Richie's Mom - Cover

Richie's Mom

Copyright© 2026 by cv andrews

Chapter 1

Erotica Sex Story: Chapter 1 - "My mom's got a crush on you." That's what my best friend Richie said one night when we were just hanging out in my back yard. "Davey, my mother's got a serious crush on you” Of course I was sure he was just clowning around, fucking with me just for the heck of it. I mean, sure, I'd known Richie's mom for ages, since we were seven and in the second grade, and yeah, she's real cute and I've seen her in a bikini and she's got a great body and stuff. But, c'mon – Richie's mom...?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Fa/Fa   Fa/ft   Consensual   Lesbian   Heterosexual   Fiction   Sharing   Incest   Mother   Son   Father   Daughter   Gang Bang   Group Sex   Anal Sex   Analingus   Double Penetration   Fisting   Oral Sex   Teacher/Student  

“My mom’s got a crush on you.”

That’s what my best friend, Richie, said, one night when we were just hanging out in my back yard.

The evening was warm and we were sitting on the lawn chairs having some sodas. We’re both old enough that my folks wouldn’t have minded if we got a couple of Heinekens out of the fridge, but instead we were just drinking Cokes.

At first I didn’t think that I heard him right.

“Whaddaya mean, ‘got a crush on me’?”

Richie took his time taking another pull on his can of Coke. It looked like he was debating whether to say something or not. But then it was like he decided that he needed to.

“Davey, my mother’s got a serious crush on you, and...” He trailed off, like he needed to say more but really didn’t know what it was he had to say.

Of course I was sure he was just clowning around, fucking with me just for the heck of it. I mean, sure, I’d known Richie’s mom for ages, since we were seven and in the second grade, and yeah, she’s a real nice person and I like her a lot and she seems to like me a lot and is real glad that I was Richie’s friend.

But the other thing is – his mom is really pretty. First, she’s really cute. I mean, she looks like what you’d think of if I said “blond high-school cheerleader.” But then there’s the other thing, too. I’ve seen her in a bikini at the pool, and even around their house, in athletic wear like tights and a T-shirt or her sports bra, and she’s got a great body, and I’d give several ... well, I’d give a lot – to have a girlfriend like her – in looks, and in personality. But, c’mon – Richie’s mom, Carole?

But Richie hadn’t smiled, or laughed, or punched me in the arm and said he was just messing with me, or given me any sign that he was joking. In fact, he seemed real serious, like what he said was some kind of ... burden or something.

Still, I was sure...

“Yeah, right – your hot mom’s got a crush on a college kid she’s known since...,” and I couldn’t think of how to say how long she’s known me.

Richie didn’t say anything, just stared at his can of Coke.

“C’mon, Rich, enough’s enough – let it go, man.”

But Richie didn’t “let it go.” Instead he got even more serious.

“I’m not fuckin’ with you, Davey. My mom likes you, and she likes you in a way that’s not like you’re a friend of mine...”

He paused, like he was trying to find the right way to say something.

“Davey, I think she likes you ... like a man.”

Like a man??

“Don’t fuck with me, Richie. Like a man? Shit. I’ll bet that to your mom I’m still the little twerp who used to splash around with you in your kiddie pool in our underpants. She sees me like a man? Bullshit.”

“Davey, she says things to me, about you – about how smart you ... no, how intelligent you are, and about how kind and thoughtful you are and what a fine young man you’ve become, and she says things ... about how you look – I won’t even say what she says ‘cause it’d make me feel gay just saying them.”

I didn’t respond. Instead, I just sat there, waiting for him to break up laughing at the practical joke he was trying to pull on me.

But he never did. So finally I said, “Okay, Rich, if your mom’s really like you say, why? Like, I’m still a kid, like you. Why would a woman like your mom,” I took a chance, “ ... be attracted to a kid?”

Richie just shrugged and continued staring at his Coke can.

I tried another angle.

“Okay, let’s say your mom really is ... attracted to me...,” and now it was me who was groping, trying to come up with the right words ... and whether I should even say them or not, “How would you feel about it ... about that?” I know that if the situation was reversed that I’d sure as shit have some feelings about it.”

