Strictly Anonymous Confessions - 1590 - Mark Slept with His Former High School Teacher, Her Friend, His Friends’ Moms & More?!
Episode Date: September 15, 2026Mark slept with his former high school teacher, her friend, his friends’ moms and more and he called in to talk all about it. Tune in to hear all the details including the crush he had on his teache...r during his senior year, what he accidentally walked in on that made his crush even stronger, how they wound up bumping into each other after he graduated, how he asked her out for a drink and how she reacted, the first time they hooked up and exactly what went down, how and where they continued hooking up for years while keeping their fling a secret, the feelings he developed for her and why he never acted on them, how he started sleeping with one of her friends, how the three of them wound up having a threesome and exactly what went down, how he got passed around to tons of other MILFs including married women he slept with while their husbands watched, how he hooked up with two of his friends’ moms and what went down, how and why his fling with his former teacher eventually ended, who he is married to now and why nobody in his life knows about his wild MILF filled past plus a whole lot more. GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: https://amzn.to/4i7hBCd To see HOT pics of VANESSA plus my other female guests + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast and when you join, I'll throw in a complimentary link to my private Discord! To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at strictlyanonymouspodcast@gmail.com or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed. Sponsors: https://beduc.at/pd2634-anonymous Click here to take the quiz and get your personalized SUMMER roadmap to sexual happiness https://TakeLean.com - 20% off + FREE rush shipping on Lean weighloss https://VB.HEALTH- To get 10% off DRIVE BOOST by VB Health, use code: STRICTLY https://inda.shop/STRICTLY If you’re 21 or older, get 30% OFF your first order @IndaCloud with code STRICTLY #indacloud https://bluechew.com — Buy 2 months of Bluechew GOLD and get the third month FREE! Use code: STRICTLYANON Follow me! Instagram https://www.instagram.com/strictanonymous/ X https://twitter.com/strictanonymous?lang=en Website http://www.strictlyanonymouspodcast.com/ Everything else: https://linktr.ee/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices
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You go to Sanpore or Thailand.
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Here is your host, Kathy.
Hey, welcome to the Strictly Anonymous podcast with Kathy.
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description and click on the link. Okay, today I have a crazy story. This one's taboo story, for sure. I mean,
it's all legal, okay, but it is something like straight out of a porn. This guy, Mark, he emailed me because
he's like, oh my God, I would like, hooked up with my high school teacher, but not when he was in
high school, okay, it wasn't when he was in high school. It was like way later after, but, you know,
they live in the same town and they wound up bump it into each other and they wound up hook it up,
but it's like the whole buildup to how he met her.
And he talks about sort of the buildup and what was going down that whole senior year
and how he was feeling about his teacher who was definitely a Melfth and then he winds up with her.
And it's so crazy.
I mean, fucks her and then her friend and then they have a threesome.
And then he was like with so many other MILFs.
He wound up bartending in his town and he wound up doing so many older women.
He became obsessed with MILFs and had many.
And like I said, wasn't just having threasons with a teacher and her friend.
he was doing couples while their husbands watched.
He also was with some of his friends' moms.
I mean, I was like, I just couldn't believe how the story unfolded.
He's somebody that never told anybody about anything.
He's married with kids now, older guy.
Well, not that much older.
He's like in his late 30s, but this all went down in his 20s,
and you're just not going to believe, like, you know,
what he got access to once he got into the Melfth world.
So anyway, I'm not going to waste your time talking about it anymore.
I'm going to get right to the story.
be right back on with Mark.
This is the strictly
anonymous podcast.
Strictly anonymous podcast.
Hey Mark,
welcome to the strictly anonymous podcast.
How are you today?
I'm great yourself,
Kathy.
So listen,
you got a story that like,
you know,
reads like a porn,
you know,
it's like a basic story,
but it is a taboo story,
I would say,
but it's legal.
I mean, like,
you didn't do anything like,
because like when you email me like,
oh, I fucked my teacher,
I was like, you know,
were you 14, 16?
Like, I can't have those stories.
on my show and I don't. I would not, you know, because to me, that's the non-consensual, but you wound up
hooking up with your high school teacher, but like when you were, like way later when you were out
of school, which to me is like interesting, you know what I mean? Yeah, it, it was a really cool buildup
to the whole thing, to be honest with you got. We need the buildup, because this is like straight up
porn, you know what I mean? Like, you know, there's these kinds of stories that are like, I say,
like, taboo, but porn, you know, and you kind of like lived it. Like, people are going to be clicking
on it just because, like, oh my God.
fucked his high school teacher because I'm sure there's plenty of guys out there that had crushes
on their teacher, right? I don't know, you know. So, uh, we're going to go through the whole story.
So let's see, because there's some twists to the story. I don't know what they are, but there's
some twist, you said. Uh, there is an interesting kind of ending. But let's do the hold buildup.
She's your high school teacher, okay? And somehow you hook up with her. How old was she?
Like, because you're like 18 around that time. I'm wondering how much older she is than you.
Yeah, so she would have been, I'm trying to remember her exact age, but I believe she would have been around that time early 40s.
Oh, so she's way older than you.
Way older.
She's not like a 27-year-old high school teacher.
No, she was older for sure.
As a matter of fact, she had kids that were, you know, my age.
She's a milf.
Melf, 100%.
Was she hot?
Yeah, she was gorgeous.
She was easily one of the hottest years of my high school, no doubt about it.
But were you into old women?
Because some people at 18 wouldn't see a 40-year-old woman and think she's hot, even if she's hot.
You know what I mean?
Like it would be too old for them.
Were you just into older women?
I didn't know what I was missing, Kathy.
That's really what it came down to.
I didn't know what I was missing.
And I, for a lot of my, I was a late bloomer sexually.
So, like, for me, I had a girlfriend in high school that I was loyal to for a couple of years.
And she made me wait for it, which I did.
And I didn't lose my virginity until I was.
you know, I was 17 years old.
