In college, she just wanted to stay friends. Now, her little sister calls me Daddy.

Chloe moaned softly as she wrapped her thighs around my waist and bucked her hips against my belly, almost against my rib cage. She squeezed tight, with the muscles from horse riding she’d built up all her life, and for a second, I half-expected a sudden loud pop, followed by sharp, unrelenting agony as she snapped my ribs in her quest to stimulate herself against me through her jean shorts.

I say half expected because I was busy groping her generous boobs underneath her sweater while I sucked the side of her throat. I’d sort of dislodged her bra, digging my hands up and beneath it to grip at that warm underboob flesh, feeling around with my fingers until they closed on a hardening nodule of goose-pimpled flesh. When I tweaked it, she yelped, and I responded by kissing her neck even harder.

After nearly an entire semester’s worth of flirting and will-we-won’t-we, I finally had my college crush in my lap. It was the night before we all went home for Thanksgiving break and somehow, watching The Office in my room on my laptop—a fairly new-fangled concept at the time, this being 2007—had turned into cuddling on my bed and then I’d gotten up the courage to run my hands over her thighs until she started moaning and then, dear reader, we were off to the races.

“Wait,” she gasped, placing a hand on my chest.

“What’s wrong? Did I hurt you?”

I remember an early challenge of my sex-having life being my inability to find a middle-ground between how much I wanted to twist and bite a girl’s nipples and, well, how much she actually enjoyed it. I assumed I’d been too enthusiastic once again. These days, I just look for girls who like the pain, but let’s table that for now.

“No, no, dude, it’s not that. I just don’t think we should be doing this.”

She’d been bucking against me still as she said that.

I loosened my embrace and we regarded one another. It’s hard for me to overstate how attracted I was to Chloe—she had this kind of girl-next-door tomboy thing going on. A bawdy sense of humor, always down to watch football or play videogames or do shots, but whip-smart too, and quick with the lolcat in an email (again, it was 2007). Maybe she wouldn’t have stood out in the crowd, but she had this adorable, impish face, always animated, straight brown hair, and here I’m stalling before telling you what you really want to hear—an incredible body. It wasn’t clear immediately, because she tended to dress a bit sloppy (itself kind of hot) in hoodies and rugby shirts, but she was short, with a plump ass and boobs too big for her frame. A few times, living in the dorms with her, I’d glimpsed her in a sports bra or while heading to the pool, and her flirty blushing winks suggested to me that she both knew how hot she was, and didn’t quite know what to do with it.

“Are you okay?” I asked, not knowing what else to say as she climbed off my lap and sat next to me. She leaned on my shoulder.

“We’re really good friends,” she blurted out. “And I do kind of really want to get on you. But, like, it’s going to be so awkward afterwards. It feels like making a mistake.”

“Personally,” I said. “I think we should make a mistake.”

“See, when you joke around like that, it makes me want to fuck you, but I don’t want to lose you as a friend. I don’t know. Maybe that wouldn’t happen?”

I sighed.

“Listen, Chloe, I don’t think it would,” I said. “But I don’t want you to do anything you’re not into so, like, why don’t you think about it over break?”

“Dude, you’re so fucking sweet,” she said, and kissed my cheek. “You, like, make me want to go out with you. No fair.”

We hugged and she left my room. Later, of course, I found out she’d ended up sleeping with my good pal, Tony, that night and they’d texted nonstop over Thanksgiving, and decided they were going out by the time we were all back on campus.

But this story is not really about Chloe.

No, it’s about her little sister.

If we were to watch a cinematic montage of the years that followed (set to Blink-182’s Dammit, let’s say), it’d show me having a string of girlfriends in college, invariably meeting up with Tony and Chloe over beers to commiserate when things go south. You’d see me studying abroad with Tony, camping with the two of them the summer before our senior year, hugging Chloe’s mom and shaking her dad’s hand at the party they through for Chloe and her friends at a popular bar in town the night we before we graduated. You’d see me working a series of shitty, stressful jobs, and then going to graduate school, spending hours reading in the library, starting to teach undergrads. You’d also see me start to develop my own, ahem, preferences—going from spanking and hair-pulling and nipple tweaking to leather and whips and safe words.

Fortunately, my young adulthood coincided with the popularity of 50 Shades of Grey, so suddenly, ever girl I slept with was interested in getting tied up.