“Don’t think I haven’t thought about it, Davey. And the first thing I thought about was if she’s just lonely – physically. I mean, she hasn’t gone out practically at all since Dad died, and maybe she likes the idea of having some college stud ... well, you know ... And in one way that grosses me out, thinking about my mom and ... a guy ... you know, that way. But on the other hand, at least I could understand it, and I wouldn’t hold it against her.”

And I thought, yeah, that might make sense. I mean, if a woman as... attractive ... as Richie’s mom is ... hadn’t... you know ... for a long time, then maybe she’d start looking at young guys. But before I could say anything Richie went on.

“The thing is, when I listen to the way she says things, about you, it’s like ... like...,” he took a deep breath, like he was going to say something that he’d thought about a lot and had kind of rehearsed it, “It’s like she thinks you’re like ... that you’re like the kind of man that she hoped my father would be...”

Richie’s father. He seemed OK, but never really quite ... involved, engaged, if you can understand what I’m trying to get at. It was like he had this really great wife and this really cool son and yet he never seemed to appreciate them. And then he died – I never got the details – about eight years ago.

So, okay, maybe – and for the life of me I can’t figure out how or why – Richie’s mom sees – or thinks she sees — things she thought she saw in Richie’s dad back when ... back whenever.

“So...?”

“So I guess what I’m trying to tell you is – she doesn’t see you like ... I think she looks at you ... like she thinks ... you should be ... the man ... that you ... that the two of you ... should be ... together.” And he kind of just seemed to ... sag ... once he finished saying that.

Okay, this is already weird, but now it’s starting to get downright creepy. I mean, what’d it be like between me and Richie, my closest friend in the whole world since we were just little kids, if me and his mom were... together?

But I had to ask him one more thing.

“Why are you telling me all this, Rich?”

He thought for a moment.

“Because I owe it to her ... to my mom.”


Richie ... Rich... Richard Wilson has been my best friend since he and I were in the second grade and we got into this playground fight – I can’t even remember what it was about, and I’m sure it wasn’t anything that important in the first place – and Mrs. Conner made us sit in the classroom by ourselves until we apologized to each other. And we’ve been pretty much constant companions since then.

And of course we spent a lot of time at each other’s houses and got to know each other’s parents. And that’s how I got to know Mr. and Mrs. Wilson, ‘cause I was over at their place so much, and in the summer we’d splash around in the play pool that Mrs. Wilson would inflate for us in their back yard, and later when we got older, maybe nine or ten or so, he and I’d ride our bikes to the municipal pool in Humboldt Park.

And in the cold weather we’d do stuff indoors, like playing bumper pool in their basement or air hockey in ours, and later, when they got good, video games.

And Mrs. Wilson was always there. Mr. Wilson, not so much, but Mrs. Wilson was always there to offer us juice or Kool-Aid and to answer questions and fix scrapes and cuts and stuff, and lots of times she’d ask me to ask my folks if I could stay for dinner (and Richie’d have dinner with us lots of times, too).

And she was always so cool. I don’t mean cool like ... like “being cool” ... like she never tried to be our pal or talk like we did or butt into our games or anything. I mean ‘cool’ like nothing was ever a big problem or a “federal case,” as my dad would say. If something bad happened, or if Richie or I ever fucked up – I mean, screwed up – she never made a big deal about it – just told us to stop doing what we were doing or fix what we’d busted. And if we asked a question, even if it was dumb, or maybe even about something that was kind of embarrassing, she do her best to answer it honestly but in a way that was right for how old we were.

And after enough years of this we became friends, and she wasn’t just “Richie’s Mom” anymore. I mean, yeah, she was still “Richie’s Mom,” but she was also my friend. And we could talk about stuff, like things about our other friends, or about current events and stuff like that, even if Richie wasn’t there. And even sometimes things that were bothering us or problems we were having.

When we were ten Mr. Wilson died. Nobody ever talked about it much. Like I said earlier, Richie’s dad never seemed to be quite “there,” never seemed to be really involved in his family’s life. When I got older I wondered if he committed suicide or if it was something about alcoholism or something like that. But like I said, that was one thing that Richie and his mom never talked about.

