I Won Hands Down Pt. 01

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Older woman teaches shy college student the art of sex.
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MaxiMilf
MaxiMilf
230 Followers

Author's note: The first part of this tale will be placed into the LW "Mature" section. The second part, when written, will be placed into the "Loving Wives" section. So, if you're following the story, you'll need to keep an eye out for part 2 in another category.

I never thought in a million years that my wife of ten years would be unfaithful to me. "Not a chance," I naively thought. After fifteen years of marriage, I really believed we were on a firm footing. My problems began about three months ago. Up until that time things were okay, though I did notice some subtle changes a few months prior to that. But I just chalked that up to the normal ups and downs of a marriage that was well into its second decade. My name is Leo Tatum and my wife is Kate Jackson.

Before I get to the problem surrounding the implosion of my marriage, it's really important that I go back and tell you a story from over twenty years ago. I know that's going to turn some of you off, but the events of those days have a direct bearing on today's troubles and are integral to the story.

Back in 1999, I was in my sophomore year at a well-known university in upstate New York, in a town not too far from Albany. I was a pretty shy nineteen year-old kid, lacking in any significant carnal experience with the fairer sex. Hell. Who am I kidding? I didn't have any experience with women. In high school, while I was very involved in two varsity sports, football and baseball, I was a loner. I was a fit, good looking kid. But I was considered a bit of an oddball. I never liked the party scene and didn't see the point in alcohol induced comas after a Friday night of football games and teenage debauchery. And since I had gone to an all-boys Catholic high school, to say I was awkward with the opposite sex would be an understatement. Still a virgin in college in my nineteenth year, my hormones were raging, and I walked around campus with a hard on for most of my freshman and sophomore years.

Since I was a journalism major, and given that the Internet was no where near as sophisticated as it is today, I spent a lot of time doing research in the college library's reference department. Back then, you really had to work hard to get any information for term papers and assignments. Toward the end of the first semester of my sophomore year, the college hired a new reference librarian, Mrs. Patricia Walsh. She caused me to spend even more time in the library than I needed to. Back then, I guessed that she was somewhere in her late 40s. Turns out she was 47 when she started at the college library. Mrs. Walsh fueled many a late night fantasy back in those days when I dated my right hand. Why, with all of the hot coeds cavorting around campus, would I develop a secret hot crush for someone who was twenty-eight years my senior? I guess it had something to do with the fact that I was comfortable speaking with older women, and I was profoundly bashful and insecure around women that were closer to my age.

But it was much more than that. The librarian was, quite simply, a smoking hot MILF wrapped up in a very conservative package. Mrs. Walsh was about five feet, four inches tall, with straight brunette hair down to her shoulders and bangs over her forehead. She wore the typical librarian "granny" wire framed glasses, which were in front of the two most gorgeous emerald-green eyes you can possibly imagine. Those eyes, combined with fair skin, her little turned up nose, and pouty mouth made it very obvious that she was of Irish descent. She consistently dressed in a very modest, age-appropriate professional outfit, and she always wore stockings and black business pumps with a low heel, something which has fallen out of fashion as of late. Mrs. Walsh didn't have much on top. But man, what an incredible ass! I have never seen anything so magnificent before or since. On rare occasion when she wore slacks, I would sit in the reference room staring as she walked away and would nearly come in my pants. Her backside was so incredible, you would be inclined to get down on your knees and give thanks to the Lord God for his magnificent creation. She had wide hips to complete her stupendous ass. They may have been a bit too wide for many guys, but they were just right for me. Many a time I imagined myself pounding into her from behind gripping those hips like a steering wheel. And, in my adolescent fantasy world, I pictured that with each thrust, her ass cheeks would jiggle a little.

It was on a late Friday afternoon that she caught me staring at her. Little did I know at the time how lucky I was that she took notice, though, at the time, I wanted to crawl under the table and hide in embarrassment when she first approached me.

"Young man," she said in a soft, demure voice, "I'd like to speak with you in my office, please."

This was it. She was going to bar me from the library. I didn't think I was that obvious.

