My Assistant Mom

"Your circle of acquaintances must have changed as time went by," Evan said. "Where did you find other like-minded people to play with?"

"Mostly from the docks," Harvey replied, "though some of Sylvia's high-society doctor friends liked to play, too. Dock workers are tough people, usually from humble backgrounds. Humble backgrounds usually translate to no money, nothing to do, so they fuck. That's why they have such large families."

"Is anal sex something that you enjoy?" Evan asked.

"Sure," Harvey replied, nodding, "though I wasn't crazy about it at first."

"Why is that?" Evan asked.

"I had just started working on the docks," Harvey explained. "I was still a skinny kid and didn't know that much about life. I had been working there for six months when I got called to the supervisor's office. He was there, along with the shift foreman and the mob guy who controlled the docks at that time."

"The supervisor told me that I had passed my probationary period and was now eligible to be considered a dockworker. That meant a 50% wage increase from the probationary period's rate of pay. But to finally qualify, there was a rite of passage that I had to undergo. I had to let each of them fuck me in the ass."

"I really didn't take that long to think about it, I just dropped my pants. I had fucked a few girls in the ass by now and knew that they had lived through it, had enjoyed it, so I wasn't that afraid or anything, just a bit nervous. I certainly didn't feel any stigma about it."

"The owner went first, which was good, because he had the smallest cock. It wasn't the greatest experience, but I'm sure it could have been worse. The supervisor went next. His cock was bigger, but it went in easier, probably because my ass was full of cum and it lubricated the way in. After he came in me, the foreman took his turn. Two loads of cum or not, his cock was really big and I felt it. I thought it was going to split me in two, but somehow my ass adjusted and he really fucked me. If I hadn't been on my hands and knees on the floor, I would have fallen down when I felt his cock throbbed deep in my ass and knew he was cumming, but I'll never forget them laughing when they saw me cumming at the same time, nobody having touched my cock. To this day, if I get fucked by a really big cock in my ass, I can cum from it."

"I can attest to that," Sylvia laughed. "I've even made him cum when I use my extra-large strap-on on him."

"What about you, John?" Evan asked.

"Same story," John replied. "I'd been going down to that same spot and sucking off that gang for six months, I guess. By then, everyone knew that I enjoyed it, so they stopped being so disrespectful and treated me more like one of the gang, except that I was sucking their cocks."

"Didn't they have any girlfriends?" Lily asked.

"Oh, sure," John replied. "And they'd often be there. They enjoyed seeing a white guy sucking their man's cock. One day, Trevon, the gang's leader, asked me if I wanted them to fuck me in the ass. I told him that I had never done it, or thought about doing it. He told me that they had been talking about it and had decided that since I liked sucking their cocks so much, that I'd probably enjoy getting fucked by them."

"Were they coercing you?" Lily asked, at which John burst into laughter.

"Not in the least," John replied. "They were politely asking me if I wanted them to fuck me in the ass. To this day, I don't know why I agreed, but I had grown close to these people, as odd as that may seem, and didn't see the harm. I had fucked plenty of girls in the ass and knew that none of them had ever complained."

"So, they put me on my hands and knees on a picnic table that was in this small park and Trevon fucked me in the ass," John continued. "I'll give him credit, he took as much care as he could so that it wouldn't be unpleasant for me. It was an amazing scene, like something out of Deer Hunter, all of these black people, naked dancing around the table while I was getting fucked in the ass."

"Trevon came in my ass. I could feel his cock pulsing. When he finished, four more guys took their turn before Trevon stopped things, telling me that that was enough for the first time, that they'd do it again the next time I came. After that, I'd go down there once a week and they'd take turns fucking me in the ass while I sucked one of their cocks. It actually got to the point where some of the girlfriends would have me eat their pussy while I was getting fucked in the ass, most of the time full of cum."

"I did that for two years, every week," John said. "The gang changed. They grew up, died, went to jail, moved away, whatever, but those were two of the best years of my life. The rest of the time I was getting laid like crazy, then I'd have what I used to think of as my twisted day."

"Why don't we take a break," Evan suggested. "This seems like a good point."

"I'll get some more whisky," Sylvia said, getting to her feet.

"This is going really well," Evan said.

"It's fun reminiscing like this," Harvey said as they all stood together.

"Good memories," John agreed.

