The Chaperone

The Chaperone The Chaperone

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


Hubie couldn't have imagined that doing a favor for his son could ever turn into a night this amazing.


Hubie couldn't have imagined that doing a favor for his son could ever turn into a night this amazing.


Submitted: October 25, 2015

A A A | A A A


Submitted: October 25, 2015



Hubie sat there smiling at his 13 year old son, Sam, as he nervously waited for him to answer whether he would agree to chaperone the boy’s first school dance.  He hated this kind of thing but since his divorce, he’d been trying to do anything reasonable to make it easier on his two sons. 

He finally asked, “What about your mom?  She’s going to be upset that you asked me and not her.  Plus, the dance is on a weekend when I’m not supposed to have you so that might be a problem.” 

His 11 year old son, Tony, who had the same sort of smart ass sense of humor as Hubie did, smiled that infectious smile of his and said, “Let us handle, Mom.  We’ll blame it on you and she’s used to you disappointing her so it won’t be a big surprise for her.” 

Both of his sons were waiting for his reaction; to see if he was going to be mad or not at Tony’s smart ass comment.  He couldn’t help himself and he burst out laughing as it was just too perfect of a comment.  They all joined in and had a good laugh for a minute or so and then he told Sam that he’d be honored to chaperone the dance for him.  Sam’s smile and look of relief told him it was the right thing to do.  His son would never vocalize this but they both knew his mom would have driven him crazy at the dance by interfering the entire time, whereas Hubie would stay out of the way unless Sam asked him for advice. 

The dance was the following week and so they planned on how they would tell their mom and whether there was anything Hubie needed to know.  When he needed to be there and was there a dress code and what did he actually have to do.  True to form, Tony told him about a girl that Sam really liked so he needed to know that.  Sam blushed and admitted that a girl named Megan was really cute and he was hoping to dance with her.  Hubie remembered how this age was so terrifying for him so he hoped that Sam’s wish came true and he would get to dance with his crush. 

He had the expected argument with his ex-wife the next day but she finally relented because even she could see that Sam preferred that he be there and not her.  She insisted that she would drop him off and pick him up from the dance even though it would have made more sense for Hubie to do it, but he wasn’t going to argue about that.  The day of the dance, Sam called him and told him that his mom was driving him crazy with the clothes she wanted him to wear and so Hubie told him that he’d bring him a different shirt for him and he could hear the relief in his son’s voice.  Hubie kept getting more and more nervous about this big moment for his son. 

He was pacing the school hallway waiting for his son and when he walked in he saw the issue.  She’d dressed him in a bulky sweater and he was going to be hot all night.  She was fussing with his hair until he finally told her in an exasperated voice, “Please stop, Mom!  I’m fine; I’ll see you later.” 

Sam was frowning until he saw him and Hubie herded him quickly into a bathroom and they made the wardrobe change and Sam finally got his trademark smile back and said, “Thanks Dad; I really appreciate this.  You’re a life saver.” 

Hubie smiled, but bent down so he could look his oldest boy in the eyes and said, “Sam, I’m always here for you and I know this is all really hard on you, but try and keep in mind, it’s a dance.  Try and take a few deep breaths and go have fun.” 

They did their customary fist bump and as soon as Sam walked into the gym he disappeared and Hubie made his way over to where the other adults were.  He knew none of them but he introduced himself and then found out he was in charge of hallway and bathroom monitoring for the first part of the dance.  He was more than happy to give Sam his distance and not having to hear the horrible music that was being played was a bonus and he immediately started wandering the halls looking for troublemakers.  As he did so, he was on his phone checking scores and texting a few different lady friends.

He managed to kill an hour without it being too painful and he made his way back into the gym to see if Sam needed anything.  As he walked over to the refreshment table, he noticed a woman that hadn’t been there earlier.  She looked like a bit of a hot mess as she was wearing a baby blue shirt dress over what he gathered was a yoga outfit as she was wearing yoga pants, sneakers and what must have been a sports bra under the slightly sheer thin material of the dress.  Her hair was wild, but he thought she looked stunning.  As he tried to steel up his nerves to go talk to her, Sam came running over with one of his friends.

He looked like a jumble of nerves as he whispered, “Dad, Megan got here a few minutes ago and I don’t know what to do.” 

