A Boots of Confidence

[superevil7]

Description

Max wants to ask the girl he has a crush on out to the school dance, but feels too shy to do it. His friend, Chloe, offers to help him become more confident in himself, by having him go naked in front of her.

A Boots of Confidence

“So, have you asked a certain pretty blonde girl to the dance yet?” Chloe asked, as her friend and 16-year-old classmate, Max, sat down at the lunch table across from her.

“No.” Max looked down at his food, blushing a little. Chloe had been pushing her friend to ask the girl out since she found out he had a crush on her last week. “It’s just… There’s no way she’d say yes.”

“You’ll never know if you don’t try. You miss one hundred percent of the shots you don’t take, Max.” The 15-year-old girl looked across the lunchroom, seeing Vicki sitting down at her table. “There she is now. Go! Go ask her!” and she kicked his shin under the table a couple of times.

“Ow! Ok, I’m going!” He said, getting up from his seat, and heading over towards Vicki’s table. Just as he neared the table, Vicki looked up towards him, a beaming smile on her face, laughing at a joke one of her friends just told her. His nerves got the better of him, and he turned quickly, heading over to the condiments table.

He came back over and sat back down across from Chloe again. “What are you going to do with all that ketchup? You brought a peanut butter and jelly sandwich, and a banana today.” she said, with an amused look on her face.

“Nothing.” He took a bite of his sandwich, feeling pretty dumb.

Chloe dipped her finger into one of the paper cups of ketchup, licking it off. “Well, why did you grab three of them?” She laughed. Max shrugged his shoulders, and slumped a little. “Don’t get down, Max, you still have a week until the dance.”

“Aww, what’s the use? There’s no way I’m going to be brave enough to ask her.”

“Hey! Maybe I could help you or something, to get braver, more confident in yourself.”

“How would you do that?”

“I don’t know. I could pretend to be Vicki, and you could practice what you’re going to say.”

“We did that on Saturday, remember?”

“Oh yeah. Well, give me some time to think of something. Maybe I can find something to help you on the internet. Why don’t you come over to my house after school today? My mom’s working the evening shift ‘til 8.”

Chloe ended up spending her whole free period in the library, searching with different terms. ‘How to be less shy.’ ‘How to be brave.’ ‘How to be more confident.’ She was just about to give up, when she came across a website claiming a one hundred percent guarantee to work, or your money back. She was about to click off, not really sure where she could come up with the money they were asking for, but the description of the process caught her eye. ‘Spend the session in only your underwear with our licensed therapist.’ it read. The thought intrigued her. “No reason Max couldn’t do that in front of me.” she said quietly to herself, and giggled a little. “I’ll just have to take it slowly with him.”

The next time the two got a chance to talk about it was on the walk home. “Max, I found a fascinating therapy that might work for you, but you’re going to have to really trust me.”

“What’s that?” She pulled her phone out, handing it over to him. “In my underwear!? No way, Chloe!”

“Max, we’re running out of options, and out of time. The dance is this Friday.” She took her phone back from him, before he had been able to see the full website. “It’s either this or nothing. Nothing else I looked at even seemed worth trying. This has got a hundred percent guarantee to work.”

“Well, where are we going to come up with the money for this?”

“We don’t need to. I read through the whole website. You can just do it in front of me.”

“You!?” He gulped a little.

“Yeah, me. You’d rather do it in front of some stranger? Look, it won’t be any worse than going to the beach. And we’ve been there hundreds of times. I promise, I will not tell a soul you’re trying this. Ok? You can trust me.”

"How is being in my underwear in front of you supposed to help me ask Vicki to the dance, anyway?"

"Cause, it's all about helping you become at ease with yourself. If you can do that confidently in front of me, then asking Vicki out will be a piece of cake."

They had just reached the front of Chloe’s house. Max considered his options for a moment, and let out a sigh. “Fine. What do I gotta do?”

“Just come inside, and I’ll explain everything.” The girl said with a little smirk on her lips. Once the two were inside and settled in, Chloe said. “Alright, first things first. Strip down to your underwear. Are you wearing boxers or briefs?” She asked with an amused look on her face.

“Boxer-briefs.” He answered, getting really nervous.