So when we broke up, that's sort of when I started realizing what was,
what else was out there and what else I was missing out on.
But I mean, the fact that you looked at that, like, was word on the street, this teacher's hot,
or were you the only one that thought she was hot?
No, no, where on the street was, you know, I mean, she was, you know, early 40s.
There was definitely some hotter teachers at my high school that were younger,
but she was definitely, you know, a lot of the guys would talk shit and say, you know,
She's definitely a milf and whatever else.
And I say, yeah.
But the thing, Kathy, is she didn't, like, dress overly.
Provocative.
Yeah.
Like, she didn't until, like, it was weird.
It's almost like she started doing it that semester.
It's very bizarre.
You think she was doing it for you?
I don't know.
Yeah, because if, you know, you think back to the timeline, right,
I would have started that semester in January,
and the school year would have ran out in June.
So basically from January to June, I had her as a teacher.
Never had her before that for anything.
But I definitely noticed her around the school.
And, you know, she had, she was blonde, probably about 5'5, just beautiful, beautiful body.
She had two kids.
Was she married?
She was divorced.
Okay.
Yeah.
So she never had an affair or anything like that.
She was divorced for, I want to say, about four years prior to me.
doing this with her.
And I would assume you find all that out
when you're banging her because, like, how do you know your
teacher's life story when you're
in the class?
Yeah. So the way it all
sort of started was,
you know, for a little
while, I'm like, I kind of would start
thinking, I'm like, because I was,
after I got into my relationship
with my girlfriend at the time,
it would have been about
October of grade 12 for me.
So give or take,
right for the school year started.
And then I started, you know,
banging other girls in school.
And I'm like, okay, this is great.
And, you know, I was definitely not looking for anything serious at the time.
I was going to college the year after.
So for me, I wasn't looking for anything serious.
Yeah.
I had just got out of a serious relationship for three years.
So I really wasn't looking for anything serious.
But then I started kind of noticing her a little bit more in class.
And, you know, just something about her drew me to her.
like I just couldn't stay away from her.
Like I just liked to be in her class.
Like I fuck,
I didn't want to skip her class.
I had all the ones I skipped back in the day.
I didn't want to skip hers at all because I wanted to see her.
Right.
So she was definitely,
you know,
a beautiful woman.
I mean,
definitely.
Yeah,
but what about you?
Who were you in high school?
Were you like a hot jock?
Were you,
you know,
like were you hot?
You know,
what was your story in high school?
I mean,
yeah,
like I got laid a lot in high school.
I,
uh,
I had a part.
time job I was a hockey player. I was popular for sure. I had a lot of friends, a lot of girls that,
you know, but I was a bit of a player. Be honest with you, like that was probably my downside.
I was a bit of a player. No, that's an upside to girls. Your player attitude probably got you a lot
of checks. That's why you're a player. And now how did you, like, what was the vibe in this
classroom? She had these beautiful blue eyes. And I noticed them and one day I asked her.
because at the time it was kind of popular
were those, remember those like color changing
contact lenses? Yeah, totally.
Yeah. So I asked her, I said, like,
do you, are you wearing
like those, those color changing contact lenses?
Because like your eyes are just really blue.
Like I just, I wasn't saying it like a sexual way or anything.
I just, I just happened, noticed they were really sparkly.
And I asked her and she said they weren't.
But did you ask her in front of the whole class or like privately?
Like, how do you ask a question like that to a teacher?
Not in front of the whole class, but just kind of like,
at her desk, like just kind of away from the students.
Like, just asked her to just make in conversation because I don't know.
And then, you know, you watch a lot of porn when you're, you know, 17, 18 years old.
You're like, fuck, like, you know what?
I started to think about it a couple times.
You're like, no, there's no way.
Like, there's no way it's ever going to happen, right?
Like, no, no, we're not that it's happening.
You just told her about her fucking eyes.
But you're not like doing that for flirting.
Like, you're genuinely just have that as a question, right?
That's right.
100% and to be completely honest my high school had two
two teacher and student affairs happened that same year that the teachers were charged
you're kidding you're fucking no not at all I didn't want to like didn't want to start shit or
like be that third person or even be involved in anything to do with that wait real quick
because I just need to know I'm so curious like those other two things like did you know
the teachers and the kids like what were the stories yeah yeah I knew actually
I knew both teachers I had and both students I knew really well too.
You're fucking, and what were the age gaps with those?
Do you remember?
The one was probably a little closer, like to like 12 or 13 years.
I think that the guy with the chick in my grade, I think he was like 30 something.
Wait, wait, wait, this is important.
It was a male teacher with a female student.
Correct.
Okay, and he was in his 30s.
Yeah.
Okay.
And you knew her, and you.
had him as a teacher.
Correct.
Oh my God.
Did she ever, like, did you ever get the story from her?
Never.
No, like, I, yeah, after everything went down, I didn't really, yeah, like, I never really,
she kind of fucked off two different school, like, never talked to her again.
So, like, I didn't really get the full story from her ever, but I did know something
was gone, something went down.
And he lost his job, obviously, got charged.
Okay, what was the other one?
And the other one was a, uh, the other one, um, the other one,
was also female with a male teacher as well.
And that teacher was probably close to the age range
of the one that I'm talking to you about.
So probably early 40s as well.
Oh my God.
And another girl.
And you knew that girl too.
I knew her.
I knew that girl better.
And weirdly enough, she's actually,
she was, I don't know if she was confused,
but she's actually, she's lesbian now.
So she's not even straight.
So like, I don't even know.
Maybe that traumatized her.
Maybe that turned her off.
Okay.
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Okay, so you, so you didn't want to have that again,
but the whole semester, that whole six months while you're in her class,
you're thinking about her.
Yeah, like it was a weird, it was kind of a kind of a,
kind of a weird series of events that happened.
This is where it kind of takes a bit of a turn.
True story.
This is how I really, this is how it really amped up.
So we, it was one of those days where it started out really cool in April, but it was a warmer day.
