Confidence Building 101

by Matt Tims

  And just like that, Kevin experienced the greatest moment of his life. It took all of two seconds for that perfect mouth to begin bobbing on his erection, and it was already the best blowjob he’d ever experienced. This wasn’t just some random hot chick. This was Ms. B! This was his fantasy girl of eleven years!

  Her hands gripped his bare thighs as she continued to make him feel things he didn’t know were possible. Half his cock disappeared each and every time her face moved nearer to his stomach. It was an effortless sensation of immense pleasure. Should that have surprised him though? Everything this woman did was amazing, so why wouldn’t her blowjobs be just as great?

  The moans and groans coming from above her were empowering. When was the last time a man reacted to one of her blowjobs like this? The idea of bringing this amazing guy pleasure was tapping into a part of her that she didn’t experience with men her own age. So many of those guys were jaded and unappreciative. She could still recall a few of them who were silent while she had their dicks in her mouth, and where’s the fun in that? She wanted to know what she was doing was being enjoyed, and Kevin was definitely letting her know. All she wanted was for that intense reaction to continue growing.

  She wrapped her hands around the back of his thighs and pulled herself into him. Seventy-five percent of his hard meat vanished deep down her throat as those moderate moans quickly turned to gasps. She held herself in place, her palms soaking in the pulsations from his legs. She wanted him thinking about this moment thirty years from now. She needed to wipe his mind of that Rachel girl who’d absolutely regret her decision to leave his life after realizing what else was out there. And yes, while this entire experience was for him, she would be lying if she didn’t admit to having fun being the hot mom every boy fantasized about.

  She finally pulled off of him and couldn’t help but laugh at his flabbergasted expression. “I’d love to deepthroat you, but, sweetheart, I don’t think I can get that thing all the way down my throat.”

  “Well, maybe I can give you a hand with that,” he boldly stated.

  His right hand reached out and firmly gripped the back of her head. He pulled her into him before stopping just inches in front of his cock. He didn’t want to be that guy.

  “If you’re okay with it,” he added.

  She reached behind her and removed his hand from her head before glaring up at him. Why couldn’t he get past this hurdle? “What did I just tell you? Huh? And what did I tell you last night?”

  “Yeah, but I don’t want to make you do something you’re not comfortable with,” he said.

  Maybe she was the jaded one? The guys she dated and hooked up with weren’t exactly gentlemen. Her urges and desires were usually pushed to the back-burner for their own needs, so perhaps that was why she interpreted his chivalry for weakness? At the end of the day, Kevin was just looking out for her, and wasn’t that her favorite quality of his?

  “You’re a sweetheart,” she told him. “You really are, you know that? Listen, while women don’t want to be forced to do things they aren’t comfortable with, we like when men take charge. It’s a fine line. Some girls like when you grab them by the head and make them choke on your dick, and others don’t want a hand anywhere near their head. You need to be able to read the person you’re with, and you should know what kind of girl I am by now.”

  “You’re probably more like the first kind…” he quietly noted.

  “I’m more like the first kind,” she verified with a big smile. “I want to make you happy; and if my boyfriend wants me to gag on his big cock, then I’m more than happy to do just that.”

  What sounded better coming out of her mouth? That he was her boyfriend, or that she was going to gag on his dick? They were both pretty freakin’ awesome, to be honest.

  His hand made its way to the back of her head once again before he pulled that pretty mouth back around his sensitive penis. Electricity shot throughout every inch of his body as he carefully inched his hips forward, the back of her throat contracting the deeper he probed. Her tight and gripping throat only added to the overwhelming sensation he was currently experiencing.

  A disappointed glance was there to meet him after releasing his hold at the first sound of gagging. Once again, she wasn’t a happy camper.

  “Did that feel good?” she asked, both audibly and visually annoyed.

  He nodded.

  “Then why’d you let me go?”

  He was having a difficult time understanding her frustration. “Because you were choking. I don’t want to hurt you.”

  Lisa took a moment to think of the best way to word her thoughts. She was just going to say it. That seemed to work pretty well last night. “You have two choices. Your first option is to be this timid little boy I’m looking at now. If that’s what you want, then you can go grab your notebook and head on home. Your second option is to be the guy I know you’re capable of being. Kevin, I promise that we’re going to have an awesome day together if you just act like the man I know you’re holding back from being. Because, sweetheart, I’m getting tired of having to hold your hand through every step of the process. You aren’t going to hurt me so stop worrying about that. Now, what is it you want?”

  “A blowjob…” he answered after taking a gulp, his faint voice barely loud enough to be heard.

  “And does it feel good when I take you deep?”

  “Yeah, it-it does-does,” he stuttered.

  “So, what’s the problem?” she asked. “Make me take you deep then.”

  “Even if you gag?”

  She did her best to send a reassuring smile up to him. “Honey, I want to gag on you. It makes me feel submissive. I love that! Now, make me choke on that big dick of yours before I run out of patience.”

  He laughed to himself before gripping the back of her head again. She really was something else.

  He watched the majority of his penis disappear once more before the sounds of choking were accompanied by wads of spit falling from her mouth and landing on her bathrobe below. Another glob of saliva dropped to the hardwood floor as his hips gave the back of her throat a few quick pumps. He eased his hold to allow her to breathe.

