Getting Comfortable

"Alright guys, I am off, gotta clean house." Charlie said as his monitor displayed the end of match scorecard.

"Twenty years old and the man still has chores." Luke ribbed him through the PC headset.

"That's what happens when you live in your mom's basement!" Dale joined in.

"Yeah, yeah, yeah... at least my place doesn't look like a biohazard." He threw back at them. They tossed a few more jokes and he closed out the game and put the computer to sleep.

Charlie worked part time at a local nursery down the street and they had slowed down as fall came to a close. Which meant more time for gaming with his friends in college, but as his mom liked to point out, also more time to help around the house. There was plenty to do and with it just being him and his mother, extra free time meant more for him. It was one of the reasons he stayed living at home when he graduated. His father had left the summer after graduation. Their divorce was amicable but Charlie had decided to stay with his mother Lindsay rather than his father. She worked so much and he knew she would appreciate the help and company.

Charlie had no issue with his father. He was a good dad, but his parents had drifted apart years ago. He now lived a few hours away, but Charlie would call every couple weeks and make the trip to see him a couple times a year. His father was always supportive of him, always there when he needed. He even encouraged Charlie to take time after highschool to just relax and enjoy himself.

His mother, Lindsay, worked later hours, often home at 8 or later each night. His father had encouraged him to work on their relationship, and offered to pay his mother's half of the mortgage as long as Charlie still lived there.

With almost no bills, it was easy getting by on a part time job. And it let him get plenty of quality time with his mother. Since the divorce, they spent more and more evenings having a late dinner together. They would talk and watch movies on the couch together or if the weather was good enough, take a walk, hop in the hot tub. His mother loved every moment of it, and genuinely was happier than Charlie had ever seen her. He had become much closer to her in a short time than he had been all those years growing up with his father around.

As time went on, he saw how much his mother appreciated his help around the house. She would brighten up when she came home to dinner and some task or other she had been meaning to do suddenly handled. It became almost addictive for him. He built a rhythm to his days off. Cleaning the kitchen of the prior nights meal prep first thing as his coffee brewed. Then laundry, main rooms, every other day a bathroom. After lunch, was gaming for a couple hours. After, he'd run any house errands, or work the yard. By 7 he would be started on dinner. All just to make her happy. To see her smile and know it was because of him.

Today he had cleaned and balanced the hot tub. He would want it over the next couple nights. With all the yard work he had planned and his two split shifts this weekend, Charlie was definitely going to be using it to recover. Maybe his mother would get him another case of beer. He would just need to find something she wanted done.

He kept the hot tub well year round so he was finished early. Well what to do now? He asked himself. He checked the clock, it was only 4:30. He considered gaming again. But he had so much time still and the house to himself. He went down to his room in the basement. Waking the computer up, he put on the headset. Volume up. Browser to private.

Charlie had so much time. So he eased in to it, browsing slowly. Previewing, letting the desire slowly build. He preferred to draw it out, to take his time and work himself up as long as he could. He started slowly stroking through his jeans as his dick began to tense in to form. He was looking for something with story, a longer build up to a longer fuck. There were filters he could use, but the hunt was half the pleasure. Once he started getting truly hard he decided to try 'Milf maid takes master's giant cock'.

It was a long curly haired busty brunette in a French maid costume. For 15 minutes she teased and temped her employer. Flashes of skin, "accidentally" grazing him. Charlie was quite hard at this point. His strokes were slow, deliberate and tight. Trying to hold back and take his time.

When her master finally gave in and ripped her panties off Charlie had to pause it, his strokes had become too fast and his cock was throbbing wanting release. Not yet, he told himself. He continued this for another hour, the build up of one video, hunt for another. Repeat and repeat. 'Bust milf teacher' 'Brunette swallows bosses load' a few others.

Charlie was able to build his orgasm for over a hour and 15 minutes, he was in bliss. Finally he returned to maid and listened to her moan as he opened a new piece of erotica from his favorite author on literotica. It was a slow story about a young man seducing his mother's best friend. With little success seducing the friend himself, the main character convinces his mother to help him. By the fifth page his cock was raging red, streaming precum in to his fist.

