A Day By The Pool Pt 07

While waiting for Daniella to recover from her big night of dirty sex, Theo goes for a walk and meets Georgina's mature English friend Sylvia who secretly directs porn films. After showing Theo her award-winning film 'Big Dick Boat Bangers,' she shows him her latest 'Lunch Lady' fetish project.

Chapter 7 is set immediately after Sylvia finishes showing Theo the porn film she directed. Although the two chapters could have easily been combined into one and I strongly encourage you to read them together, I split them to keep the Comic Gay Sex and Mature Older Ladies themes separate.

Enjoy.

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"Whoa. That was deep," I said as Sylvia's film Big Dick Boat Bangers ended.

The two of us sat there in silence for a moment as I continued to rub Sylvia's sore foot. I admit that I was supporting the start of an erection and Sylvia's right hand was now firmly clutching a wad of her skirt between her thighs. Sylvia smiled at me from behind her red rimmed glasses, then she shifted her sore foot over and placed it firmly on the bulge that was forming in my shorts.

"Say," Sylvia paused for a second, "I know how you men are with your pornography. If you need to masturbate, you may, but be careful with the mess. I've just bought this settee and it cost me a fortune to ship it all the way from England," she warned me while she lovingly patted the back of her couch.

A year ago, if a sexy older woman--or if I am honest, any woman for that matter--would have said it was okay for me to masturbate while we watched porn together, I would have pulled my cock out right then and there and jacked off on to her foot, but I must have grown over the last couple of months. Besides what would Daniella, the lady who spent the better part of the night fist fucking this lady's younger lesbian friend, say?

I thought about it for a split second before I knew exactly what Daniella would do. She would jack off on Sylvia's foot too. Or probably something worse like stuff Sylvia's big toe in her ass. I poured a little more hand cream on to Sylvia's big toe and stroked it for a second as I tried deciding if that was something I would want to try.

Eventually a more mundane thought crossed my mine. I came twice yesterday and already once this morning in Georgina's bum, and it nearly killed me. God only knows how many more times I would need to cum today.

"I'm not sure I should," I said a little downbeat. "I already came once this morning, and if today is anything like yesterday, it's going to be a busy day. The last thing I want is to be the limp dick cuckold boyfriend standing around while his girlfriend does other guys, and now girls for that matter."

Sylvia pulled her foot away from my crotch and her hand away from hers. "Oh, yes of course."

"No, no. It's your house, and I love your films. If you want, or need, to take care of anything..." I said as I motion towards her privates, "I'm happy to help out and to rub your foot." I reached out, pulled her foot back to my lap and dug my thumbs into the sole of her foot.

Sylvia eyed me for a second then her eyes twitched when I hit a particularly sore spot on her foot and her hand fell back down to her lap.

"What are you working on now?" I asked as I continued to rub her injured foot.

"Okay. I will show you another film, but first you must do me a favour and grab my vibrator from the nightstand in my bedroom."

"I would love too." I put her foot down and got up. "Where is your bedroom?"

Sylvia motioned to the hallway. "Down the hallway. It is the last door on the right."

I walked down the short hallway past the bathroom and a small study full of books. At the end of the hallway there was two doors to two rooms. The door on the right to her bedroom was closed, but the door to the room to the left was open enough for me to see what looked like some sort of medical examination chair with rubber sheeting on the ground. "I'm not going to ask," I muttered to myself before turning to the door to the right.

I tried the door and it opened easily. The slats over the windows were open allowing the spring sunshine in. From the windows, I peeked out and was given a great view of the street below. The room was tasteful and clean. On either side of the large king-sized bed there was a nightstand. One was piled high with books and the other just had an alarm clock on it. I tried the latter first, but other than some pill bottles and other medical supplies it was empty. I then tried the second one. To my shock, there on top of several old girly magazine there were two vibrators. One was just a small bullet sized, golden vibrator. The other was a much larger and smooth, black vibrator. I scratched my head for a second. "Which one did she want?"

Just to be cautious, I grabbed both and returned to the living room. The movie on the TV had changed from Big Dick Boat Bangers to something else. This time there was an older Greek woman, maybe in her late forties with dark, tight curly hair pulled back into a ponytail. She was short and stocky, and not the prettiest if I was honest. The lady had just finished her shower and was slowly getting dressed for work.