"Your name is Leo Tatum. I noticed that you spend quite a bit of time here, and I can tell you are quite studious and dedicated to your studies. That shows character. The other librarians who know you have told me that you are a very polite young man."

"Here it comes," I thought. But instead, she stopped and smiled at me. Was it a seductive smile? Hell...I imagined that everything she did was seductive. But the smile from her pouty little lips did signal that she wasn't mad at me at all.

"I need some help around the house, and I was hoping to hire you for some odd jobs on Saturdays."

"Wait. What?" I replied incredulously.

"You know...mowing the lawn, weeding, the odd repair here and there. What do you say? Interested? I'll pay you a fair wage, comparable to what the other kids your age are making at their off campus jobs. Sadly, my husband was killed tragically two years ago, and there's no one around to help me. I've held off as long as I could, trying to do everything myself. But I just can't manage anymore. And I don't want to hire just anyone. You come highly recommended as somewhat who is polite and pleasant."

Anxiously, perhaps a bit too anxiously, I replied, "Yeah. That'll be fine." I'm sure she noticed how my voice cracked nervously with that response.

"Okay. I'll see you tomorrow morning at 10 a.m. Here's the address. You are available tomorrow, yes? I just realize it's short notice."

"Hell yes!" Oops, sorry. I mean, yes, I'm available. I don't have anything going on."

She handed me a piece of paper with her address and phone number and signed it "Patricia," not "Mrs. Walsh." From the library, I went straight to my dorm and jerked myself off into oblivion with thoughts of Mrs. Walsh in tight jeans and a t-shirt, something she never wore to her library job.

Turns out that my fantasy of Mrs. Walsh in the outfit that I jerked off to was exactly how she greeted me when I rang her doorbell precisely at 10 a.m. I was up half the night in anticipation, and arrived at her house much earlier than the appointed hour. I nervously paced around her block hoping to ward off the jitters so that they wouldn't be too obvious. Her ass looked even more glorious in jeans. She had to notice the hard on that I was sporting. There's no way she could have missed it. Before the end of that first day with her, my balls were so blue I was nearly doubled over in pain, and my underwear was soaked with pre cum.

"Hi, Mrs. Walsh!" I shouted out a little too fervently.

"Right on time, I see. Punctuality is important. I like that. And it's 'Patricia' here at my home. Let's ditch the 'Mrs. Walsh' thing when we're working together. It makes me feel ancient."

We spent the better part of three hours working together in the garden. When we were done, she thanked me, paid me in cash, and asked if I would come back the following Saturday. You bet I was going back!

As we got to know each other a bit better, Patricia became very friendly. She would always make sure to give me lunch and keep me hydrated. For all the sexual fantasy floating around in my head, I learned that she was a genuinely nice person. Once I got my hormones under control, we developed a very pleasant rapport and friendship. Dealt with a bad break on the untimely death of her husband, she weathered that problem and soldiered on. We often spoke of her husband and any possibility of another long-term relationship. Honestly, she could have had her pick of suitors, but she wasn't interested. She told me that there was only one man for her and that she could never love another.

One Saturday, after a particularly humid day out in the garden, it was obvious to her that I was perspiring profusely. She insisted that I take a shower. By now, I learned to control myself around Patricia, but a shower in her house got me going and my cock grew hard before she handed me a towel. When I finished up in the shower, I noticed that my clothes were missing.

I heard a gentle knock on the door and she said, "Leo...your clothes were pretty wet. I hope you don't mind, but I took the liberty of throwing them into the washer. Why don't you stay for dinner? By the time we're done eating, your clothes will be dry. I'll leave a pair of my husband's sweats hanging on the door knob. I'll leave you alone and let you get into them. Come down stairs when you're ready."

By the time I got down the stairs, Patricia had two steaks in the broiler. But something was different. She changed into a cute little sundress and sandals. Of course, my cock was still at attention when I got downstairs. Her outfit did nothing to keep it under control, especially since I didn't have any underwear on. And with nothing to restrain it, it was clear to anyone who looked in my direction that it was at full mast. I sat down and tried as best I could to cover it up with my hands.

"Leo," she asked. "You've never told me if you have a girlfriend. Nice good looking young man like you probably has his pick of the ladies. Saturday night is a big night on campus and I'm afraid I wear you out here. Do you have any energy left for your gal when you get back to your dorm?"

