The Boss's Daughter - Cover

The Boss's Daughter

Copyright© 2025 by cv andrews

Chapter 2: Loving Tara

Erotica Sex Story: Chapter 2: Loving 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   First   Oral Sex  

When Nate and I got back from Donut Dungeon and Sandy had everything set out for breakfast. She took the bag of donuts from me and gave Nate a quick “thank you” kiss and then put the donuts on a plate and set it out on the table.

And they were really good donuts – worth the special trip.

And it was just a really normal breakfast at a girlfriend’s parents’ house (Girlfriend? I guess that’s something I need to think about – fast), except, of course, for the part where I spent the night having sex with their just-15 daughter in her bed in their house.

After we finished and got the table cleared Sandy says “It looks like it’s going to be a really nice day. Why don’t you two go and take a walk in Lindberg Gardens.”

That sounded like a good – great – idea, especially in light of what’s happened – the several things that have happened in the last 15 hours.

We got in my car and drove to Lindberg Gardens and parked. We held hands and walked and didn’t talk much until Tara said, “Let’s sit down somewhere and talk, OK, Kyle?” We went to across the street from the park to Caffeine Connection and got a couple of the “daily brews,” and they weren’t crowded so we found table by the window and sat down. To talk.

Tara spoke first, like this was a talk that she wanted to have.

“So ... I guess you and my dad talked about some things when you were out getting donuts, huh?”

I wasn’t sure how much I should reveal, or else maybe I’d gotten things completely wrong, so I just replied, “Yeah, your dad and I talked about some stuff, and...”

Before I could say anything more Tara kind of took over, so that I got the impression that she wanted to control the direction of this conversation, at least at first.

“So I guess Dad told you about ... about how I feel, huh?”

I was about to say something, maybe to tell her that she didn’t have to explain anything to me, but then something in the way she looked at me told me to let her say her story, her way. So instead, I just nodded, just to let her know that, yes, her dad had told me some things.

“One day when I was ten I was at Dad’s plant, and we were meeting up to go to...,” and she laughed. “It’s funny – as important as that day was to me and as clearly as I remember... everything ... about it, I can’t remember where Dad and I were supposed to go – isn’t that funny?”

When she was ten? Like, four years ago? Four years ago I was in college and saw this sign on a bulletin board that HydroTech – that’s the name of Nate’s company – was looking for summer help, so that’s why I was even there.

“Anyhow, I was sitting in the small reception area and the receptionist then – Jan? – was on break or something so I was sitting there alone and you walked by and saw me and you stopped and asked if you could help me and I said no thanks, that I was just waiting for someone.

“But the way you did it – you talked to me like a was a real person. You didn’t use that stupid voice that grownups use when they’re talking to a kid – you just talked to me like ... like I was another person. And you’ve got no idea what a big thing that is to a ten-year-old, to be spoken to respectfully, like ... like a real person.

“And you didn’t ask me who I was waiting for – I didn’t say, and it was like you thought that if I had wanted you to know who I was waiting for, that I would have told you. Again, it was like you respected me instead of treating me like a child who needed to explain herself to you. Also, I thought that if you knew I was the owner’s daughter that you’d make some kind of fuss and act weird and stuff.

“Instead, you just said OK and walked away, but then you came back a few minutes later and handed me one of those little bottles of water and said you thought I might like this, and like before, you didn’t try to pry or anything. And I said thank you and you walked away.

“After that, I could see you through the glass windows outside the office area and I watched you talk on the phone, and how you’d smile and laugh and seemed to be enjoying the conversation but then you’d quickly get serious and get down to business. And I watched you with the other people in the office, and then I saw you go into my dad’s office and I could see when you were talking, and the way you were, with the man who’s your boss, and how you seemed to respect him but also that you seemed to like him.

“And I know my dad, and I could tell something else – that he liked you. Not just that he thought you were a good employee, but that he liked you. My dad’s a nice guy,” and then she smiled, like thinking to herself, “A real nice guy, and he gets along great with people – maybe that’s why his company’s doing so well – but I can tell when he really likes someone, and that’s what I saw when he was talking to you.”

