Swim Season Ch. 01

Story Info
A cocky young man learns about consequences.
8.9k words
4.35
115k
39
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I'd like to tell you a story about a certain evening in mid-January a few years ago. I was a senior in high school and at the time a freestyle swimmer on our swim team. Where I'm from, swimming season occurs from October to March and it's always cold. I had just turned eighteen 4 months before and I guess you could say that the world was my oyster. I was strong, cocky, yet perhaps a little inexperienced when it came to life in general.

Our team had a coach who could be a total asshole. (At least we thought so). If he didn't like the way you were training on any particular evening he'd simply force you to swim laps for an hour after practice was supposed to be over. Usually we swam from 3pm-6pm, but sometimes if you got picked on by coach you'd be in the pool till 7pm. On this particular evening I was out of the water on time. Seven of my buddies however, weren't as lucky.

In the locker room those of us out of the water cleaned ourselves up quickly. Coach had this bad habit of wandering in to tell someone how badly they preformed on any given day and frankly, nobody wanted to hear it. I was the last out, preferring to take a full shower and clean up. (I guess I prefer the smell AXE shower gel to pool water) After washing I realized that my cock was pretty hard. In the water we swimmers endure what most would call "shrinkage". After a warm shower though, I could feel my hardness forming and realized that I hadn't had any kind of a release for a while. Two days? Was it three? It didn't matter to me at the time but what DID matter was that I could hear coach yelling in the pool area at Dusty, one of my teammates, for missing a split time. Since I couldn't stand the thought of him walking in on me, I pulled on my clothes, put on my coat, slung my bag across my chest and put my IPOD buds in my ears. One winter cap on my head pulled down did the last trick and I was ready to face the long cold walk home. I figured I could take care of myself once I got to my bedroom. I never imagined what was going to happen next.

As I exited the pool doors they locked behind me and I was greeted with the sight of Dusty's mom. To this day I still don't know her first name, but I think it started with an 'A'. In any case, we always just called her Mrs. Michaels. She was an absolute milf. All the guys on the team thought so and that totally pissed Dusty off. I suppose I'd be mad too if I'd been him. Mrs. Michaels seemed to like the attention though, always going out of her way to talk to us. I clearly remember times when she'd flirt with some of my teammates, coyly asking if something she was wearing was attractive or touching someone's arm during a conversation. When she did these things it was always subtle and if someone interrupted she'd act innocent about it. Once, she even did something to me. After a meet in a crowded area she rubbed up against me and I SWEAR she deliberately pushed her firm backside into my Speedo while acting like nothing was amiss. I still recall the sensation of my cock pressing into the fold of her hot married ass. Long story short: I wanted her.

This evening she was bundled up under an expensive looking black winter coat. I could tell she was probably going somewhere since she was dressed to kill. She always looked good, a result of the fact that Dusty's dad made lots of money. Tonight I could see through her coat that she had on what looked to be a red silk blouse and a business skirt. Dark hose-clad legs ended in some red heels, the kind with the little spike on the end. The heels were about as high as one could go before looking slutty. Perhaps 3" tall edging toward 4". She had a cell phone to her right ear and a Starbucks coffee in her left hand. When she saw me she smiled and motioned me over. I could hear her speaking to someone I believe was Dusty's dad.

"No I'm not going to be on time. Dustin is being held after practice. Yes, that's right...I was told he's not being allowed to leave until 7"

She was making gestures with her hands as she spoke and I watched light wink off the 1 Karat wedding ring she wore. While it was certainly impressive, something else held my firm attention. Mrs. Michaels always wore the reddest lipstick of any woman I've known before or since. As she talked on the phone I watched the glossy red reflect light shining down from a pool door lamp. If ever I fantasized about Mrs. Michaels when alone, cock in hand, I usually thought about her hot mouth. I covertly watched as she took a sip of her coffee and caught a glimpse of a lipstick mark left behind on the black plastic lid.

"Well, I don't know honey, I guess I'll have to wait until he gets out" She was saying. "You just go without me, if I get him home soon enough I'll follow." Then he said something to her I couldn't hear and she looked directly at me. My heart skipped about 2 beats at the eye contact. She held me with her gaze while responding "Well, I've got an idea of how to kill the time so don't worry. I'll see you there." She was now smiling my way as she finished "I love you too. Bye" With that she snapped the phone shut.

