The Boss's Daughter - Cover

The Boss's Daughter

Copyright© 2025 by cv andrews

Chapter 5: Loving Tara - and Sandy - and Tara!

Erotica Sex Story: Chapter 5: Loving Tara - and Sandy - and Tara! - My boss, Nate, who I really like, invites me to his house to meet his cute wife, Sandy, and his 14-year-old daughter, Tara - who I find out has had a crush on me since she was 10.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Heterosexual   Fiction   Sharing   Incest   Mother   Daughter   InLaws   Anal Sex   Analingus   Double Penetration   First   Oral Sex  

“Kyle, I don’t want to fall in love with you.

“I love Nate, and anything more would be just too complicated. And I don’t want you to fall in love with me. It would be so easy, you know – we really like each other, and add to that the fucking ... well, it would be so natural for us to fall in love. So,...”

~ ~ ~

That’s what Sandy said that Friday night – our third night together. And she was right. Sandy and I can’t fall in love with each other. I’m not experienced enough in the ways of life and love to have anticipated that problem. In fact, like most people, I guess, I view “falling in love” as a good, desirable thing.

But Sandy was right – anything more between her and me beyond “just fucking” would, indeed, be “too complicated.”

And yet that is what I was starting to feel. I just didn’t recognize it at first.

I found myself starting to get these feelings of – “fondness,” I guess you’d say – toward Sandy. I mean, I’ve always liked her – liked her a lot – but that was always as a person. From the very first time I came to visit she had welcomed me into her home and welcomed me as her daughter’s “boyfriend” – and now, more. She was always cheerful and upbeat and funny with me, and, yeah, I like her a lot.

But now, I was starting to get these feelings...

What it took me a while to see is that Sandy was starting to get feelings, too.

After we ... after we’d ... alright, after I’d cum in her! ... we always stayed lying there in bed and we’d usually snuggle. But lately Sandy has been wanting to stay like that, snuggling and stuff, longer and longer. And it seemed like when it was time for her to send me upstairs to my “wife,” that now there was a kind of... reluctance ... in her voice, like she really didn’t want me to go.

I think the thing that really caught my attention was one time after I’d just cum in her and we were lying next to each other like usual when she started to say, “Kyle, would you please ho...” And it was like she suddenly stopped herself from saying what she was going to say and instead said, “Please – put your arms around me.”

And it hit me right there and then: She was going to say, “Kyle, please hold me,” but then she stopped herself and instead said, “ ... put your arms around me.” And I realized, there’s a big difference between “put your arms around me,” which is a physical instruction, versus “hold me.” “Holding” someone is more... personal. Holding someone implies some kind of personal feelings the “holder” has toward the person being held.

And Sandy was asking for the second kind – the kind that would tell her that I had feelings toward her that were “special.”

And the thing was, I realized that I wanted to hold her – hold Sandy – “that way.”

And that’s a good thing, to feel that way about her. But in another way, that’s a very bad thing. She’s not supposed to fall in love with me – and I’m not supposed to fall in love with her. As Sandy said, that night so many nights ago, that would make things “just too complicated,” and our... arrangement was supposed to be “simple” – to get Sandy pregnant and to have some fun doing it.

I surprised myself, catching this, this little “slip” on Sandy’s part, a little slip that was a sign that maybe things were getting out of control, maybe going farther than both of us knew they should go. Then I started thinking, and I remembered some other things that are different. When we started ... this ... Sandy was always sure not to let us linger in bed too long and to send me back upstairs, to “my wife.” The past several nights, though, like I said, she’s seemed ... reluctant ... to let me leave ... to “return me” to Tara.

What to do?

How can I get her – and us – and me – back to the original ... arrangement?

~ ~ ~

But in spite of this, after every time, Sandy still places those two little yellow teardrop-shaped pills in my hand and sends me upstairs, to Tara – to my wife.

And every night, when I come back to our room – Tara’s and my room – the first thing we do is kiss and hold each other and let each other know that, no matter what just happened in the bedroom downstairs, that she and I are together, and that we love each other.

And I haven’t done anything different. Or at least I don’t think I have. But I think Tara may be starting to suspect something, too.

Maybe Sandy’s solution, way back “then,” is the best way. So starting the next night we were together I went back to treating Sandy – and thinking of her – as a piece of ass.

The strange thing is, I think maybe Sandy had come to the same conclusion...

