

Windsor Academy
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REED
“Merry Christmas.”
I look up at the sound of Ainsley’s voice, and I swear to Christ, I feel like I’m choking on my tongue all of a sudden.
Goddamn.
“Holy hell,” I somehow manage to get out.
Ains is standing in the doorway to our ensuite, wearing a matching red lace bra and panty set, her wavy brown hair topped with a sequined Santa hat. I find myself suddenly thankful my sister and her fiancée went out tonight. We’re staying at their place for the holiday, so Ainsley and I had to watch our volume when we had sex each night. With the way she looks right now, I know there’s no way either one of us will be capable of discretion.
Ainsley nibbles her bee-stung lips. “Does that mean you approve?”
Fuck. How could she have any doubt?
I close the distance between us in two long strides and pull her closer. “I really fucking approve. You look incredible, Ains.”
A blush stains her cheeks. “You haven’t seen the best part yet.”
I step back a little, so my eyes can travel the length of her body, from her long, toned dancer’s legs to her trim waist. Her panties' lace pattern is so open that I can slightly make out the thin landing strip beneath. My eyes continue their ascent until they reach her perky tits, pushed up like an offering. My fists clench, itching to get my hands on them. I’m an ass man through and through, so I never gave a woman’s chest any real consideration until Ainsley. When I felt how perfectly her breasts fit in my palms, when I got to wrap my lips around her rosy pink nipples, I was officially an equal opportunity kind of guy when it came to her T and A.
I raise my eyebrows. “Oh yeah? What’s that?”
Ainsley slowly turns until she’s giving me her back. “This.”
“Fuck.”
I bite my knuckles, staring at her heart-shaped ass. From the front, the lacy material appears to be bikini-style underwear. But as she turns around, I see that the back is totally open. The only thing preventing her luscious ass from being completely bare is a series of sexy little straps.
She flattens her palms on the wall and arches her back, which puts those muscular globes on display. “Go ahead, Reed. Show me how much you like ‘em.”
My palm is twitching, begging me to touch her. I reach out, unable to help myself, gently caressing her, right before I wind my hand back and pinken her creamy skin.
Ainsely moans. “Do it again.”
I groan right before giving the other cheek the same treatment. “I am one lucky sonuvabitch, Ains. I don’t know what I did to deserve you, but I’m so fucking grateful. You know that, right?”
She turns her head, her round hazel eyes meeting mine. “I know, Reed. I feel the same. And I’m ready.”
“Ready for what, exactly?”
Ains wiggles her butt. “Raegan and Cassidy will be gone for hours. I figured this was the perfect time to give you your final gift. I’m ready to take that step with you, Reed. I’m ready to give you what you need.”
I freeze, trying not to assume and getting my hopes up. Ainsley and I have had mind-blowing sex many times now. We’ve explored lots of things together, but there is one area of this beautiful woman’s body I haven’t played with nearly as much as I’d like to. Like I said before, I’m an ass man. And when I say that, I mean that I have a healthy appetite for anal and ass play. Spanking, rim jobs, fingers, toys, you name it, if it has anything to do with that part of the body, odds are I’ll love it.
But nothing compares to the feeling of being fully sheathed inside a woman’s ass. I can honestly say no matter how good conventional sex is—and with Ainsley, it’s the best I’ve ever had—I won’t ever be completely satisfied without anal on a regular rotation. I don't know why I feel this way, but I couldn't go back after my first time experimenting with it. I feel so strongly about it, in fact, that it almost prevented us from being together because I couldn’t nut up and tell her about my kinks. Considering Ainsley’s prior sexual inexperience, I was terrified she’d think I was a freak or something. I’ve been head over heels in love with this girl for years. I had convinced myself that it was better to love her from afar and still be in her life than have her reject me.
Even though anal is barely taboo anymore, I’ve been raised by religious extremists who think sex’s only purpose is procreation. Only purely vanilla hetero sex is acceptable. If you venture outside of that, you’re a deviant. While I don’t share their beliefs, it’s been drilled into me for years, especially after my sister came out as bisexual. I’ve learned to tune out my parents for the most part, but there will always be a small part of me that doubts whether or not my preferences are normal.
Ainsley has been incredible, assuring me she thinks there’s nothing wrong with desiring certain things in bed, as long as your partner is willing. And she’s been extraordinarily open-minded and enthusiastic about it. I can confidently say she’s enjoyed the light ass play we’ve engaged in so far. But I’ve been allowing her to set the pace on this particular front. The last thing I’d ever want is to cause her discomfort in any way.