"Well hello Pete, I assume you weren't held over like Dustin? When you didn't come out with the other guys I figured you were."

I told her that I'd been lucky then mentioned that she looked like she was going out.

"Oh..I'm supposed to attend a political gathering tonight at 7, but with this new problem at hand I guess I'm not going."

From there we made small talk for 5 minutes or so. As she talked I found myself looking her up and down while pretending I wasn't. Everything about Mrs. Michaels spoke of wealth right down to her perfectly French-manicured nails. I imagined what it might be like if those fingertips were wrapped around my cock instead of a Starbucks coffee cup. When the conversation turned back to the coach's temper I explained how I had dodged his wrath.

"Besides", I finished "He's all bluster anyway. He doesn't scare me"

"Oh so you're not scared of him then?" She asked. "Dusty says you all are." I saw a smile play at the edge of her hot looking mouth. God I wanted her.

"Well I figure his problem is..."

I started the sentence but held back a moment, not sure if I was brave enough to say what was really going through my mind. But then I figured: what the hell? So I looked her square in the eye and finished my thought in full.

"I figure his problem is that he's divorced and doesn't have a hot looking wife like you to go home to."

At this point dear reader, insert a 4 second pause. Her mouth opened a slight bit and she just looked at me before saying. "My my, you are one self-assured young man aren't you?"

"4 years of swim team will do that to you ma'am" I replied, now feeling a shot of adrenaline in my chest at what I'd done.

"Oh really?" she asked. "You just say what you think hmm?"

I looked back and said "Sometimes. You're a milf Mrs. Michaels. All the guys think so. I'm just the only one with the balls to say it."

"Perhaps you didn't notice that I'm married?" She said, flashing her ring at me.

The diamond caught the light and sparkled. It was obviously expensive, a D or E color stone at the least. Wow. She wasn't smiling anymore and her eyes bored into me, like cougar examining prey. I think she was waiting to see what I was going to do. So I responded,

"Like I said Mrs. Michaels, sometimes you just gotta say what you think."

She considered that for a moment before pulling her car keys out of an expensive black leather Gucci purse while saying,

"Tsk, Tsk. You're a cocky one. Arrogant might be a better word. I wonder what your mother might think of this the next time I speak to her at a meet?"

I wasn't sure if she was angry or not. Perhaps I took things too far? My cock was raging in my pants so logic wasn't exactly playing in the front of my mind. Not sure what to say at this point, I said nothing. But I guess words weren't needed because she turned on her heel and began walking to her SUV. I now figured I'd made a big mistake and was starting to regret my indiscreetness. Her heels made about five 'clip-clops' before she stopped, turned, and asked,

"Are you coming or not?"

I felt another surge of adrenaline when I realized what she was asking.

"Um..OK" I said. (That's me, master of the English language)

Without waiting for me to follow she turned and continued into the parking lot. The 'clip clops' of her high heeled shoes echoed off cold brick walls like a mating call. As I moved up next to her, perfume filled my head. I saw her SUV parked against the wall of the pool building under a lamp post.

"Get in the passenger side Pete" came the sharp directive as she disarmed the vehicle alarm system with the press of a keychain button. "I think you and I need to have a conversation."

At this point I was starting to seriously question what the hell I was doing. Was I about to get in trouble? Why was I getting in her vehicle? What is going on?

I guess I paused too long because she looked back as she opened her door and asked, "Am I stuttering?"

I shook my head no.

"I wasn't sure." She continued. "Because when I told you to get in the passenger side, you instead stood there looking at me."

And so it came to pass that I found myself sitting in the passenger seat of Mrs. Michaels' luxury Cadillac Escalade. I looked around as I took off my cap and coat to set them on the floor with my bag. The entire interior was leather seating. The windows were heavily tinted. I was sure this vehicle priced somewhere between 70K-83K. It would have had that new car smell if not for her perfume which filled the air as she started the engine.

"I just want to make sure it doesn't get cold in here Pete" she said as she set her coffee in a drink holder. "We're not going anywhere."

I nodded and kept looking around. I knew that Dusty had a brother and a couple sisters, all younger. I'd seen them before at swim meets. That explained the Barney coloring book on back seat and the transformer toys on the floor.

