Coworker Sleepover Ch 01

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.

On one of these occasions when I had a hotel room booked, I was at the project office much later than I typically would be and it didn't go unnoticed. Jennifer was the Environmental Task Lead for the project and at the very least we were in the weekly status meeting together. She had dark blond hair and some nice curves and appeared to be about the same age as me. Aside from the weekly meeting, we hadn't interacted a lot since the project had started but that quickly changed.

"What are you doing here so late?" she asked after almost running into me in the hallway.

"Just got out of a meeting," I replied, "and I've got another first thing tomorrow so I figured I'd just hang out until then."

"You're just going to hang around the office until tomorrow morning?" she asked, well aware that I wasn't serious.

"Sure," I replied, "once everyone has gone it should be fun. I'll probably start by going through everyone's desks."

"That'd take care of the first hour," she said, "then what?"

"Probably a fine dinner made from all the food stashes I discover while going through desks," I replied.

"Then you'd be totally bored," she said, "What are you actually doing?"

"I've actually got a hotel room booked so I don't have to drive back tonight then come right back here again in the morning," I confessed.

"Now that actually does sound like fun," she said.

"Oh, yeah," I replied, "hanging out in a hotel by myself should be a blast."

"You don't have to hang out by yourself," she said, lowering her voice and glancing around, "In fact, you probably have a coworker who lives nearby who thinks hanging out in a hotel room for the night would be a fun change of pace."

"What kind of fun are we talking about?" I asked, also in a low voice.

"The kind of fun that two consenting adults would generally have in a hotel room," she said, barely above a whisper then gave me a look that almost implored me to be interested.

"Would you like to come hang out in my hotel room tonight?" I asked, keeping my voice low.

"I thought you'd never ask," she replied so we exchanged contact information. She wanted to go home and grab a change of clothes so I was just going to text her my room number once I was checked in. Now that I had something interesting going on at the hotel, I was more eager to get over there and get checked in. I got wrapped up there at the project office and drove the five miles to the hotel. Once I was checked in and up in my room, I texted the room number to Jennifer and she said she'd be there soon. I propped the door open with the deadbolt and unpacked my toiletries but didn't actually have much else to unpack since it was just the one night.

When she arrived a little while later, she knocked as she walked in then locked the door behind her. She was wearing the same blouse and skirt she'd had on earlier but had a small bag with her.

"I hope you don't mind that I didn't change clothes," she said, "I wasn't planning to still have them on for very long. This is a nice room and a nice bed."

"Shall we try it out?" I asked, so she set her bag down and we got onto the king-size bed on our knees, slipping into each other's arms in the middle and bringing our lips together. As we went from kissing to making out, my hands dropped down to her ass and, as I caressed it, I pulled her against my stiffening cock. As I was massaging her ass, I started pulling the hem of her skirt up so I could get my hands under it. I continued to caress her ass through her panties, still pulling her against my cock, but soon brought one hand around and massaged her pussy through her panties. I could feel the course texture of her bush then the moist heat emanating from her pussy. I ended up slipping my hand into her panties, my fingertips running through her trim bush, then lightly caressing her clit. She pulled her mouth from mine to let out a moan and I realized that I could probably make her cum like this but, since she appeared to already be thoroughly worked up, I figured that I could do better.

Slipping my hand out of her panties, I maneuvered her around so that she was lying on her back and I was between her spread legs. I pushed the hem of her skirt up around her waist, revealing that she was wearing bikini panties, which I then started to slide down. She brought her legs together to allow me to remove them completely then parted her legs again and bent her knees. I was gazing down at her trim, dark blond bush as I tossed her panties aside then lowered my face toward it. I ran my tongue along her slit, tasting the copious juices that she was producing and making her moan loudly. Just a couple of hours prior, I'd have had no reason to ever think that I'd be in this position. Since I was, however, I was going to savor this opportunity to devour a pussy I'd not only never tasted before but had never even imagined tasting.

