back and forth. Anna had quit rolling her hips, allowing him to take full control as the one doing the fucking.

"Fuck, ohhhhhh fuck! FUCK!!"

When the pitch of her voice raised higher, that was the small sign for Matt that she was close to reaching her climax. He began to buck his hips harder, faster in an attempt to pound every bit of strength he had in him to making Anna cum. Whimpering, she bit down on her lower lip and closed her eyes before belting out an epic scream, just as he felt a sense of warmness from her juices unleashing to flood his cock.

"OHHHHHHHHHHH... FUCKKKK!!"

He came to a stop and suddenly gasped. Anna's body shook as she gripped his shoulders so hard her fingernails sunk down, breaking the flesh and creating small cuts. The pain was felt, but beyond that was Matt feeling the rush of her juices from within her. He grunted, gritting his teeth as he came to the sudden force of trying to hold back his own orgasm. The sentiment of having his cock lodged inside of a woman as she reached her climax was such a wonderful experience, one he would never forget and would be left craving again after this day was over. Anna had to catch her breath, panting wildly as she opened her eyes and witnessed his face all curled up, trying to hold back. He didn't cum inside of her, yet. Another impression had been left on her as she pushed herself upward and began to climb up from him. Matt was given the view of watching his cock slowly slither out of her pussy, covered in her sticky juices.

"Oh my god, that was so fucking good. You didn't cum inside of me either, so congratulations! You still get your chance to cover my face later!"

Cracking a smile, he couldn't stop himself from giggling at her 'congratulations' remark. Anna lowered herself down to her knees and then proceeded to grip his cock and feed it to her mouth. Slowly, she sucked him to clean up her own juices. He witnessed her pull his shaft from her lips, making a popping sound before she audibly swallowed her own love nectar. Matt witnessed her throat muscles move, indicating to him that she did, indeed swallow her own juices down.

"Damn, I didn't know you were gonna do that."

"I don't like to waste cum, whether it's yours or my own."

"Funny girl."

"You aren't the first person to call me that."

Anna kissed the head of his cock, gazing up at him with her big blue eyes. All Matt could do was smirk.

"I won't be the last either."

Rising up from the couch, he watched her take a few steps back from her knees. Matt reached down and gripped Anna's hair with his right hand, digging in a tight grip that caused her to let out a soft moan.

"Ohhh, fuck! You know something? For a virgin, you sure do know how to grab a girl by the hair. You're going to be one hell of a man with handling girls, I can tell you that."

He smiled in pride at that comment.

"Well, what can I say? I've spent years learning and knowing exactly how I would handle you if I ever got the opportunity. Come on, crawl..."

Stepping forward, he pulled her hair before turning backwards to watch her crawl towards him. Anna let out an exaggerated but whimpering moan.

"Uhhhh, where are we going?"

"The stairs babe, where else?"

"Ohhh, so you wanna fuck on the stairs, huh? I wasn't expecting this."

Moving forward, he got behind her but still gripped her hair. Anna was crawling like an animal in the process of being tamed, stepping forward with her hands while her knees pounded over the hard floor. Matt bit down on his lower lip and then used his other hand to spank her ass. All she did was moan upon reaching the first step of the wooden stairs.

"Go up them, baby. I'll tell you when to stop."

He let go of her hair, allowing some freedom for her to move. Anna still wasn't sure exactly what position he wanted her in, but she would be made aware in the following seconds. After climbing three steps of the stairs, she balanced her knees on one below with her hands pressing down on the next one.

"Stop! Right there is perfect!"

A thunderous boom was heard from behind Anna as Matt stomped his feet down over the wooden surface of the stairs behind him. Smirking to himself, he moved his hands over her ass. Anna raised it up and began to twerk again, rotating her hips to tease him with her ass cheeks clapping. He was forced to move his hands away, allowing her ass all the freedom it needed to shake and bounce.

"You like it when I do this, huh?"

"Fuck yeah I do!"

It was impossible for the young man to resist stepping forward and allowing her to twerk up against his cock, shoving it between the crack of her ass to create a subtle hint of what he wanted. Anna moaned at the feeling of Matt's thick rod sandwiched between her firm ass cheeks, right in the crack. She stopped twerking and only raised her ass up a bit to feel his entire length sliding a bit into the crack. Taking a deep breath, unable to take his view off the sight of his cock lodged into the crack of her ass, Matt flat out told her why he had her on the staircase to begin with.

