Normally I hate Mondays, but something was special about today. I could feel it. My boss is Kate, who is also my best friend, is 35 years old, has a kid, and is adorable as hell. She is definitely a MILF, and I’ve had a crush on her since I met her. She is absolutely gorgeous, and super funny. Kate just got off work and I am driving her home as we live next door to each other. On the drive she’s telling me a bunch of awful dad jokes, but as always they still make me laugh. She is so proud of them too. When we get home she goes back to her place to change and then walks over to my apartment. She is wearing a white tank top and jeans, with her hair up in her bun as usual. I can’t help but think how sexy she looks, with her ass tight in her pants. Kate knocks on the door and I walk over to let her in. She sits on the chair with a bottle of hard cider in one hand and a cigarette in the other. I know cigarettes are bad but something about the way she does it is just so sexy. I walk over to my bar and make myself a stiff drink, sitting down on the edge of my bed facing Kate. I can’t stop smiling, because I always love when she comes over. She is my best friend, so how could I not get excited when we chill together. Obviously there’s often the hope that something more might happen between us running through my thoughts. We start talking about how her day at work went and somehow we end up in the conversation of sharing our sexual fantasies. I’m not sure how our verbal interactions end up sexual in nature so often, but I’m not going to complain about it. It turns out that we would be a perfect match, as she leans to the submissive side and I am much more of a dominant. So we continue talking about fantasies and I tell her I’ve had thoughts and dreams about her. She doesn’t seem surprised. She finishes her cigarette, drops it in the ashtray, and comes over to sit next to me on the bed. Kate takes a swig from her bottle and leans into my ear, whispering “I’ve thought about fucking you for a long time”. My heart drops a beat, and my hands start twitching, realizing it’s now or never. I turn to face her, and I smell an intoxicating combination of slight sweat, alcohol, cigarettes and lust. I reach out to flip a strand of hair over her ear, and twist my hand back around her head to pull her closer. I bring her in and put my lips to hers. Our eyes lock and we begin to slowly kiss. It’s passionate at first but it gradually turns into a crazed lust-filled moment. I can feel the need in her movements and twitches, and can see the want in those gorgeous eyes. My tongue wiggles in and out, playfully toying with Kate’s, flicking around the inside of our intertwined mouths. I can feel the warmth and her taste is a mix of salt, and the sting of tobacco. She puts her hand on the front of my pants and her fingers rub along my hard dick. My hands instinctively reach up and start massaging her firm breasts. As the kissing intensifies, so does the groping. I push my hands up under her top and around her bra to start playing with her nipples, which causes Kate to moan softly, making me even harder. In response she unbuttons my jeans, and her hand wiggles down onto my member. She starts to gently stroke up and down, which takes me to a slow moan as well; Kate brimming with pride at the sound. I pull my hands from their warm and cozy spot, grabbing the tank top and taking it off. As I reach around for the bra straps, she pulls down my jeans to my ankles and pulls my boxers down with it. As the elastic of my briefs fall, my cock springs out at full length and slaps her in the face from the momentum. She stares at it in awe. “I had no idea you would be this big!”, she says in shock. I grab her hair again and bring her back in. I softly nibble her lips and pinch her cute nipples. Kate whimpers slowly, with unsteady breath, and I can feel her body trembling; wanting more. I lower my mouth and start kissing her neck, biting her ears, and follow the trail down to start sucking on her supple breasts. I can still feel one hand rubbing my shaft and then feel the other hand reach up and start fondling my balls. God she is fucking good at this. I abruptly stop, and she looks at me confused. With a smirk, my hand wraps around her throat, and I flip her down on the bed. I climb on top of her and pin her arms to the sides with my legs, as I straddle her. My hand reaches down and pulls off her jeans and I throw them to the side of the bed. Then my teeth clench around her purple laced panties and yank them down too, revealing the neatly trimmed triangle of glistening black bush. Moisture has been building around the cute pink folds, causing a trickle of delicious juice to travel slowly down her body. Quickly my tongue races to lap it up, tasting the angelic sweet tang. I hover there, building the anticipation until Kate can’t take it anymore, and begs “please daddy”. That sets me off, and I bury my face into her pussy. The smell alone is enough to make me salivate, and I am mesmerized, savoring the moment. My tongue flicked over her clit. Kates hips buck back and forth in the rhythm of my licking. I push two fingers in to her warm cave, slipping them in without resistance. I rock my tongue up and down, teasing the entrance, and then shove it in deep. My mouth goes from her quivering pussy to her clit, sucking and nibbling while I continue to thrust with my fingers. Now I have four fingers in and Kate’s moans are becoming faster and more intense. What feels like an hour passes, and she grabs my head, shoving my tongue in as deep as it will go. Her back arches and her toes curl as she lets out a groan of pleasure and pain as I clamp down on her clit with my front teeth. I can taste the heavenly cum before I even hear her scream. Her sexy eyes roll back and her mouth is agape. I keep going though, pushing