The Affair (closed)

[musicankane]

I never thought I would go to my high school prom with a 27-year-old beautiful woman. Hell I was never planning to go to my prom at all. My name is Jake and I am a nerd, a shut-in, a dork, and many many other negative things that people at school seem to think about me. Am I a nerd? Well if playing Warcraft online makes me a nerd....then yeah I probably am. Am I a shut-in? Not even in the least. I was raised by my parents before they died to always be thankful and give back to those who didn't have your luck in life. Funny moral coming from a kid who lost his parents at such a young age. But I was lucky enough to have my grandparents still and we lived in a nice house, in a nice neighborhood (Where the neighbor's wife was a hot as a fucking supermodel) and I was a lucky guy.

So I gave back. I gave back to kids with cancer at a local hospital on every other Saturday by reading them stories or playing board games with them. I give back to the neighborhood, by cutting everyone's grass for free. Although the grass cutting usually ends up with some money in my pocket because people like to pay me anyway. Which is fine, it supports my video game crack habit.

I especially like to help out with my neighbor's extra little things. I will help them with yard work, or clean the pool or other extra bullshit around, just because this woman is fucking hot.

We became a kind of friend. She and i would talk over lemonade when I got home from school just for the hell of it. I think she was bored, and I liked talking to her because she was almost as smart as she was hot. Maybe it was weird hanging with someone older than me, but she didn't look twenty-seven. Hell she could have enrolled in my school as a senior and nobody would really question it. Girl was hot.

Have I said that yet?

Anyway one day we were talking about the prom coming up. We lived in a small enough town that the whole world knew when prom was about to go down. She asked me if I was going and I told her that I wasn't. I couldn't get a date for the life of me, I was picked on constantly, and girls aren't attracted to pussys as it turns out.

We were standing in front of her lawn, watching the sprinkler in her front yard spray over grass. "Yeah I mean it's okay. Prom isn't that big of a deal anyway, plus tickets are like a hundred bucks a pop and I'd rather save up for a playstation 4 then go to a dance where I'd probably end up with a bunch of goat blood all over and have to go on a murder spree like Carrie." I explained to her as the afternoon breeze blew down the street.

 

[midnight_toy]

Jacky yeah that’s my name Jacky Witherspoon and my life went by fast like the feel of it, yesterday I was a young girl flirting with all the guys in school and the next I am married to a man I used to love.

Don’t get me wrong I love him but somehow I believe our interests don’t point in the same direction any longer. I know he loves me and he will never stop loving me I’m come one look at me but also for my heart. I don’t know when I noticed it but I think it was one day I believe when we were having sex, he wasn’t as big as he used to be and his energy was well just gone. he was pleased and had cum and I wasn’t even half way there yet but he was too tired. Well enough of the sad story I’m here to tell about this one day I was sitting with a couple of friends and talking about what we girls always talk about.

Sex husbands kids and all those boring naughty funny things, and they all told me it was something normal they said we were married already over 5 years now and he wasn’t the youngest any longer. They never could understand why I married him in the first place but they didn’t see him like I did. ok I’m trailing off again well they told me to get a toy boy or like the most wives called them a pool boy.

How the fuck was I supposed to get a pool boy around this little town all the good ones were already gone and the others well then I rather keep fucking my husband and then finis the job off myself. on that day I went home from this brunch we always have once a week and saw him my future pool boy at least for my eyes and thoughts. I didn’t have interest to fuck him he was young and I would even believe a virgin but you can’t always see that in boys these days.

but he would be someone I could talk to and be able to get things done around here that I don’t want to do or just can’t do. maybe even a little more for my eyes and thoughts then work but why not. after some time he really worked good I even got the feeling that he was liking this a lot I mean come one I don’t even pay him really ok I cook sometimes for him and bring him things to drink while he works but I’m not like the others he didn’t want to get paid so why should I. after some time I even started giving him little things as payment as thank yours and all but I still had this feeling he came to work for me just because he wanted to be close to me I didn’t mind at all.