As we all started our careers, I naturally grew distant from Tony and Chloe, who’d moved in together. They were clearly the it-couple of our friend group, and we all expected them to get married before too long, which they did—the first of our friend group to get hitched. I went to their wedding on my own, so imagine Blink-182 singing “I guess this is growing up!” over and over as I watch Chloe and Tony share their first dance, sipping a glass of champagne thoughtfully, as the band played a Mumford and Sons song.

As the band leader invited other couples to join Tony and Chloe on the dance floor, I was about to take a step back, letting their aunts and uncles and cousins engulf them, when I realized someone was standing at my elbow.

She had a dark tan, a beauty mark on her lip, and the same animated, almost cartoonishly large eyes that Chloe had. She smiled at me with a mouth full of braces. From the satiny, dusty pink dress she wore, I knew she was in the bridal party.

“Hi,” she said.

“Hi,” I said.

At that moment, Tony and Chloe spun nearby us, and Chloe reached out to grab my sleeve.

“Dance with her,” she commanded. Then, turning to the girl, she said: “Lizzie, dance with him; he doesn’t have a date!”

Thanks, Chlo.

Now, everything made sense—this was Chloe’s little sister, eighteen years old and a senior in high school. I remember her talking a lot to me while we danced, but I can’t for the life of me remember what she was telling me about. I’m sure I asked her the usual questions—where does she want to go to college, what does she think she’ll major in, and so on, but I was simultaneously distracted by the softness of her arms and shoulders and how she clung to me a little too closely.

That gambit ended up being successful, and after I politely extracted myself from Lizzie’s teenaged embrace, I didn’t think about her for eight years.

For the next montage, let’s do All Star, by Smashmouth, RIP Steve Harwell. The years start coming and they don’t stop coming. I finished grad school, ran the gamut of postdocs, published, got a job, then got a better job, and ended up in the same city as Tony and Chloe.

When I met up with them for drinks, I found myself appreciating, quietly, how Chloe had grown up—she dressed more professionally now, a bit more feminine, wore perfume and cute glasses, and as jealous as I still was, I had to admit she and Tony made a sweet couple.

“We’ve got to find you a girlfriend,” Chloe said over pizza, once the first pitcher had been drained.

“Aw, let him enjoy being single,” Tony said. “I haven’t been single since I was eighteen!”

“Yeah, we don’t know what dating is like now,” Chloe admitted. “But look, you’re such a catch. There are so many girls who’d just go crazy for a guy who didn’t vote for Trump, has a full head of a hair, and, like, has read a book in his life.”

“Oh, I’m still settling in, you know,” I said. This was partially true. I was building new courses from scratch for my new position, editing a volume of essays, and assembling my new Wayfair furniture.

“You know who we should set him up with?” Tony said, as the next pitcher descended on the table. Chloe gasped and covered her mouth.

“Oh my god, you’re right!” she exclaimed, still adorably cartoonish as ever. “Lizzie could use a nice guy.”

I actually had to wrack my brain to remember who Lizzie was.

“You danced with her at the wedding!” Tony and Chloe, they’re the kind of couple who are so confident in their centrality to the lives of their friends and family that they always say “the wedding,” and not “our wedding.”

“Oh, I guess I did. But she’s quite a bit younger than me—”

“Dude, we’re all getting older. She’s twenty-six now.”

Chloe quickly summarized for me: Lizzie had also just moved to the city for grad school, at a different university. Her ex-boyfriend was supposed to come with her but got cold feet about moving without a job lined up, and they’d broken up. They’d been able to get out of their lease, but that meant Lizzie was staying in Tony and Chloe’s guest bedroom for the foreseeable future.

Finally, I agreed that I’d take Lizzie out. I was pleased to see she’d grown up nicely too, looking at the pictures on her social media Chloe had thrust under my nose sometime around when the third picture arrived. There was Lizzie in a bikini at a beach, with that petite-curvy build shared by her older sister, and some glamor shots from a friend practicing for a photography course: Lizzie’s hair was longer than Chloe’s, and she looked over her shoulder at the camera with a pensive, hesitant look, as though just about to bite her lip. In another series of pictures at a more recent wedding, she wore an androgynous suit, and a top that showed off her tanned midriff.

I wanted to ask if Lizzie and Chloe were step-sisters, since, even though you could see the similarity, Lizzie really was much darker than Chloe. Not that I was complaining.

