The Best 24 Hours Doc Ever Spent

by Pettybox

Copyright© 2016 by Pettybox

Sex Story: A man gets an unexpected flirt by a MILF he has no idea has checked him out, vetted, and set her sights on. She wants to cure some loneliness, and horniness with no strings attached.

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Fiction   Oral Sex   Squirting   .

For as long as I can remember I’ve always been known as “Doc”. Stories of where that all started go back to a couple different tales, one of a doctor kit I got when I was 3 or 4, another is me mimicking Bugs Bunny from the old cartoons that were on every weekday afternoon and Saturday morning. No matter where it came from, it was better than Stanley Orvis Stemberg. Everyone always called me Doc, even teachers in school. I pitched a little minor league baseball and in the one really good year I had with the Piedmont Phillies in homey Kannapolis, North Carolina the newspapers started calling me Stanley Steamer. Kannapolis is a suburb of Charlotte, and I suppose Southern homespun folks thought that was a cute name. The year after I blew out my shoulder and became a knuckleballing reliever, Stanley had no more steam. I was only retained because I was so well liked in the organization with coaches and instructors. I actually could have hung on and even got a shot at the majors as a relief specialist, but no matter how I looked at it, that eventuality was 3 or 4 years away and the pay in 1995 was nowhere in the modern strata of ball player salaries. I kicked around a few years as a player-coach in the Phils system, but I had background in plumbing and auto-repair from summers working with my Dad and Uncle before I got signed. So I made a decent living, having opened my own plumbing business, and leased my Dad’s garage out (that I sort of inherited) to a Mobil franchise.

My year as “Stanley Steamer” I met and married Arlene. We stayed married for 5 years. Once I was no longer a serious prospect and began looking for other ways to support us, I guess the shine wore off of me. We weren’t married much more than a year when we both knew we had made a mistake. We didn’t talk much, or act as if we had much in common very often. However, we did like to sweat up the sheets, even right up to the day we went to sign the papers on our divorce. She only wanted half of what we had, except for the bills. We didn’t own a home, or have kids, and had two 3-year-old cars complete with payment books. She got the better car, I got both payment books (lucky me). There was no real malice between us, and I don’t think either of us ever cheated. It was as amicable a separation and dissolution of a marriage as you could imagine. We’re still friends, easy because she stayed in Charlotte (has married and divorced another ballplayer) and I ended up back home in Watertown, New York.

Before I married Arlene I was a lady killer of sorts, never having much of a problem finding female company as a local star athlete (in my own mind) and a pretty good looking guy. I was going home to New York every Fall and getting back to the Charlotte area just before pitchers and catchers reported to Spring Training. There was always a Femme Jolie looking to go to Florida for 6 weeks with an athlete roommate. That girlfriend usually lasted until she met one of the guys on the Major League team, or a guy who might get promoted up the line faster (maybe Reading or Scranton – neither as good as Charlotte, IMHO), but they got payed better and got better meal money.

After I was no longer a sports super hero and retired from the game at the ripe old age of 29 finding female companionship was a bit tougher, but I usually did well. When I’m not working I usually dress well, nothing too foo foo, but always nice jeans and a nice shirt that fit my body nicely. I’m still in good shape, only 10 more pounds from when I played ball, but I’m down some hair, for sure. But, my days of flirtatious females coming on to me was long passed, or so I thought.

It was the Saturday of Memorial Day weekend and I was out running errands before I went to my favorite brew pub to help them celebrate their 2nd anniversary. I hadn’t had much of a breakfast so when I went by Sam’s Drive-In I stopped to get some protein and carbs working in my belly. Sam’s is a place where you can get a burger and fries and little else. Sam runs the place with one or two helpers and if you order a hamburger it comes with ketchup and a pile of fried onions, unless you ask otherwise. Sam’s son leans out the window to the constant lines of people and takes the orders, 7 to 10 at a time and he never messes up.

As I walked up to the end of the line going through my pockets to be sure I had enough cash. I didn’t and I had to go back to my car to see if I had my stash. (Sam doesn’t do credit cards). I usually have a $50 bill in the glove box for emergencys. When I walked back up to the line I heard a friendly voice call out.

“Oooo, I LOVE that place, my husband and I used to go there all the time.”

