From St Kilda to a Fling
Copyright© 2026 by CreameryCentral
Chapter 1
Erotica Sex Story: Chapter 1 - A woman's game of strip poker with her son and his friends ends up having unintended consequences on a trip from Melbourne to Sydney
Caution: This Erotica Sex Story contains strong sexual content, including Mult Drunk/Drugged Heterosexual Fiction Incest Mother Son Group Sex Double Penetration BBW
“God, I’m tired” thought Margaret Davenport as she peered up the road through the gathering gloom. She yawned as she tapped her fingers on the steering wheel.
“You okay, Mum?” asked Tim, her 18-year old son, from the back seat. “Fine, fine” Margaret answered with a smile. “It feels like a long day, that’s all. But we shall be stopping soon.”
Margaret was driving down from Melbourne to Sydney to see her Mum, Amanda. With her was Tim and two of his friends, Mark and Jake, also the same age as him. Tim asked whether they could come along to visit Sydney and Margaret didn’t have any objections. On arrival at Sydney, Mark and Jake were expecting to stay somewhere nearby Jackie’s mother’s house and see the sights with Tim.
Margaret knew both Mark and Jake since they were young but she hasn’t seen them for a while and marveled at what strapping young men they have become. The amazing thing is that they appeared to be marveling at her particular charms as well. Margaret initially caught their stares on her as they were getting ready to leave and during the trip she caught whispers from the back seat that made her first blush but also sent an unfamiliar thrill through her core. She was confused about her feelings, other than the boys were certainly well built. Margarethas been finding that her husband has been showing almost no interest in her lately. She has gained weight, she knew, (natural at 45 years old) but when she looked in the mirror, she still saw an attractive, confident woman. Well, at least a confident one, she mentally amended. Truth to tell, she was fairly overweight. But looks weren’t everything, she thought indignantly.
What Margaret neglected to think of is that she was also tremendously well-endowed. She was around 32H and her bust was always the first thing that entered the room. And Mark and Jake were very much breast men. Couple that with Jackie’s large eyes, a cloud of curly red hair and a ready smile and they had a lot of time for Tim’s Mum. Margaret couldn’t help but engage in a bit of innocent flirting during the drive, feeling reinvigorated from some male attention. She reminded herself that it was all in good fun as she shifted in her seat, her pussy tingling.
The car pulled into the parking lot of a motel. As Tim and his friends stretched their legs, Margaret went to the office and booked them into a room for the night. As she walked out to the car, her eyes involuntarily strayed towards the muscular figures of the boys, who were clowning around. Jake turned around, giving her a smile, as his gaze flicked to her legs extending below her pleated skirt. Margaretwas suddenly torn between wishing she wore something more conservative and being pleased that her body was still something that could attract the male gaze.
Margaret got two rooms, one for herself and one for Tim and the boys. Mark opened the boot and got out a six-pack of beer he brought along. Slightly shyly, he asked if Margaret would like to join them in their room for the evening. Feeling the need to unwind after the drive, she agreed, noticing how Mark’s face lit up at her answer.
As the evening progressed, Margaretfound herself relaxing, laughing at Mark and Jake’s jokes. Mark found a game of Twister in the cupboard and suggested they play. Margaret felt silly but decided to go along with the events, despite some misgivings about her size. She didn’t see when, the first time she had to bend over, Mark and Jake ogling her considerable ass pushing out against her skirt. For his part, Tim felt conflicted but excited. He didn’t know how to deal with his feelings but for a long time, he found himself thinking of his mother in a sexual way. Now, watching his friends salivating over her, he should have felt annoyed. Instead, he felt like joining in. He found his eyes also crawling over her rear as Mark and Jake grinned at him.
As the game progressed, Margaret found different parts of her anatomy pressed against the boys. It was all innocent, of course, but at a particular point, she found herself barely supporting herself while sprawled over Jake’s back. To her horror, she found her nipples were hardening. She was thankful that she was wearing her bra. For his part, Jake was enjoying the feeling of Mrs Davenport’s breasts resting on his back. Meanwhile, Mark was finding plenty of ways to make accidental contact with Margaret as they were playing. By the time the game done (Margaret taking more than a few tumbles), she was feeling quite warm and not just because of her exertions.
