It Happened Gradually
by hellainiceland
Copyright© 2026 by hellainiceland
Incest Sex Story: My employer opens a whole new world to my son and me.
Caution: This Incest Sex Story contains strong sexual content, including Incest Mother Son Big Breasts .
If you hate this story, see my other works here to hate them more:
https://storiesonline.net/a/Happenstance
https://storiesonline.net/a/rathskeller
Your comments are always welcome. Thank you.
It was nearly a year ago when I first met her. I had arrived in this city around a month ago with my son after being laid off from a hotel in my hometown, where I used to work as a housekeeper.
I was desperately looking for a job when a woman working at a salon told me about a woman who ran some sort of employment agency. So I went to meet her.
After interviewing me for more than 20 minutes, she told me that the only job available was that of a maid at a woman’s house whose name was Rosemary. Since I had no other option, I said yes.
The next morning, I took a bus, subway, and then walked to the address she had given me. It was a 20-plus-story building with a glass façade and black and gold doors. When I pressed the buzzer, a woman answered and told me to come to the 18th floor.
“Hello,” she greeted me and introduced herself as she opened the apartment door.
She was wearing black pants and a white shirt under a black coat.
“Sit down,” Rosemary said, gesturing toward a very expensive-looking brown sofa.
Her walk had grace, she spoke with an upper-class accent, and everything in her house whispered old money. It was apparent that she was born with a golden spoon.
As she applied makeup and put on her stilettos, she fired a rapid round of questions ranging from my childhood to my son to my work. She told me all the terms and conditions and said she’d call my references and let me know. Five days later, I received her call, and she asked me to come to work the next day.
From that day onwards, I began working in her apartment every day, but it wasn’t until the next week that I saw her again.
I was cleaning the kitchen when a 50-something man came out of her room. He gave a sheepish smile when he saw me and tiptoed out of the house. A little, Rosemary emerged. As she sat down on the couch, her short nightgown loosely tightened with a belt parted, revealing the top part of her braless chest.
“Do you like working here, Molly?” Rosemary asked as she took out a cigarette from a silver box and crossed her tanned thighs.
“Yes.”
“Good. I want you to be here full-time, from morning to evening. I’m expecting lots of visitors, so I need help. Don’t worry, I’ll pay you well.”
With my son, Jim, starting school, rent and other expenses, I obviously needed the money, so I immediately agreed.
With that, I became a permanent fixture.
I soon noticed two things: she had a small group of friends, three males and two females, and all of them were very close. I saw them several times hugging, kissing, and touching each other all over the apartment.
One morning, I had been working there for four months, and I saw Rosemary come out of her room, followed by her friend Chris and his wife Susan. Rosemary was making coffee next to me in the kitchen when Chris came and, hugging her from behind, pressed the front part of his body against her back.
“I want it with milk,” he said, cupping her buxom chest over the top.
“Will soon get you fresh milk, I promise. Now get that butter,” she replied as she tilted her head and kissed his neck.
“OK, your highness,” Chris said, running his hands over her bare thighs.
Susan, who was also in her 50s and on the heavy side like her husband, was sitting on the couch in shorts and a top with a cigarette dangling from her fingers.
“I hope Rose isn’t giving you too much trouble,” she said to me.
“No, of course not,” I replied.
After breakfast, both Chris and Susan went home. When I was done cleaning the house, Rosemary called me into the bedroom and, pointing toward a bundle of notes on the coffee table, told me to take it.
“Go buy clothes. You’re always wearing these same jeans.”
“No, it’s OK. I have other clothes.”
“Don’t argue,” she said and went into the bathroom.
Truth be told, she was already paying me nearly double the amount she had initially said. Plus, I could eat or drink whatever I wanted. So I didn’t want to take the money, but her voice told me that she wouldn’t hear no.
Around three days later, she pointed out that I was still wearing the old clothes. I replied that I didn’t get the time to go shopping, though the fact was that I wanted to spend the money on daily expenses.
“OK. Let’s do the shopping now.”
“Now?”
“Yes, now. You can do the rest of the work later.”
