Field Trip Chaperone

I was sitting in the hotel bar, enjoying a local craft beer, when she walked in and ordered whiskey on the rocks. She was blonde, maybe a little older than me, with big boobs, fair skin and just the right amount of curves. It was her choice of cocktail that drew my attention, however. When she caught me staring, she raised her glass toward me.

"To day drinking," she said and I raised my glass in return.

"Must be a hell of a day if you need some whiskey already," I replied after sipping my beer.

"Three-and-a-half hours on a school bus full of middle schoolers," she stated, sipping her whiskey.

"That'd do it, I imagine," I replied, "but, fortunately, I've never experienced it."

"I wouldn't wish it on anyone," she said, "and I'll be doing it again tomorrow when we leave. Don't get me wrong, I love those kids, just not for so long in a small, enclosed space."

We laughed and she moved to sit on a stool closer to me.

"What is going on that brings you here with a busload of middle schoolers?" I asked.

"It's a class trip to come to Denver, get dressed up, eat at a nice restaurant and see a play," she explained, "Fortunately, there were a lot of parents interested in joining us so we've got a good chaperone to student ratio, which has allowed me a few minutes to enjoy this, by which I mean not only the whiskey but the company as well. Is it safe to assume you're not a local since you're drinking in a hotel bar?"

"I'm here on business, though we wrapped up early today," I replied, "I figured, rather than rush to the airport, try to change my flight and get home late, I'd stick with my morning flight and have a relaxing evening."

"Serendipitous," she said.

"It's feeling that way," I replied. There was definitely a bit of chemistry between us, evident even in the short time we'd been talking. I had nothing planned for that night and would have suggested going out and doing something fun to see where it led but she obviously was pretty busy so I wasn't really sure what to do. Fortunately, she came up with something on the fly.

"My plan was to savor this drink then go back upstairs to freshen up and get dressed for tonight," she said, "but now I'm thinking of inviting you upstairs to help me get ready. If you're in, it'll be bottoms up."

"Are you talking about the drink or..." I trailed off. She just raised her eyebrows so I downed my beer and she followed suit with her whiskey.

"We'll need to be super discreet," she said, "so let me go up first, we're on the sixth floor, and I'll get my door unlocked and make sure the hallway is clear. You just follow and walk down the hallway like you belong there, whether it's empty or not. If it's empty, I'll be waiting to drag you into my room. If it isn't, I'll be working on clearing it so I can drag you into my room."

"Sounds like a plan," I replied, "see you up there..."

"Oh...Jocilyn," she said with a laugh so I offered my name, which she repeated with a smile, then she took off. I followed slightly behind and took the next elevator after hers. Fortunately, when I arrived on her floor, the coast was clear and she was peeking out from her room making sure it remained that way. Once I'd slipped in, she locked the door behind us and followed me to the foot of her bed. We were then in each other's arms, kissing then making out passionately. My cock stiffened and I figured she had to be feeling it against her abdomen as I pulled her closer with my hands on her ass. Assuming that we didn't have an abundance of time, I soon began to raise her blouse up so we parted as she lifted her arms to allow me to remove it. Her tits were substantial, supported in what I thought was a very sexy bra, though she may not have put it on that day with the intention of anyone seeing it. I fondled her tits, feeling her hard nipples pressing outward, then reached behind her and unfastened her bra. I watched those big beauties as they were revealed, topped with large areolas and stiff nipples. As her bra dropped to the floor, I was fondling the soft smooth flesh and running my palms over her hard nipples before lowering my head to lick and suck them.

I could have gone on for longer but, again, I wasn't sure she had the time for indulging so, as I was slobbering on her tits, I was working on getting her jeans open. As I started to slide them over her hips, I dropped down before her and watched her panties come into view. Again, I found them very sexy but they probably weren't the ones she'd have put on that morning if she'd known that someone else would be seeing them. I helped her step out of her jeans then briefly admired her wearing just her panties before sliding them down. Her bush was surprisingly blonde and well-groomed, which made me not only want to devour her pussy but also take a picture of it. First things first, though, so I had her sit on the edge of the bed while I moved in closer. After admiring her pussy for a moment, I lowered my face toward it then ran my tongue along her slit. She was overflowing with juices and moaned softly as I worked on lapping them up.

