Over the years he's found himself in the beds of many women, but there's something different about the Bennett women. Perhaps it's because of their power; after all they are one of the oldest and most powerful witch lines in existence. Maybe it's the fact that they are all beautiful and he's always made a point of going after beautiful women. Or it could even be because he enjoys the danger of being with women that are technically supposed to be his enemy. Stefan doesn't know what it is about the Bennett women that draw him in, but he has never had a problem walking into the fire.
Emily ─ Mystic Falls, 1864
Emily is the first.
She's the first person he beds after he's turned and if he's really honest he can admit that she's the first woman he's slept with willingly. In his mind Katherine doesn't count because he had been compelled at the time.
It happens not long after he's turned.
He's covered with blood and she's telling him that he has a pure heart. He doesn't believe her, how could a monster like him have a pure heart? Yet when Emily decides to take him an old cabin to clean him up, he goes with her. She has him remove his bloody clothes and he's a bit surprised that she doesn't seem bothered by his nakedness. Instead she helps him clean the blood splatters from his body, not noticing his increasing arousal.
"You'll have to be more careful, Stefan." She says as she's cleaning off the blood from his face.
She's close enough that Stefan can smell the blood rushing through her veins, making all the more tempting and he decides he has to do something about it.
She's has just finished cleaning the blood from his face when he leans in and kisses her.
"Why did you do that?" She asks when he pulls back.
"I always wanted to know what it would be like to kiss you." He says simply.
Though she seems shocked by the answer, when he pulls her in again she kisses him back passionately. It grows until their bodies are tense with arousal and when he pulls back her eyes are begging him to make love to her. So he undresses her quickly and within seconds he's embedded inside of her.
It starts out slow, them on the floor of the one room cabin with only a blanket beneath her. Immediately he feels a change in the air and he's slightly startled when the candles start to flicker in the small room. He quickly realizes that she's using her magic, heightening the pleasure between them.
It sets him off and he feels his fangs extend and before he can stop himself, he's drinking from her. The taste of her blood is like nothing he's ever tasted before. It's as though her blood is mixed with the tastiest treats he had been fond of when he had still been human. She tastes so amazing that it makes the sex between them even more explosive and it's not long before he's spilling his undead seed into her womb.
He's slightly embarrassed that he finished before her, but Emily only laughs and points out that he has vampire stamina now. The words are barely out of her mouth before he's hardening inside of her. When she rolls him onto his back and starts to ride him like he's a stallion he's only too happy to let her.
Her head falls back she rides him, her normally pinned up hair spilling down her back, making him see her in slightly new light. She's breathtaking like this and he makes it his mission to push her over the edge so he can see just how breathtaking she'll be at that moment as well.
When she comes it's long and drawn out, her brown eyes are bright with arousal and something else he can't describe. It's like her magic has taken over for a brief moment and the thought of her letting all of that out pushes him over the edge as well.
After that night, they find every chance they can to be together and it's so great that he's actually happy with her. It's much different from his what he had with Katherine. Aside from the fact that it's completely his choice this time, he feels wild and free when it comes to expressing himself sexually. Underneath Emily's calm demeanor, there's a woman that is full of sensuality and he finds himself trying to experience as much of her as he can.
He loses track of the amount of places they fuck as well as the amount of her blood he drinks. It's the first time he drinks from a witch and he quickly finds himself addicted to the taste. It's unlike anything he's ever had before and years later when he's at the height of his addiction to blood; he'll realize that he's been trying to regain the euphoria he felt whenever he and Emily were together and she allowed him to drink from her.
The affair doesn't last long because just a few weeks later she's dead and he leaves town soon after. He doesn't think about it at the time, but now years later he suspects that the reason Katherine allowed Emily to be burned at the stake had partially been because of their affair.
He also doesn't admit it until much later that deep down the loss of Emily had been just one of the catalysts of him becoming the ripper.
Sheila ─ Mystic Falls, 1969
The world has changed a lot since the last time he was in Mystic Falls. Despite this when he returns to town, he finds that some things have stayed the same. There is still a lot of discrimination and hate within the town (and the country in general) and as a result many of the younger people stage protest rallies in an effort to change things.
One night he makes the decision to attend one of those rallies and that's when he first meets Sheila Bennett.
He hears her speaking at a protest rally for the Vietnam War and is mesmerized by her speech. She commands the crowd with her words, the sound of her voice, and her overall demeanor. It also doesn't hurt that she's a very beautiful woman.
After the rally is over, Stefan approaches her and finds that's Sheila is just as mesmerizing up close. He tells her how much he enjoyed her speech and asks when she'll be speaking again. She tells him and surprises him by changing the subject and revealing she knows about his past affair with Emily.