I looked up to see a nice looking woman pointing to my hat and I had to take it off to see which one I was wearing. It was for Rare Brews, the brew pub I was headed to.

“Oh, I’m just heading there for their anniversary celebration, they’re releasing their most popular brews in cans today for the first time.”

“That’s great for them, I should get there, but I have the kids and their Aunt Rona today. Rona’s from Baltimore and loves our little treasures around here. We’re bringing her to Rosie’s Pizza for dinner tonight.”

“Oh, you can’t go wrong bringing her here and then to Rosie’s, the best pizza I’ve ever had.” I said still wondering; “Did I know her? Does she think I’m someone else?”

Then the woman turned back and spoke with her kids, her friend Rona (not a real Aunt I found out later), and I went about minding my own business when she turned back.

“Really nice what they’re doing downtown, at the brew pub and all the new little eating places. Have you tried Two Bagger Sliders? That was another of our favorites.” She asked brightly.

“Oh yeah, their cheese steaks are great and Beef Wellington egg rolls are to die for.” I added, still stymied how this woman, way out of my league, and at least 15 years younger than me, was so taken by my presence. She HAD to think I was someone else, so I asked an obvious question hoping the answer wouldn’t dissuade her from continuing the conversation, making her realize she did not know me.

“He doesn’t bring you to those places anymore?” I wondered aloud to her.

“No, he left me and the kids about 6 months ago.”

“I’m so sorry to hear that.” I said figuring it would be the end of the conversation.

“Oh, don’t be. He led a double life, was an embezzler and total fraud. He might be in Mexico for all we know. If he ever comes back he’ll go to jail.” They were just getting to our spots in the line and she gave the young Sammy a complicated order for 3 children, herself and “Aunt” Rona. He got to me and I just held up 3 fingers and then crossed two. It was Sammy sign for 3 burgers and fries. The fries came with a spurt of ketchup in the corner unless you asked otherwise.

As they began to fill the orders in front of us young Sam would pause and look up and take a few more orders. Rona who was in front of the 3 girls, looked back to her and said “I don’t know how he keeps track.”

“He just does!” She answered and then she turned to me.

“She was my roommate in college and just loves the girls and coming here to get all the great food.” (and Rona from Baltimore piped up as she kibitzed with the kids) “Stuff that’s NOT crab!”

I just smiled as Sammy had her order ready and Rona was paying for it as the kids were delighted that each of their orders was on a separate paper plate on the tray. I knew this was the end of our little tete-a-tete so I asked the most awkward of questions.

“I’m sorry, but do I know you?”

“No, but can’t a girl flirt with a good looking guy? It was nice talking with you.” She said as Rona shouted back “Come on Kailynn, I paid for it all and the kids are getting a table.”

Young Sammie called out “3 with fries, do you need a drink?”

“Uh, NO!” I said as I watched “Kailynn” walk away in her little jean shorts and yellow t-shirt that she filled just fine.

I paid for my food and realized as I walked to my car I had a little chubby on my pants. It was hot enough for early June that I was glad to have an air-conditioned car where I had a cold bottle of water to wash it all down with. I was parked on the opposite side of the drive-in so I didn’t see the table or car where these two women and the 3 kids were. I was downright flummoxed, and I do mean FLU-MOXED.

I am 45 and I don’t want to fool you into thinking that I look a day younger. I may still have somewhat of a build, but my face, hairline, and overall demeanor shouts “Approaching 50 – proceed with caution”. Why was this very good looking woman, who was maybe 30-33, tops, who had 3 kids, the oldest being 8 or 9, openly flirting with me in front of her kids, her “best friend from college” (she also appeared to be 30-ish, so there was no mistaking age), and the rest of the people standing around us. Did I imagine the flirt? Was it just idle conversation? I told myself that if I were her husband and saw the banter between us I would have walked up and stepped in to see what was going on. It really was that blatant. She was so fresh, so reeking of youth with her flat belly, sexy bust line, bright eyes, cheery smile, and melodic voice, ... and she was speaking to me as if I were her boyfriend. I had to admit that for the first time in ages, just the thought of a woman had me excited in my pants.