"I wasn't sure which one you wanted," I said as I rounded the couch.

Sylvia looked up at me with her big blue eyes from behind her red rimmed glasses. Her skirt was pulled up above her waist and a pair of white cotton panties were laying on the floor. Other than a tuff of grey hair on her pubic mound, her pussy was absolutely smooth as well as red and glistening from where she had just been rubbing it. She quickly eyed the two vibrators I held up. "I'll take that one," she motioned to the big black one.

I sat the other one on the coffee table beside us and sat back down. Sylvia thrust her foot back into my lap. "What's this film?" I asked as I reached for the lotion.

"Ah, this is a strange one," Sylvia pointed to the film on the TV, using the large vibrator as an odd visual pointer. "Early last winter, I was downstairs in my shop when this American lady came in. Right away I notice that she was dressed too nice to be one of the usual tourists. She started up a conversation--like you Americans always do--while she poked around my shop for a few minutes. She casually inquired about a few paintings, then out of the blue, she brought up my recent film work."

"She knew about Big Dick Boat Bangers?" I asked.

"Indeed, she did."

"But I thought that you did it anonymously?"

"So did I." Sylvia casually reached down and slid her middle finger between her labia and gave her rapidly engorging clit a swirl. "At first, I was worried that she was the Tax Man, but she quickly assured me that she was not. Apparently, she has a client, an American I presumed, that was looking for someone to produce a series of custom fetish movies for him."

"Oh god, that sounds suspicious," I shot out.

"I agree completely. I too was worried that it was something horrible, but no. As it turned out, he has a fetish for older women, more specifically, lunch ladies." With the big black vibrator, Sylvia pointed to the lady on the film. The lady was now fully dressed as a cook, with white cotton pants, and a white button up smock that did nothing for her figure. Across her large hips there was tied a red and white checker apron, while a mesh hairnet covered her dark curly hair. She wore next to no makeup except for some dark eye liner and red lipstick. The lady stood in an alleyway next to a large restaurant sized garbage bin smoking a cigarette.

"Lunch ladies?"

"Yes, I know." Sylvia confirmed before she casually popped the sizable vibrator into her mouth to lube it up with her spit. She moved it suggestively back and forth for a few seconds before she pulled it out of her mouth. Using her foot in my lap for leverage, she wriggled a little further down the couch to give herself better access to her bottom half. In the process I was given a wonderful view of her pussy. Her lips were red and swollen and naturally gaped open. Sylvia pressed the tip of her big vibrator onto her prominent clit and then turned it on. The machine let out a wonderful buzz as it went to work.

Sylvia gasped and a little breathless continued. "Apparently something happened to him when he was young, and his first sexual feelings were towards his school's lunch lady. She was much older than him, of Mediterranean, most likely Greek descent. The American lady who came to speak to me had been trying for nearly a year to produce something that her client would like, but with only moderate success. So, she began discretely asking around for someone who could make proper films for her client." Sylvia positioned the head of the large vibrator at the opening of her pussy and slowly began to insert it. Her eyes closed as I continued to work on her foot. The vibrator made it only about a third of the way in before it stopped. She had hit a dry patch. Her eyes instantly flipped opened in which I could see a little panic.

My training as lube boy for Daniella kicked in and I instantly grabbed for the lotion that I had been using on her foot. I snapped the bottle open, leaned in and poured a long line of creamy white lotion over the shaft of the big black vibrator. Sylvia eased the big vibrator out of her pussy. I quickly rubbed the lotion up and down the shaft of the vibrator before she eased it in a second time. This time it went in much deeper, causing her eyes to flutter when she bottomed out.

"Thank you," she whimpered before she continued with her story. "We sat on this very spot, and she showed me the films she had been making. Not bad for an amateur, but they screamed 'old, fat American women getting fucked in a dirty hotel' more than high quality sexual fantasy."

The lunch lady on the screen finished her cigarette and entered through an old beat up backdoor to a lunchroom. The place was full of men dressed as English school boys in blazers and shorts. I looked over at Sylvia. She was laying a little further back with her right leg still draped over the right arm of her couch. She slowly rocked back and forth as she casually worked the big black vibrator in and out of her hungry vagina.