Patricia was surprised that not only didn't I have a girlfriend, but also that I was so shy around women. We ate and continued to talk about my shyness problem. She encouraged me by telling me that I was a handsome young man with a terrific personality. She said that I would be a "catch" for any of the girls on campus. Then Patricia "crossed the great divide" and I nearly came in my pants.

"I don't want to embarrass you, Leo. But it must be awful that you don't have any sexual outlet. I see the way you stare at me and I always notice a bulge in your pants. While I'm flattered by that, I worry that you're missing out on what should be a very active time in your sex life."

With that, Patricia sidled up next to me and put her hand on the sweat pants with a firm grip on my cock.

"I'm sorry to be so blunt, but you're doing a poor job of hiding your arousal. This is going to sound abrupt, and please forgive me if I'm crossing some kind of line here. But I am very attracted to you. Don't worry. I have no delusions here. I know I'm a lot older. But I can easily take care of you in that area. Walking around with that monster in your pants at full throttle is not healthy. Are you okay with that? Am I being too forward? Please forgive me. It's been a long time since I've been with a man. I guess I'm out of practice and just as nervous as you are around young girls."

Completely speechless, I simply nodded and said "Uh huh." My mouth turned to cotton and my heart was about to beat out of my chest.

She told me to pull myself away from the table, and then she pulled the sweats down. Patricia gently rubbed the pad of her index finger from the base of my cock up to the tip.

"Wow. You have an impressive cock. It's a about average in length, but I don't think I've ever seen one quite as thick and fat as yours. This is enough to keep any woman satisfied."

The tip of her finger trailed behind her nail and sent shivers up my spine as it worked its way slowly to the top. Her soft fingertip tickled my frenulum slightly. Patricia had the sexiest hands I had ever seen. She never wore nail polish, but had the most perfectly manicured nails, squared off at the top. Can you guess what happened? Yep. I blew my load before her finger had a chance to circle my head. And in this case, "load" is a perfectly apt description of the amount of come that jetted out. The first shot had to have gone about three feet up in the air. That was followed by four successive spurts that were more like thick white ropes, landing on her lap on their descent. She jumped back a bit, startled at the sudden onset of my cumshot.

Completely overcome with my humiliation, I jumped up, pulled up the sweats and ran to the bedroom where Patricia had left my clean clothes. My plan was to run out of the house and never return. But there was Patricia when I came down, at the bottom of the steps, blocking the front door.

"Hold on, young man! I know you're embarrassed by what just happened. But that's fairly normal for guys your age who don't have any experience."

"That's not what the guys in the dorm say. They're always bragging about the size of their cocks and their staying power. Right now, I feel like I just want to run away and hide. I'll never be able to satisfy a woman. And I'm so embarrassed that you saw me that way."

"First of all," she replied. "Those guys are all full of shit. Macho men like to brag. Given the same situation that just happened here, I'm sure they wouldn't have been able to last much longer than you. Look...You're too nice of a guy to let this bother you. I'm going to help you with this problem. Tomorrow's Sunday and I'm busy in the morning. But come back at around 3 o'clock. I promise you this will get better."

Patricia had a very calming way about her. My anxiety and stress level went down a few notches following her kind words. I had no idea how she was going to help me, but it was another chance to be with her. She kissed me on the cheek and told me she would see me tomorrow.

When I arrived at her house the next day, she was once again dressed in a very casual and flattering summer outfit and sandals. She had lunch ready and she said that we would talk while we were eating.

"I hope you don't still feel bad about what happened yesterday. The good news is that, as I explained, this is all quite normal and easily remedied with a bit of work and practice. You have to train your body to relax and resist the urge to come so quickly. My husband and I weren't very experienced sexually when we first met, so we were forced to learn together. It's going to take time and patience, but if you'll let me, I'll help you. We'll start today and practice every Saturday after we're done around the house. Sound like a plan?"

"Sure," I said, wondering what in the world the plan really was.