This lovely day we were sitting on the porch talking as we usually did it was more a friendship now then what my thoughts had in mind on that first day. he talked about this prom coming up and that he wasn’t going that can’t happen. everyone should have been at their prom I mean it is something that won’t happen again other than you stay behind in class and have to do it over again but normally it doesn’t come twice in life.

"Hey no come on that won’t happen at all! and Carrie Really?!"

he was funny most of the times and I even enjoyed talking to him I was always happy to see him come home knowing after a few minutes he would come over and ask if anything needs to be done and that always made me smile.

"What if a girl asks you to go with her there would you then go to your prom the one and only prom you probly will have in your life ok its more important for the girls then the guys but believe me you’ll be missing out if you don’t go....I promise !"

 

[musicankane]

I snorted in laughter when Jacky suggested that a girl might ask me out. Me? Yeah right. I mean I was nothing but a dork and I couldn't think of one girl at school who would give me the time of day let alone ask me to prom.

"A girl asking me out? A meteor would crash into the Earth before that happened. Look this may be hard to believe Jacky but I am one of those.....loser dorks. I'm sure you had them in high school. Maybe members of the chess club or something. No nobody is going to ask my ass to prom."

I leaned back and took a pull from the lemonade she had made earlier in the day. It was sour, yet sweet, it was just perfect. Much like Jacky herself. I was really shy coming over to do work for her at first. I mean Jacky was stunningly beautiful and though she never showed it off to me, as she normally dressed pretty conservatively, I knew her body was amazing.

It took a while for me to warm up to talking to her without fearing she might snap at me. But now that I could talk to someone as beautiful as she was....well I felt better around her. I felt more like a person when I was with her. It meant everything to me.

"Even if I went. The football team would be there and I would end up with a wedgie or some such horrible shit. They treat me like shit and I get enough of it when I have to be in school. I don't need to be volunteering for bullying overtime." I explained.

 

[midnight_toy]

I felt really bad now, I didn’t think that school was even worse now then when she went to high school some how it was all just getting worse before better.

I had to do something the poor boy had no good memories of school and I would be damn if it can’t help him out with that. I thought for a few seconds and then I knew what to do.

the football team would be so jealous of him seeing him come to prom with a girl older then he was and prettier then most girls on the school.

so now how am I going to sell him this so he won’t think I am just joking around here and instead trying to help him out and make the rest of the time he had to spend in school better.

"Hey why not go to prom with me...I mean the boys they will fall to your feet if you show up with a older girl and all and then well just say everything they need to hear to think your the coolest guy around what do you say will you go to prom with me...Jake!?"

I smiled and tried to look all innocent and that I’m not joking as I touch his leg shaking it some .

"come on you won’t die and ill have a nice night again able to feel younger again and maybe you will even be the prom king....it is possible..."

 

[musicankane]

I was sipping the lemonade again as she suggested that I go to prom with her. With a gasp then a terrible cough, lemonade burned up into my nose and out the front of my face. I screamed in pain, however it just came out as a hacking cough.

When I had recovered enough to speak I turned to her and stared in disbelief. "You want to go to prom with me? You got to be joking, I mean....why? Didnt you already...?" I stammered.

My mind reeled, could going to the prom with Jacky work? Surely she would be the hottest girl there...at worst she'd be a close second because Ashley Miller was straight out of a Victoria Secret catalog. Which made going to the prom with Jacky a problem. No one would believe I was there with her as a date. They would think she was my aunt or cousin or something.

I frowned and said, "Thanks Jacky really. But I don't think that is a good idea. Even if people didn't assume you were a cousin of mine just doing me a favor...they would probably just pick on me anyway and try to break us apart. Really it is cool of you to offer but...I really don't even like those people and would rather not deal with them. It can only end badly if I go." I sighed and hung my head. Jacky had no idea the nightmare high school was for me. I didn't want to face that fucker if I didn't have too.

Especially Derek Franklin, star quarterback already going to UCLA on full scholarship, he was a fucking cock suckered and three times my size.

 

[midnight_toy]

Jacky felt bad now even bring it up but how could I know how he would react when I ask him. she patted his back until he breathed normal and stopped coughing.