I had to admit, that if I were just going on looks alone, Lizzie was cuter than Chloe had ever been. I saw the phantom of the Chloe I’d craved in her face, in her figure, but it was as though she’d refined it, taking everything that was entrancing about her sister and distilling it: the tomboy vibe; the big, beautiful anime waifu eyes; and, of course, a set of tits and an ass that had no business being attached to a five-foot-one frame.

And so, later that weekend, I met Lizzie at a local museum where I knew the curator. She wore a sleek dress that showed off her chest and legs without giving away too much and beamed at me when she climbed out of her Uber.

“Hi!” she cried, waving, even though I was right in front of her. Like her sister, she was prone to becoming animated and excited and she hugged me as though we were old friends. “I can’t believe it! It’s been so long!”

“I guess,” I said. “Since the wedding?”

“Yeah, I was like, so excited to dance with one of Chloe’s college friends,” she said. “I bet I was such a dork. I mean, more than I am now.”

“No, I remember you being very cute,” I said, even though I remembered fairly little of that night.

Lizzie seemed like she wanted to say more, but caught herself, blushing, and giggled. I led her into the museum and we met up with a friend of mine, a curator, who gave us an impromptu private tour. I must admit to being an enthusiastic student, and eager to impress in all things—I’d done some research on the pieces we were to see, and Lizzie turned to me with questions almost as much as she did our curator.

Afterwards, we went for cocktails at a bar down the street, and Lizzie produced an envelope from her purse.

“Chloe made, uh, ice breaker cards for us, and she made me promise to use them.”

Lizzie handed me the envelop and I read the first ice breaker card.

“Describe your ideal lover, and don’t skimp on the details. Jesus, Chlo.”

Lizzie broke into giggles and I was about to suggest we forget the card when she launched into her answer.

“I guess I definitely have some daddy issues, so I’d like a guy who’s a bit older than me… Maybe kind of dominant. Takes charge, takes the lead… What about you?”

My ears perked up at this. While I’d initially imagined Chloe, bound and gagged and dripping, in answer to the question of my ideal lover, now I was starting to imagine her sister.

Before I could answer, though, Lizzie stepped in again.

“You have a big crush on my sister, right? Is she, like, your ideal lover?”

For once, I was flustered.

“No, I mean—it was just in college. We hooked up. Kind of. Barely.”

“She says you hooked up.”

“We made out and I felt her boobs, and then she said she just wanted to be friends and went off to fuck Tony instead.”

Lizzie was grinning, and bit her lip as I told her this.

“Bitch,” she said, and somehow, hearing her say that—such a departure from how she related to her beloved older sister up until now, such a departure from how Chloe had gushed over her. “That’s just like her. She had big main character energy.”

“I can see that.”

“But wait—answer the question.” Lizzie tapped the card. I was suddenly very aware of how we were sitting in the corner of a mostly empty bar, on a Sunday afternoon, her bare thigh extended out from beneath her dress and her knee touching mine.

“I have some dominant tendencies,” I said. “And I like someone who complements that. Submissive, eager to please. Willing to try new things. I’m sure I sound like a serial killer.”

“Totally,” Lizzie said, giggling.

“Hey, can I ask you a question—” I began suddenly but Lizzie filled in for me.

“Do Chloe and I have the same dad?” she asked. She gave an exaggerated grimace. “We don’t know. Mom and dad won’t talk about it. I know our grandpa was adopted, but he was full-blood Cherokee, or so the story in the family went, so maybe I got some of his looks? We seriously don’t know.” She paused to take a healthy slurp of her rosé. “But dad always liked Chloe better than me. They’ll deny it but you can, like, tell, you know?”

“Hence the daddy issues.”

“I know, I’m such a cliché.” She picked up another one of the ice breaker cards. “Oh my god, Chloe… Here goes: Imagine your date has told you that anything is on the table for twenty-four hours, sexual or otherwise. What do you do?” She put her face in her hands, squirming.

“I’ve got some murders I’d like to commit, so you’ll be providing me an alibi.”

“No, answer for real.”

“Ladies first.”

“My answer isn’t interesting,” she said, jerking a pinky-finger in my face. “Because I’ll just be letting you do whatever you want to me anyway, because that’s what sounds good to me. So long as you let me call you Daddy and you tell me what a good girl I am.” She bit her lip again. I was finding I quite liked this tic of hers. “Is that too freaky?”

“Not at all. I was thinking, after I’m done with my murders—they’ll only take a couple hours—I’d tie you up to celebrate. We have twenty-fours hours, after all.”

“Yeah?” Lizzie said, leaning closer, so I could smell the wine on her breath—not at all unpleasant. “What else?”