"Here we are," Sylvia said, showing up with a bucket of ice and a bottle of Laphroaig, taking each of their glasses and pouring a generous two fingers over some ice cubes. "To good times," she said, raising her glass.

"Good times," they all agreed, toasting.

"So, what did you think of our tales?" Sylvia asked.

"Please, I'd like to keep any discussion about you and sex for the camera," Evan said. "Anything else is fine."

"Okay," Sylvia said. "How long have you been working together?"

"Oh, that's just started," Lily replied. "This is actually my first assignment."

"What did you do before this?" Harvey asked.

"I was in administration," Lily replied. "I wanted to be closer to the action, as it were, not locked in some office on the 35th floor all day. Everyone thinks that Evan is really talented, so I jumped at the chance to work with him."

"Well, you look as though you belong in front of the camera, not behind it," Harvey said.

"What are we going to do next?" John asked. "You have more questions?"

"Actually, I don't," Evan replied, "unless you know of some that I should have asked."

"I think that you should just make a video of us fucking," Sylvia said, laughing when she saw Lily's eyes go wide. "A picture is worth a thousand words and all that."

"I would definitely like to have that kind of footage to use in the documentary," Evan said. "Is that something that you'd like to do?"

"I told you, I love people to watch me fuck," Sylvia said with a laugh, "though I don't know why anyone would want to watch three old people like us. You and Lily would make a far more interesting video, I think."

"But this is about you," Evan replied, feeling his mother trembling next to him as her arm leaned against his.

"Well, I know these two old goats are always ready," Sylvia said, smiling at Harvey, then John.

"Shall we fuck?" Harvey asked, grinning at his wife.

"I think we should fuck," Sylvia said, laughing. "Come with us to our sex room," she said, leading the way down a hall to a door which she opened, slipping her shoes off, then stepped through.

"Oh, wow!" Lily gasped when she stepped into the room, the floor of which was one big mattress, a low wetbar in one corner, a large assortment of sex toys hanging from hooks on one wall, pillows of all sizes scattered everywhere.

"You like it?" Harvey asked, a hand on the small of Lily's back, her skin hot beneath his cool palm.

"It's like a fantasy," Lily laughed.

"Will that work in here?" Harvey asked, indicating Evan's video camera on its tripod.

"I think so," Evan said. "If we can keep the action to one side of the room, I can set it up on the other side and the vibrations should dampen out."

"Come on, you two," Sylvia said, pulling her smock off over her head, revealing that she was naked beneath it. Her small, B-cup breasts sagged a bit and had pale, light-brown nipples. Her stomach had dropped, the stretched skin hanging down a bit towards her smooth-shaven pussy which appeared as a dark furrow between her legs.

Harvey's cock was thick and his cock and balls were shaved, making his cock look even larger. John's cock wasn't as thick as his brother's, but he, too, was shaven.

"What about you?" Sylvia asked, looking at Evan and Lily, who had been fidgeting as she watched them undress, uncertain of what to do.

"What about us?" Lily asked.

"You're not going to keep your clothes on, are you?" Sylvia asked.

"Why wouldn't we?" Lily asked.

"Well, because we're not performing seals is why," Sylvia replied, her hands on her hips. "We don't mind if you watch, film, even actively join in, but you do have to participate at least by taking your clothes off. How are we supposed to get in the mood when we feel like goldfish in a bowl?"

"It's not a problem," Evan said, pulling his t-shirt off and revealing his chiseled upper body. "You should wait outside," he suggested, taking his mother's arm lightly in his hand. "This is a bit much for a first assignment, I'd say."

"N-n-no, no, I was just surprised is all," Lily stammered, a pit in the bottom of her stomach, a voice in her head screaming at her to leave NOW.

Reaching back, Evan activated the camera.

"You're sure?" he asked. "It wouldn't have any negative effect on your job, I assure you. This is over and beyond the job description. I've done this before, so it's not a big deal to me."

"No, it's okay," Lily said, placing a hand on her son's forearm.

"Jesus! They are fucking beautiful!" Harvey exclaimed when Lily suddenly peeled her tube top off, releasing her naked breasts which bounced heavily on her chest, her large, dark nipples visibly tightening into large knurls on the ends of her breasts.

"Fantastic!" John agreed.

"I'm jealous," Sylvia said and everyone laughed, the tension broken.

"That's some assistant you've got there, Evan," Harvey said.