Wonder if mom would mind if I fucked her friend? He thought. Maybe, Julie? Her tits were smaller than he normally liked but that ass is amazing. He loved a bubble butt and thick toned thighs. Both of which Julie was a fine example of.

He began to fantasize of seducing Julie. Charlie pictured he was fucking on the living room couch. What would mom think? Would she rage or maybe it would turn her on? Fuck! He was so close now, his dick pulsed and though he stroked rabidly he held off his orgasm just a bit more. The maid screamed with passion as she approached orgasm in the background. Charlie was in heaven and nearly ready to cum. Somewhere in there his phone buzzed but he didn't hear it.

Lindsay worked for a small international investment firm. Because of where her clients were located, most nights she wasn't out of the office till 7:30. Today though, their servers had to be shut down suddenly for repair. It quickly became clear this would not be a quick fix. A little after 5:30, with nothing more to do, Lindsay texted her son Charlie and headed home.

It was a pleasant surprise for a Thursday evening. The traffic was worse than her normal commute, but less than terrible and only slowed her down a few minutes.

Charlie's phone buzzed when the video doorbell detected Lindsay walking to the door pulling her keys from her purse. He was in the final moments before cumming. His imagination had run rampant with this story. Quickly shifting from his mother secretly watching and getting turned on. She helped seduce Julie. 6:00 PM read the clock on his computer. She held Julie's hair while her friend swallowed his cock. She fucked his cock with Julie's mouth. 6:03. She told Julie how to fuck him, commanded her to worship his dick. 6:04 Now he imagined her touching herself as she watched and commanded. He was barely picturing Julie by this point. He could tell he was going to cum any second and it would be massive. He had held it at the edge for 15 minutes now.

6:06 the clock blinked, he had to cum now. That was when the second stair down to his room creaked. Fuck! In a panic he stuffed his cock back in to his jeans with one hand and closed the browser with his other, then fumbled to close up his fly. With a quick toss he threw his tissue in closet across the room. A soft knock came at his bedroom door.

"Don't know if you saw my text," his mother said as she entered the room, not waiting after the knock. "But I got off er.." she looked up and froze half a step in to the room. She saw Charlie sitting at his computer, 6'2", lean athletic, headphones on and face flushed. Nothing on the computer screen but his desktop. The leg closest to her bent up to block the view of his lap. Oh my, she thought. It has been years since she had surprised him in this way.

"Sorry, I should have waited..." she stuttered and froze for a moment as he turned slightly toward her. Was that bulge all him? No, it couldn't be. She looked up after a breath and collected her thoughts. "Anyhow I was just going to say, um, I got off work early and ... umm..." peak "how about I take care of dinner tonight."

"Uh, uhm yeah." Charlie cleared his throat and said "that sounds great mom." A little quietly, but he was trying to appear normal and not like he was just about to get off to her pleasing herself as he pounded her best friend. "I pulled out some steaks, if you fire up the grill I'll cook those and you can do the rest." He thought he sounded mostly normal. He looked at his mother, she was stunning.

Lindsay wasn't yet 40, but she worked out and took great care of herself. She was 5'6" with tits Charlie guessed were DDD. Long brunette hair, a light tan left from summer, and full lips. She was in shape, toned from the regular exercise, but thick. Her ass was probably the only firm ass bigger than Julie's that Charlie knew of. Tonight she was wearing a dark grey pant suit with red blouse buttoned high.

"Sounds good son. I am going to get out of these close and I'll start it up." Lindsay made the excuse to give him some time to finish, then again she probably could have come up with a less suggestive excuse. Whenever she came home and he was gaming at his computer she would walk up and kiss the top of his head. Even though he was facing her and not the monitor; even in this situation, knowing how embarrassed he probably was, she decided to use it as an excuse to get a closer look. She walked to his desk and leaned over. She kissed him gently atop his head. And as she drew away, she didn't notice him blushing, she was too busy sneaking another look at the tent in his lap.

It seemed large. Not massive but long, longer than his father's maybe. What surprised her was the thickness of the tent. No it couldn't be that thick. That's just how he pulled at his pants to hide it. She thought. That thing would split a girl in half.