“Goes without saying that you’ll be naked. I’d start by teasing you all over. Your lips. Your neck and ears. Your hair. Stroking, pulling, twisting, tugging… Then down over your breasts. Getting close to your nipples but not touching you until you beg me to.”

Slowly, Lizzie’s breath was growing deeper, slower. Her wine glass was suspended next to her lips, as though she were frozen in the act of drinking, but her eyes clung to my gaze.

“Yeah?”

“And even then, I’d keep from touching your nipples. Maybe I’d just blow on them, and then I’d kiss and stroke your belly and then down between your legs…”

“Yeah?” she asked, the pitch of her voice rising.

“And I’d tease your inner thighs… Lick and suck and bite your all over but not on your pussy yet.”

“Please,” she said.

“Please what?”

“Do that.”

“Do what.”

“Everything,” she said, breathily, and took a very unladylike swig of wine. “And tell me more.”

“I bet you’ve got toys. I bet you’ve got one of those toys that sucks your clit until you cum.”

She broke into a smile. “How’d you know?”

“Once I’m done licking you—devouring you, letting you feel my tongue and fingers inside of you, slurping up your unique flavor and scent, I’m going to use that toy on you over and over again, stopping right before you cum until you’re begging me. Absolutely, shamelessly begging. Telling me you’ll do whatever I want, so long as I let you cum.”

For a moment, I wondered if I’d gone too far. Lizzie flagged down the bartender and asked for a check.

“Is everything okay?”

“Yes,” she said, still breathy. I noticed a slight sheen of sweat had broken out on her face, making her glow all the more enticingly. “Move our dinner reservation back.” She finished her wine. “Please, Daddy.”

I didn’t need a formal, written invitation. I called the restaurant, then summoned an uber back to my place.

Once we tumbled into the backseat, I slid my hand between her thighs, and she, silently, not looking at me, spread her legs, giving me access beneath her dress as I began to explore. She turned to look out the window, covering her mouth with her hand, leaning against the door opposite me.

I found her pussy covered in lacy fabric that easily slid to the side as she shifted for me. I felt heat radiating off her hole, and I was silently thankful for the Uber driver’s intense patchouli incense, no doubt covering up some other rider’s digestive indiscretion, which now masked the increasingly unsubtle scent of Lizzie’s arousal. Likewise, I was thankful that he was playing loud Christian reggae that drowned out Lizzie’s soft squeals and squeaks. She was cumming by the time we were approaching my block, and I felt her grip my thigh, digging her nails through my jeans as though trying to displace everything she was feeling.

“Thank you, five stars,” our driver said, completely uninterested in us as we climbed out. I noticed the glimmer of a small wet spot where Lizzie had been sitting, and while it could easily have been mistaken for sweat, I added another few bucks to the driver’s tip just in case.

In my building’s elevator, I took her in my arms for the first time in years, and kissed her, tasting wine and eagerness on her lips.

“So fucking hot,” she whimpered as I ran a hand up her dress, over her thigh. “I can’t believe you did that.”

“You came for me like a good girl,” I whispered in her ear. She let out a soft chortle of pleasure as I caught her by the hair, pulled her head back, and kissed her throat, while pinning her to the wall of the elevator.

The first thing she did when we got inside was drop to her knees. She began undoing my jeans and pushed me back against the door, grinning up at my like a kid with a new toy as she pulled my cock out of my boxers.

I groaned as she ran her tongue over me, gazing up at me.

“Like this, Daddy?” she asked, rubbing the tip of my cock against her tongue, not smiling, almost pouting.

“That’s a good girl,” I grunted like an animal, gripping her by the back of her head, filling my fist with her hair and guiding my cock into her mouth. “Make Daddy feel good.”

As much as I wanted to face fuck her, I wasn’t about to actually orally assault this girl—but Lizzie had other ideas. I let go of her head, but she caught my hand and replaced it, sliding her mouth off my cock for a second.

“It’s okay,” she said, panting huskily. “You can be rough.”

“Are you sure? I can be very rough.”

She lapped at the tip of my cock.

“I want to be a good girl for you, Daddy,” she whispered. “Make me your good girl.”

I pressed my cock into her mouth and felt her start to gag, so I slowed down. Her eyebrows furrowed and I saw her big, brown eyes start to water as she gazed up at me.