So like, I wore a hoodie in the morning to school, like a sweater and, you know,
took it off in class, left it on the back of my chair, you know, went out with my day.
And this was, this was the last, this class was the last period of the day.
So basically took me right at the end of the day.
So, like, you know, we were going home after his class was over, right?
Every day.
And I left my sweater in the classroom.
So I left the classroom, walked out on the, it was on the fifth floor of my high school,
walked out, went down the stairs, realized, shit, I forgot my sweater.
I went back into the class, knocked first, not loudly enough, I guess,
because the room was dark, I don't think it was in there, walked in the classroom,
and she was changing her shirt herself.
Oh, my God.
What do you mean she's changing her shirt?
She had to change of clothes?
When I came back into the classroom.
No, I know what you're saying.
She's like, but she's literally her top of office.
She has like a change of clothes.
She's not going home in the same clothes she was wearing?
Yeah, like she was changing her shirt into something different.
So I don't know if she's going to the gym or why she was doing it.
But yeah, so I walked in the room.
She had her pants on.
She had her shirt off.
She was wearing her bra.
That's it.
So a bra.
So she wasn't naked.
She just had her bra on.
But like,
my God, like I was like fucking just
walked in my, did my imagining this or is this
actually happening? Oh my.
And what did she do when she saw you? Because you
knocked, she let you come in? She was
spooked and I said, oh my God, I'm so
sorry. I knocked and the lights
were off. I didn't think anybody was in here. I was
grabbed my sweater. So I looked
at her, but I could not get
that image out of my head. Grab my sweater
walked out the fucking door
and went home. That's it. Yeah.
Did you have big boobs?
She, yeah. She had
She had a great set of boobs on her.
Like, not overly big, but like nice.
Yeah, yeah, yeah, yeah.
Yeah, I think other guys listening right now can't get that whole scenario out of their heads either.
Yeah, I remember just a black lacy bra.
Oh, my God.
She had like a nice, like, she, just a beautiful body.
Like, I'm just like, fuck.
Like, this is incredible.
Like, what am I?
Like, how did I walk into this?
And, like, nothing kind of came.
I said, I'm sorry.
I said, I didn't see anything.
anything, I'm walking at the door, have a great night, and that was it. I left.
Because like, nothing's going to happen right then and there. Like, I just, I couldn't do that
to her. And with everything going on my school that same year, I couldn't do it either. So I'm like,
I'm like, no, I can't. So I got to, you know, I got to make sure that I get the fuck out of
here and go, right? Yeah. Yeah. And you went. But did, was she genuinely like,
like, shocked when you walked in? Genuinely shocked. I don't think, I really don't think
she expect me to walk in on her. And it was like one of those things. So from like, of course,
now at this point, I've seen what I'm missing.
He never really warring that provocative before.
So I'm like, I'm like, all I could fucking think about now is just what I saw for weeks.
Yeah, can she even look at you in the face the next time you see her and what about you?
Like, because that's like a weird, now you have this weird thing that happened between you two and you have to be in class and act like everything's normal.
Exactly.
And I like, you know, I, after class one day, I was nobody in the classroom I said to her look.
Like, I know what happened.
I'm so sorry about that.
I'm not going to make it something.
It's not, you know, that's it.
Like, I left it alone.
Like, I left it alone and that was, that was it.
Okay.
Yeah, and that was, you know, what it came down to.
But, but yeah, like, it was the next little while going by.
I just couldn't stop staring.
And, like, then it got weird.
Then her outfits started getting a little more show, provocative, a little more showy.
That's when, because the,
weather was getting warmer, you know, she was wearing a lot more.
Yeah, but you don't know that every year she didn't dress more provocatively in the warmer weather,
no?
Exactly.
That's my thought process exactly.
You know what, it's getting warmer, but she's looking fucking great.
So I want to, you know, I'm going to keep staring at this and just imagining.
So, like, of course, I'm fantasizing and thinking about this more and more often and, like,
thinking about, like, you know, what could happen.
And, of course, not telling anybody this story at all.
Like, nobody knows a story.
Like, not one person has heard the story before.
Right.
You didn't even tell anyone that you walked in on your teacher, like, Toplas.
No, I just didn't want to make it anything.
You're like the type of person that you could tell a secret to.
Like, the fact that you keep that shit to yourself, I don't know.
I would have blabbed to everybody at that age.
People don't keep their mouth shut at 18, but you certainly did.
It's interesting.
Yeah, it was an interesting time.
And, you know, I just, I was one of those people that definitely could keep a secret.
for sure. Yeah, you're good. I was a trustworthy and loyal friends. So for most people, and I've a lot of
because I've been told and they've never left the vault. Yeah, obviously. I mean, I'm not a person too,
but not when I was 18. Fuck that. I would have been outblower. Okay. So go on. All right. So the whole
time she's like, so it's just like for you, it's like pent up because you're like, you know, after
that, seeing her and, you know, now she's revealing more. You could really fantasize about her the
rest of the year. But I got to say, like, it was probably the best six months, like, ending of school
ever because, like, I don't know. I've, like, had crushes at work and places, and it just makes,
like, that place going to, like, so much better if you like somebody there, you know what I mean?
So it's, like, the fact that you, like, had this crush in high school probably just made going to
school, like, so much better than all your friends. Like, typically, you fucking hate going to school.
You were probably so happy on Sundays to go to on school Monday. You know what I mean, to see that
check, but, like, most people fucking dread it. But, but, but, but, but.
for you, it was probably like the best six months of your young life in school when normally it's torture.
Yeah, it was a great semester and loved it.
Of course, I'm, this semester, you got to think, Kathy, like I wasn't re-fucking really anybody.
I mean, I broke up with my girlfriend like, you know, the semester before.
So for me, I'm having all this sex.
I'm thinking about this hot teacher.
I'm doing really well school-wise.
I got my acceptance of college.
Like, it's a good semester overall.
