Looking Back

It was a Tuesday, just after lunch, and Louise and I had just returned from a morning's shopping at a nearby mall (Okay, yes, we really were spoiled brats then. Just because I was eighteen didn't mean I had actually grown up into a mature, responsible adult.). We had changed into our bikinis and were stretched out alongside the pool, soaking up rays. Louise had stripped off her top and was lying on her back, while I lay on my stomach with the straps to my top untied. We were both about to fall asleep when we heard the gate open as the Pool Boy entered to do his weekly cleanup of the pool.

"Excuse me ladies, I need to clean the pool," stating the obvious in an effort to get us to put our clothes back on. There was just a trace of a Spanish accent in his speech.

Louise pushed her sunglasses back on her head and, seeing that it was the Pool Boy, said, "Go ahead. We're fine."

I rose up on my elbows facing him, which exposed most of my 38 C breasts, and then put my head back down, assuming that Louise had things handled.

"Don't you want to put your clothes on?" the Pool Boy asked. I guess he was trying to make sure we understood that he was coming in.

Louise sat up and said, "Not unless you insist." As she spoke, she pulled the bottoms of her suit down around her knees and then let them drop to her feet so she was now completely naked. She really was a little slut even then.

The Pool Boy stood on the opposite side of the pool staring at Louise who sat naked and staring back with her legs spread so there was no impediment to a full view of all she had to offer. For the longest time he just stood and stared with this "what the fuck," look on his face.

Finally he began walking around the pool towards us with his eyes still fixed on Louise, who was now slowly stroking her pussy and smiling at the Pool Boy. As he arrived, I sat up and fastened the top of my suit. It was obvious that he was fixated on Louise and ignoring me, so I just wanted to see what was going to happen.

He came to a halt directly in front of Louise, who was now using both hands to hold her plump breasts out to the Pool Boy like an offering. Based on the bulge in his shorts, it was obvious to both of us that he was getting her message. It was clear his dick wanted to fuck her as bad as Louise wanted it to fuck her, but as it turned out, unlike most men, the Pool Boy wasn't ready to let his dick do his thinking—at least not on that day.

He just stood before her staring for the longest time. Then he turned and looked at me and said with a smile, "Is your friend really this much of a slut?"

I smiled in response and shrugged my shoulders, as if to say, "Pretty much."

The Pool Boy turned back to Louise and stared a bit longer.

Louise said, "Well, are you just going to stand there and stare?"

He stepped forward and swept Louise up in his arms. Louise, grossly misinterpreting his intentions, threw her arms around his neck and tried to kiss him. He leaned back onto one foot, avoiding her, and then spun and threw Louise into the pool, her long blonde hair flying outward as he turned and she sailed towards the pool. She screamed as she flew toward the water, and I was trying, and failing, to suppress a laugh.

Louise came up wet and swearing like a logger. My laughter just made her madder. Her heavy eye make-up (remember how much we wore in those days?) was streaming down her face. The Pool Boy stood with his hands on his hips looking at her with a smile. He waited until she finally ran out of invective, and then he said, "Listen puta. I have daughters your age, and I work around puta like you at the high school where I teach. You are lovely, but you have a lot to learn about men."

Louise just stood naked in the waist deep water and stared back looking pissed. She knew enough Spanish to know he had called her a slut. Finally the Pool Boy grabbed a beach towel and tossed it to her. "Your make-up is running," he said. "Don't get it on the towel. You'll ruin it."

"Fuck you!" Louise said in response.

The Pool Boy laughed and then turned towards me, "Kate, I think I should leave now. I have time to come back and clean your pool tomorrow morning. It would be good if your little friend was not here then, Sí?"

I was still laughing, but I managed to get out a brief, "Okay, sure," as he turned and strode around the pool to gather his tools on the other side.

Louise took off in a major huff right after the Pool Boy left, and I continued to sun myself while I thought about what had just happened. Frankly, the whole thing was a mystery to me. Louise was a total fox. I knew any number of guys who would have done almost anything to get into her pants. So why did the Pool Boy spurn her advances and why in such rude way? Was he gay? Given the size of the erection he was sporting beneath his shorts, I was certain he wasn't gay. So what was it?