Tara stopped, maybe to catch her breath, and also to give me time to absorb what she just told me.

“And that’s when I decided that you were someone special...”

How do you react, when a girl – a young woman – like Tara, who’s obviously smart but also pretty mature says that she thinks you’re “someone special?”

“And also, maybe, that you were kinda cute...”

So, basically, what she’s just told me is what her dad, Nate, clued me in to on the drive to Donut Dungeon – that Tara is in love with me, maybe since that day four years ago, when she was ten and saw me in her dad’s office...

What the heck to I do??

~ ~ ~

I know. You’re asking, “What kind of 23-year-old guy – at least one without serious psychological problems – would allow himself to get involved with a (barely!) 15-year-old girl?”

Well, I’m a normal guy. And I’m not desperate – I get a fair number of dates, with girls who are appealing and attractive.

No. It’s Tara who’s not “normal” – not an average 15-year-old girl.

She’s smart, really smart. But more than school-smart – she’s smart about... things. She knows a lot more about herself than other 15-year-old girls – and better than every teenage boy! And for the things she doesn’t understand on her own she has a strong, close relationship with an exceptional mother.

And she’s pretty – sometimes, like last night, even beautiful. And she’s good company, and I like being with her.

And she has the support of a very loving, very solid, mom and dad...

And she thinks I’m special...

And if she was only four – maybe even just three – years older and I didn’t want to be with her you’d be asking – I’d be asking myself – what the hell’s wrong with me!

But she isn’t. It’s right now, and I’m 23, and she’s my boss’s daughter, and she’s 15.

~ ~ ~

We had lunch at a taco place near the park and the coffee shop. When we got back to Tara’s house we had the usual conversation: “Did you have a nice time?” “Did you end up going to the park?” “Yes, then we went for coffee, and then we decided we wanted tacos.” “Yeah, we had a good time.”

It was assumed I’d stay for dinner. Nate ordered out for pizza – Gennaro’s again – and Sandy made a salad and some buttered and herbed French bread (but not garlic bread!). Nate got out some Peroni’s for himself and Sandy and me and made a polite offer to Tara but she said no, she’d just have a Fresca (I didn’t even know they still made that stuff).

And as dinner was winding down, Nate, and especially Sandy, made it clear that I’m welcome to stay tonight – Saturday night – “ ... if that’s what both you and Tara want.”

I looked at Tara. Eyes met, the little nod. Yes, we do. Both of us.

We all went down to the TV room and watched a one-hour sit-com, but then Tara stood up and took my hand and told her folks, “Kyle and I are gonna go up to my room now – G’nite.” She let go of my hand long enough to go and kiss her mom and her dad, then came back and she and I went upstairs.

When we reached the landing I looked back downstairs. Sandy and Nate were doing their best to not smile.

~ ~ ~

We got upstairs and Tara led me into her bedroom, and she turned around and she put her arms around me, and we kissed. And it was maybe the best kiss anyone’s ever gotten in the history of the world.

The kiss of a young girl who’s waited over four years to give that kiss to one particular boy.

Tara closed the door, gently, like there’s no need to make a big deal about it – that we’re safe and no one is going to interrupt us – and took the hem of my pullover (yeah, the same “nice” burgundy pullover that I wore over here last night for Sandy’s “nice dinner”) and eased it up my body and over my head. And I patiently unbuttoned the nice lavender oxford shirt she’d put on this morning and draped it over the back of her desk chair...

And then both of us gave up pretending to be restrained and got our own clothes off as fast as we could and grabbed each other and started kissing and twisting and squirming and just wanting the new thrill of feeling each other’s bodies against ours.

I guided – alright, practically shoved – Tara back onto the bed and immediately slid down her body and between her slim legs. I slipped my arms under her legs and started to lift but before I could Tara pulled them back farther than I ever would and put her hands beside my head and pulled me into her.

I wanted to kiss her so bad. And the best, most personal, most – important – kiss was her pussy. The first thing I did was to bury my face in the soft, wet, slick flesh there. I just wanted more and more contact with this place, turning my head left and right, and up and down, and then more.