“Tap my leg if you need me to stop,” I whispered to her, and she nodded. I slid out of her mouth for a second, letting her breath, before fucking it back into her. She gagged, but held on, as I fucked her face like it was a pussy. Soon, tears were streaming down her cheeks—I couldn’t believe I was doing this with a girl before our first date was even technically over, let alone the fact that she was my friend’s little sister, and truth be told, I felt a little bad, but when I stopped to check in with her, she kissed me eagerly.

“I don’t care where you put it,” she whimpered. Her voice was a little hoarse after the throat-fucking, I noticed with pleasure. “But I need you inside of me.”

I stooped down and threw her over my shoulder, much to her delight as she squealed and kicked her feet. Not to brag, but I’ve got a pretty solid squat and deadlift, and I could’ve carried her around all day. Her shoes clattered behind me as I carried her into my living room and put her down in an armchair.

In a flash, I’d lost my jeans, my shirt, my socks, and my shoes, while Lizzie wriggled out of her dress, and then sat forward, looking at me expectantly and thrusting her chest forward. She wore a strappy black bra that looked great against her dusky skin but I was happy to see it go. She shook herself free once I’d undone the clasp and her tits sat, proud and liberated, before me—she was easily a DD cup, with hardening, dark red nipples that absolutely seemed to crave my touch. When I reached for one—trying not to think too much about how her nipples felt like Chloe’s—and twisted, she gasped, moaning.

“Yes,” she whimpered, pulling my other hand to her mouth, starting to suckle on my fingers. “Do whatever you want to me.”

“What if it hurts?”

“Then tell me I’m a good girl when I’m crying,” she said, not losing my gaze as I twisted her nipple hard. Finally, she winced and her eyes fluttered closed, and she leaned her head back, moaning.

I let her nipple rest, and took it in my mouth, suckling it gently, as though apologizing for torturing her. After a moment, she drew my face to her other breast, stroking my hair as I suckled her.

“Feels so good,” she whimpered. “You make me want to be such a slut for you. As soon as I saw you today, I got wet. I’d gotten all excited about this date, and then I’d been trying to calm myself down and as soon as I saw you, I was like… Yeah, I need him inside of me.”

I kissed her again, putting my hand around her throat—gently, at first, and then tightening my grip as she moaned and nodded into the kiss.

I broke the kiss and knelt between her legs. I lifted them and had her spread them, had her hold them, so she was doubled up and exposed to me: her tawny skin giving way to a meaty set of pussy lips, swollen and dripping with arousal, beneath a tightly groomed landing-strip of dark brown hair. The intoxicating scent of her young womanhood filled my senses: earthy and musky, tangy, and sour, so strong I could almost taste her before I’d even set my tongue to her.

“I’m a bit sweaty so you don’t have to,” she started saying, but her voice dissolved into a moan as I drew my tongue over her slit, curving into the shallow pit of her body, where her tanned skin turned soft, pink, and glistening.

She was on the verge of cumming quickly, and so I retreated, letting her calm down a bit.

“Fuck, you’re doing that,” she exclaimed breathily.

“Yes, Lizzie, I’m doing that.”

I began to lick her again, and within minutes, I could tell she was going to burst, and I stopped. This time, I traced a finger around the tight knot of her asshole and she shivered.

“Is that okay?”

“Yes, Daddy,” she murmured. “Anything you want.”

I dipped a finger inside her pussy and, with the lubrication, pressed it into her ass as I began to lick her again. She grunted, bucking her pelvis against my face and moaning as I slurped at her slit, not trying to get her close yet, before landing my tongue on that divine spot two millimeters off her clit that drove her wild.

When she started to cum this time, I didn’t stop—I let her ride out the orgasm, moaning and sputtering for me, the muscles in her ass spasming around my finger.

“God, that’s good,” Lizzie moaned as I slid my finger out of her. “With, you know, my butt.”

“Have you ever taken it in the ass?”

She shook her head. “No, Daddy. Always been scared to.” But then she grinned at me. “But that kind of felt good so…”

I ducked out of the living room to wash my ass-finger, and when I returned, Lizzie was sitting up attentatively, like the best student in the class.

“Where do you want me?”

“Legs back, how you were. I want to look at my girl’s pretty face while I make you mine,” I said, leaning down to kiss her. She pulled her legs back, and was almost able to get them behind her elbows.

“Not flexible enough,” she said. “But I can hold them.” She glanced down. “This shows off my belly rolls. Are you sure you want to see me like this, Daddy?”