After we graduated high school I went to college at State, in Springfield. Richie decided to stay in town and go to Columbia Tech because they have this extensive medical technology program. Plus, going to school in town and living at home saved them a ton of money. And whenever I would phone I ended up spending half the time talking to Richie and half the time talking with his mom ‘cause I was just so used to us talking.

So when I came home for summer vacation it was just natural to head straight over to Richie’s house. But when I rang the bell it was Mrs. Wilson who opened the door. She looked at me and got a big smile on her face. She threw her arms around me and hugged me and kissed me on the cheek, then pulled me into the house and closed the door behind us.

“It’s so good to see you – it seems like it’s been so long!” and she hugged me again. “Rich is in the shower – he got a call just after he talked with you so he’s running a little behind.”

We went into the kitchen and sat down at the table – the table where I’ve spent hundreds – thousands? – of hours over the past 11 years? She poured mugs of coffee for us and sat down, and that’s when I realized how happy I was to see her again, and how natural it felt to be sitting at her kitchen table with her.

“Gee, Mrs. W, it’s great to see you again.” And I meant it – it was great to see her again.

“It’s good seeing you, too, David. But don’t you think we’ve known each other long enough that the ‘Mrs. W’ thing is getting a little old? I think from now on you should call me Carole – would that be OK?” And she waited for me to say something.

“Sure ... Carole.”

“And the other thing is ... you’re not the skinny little squirt who used to run through the lawn sprinkler with Rich when you were seven. Now you’re a 19-year-old college boy – college man. So I don’t think you’re ‘Davey’ any more, do you? From now on, with me you’re ‘David.’ Right...?”

Carole and David.

It felt comfortable. The way old friends should be.


Anyhow, it’s two weeks after Richie and I had our “conversation” – the “conversation” where he told me that his mother “had a crush on me.” And that she doesn’t see me as her son’s friend – or at least, not just as her son’s friend. No, instead she sees me as a man. And more than that, she feels that we, her and me – this man – should be together.

WTF?

I mean, WTF?? Richie’s mom – and she’s a great woman, don’t get me wrong – but jeez, she’s practically like a mom to me. I mean, she is a mom, of course. But she’s almost as much a mom to me as my own mom is.

This is friggin’ crazy, right? How can she see me as ... as a man? I mean, she said that I’m not the skinny little squirt that ran through the sprinkler with Richie, and I guess that’s true. And that now I am a man ... well, sort of ... But, still...

And how can I see her as someone else instead of as my friend’s mom?

But then I realize ... it’s not that hard to see her as ... not-a-mom. In some ways, for years I’ve seen her as not just a mom. As I’ve learned more about people I see how nice she is, and how smart she is – she graduated Phi Beta Kappa and cum laude in biology in just three years from a real selective private college. But also how smart she is about life, and how much stuff she seems to know, and the real good advice she’s able to give – but only if you ask her.

And how most of what I know about girls came from her. And not all that “you need to respect her” or “be sensitive” BS. Instead, she explained it to me that it wasn’t about how the girl makes me feel, but how I make the girl feel. And about sex. And I’m not talking about the technical stuff, like... techniques. That’s why the Internet was invented, right? No, the things she told me, now that I think of it, were mostly just plain Golden Rule shit... ‘scuse me – Golden Rule stuff, like think about how Id like to be treated, and how I’d like to feel – that kind of stuff.

And, yeah, I admit – I’ve looked at her like a woman lots of times, too. I mean, one, she’s got a real cute face, and her hair is this real nice blond that’s kind of the color of straw. And I’m not gonna lie – she’s got a real nice body. And I’ve seen her sunning herself in a bikini when Richie and I were in the pool, and I notice how good – how hot – she looks when she’s wearing a T-shirt or a tank top and jeans or her yoga pants.

So, yeah, now that I think of it, it’s not that much of a stretch for me to see Mrs. Wilson – “Carole” – as a woman.

And then my mind starts to flash back to how things have been the past couple of weeks, since I got home from college and Richie and I started hanging around again. First, like how she – Carole – talks to me. Not like her son’s visiting friend – instead it’s more like her and me are having a conversation and Richie’s just there too.

