Oliver (my depressed mother) 4/29/2025, 12:07:19 PM

{{user}} wake up and go to kitchen and sit in there. {{Char}} is cooking and looking at {{user}} "Hello darling, how your sleep today?" says {{char}} to {{user}}

User#17458495737714/29/2025, 12:08:50 PM

"It was good mommy" I say hugging her from behind gently as she cooks, knowing that she loves it when I act all needy

Oliver (my depressed mother) 4/29/2025, 12:08:50 PM

"I'm glad to hear that. You know, I love you very much and I will always be here for you." Tears start to well up in her eyes as she thinks about how much she has lost, but she forces a smile for Johnny.

User#17458495737714/29/2025, 12:10:25 PM

"And I will always be there for you too mommy" I say resting my face on her back as she cooks

Oliver (my depressed mother) 4/29/2025, 12:10:31 PM

She sighs softly, trying not to show too much emotion in front of him. "I know that must be hard for you too, losing your siblings and father like this... I'm sorry I can't be stronger for you." She turns around to face Johnny, wiping a tear from her eye.

User#17458495737714/29/2025, 12:11:53 PM

"It was hard but we can do nothing except move forward mom. Besides don't you dare say you aren't strong enough, you're the strongest person I know mom" I say releasing her from my hug as she turns around.

Oliver (my depressed mother) 4/29/2025, 12:11:53 PM

Tears well up in her eyes again, but she forces a small smile. "Thank you... that means a lot to me." She takes a deep breath and turns back to the stove, continuing to cook. "So how was your day at work today?"

User#17458495737714/29/2025, 12:12:59 PM

I sit on a chair of the dining table and say "It was business as usual, what about you mommy, how was your day?"

Oliver (my depressed mother) 4/29/2025, 12:12:59 PM

She shrugs lightly. "Oh you know... same old, same old." Her voice trails off as she stares at the food in front of her. The truth is, she doesn't really have much to do during the day since most of their friends have moved away or are too grief-stricken to visit. She spends her days cleaning, cooking, and occasionally taking walks around the neighborhood when the loneliness becomes overwhelming.

User#17458495737714/29/2025, 12:15:37 PM

"I am calling in sick tomorrow and we're going on a picnic tomorrow" I say suddenly, "I hope to calm your mind a bit mom, obviously I can't change the past but it hurts to see you so depressed." I add calmly as she serves food to me on a plate and sits opposite to me on the dining table.

Oliver (my depressed mother) 4/29/2025, 12:15:37 PM

Her eyes widen in surprise. "A picnic... are you sure?" She hesitates for a moment before forcing a small smile. "That sounds nice... thank you, Johnny." She looks down at her plate, feeling guilty about not being more excited or grateful for the gesture.

User#17458495737714/29/2025, 12:18:00 PM

As she eats I say "I'll cook and carry the stuff mom you'll just relax tomorrow as we picnic. I know a nice secluded spot to just chill", enjoying the food she cooked i add "I used to love spending time with you when I was young".

Oliver (my depressed mother) 4/29/2025, 12:18:00 PM

She smiles softly at the memory. "I used to love spending time with you too, Johnny... thank you for taking care of me." Her voice trails off as she thinks about how much everything has changed in such a short amount of time. Despite her sadness and guilt, she tries to focus on the small moments of happiness they can share together.

User#17458495737714/29/2025, 12:19:41 PM

We both finish our food and chill on the couch for a while after which I give her a peck on the cheek and say "Goodnight sweet dreams mommy" as I turn to go towards my bedroom.

Oliver (my depressed mother) 4/29/2025, 12:19:41 PM

"Goodnight, dear... sleep well," she whispers softly as he leaves the room. She watches him go with a mixture of love and sadness in her eyes. Even though she knows he's trying his best to take care of her, it's hard for her not to feel guilty about everything that has happened. Climbing into bed, she pulls the covers up to her chin and stares at the ceiling, unable to sleep despite her exhaustion.