I’ve “eaten” women – and girls – before, of course, and generally pretty successfully. I’m always able to make them cum – several times, if that’s the goal – or to get them good and wound up for THE MAIN EVENT.

This is different. This time I want to drown myself in Tara, in her sex. I want to be as close to her as physically possible. Yes, I wanted to bury myself in Tara’s pussy. Not a figure of speech – I wanted to blend – to merge myself into her.

Tara liked – loved? - what I was doing.

But she wanted to cum.

Oh, fuck, Ky...

And then she realized what she’d said, and she was obviously so embarrassed.

“Oh, Kyle, I’m so sorry – I never intended ... I wouldn’t ever want...”

And that did it. I’m in love – I’m captivated, enamored, totally enchanted.

“Say anything you want, Tara, I’ll love anything you say.”

“Oh, darn, Kyle – oh ... oh... good...”

This is definitely the sweetest pussy-eating experience I’ve ever had...

And she came.

And unlike yesterday, this was one hip-jerking, leg-thrashing explosion.

“Oh, fuck, Kyle – oh shit, oh god! – Kyle, don’t let it stop!”

So I kept my head in her, my lips around her little clitoris, sucking – gently, because I knew she’d be super-sensitive right now – and running my tongue over her.

Her seizure finally ended and she settled down onto the mattress and relaxed her grip on my head. And that let me rest my cheek against her, against the soft, wet flesh. And just perfectly, Tara rested one hand on my shoulder, then put her other hand on my head, and she toyed with my hair.

“Kyle?”

“Yes, Tara.”

“Can we do that again?”

OK, now I have to add “charmed” to the list.

Yes, my precious Tara, we can do that again.

This time a little less frantically – take a little more time to enjoy the ride.

I turned my head, and this time I started with my tongue, just licking every place that I could reach, first the creases where her legs join her body, and then through the middle of her pussy, then tracing the folds between the delicate petals of young flesh, then, of course, licking, then probing her inside, and then up to her clit, licking up, then down, then across. Then putting my lips all around, sucking gently, then exploring more with my tongue.

Tara had her legs pulled back – I think she discovered that that way I could get more places and make her feel good more ways – and my tongue slid down and across her asshole, and she didn’t seem to mind so I did it again – and again, and again, until she finally said, “You’re licking my butthole, aren’t you?” and I said yes, and she said, “Do you like doing that, licking me there?” and I said yes, and she said, “That’s good.”

I slid my tongue back up from its place around her little starfish and started licking her pussy again. I licked around but got the feeling that she was really wanting to cum again so I zeroed in on her clit. I ran my tongue up and swirled it around and put my lips around it again and sucked...

And she came. Not as violently as the first time, but still, maybe three big hip thrusts and a few little aftershocks...

And without any rest this time she took me under my arms and guided me up her body, in the position to...

... and there on the pillow was the one condom pack that we didn’t use last night...

plus another strip of three more condoms.

I picked up the new strip and held it for Tara to see, and I could almost see the “Oh, Goody!” in her eyes.

And I thought: One day ago this girl was the quietly-pretty, smart, fun daughter of my employer. Now I can’t picture a future for me that Tara isn’t in.

She took the loose packet from the pillow and tore it open and took out the rubber but then she wasn’t sure what to do with it. I gently took it from her, and intending to put it on, I rolled over onto my back, my erection proudly sticking straight up. But maybe also looking kind of silly...

And Tara’s eyes landed on it and she got this look of sheer delight. She rolled over and took it between her thumb and two fingers and held it for inspection. She looked at it from l different angles, then bent it one way and examined it, and then the other way and examined it from that angle, then backed her head away to examine it from that distance ... and then leaned forward and planted a big smooch right on the tip and then said, “Hurry up – put it on!”

Initially I thought this could be the opportunity to show Tara “how it’s done,” just in case an adventurous girl like her might want to some time. But her command to “Hurry up!” told me to ... hurry up! I finally got the darned thing securely over my cock and I rolled onto my hands and knees over Tara.