~ ~ ~

It was a Friday, and both Sandy and I were excited about ... well, I don’t have to explain to you what we were “excited” about. As soon as I slipped my robe off we headed straight to bed. First Sandy, on her back, legs spread, to welcome me – and to let me get a good look at what was waiting for me.

“Kiss me, Kyle.”

I moved in between those sexy legs, spread so invitingly for me, for my cock, and leaned over to kiss her. She guided me down to her and put her arms around my head and pulled me so my face was an inch from hers. And then she kissed me, one of her amazing, warm, wet, open-mouthed kiss.

And then she started talking. The nasty, slutty talk – the talk of a woman who wants you to treat her like she’s a piece of ass.

“Kyle – I know you can only cum in my cunt...,” and she got this kind of wicked smile, “But we can still fuck other places just as long as you don’t cum...”

It took a few seconds for me to understand what she was saying – what she was telling me. As soon as she saw the look of understanding on my face she smiled, that wicked smile again, and pulled her legs back – wayyy back – back so that my cock was now lined up with her asshole which, come to think of it, looked kind of glisten-y.

“You know, Kyle – Nate and I can hear you and Tara. We can especially hear you when you’re having anal sex. You know that you two get louder when you’re ass-fucking, don’t you. And we see how Tara looks the next morning. And when I hear you two like that it makes me think about us – about you and me, and about you fucking me in the ass. Do you ever think about that, Kyle – about fucking me in the ass?”

Well, if I didn’t think about it before I’m sure going to think about it now!

“Because I think of you doing that to me, Kyle, I think about you fucking me in the ass – a lot. And I know we can’t do it now, Kyle, but after I’m pregnant – after you get me pregnant with our beautiful baby – you can fuck me in the ass all we want. Would you like that, Kyle – that you can fuck me and cum in my ass anytime you want, all you want...?

“So how about it, Kyle? You ready to share some of that good anal sex with me – you ready to put that fine cock up up my hot asshole?”

I didn’t think I needed to answer – especially since she – and Nate, Tara’s father – seem to be pretty well aware of our anal activities. I moved my cock closer, almost next to her asshole, and Sandy reached down and guided it the rest of the way in.

“Now, Kyle, do it – fuck my hot ass.”

Okay, this has nothing to do with getting Sandy pregnant. This is about a hot, sexual woman who wants to feel a cock up in her ass. My cock!

Sandy’s fingers already had me in position so all there was for me to do was push – and, amazingly, I was half-way in! I sensed something cool and creamy and I realized that Sandy must have lubed her ass earlier in the evening, before I came in.

And that just made it even hotter – the idea that she started this evening, maybe even thought about it the last time, maybe even while we were still together – wanting to feel my cock filling her ass.

And she was right – it was hot, maybe even hotter than her daughter’s ... ass.

“Is this what you want, Sandy – is this what you were hoping for?” I hoped I wasn’t going too far by talking like this.

“Mmmm ... Kyle – I’ve been wanting to feel this for...” She didn’t finish what she’d started to say.

Just how long has Sandy wanted to feel “this” – feel my cock in her ass?

“Don’t stop now, Kyle – put it the rest of the way in – I want to feel all of your cock – I want you to fill my dirty little asshole with your cock.”

Now that I knew that everything was okay, that I wasn’t being out of line in doing this, that we weren’t breaking any rules, as least as far as Sandy was concerned, I leaned into her, and in a few seconds my groin was pressed up against her and my cock was all the way inside her – I was filling her asshole, her “dirty little asshole,” with my cock.

God, it felt good! She might be an “experienced” woman, but she – her asshole – was tight, as tight as her daughter’s. And hot. I don’t think I ever felt my cock grasped in such heat. I stopped moving just so I could experience the heat that lived deep inside Sandy’s rectum...

Until I heard he voice saying, “Don’t stop, Kyle, keep fucking me. I want to feel that lovely cock sliding in and out. Don’t you want to do that, Kyle – feeling your cock sliding in and out of my tight ass?”

I began to move my hips, first feeling the velvet-like lining of Sandy’s rectum, and then the pressure, the grasp, of her anal ring – and then back, through the tight ring of muscle that was like another hand squeezing my cock as it slid through, only to end up in that velvet, hot sleeve of her rectum again. And again, and again, getting lost in the experience, of the beautiful glove of Sandy’s ass...

