A Teenage Rake Ch. 04

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Eyl 6, 2023 // By:analsex // No Comment

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Been awhile since I’ve put out a story and I thought I would change this up a bit and get a little reality in. I’ve had a lot of folks ask me to do a story based on the relationship I had with a friend of my father, which I had written of in my Bio. It was my first time with a man and I’ve been thinking a lot about it recently. I had been talking about first times with a friend the other evening and it began to occur to me how utterly unique and hot the situation had been, even if I really should have thought about the potential problems that could have come about. What I am about to tell is the honest to Hoyle truth, with a change to only the names. I tend to write rather vague for a reason, since it is the reader who determines what the characters look like in their mind’s eye, and tend to fill in a lot of situations with their own inner commentating. I’ve tried my best, in the last three stories, to give the reader what they need to make the necessary progression, while allowing them to fill in the gaps with those things that truly turn them on. This is not the case this time around. The events themselves really took place and I do mean everything. For my first affair, I really did get quite a crash course…

Mr. Jones is what I’ll call him. Medium height, dark hair, graying at the temples a little early, with a wife and two very young kids at home… this was my first time. For all intents and purposes, as I’m sure with most female writers discussing their first time in a public setting, I was eighteen. He was twelve years older than me.

Malcolm Jones was a friend of my father and lived three houses down from us in Jackson, Mississippi where I was born. My father and Mr. Jones had worked construction together for the last few years, as daddy had helped Mal get a job when his own construction company went bankrupt.

In the evenings daddy and Mal would come back to the house after work and enjoy life on our back porch with a few beers and guy talk. My crush came in small doses and slowly developed into an outright need over the last year of seeing that hulking man treading through my house almost every weekday evening. Being young and inexperienced, I was truly unable to apply any womanly wiles to get what I wanted, since I couldn’t even begin to tell you what a womanly wile was, but I was a quick learner. I’d been masturbating for a few years now, and I had found two separate stashes of porno magazines in the house. One in my brother’s bedroom and one in my parent’s bedroom, which I assumed was my father’s collection (little did I know that mom enjoyed them as well). At the time, the Internet wasn’t quite the market place for adult entertainment that it is today, so I explored every dirty magazine I could sneak away with. Anything from airbrushed Playboy models with their plastic boobs to the rare copy of Hawk, where young girls were the object of fancy. I had found a few copies of the latter in daddy’s collection, which began the wheels turning. I mean after all, if an old dodger like daddy thought ‘the younger the better’, then how might Mr. Jones feel on the topic?

To get this out of the way, when my crush first started to develop, I did have several reservations about the fact that this was a married man with two adorable children. As with all girls, I wanted to be happily married one day and didn’t want to think about some young hussy setting her sites on my man. These hesitations slowly began to fade away the more time I spent around Mal. His tight jeans, thick workboots, and that oh so delectable build that comes with years of working in construction just drained away my resolve to do nothing but fantasize about the man my daddy called a friend. It might also be a good time to mention that I’ve always had a crush on my daddy, as some girls do. Nothing has ever happened there (though I did make a small effort awhile back, which failed miserably), and seeing Mr. Jones in the same light as my father, this didn’t help my feelings towards our neighbor down the street.

Fast forward about six months. I had gone through every magazine of the men in my family and learned a bit of what turns men on and off (my brother used to dog-ear the pages in his magazines I suppose he thought were extra hot). I’ve also paid attention to my girlfriends a lot lately and listened carefully to what they had described regarding their boyfriends and what they like and what they do together. Although, most of the conversations just re-enforced the fact that highschool boys really don’t know what they are doing most of the time. I’d also stumbled into a bit of a special relationship with my brother.

This started at the beginning of summer vacation, which was a couple of months before Mr. Jones fell under my spell. Mike and I were left alone all day, since my mom runs a clothing store for posh residents of Jackson, and works about the same number of hours as my daddy. Mike and I often find ourselves bored around the house, which is why most days saw my brother spending time down at the rec center trying to get in some girl’s pants, or hunting. Most of my friends were istanbul esc in summer school, since they didn’t keep up on their grades like I did. All of this leaving me to roam the house, searching through magazines and fingering myself to ecstasy with thoughts of Mr. Jones, daddy, Mike, and sometimes a few of my girlfriends (some of the lesbian pictorials really got me thinking about Mira and Stacy).