Like, it was a great year, like, to be honest with you.
Yeah.
Yeah. But you, but nothing ever happens and you do graduate, right?
Nope. No, nothing ever happens. I graduate from high school. It's the end of June at this point. I have my summer job lined up. Everything's going good. And I'm thinking, you know, it was just one of those fantasies. And I'm like, ah, you know, it was great while it's over. Yeah. Yeah. It's over, right? It's in the past. Yeah. And then how much time goes by before somehow you guys get back connected, which I have no fucking clue how that happened.
Well, I stayed in my hometown for college.
So that's kind of, I didn't go away to school.
A lot of my friends did.
I did.
And I stayed home.
I mean, I was an only child.
So like I had, you know, a place to myself.
I didn't really feel the need to go away.
I was kind of cool to stay home.
I had my car at home.
I had everything at home.
So I'm like, fucking, I'll stay here.
And, you know, I'll just have to be experience here.
And my parents pretty chill for the most part.
They didn't really give a fuck what I was doing too often.
So the following year, I'm, I'm in college.
college and I am working out at the gym. And it's been a long time since I've seen her and I see her at the gym working out.
Oh, interesting. Right. She lives in your neighborhood and you're still there.
Yeah, like I didn't grow up in a overly large city. So like, you know, there wasn't a ton of gyms.
Yeah, the chances of that happening for anyone is possible if like, you know, she's going to the gym and other people are, right, for her to bump into people that she were.
students. Yeah, absolutely. So of course at this point, college is going on. I'm not in a relationship
with anybody. So it's lots of fun for me. And I run into her and she's looking so good and I'm like,
fuck, she's here working out. So of course, I go over and say hi to her. I get to gym and, you know,
ask me to start spark up a conversation and, you know, nothing really happens from that. So I figure I'll
probably see her here again.
This were both members.
Yeah.
But I kept it pretty casual.
I just kind of said hi.
She asked what I was doing.
I said, you know, when I was taking what my major was in school and everything else,
you know,
just kind of had that very,
very casual conversation with her, right?
At the gym in a public place with lots of people around.
Mm-hmm.
And so I start seeing her a lot more often.
So it's now, you know, now I'm seeing her,
you know, pretty much weekly at the gym.
Like I'm seeing her at least once or twice a week.
week at the gym. So I'm seeing her all the time. You know, it's just like, and then I'm thinking
to myself, it's like, you know what? It's been a while. I should see if she wants to grab a drink.
Just for shits and giggles, let's just see if she wants to get a drink. And she says, she starts like,
I don't know. She turned like red. She was kind of nervous about it. But she said yes. She said she would
go for a drink with me. What did she say first, though? Like, she was just kind of nervous about it.
she's just like, oh, she goes, you're a little bit young for me.
And I said, well, I said, to be honest with you, it's just a drink.
And I love to buy you a drink because you were such a helpful teacher.
And I love you.
I love you.
How much as you as a teacher.
So the least I could do is buy you a drink.
Would you be up for that?
Okay.
And so she says, okay, she takes you up on the offer.
Takes me up on the offer.
Gives me your phone number.
And yeah, that's when we met up for a drink and we chatted.
And nothing happened that night.
So nothing happened that night.
We had a drink.
That was it.
We had a drink.
We said, hey, let's stay in touch.
Maybe I'll see you around the gym.
Maybe I'll see you around wherever.
And that was it.
So a couple days go by and she texts me again.
And she goes, hey, would you want to grab another drink?
Maybe I could buy you this one.
Mm-hmm.
Oh, like, fuck.
I'm like, it's happening again.
And so we're going to now actually go for a, we're going to actually go for a drink.
And so we go, we go for a drink, ends up being two, three drinks.
And with some touch at the table and some leg rubbing at the table and a few things start
happening, I knew exactly what was going.
Like I knew exactly what was going to happen next.
Mm-hmm.
What happens?
So she says to me, she goes, you know, I don't live too far from here.
you want to come over and we could have another drink at my place.
So we did.
We'd go back to her place and, and yeah, that's when we started making out right in her,
right in her front entrance of her house and nobody was home because, you know, she's,
she was just, she was divorced, right?
She didn't have anybody there.
So we started making out right in her, right in her, right in the front entrance way of the house.
Mm-hmm.
And ends up happening the first time.
that night.
And how was it?
Incredible.
I've had sex I ever had 100% of the time.
Oh, thank you.
Like it was, it opened up, it opened up so many doors for me sexually where like I think
I was just a much better.
I think I actually got better at sex just from knowing her.
Like she opened so many doors and show me so many things as a young man.
I'm like, this isn't what I'm getting in college.
just as a completely different level of sex I've never had before.
Mm-hmm.
Right.
Well, she's way older than you.
You know what I mean?
It's very different experience, right?
Absolutely.
And in fairness, like, you know, we started doing that,
and it opened up a whole new level of,
not obsession, but, like, just curiosity as to what other women that age would be like.
so of course I didn't want to stop and didn't want to just leave it with just her
I wanted more 40-somethings like you wouldn't believe it was like what I wanted more than
anything right and what did you so what did you do about it did you get I'm assuming did you
continue to see her did I what sorry did you continue to see her I know you want more 40
year olds but do you continue to see her or was it a one-time thing oh no we we saw each other
at this point it was all the time it was it was you know
And at this point, like, we're, we're fucking in her car.
We're fucking in my car.
We're, I go, we're, we're, we're going to different cities for a little, little day
trips, her and I, we're fucking hotel rooms.
We're going all over the place.
And we're, we're, we're, we're just, she's having a fling with me.
And, you know, it's, it's insanely fun.
Like, we're just having such a, such a, such a wild time.
And I'm still not telling anybody about this.
I, you know, I may have told people, you know, I'm, I'm,
I'm fucking an older woman, but I didn't say who it was or where I knew her from.
Right.
But I told people I was at this point fucking somebody who was older.
But I didn't say, I didn't really give them a whole lot of details at that time.