“What’s that?”

“They’re like, I don’t know... A mix between boxers and briefs.” and he shrugged his shoulders, blushing a bit.

“Well, strip down to your boxer-briefs then.” she said, still smirking at him.

“I, uh… Come on, Chloe. This is too weird!”

Well, she did figure she would have to go slowly with him. "Alright. Why don't you start with just your shirt? That won't be so bad, right?"

"I guess not." He said, letting out a slow breath. He grabbed the back of his t-shirt, slowly pulling it over his head.

"See, not so bad." She said, checking out his bare torso. It had been about 6 months since they were last at the beach, and the situation was a bit different, with him removing his clothes right in her living room. "Come sit down on the couch next to me." She sat down herself, and patted the seat next to her.

"Alright." Max dropped his t-shirt on the floor, taking the seat she just patted. He was completely tense, blushing pretty hard.

Chloe spent the next ten minutes chatting with him, about school stuff, and other mundane topics, hoping to help him relax even a little. When Max finally seemed to relax a bit, she said, “Ok, Max. Time for you to get up and take off your pants.”

“Already???” He asked, getting a little wide-eyed.

“Yes, Max. Just take them off. You won’t get the full benefit of this program until you do.”

Max stood up, facing away from her. He let out one last sigh before he started undoing the belt of his jeans. He hesitated again, before lowering his jeans down, and stepping out of them. He turned back around, facing her, cupping his manhood in his hands.

“Move your hands out of the way.” She said, her smirk turning into a grin. The boy did as told, starting to blush about as hard as before. “So that’s what boxer-briefs are.” She eyed the bulge of his package through his underwear, impressed. “Come on. Sit back down.”

Max sat back down next to her, feeling even more anxious to be wearing so little now, so close to the girl. “What now?”

Chloe rested her arm on the back of the couch, turning to face him. “Now you need to stay like this for at least an hour while we continue having a normal conversation.”

“What…? What should we talk about?”

“Why don’t you practice what you’re going to ask Vicki again? Except this time you can pretend you’re asking her in only your underwear.” and she giggled.

“Chloe!” the boy exclaimed, blushing again.

“Relax, Max. That’s what this therapy is all about. To help you get over being so shy. I have to push your buttons a little in order for it to work.”

“I guess… If that’s how it’s meant to work.”

“Good. Ok, I know I’m brunette instead of blonde, but why don’t you give what you’re going to say a try.”

“Ok… Hi, Vicki.” He said timidly.

“Hi, Max” Chloe fluttered her eyelashes at him.

“I was, uh, wondering if you would, uh, go to the dance this Friday, uh, with me?” He asked with a jitter in his voice.

“Hmmm… I don’t know. I think you’ll have to ask me better than that.” Chloe pushed his buttons again.

“Come on, Chloe…”

“Alright. Try again. More confident this time.”

“Umm… Hey, Vicki.”

“Hey, Max.” Chloe answered, more aloof this time.

“Would you like to go to the dance with me?”

“I don’t know. I think I’m washing my hair that night,” and she giggled.

“Chloe! I’m not doing this if you’re not going to take it seriously!”

“Alright. Sorry, Max. But you do need to be prepared if she says no. Go ahead. Try one more time.”

“Hey, Vicki. I was wondering if you wanted to go to the dance with me on Friday?” he asked in a hopeful tone this time.

“Yes, Max! I’d love to go to the dance with you!” She said, twirling a bit of her long brown hair around her finger. “Max! That was perfect!” She said, dropping her act. “If you ask her just like that, there’s no way she’ll turn you down.”

“Really?” He asked, blushing with a bit of pride this time. “You’re not just saying that?”

“I mean it.” She smiled at him. “But more practice never hurts. Keep going.”

So Max continued practicing asking Vicki to the dance, with Chloe giving him a variation of answers each time, to try and throw him off a little. She noticed with each consecutive time he asked, his confidence was actually going up. She also noticed that the small bulge in his underwear had turned into a bit of a tent. She was tempted to call him out on it, but decided that would be too much for the boy, instead just smirking to herself about it. After a while, Max felt he was all practiced out, and the topic switched to the normal things they would usually discuss.