As I lay there alone in the sun puzzling over the events of the last half an hour, my mind eventually gave up on finding an answer and became a good deal more focused on the Pool Boy as a sex object, especially the bulge beneath his shorts that had been so obvious as he confronted Louise. The more I thought about him, the hornier I got.

I had stripped off my bikini top after Louise and the Pool Boy left, with a plan to get a bit more sun on my chest. As I lay on my back thinking about the Pool Boy, his muscular build, his penetrating blue eyes, and especially the bulge under his shorts, I began to absent-mindedly massage my tits and then to pinch and pull on my nipples. I hadn't really intended to masturbate, and I certainly didn't want to do it to a fantasy about the Pool Boy, who I was pissed at because of the way he had treated Louise, but . . . oh, he was so hot when he had lectured Louise and thrown her in the pool, and my massage of my tits was lighting a fire in my pussy. Well, to be fair to it, the Pool Boy had lit the fire some time ago. I was just stoking it as I played with my tits.

Finally, after telling myself no several times, I slid the fingers of my right hand beneath the bottoms of my swimsuit. Fuck I was wet. "Okay," I told myself. "I'll think about Jimmy Richards," a tall blonde jock who lived down the street. "Yeah. I'll get off on him." With that, I quickly stripped the bottoms of my swimsuit off so I was lying completely naked on the chaise longue. I spread my legs and slipped a couple of fingers into my wet slippery pussy.

"Damn it! This isn't working," I said aloud to no one in particular. My mind kept returning to the Pool Boy. I had this image of his tight muscular hips atop his heavily muscled legs as he had turned away from me and thrown Louise in the pool. I was imagining that cute butt naked between my spread legs with both my hands on it pulling him and his cock further into my hungry cunt. Oh fuck, the image was hot.

I pulled my knees up and spread my legs so that my heels were touching, beginning to use both hands to masturbate. Two fingers and then three were buried deep in my cunt, twisting and turning and stroking the G-spot at the front of my vagina. The other hand was stroking the now slippery wet labia above my cunt and flicking my now fully aroused clit.

I recognized that there was no turning back from this, so I surrendered to a fantasy in which I watched the Pool Boy disrobe before me, while I lay naked masturbating, just as I was now. First he pulled off his T-shirt, exposing his chiseled chest and abs. Fuck, he was hot! Then he released his shorts and let them drop to his feet. He was wearing a pair of white jockey shorts that did nothing to disguise the large erection beneath them. As he stood before me he stroked his erection through the soft cotton of his shorts.

"Is this what you want" he asked, pushing his hips toward me. "Do you want to see it?"

"I want to fuck it," I responded in my fantasy. I think I actually said it aloud as I lay by the pool fantasying about the Pool Boy. When my masturbation fantasies get really hot, like this one, fantasy and reality begin to blur.

He pushed his jockey shorts down, releasing his cock. It wasn't huge, but it was far from small, and it bobbed a bit as it was released from the bondage of his shorts. Then it just stood straight and tall, leaning away from his stomach at a steep angle. The Pool Boy kicked his shorts and underwear away and stood before me stroking his rigid cock.

My fantasy was totally out of control now. "Get over here and cum on my tits!" I snarled in a command to him. Oh God, what a fantasy. I was so close to cumming. I imagined him standing next to me with his prick pointed down towards my chest, stroking it with his right hand as hard and fast as he could. Then it spurted stream after stream of white pearly liquid onto my naked tits, as the Pool Boy gave out a groan that could be heard two houses down the block.

That did it for me. I came with a scream that matched my fantasy of the Pool Boy's groan. It was probably the most intense orgasm I'd ever had up to that point in my young life.

The Pool Boy came early the next morning to do the work Louise had interrupted the day before. Like any good eighteen-year-old, I was still in bed sleeping off the effects of the prior night's party, so I missed him.