I slurped up her juices for a bit before slipping a finger into her, finding her pussy both incredibly slick and quite snug. My cock was already throbbing but the thought of slipping into such a tight, slippery pussy made it even harder. First, however, I knew I needed to make sure she had a highly pleasurable orgasm because I had a very strong feeling that, once I slipped my cock into her, I'd be cumming pretty quickly. While sliding my finger in and out, I was licking and sucking her clit which, based on the sounds she was making, was definitely doing the trick for her. She reached down and grabbed my head while rocking her pussy toward my face, moaning even louder and longer. I glanced up and, despite still being covered by her blouse and bra, her tits were squeezed together between her arms, making them look pretty substantial. She never dressed to show off her tits so I hadn't realized how big they were and now I was even more eager to get her undressed.

As she was apparently getting closer to cumming, she went from rocking her hips toward my face to tensing up more and gripping my head tighter. I didn't change my technique any since it seemed to be working quite well and I wasn't really trying to draw out the pleasure since we had the entire night ahead of us still. I figured I'd try to give her a quick orgasm since I was pretty sure the anticipation had her pretty worked up before she even got to the hotel. Likewise, I knew my own first orgasm would be a quick one but I was confident that any that followed would allow me more time to enjoy whatever pleasure I happened to feel for much longer. When she went nearly rigid and it sounded as though she briefly held her breath, I was pretty certain that she was right on the verge of cumming. Sure enough, a moment later she cried out and went limp then her body started shaking. I continued to eat her as she was cumming and her orgasm was a pretty long and apparently intensely pleasurable one. Only when I was absolutely certain that she'd finished cumming did I raise my head and slip my finger from her pussy into my mouth to suck her juices off of it.

As she was recovering, I got up onto my knees and unfastened my jeans, pushing them down along with my underwear until my rigid cock sprung out. She was watching and her eyes went wide when she saw how ready I was so she beckoned for me toward her. I guided my cock to her pussy as I lowered myself over her, easily slipping inside despite how snug she was due to all of the natural lubrication. We both moaned as I slid my cock all the way in but it only became even more clear that I wouldn't be good for very long so I figured I should warn her.

"This first one is going to be pretty quick," I said as I started to slowly slide my cock in and out of her.

"That's okay with me," she replied, "we have the whole night ahead of us. Why don't you just go ahead and fuck me hard and fast?"

I brought my lips to hers and kissed her then we briefly made out as I started to fuck her harder and faster. Once I got to the point where it was difficult to continue making out, I moved my lips from hers and raised up a bit, hooking her legs over my arms so that her knees were about touching her tits. She continued to moan as I was pounding her pussy while savoring the grip it had on my throbbing cock. The bed proved to be sturdy as it neither squeaked nor banged against the wall as I was fucking her hard but rhythmically. I was actually lasting longer than I had expected, maybe because I'd told her so I wasn't concerned about cumming too quickly, but the bigger surprise was when she had another orgasm before I came. She had her eyes closed but I was looking down at her and her face kind of tightened up at the same time that her grip on me tightened up. It was only for the briefest of moments then everything relaxed as she cried out and started shaking. Her pussy was flooded with even more lubrication so, as I continued to fuck her, my cock was thickening even more until I suddenly started to spew. I slowed down my thrusting, timing it with each spurt from my cock, then held my cock inside her until I was completely spent. I released her legs and moved off to lie next to her.

We lay there recovering and catching our breath but we were still almost completely dressed. After reaching over to caress her tits through her blouse and bra, I was soon unbuttoning her blouse and caressing them through just her bra. It wasn't a front clasp so I had her roll toward me briefly as I reached around and unhooked it then I slipped my hand up under the cups as she rolled back. Feeling the soft, smooth flesh and her hard nipples had the blood returning to my spent cock but I knew getting her completely naked would get me there even quicker. Before I did that, though, I pushed the cups up on her chest and leaned over to lick and suck her hard nipples, which made her moan and I figured was probably helping to keep her pussy nice and wet.

