OnlyFans for Fun and Profit - but mostly for fun - (Lip_tease and DreamingOfMyEx)

[DreamingOfMyEx]

This story is, in a way, a spin-off of a group roleplay started a few months ago but ended prematurely. I had such wonderful hopes for my character that it seemed a shame to let her disappear.
Only the character I created (Anne Marie) will be carried forward into this new story, and she will have no interaction with any characters created by anyone else from that group roleplay. The name of the town came from the originator of the group play, but virtually all the work done creating the details of the town were mine.
I have tried contacting the member who started the group play, but to no avail. All that having been said, if anyone thinks I'm encroaching on anyone else's intellectual property - you're probably wrong, but feel free to let me know anyway.

 

[DreamingOfMyEx]

Anne Marie Wilson (Maiden name - Peterson) - Recently Widowed - Former teacher, Former church secretary, Stay at home mom.



Physical Description:

• Anne Marie Wilson
• 31 years old – female - (born 1994).
• Height: 5'6", Weight: 127

Childhood and Family:

• She grew up in Toland, her only significant time away was when she went to college.
• Hers was a happy, healthy household with three girls, all approximately two years apart in age. Her older sister Jeanette married a lawyer and lives in Hawaii. Her younger sister Felicia married a Navy pilot and lives in Virginia in a suburb of Washington DC.
• Her father, Marcus, is a Family Practice physician. Her mother, Mary, was/is the stay at home housewife/mother type who after all three girls were in school, volunteered for numerous charities – setting the example for how the wife of a prominent man in the community should “give back” to the community. “Doctor Mark” and his wife moved to Toland a week after completing his residency (which was one week before their first child was born.) He worked in both the Family Practice clinic in Toland, and the County Hospital in Carlson Creek. As soon as their youngest graduated high school, they moved to Capital City where he is now an administrator at the big teaching hospital associated with the medical school at the big university there.
• The Peterson family had no relatives in or around Toland and no close ties before moving there.

High School:

• Anne Marie was a star pupil, graduating second in her class.
• She played catcher on the Girl’s Softball Team, and was captain of the Academic Decathlon team for her last two years.
• She played clarinet in the Marching Band, and Violin in the Orchestra.
• Her Senior Year she was voted “Most Likely to Win a Grammy”, “Most Likely to Travel the World”, and “Most Likely to Win a Presidential Debate”. It was a small school, and most seniors averaged three “yearbook superlatives”.
• She started gaining weight in her Sophomore year. Given that both sisters were considered much “prettier” than her, it affected her self-image greatly. She dated very little, and poured herself into music and academics.
• She graduated in 2012.

College:

• She attended Baylor University on a music scholarship.
• At Baylor she played clarinet in the Marching Band.
• She graduated in 2016 with a Bachelor of Fine Arts degree and a teaching certificate.

Professional Life:

• She slipped right into an open teaching position at Toland Middle School as soon as she graduated from Baylor. She taught music, directed the Middle School Marching Band, and also taught an English class. She was the faculty sponsor of the Debate Club which included both High School and Middle School.
• The schools closed in Toland in 2018. That’s when she learned she was pregnant. Instead of fighting for a position in a nearby district, she elected to be a stay-at-home mom.
• Anne Marie used to volunteer as a part-time secretary and receptionist at the First Baptist Church of Toland. One year earlier, she lost her husband in an accident. She moved to Capital City to be close to her parents, where she did not work but concentrated on her three boys and helping them deal with the loss of their father. She has just moved back to Toland.