She barely had any belly rolls, but what she did have looked quite enticing: she had a small frame, and I think her figure would count as “slim-thicc,” if people still say that—she had a soft, lean belly that rolled over herself when I tied her up in this knot, doubled over, thighs spread for me. She looked up at me with a quizzical expression on her face, her lips glistening from the sloppy face-fuck I’d just subjected her too.

“There’s nothing I’d rather see more,” I growled, balancing myself leaned on the armchair as well. I dug two fingers into her pussy, rough, feeling her body clench around me as she groaned, then slid them out and smeared them over her face and lips as she suckled at my digits, moaning. “Let me grab a—”

“Hey, you don’t have any terrible diseases, right?” she said. There was a note of urgency in her voice. Like a kid whispering in class, afraid the teacher might overhear. “I don’t either, and I’ve got Nexplanon so…”

“You want to skip protection? With a man you just met?” I said, feigning shock, clutching my figurative pearls. Lizzie scowled, but her scowl turned into a moan.

“I want you in me, Daddy,” she whined. “I’ve known you for a long time. We’re friends. Kind of. And I want to feel… all of it. You know. I want you to finish in me.” Suddenly, her demeanor changed: “But if you’re lying to me and you give me something, you know Chloe is going to kill you.”

I didn’t have any doubts about that. I slid the tip of my cock over her wet hole, teasing her for a few moments before sinking into that glorious, tight warmth. It was like lowering myself into a hot bath after coming in from shoveling snow—her slick wetness absolutely engulfed me, all but sucking my cock inside as I began to fuck her. Lizzie’s face was frozen in a silent scream of pleasure, a scream that was gradually becoming less and less silent as I pumped into her. I gripped her generous tits in both hands, digging my fingers hard into her flesh as I saw a tear roll down her cheek. She bit her lip, sputtering and moaning as I drove into her.

While my ability to feel fine details with my penis is, admittedly, lacking, even I could tell that I was hitting the backboard, so to speak.

“How does that feel?” I snarled. “Is it too deep?”

“Feels good,” she whined. “Really good, Daddy.” She was digging new nails hard into her calves, holding back her legs in the position I’d placed her in. “You’re so deep… Like so deep… You’re at the back… Don’t know what I’m saying, don’t listen to me, oh my god.”

Now, I held her around the waist, giving her poor boobs a break, as I threw myself into her. Finally, orgasm snuck up on me and I plunged myself into her a few more times, cumming as I did so, releasing myself into her warm, wet hole and continuing to fuck my tool into her sloppy cunt as my cum overflowed her, growing creamy and frothy from the friction. I only stopped thrusting not when I started to grow soft—in the back of my head, I thought I could probably power through and cum in her a second time—but when I heard the jingle of my alarm reminding us that our dinner reservations were in half an hour and we were on the other side of the city.

Lizzie made herself presentable in less then ten minutes, despite my attempts to bend her over my sink and fuck her again. She didn’t put on lipstick until we got in the uber so we could make out in the elevator on the way down, and we all but skipped into the restaurant like a couple of giggling teens fresh off their first roll in the hay.

Sitting down, I felt something touch my leg, and Lizzie grinned at me, running her bare leg up my thigh. I felt her bare foot in my crotch and she pressed the approximate location of my half-hard cock with her big toe and giggled.

“I want you to know,” she said, suddenly growing serious. “That I don’t do that with everyone.”

“Who’s everyone?”

“Guys. I mean, people I go out with. I mean, this is unusual for me. You get it? Sorry, I’m like, still overstimmied, someone fucked me really, really hard and I think I’ve got a bruise forming on my cervix.”

“So, you’re saying you were a virgin, waiting for marriage, until I came along?”

“Ha. Ha,” Lizzie said, and stuck out her tongue. “I mean, I don’t have a lot of one-night stands. Or hook ups. I’m a relationship gal. I’ve slept with seven guys, and I’ve had relationships with five of them, so…”

“Eight guys, now.”

“You’re right. Eight.”

“I did think maybe I’d let myself be a little slutty with you,” Lizzie said, wringing her hands in her lap a bit, a child sent to the principal’s office and explaining herself. The twink waiter assigned to our table approached behind her, showing up so suddenly I couldn’t warn her. “Since I just got out of a relationship. But I wasn’t planning on going this far. But I’m glad I did. I think that was maybe the best sex of my life.”