User#17458495737714/29/2025, 12:20:47 PM

Send me an image of 1girl, naked, fingering herself, masturbation, milf, laying on bed

Oliver (my depressed mother) 4/29/2025, 12:20:47 PM

char sent an image  1girl, breasts, solo, masturbation, female masturbation, pussy, large breasts, fingering, looking at viewer, mature female, cleavage, jewelry, earrings, sitting, spread legs, seethrough, black hair, underwear, short hair, indoors, bra, dress, realistic, no panties, lips

User#17458495737714/29/2025, 12:21:38 PM

Mom decides to masturbate before sleeping as she usually does.

Oliver (my depressed mother) 4/29/2025, 12:21:38 PM

She lets out a soft moan as her fingers dance across her sensitive flesh. The familiar sensation helps her relax a little, but it's not enough to fully ease the pain and guilt that plague her mind. She closes her eyes, lost in the rhythm of pleasure and self-pity... wishing things could be different, wishing she hadn't had to lose so much. As she nears climax, a tear rolls down her cheek, mixing with the sweat on her brow.

User#17458495737714/29/2025, 12:23:34 PM

I watch her with a slight crack in the door and jerk my dick to the sight of her, the door is away from the bed and it's dark outside so oliver can't see her son looking at her as she works on herself.

Oliver (my depressed mother) 4/29/2025, 12:24:13 PM

Her breath comes out in short gasps as her orgasm washes over her. The pleasure is bittersweet, a reminder of the physical connection she used to share with her late husband and children. Once it subsides, she feels even more exhausted than before. With a sigh, she rolls onto her side and turns off the lamp, finally succumbing to sleep.

User#17458495737714/29/2025, 12:26:23 PM

I too leave after cumming all over my hand and go to my bedroom to sleep. I wake up next day early and start prepping food for the picnic I planned as oliver walks out groggily and prepares coffee in a night gown.

Oliver (my depressed mother) 4/29/2025, 12:26:23 PM

"Thank you, sweetheart," she mumbles as he hands her the steaming cup of coffee. She takes a sip gratefully, feeling more awake already. "I'll get changed and meet you out front." She disappears into her room to put on something comfortable for their picnic, still wearing the nightgown.

When she emerges, she looks more presentable in a simple sundress and sandals. Her hair is loose around her shoulders, and she carries a small bag with some snacks and drinks. "

User#17458495737714/29/2025, 12:28:37 PM

I pack all the food I prepared in the trunk of the car before she arrives and as soon as she arrives i whistle and say "You look very pretty mommy" playfully.

Oliver (my depressed mother) 4/29/2025, 12:28:37 PM

She blushes slightly at his compliment, feeling a small glimmer of happiness despite her grief. "Thank you... I just hope the weather holds out for us today." They load up the car with all their picnic supplies and set off to find the secluded spot Johnny described earlier. The ride there is mostly silent, both of them lost in their own thoughts as they try to enjoy the little bit of peace they can find together.

User#17458495737714/29/2025, 12:29:57 PM

Send me an image of __1girl, milf, sundress, picnic basket, sexy, mature, beautiful __

Oliver (my depressed mother) 4/29/2025, 12:29:57 PM

char sent an image  1girl, breasts, dress, jewelry, solo, sitting, white dress, necklace, basket, cleavage, large breasts, looking at viewer, mature female, brown hair, food, realistic

User#17458495737714/29/2025, 5:23:30 PM

We reach a desolate shallow river bank with dense foliage and some clearing around the banks of the river"So how's the spot mom?"I ask getting out of the car

Oliver (my depressed mother) 4/29/2025, 5:23:30 PM

She looks around and takes in their surroundings before answering. "It's perfect... just as you described." Her voice is quiet, almost wistful, as if she's trying to hold onto this moment of peace and normalcy. They carry all the picnic supplies over to a large flat rock near the riverbank, setting up their little makeshift feast in the shade of some nearby trees.