It wasn’t that I hadn’t been laid in a long time, it was Saturday and I had spent Monday to Thursday nights with Sara, who I guess I can describe as a girlfriend of sorts, but we have no ties. I may not hear from her for a week or two, and then she calls and we spend anywhere from a night to a week together. When she does we share any expenses if we go out, there’s no quid pro quo for each other’s company. I met her when I started playing some Roy Hobbs baseball, her Dad was the manager. She always watched the games and helped her Dad out, bringing water, GatorAid, seeds, and a cooler of gel packs for any aches or pains that us old guys experienced in playing. She even warmed up a lot of the players before games, she probably could have played, she is that athletic

After her Dad passed we kept in touch as friends. She would come over “for a catch”, just throwing the ball around reminded her of her Dad, but one hot afternoon she came in the house for a beer and we ended up doing things that decidedly did not remind her of her father. Besides sex and companionship, we expect little of each other, never show up unexpectedly or have expressed any jealousies. Despite being a tomboy, Sara is all woman, for sure. Not much in the breast department, but can fill out a pair of jeans as well as any woman. Always a great companion for any situation, we just fit together well and expect little of each other if we aren’t at each other’s side. The only caveat of our relationship was condoms, we didn’t use them, but agreed if we happened to be “with” someone else, we would. She was on the pill, and I was “fixed”, but were wary of STD’s.

I finished my burgers and fries and took my mess and balled it together and headed for the trash bin so I could head to Rare Brews. I was about to throw it in the can in front of the car, but decided to bring to the front of the drive-in to get another peek at Kailynn. The 5 of them were around a table, Kailynn to my back and Rona was picking up things to clear the table clutter. She saw me and quickly looked away, but did look right at Kailynn and nod towards me. Kailynn began to turn around, but I think she saw her oldest, sitting next to her, and thought better of a flirtatious blatant look back. The way Rona acknowledged me, I was sure the two exchanged a few whispers about me.

I was sure my little affair in my mind was over not knowing anything of her or she of me and I went to my car and drove to Rare Brews where I got a place at the bar and sampled 2 of their new brews and had 3 of my normal favorite, a Scottish Ale, to pass the afternoon. It was an old home week of sorts there for the anniversary, seeing friends I rarely come across in my day to day life. By 5:00 pm I felt confidently sober to drive home. I knew all of the local cops and unless I was falling down drunk, they knew I didn’t have far to go if I was stopped, but I was careful not to drive if I thought I couldn’t pass a sobriety test.

When I got home and out of the car I saw the bags of mulch I had delivered earlier in the week and set about to mulch the shrub line beside the drive way. The mulching went fast and easy and also provided enough exercise to clear any alcohol from my system, not that I was ever drunk, per se, that afternoon. But I felt rejuvenated and now, at a bit after 6:00, hungry again. I thought of firing up the grill, but I remembered a sign at Rare Brews reading “Our Anniversary Ale available at Rosie’s Pizza, while it lasts.”

Hmmm, a trip to Rosie’s WAS in order, and maybe I could run into Kailynn again. It should be said that I still thought that if she saw me in the bar lighting I wouldn’t look as familiar as she thought this afternoon. She truly acted as if she already knew me and her line “can’t a girl flirt with a good looking guy?” was supposed to remind me of where or who she knew me through. She was just that far out of my league, I was almost 20 years older than she!

I went in and showered, dressed and headed to Rosie’s. After spinning their lot and the block I finally found a parking place at Rosie’s just after 7. I got a beer and stood behind the occupied bar stools watching my pitiful Yankees fall behind in the 1st inning (again!) until a patrons table was called or to go pizza was ready to get a spot. It didn’t take long before I got a stool right at the end, to the right of the waitress access rails so I could have elbow room when I ate. (I’m a lefty) I ordered a small pie, a “Rosie Special” (double onion, sausage and mushrooms), got my anniversary ale and got into the game exchanging comments with fellow Yankee fans down the bar, all as disgusted as me.

Two bites into my 2nd slice a hand went to my shoulder and I turned to hear, “Hello my friend! You’re a guy who pays attention. How’s your pizza?”

It was Kailynn and before I could react or answer she slipped by and went to the Ladies room.

I quickly wanted to figure a strategy if she came by and stopped again, and told myself NOT to get disappointed if she just went back to her table. I was using the mirror on the back of the bar to see if I could see the table where her friend and kids were seated, but that was for naught as I wasn’t sure I could recognize any of them from the back of their heads.