He pointed over towards her and Hubie smiled as she was a cute girl and she glanced over and gave his son a big smile and a wave.  He squeezed Sam’s shoulder lightly and said, “Sam, I think she’s probably as nervous as you are.  Go say hi and ask her if she wants to get something to drink.  If a song comes on that she seems to like, ask her if she wants to dance.  And don’t forget to breathe, big guy.” 

Sam looked up at Hubie and said incredulously, “That’s it?  You think it’s going to be that simple?” 

Hubie laughed and said, “Trust me Sam; just trust your old man.” 

Sam finally laughed and moments later Hubie was smiling even more when he saw his son walking over to the refreshment table with the young lady.  He sauntered over, but keeping his distance from Sam and Megan.  As he got closer, he noticed the woman he’d been eyeing was taking a keen interest to the two lovebirds so he made an assumption and when he was close enough, he asked softly, “Don’t tell me; is that your daughter my son is talking to?” 

The woman smiled and said, “You’re Sam’s dad?  Megan has been talking my ear off about him.” 

Hubie laughed and said, “I’ve heard quite a bit about your daughter as well.  I’m Hubie.” 

She took his offered hand and he felt a spark as their hands met.  “I’m Faith, it’s a pleasure to meet you.” 

She caught his eyes roaming her as they chatted and was instantly self-conscious as she fussed with her hair and smoothed her dress before saying, “Megan told me I looked horrible and I was embarrassing her.  My yoga class ran late and I didn’t have a chance to freshen up; will you excuse me for a little while?” 

He smiled and as she walked by, he softly said, “Sam told me that your daughter was both cute and really smart, but she’s way wrong about that.” 

Faith stopped and gave him a confused look and he added, “You are definitely not horrible looking.” 

Her smile was amazing and he gazed at her brown and green eyes as she blushed slightly before she softly said, “That’s a very nice thing to say, but if your son is this smooth, I might have to keep a closer eye on him.”

Hubie chuckled and said, “Don’t worry.  Sam is the sweetest boy on the planet.  And I am definitely not smooth.  I just wanted you to know that I think you look incredible as you are right now.  You have a natural beauty that will always shine through.” 

Her smile displayed her appreciation for his compliment and she asked, “You’re not going anywhere are you?” 

He shook his head and whispered, “Not a chance.” 

Without Faith to chat with Hubie fought hard not to stare at Sam because he didn’t want him to think he was worried about him, but he did notice him walk out on the dance floor with Megan and he finally started to relax.  He hadn’t realized how stressed out he was worrying that Sam would have a good time this evening. 

He lost track of time when suddenly he heard Faith clear her throat.  He spun around and all he could say was wow. 

She smiled and he was able to quickly add, “See, I’m not smooth at all.” 

She laughed this time and then asked, “So, it was time well spent cleaning up a little bit?” 

He tried not to leer, but he glanced at her quickly and nodded as he fought the urge to take another longer look because what he’d seen was amazing.  Without the bulky yoga clothes under it, the dress now hugged her curves like it should and he had noticed that the shirt dress didn’t have buttons, but snaps and all he could think about was how easy it would be to remove her dress.  She was incredibly intuitive as she whispered, “It’s okay if you want to take a closer look; I don’t mind as I’d really like to know what you think of my new dress.” 

He smiled and said, “Well, as long as you won’t accuse me of being some lecherous old man, I’d be happy to give you my opinion.” 

He could feel his heart hammering in his chest as he noted that she had the body of an athlete; full B cup breasts and he noticed immediately that she was wearing a slip now and it was a darker blue than the dress and he thought that was sexy as hell.  The dress was perfect for her toned body and without thinking he made a motion with his hand and she took the hint and turned so he could see the back as well.  And what a back it was!  The material hugged what was without a doubt one amazing ass and he had to fight his cock to be still because as he eyed her wonderful ass he couldn’t see any trace of panty line and the idea that she might be nude underneath was an intoxicating thought. 

She finally turned back around and even in the dimly lit room he could see she was blushing.  “I didn’t over do my inspection, did I?” he asked softly. 

She shook her head emphatically and whispered, “No, I’m just nervous about what you’re going to say.” 