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Right, right. But they knew. And so would you just see her, like you weren't dating any
else, correct?
No.
Like you weren't dating girls your own age or in a relationship cheating on anybody with her.
How long did you wind up sleeping with her for?
Until I graduated college.
So like we were.
Yeah, go on.
And yeah, like, and at that point I had to move away for a job.
So I moved about five hours away from where I grew up.
Yeah.
But I ended up, she ended up coming to visit me, like where I live now when I had my apartment.
So I was still fucking younger women.
and college girls.
Yeah.
But I was also still fucking her.
Right.
So like it was, I was, I wasn't committed to anybody while I was in college.
I, I made sure that I didn't.
I wasn't, I wasn't in a exclusive relationship when I was in college at all.
Right.
Right, right.
You were having fun.
And let me ask you this with this woman, you know, was it always like at her place on the DL?
Like you guys never went out or anything like that, correct?
Well, we would go to different things.
cities. So like we would go to like neighboring cities, go to like a hotel, get food, fuck in her room.
Fuck it. Like we would get a hotel room. We'd fuck in there. We'd go on like little one night
trips away. So that nobody would see you guys in your own town. But you would go out other places.
Correct. Like what kind of places?
Restaurants, bars, you know, like more intimate settings, to be honest, like more like, you know,
we wouldn't go to like a really busy bar. We would go to like a quieter place and find a table
somewhere. Like we wouldn't go to like a bumping club or something and like run into like 10 people I
knew from school. Like to be honest with you, we never actually ran to anybody ever, which was
incredibly hard to believe her being, even though we were in different cities, it's not like we
were going hours away. We're talking 30, 40 minutes, maybe an hour away max for little
times away, right? Yeah. Let me ask you that. She was still a teacher, correct, during all that time?
Absolutely. Yep. Right. Were there ever any?
kind of feelings that were like happening on either side more than just like oh this is a great you know this
is great sex yeah i don't think she was looking for anything serious either yeah i believe she was still
dating but she was getting and she told me she was getting she wasn't getting great sex out there
with other men her age she wasn't she was going out with people and you know seeing other guys
but she there was many times where she would call me for a bad date and say just
come fuck my brains out and I would. Yeah, yeah. No, I mean, listen, I was more thinking maybe you wound up
feeling feelings for her. I, I, I would think, I was 40 and fucked a younger guy, like, I was not
going to have feelings for him, really. You know what I mean? But sometimes it could happen. But, you know,
like, did you ever develop any feelings for her? Oh, of course, but I never, I mean, I, I did
have feelings for her for sure, but I knew that I wasn't going to be a, you know, a 30 year old with a 60 year old,
It wasn't really my thing.
Yeah, you knew it could have to be serious.
But you did develop feelings for her.
100%.
And it opened up, like, my insane milf obsession that I still have today.
Oh, really?
Yeah.
I can imagine.
I'm a married man.
And I'm a married man now with kids.
And it's a complete.
But, like, my wife's like that age where it's like, I really, you know, we're in our late 30s, her and I.
Right?
So it's like now thinking about it, it's like,
fuck like this is like the prime age where I could be dating with my age and actually get it
what I want but I'm married to one so I think I married the right one I just you know of course
you can't never not think about what it was and how often it happened and just the crazy
story of how it all kind of unfolded where were the twists oh oh the twists well with her so
I I was a bartender what was my my job
when I was in college. I was a bartender. And I did private parties. I used to do private
parties. I also worked at a restaurant as well. So for me, it was, you know, I would do this for extra money
while I was in school to help pay for my tuition, everything else. But she actually had a party
at her, at her house where she wanted a bartender in the backyard. She hired me. She hired me as the
bartender. And the fucked up thing about this whole, this whole thing was a lot of people were there
that were teachers at my school. And a lot of people that like, you know, fuck, like people my
parents might have known from that age, right? Like my parents might have even known were at this,
we're at this backyard party. It was a, it was a retirement party for somebody she threw it for
at her house. She had a beautiful backyard. I bartended. And then this woman who wasn't a teacher was there,
and I guess told
she told my teacher
or let's keep calling her my teacher
I'm just going to call her Ms. Driscoll
because that was what we're going to go with
Ms. Driscoll was there
and she had a friend
who went to her
and confided her and said you know
the bartender you hired is really hot
is he single
to the teacher that you're secretly sleeping with
yeah she who has no idea
that we're sleeping together
of course right that's a writer
or she would never said it
so she goes up to that teacher's
And what does the teacher say to her?
Oh, he used to be my student.
He goes, yeah, he was a student, but I'm pretty sure he's single.
But as she says, I don't know his relationship status.
The best thing is to probably ask him.
So I got asked at the party.
Yeah.
I got asked at the party when I was bartending, you know, if I would go out with this, this friend of hers.
So I did.
But as we started to get it.
I did.
Yeah.
This was woman who was not a team.
her who was a friend of her so same age roughly like she was maybe a year or two younger maybe or
around the same age as her i think yeah and i started sleeping with her too yeah she shared you
with a friend she shared you i would have done that when i was her age yeah that's fun i roll i roll just like
her i like her she was like yeah i'd take this young guy for a fucking ride he's good yeah so we start
fucking and I
being very ballsy at this point
and I've had them before
I start I start thinking like
you know do you have any friends
like I've got a thing for older women do you have any friends
who you think would want to like
you know we could do a threesome with
yeah to the teacher lady right
no no to the friend okay okay
oh I see where you're going
because the teacher oh right because
the teacher can't say that
she still didn't tell the other woman that she's with
no right okay so she says
Oh, yeah, let's do it with the teacher.
Correct.
Oh, my gosh.
That's hilarious.
Oh, my God.
That would be awesome.
She was really fucking hot.
So, like, I said, yeah, like, I mean, if she's up for it, I'm up for it kind of thing.
And it ended up happening.
You're kidding.
You were going to forget about this?
I had to fucking ask you for the twist.
