Her Stepfather’s Flirting Got Intense

[betimisho]

Patty’s been in the lifestyle with me for over a year, and we’ve had some incredible experiences, but this new development with her mom’s boyfriend—let’s call him her stepfather has us intrigued.

Patty’s mom, Lisa, started dating a new guy about six months ago. Let’s call him Tom, mid-40s, charming, fit, and a successful real estate guy with a smooth-talking vibe. He’s technically her stepfather, though Patty doesn’t call him that since her mom and Tom aren’t married yet. They’ve been living together for a few months, and Patty visits her mom’s place regularly for family dinners or casual hangouts. Tom’s always been friendly—maybe a bit too friendly—but we chalked it up to him trying to bond with his girlfriend’s daughter. Patty’s gorgeous, so it wasn’t surprising he’d notice her, but we figured he was just being overly warm to make a good impression.

Things started shifting a couple of months ago. Patty noticed Tom’s compliments getting more personal. At first, it was stuff like, “You look nice in that dress,” or “You must drive the guys crazy.” Innocent enough, but there was a tone—a lingering look, a smirk—that made her feel like he was testing the waters. She mentioned it to me, and we laughed it off, thinking he was just a flirty guy. But then it escalated. During a family dinner in July, he brushed against her in the hallway, his hand lingering on her lower back a bit too long. She said it gave her a weird thrill, not because she was into him, but because it felt forbidden. She didn’t tell her mom, not wanting to stir up drama, but she told me everything, and we talked about how to handle it. We decided she’d keep her distance and stay polite but firm.

Fast forward to last weekend, when things went from subtle to undeniable. Patty’s mom hosted a barbecue at their house, a mix of family and friends. I was there, helping with the grill, while Patty was mingling. She was wearing a sundress—nothing crazy, but it hugged her curves, and she looked stunning. I caught Tom staring at her a few times, but I figured I was being paranoid. Later, Patty went inside to grab some drinks from the kitchen, and Tom followed her. She told me later that he cornered her near the fridge, standing way too close, and said, “You know, Patty, I could show you things those young guys can’t. I’d treat you better than any of them.” His voice was low, suggestive, and he touched her arm lightly. She froze, not out of fear, but because she was caught off guard. She mumbled something about needing to get back outside and left, but not before he gave her this knowing smile, like he’d planted a seed.

When she told me that night, I was floored. Part of me was pissed,how dare this guy cross that line? But another part, the cuckold part, was buzzing with this excitement. The idea of Patty , being pursued by her mom’s boyfriend is so far outside our usual dynamic that it’s both thrilling and terrifying. Patty’s reaction was even more complicated. She admitted she felt a rush when he said it—not because she’s attracted to Tom, but because the taboo nature of it tapped into her love for pushing boundaries. She said it’s like the ultimate forbidden fruit, and the fact that he’s confident enough to make a move makes her curious about what he’s like. But she’s also freaked out, worried about her mom finding out, and unsure if this is a line we should even consider crossing.

Here’s where we’re at now: we’re talking about what to do next. Patty’s not ready to shut it down completely, but she’s not jumping into anything either. She’s intrigued by the idea of playing with this dynamic, maybe flirting back to see how far he’ll go, but only if we can keep it discreet and safe. I’m torn. The cuckold in me is screaming to let this unfold—imagine her with Tom, this older, experienced guy who’s technically family, taking her while I watch, knowing it’s so wrong. But the rational part of me is screaming red flags: what if her mom finds out? What if Tom’s not trustworthy? What if this blows up their family or our relationship? We’ve always been careful to keep the lifestyle separate from our personal lives, and this feels like a minefield.

So, Cuckold Forum, I’m turning to you for help. Has anyone here dealt with a stepfather or family-adjacent figure entering the hotwife/cuckold dynamic? How did you handle the ethical and emotional complexities? Did it work out, or did it crash and burn? For those who’ve played with taboo dynamics, how do you set boundaries to avoid drama? We’re also wondering about practical stuff: if we did explore this, how would we even start? Invite him to a neutral setting? Let Patty flirt and see if he escalates? And how do we keep it from blowing up in our faces? Patty’s reading this thread with me, and she’s curious about your advice. She’s especially interested in hearing from hotwives who’ve navigated something similar—how did it feel to cross that line?

I know this is a lot, but this community’s insights have helped us before, even just from lurking

[Tryn]

I understand why you and Patty are intrigued by this. However! You’re talking about a guy that is completely and totally disrespecting Patty’s mom. That’s not cool and should be addressed with Patty’s mom. If he’s trying to hook up with Patty, he’s obviously not committed to her mom. Going down that path with him, assuming Patty’s mom is like most women, will ultimately lead to some incredibly hurt feelings. You both need to use your rational brain here! Please don’t be complicit in hurting Patty’s mom, possibly destroying the mother/daughter relationship, over a kink. That’s going way too far! Her mom deserves better from a boyfriend and her family! If her mom is on board with it, then by all means, but that’s unlikely.