He couldn’t help but chuckle because now that he was looking into her eyes he saw that she’d freshened her makeup and she was just completely stunning so how she could be nervous about what a man was going to say about how she looked he couldn’t understand. 

He took a deep breath as his heart was still pounding and he said, “Faith, you look fucking sensational.”  He paused as he hadn’t planned on swearing but her eyes seemed to be sparkling at his first statement so he asked, “Would you like my full analysis?” 

She smiled sexily and moved a bit closer and squeezed his arm as she softly said, “Of course.” 

Christ this woman is sexy, he thought as he gathered his thoughts and said, “I have to admit a few things first.  I love that color of blue and anything slightly sheer on a beautiful woman I think is very….um, appealing so the dress already has a couple things going for it.” 

She was smiling in a very seductive way and he wondered about that but he added, “But, like I said earlier, wow!  The way the fabric hugs your body, the slightly different color slip underneath, the fact that those appear to be snaps and not buttons; it’s certainly appropriate for the office, but you’re sexy as hell in it.  Add in the subtle freshening of your makeup and how your eyes really stand out even more than they do naturally and that soft shade of red lipstick……oops, I was supposed to be talking about your new dress wasn’t I?” 

She was chewing her lower lip and it looked both sexy and adorable and she was blushing again and she made him wait a good long minute before she replied.  “Noooo, that’s perfectly fine that you commented on my makeup also, Hubie.  I asked for the full analysis, remember?” 

He nodded and smiled and was surprised at how relaxed he felt around this woman.  He was usually a complete bundle of nerves but there was an inherent sweetness to her that made him feel like he’d known her for a while.  They eyed each other and then she said, “Might I ask some follow up questions?”  

He quickly nodded and she dove right in, “You mentioned my eyes; I’ve always thought they were ordinary…” she said and then paused seeming to struggle with what she wanted to ask.

He smiled and squeezed her arm and said, “I’ve always had a thing for eyes and yours are truly remarkable.  They sparkle when you’re amused; I could see the concern in them when we were watching our kids talking and every now and again I’ve noticed a different look tonight that is hard to put a word on, but they were really breathtaking during those moments.  So, trust me they are far from ordinary.  In fact, there’s nothing ordinary about you.”  He wondered if she would press him on the last part because he was sure that her eyes had betrayed her attraction to him.  “Does that answer your question?” he finally said. 

“Definitely” she said with a warm smile.  She then asked, “You mentioned the fabric hugging my body; is it too tight in any areas… know like in the back?” 

He couldn’t help but chuckle and he quickly replied so she didn’t think he was laughing at her, “Oh hell no, it’s not too tight anywhere; especially in the back.  I hope I’m not being too forward, but just to be clear, you have an amazing body; especially your ass.” 

She gasped slightly and he instinctively knew that he shouldn’t apologize because she had loved that he was being so direct.  She seemed a bit speechless and so he asked, “Was that all your questions, Faith?” 

Using her name seemed to bring her out of her fog and she smiled sexily.  “I have two left.  When you mentioned my slip, I smiled because I haven’t worn one for the longest time since most dresses are lined.”  She paused and he found himself getting nervous and then she added, “As you said it your eyes kind of lit up and you got a little breathless ……so I guess I’m wondering if you have a little thing for them?” 

Her smile was so damn seductive and she seemed a little nervous and he felt a chill in his spine as he moved closer and said, “Wow! Did you just ask if I have a little thing?” 

She giggled loudly and covered her mouth which was unfortunate as Hubie thought she had a wonderful smile.  He leaned in and said, “I thought it was noteworthy to mention the slip as the darker shade of blue does add something to your outfit and also that dress would be positively scandalous on you without the slip because it is fairly sheer.” 

She seemed to smile her agreement with the scandalous comment and then he added, “But to be completely honest, I do think that a slip on the right woman can be sexy as fuck so yes, I guess I do have a ‘little thing’ for the one you’re wearing. 

He emphasized the words little thing and she smiled, but he could tell that they were both getting very lost in this special moment they were sharing.  He reached out and his hand moved along her lower back as he whispered, “Watch out; someone’s trying to get by.” 

