We probably should have talked about our plans for the conference before we arrived. For whatever reason, I had assumed that, because we were going to be at the conference together, my coworkers and I would be hanging out during our off time and that it would be a good non-work opportunity for bonding. I was apparently the only one thinking that. Once we arrived at the hotel in Maryland and got checked in, I asked what the plan was once we dropped off our luggage in our rooms. The conference didn't start until the next morning so we had that evening to go out and do something. As it turned out, everyone else had already made plans for the evening, with friends or family who were nearby, but no one had said anything about it to anyone else. I was just as guilty, assuming we were going to hang out but never actually bringing it up for discussion.
While I had no issue going out on my own and finding something to do, I did know that an acquaintance from my hometown lived somewhere in the area. I got on my laptop, did a bit of digging on social media, checked the local map then reached out to Sherry on social media without really expecting much on such short notice. I hadn't gotten very far in coming up with a contingency plan when I got a notification from Sherry. She'd replied to my message that she was nearby and was actually available that evening. She suggested that she come and pick me up at the hotel and that we go to a nearby brewpub. Even if we hadn't seen each other in person in years, she was apparently able to glean enough about me from my social media profile to know that I'm a total beer snob and that a brewpub would totally be my jam.
I freshened up a little then headed for the lobby and kept an eye out for her car. When she pulled up, I got in the passenger seat and we hugged, a bit longer than I was expecting but I had no complaints. As she drove and we were catching up, I noted that she was wearing a sundress that, while it wasn't revealing per se, didn't hide how big her boobs were and had slid up enough to show off her legs. I realized pretty quickly that, if I wasn't careful, I'd be pitching a tent in my shorts. I refocused on the scenery, occasionally glancing at just her face, which was cute but not as likely to get me aroused. It wasn't a long drive anyway and we were soon parked and headed inside. Sitting across from each other in a booth, we continued catching up with a couple of cold beers that had been brewed on the premises.
We each had a second beer along with our food but I declined a third, since I knew I had a full day of conference sessions to attend starting early the next morning and didn't want to be hungover or dehydrated. Since we weren't ready to head out quite yet, there was time for her to steer the conversation to the hotel where I was staying and where the conference was taking place. It took probably way too many subtle hints about the hotel and my room and the view before I realized she was angling for an invitation up to my room.
"Why don't you come up and check out my room when we get back to the hotel?" I asked, to let her know that I'd finally caught on.
"That sounds like a great idea," she replied, with an expression of relief that said she had been running short on subtlety.
We left the brewpub soon after and, when we arrived back at the hotel, I was able to get her into the underground parking garage with my room key. I wasn't 100% certain of where this was going so I held back from doing anything while she was driving, like sliding my hand up along her smooth thigh. Once she'd parked, though, and we were in the parking garage waiting for the elevator, we were quickly in each other's arms, our lips coming together. I ran my hands over her ass to pull her against my stiffening cock and was pleasantly surprised by how toned it was, having somehow forgotten about all of the yoga she often posted about. It was also quite apparent that she was not wearing panties under her sundress, which just caused my cock to stiffen even more.
"So no panties, huh?" I said as we entered the empty elevator once it finally arrived.
"No bra, either," she replied, "but I knew my panties would have just been really wet so I decided to skip both."
"Are you a little fired up?" I asked, maybe still a little dense about what was on her mind.
"You know I had a huge crush on you back in high school, right?" she asked, "I'm not about to let this opportunity slip by so I've been thinking about it since you messaged me."
"Wait...what?" I eloquently replied, "Don't get me wrong; I am completely on board. But this is a complete surprise to me."
"Oh, really?" she asked, "I thought it was written on my face every day but I was just a sophomore so you probably didn't even notice me anyway."
"It would be hard not to notice you now," I said, wanting to reassure her because, although a surprise, I was completely into this happening. We were still riding the elevator but it seemed like there would be time for some kissing before we reached my floor so I took her in my arms and planted one on her. She was grinding against my stiff cock as we made out then, as the elevator was slowing down, we parted. She looked a little flushed and I'm sure that I did, too. As the elevator opened, I took her hand and led her down the hall to my room. I unlocked the door then had her go in first so, as I was locking up, she was checking out the view. I joined her at the window, standing behind her, then cupped her big boobs and pressed my stiff cock against her ass. She ground her ass against my cock and, while it was tempting to just pull her dress up and fuck here there in front of the window, there was a big bed that would work really well instead.
