The Boss's Daughter - Loving Sandy... and Tara!
Copyright© 2025 by cv andrews
Chapter 1
Erotica Sex Story: Chapter 1 - My boss's daughter, Tara, has become my serious girlfriend. Then Tara's parents announce that they want to have another child and they can't do it on their own so with Tara's support I happily undertake the job! Years later, Tara invites a friend from yoga class over - and it turns out to be my old college girlfriend! More amazing, her husband turns out to be the boy who took Tara to the prom years before.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Heterosexual Fiction Sharing Incest Mother Father Daughter InLaws Group Sex Anal Sex Double Penetration Pegging
“We want to stay here, with the two of you.”
It was shortly after Tara’s eighteenth birthday that Sandy and Nate, Tara’s mother and father, made their announcement – that seeing what a beautiful young woman Tara had become, they decided that they wanted a try at having one more child.
And because of Sandy and Nate’s genetic relationship, they wanted me to be the one to make Sandy pregnant.
So for months now Sandy and I have continued our efforts to make a baby for her and Nate. And, yes, we had fun – a lot of fun! – trying to do it.
And, yes, we continually had to be on guard against ... falling in love.
And it was tough. Sandy and I have always liked each other – really liked each other – from the very beginning. And Sandy is eminently lovable. And she’s eminently fuckable, and with the fucking, well,...
But we’ve managed to keep our minds right and our obligations to Nate and Tara in front of us, and we always manage to approach that line without ever crossing it.
So I spend the first part of every Friday and Saturday night in bed – and sometimes elsewhere – with Sandy, doing ... well, doing everything, but always with me cumming in her in the place where it could ... might... will make a baby.
And every Friday and Saturday night, after Sandy and I are finished with our lusty, riotous, baby-making sex, Sandy kisses me and hands me the two little pills and sends me upstairs to my “wife,” Tara, and she returns to the arms of the man who has been her mate for so many years.
And that brings me to the words that Tara said, to Sandy and me, one night as we were about to commence our baby-making duties.
Sandy and I were having sex, “the old fashioned way” – Sandy, lying on her back, her legs spread to welcome me – me, lying in between those sexy, soft, welcoming legs, my cock in her cunt, her arms around me as we fuck in the smooth rocking motion that we’ve become very good at over the past several months...
When something caught Sandy’s attention. A flick of her eyes told me I should look over toward the doorway.
And standing there was Tara. With her was Nate.
Also, they were holding hands. I guess that whatever this is, they’re in it together.
Sandy and I didn’t have to talk about it, or even look at each other.
We knew.
Her Nate and “my” Tara had every right to ask for this. Despite how much fun Sandy and I have when we’re in bed together – and believe me, we do have fun – the fact is, we’re not there for the purpose of having fun. We’re there to accomplish a specific objective: for me to get Sandy, Nate’s wife, pregnant.
So, yes, Nate and Tara had a right to be with us, with Sandy and me, when we’re ... when we’re “together.”
And we knew why.
They weren’t angry – we’d all agreed on this ... this arrangement. We weren’t sneaking around, weren’t hiding anything.
And they weren’t jealous.
We know they weren’t. Because we knew how we would feel if the situation were reversed.
We’d feel left out.
And that’s what Tara and Nate were feeling – they were feeling left out.
And that can’t happen.
“Kyle, sweetheart – while you and I are in here having sex,” she smiled as she added, “really good sex – my husband and your wife are kind of left out in the cold. Kyle, darling, how would you feel about – what would you think if Tara and her dad were...,” she hesitated, like she was trying to find a gentle way of saying it, “like you and I are doing?”
Sandy turned her head toward Tara and Nate – her daughter and her husband – still standing there in the doorway, watching us. She patted the empty expanse of bed beside to us.
“Come, you two – join us.”
Tara and her dad looked at each other, a final “should we?” And then Tara reached for the waist of her dad’s slacks and started undoing the belt and zipper while Nate grasped the hem of his daughter’s T-shirt and lifted. Tara let go of Nate’s slacks and raised her arms so that he could pull the shirt off over her head. That left them standing there, with Nate looking at his daughter’s bare, beautiful young breasts before she kneeled to help him step out of his trousers. I guess they were eager to join us, and for the sake of... efficiency, I guess ... stripped off the rest of their clothes themselves. Then Nate took Tara’s hand, and together they walked to the bed.
They looked at each other again, and they seemed to reach some kind of agreement.
Tara went first. She crawled onto the bed and lay down on her back and relaxed her legs – and then held out her arms to her father, who climbed onto the bed and in between his daughter’s open legs, then lowered himself while Tara took his cock and guided him to – and then into – her pussy, saying “I love you, Dad.”
Nate replied, “I love you, Sweetheart.”