[Greywolf and Vixen]

Most of the time if the guy is married or in a relationship, that's not our problem. In this case though, it's her mom. It's definitely a problem.

[Tryagain]

This is about as exciting as things get! What a rush for Patty - and you - if intense flirting was allowed to continue. Unfortunately, she has a duty to her mom to let her know this guy is a real sleeve and will undoubtedly cheat on her every chance he gets. Go get another boyfriend instead.

As far as telling her mom now, that is a tough call. If he continues, and I am sure he will, then let her know. I am sorry this kills a very, very hot story.

[betimisho]

Thanks for the responses so far, Tryn, Greywolf and Vixen, and Tryagain.

We really appreciate the perspectives, especially since this is such a tricky situation. Patty and I have been reading through your replies together, and they’ve given us a lot to think about.

Tryn and Greywolf and Vixen, you both hit on the biggest red flag here: Patty’s mom. We completely agree that disrespecting her mom is a serious issue, and the last thing we want is to hurt her or damage their relationship. Patty’s super close with her mom, and the idea of causing her pain or breaking her trust is a hard stop for us. Your points about Tom’s behavior showing a lack of commitment to Lisa really resonate.

It’s not just about the thrill of the taboo—it’s about the real-world consequences, and we’re not okay with being complicit in something that could devastate her mom.

Tryagain, you nailed the excitement factor—this scenario is undeniably hot in theory, and the taboo vibe is what’s been pulling at both of us. But you’re also right that Patty has a responsibility to her mom.

After reading your replies and talking it over, we’re considering a cautious approach. Patty’s thinking about testing the waters with Tom—not diving in headfirst, but maybe responding to his flirting in a controlled way to gauge his intentions. The goal wouldn’t be to start something right away but to see if this could ever be explored openly and honestly, maybe even with Lisa’s knowledge and consent down the line (we know that’s a long shot, but we’ve heard of crazier things in the lifestyle!). For now, Patty’s planning to keep any interactions light and public, like at family events, to avoid anything secretive that could hurt her mom. If Tom pushes too far or shows he’s not trustworthy, we’re prepared to shut it down hard and, if needed, loop Lisa in to protect her.

Thanks again for the reality checks and the support, everyone. This forum’s always been a goldmine for balancing fantasy and reality, and we’re eager to hear more stories or advice. Patty’s especially curious about other hotwives’ experiences with pushing boundaries like this. We’ll keep you updated as we figure out our next steps!

[Archie457]

For you and Patty, guys like Tom are a dime a dozen. Her mother will be the only mother she will ever have and is irreplaceable. Prioritize accordingly so you don't lose the valuable relationship for the throwaway relationship. Besides, if Patty ever feels like she has to tell her mom about Tom cheating on her, it will be easier if Patty hasn't screwed him. Personally, if I were in your shoes, I would shut this down now and shut it down hard.

[monraccoon]

y’all are scary. that you would entertain this at all is sooooo disrespectful to her mom. the proper move would be to tell her mom what this creep is up to so she can jettison him. this is just icky.

[PussyFiller]

I agree with most of the comments. The trill of "forbidden fruit" can NOT be a higher priority the Patty and her mom, Lisa - even a "cautious approach" should not be considered.

Yes... on the forum stranger things may have happened... so the ONLY way this should proceed is if Lisa is into the LS at least some, and would be open to Patty and him playing. That would require a conversation between the two of them. Otherwise... don't even play with it. It's just leading him on (which would be his excuse when it blows up)... and it WILL blow up.

Two thumbs down!

[Lucky Dog]

I also found this highly erotic but if you and Patty have any regards for her mom, this is a very bad idea. Her mom is going to be very upset when she learns her serious boyfriend is trying to cheat on her - or already has. To learn further that her daughter, whom she loves and trusts, is a part of this could be even more upsetting. Unless her mom is into this kind of thing (possible but unlikely), this has to be a hard NO. Patty can find another older, experienced lover to rock her boat without risking collateral damage to her family. (Patty is pretty and older men can't resist - you've heard this one before.)

[rascalnvixen]

If Tom is making this play behind her mom's back, he has little to no integrity. If he has no integrity, chances are he won't keep the play confidential and Mom is likely to find out and break that close relationship between mom and daughter. I'd suggest to ignore him. Now, if mom is a player too.........