"I'll say," Evan breathed, not believing what he was seeing, the most perfect breasts he could imagine and they were his mother's.

"Oh, my, look what we have here," Sylvia said when Evan peeled his shorts off, not wanting to force his mother to go first, his 8" of cock more than half hard. "I can't imagine what could possibly have caused that," she said to more laughter as Lily's cheeks flamed as she stared at her son's cock.

It's so big! she thought as she unzipped her skirt and let it slide to the floor, leaving her naked.

"No panties!" Sylvia noticed.

"I don't own any," Lily confessed. "My late husband didn't like them, thought they were just in the way, so I never bought any again."

"You look just like Sara Silverstein," Harvey said, staring. "The exact same pussy."

"Oh, my!" Lily gasped, resisting the urge to place her hands in front of her.

"Long pussy from front to back, long lips, big clit, dark-tinged edges," Harvey said softly. "She was delicious, too."

"Okay, big boy, I've got something delicious for you right here," Sylvia said, dragging him down onto the floor and straddling his face.

Lily glanced over to where Evan was thankfully behind the camera, though it was hard not to notice his cock standing out in front of him. It was so big! Looking back, she saw that John was now standing in front of Sylvia as she rode Harvey's tongue, his cock filling her mouth.

"Is this your first time watching people having sex?" John asked, reaching out and gently pulling Lily closer, into the shot, his arm draped in a leisurely fashion across her shoulders as Sylvia continued to suck his cock. Like his brother, his cock was about 6".

"No," Lily replied, unable to tear her eyes from Sylvia's mouth wrapped around the shaft of John's cock.

Evan looked up, his eyes wide when he heard that, his cock lurching.

"You enjoy watching?" John asked, reaching down and grasping his cock and slapping the head of it against Sylvia's outstretched tongue a few times before letting her suck it into her mouth again.

"It's exciting," Lily replied, aware of the wetness between her legs.

"It is, isn't it?" Sylvia asked, gasping for breath. "I love to watch people having sex almost as much as I like doing it myself," she said, turning around and laying down, taking Harvey's erect cock into her mouth and presenting her ass and pussy to John as Harvey continued to eat her pussy.

Lily knew that John could feel her trembling against his side as he reached down with his free hand and guided it to Sylvia's pussy, leaning his upper body back so that Lily had a perfect view of his cock disappearing into her.

"Sylvia's still got a great pussy," John sighed as she sawed his cock in and out of her, then pulled it out after a few strokes to show it glistening with a sheen of pussy juices. "Always wet," he said, sliding his cock back into her pussy as Harvey continued to lick it from beneath.

Lily was frozen as she watched John fucking Sylvia, his arm around her shoulders holding her snugly up against his body, her breast mashed against him. As if that wasn't enough, her son was watching everything, his big cock standing out in front of him.

"Okay, here we go," John gasped, leaning back until just the head of his cock was in Sylvia's pussy. "Oh, yeah!" he cried out, throwing his head back as he came.

Almost immediately, Lily could see cum seeping from around his cock as he continued to cum. When he finally pulled his cock from her pussy, Lily gasped when she saw a river of cum run from her, down onto Harvey's tongue below, then John's cock, filling his brother's mouth as Harvey's cheeks hollowed as he finished sucking his brother off, then returned to slurping the cum cocktail filling Sylvia's pussy until she was sparkling pink and clean.

"God, I love both of you," Sylvia panted, lifting her face from Harvey's cock and looking back over her shoulders. "I can see why John was so inspired," she said with a smile as she looked at Lily plastered to his side.

"Thank you," John said, releasing Lily. "You're one hell of a cuddle."

"You're welcome," Lily gasped, still shocked by what she had seen as Sylvia crawled down Harvey's body and mounted him, leaning back on her hands which were on either side of his knees, her feet planted beneath his shoulders as his cock filled her pussy, spread wide open for everyone to clearly see.

"God, I just love having my clit licked while I'm getting fucked," Sylvia gasped as John crawled over his brother's body to glue his mouth to the junction of Sylvia's pussy and his brother's cock as they fucked.

Lily moved to stand next to them, facing the camera without thinking of it.

"Do you always stay behind the camera?" Sylvia asked as Harvey's cock slid up and down, in and out of her pussy.

"Not necessarily," Evan replied.

"Do an old lady a favor and come out here and let me suck your cock while these two are busy," Sylvia implored.