"is it really that bad ...that you would even deny me a wish as of going with you to a prom .....I’m sorry to hear that...."

I thought for a few mins and then smiled looking at him and then leaning close to him to whisper in his ear.

"Ok don’t drink don’t want you to choke now...umm what if I promise you something...you go to the prom with me and if...."

I pause for a second to make sure he wasn’t drinking as I cup his hear so my whisper is only heard from him.

"if they do what you say then you get to wish something of me as a sorry...anything you wish and so they might really think I’m not your family I could kiss you in front of them all..."

I look at you and smile watching his reaction and to see what he might be thinking after what I said.

 

[musicankane]

I felt better as she rubbed my back. I knew that Jacky meant well and I could tell she really wanted to help me. Prom was a youth defining experience, or at least that is what the posters all around campus want you to believe. There have been many movies about it, some scary, some funny, and some just plain fun. Maybe prom wouldn't be so bad. Hell everyone would probably just be dancing and having too good of a time to pay attention to me in anyway.

It seemed to mean a lot to Jacky for me to go. I trusted her, I mean I haven't known her long, but she was a beautiful women who didn't treat or talk to me like dirt. In fact she often spoke to me like an equal, an adult even. Hell I was eighteen and I should be an adult anyway right.

Prom was something I should at least try to experience. What if I went and had a great time? I would be sorry to not go right?

I looked at her and sighed, "Alright, but I hope you wont have to do anything like that. Hell if prom is as awesome as you say then maybe people will be too busy having their own fun to fuck with mine? Right?"

 

[midnight_toy]

I couldn’t believe what he just said he hoped I wouldn’t have to do that. Was I not beautiful or erotic enough to kiss him or did he just see me as a big sister or so. I don’t know how to show him that he is a good looking guy maybe pretty young and naïve but still good looking and when he works in the garden or on the pool. I cant keep my eyes off him as I then poke his side and laugh some.

“Hey are you saying that it wouldn’t be nice to kiss me……that’s not nice and that’s picking o me like they do to you in school you bully…! Maybe I should make you buy me a dress for the prom now too………..”


I couldn’t help myself but to make a joke about it, I nudged him slightly with my shoulder and then I stand up taking his glass and walking to the door.

“Kidding with the dress………Soooo since you don’t want to kiss me then I believe you have work to do and afterwards you may drink the rest of your lemonade….ok ?!”

I open the door and walk inside and go to the kitchen and think of what I just did and what I said. I just hoped he didn’t think wrong of me now or did I make him do something he wouldn’t want to do or feels like I am forcing him to something that was never my means of all that.

 

[musicankane]

I hung my head as JAcky got up and left. I didn't mean to upset her, and I didn't know what she had implied. Of course I would like to kiss her, I've never kissed a girl before and Jacky was fucking smoking hot. It would be like kissing a celebrity to be honest. She was fun, beautiful, kind, caring, and she really wanted to do me a favor.

"Jacky wait!" I said, jumping off the seat and heading inside with her. "I didn't mean that at all. You are the most beautiful woman I've ever seen and I would die to kiss you. I just hate school, and I'm honestly a bit terrified of the people there. Call it social anxiety or whatever, but being bullied everyday for the last 8 years will kill a kid."

I sighed and walked up to her. "Look let's do it okay." I paused, "The prom not sex...I mean wow....I am a fucking retard....Why did I just say that?" I turned bright red and sighed, "No wonder I get picked up, I say stupid shit."

I reached out and took her hand. "Jacky, will you go to prom with me? Despite me being a dumb dumb?"

 

[midnight_toy]

I had to laugh thou I really didn’t want to laugh I didn’t want him to think I was laughing at him and not with him. He took my hand and asked me to go to prom with him she smiled and nodded.

"If you beg like that Jack I just can’t say no...hey and don’t say that your just nervous ...ok kiss me now and then you might be able to ease the nervousness and be able to be normal again...what do you say..."