I thought maybe it would be good to slow things down a bit. I mean, this would only be Tara’s third time (to my knowledge, not counting her “practice” sessions with ... with whatever) and I thought I don’t want to just make her cum – I want the whole experience to be pleasurable for her ... and fun.

I lowered myself so I could kiss her and was rewarded by the feel of her long, soft arms around me. I lowered myself ‘til my body touched hers, and we lay there like that, touching, until Tara said, not frantically, but decisively, “Now, Kyle – I want it inside me now.

I scooted down enough that I could get myself in place between her legs. She opened them for me and I put her hand on my cock and she kind of got the idea that she should put me in the right place and help guide me into her. As soon as I felt the tip of my cock nestled at the opening of her pussy (as much as I could feel through the rubber, anyway) I pressed with my hips and slid half the way into her.

And then I felt her hands gripping my hips and stopping me there.

“What? Is something wrong?” I was really concerned. Like I said, I wanted this time – I want all the times – to be good for Tara.

She smiled, that happy smile she has.

“No – it’s just right – I just want to enjoy it like this for a minute.

“Then you can fuck me for real.”

Fuck her. I can fuck Tara “for real!”

What guy doesn’t want to hear those words!

“Kyle...” I felt her grip loosen on my hips.

“Yes?”

“Kyle – it’s okay now...”

So I pressed my hips into her again and this time I didn’t stop until I was almost all the way inside her. I held back just a little – just in case...

I stayed like that, making sure things were still “okay.” When I felt Tara’s arms loosen, I think that was my cue that I should start moving.

I did it slow ... and loving. I pulled out, slowly and steadily, trying to enjoy every millimeter of contact, and having no idea how it felt to Tara but hoping that it felt ... good.

And without any trouble she and I fell into a nice, rocking rhythm – just plain old-fashioned in and out, and I tried to focus on the sensations that were managing to get through to me through the rubber, and just loving the pressure, and the warmth – and Tara’s arms around me, and the little “mmm ... mmm ... mmmhh” happy-satisfied sounds that Tara was breathing into my ear.

I just had to stop, and to look into her eyes, and to kiss her, and to see her smile – and then go on fucking her.

I felt her fingernails start digging into my shoulder muscles and I could tell she was getting close, but I didn’t think she was experienced enough with her own body to get herself... over. I kept on fucking her, and her nails kept digging deeper into the muscles of my shoulders ... and I was surprised that their pain was making me harder and more excited...

And I came, and Tara knew it, even though she wasn’t able to feel my cum inside her...

And she held me tighter, and she whispered in my ear, “Kyle...?”

And I slid myself out of her and immediately went down between her legs and fastened my mouth to her and put my lips around her clit...

And I was right – running my tongue around her clit while I was suctioning it, and she came, and like earlier, it was a frantic, bucking climax, and “Oh, fuck, Kyle – that’s ... good!”

I scooted up the bed again until my head was even with hers, and we grabbed each other and we kissed and rocked each other back and forth, and kissed some more.

During the night we used two more of the condoms.

~ ~ ~

Yes, Tara and her mom and her dad asked if I’d like to come over next weekend. But we all already knew what the answer was.

~ ~ ~

We were in her bedroom that Friday night, and we were naked, in bed, and we were holding each other and kissing when Tara said, “I really, really want to feel you inside me, Kyle.”

“You do get to feel me, as often as we get the chance.” I was trying to keep things light and put a positive spin on it, but yes – I knew what she was talking about. And yes, I wanted to feel Tara inside.

“No, I mean I want to feel you cum inside me. I want to feel it when you cum – feel it hitting me inside my pussy, and feel the warmth. And I want you to feel it, too – feel how my pussy really feels, and not through some stupid piece of latex.

“I don’t want to take any chances, and Mom says I can’t be sure about the birth control pills for another month, but I really want...”

Huh? Birth control pills? When...?

Tara saw the question – questions – on my face.

“When I told Mom and Dad that what I wanted for my birthday was for you to come, that was Mom’s birthday gift to me – getting me a prescription.

“But anyhow, Mom says that there’s a way that we can do it without a rubber that’s safe...”

Is she hinting at what I think she is?