two of my fingers into her little pink butthole, and she sucks in a breath. I thrust my fingers in both her holes now, still sucking and biting her clit, even more sensitive than before. My tongue goes further down and wiggles into her backdoor, now covered in pussy juice and spit. Kate lets out a gasp and sticks a few of her own fingers into herself to match the rhythm of my tongue. I move my head up and look at her eyes. She is having the time of her life, face awash with ecstasy. I maneuver her into a position on all fours on the bed. I bring my steel hard cock to her lips and instinctively she wraps them around the throbbing head. Kate begins to play with my dick, flicking her tongue up and down, circling the sensitive tip. Her hand reaches up to cup my full balls, rubbing them, and her other hand begins to stroke me while she sucks. She goes slowly at first, taking in just a few inches of my warm rod, while her tongue laps the underside. Then in one smooth movement, she drops down all the way to my balls, swallowing my whole shaft. She bobs her head slightly, letting me feel the warm tight embrace of her throat. The pleasure makes me moan loudly. My hips move in rhythm, pushing deeper in her mouth. With each thrust, she gags and chokes, struggling to handle all eight inches of dick. I grab her hair and start to facefuck her, bouncing her head forcefully on my erect cock, savoring in the sounds she is making. I push her down to the base, and hold her nose with my fingers, watching as she struggles to find air. Her eyes roll back and I release my fingers, but keep her head firmly in place. She still finds it hard to breathe with my meat deep in her throat, as she gags. She pulls off, and wraps her spit covered mouth around my nuts, sucking them each slowly. Her hands reach up to stroke me, her eyes filled with joy. As she chokes on my rigid erection, I can see all the muscles in her neck tighten and contort. I keep fucking her warm mouth, my balls slapping against her chin. As if realizing I was close, she wraps her hands around my ass, pulling me in faster and deeper, circling her tongue around my balls. With a final thrust, my jizz explodes down Kate’s throat as her eyes roll back. I reach behind me quickly to grab a large metal buttplug from my bedside table, rub it along her glistening slit, and slide it into her ass. She gasps with a smile, squirming around in pleasure. I flip her over on the bed, with her legs wrapping around my waist, and impale her with my shaft. I enter her with little effort, and begin a steady pumping of her warm pussy. Her moans echo against the walls, making me grin. Sweat is shining on our skin as our bodies connect with each thrust. I keep a hard but steady pace, fucking her with all my strength. My hands wrap tightly around Kate’s neck, choking her as I slam in and out. I melt at the sound of her moans, as they become stuttered with the lack of air entering her lungs. I reach one of my hands down from her neck, and begin to rub her pleasure button. I can see and feel her whole body shiver as I fuck her. As Kate gets closer to orgasm, I feel her pussy tighten around my cock. I start to move faster and with more power to each pump, bringing her moans to a crescendo. She explodes with moans and screams as she cums again. I quickly pull out, and bring my mouth to her cunt, licking up the various juices lining it, before flipping her ass up to face me. I grab my whip from next to the bed and begin to hit her plump cheeks with the spiked metal strands, leaving red marks all along her taut butt. She lets out sharp yelps of pain, but I can tell she is still enjoying herself, looking at the sheer ecstasy on her face. After feeling satisfied with the redness on her ass, I throw aside the whip. Then I cuff her hands behind her back, plant her face down, and pull that heavenly ass up to face me. Hastily I remove the plug efficiently with my teeth, before sinking my tongue into the warm hole. She tastes like perfection, and I go to town on her little pink starfish, lapping up all the juices that had collected there. I stuff myself in her pussy one more time to cover my dick in her cum, and slowly slide into her ass, garnering a moan. Burying myself in to the hilt, and pulling back to the tip, I keep up a steady rhythm of pumping. Her tight hole is inviting, wrapping around me and pulsing with pleasure. I reach up with one hand to tightly wrap around Kate’s throat, choking her while I’m balls deep in her ass. She tightens on me gradually, like a vice grip, until I can’t take it anymore. With a groan I push all the way in, and let loose a rocket of cum in her gorgeous ass. I pull out slowly, watching the jizz spurt out as her muscles contort. I flip her over to face me and bring my lips to hers, kissing her softly. Pulling away I ask “was that as good as you’ve imagined?” She replies with “It was everything I wanted and more.” We collapse next to each other on the bed, covered in sweat and various other fluids, and I pull her up against me. I wrap my arms around her chest, snuggling up next to her. I lay there, holding her, with nothing in my mind but happiness. The sight of her angelic body right here makes me wonder if this is a dream. How could someone like Kate, ever want someone like me? I brush some hair back behind her ear, and lean my head on her shoulder. The smell of the room is intoxicating. I think I love her, and I don’t know what that means. I kiss Kate on the neck, and lean back into the pillow, feeling the warmth of her body against mine. After a while we get up, take a shower and she gets dressed. As she leaves she says she would love to do it again soon. I smile and nod my head, too exhausted to reply. I couldn’t have pictured this day going any better.
Source: reddit.com/r/eroticliterature/comments/rfm38n/my_boss_is_a_milf