"Okay. Here's what we'll do. Every time we get together, starting today, I'll stimulate you with my hands. Your goal is to hold off for one minute today. Then each time, we'll see if you can't last just another couple of minutes."

"That seems impossible, Patricia."

"Nonsense. You'll see. Let's go up to the bedroom. Get undressed and on the bed. I'll be up in a moment."

"Holy shit," I thought. "What the fuck just happened? Am I in some kind of a weird wet dream?"

Patricia came up to the bedroom a few minutes later dressed in a pink camisole and panty set. God, she looked smoking hot. She told me she was going to repeat what she did the day before, but she wanted me to try real hard to relax and not come. She said what happened yesterday was due partially to the newness of it. She had me get in the right frame of mind.

"Remember, don't stress about how long you're going to last. Your goal is simply to hold on for one minute. Then just let go."

Patricia again ran her finger tip from the base to my head. The urge to come didn't seem as strong as yesterday. She kept reassuring me as her finger made the ascent. Then, she swirled it around my head, which was already leaking pre-cum, and trailed down the front of my cock. She repeated this several times and continued to offer supportive words. By what seemed like the tenth or eleventh time, she told me that three minutes had passed and she wanted me to come. She gripped my cock and stroked it twice before it erupted. Once again, she complimented me on what she described as an amazing load of come. She wiped me clean, told me to get dressed and meet her downstairs.

"Leo, that was absolutely awesome. See how much better that was? Next week, we'll go for five minutes. And then our goal will be to increase it by two or three minutes each time."

"Patricia, I can't imagine how I'll ever be able to get to a respectable time, enough for me to satisfy a woman."

"Stop being so negative, silly. I'll help you. And here's an incentive. When you get to ten minutes, I'll make you come with my mouth. When you get to fifteen minutes, I'll make you come in between my breasts. And when you get to twenty minutes, we'll see about actually using that fat cock of yours in my pussy."

Over the next week, I must have jerked off ten times hoping that it would help me get to my ultimate goal of twenty minutes. I had no illusions that it would happen right away. But I was certainly going to try.

The following Saturday started out the same as the week before. I made it to five minutes with her index finger slowly and sensually going up and down my cock. No gripping or tugging, just teasing. But something interesting happened. I felt like I could go longer and I told her so.

"Okay, let's try something different."

Patricia went to the bathroom and retrieved a bottle of baby oil. She poured some on her hands and then wrapped both of them around my cock, kind of like as if she was praying with them. She applied a little pressure and began to mover her hands up and down.

"See if you can tell me when you feel like you are starting to get the sensation of coming. I will stop and you try to hold back."

Sure enough, it worked. For the next five minutes, she stroked me lightly, applying a bit more pressure each time. She stopped occasionally after brought me to the edge and back. This went on about ten times. She had her timer going and I was up to ten minutes easily. Since she hadn't applied any more oil, my cock had dried up. But it still had some sticky residue on it. She tried something new then that drove me nuts. She gripped my cock tightly with her right hand, held it for two or three seconds, and then released it completely. This made the dry oil adhere partially to the palm of her hand. And when she released my cock, some skin stuck to her hand and was pulled out with it. By the time the skin of my cock went back to normal position, Patricia's hand was on it again in a vise-like grip. With each release I felt like my nuts would explode. But then that feeling quickly subsided. She did this four or five times. Then she added a bit more baby oil and then lightly stroked upward. When her right hand was at the top of my cock, the left hand took over and stroked up. She did this so lightly that she managed to keep me on the edge again. Then she started stroking me quickly with both hands together, one on top of the other, while rubbing her thumb in circles on my frenulum. That was it. I just let go.

When I came down from my orgasm, Patricia noticed that I had a sad look on my face.

"What's with the sad face? I think if I let you, you could have gone another five minutes easy."

"Well, you told me that if I lasted ten minutes, you'd make me come with your mouth next time. I never had a blow job before, and if you put your mouth on my cock next week, I'll come faster than the first time you touched me."

She smiled and told me that her plan was to use her mouth on me to make me come a second time immediately following my reaching ten minutes. And she wasn't going to count how long that come took, so it wouldn't be held against me for the next milestone.

MaxiMilf
MaxiMilf
230 Followers
12