She looked at him and her eyes were positively smoldering and then she realized an older man was pushing a woman in a wheelchair and she stepped closer to him as he added, “I think you had one more question.” 

Her pelvis was pressed against the side of his leg and if she moved more to the front she was going to feel his hard on, but she moved a step back and smiled and said, “I’m pretty sure I know why you mentioned the snaps now.” 

He couldn’t help but laugh out loud and then she did as well.  They shared a long amused and interested look before she leaned back towards him and said, “In case you’re curious, this slip is one I’ve had for a long time but I’ve rarely worn it.  So, I guess you’d called it vintage and it’s incredibly silky against my skin and has some really beautiful lace in all the right spots.” 

An image of ripping open the snaps on her dress and pulling her to him flashed through his head, but just then their kids ran up and Megan excitedly asked if Sam and some others could come over after the dance.  Faith explained that she’d have to talk to Hubie and the other parents first.  Sam was looking up at him and he knew he didn’t want to ask in front of Megan and so Hubie smiled and whispered just so he could hear, “Let me make a call.” 

Sam’s face was overjoyed and Hubie hoped his ex-wife wouldn’t mess this up.  He called and wasn’t surprised when she answered immediately as she was probably worried as well as mad that she wasn’t asked to chaperone by Sam.  She was clearly perturbed that it wasn’t Sam on the phone and Hubie quickly explained the deal.  At first she was insistent that she come pick up Sam like they originally agreed, but he was able to mostly convince her that it was crazy to bring Tony out late at night since it wasn’t necessary.  She wanted to talk to Sam and so Hubie found him and handed him the phone. 

Sam made several faces of disgust as he listened to his mom, but he controlled his voice and said all the right things and even offered, “I’m sure Dad will give up one night next weekend with us so it all evens out.” 

Hubie didn’t like the sounds of that as he saw his boys way too infrequently already but he knew it was important to Sam and so he nodded and Sam reached out for a fist bump before saying he loved her and goodbye. 

“Sorry Dad, but I’m desperate here” he offered.  Hubie simply laughed and told him not to worry about it.  Sam raced off to tell Megan the good news and Hubie walked over to Faith and told her.  She gave her address and he was happy to realize it wasn’t far from the school or his house and then Faith offered, “Divorce can be hard, huh?” 

He was about to respond when he noticed her left hand and realized for the first time that she was wearing a wedding ring.  He thought, “Holy crap, I’ve been hitting on a married woman and damn, she’s awfully flirtatious for being married.”  His facial expression must have betrayed his thoughts because she saw where his eyes were and then looked at her hand absentmindedly before quickly saying, “Wait; let me explain.”  He thought she looked positively adorable as she hurriedly explained that she was wearing her grandmother’s wedding ring as she normally did because it kept many of the jerks at bay. 

He laughed and said, “That’ great to hear because I was starting to feel a little guilty about how flirty I’ve been and you being a married woman.”  She smiled and then he added, “Wait a minute!  So you put that on to keep me at bay, didn’t you?” 

She laughed and actually reached out and slugged him playfully before saying, “Oh shut up, Hubie!  It was in my makeup case and I didn’t want to lose it.” 

Her eyes were absolutely electric and he was getting mesmerized by them when she leaned into him and with her soft lips grazing his ear added, “I wear it to keep people like that away from me” as she pointed to a creepy looking dad standing across the room. 

Hubie laughed and as he whispered, “Well, I’m glad you have higher standards than that” he let his hand move to her lower back again and his fingers crept a bit lower. 

She looked up at him and pressed herself a bit closer to him and her eyes lit up when she realized what she was pressing against.  Her eyelids flickered shut for a moment and that image would be seared into his memory as she looked incredibly sultry but then she quipped, “Don’t get ahead of yourself, Hubie; I haven’t decided if you meet my standards yet.”

He was so close to reaching down and squeezing her ass, but he laughed and said, “I don’t blame you one bit for withholding your judgement for a while.” 

They shared a laugh, but she quickly asked, “You’re not planning on just dropping Sam off, are you?  I have wine and beer and you’re welcome to stay while the kids tear up my basement.”  She paused and then much to Hubie’s delight, she added, “And I’d love the company.”

