About a week ago I was on a work trip conference with a co worker, Alison. Alison is about 5 years older than me, attractive, but professional. She's short, has blonde hair she often keeps in some type of braid, and as I mostly know and only see her at work, so she is mostly always in some professional attire, nothing overly revealing or sexual. We have been working together for a few years now and have always gotten along well, and when offered to travel for this conference, it was an easy decision. We met up at the airport, sat in different rows for the flight, but quickly met back up afterwards, gathered our things, and shared an uber to the hotel. That is where we met our snafu that put us into our stories position. So as we get to the hotel, we pull up our confirmation emails, Alison quickly finds out that she booked the right hotel but in the wrong city, one that was a few states away. Unable to find a room that matches her reservation as they were all taken, Alison quickly became embarrassed and frustrated of herself and the situation. I offer her to stay in my room, which was a large king bed room, figuring the mattress would be big enough to share, but that only seemed to weight too much on her. Luckily, the front desk offered us a room that had 2 full mattresses, about the same price as my current room, and that they can adjust my reservation now. That seems to work easier for her, and we agree to it, grabbing our card keys and heading up.
We finally settle in, unpack and each shower from traveling, before heading out for some dinner. We find a nice place, split a bottle of wine over some food, and laugh about us now adding room mates for the trip. We finally make our way back to the hotel, Alison heads into the bathroom and I take the opportunity to change. I do, however, stop half way and just lay on the bed in my boxers and scrolling my phone, and catching up with Katy, completely oblivious to the fact that I only got half way in my "change your clothes" plan and that I now have a female room mate. Alison eventually walks out and goes "Oh my god!" when she sees me laying in my boxers. I look to see her and look down to realize my mistake and embarrassment and hop up out of bed to quickly find some shorts and a shirt, Alison continuing to stand in our foyer and watch. "Alison, I am so sorry! I didn't mean to make you uncomfortable or to be like this. It's a force of habit and I think with the exhaustion from the day put me on autopilot." Alison calms the situation saying it is fine, and that she understands it was an accident. "I'm sure you'll see a bra or underwear of mine at some point laying around. Accidents happen when put in an unusual situation," she says, putting it behind us. We lay in our respective beds, chat more about nonsense. I chuckle and say after a while, that it was good I was still in my boxers, as I prefer to sleep naked and being found in that state would've been much worse." She laughs and says she can't imagine, and then we go into a discussion about sleeping preferences, our spouses, and other mundane topics before we finally go to bed.
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The next morning is where we really hit our biggest snag, and what truly shifted the remainder of the trip. So that day was day 1 of the conference. We wake up, get ourselves going. I opt for the shower to freshen up before hand, while Alison plans to iron out her clothes after being folded up in the garment bags, offering to do mine as she showered fully last night. The bathroom is one that has a sliding door as its door, the shower stall surrounded by glass, being able to view in from the bed half of the room and hallway. All was going well until the sliding door opens. I can see Alison at the edge of it, turning her head but raising her voice so that I can hear her over the shower. "There is no plug in the hall for the iron, and the only place for the board is either in the bathroom or in the hall. On account that you are showering, I clearly only have one option, but the closest outlet is in the bathroom, and it won't fit without the door open." I ask back how much time do we have, and the answer is not enough if we expect to look decent and professional.
I sigh, tell her it is fine and she should just get to it so we can get going asap, and she gets to work. I still have to wash most of my body, and while doing so, with the bathroom door wide open, the steam begins to vent and the condensation on the door clears, and I realize she has a direct line of sight to my naked. "This is really starting off great with how much you are exposing yourself", I think to myself. I try to tell myself, it's not that bad, I can just finish up with showering, she is busy ironing and not paying attention to me, I can just wrap up and then grab my tow--my towel! In all of this, I forgot that I did not grab my towel to hang outside the shower door, on account I was not anticipating not having privacy. No great way to do this, as Alison is trapped behind the ironing board in the small corridor, with no space to put the iron down easily enough for her to assist me. Which would then just result in her seeing me naked anyway if she were to walk into the bathroom. I inform her of my dilemma, I tell her to just finish up with the clothes, I am going to step out quick and just grab a towel. I finally muster up the courage to do that damn thing, and I quickly slide the door back and step up fast towards the towels on the opposite side of the bathroom. There was no way she didn't see me naked, as she was 3 ft away and had a direct view, but I tried to minimize the exposure as much as possible.