While I was enjoying fondling her tits and licking and sucking her nipples, I figured I'd enjoy even more having her completely naked. I pushed her blouse off of her shoulders and helped her to slip completely out of it then slid her bra along her arms and tossed it aside. I then got up on my knees and unfastened her skirt before sliding it down, leaving her fully naked. Looking over her as I was still on my knees, I could again feel the blood surging toward my now recovering cock. Her dark blond bush was nicely groomed and her tits, topped with large areolas and hard nipples, were still pointing toward the ceiling, despite their size. She gave me a moment to admire her body before sitting up and starting to lift my shirt. I pulled it up over my head then flopped beside her on my back while she got onto her knees to work my jeans and underwear further down. I watched raptly as her tits were bouncing and swinging until I was as naked as she was.

I wasn't quite fully rigid by that point so, rather than straddle me, she gripped my cock and pumped it briefly before lowering her head and taking it into her mouth. I moaned as her warm mouth engulfed my tool and she slowly slid her lips up and down my shaft. Between the pleasurable feeling of her sucking my cock and the visual of my cock disappearing into her mouth, I was fully rigid in no time at all. She didn't stop as soon as my cock was hard enough for fucking, though; she continued to suck it as though she was having trouble making herself stop. Finally, though, she raised her head and smiled sheepishly at me while moving up to straddle my hips. She gripped my cock and guided it to her pussy then lowered herself down on it, both of us moaning.

I wouldn't have thought it possible but her pussy felt even more amazing than it had when I'd slipped into it earlier. She was hot and wet and snug so having my throbbing cock engulfed as she lowered herself onto me was so incredibly pleasurable. She sat there for a moment with my cock embedded inside her then began to slowly move up and down on it. I reached up for her tits and caressed the soft, smooth flesh and her hard nipples while relishing the pleasure of having her pussy sliding up and down my cock. I was glad that my first quick orgasm was out of the way so that I could enjoy the feel of her hot, wet pussy for even longer this time. As much as I was enjoying her pussy, based on her moaning and the expression on her face, Jennifer was enjoying my cock at least as much. She was gradually riding me harder and faster and, once her boobs started to bounce, I moved my hands around to caress her ass so that I could watch them.

I was pushing up into her each time she dropped down to ensure that she was receiving the full length of my cock inside her. Of course, this was for my benefit as well as I wanted to feel her hot, wet pussy sliding up and down the full length of my shaft. Again the bed proved to be sturdy as it remained quiet even as she was getting louder the longer and harder she was riding me. I wasn't feeling the stirring of an orgasm yet so I was focused this time on the pleasure I was experiencing since it appeared that she was building toward her own orgasm without any extra effort or attention from me. If I had any neighbors in that hotel, I had no doubt that they were hearing Jennifer as she was getting closer to cumming because she wasn't even remotely shy about expressing herself.

She did go silent briefly when she dropped down on my cock and just remained there momentarily, motionless and quiet. As I brought my hands back around from her ass to fondle her titties again, she let out a cry and her entire body started shaking. It appeared to be a highly pleasurable orgasm, as well as pretty long, so I was happy that I'd been able to help her achieve it. As she rode it out, I just lay there playing with her titties while waiting to see what she'd want to do next. When she finally went still and silent again, she sat there on my still rigid cock, catching her breath and recovering. She smiled down at me then leaned forward and kissed me on the mouth before beginning to kiss her way down my body. She ended up kneeling between my legs where she gripped the base of my cock and, as she slowly pumped it, wrapped her lips around it and engulfed it in her mouth. I let out a moan as I watched my cock disappearing repeatedly into her mouth.

I wasn't sure whether she planned to suck me to completion since she'd cum while riding me but I figured that, if she did, it wouldn't take long for me to recover and fuck her again and I definitely wanted to fuck her some more. As it turned out, she wanted me to fuck her some more, too. She sucked my cock for a few highly-pleasurable minutes then gave me a choice.

"I'm going to stay in this position," she said, kneeling while leaning forward with her ass up in the air, "so I can either continue to suck your cock or you can move around behind me. You can choose."