Marriage, Family Life, and things that happen behind closed doors:

• She is a widow with three children (all boys). She married Kyle Wilson in 2018. He died one year ago.
• Her home address is 1009 Murphy Street. This is located near D-7 on the map. On the south side of the road, next to the city limits. Two stories (all bedrooms upstairs) with an attached garage. She and Kyle lived there since they got married. Unoccupied, it was well-maintained by a realtor from Magnus who also manages properties. Getting it dirt cheap as Toland's economy was tanking, she recently paid it off with insurance money from her husband's death, and has quite a bit of money left over.
• She also owns the house next door (1005 Murphy Street) which needs work, but is livable. Purchased with insurance money, she recently closed the deal the last week of February, 2025.
• It is a walk of nine residential blocks to the First Baptist Church, where she is still a member despite having been away for a year.
• Though it is a relatively safe town where she grew up and knows everybody, she carries pepper spray on her walks or jogs. And a taser gun - the kind that will fire electrodes several feet instead of having to wait for the assailant to get within arm's reach.
• Children: She is proud mother to three rambunctious boys - Andrew Kyle (6), John Marcus (4), and Thomas Michael (2). She calls them Andrew, John Marcus, and T.M. - Though others might call them by other names (Andy or Drew instead of Andrew, etc.)
• She is finished having children - that's the plan anyway. She is on birth control, not because she is sexually active, but for other reasons. Termination of a pregnancy is out of the question.
• Her sex life is non-existent.

Relations within the community:

• The town is small enough that she knows just about everyone - especially since she grew up and went to school there, AND taught school there for a couple of years before the school was closed.
• She tries to be a good example - especially since she is so closely associated with the Church. She generally reads who will and won't be receptive to invitations to attend church, but is always like "I hope to see you at the Christmas Pageant this year, do you think your children would like to be in the show?" for those who aren't interested in regular attendance but who will go for special occasions.
• She isn't as active in the community as she would like to be - with the three young boys making demands.

Other noteworthy things:

• Early on in their marriage, her husband introduced her to his favorite kink: Femdom roleplay.
• She didn't enjoy the Femdom roleplay, but she did it for him, and got good at it.
• She has, over the past three years, lost a lot of weight, going from this to this.
• Has she had a little "work" done? Speculate all you want. She still dresses modestly.

 

[Lip_tease]

Austin Remington - Former Student - Owner Of The local Theatre - Currently Homeless.

Physical Description:

Austin Remington
18 years old – male - (born 2007).
Height: 6'1", Weight: 170

Childhood and Family:

• Born and brought up in Toland. He doesn't hate his hometown but isn't very fond of it either. He spent a few years in the city for his college.
• He's the youngest of the two. His father, Harold Remington, and mother, Maggie Remington, were high school sweethearts who were infamous in the town for getting married within days after their high school graduation. They are still married and live with their daughter in the city.
• The eldest, his sister, Olivia Smith, is now married and lives in the city.
• His grandfather, Richard Remington, was the one who gave Austin his name. He passed away when Austin was sixteen years old.

Relations within the community:

• The Remingtons were among Toland's original founding families. Austin Remington, a sixth-generation member, is the only descendant of the initial settlers still living in town.
• In the early 90s, when the town's economy was booming, Richard Remington, Austin's grandfather, built the first and only theater in Toland. The theater has since been the cornerstone of the town's entertainment and the Remington family's wealth.

Marriage, Family Life, and things that happen behind closed doors:

• Seeing how carefree his son Harold was, Richard refused to pass over the ownership deed of the theater to his son and left it all to his grandson, who was the only person that took care of him in his final days.
• Soon after Richard died, the rest of the Remington family sued Austin for their claim on the theater and lost pretty badly. This drove a wedge between Austin and the rest of the family.
• Unable to stay with his own family Austin used the theater's revenue and moved to the city to pursue his passion for fine arts film production.
• This gift soon turned into a curse for Austin, whose college tuition fee relied solely on its revenue. As the town's economy tanked, Austin had to quit his studies and return back to Toland. Shunned by his own family, he lived in the poorly maintained theater for the past few years.

Other noteworthy things:

• Thanks to his college days, Austin is a bit experienced in screenplay and videography.
• His life's goal is to make it into the film industry. So he frequently writes stories and screenplays and sends them to his old theater contacts.

 

[DreamingOfMyEx]

Link to Map of the town:

https://imgur.com/4DJE9Z6

History, descriptions, etc, will come later, as needed.