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The rest of the day goes smoothly, no awkwardness between us after our fiasco of a morning, and we enjoy the conference together. We get back later in the evening and plan for dinner again. Alison takes her turn in the bathroom, joking with me to not need to iron anything right now as a way to get revenge. I joke I wouldn't dream of it, but of course now that the thought was put in my head, I did imagine what she looked like under the shower, water running through her hair, her braid undone and wet hair clinging to her body, trickles and lines of water rolling over her nipples and down her stomach to her vagina. I had to pull myself back unless I really wanted to make matters worse, only for her to walk out in a bathrobe once I did, her eyes matching mine and winking after she gathered up a bra for herself. Dinner once again was nice, a bottle was split, and our conversation became a bit flirtier. Not outright direct with it, but teasing or provoking comments as we became more relaxed with each other.
We get back to the room for the night, Alison claims the bathroom first before bed and heads in. While sitting on the bed awaiting my turn, Alison suddenly comes out in just her jeans and her bra on, toothbrush in her mouth, and rushes to her bag to grab an oversized shirt. "What, a girl can't relax without a bra on?" she said, "I forgot to grab a sleep shirt for myself to change into." and I just nod and stare back at her new boldness. We get ready for the night, laying in our respective beds, chatting once more. As we decide to finally go to sleep, Alison tells me "If you want to sleep in your boxers, or I guess, if you feel comfortable enough to be nude, you can do it. Just don't make it obvious to me and make sure you pack yourself back up if you were to leave your bed with me present." I laugh and tell her not to worry, I'll be decent, and as the light turns off, I opt to kick my shorts off under the covers, leaving me in my boxers. However, the mix of the memories of seeing her earlier in the day, my fantasy of her showering, her recent shirtless image in my head, and sleeping in minimal clothing less than 5ft away from a women was thrilling, and I ultimately work my boxers off too to satisfy my building lust, but keeping them near by in case I wake up in a panic.
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The next morning I wake up to an empty room, Alison no where to be seen, nor hear her in the shower. I text her where she went, figuring coffee, and she says she went for a quick run, and can grab some on the way back. I take this opportunity to get myself ready while I have the freedom of an empty room, hop out of bed, and get showered and dressed. I manage to finish my tasks, standing in the bathroom in my pants, no shirt on, when Alison comes back, coffees in hand. We chat about her run over the coffee, when she notices and points out my boxers laying out in the open on my unmade bed. "So did you go through with sleeping nude or did you just toss them real quick before you showered?" she asked. I think over my response in my head, where I easily and safely should just go with the latter option, but I decide to tease it and inform her of the former. She raises her eyebrows up at my response, telling me I am bolder than her to admit that, let alone sleep like that in a hotel. She then gets up and says she is going to shower, and pulls her shirt off right there. She had her sports bra on, so nothing crazy was happening, especially after how I saw her last night, but then she drops her shorts to reveal a small pair of compression shorts just barely covering her hips. I lag my eyes at her waist and more exposed navel and lower abdomen before she smiles softly and walks pass to get in the shower so we can go to the conference.
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The day goes as I have described previously, good day, fun, we go for dinner, wine, chatting, sprinkle of flirty, the works. We go to bed the same as the night before, we lounge for a bit on our beds, I'm just in shorts at this point as she has seen my plenty of times by now without my shirt on, Alison laying in a cami top and loose shorts, before knocking out. I work my way down to my boxers and ultimately nothing again. About half way through the night, I hear Alison call my name, waking me up. I push up a little in bed and ask her what is wrong. "I'm cold." she says. Still half asleep, I take a moment to answer, "Do you want me to raise the heat?", being the closer of the two to the thermostat. Silence fills the room as I weigh between needing to throw on boxers at least or if that I can step out naked in darkness without risk. Just as I was about to just go for it, Alison says, "Can we share the same bed instead?" I am still very tired and groggy, but I am slowing coming back to it. She is asking to share the same bed, a full bed, for warmth. I don't think clearly enough and just say "Uhhh, sure." Before I realize my very immediate need to throw my boxers back on, Alison gets out of her bed and gets into mine. Back facing me, quickly filling in the space I needed to get dressed. She says thanks and I tell her a shaky welcome, as I now need to remain calm that this women, who is not my wife, is sleeping inches away from my uncovered dick. And that I most certainly should not get a boner right now.