Was she goofing on me just to tease? did she really think I was someone she knew? or once knew, or did she really have the hots for a guy who could almost be her father? When I chose my options I really thought of picking up my beer and pizza and just leaving. I didn’t need to be made a fool of, or the butt of an inside joke between she and her friend.

I took a couple long swallows on my beer and pushed my glass to the bar gutter and the bar tender nodded and filled another for me when I saw the Ladies Room door open Kailynn walk out, but not even look to the bar and go to the back room, presumably to join her table.

I was a regular at Rosie’s so when one of the waitresses I knew, Brianna, (a ball buster, she and her husband were neighbors) came into the rails I asked her, “Do you have the table with 2 chicks, 3 kids and one of the women is knock down pretty with a yellow tee shirt and jean short-shorts.”

“Not my table, but I did see them. When she went to the Ladies room every guy in the place followed her behind.” Brianna said with head shaking while she chuckled, “You too?” She added, “You’re twice her age.”

“Thanks Bree, but I think she’s trying to either pick me up or make a fool of me.”

Brianna shook her head. “You’re dreaming Doc, go home and meet your hand.” She said as she winked and took her tray of drinks.

Actually her advice was probably my best option. I took my new beer and dove into my third slice of pizza. I was resolved to eat this third and final fourth slice, quaff my beer and leave.

I set about to accomplish that without rushing and upsetting my stomach. Two beers are my limit to drive home from a bar at night anyway, so I decided to just end her game myself. While finishing my last slice of my “Rosie Special” personal size and saving the last few ounces of my beer to wash it all down I was turning on my stool to hop down and leave when I noticed someone (I presumed a waitress) fill the rails. I looked back to see if it were Brianna so I could say goodnight, but there stood the woman I knew to be “Aunt Rona”.

With no expression whatsoever she simply said, “She’s bringing her kids to stay with me at the Hilton, they have a water slide pool. She’ll drive back here if you’re staying. Give her a half hour.”

I froze and looked down to gather my thoughts, but when I looked up, Rona was gone and I turned to see them all leaving with Kailynn’s round jean covered ass bringing up the rear.

When I turned back to re-assume my stool Brianna was there, “Got that in your spank bank?”

I smiled and shook my head and asked the bartender for an N/A beer. I would sip that and watch the game for another half hour, then go home.

The game got interesting with both the Yankees and Rays filling the bases each in consecutive innings and not scoring, all without the benefit of a hit. It was just over a half hour and I pushed my bottle and a 10 spot in the bar gutter to go home. I turned to leave and there stood Kailynn.

“Hi sexy man, my name is Kailynn. I haven’t meant to be a tease, but I did have my kids with me.” She said and waited for my reaction before extending her hand.

“Doc!” I announced, “ and Yes, you have been playing a game with me.”

“Not a game, an obsession. When you showed up here, I figured you were in.” She smiled sweetly.

“In what?”

Kailynn blushed. “In most anything.”

I pointed toward the half wall that separated the bar and restaurant, “Let’s take that high top and talk.” She turned and went as I asked and we sat.

She held up a hand, “I’ll talk.”

“Have you ever seen something, or someone you just HAD to get to know, ... or have? That was you this morning. It was one of the great coincidences. I’ve seen you around town many times before, working out of the back of your plumbers’ truck, in the gas station, and in the grocery store. I told myself that if I had a chance at you, I would look you up. Why? I don’t know, something in your face and, (she giggles) ... your butt.”

“I’m not buying it. Look at me, look at you.” I said.

“That’s what Rona said you would say. She thinks I’m crazy, but says I have good taste. It reminded her of our college days. She wanted to help me.”

“Help you what?” I asked.

Kailynn turned bright red in a hard blush, and through pursed lips she almost whispered, “Get laid.”

“You can’t have a problem in that department. You could have had a dozen volunteers in here alone.” I said, beginning to think that this was all too serious for a prank.

She leaned up as if she were going to try and kiss me but she cupped a hand and spoke,

“Since my husband left my only friend has been my hand. I’m going a bit crazy and all my fantasies are you. Don’t ask me why, but I’m stuck on this. I know I could have other men. When Rona flew in here Wednesday we went to lunch and by chance saw you working from the back of your truck near my neighborhood. I pointed you out then and even told her of my fantasies. When you walked up in line at Sam’s I figured it was kismet.”