You never even brought this up.
Yeah, I wanted to make sure I brought it out to you with, I wanted to make sure you knew.
Like, that was a twist.
So, yeah, we had a, we had a, we had a, we had a, we had a, we had a,
threesome so with this friend but what ended up happening was the friend started introducing me to
other women her age who i was i was fucking married women divorced women always women they were like
i was in fucking milf heaven i was fucking like a dozen i like probably over the whole course of it
probably 10 to 12 women yeah who were in that age bracket yeah i have another guy you should listen
to him i think his name was dave when he got into the milf world and once he get in and if someone
recommends you. You get passed around and he was passed around. He did the same, he had the same
kind of experience as you, you know? It was, oh, it was insane. Like I was fucking these married women who
I had women that were in open marriages before even what the fuck don't even look like. Yeah.
So young, like they were in open marriages. I had a couple husbands watch. You're kidding.
You took all this time to get to that shit. So yeah, some women, some women, some women,
And these husbands, like the husbands wanted to watch.
And I didn't really, at first I'm like, it's kind of weird.
But like, the more I did it, the more I'm like, this is fucking awesome.
Like, I'm fucking the shit of your wife and you're just watching me do it.
It's fucking great.
Oh, my God.
Can you believe like all that shit that was going down?
And is this all in like your little town?
It's all my little town.
And you didn't tell one guy, friend, nobody knew?
I don't know.
I was recommended.
I don't know.
I was just, I was charismatic.
I was a good.
bartender, I was flirty, I was just easy to talk to.
So people kind of gravitate towards me all the time.
And that's just sort of how it happened.
Yeah, but how did that one lady, the friend of the teacher, right?
Well, you've got to get some details on the threesome.
But did the one lady that was the second one, is she the one that said, oh, I know another
woman and that woman connected and then another one would reach out because she heard,
like, was it word on the street or was it just like when you were bartending that you'd
get picked up?
Bartending when I got picked up mostly.
It wasn't really, like people would come and, you know, if I was bartending,
somewhere people would show up and be like there's a really hot bartender you know i and then they
don't know if she would say you know i don't really know they would tell all the fucking details
but like i mean i was definitely fucking a lot of these women who are showing up and you know
at this point like i was having such a fucking good time that i didn't really give a shit with
repercussions of it i was just having fun well were there weren't it doesn't sound like there were
any repercussions no no i mean it was you know there was times where like it was
really easy. You know, if you had somebody, there were times where my people that were, you know,
doing this with me, they knew my parents. So like, these are people my parents knew that I was
fucking. And in certain cases, there were people where I may have known the sons of the daughters.
So I had a few friends where the moms might have been hooking up with me. No, no, no, no. How many
moms of sons and daughters? I mean, give me a brain. How many moms of your friends or people
that you knew in town did you fuck? First.
give me the number and then tell me the stories.
There was only two.
There was only two with my friend's mom.
So where people actually knew the moms, there was only two.
And, you know, it kind of became a very time.
I'm sorry, but listen, most people, the answer would be zero.
Okay, so that's a lot more than most people.
So two is a lot, if you asked me.
Two of like your direct friends or just people in the town that you knew?
Well, there was one guy that I knew, and I don't know, I always kind of had a thing for you
mom.
Oh, my gosh.
And I knew she, I knew she was divorced.
Mm-hmm.
So you remember back when this is going back to the MSN Messenger days is where this kind of all went down.
And I had her on MSN Messenger at the time.
So we're really date, I'm really dating myself now.
But I had her on MSN Messenger.
and we ended up kind of chatting online and it turned into a face-to-face meeting.
Who, like, made the first move in that situation?
Because this is your friend's mom.
So, like, how does it go from, like, you're my friend's mom to something more?
Well, I kind of started out to saying I'm a real piece of shit for sending you this message.
But, you know, I know I'm friends with so-and-so.
but I love to
you know
I love to take you out some time
like literally I think she thought I was kidding
when it first
when it first happened
but I had this thing for his mom
she was she was so gorgeous
and like I just had to have her
I you know you have your friend's mom on
on MSN messenger I don't know why I did
but I pursued her on
on MSN and we started talking a little bit on there
and it just became more of this thing where that did happen.
And my confidence from being with some older women at the time
started to kind of get to my head a little bit
where I really wanted to be more affiliated with some of these,
some of these moms.
And I guess I didn't really give a shit who their kids were at this point.
You just, you got balls from all of this happening.
Yeah, like it really opened a lot of doors for me.
And I just, it was a whole complete,
different demographic than what I was used to with women, right?
Like I was going after a lot.
Like I was, of course, still with a lot of younger women as well,
but I had this side of me that nobody really knew about
where I was going and actually sleeping with women who were twice my age.
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Right.
But wait, let's get back to the mom.
How did that...
How did it go down?
Where did it?
Go down?
Was it in a car or a parking lot?
Was that your friend's house?
Like, where the fuck did that?
What happened?
Exactly.
well this guy and I aren't friends anymore but not for that reason not for the reason you'd think he never he never found out about it left maybe he did but what happened was their family had a cottage and I guess she got that as part of her divorce she had the family cottage where she held on to that and I used to go there with my buddy all the time and you know I used to see his mom there all the time and what happened was the cottage was about a 45 minute drive away from where I lived
So one weekend I met her down there without my friend.
It was just her and I.
And we had a little night together, her and I, where, you know,
we had a drink on the deck, on the dock story, I should say, you know,
we just kind of hung out.
And it ended up being, she ended up, you know, wanting to be with me,
which was pretty cool at the time.
But nobody ever knew about it.
Like she was divorced.
I know she was sleep without her men as well.
Where did you guys talk?
for me to...
Pardon me?
Where do you guys fuck?
Where do we...
We fuck inside the cottage.
Okay.
Okay.
How was it?
Phenomenal.
Like, she...
This was at a point where, like, I had already been sleeping with a lot of milk.