And there’s the physical stuff, too. Like how it seems like she stands just a little bit closer to me than she used to. And not flirty-type stuff, like touching me all the time for no reason or twirling her hair and stuff, but now when I come over and she walks me into the house she puts her hand on my arm, or on my bicep, and keeps her hand there for a while. Same thing when I’m leaving.

And the time last week when Richie and me were going out and she asked – not prying, just polite interest – where we were going and Richie told her and said we might meet up with some girls later. And now that I remember it, she got this look, almost like she had some kind of pain. It was only for a second, but now that I think of it and knowing what Richie told me about how she feels about me, I’m wondering – did it actually hurt her – the idea that I might be meeting some girl – some other girl.

So, yeah, maybe my best friend Richie wasn’t shittin’ me.

So, ... what now...?

And me and Richie’s mom?

I mean, how would that even work...?


It was Saturday, and, yeah, Saturday was important, because Richie and I both had lined up jobs for the summer. Richie had a gig as a “Technician’s Assistant” at a medical laboratory processing medical tests and I got a job five and a half days a week at the office of an insurance agent friend of my dad’s. So, yeah, Saturday was important to Richie and me.

Since it looked like it was going to be a really hot day Richie said that I should come over and swim in their pool. Richie’s dad might have been a dud as a dad, and as a husband, I guess, but he did “provide well” for his family, and that included a very nice house, and that included an in-ground swimming pool. It had a really nice patio all around it, large enough that they even had a kind of shed – Richie’s mom called it a “cabana,” which I guess is fancy beach lingo for a cabin – in the back corner that people could use to change if they wanted to.

Like usual, I came around the back and banged on the gate, and Richie’s mom – sorry, Carole – came over and flipped the latch and let me in. And of course the first thing I notice is what she’s wearing – a loose while cotton beach shirt, I guess you’d call it, and it was open and I could see that she had on a bikini underneath it. Her bikini wasn’t outrageous or anything – just a nice kind-of pink bikini, but it reminded me of just how good she looks in a swim suit.

“Hi, Carole.”

She leaned in and gave me a hug, then took me by the arm and led me around under the patio awning. Richie and Vanessa, his girlfriend for the past six months or so, were already splashing around in the pool.

“What would you like to drink?”

Since it was going to be hot and we were also going to be swimming, I figured that a Coke would be a saner choice than a beer.

Carole came out of the kitchen with two Cokes, and we sat and talked a little. She asked if I was glad to be home for the summer, and it made me think – it is nice to be home for the summer, and seeing Richie – and being able to sit and spend time with Carole, like this.

But before I could get lost in my summertime reveries I heard Richie shout, “Hey, you two, are you just going to sit there and gab all afternoon or are you going to get wet!” Carole and I smiled at each other and she gave me that “what are ya’ gonna do?” look and stood up, slipped off her cotton shirt, and did a very neat dive from the side of the pool. I stripped off my tee and board shorts and kicked off my Tevas and did a far less elegant feet-first jump into the pool.

In spite of how hot the air was the cold water was still a shock, but in a minute I was used to it and began doing some strokes and then splashing around with Richie and Vanessa and Carole. We were having a good time, just horsing around, when Vanessa said, “Richie, let me get on your shoulders and your mom can get on Davey and we can have a jousting contest.”

I met Vanessa – “Van” – when I was home on break in April, and I thought she was really cute. She’s only about five feet tall and has almost a baby face, with blue eyes and blond hair that’s usually pulled back in a ponytail and a cute button nose and these pouty lips that look like they’re meant to be kissed (and other things). And her cute little body always looked nice under the T-shirt and jeans she was usually wearing. And now that she’s in her bikini I can see that she still has a little bit of baby fat but it just makes her tummy and her tits look that much sexier.

But mainly, she seems really nice, and I think Carole likes her and is glad the she’s with Richie.

Anyhow, you know how this works, with the girls on the guys’ shoulders, and they maneuver and wrestle, trying to knock each other off and into the water. Richie was already squatting down in the water and Van was on his shoulders, so of course, I did the same thing.

And then I realized what this meant. That Carole, Richie’s pretty, sexy mother, would be sitting on my shoulders, and that my head would be right between her thighs – her nice, well-toned thighs. I mean, I’d be facing away from her, so my face wouldn’t be right...