“Well, Max. You’ve made it the full hour in just your underwear. How do you feel?” she gazed at his crotch again, seeing his erection had gone down.

“Not so bad, actually. I think this is really working.” He answered, reddening a little to have the topic of him being in his underwear brought back up.

“Great, Max. I think that…” she started to say he could get dressed, then looked back down at his package, only covered by the thin layer of blue material. She realized she hadn’t really let him look over the full website. She wondered if she could get away with getting him to do more. “That you’re ready for the next step.”

“Next step?” He asked, with a bit of confusion. “I didn’t know there was a next step.”

“Well, I didn’t want you getting freaked out.”

“Oh. So what is the next step?”

“Well, this therapy is actually supposed to be done with you… in the nude.” she said, a little bashfully.

“What!? Are you out of your mind!” he said, getting up from the sofa.

“Max, look at how far you’ve come already in such a short amount of time. You didn't even know that you'd spent a full hour in front of me in just your underwear until I told you. Trust me. It’ll be worth it when everything is said and done. This therapy really works!”

“I don’t know, Chloe… Naked…? In front of you...??” He said, his skittish demeanor coming back.

“Max, I know you can do this. I’ve been so proud of you over the last hour or so.” When he just seemed to stand there, she added, “And if you’re worried about me seeing you like that, you don’t have to be. I’ve seen plenty of boys naked before.” She lied.

“You have?” he asked with a bit of shock.

“Yeah. My male cousins spend the majority of their summer vacations naked. Why, whenever I visit, it's cocks and balls here, and cocks and balls there, cocks and balls everywhere! I can hardly escape them!”

“Ok, ok, I get the picture!” He shuddered a little with disgust, not wanting to imagine all the boys Chloe must have seen naked. “Well… I guess… If I do this, you promise not to make fun of me, Chloe!?” He said, almost as a statement.

“Max, I promise I will never make fun of you. You are so super brave to be doing this. I can’t imagine what it must be like to be you right now. But I do need to keep pushing your buttons a little, like I said before. Ok?”

“Ok…” and he turned around, facing away from the girl. He hooked his thumbs into the waistband of the only article of clothing he was wearing. “I…” he started to say, but then let out a sigh, and lowered his underwear down to his ankles.

Chloe let out a little gasp he didn’t hear, not really believing he had actually done it! She had really gotten him to bare himself in front of her! She took in the sight of his bare butt before her. She thought it looked good, nice and firm. “You have to turn around, Max.” she said after a bit, wanting to see what boys really kept hidden down there. He turned around, hiding his genitals best he could with both his hands, but he was already at half-mast, knowing she was looking at him. She sighed and smiled, not sure how she was able to keep her excitement in. She was actually seeing a boy's privates bare! “You’re not supposed to cover up either.” she informed him, with a soft voice, still managing to keep her composure, but just barely.

Max dropped his hands, letting out a little whimper, and looked down at the floor in shame. Chloe sucked in a little air at the sight of his naked privates in front of her, opening her mouth in a huge grin. She was shaking with excitement, happy to see that he wasn't looking at her at the moment. He squirmed a bit, knowing what she must be looking at, but not brave enough to look up and check. He got a bit impatient, though, and finally had the nerve to ask, “Now what?” in a quiet voice.

“Oh, uh…” Chloe fidgeted in her seat, surprised at how wet her panties were starting to get. She knew she needed to come up with something, and fast, or he was going to start getting suspicious. “Now we’re both supposed to have a frank and detailed discussion about your privates.” She came up with that off the top of her head, hoping he'd be too embarrassed to back out now. “You know. How they look. What we each like about them. And, uh, you can talk about how they feel too.” With each word she spoke, he seemed to get harder and harder. Chloe took that as a sign that he was going to go along with whatever she said, gaining confidence in her position. He was the one that was naked, while she was totally covered. Why should she be nervous? She almost giggled out loud at that.

“I, uhhh…” He finally looked up at her, with dread all over his face.

“Don’t worry. I’ll start us off.” She got up, kneeling down in front of him, taking in his privates with a much closer view. She was feeling totally confident and in control now. “Your penis is very handsome, Max. I like the way it curls upward when it's hard.” She looked up at him and smiled, then her eyes darted back to his exposed genitals. “Now, you say something about your penis.”

