One of my favorite thoughts is for her to meet her first bf on a longer work trip abroad.
They first fucked when she was 15, and they were together for a few years, but now she is 30.
They would go out for drinks and chat about old times. She would get wasted, and he would push the subject more and more toward how they fucked when they were young, and how fun it was. She would become more comfortable with talking about all the crazy things they tried as horny teens, while he would get closer and closer to her physically, like putting an arm around her, holding her hand, then putting his hand on her leg a bit later and gently caressing it.
Deep in the night, she would be very horny from her memories and deep in her drink. Enough so that he could convince her to go with him to his hotel room.
Once there, they would start making out as soon as he closed the doors, their tongues entwining while he led her to the bed.
While kissing her, he would tell her how much he had missed her, how amazing she looked right now, how hot her body had become, and how much he would like to see her naked.
In response to that, she would get up and drunkenly undress in front of him, while he does the same.
They would spend a moment taking each other in.
He would look at her curves, her now-matured body, just exuding an aura of being ready for breeding, her ass now big and round, her once super-tight pussy now a little more loose, but still glistening invitingly and clean-shaven, her tits now noticeably bigger and fuller.
His nice thick shaft already rock-hard for some time, now pointing directly at her.
And then the moment is broken as she falls on top of him and they resume making out while rolling naked in the sheets.
He's sucking on her firm tits, putting her entire puffy nipples in his mouth, then going down and eating her pussy and ass.
Back in the day, he had fucked all her holes bareback, depositing in her mouth and ass, and playing the pull-out game when in her cunt. She liked the feeling and they almost never used rubber.
She lets him please her for a good moment and then pulls him up, kisses him, and goes down to re-introduce herself to his cock, while all the memories of her sucking this man all those years ago come rushing back. She wraps her lips around his shaft and starts sucking eagerly, perhaps too eagerly as she goes for a deep throat and suddenly hears him groan and tense up, and a second later her mouth fills up in a familiar way with his hot semen. There is a lot of it, but she has had a lot of practice over the years, so she starts swallowing and manages it all.
She comes up for a kiss, and he smiles and says, "Just like the old days, huh?"
She blushes a bit.
However, they are not done, in fact, they go at it for most of the night. Licking, sucking, teasing.
Once he is hard again, he looks at her, and there is an unspoken understanding. She sucks his dick just enough to make it wet with her saliva and then spreads her legs. He quickly takes his place between them, and just like in the old days he lines himself up to her opening and starts pushing in. She has been ready to accommodate for some time now, so he easily slides his entire length in her hot wet cunt. She feels his balls pressing against her ass and the familiar sensation of fulfillment inside her. He fucks her gently at first but then increases the speed and force until he is gripping her by her hips, and furiously slamming his cock inside her, making their bodies clap loudly and her tits flop around wildly.
He fucks her good and long, she reaches out, hugs him, and pulls him in closer, she moans and squirms as pleasure takes over her body again and again. Then he slows down, and as she is still panting and half-lost in pleasure, looks her in the eyes and says, "You know, there was one hole of yours that I never got to fill. I have been dreaming about it ever since. Can I?"
She snaps out of it immediately, her eyes going wide. She looks at his panting face, right up against her, looking at her with such lust, she also feels his thick shaft embedded deep between her legs.
"Please, Alice! For old time's sake."
A thousand thoughts are running through her head. She is silent for what seems like an eternity, and then... she nods.
That is all he needs, as he picks up the pace again, now one goal in his mind.
She is moaning so sweetly yet again, when he suddenly grunts, tenses up, and she can feel his cock twitch inside her, and a second later, a wave of hot semen shoots out deep inside her.
She can't help but shudder as he keeps on releasing spurt after spurt of his seed - this feels so familiar and yet so different. She has taken loads in other holes, but he is the first man, other than her now-husband to cum inside her pussy.
As he finally removes himself from her, his cock leaves with a lewd squelching sound, and the next moment she feels his cum oozing out of her well-fucked pussy, running over her ass and then making a mess on the sheets.
They kiss again, holding each other, not bothering to go wash just yet.
Plus he is not yet done, if he has her here and she is so willing, he wants it all. The memories of how good her tight little asshole feels are embedded in his mind.
He keeps kissing her, playing with her, finger fucking her pussy, and now her ass as well, using the mess between her legs as a lubricant. She knows him well enough, she knows what he is going for. She used to take it up her ass quite a lot when she was younger, but now she does it very rarely, and she is quite tired already. However, she knows she will spend the night here, and if he can still manage another hard-on for her why deny him the pleasure of conquering her every hole now?
He is very good at preparing her for what's to come, and soon she can feel his cock stiffening and poking at her leg.
She just lazily turns her back to him and sticks her ass out, grinding it against his shaft.
With practiced moves, he spits on his cock, spreads her cheeks, aligns himself with her little pink starfish, and starts pushing in.
She grits her teeth and yelps a little when finally he breaks the tension and his tip pops inside her, followed quickly by his entire length.
One of her hands is on her breasts, squeezing and pinching, while the other is helping him keep her cheeks open. She is just lying there, taking it... enjoying it. It has been so long since he did this to her last.
He fucks her ass with as much enthusiasm if perhaps a little less power. This time he does not even ask her before filling her ass with cum.
As the last rope of cum shoots out deep in her ass, and he starts pulling out his already softening cock, he can't help but think that he has finally done it. He has finally filled all the holes of his very first girlfriend, and in one go nonetheless. Something he had regretted not doing ever since they broke up.
And even though she's married now, who knows? Seeing how willing she was, perhaps it's not the last time...