Mike had injured his leg in a small car accident, which left him in my capable hands. Bored as we both were, and with the opportunity to pleasure myself cut in half, I started to get a little heated up during the day. A girl can’t spend all day in her room or taking a shower with the 10 speed shower massager, so much of the day saw me in a constant state of arousal. It didn’t help that on more than one occasion one of my brother’s bimbo girlfriends would drop by to check on him. With the door shut and locked, I could hear the two of them fucking for all they were worth in his room. One girl Cheryl was so loud I could hear her downstairs, over Montel. And of course, this would just lead to a lengthy session of letting my fingers do the walking.

One fateful day, I decided to get a better idea of what men liked. I was horny and Mike hadn’t had any female companionship in days, so I figured now would be a good time to ask a few key questions on how to seduce a guy. I was given a laundry list of things that could be attempted, though at first I was given the typical big brother lecture about being too young for sex. The last item on the list was simply, ‘if all else fails, you could blow him’. Though meant as a joke, this particular option appealed to me. I knew what blow jobs were through porn and my girlfriends, but to actually perform the act was something that made me very curious and very nervous. So I decide to try out a few tactics around the house to see if they would work.

It really didn’t take much. I showered, changed into a pair of tight, white shorts with a black thong, and a baby doll t-shirt. I made lunch for Mike and brought it to him in the living room. I bent over as much as I could to show off my ass and hopefully give him full view up under my shirt to my tits, which I had intentionally left unchained by a bra.

I sat on the couch next to him and spoon fed him his lunch, making sure to push my breasts out as much as possible. It took my brother one whole hour before he put his hand on the back of my head and taught me how to properly suck a man’s cock.

We had become a regular entanglement of flesh since. He never took my virginity, as I think he was a either a bit too gentlemanly, or he was nervous about being his own sister’s first time, but we spent every waking moment giving eachother head. He would come into my room as soon as my parents left for work and slip his tongue between my legs until I woke up enough to roll over and sixty-nine him, sliding his cock past my tongue and into my throat. It didn’t take long for me to realize I really liked the taste of cum and as he told me on so many occasions, I had been a natural born cocksucker, and he was sooooo glad I was his sister. He didn’t even hunt bimbos at the rec center any longer. He may not have fucked me, but he knew I would drop to my knees at the drop of a hat.

Developing a sexual relationship with my brother only encouraged me to want Mr. Jones (and daddy I must admit) even more. I’d found I could easily conquer boys like my brother if I wanted to, but it was my brother, not some fumbling highschool boy, so I must have something worthwhile if my own brother had taken such a horny interest in me. It didn’t help that I had wanted Mike to take my virginity and every time the subject was brought up, or in the heat of things I would try to put him inside me, he would back out. While I enjoyed sucking his dick and drinking his cum, I needed something more. It was now that I focused on Mr. Jones with a serious desire to have my needs satisfied.

I had always dressed a little moderate but cute around the house. Denim skirts, sundresses, shorts that were mid thigh, and plain t-shirts or polos had made up my typical teen fashion when relaxing at home. With my new mission in mind, it was time to spice things up a bit. I spent a lot of time at the mall with my girlfriends shopping at all the right places that liked to sell clothes to little girls like me that guaranteed every dirty old man within 5 miles would want a taste. It was easy to test my new style, as every time we walked through the mall, I could see middle aged men turning their head, obviously giving their marriage a second though for just a peek at the bouncing girls that strutted around them in short shorts, short skirts, low cut shirts, tied off shirts, and braless. We would sit and flash men right in front of their wives and girlfriends and watch them try not to squirm, knowing they shouldn’t be looking, but trying to steal glances at our tender flesh when they could. My friend Mira even got a belly button piercing at this slimy tattoo shop in downtown Jackson one Friday night. The whole time she was in the türbanlı escort chair, she had her legs spread, giving the guy a view straight up her skirt. The tattoo man asked us to exit the room after the piercing, leaving him and Mira alone for what turned out to be half an hour. They both exited the room with smiles on their face and she never got charged for the piercing or the body jewelry. She told both of us as we walked out of the shop that the guy had gotten so turned on staring up her skirt he offered to give her everything on the house if she would give him head. Mira being the rowdy one out of our little trio, readily agreed. This was what I needed. This kind of brash and brazen attitude that men, even the older ones, are nothing but playthings and that we hold all of the power. That was the event that helped cement everything in place for me. The idea that Mira could trade sex to some strange, older man and get what she wanted helped me realize that a guy like Mr. Jones and his male ego could be no challenge for me.