“That sounds great, Faith; I’d like that” was his quick response and then he had to add, “It will give us more time to find out if I meet your lofty standards.” 

Her eyes spoke volumes, but two other parents of kids that Megan had invited over stopped by to introduce themselves and Hubie smiled as Faith told them that they should drop off their kids and be back by midnight to get them.  He hoped he’d be the only other parent there as he really wanted to spend some time alone with her.  They obviously wouldn’t be able to do anything with kids in the house, but he could spend some time imagining it. 

The rest of the dance went quickly and he stood nervously at Faith’s front door wondering if he should say something to Sam, but his perceptive son beat him to the punch and said, “Hey Dad, it’s cool with me if you and Megan’s mom want to be friends; I know you won’t do anything to mess up my friendship with Megan.” 

He smiled and gave Sam a quick hug and said, “You’re growing up too fast, big guy.  I hope you know how proud I am to be your dad.” 

The door swung open and Sam was led to the basement by Megan and Faith called out for him to come into the kitchen.  He walked in and in the full light of her kitchen he marveled at how amazing she looked.  She was leaning over as she looked in the fridge.  The dress was pulled tight against her ass and the hem of her dress was well up the back of her legs and he took a really long look. 

She glanced over, smiled and said, “Want to come over and see if there’s anything you like?”

He chuckled and said, “I already see what I like, Faith.” 

They shared another long look and she added in a breathless voice, “Help me get some snacks for the kids and maybe we’ll get lucky and they’ll leave us alone for a while.” 

He walked over and barely resisted the urge to let his hand move down over her sweet ass and they quickly had bowls of chips and salsa along with popcorn and drinks; enough to feed an army.  He helped her carry it downstairs and when they returned upstairs, she slipped off her shoes and they relaxed on the couch.  She flicked on the TV, but kept the volume down low. 

He turned and looked into her sparkling eyes and he couldn’t help himself and he reached out and pulled some of her hair away from her neck.  She visibly trembled and he whispered, “Faith, I’m incredibly attracted to you; in fact I haven’t felt this attracted to anyone in a long time.”  He paused and saw the smile and the blush in her cheeks and he finally added, “And, if it isn’t a problem, I’d really like to kiss you.” 

Her only response was to lean into him and soon their lips were softly exploring each other.  Most first kisses have a certain electricity to them if there is a shared attraction, but this one was positively supercharged.  The kiss slowly built to higher and higher levels of urgency and as their tongues danced, his hands roamed.  He felt like a teenager again but instead of worrying about Faith’s parents catching them, he was worried about their kids catching them.  It likely added a bit of a thrill for both of them and he finally broke the kiss and whispered, “Holy fuck, Faith, if we don’t stop, our kids are going to find us naked on this couch.” 

She giggled and took a deep breath and whispered, “I know; I wish we were alone.”  She played with her hair as she bit down on her lower lip, she finally purred, “In case you haven’t noticed, you definitely exceeded my standards.”

He chuckled and whispered, “I’m happy to hear that, Faith; I really am.  I hope I will continue to do so.” 

She simply gazed into his eyes and then he moved a little closer to her on the couch and as his fingers teased one nipple through her dress his other hand undid two snaps at the bottom of her dress.  She sighed contentedly but then whispered, “Hubie…..we can’t.” 

As his hand pushed her dress and slip up her thighs he said, “You’re right, we can’t, but I can.  I can make you cum; I’d very much like to watch your beautiful face as you cum.  Would that be okay, you incredibly sexy woman?” 

She had already slumped down on the couch as she spread her legs and as she moaned a “Yes” his fingers moved along her wet pussy.  As his fingers entered her, he marveled at her wetness and how tight she felt.  He paused letting his fingers move ever so slowly as she studied her face.  Her eyes were closed and she was breathing heavily and he listened for a second and was happy to hear that the kids had started a movie. 

He leaned in and kissed her mouth again as he started fingering her.  She moved against his hand and he thought it was sexy as hell to see her giving herself to him.  He moved his mouth to her ear and after nipping her lobe, he began whispering into it.  He loved to tell women exactly what he was going to do to them and he wanted to see if Faith responded to his words. 

He whispered, “Would you like to know what I wish we were doing, beautiful?” 