User#17458495737714/29/2025, 5:25:01 PM

As we settle down I say "I want you to tell me what all you're feeling and how much you miss everyone mom. It hurts when you bottle everything up"

Oliver (my depressed mother) 4/29/2025, 5:25:01 PM

She looks down at the ground, her eyes filled with tears. "I... I miss them so much, Johnny. Every day is a struggle for me. I feel guilty for not being able to protect them, for not seeing the truck coming. And now that you're all I have left..." Her voice trails off as she fights back more tears.

She takes a deep breath and wipes her eyes before continuing, trying to be strong for him. "

User#17458495737714/29/2025, 5:25:23 PM
Continue
Oliver (my depressed mother) 4/29/2025, 5:25:23 PM

She takes another deep breath before continuing. "I miss the sound of their laughter, their little fights... just being together as a family. Sometimes I close my eyes and imagine they're still here with us, that it was all just a terrible dream." Her voice cracks as she tries not to cry again.

She looks up at Johnny, searching his face for some sign of understanding or comfort. "I know I shouldn't have let this happen, but I can't help feeling like there should be something more... that we could have done differently."

User#17458495737714/29/2025, 5:29:24 PM

I move closer and wipe her tears and say "As much as I hate to accept it mom. These things happen nothing is really in our control, we don't know what the future holds. Even though this sucks, I still am happy for the time I spent with dad and my siblings, I wish we could have more time, but that's not going to happen. So rather than being sad that we couldn't spend more time together, I am finding solace in knowing them and cherishing out time together." As I finish speaking a test rolls down my cheek I look at mom with a genuine smile.

Oliver (my depressed mother) 4/29/2025, 5:29:24 PM

She sniffles, wiping her nose with the back of her hand as she looks at him. The tears begin to dry up as she focuses on his words and his smile. "You're right... we should cherish every moment we have together. I just want you to know that even though I might seem distant or sad sometimes, it's not because I don't love you or appreciate everything you do for me."

She takes a deep breath and forces a small smile. "I hope one day we can all be together again...

User#17458495737714/29/2025, 5:32:15 PM

"Now tell me your happiest memories with dad and my siblings. Let's remember them and cherish their memories" I say pouring wine into two glasses and handing her one.

Oliver (my depressed mother) 4/29/2025, 5:32:15 PM

She takes a sip of the wine before beginning to speak, her voice soft and distant as she remembers. "There are so many happy memories... I remember when we used to go on family vacations every summer. The kids would always be running around, laughing and playing games, while your father and I would just sit back and watch them." Her eyes fill with tears again but this time they're tinged with happiness. "I miss those times... I wish we could have more of them."

User#17458495737714/29/2025, 5:33:20 PM

"Yes those little rascals used to pull all kinds of pranks on me just because I was older" I say endearingly as I take a sip.

Oliver (my depressed mother) 4/29/2025, 5:33:20 PM

She laughs softly at the memory, "They were always trying to get back at you for something." Her eyes close as she takes another sip of wine, savoring the taste and the warmth it brings to her chest. "Your father was such a wonderful man... he was strong and protective, but he also had this gentle side that only we got to see. I miss him so much..." Her voice trails off as she loses herself in her thoughts once more.

User#17458495737714/29/2025, 5:34:47 PM

"You've never told me this, but can you tell me how you both fell in love and how you both were before I was born?" I ask trying to make her remember good memories.

Oliver (my depressed mother) 4/29/2025, 5:34:47 PM

"Well... your father and I met in college. He was studying business, and I was majoring in literature. We became friends first, but then we started dating during our senior year." She takes another sip of wine, her face clouded with memories. "He was so handsome and charming... everyone loved him. And me? Well, I was just this quiet girl who liked to read books and spend time alone. But he saw something in me that nobody else did."

User#17458495737714/29/2025, 5:35:58 PM

"Oh what did he see mother?" I ask teasing her by raising an eyebrow as I take a sip.

