Long Overdue with Laura

More than twenty years had passed since Laura and I were last coworkers but we'd remained friends even after she'd moved from the Denver area to Missoula. Social media certainly played a part, and email before that, but we were also both still in the same industry so we would occasionally cross paths in one way or another professionally. She was in town for a training and had reached out as soon as she'd booked it to make sure I'd be around to meet up for drinks or dinner or both. Although we'd known each other for a long time and were both heterosexuals of opposite genders, nothing romantic or sexual had ever happened between us. That, of course, doesn't mean that I'd never thought about her in that way; I'd just never acted on it and never expected to, in the interest of maintaining our friendship.

Laura was arriving the afternoon before her training started so, once she'd checked in at her hotel, I was going to meet her there then we'd go out and get something to eat. I texted her when I arrived in the lobby and a few minutes later she was exiting the elevator. We both went in for a hug, which wasn't unusual since we'd ceased being coworkers, but this one was a little different. We were nearly the same height so, when our bodies came into contact, my cock was at about the same level as her pussy. For whatever reason, as we hugged this time, I could feel the softness of her pussy against my cock, as well as her boobs between us, and my cock reacted by stiffening a bit. It all happened so quickly that there was nothing I could have done to prevent her from feeling it. Oddly, she seemed to hang onto me for what seemed like a bit longer than a typical hug between two platonic friends and I totally didn't mind it. When we did finally part, she looked a bit flushed and had a big smile on her face, which I assumed I did as well.

"Maybe we go upstairs and you show me your room before we go eat?" I asked.

"I think that sounds like a great idea," she replied so we headed back to the elevators. We stepped inside when one arrived and I was thinking that I'd take her in my arms again and plant a kiss on her. Unfortunately, just as the door had almost closed completely, an arm shot into the gap and the doors popped open again. A family and all of their luggage joined us so we backed up against the back wall but, while we were ascending, I reached behind her and caressed her ass. My cock remained at half-mast as a result, even once we were out of the elevator and heading down the hall to her room. Inside with the door locked behind us, we stood at the end of her bed, wrapped our arms around each other and brought our lips together. We progressed quickly from kissing to making out, our tongues exploring each other's mouths. My hands were on her ass, pulling her against my stiff cock this time, though she was subtly grinding against it of her own free will.

We parted and crawled onto the bed, lying side-by-side in the middle and going back to making out. I was wearing shorts and a short-sleeved, button-down shirt while she had on a long skirt and a blouse with buttons. Instead of her ass, in this position I caressed her boobs, which were on the smaller side of average, but I was still psyched to get my hands on them since I never would have bet that we'd be doing this when she came to town. I could feel her hard nipples through her blouse and bra so I was thinking about unbuttoning her blouse and slipping my hand inside. When she reached down and began to massage my stiff cock through my shorts, though, I realized that there was no reason to take this slow. As much as I wanted to savor experiencing her body now that I had the chance, I was okay with following her lead and moving things along more quickly. I knew that I was pretty fired up and it seemed like she was, too.

Rather than opening her blouse and sticking with fondling her boobs, I slid my hand down and pulled up the hem of her skirt then caressed her pussy through her panties. I could feel the coarse texture of her bush as well as a moist heat and she responded with a soft moan even as we continued making out. I then slipped my hand into her panties, finding what seemed to be a well-groomed bush, before encountering her hot, wet pussy and slipping a finger into her. She moaned again as I was sliding my finger in and out then pulled her mouth from mine to moan even louder and longer when I started to lightly caress her clit. As she was gripping me tighter, she pressed her face into my neck and, although she'd abandoned my stiff cock in pursuit of her own orgasm, I was okay with that because I suspected very strongly that it would only be briefly. She was so fired up that I didn't expect it to take too long before she was cumming and I was confident that she'd take care of me in some way once she'd cum and recovered.

I was still pretty astounded that this was actually happening and I definitely wanted it to be a positive experience for both of us so my focus was on making sure she had a highly pleasurable orgasm. I wasn't trying to draw it out at this point, I just wanted it to happen then see where things went from there. It's always been a happy moment for me whenever I was able to slip my hand into a woman's panties and this was no exception. The fact that it was someone I'd known for so long but had never expected to be in this position was an added bonus. As she was moaning louder and gripping me even tighter, she was tensing up a bit so I figured she had to be really close to cumming. When she finally did, she briefly went silent then the tension left her body and she started shaking as she cried out. It appeared to be a long and intensely pleasurable orgasm, which I thought was great given that I was only using my finger. With my cock completely rigid, I was thinking more about fucking her at that moment but I'd still want to eat her to an orgasm or several, too.