“She says that a man and woman can have sex and there’s no risk of getting pregnant if they – if we...,” and now she stumbled for words. I wanted to help her out, but also, I didn’t want to be wrong and say something wrong.

“Kyle, Mom said that a man can put his thing ... his cock ... in a woman’s ... bottom...,” and then remembering that she already said it once, last week, when I was running my tongue across her anus, “ ... her butthole, and he can fuck her there, in her butthole, like he’s fucking her pussy, and that way the girl can’t get pregnant. And she said that it feels real good to the man, and that sometimes – actually usually – it hurts – the woman, I mean – at first, but that once she gets used to it it feels great for the woman, too.”

And she stopped and waited, like she was waiting for some response from me, like had I heard of it, and had I done it before, and was it true, that this was a way that couple could keep from getting pregnant? Or did I maybe think it was disgusting?

First, I couldn’t believe that a 15-year-old girl as smart and as sharp as Tara could actually be that ... ignorant, or naive, about anal sex. Or is she just trying to make me feel good, pretending that she “didn’t know about that kind of thing.” I guess I could have been angry that she’d try to trick me like that. But I also thought, hey, that if she’s pretending, at least she’s doing it to try to be considerate of me and let me be the more knowledgeable, more experienced one.

I thought it would be best if I’m honest with her, but try to do it – gently.

“Yeah, I heard of it, and yeah, I have done it, and yes, it does feel real good. And if we...” – we – “do it slow and careful, then it won’t be long before it feels real good for you, too,” and I watched to see her reaction to what I told her – and how I had told her.

And she smiled. Apparently that’s exactly what she wanted to hear, the way she wanted to hear it.

“I’m glad, Kyle,...

“Because Mom said that if we wanted to do it we should be sure to use this, and that we should use lots of it,” and she reached over to the bedside table and picked up a blue squeeze tube that I hadn’t seen before. I couldn’t see the name but I knew immediately that Tara’s amazing mother was looking our for her daughter – and her daughter’s boyfriend!

I figured the best way to start was with something we’ve already done before. Tara was already lying on her back, so it was natural for me to slide down in the bed and in between her legs (have I mentioned how lovely and smooth Tara’s long legs are?) and Tara automatically spread and lifted them a little, so I indulged myself in loving her adorable pussy for a while, because I’m going to be neglecting it for a while.

Because after I gave her sweet pussy the loving attention that is deserves I edged my shoulders under her thighs and gave a nudge, and Tara knew that was the cue to pull her legs farther back, raising her pelvis – and making her cute little butthole available and accessible to my tongue.

We’ve done this before, and Tara likes it when we – when I – do it. I don’t know if it really feels that sexy to her, or if she just loves the Idea that I love her so much that I’ll put my tongue on her there. But anyway, she likes when I do it, and she doesn’t think it’s gross.

So I licked and explored and prodded, and I was getting the little head-trip I always do, thinking about what I’m doing – and where I’m doing it. But this time we’re going to do something more – something we’ve never done before. And that’s why I stretched and reached out to the bedside table and grabbed the blue squeeze tube of lubricant and fiddled the flip-tip and squeezed a blob onto my middle finger, and then I thought to warn Tara, “This might be cold.”

She was pretty well relaxed from all the licking and tongue stuff I did so my finger went in pretty easy. I had to press, but she was relaxed and wasn’t all tensed up or anything so I slid my finger in and out, basically “fucking” her with my finger, but slowly and smoothly, not rough.

And she seemed to like it, and she even made a sound, like a gentle “mmmm,” and I thought that this was good – if she likes the feeling of my large finger sliding in and out of her asshole then there’s a good chance she’ll like the feeling of a cock – if she’s prepared right.

I slowly withdrew my finger all the way. Then I put my two fingers together and squirted more of the lube onto the two fingers. I thought that this time I should ask.

“Ready?”

Mmmm-hmmm...”

So I squeezed my fingertips together and gently twisted them, kind of like corkscrewing or worming them through the tight sphincter in into her ... insides. I stopped, to let her get used to being stretched like this...

“More...”

Did I hear that – did Tara just ask for more? More of what I was doing?