And my mind wandered, to a place where I was almost looking down on me, watching me doing this. And what am I doing? I’m bare-ass naked, between the legs of my girlfriend’s – “my wife”’s – mother, and I have my cock buried deep in her asshole. and I’m fucking her – I’m fucking my “wife’s” mother in the ass! And it’s me that she wants – she wants it to be my cock that’s fucking her in the ass.

And while I’m doing this she’s saying things like,

Fuck, fuck, fuck – fuck my nasty ass, Kyle.

“Tell me – tell me how much you love fucking my dirty little ass.”

Yeah, we’re a long way from me being with Sandy for the purpose of getting my boss’s wife pregnant.

“Yeah – your ass feels so good. My cock loves fucking you in your dirty little ass.”

When I said that, said those words, Sandy reached up and pulled me down to her, to her face. And when or mouths were against each other she started kissing me, open-mouthed, sloppy, licking my face, squeezing on my lip with her teeth, then licking my around my mouth, and I started licking her the same way, and it was like our mouths were fucking each other while Imy cock was fucking her ass.

While we were doing this – kissing – mouth-fucking – she was clenching the muscles of her ass, making herself even tighter, forcing me to really exert some pressure if I was going to move, to really fuck her...

And I started to get those feelings. You know – the ones that tell you you’re going over the top in just a few moments...

And that’s when she stopped. Stopped licking and sucking my mouth, stopped clenching the muscles in her ass, and put her hands on my chest to steady me. I stopped, then gradually pulled my cock, still hard and unsatisfied, out from the grasp of her rectum before an “accident” happened.

“We were just about to break the rules, weren’t we, Kyle?”

I smiled, at the way she put it.

“Yeah, I was about ready to break the rules.’

She pulled me back down to her for a kiss.

“Don’t worry, Sweetheart – once you get me pregnant well have plenty of opportunities to break the rules.”

... and that was the first time it ever came up – what are we going to do – what will... things ... be like... after the mission is accomplished and Sandy is pregnant? Is she saying that...?

But before I could get lost in those thoughts Sandy slowly, gently, pulled away from me and guided me up till I was straddling her, my hips almost even with her face. She looked at my cock and took it between her thumb and one finger.

“I think it would be a good idea to clean that lovely thing off a bit before you put it in me again – don’t you think so, Kyle?” She opened her mouth and pulled me to her, and she took my cock, straight out of her hot, slippery ass hole, into her mouth and started moving my hips so my cock slid in and out of her mouth, between her lips, like I was fucking her mouth. And I felt her tongue as she licked – almost swirled it – around the crown...

And what she was doing – sucking and licking my cock that had just been up her asshole – was so... filthy ... and so... wanton that I quickly regained any hardness I might have lost, and then some.

“Fuck me, Kyle. Put your big dick in my cunt and fuck me till you but a baby in there.”

She scooted up in the bed till her head was on the pillows and she spread her legs and held out her arms to me, and I slid in between those sexy spread legs and into those welcoming arms.

“You and I’ve wanted to do this for a long time, haven’t we, Kyle. Admit it – you wanted to fuck me that very first time, that time when we danced together on Tara’s birthday. You’ve wanted to fuck your girlfriend’s mother all along, since that first time you touched her and got hard, you’ve wanted to fuck me...”

And I thought: Maybe I have. Even though I’d never think of cheating on Tara – or betray Nate, for that matter – still, maybe all along I’ve unconsciously been harboring the thought of how hot, and how sexy, Sandy is, and how much I’d really like to fuck my girlfriend’s mother.

“You can do it now, Kyle. You know that now it’s okay to do what you’ve wanted to all this time – to fuck your little girlfriend’s hot, slutty mother.”

So I did it. I fucked my girlfriend’s hot, and now slutty, mother, and tried for all I was worth to put a baby “in there.”

And Sandy’s words worked. I came so hard I think I unloaded more cum into her than ever before. And if I did, if I gave her enough of my sperm to finally get her pregnant – then we’re that much closer to the time when I can fuck Sandy in the ass, “anytime I want, all I want.”

~ ~ ~

After that night things between Sandy and me seemed to return to “normal,” which for us, I guess, means just good, nasty, fun sex. There were never any more hints of “romantic” feelings, and if I caught myself starting to get any feelings toward Sandy that were more than just lust and simple liking I immediately turned my thoughts to other, “less romantic” images.

Like the night when Sandy was lying on top of me, and we’ve done it like this lots of times. Except this time for some reason Sandy felt “different” – inside.