“I…” He was feeling light-headed! It wasn't just the fact that, down on her knees, she was getting a closer look at his privates, it was also the way she was positioned! She was at the perfect angle for… The word blowjob kept flashing in his mind, despite him trying to think about anything else! He looked down at her big doe eyes, staring at him and his cock, and the little smirk on her lips, and couldn't remember ever being in a more sexually charged situation in his life! His cock was now fully erect, and right in her face! “Chloe…” He said her name, dry mouthed, unsure what else to say.

“Go on.” Chloe giggled at his nervousness. “Do you like your penis?”

“I guess. Yeah.” Max had just finished turning beat red. He couldn't get his mind off of how pretty she looked while staring at his privates, down on her knees.

“What do you like about it?” She asked, still just staring directly at his bare privates.

“I, well… I don’t know…?”

“There must be some reason you like it. Do you like how it looks? Maybe you like how it feels when you touch it?”

“What? I don’t do that!” He gave her a disconcerted look.

“Don’t lie to me. This therapy doesn’t work if you lie. I know all boys do that, and if it will help you relax a little... I do it too, with my own parts of course.” she blushed a little at admitting that, and then smiled at him. “I don't have a penis like you… So, is that a yes?”

“Yes…”

“Yes, what?”

“Yes, it does feel good when I… touch it.” he admitted.

“There, see. You’re starting to get comfortable with this. Now it’s my turn to say something again. Let’s see… I like the bit of dark brown hair you have above your penis. It’s cute, nice and curly. And I also like the way your balls hang down a bit below. Oh, I guess that was two things.” She gave an impish giggle. “Your turn again.”

“Ok, uh… This is really hard, Chloe! Have you ever spoken out loud about your privates before?”

“It is really hard!” She laughed, and he gave her an irritated look. “Ok, ok. How about if I say something and then just ask you a question about it? Would that help?”

“Yeah, I guess.”

“Ok. What is the length of your penis?”

“What? I don’t know?”

“You’ve never checked?”

“No…”

“Well, then hang out here for a minute.” She giggled at the idea, as he was already hanging it all out. He blushed at her giggling. “I’ll be right back!” She rushed off. She returned in a minute, carrying a cloth tape measure, from her mother’s sewing kit. “Ok, here.” She held it out to him.

“What do you want me to do with this?”

“Measure yourself. Unless you’d rather I do it.” she said with a devilish grin, wondering if he'd really let her touch his cock.

"No!" He yanked the tape measure from her hand, and ran it along the top of his penis, from tip to bush. “5 point 6 inches.” He muttered out.

“What was that?” She asked, as her grin got even wider.

“5 point 6 inches.” He repeated, louder this time.

“Oh! Good!” She clapped her hands and giggled a little, to Max’s mortification. She wasn't sure if that was big or small, but she wanted to encourage him. “Now you need to measure the width, or circumference, or whatever it’s called.”

He wrapped the tape measure around his swollen member once, at the widest part, staring down at his own bare privates with shame. How had she ever talked him into this!? Not just getting naked for her, but measuring his dick for her!? “5 point 2 inches, around.” He informed her, very red, as he looked back up at her, only to find her eyes still locked onto his naked cock and balls.

“Is that big?” Max just shrugged his shoulders, unsure himself, too embarrassed to speak. Chloe finally looked up at his face and smiled at him, but her eyes didn't leave his privates for long. “Alright. I can tell you’ve had enough talking about your privates for now. Let’s sit back down for a while.” Chloe sat back down in the middle of the couch, so Max wasn’t really sure where to sit. He spotted a chair off to the side and made a move towards it. “No. Next to me, silly.” Chloe called after him, with a little giggle. When he turned back around, she patted the cushion next to her. Since she was already seated in the middle, Max had very little choice in where he could sit.

He took the seat to the left of her, and Chloe smiled at him, before smoothing out her skirt and inching closer to him until their bare thighs were both touching! She was having a lot of fun at her friend's expense now, teasing him, as she could see his cheeks glowing! He gulped again, when he noticed she hadn’t taken her eyes from his privates since he sat down. “Do you have to stare at me like that?”

