Sometimes reality goes above and beyond one’s own inner fantasy life. I was near the end of my college years, was working a summer job that was a mix of groundskeeping and, in the afternoons and early evenings, filling the role of a makeshift lifeguard at the apartment complex community pool. I’d get hot and sweaty cutting grass and hauling garbage in the mornings and then strip down to my swim trunks in the afternoon and report for duty at the fenced-in pool area in the hot afternoons. More than anything my bosses wanted me to check IDs and make sure that non-residents weren’t sneaking in and using the pool. If there was an emergency I would do my best to assist, but I actually wasn’t certified.

Naturally, I quickly developed a dark all-over tan over the days in the sun, and indeed I did prevent all manner of non-invited “guests” from over running the smallish private pool. The unintended side effects of this were that the residents treated me with a kind of sweet-talking deference to get their friends in. Still, a number of the single gals who lived there, both with and without children would casually chat with me for reasons I can only imagine. It was a pretty ideal summer job for a well-mannered, well-read, slender-but-fit young guy to have back then.

Not too far away, and simultaneously, the business office staff of the complex had several women who managed all things related to the residents and the maintenance of the facility. One of them was a young, attractive Asian-mix lady in her early thirties who happened also to be the wife of the grounds maintenance manager, who was my immediate boss. Tara was shorter than me, nicely proportioned with a nice figure and silky-smooth skin. She was, looking back on it, the ideal milf as it were; an elegant dresser, professional, but also had a sassy or snarky side. She could be critical and “bossy” at certain moments, but also strangely nosy, asking personal questions and wanting to know more about one’s personal life. She was also known as the queen of local gossip. Since she was married to my boss I generally tried to ignore her, even though quietly I did find her sexy and interesting.

One time, toward the end of my summer tenure there Tara showed up unexpectedly at the poolside and came inside the closure, seating herself down next to me on a recliner lounge chair in the warm sunshine. This wouldn’t be too unusual in that we had a policy that around 5 pm the younger children were sent out and the pool hosted an ‘adult swim hour’, to be mostly noise and commotion-free. The office closed around that time and Tara and her family lived in one of the nearby surrounding apartments, one of the perks of working there.

What was unexpected, and a bit of a surprise to me was that she showed up in a floral bikini, wearing designer sunglasses and carrying a large towel that she spread out over the chair. That was all a secret thrill to witness, but my first thought was that she was there to check up on me, to see if I was doing my job properly or professionally. We chatted in a friendly manner, but I was extra careful not to sound too cheeky or casual. I thought it odd though when she said, out of the blue, “I’ll bet you get a lot of ladies hitting on you here at the pool. I can only imagine so-and-so trying to get you back to her place and trapping you into becoming her boyfriend. You’d better watch out. Single mothers will do that to you.”

I wasn’t sure how to take that advice. Was she baiting me to spill the beans and talk about my possible indiscreet ways here at the pool? Or was this part of something else? I just sort of laughed it off. “Oh, they’ve never done stuff like that!,” although some of the ladies, and younger women actually did flirt with me there. This conversation made me feel a bit self-conscious and I happened to notice at that moment that my bathing suit did look rather tight, and more than that if I had to be honest, my package down there was more three-dimensional and ‘defined’ than what might be appropriate for a pool attendant. This was a phase of life when 24/7, my wiener was always one hair trigger from ballooning onto something much larger.

“Come on,” she prodded me, “There’s no way you couldn’t be hit on by these people!” I almost thought I could discern her taking sneak-peeks at my crotch here and there beneath her stylish designer sunglasses. Sure enough, my smallish suit wasn’t leaving too much to the imagination. In my mind, I thought what a fool I was for not having gone to the mall to purchase a new, more proper-fitting bathing suit when I’d first been given this job.

But the conversation continued while the last of the family swimmers cleared out of the fenced-in pool area. Soon we were alone in the late afternoon sun. At one point, she took a dip in the glistening, well-skimmed water, one of my other assigned tasks, and when she emerged her bathing suit seemed noticeably thinner and more revealing, or was it just my imagination? After toweling off her skin appeared more delightful and sensual than before, showing the “goose bumps” that always turned me on, even as a small kid. She was crossing and uncrossing her legs, something I had a hard time ignoring.

She asked me questions about my girlfriend and sheepishly I admitted that recently we had broken up, although we had talked about getting married for almost two years, and that I always felt frustrated. In a moment of weakness, I admitted to Tara that the physical relationship could only advance so far because my girlfriend wanted to save herself for marriage. This drew out a good hearty laugh from Tara. “How could you be such a fool? Girls will always do that to their boyfriends, teasing the hell out them and until they finally give in and tie the knot.”

Then came the first big surprise in our increasingly intimate chat. She went into a kind of confessional: “You know, Rob and I are now separated, and he’s seeing that young bitch over in apartment 113. But it doesn’t really bother me that bad because I have a new boyfriend too that I really have a lot of fun with.” I nervously swallowed, and almost coughed.

“Oh wow, I had no idea,” I stammered. She adjusted her bathing suit top and went on.

“Yeah, we just argued too much. My new man-friend is an older guy, in his fifties and likes all kinds of things that Rob was too clueless to do or think about. And he’s just totally laid back.”

I sat, stunned in silence. “Wow,” I repeated, inanely. Now I somehow knew I was out of the rough in terms of testing and into some new, wild and unexplored, even novel territory with this ethnic Filipina co-worker of mine, who up until that afternoon seemed like an demanding taskmaster. “Gosh,” I said, “After what I went through with my former girlfriend I would love to experience a dating partner like that.” I could hardly believe those words had just rolled out of my mouth. But clearly, some kind of switch had just been tripped in my head. Hormones must have played a part.