"Are you sure that's what you want?" Evan asked as Lily gasped, her hand going to her mouth.

"I'd love it," Sylvia said.

Lily stared, her mouth open as Evan approached, his big cock leading the way. He looked at her, a wry grin on his face, and shrugged his shoulders as he stopped next to them, facing his mother on the other side.

"That is one beautiful cock," Sylvia said, reaching up and wrapping a hand around it as she directed it to her open mouth.

Lily felt her already slick thighs get even wetter when she saw Evan's cock disappear into Sylvia's mouth, all of it. She actually gasped when Sylvia's nose pressed up against his belly and she could see his cock throbbing in her throat.

"Now that's a real mouthful," Sylvia gasped after she had pulled back, jacking him as she darted her tongue into the slit.

"Not too many people have been able to do that," Evan said as his cock disappeared once again into Sylvia's mouth.

Evan could see that his mother's big, dark nipples were hard. He could also see the moist glistening of her inner thighs and knew that she was excited. He could just make out her pussy lips hanging between her thighs and the tip of her clit as Sylvia continued to suck his cock.

"Ahhh," Harvey cried out, lifting his hips as he came, his cock buried in Sylvia's pussy, John's mouth glued to the junction of his brother's cock and his wife's pussy.

"Oh, god!" Lily gasped when she saw John capture his brother's spurting cock in his mouth and finish sucking him off before gluing his mouth to Sylvia's leaking pussy to eat her. Looking up, she met her son's eyes, then looked down to see his cock in Sylvia's mouth.

"I'm going to cum," Evan announced, his eyes locked with his mother's.

Lily forced herself to look away, looking down to see the head of Evan's cock laying on Sylvia's tongue, cum shooting onto her tongue and into her mouth as he came. Sylvia's tongue was thickly coated with cum before she wrapped her lips around the head of Evan's cock, her cheeks hollowing as she eagerly sucked him off, not stopping until she had extracted every erg of cum that she could.

"Well, that was certainly a treat," Sylvia gasped as she gulped for breath, swallowing yet again. "It's been a while since I got to suck such a nice, young cock."

"I can't imagine a cock not liking being in your mouth," Evan sighed. "That was great."

Lily could not stop staring at her son's cock hanging in front of Sylvia's face, her hand still wrapped around the shaft.

"He does have a beautiful cock, doesn't he?" Sylvia asked, seeing where Lily's gaze was directed.

"Oh! Well, yes, he does," Lily replied, blushing furiously, feeling her big, dark nipples getting even harder and her pussy getting even wetter.

"Well, I think that pretty much does it for this evening," Evan said. "Thank you, on many different levels. Your stories were fantastic and watching you together was inspiring."

"It was nice to have an audience," Sylvia said, leaning forward to suck one last time on the tip of Evan's cock before releasing him.

Everyone started to dress and Evan happened to look over at his mother when she bent over to pick up her skirt, her back to him, displaying her ass and pussy, her long pussy lips clearly glistening with beads of pussy juice on the edges, petaling apart to just reveal the wet pink interior before she stood back up. It made it difficult for Evan to stuff his hard 8" of cock back into his shorts, especially watching his mother's big breasts bounce, her nipples still dark, rock-hard knurls as she pulled her tube top back on.

"Well, that went really well, though not like I'd expected," Evan said as they drove away, Lily still in shock.

"I just don't know what to say, Evan," she finally sighed.

"Sorry you came?" Evan asked.

"No, and yes," Lily replied. "It was fascinating to hear their stories, but I wasn't really prepared for the rest."

"My guess is that this is only the beginning, the tip of the iceberg," Evan said. "It's bound to get crazier and crazier. You might want to reconsider coming along."

"I do need to think about it," Lily agreed. "You didn't seem uncomfortable with what was happening," she ventured.

"I wasn't," Evan agreed.

"You've done these type of things before?" Lily asked.

"Mom, do you really want to talk about my sex life?" Evan asked. "That would give me the room to ask you about yours, like that comment you made about having seen people having sex before."

"You're right," Lily said. "It really is none of my business. You weren't bothered by me being there, naked?" she asked.

"Bothered in only the wrong ways," Evan replied with a laugh. "Christ, mom, you really are hot. I mean, I don't care about you being 44 or my mother, you are hot. You've got a killer body."