With a gentle head shake she turned round and exited the room. Charlie let out a massive sigh when he heard her reach the top of the stairs. Did that just happen? How could he be so dumb? He should not have stretched it out for so long, now he hasn't cum and is going to help cook. He was kicking himself in his thoughts, especially for offering to grill the steaks when he could so easily have finished while his mom cooked.

The embarrassment helped calm down his cock enough he could reasonably hide it in his jeans. When more blood flow left his crotch and he could think a bit more clearly again, he replayed what had just happened over in his head. Had she checked out his crotch? Twice? It couldn't be. He was just caught up in the fantasy.

Charlie had thought of his mother like that before, when he was younger but had gotten over it. Online he had seen the typical "stepmom" videos, but it had been years since he made the jump to thinking of his own mother like that. His heart was pounding still and he wanted to cum but he took a few breaths, adjusted himself once more. Then went upstairs.

Lindsay quickly got out of her work clothes and set out some sweats and a tank top. She was thinking of what had just happened. It wasn't the first time she had found him like that, but it had been several years. Give him some time to finish up, she thought, unless maybe her interruption had killed the mood. Though gauging by the size of what she saw, he was probably still good to go. She chuckled to herself lightly.

She felt like being a little naughty and decided to change up her pajamas. Grabbing some yoga pants she put the sweats back. Then she stepped out of her classic style panties and pulled out a red thong with lace seams. When she was dressed she stopped and checked her ass out in the pants. Her thick full ass looked sculpted, the pants wedging up her crack just enough to show the full shape. The lace panty line stood out at the top, Charlie would need very little imagination.

There was a wicked smirk on her face when she decided to remove her bra. Her DDD tits hung lower than when she had met Charlie's father, but in that light blue tank top they were squeezed nicely together. A large crevasse of cleavage on display. 'What am I doing?' She thought as she looked herself over once more in the mirror. 'It's harmless teasing. Hell, he probably won't even notice his old mother!' twisting round again to check her ass out a final time she thought he just might notice.

Lindsay grabbed a hard seltzer from the fridge on her way to the grill. Once fired up she headed back in to the kitchen. Charlie walked in from the hall as she shut the back door. Having decided not to finish, he did his best to calm his throbbing member down. It wasn't completely stiff anymore, just soft enough to hide in his boxer briefs and jeans. Seeing his mother, he wasn't so sure how long that would last. Her tits were practically falling out of that top, deep plunging cleavage squeezed up and out. He could see hints of her nipples through the thin blue cotton. Those pants were just as bad. They hugged every inch of her thick thighs, putting her lace panty line on full display. 'Was that a thong?' He thought.

"I will get some fries going" she said with a smile. "And I am going to make a salad in a minute. Sound good?" She popped out her hip to the side, drawing attention to her delicious curves. Charlie was transfixed and didn't respond. His eyes were glued to her full hips and thick thighs. She laugh, her full tits jiggling freely as she said "earth to Charlie!"

"Sorry, um" he stuttered and forced his gaze away from her body. "Yeah sounds good."

They cooked together, chatting and Charlie tried not to stare. Lindsay did not make that easy, finding any excuse to bend over at the waist in front of him. Or lean over the counter and press her tits together. He was getter harder and harder. Lindsay turned to the sink and Charlie was quick to tuck the head of his dick in waistband to try and restrain the swelling beast in his pants. It helped some but fell back when he moved too much.

Lindsay definitely noticed. It was impossible not to catch him staring nor trying to hide his erection. She was getting a terrible kick out of how flustered he was getting. It felt good to get this type of a reaction from a handsome young man. Even if it was her son.

Dinner was just as challenging for Charlie. Lindsay tried to eat as slowly and sensually as she could. Licking her fork clean every few bites, moaning how good the steaks were. Leaning in or squeezing her tits ever so slightly together when she caught him glancing. She was enjoying this too much. Her nipples were hard and Charlie definitely noticed. Her son was barely touching his plate.