As stated elsewhere, the town suffered the loss of the main industry. The population was once approaching 10,000. Now it has only a few hundred. Anne Marie Wilson's residence is on the south side of town, quite literally at the City Limits, and just north of the closed community college complex. (D-7 on the map)

 

[DreamingOfMyEx]

Middle School boys. The one thing that could be counted on was they would always try to get a peek down the female teacher’s blouse. The more “well-endowed” the teacher, the more peeking attempts. Try as they may to be subtle about it – they were never as subtle as they thought they were being.

Anne Marie had been one of those “well endowed” teachers, though she hardly considered herself attractive to the opposite sex. She was “pretty” in a way - pretty in the face one might say, but frankly – carried way too much weight and didn’t carry it well. But times change. Anne Marie had transformed herself into something far more desirable over the past three years, and Austin (one of her former students) was all grown up and graduated. For all intents and purposes, he was an adult, and Anne Marie had invited him to her house for dinner on an evening the children would be away.

Dressing for dinner, she was faced with the decision of how much cleavage to display for the now-adult Austin. The dinner wasn’t a “date” – it wasn’t about romance or sex – it was strictly business. She had a couple of propositions to make which could be mutually beneficial to them, and she would have to make it clear that sex wasn’t on the table (or any of the other furniture).

In the end, she decided to do the right thing. It was two friends getting together for a bite to eat and a chat. She didn’t need to use her sensuality to “entice” him to do anything. He would either recognize the opportunity as a good deal, or not. Besides, it wasn’t as if Anne Marie’s wardrobe was full of outfits created to get a rise out of healthy young males. She was still a good Christian woman dealing with lingering sadness over the death of her husband.

Kyle had been a good man, a loving husband, an awesome dad, and his work on the offshore oil rig provided them with an income which enabled them to live like nobility in this economically depressed town. The accident on the rig was devastating, but at least the life insurance money enabled her to provide for her and her children. However, it wouldn’t last forever. That’s why she came up with the idea she was going to pitch to Austin.

When she answered the door, Austin would be hit with the smell of spaghetti sauce and garlic bread, not overwhelmed by Anne Marie’s sensuality. Still, she didn’t want to dress like a slob. Her jeans were not too tight, but they were not so baggy that one couldn’t see she had a very feminine figure underneath. Her usual sneakers were replaced with heels – though not too tall. And her usual college sweatshirt had been tossed aside for a nice blouse with buttons. Like the jeans, it wasn’t too tight, but the sight would have been inspiring back in the day when she was still teaching, and she hoped it would be appreciated by her former student on this evening.

“Hello Austin, come in, thank you for coming. I hope you’re hungry…”

There was wine on the table, too. At 18, Austin technically couldn’t drink legally, but this wasn’t exactly Al Capone taking over all the speakeasies in Chicago – it was a glass of wine at dinner. A “welcome to adulthood in my eyes” gesture. A prelude to a very adult business proposition.

One of those propositions would become public enough very soon - she had already mentioned it to Austin in passing at the local convenience store - the possibility of him "renting" her other house in exchange for doing some work for her. The other proposition - that was something she planned to keep hidden from the good citizens of Toland (and everyone else she know) forever.

 

[Lip_tease]

Have you heard of the phrase "Angels are just ordinary people that help us believe in miracles again"? Austin experienced something similar to that when he met Mrs. Peterson, his middle school teacher, at the local convenience store. For a good minute, Austin failed to recognize her. He knew that face from somewhere but wasn't really sure on the where part until she recognized him and introduced herself. Not to blame Austin, but her transformation was on another level that he had ever seen before in his life. They stayed talking about each other's lives for a few hours. By the end of their conversation, Mrs. Peterson invited him to have dinner at her place and discuss the possibility of him renting her other house.

