Jack's Beginning

If you have not read the "Conquering the Fearsome Foursome" series, this is how I became interested, sexually, in the mature women. After reading this one, I invite you to read that series as well.

Also, I have received a few comments regarding the spelling of the area that surround the nipple. In my stories, I have been told the correct spelling is "aureola". According to "The American Heritage Dictionary, that is an alternative spelling for aureole, which is defined as "a circle of light surrounding the head, a halo, or around a celestial body. I am using "areola" which is defined as "a small, dark-colored area around a center portion, as about a nipple or part of the iris of the eye." Since I am an American, I will continue to use the latter spelling. If this is a problem, get over it, and just enjoy the story. I do, however, thank you for your note, forcing me to double-check myself.

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For those who have not read the series, my name is Jack. At the time of this story, I had just graduated from high school and preparing to go to college in the fall. I started school a year later than most of my classmates, so I was about to turn 19 at the end of that summer. During high school, I was anything but a ladies man. I was about 5'10", fluctuated from 180 to 195 depending on the amount of beer I drank, with a fairly athletic physique. I played most of the major sports, but wasn't one of the marquis players on any of the teams. My problem with all the girls was that I looked like the guy next door. I was everyone's friend. I lacked that "bad boy" personae that seemed to get my friends laid…a lot. I did have dates and even found myself getting some here and there, but it was just not as often as I would have liked. But then again, if I got it 24/7, it probably wouldn't have been often enough. Ah, youth and hormones!

During that summer, rather than get a physically or mentally demanding job before heading off to college, I got a job as a life guard at the local swimming pool. As luck would have it, the pool was just down the road from my house so that I could roll out of bed at 8:45 AM and be at work by 9:00, which was really helpful on those mornings after some wild nights on the town. My hours would alternate each day. Mondays, Wednesdays and Saturdays, I would work 9:00 AM – 3:00PM and on Tuesdays and Thursdays, I had 3:00 PM – 9:00 PM, with Fridays and Sundays off. Being one of the oldest guards, most were rising juniors and seniors in high school, I was given a set of keys to open or close, depending on the days I worked.

Since this pool was also my neighborhood pool, it was the one I grew up swimming at every summer. You could say that I was a "pool rat", in that I rarely left except for meals. I was even a member of the swim team. My history with that team is how this all began.

That particular year, the team did not have enough older guys. Without at least 4, they would have to forfeit too many races and therefore would not be very competitive as a whole. The team mom, a mother that basically keeps all the parents and kids in line when not swimming, recruited me and another guard to swim, and they would see to it that my work schedule could be altered to accommodate the meets. And since I was at the pool most of the day anyway, I wouldn't have to go to practice. I half-heartedly agreed, seeing that she asked me in front of a dozen other moms, including my own.

The first meet came and, when it was my turn to swim, the entire team and gallery were amused by the fact that I took my place wearing a pair of swim trunks that went down to mid-thigh, and not those ball busting racing suits. I took a respectable second place in the race. Given that there were only two of us, I was happy just not to get disqualified.

The following Monday I was collared by the team mom. "I want you to try this on." It was one of those racing suits.

"No ma'am! I am NOT putting one of those things on. I will look ridiculous. Really!"

"I am not asking you to wear it at the meet, just try it on and see if it fits. That's all."

Knowing better, I again caved and did as she asked. I went into the guard's locker room and changed. The suit would have fit except for the bulge in the front. I never considered myself to be other than average, if 7" on a guy my height is average. What I did know was I was thicker than most, a lot thicker. And with this suit on, it looked even thicker. There was no way I was going to wear this out in public, much less at a swim meet where there would be families that I knew since grammar school.

"Mrs. M.," I called out, "this thing does not fit me right." Mrs. M., short for some long eastern European name that had a bunch of consonants and no vowels, was the team mom. In order to be the team mom, she had to be on the pushy side; otherwise she would never have been able to get anything done. So before I knew it, she had walked in the locker room, "Let me see, maybe you just need the next size."

She stopped short once she got an eyeful. It was of no use trying to cover up now, since the damage was done, so I just stood there and said, "See."