“What I think I really need at this point in my life is someone slightly older with more experience who can teach me the ways of being more physical, more creative, and more skillful when it comes to intimacy. I also really want a time in my life where I can just be…physical, you know? No strings attached. I want a kind of teacher, as it were.”

“Oh for sure,” she said, as if we were now buddies talking about favorite fast food restaurants. “So what’s been keeping you from going out and opening up your life a bit? You could have a lot of fun, and just learn how to relax and be your true self. Of course, you gotta be careful not to get trapped,” she finished with a chuckle.

And here’s where I got a bit dopey perhaps, went off the proverbial deep end. As if almost in a dream I said, “I’d really love to try that. I’d really love to find that strings-free lover, but…” I stammered, “I’m a bit worried about my size down there,” pointing toward my slightly piqued and growing wiener.

“What?! Oh my,” she laughed, but then quickly shifted into a sultry, lower voice, not missing a beat. “Well now you’ve got me curious. I’d be curious to see what you mean by that,” she said with a wry smile. “I’d like to take a look sometime and see for myself.”

“Are you sure?” I replied, incredulous. Things had gotten so surreal so quickly. I felt like I was in over my head, yet somehow my quick, possibly juvenile thinking kept me moving ahead. I knew that right behind us, alongside the end of the pool itself was the bathroom, shower, and changing facility, for which I was given a key. “Shall we go into the men’s bath? I could give you a quick peak there.”

She smiled, nodded, chuckled, and said some words that gave the affirmative. I think she was just as surprised as I was. In the most inconspicuous, casual way possible we got out of our sun chairs and sauntered over to the metal door. I went in first and she followed, then locked the door. The tiled room was empty, each squeak or footstep making an echo. Without missing a beat I went into the separate shower room and instinctively pushed in the metal button that activated the water. Within seconds warm spray was flowing down my tanned torso and now soaking suit.

Tara mirrored me perfectly and went to the shower head next to mine and turned on the water. We were both facing the wall beneath the shower heads, instinctively as if this was just another PE class locker room shower. I was strongly aware that my penis was now sticking down and out of my bulging suit, heading toward a more complete erection. Finally, after what seemed like an eternity I called over through the watery noise, “Are you sure?” She nodded and smiled. I noticed she had taken some liquid soap and was now lathering her arms and chest.

I reached down and began to pull down on my clingy, sodden, ill-fitting garment. My rod was gaining size with each second and I could sense that she was mesmerized with anticipation. I must have turned slightly away from her for a moment, perhaps to get down some hand soap, and she blurted out, “That is a nice ass, my friend.” Almost as if by remote control, my hands went back behind me and began soaping up my buttocks.

“Are you ready?” I replied, awkwardly.

“Oh totally,” she said in what seemed like a whisper. “It’s like I’m getting a female hard-on.”

I modestly rotated toward her and noticed her eyes widen, and her grin as she perused my form up and down. “Nice.” She paused for a moment, soaking it all in. “May I?” she inquired.

“Sure” I replied. My instincts told me what was next. Her arm reached over and her hand took hold of my wet, soaking cock, now fully flagstaff erect, and slowly began sizing it up. “That feels good,” I shivered as her palms slowly slid up and down the length of my shaft. I could’ve come instantaneously, explosively if I hadn’t been in such a freaked-out state of mind.

She must have sensed this and looked deeply into my eyes and replied, “Would It help you if you could feel these?” She instinctively unsnapped her bikini top, slid it off, and tossed it over a nearby bench. “Go ahead,” she urged.

This was nothing short of amazing for a guy who had only groped his girlfriend’s smallish tits in the darkness of a car. The moment seemed timeless. My hands went to autopilot as I caressed and washed her astounding, firm boobs. simultaneously I felt and watched her stroking my pulsing rod. I must have sighed, and then reached behind her shoulders and pulled her in close. I could now smell her cologne and her tied-up hair brushed against my face. It was too much, my nervous system exploded into a tight, arching, lightning-fast orgasm, spraying my globular flow all over her hands. I could hear my echoing moan in the shower room, almost as if I were outside of myself. My hands slid down to her waist, then buttocks, still covered by her bikini bottom. How deliciously perfect they felt in my lightly massaging fingers.

“Well, well,” she chided, “That is some serious jism.” Unexpectedly she knelt down in the shower in front of me. “You weren’t lying,” she continued, “but I’m gonna be honest- it would be fun to try this thing out and see how it really feels.

Her next move also caught me off guard. “Can I taste it?” she said as she pulled my still fully erect rod toward her mouth. Before I knew it she was licking the come off my head and gently sliding the tip in and out of her mouth. “Tell you what. After we finish here and after you clock out you should come over to my apartment. I think it would be fun to take you for a test ride.”

I hardly knew what to say I was so entranced and in the throes of electric release. “Don't worry about my son. He’s out with my mother tonight, and Rob is out with his bitch.”

“Okay,” I could only reply. “You want me to just show up?”

“You can come around by the back sliding door,” she ventured. “I might have some leftovers I can feed you, and then we can play.”

Fifteen minutes later I awkwardly rapped on her back glass door, hoping none of the neighbors were paying attention. I was still in a state of shock and awe. But in actuality, this was just the beginning. In a moment she appeared behind the glass door, then slid it open.

“Glad you decided to show up,” she blurted, wearing only a short, white bathrobe, one that barely covered her vulvic area. Her bare hips seemed to glow with a newfound tan hue. The top and front of her robe hung partly open and I could glimpse that warm, wonderful cleavage. “Come in,” she stated matter-of-factly. “Follow me.”

And indeed I followed her command.

(To Be Continued In Part 2)