He initially tried to refuse her invitation, thinking she was just trying to be kind and polite, but when her tone changed, Austin's middle school memories of the sweet but strict Mrs. Peterson came flooding back; after that, he just quietly accepted. Also, home-cooked meals were a luxury for him. After being shunned by his own family, Austin was just barely getting by, living in his theater and also renting it out as a convention hall for public or corporate gatherings, which ended up being the only way he was able to get some profit from the theater. The last time a movie was screened in that theater was more than a couple of years ago. With no money to pay the bills, Austin had to take the theater off the power grid and rely solely on the old diesel generator for all of his electrical needs. In fact, the reason he was there at the convenience store was to get some free air conditioning while no one judged him for being there.

Today Austin was supposed to meet Mrs. Peterson or Anne, at her house for dinner. He nervously checked his outfit, wearing a red checked shirt, black jeans and a pair of blue faded converse, infront his huge mirror to see if there are any holes or marks on it. The mirror was one of a kind, set inside an eight by eight wooden frame and was mostly used for classical theater performances. After finishing his check he grabbed his deodorant and sprayed it all over his cloths, trying to concel the smell of old wallpaper and left his theater in high spirits. It was a long time since he felt this happy, walking throught the desolate residential area. As he approached her house, his nervousness crept back in.

He stood there for a minute and calmed himself down before pressing the calling bell. While waiting the smell of freshly baked bread and home made cooking leaked throught the front door and filled the patio, instantly churned up his appetite. When the door swung open he was awe stuck, looking at his old teacher, who looked nothing like a 30 year old. She wasn't exactly dressed to get a raised out of him, but her fit jeans, buttoned blouse was enough to accomplish it. Austin could feel his face and body heating up by just looking at her.

“Hello Austin, come in, thank you for coming. I hope you’re hungry…” Anne smiled graciously, welcoming Austin inside the house.

"Thank you for inviting me, Mrs. Peterson." Austin's eyes struggled to maintain eye contact. Anne picked up on it instantly.

"Please, call me Anne. We are both adults now, aren't we? Come on, the dinner's ready." She guided him towards the dining table.

 

[DreamingOfMyEx]

During dinner they had a pleasant enough conversation about growing up in Toland, their time away from town, and what brought them both back. Anne Marie didn’t hide the fact that while she would never completely get over her husband’s untimely death, the insurance money she got ensured she and her children would live comfortably for quite a while. Quite a while, but not forever. Eventually, she would have to go back to work, and she didn’t want to wait until the last minute.

Then she shifted the conversation to the house she had “for rent”. Though she tried not to come across as “controlling”, she found it easy to control the conversation. After all, she had been a teacher (one of Austin’s teachers) which gave her a certain authority in his mind. And she had boobs. Just a tiny hint of cleavage, but it did continue to draw his eyes – and mind. Plus, there was the age difference – she was more accustomed to talking to men than he was accustomed to talking to women.

“I really don’t think we need to worry about any sort of formal agreements, no contract or anything. I know you don’t have a lot of income coming in, and I don’t really need the money. I’m more concerned about having someone in the house. Empty houses can deteriorate more quickly than a house that’s lived in. You’d just be doing little things like upkeep, keeping the lawns looking good, that sort of thing. Plus, I’d feel safer with you next door. If you feel I’m asking too much you let me know, and if I feel you’re not doing enough, I’ll let you know, and we work things out to our mutual benefit. And if need be, you still have the theater, so if this doesn’t work out it’s not like you’ll be homeless.”

She also pointed out that she would pay for any materials needed. All he had to do was the labor, which she was confident he could do thanks to helping his grandfather maintain the theater throughout much of his childhood.

Anne Marie appeared confident enough, but the closer they came to the end of the meal, the more nervous she got. Her plan was to introduce unusual part of her proposals after dinner – over a glass of wine in a more relaxed setting. Maybe she should have applied a little more lipstick, or left an additional button undone, but it was too late for that now without being too obvious.