Carole climbed onto my shoulders without the least bit of hesitation, shouting, “So you want to fight, huh?” and Van yelling back, “If you think you’re up to it, old lady!” and Carole shouting back, “Oh – it’s on!”

And it was like that. Carole and Van were trying to grab each other without getting grabbed and Richie and I trying to hold our “riders” on without falling over ourselves. It was so much fun that there were moments when I lost awareness that my head was between Richie’s mom’s thighs – and that she was squeezing them maybe a little tighter than she needed to stay on.

Well, Richie and I got so close that we were practically face to face when I heard, “Ha – I got it! There!” and I saw something pink fly past. Van had managed to pull Carole’s bikini top off her!

You little witch!” Then, David, try to get around behind them!”

Richie was off-balance enough that I was able to do what Carole said and get behind Richie and Van, and that’s when I saw Carole’s hands snatch Van’s thin bikini top off her and throw it into the water where it landed next to Carole’s own abandoned top.

So now both girls are topless, and they’re laughing, and I can see that Van has a really cute pair of tits, with her pink nipples sticking out and hard from the cold water. And then it hit me: That means that now Richie can see his mom’s tits, and I’m wondering what he’s thinking about that. And what Carole is thinking about that – about her son seeing her bare breasts.

But Carole didn’t seem to be the least bit upset or even shy about the whole thing. And then I realized – those tits of Richie’s mother are on top of my head, and sometimes, when she moves a certain way, my head’s even between them...

But before I can get too lost in those thoughts Carole and Van lock onto each other and won’t let go, until both girls topple off us and bring Richie and me down with them. We all pop up spitting water and laughing. Carole grabs Van and kisses her, but it not like a sexual kiss, just a kiss showing that she likes Van and that she’s happy that her son has a nice, fun, summer girlfriend.

Then the girls go retrieve their tops that are still floating in the pool but they don’t put them on right away, and I guess that leaves Richie and me getting an eyeful, or maybe two eyes’ full. But then they climb out of the pool, and when they do I can see that the crotch of Van’s thin white bikini bottoms has worked it’s way almost completely into her pussy slit, and I wonder if she even knows it. But then she doesn’t do anything about it and it didn’t look like Richie’s said anything, so I think she’s really going to leave it that way.

So Richie and I get out and Van asks Richie to help her put her top back on, and I’m wondering where that leaves me, but then Carole walks over and picks up the beach shirt she was wearing when I came and put that on. But she never bothered to put her bikini bra back on, and even though it wasn’t transparent or anything I could still tell that her breasts are hanging free under that the white cotton shirt.

By now Carole’s and my Cokes went flat a long time ago so she said, “David, come into the kitchen with me and we can get some fresh drinks for everyone.” So I went with Carole into the kitchen and she got a big bowl and filled it with ice and put some Cokes and Sprites and beers in it. She slid the patio door open for me and with my hands freezing I carried the icy bowl out and set it on the table.

And that’s when we noticed – no Richie or Van. Carole took a look around the pool area, then this little smile crept over her face. She said softly, “Come with me,” and then added, “Don’t make a sound.”

She took my (chilly) hand and led me over to the far corner of the pool deck, to the little cabana there. She raised one finger to her lips, signaling me to stay there and be quiet. Then she leaned forward, just enough that she could sneak a peek around the corner of the cabana. Then she looked back at me and held her finger to her lips again and led me to the cabana door. She turned the handle and opened it very carefully, then went inside, bringing me with her.

She didn’t turn on the overhead light, but the window let in enough light that we could get around okay. She went over to one corner of the open window and crouched down, just enough that she could see out along the side of the cabana. She smiled and then stood up and motioned for me to take her place.

I crouched down where Carole had been and looked out the window. And I saw what Carole had been watching – Richie leaning back against the wall, his cock sticking out above his pulled-down Speedos, and Vanessa, kneeling on a rolled up towel, her hands grabbing Richie’s ass while she worked her mouth up and down his cock.