* * * * *

That was the beginning of my obsession with the Pool Boy. I'm sure I masturbated a couple of times a day for the week that followed, and the Pool Boy was the subject of my fantasies accompanying every one of those masturbation sessions. I dreamed about sucking his cock and about fucking him in every position and place my young imagination could conjure up. I dreamed about having him eat my pussy. I even imagined a threesome with Louise and the Pool Boy, where he fucked her just because I told him to and then immediately turned and began fucking me with his magically recovered erection.

By the end of the week I was determined to find a way to seduce him, but given Louise's experience, I could see it was not going to be easy. This was frustrating, because I was used to being able to get laid whenever I wanted by pretty much whomever I wanted. After all, it was 1968, and I was living just over the hill from Berkeley. All I had to do was to go over there and look winsome, and some guy would pick me up and take me back to his apartment for an afternoon fuck (but more on that later). Now the question was how to seduce a guy who, even though obviously turned on by Louise's wanton display of her naked body, still had turned her down. What made this guy tick? I couldn't figure him out.

He was due to clean the pool again on Tuesday afternoon. I called Louise and made up some excuse about why we couldn't get together that afternoon. She was still really pissed about being rejected and thrown in the pool, so I didn't want her around. It was obvious that lounging around the pool in a skimpy bikini as he worked wasn't going to get the job done, so after spending most of the morning digging through my closet, I decided to try a very different approach. First I tried on a pretty sundress with a string top. Nice, I thought as I looked in the mirror, but I couldn't see how that outfit was going to seduce him.

Then I had an inspiration. I peeled off the sundress, tossed it on the bed, and dived deep into the back of my closet. Yes! I still had the uniform I had worn to the Catholic girls high school I had attended. Perfect, I thought. He works in a high school, and I bet the girls drive him nuts, but he doesn't have to deal with girls dressed like I did at the Catholic school I attended. He won't be able to turn me down in the outfit I had worn to school only a few weeks ago.

It took a little more digging in the back of the closet, but well before the Pool Boy was scheduled to arrive, I was dressed in the classic school girl outfit: short grey and blue plaid skirt; white knee socks; Mary Janes; and a white blouse that was old enough so that it wasn't hard to see the lacy bra I wore beneath it. I combed out my long hair, wove it into two braids and then put them up on top of my head. My makeup was light, but I made sure he would notice my blue eyes. And for a final touch, classic white cotton panties. Perfect, I thought. Then I waited for him to arrive.

Looking back now, I think waiting for him was the hardest part. The longer I waited, the hornier I got and the wilder my imagination got. I actually had to change my panties because I soaked the first pair just thinking about what I wanted to do with the Pool Boy.

When he did show up, I forced myself to remain inside, watching him work but not showing myself until he had the job done and was beginning to collect his tools. Then I stepped outside carrying a tray with two glasses of iced tea on it and asked him if he would like a drink of something cold.

He was standing across the pool from me and looked a little surprised. I guess he had never seen me with that much clothing on before. Then he did a double-take as he realized what I was wearing. He thought for a moment, mopped the sweat from his brow, and said, "Yeah, okay. That sounds good."

I set the tray and drinks on a table and responded, "Come over here and take a break while you have some iced tea." I sat in a chair along side the table taking care to keep my short skirt as far down as I could get it, while the Pool Boy walked around the pool. God, he looked as sexy in the flesh as he had in all the fantasies I had spun out about him during the prior week, except he had more clothes on.

He sat opposite me, each of us alongside the table. This allowed the Pool Boy to see all of me. Nothing was hidden behind or beneath the patio table. I carefully crossed my legs, which caused my short skirt to slide up my thighs, but I quickly tugged on it to get all the coverage the scant piece of cloth would give me. He seemed a bit tongue-tied as his eyes roamed up and down my body.

Finally, after a couple of gulps of iced tea, he tore his eyes away from my tits and said, "You look very nice today."

"Thank you. I hoped you would like it. You didn't seem to like the swimsuits my friend and I were wearing last week."

He smiled and pulled his eyes back up from my legs. He actually blushed as he said, "Oh, I guess I got a little carried away. Your friend was just being a bit too aggressive for my taste. I teach in a high school, and some of the girls do things like that to us all the time, even though they know we can't respond. It gets very frustrating."

