Double Occupancy

I was working on a job that had a project office about sixty miles from my home office. I had to be at the project office at least once a week for a status meeting but some weeks there were other meetings or trainings that required my presence. Typically, I'd just drive up for a meeting or training and drive back to my home office after but there was the rare occasion when I'd have something late one day and something else early the following day. On those rare occasions, I would book a hotel room nearby and the project would pay for it. I only did this when I absolutely had to but it sure beat driving through rush hour traffic twice. Occasionally there was also a project happy hour, which I typically wouldn't go out of my way to drive the sixty miles to attend but, if I happened to be at the project office already, I'd definitely be up for some socializing with the team. The problem, of course, was that I'd have to refrain from drinking to make the drive back afterwards, which would typically be pretty late. If I wanted enjoy a few cocktails, I'd need to get a hotel room which, in a case like this, the project would not pay for. It was well worth the cost as far as I was concerned, however and, on one particular occasion, it proved to be even more than worth the cost.

This particular happy hour was to celebrate the retirement of the Project Director so I'd made an extra effort to make sure that I was there and that I had a hotel room. I was on my second drink when I ended up in a conversation with Alyssa, who was one of the construction inspectors. We were typically in the same meetings but we didn't often have a chance to chat one-on-one. Although I didn't intentionally avoid having conversations with her, I also didn't necessarily make any extra effort since I thought she was pretty cute and I didn't trust myself not to flirt with her. As a woman on a construction site, I was sure that she had to deal with a lot worse than unconscious flirting when she was out in the field so I didn't want her subjected to it in the office, as well. Technically it was also inappropriate for me to treat her any differently from any other colleagues on the job but probably not equally inappropriate. As we started chatting at the happy hour, I was feeling a little more relaxed due to the first drink but I was still trying to be careful.

"Do you have a long drive home after this?" she finally asked, since we'd never talked before about where either of us lived.

"No, actually," I replied, "I booked a room just down the road for the night so I wouldn't have to worry about driving."

"You just have to be able to make it back to the hotel," she said.

"My vehicle is parked over there now," I explained, "I caught a rideshare over here after I checked in."

"Ugh, I wish I had thought to do that instead of planning to drive home," she replied.

"You could probably get on your phone and book a room," I suggested, "I doubt they're full tonight."

"Or maybe I know somebody who'd be willing to share a room they already have booked," she said, acting like she was trying to think of who that could be.

"Unless that person booked a room with just a single king size bed," I replied, trying to be extremely careful where this was going.

"Maybe somebody willing to share a room," she suggested, "might also be willing to share a bed."

"Is it safe to assume you also don't have pajamas out in your truck?" I asked.

"If you're willing to share your room and your bed," she replied, "maybe there won't be enough sleeping going on to even need pajamas."

"Are you serious or are you just playing around?" I finally asked.

"I'm totally serious," she replied, "I think it'd be a lot of fun."

"I completely agree," I said, "but I want to be sure that we're both on the same page."

She confirmed not only that she'd barely had anything to drink because she was expecting to drive home, so she was completely of sound mind, but that she wanted to spend the night with me in my hotel room in the king size bed without any pajamas. I was ready to leave immediately be we agreed that we should probably be respectful of the guest of honor and not run right out, though we also knew we couldn't wait until a lot of people were leaving who might see us leave together. We decided to part and mingle then, when the time was right, we both slipped out but not together. She was already in her vehicle when I got to it so I climbed in and we made out for a few minutes before heading down the road to the hotel. She parked around the side of the building, out of sight from the main road, and we slipped in a side entrance using my keycard.

We resumed making out in the elevator on the way up to my room then I led her down the hall and unlocked the door. Inside with the door locked behind us, we made out briefly at the foot of the bed then I had her sit down as I knelt. She was still dressed for her field work, which meant heavy-duty work boots, jeans and a flannel shirt over another shirt. She was fair-skinned with strawberry-blond hair and blue eyes and was very fit, no doubt in part due to all of the time she spent out on the job site. I started to untie her boots then removed each of them and her socks as she looked down, watching me. Standing again, I kicked off my own shoes then crawled onto the bed and had her crawl to the middle and lay with me, where we went back to making out.