I stepped up my dress code around the house within the upcoming weeks, some of it for my brother (who had been filling my mouth two or three times a day with cock), but mostly for my target, Mr. Jones. The same short, revealing clothes used to tantalize men at the mall were the order of the day in my household. I would make sure I smelled fresh as a daisy for when daddy and Mr. Jones inevitably walked through the door, knowing I would have a good hour or so before mom came home. Mike would sometimes join them for a beer or four, though daddy didn’t like to have him drinking too much in case mom found out, but these days he napped in his room until dinner (I think I had been wearing him out lately). This gave me plenty of time to spice things up for these two gorgeous, older men. Within days, I had noticed Mr. Jones eyeing me up and down like a piece of meat, and on more than one occasion, I had even seen daddy run his eyes up the length of my body through his drinking courage. To say this turned me on would be an understatement. My nipples would be in a constant state of erection, poking through my shirt, with no bra to protect them, and the horniness of two men ogling me while I brought them beers and snacks did nothing to calm my wet pussy. I flirted more and more with each of them. From flinging my hair back, to bending over in front of them to set beers on the glass patio table, to bringing them bowls of chips and dip, knowing the whole time they were both staring straight down my shirt.

One day, as I had closed the screen door behind me and headed to the kitchen to grab myself a drink, I heard Mr. Jones tell my father that I had certainly grown up a lot over the years. My fatherly agreed through slightly slurred speech, ‘She sure has. I’m going to have to keep the shotgun loaded for the little bastards that come knocking on the door for her.” They both laughed and before returning outside to relax with them, I undid two more buttons on my shirt and sat across from Mr. Jones, letting him have little flashes of my red panties, while watching him try to conceal his growing erection… Yep, like shooting fish in a barrel. Why I never tried this before, I have no idea, but my brother would get a really special blow job for his wonderful advice.

It all happened suddenly. I found myself in a white button up shirt, tied off at my tummy and a pair of blue jean shorts that went up the crack of my ass. My hair was back in a pony tail and I had just the right amount of what my brother calls, ‘Whore red’ lipstick on, as I knocked on the door of the Jones house.

Daddy had called and asked him to borrow his VCR to record a baseball game, since ours had busted. Here I was, dressed like a virgin tart, waiting for the man of my dreams to open the door and hand me some appliance, when I really wanted something else from him.

Devious as I had been, I even waited until I saw that Mrs. Jones had left to go out with my mom to their Friday night movies. Mr. Jones was due to come over later tonight, but I immediately volunteered to go pick up the VCR as soon as I heard daddy on the phone. The door opened, and there he was in all his glory. Black t-shirt, blue jeans, and work boots, and with a build that would make any woman cream. He took a few seconds to look me over and smiled a bit.

“Hey sweetie. C’mon in and lemme get that VCR for your daddy.”

“OK Mr. Jones. Thanks for the loan.”

“No problem darlin’. I gotta unhook it, so this will take a minute. You wanna come down here with me while I get it?”

“Absolutely”, trying as best I could not to sound too excited.

I walked down the stairs into the family room, as he crossed to the entertainment center and bent over to begin unhooking cables. “You sure you wanna lug this thing all the way back home? I can bring it over in a bit.”

My mouth had gone dry and I was panic stricken. Here was my moment of truth and I was petrified. All my flirting and teasing this man had been for nothing if I couldn’t control this moment. I stammered a bit while aksaray escort trying to regain some of my determination, “Actually… I wanted to come over personally. There’s something I wanted to ask you…”

The words were on the tip of my tongue, but were constantly escaping me, as I fidgeted there in the middle of his living room.

“I kinda figured there was.” He said calmly. His back to me as he worked on the VCR and utter surprise ran through me.

“What do you mean?”