She just stood there, gawking for about 10 seconds. Finally she realized what she was doing; blushed, mumbled as quick "Sorry", and made a hasty retreat out of the same door she entered.

For a quick second, I was sort of proud, but then the realization set in that she was one of the women that I would have to face on a daily basis. I began to feel the embarrassment of it all overtake me. I speedily changed back into my trunks, which hid what needed to be hidden very effectively, and walked back out. If I hadn't been embarrassed before, I was now. In the corner Mrs. M. was in a huddle with a group of other women, talking in that hushed voice that women who are telling secrets use, and looking over there shoulder at the locker room door. When they saw me, they stopped, straightened themselves up and separated.

Great! And to make it all worse, the Chairperson of the Pool Operations Committee, Marie Pardoe, my boss, was one of them. I could only suck in my pride and head for cover, the guard's office. When I related the story to one of the other guys, hoping for some type of male consolation, he just broke into hysterics and said "Man that sucks!" Looking back, that really was male consolation at its best.

For the rest of the week, as I walked around the pool doing my tasks, I would catch the glimpses of those same women. Thankfully, they hadn't spread it further, because if they had, I am positive it would have gotten back to my mother, the queen of the rumor mill. I tried my best to smile, but most of the time I ignored it.

On Friday, normally my day off, I had volunteered to work the afternoon shift and help set up for the swim meet the following morning because I needed the cash. I got all the lanes in the water, the team areas cordoned off, and the chairs set up for the spectators. I went off to lock the back gate, and on my way, I saw Mrs. Pardoe walking up the sidewalk. I was a little taken back by seeing her, not only because it was after closing hours but because she was dressed really nicely.

I should tell you about Mrs. Marie Pardoe. First, she really isn't a Missus, at least not any more. She lost her husband to cancer a few years earlier, but we all continued to use the Missus out of respect. She is a fiery little woman in her mid to late 30's. She stands about 5'3, big Texas-style red hair, which is probably colored since every now and then the tint changes slightly. Her body type would be characterized in today's politically correct terminology as "thick". She wasn't fat by any means, there weren't any signs of varicose veins or cellulite on her legs, nor did she have the arm wings or sagging cheeks etc. What made her appear to be that way were her enormous tits. The guys would always joke that those things entered a room a good 5 minutes before she did. They were THAT big. And when she went swimming, if she did the backstroke, they would protrude out over the water like two buoys in the ocean. It was pure joy to see her walk around the pool deck in her bathing suit because with each step, those tits took on a life of their own.

Her personality was great though. She had 2 young pre-teenage girls at home so she knew all the slang, dirty jokes and culture of my generation. On occasion, she even told me a few jokes that I hadn't heard before, complete with the profanity. At first, it was weird having an adult talk to me that way, but I soon realized she was treating me as an adult too.

As she walked up the sidewalk under the lampposts I couldn't help but notice her attire. She was wearing a bright yellow sundress, medium heels and carrying a large cocktail glass with some kind of tropical fruit drink. Her hair was done impeccably, as was her make-up, but then it usually was.

"Hi Mrs. Pardoe, what are you doing out so late? And, might I add, looking like an ad for a tropical vacation?"

"Oh Jack, you are the charmer, aren't you? I was just in the mood to put on something colorful. How are all the preparations for tomorrow coming?"

"I'm all done. I just finished locking the back gate and was going to lock up in here next. Is there anything else I need to do?"

She walked through the office and out onto the pool deck, looking around the dimly light area as if she actually knew what to look for. Her expertise in pool operations came from going to the pool every summer, but since the homeowners association that ran the pool was in desperate need of volunteers, she was given the chairpersons job. The guards really ran everything anyway, so unless there were complaints, she just made sure the vendors and the guards were paid. "Looks like you have everything covered." She turned and headed back into the office. She pulled out the next weeks schedule and looked it over as I went about locking up cabinets and storage closets. I thought it odd that she would be looking at the schedule like she was; she never did that during the day, much less after closing.