"I wanna fuck you in the ass."

"Oh really?"

The tone of Anna's voice was somewhere between a serious answer and playing it on with her goofy demeanor.

"What the fuck are you waiting for then, Matt? You spanked it enough, so go ahead and shove that big fucking cock right up my ass and take it!"

Her shouted demand was just enough to force him into planting his hands back over her ass cheeks and pulling them apart. Realistically, all Matt had to do was thrust forward from the crack of her ass to find her little hole, but he didn't know that just yet. Once he caught a look of her dark little hole, he gripped his shaft and pushed the head of his cock right to the entrance. Anna gasped upon feeling his rod penetrate her, shoving up inside of her ass. Matt didn't expect the feeling he received upon entering her dark little hole for the first time.

"Holy shit, this is so fucking tight!"

Anna moaned.

"Well, yeah! It's my ass, it's supposed to be tight!"

Her response had forced him to laugh a bit but also blush. Anna had a funny way of relieving tension in these situations as Matt was becoming free of his virginity and evolving from a boy into a young man. Being this was his first time having his cock inside of a woman's ass, he figured to take it slow. Planting his hands over her ass cheeks, he spread his legs out a bit and began to slowly pump his cock into her ass. Matt listened as Anna made another gasp and then moaned.

"Mmmmmmmm, take it slow honey. Nice and slow... Mmmmmmm, that's it. This feels so fucking good, but I know it's your first time. I don't want you to get over excited and blow that load in my ass. You're saving that for my face."

"That's right, baby."

Taking in a deep breath, Matt gasped as he slowly pumped his shaft into her ass and moved it back and forth. He watched every inch of his fat cock disappear with his balls rubbing up against the undersides of her cheeks. Anna had given him good advice, playing herself into the role of a sexual mentor. He continued to pump slowly into her ass, but soon gave into the urge to go a little faster.

"Slow, Matt! Go slow!"

Her calls for him to slow down had come and gone. Matt felt that he was in perfect control, so he raised his right and slapped her ass with it.

"Don't worry, I'm not going to cum up your ass, I know when to stop. You don't tell me what to do!"

Anna moaned, soon feeling his right hand reach up and grab her by the hair. Matt was pumping his cock into her ass at a moderate pace now, gone with the idea of fucking it slowly.

"Mmmmm, fuck!!"

Her moans had come with a whimper but ended with a growling taunt, almost as if she was uncomfortable with him in control like this. Perhaps it was the odd position of the staircase, Matt didn't care. How could he? Here he was fucking the woman of his dreams up the ass, right on the stairs that she had climbed so many times before in the years she had to babysit him. Rocking in a steady pace, he continued to thrust his cock into her ass while the sounds of their breathing, moans and movement over the staircase was all that was heard throughout the house. A bead of sweat dripped from his forehead, but his concentration could not be disturbed from this moment. When he felt his orgasm beginning to build up, that was the sign for Matt that he should come to a sudden halt. Wiping his forehead, he stopped and then snatched his cock free from her ass.

"Turn around."

Still gripping her hair with his right hand, Matt pulled it to force Anna began to turn around over the staircase. She moved into a wonky position before setting her buttocks down over the cold surface of the wooden step. His fat cock was right in her face by the time she got situated and before she could utter a single word, Matt fed it between her lips, forcing her to go from ass to mouth.

"That's it, that's it. Suck it. Suck my cock, Anna!"

He didn't give her a choice, though she knew it was coming eventually from the desire he had of wanting to finish the day with decorating her face in his seed. Placing both of his hands on the side of her head, Matt proceeded to thrust his cock and truly fuck her mouth like before. Taking inch after inch of his shaft between her lips, Anna struggled to hold herself from choking, but she took it like a champion while closing her eyes. Over and over, he drove his cock into her mouth, knowing when he wanted to stop.

"Just like that, just like that..."