“I think we need more drinks to cool ourselves down!” Mark announced. “Okay” Margaret giggled. “I think I had enough beer for now, though”. She decided that she best start controlling herself. “I will pour some juice for us” Mark announced. However, when he was in the kitchen, he brought out a small flask of vodka from his coat pocket, putting a bit into Margaret’s juice.
As Margaret sipped the juice, she felt herself grow even more giddy. “What is happening?” she thought. But then Mark grinned at her and she smiled back, suddenly in her happy place. She shifted in her seat as her panties slowly gathered moisture. “Oh God” she thought. “Maybe I should call it a night?”. But she stayed where she was, laughing at the boys’ jokes.
Margaret had a hard time remembering who first referenced strip poker. It might have even been her as she made a joke about her college days. But suddenly the conversation was all about that and then Mark actually suggested they play. Not for real, of course, he was quick to averr. Just a bit of stupid fun for a few hands. Margaret ummed and aahhed, more for show than anything, and then laughingly gave in. “But no one be naughty!” she jokingly admonished. Mark refilled her spiked orange juice and winked. “Of course, Mrs Davenport” he exclaimed. “All above board!”
The game started off innocently enough. The first time Margaret lost, she made a big show of removing her shoes. Mark and Jake also lost and ended up removing their shirts. Margaret found her eyes roving over their bodies, her panties once again getting moist as she tried to get herself under control once again. Tim eventually had to take off his shirt as well and Margaret found herself staring at him with the same interest. “What is wrong with me?” she thought desperately.
The game came to a point where Margarethas taken off all possible knick-knacks and loose items and now suddenly she had to remove her own shirt. The atmosphere in a room suddenly seemed to shift. Margaret realised that she had a decision to make. A voice of reason screamed at her from the inside to declare the game closed. The less reasonable parts of her mind had other ideas. The truth was that she was getting more and more aroused in the course of the evening and now the thought of it finishing just like this felt unbearable. It surely couldn’t hurt to remove her shirt as well and keep the evening going, Margaret thought. She had no problem wearing a bikini so how was this any different?
The boys cheered as her hands went down to the buttons of her shirt. No shimmying or play acting this time. It was all she could do to keep her hands from shaking. She slid her shirt down her shoulders and defiantly shuffled her cards. All three boys, including Tim, immediately found their eyes sliding down to examine her mounds, clad in a conservative white bra. What Margaret didn’t quite notice was the look that Mark gave Jake as he noticed the bumps where Jackie’s hard nipples pressed against the fabric. For her part, Margaret found the scrutiny both embarrassing and exhilarating. In truth, she did not quite expect this reaction and now the thought that these virile young men were approving of her body was quite a turn on.
The next loss for Mark came and he had to take off his pants. Clowning around, he slid them down his legs and chucked them behind him. Shortly, Tim and Jake had to do the same. Margaret was feeling more and more like she had to stop what was happening. Instead, she sat there holding her cards, her gaze occasionally slipping to the bulges all the boys were sporting in their underwear. The room seemed to always grow smaller and hotter.
The turn of Jackie’s jeans came. Surprisingly, the decision to part with them was a lot easier. Just like a bikini, she reminded herself. It’s only when they were off, she realised, looking down, that she was sporting a small but obvious wet spot on her underwear. She quickly sat down, her face burning, hoping the boys didn’t notice anything. Of course, her hope was in vain as Mark and Jake again exchanged meaningful glances.
Margaret dealt the cards and the next hand commenced. By now, the married mother could barely focus on the game itself. All she was consumed by was the battle between her head and other parts of her anatomy. The former told her that the game must end this round. The latter was suddenly sending more moisture into her nether regions as she ogled the boys from behind her cards.