I came back into the office and she was now sitting at the desk with her drink in one hand, the schedule in the other, her legs crossed and her dress high on her thigh. I had to stop a second to take it in, and then proceeded to gather my gear. I threw on my old "Lifeguard" t-shirt and headed for the door.

"Jack, I wanted to talk to you a second." Oh, shit here it comes, I knew it.

"I heard what happened in the locker room with Mrs. M., and I wanted to let you know how sorry I was. I know this week has been tough with all the stares you've been getting. Let me tell you, I know all about stares." She smiled and continued, "With these things, I have rarely ever spoken to a male without having his eyes leave mine and venture south. And linger too. So believe me, when I say, you will get used to it, and eventually, you might even enjoy it."

I could feel the blood rushing to my cheeks and she could see my face redden. I hated the fact that I blushed so easily, announcing to the world my emotions. She saw my embarrassment, stood up and came over directly in front of me.

"Don't be embarrassed, Jack. I'm really only trying to ease your mind a bit." She took a step forward, now close enough that the tips of her tits were touching me. I stiffened my back slightly as she placed a hand on my chest. "To be honest Jack, I think we can actually help each other."

Looking at her questioningly, "How could I…?"

"Well, you see. You and I have a lot in common here. We both have been 'blessed' with features that, well, are pleasing to the opposite sex, am I right?" I nodded slowly, not wanting to be overly agreeable yet.

"I was just thinking that maybe…well… we could share, so to speak, ourselves with each other. Have some fun, maybe even a lot of fun."

At first I didn't really understand where she was going, my naiveté showing again, but then it hit me. I couldn't believe an older woman like her would be remotely interested in someone my age.

"I… don't … under…" She cut me off before I could finish. "Jack, I should also tell you that I am rather talented in ways that are pleasing to men." She licked her lips seductively and then flashed me a smile that could kill. Her hand was still on my chest through all this and now had begun to circle my nipple, flicking it lightly occasionally. My cock was probably more in tune to what was happening than my brain was, because it began to grow. It didn't help that she pressed herself into me further. And before I could answer her, her other hand had made its way to the drawstrings of my suit. I took a deep breath, put my hands on the counter behind me, and looked up at the ceiling, waiting for what was going to happen next.

"Relax, Jack. Look at me. Better yet, look at my breasts." As she said this, I did as I was told. When I looked at her chest, the pressure she was putting on me forced her tits upward, creating an incredible cleavage. My cock was now beyond return and was following a path down my leg. "Now touch them." I reached up and placed a hand on the side of each tit. They were soft and supple. I pressed my hands in harder and gave each one a gentle squeeze.

Amazingly, there was still space between us, even though her tits were pressed hard against me. Her lower hand moved downward in search of her prize. She didn't have to go far to reach gold. A look of wonder came over her face when she reached my crotch. I guess she was expecting my cock to be pointing up or out, rather than down because she said, "Where is it?"

I bashfully said, "It's going down my…" She let her hand travel a bit further and felt the base of my cock under her fingers. She quickly spread her fingers out to fully comprehend the girth of my dick. I let out a soft groan as she took my manhood into her hand, even though it was still covered by my bathing suit.

She looked up at me with a bright smile, "I think I can safely say that the rumors are definitely true, maybe even a bit understated." Of course, I blushed again but held my gaze into her eyes.

She felt along the entire length and back up again, "Would you mind if I took this suit of yours off?" To my surprise, I heard myself say nonchalantly, "Not at all." Both her hands were soon tugging on the drawstrings and as she slid the suit down, bent over to see what she had heard about and had been feeling. When she pulled the suit down over my thighs and when my cock head finally cleared the bathing suit, it sprang upwards and grazed her cheek. She let the suit go and it fell to my ankles where I kicked my way clear of them. Standing there now in only a t-shirt, she uttered "Holy shit." I took that as a good sign. "You're…a lot bigger than my husband was…!"

She ran her fingers gently along the shaft, scraping her polished nails lightly. I couldn't help myself and I let out a moan. "You like this, huh?" she whispered.

"Uh huh. Mmm."

She reached around behind her and pulled a chair up and sat down with me standing between her legs, my cock level with her tits. She moved her face in closer until I could feel her hot breath on the head. She pulled my cock down and pressed it into her cleavage.