Rascal

[rascalnvixen]

If Tom is making this play behind her mom's back, he has little to no integrity. If he has no integrity, chances are he won't keep the play confidential and Mom is likely to find out and break that close relationship between mom and daughter. I'd suggest to ignore him. Now, if mom is a player too.........

Rascal

[joel68]

I agree to not pursue this at this time. You don’t fish off the company pier, lol. Way too close to home.

But, as Rascal suggested, if Mom is into that, then maybe. Or if Mom eventually dumps him, then that could be a maybe as well. But not sure as long as Mom doesn’t find out or tell her up front before doing it.

Complicated to say the least.

But under the present circumstances, if you do proceed and Mom finds out it would not be good at all.

[wannabecUKold]

All the above comments are well made but there is much that can be allowed before it becomes a major problem.
Patty can wear her sundress without a bra or pants and be available for his hands above and below. Patty can sunbathe with her mom and take her top off. She can let him put sun cream on her. See what her mom says. Mom might be fine with it. Or if not then she will speak to her boyfriend.
OP will also be involved: he can pretend not to see, or be really bold and tell Tom to carry on, it’s fine.
Step by step, this can become known and accepted in the family within what limits Mom imposes.

[mundyman]

Thanks for the responses so far, Tryn, Greywolf and Vixen, and Tryagain.

We really appreciate the perspectives, especially since this is such a tricky situation. Patty and I have been reading through your replies together, and they’ve given us a lot to think about.

Tryn and Greywolf and Vixen, you both hit on the biggest red flag here: Patty’s mom. We completely agree that disrespecting her mom is a serious issue, and the last thing we want is to hurt her or damage their relationship. Patty’s super close with her mom, and the idea of causing her pain or breaking her trust is a hard stop for us. Your points about Tom’s behavior showing a lack of commitment to Lisa really resonate.

It’s not just about the thrill of the taboo—it’s about the real-world consequences, and we’re not okay with being complicit in something that could devastate her mom.

Tryagain, you nailed the excitement factor—this scenario is undeniably hot in theory, and the taboo vibe is what’s been pulling at both of us. But you’re also right that Patty has a responsibility to her mom.

After reading your replies and talking it over, we’re considering a cautious approach. Patty’s thinking about testing the waters with Tom—not diving in headfirst, but maybe responding to his flirting in a controlled way to gauge his intentions. The goal wouldn’t be to start something right away but to see if this could ever be explored openly and honestly, maybe even with Lisa’s knowledge and consent down the line (we know that’s a long shot, but we’ve heard of crazier things in the lifestyle!). For now, Patty’s planning to keep any interactions light and public, like at family events, to avoid anything secretive that could hurt her mom. If Tom pushes too far or shows he’s not trustworthy, we’re prepared to shut it down hard and, if needed, loop Lisa in to protect her.

Thanks again for the reality checks and the support, everyone. This forum’s always been a goldmine for balancing fantasy and reality, and we’re eager to hear more stories or advice. Patty’s especially curious about other hotwives’ experiences with pushing boundaries like this. We’ll keep you updated as we figure out our next steps!

I’m wondering after how many drinks did Tom do this?
Sometimes alcohol loosens lips, and people say things they normally never would.
It will be interesting to see if he keeps it up, or acts guilty the next time you see him.

[betimisho]

Patty and I have been glued to this thread over the last couple of days, and your input has been invaluable. We've had some deep conversations sparked by your comments, and things have progressed a bit since my last post

You're all echoing the same core advice—prioritize Patty's relationship with her mom above all else, avoid anything that could blow up the family, and recognize Tom's lack of integrity as a massive red flag. We hear you loud and clear

wannabecUKold: Your suggestions about gradual, public escalation sound tempting in a fantasy sense, like testing boundaries with sunbathing or casual touches in front of her mom to gauge reactions
mundyman: Great question about the alcohol. At the barbecue last weekend, yeah, there were drinks flowing—beers for most folks, including Tom. He wasn't sloshed or anything, but he had a few, which might've loosened him up to make that bold move in the kitchen

Not much has happened action-wise since the barbecue, but we've had a couple of developments. Patty texted her mom yesterday just to check in (nothing about Tom), and Lisa mentioned they're planning another family dinner this Friday—nothing big, just the four of us.

Patty's a bit anxious about it, wondering if Tom will pick up where he left off or if he'll play it cool after seeing her brush him off.

[ShyBiGuy954]

Not much has happened action-wise since the barbecue, but we've had a couple of developments. Patty texted her mom yesterday just to check in (nothing about Tom), and Lisa mentioned they're planning another family dinner this Friday—nothing big, just the four of us.