And then Tara said, “Fuck me, Dad, fuck your little girl like you really love her.”
And he did. They did.
And this really wasn’t new. After all, Tara and her dad had had sex – fucked – before, when Tara wanted to know what it felt like – to experience what her mother experienced – when Nate and I were DP’ing Sandy.
So, no, this wasn’t something completely new.
On the other hand, to do this Tara didn’t “need” her father like we needed a second man to accomplish double penetration on her.
No, this was Tara, simply wanting to experience sex with her father as her partner.
And under the circumstances – those “circumstances” being that every weekend night I am leaving her alone in order to have regular, frequent sex with her mother – I couldn’t begrudge Tara that.
So Sandy and I watched her daughter and her husband fuck like they really love each other.
That’s when Sandy said, “Fuck me like that, Kyle – fuck me like you really lo...” and then she caught herself. “Fuck me like that, Kyle.”
She reached out her hand toward her daughter and Tara reached over and took Sandy’s hand, and like that, with my “wife”--Sandy’s daughter, and her father--Sandy’s husband, two feet away from us, Sandy and I fucked like we ... . we fucked “like that.”
And for some strange reason, I had this thought:
“This could be it – this could be the night that Sandy gets pregnant.”
And, no, Sandy and Tara have not forgotten, and every now and then one – or both – will want to experience that special feeling – the feeling of having two men inside of them.
This time, it’s Sandy who’s craving that “special feeling.” Or maybe more accurately, those special feelings!
She started by asking, “Tara, Sweetheart, would it be alright, just for tonight, if I could have both of our lovely, sexy men?” Then she added, although it wasn’t necessary, “Next time, it’ll be your turn – promise.”
She guided Nate down and onto his back, his cock already sticking straight up from his muscular thighs. His wife – his insanely hot wife – lowered herself onto him, and in three moves she had that hard cock completely buried inside her asshole. Remember that until she’s pregnant, Nate can’t cum in Sandy’s cunt. And you know that Nate is going to cum!
And so with Nate on his back and Sandy lying back on top of him with his cock up her ass, it was for me to lie on top, facing her – fucking her.
And Tara right there next to us, a ringside seat to watching her mother getting fucked by “their” two men.
Until Sandy turned her head toward Tara and said, “Tara, honey, I’ll bet that Kyle would like it if you gave him a little extra stimulation...,” she looked at me and smiled, “Not that he needs any more, the nasty boy,” and gave me a little play-slap.
I can’t help it – I do love Sandy.
“You know that girls aren’t the only ones who enjoy getting their...,” and I could tell that Sandy was searching for the word that would communicate what she meant but wasn’t so ... crude ... that it would turn her daughter off, “ ... their bottoms ... played with.” Then, “See that tube of lube there on the bed stand – yes, that one.”
Then she started to give Tara directions – or, perhaps, instructions.
“Tara, honey, why don’t you put some of that lubricant – maybe a lot of lubricant – on your fingers and ... put them between your man’s beautiful ... ass cheeks, and I felt as Tara’s hand brushed against the light hairs on my butt and approached my ... crack.
I felt Tara’s hand hesitate, and that’s when Sandy instructed her, “That’s it, Sweetheart, apply a nice layer of that slippery lube to that cute wrinkled little butthole of his ... yes, like that,” as I felt Tara’s cool, slick fingers touch “my cute, wrinkled little butthole.”
And, yes, the touch felt good.
It felt even better as Tara’s slim fingers began sliding around, working the slick gel around, and then into, my ass, slowly, cautiously at first, but then more forcefully, more “assertively.
“That’s it, Darling – he’s liking it – I can see it in his face,” and then she smiled, “And I can also feel it in the way he’s fucking me.” She closed her eyes and strained against me, like she was trying to feel through my cock what Tara’s long fingers were doing to me.
Tara and i’ve done this before. But this is different, because right now my cock is buried deep inside the cunt of another woman. Before, Tara might finger my ass while I’m fucking her – which I really like, and when I cum, it seems to go on forever. Or sometimes she’ll basically finger-fuck my ass, usually when she’s sucking me, but not always. And she likes it because she says that when we do it that way, that I cum really hard – by which she mean, I cum lots.
But now, this time, Tara seems to be getting into it, in a way she never has before. This time, she’s doing “it” – finger-fucking my ass – with a “ferocity” like she’s never demonstrated before. I don’t know if she’s doing it to give me more intense stimulation, or if it’s to get me to fuck Sandy even more and cum even harder.
Which I did. Like I’ve never cum before.
And I wonder how long it will before I cum like this again.
The next time it was Tara.