As he talked his eyes wandered down to my tits again. His eyes seemingly had a mind of their own. They were going to focus on my tits and my legs, no matter how hard he tried to do otherwise.

I uncrossed my legs and then pulled my feet and my knees together tightly while I tugged on the skirt again. I wondered if he had gotten a glimpse of my white cotton panties in the process. I certainly hoped he had.

"Well, Louise can do that," I said.

"What?" he asked jerking his eyes back up to my face.

I smiled inwardly. The schoolgirl outfit was having its desired effect. His attention span was almost gone. He had completely forgotten we were talking about Louise.

I deliberately delayed responding as I let my eyes wander down to the bulge in his pants caused by his growing erection. That vision distracted me for a moment, but I pulled my eyes back to his face and said, "Oh, I just meant that Louise can be very aggressive—sexually that is."

"Do you wear that outfit to school?" he asked after another pause, while his eyes scanned my body. The change in subject indicated that he clearly was more interested in me and my schoolgirl outfit than he was in the naked Louise.

"Not any more. I graduated from St. Andrews earlier this year. I'll be going to Cal this fall." As I spoke, I crossed my legs again. I could see that his eyes were focused on my legs as I moved, probably hoping to get another peek at my white cotton panties. This time I made no effort to tug my skirt down, letting it slide well up my thighs. The Pool Boy's eyes remained glued to my legs. As I watched, he licked his lips.

Finally after a long silence he looked back at my eyes. "That's good."

"What's good?" I asked with all the innocence I could muster. This was really becoming fun. His eyes had wandered down to my tits again.

He jerked his eyes back up and said, "Oh, I meant it's good that you graduated from high school."

"Yup," I agreed. "I'm not jail bait any more,"

More blushing by the Pool Boy. "Oh. No, no. I just meant that everyone should finish high school."

"Yes, that's true . . . too," I said with unnecessary emphasis on the word "too."

I leaned back and pulled my sunglasses down off the top of my head in front of my eyes. "This sun feels so good." I uncrossed my legs and let them fall open just a bit as I pulled my skirt up a bit more—not enough to show him my panties, but enough to look like I was just working on my tan, maybe.

There was a long silence. I guess he forgot that I could see him through my sunglasses because he was blatantly staring at my legs stretched out from my chair. He licked his lips again. Finally he said, "You have nice legs."

"Thank you," I said. "You saw more of them last week." As I spoke I sat upright again and removed my glasses setting them on the table.

"That's not the same," he said. "Women can be much sexier with more clothes on than less. That's the lesson your friend Louise needs to learn."

I waited a moment. He was blatantly staring at my tits now. The whole conversation had been so fucking erotic that my nipples had grown rock hard and were making an obvious pair of little tents through my bra and blouse. Every time I moved my legs I could feel the juices from my pussy lubricating its lips. God I was horny.

"Oh. So you think I'm sexy?"

"Very," he said. He licked his lips again.

"Sexier than Louise?" I asked. As I spoke I released two buttons at the top of my blouse, exposing a minor amount of cleavage.

"Much."

"So if I took my clothes off you wouldn't throw me in the pool?" I asked.

"No, but it would be a shame for you to just undress and become naked like your silly little friend. You are very sexy the way you are."

"I've never understood how a woman can be sexier with her clothes on than without them," I said. As I spoke, I pulled my knees up into my chest and hooked the low heels of my Mary Janes on the edge of the chair. I could feel the warm air on the backs of my thighs all the way up to my panties, so I knew he was getting a good view.

There was a long silence and it was obvious that his eyes were fixed on my panty-clad pussy. Finally he spoke very softly, "Oh, but it's true. Some women just take your breath away with the right outfit."

"You mean like this one?"

Another long silence followed finally by a very soft, "Yes."

"So is this maybe even better?" I asked as I pulled the skirt up above my hips and spread my legs so he had an unimpeded view of my white cotton panties, stretched tight across my mound.