He palmed her clit as his words echoed in her head and she gasped, “Oh fuck yes; tell me.” 

He lowered his voice even more to ensure the kids would never be able to hear him and he whispered, “If I hadn’t broken that kiss, you dress would already be draped over that chair, but I’d leave your slip on because I want to see how you look in it later as I fuck you doggy style.”  She groaned an “Oh my” right then but it wasn’t clear if it was from that mental image or his fingers which were slowly circling her clit. 

He continued, “I would need to taste you as I bet you have the sweetest pussy ever, so I’d be kneeling on the floor right now with your legs over my shoulder as I feasted on you.  As I sucked your clit, I’d be thumb fucking you; hoping that you’ll cum hard and wet so I can lap all of your honey up.” 

Her hand was wildly groping his crotch and he relished how out of control she was.  She was a woman that he hoped he would be able to tease for hours; or even days and he whispered that as well and then as he plunged two of his fingers back inside her, he added, “Fuck my fingers baby.” 

She did just that and as her wetness slurped around his fingers, his thumb reached up and simply pressed down onto her clit.  Just as he hoped she reached down and using two of her fingers, she guided his thumb and showed him just how she loved to be touched.  He could feel she was close and he looked into her beautiful face; enjoying how her face was ablaze with the pleasure she was feeling and then he whispered, “Faith, baby; if this cum leaves you seeing fireworks, will you suck my cock?” 

Her eyes flashed open and she groaned, “Jesus, Hubie; you’re trouble, aren’t you?” 

He pulled his fingers out of her and she gasped in disbelief but when he pushed his fingers into her mouth she sucked greedily; thrilled at her own taste. 

“Yes or no, beautiful” he purred.

“Fuck yes” she gasped and then he did what he had wanted to do all night, he slid to the floor and after one slow lick with his tongue, he plunged his fingers into her as his lips found Faith’s clit.  He had to reach his free hand up to cover her mouth as he could tell she was going to get loud and as she humped his mouth frantically, she came and flooded his fingers and mouth with her honey.  She had clamped her thighs around his face and although breathing was made difficult, he loved every wonderful moment of it. 

When her movements finally abated, he crawled onto the couch and kissed her softly as he opened her dress so he could finally see her tits.  He opened her front hook bra and palmed one breast as he whispered, “Fireworks, baby?” 

“It was like the 4th of July, stud” and she slid to her knees as her hands opened his slacks.  She kept looking up at him the entire time and that just added to the thrill of it for him as her eyes had never looked more sensational. 

As her hand moved slowly up and down the length of his shaft, her tongue slid along his head and lapped up the copious amount of pre-cum that was oozing out.  She paused long enough to coo, “Oh Hubie, you definitely exceed my standards.” 

Her message was clear and he smiled as she finally took him into her mouth.  As good as it felt, he wanted to be in her pussy and as his fingers played with her hair he whispered that very thing to her.  That seemed to drive her crazy and she sucked him eagerly.  He began thrusting up into her mouth and he knew he wouldn’t last long.  He began softly moaning her name and she glanced up at him and the look on her face told him that she loved doing this just as he had loved making her cum. 

She pulled off of him and as she held the base of his shaft tightly, she purred, “Do you really wish you were inside me, Hubie?” 

He looked over his shoulder at the stairs to the basement and he growled, “Yes, Faith; I hope we’ll be able to do that soon.” 

She smiled and as he felt a shiver running up his spine, he watched her stand on wobbly legs.  She straddled him and then slowly impaled herself down onto him.  He moaned in delight as her pussy gripped him in a velvety vise and as his mouth found a nipple, she rode him slowly and sensuously.  His head whipped up and he tenderly cradled her face in his hand as he gasped, “I can’t stop; oh Faith, you feel so fucking good.” 

“Cum inside me Hubie” she purred and he did just that.  The pleasure was intense and he kept thrusting for what seemed like forever as he emptied himself inside her.  They kissed tenderly until she finally pulled up and off of him and as she settled onto the couch next to him, he whispered, “I can’t believe that chaperoning a dance can be this much fun.” 

She giggled softly and it was an amazing sound.She kissed him again and whispered, “I should probably go clean up a little bit so I’m not greeting parents with your jizz sliding down the inside of my thighs.”

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