"I can see why Emily liked you." She smiles at him flirtatiously and asks him over for coffee.
They get to talking about witches and spells and he learns a lot of important things. Things that will stay with him forever and will eventually be useful when he's dealing with various messes throughout the years.
Talking to her is different than talking to Emily had been. Though it's been very easy to talk to them both, he finds that Sheila is more of a teacher than Emily had been. The one thing that had stayed the same is that overwhelming attraction he felt for Emily is just as overwhelming with Sheila.
Having more than a century of experience, Stefan's approach of Sheila is a lot different than it been hundred years ago with Emily. Instead laying an unexpected kiss on her, he's honest about what he wants.
"I hope this isn't forward, but I would really like to kiss you." He asks when he's getting ready to leave. She says okay and he presses a brief kiss to her lips.
Of course it leads to more and they end up spending the night together in her home. The next morning he cooks her breakfast and after another round of sex, she's off to another protest rally. He goes with her and it's the start of a three week fling.
They know going in that it's not serious so they have no problems finding time to fuck in between rallies and sit-ins, and picketing. There are a wide variety of things to protest and Sheila takes on many of them. While he's there he's attends rallies that deal with racial discrimination, gender inequality, the Vietnam War, and many other topics.
After her speeches Sheila is always charged up so he decides to take the edge off by devouring her lower lips with his mouth or fucking her in the backseat of his 1969 Camaro. It's easily the most fun he's had in a while.
At one point he even remembers them fucking while she came up with of her amazing speeches.
It's for another rally, this time it's to allow occult courses to be taken at Whitmore college and he has to admit he's a little miffed when she starts to utter out phrases while he while he moves deep inside of her. At least until she clenches her pussy around him in a way that makes his eyes roll in the back of his head and she floods his cock with her arousal. It's then that he realizes that she's just really good at multitasking and he continues trying to get her off.
Later that day when she gives the speech, she once again mesmerizes the crowd with her words, but all he can think about his the way her voice sounded earlier when she was coming up with the speech and he was having his way with her. It takes everything in him not to come right in his pants.
It's barely a week later when she meets the man who will become her husband at one of those rallies and Stefan can tell right away that the two of them will be something special. So when Sheila ends things, he's graceful about it despite the slight jealously he feels, knowing a vampire and witch ending up together is highly unlikely.
Still when he leaves Mystic Falls that day he's inspired and he moves to London for a little while so he can learn more about the supernatural.
Lucy ─ New York, 2007
He's spent the last ten years traveling across the world, not staying in once place for too long. It's different this time because he's no longer leaving a trail of bodies behind him like he had before, though he does leave a few broken hearts. His sexual appetite is high and since he's a vampire that will likely live forever, he plans on indulging as much as he can. With each city he visits, comes a new woman or two (or three and four in some cases) to spend the night with and he can honestly say he's having a great time.
After leaving Boston he decides to head to New York, making a point of going to one of the most exclusive clubs in the city. That night he meets Lucy in a club and is immediately taken by the woman. She's taller than the previous Bennett women, only a couple inches shorter than him, but just as beautiful as her ancestors.
He enjoys the fact that unlike most of his recent bed partners she knows what he is and they spend time drinking and talking about the supernatural. It's obvious not only to them, but to those surrounding them that there is a lot of sexual chemistry there and on one is surprised when they leave the club arm and arm. What does surprise him is that she's the one to make the first move.
"Think you're strong enough to fuck me for a few hours?" She asks with a challenge in her eyes.
"I can do better than that. How about I fuck you the entire night?" Is his response.
An hour later, his stomach is full of blood and bourbon and he's buried balls deep inside of her as she claws his back in an expensive hotel room. She makes a point of staying quiet, not wanting to give him the satisfaction of screaming his name, but he knows it's good for her based on the way she's writhing underneath him. So when she comes and the glass sculptures in the room shatter, he is unable to suppress the smug grin on his face.
For him it's the best sex he's had in while and true to his promise, he makes a point of spending the night fucking her in every position imaginable, on every flat surface of the hotel room. Much of the night is spent with his head between her legs, her lips wrapped around his cock and his cock pounding her until they eventually collapse on the bed and fall asleep tangled around each other.
The next morning she's gone and he's off to visit another city. He decides on Prague and in a surprising twist, the encounter with Lucy is apparently enough to stave off his sexual appetite for a while. As a result it's the first place he's visits in long time where he doesn't bed a woman.
Bonnie ─ Mystic Falls, 2009
Stefan feels a jolt throughout his body when he first sees Bonnie at Mystic Falls High. All eyes are on him when he walks into the school including hers, but he pretends not to notice because he needs to figure out whether or not the Katherine look alike is actually the real thing or some kind of doppelganger. But he vows to chat Bonnie up later once he's taken care of the situation. At the time he's unaware that she's a Bennett, but he does know there is something special about her.