“Uh, you lost, Mrs. Davenport” Jake stammered. Margaret sat with her head down for a moment, her mind blank. “Um...” she said, finally looking around. “Looks like you got me, guys ... I don’t have anything else to take off!”. “Are you sure, Mrs. Davenport?” asked Mark. He tried to keep up the joking light-hearted tone that seemed to disappear into the heavy atmosphere of the room. He tried again, more seriously this time. “Mrs Davenport ... look, it’s just a fun game, isn’t it? Why don’t we just keep it going and no one has to know?”. All the boys stared at Margaret. She looked back at them, focusing on Tim. Her son quickly tried to change his expression to that of concern but to her shock (and another rush of arousal through her core), it was momentarily identical to Mark and Jake. “Even he wants to see them?!” she thought incredulously.
“Boys, boys” she pleaded, wishing that they would stop staring at her, but more importantly, that her body wasn’t responding in ways that were natural in her younger days when she was the object of male sexual desire. “I’m old enough to be your mother ... heck, I am Tim’s mother!”. Mark, who was observing Jackie’s hard nipples with interest throughout the night, respectfully nodded. “Well, how about we make it fair? If we keep going, one of us will remove an item for each one you remove”. Given that all the boys were down to their underwear already, this could only mean one thing. Margaret swallowed as the idea hit her full-force. Little did Mark know that her already drunk and lust-addled mind couldn’t handle this additional temptation.
“All right” she exhaled in a shaky voice. “But don’t you even dare breathe a word to another living soul about this!”. “Nothing here tonight leaves this room!” Mark assured her. “I can go first, Mrs Davenport” Jake chimed in. Margaret nodded slowly. Jake stood up, slowly rolling his underwear down his legs and stepping out of it. Inside he was desperately trying to keep his erection down by the power of his will but he wasn’t being very successful. On seeing this, Margaretfelt her pussy becoming moister by the second. She squeezed her thighs together as her eyes were glued to this spectacle, herself seemingly powerless to do anything about her reactions.
“Okay, boys” she said in mock resignation, reaching behind her. She performed a sexy shimmy with her upper body, her rolls of fat shaking, as she unclasped her bra, dropping it into her lap. Everyone’s eyes buldged out of their sockets as her tits rolled free, her nipples obviously erect. Her age and their size meant that they were saggy enough but that hardly mattered to the three hormonal young men. Everyone was by now breathing heavily, all the guys, including Tim, sporting huge erections. For her part, Margaret found the reaction utterly gratifying. It was a long time since she felt sexy and desired and now she delighted in the feeling.
Trying to ignore the growing fire in her groin and her hard puckered nipples and pushing away the thought that she was sitting topless in front of her son and his best friends, she picked up the cards and dealt them out. She felt adrift on the ocean of lust, completely at loss to know as to how to proceed if she didn’t win. Her thoughts came thick and fast. “I know where this is going ... can I really ... I’ve never felt so horny in my life ... I need to stop ... I can’t...”. Needless to say, she quickly lost again. Once again, she dropped her head, trying to regain her composure. All to no avail as she met their eyes. The lust that blazed in them was such as to take her breath away. All thoughts of backing down were wiped as her pussy flooded.
Suddenly, both Mark and Jake were at her side. Mark put his arm around her. “Can we help you with these, Mrs. Davenport?” he asked with a leer. As if hypnotised, Margaret nodded slowly. She stood up on shaking legs, almost supporting herself on their shoulders as they reached down, grabbing her panties and pushing them down.
Her rolls of fat could not hide her voluptuous figure as it presented itself to the boys in all its glory, complete with the flush creeping down her huge tits and an obviously wet pussy. They devoured it with their eyes as Mark quickly got rid of his own underwear. Both boys stood there as if letting Margaret make the decision. It was this that undone her. If she felt pressured or had to fight off their advances, that might have allowed Margaret’s rational mind to reassert itself. Instead, having to muster all her willpower to stop proved insufficient. Margaret could barely believe what she was doing as her hands reached down, stroking Mark and Jake’s erect cocks, which pointed straight in the air.