This happened several years ago, in my late 20s. Names, dialogue and details have been adjusted to preserve anonymity and story flow. A bit about me: I’m average height, weight, and dick; long wavy brown hair, a beard, and big blue eyes. Teddy bear vibes. I’m a licensed massage therapist, and every so often I’ll find myself at a conference of fellow professionals. During the day this involves seminars, classes, demonstrations, sales, etc. At night things sometimes get a little nuts.
This particular conference was for a luxury spa brand I worked for at the time, a training weekend for myself and 50 of my colleagues from around the country on new services and products for the coming year. The company had me sharing a room with a quiet dude from Maryland named Tom. Nice enough guy but we didn’t really make a solid connection at first. First night of the conference there’s an open bar cocktail hour that I and almost every therapist there make the most of, so we’re all getting very comfortable with one another pretty quickly. Massage therapists can be a pretty physically affectionate crowd, and I’m never great at picking up signals, so it takes me an embarrassingly long time to realize that this red-headed therapist named Jess has been flirting with me.
Jess is older than me, maybe ten years, and has a couple of kids in their teens. She stands an inch taller than me, a little more in heels, with mischievous hazel eyes and a lightly freckled face. The low cut of the sparkly black top she’s wearing accentuates her c-cup breasts, and I’m yammering on, oblivious, until she puts a hand on my forearm and strokes it playfully with a finger. I trail off whatever I’m saying, returning her smile. “Want to go up to my room?” I ask, hopeful. She rolls her eyes playfully, takes my arm and laughs “Finally!”
We begin making out as soon as the elevator doors close behind us. Buzzed and horny, our hands are all over each other as we kiss, one of hers rubbing the bulge in my jeans. We compose ourselves as our floor dings, the doors opening to reveal a mercifully empty hall. Giggling like teenagers, we play grab ass as we hurry to my door. I have the key in my hand when I remember my roommate.
“Uh, shit. My roommate might still be awake.” She shrugs. “Well mine definitely is, so my room wont work.” I let out a sigh, hoping this night will still end well. Opening the door, however, it’s clear my roommate is still awake, reading in bed.
We exchange pleasantries. They had already met earlier in the day, and whether he takes a hint or is genuinely tired, he soon turns off his bedside light and closes his eyes. Jess and I chit-chat for a few minutes, but the moment Tom seems asleep we’re making out again. Her pants and panties come off quickly and I direct her to sit on the edge of my bed, legs parted for me. I kiss her inner thighs, enjoying the pleasures of discovering her touch, her scent, her taste. Ever eager-to-please, I can’t long resist the urge to start eating her out. My tongue teases her entrance before I slowly draw it up to her clit, my hands gripping the top of her thighs, her hands gripping my head. She tries her best to be quiet. We’ve been periodically checking to see if Tom is still sleeping, but now we’re too preoccupied. My tongue is a flurry against her, my hands hold her hips firmly as my efforts make her writhe in quiet ecstasy. Her breath is ragged, head nodding a silent “yes” over and over as her fingers grip my hair more tightly. She gasps, her pelvis bucks against my face, legs shaking a little as she attempts to orgasm quietly.
After a few moments of breath-catching, I kiss my way up her abdomen, raising her shirt as I move slowly higher. Coming down from her orgasmic high, she takes her top and bra off, allowing my mouth access to the rest of her. I take my time appreciating her breasts and nipples with my mouth and hands. Her breathing grows increasingly excited again. Her eyes are closed, hands gripping the bed sheets beneath her. My lips trace her collarbone, then a path up her neck to her left ear. I nibble a little, and whisper into her ear, letting her know how much I enjoy making her feel good, how good she feels and tastes. Her only reply is a breathy “fuck…”
Next thing I know, she’s fumbling with my pants, still on for some reason. We share a chuckle as she struggles a bit with the belt, and I take a step back from the bed to undress properly. I love the look of anticipation on her face. The moment my pants and underwear hit my ankles she sits up and smoothly slides herself to a kneeling position in front of me on the floor. “I like the curve of your cock,” she says, and I feel her tongue press against it as she slowly licks her way from base to tip. Reaching the head, she quickly deepthroats me, eliciting a surprised gasp of pleasure. When I feel the tip of her tongue graze my balls I can’t help myself: a full-volume “holy shit” slips out of my mouth. She giggles and moans with me in her mouth, and I’m feeling ready for the Rapture. She takes me out, slides her tongue all around my shaft and head before taking me all in again. My right hand touches the side of her head, my thumb traces her ear and my fingers slip behind her head, gripping some of her hair. She pops me out of her mouth long enough to say, “yes, do that” before swallowing me whole again. Communication is important! I tighten my grip on her head, fingers entwined in her hair as she encourages me through increasingly rough facefucking (something I had little experience with but I was so turned on by how much she enjoyed it).