I pull your hand to pull you a bit closer watching your reaction feeling how your hand starts to shiver and you hesitate. that makes me feel bad I get the feeling that this would be the first kiss he becomes or gives to a girl. knowing somehow he wasn’t going to do it I lean forward cupping his cheek with my free hand and lean up pressing my lushes silken lips against his.

my lips don’t part or pull right away I let them rest slightly on his lips and then pull slowly away as my lips stick slightly to his and get pulled off slowly as I then smile and ask quietly.

"sooo was that so bad?!"

 

[musicankane]

I completely froze up when she suggested that I kiss her now, like ripping the band-aid of a hairy arm. Just get it over with and then kissing next time wont be such a big deal. Yet part of me just didn't think she was being serious, that is, until she took my hand and pulled me close. I was a deer in headlights as she leaned toward and pressed her lips to mine.

Wow! My eyes went wide, her soft lips pressed against hers, it was awesome. She was so close I could smell her skin, and I couldn't believe how wonderful it was. Even if the kiss was fairly plain, just a mere touching of lips, it was wonderful. She pulled away slowly and I felt my lips try to go with hers as they stuck together for a moment as the kiss broke.

I stood there kind of wobbling and a slow grin spread across my face. "That was so cool. Your lips feel so warm and soft. That's just wow. I am missing out on girls Jacky. Holy hell, that was just a kiss too! I can't even big to imagine how good other things feel." I said grinning at her.

 

[midnight_toy]

I had to laugh grabbing his shoulders I shock him slightly.

“Hey Jake! One step at a time….. don’t get your panties in a bunch it was only a kiss and not even with tongue…!”

I looked at him and smiled knowing this was going to be fun going with him to prom. I would just have to make sure he doesn’t do something like that there then there would be no more holding the others back from laughing even more over him they all probly already thought he was a virgin but they didn’t need to have proof of it.

I step back some and smile softly and say.

“And thank you my lushes lips are well taken cared of and that’s why they are so soft and warm because I am a living person….”

I giggle softly and then lean forward as if to kiss him again but reach around him for the glass I had put there while my eyes are locked to his.

 

[musicankane]

(I am Jake in this thread lol)

I smiled as she laughed at me. My first kiss had been with a hot older girl. That was cool. I mean she wasn't even my cousin or anything either. She was just another completely separate person that I could kiss more and more.

I was going to prom. I couldn't believe that shit. A little kiss was all it took apparently. I only hoped this wouldn't become a huge mistake. Although even if I did get bullied, getting to kiss Jacky again would make it work it. Oh I wondered if she would let me touch her boobs.

Okay slow down Jake she wasn't saying anything about going that far.

"Well then Jacky....I should go. I need to reserve tickets and tell my mom that I will need to get a prom suit afterall." I told her still heady from the chaste kiss.

 

[midnight_toy]

I couldn’t help myself from smirking as she could feel his excitement about the prom suddenly grow as if he was one that waited for it the hole year that finally the night was so close and then there.

“Ok Jake then go tell your mom but wont she ask with whom your going…? Wont she be mad or something if your going with a old lady like me?!”

Jacky giggled some while waiting for his response on what was just said. I couldn’t stop smiling as I already was thinking about my last prom night and what I wore and now the same problem like back then what to wear. I knew I had to go shopping tomorrow to find the perfect dress I knew it had to be something amazing so Jake would get all eyes on him for bringing the most beautiful girl to prom but not to much that all eyes where only on me. That was going to be hard I knew it but I did want to help him and show him not all proms and students that may be hard on him everyday can’t be nice to him once or at least she hoped it would go so.

“Tomorrow I’m going shopping you don’t have to work if you want you can spend your after noon doing something nice if you wish Jake but if you do want to work you know where the spar key is to get in the house for the things you need to work with…”

I called after him before he disappeared in the house.

 

[musicankane]

I told my parents that I would be going to prom after all at dinner. They were happy but skeptical when I told them that Jacky from next door would be going with me. My mom worried that it wouldn't be healthy for me to go with her for the novelty of simply going and that I should be going with someone my own age. I argued with her and told her that if it weren't for Jacky, I wouldn't be going at all.

My father shrugged and thought that it would be good for me to at least be going out for something social rather than play video games or whatever in my room. Though in his voice he seemed pleased that I was going with Jacky, after all he knew how hot Jacky was, he understood her appeal because he was a guy. Hell he even gave me a wink.