  “Perfect!” Lisa exclaimed. “Yes! Oh my God, yes! I love that!” Her blue eyes couldn’t appear more enthralled with what was happening. “Make me choke on it again!”

  He was well aware as to what she desired by this point. Not only did she want him to be confident and dominant, but she yearned to play the submissive role as well. In theory, they should be a perfect match, but he was still jumping mental hurdles in his mind. She was too special to harm. He just had to find her line; and, well, maybe something would help him relax a little.

  “Take your robe off.”

  She shot to feet and slipped out of her robe, throwing it over the stairway railing behind her. Seconds later, she was back to kneeling in front of her boyfriend for the day. Something about that sounded right.

  Kevin’s plan had backfired big time. Seeing her in her nightie had the complete opposite effect on him than the one he’d anticipated. While it was far from the tightest or most revealing outfit he’d witnessed her in over the years, that tiny hint of cleavage had turned his cock into a coffin nail, and those sexy legs had him feeling weak before she even dropped back down to her knees. Relaxing was the furthest thing from his mind now. The sudden urge to take control of this stunning woman had overwhelmed his body.

  He thrust back into her mouth, roughly pumping her throat as the sounds of gagging and choking filled the front entrance of the house. A few days ago he’d leaned against this very same door while waiting for Scott to grab something from his room. Now, he was fucking his dream girl’s mouth with his back pressed against that same wood. It’s weird how fast things can change.

  She wrapped her right hand around her left waist and placed them behind her back. She was sending a clear message. This was the exact thing she craved, and she by no means wanted it to stop. Feeling this previously shy high s
chool kid control her mouth was exhilarating. She changed him! She took a cub and turned him into a lion!

  “Fuck yeah, Ms. B…”

  She wanted to scream! Did he really just grunt that at her while he continued to pump her throat? And what about those two handfuls of hair he was holding her up by? She felt like such a slut—but a good kind of slut. Being a slut for a guy who loves and respects you doesn’t make you a slut at all. It just means that a really fun day is in store for everyone involved!

  “You like gagging on that big cock?”

  She wanted nothing more than to tell him yes, but the big piece of meat lodged down her throat was preventing her from doing that. Kevin’s next girlfriend might like to give reserved blowjobs, but maybe she wouldn’t. It was her responsibility to prepare him for every kind of woman. It wouldn’t hurt anyone to have her personal needs attended to at the same time either.

  Her blue eyes were locked on him the entire time. No makeup, messy hair, and she still looked flawless. And she was even more perfect with his dick in her mouth. His thrusting came to a stop as he firmly pulled her into him, inching her cute little nose closer to his stomach. Her pulsating throat gave way to a pair of dimming eyes which caused him to release his grip.

  Her mouth sprang off of him and quickly panted as she attempted to catch her breath. “Yes! Oh my God, Yes! That is—”

  “Stick out your tongue.”

  He was interrupting her with orders now? This was the side of this stud that she wanted to see. She quickly moved back in front of him and stuck out her tongue.

  Kevin gripped his rock hard member and firmly slapped it down on the soft, wet surface.

  Every part of her tingled and shivered. Where in the world had he picked that move up from? Who knows, but she loved it! He was so hard and he was showing her that. And she was the one who’d caused that!

  “Again!” she begged.

  The head of his manhood slammed down on her accepting tongue once more before he watched that amazing mouth slide along the bottom of his cock and turn its attention to his balls. Sloppy kisses and long licks soon wet his testicles in an onslaught of pleasure. There wasn’t one wasted movement from this perfect woman. Everything was done with the intent to please, and she was quite the expert in that field.

  Her mouth moved back to the head of his cock while both her hands wrapped around his thick shaft. She simultaneously began sucking and stroking, resulting in him seeing stars. He’d never felt anything like this before. Even her deepthroating didn’t compare to the feel of her hands and mouth working in unison to get him off; and with how great this felt, the growing urge to explode was becoming too much.

  “I’m gonna cum…”

  She didn’t stop for a single second. The first splash of cum hit her mouth, and the manly grunts sounding from above only urged her to keep at it. Shot after shot of semen promptly followed as she desperately worked to drain every drop from his precious manhood. A dream girlfriend doesn’t shy away from a mouthful of her man. No, she welcomes it.

  She kept on sucking as the last burst of fluids exploded from the unbelievably sensitive tip of his cock. She was relentless. Her mouth was a wanderer lost in the desert, and his dick was the only source of water for miles around. He was being worshipped and cherished. This amazing woman treated his manhood like a prize; and in turn, it made him feel like a million dollars. He didn’t want to come down from his high, but the buzz from his orgasm was unfortunately subsiding. The only thing he could do was glance down to find those stunning eyes staring up at him.

  Lisa opened her mouth to allow him a quick peek to see just how much had gathered inside. Moments later, she swallowed, grinning up at him before revealing her big finale. She parted her lips to reveal the end results.

  It was empty.