She took me to one of those high-end stores that I would have never even dreamed of going to. Inside, there were rows of extremely beautiful but very expensive clothes. A sales assistant, who immediately recognized Rosemary, came toward us, and Rosemary told her to help me select whatever I wanted.
“Buy whatever you want for yourself and for your kid; I’ll be back in an hour.”
I didn’t want to buy anything, as even a top was worth more than all my clothes, but the assistant kept pushing me. The imposing store, the beautiful clothes, and the wine she kept giving me made me so nervous that I just said yes to whatever she suggested. In the end, I picked clothes for Jim and a couple of jeans, tops, and skirts for me.
When Rosemary returned, she asked me what I had bought.
“This is how you do shopping? What’s wrong with you? Come with me.”
She took me to the shoe aisle and made me buy two pairs of shoes, and then back to the clothes section where she selected a couple of tank tops, really short skirts, and gowns. Then she picked out a strapless brown dress and told me to try it on.
I went to the fitting room and put it on. I saw that, though beautiful, it was exposing half of my cleavage and was just covering my inner thighs. When I looked in the mirror, I could see each and every curve of my body.
“Wow! You look gorgeous,” Rosemary said, peeking inside the fitting room.
Coming near me, her face was directly opposite my chest as she was shorter compared to my 5’8” height. She gripped the sides of the dress with her fingers and pulled it slightly down.
“There you go.”
“It’s too short,” I whispered.
“No, it’s not. It’s perfect,” she replied as she stepped back a little and looked at me from all angles.
Taking my hand, she dragged me to the lingerie section where she selected bras and panties, including some lace and racy ones, for me.
Then, just as I turned to go to the fitting room to take off the dress, she asked me where I was going.
“To change.”
“No, you aren’t. Let’s go. Tamara and Smith are waiting at their place.”
Tamara and Smith were part of the close-knit group. She hurried me to her car. Inside the vehicle, she took out a pearl necklace from her bag and put it on me.
When Smith saw me, he let out a loud whistle and said, “Who’s this beautiful creature?”
“You’re looking amazing,” Tamara said as she came near me and looked at my 38-year-old body from head to toe.
“And she didn’t want to wear it,” Rosemary added.
With their eyes on me, I should have felt embarrassed, but instead, a shiver ran down my spine. Somebody was appreciating me after many years – and it felt really good.
Putting her hands on me, Tamara turned me around, and they inspected my back.
“Well, she’s got a great caboose,” Smith said, handing each of us a glass of wine.
We stayed there for more than 30 minutes, and I enjoyed each second of it as they admired my body from every angle, including my half-naked cleavage and bare thighs.
“Come on, I’ll drop you home,” Rosemary said when we were back in the car.
“No, I’ll take the bus, don’t worry.”
“Don’t be stupid. You’re drunk.”
That was true. After so much wine, I was a bit drunk. But even then, I didn’t want her to drop me off at home, partly because my house was nothing compared to hers, and since it was a Sunday, Jim would be home, and I didn’t want him to see me like this. However, there was no getting out of it.
I opened the door and went in with Rosemary. Jim came out of the room and stood there watching me with no expression on his face, and said nothing.
“Aren’t you going say hello?” Rosemary asked, breaking the pin-drop silence.
He greeted her, but his eyes stayed on me.
“So this is where you live?” she said as she looked around the one-room apartment. There wasn’t much to look around, to be honest, as there was just an old couch in the living room, where Jim slept, and a cupboard and a TV. In the bedroom, there was a bed and a cupboard. Apart from that, there was a small kitchen and even a smaller bathroom.
“Quit staring at your mom and get ready, as we are going out for lunch,” Rosemary ordered, giving him the shopping bags that I had put on the floor.
He quickly darted his eyes away from the body and took the bags.
I knew from his red cheeks that he was surprised to see me dressed like that, especially as he had always seen me dress prudishly. Given my new boldness, I wasn’t surprised that he was staring at my chest and legs so much.
“Are we going out for lunch?” I asked, somewhat surprised as I didn’t expect that.
“Yes. Jim, are you going to change your clothes or not?”
Putting the shopping bags on the table, I began taking out his clothes, fully aware that I was now bending down and giving Jim a much better view of my voluptuous breasts. As he stood there and looked at my boobs, I picked out a shirt and jeans.