So, like, for me, it wasn't anything new, so I was used to it.
But it was so much better because I've seen her so many times before.
And I don't know.
It was, like, one of those things where it's like, I can't believe I'm fucking my friend's
mom. Yeah, who was that? Stiffler's
my head. What's that movie?
You know, it's like American Pie, Stiffler's
mom, like, you know, it's like, uh, didn't you
grow up with that movie watching it? Now
you're like living it. Yeah.
Oh, these guys look up in the lake. What an idiot.
The lake's right there. I love that part of the movie.
Yeah, but you know what I mean? It's like,
that's when guys, I think, got into,
you know, uh, moms. So
who was the other one?
So that one
I got introduced to and I'm,
and I made it very clear. I'm like,
Like, look, I know your son.
I don't know if it's a big deal or not, but he doesn't have to know.
But I just couldn't believe how slutty these milks were in my town because it was happening a lot more often than I thought it would, to be quite honest with you.
But wait a second, how was that threesome?
Like, when you go back to the teacher lady, are you like, oh my God, can you believe she, like, recommended you?
Because, like, you and her know that you're together, but the other one doesn't know.
No. Like, did you go back to the teacher and say, oh my God, she, like, you know, offered you up for a threesome? Let's like do it.
yeah exactly so i i went to her and i said hey you're not going to believe this yeah but your friend
so and so yeah want i because you know she wants to fuck me you know we're we were already
we already fucked at this point yeah but she's i asked her if she wanted a threesome and she actually
thought to invite you she was hysterically laughing about it the teacher because i think
she really thought that was a good i mean and the funny thing is the teacher had never had a
threesome before right she never did and she told me she never did
Maybe she just didn't tell me.
I don't know.
It doesn't really matter.
But at that time, she did not tell me that she had a three-sum before.
So this was the first time for her.
Yeah.
But not for the friend.
The friend is at many.
And how was it?
Incredible.
Like, you know, that's where I really got a bit more exposed to the BDSM side of things.
You know, I was that younger guy who was fucking these two middle-aged women and I fucking loved it.
But yeah, we had the three-sum.
Matter of fact, my parents were out of town.
so at my parents' house.
Oh, my God.
They're out of town.
So, like, I had my own little space at the basement at the time.
So, like, I was, you know, 19, right?
So we had a threesome.
My parents of a pool.
So, like, we were doing a couple dirty swims out there.
We're all in the backyard naked.
Only my fuck, did you imagine my parents fucking came home?
No.
Or your neighbors were looking out their window.
The good thing about having a private backyard is you don't really see anything.
You just hear it.
That's good.
That's good.
That was the thing.
Oh, my.
So yeah, we were, we were having a fucking blast.
It was incredible.
The threesome was, was, you know, that's where, you know, the friend was into a lot more
freakier shit.
So it was really fucking hot.
Like, I'll be honest, I, this evolved in a way more than I thought it ever would.
Yeah, it evolved a lot more than I thought it would too.
I thought it was just the one teacher.
I didn't know.
It went into couples and other mills and three.
You know what I mean?
I had no idea.
I don't know.
Sometimes people send me long.
winded emails and I just like just come on the show I don't even read because I'm going to get
the whole story when I talk to somebody you know what I mean so I like to be genuinely surprised I don't
need to have questions ahead of time or anything you know what I mean I'm naturally curious so I love
the whole way it happened because I I was just as shocked as you were yeah absolutely it's like
the quote that she left with like she always would say is she goes you know I'm just not getting
the level of sex that you're giving me that's why I keep coming back yeah because she
was at this point in her late 40s or early 40s?
It would have been like mid by this point, like early to mid 40s.
Yeah.
Yeah.
So she was just not getting it.
And like I was a fucking, you know, I'm in college.
Like I'm able to fuck really well.
And a lot of times.
No, no.
And also a lot of times.
When guys hit like late 40s, early 50s, like they're like kind of one and done.
Like they can't do you five times a night.
But a young guy at 18, like a 20 year old, a 25 year old can.
You know what I mean?
Like they can.
So it's a big difference.
Absolutely.
And it just, yeah, I think she just wasn't getting and, you know, she wasn't getting that.
Like, I think she just crave the excitement so much that she didn't give a shit about, you know, what could happen.
It was more like, I am just fucking you so good that you don't even want to look anywhere else.
Or you do, but you just come back to me anyways.
Right.
Yeah, I can't.
About at times.
Yeah.
My phone would be a text from her.
Late night text.
You know, oh, I was at this family event.
It was fucking terrible.
My ex was there.
I don't even want to think about it.
Just come over and fuck me.
Yeah.
I'm coming to your place, pick you up.
Fuck me my car.
Like, it was all the fucking time.
Yeah.
Yeah.
And that's what you get.
That's why I like younger guys are attracted to older women because that's the kind
of hookup you're going to get.
Like, no nonsense.
You know what I mean?
Let's take care of business.
Only the, you know what I mean?
There's nothing negative about it.
And it's pretty easy, stress-free, you know?
Absolutely.
Yeah, but not what you're going to get with your wife and somebody that you're going to marry and everything's going to be a totally different ballgame.
But that could be fun for if that's all you want at the time.
You know what I mean?
Absolutely.
No, for sure.
And it was just, you know, it's the weirdest part of the whole thing, though, I think, is her daughter was like two years younger than me.
Oh, my God.
Yeah.
Yeah, it's crazy.
I mean, the whole thing is crazy.
That never happened.
That never happened.
I didn't keep the family, but definitely crossed my mind once I was like, you know,
it would be fucking funny to bang her daughter.
But like, no, I wouldn't, I would never, I wouldn't go that far.
Because I just think that would have been a pretty awfully to do.
How and why did it end?
Because you moved away?
Or you got married?
Well, I was in my early 20s.
She came down a couple times to my apartment in the new city I lived in.
She visited for a weekend.
But it didn't end.
It didn't end.
And badly, it ended, I would say it ended pretty respectfully, to be quite honest.