“There’s a video I’d like you to watch,” she said as Austin settled onto one end of the sofa, an end table positioned next to it for his wine glass. Anne Marie, instead of sitting next to him on the sofa, took a chair. Beside her was a laptop computer connected to the television with a long HDMI cable, and the television remote. She pressed a few buttons and a YouTube video popped up onscreen. It was titled "Crushing and ripping Andy bear with black high heels"

"I know it may seem a little strange, but there's a reason I want you to see this." As she started the video, she discretely watched Austin to see how the video affected him. Specifically, she looked for clues he was getting aroused. Clues that he might harbor submissive tendencies. Meanwhile, she simply sat there looking pretty, and sipping her wine.

--

When the video ended, she softly whispered - "So, tell me your thoughts."

She knew boys of his age rarely admitted to anything - even masturbating (which Kyle assured her every guy does it, frequently, from puberty to old age) - so she hardly expected Austin to admit to being a submissive. And it's not that she even wanted him as a sub. She just wanted someone who would help her make her own videos. Understanding the appeal of the videos - that would be useful.

 

[Lip_tease]

It was a great evening. In fact, it went better than Austin imagined. Austin ate some of the best food he'd had in a really long time, served by the most gorgeous-looking woman he'd met in his entire life. He half expected it to be a family dinner with her kids running around and asking some brutally honest questions kids would often ask. But it was just the two of them for the entire evening. Though Austin was fully attentive in their conversation, sometimes he would be completely distracted by her body. Whenever she leaned over, which she did a lot to serve and pass the food back and forth, her buttoned blouse barely held and would push her boobs up, making them slightly pop out of the cleavage for a quick second. Austin tried his best to be discreet while looking, however Anne would always meet his eyes and shoot him a smile. The kind of smile that indicated she knew what his eyes were watching.

Anne moved the conversations throughout the dinner. She addressed everything from her past, the Toland's past, and her expectations for renting the place and she did it all with ease. Anne was practically offering him a place to stay with no requirement for rent or deposit. Even though, looking from the outside, Austin knew there are a bunch of repairs to be made before it becomes livable. The cherry on top? She even offered to cover the repairs. Everything was perfect until they moved to the living room and watched the video.

The room was quiet except for the low hum produced by the AC unit on the wall. He felt a mix of emotions watching the video. Whenever the lady stepped on the doll, unbeknownst to him, his breathing would change. Austin's body shifted multiple times due to some unknown discomfort, but his eyes were stuck to the screen. At the corner of his eyes, he noticed Anne sitting in a separate chair, where her red lips sipped on wine, and she kept looking more at him more than she looked at the T.V. Austin was no stranger to kinks, sensuality and porn in general. Even now he would regularly steal the wifi from the church, which is next to his theater, to watch games, movies, and of course porn.

"So, tell me your thoughts." Anne whispered at the end, eagerly looking at Austin for an answer.

He had some idea of what the video was representing, yet he wasn't sure if it's the same answer Anne was looking for. Naturally, he started overthinking. Would Anne, who Austin knew for a fact was a devoted Christian who goes to church regularly with her family, be into something like domination play? No, right? Right? But what if? For Austin, the "what if?" was very intriguing, but Austin decides to play it down. His brain tamed his tongue after fully processing all the outcomes of his action, including the one where he would have to go back to living in his dilapidated theater.

"Well... Mrs… I mean Anne. I liked her heels." Austin said, looking at the screen and looking back at Anne. He felt it was a good place to start.

"Okay... What else?" She questioned, without changing her look and taking a swig of wine.

"I think it was a waste of a perfectly good toy, and I honestly don't know why she stepped on that many times on the poor toy or why people even watch these." Austin's hands squeezed his knees. "If she wanted to rip it apart, there were easier ways to do it."

"Interesting," was all Anne said, looking at Austin, because now she had everything she wanted.

The reason why she distinctively remembers Austin is because of his telltale gesture he does whenever he lies. While she was his middle school teacher, she noticed that whenever Austin tried to lie, he would grasp something and squeeze it a little. Whether it be a book, his bag straps, or even his own arms and legs, his hands would always tighten their grip. Anne always found it cute and innocent.