Taking the clothes, he went to the bathroom.
“He’s a big boy. How old is he?” Rosemary asked as she sat down on the couch.
“Seventeen.”
“He doesn’t look 17.”
“Yes, he’s big,” I said.
When I said that, she raised her eyebrow and smiled. I simply shook my head as I obviously didn’t mean that. Jim came out in his new clothes, and off we went to the restaurant.
When Rosemary went to the ladies’ room, I said, “Stop looking at me like that.”
“You are looking weird,” he remarked.
“Shut up! Eat your food. Do you like your new clothes?”
“Yes,” he replied without looking at me.
“Did you buy them?”
“She did.”
“They are great. But why are you wearing this?” he asked, pointing at my half-naked chest with his eyes.
Instead of replying, I took a sip of the wine she had ordered.
During lunch, she asked Jim lots of questions about his school, girls, and hometown.
By the time we returned from the restaurant, I was totally drunk. Rosemary and Jim held me by my arms and gently laid me down on the bed.
“Take off her shoes,” I heard her say to him.
Then she rolled me over and began unzipping my dress. Though I could hear her and was also aware that Jim was there while she was undressing me, I didn’t have the strength to say anything.
“Get some top or something, she ordered as she buried my face into her chest and took off the dress, leaving only my bra and panties on.
“OK, now help me put it on,” she said, taking the shirt from him.
He placed his arms around my stomach from behind, with his face touching the bare skin of my shoulder, and helped her.
Rosemary got up from the bed and left the house after telling him to button up my shirt.
He sat down opposite me and began to button it up, but I told him to leave it and, rolling over to my side, went to sleep.
When I woke up, he was sitting on the couch listening to music on headphones.
“Please get me that medicine for the headache from the cabinet,” I said without getting up or buttoning up my shirt.
When he brought the medicine with a glass of water, I sat up and, pulling the shirt together, swallowed the pill. A little later, I went to take a shower while he went downstairs to get Chinese food.
Three or four days later, I was at Rosemary’s place cleaning the house when she called me from the bathroom.
“Today, my daughter and her husband have come with their baby, and my shoulders are hurting. Could you please massage them?” she was sitting in her huge hot tub, completely naked.
On the first day, during the interview, I had mentioned that I used to give massages to my late husband, but I didn’t expect her to ask me. Now I was in a bind.
I sat down on the edge of the tub and slowly started rubbing her shoulders. I also noticed that she had a thick bush down there, and though not as big as mine, her breasts were a handful.
As the water caressed her brown nipples, the door opened, and in walked a woman wearing a top and pajamas.
“Is he sleeping?” Rosemary asked.
“Yes, finally.”
“Molly, meet my daughter, Anna.”
“Your clothes will get wet,” Anna said as she took off her top, revealing a perky and round pair of boobs.
She was in her late 20s, and her sharp features, height, and walk were very much like her mother’s.
“Yes, get in and massage me properly,” Rosemary said in her sharp, matron-like voice.
I was a little hesitant, but also knew that my clothes would get wet, so I took everything off and quickly got into the tub and hid behind Rosemary’s back.
“So, how are things with the baby?”
“Oh! Don’t ask,” Anna replied as she got into it butt naked.
“I haven’t slept properly in days. All he does is cry, and all I do is feed him. Richard’s also becoming cranky.”
“Well, I’m sure he’s becoming cranky for another reason,” Rosemary said.
“Yeah, but I’m too tired for that.”
“How long has it been?”
“Months,” Anna replied.
It was then that I noticed that she was clean-shaven. But I immediately shifted my eyes as I didn’t want her to catch me looking at her.
“Poor Richard.”
“Why poor Richard?” I heard a voice as a man walked in. I intuitively hid myself as much as I could behind Rosemary and began praying that he wouldn’t see me.
“Your wife was just now telling me that you haven’t seen action in months.”
“That’s true. Who’s she?” Richard asked, pointing at me with his eyes.
“She’s the one I told you about. She’s not only hardworking but also gives a good massage.”
“Oh, that’s fantastic. I’d love a massage,” he replied, taking off his shorts and T-shirt.