She smiled a large smile at him, and tucked a strand of her long brunette hair behind her ear. “Yes. That’s all part of the therapy, Max. Your privates need to be looked at by me as much as possible.” She explained, never looking up at his face. “In fact…” she moved, switching to lying on her stomach, and put her arm on his thigh, and rested her chin on her arm, still never taking her eyes off of his erect cock as she moved. “There. The view is much better like this. I can see your cock, your penis, a lot more clearly now.” She held her feet up in the air, with her knees bent, and kicked her bare legs back and forth playfully. Max could now feel her warm breath on his genitals, as she spoke. He shut his eyes, and stiffened up at the sensation. “What is it?” She asked coyly, enjoying the way his cock seemed to be straining and twitching for her every time she spoke.

“I can… I can feel you breathing on me. On it…”

“Oh, does it feel good?” He squirmed around with every word she spoke. “It must feel good. What if I do this?” She blew on his hard cock, making him fidget uncontrollably.

“OH!” He let out a loud moan. “Please, Chloe!!” He begged, his cock straining at maximum hardness! She giggled at the way he was fidgeting, and at the way his one hand was grasping the armrest of the couch! As soon as he stopped twitching around, she made another soft little blow on his privates. All of a sudden, he was shooting his creamy white liquid all over the place!!! “AHH! AHH!”

“OH WOW!” Chloe exclaimed, in amazement and delight. She'd learned about how males ejaculate, but this was the first time she had ever actually seen it. She watched her friend cum with bated breath, finding it was the most fascinating and exciting thing she'd ever witnessed in her life! She rubbed her thighs together, as her pussy tingled, not believing that she had gotten him to cum by just blowing some air on his privates alone! Truth be told, she was only about as experienced as him. Which is to say, not at all. She didn’t know what it would normally take to set him off like this. "Oh my gosh, Max! This is amazing!"

Max jerked and shuttered, his dick twitching and bobbing around all on its own as it sprayed its seed! He couldn't remember ever coming this hard before, and he hadn't even touched himself in order to achieve such a powerful orgasm! His cum ended up going everywhere! Some landed on his stomach, some on his lap and the couch below him. Most mortifying of all, was the great big glob that landed on top of Chloe's head! He looked down at her with just about the most horrified expression she had ever seen him make. "Chloe, I'm… I'm sorry."

Chloe was hardly upset with him, though, instead just laughing it off. Soon the two were both giggling at the situation they had somehow ended up in. “Think you are ready to ask Vicky out?” She asked, after returning from the bathroom with a washcloth. She knelt down in front of him, scooping up the little bits of his cum off his stomach and lap.

“Who??” He asked, feeling a warmth inside of him, like he had never felt before, as she cleaned him up. “Oh, Vicky! Yeah, after this, I don't think I'll have any problems.” He laughed.

The next day at lunch, Chloe watched as Max approached Vicky, with sadness in her heart. After he had gone home for the evening, she had wrestled with both her conscience and her logical brain. What she had put him through had been a nasty, mean trick, she had eventually decided, feeling guilty towards her friend, and yet, she had never had a better time in her life! He was her friend, and how could she have done that to him?? But at the same time, she had to marvel at what she had accomplished. She just had to make sure that he never found out the truth about her little therapy scheme.

Last night in bed, she had had the most wonderful orgasm of her life too! It wasn't just because she had manipulated her friend into going naked, but she was also genuinely attracted to him. Max had never really been on her radar before now, but now that she had really seen him… So, that's why she was feeling great sadness as she watched her friend speaking to Vicky with a confidence about him that she'd never seen before. This naked therapy couldn't have really worked for him, could it have?

Max came back over to Chloe's table, wearing a huge grin on his face. Vicky had obviously said yes. “Hey. Looks like you got everything you always wanted…” She greeted him, as he sat down across from her. She pushed her scalloped potatoes around on her tray, not feeling very hungry right at the moment.

"Chloe, I need to ask you something." Chloe froze. The jig was up! He had figured out that her therapy was all bullshit!

“Listen, Max…” She tried to explain.