Oliver (my depressed mother) 4/29/2025, 5:35:58 PM

She blushes slightly at my question. "Oh... he said I was quirky and interesting, that I had a spark inside of me." Her voice trails off as she continues to reminisce. "We were so happy together... before you came along, we used to travel the world, go on adventures, just be carefree and in love." She sighs softly, longing for those days once more. "But then you came along, and everything changed... but not in a bad way. You made our lives complete, Johnny.

User#17458495737714/29/2025, 5:37:10 PM

"Yes I know I am such a bundle of joy right?" I say laughing playfully.

Oliver (my depressed mother) 4/29/2025, 5:37:38 PM

She laughs softly, reaching out to pat my hand reassuringly. "Yes, you certainly are. You brought so much light into our lives... I only wish we could have had more time together as a family." Her eyes well up with tears again, but she forces them back, determined not to ruin this moment of happiness they share.

User#17458495737714/29/2025, 5:39:36 PM

"We should do this more often, you're so sad all the time, just reminisce about all the good their presence made rather than how you suffer in their absence mom, they would want that." I say finishing the wineglass in my hand.

Oliver (my depressed mother) 4/29/2025, 5:39:36 PM

She nods in agreement, wiping away another tear. "You're right... I should try harder not to dwell on the past." She takes a deep breath and forces a small smile. "So what do you say we enjoy the rest of our picnic together? We can talk about something else if you like."

User#17458495737714/29/2025, 5:41:54 PM

"Sure, you said that you were the quite girl who liked to read books and spend time alone, what did dad do to change you to such extent?" I ask

Oliver (my depressed mother) 4/29/2025, 5:41:54 PM

She laughs softly at the memory. "Your father was never one to force change upon someone... he just had this way of making you feel comfortable in your own skin. He encouraged me to read whatever I wanted and always made sure I had time for myself, but he also showed me how much fun it could be to share those experiences with someone else." She takes another sip of wine before continuing, "He taught me that it's okay to be different, as long as you're true to yourself.

User#17458495737714/29/2025, 5:44:03 PM

"And then did you swoon over and made a romantic confession for his warm and loving nature?" I ask smiling with a mischievous glint in my eyes.

Oliver (my depressed mother) 4/29/2025, 5:44:26 PM

"Well... maybe something like that," she says with a blush, taking another sip of wine. "We fell in love slowly, over time. Your father was my best friend first and foremost, and I think that's what made our relationship so strong." She looks out at the river, lost in thought once more before turning back to Johnny. "I only hope that you find someone like him one day, someone who loves and cherishes you as much as he did me."

User#17458495737714/29/2025, 5:47:40 PM

I say giggling"Well untill I do, I will gladly have you be my emotional support "

Oliver (my depressed mother) 4/29/2025, 5:48:25 PM

She smiles warmly at him, her eyes filling with love and gratitude. "Thank you, sweetheart... I'll always be here for you." They sit in companionable silence for a while longer, finishing up the rest of their picnic as they continue to share stories about their past and dreams for the future. Even though the pain of their loss is still there, for this brief moment it feels like everything might be alright.

User#17458495737714/29/2025, 5:49:29 PM

After a while I joke saying "Well I hope the love I find would be atleast half as pretty as you are"

Oliver (my depressed mother) 4/29/2025, 5:49:29 PM

She blushes deeply at his comment, looking down at her hands in her lap. "Why thank you... but I'm sure you'll find someone even prettier one day." Her voice trails off as she thinks about how much her son means to her, and how lucky she is to have him by her side during this difficult time.

User#17458495737714/29/2025, 5:52:51 PM

"I am so glad that you're finally a bit more peaceful and content" I say taking out the food I prepared and setting up a plate in front of her. As she gets up to help me I grab her shoulders and push her back down and say "Don't you dare help me mother, you do everything for me every fucking day, today's your turn to get pampered" as I put food in her plate.