"So um...Mrs. Michaels. What are we doing here?" I asked. I glanced at the dash clock. It read 6:23pm. Dusty would be out of the pool in about 35 minutes.

"We'll be getting to that in a moment Pete," she began as she pulled her hair back into a ponytail, "but first I need some light."

She flipped a switch on the dash and a central ceiling panel slid back revealing a glass moonroof. The adjacent halogen light pole spilled its illumination down into the interior. The windows were tinted pretty deep though, and I knew that someone in the parking lot would still have a hard time seeing inside. Not that anybody was around. A dashboard LED display indicated an outside air temperature of 19 F.

"Now then" she began, "It seems I have to wait until 7 for my son. Which is not only terribly inconvenient for me, but also boring if I'm to spend it alone. So I thought that this would be a great time to have a conversation about your arrogance."

She set her purse in her lap and started fishing around in it.

"You presume too much I think" she continued. "I'm a wealthy woman and the wife of a prominent man in this town, and I know you know this."

She continued to look for something while talking.

"My husband is a friend of the mayor; they've known each other 15 years. One phone call placed from my cell and I can pretty much have anything I want. Ah, there it is..."

She paused since she'd just found the object of her search. It was an oval lipstick tube, golden and black. She removed the cap off with an audible 'pop' and twisted up a dark red color with expert fingers, before flipping down a vanity mirror to begin an application. I could see a letter 'M' stamped on the cap in a French-style font. First she applied one side of the top of her mouth, and then slowly the second was given similar attention. The golden tube reflected light as it moved.

As she did this she said, "Don't think that just because you're friends with Dusty" (Insert a slight pause as she swept across her lower lip three times, back-forth-back) "That I'm going to let you get away with saying what you said to me back there".

She pressed her lips together while looking in the mirror, examined the result, and decided that a second application was needed. I couldn't believe that I was actually watching Mrs. Michaels put on red lipstick in front of me! But I could also tell that this wasn't the usual color she wore. It was a bolder, darker red. I assumed that she didn't use it often since she had to fish around to find it. As she began again sweeping her lower lip I touched myself without thinking. I could feel the little sensation indicating a pre-cum leak. There might also have been a slight stain appearing on my pants but I didn't care. I was paying full attention to Mrs. Michaels and her glossy red lipstick. After again pressing her lips together and using a pinky to correct an imperfection I couldn't even see, she seemed satisfied. The cap went back on with a 'click' and she dropped the lipstick into her purse before turning towards me.

I'm going to pause at this point to try to paint a better picture of what this whole situation now looked like. Firstly I'm going to ask you to picture in your mind what "fire-engine-red" really appears as. If you've ever put your face up close to a real engine, the true red of a fire truck is a deep, hot, crimson red. This is the best way to explain the new appearance of Mrs. Michaels' lips. During swim meets, her lipstick always turned heads, but the way she looked to me now was simply unbelievable. Continue now to imagine the rest of her. Here was a rich married woman, alone in her luxury SUV with a teenage friend to her son. She's turned towards the young man with her skirt slightly hiked up showing more of her dark hose-clad legs than is appropriate. The top 2 buttons of her red silk blouse are undone displaying an ample cleavage pressed together. Her glossy lipstick, the glistening dark crimson of a true 'Fire-engine-red', refracts illumination from a nearby lamp post a thousand different ways. As her mouth moves to speak, light dances tricks off subtle sexy textures. If you can picture that, then you know in truth what I saw before me. And you more than likely understand why I didn't hear a word of what she was saying.

"Are you listening to me young man?" she asked pointedly.

I snapped out of my momentary trance to issue an awkward "Uh..um..what?"

She took upon herself a look of sternness. "I just told you to go to the back and sit in the middle. Its 6:27 and Dusty will be here soon."

She tapped the clock display with a manicured nail to drive home her point. I felt frozen to my seat as I watched her glistening lips issue instructions. When I still hadn't moved she lifted the arm of my seat saying,

"You are about to find out what happens to cocky young boys who forget their place. Now move it. And take off your shoes too."

Somehow I managed to tear my eyes from her and make my way to the back. She followed and folded the 2 middle seats down to create more space then set her purse on one of them. I kicked off my shoes and socks while tossing the coloring book aside but before it hit the floor I could feel Mrs. Michaels opening up my pants. I looked down in shock, surprised that she had knelt between my legs

"WOOO Mrs. Michaels, What..What are you doing?" I stammered.