"The next day the lady returned with €20,000 in cash." Sylvia paused for a second and took a deep breath on mention of the cash. Her foot in my hands gave a little spasm as she fought off a small orgasm. "We agreed to an informal, off the books contract. Her client was happy to informally bank roll our little venture, and money--to a reasonable extent--was no object. I would put together these little films and release them through my media company, but they, or he I guess, would have creative control over what got made."

"What does that mean?" I asked a little confused.

"Like this scene here," Sylvia motioned to the TV. Amongst the dozen schoolboys eating lunch, stood a younger looking guy completely naked holding a red lunch tray with an empty plastic plate on it. He stood there completely unnoticed for a second or two until suddenly everyone in the lunchroom turned to look at him at the same time and began laughing and pointing at him while he stood there naked in the lunch line.

I instantly recognized the scene as a variation of the standard stress dream everyone has from school. The one where you show up naked to class only to be humiliated in front of the whole school. The boy stepped up to the lunch lady and pointed at the red vat of spaghetti bolognaise she was serving to the students. In an odd sensual way, she stirred the red pasta mess several times while she eyed him up and down. Finally, she served him a heaping double portion of spaghetti and then gave him a wink. He smiled back at her and went to step away, only to come face-to-face with a boy twice his size. The giant boy sneered at him and then slapped the tray out of his hands, leaving his tiny cock exposed.

Sylvia twisted the big vibrator around a bit before continuing. "I originally casted Fabrizio from Big Dick Boat Bangers in the part of the boy."

"What? I thought Fabrizio was gay?" I asked.

"No. Trust me. For the right amount of money, he would fuck anything." Sylvia laughed, and when she did, her pussy contorted and pushed the big vibrator out with a soft pop. Sylvia stuffed it back in and then continued, "We shot this whole scene including the gangbang that followed, but when I set the rough cuts to the client, he insisted on reshooting the whole thing using actors with much smaller penises. It took me a whole week to recast the film. At first, I was deeply upset," she pushed hard on the vibrator and let out a little grunt to emphasise how mad she was, "but, good to his word, he completely covered the excess costs of the shoot."

The scene shifted to a darken room. The Lunch Lady who was now wearing a pair of bright yellow rubber gloves was starting to carefully rub the naked boy down with a used dish cloth. The boy stood their stiffly while she slowly began to work her way down from his face, across his chest and eventually down to his small cock. The lunch lady squatted down until her red lips where only inches away from his still soft cock.

'FAP, FAP, FAP,' came the sounds of Sylvia starting to work her pussy hard with the dildo.

I dug my thumbs into her foot again as I watched the lunch lady start to suck the guy's soft cock. "Who is the Lunch Lady? Is she a porn actress?" I asked trying not to get hard.

"No," gasped Sylvia. "Her name is Petra, and she drives a tourist bus a couple islands over. I had spent a month traveling all over Greece doing casting shoot after casting shoot with all the dirty mature Greek women I could get my hands on, trying find the perfect lunch lady for our client, but no luck. Then I accidently ended up on her bus."

We both paused for a second and watched as Petra, still on her knees with her hairnet on, expertly worked the young man's small cock in and out of her dirty mouth.

"I had unknowingly arranged three casting shoots on the Island on which Petra lives. As luck would have it, I was staying in the same hotel at which Petra works driving guest back and forth from the hotel to the port. My ferry was late due to bad weather, and it was nearly dark by the time I arrived. I had called the hotel earlier to tell them I would be late, so they had Petra waiting for me at the port when I arrived."

"At first it was just me and her on the small little bus she drove. I was feeling a little seasick from my rough trip, so I wasn't very talkative. Plus, her English isn't that good. So, for most of the trip I just sat quietly in back. Then, out of the blue, she stopped and picked up this anxious young man. The two obviously knew each other. At first, I thought that they could have been boyfriend and girlfriend, but he seemed too nervous about me being in the bus, and he was far too awkward towards her. Then I heard him ask her if I 'knew Greek?' and she said 'no.' My curiosity was now peeked, but I didn't yet let on that I knew Greek. Then to my astonishment the anxious young man asked her if he 'could get a blow job after they drop the old lady off.' Old Lady!" pouted Sylvia for a second while she continued to work the big vibrator in and out of her mature pussy. "Without taking her eyes of the twisty road to the hotel Petra agreed but said that it 'would cost €50.'