Whispering words of approval had caused Anna to open her eyes and gaze up at him. Matt was smiling down at her, but was firmly in control. This was another sign to her just what kind of man she had awakened from inside the boy she watched grow up. His balls shoved against her chin with each full thrust he sent into her before he came to a stop. Matt groaned and then slid his cock from her mouth, snatching it out and into his right hand. He took a deep breath, knowing that he was merely seconds away from blowing his load. Anna was well aware of what was about to come. She sat on the staircase step, leaning herself upward.

"Are you ready to cum for me?"

"Yes I am."

It was a dumb question, but the way she spoke to him in a low, seductive tone was just enough to make a bit of pre-cum ooze from the head of his thick rod. Anna closed her eyes after gazing directly at his cock aimed towards her face. She knew what was coming as he had gripped his meat pole and began stroking it hard with his right hand. All those times that Matt had masturbated to her photos; all the memories he carried from wanking himself to watching video clips of her, all the times he stayed up late nights to watch porn fantasizing about her, all that was coming to a head now as he knew within seconds his cum wouldn't be flying into a rag or over his own skin. It was going directly onto the face of the only woman on the face of the planet who was worthy of taking his virginity and making him into the man he was now.

"Cum for me, cum on my face. Cum all over me, Matt..."

Parting her lips, she stuck her tongue out for him, going 'ahhhhh', as he began to pant and grunt.

"Oh god, OHHHHHH GOD! FUCK!!"

Taking in a deep breath, Matt grunted as he watched the first wad of his cum fly from his cock and splatter directly over Anna's forehead and streak into her hair. She gasped, completely surprised from the direct force of his initial wave. Anna moved her face slightly up, causing the next string of his cum to go into her left side closed eyelid and drip down her cheek.

"Oh, shit!"

Crying out to him, Anna soon felt another wad of cum splash over her left eyebrow and streak into her hair again. Witnessing her face get plastered in his cum so far was enough to satisfy Matt. He shoved the head of his cock over her tongue and stroked it again, milking out another wad into Anna's open mouth. She slowly began to open her eyes, blinking from the cum over her left eyelid that was dripping down. He finished himself off with the last spurts of his sticky seed filling her mouth. Once he felt he was done, Matt squeezed his cock one final time to make sure the final drops made into her mouth. He pulled it away when he was done and watched as Anna closed her lips and swallowed his seed down her throat. Out of breath and feeling a level of fatigue through his body, Matt smiled down at her and flashed his teeth.

"Atta girl, love that I just got to watch you swallow that down."

She didn't reply back to him. Anna simply used her hands to collectively wipe up the cum from her cheeks and then fed her fingers into her mouth, sucking them clean. One by one, she licked and sucked her fingers dry of his seed. The only bit left on her now was the excess drops that went into her hair.

"Mmmmmmm, I don't wanna miss a drop."

After sucking her hands clean, she grabbed his used cock and then placed a soft kiss over the head. Glancing back up at him, Anna offered a smile before speaking.

"I think you're a man now, honey. You know how to handle yourself with a woman, I'm glad I got to be the one to break you in."

******************

1 DAY LATER

A slow afternoon had proceeded into hot summer day. With an empty house all to himself, Matt had found himself relaxing in the bath tub, soaking in hot water while the stereo in his bedroom was turned up to a moderate volume. He wasn't in a hurry to get out, finding himself more relaxed than ever while going over the events that had occurred yesterday. What sense of mind washed over someone upon achieving a perceived impossible goal? That was a question he didn't know how to answer. From the minute he woke up and as the hours ran by, something had truly felt different about life. Getting to fuck the woman of his dreams, Anna Kendrick and shed away his virginity to become a man was something he didn't believe would ever happen in his life, but it did. Yesterday wasn't a dream, no matter how much it felt like one when he went over the events in his head again.

Before Anna had left, she had given Matt her panties as a way to leave a memento for this landmark in his life. They would be kept in the corner of the underwear drawer to his dresser, at least for now until he could find a special place for them. One thing he couldn't deny from yesterday was that she lived up to every bit of the expectations he had of her from his fantasy. One thing Matt knew for sure after this experience with his dream woman, he had the means of handling himself with women. Anna was right, he was going to be a hell of a companion in the bedroom, but only for the right ladies. Becoming a man now in his life, he was anticipating getting out into the real world in the near future.

THE END