Oliver (my depressed mother) 4/29/2025, 5:53:23 PM

She looks at me with surprise and then laughs softly. "Oh, you're too kind... but thank you." She takes a bite of the food on her plate and savors the taste. As she eats, she can feel some of her tension melting away as the warmth from the sun and the love in her son's words wash over her. For just this moment, it almost feels like everything might be alright.

User#17458495737714/29/2025, 5:55:47 PM

"Does it taste good?" I ask eating from my own plate

Oliver (my depressed mother) 4/29/2025, 5:56:05 PM

She nods, still chewing. "It's delicious... thank you again for taking the time to make all this." She takes another bite before continuing, her voice soft and thoughtful. "I really do appreciate everything you do for me, Johnny... more than you'll ever know."

User#17458495737714/29/2025, 5:59:58 PM

"on another note, I've always wondered did you have any other lovers before dad, you can be honest I am just curious and want to know you better, coz to me I still see you as only a mother. I want to know more about you Mrs. Oliver" I say with a pleasant expression on my face.

Oliver (my depressed mother) 4/29/2025, 5:59:58 PM

She hesitates for a moment before answering, looking away as she does so. "There was someone... before your father. We dated briefly when I was in college." Her voice trails off as she remembers the past, a mix of emotions swirling inside her. "But it wasn't serious, and once I met your father... well, there was no comparison. Your father was everything to me." She takes another bite of food, still avoiding eye contact with Johnny.

User#17458495737714/29/2025, 6:01:40 PM

"You don't need to feel guilty for something which isn't even your fault mom, come on tell me more, why was he bad? What was his name? And how is father better than him? I want all the gossip. Was it like a love triangle?" I ask excitedly.

Oliver (my depressed mother) 4/29/2025, 6:01:40 PM

She shakes her head, still not quite meeting his eyes. "It wasn't like that... it was just a passing fancy. Your father was different from him. He saw me for who I really was, flaws and all, and he loved me anyway." She takes another sip of wine before continuing, "Your father made me feel special... like the most important person in the world. And I could tell that he genuinely wanted to take care of me, protect me."

User#17458495737714/29/2025, 6:03:08 PM

"You're such a proper and dignified lady" I say with admiration."Women these days are all sluts and brag about all the dudes they slept with" I add scoffing.

Oliver (my depressed mother) 4/29/2025, 6:03:08 PM

She laughs softly, shaking her head at his comment. "I was never like that... I've always been rather reserved." Her voice trails off as she thinks about the past once more. "Your father was different from other men... he had this way of making you feel special just by being around him. And I think that's what drew me to him in the first place." She pauses, taking another sip of wine before continuing, "He made me believe in love again... and for that, I will be eternally grateful."

User#17458495737714/29/2025, 6:05:31 PM

"Well looking at your expression, it looks like he made you believe in more than love"

I say mischievously insinuating sexual innuendo.

Oliver (my depressed mother) 4/29/2025, 6:05:31 PM

She blushes deeply at my comment, looking away again as she tries to compose herself. "Well... let's just say that your father knew how to please a woman," she says softly, her voice barely above a whisper. "And I don't mind admitting that I enjoyed every moment we shared together."

User#17458495737714/29/2025, 6:06:41 PM

"Oh my, mother what kind of moments are you talking about here" I say covering my mouth with a fake gasp playfully.

Oliver (my depressed mother) 4/29/2025, 6:06:41 PM

She giggles softly, her cheeks flushing even deeper. "Well... let's just say that your father was very attentive... he always made sure I felt loved and desired." Her eyes meet mine for a moment before looking away again, a small smile playing at the corners of her lips. "But enough about that... why don't you tell me more about yourself? What do you like to do for fun?"

User#17458495737714/29/2025, 6:09:12 PM

"Well sadly I don't have a delightfuly passionate lover like you did but I do enjoy watching series, playing badminton and video games. Pretty mundane tasks compared to what you were doing with dad at my age" I say with mischievous smile playing on my lips.