I unbuttoned her flannel and slipped my hand in to caress her boobs through the thinner shirt she wore under it. There had been a meeting we'd been sitting in one day during warm weather and she slipped off her heavier overshirt giving me my first peek at just how big her boobs were. For some reason I'd been under the impression that she had small boobs but I realized on that day that, while they weren't huge, they were definitely substantial. I could completely understand why she'd keep them hidden working on a construction site. Getting a hand on those big beauties was pretty monumental so I only briefly caressed each of them through that thinner shirt before slipping my hand up under it. I could feel her hard nipples through her bra and, as I felt my cock stiffening, I suspected that her pussy was probably quite wet. While I was eager to confirm that, I wasn't done with her succulent boobs yet. As we continued making out, I got her bra unfastened and my hand was quickly on her bare flesh and feeling her hard nipples against my palm.

The only thing that could possibly draw my hand away from caressing her sweet boobs was the prospect of a very wet pussy. After thoroughly fondling her bare boobs, I slid my hand down over her stomach to the waist of her jeans, which I then unfastened and slip my hand into. I briefly caressed her pussy through her panties then slipped my hand inside them and through her trim bush. No surprise, her pussy was flooded with juices and completely engorged. I easily slipped a finger into her then slid it in and out before alternating that with gently caressing her clit. She was moaning into my mouth as we continued making out but eventually pulled her mouth from mine and pushed her face into my neck while moaning louder and longer. My cock was rigid and the thought of slipping it into such a hot, wet, snug pussy was incredibly appealing but I was in no rush and wanted to make sure that she came, hopefully a couple of times, before I slipped into her in case her pussy felt so incredible that I blew my load immediately.

She held me more tightly as she was tensing up then abruptly went silent, briefly holding her breath before letting out a cry as her entire body started shaking. I continued lightly caressing her clit as she was cumming, hoping to either prolong her orgasm or make it even more pleasurable. When she finally went still after what appeared to be both a long and highly pleasurable orgasm, I slipped my hand out of her panties and licked her flavor off of my finger. My cock was still rigid but there was something else I wanted to do before taking care of myself, which started with getting her naked. While she was recovering, I got up on my knees and slid her jeans down followed by her panties, revealing her well-groomed, strawberry-blond bush. I moved between her legs then lowered my head and kissed along her soft, smooth inner thighs toward her pussy.

I don't know if her orgasm got her a little heated up but, as I was getting comfortable between her parted thighs, she started pulling her shirts off and casting them aside. Of course, I had to take a moment to watch as she shed her bra since I hadn't seen her boobs yet. They were impressive; large with big, light pink areolas but still standing firmly even when she reclined again. I was glad that we had the rest of the night ahead of us so that I could enjoy them some more. In the meantime, with her hot, wet pussy right in front of me, I ran my tongue along her slit, tasting her juices and making her moan again. I slurped up her juices, lapping at her pussy, before slipping a finger into her again, once more finding her hot, wet and snug. While sliding my finger in and out, I was licking and sucking her clit, which had her moaning louder and longer.

When she reached down to hold my head while humping her pussy toward my face, I glanced up and saw her luscious boobs squeezed between her arms, which made me realize there was another thing that I wanted to do while we had that hotel room. For the moment, though, I was going to relish eating her pussy and make sure that she enjoyed it enough that she'd want me to do it again whenever possible. I was a big fan of eating pussy and enjoying one that was new to me was always a special treat. As much as I was looking forward to slipping my cock into Alyssa's pussy and her mouth and between her tits, I was also thoroughly appreciating the opportunity to devour her pussy. Based on the noises she was making, she was quite obviously appreciating it, as well. She was rocking her pussy toward my face while moaning louder and longer as she was apparently getting closer to cumming again.