She turns around to face me. “Reed? Did you hear me?”
“I heard you.” I swallow. “But are you sure? I don’t want you to feel pressured to—”
Ainsley gently pinches my lips together. “I’m sure, Reed. I’ve been ready for a while now...but since Christmas was coming up, I figured I’d make it one of your presents.”
I smirk. “You’re giving me the gift of anal for Christmas?”
She rolls her eyes. “Oh my God, that’s exactly what Jazz said.”
I release a shocked laugh. “You told Jazz?!”
Ainsley smiles. “There’s not much we don’t share. Unless it has to do with her sex life with my brother because...gross. Kingston and I may have shared a womb, but I don’t need to know that shit.”
Now I really laugh. “Don’t worry; he feels the same about it. We’ve adopted a don’t ask, don’t tell policy.”
I’ll admit, dating my best friend’s twin sister can be challenging at times, namely because I can’t be nearly as open with him anymore. But Kingston has been cool with it for the most part. He knows that I’m in this for the long-haul with Ains. As long as she’ll have me, I’ll be here to worship the ground she walks on. It’s a good thing I have another best friend as a backup, though. I’ve never been a kiss and tell kind of guy, but sometimes, you just need to discuss certain things with another dude.
“Can we stop talking and move on to the fun part now? I put some goodies in the nightstand drawer. You should check ‘em out.” She’s bouncing on the balls of her feet.
I grab the back of her neck and pull her in for a hard kiss. “God, I fucking love you.”
Ainsley’s mouth curves into a soft smile. “I love you, too, Reed. Now, fuck me in the ass.”
Ainsley squeals when I pick her up and toss her haphazardly on the mattress. “Yes, ma’am.”
Before joining the gorgeous woman on the bed, I walk over to the nightstand to see what kind of goodies she’s planted. I smile as I retrieve the bottle of lube and a jeweled butt plug. Ains has a spectacular ass, but my God, it’s going to be out of this world with that ruby stone winking back at me as I pound her pussy from behind.
I toss the plug and lube on the bed and start removing my clothes. “If you want to stop at any time, you need to tell me, okay?”
She licks her lower lip as she watches me undress. "I'm not going to change my mind, Reed. I want this, and I trust you to make it feel good.”
I nod, telling myself to shut up and stop questioning everything. She loves it when I take control, so that’s what I’m going to do. “Face down, ass up, Ains.”
Her eyes glitter with excitement as she rolls onto her stomach, propping her ass in the air. “Come get it, babe.”
I growl as I join her on the bed, spreading her round cheeks with my palms. I don’t hesitate for a second. I flatten my tongue and immediately start licking her pink rosebud until she’s moaning and mumbling incoherently. Her limbs flail wildly, and she screams my name as I insert two fingers into her pussy. Damn, crotchless panties come in handy, don’t they? I pump my fingers in and out while I eat Ainsley’s ass like it’s the most delectable ice cream cone on the planet.
“Soooooo good,” she groans. “So, so good.”
“Mmm,” I agree.
I remove my fingers from Ainsley's cunt and push her forward a bit, so I can eat her pussy. My finger is slick from her juices, so I use it to tease her tight asshole as I suck on her clit. Right before she comes all over my tongue, I push my index finger up to the second knuckle. Fuck, I love how she tastes. I’d eat Ainsley’s pussy—or ass for that matter—every day for breakfast, lunch, and dinner if she’d let me. I pump my finger in her ass while she slowly comes to a stop on the O-Train. When her shudders finally cease, I move on to stage two of prep work.
“God,” Ainsley pants. “You’re so fucking good at that.”
“Baby, we’re just getting started.”
She turns her face to the side, giving me a lazy smile. “I can’t wait to see what you’ve got.”
Without any kind of warning, I smack her ass in rapid succession, alternating cheeks. Ainsley moans as her skin warms and a quick dip between her thighs confirms how much she enjoyed that. I would’ve never guessed Ainsley got off on being spanked, but I can’t say I’m not super fucking happy about that fact. I massage the soreness away with one hand as I roll the pad of my finger over her swollen clit. A few more spanks coupled with some clitoral stimulation, and she’s coming a second time, soaking my hand.