However a moment later she wiggles and adjusts herself under the covers, figuring she was going to get more comfortable, however I soon realize she is inching herself towards me. I try and move back as well, trying to avoid contact, and I soon run out of room on the smaller full mattress, finding myself right near the edge. "Al-" is all I manage to say before I feel her finally make contact on my dick. Direct skin to skin, I was now fully awake and confused and floored. I feel her soft skin on my flaccid dick, putting pressure on it as our bodies became close. I slowly move my hand so just my finger tips find her back, which is still wearing her cami, but as I slide it down her back, I find her to be bottomless, and soon determine that my dick is right up against her ass. Before I can speak again, she says "I just want to get warmer" and she begins wiggling her ass up and down, rubbing my dick along it, progressively getting me harder.
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It wasn't much longer until I was fully erect, my dick completely resting along her back side. Alison moves herself up so that my dick is now resting fully between her asscheeks, and starts moving her pelvis to slide up and down my shaft. It being completely dark and having this happen is driving my arousal way up. But what does she want? We are both married, the fact that this is happening already is insane, let alone without any prior discussion besides my sleeping habits and brief visuals of us in various stages of undressed. Should I grab my dick and position it between her legs for a thigh job? Should I just raise her left leg up and slide in and start fucking her? If that was the case she probably would've turned to face me or with how much she is leading this so far, put me in her herself.
While I am thinking all of this, I hear her fingering herself. Holy shit, she is trying to jerk me of with her ass and is getting herself off as well. I stop thinking about what to do and just focus on what is happening right now, my co-worker wants to make me cum while fingering herself. I let the pleasure fully take over in my mind, only letting it wander to imagine how Alison is. I can hear how wet she is, and I imagine what her pussy looks like, soaking wet, how it feels with my own fingers, how it tastes with my tongue, how it fits on my dick. I imagine how she looks completely naked, how fat her ass is to be able to massage my dick so deftly, how her pelvis and stomach must look to move like this, how her tits look and feel when horny. I realize that I can help her pleasuring out as well, and I move my hand to her tits, grabbing one over her cami. She gasps into a long moan as my hand encompasses her breast, my fingers quickly finding her nipple. Her fingering intensifies as I massage her nipple, her breathing getting heavier. I can smell her light fragrance from her shower on her skin and hair, and I move closer to her neck and exhale slowly over her nape, hearing her shudder as I imagine the goosebumps rolling over her bare skin.
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Her pelvic motion slows as I begin distracting her too much, but I feel myself starting to become overloaded with pleasure and look to finish what she started. I move my opposite hand towards her ass, feeling how soft it is and plump in my palm, and push it to make sure my dick is square where it should be. I begin to move my hips now, fucking her cheeks back to take control of my pleasure. My use of her brings her moaning to become more intense, her breath becoming frantic. I pull the breast that I had been playing with out from her top, feeling its warmth and softness. I move my position from her nape to her ear, breathing on it as well, pushing the boundaries more with licking and teasing the edge of it with my lips. Her fingering becomes manic as her hips rejoin my movement, looking to bring me to completion and share this orgasm. I soon feel my load getting beyond my ability to hold and let it erupt out of me with a resounding moan of my own, not wanting to announce "I'm cumming" to interrupt our ecstasy, my cum firing up along her back and the bed, the last few drops trickling down onto her ass. Her fingering slows down as we calm our breathing, eventually falling asleep while spooning in our filth.
I wake up and find Alison is not in bed, soon hearing the shower running. I remain in bed, still naked, for at this point, I've been laying in my cum and who cares if she sees me naked. I lay in bed until she comes out, wearing a bathrobe, and sees me looking back at her. She breaks the silence by saying, "I'm sorry about last night, it's been a few days since I last came and just couldn't contain my horniness. It seemed to be the same for you, too." I answer, "We are both married, isn't this cheating since you jerked me off?" "My hands never touched you, so I don't see how that is cheating. You just used my ass to satisfy your needs, I wouldn't see that as any different than using a toy," she says back, "If anything, you were the one who put direct hands on me and bit my ear." Shit, she got me there. While her logic was loose its true that I was the only one to actually feel and grab the other with my hands. "But it made my orgasm feel so much more electric, that I don't mind at all. I loved it. It was so exhilarating." I agree and tell her the whole time I was going insane imaging what she looked like as I let my hands help guide my imagination as I humped her.