He's a bit weirded out once he finds out she's Sheila's granddaughter, but it doesn't stop him from finding her attractive nor does it stop him from wanting to pursue her. All of that changes when Bonnie touches him one day, freaks out and starts avoiding him afterwards. He resigns himself into the idea that she's the one Bennett he's met that isn't susceptible to his charms. So after a while he focuses his attention on Elena and eventually falls in love with her.
Still it doesn't stop him from trying to earn Bonnie's trust and he succeeds a little one night when he saves Bonnie and they talk a little before he takes her to Sheila.
Seeing Sheila again is interesting because most of his bed partners have either been other vampire's like him that never age or humans that didn't live long enough to grow older. So seeing an older, but no less attractive Sheila Bennett is an interesting concept.
She smiles as he recounts the day they first met and their brief time together, but they agree that the past should stay in the past. Instead she makes a point of trying to draw him and Bonnie closer and it works.
At least until Sheila dies helping himself, Elena, and Damon.
Lucy ─ Mystic Falls, 2010
When Lucy breezes into to town, he's at the point where he's devoted to Elena, Bonnie is dating Jeremy, and they are working on their tentative friendship after months of tension.
One night during her brief stay they all end up at a Masquerade Ball despite Katherine being a problem. In the midst of trying to stop Katherine, when she saunters into the ball.
He's shocked to see Lucy there wearing an engagement ring, but he's even more shocked when he finds out that she's been helping Katherine, not realizing just how ruthless the vampire can be. When she finally does figure it out, she is contrite and she decides on helping the group in the end.
Because of what's going on with Katherine and her getting to know Bonnie, they really have no time to talk, but before she leaves town their eyes meet one last time and he knows she remembers that one night together.
Bonnie─ Mystic Falls 2011
He comes close to pursuing Bonnie when he returns to Mystic Falls after spending the summer with Klaus. His emotions are turned off which means the things that usually hold him back from seriously thinking about her in that way no longer plague him.
Without his conscience poking at him, he thinks about how her hair would look spread out across his bed, with him above her fucking her into the mattress. He wonders how amazing her lips, the ones attached to her mouth as well as the ones between her legs would taste as he plunders them with his lips and tongue. He imagines her gripping at his hair as he brings her to orgasm after orgasm with his mouth.
It gets worse once they start working together to get Klaus' family coffins open and are alone in the old witches' house on a regular basis.
While she's working he thinks about taking her right there on the floor, pounding in and out of her until she comes hard and fast around him. Then he would pull out of her and thrust into her from behind, taking her over and over until they both are coming so loudly that the old house starts to rattle.
He fantasizes about having her small frame wrapped around his larger one as he fucks her against the wall. Would she scream his name? Would she ask him to take her harder? He has a feeling she's a screamer.
He seriously considers making his fantasies a reality until then she blabs about their secret partnership to Elena. After that he's so angry he forgets about wanting to fuck her.
At least for a while.
Bonnie─ Mystic Falls, 2012
He's a few weeks into his breakup with Elena and he's angry, hurt, and wanting to lash out. So he goes to see Bonnie since he knows she's going through her own little dark phase as well.
Stefan's barely there twenty minutes before they are all over each other. His lips are on hers, her tongue is in his mouth, and his hands are up her shirt, they are seconds away from stripping down and fucking right on her couch.
The only reason it doesn't happen is because Elena chooses that moment to call, shattering the sexual tension. Bonnie immediately comes to her senses and goes off to help her best friend, while he comes to realization that dragging Bonnie into his hurt over Elena would be unfair. As much as he wants her he can't and won't bring her down to his level, into the darkness that he's surrounded by.
So later on when she makes it clear she wants to pretend it never happened, he agrees and focuses his attention on Rebekah instead.
Qetsiyah ─Mystic Falls, 2013
It only makes sense that he ends up with the first Bennett witch, especially since she was responsible for rescuing him from Silas' prison. She marvels at how different he seems from Silas despite their identical faces and he's slightly in awe of the power that radiates from her. They bond over their hatred for Silas and the decision they make to team up in order to kill him quickly turns into a more personal team up.
The sex is explosive and he suspects that she's using him somewhat as a substitute for Silas, but when her pussy clenches tightly around his cock in a way that makes his fangs come out, he doesn't really care. Besides there is a part of him that's using her as a way to get over Bonnie's death.
After finding herself in the 21st century, Qetsiyah decides to change her name to Tessa to make things easier.
"It rolls off the tongue better." She says with smirk when he asks why.
Still he decides to call her by her given name because he likes the way it sounds on his lips. And from the way she goes crazy whenever he utters it while they're fucking and he's pounding her into the mattress, he knows she does too.