She lay back and, as I glanced up along her body, her tits were begging to be fucked so I hoped I'd get the opportunity. She wasn't watching as I was eating her pussy, presumably as she focused more on just the pleasure she was feeling. Her soft moaning was continuous and her hips were starting to rock subtly. When I slipped a couple of fingers into her and focused my lips and tongue on her clit, a louder moan slipped out but she quickly got herself under control again. She reached down to hold my head with both hands, though, humping her pussy toward my face. Glancing up again, her tits were now squeezed between her arms and pointing at the ceiling nearly causing me to moan. I knew if we ran out of time, I'd never get to fuck those beauties so I was focused more on giving her a highly pleasurable but quick orgasm rather than drawing out the pleasure. As she was writhing more actively before she began tensing up, I figured I was on the right track.

Her pussy was becoming even wetter and more engorged the longer I was eating it so I was looking forward to fucking it as well as fucking her tits. When the tension suddenly left her body and she started shaking, I knew it wouldn't be much longer. Her orgasm was long and appeared to be intensely pleasurable, just as I'd hoped it would be. I continued licking and sucking her clit while sliding my fingers in and out of her pussy until she went still and let out a sigh. At that point, I slipped my fingers from her pussy and sucked her juices off of them as I stood. As she gazed at me sort of dazedly, I pulled off my polo then opened my jeans and let them drop to the floor. Before I'd even stepped out of them, I was pushing my briefs down to join them, my rigid cock springing out. Her eyes went wide and she sat up, briefly stroking my cock and cupping my balls before turning to crawl to the middle of the bed. I yanked off my socks, leaving all of my clothes in a pile and followed her. She remained on all-fours, looking over her shoulder, while I moved up behind her on my knees, my cock sticking out ahead of me.

I ran my hands over her ass before guiding my cock into her pussy, making both of us moan. She was so incredibly hot and wet that it felt even better than I'd expected. Once I was fully embedded, I wasted no time in grabbing her hips and starting to fuck her. It wasn't hard and fast, at least not immediately; it was more like long, full strokes as I relished the feel of her pussy along my achingly hard cock. She dropped her head down onto the bedspread and reached back between her legs, presumably to caress her clit. Once I had a steady rhythm going, I moved my hands up to cup her swinging tits. Feeling them again reminded me that I could not miss the opportunity to fuck them so my goal was to make sure that she came again then fuck her tits. It didn't end up happening exactly like that but I didn't have any complaints about how it did end up going.

She started pushing back against my thrusting and essentially set a faster pace as her soft moaning was becoming more continuous. I straightened up and held her hips again, basically just thrusting each time she pushed backwards while watching her ass jiggle as it hit my hips. I could feel her pussy becoming wetter and more engorged again so I knew she was close to having another orgasm pretty quickly. Fortunately, while I was absolutely enjoying the opportunity to fuck her, I wasn't in any danger of cumming quite yet. Her pace continued to increase, her ass smacking against my hips, until she abruptly gasped and went into slow motion, her body quivering as she came again. I just savored the increased lubrication as her pussy continued moving slowly up and down my cock.

When she finished cumming, I slipped my cock free, intending to flip her over and fuck her tits. She rolled onto her back without any prompting but spread her legs and beckoned for me to continue fucking her. Looking over her naked body laid out before me, I couldn't resist the allure of fucking her hot pussy some more but resolved to not get so engrossed that I forgot about laying my cock within her undoubtedly soft, smooth cleavage. I lowered myself over her while guiding my cock back into her hot, wet pussy. We started kissing as I commenced fucking her again and, feeling her naked body against my own, as well as her tits between us, I knew I wouldn't forget about fucking them. Our tongues were soon exploring each other's mouths as she was raising her hips to accept my thrusts. Again I started with long, full strokes in and out of her hot, wet pussy but it wasn't long before I was fucking her harder. The sturdy hotel bed remained quiet but Jocilyn didn't; she pulled her mouth from mine so that she could moan as she appeared to be approaching another orgasm, although she did so quite softly. I hadn't expected this but she was clearly very worked up and I was pretty sure it wasn't my technique, at least not completely.