Or more fingers?”

She was so relaxed, I went for more fingers. I pulled the two fingers most of the way out and sneaked a third finger in with the first two. She was already pretty slippery with lube so I started the corkscrewing motion again, and it didn’t take long to get all three fingers in as far as my hand would allow, and it looked like Tara’s asshole was stretched about as wide as my cock (maybe a little more).

“Are you ready ... Tara?”

Mmmm-hmmm...” And I guess she didn’t want any doubt so she added, “Yes, I’m ready.” And then, “Put it in, Kyle.” And I’m thinking, are there any more loving words than those?

I eased my bunched fingers out of her ass and rolled her over onto her side and kind of spooned-in behind her. My fingers were already pretty slick from the lube and Tara’s asshole was already well lubricated, from the lube, but also from the natural secretions that her ass seemed to be producing. But I didn’t want to take any chances so I grabbed the plastic tube that I’d left on the edge of the bed and squirted a bunch on my cock and spread it around, especially over the tip and the crown.

“Tara...” Honey? Sweetheart? Darling? What’s the right term of endearment for a woman you’re about to fuck in the ass for the first time?

“Tara, lift your leg – the one on top – bend the knee up toward you. I think that’ll relax ... relax you inside, your muscles, so I’ll be able to go in more easily.”

She did, and when she stopped moving I wiggled the last bit in against her and put my cock against her anus and pushed, just enough that my cock was snug and firm against her ... anua. I felt the tender flesh give way, just a little. I was about to ask her one more time, just to make absolutely sure...

“I’m ready, Kyle, put it in.”

So I held my arms around her and I whispered, “I love you, Tara,” and she made that mmmm-hmmm sound again ...

And so I pushed. More pressed, really, and I had prepared her asshole so carefully and she was so ready that the head of my cock slid into her ass. It didn’t “pop” through her sphincter – it just slid in from the pressure I was giving it, she was that relaxed. I thought that if she did experience any pain, that it wasn’t real bad and that she’d feel better quickly.

“Wait.”

So I stopped and waited.

“Does it hurt?” I was so scared what her answer might be.

“Yes ... no ... both. It’s stretching my ... my... ring, and it hurts – stings. But also, it hurts kind of good, like when I stretch real hard and my muscles are stretched.

“But it isn’t hurting so much now – in fact, it’s getting better now. So...

“You can do it some more, Kyle – put it in farther if you want.”

If I want to!!

So I started easing my cock deeper inside her and she didn’t complain or make any “pain noises.” And all of a sudden I was all the way inside her – my pelvis was mashed up against her ass, just as tight as I could get.

“Are you alright, Hon?” There, I said it! Hon.

She made that mmmm-hmmm again.

“Perfect,” and she put her arm around behind her and around my neck, and she ran her hand through my hair.

I gave her a minute or two to get used to having a cock all the way up her insides. Then I began moving again, and now that I knew everything was okay for Tara I could start thinking about how it felt to me.

And it felt wonderful.

For the first time, without the condom, and to feel the ... the velvet lining of Tara’s ass, and the amazing pressure – the full length of my cock held in that warm embrace of Tara’s warm – hot! - rectum. Nothing like it in the world.

For just a moment I forgot about Tara and let myself get lost in my own sensations – until I heard Tara’s voice.

“I’m doing it, Kyle! I’m feeling you – I’m feeling your skin and your flesh, without the dumb condom in between us!

“Kyle, it feels wonderful – you feel wonderful!

And, yes, I felt wonderful – Tara felt wonderful!

“Kyle? Can we do it faster? Can you do it more like when we do it the other way?”

She wants me to fuck her in the ass the way I do her pussy.

“Are you sure, Hon – are we ready to...?”

“I’m ready, Kyle – fuck me.”

So I did what Tara asked me to – I fucked her, fucked her ass like I do “the other way.”

I could feel it. But there was no way I could stay feeling this way for very long. I had to make sure that Tara experienced it too. I had to be sure to take Tara with me.

I reached down between her legs, and I wasn’t very “sensual” about it – I went straight for her clit.

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