“Well, looks like you folks have had an eventful Sunday!” our waiter chirped, not unapproving. “Have y’all dined with us before? We do things a little differently here—”

“No,” I said. “But I’m familiar with the concept of small plates and sharing food. I’ll take a gin martini, lemon peel, and the lady will have a glass of rosé. French, mineraly, not too sweet. Please and thank you.”

I’d remembered that she liked the rosé at the bar prior, which she described as “tasting like rain,” and it was a Côtes du Rhône, so I was just making educated guesses, but she grabbed my hand and applied a death grip.

“That was. So. Fucking. Hot. Daddy. Oh my god. If I weren’t already soaked from before, I’d be wet now.”

“Good girl,” I teased.

Over dinner, we actually got to know each other. It turned out that we’d started with Chloe’s ice breaker cards backwards, and they actually began with far more innocuous questions. I learned that Lizzie was doing a master’s program in environmental technology and design—I hadn’t even realized that, like Chloe, she’d gone into tech—and I got to talk for a bit about what I teach and write about.

“Do you have students my age?” she asked, suddenly. “Grad students, maybe?”

“I’ve got grad students my age, so it’s a wide range.”

“I probably wouldn’t be able to concentrate in class if you were my professor. And that’d stress me out, because I’d really want to impress you. I’d always be coming to office hours, first to raise my hand in class.”

Near the end of dinner, I asked if she wanted to go for a walk, or if she’d grab an uber back to her sister’s.

“Is there a third option?” Lizzie asked.

I couldn’t help but smirk.

“Yes, you can come over again.”

And she did. Once I had her home, it seemed like her clothes melted off. There was a kind of childish joy to fucking her, like we were on a playdate—she was so eager and excited to try and do whatever I wanted, as though I were showing her new toys, new games. She didn’t hesitate to throw herself over my lap, ass up in the air, when I asked when the last time she’d been spanked was.

Her ass practically glowed for me. As I gripped her fat and muscle, she grunted—not unappreciatively.

“Do you ride, like Chloe?” I asked.

“I’ll ride you whenever you want, Daddy. Just say the word.” She giggled. “Yes. Sorry, but you’re fucking a horse girl. You’re going to get lots of pics of me at the family stable over Thanksgiving—ow!”

I slapped her ass hard, delighted by the abbreviated jiggle of her cheeks. I alternated spanking her and rubbing her ass, spreading her thighs and playing with her cunt, teasing a finger and then two into the tightness of her asshole with only spit and pussy juice to lubricate my digits. She had a mole on the inside of her ass cheek (yes, just a mole) that reminded me of the beauty mark on her lip, but I decided I’d keep that observation to myself—as admiring of it as I was, I could see it could be taken the wrong way. Lizzie whimpered shamelessly for me, gripping my thigh at first and then biting down, as though teething, drooling over me.

“Hey,” she said, in between slaps. “Do you still like my sister?”

“We’re close friends.”

I slapped her butt hard. She yelped.

“Yeah, but do you LIKE her. Like, if she wanted to cheat on Tony with you, would you do it?”

I hesitated. I had fantasized about that very scenario, and then felt bad about it. They were both good friends, and now I was the one who didn’t want to jeopardize what we had—in that instant, I felt I understood Chloe a bit better all those years ago, and I felt a bit silly for the mild sense of resentment I’d nursed for a decade and a half.

“No,” I said. “I feel like it’d blow up in my face, and probably not in a fun away.”

I realized Lizzie was breathing more heavily, had gotten sweatier—almost clammy in the last few moments.

“Are you alright—do you need a break?”

“No,” she said, her voice strangely firm and determined. “No, I just had an idea of something I want to do and I can’t decide if I should tell you.”

She sat up, rubbing her backside, and looked up at me, bottomless brown orbs beseeching me.

“What if you pretended I were Chloe and you fucked me? Like, really hard. In my butt, even. Like you’re punishing me for being a bitch to you.”

Fuck. Lizzie stared at me the way you stare down a wild animal, mixing a cocktail of fear and bravado.

“That sounds pretty hot,” I admitted. “But afterwards, I think you should talk to your therapist about your feelings regarding Chloe.”

“Oh, we talk about that all the time,” Lizzie said with a shrug. “So, you want to do it—you wanna’ fuck me like I’m Chloe? You can be rough with her. I mean, me. You get it.”

We had a short discussion about safe words, and then talked about prep for anal. I was still apprehensive about it, and probably should have tabled it for another encounter, but the doubly taboo nature of what Lizzie was proposing was too enticing.