"Ah," I mumbled in approval as I watched Petra on the screen slowly turn the bewildered young man around before she pulled his smooth butt cheeks apart and inserted her tongue between his crack.

"I couldn't bite my tongue any longer," Sylvia continued. "That was when I said in Greek, that I would pay double if I could watch and take a few photos. The rest was history," Sylvia waved at the screen before she continued masturbating.

"Whoa, wait," my head was starting to spin from trying to keep one eye on the TV as Petra the Lunch Lady finished licking the young man's ass and demanded that he do the same to her, while the other eye watched as Sylvia pumped her pussy harder and harder while telling dirty stories. "Did they let you watch?" I stammered out.

"Oh yes," Sylvia grunted. "The man didn't want too but Petra insisted. She pulled the bus over straight away near some deserted sheep farm she knew. Then she made him crawl in back with me and she pulled down his pants. His cock wasn't that impressive, and he had a very hard time keeping his erection, but Petra was a real champ. She wasn't afraid of the camera, and she knew how to work a cock. By the time she made him cum in her mouth, I knew that she was perfect for my film." Sylvia nodded to the film as Petra laid on her back and began preparing her well used asshole for the young man's small cock by fingering it.

"After the man on the bus orgasmed, he ran off into the darkness, leaving me alone with Petra. With her mouth still tasting of his cum, Petra offered to eat my pussy for 'only €25' because she liked me. I paid her €50, and came twice," Sylvia said with a grin.

Sylvia's pace was starting to pick up. Each thrust from the big black vibrator caused the couch to shake more and more. She pulled her right leg up and put her foot on the arm of the couch. She twisted towards me, to give me a better view of her pussy and asshole. I kept a hold of her foot and did my best to work all of her sore spots with my thumbs. This seemed to work for her, and she pushed herself back as far as she would go into the corner of the couch. Her glasses began to fog up as she snaked her free hand around to her ass and began to rub her index finger around her brown asshole.

The action on the TV was quickly reaching a climax too. Petra the Lunch Lady was lying on her back on top of a metal meat cart with her knees squashed to her chest as the young man with a tiny cock pummelled her fat ass. Then there came a massive grunt from the young man as he pulled his dirty cock from her violated ass and pointed it towards her face. In a flash, Petra was back on her knees with her dirty red mouth wide open, as she snaked her big tongue in and out begging for his cum. He frantically jerked on his little cock for several second, until he stopped breathing and with a great splash, he shot a great stream of cum over Petra's hungry face.

I quickly turned back to Sylvia. Her eyes went wide as she pushed the big vibrator in as far as it would go. She pulled her hand away from her ass and started frantically strumming her clit like mad. "Put a finger in my ass!" She demanded.

Without hesitating, I shot forward with my left hand and in a single thrust pushed my already lubed middle finger deep into Sylvia hot and dirty hole. About halfway up I hit something semi-solid, but this wasn't the moment to get squeamish, so I just pressed on.

Instantly Sylvia gasped, cinched down, her asshole began to spasm, and her legs began to shake. "Oh god, oh god," she whimpered as her orgasm began to hit. With her left hand, she jammed the big black vibrator in as deep as it would go inside her pussy, allowing me to feel its intense vibrations threw her thin pelvic floor. With her right hand, she continued to strum her clit like mad, until suddenly she couldn't control her orgasm any longer and she let go.

A great flood a piss shot forth from her pussy and was flicked everywhere by her hand as she orgasmed. My hand near her butt was directly in the firing line and was instantly soaking wet. Heavy drops hit me in the face, mouth, and even in my eye. The drop in my eye stung like mad, but I was too excited by the site of watching Sylvia orgasm to care.

Sylvia's whole body shook with aftershocks until her orgasm eventually subsided. For the longest time she lost her powers of speech, and just sprawled out on the couch semi catatonic staring up at the ceiling. Eventually in a raspy voice she croaked out, "you can take your finger out of my bum now."