“I’m a lot older than you.”

She rolled her eyes and put a stern look on. “Are you interested or not. I’ve never thought I would have to beg anyone. The way your face lit up, and the front of your pants reacted at Sam’s, I thought you were interested in me as well”

I had enough cat and mouse. I said, “Let’s go!” and got up from the stool and headed for the door with her in front of me. As soon as we got outside she asked, “Doc, right?”

I nodded and she asked, showing just a bit of fear or trepidation for the first time, “My place or yours, leave a car or follow?”

“Lock your car up and come with me. I’ll bring you back in the morning, ... or afternoon.”

“Why can’t I follow?”

“Don’t want you to leave in the middle of the night. You’ve jerked me around enough today; this is your commitment to me.” I said bruskly.

She paused to think a moment and looked back into Rosie’s. I turned and looked as well and saw Brianna, perhaps a little stunned, standing in the doorway behind the squeaky screen door. She waved to me and smiled.

“She knows I’m leaving with you.” Kailynn warned me

“Kailynn, you must have done some due diligence on me, you’ve never been in better, or more grateful hands.” I said.

She locked her car and came with me to my car. I opened her door and shut her in.

I started the car and the 70’s on 7 on my XM Satellite was playing “Third Rate Romance”. We no more than got backed out and she chuckled as she heard the line in the song “I’ve never really done this kind of thing before—have you?”

She looked straight ahead and said, “That line of that song is true.”

“For me too, at least not like this. One night stands were a college thing.”

“Are we just one night?” She asked.

“Up to you, ... and me. Things aren’t always as they seem. Whenever I’m out with the boys and we see a woman as hot as you look, one of us invariably says “Somewhere there’s a man who hates her guts.”

“Do I look like a heartbreaker?” she asked.

“No, but I’ll bet you’ve turned down a lot of pick-up lines.”

“Not as many as you think. I was involved with Rona for a while in college, how about THAT confession? But we decided we both loved men more, but it was convenient at the time ... and by the way she isn’t here for me NOW in that way. She has a man at home. After I got married I rarely ever was out without my husband.”

“Did he leave you flat broke?”

“After he was caught I still believed in him until other women wanted a piece of him. I found out he had another wife in another state, and I thought I was pretty stupid.”

“Did he leave you flat broke?”

“Are you a cop? ... and am I being recorded?”

“Paranoid? No of course not, I am what I am. Remember YOU picked ME up.”

“Well after they searched everywhere for him, and tore my house apart looking for ill-gotten booty or merchandise. They took anything major that we bought after his first score, but that wasn’t much, just a couple TV’s. They figure he’s got all the money.”

“Did they figure right?” I asked, my third attempt at the similar question.

“You’re pretty smart Doc. No, they didn’t figure right, and at least I know he had some sort of conscience. I started selling his record collection on Ebay. The first person who bought one wrote and said I must have hidden mad money inside the album and forgot it. They sent back a crisp $100 bill. I started checking the other albums. He had over 5000 in library racks in the basement.”

“They never checked them?”

“They did, just randomly like the B’s, the S’s, the two biggest sections. One detective found one bill and slipped it in his pocket, and my girls saw him do it. That was the end of checking them after I threatened to have him arrested. It was assumed to be random mad money anyway. We still thought nothing of that one bill in an album, until we sold that first LP. Then I started checking. I remember he said in his consolation and apology call to me, “Enjoy the record collection.” I almost gave them all away to spite him.”

“Your secret is safe with me.” I said as we pulled into my driveway.

“Even if you told someone, they would never find it now. I’m told if I can bring him in I can collect the 50K reward his company has for his return. I don’t need that little taste when I’ve got the whole damn meal. But the promise of the reward assures them I don’t know where he is.”

“Kailynn I barely know you, but I like your style. You’re smart and know how to take care of yourself. I just wonder why you would tell a total stranger this.” I wondered.

“I may be a stranger to you, but I’ve been checking you out, looking into who you are, for a few weeks. You’re cool, asking if you were a cop was just to cover my ass.” She said confidently.