Maybe she saw something in my expression because she stopped riding my cock and asked, “Do I feel different, Kyle? Do I feel different to you – inside? Do I feel tighter to you? Because I want to be nice and tight for you, Kyle, I want that.”

Yeah, that was it. Her cunt always feels nice and snug, but now it also feels – tighter. Sandy didn’t wait for me to say anything – she could see the realization on my face.

“That’s because I want my cunt to be nice and tight for you, Kyle. So I did something – I hope you like it,” and she took my hand and guided it around back, to her ass, and then to the crease – and then to the spot in between, where my fingers touched something solid.

“See what I did for you, Kyle? I did something so my cunt would be nice and tight for you. Do you like it, Kyle – do you like what I did for you?”

Yes, what she’d done was to insert some kind of object into her ass – a butt plug. But not the kind of butt plug that’s shaped like a cone. This one was shaped more like a “regular” dildo, but with an indent at the end so you can put it in and it’ll stay in, in-place.

And yes, I do like what Sandy did for me.

And now I’m wondering if what she did tonight, with the dildo in her ass, was preparing me for what would happen several nights later.

~ ~ ~

Once again, I’m lying on my back and Sandy is on top of me, fucking herself until it’s time for me to cum, and then we roll over so that I’m on top of her ‘cause Sandy feels that this way more of my sperm will find their way to their target and she’ll get pregnant that much sooner.

Except this time, the bedroom door opens – we don’t actually close it all the way – somehow that seems to both of us like we’re trying to hide something – and Nate eases himself into the room.

Yeah, Sandy’s husband, Nate. My boss.

And a few steps behind him, standing in the doorway, is Tara, my...?

Nate skims off his sweats and T-shirt and announces that he’d like to fuck his girl, too.

Well, you can imagine the effect this has on me. Or maybe you can’t imagine. But anyhow, Sandy – she’s amazing – manages to keep my focus on her and not lose my hard-on.

“Look, Kyle, visitors. I guess they heard how much fun you and I are having and they just couldn’t bear to be left out.”

And that tells me right away that this is something Sandy and Nate had already arranged between them so it’s not like Sandy and I have been “caught” doing something ... something that we shouldn’t be doing. So that helped keep me from going soft all of a sudden.

Nate comes over to beside where we are and Sandy turns her head to the side and Nate kisses her. Yeah, Sandy’s husband kisses her while she’s riding my cock! And since he’s standing right next to where her head is, his cock is right next to her, Sandy doesn’t waste any time. She lets her mouth drop open and Nate puts his hard-on next to her lips, and without taking her hands off my shoulders Sandy lets her husband fuck his cock in and out of her mouth, and she seems to be making sure that it’s getting good and wet.

And all the while I’m wondering how this is going to play out, or work out, or ... whatever, when Nate backs away from Sandy, from Sandy’s loving lips, and gets on the bed and kneels over her.

“Kyle, there’s this thing, and I’ve always wondered what it would feel like, but, well, Nate and I have never had the chance – or the opportunity, I guess, but then when you started coming around Nate and I talked again, and we decided that if there was ever anyone we’d want to do it with, that it would be you.”

And by now I’m starting to get the picture. Sandy wants to have two men – wants to try sex with two men at the same time. And they – she and Nate – have decided that I’m the guy they want to try it with.

But what I don’t know is, exactly how they want to do “this” ... this whatever it is.

Well, Nate put that question to rest pretty quickly.

Like I said, he’s already on the bed, kneeling over Sandy. And in his hand is something I recognize right away, because it’s exactly like that blue and white squeeze tube that Tara now keeps on the bedside table the nights – and days – that we’re going to be together.

And that makes me remember: Tara!

She’s still standing in the doorway, not leaving, but not ready to step farther into the room – yet. And from where she’s standing she sees her dad squirt a generous glob of lubricant from that tube, and she watches him – them – as he lovingly massages the slippery gel into her mother’s rosebud asshole at the same time she’s fucking herself on my cock.

And once again, it’s Sandy who sees to it that everyone is taken care of and that nobody is left out. She sees Tara standing in the doorway, and she knows that Tara and her dad talked about this, and even though Tara wasn’t going to be involved her dad was concerned about how she’d feel about this – whatever “this” is.

“Come in, Darling. There’s no need for you to be left out, just standing there while we’re ... Come in, Darling – be with us, here.”

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