She gasped and started shaking below me as I continued to fuck her, relishing the increased lubrication that flooded her pussy. Even as good as that felt, as soon as I was certain that she'd finished cumming, I extracted my cock and moved up to straddle her. As I lay my cock between her succulent tits, she realized what I was up to and smiled. I squeezed her tits against my cock and started to slowly fuck them while gently brushing my thumbs over her hard nipples. Even after her amazingly hot and wet pussy, the soft, smooth flesh of her tits felt outstanding as my cock slid against them. If somebody had come knocking on her door, I don't know that I would have been able to make myself stop fucking her tits but, fortunately, we were not interrupted. I savored the feeling as my orgasm begin to gradually build in earnest. She was watching as my cockhead disappeared and reappeared, her tongue jutting out occasionally and reminding me that I hadn't slipped my cock into her mouth. As much as I was enjoying the experience of fucking her tits, the idea of cumming in her mouth was quite appealing. I was pretty sure that this was going to be a one-time thing so I figured I should try to experience it all.

As my orgasm drew closer, I was relishing the build-up and the feel of her tits against my cock. It wasn't easy to make myself quit but, seeing her tongue, I knew it was going to feel pretty awesome as well which made it a bit easier. I finally released her tits and moved forward, aiming my rigid cock toward her mouth. She raised her head and engulfed it while gripping the base as I grabbed the headboard. I didn't even have to fuck her mouth because she started to voraciously suck me off immediately. Her cocksucking was skilled and pleasurable and looking down to watch her only heightened the intensity. My orgasm was building steadily and I was looking forward to blowing my load down her throat. I had to consciously refrain from moaning so I was whispering softly to let her know how awesome it felt. The fact that my cock was so rigid may have given her a clue, as well. As I was getting closer to cumming, it was swelling even more but that had no effect on her cocksucking; she continued to steadily inhale it.

When I started to spew, I did let out a groan of sorts, but I don't believe that it was loud enough to be heard outside of her room. She swallowed my load and continued to suck me off as I was spurting repeatedly into her mouth. Only once I was finally completely spent did I move back so that my softening cock slipped out. I knelt beside her rather than lying down so that I could resume admiring her naked body.

"That was absolutely outstanding," I finally said.

"Agreed," she replied, "It has crossed my mind to pretend I'm not feeling well so I can stay here with you."

"You can't do that," I protested, "as much as I would enjoy it. You came all the way down here on the bus with the kids; you can't miss the big night out with them."

"I know," she said, "but do you think you'll be around later when we get back?"

"I will absolutely make it a point to be here if it means spending more time with you," I replied and she smiled so I leaned down to kiss her.

"You're probably going to have to leave, though," she finally said, "so I can get ready. Otherwise, I'll still be tempted to bail."

"Okay, okay," I replied, "I will write down my contact info and room number but I suggest you don't leave it sitting out if you expect anyone to be in here. There's also one thing I'll need before I take off."

I grabbed my phone from my pile of clothes and took a couple of pictures of her, naked and still sprawled out on the bed. Then I grabbed the pad and pen provided by the hotel and jotted down my name, cell number and room number before starting to get dressed. She peeked through the peephole to make sure the immediate area was clear, then opened the door and cautiously stuck her head out, still naked. The hallway was empty so I slipped out and she immediately closed the door behind me. Before I'd made it back to my room, I had a text from an unknown number which turned out to be a naked mirror selfie from Jocilyn. I smiled as I felt the blood trying to return to my spent cock.

I had a rough idea of when the play they were seeing would be over and estimated how long after that she'd have the kids back at the hotel and not need to be chaperoning them anymore. In the meantime, I went out and wandered around downtown Denver and had something to eat but I was back at the hotel with plenty of time before I expected to hear from her. I was sitting in bed, propped up against the headboard and dinking around on my laptop when she texted and said she was on her way. I had already done my nightly ablutions and was in a pair of lounge pants and a t-shirt so I set my laptop aside and propped the door open with the deadbolt then sat back on the bed. I didn't hear the door open but I heard it close followed by the deadbolt being turned then Jocilyn came around the corner. She was wearing a knee-length, sleeveless dress that was conservative enough for being around schoolkids but that I found very sexy. It was even sexier when she raised the skirt and slipped off her panties. I caught a really quick glimpse of her blonde bush before her skirt covered it again but my cock immediately started to stiffen.

