Plunder that ass.

You throw Tara's trembling body off your cock, and she collapses onto her face on the pillow, gasping for air.
"Oh my..o my g....oh...." her eyes are rolling wildly as she comes down. "That was... i need another rip after that..." She starts to rise, but you grip the back of her neck, picking up her haunches with your other hand so that she's "face down, ass up" as the kids say.
"I'm not done yet, little slut." your voice is flat, but with a hardness that sends a shiver through Tara's body. She looks at you sideways, as much as your grip allows.
"....yes, daddy."
"Where is Jared's lube, I know he has some." She reaches out feebly to the nightstand drawer. You pull it open to reveal several spent condom wrappers, a few unused condoms, and a bottle of Astroglide.
"You two use condoms?" You inquire as you grab the half full bottle.
"I'm...switching to a new pill...haven't filled it yet..." there's a thread of worry in her voice.
You chuckle evilly. Not going to matter with what you have planned. You pop the top and liberally coat her taint and asscrack with the slippery lube. A dripping puddle forms on the bedsheet.
As you rub your tip against that tight starfish, Tara whimpers.
"Oh...James, I've never...." you grip her neck tighter as you put pressure on her anal opening. Wow. A fresh, untapped asshole. Jenna had let her only other boyfriend before you take her ass, so this would technically be your first time deflowering a girl's butthole.
"Relax, little slut. If you tense up, it's going to be bad....for you. Not for me, you understand?" she nods emphatically, and you feel her attempting to relax her sphincter.

You spear your way inside with the help of the lube, and low pitched whine begins to drone from Tara's throat. "Ahhhhh......." You have the head all the way in, pushing past her o-ring and deeper into the spongy nethers of her ass. "Owww...."
"Does it hurt, baby girl?"
"Mmmhmm!!" she's got a mouthful of Jared's pillow in her teeth, and she's nodding.
"You want me to stop?" you will, you realize, if she asks. No sense in ruining a good thing.
".....no. It's ok. It feels...so strange. So....full." Her free hand rubs her pussy. "Just let me get used to your thickness, please daddy?"
You slowly pump, eliciting a groan from Tara every time you press a little deeper. She's such a trooper. She bites the pillow whenever it's bad, but eventually, her rear tunnel is actually squeezing you rhythmically, and she's starting to gyrate her hips and buck back against you when you retreat.
"I'm such a bad girl. Mom said only bad girls like it in their ass." she's halfway between whining and moaning.
"She's just never been fucked proper, sounds like to me." You pick up the pace. "Maybe when we're done here, I'll pay your momma a visit." No idea where this is coming from. You're just saying any vile thought that comes into your head.
"No...." she starts to protest. "I don't want to share...she can't have you, daddy!" She looks at you, her face still showing pain, but mixed with pure lust.
"I'll do what I like, little girl! If you don't want to share me, then you better be a good little fuck. Otherwise I'm going to take this thick cock and stick it in your mommy while you watch!" Who the fuck are you right now? You're a **** to your lizard brain. You can't stop.
In response, Tara takes a deep breath, and rams herself all the way down onto your cock.
"AHHHHHHHHHHHHHHHHHH!!! FUCKKKKKKKKKKKKKKKKKKKKKKK!" Her face is twisted with pain, but when her eyes open, they are filled with pure ecstasy. "FILL MY ASS, DADDY! I'll show you! I'm the only one who deserves this cock!"

That's going to do it. You can't stop yourself from filling her anal cavity with your spunk as you go balls deep against her ass. Tara surprises you by squirting her second orgasm, forming a large puddle on the bed. Your knees give out, and you fall onto the bed next to her. Her shivering, well-fucked body lies next to you. She's panting and groaning, rubbing her raw asshole with one hand.
"Ow...that's.....gonna take some getting used to....ah....." she gingerly gathers the cum leaking out of her butthole. Her hole is so fresh and tight that it has already snapped completely shut, trapping most of your cum inside. "I can feel it inside...so full." She rolls over to look into your eyes. "That was incredible, daddy."
"You too." It doesn't really make sense. "But...this is probably best kept to a one time thing, Tara. I can't fuck up my whole life, you get that, right?"
The disappointment on her face stings. Underneath the wanton sex kitten, there's a **** little girl. "Oh. Yeah, of....of course, Ja....Mr. Sinclair."
You take her cheek in your hand, making her look at you. "You were incredible, and I think there's more to you than just a good fuck, too. But I still love Jenna." It's not a lie. Your emotions are very confused right now. "You don't want to be a homewrecker, do you?"
Tara shakes her head, "No! But this was so good, and I love the way you take charge. Boys my age are so timid. I don't want to make trouble. I don't mind sharing you..." she traces a finger along your pecs, as she defies the words she had said moments ago while fucking. "Just please don't say 'never again'. Please?.....Daddy?"
How can you refuse that face? You pull her on top of you, kissing her lips and squeezing her tight. "Ok. We'll see. But for right now, we gotta clean up, and you can help me get this house ready for tonight, ok?"
She looks down into your face, and smiles like a girl who's made her daddy proud. "Of course daddy."
"Probably call me James, ok?"
"Yeah. you're right."
You clear your throat and push her off your lap, standing up to locate your towel.
"Time to get dressed and tidy up. You'll give me a hand getting this place ready?" It's closer to an instruction than a request. Tara is pulling on her tight black cotton thong over her heavenly rear end, and you watch with interest.
"Sure thing, James. I have to scoot out of here by 2:00, so I can go home and get ready for work, but that's plenty of time." You're staring at her in James's mirror as she pulls on a tight black v-neck t-shirt, and ties her hair up into a ponytail.
"Uh...yeah...it's a shame you won't be able to stick around...for dinner." You're still in a towel. Your shorts are in the bathroom.
"Alright then!" you clap your hands together and leave Jared's room.
What have you gotten yourself in to?
You spend the rest of the morning cleaning and tidying up, trying to return your headspace to normal. Tara helps, and then plops down on the couch to watch TV. When Jenna returns, you all help put away the groceries, and just as you finish that, twin car horns honk as they pull into your driveway.

(ACHIEVEMENT UNLOCKED! Broken Cherry: Took Tara's anal virginity before noon on the first day)