I did everything I knew how to draw out the pleasure she was feeling without it seeming like I was denying her an orgasm. My goal was for her to feel the pleasure building for an extended period which would then culminate in an even more intense explosion of pleasure. It felt like things were going that way as she gradually began to tense up and arch her back while moaning louder and longer. I didn't necessarily want to be done eating her pussy but I was eager to slip my cock into her and, since she was staying overnight, there might still be additional opportunities. Given that she seemed to be getting close even as I was still trying to draw out the pleasure, I did end up switching gears to pushing her the rest of the way there. It wasn't much of a change in technique but it was apparently enough.

When she was right on the verge of cumming, she went still and silent momentarily then let out a cry as all the tension left her body. She went limp on the bed but started shaking while I continued to lick and suck her clit while sliding my finger in and out of her now even hotter and wetter pussy. It was another long and apparently highly pleasurable orgasm so I was happy to have helped her achieve it. Only once she'd gone still and silent again did I raise my head and slip my finger from her pussy. As I raised up, looking over her naked body, I sucked her juices off of my finger then pulled my shirt up over my head and tossed it aside. She was watching me, though looking a bit dazed, as I then opened my jeans and pushed them down, followed by my briefs. Her eyes went wide as my stiff cock sprung out and she was just beginning to sit up when I flopped onto my back to get my jeans and underwear completely off.

She reached for my cock and stroked it as she was getting up on her knees while I was watching her tits bouncing and swinging. She straddled me and guided my stiff cock toward her pussy so I reached up to fondle her big boobs. We both moaned as she lowered herself onto my cock, my full length slipping easily inside her. She just sat on it for a moment then slowly began to move up and down. Her snug, slippery pussy felt amazing as it slid up and down my stiff tool and the soft, smooth flesh of her titties felt incredible as well. I would move my hands slightly so that I could check out her large areolas and hard nipples then my gaze would travel down to her well-groomed, strawberry-blond bush. It seemed like my cock just continued getting even harder the longer she was riding me and, based on the sounds she was making, it was a safe bet that she felt it.

I finally moved my hands from her luscious tits as they were bouncing due to her riding me so hard because I could no longer resist watching them. I ran my hands down along her waist and around to her toned ass, holding it as I pushed up into her each time she dropped down. The bed proved to be sturdy and well-built, remaining quiet and not moving excessively as our fucking became even more enthusiastic. Her pussy was becoming even hotter and wetter the longer she was riding me so I could feel my orgasm slowly beginning to build. I was sure that hers was building, too, but I had no idea how close she was to cumming again. On one hand, I hoped that she'd easily have another intensely pleasurable orgasm but, on the other hand, I wanted to continue having her ride me for as long as possible. I really was thoroughly enjoying feeling her pussy sliding up and down my tool while watching her tits bouncing.

When she finally dropped down on my cock and just sat there with her eyes closed and her mouth open, I wasn't that close to cumming myself so I figured we'd be switching things up and was pretty psyched about that. I was also psyched that she was cumming again, which was very obvious when she cried out and started shaking. Since they were no longer bouncing, I brought my hands back around and resumed fondling her luscious titties. I doubt this helped with the pleasure she was feeling but it didn't sound as though she needed any help anyway. Her orgasm was clearly another long and highly pleasurable one and, as she was cumming, my orgasm was backing off a little so I was happy that I'd be able to enjoy more pleasure for longer once she'd finished and we'd figured out what we were doing next.

It turned out that she apparently already knew what she wanted to do next because, when she finally finished cumming and had taken a moment to recover, she climbed off of my cock and moved backward down the bed, kissing her way down to my stiff cock. As she lay between my spread legs, she gripped my stiff tool, pumped it a couple of times, then engulfed it in her hot mouth. I was immediately moaning as her mouth moved up and down my shaft while she gently pumped the base. I pulled the pillows over to prop up my head so that I could watch and watching her suck my cock was even hotter than just feeling it.

