Hooking up with my hot boss on a business trip [F/F] | 2016

I'm a long time lurker on this subreddit and never thought I'd have anything of interest to share, and I can't believe I'm even here now... but something happened.

So here's the backstory. I've known my boss for about two years now. She started out as my close mentor, and then I applied for a position at the company where she worked. Even though I call her my 'boss', she isn't technically in charge of me - our departments work closely together, but I have a different manager. We discussed this late one night last October as we were working on a project and our conversation turned pretty personal (though non-sexual). We'll call my boss Leisha - she's in her early 40's, recently divorced, and looks amazing for her age. Fiery red hair, tight body, and always looks damn fine in a business suit. I'm in my early 20's, thin, androgynous, blonde hair in a short-ish cut.

Leisha invited me to go with her on a business trip to a conference. She and I always saw eye-to-eye on a lot of aspects of our company, and that's why she wanted me to go along (so she said). The hotel is in a gorgeous tropical locale - sandy beaches, palm trees, the works. Leisha told me we'd be sharing a room to cut costs. When we get to the hotel room, we discover that there is a jacuzzi tub in the bedroom. A literal hot tub in the corner, next to the balcony and the two queen beds. I start joking about this and tell her she booked us a "lover's suite". This is all in fun - Leisha's straight as a board and I'm just the funny lesbian, no harm done. So over the first two days of the conference everything is a complete whirlwind and we're rarely in the room together (it's a five day event). On the third day... things begin.

It was early evening and I was out on the balcony, watching the sunset (I know, how Nicholas Sparks movie of me). The balcony has a nice padded couch-style bench instead of just chairs. I'm sitting out there, sipping a beer, when I hear Leisha come into the room. After a few seconds, she peeks her head out and walks on to the balcony. I'm trying not to stare - she's put on 'pajamas' that are just a thin black tank top and incredibly short athletic shorts. She sits next to me and is drinking some sort of tropical drink from the hotel bar, and we start discussing the conference overall and laughing about it. I notice that she's sitting very close to me, and has her arm draped over the bench behind me. I'm overdressed, still in my button down and slacks from the day, and I joke with her that I have to get more casual as I take off the button down. I'm just wearing a thin gray tank underneath.

She tells me that she's annoyed at one of the conference-goers that kept hitting on her, some older man with one of our competitors. And then she says coolly, "I'm not into guys that old. Frankly I think I'm giving up on men entirely." I cheers with her and laugh. "Well I'm definitely there with you. No wonder you got us the lover's suite, huh?" At this point my heart is pounding, because suddenly our joking feels a lot more real. There's a few layers of vulnerability happening all at once - we're miles from home, sharing a room, both drinking and both wearing a lot less clothes than we usually do around each other. But the conversation doesn't go completely to flirting yet. She starts talking about how the last time she had a lover's suite was with her ex-husband, on a trip they took to try and save their non-existent sex life. Suddenly we're both talking about general sex things, more just "girl talk". (At this point she's also gotten us more drinks from room service). I start talking about how amazing sex is with women - you just connect more, it's so much fun, and I mention my affinity and stamina for oral. We lock eyes and she says, "You know, I've always wanted to try it with a woman. Just never got the chance." "Well, just let me know anytime." I can't even believe I manage to say this, it's really the alcohol talking, but then she pulls me in by the back of the neck and kisses me.

We start kissing hard - tongues everywhere, hands pulling each other close, I start nibbling along her neck. She tastes like pineapple and her skin is so perfect - smooth, hot, smelling like fancy perfume. Her hands are under my shirt in an instant, grabbing my tits roughly. I pull back for a second and say "Not that I don't love the scenic view, but this might work better on a bed." She nods and we quickly walk inside.

She sits down on the edge of her bed (closest to the window) and I quickly comment that my slacks feel ridiculous and slide them off. She strips of her tank top in return and I get my first look at her gorgeous tits: huge with perky pinkish-red nipples. I get on top of her and kiss her again, then start kissing towards her chest, and flick her nipple with my tongue. She cries out and balls my hair in her fist, pulling me closer. I start playing with both her tits, squeezing them gently with my hands, sliding my tongue over her nipples, sucking them hard. I sit up a bit and slide off my shirt and bra. When I come back down she slides underneath me and hungrily grabs my breasts and starts playing with me, commenting "God, these are fun!" She seems to be getting really turned on, and I decide to test the waters. I trail my fingers up her inner thigh and lightly grab her pussy over her shorts, and she immediately humps my hand hard. I rub her some more, then slip my hand under her panties and feel her wet pussy in my hand. She's completely soaking, and surprisingly bare (I truly was expecting hair and that threw me off). She looks up at me and says, "So you're really into oral, right?"