Since I definitely wanted to fuck some more, I figured I could do that then have her suck my cock more, too. I got up and moved around behind her on my knees while she let her head drop down onto the bedspread. I ran my hands over her ass briefly before guiding my cock back into her hot, wet pussy. Holding her hips, I started to slowly slide in and out as she reached under herself and gently massaged her clit. Once again I was savoring the pleasurable feeling of fucking her, thinking that I'd be happy to do this for the rest of the night. I got a good, steady rhythm going then slid my hands up to cup her dangling boobs. I hefted their weight as I continued fucking her, caressing the soft, smooth flesh and her hard nipples. Fondling her big boobs seemed to make my cock even harder which she appeared to notice, too. She started pushing back harder and moaning louder, though that could also have been due to me stimulating her hard nipples. I suspect that it was a little of both but I just did my best to match her pace while continuing to fondle her tits.

When it appeared as though she was right on the brink of cumming again, I straightened up and held her hips. As she was pushing back harder and faster, I ceased trying to match her pace and would just thrust into her each time her ass smacked into my hips. Looking down, I was watching her ass jiggle each time it connected with my hips and figured that her tits were probably swinging like crazy, too. Although I was enjoying the pleasure that I was experiencing, I wasn't close to cumming yet and I had a good idea of how to get the rest of the way there once she'd cum. We abruptly went from hard, fast fucking to her pushing back and holding there so I just kept my cock fully embedded inside her. She suddenly let out a cry and her body started shaking so I gave a few thrusts as she was cumming and found her pussy flooded with even more lubrication.

It was another long and apparently highly pleasurable orgasm so, when it finally tapered off, she just remained there on her knees as she was recovering. I gave her another minute then figured she could continue to recover with what I wanted to do next. I slipped my cock out of her and had her roll onto her back then moved up to straddle her. I lay my cock between her tits and squeezed them together against it then began to slowly fuck them. Compared to her pussy and her mouth, fucking her tits was still incredible and feeling those big beauties in my hands only heightened the level of arousal. This position also gave me a good opportunity to just openly stare at her big tits, large areolas and hard nipples as I was both caressing and fucking them.

I knew it was unlikely that she was getting anything out of this position but she was attentive to my cockhead as it peeked repeatedly from her cleavage. Not that I was keeping score, but she also had experienced a couple more orgasms than I had so I felt no guilt about indulging myself and I doubted that she was put off by it. As I was savoring the feel of the soft, smooth flesh along the length of my shaft, I was debating internally whether I wanted to spew onto her chest. Her mouth had felt so good the couple of times I'd already briefly experienced it but I wasn't sure I'd be able to stop myself from fucking her luscious tits when I was getting close to cumming. Again, we had the whole night ahead of us still so, whatever I chose, there would still be plenty of time for the other.

When I was nearly on the verge, it was just the simple act of her opening her mouth, whether to encourage me to stick my cock in it or in anticipation of a load that would presumably be shooting toward it, that essentially made up my mind for me. I saw her mouth open up and I didn't even consciously make a decision; I just started moving forward as I released her tits. As my cock approached her face, she gripped the base of my shaft and guided it into her mouth. I moaned as she inhaled my cock and immediately felt it begin to swell even more as she commenced enthusiastically sucking it. There wasn't going to be any drawing out the pleasure, partly because I was so close to cumming already and partly because she was clearly pretty excited to have my cock in her mouth.

I savored the building pleasure as my orgasm continued to get closer, so glad that Jennifer had expressed interest in joining me at the hotel. I'd likely have had a couple of orgasms that night, anyway, but due to my own hand rather than her mouth or her tits or her hot, wet pussy. Once my orgasm was imminent, my cock swelled even more but she was not fazed in the slightest. She continued to voraciously suck me off and, even as I blasted into her mouth, she just swallowed my load while continuing to inhale my cock. It wasn't until I was completely spent that she released my cock from her mouth so I moved off beside her.