She looked at me sternly and instructed me to be silent by saying, "You haven't been listening. I told you, I'm going to show you what happens to arrogant boys. Now sit down!"

My pants now fully opened were pulled off by her in one smooth motion as I fell back into the seat. My cock was straining hard against my boxers and pitching a tent. Mrs. Michaels slipped a hand underneath and deftly achieved the sensation of flesh on flesh. Then she firmly gripped the base of my cock and slipped in another to begin a slow gentle stroking of my shaft. As she did this she said,

"Don't think I haven't noticed you guys watching me. I know you want to fuck me. I bet you talk about it in the locker room when Dusty's not around. You do, don't you?"

I nodded, it was true.

"What do you guys say? Tell me." She demanded.

I told her about the teenage talk of my buddies. I described how my friends Nate and Gavin would talk about her perfect ass and what they wanted to do to it. I told her about how Adam, another teammate, once asked Dusty if his mom sucked cock and how Dusty fought him briefly before we broke it up. There were surely a hundred different teenage fantasies we all had but I couldn't describe each one with her stroking my cock as she was! But I did mention the day she pressed her ass into me.

"Oh you noticed that, Pete?" she asked innocently.

Of course I did! How could I not? My cock had been bulged against the inside of my Speedo like a 5 lb sausage in a 3 lb zip-lock bag and she had deliberately pushed herself up against it!

"Did it make you hard that day? Did it excite you to be in a crowded hallway with people everywhere not noticing what was happening? Did you like it when you felt your swollen teenmeat press itself between these married ass cheeks?" She bent herself in the SUV and thrust her perfect butt into the air to make her point.

I was stunned. I could not believe I was seeing Mrs. Michaels, a respected mother of four, do this. I nodded mutely in response.

"And tell me, what was that word you used to describe me? Milf was it?"

I again nodded.

"I can't believe you even said such a thing to me!" She said sharply. "When I overheard you use that word to a teammate last week I went home and looked it up online. Milf means 'Mom I'd Like To Fuck'. Since you just now used that word to describe me tonight I'd bet that you fantasize about us fucking. If you had things your way I'm sure you'd want me on this seat instead of you. You'd have me on my back with high heels in the air, skirt hiked up, blouse pulled open, and your teenmeat plunging in and out of me. Is that what you want?

I didn't know what to say. "Um..uh...whaa.." Was the intellectual depth of my response.

"I'm a wealthy married woman Pete, what the hell is wrong with you?" She finished as she pulled my boxers all the way off and tossed them away.

Mrs. Michaels was a woman of standing and to hear her talking like a slut that lived in a trailer made my cock as stiff as a steel rod. She started stroking me harder with her right hand as her left moved to caress a breast through her silk blouse. Light winked off her wedding ring as she tweaked a nipple. I reached out to feel the heaven that must have been her chest behind the silk but she slapped my hand back.

"I told you Pete, I'm a married woman...."

Pausing she bent down and flicked the head of my cock with her tongue-tip to remove a growing bead of pre-cum before adding,

"If you try do something stupid like that again..." She lifted her cell and continued "I'll place a call to my husband and say you tried to rape me. You'll be in the worst trouble of your young life. Do you understand?"

I responded with a quick nod. I'd never been so simultaneously excited and scared in all my life.

"Good." She said satisfied "We are now going to establish some ground rules. Firstly, from now on you will refer to me as Mrs. Michaels. Not 'MILF' or 'Dusty's Mom' or whatever the hell else you boys say about me when you're together. You're going to accord me the respect due a wealthy woman and the only adult here present. Understood?" She gripped my aching shaft harder to accent her point. I nodded quickly. "Good" she said as she loosened her grip and started stroking again. "Second, you'll not touch me unless I tell you to do so. I'm married and I'm not about to start cheating on my husband." She lifted her stroking hand then from my twitching cock and pursed her glossy lips. 'Pa-thu!' came the sound as she spit into her hand. When she returned to stroking me I felt my tool become slick from her salvia. I could hear wet 'slick slack' noises and my balls ached from pressures within. "Tell me what you understand, Pete" she finished.