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"Oh, so you wouldn't be opposed to putting your imagination to rest?" Alison then asks. "What?" I return. "I guess what I am asking is," her hands pulling her bathrobe belt apart while speaking, opening her robe and letting it fall off her body, "is there anything else you would like to no longer imagine about me?" She is gorgeous, her smooth stomach running from her long legs and shaven pelvis to her tits hanging with small perky nipples. My close my mouth and swallow before reiterating, "But we are married." She answers, "I understand that completely. And I do not want to take this beyond where we should go. But what I want is for us to watch each other cum together. Do you watch porn? This won't be any different than that in my mind, just simply watching the other masturbate." Alison walks over to one of the chairs, sits down, and raises a leg to rest over an arm, spreading her legs wide open and revealing her pussy to me. "Please." she says. "I want to see that cock that drenched my back last night." The whole time we were talking my boner was growing, and all thought was stemming from it. I wanted this, whether it was wrong or as simple as she said, I wanted it. I pulled the comforter off and got up, my dick fully erect and walked over to sit on the edge of her bed, her eyes trained on my dick the whole time, as I position myself 3ft away from her. She leans back in the chair, placing her other leg on the other arm, sliding her pelvis forward to reveal her anus to me as well. I lean back, moving my pelvis forward as well to do the same, and grab my dick and start slowly rubbing it, Alison taking that as her cue to rub her pussy.
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One of her hands quickly finds her tit and she massages it as she runs her fingers through her lips and over her clit, getting herself wetter and wetter. I continue to slowly stroke my cock, increasing my grip each time she spread her lips wide and gave me a view inside. Alison then sends a finger inside of herself, then two, and finally three as I increase the pace on my dick. I move a hand down to my perineum and massage that, making my dick swell. As I watched her finger fuck herself, I imagine it being my dick thrusting into her, turning her amazing moans into screams. She moves her hand from her tit to her clit, her breathing becoming ragged as we both work each other to the opposite's pleasure. I wanted to have more, I wanted to be deep inside of her but knowing it was wrong. I have an epiphany, somehow, during all of this.
"Let me finish fingering you" I tell her. "Excuse me?" She says, trying to keep her pleasure going as I propose this dare. "You helped finish me off last night, working your ass back and forth with me, its only right if I were to help you now. I can finger you while you rub your clit." Alison keeps her hands going on herself for a moment before biting her lip and nodding. I get up from the bed, swap which hand I am using on my dick and crouch in front of her pussy. Her top hand still rubbing her clitoris, the other pulling herself side open. I immediately throw two fingers in and feel her warmth and tightness, my fingers immediately soaked from her own work. I slowly maintain a deliberate stroke on my dick as I shift my attention to her. She tells me more, and I slide a third finger in, thrusting and curling my fingers at once, her walls tightening around my fingers as she moans into louder gasps. I feel her getting close with how tight she is becoming, her lips dripping, and I slide a fourth finger in. She yelps, removes her hand off her clit to sit up taller and brace herself, as I now move my fingers independently and run along the top of her vaginal wall. Her hand finds clit again and she begs me to not stop, yes's filling her lungs and loud, intense moans come out. She contracts and cums, her legs tensing inwards as her body shudders from my continued stimulation, her breathing in high, short peaks as she slowly comes down from her orgasm.
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"Cover me." She says, opening her legs again as she allows me to use her body as my target for my own orgasm. I pull my fingers out and use her wetness to grab my dick and finish my stimulation. I stand over her and watch as she plays with her tits as my final strokes come to fruition. In my orgasm, I lurch forward, catching myself on the chair as I frantically jerk myself as my cum fires out in heavy bursts, landing on her chest and stomach, as it begins to slowly drip down her navel. I look up from my work and find Alison only inches from my face, close enough to see the moisture on her lips, the sweat on her brow, and feel her breath as we hold our tension for longer.
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Needless to say we did not go to the conference on the final day. We didn't fuck either, holding ourselves accountable to some degree. We did basically stay naked in front of each other at that point, but once we finally cleaned up we spent most of the day apart. Our trip back home was quieter too, being together in the uber and at the airport, but once we landed back home we quickly went our separate ways. I've been anxious with seeing her at work, and she seems to hold the same anxiety, but we have continued to remain cordial when working together. But a voice in the back of my mind can not wait for the next work trip opportunity.