“Well, not to be too forward, but I been noticing the way you’ve been prancing around me and your daddy lately whenever I’m around. I began to wonder if it was just my imagination, but the other night when you were flashing those panties at me and smilin’, I figured you might be up to somethin’ more.”

I didn’t know what to say now. I was completely speechless. Had I been so transparent? I guess I had, but to be figured out like this… was it a bad thing? After all, this is what I had wanted.

“Am I wrong lil’ girl?”

“No sir.”

He turned around, leaving the VCR in place. “I like that ‘sir’ part.” He said with a half smile, and walked a few steps toward me. “You know I have a wife and kids. So I need to know… what are your intentions?”

“Ummm… I don’t know… I – ” but he cut me off.

“I’m a very direct man and I know what I like and what I want. My question is, what do you want from me? Sex or Love?”

I knew it wasn’t love, so I said the most truthful thing I could, and tried to recapture a bit of strength at the same time by sounding more adult about it. “Just a fuck.” I blushed at my own vulgarity and I knew he could tell I wasn’t accustomed to talking so bluntly.

“Good. That’s all I’m willing to give. So I don’t wanna hear nothin’ about me leaving my wife or anything like that, understand?”

“Yes sir.”

“Good… Now, you a virgin?”

“N-yes… kinda” a bit embarrassed.

He smiled and closed the distance between us, placing his hands on my shoulders. “I figured as much, but don’t worry. You’re gonna be just fine.” And with that he kissed me so good I felt it in my toes. I was complete butter and every bone in my body melted in his arms. I could feel his hands slide down my back to my firm, little ass, but it all felt so unreal. After a few moments of dancing our tongues in eachother’s mouth, he pulled his lips from mine, leaving me wanting more. “You’re a good kisser girl. What else does ‘kinda’ mean?”

It took me a second to realize what he meant and I blurted out the only thing that came to mind, “I can suck your dick.” I immediately flushed and looked to the ground at my crass words. He placed his fingers under my chin and brought me eyes back up to his.

“Don’t ever be embarrassed for talking dirty to your lover. It’s sexy and you’ll find that I really like my girls to be dirty as they can be.” I smiled a bit, as his hands found my ponytail and his zipper at the same time. “Now show me how good a job you can do suckin’ cock lil girl.”

A bit intimidated, but so wet I couldn’t back out now if I were on fire, I allowed him to push me to my knees, as he fed me his cock. At first, I held still while he fucked my face in slow, steady strokes, with my hands on his legs for sturdiness. After a few moments, I found my own pace and began moving my head back and forth with increasing vigor. He unbuttoned his pants and began to slide them down to his ankles. It was now that I realized the true size of what seemed to me a massive cock. He was about seven and a half inches long and had a lot of fur around him, more than my brother could every dream. That strong, male musk just drove my intensity and I began to attempt taking Mr. Jones into the back of my throat as my brother had taught me. It was no easy task given his length and girth, and the best I could do was get him to appoint where the tip was hitting just past my tonsils. I quickly began to use my hands to jack the rest of that beautiful dick.

The whole time, I could hear him moan, even over my own loud breathing and groaning. His hand rested on my ponytail, helping me steer up and down his fuckpole, while slipping my tongue around his meat and trying to maintain suction on him. I was literally so wet, I could feel tiny rivulets of my juices dribble down my legs. My panties were that soaked.

I tried my best to keep in mind everything I’d been taught. My mouth was filled with saliva, my tongue constantly moving over every part of foreskin that came into my mouth, and the firm, but not to hard sucking that was required to make a man deliver that searing hot cum into my waiting little mouth. Mr. Jones had a tight grip on my ponytail, keeping the pace of my mouth on his cock whenever I showed signs of slowing. Every once in awhile, he would loosen up just enough to let me flick my tongue over the tip and use both hands to stroke his meat. Here I was, on my knees with my daddy’s best friend burying his dick in my mouth like I was a common whore, and I loved it. He was so strong and confident. He didn’t chat me up or try to make dumb small talk the way boys at school did, or pervos at the mall. He was what he said he was… direct. A man who knew what he wanted. And that’s when I heard something that would open my floodgates now and forever. Mr. Jones began to show me what real dirty talk was.

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