Once she’d had a taste of “that special feeling” of having two men inside her at the same time it seemed like she could scarcely wait to feel it again. Sandy took over directing her daughter’s DP experience. She decided that this time the best way would be for me to lay on my back and then Tara would sit on me, backward, and lower herself – her ass – onto me, onto my cock. Then, with my cock in her ass, Nate would get on top of her and fuck her missionary style (assuming, that is, that there’s a second missionary fucking her ass).
It turns out that Sandy had a particular reason for arranging the “event” this way.
Nate kneeled in between Tara’s legs, as Sandy had directed. And I’m sure he was able to see my cock in his daughter’s asshole. Even though he knew that Tara and I did this, that we did – do – have anal sex (and from what Sandy said about the sounds they could hear from out bedroom, when and how often we have anal sex), I wondered how he felt now, actually seeing a man’s cock in his precious daughter’s rectum.
However he felt, he wasn’t taking time to think about it. He moved in between Tara’s open legs and put his cock right up against the sweet pussy that I know so well.
“Ready, Princess.”
“You don’t know how ready, Daddy!”
Yeah, I guess Tara has waited long enough to get that “special feeling” again.
Her dad pressed his hips into to her, and through the thin membrane separating Tara’s hot rectum from her cunt I can feel every inch of Nate’s cock as he invades his daughter. And as I’m lying there I’m picturing it. I can almost see Nate’s grown-man cock sliding into Tara, and my cock in her ass, pressing against that thin elastic tissue that separates us, and I’m trying to imagine what it feels like to Tara, to have two swollen dicks rubbing, pressing against each other inside her, filling her inside more than she’s ever been filled...
And now I realize why Sandy wanted us the way we are. Because in this position, with Tara on her back, facing up, she is able to see what her mother is doing. And so can I. And what we see is that Sandy has somehow grown a big black cock, which is now sticking out erect and threatening from between her legs.
Tara and I watch as Sandy lubes up the strap-on dildo, and then we watch – Tara watches – Sandy as she works a ton of lubricant into Nate’s ass – just like Sandy had Tara do to me, to my ass, when I was fucking Sandy. She’s doing it in a way that has her husband moaning in pain – but also working his ass like he’s trying to get more and more of her hand inside of him.
When Nate started to make sounds like he was going to cum, Sandy backed her hand out of him with a final twist, then moved in closer behind him, to his hips that are plunging in and out of his – their – daughter. She moved in close behind Nate and she steadied herself. And Tara and I can see Sandy as she placed the tip of “her” cock against her husband’s gaped-open asshole. She grimaced as she pressed her cock into her husband’s dreading, eager asshole.
And Tara and I get to watch Sandy’s expressions while she fucks her husband in the ass, and to see – and feel – Nate reacting, as he takes his wife’s “cock” up his ass – again, and again, and again.
So now there are four of us – Sandy, fucking her husband’s ass while he’s fucking their daughter while she’s lying on her back with my cock buried in her ass. In my entire life I never imagined that I would ever find myself in a situation so... pornographic – and so out-and-out raw!
And so insanely exciting!
Fortunately, Nate is strong enough to keep his weight – and Sandy’s – from pressing down on Tara and me. And that made it possible for me to fuck Tara’s ass – and for her to fuck me back. Just like we’ve done so many times before from this position. And it’s just as thrilling as always.
I think Tara came first, under the dual stimulation of Nate’s and my cocks. Nate managed to hold himself back long enough to make sure that Tara came before he lost control and came into his daughter.
And Sandy came. The excitement of the whole situation plus the pressure of the dildo against her clit and the sensation from her “apparatus” as she felt the resistance of Nate’s ass each time she forced her “cock” into him and feel his ass cling to her every time she pulled out were enough to make her orgasm.
Sandy was the first to come down from her orgasm. She carefully, lovingly, withdrew her cock from her husband’s stretched, relaxed ass, still dripping from all the lube she put in him. That let Nate back out of his daughter. Saying “I love you, Princess,” he kissed Tara on the tip of her nose and carefully raised himself off her, leaving Tara there, lying back on me, my arms holding her, one of her arms thrown back, holding my head, stroking my hair.
I kissed Sandy and Tara kissed her mom and dad. I took her hand, and like that we walked upstairs, to our room.
When we got to our room, Tara turned to me and we held each other.
“I love you, Kyle.”
“I love you, Tara.”
“We’re very lucky, aren’t we, Kyle?”
“Yes, Tara – we’re very lucky.”
We were both too physically and emotionally drained to do much more. Instead, together we turned down the covers, turned out the lights, and slipped into bed. We both fell asleep almost immediately, even thought it wasn’t even ten o’clock yet.
Sometime during the night I felt something around my middle. As I woke a little more I realized that the “something” was Tara’s long fingers. They were playing with my cock. Nothing intense, just a little. Butterfly touches, little flutters on the tip – and then lower. Lower, in fact, to the point where those butterfly fingers started fluttering around the base of my scrotum. Or more precisely, at that expanse between my ballsack and my asshole.