"No, you listen, Chloe…" He cut her off, and she gulped. He must be totally pissed, she thought. “I don't know if I'll ever have the confidence to ask this again, so… Would you go to the dance with me?...”

“What???” Chloe was so caught off guard by his question, that she ended up spilling her chocolate milk all over the table. “Shit!!”

“Don't worry! I'll get some napkins!" He offered quickly, not waiting for her response. He was back in a moment, soaking up all the spilled milk with the napkins. “I guess that's a no??” He started kicking himself. “I knew I shouldn't have asked. This is going to ruin our friendship!"

“Max!...” She interrupted him now. “Yes, I'll go to the dance with you.” She smiled brightly at him.

“You will?” He stopped wiping up the milk, just staring at her. “I mean, you will!” She nodded, and so he rushed over to the side of her table, and grabbed her in a big hug, spinning her around in his arms.

The two couldn't help laughing and giggling to one another. “What happened? I thought I just watched you ask Vicky to the dance.”

"Well, the strangest thing happened. As I got closer to her table, the only thing on my mind was you. The only thing I ended up asking her, was if she thought you would go to the dance with me.” He smiled sheepishly, rubbing the back of his neck.

"I guess she said yes?” He just nodded, looking into her eyes dreamily. "Alright, I'll go to the dance with you Max, under one condition…”

Chloe couldn't believe what she was doing, as she lowered her panties down to her ankles in front of her best friend, Max. Her new boyfriend, she realized! She was now standing before him, in nothing but her birthday suit, right in his living room! Her face hadn't blushed this hard since she had forgotten her lines in the second grade play!

Max patted the seat cushion on the couch, next to him, confidently. "Come sit down, Chloe, so that we can have a frank and open discussion about all of your private parts.” It was a good look for him, she decided, as she fought with herself to keep her arms at her sides. The confidence he's exuding makes him so handsome now!

The End

[Lola]

Great story. So funny and fascination that she made him cum just by blowing and i loved that she had the most wonderful orgasm of her life

[blogomatic]

This was really cute! I liked this story alot. The ENM aspects were great and I love her making it up to him.

[NudeBaG]

Great story!
Sweet and cute

[superevil7]

Great story. So funny and fascination that she made him cum just by blowing and i loved that she had the most wonderful orgasm of her life

This was really cute! I liked this story alot. The ENM aspects were great and I love her making it up to him.

Great story!
Sweet and cute

Thank you all! I'm glad you all liked the story! Sometimes I just like doing something short and sweet like this, that doesn't drag on forever, like some of my other stories, lol. I actually wrote most of this about 3 or 4 years ago. Now I finally came up with an ending for it. I wonder if it's noticeable where I started adding the new bits. I hope my writing has improved noticeably since then

[Brent Sickel]

I really , really like this story a lot . I like the shorter stories with few characters and one main storyline going on . I like the characters and story and it’s so good .

I like the ending choice . We don’t know Vicky very well , but she is a good character . But I like how he picked Chloe . I was saying “ No, Max, pick Chloe . You have this awesome great girl right in front of your face . Ask her to the dance . Ask her to be your girlfriend. She’s awesome .” So I am glad you made her pick her .

The ending is a little confusing . They are in the school cafeteria and all of a sudden , Chloe is stripping naked . I was like , whoa , is she stripping nude in the school cafeteria in front of everyone ? She could get in big trouble . But then it’s revealed that they are now in his living room .


It was very confusing and a strange transition. But I really liked the story and it was very good . I like the story and characters a lot . I really like your short stories with less characters and storylines the most of all .

[superevil7]

It was very confusing and a strange transition.

Yeah, I probably could have done something a bit better there. I tend to think of my writing like a TV show, so I was imagining a wipe to transition into the closing scene there.

[blogomatic]

It was very confusing and a strange transition.

Yeah, I probably could have done something a bit better there. I tend to think of my writing like a TV show, so I was imagining a wipe to transition into the closing scene there.

I think it works fine as is, but if its a genuine concern some kind visual signifier like a few extra buffer lines or a line of punctuation as a barrier would go a long way for clarity. That said, I think it'd also be a fun idea to lean into the misdirection a little.