"Looks like a perfect picture for a porn magazine, doesn't it?" I could only nod and smile, desperately trying not to thrust forward and ruin it.

She guided it over the exposed skin of her breasts, leaving a small trail of pre-cum. We both moaned softly as we watched together what she was doing.

"I love the feeling of a cock on my tits. It makes me feel so sexy. Do you like it?"

"Oh, yea. It feels amazing."

Marie pulled it up to her face and lightly kissed the head, licking off any remnants of pre-cum. She turned her head slightly and ran my cock across her cheek. Up and down her head went, making sure she got all of my cock against her face, before turning the other way and doing it all over again against her other cheek. No female had ever done anything like this to me before, so I was enraptured in it all.

"Mmm, you cock is so…." Unable to think a word, she just took the head into her mouth and moaned. She pulled it back out with a loud slurping noise, took a breath and put it back in. This time she used her tongue to explore the contours of me, taking me further into her mouth little by little. I held onto the counter behind me tightly for fear of collapsing if I let go.

She started out with both hands around my shaft, but as she took more of me into her mouth, she used only one. Slowly, she sucked me, moving her head back and forth, savoring every inch she had in her mouth. I watched her take me as far into her mouth as she could, hold it there, using her tongue to massage the sensitive areas of my pole before pulling back to do the same to the head.

She began to moan softly on my dick, then with more intensity. Still holding the base with one hand, she took me out of her mouth. She was now only licking me, but with a lot of passion and urgency.

"Mmm. What a wonderful cock you have. Mmm. Ooh…Mmm." She licked it a few more times and then stuffed it back into her mouth. She was moaning almost continuously and she pumped my cock with both her mouth and hand. Her eyes were shut and she began to shudder uncontrollably. She held me in her mouth until she stopped, her lips pressed tightly around me. The vibrations were almost too much for me. I was on the verge of exploding when she gave the base of my cock a squeeze and let me fall from her mouth, trying to catch her breath.

She licked me from base to tip, being sure to flick the tip, causing a shiver to run up my back. She put her other hand back onto my shaft and I noticed her fingertips were wet. Then I dawned on me that she was playing with herself while she was sucking me.

"I want you cum, Jack." She licked me again, flicking her tongue quickly on the tip. "Let me have it." She put it back in her mouth and slurped it loudly as she withdrew. "Are you close?" She grabbed my balls and rubbed them softly.

"Very!" It was all I could manage. My balls were tightening with each stroke. She stuffed me back into her mouth and sucked me with fervor. She'd pull it out of her mouth every few strokes to tell me how good I tasted or how much she wanted my cum. It was all I could take.

"Ooooh, yes, Mmm, ahhhh, yessss. I'm…I'm…" I couldn't finish the sentence because she knew what I was going to say. She already had a mouthful of my cum hitting the back of her throat. She took two spurts in her mouth before pushing my cock down into her cleavage. I let two more surges go into that chasm before I nearly crumpled to the floor.

She swallowed every drop and continued to kiss and suck me, getting every drop she could. When she finished, she rubbed the cum that was on her chest into her skin like it was lotion. I stood there watching her in awe, still not believing this was happening to me.

Once finished, she stood up, pushing the chair away from herself and wrapped her arms around me, hugging me firmly to her body. I put my hands on her tits again, kneading them as much as I could before she released me.

"Oh, that was so wonderful, Jack. And that feels so good too. I hope you enjoyed it as much as I did?"

"I think I enjoyed it more," I said with a laugh. "I seriously doubt that," she replied.

I didn't want this to end so I asked her, "Is there anything I can do to you?" hoping to get inside her dress.

She released me from her embrace and stepped back, "You have no idea what you have already done for me. I think that's all I can take right now. Besides, it's getting late and we need to get this pool closed up before someone thinks there are trespassers in here and calls the cops."

She straightened herself up and headed for the door. She turned and looked at me, still standing there with only my t-shirt on and my dick softening, smiled and said, "Now that is a wonderful sight." I looked at myself and quickly pulled on my suit. "Good night, Jack and thanks."