Patty's a bit anxious about it, wondering if Tom will pick up where he left off or if he'll play it cool after seeing her brush him off.

My thinking is that the way Patty will dress for this event may play into it a bit.

If she chooses to wear something quite revealing/enticing tight/low cut, make-up, lipstick etc etc that might lead Tom on a bit.

But, if something much more conservative, bang around the house jeans, baggy T shirt etc ...

You get the point.

[monraccoon]

ffs, if you have any respect for this woman, tell her that her bf is a lecherous douche so she can show him the door.
your continued interest in playing with this is just… ew!

[surry]

Maybe the three of you can figure out a way to include your Patty's mom? Start discussing the idea of an open relationship. Open up talking about cuckolding, and other exciting sex stuff. Get her mom talking about what she has done or thinks about. Start with a kissing contest. Which girl kisses better?

[dollarboi789]

Patty and I have been glued to this thread over the last couple of days, and your input has been invaluable. We've had some deep conversations sparked by your comments, and things have progressed a bit since my last post

You're all echoing the same core advice—prioritize Patty's relationship with her mom above all else, avoid anything that could blow up the family, and recognize Tom's lack of integrity as a massive red flag. We hear you loud and clear

wannabecUKold: Your suggestions about gradual, public escalation sound tempting in a fantasy sense, like testing boundaries with sunbathing or casual touches in front of her mom to gauge reactions
mundyman: Great question about the alcohol. At the barbecue last weekend, yeah, there were drinks flowing—beers for most folks, including Tom. He wasn't sloshed or anything, but he had a few, which might've loosened him up to make that bold move in the kitchen

Not much has happened action-wise since the barbecue, but we've had a couple of developments. Patty texted her mom yesterday just to check in (nothing about Tom), and Lisa mentioned they're planning another family dinner this Friday—nothing big, just the four of us.

Patty's a bit anxious about it, wondering if Tom will pick up where he left off or if he'll play it cool after seeing her brush him off.

This children is what an avoidable train wreak looks like take notes

[SheLikesWhenIWatch]

My aunt and uncle opened their marriage up. My aunt started dating her daughter’s (my cousin’s) boyfriend.

My cousin broke up with him (and didn’t talk to her mom or him) when she found out. It completely estranged them. (Is that a verb? Estranged?)

The boyfriend is long gone, now. Took a job in another city. Aunt and uncle re-closed their marriage when he left. (Between my aunt and my cousin, he had a good three-year run fucking the both of them. I guess you could say he was a real mother-fucker!)

My cousin has never gotten over it. She has re-established a relationship with her mother, but it’s just not the same. Just knowing that your mom “stole” your boyfriend (even though it was *really* on the boyfriend to shut that shit down) so she could cuck your dad completely destroyed all sense of trust…..and really made her think of her dad in a different light, to boot. (I totally understand him. He’s a cuck….like me. Likes watching his wife taking another man’s dick. But most people don’t understand us!)

I feel sad for them. They’ll never be the same.

My advice? Don’t get family involved unless EVERYONE is clear.

[dannyvee]

TELL HER MOM. I repeat TELL HER MOM. Got it?
P.S. TELL HER! NOW!

[Tryagain]

As I said before, this is a most exciting sexual situation. And I have said, as others, you should tell your mom. But how can you pass up some (cheap ?) thrills. Love the idea of dressing very sexy for the next meeting. Of course you run the risk of your mom asking why are you dressed like that. Maneuver so you get moments to spend alone with him.

I like others’ suggestions to start talking about what you read about different lifestyles. THAT should also be exciting. I am just having a hard time if you guys actually kissed. I guess at that point you should tell mom.

[venus-can99]

Does Patty's mom, Lisa, know about her hotwifing? If Lisa does then it may be worth discussing Tom's advances. If not, and Patty would like to keep it a secret for now, you both need to shut Tom's overtures down. Perhaps let Lisa know that Tom makes her uncomfortable.

[monraccoon]

any of y’all, the couple in question and, more importantly to this point, my fellow commenters, ever heard of the shopping cart test? in a nutshell, it’s a test which reveals character. you’re not breaking the law if you just leave the shopping cart next to your car and drive away, but what kind of person does that? obviously, our society is rife with this kind of person. in this same way, the commenters who sound like they’re typing with one hand, who entertain the entertainment of this, condoning the major disrespect to this woman’s mother: this shows what kind of person you are. seen and noted.

[realcucklife]

Surely Lisa sees him being flirty with more than just Patty.
Can’t Patty comment to her that he’s a smooth talker?
They might both be open, and he’s pushing a boundary also.
An alternative, if he is chasing Patty he would be chasing other women, does mum need to know to avoid being hurt?