She didn't resist as I took her hand again and led her back to the bed where we both crawled onto it on our knees. We made out briefly while kneeling in the middle of the bed but then I lay her down and pushed the hem of her dress up to expose her pussy. Her light brown bush was well groomed and, once I was positioned between her spread legs, I leaned in and ran my tongue along her slit. She moaned and reached down to hold my head as she subtly humped her pussy toward my face. She hadn't been kidding about being wet; she was practically overflowing with juices, which I was eagerly lapping up. Her moaning was long and loud pretty quickly, which I was attributing more to how fired up she was than to any particular skill on my part. In fact, it was only a couple of minutes after I started licking her pussy when her moan became a wail and her body started shaking.
That took a bit of pressure off but I wasn't ready to be done so, as she was cumming, I was still licking her slit and hoping that it was increasing the level of pleasure she was feeling. Regardless, it appeared to be a long and highly pleasurable orgasm and, when she finished cumming, it sounded like she was immediately building toward another one. I slipped a finger into her pussy, discovering how snug it was, but still easily sliding in due to how wet she was, which had me thinking about slipping my hard cock into her. I still wanted to continue eating her, though, and figured there would be ample opportunity for fucking as well as for eating her pussy some more. Her moaning was getting louder and longer again after a brief respite while she came and recovered but I wasn't doing anything to draw out the pleasure since she'd already cum.
When she went briefly still and silent then cried out as her body was shaking again only a short time later, I was not surprised and just continued to devour her pussy. In fact, when she came down from that orgasm, I just kept going and enjoyed eating her pussy through a couple more. When I finally raised my head, it wasn't because I was ready to be done necessarily but I was suffering a bit of tongue fatigue by then and I was also ready to fuck, plus she seemed like she was barely coherent any longer. I straightened up on my knees but was gazing down at her pussy as well as her toned legs and abs when I realized that I had yet to see her big boobs. There was a row of buttons that ran up the front of her sundress so, as she was recovering, I started at the hem and unbuttoned toward the collar.
When her big boobs were finally revealed, they did not disappoint. The dress fell away to each side but her boobs stood firmly upright despite their size. Her areolas were large and her nipples hard so, after caressing the soft, smooth flesh, I couldn't resist lowering my head to lick and suck her nipples. She moaned and ran her fingers through my hair, indulging me for a bit before she was ready to move things along. When she started to pull my shirt up, I raised my head and released her boobs but, rather than going back to her boobs once it was off, I flopped onto my back beside her so that we could get my shorts off. She shed her dress as she got up on her knees while I watched her big boobs bouncing and swaying. My shorts were quickly opened, then she slid them down along with my briefs, my stiff cock popping out.
After making sure that I was as naked as she was, she gently pumped my cock before briefly engulfing it in her mouth, sliding her lips up and down it a few times. I'd have been more than happy to blow a load down her throat but she had other plans and soon straightened up, straddling me then guiding my cock toward her pussy. We both moaned as she lowered herself down onto it then I reached for her boobs again, fondling the soft, smooth flesh and caressing her hard nipples as she was beginning to slowly ride me. With my hands covering them, I couldn't admire her big, beautiful boobs and, when I glanced up at her cute face, I saw a smile that strongly suggested that she was having the time of her life. It seemed so improbable that, after being ditched by my colleagues, the only person I ended up knowing in the area was someone who was clearly eager to jump my bones. There was no way that this was a coincidence; other forces had to have been at work and I obviously did not have a problem with that.
Her snug, slippery pussy felt outstanding as she moved up and down on my stiff cock and, as she was gradually picking up her pace, I could feel her boobs starting to bounce. I moved my hands so that I could watch, sliding them down and around to caress her ass instead, reminding me once again how toned it was. Her boobs were pretty spectacular as it was but watching them bounce was nearly hypnotizing. As she continued to ride me harder and faster, moaning even louder and longer as she did, I was pushing up into her with my hands on her ass while fixated on her bouncing boobs. Her pussy was feeling even hotter and wetter but I was not building toward an orgasm of my own quite yet, which was a pleasant surprise. I was more focused on making sure that she was enjoying herself and keeping that smile on her face. I had no idea at that point whether she'd ever imagined herself in this position but, just in case she had, I wanted it to live up to her expectations.
Even with the multiple orgasms she'd experienced as I'd been eating her pussy, I still wanted her to cum while we were fucking and it seemed like that was close to happening. She was not shy about expressing herself and, between that and her pace, she was obviously right on the verge of cumming. When she dropped down and stayed there while abruptly going silent, I brought my hands back around to fondle her boobs again since they'd stopped bouncing. A moment later, she cried out and started shaking as her orgasm overtook her. Since I was just fondling her boobs for this one, I was able to observe a bit more and, while the smile never left her face, it somehow looked more ecstatic than happy as she was cumming. It was a long orgasm and appeared to be highly pleasurable so that came as a relief to me.