I pop the top on the lube bottle and apply a generous amount on the steel plug. This one is somewhat intimidating to an ass play novice, but Ains and I have gone through two smaller sizes already, so this is a good progression. I usually supply the toys, so I was a bit surprised when I opened that drawer and saw this.
I squirt some lube directly down her crack and work a bit inside her hole with my finger. “Where did you get this stuff anyway?”
“Online.” She gasps as I remove my finger and press the cool tip of the butt plug against her puckered hole. “Fuck, Reed.” She stretches the first word out as I carefully ease the plug inside.
“You doin’ okay?”
Ainsley nods. “More than okay. Keep going.”
Slow and steady wins the race, I remind myself as I slide it in more and more until the jewel is resting between her cheeks.
“You still good?”
“Amazing.”
I lean over until my chest is pressed against her back, sucking on her delicate earlobe. “You want my cock in your pussy, baby? You wanna feel what it’s like having both holes stuffed at the same time?”
We've used several different kinds of toys, but double penetration would be a new thing for us.
Ainsley shivers as I trail biting kisses down her neck. “God, yes.”
I stay close as I ease my dick inside, groaning as I feel the plug on the other side of that thin wall. Ainsley curses and gasps and moans as I move inside of her sweet cunt. Fuck, she's so tight like this; I'm not going to last if I keep up this pace. I know I need to make her come quickly so my cock can trade places with the plug.
“Rub your clit for me, baby. I need you to fucking come, Ains.”
Ainsley's arm moves beneath her until she's in a position to heed my command.
When she starts rubbing her slick flesh, I pull out to almost the tip before slamming myself back inside. As I feel her clenching around me, I finger the jeweled end of the plug, moving it around.
“Reed...God...right there. Don’t stop. Gonna...come.”
After she comes for a third time with my name on her lips, I ease the plug out of her ass, loving the sight it leaves behind. She's definitely ready to take my dick now, and I can't fucking wait.
I press the flared head between her ass cheeks. “You ready, Ains?”
“Do it, Reed.”
We both groan as I ease inside her tight channel.
I rest my forehead on her shoulder once I’m fully seated. “Fuuuuuuck.”
Holy shit. This is pure fucking ecstasy. Who needs drugs when you have this?
I give Ainsley a moment to adjust before I start to move. I experiment with shallow thrusts, allowing her to get used to the feeling before lengthening my strokes. When I'm finally giving her all of me, Ainsley's shouting obscenities, telling me how incredible it feels, how much she loves my dick up her ass. I can't even manage to say that I think the same because I'm too busy trying not to blow my load. Christ, I'm not going to last much longer. She feels too good wrapped around me.
After she comes for the fourth time, I rise up, wrapping my fist around the band of her bra for leverage. The need to get off is severe as I pound into her fast and hard. After only a few more thrusts, I feel the ache building in my balls, so I pull out, jerking my dick to completion.
As I jizz all over her ass, I say, “Now, that’s a fucking beautiful sight. I love seeing my handprints on your ass mixed with my cum.”
I swipe a finger through the sticky substance, trailing it down the crack of her ass.
Ainsley giggles. “It’s always the quiet ones.”
I chuckle. “What?”
I grab my shirt off the floor and start wiping up the mess I made. When I’m done, Ainsley rolls onto her back and motions me closer.
"Come here, and I'll tell you."
I crawl on top of her, careful not to smush her with my weight. “Now, what were you saying?”
She flashy a toothy grin. “I’d said, it’s always the quiet ones.”
I quirk my head to the side. “What does that mean?”
Ainsley stretches her neck to place a kiss on my jaw. “It means that you’re my kinky-as-fuck, dirty-talking, deliciously filthy boy. But you’re usually so quiet and reserved, I would’ve never thought you’d be this way in bed.”
“Are you complaining?”
She shakes her head. “Hell no, I’m not complaining. I love everything we do sexually, especially what just happened. I never thought anal would be so awesome.”
I raise a brow. “Does that mean you’re open to doing it again?”
“I’m definitely open to doing it again." Ainsley scrunches her button nose. "I mean, not right this second because your dick is big, and my ass needs time to recover, but soon, yes.”
I laugh, trailing kisses along the slope of her neck. “I fucking love you, Ainsley Davenport.”
She gasps when I move down and pull her peaked nipple into my mouth. “I fucking love you too, Reed. Merry Christmas.”
I smile. “Merry fucking Christmas, baby.”
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©2020 Laura Lee