After dinner they moved to the living room couch. Lindsay grabbed a throw pillow and laid down on the couch, with her legs tucked up leaving room for her son on the end. Charlie sat to her left and reached for the remote but Lindsay took it first. She stuck out her tongue playfully and started to flip through the movie channels.

Charlie didn't care what she put on. The way his mother was laying put her ass on fantastic display in those pants. He thought to himself 'she definitely is wearing a thong' as he stared at the lace of her panty line. He was trying to position himself so he could stare at her ass while looking like he was watching the tv. It wasn't working, and finally his mother said "stop fidgeting." And gave a light kick to his thigh. Finally he just slouched back enough that when he glanced over he hoped it wasn't too obvious.

He was too busy staring when he realized she had turned on a streaming service and picked some chick flick. He didn't care or complain like he normally would have. This wasn't the first time he had looked at her like this, but never had it just overtaken every other thought like it had tonight. It was a good forty five minutes before he realized the way he was slouching made his hard on very obvious.

Lindsay glanced down the couch again, he was STILL hard, "goodness the gifts of young men" she thought. With how many times she caught him staring she had to be very careful sneaking glances. It was so big, much bigger than his fathers, it had to be.

She peeked again and bit her lip for just a moment as she saw it twitch through his pants. She jumped ever so slightly when he placed his hands on his lap and pressed it down. She looked away. After a couple of minutes she sat up without looking over. She tucked one leg under herself. Keeping her gaze on the tv was so challenging.

"Charlie, I think we should talk about earlier..." she said softly, trying not to startle him.

"What do you mean?" He asked and sat up straighter and they both looked at each other.

"When I came home and walked in your room."

"Oh."

"You were masturbating. I'm not an idiot." She said and chuckled. She could see he was getting uncomfortable, and squirming more than he had at dinner. "It's okay honey. Perfectly natural."

"I know that but, you are my mom... you know. It's awkward."

"Well it shouldn't be. Everyone masturbates. And who else should you be able to talk to? Your parents should be someone you can talk about anything with." She turned and faced him more. One leg under, one on the floor, her thighs were wide open, and a clear crease at her crotch showed Charlie the full shape of her through the yoga pants. He turned to face her too, and soak in the sight as much as he could.

"Ok, I was masturbating... I don't know what else there is to say." He squirmed and glanced at her mound again. 'God she is hot' he thought. And now they were talking about him jacking off.

"Well we clearly need to be more open about it and talk about it, so it isn't awkward next time." His mother leaned forward a bit.

'Did she say next time?' Charlie thought. "What?" Was all he said.

"We need to talk about it and make it okay and comfortable so that when it happens again... it won't be awkward."

"It's always going to be awkward to stop and chat with my mom with my dick hard." Let alone hard after fantasizing of me pounding your bestie on this couch as you watch he thought. Charlie was surprised he had not only swore in front of her but in reference to his own penis. But his pulse was up and he had been hard for hours now. He could swear her eyes lit up and looked at his crotch when he said it.

"It doesn't have to be!" She slapped his shoulder playfully. "That's my point. I wouldn't think it was weird if you came and talked to me when I had my toys out."

"Sure..." he sounded skeptical, but all he could think of at that moment was her using those toys right then on the couch. "But... it like kinda ruins the whole... process. To just stop and have a chat. Seriously, just stop stroking... my hard cock..." he said the last a little slower than the rest. He thought "did she just bite her lip?" He was certain she did. He continued "and let go, put it away, and focus on my mother."

Lindsay was silent a moment, breathing heavy. She questioned what she was doing. This conversation was going in a way she had not anticipated. And the way he was talking made her pussy start to moisten. 'What is coming over me,' she thought, she felt like a different woman. But it felt good, and what was the harm with her son being more open or swearing now and then.

"You can finish after." She was trying to sound sensible, bring the conversation back a bit. "I don't mind if you are hard when I am talking to you. You shouldn't need to hide it, it's a natural reaction."

Charlie laughed and said "sure... I am just going to sit there with my throbbing hard cock out while I talk to you." Oh she definitely bit her lip again. "Talk about dinner with it pointing at you. That's not awkward at all."