So now not only was I naked in front of a strange man, but a mother-in-law was naked in front of her son-in-law, a daughter in front of her mother, and a son-in-law in front of his mother-in-law.
What was more perplexing was that none of them made any effort to hide their nudity in any way. Richard calmly walked toward the tub with his half-erect cock bobbing up and down.
Sliding next to his mother-in-law, he turned his back toward me and asked me to massage his back after I was done with Rosemary. Anna, meanwhile, had closed her eyes and was apparently trying to get some rest.
“You know it’s not good for either of you. Do you understand what I’m saying?” Rosemary said.
But Anna kept her eyes closed and didn’t reply.
“Answer me.”
“Yes, Mom.”
“Sometimes it feels as if all my training has gone to waste. Come here.”
“Mom, I’m not in the mood,” she replied, opening her eyes.
“Just come here,” said Rosemary as she stretched across Richard to pick a cigarette from the box.
When she stretched her body, her left nipple brushed against his arm, but there was no reaction from either of them, which meant they were used to these “touchings.”
Anna slid down the tub and came near us.
“What has happened to you? You always obeyed me and now ... Be a good girl and help him.”
Anna playfully smirked at her husband and placed her hands on his thing.
“That’s the maximum she does nowadays,” Richard complained as his cock began to become bigger.
“She needs a good beating, that’s all,” said Rosemary, putting her hands behind Anna’s head and pushing her face toward his thing.
It was getting too much for me, so I began to stand up, but Rosemary pulled me down and told me to continue massaging her.
Anna’s mouth was now filled with her husband’s cock while his hands were squeezing and cupping her tits right in front of us.
“Stop,” Rosemary ordered after a minute or so.
“Now go to bed with him.”
“Mom, please, I’m really tired.”
“Oh, stop moaning. I’m not asking you to climb a mountain. It will take two minutes.”
Richard took Anna’s hand, and both of them left the bathroom. Meanwhile, Rosemary and I put on our clothes and got out.
In the evening, Richard went home as he had work in the morning, but Anna stayed back. For the next three days, Rosemary took care of her baby as she wanted Anna to rest.
In the afternoon of the third day, Rosemary’s friends came over, all five of them. They were sitting around and talking, and I was helping Rosemary serve drinks, when the baby began to cry.
Anna went to the room and brought him to the living room. Sitting down next to Smith, a big, burly 50-something man with a thick moustache, Anna lifted her top and, pulling down her bra, began feeding him right in front of everybody.
“You’ve got bigger,” Tamara, Smith’s petite wife, said.
“Richard must be happy.”
“He wasn’t until three days ago,” Rosemary interjected.
“Why?” Susan, a tall, broad woman with an infectious laugh, asked.
“Guess,” Rosemary said.
“Were you disobeying him?”
“No, Aunt Susan, I was too tired.”
“That’s no excuse,” Chris, Susan’s husband and a former air force pilot who still had a youthful face, said.
“Are you forgetting your lessons?”
“Yes, she is. She needs a good beating; that’s what she needs,” Rosemary added.
“No, Rose, you’ve taught her well. I’m sure she won’t repeat it again,” Frank, a divorcee, remarked.
“Yes, I won’t,” Anna promised as she pulled her bra up, covered her chest, and placed the baby in the stroller.
“I know you won’t. Come here,” Frank told her, patting his thigh.
“Uncle Frank, I’m not a little girl anymore,” she replied with a smile on her face.
“You’ll always be a little girl for us. Now come here.”
“OK,” she said as she sat down on his lap.
“I wish my girl were like you,” Frank commented as he put his arm around her waist and hugged her tightly.
“Only Rose and we have trained our children well,” Tamara said.
“That’s true. Charles always obeys us. By the way, haven’t seen him in a while?” Frank inquired.
“He’s insisting that I go to Zurich and get myself tightened,” Tamara said, referring to her son.
“Yeah, he’s persistent,” her husband, Smith, added.
“I credit my mother for teaching me. Now I hope Anna will teach Keith,” Rosemary stated, referring to Anna’s child.
“You will, won’t you?” Frank, who was caressing Anna’s thigh over her shorts, wondered.
“Yes, Uncle Frank.”
“Good girl,” he said as he moved one hand toward her boobs, and with the other, he placed her hand over his groin.