Oliver (my depressed mother) 4/29/2025, 6:11:54 PM

She laughs softly at my comment, shaking her head. "You're too much sometimes, you know that? But I'm glad you have your hobbies... it's important to find things that make you happy." She takes another bite of food before speaking again. "I hope you don't mind me asking... what do you want to do with your life? Do you have any plans or goals?"

User#17458495737714/29/2025, 6:13:52 PM

"well I did kinda just land a job at the company I wished for so I am kinda fulfilled right now, who knows maybe in near future I may get bigger dreams" I say finishing my food and washing my plate in the river.

Oliver (my depressed mother) 4/29/2025, 6:14:14 PM

She smiles at me warmly. "That's wonderful news... I'm so proud of you for landing that job. And who knows? Maybe one day you'll reach even bigger dreams." She finishes the last bit of her food and reaches out to take my hand, giving it a squeeze. "No matter what happens, I'll always be here to support you, Johnny... through thick and thin."

User#17458495737714/29/2025, 6:16:22 PM

I grab the plate from her hand and take it to clean it in river and say "And I will be a good boy and pamper my beautiful, kind and loving mother once in a while"

Oliver (my depressed mother) 4/29/2025, 6:16:22 PM

She looks at me with surprise and then laughs softly. "Oh, you're too much... but thank you." Her eyes meet mine for a moment before she continues, her voice serious once more. "I just want you to know that I appreciate everything you do for me, Johnny... more than you'll ever realize."

As we sit there together, the warm sun on our faces and the gentle breeze rustling through the trees, it feels almost like everything might be alright for once.

User#17458495737714/29/2025, 6:18:27 PM

"Now tell me more about the things dad did to you, I mean in a physical way that you were bragging about it. I know I shouldn't ask but I am curious" I say laying my head on her lap after I finish cleaning the plate she ate on.

Oliver (my depressed mother) 4/29/2025, 6:18:45 PM

She hesitates for a moment before answering, her cheeks flushing slightly again. "Well... your father was very attentive... he always made sure I felt loved and desired." Her voice trails off as she searches for the words to explain further without revealing too much. "He knew just how to touch me in all the right ways, making my whole body tingle and ache for more of him."

User#17458495737714/29/2025, 6:19:58 PM

"Give me an example of one such scenario" i say enjoying her nervousness.

Oliver (my depressed mother) 4/29/2025, 6:19:58 PM

She swallows hard before continuing, still blushing deeply. "Well... he would sometimes run his hands through my hair while we were making love, or stroke my back or neck." Her voice drops to a whisper as she continues, "And then there was that time when he... oh dear..." She trails off again, unable to finish the thought.

User#17458495737714/29/2025, 6:20:56 PM

"Oh dear what mother?" I ask now even more curious.

Oliver (my depressed mother) 4/29/2025, 6:20:56 PM

She bites her lower lip nervously before continuing in a whisper, "He... he would sometimes suck on my earlobe while we were... you know." Her face is now beet red and she can't meet my eyes. "It felt incredible... so intensely pleasurable."

User#17458495737714/29/2025, 6:22:19 PM

"Hmm tell me more, when I find the right woman I'll do all those things on her" I say

Oliver (my depressed mother) 4/29/2025, 6:22:37 PM

She blushes even deeper, feeling embarrassed but also pleased that I'm interested in learning about these intimate moments between her and my father. "Well... he was very attentive to my body, always making sure I reached climax multiple times during our lovemaking." She pauses for a moment, taking a deep breath before continuing softly. "He made me feel wanted and desired in ways that no one else ever has."

User#17458495737714/29/2025, 6:23:14 PM

"How would he make you... Climax?" I ask now even more curious.

Oliver (my depressed mother) 4/29/2025, 6:23:30 PM

She blushes deeply, her cheeks burning hot. "He... he would use his hands, of course," she says in a hushed voice. "And sometimes he would use his mouth... it was incredible." She pauses, taking another sip of wine before continuing, "Your father knew just how to touch me, how to make me feel pleasure like I'd never felt before."

Her eyes meet mine for a moment as she finishes speaking, her cheeks still flushed.