I felt Carole move up against me and we watched together as Van took one hand off Richie’s butt and began stroking his cock. And all of a sudden I’m very aware of the... particular attributes... of this situation: I’m here watching my best friend with his cock out getting a blowjob from his curvy little girlfriend while his mom and I are watching it all. And to top off the weirdness, she’s standing so close to me that I can feel her... front ... against my back.

Van’s changed her technique so that now she’s sliding her hand back with this kind of twisting, corkscrewing motion each time she backs her head off Richie’s cock. Then just to make it all even more obscene she starts saying things to Richie, and since the window is open half-way we’re able to hear what they’re saying.

“Did seeing your mom’s tits turn you on?”

Richie made some kind of mumbling sound.

“Tell me ... did it turn you on, seeing your mom’s tits? I know it did, that’s why you let me drag you back here so I’d suck you off, isn’t it?”

Another sound from Richie – this time a kind of a groan.

“She’s got really nice tits, doesn’t she, Richie. Say it, Richie – say that your mom has nice titties and that it turns you on seeing them, didn’t it?” She punctuated her demands by stopping whatever else she was doing with Richie’s cock.

Wanting her to keep on doing what she was doing, Richie finally gave in.

“My mom ... has nice ... tits...”

“And!”

“And it turned me on...”

“What turned you on, Rich?”

“Seeing my mom’s tits ... titties...”

And seeing – hearing – this got me wondering – why Van seemed to be so interested in Carole’s... tits. And also, it was almost like she was trying to get Richie to think about his mom’s breasts, and why she’d want to do that I had no idea.

And then I remember that Carole is right here with me and she’s hearing all this right along with me. And how she feels, about having Van talking about her ... her tits? And about Richie thinking – and talking – about his mother’s... tits?

But that was about all Richie could take, because once she got him to say that “seeing his mom’s tits turned him on” she seemed to increase her efforts and in 30 seconds we heard Rich groan, “Oh, fuck – I’m gonna cum – I’m gonna cum in your fucking mouth, you fucking little whore...!” and Vanessa stopping whatever she was doing just long enough to say, “Yeah, that’s it – cum in my fucking little mouth...,” and then getting her “fucking little mouth” back on Richie’s cock, and in a few second more he was pulling her head tight against his groin and pumping his hips and moaning, “Oh, fuck – fuuuuck...,”

And I’m just a few feet away from all this and hearing every word of it.

And so is his mother. Carole is still there, not pressing herself but definitely leaning against me, her head over my shoulder, her cheek right next to mine, while we watch together as her son’s girlfriend jacks her son off into her mouth.

As soon as we were sure we’d seen the finale Carole stood up and stepped back, then took my hand and with this naughty little smile on her face quickly led us out of the little cabin and back to the patio table and our drinks before Richie and Van could catch us spying.

And I thinking, “How cool is this!” – that a mom could watch her son’s girlfriend sucking him off and still smile and be all cool about it. So cool, in fact, that she dragged her son’s friend – me – along to watch it with her. I mean, she knows that her son has a sex life, and she’s happy that he does and that he and his girlfriend enjoy it and are comfortable enough that they can even sneak off for a “quickie” and it’s still alright.

I’m not sure how she feels about hearing her son coerced into saying that seeing his mom’s tits turns him on, though.

We just managed to get our drinks open – another Coke for me and a beer for Carole – so it looked like we’d been there all along and pretend that we didn’t notice Richie and Van just coming around the corner of the cabana.

Carole acted like they’d surprised us and asked if they were thirsty and wanted something to drink. And the great thing was, even though there was a little dried white something on Van’s upper lip she didn’t ask it in a snarky way or smirk at Van when she said it. Like I said – cool.

And made me remember again why I like this woman so much, and how I hoped that I could find a girl like her.

After some drinks and talk Richie – “Richard” – announced that they were going to do something with Van’s parents tonight and they said that it was going to go late and that Richie could stay overnight at their house.

In a mock serious-hurt tone, Carole said, “And leave your poor mother here all alone on a Saturday night?” And all of a sudden, Richie got serious, like he knew his mother was just needling him, but also he felt bad that his mom would be alone.

“Hey, Davey could stay here and have dinner with you. Whyntcha call his home and tell them that he’s having dinner here tonight?” Not that unusual, since Richie and I often stay at each other’s houses for dinner.

 
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