“I think you’re cool too.”

“We’ll see if you still feel that way in the morning. You’ll only be the third guy I’ve ever been with, but I’ve been around the same block a lot.” She said with that sexy chuckle as she got out of the car and walked to my side and I showed her in.

As I turned on lights and asked about drinks etc. I ran through my mind if I should be creeped out by her “checking into” me. I’m well known right here in town, even somewhat of a local hero, via sports and reputable business and I really have no skeletons. I do a lot of pro bono work and have never harassed an individual for payment for services. I help who I can, being careful not to be taken advantage of.

I showed her to the living room sofa and switched on a little late night jazz and turned to face her, asking “So what is it about me that you find so fascinating?”

“I knew you would ask this and I hope I can give you a satisfying answer. After being married for 9 years and finding I really didn’t know the real person my husband was, one thing stuck out in my mind. We had great sex and that may have clouded a lot of the obvious things I missed in my judgement of him. After he was gone for 4 months I was really getting tired of being in a relationship with my fingers and a few little toys I had. In college and before, my masturbating subjects were always fantasy men and women. So after the kids were off to school in the morning I would go shopping, or for a walk, or just for a sit on a bench downtown or in the park. I would pick a number from 1 to10 and say maybe “the 7th guy I see I’ll mentally undress and take to bed.” Only a couple times did I end up with a fantasy I could really bring home in my mind to enjoy. I did it twice with you, both randomly, once at Shop and Save, and then once downtown, you were coincidentally the magic number again. That day you stopped right in front of me when your phone rang. You leaned on a pole and spoke a few minutes and then sat on the bench that backed mine.”

“Right by Lou’s Cafe and City Hall, I remember that day. My ex-wife Arlene called to tell me she was moving after her 2nd divorce became final. We’ve always remained friendly.” I interjected.

“You sounded so nice on the phone, talked so sweetly to her, I closed my eyes and imagined you were talking to me that way. I rushed home afterwards and played that fantasy out in my mind. I saw you get in your plumbing truck and I found out who you were. I was sold then. I haven’t been able to get you out of my mind since.” She said finishing her confession as she blushed deeply.

“You aren’t looking for a boyfriend, sugar daddy or husband, are you?” I asked.

“No, no, no! Just some satisfaction and memories to last until I do jump back in that pool. I have 3 daughters and trying to raise them without the help of a husband is hard enough. I don’t think I have the time for any of those options, but maybe someday.” She said as she sipped the wine I had chosen for both of us.

Then she startled a bit asking, “You wouldn’t want me for a girlfriend? I know how good I look and have been asked out and propositioned left and right since he left.”

“If you were my girlfriend I wouldn’t want you to leave the house, besides, when I’m an old fart of 60, you’ll just be...”

“Thirty-nine. That doesn’t matter to me, but right now I just wouldn’t have the time to build a good relationship. Tomorrow morning when you bring me to my car we can decide if we ever want to do this again. I know you have a girl of sorts; I’ve heard that story. This will never be of the heart, it’s physical, and its fantasy. My girls are ALWAYS number one. But I do think we can be friends, if you can do that without causing any trouble with your other friend.”

There was a long pause in our repartee and after we each drained our glasses I asked, “So, how does your fantasy start, and let me add, there are no guarantees for either of us, agreed? (she nodded) If it isn’t right, we’ll know.” She turned and offered her mouth to mine saying “I’m not worried.” Just before our lips touched.

Her kiss was that of a woman who hadn’t had been with a man for 6 months. I thought she might eat my face, but the kiss was long, erotic, and extremely sensual. When it broke I was blushing. I smiled at her and said, “Wow, that was quite the kiss, and you smell terrific.”

“I showered after I dropped the kids at The Hilton, that’s why I was a few minutes late getting back to Rosie’s.”

“I showered just before I got there, I can take another if you want.”

“No, I want that man smell, man taste.”

“Mmmmmm, we’re going to taste?” I asked, somewhat facetiously.

“Listen, a ... Doc. This isn’t going to be a first time with the new girlfriend ripping off a condom with a sloppy splash on my belly. This is going to be like a hot married man and woman, who’ve had sex a 1000 times, love making session. I sort of thought we had that straight, I guess I didn’t quite put it into words.”

 
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