"Old habits really do die hard, huh." Anne thought to herself, happily downing the last of her wine.

 

[DreamingOfMyEx]

Anne Marie wondered if Austin was confused about what he was experiencing, or if he knew exactly what he’d just watched and was trying to appear more innocent than he really was. Either way, he was obviously nervous about it – and that was a bit exciting for her. Anne Marie’s goal was not to dominate the young man, but she couldn’t help but feel that little thrill that came from being in control of the situation.

She tried to maintain a professional demeanor as she spoke.

“Now that you’re an adult, I’m sure you understand that people have a wide variety of interests when it comes to … sexuality.” She paused for a moment. After all, she’d just brought up the subject of sex – not something to rush through the first time talking to a former student. “A lot of men love the idea of submitting to a woman – Whether they want it for real, or if it’s just a fantasy, it can be a very powerful motivator in a lot of men. It’s referred to as ‘Female Domination’ or FemDom for short. Have you ever heard of it?”

Maybe he hadn’t – or maybe his computer was full of images of women in latex beating naked men suspended from the ceiling. Either way, FemDom was about to become a part of his life in a way he never could have imagined.

“This video? It could be she just doesn’t like teddy bears – but I’m pretty sure that isn’t the case. This is the sort of thing that appeals to a great many men. Sexy heels project power. The teddy bear is innocent and helpless. There’s no doubt in my mind that more than one man has gotten himself off while watching this video.”

If we’re going to have an adult conversation, there’s no sense in beating around the bush, right?

“The comments for this video are disabled, but if you watch others like it you’ll see men saying things like ‘do this to me, mistress’ – by the hundreds. I’m sure most of them don’t really want their insides ripped out by a pair of high heels, no matter how sexy they look – but nevertheless, the men find it titillating.”

She paused again for effect, and to take another sip of her wine.

“There are a lot of women” she continued, inserting a thumb drive into her computer, “who make a great deal of money just by talking dirty to men on platforms like OnlyFans. It’s really astonishing to me how many men out there are willing to pay money for … well, some just to see women doing sexy things, and some to experience something more specific – something FemDom related.”

--

Another video started – showing just a chair sitting in the middle of what appeared to be an empty room. It was a little blurry – as if perhaps the lens was dirty. Then, the clicking of heels on the hardwood floor announced the approach of a woman. A moment later she came into view – wearing nothing but black lace lingerie, sexy black heels, with a black veil covering her face. She was even wearing a matching garter belt and stockings. Her long blonde hair was tied in a ponytail – and her nails were long – almost impossibly long – and painted glossy black to rival the shine on her shoes. They were sharp and wicked-looking.

Her breasts were barely contained in the lacy bra – threatening to spill out should the woman make the wrong move … or the right one. They were large – quite large, and much more firm than one would expect of breasts of that size.

Even though her face was covered by a veil, it was obvious she was quite beautiful. Her makeup was quite heavy, but not so heavy it could be considered overdone.

When the woman sat, she crossed her legs and smiled at the camera.

“Good evening, my pet.” She spoke with an accent. Eastern European. Mysterious and oh so sexy. “I do hope you enjoyed your dinner ….”

Dinner? How would she know in advance about dinner? Is this woman somehow a friend of Anne Marie, knowing she would invite him to dinner???

“Tell me, Austin. Had I looked anything like this when I taught your Seventh Grade English class, do you think the boys would have paid more attention ….”

Miss Peterson??? Anne Marie??? Impossible.

“… or” she reached down to adjust the garter strap on one of her stockings, giving the viewer a much more generous look at her breasts … “would little mannerisms like this been too much of a distraction for their little hormone-soaked male brains?”

She looked back at the camera, winked, then stood and walked away – the clicking of heels growing more distant until they stopped altogether.

-

Anne Marie smiled at Austin. Whatever nervousness she’d felt earlier had disappeared.

“Well???”