She tossed her panties onto the bed then got on it herself on her knees as I slid down so that I was flat on my back. She didn't fail to notice that my lounge pants were beginning to tent so she caressed my stiffening cock, causing it to stiffen even more, before she slid my lounge pants down. My cock sprung out but she slid my lounge pants all the way off before reaching for it and briefly stroking it. I slipped out of my t-shirt, too, as she moved up to straddle me, still wearing her dress. She reached under the skirt and guided my cock to her pussy then lowered herself onto it. She was ridiculously hot and wet and I suspected that her panties were probably a bit damp. We both moaned as my cock was engulfed within her, more loudly here in my room than we would have in hers.

I slipped my hands up under her dress to caress her ass as she started to slowly ride my cock but I knew I'd need to free her succulent tits. It looked like they were pretty well restrained so I assumed they were yearning for freedom. As she got a steady pace going, I knew her tits would be bouncing nicely if they were free so I set about to release them. I unzipped the back of her dress and pulled the top of it down, exposing her bra. I briefly caressed her tits through her bra before reaching behind her to unfasten it. As I slid her bra down her arms and those beauties were exposed, I'm sure my eyes got wide as did my smile. After tossing her bra aside, I watched them bouncing for a moment before my hands were drawn to them. I caressed the soft, smooth flesh and ran my palms over her thick, hard nipples.

It got even better when she leaned forward, planting a hand on either side of my head, as she continued to ride me harder and faster. This had her tits swinging like crazy but they were right in my face so I could caress the soft, smooth flesh while licking and sucking her hard nipples. I'm not sure if this was helping her toward her obviously building orgasm, but I'm sure it didn't hurt and I was certainly enjoying it. She was getting louder the longer she was riding me and I got the impression that she was appreciating the opportunity to express herself more freely. Her pussy continued to become even hotter and wetter and, as much as I was enjoying her big titties, I was also relishing the feel of her pussy moving up and down my cock. I started pushing up into her each time she came down on my cock so that she was getting my full length and I think this may have helped her toward her orgasm, as well.

When she slammed herself back and just stayed there, it was only a moment later that she let out a cry and started shaking. I continued to lick and suck her nipples as she was cumming, glad that she was having another obviously highly pleasurable orgasm. When she finished cumming, she straightened up but remained sitting on my cock as she recovered. Her tits were still within reach, though I could no longer lick and suck her nipples, so I contented myself with just fondling them. Once her head had apparently cleared enough, she smiled at me then stood, my cock vacating her pussy but remaining rigid. Standing on the bed beside me, she pushed the dress down over her hips, her tits swaying enticingly as she leaned forward to help it down her legs. After stepping out of it, while I admired her fully naked and looming over me, she turned and straddled my head, lowering herself down into a sixty-nine.

I was gazing up at her blonde bush as she gripped my cock and briefly pumped it before lowering her head to take it into her mouth. It felt so good that I couldn't remain silent so I let her know how much I was enjoying it before raising my head to lick her pussy. I was running my hands over her ass as I ran my tongue along her slit, tasting the copious juices she was producing. She moaned as she continued to suck my cock while gently pumping the base. I brought one hand down from her ass and slipped a finger into her hot, wet pussy while licking and sucking her clit, which caused her to moan even more. As her mouth moved up and down my rigid cock, I could feel my orgasm beginning to build up and was savoring the pleasure I was feeling.

I don't think that she was trying to make me cum quickly; I think she just couldn't help it because she was so good at sucking cock. She was so skilled, in fact, that when my cock started to swell more and my orgasm was nearly imminent, she modified her technique to draw out the pleasure I was feeling for even longer. She wasn't necessarily denying me an orgasm, per se, but was prolonging the build-up which, of course, meant that I was licking and sucking her clit while fingering her pussy for longer, too. I could feel her pussy not only becoming hotter and wetter but more engorged as well while I continued to enjoy devouring it. I was still pretty sure that I would be cumming before she did, though, which was fine since she'd already had one orgasm and I intended to eat her to another one once I'd cum.