Then those fingers ceased being “butterflies” and began to press, gently, at first, then more firmly, and then very firmly against that place. And I was surprised to find that the pressure, which sometimes reached the point of pain, had another effect that I wouldn’t have expected.
Because what Tara’s fingerings were doing was make my asshole... tingle. Yes, my asshole was getting “aroused.” And it wanted something more.
And Tara’s fingers provided it. She touched me there, my asshole, and I immediately recognized the cool feel of the lubricant get that we use when we ... and the same gel that Tara used last week to provide me with more “stimulation” while I was DP’ing Sandy, along with Nate.
And, yes, the same gel lube that Sandy used earlier tonight to grease up her artificial cock and fuck her husband in the ass.
I thought, okay, I wouldn’t mind a little asshole action now. I mean, I’m still excited from the hot foursome of a few hours ago, and what Tara’s fingers are doing to me now feel real good.
And that’s what she was doing – she’d moved from rubbing her finger around the wrinkly flesh of my anus to actually reaming me, sliding her long finger in and out of my ass just like she was fucking me...
Holy shit!
Like she was fucking me.
And after this evening, and seeing her mother in action on her father’s ass, she knows that now it doesn’t have to be “as if” any more!
There was a dim light in the room. That was unusual, because we usually don’t use a nightlight. I guess tonight Tara had turned it on for some reason or another.
I realized part of that reason when I saw Tara. Because backlit in the soft glow of the nightlight I could her – and see the hard black cock that stuck straight out from her “pussy.” And I knew then that I was going to be experiencing the same thing that Nate experienced – and, apparently, enjoyed – only a few hours ago downstairs.
“Get on your back, Baby.”
I rolled onto my back, fearful ... and curious. And excited.
She guided me onto my back and then nudged me under my thighs, and I knew that meant I should pull my legs back, knees toward my chest. She reached over to the bedside table for the ever-present tube of lube and squeezed another generous glob onto her finger – her fingers.
“Relax, Darling.”
I relaxed. Sort of.
I trust Tara. But I wasn’t sure how ready I was for this.
On the other hand, I wasn’t sure if Tara was any more ready, that first time when she and I...
The creamy gel was cold when it touched my anus, but then as Tara spread it around the shock diminished, and I hate to admit it, but Tara’s long slim finger felt good as she worked it around, then in, my relaxing asshole.
Then a second slim finger joined the first, and it felt good, too. Tara seemed to know this because she smiled as she worked the two fingers in and around – and then in and out – of my ass.
But I knew what was coming. I saw Tara squirt the lube on three of her fingers, and I knew that there was no way that that third finger wasn’t going to find it’s way into my ass.
My anus strained to admit that third finger inside me. She paused for a few seconds to let me get used to the feeling – and the fact – that my asshole was now good and stretched.
But what surprised me was – the “stretching” felt good. Like when you stretch your muscles when you get up in the morning. The stretching actually hurts, but it hurts “in a good way,” if you get what I’m trying to say.
And that’s what this was like. Tara’s three fingers were straining my ass in a way it’s never been stretched before. But I was starting to like the stretched feeling, and I wondered – how would it feel to be stretched even more...?
Then she took her three bunched fingers and began working them farther into me, corkscrewing them around inside me, stretching my ass even further...
And getting me ready for...
With a final twist she removed her bunched fingers and put one hand on the bed beside me to support her weight, and with her other hand she took the cock that was sticking out of her crotch and placed it – seated it – against my asshole. She leaned down, and she kissed me – one of her “best kiss in the world” kisses.
“I love you, Kyle.”
And then she pressed her hips, and three inches of “her” cock slipped into my asshole that she had so lovingly prepared.
I love you, too, Tara...
And the next three inches of my wife’s cock penetrated into my ass.
And my wife fucked me. Not brutally – but not exactly gently and lovingly, either, but she fucked me – fucked her man in the ass – with her big ... hard ... cock...
And it hurt.
At first I thought she was going to tear me open. Literally. I didn’t know how I could take it.
And then I remembered: This is probably what Tara felt the first time ... the first time we ... alright, the first time I fucked her in the ass.
And how that first time, she took it, for me. And how if Tara’s slim body could take my cock – and she didn’t complain – then I could certainly do the same.
And how it wasn’t too long before she began to like it – really like it.
And I wondered how long it would be before I began to like it – really like it.
The weekend was just beginning. It was Friday evening, and as usual we were all sitting around the dining room table enjoying yet another one of Sandy’s amazing dinners. Tonight it was baked walleye – a favorite of all of ours, and Sandy makes it a point to get it whenever it’s available – along with some roasted vegetables – cut-up broccoli, yellow squash, and red bell peppers – that tasted great in the buttery juices from the fish.