That's all the encouragement I need to dive in. She moves up on the bed to rest her head on the pillows, and I slide off her shorts and underwear. Her pussy looks so good, and I lay down flat, slipping my shoulders underneath her legs and giving her a long lick from her opening to her clit. I swear I've never even tasted better - she just tasted so CLEAN, like completely fresh with only a hint of saltiness. I start sucking her clit as I side two fingers into her. She's moaning so loud now I'm worried we're gonna get the hotel called. She starts moaning and crying out louder, pulling me closer, and begs me to fuck her hard. I'm slamming 3 fingers into her as I suck up and down on her clit and I feel her cum hard against me. But as she comes down... I keep going. I start slow, but never take my mouth off her, as I flick my tongue over her clit, and I start to fuck her differently - instead of slamming in and out, I'm moving my fingers in a curling motion inside her. She says, "Holy fuck, what are you doing?" I pause for a second and look up, "Is this okay?" She responds "Damn straight it's okay, please don't stop". I keep going like that, slower, almost a deeper fucking, and she cums again even harder, her whole body shaking. This time I still don't stop and I'm not letting her come down, instead I start slamming in and out of her again and start sucking her clit damn hard, and she's crying out and saying my name and lifting off the bed and says, "fuck, I'm cumming again, oh god" and her voice barely sounds like her anymore as she shudders, slamming back onto the bed and curling herself around me so tight that she's biting along my spine. She finally pushes me away and I slide off my underwear and curl up beside her, resting my throbbing pussy against her thigh. We start bedroom talking - she tells me she's never cum like that before, we joke about how she bagged this younger 'stud' and about her being a cougar, I tell her how amazing she tastes. She says she kind of wants to know how I taste, and reaches down and cups my whole pussy in her hand. I'm rendered a bit incoherent because I'm so turned on. She pushes me back and I lay down and spread my legs.

"Now I've never done this, so I might suck, please don't make fun of me." I laugh and quip back "Well sucking is the whole point, so you can't be that bad." I like that we can just laugh and joke together. She playfully slaps my thigh, then leans down and places her mouth over my pussy. She licks my clit, then starts putting her tongue inside me, firmly sliding it as far in as it'll go. This feels incredibly and I'm humping against her. She plays with my clit in her hand and keeps sliding her tongue in and out of me and I cum much faster than I expect - it washes over me suddenly and I groan out. I practically gush.

She kisses my thigh and looks up at me and nearly deadpan asks me "could I eat your ass, too?" I'm completely floored and have rarely tried anal, but I'm so turned on I'll go for anything. I flip over and she slides a pillow under me. She starts rimming me gently, then is sliding her tongue into my ass just like she did my pussy. I'm overall so surprised that she wants to play with my ass, but she's so enthusiastic, gripping my asscheeks hard and really eating my hole. When I get a coherent moment I ask her if she'll fuck me too, and she slides two fingers into me as she keeps tongueing my ass. She fucks me slow but deep, same with her tongue, and soon I'm cumming hard all over her face, I'm so wet. I flip over and she slides her fingers back inside. "Do you want me to keep going, like you did to me?" she asks.

I tell her yes and she smiles and says "Good" and begins fingerfucking me hard. She's on her knees above me, her hand next to my face and red hair falling around me, as she completely slams into my now well-fucked pussy. She starts talking even more: telling me how hot and young I am, how she loves how my pussy feels, how she wants to make me cum until I beg her to stop, and wants me to fuck her until she can't take it. I don't even have the energy to moan anymore, just breathe hard, and as I get closer, I quickly ask her to move her fingers inside me as I did to her. She gets it fast and is flexing inside me, hitting my g-spot, and I cum hard and squirt hard, gushing over the bed, letting out one loud scream. She slams four fingers into me suddenly and hard, telling me how fucking hot that was. She doesn't let up and keeps fucking me, this time deeper and slower, then leans down and starts biting my chest and nipples and tits, telling me she's going to mark me.

I'm pretty sure I can't even cum again, and kind of want to wind down, so I ask her if she wants to 69. She climbs on top of me and hovers her pussy over my face as she starts to lick me. Pretty soon we're both humping each other's faces and sucking hard - I manage to put my tongue in her as she did to me and fuck her with it, even though I've got a smaller tongue she really seems to love it, and she cums again, quieter and softer but it's definitely there. I manage to cum once more, holding her head with both hands and moaning, almost tearing up.

We finally lay back on the bed, both completely and utterly spent, and snuggle up together. It takes us quite a while to catch our breath. We end up just laying in bed together before we go to sleep, both chugging water and cuddling.

Let me know in comments if you want to know more about our adventures, including a trip to the in-room hot tub ;)