As he began squeezing her perky and round tits, she unzipped his jeans and took out his cock, and began stroking it right in front of us.
She then went down on her knees and took it in her mouth, while he continued playing with her breasts with both hands.
Placing her hands on his inner thighs, she swallowed every drop of his cum as her mother and we watched.
Getting up, she tucked her boobs under her bra and went to the bathroom to rinse her mouth. When she came back, Smith already had his cock out and was stroking it.
Standing on the edge of the carpet, she took off her top and then, dropping her bra on the floor, began walking toward him.
“Take off your jeans too,” he ordered in his baritone voice.
“Uncle Smith, please no.”
“Don’t make me repeat it.”
She looked at her mom, but she and the others were busy discussing someone called Christina who was going through a divorce.
Anna took off her jeans and panties and lay down on her back in the center of the carpet. I watched from the kitchen as he got undressed and lay down beside Anna.
“She’s still tight,” he commented, slipping his finger in her pussy.
“That’s because you all have made her back hole loose,” his wife remarked, looking at her husband finger fucking Anna.
“That day, he and Smith were trying to enter her back hole together,” Chris’ wife commented, pointing at Frank.
“It’s called DP,” Frank told her.
“What’s that?” Rosemary inquired.
“Double penetration,” Frank replied.
“She wants to keep it tight for her son,” Rosemary explained.
They went back to talking about other things as Smith continued fingering Anna and sucking her nipples. He then made her go on her fours and, holding her hips tightly, started fucking her back hole.
With every push, her round and milk-filled breasts were moving back and forth, and she was moaning softly. He tightened his grip and, pushing his cock as deep as he could, began coming inside her.
She stayed on her fours until he had unloaded all his cum and then straightened herself. Both of them got up and went to the bathroom to wash themselves.
After 10 minutes or so, Chris asked Rosemary, “What happened to the fresh milk you had promised?”
“There it is,” she replied, pointing toward her daughter’s breasts.
“Yes, let’s taste it,” Tamara said.
“Get a bowl,” Rosemary ordered me.
Taking it from me, Anna placed it on her naked thigh and, putting her right tit inside it, began squeezing her brown nipple with her fingers. She then repeated the process with her left tit. When there was enough milk in it, she handed it to her mother, who took a small sip and passed the bowl around.
When the bowl reached Chris, he didn’t drink it and passed it on to Smith.
“I want to drink it from the source,” Chris declared.
“OK, Uncle Chris,” Anna said as she walked toward him and, placing her hand under her breast, offered her nipple to his mouth.
Placing his head on her thighs, he tightly squeezed both her boobs and began drinking her milk like a child.
“Put some of it in some bottle or something for Charles,” Tamara requested, referring to her son.
“No. If he wants it, he’ll have to come here,” Rosemary announced.
“Yes, Mom’s right. Ask him to come here, as I want to see him.”
After spending 30 or 40 minutes more, all of them went to their homes.
I was so shocked by the whole thing, especially by Tamara’s son asking his own mother to get her vagina tightened and Anna keeping hers tight for her son, that I didn’t sleep the whole night and didn’t go to work the next day.
I went back to the employment agency, but there were either no suitable jobs or jobs that didn’t pay so well. Though Jim had started working part-time at a restaurant, his wages were nowhere near enough. With no other option, I returned to Rosemary’s place.
I was putting the clothes in the dryer when Anna said, “Tomorrow is Friday, and Mom and I are going to the lake house for the weekend, and you and your son are coming with us.”
“But I can’t.”
“Why not?”
“I’ve work at home.”
“You are, and that’s final,” she said and went to her room.
The next evening, they picked Jim and me up from the bus stop. The lake house had three rooms, but Rosemary told me to share one room with Jim. They went to meet someone and told us not to wait. I took out the dinner I had packed from the bag and ate it with Jim. Since I was sharing not only the room but also the duvet, I put on a loose shirt and shorts and went to sleep with my back toward him.
In the morning, after Rosemary and Anna had breakfast, Anna called Jim to her room, and he stayed with her for over an hour.
“Your son’s great. Twice he did and wanted to go again. I was like, slow down, dude. My whole body’s aching,” Anna, who was wearing a transparent robe over a bra and panties, said to me.