  “I only swallow guys I really, really care about,” she smiled up at him before wrapping her lips around his penis one last time to clean him off. Once she finished, she hopped to her feet and walked over to the stairs to retrieve her bathrobe. She slipped back into it and looked at her new boyfriend. “So, breakfast?”

  Kevin merely stared at her, the door behind him keeping his drained body off the floor.

  “Hey!” she snapped her fingers. “You there? You want some breakfast, honey?”

  He’d yet to move.

  “Pancakes, french toast, eggs…” she offered.

  He appeared frozen in time.

  “Cereal?” she asked. “I could go grab some donuts or something if you want too.”

  “You’re awesome.”

  That wasn’t the breakfast choice she expected to hear. “What?”

  “You’re so awesome,” he repeated with a big smile on his exhausted face. “You’re so beautiful, and nice, and smart…”

  He was really doing this again? Didn’t they already have this conversation last night? Not that she was complaining. It wasn’t like she would pass up the chance to be fawned over for the second time in the last thirteen hours.

  “And that blowjob,” he continued, glancing down at his wet cock. “That was absolutely unreal.”

  That brought a smile to her.

  “You do so much for everyone else,” he said. “Even your job. You’re a secretary. You help other people for a living, and that really sums up the kind of person you are, doesn’t it?”

  “What does that mean?” she questioned, somewhat confused.

  “You take care of everyone else,” Kevin explained. “What was last night about? Helping me become a good kisser. And what about right now? You’re teaching me how to take charge and behave in a manner women want. But you want to know what the past two days haven’t been about?”

  She had no idea.

  “You,” he said. “You just gave me a blowjob and then offered to make me breakfast. God, you’re so amazing. It’s time for things to be about you for a change.”

  “About me?” she asked.

  He moved away from the door and approached the puzzled brunette. His hand reached out and intertwined with the fingers on her right hand. He was doing the one thing she’d been repeatedly driving into his head. He was taking charge.

  She felt herself being pulled toward the stairs and willingly followed him up the steps. “Where are we going?”

  “To your bedroom,” he answered. “It’s time for things to be about you.”

  Chapter 6 – Giving Back

  The thrill of being led to her bedroom by an eighteen-year-old kid was almost paralyzing for the thirty-eight-year-old mom. There was naughtiness, there were taboo acts, and then there was this. How funny did he look naked with only his socks and sneakers on? But his goofiness was the last thing on her mind at the moment. She couldn’t stop replaying his most recent words in her head. “It’s time for things to be about you.” What did that mean? She had a feeling that it wouldn’t be long before she found out.

  Her bedroom door opened as she followed him inside by the hand. Five teenage fingers found her shoulder and discarded her bathrobe, resulting in her only being covered by her black nightie. Her new choice in wardrobe wasn’t her priority, however. It was the possessive look on Kevin’s face. It was sending chills down her spine.

  Her hands gripped the bottom of her nightwear and playfully raised it several inches up her thighs. Kevin had made his way to her bed and taken a seat on the edge of the mattress as her shoulders slowly began to move. Was she really doing this? Was she actually giving a silent striptease to a high schooler? Slow, methodical footsteps toward the stud sitting on the end of her bed answered that question as her eyes remained locked on his face.

  “You’re so hot.”

  Those words sent her into a trance. She felt hot. Maybe all the praise over the past two days had gotten to her head? Every time he opened his mouth, part of her was desperate to live up to his acclaim. If he thought she was hot, then she wanted to be hot.

  She spun so her back faced the bed, lifting the bottom of her nightie for a split second. What had she ex
pected after briefly flashing her panties to the sweetheart positioned just a few feet to her rear? Of course he would have more praise for her. It was pretty much a guarantee.

  “Jesus Christ…” he gasped.

  But she yearned for more. She wanted stronger, more passionate reactions from him. She needed remarks which would linger in her mind for years. It was clear that in order to get what she truly needed, she would have to step up her game.

  She turned so that she faced him once again. “I wanna be a bad girl today.”

  He couldn’t hide his surprised reaction. She’d even whined like some horny schoolgirl while unveiling her desires. It was heaven.

  “Like, really, really, really bad,” she continued before flashing him an innocent smirk. “But I just don’t want to be a bad girl. I want to be your bad girl.”

  “Um—”

  “How’s that sound?” she cut off his hesitation. “I’m gonna be your little plaything today. I’m a bad girl and I deserve to be punished.”

  “Nothing about you is bad,” he immediately countered. “You’re perfect. Now, take that nightie off. Slowly…”

  She bit her lower lip in an effort to conceal her smile. “But I don’t wanna…”

  “Excuse me?” he asked.

  She knew that her big grin was most likely giving away her attempt to play shy, but she really didn’t care. The situation was too hot to stress about if her acting was up to par.

  “I don’t wanna take it off…”

  “Oh, is that right?” Kevin asked.

  Her eyes locked onto the hardwood floor below. “Bad girls do what they want.”

  “Get over here,” he ordered.

  She glanced up to find the index finger on his right hand pointing to the floor at his feet. His willingness to act like a dominant man had her more turned on than she’d ever been in his life. But wait. What if he wasn’t acting? What if this was the real Kevin? What if her boyfriend for the day was everything she wanted in a man? She was about to find out.