She had my orgasm building up from the moment she started sucking my cock but she also somehow managed to draw out the pleasure she was providing, allowing me to enjoy her cocksucking for longer. I would have been more than happy to continue enjoying it through the entire night but, even though she was able to draw out the pleasure, there was only so much she could do when it felt so fucking incredible. Gradually my orgasm was building despite her efforts to prolong this blowjob though, even as my cock began to swell a bit more, she was unfazed and maintained her efforts. She did wind up adjusting her technique slightly to get me the rest of the way there rather than continue trying to draw out the pleasure when she knew I was getting close to cumming.

When I finally exploded into her mouth, the pleasure was intense and seemed to go on and on. Still unfazed, she swallowed my load while continuing to skillfully suck me off. Only when I was fully spent did she release my cock from her mouth then smile when she saw the look on my face. She crawled up to lie beside me, her naked body pressed against my naked body.

"That was outstanding," I finally managed to say, "This absolutely beats spending the night here by myself."

"I would hope so," she replied, laughing, as if there was any comparison. My only plan for the next morning was to wait until after the morning rush and drive back to my office but Alyssa still had to be out on the job site pretty early so we talked about how we should probably call it a night. She obviously didn't have any toiletries but did the best she could to accomplish her nightly ablutions with what I had and what the hotel provided. The thing was, though, that being naked around each other as we were each getting done ended up getting us both aroused again, which was clearly more obvious with me. We hadn't been shy about continuing to touch and caress each other as we'd been getting done so I was pretty sure that she was as worked up as I was.

Once we were done and heading back to the bed, my stiff cock was sticking out ahead of me, pointing the way. She climbed onto the bed and remained on all-fours with her ass up in the air so I got behind her on my knees and guided my stiff cock into her, finding that her pussy was incredibly wet. Despite how snug she was, I easily slipped all the way in until my hips were pressed against her ass. Holding her waist, I started to slowly slide my cock in and out, relishing the pleasure that I was feeling as a result. I was looking down, gazing at her sweet ass which would just barely jiggle when my hips tapped against it. Once I had a good rhythm going, though, I slid my hands forward over her ribs until I was cupping her swinging boobs. As I felt the soft, smooth flesh in my hands and her hard nipples against my palms, my cock was becoming even harder, which I wouldn't even have thought possible. She clearly felt it as well because I don't believe me fondling her boobs would have had her moaning louder and longer.

She had reached under herself when I'd slipped into her so I assumed she was caressing her clit while I fucked her. I didn't know whether this was to make her orgasm more pleasurable when it happened or if she was trying to bring it on faster because she needed to get to bed. Either way, I was glad she was being proactive about her own pleasure and I definitely wasn't taking it personally that she was helping herself along. Since I had cum once already, my own orgasm was building up nice and slow despite how incredible her snug, slippery pussy felt gripping my cock and how much I was enjoying fondling her tits.

When it sounded like she was getting closer to cumming, though, I did release her tits and straightened up, holding her waist again. I figured that this way I could make sure she was getting the full length of my cock with each thrust. Because she had her head down and was reaching under herself, she wasn't pushing back so I figured it was on me to make sure she was getting as much penetration as possible. I was gradually picking up the pace, fucking her harder and faster, but her ass still would barely jiggle, though I'm sure her tits were swinging like crazy. Her moaning was getting louder and longer which was helping to give me a sense of how close she was getting to cumming. Her pussy was also becoming even slicker than it already had been, so the pleasure I was experiencing was increasing as well.

When she finally cried out and started shaking, I continued to fuck her but it wasn't as hard and fast. I switched to long, slow strokes which I was really hoping were helping with her orgasm because they sure felt incredible to me. Whether it helped or not, her orgasm was long and appeared to be pretty pleasurable for her. I didn't stop fucking her until she'd gone still and had let out a sigh. I was getting pretty close to cumming by then but there was definitely something else I wanted to do and, since she'd already cum, I figured that now was the time. I slipped out of her then had her roll onto her back and straddled her. I lay my stiff cock between her tits and brought them together on either side of it while she watched. I moaned as I started to slide my cock between her tits because the soft, smooth flesh felt so incredible against it.