I let go of her head and take off my shirt, and she slowly slides her mouth off of my cock and stands in front of me. We kiss, our arms wrapping around each other, pressing our naked bodies together. She backs away after our passionate exchange. “Be right back,” she whispers and kisses my cheek, “go grab a condom.” She tip-toes into the bathroom and I rummage through my backpack, thankful I brought some.
I’m on my back on the bed, staring at the ceiling when Jess returns. I take her in: pale, freckled, soft curves front and back. I admire the sway of her hips as she approaches, and the desire in her eyes returns full force to my erection. She smiles at the immediate response my body has to seeing hers. “Why thank you,” she says, eyes twinkling. I tear open the condom wrapper and roll the rubber on. “Feel what you did to me,” is her quiet command as she climbs onto the bed and grabs one of my hands, guiding it between her legs. Two of my fingers slide with ease into her pussy, and I moan in aroused appreciation, and she lets out her own. I flex my fingers slightly inside her, and she squeezes them in return, giggling a little.
She wraps a hand around my shaft and leans in to kiss me, whispering, “that feels very nice, but I really need this.” I obligingly withdraw my fingers, starting to give her clit some attention with them. “Jesus, get inside me already,” she growls playfully in my ear as she impales herself on my cock. I moan again, less mindful of our volume with each ecstatic minute, “goddamn you feel so good.” “I know, right?” She grins down at me, slowly sliding herself up and down the length of my cock. I laugh, I can’t help myself. She clamps a hand over my mouth, her eyes mischievous. We both look over at Tom, who is undeniably awake, looking over at her straddling me.
I quickly glance back at Jess to gauge her reaction, but the look of wicked excitement on her face reassures me. She resumes her slow ride, taking her pleasure. “Sorry to wake you,” she says to Tom. “Don’t worry about it,” he murmurs. Jess leans back, hands braced on my legs behind, picking up her pace. Her chest is flush with excitement, her breasts bouncing lightly. “Enjoy the show I guess,” she says to Tom, who doesn’t reply, and I laugh again. She sticks her tongue out at me, “what?” Her pussy tightens around my cock. “I’m just having fun fucking you,” I replied with a smile. “Right back ‘atcha,” she said, grinding harder on top of me. Her hips rock steadily as she takes control, and I love every second of it. I glance over at Tom, who is admiring the woman on top of me almost as much as I am. I smile, enjoying being a part of the show, enjoying another pair of eyes watching us fuck.
I sit up, embracing and kissing Jess, before rolling us over so that I’m on top of her. I thrust down into her at a brisk pace, both of us moaning as her nails dig into my back. I glance at Tom, clearly stroking his own erection now. I lean in close to Jess to whisper, “I think he is enjoying the show.” She looks at Tom and makes an aroused near-growl when she sees him touching himself.