I didn't get to see Jacky again until the afternoon before prom night, I was raking leaves in her yard, as she and I talked about the plan for tomorrow evening. "I got the tickets and a tux, because my mom insisted that I wear a tux to prom." I explained, as I began to shove leaves into a trash bag. "I request that you don't make me wear the tie for too long, I hate ties."

I looked at her and smiled, "Also I am getting a hair cut in the morning, that way I can be as handsome as humanly possible for you. Though don't get your hopes too high okay?"

 

[midnight_toy]

Jacky couldn’t help but smile at the thought of him wearing a tie. I wouldn’t let him do anything he didn’t want to and if that meant that he wasn’t going to wear the tie after all just till they got out of the door it was fine with me.

“Actually Jake if you asked me men wearing a suit without a tie and the first two buttons open are so sexy….”

I then noticed what I said and turned towards the door thinking about getting something to drink for them both. He was a good looking young man that I couldn’t deny but was he old enough to please my needs. I knew for sure that I wasn’t going to force him to try but wouldn’t mind if he did.

“a Hair cut….and you think you can save what ever…”

I point at his face and make a circle movement with my finger and giggle as I add then.

“what is going on there….don’t try to hard that might just make it worse…”

I stuck out my tongue and giggled some to make sure he knew it was joke she would never pick on him truly.

 

[musicankane]

I nodded and rubbed my scruffy face. "Yeah my face is weird I have to let it get scruffy before I shave it or I can't shave it evenly. My hair is super fine and ignored the razor until it gets a little raggy." I explained with a smile. "Hey listen you are doing me a favor by making me look cool at a prom. The least I can do is try to look good enough that you would be seen in public with me right?"

I finished working on the chorus, tying off the bag of leaves and putting it in her bin. Before I left I asked her, "So since the prom starts at eight I figured I would pick you up at half past seven. Will that work for you?"


* * * *

Sure enough at seven thirty the next night I was at Jacky's door. I had my black tux on, my hair cut and combed back, my face clean shaven and smooth, and to be romantic I held a pink rose corsage for her. I had also used my allowance to rent a limo for the evening, which waited in the driveway as I rung Jacky's doorbell.

God I hoped tonight went okay.

 

[midnight_toy]

I went into town and watched some girls that looked like they could have been going to his school. They were looking for dresses for the prom, perfect I thought then I can see what the girls of today wear to a prom.

She saw that they went into the shop where she had thought about going in to look for a dress and followed them in. she looked around but kept a eye on them to see what kind of dress they would try on or even buy for the prom. While watching them I saw in the corner of the shop my dress it was so beautiful and with this dress she couldn’t mess the night up for him. Jake would love it hell I loved it that was important and I believe my body would be shown perfectly like it should be.

After trying it on I looked in the mirror and the girls stepped out to and both said.

“WOW that dress was made for you; you shouldn’t look any further that is your dress……”

I nod and decide to take it I change back into my normal clothing and go to pay for it and head home.

- - - - - - - - - -

It was almost time; I had to hurry to get done before he was there. The door bell great I slipped quickly in the dress and looked once more in the mirror and smiled.

“Yep perfect…hope he likes it!”

I walk to the door and open it slowly looking him over and smiling.

“Wow where is Jake! The nerdy kid that does my lawn work for me..?!”

I say giggling some and turning once so he could have an eye at the full package.

“And will you take me like this?!”

 

[musicankane]

Jacky opened the door and I swear my jaw hit the fucking floor. She looked incredible, stunning, like a woman walking right out of my dreams. I couldn't help but look her up and down and just be a guy for a second, totally taking in her body in that dress. I blushed as I noticed her looking at me and held out her corsage.

"I got you this." I told her, then pointed behind me, "And I used my savings to rent us a limo." I was nervous, this was like a first date except kinda sorta fake? It didn't matter though, the whole point was to try and have a good time, and dancing with Jacky should be fun. Plus when people saw the kind of girl I bagged for prom....well that would simply be a bonus.