Like, she knew that I was starting my career.
She knew that she was far away.
It wouldn't be fair to me to just, you know, kind of always be thinking about her and not really living my life so much.
But I was fine with it if she wanted to stick around.
But about a year or two after that, I met my wife.
So really, at that point, I was more committed to her anyways.
And yeah, but like, it never, it never really, it just, it was one of those things where, like,
It ended. We didn't, you know, with occasional Facebook message here and there.
She texts me, happy birthday once a year kind of thing.
But that was where it ended. We just kind of fizzled out.
So it really was one of those things where I guess the my move away and her, you know, where she, you know, where she lived,
she respectfully wanted me to kind of, you know, start my own life and, you know, didn't really, you know.
And in fairness, I mean, I wished her all the best and we didn't talk for a long time.
and then I found out she passed away, which was fucked up.
Yeah, that's crazy.
How did she pass?
Because she was probably young at that time.
Yeah, she had cancer.
I was, this would have been probably about five years ago.
She passed away.
Oh, really?
And you just heard, like, you heard through the great line, like, you didn't hear when she had cancer or anything like that.
You heard when it was like when she had already passed and then found out the story?
Or did she contact you through that time or no?
No, I, well, I, uh, I kind of was thinking about her one night.
like a few years back
I tried to find her
yeah everyone does that shit
don't be embarrassed
it's a creeper
and that's when I found the obituary
wow isn't that crazy
how old was she when she died
do you know?
I think she would have been
in her 60s I think of that point
right right oh wow
that's crazy crazy right
what a crazy story
yeah I think she would have been
early 60s I'm thinking yeah but anyway yeah
it was wild like
the thing it's
wow, it's like even to just kind of talk about like I've had to like put notes on my phone
throughout because I had to kind of reclick, like I haven't told this story before right?
So I had to kind of go and put notes to my phone of like all the different times to when it
all and think I'm like okay I have to like recollect that like I could be missing some parts of it too.
I don't even know.
It's like he gave it.
He gave enough.
It was good.
It's a good story.
Yeah.
No, it was one of those things where like I really it's yeah.
Like it was definitely opened up to many others.
But I would say like in the amount of women I've slept with in my life, I'd say it's probably
about a 50-50 mix of like women my age and women that are 20 years old at me.
Yeah, well, because you had a lot in that one time.
And then I'm assuming like, you know, you eventually got married and hung your hat with one person.
So, right?
Yeah.
And we've been married now for like 12 years.
Yeah.
And she has no idea, right?
No, she doesn't know the story.
Right.
Nobody knows the story.
No.
nobody knows the story and it's uh you know it's one of those things i never want to make something out of it
i never wanted to like but i wanted people to like i don't know if people have the same fantasy of like
fucking a teacher or like fucking somebody older like it can't happen it just takes balls to actually
put the wheels in motion if you really want to happen or just forget your fucking sweater right kathy yeah yeah
yeah i guess i don't know i think that's yeah i probably all started there
Yeah, no, it was just a wild time of my life.
And it's nice to talk about it.
It's kind of feels...
Wait till you hear back.
Yeah, no, but wait, like, you're gonna, like,
it probably was very fun for you to, like, just put it all out there.
And, like, for you, like you said, it's reminiscing,
but it's also, like, bragging a little...
You know what I mean?
Like, letting people finally know?
Because that's, like, a big thing to keep to yourself for your whole life, right?
Because a lot of guys would have high-fived you for that back in the day,
but you didn't really tell anybody, especially, like,
what followed all the milts and the couples.
You know what I mean?
To keep that all in is like kind of,
what a waste of doing fun stuff
if you can't tell anyone about it.
You know what I mean?
But now tons of people will hear it.
And you're going to get,
wait until you hear your story as a third person,
like you'll dig it.
You know what I mean?
It'll be a very interesting experience for you,
not only talking about it,
I'm sure that was like cathartic and fun,
but it's going to be even better
when you hear it outside of yourself.
Do you know what I mean?
Wait till you see,
because that's what people typically say.
It's very different experience
hearing your story as a third person, right, than telling it yourself. So you're going to enjoy
listening to this one. And thanks so much for calling in. Bye, Mark. Okay. Okay, I just want to tell you
before you go that my book, it's called Strictly Anonymous Confession, Secret Sex Lives of Total
Strangers, is now available in paperback or e-book or audiobook version. The book is basically
17 different stories taken from my show. I kind of picked one story from each category that
talk about it on my show, like there's a hot wife story. There's a cuck queen story. There's a
cuck story. There's a gang being girl story. Like I said, 17 stories. And they're all told in the
third person, and they're all true. I took the interview and rewrote it in the third person. And I
wouldn't really call it like a total erotica book. Think like penthouse letters. It's more direct.
It's not so over the top like erotica. I don't really like that kind of vibe, right? But
These are true stories, 17 of them.
They're really short chapters, easy read.
You could read, you know, one or two and then skip around.
You could read the whole book.
It's available in eback format, paperback format, and finally, the audio book is available.
And if you buy my book in any format, I will throw in a complimentary link to my Discord.
My Discord does not disappoint, okay?
There's no way you get into my Discord any other way than getting the link.
from me. Okay, I give it to people who buy my book. There's tons of people in there. Everybody shares
content with each other and that's what you get to do there. You could post your own pictures and videos.
There's tons of channels. We have lots of contests where you can win a lot of money. It's a super fun place to be.
It's a total, strictly anonymous community and you will love it. I will be giving anyone who buys my book access to my
Discord. It's private, like I said. All you got to do is email me a screenshot of your purchase.
whether you did the audiobook, the e-book, or the paperback.
Send it to me at Strictly Anonymous Podcasts at gmail.com.
That's Strictly Anonymous Podcasts at gmail.com.
And I will send you the link to Discord.
So anyway, thanks so much for tuning in.
This is the Strictly Anonymous Podcast.
Strictly Anonymous Podcast.