“Is he really good?” Rosemary wondered.
“Oh, Mom, you should try him. Trust me. He’s so young, but someone has trained him very well.”
“She must have,” Rosemary stated, looking at me.
I simply stared at her in surprise.
“You’re a lucky mother,” Anna whispered to me as she left the room.
In the late afternoon, we went on a cruise with Rosemary captaining the boat. This was the first time I had been on a boat, and I was enjoying every second of it. Anna took off her bikini top and asked Jim to apply sunscreen to her. As she lay there on her stomach, he sat down beside her in only shorts and began applying it all over her body. She turned her body, and he started putting the cream on her breasts right in front of me as she lay there with her eyes closed.
Just then, Rosemary came and asked Anna to take the helm, and took Jim to her cabin. After around 30 minutes, Jim came out of the cabin and, avoiding eye contact with me, told me that Rosemary wanted to see me.
“This should cover Jim’s school expenses. I know you are working so hard for him. Take it,” Rosemary, who was in a bikini top and bottom, said when I went to the cabin.
I looked at the amount, and it was more than enough for his school expenses. I thanked her, but told her I couldn’t accept it. She insisted so much that I finally had to take it. She then gave me the pearl necklace that she had put on me the day she took me shopping.
“This is my gift to you. You look lovely in this.”
I again refused, and she again insisted, so I accepted it.
“In the evening, there’s a party at Frank’s lake house. Chris will come to pick Jim as the boys will do all the arrangements. We’ll go later. Only my friends will be there. You’ve met all of them. Now go.”
I left the cabin. Rosemary, Anna, and Jim spent the rest of the afternoon lounging on the boat in their bare necessities.
Frank’s living room was exquisite. It had the most beautiful furniture I had ever seen in real life or in movies. The couches were worth more than the one-room apartment I was living in.
I was sitting on a couch looking at a lifelike portrait of a woman when Susan, the heavy woman with an infectious laugh, said, “That’s Frank’s ex.”
“It’s beautiful,” I replied.
“Yes, Frank’s portraits are some of the best.”
The woman in the portrait was lying on a bed with her hands locked behind her head, her hair was in a mess on the pillow, one knee was raised, and the other leg was straight. She was completely naked. That she was tall, had a buxom chest, a flat stomach, some hair down below, and ample thighs was enough to make the portrait beautiful. But what was making it much more attractive was that it was black and white.
I was admiring it when I heard Susan’s voice again.
“That’s his daughter,” she pointed to another portrait on my right side.
I got up and went closer. Unlike the black and white one, this portrait was in color.
His daughter, who must’ve been 18 or 19, was wearing horse riding boots and holding a whip in her hands. Her hair was tied in a ponytail, and she was standing with her legs wide open, like a dominatrix holding a whip. She had her mother’s features — sharp nose, high cheekbones, big eyes, big bosom, and long legs. The only difference was that she was completely shaved.
When I first spotted the nude portrait of a woman in the living room, I was taken aback. When Susan told me it was Frank’s wife, I was taken aback even more. And now, watching the lifelike naked portrait of his daughter was making my head spin. That he not only convinced his own daughter to pose nude but also decided to display her in full glory in the living room was hard to believe.
“Did Frank do this?” I asked Susan as I wanted her to confirm it once again.
“Yes. She’s just like her mother.”
I nodded my head. I knew my son, Jim, who was out buying beers with Chris, must have seen these portraits. The thought of him seeing two women revealing everything sent a chill. Rich people are different, I thought.
A little later, Jim returned carrying beer with Chris. To say the dinner was sumptuous would be an understatement. There was seafood I had never seen before, meat of exotic birds I had never tasted, and dessert to die for. It was all prepared and cooked at Frank’s house and brought here.
At the table, others were talking, but Jim was busy with only one thing: trying as many dishes as possible. I stared at him, but he ignored me.
After dinner, everyone was sitting and talking when the discussion suddenly shifted to bras.
Smith, one of Rosemary’s friends, started claiming that he can unhook a bra faster than anyone. His wife, Tamara, agreed with him. Frank and Chris didn’t believe him.
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