"You look incredible tonight." I said with a smile. I turned away from her and held out my arm, for her to hook onto like they did in the movies. "Shall we?" I asked with a wink.

 

[midnight_toy]

I turn once more and then smile seeing that Jake liked the dress I was wearing my heart jumped and I was happy. Since I was worried that I hadnt picked the right dress thou that was gone now as well.

I couldn’t help but smile that he held out his arm like a gentlemen for me to grab and walk with him to the limo.

“Jake you know you didn’t have to and why your savings if you would have asked I would have given you the money for the Limo…….Your sweet..”

I felt bad in one way if I hadn’t talked him into going he wouldn’t have given his whole savings up for a car for them to drive us to the prom and all. I looked at him and smiled and held his arm and with my other hand. I was nervous I believe even more then back then when I went to my prom.

Sitting in the limo I smile at Jake and then look around the limo and then say softly.

“Thank you but you know this is your night and not mine right?! Do they still take pictures of the couples that come and all or has the time made difference from my prom night?!”

I giggle some as my hand rests on his thigh and I cross my legs as my knee slips threw the slit in the dress showing off my thigh and long silky leg.

 

[musicankane]

I shrugged as we sat in the limo. I had only been in a limo for a cousins wedding years ago and I had forgotten how nice they are. Leather seats, television, even a fridge with soda because I wasn't of age and the limo company knew it. Bummer there I think.

Jacky put her hand on my thigh and I looked at her. She didn't know it, but that touch caused my balls to tingle. A woman's touch so close to my crotch, it couldn't help but zap through me.

I smiled, "They still take pictures. Actually I think the booth is set up to take everyone's picture as we walk in. And you said I should have a real prom experience right? Doesn't that mean I should feel broke by the end of the night?" I asked teasingly.

 

[midnight_toy]

Jacky smiled and giggled some. I couldn’t help but agree to him but wouldn’t want him to give all his money out for me or I knew I would have to give him more money for work he was going to do for me not to feel bad cause of me that he has nothing again.

“Jake do you want to kiss one or twice again before we show up so it wont be such a surprise for you again like the first time don’t want you to get embarrassed cause you act all virgin like when y lips touch yours…”

I smirk and nudge his side some as if showing I was just joking and never wanted to hurt his feelings or not.

 

[musicankane]

I looked at her as she giggled at me. Teasing that I might act too virginal if she kissed me in front of people. While that might be true, I was afraid that the virginal feeling wouldn't go away with just a couple more kisses. It was cool that she was offering her lips up so freely, I thought about taking her up on it.

"I think I should wait anyway. Want to enjoy each and every kiss I can drag out of you." I told her patting her bare knee. God her skin was smooth as silk and wonderful feeling. I let my hand linger on her knee for a moment, then when I realized I was touching her, I blushed and jerked my hand away. "Uh....Sorry."

The limo rounded a corner and I could see the school lights a ways down the road. They had rented spotlights for the prom and I could see the beams waving around in the sky.

 

[midnight_toy]

I smiled to his answer it was a true gentlemens way to answer her question and it only made him sexier and nicer to me then ever before. I felt his hand on my knee and smiled looking out of the window saying.

"Ok if that is what you wish then it is what you become just remember think of me tonight as your girl friend maybe then you will relax a bit "

With that I feel you jerk your hand away and say sorry. I smirk some and slowly and gently take his hand in mine and set it back on my leg just a bit higher then he had it earlier.

"Nothing to be sorry about...."

 

[musicankane]

I held my hand perfectly still on her sweet warm thigh. My breath caught in my throat, her skin so soft and smooth under my palm. She told me to think of her as my girlfriend so I needed to be able to touch her. So I closed my eyes as I felt the car slow down.

When I opened my eyes we were at the prom and suddenly I was less nervous about the hand on her thigh and more worried about what awaited us outside. From the window I could see couples lined up at the door, waiting for the photo to be taken before heading inside.

I glanced back at Jacky and sighed, "Moment of truth."

The driver opened the limo door and I slid out into the cool nmevening air. I turned back and held out my hand for Jacky like a gentleman should, or so my parents said, then arm in arm we got into line.