“Flip,” I tell her, pulling out. She gets on all fours and I pull her back near the bottom edge of the bed and I position myself behind her, one foot on the floor, the other on the bed next to her. “Oh fuck yes,” she says as I slide my cock against her labia and clit before entering her again. “Unghh, yes, don’t stop,” she moans. I pull almost all the way out, holding steady, eliciting a whimper from Jess, “please, I need it back.” I look at Tom, and he returns my gaze, nodding encouragement. I drive myself back into her, picking up my pace with each hard thrust. She lowers her head and shoulders to the bed, bracing with one arm as she reaches back with the other to rub her clit and touch me as I slide into her. Tom’s breathing is growing loud, he’s obviously getting worked up and has pulled the sheets off, his hand working his exposed cock. My hands slap against Jess’ ass, eliciting a gasp. “Hold on,” she manages to say, tapping my leg. I slow down, and she slides her upper body further up the bed, laying flat on her chest. She then turns on her side, facing Tom and offering him a great view as I reposition myself.
“You feel incredible,” I confess as her pussy envelops me again. She grips the bed sheets, pressing against me so she can feel every last millimeter of my cock inside her. Her eyes lock onto Tom, who is stroking his cock frantically. I can tell the dude is getting close, and so can Jess, who beckons him to the side of our bed with a curled finger. Tom practically leaps across the divide between our beds, precum glistening on the head of his cock, which Jess wastes no time taking into her mouth. The sight alone has me ready to explode, and I’m not the only one. “Uhh, I’m close,” Tom groans, and Jess moans in eager approval, gripping his ass as he fucks her mouth. “Right behind you buddy,” I laugh, hurtling towards an orgasm of my own.
Tom’s wordless exclamation announces the arrival of his load in her throat as Jess keeps her lips tight around the cock spasming in her mouth. The sight and sound and feeling are too much for me, I’m about to explode. “You’re gonna make me cum so fucking hard,” I manage, my body tingling in anticipation of release. “Mhmhmmm,” is her dick-muffled moan of reply. My hands clamp down on her ass and thigh as I thrust a final time, filling her and the condom. My body convulses in pleasure and I let out an ecstatic roar, wanting her to know how good it feels. She lets Tom slip out of her mouth, turns to smile up at me, and reaches up to press her palm against my sweat-dampened chest hair. We share several moments catching our collective breaths.
I pull out, quickly hopping out of bed to dispose of the condom and wipe up a little in the bathroom. When I return, Tom is back in his bed, eyes closed again. Jess lays on her back, one arm above her on the bed, the other on her abdomen, hand resting inches above her small red strip of pubic hair. I admire the rise and fall of her chest and she smiles at me as I wordlessly drop to my knees in front of the bed and pull her back down to the edge. “Oh!” She squeals a little in pleased surprise. “I have a bad habit of snacking before bed…” I say, and lower my head between her legs. My lips brush briefly against her clit, eliciting another squeal. I suck her clit between my lips and her hand moves from her abdomen to my hair, gripping my head. “Yes, yes,” she hisses between her teeth as I tease with my tongue and slip my right middle and ring fingers into her. My lips release her, and I shift to long, firm strokes of my tongue from my fingers back up to her clit. “Yes, stay there,” she growls, and the hand gripping my hair holds me firmly in place. She gyrates her hips, gripping my fingers inside her as her clit rubs against my eager tongue. Her breath and pace quickens and she’s in control again. “Close…close,” is all she can get out, and I moan in anticipation, my tongue subtly vibrating against her. She cries out, clamping my head between her legs as she orgasms. Her legs quiver for several moments and then relax away from my head. I give her clit a final kiss of appreciation before working my way up her body to her mouth.
We part, finally, and she hops off the bed making her way back to the bathroom. I’m almost asleep when she comes back and starts getting dressed. “Don’t want my roomie worrying about me,” she says, pulling her pants on. “Hit it and quit it, eh?” I tease. She puts her shirt on, presses her lips firmly to mine, and smiles as she pulls back and whispers, “I don’t even remember your name.” Her eyes twinkle and I snort a laugh. She picks up her remaining things. “See you in a few hours,” she says and blows me a kiss before walking towards the door. It clicks shut behind her, and I drift off to sleep, smile on my face.
Thankfully, this was not my last adventure with Jess.
Source: reddit.com/r/gonewildstories/comments/10rqji2/mfm_a_conference_hookup_gets_a_little_wild_when