In between bouts of sex they work on trying to kill Silas as well as trying to bring Bonnie back to life. Damon helps too and he's a bit surprised by how invested his older brother is. They go through many options growing despondent when each turns out to be a dead end.
The easiest way, which entailed Bonnie she becoming the anchor between the other side and earth, had been vetoed by Stefan once he found out she would have to feel the pain of every supernatural being that died.
"She doesn't deserve that kind of fate." He says when she brings it up one day and they continue to search for another way.
It's not long before they manage to find a solution and then Bonnie's back in the land of the living. And with her reappearance his affair with Qetsiyah ends. Somehow it just doesn't seem right now that Bonnie's back.
Qetsiyah leaves town soon after, coming to the realization that she wants to see the world. The day she leaves, she presses a kiss to his cheek before giving him these final partings words, "Good luck with her."
At the time he assumes she's talking about Elena, but later on he will realize that she wasn't.
Bonnie─ Mystic Falls, Present
When he and Bonnie finally get together it's a long time coming.
After her resurrection, Stefan makes a point of strengthening their relationship and gradually they start to become closer. He helps her deal with her newfound role as an immortal witch while she helps him deal with his summer trauma. He's not surprised when he falls for her hard because he knows that a part of him has always been a bit enamored with her.
This time it's different, with Elena no longer holding his heart he's able to see her as a potential love interest and he makes no secret of his attraction. Earning him ire from Jeremy, jealousy from Damon and Elena, and amusement from Matt and Caroline, the latter of whom reveals she's rooting for him.
Things change officially between about six months after Bonnie's resurrection and a few weeks after she ends things with Jeremy. They are hanging out in the dorm room she shares with Elena and Caroline when he kisses her. He pulls back; afraid that he may have overstepped his boundaries. Instead she drags him in for another kiss that quickly grows heated and they end up fucking right in her twin bed.
It breaks of course because this is a long time coming for them and neither of them are able to control themselves. The moment he hears the wood frame cracking he lifts them off the bed and they roll onto the floor, they are so wound up in passion that the move doesn't even faze them.
In fact when Bonnie's legs tighten around his waist and her nails scratch at his back, he realizes that the new location is turning her on. It turns him on as well and he strives to make the fantasies he's had about her in the past become reality.
He does however take the time to chuckle a bit when Bonnie quietly wonders how she's going to explain the broken bed.
"I can fix it later." He utters against her lips and she rewards him by shoving her tongue into his mouth and squeezing his cock with her inner muscles.
It's not long before they're erupting in an intense orgasm. He hardens immediately and he knows they would have spent the whole night fucking right there on the floor, if they hadn't been interrupted by Elena and Jeremy.
Not exactly the most ideal circumstances for their night together, but the look of rage on Elena's face when the two siblings walk into the dorm room and see him on top of Bonnie, her legs wrapped tightly around his waist as he moves in and out of her almost makes up for the interruption. What's even better is the look on Jeremy's face. The boy doesn't know whether or not to feel angry or betrayed. However once Stefan slips out of Bonnie and stands up, his cock hard and eager, Jeremy decides on anger.
Stefan helps Bonnie up and she quickly grabs the sheet off her bed to cover up. An awkward silence fills the room as the four stare at each other before Elena turns and storms out of the room. Jeremy follows, but not before glaring hatefully at Stefan.
Though the mood isn't broken, they both realize they want more privacy and somehow make to the boardinghouse without jumping each other. They waste no time resuming their activities the moment he gets her to his room.
Afterwards when they are both sated and Bonnie's asleep in his arms he ponders his life since he became a vampire. He's been with a lot of women, had a few relationships. Mostly he had a lot of one night stands and affairs, but the Bennett women were the only ones of the bunch that had a lasting impression on him.
He used to wonder why it never seemed to be in the cards for him to end up with any of them for longer than a few weeks despite how drawn to them he'd been. Now he knows it's because it had all been leading to Bonnie.
As for why he and Bonnie didn't get together until now, he knows it's because they weren't ready for each other until now. That they had to go through all of this before they would truly be good for each other.
A couple of years ago after their encounter with Lucy, Damon had once joked that Stefan would be bedding be Bennett witches for centuries to come. Though Stefan had laughed, he had secretly wondered if it were true even though he had been in love with Elena then. He never said it out loud, but the thought of being able to bed beautiful and powerful family of witches had seemed appealing idea future at the time.
But when Bonnie snuggles into his chest, wraps her arm more tightly around his waist and murmurs "I love you", he knows that she'll be the last.
"I love you, too." He responds with a wide smile.
As he falls asleep his last thought is that he's definitely looking forward to spending his future with Bonnie.