While she sat on my lap, she quite literally changed her face, making an expression that I’d seen Chloe make hundreds of times, and in an instant, she became my friend.

“Dude, you gonna’ fuck me or what?” she said, teasingly, imitating Chloe’s voice almost perfectly. Of course, she was a little sister—she was the biggest Chloe expert there was. How many hours had she spent in front of the mirror, perfecting her imitation of her big sister, just to deploy it for this twisted situation?

I kissed her and put my hand around her throat. She sputtered into the kiss, and giggled nervously when we broke apart, another Chloe tic.

Before I knew it, I was sucking her tits, biting them as she gasped, sitting in my lap and rubbing the tip of my cock over her wetness as she slid down.

“Fuck, bro,” she groaned. “Wish we’d done this back in college. I wanted your dick so bad back then.” I pulled her hair hard, forcing her head back as she yelped. “Fuck. I deserved that.”

“You think you’re so special,” I snarled into Lizzie’s ear as I felt her tighten. “Always the center of attention.” Lizzie ground herself against me—I could tell that this was exactly what she wanted. “Spoiled little bitch.”

“Fuck,” she gasped again. “You’re right. I always had to have the best of everything.”

I ran my nails down Lizzie’s back as she rode me and slapped one of her generous tits as she groaned.

“You know how cute you are. You know what it does to people, Chlo.”

“I love the way you look at me, when you can’t have me,” Lizzie replied, holding her welted tits. At this point, I stood, taking her with me—she yelped, wrapping her legs around me and holding on for dear life as I took her to my bed. There, she knelt on all fours, and reached back to hold open her ass cheeks as I began to lubricate her.

Normally, I would want to do a fair bit more prep for anal than we did, but Lizzie was so eager. Her butthole gobbled up my fingers and she pushed her hips back, taking them to the knuckle.

“How does that feel, Chloe? You like have something in your ass?”

“It feels funny…” she whimpered. “I don’t know if your dick is gonna’ fit, dude.”

I took that, via the conventions of our roleplay, as an invitation to sodomize her. Gripping her hips from behind, I pressed the slippery tip of my cock against her glistening butthole. She gasped as I worked it inside, feeling her muscles stretch around my cock, struggling involuntarily to keep me out before finally going slack.

“Just take it, Chloe. You wanted to be the center of attention? Now you are. Relax and take it.”

“Fuck,” Lizzie gasped, stifling a sob. “I deserve this. I fucking deserve this. I’ve been a bitch my whole life… Giving you my ass is the least I can do.”

I grabbed Lizzie’s hair and forced her head up—it had been hanging down—so that I could see her face. You see, I had positioned her across from my full length mirror, placed just for such situations. I saw her beautiful face, similar to Chloe’s but not the same, contorted with pain and pleasure as my cock impaled her.

“How does that feel?” I snarled into her ear, holding her close but not moving as I finished burying myself up to the hilt inside of her.

“Good… I think…” Lizzie panted. “Like I’m pooping. Like a stretch. It kind of hurts but mostly it just feels weird… I think I like it, though…” She swallowed hard, and got back into character: “I wish I’d given you my virginity back in college, dude. I know you wanted me so bad… I bet you thought about doing this to me back then too…”

As I began to thrust into Lizzie, she squealed, hanging her head, only for me to pull her hair up.

“Hey,” I whispered in her ear. “I’m not inside Chloe. I’m inside Lizzie. You’re giving your asshole to a guy you just barely met. Your Daddy owns your tight little asshole now.”

This seemed to break something on Lizzie’s face. She let out a sob and groped for me, gasping.

“Yes, Daddy, it’s all for you. Oh my god. Oh my god, you’re so deep. This is insane. This is incredible. Oh my god.”

“Touch yourself,” I told her. “I want you to cum while I’m in your ass.”

She balanced herself on her forearm, and shot her other hand between her legs. As I slid in and out of her tight hole, the gaped muscles gripping helplessly at my shaft, I felt her start to spasm in pleasure. It only took a few moments for her to cum, gasping and shaking and trembling.

She went quiet, whimpering and moaning as I pounded her, finally blowing my own load deep inside her ass while I gripped her bruised tits before collapsing on top of her in a sweaty, satisfied heap.

Lizzie and I kept up our unique relationship—not exactly boyfriend and girlfriend but more serious than a situationship—while she was in school that year, and broke it off when she moved for a job. There are plenty more stories I can tell about that time, so if you enjoyed this and want more, let me know!