When it appeared that she'd finished cumming, I removed my hand from her panties and tasted her juices on my finger. After taking a moment to recover, she was reaching for my shorts as she was getting up on her knees. She got them open and slid them down along with my underwear, my rigid cock springing out. After removing my shorts and underwear, she slipped off her panties then straddled me on her knees. Reaching under her skirt, she gently gripped my stiff cock as she guided it to her pussy. We both moaned as she lowered herself onto it. She sat there just feeling it inside her for a moment but soon began to slowly move up and down. As I enjoyed the pleasurable feeling, I reached up to unbutton her blouse. Once I'd exposed her bra, I was fondling her boobs, feeling her hard nipples through the thin material. Reaching around behind her, I unfastened her bra then slipped my hands up under the cups to caress the soft, smooth flesh.

Her nipples were big even though her boobs weren't so I knew I'd be licking and sucking them at some point, though it wasn't a priority at the moment. Her eyes were closed but her mouth was open because she was moaning again and she had an expression on her face that I thought was reflecting the pleasure that she was feeling. Once she had a steady pace going, she shed her blouse followed by her bra so I moved my hands to get a good look at her boobs. Her areolas were also on the smaller side but her boobs overall were really nice. I was watching them bounce and ended up just reaching around to caress her bare ass under her skirt instead of going back to fondling them. As she was riding me harder and faster in pursuit of another orgasm, I was becoming hypnotized by her bouncing boobs.

In addition to being tall, Laura was also athletic, so more fit than muscular but, as I caressed her ass, I was realizing just how toned it was. I had not seen her completely naked yet, nor had she seen me since I was still wearing my shirt for some reason, but I was expecting that to happen and probably pretty soon. I certainly wasn't focused on it at that moment as I watched her boobs and felt her hot, wet pussy sliding up and down my stiff cock. I was pleasantly surprised that I hadn't blown my load already given how amazing it felt as she was riding me along with the utter surprise that this was even happening. Since I wasn't feeling yet like I was getting close to cumming, I was pushing up into her each time she dropped down, making sure she was getting the full length of my stiff cock.

She was moaning louder and longer as she was riding me harder and faster so I knew it was a safe bet by this point that she'd be cumming before I did and likely very soon. I was figuring that, once she'd cum, if she didn't make a move to switch things up then I would. Not that I wasn't enjoying this position but, if we were going to do this, I felt like we should do all of it. When she did finally drop down and just remained there, she went briefly silent as well before crying out as her body started shaking. Since they were no longer bouncing, I brought my hands back around from her ass to fondle her tits again. I don't know that this provided any additional pleasure to her but I was certainly enjoying it. She moved up and down on my cock a few random times as she was cumming so I could feel that her pussy was even hotter and wetter now, which really made me want to continue fucking her, but she was in control at that moment.

When she'd apparently finished cumming, she let out a sigh and, after a very brief recovery, climbed off of my cock. She unfastened something then pushed her skirt down and slipped out of it so I removed my shirt, leaving us both naked. As she leaned forward while still on her knees, I got up and was quickly on my knees behind her. I ran my hands over her ass again before gripping my cock and guiding it back to her pussy from behind. We both moaned as I eased it in until my hips were pressed against her ass then I held her hips as I slowly slid it in and out. Once I had a steady rhythm going, I slipped my hands forward to cup her tits, feeling her hard nipples against my palms and thinking once again that I would need to find an opportunity to lick and suck them. Meanwhile, she reached back under herself, presumably to caress her clit as I was fucking her. I was happy to see her being proactive about her own pleasure.

I was content to maintain a slow pace while sliding the full length of my stiff cock in and out of her to savor the pleasurable feeling. Gradually, though, she began to push back harder and faster so initially I was just trying to match her increasing pace. Soon, though, I straightened up and was holding her hips again and just giving a thrust each time her ass smacked against my hips. I was looking down, watching my cock disappearing and reappearing but there was no jiggle at all when her ass hit against my hips. I didn't mind that she wanted things to go faster, mainly because I knew it meant she was building toward another orgasm, and I liked the sound of her ass smacking repeatedly against my hips. I was starting to feel the stirrings of my own orgasm and was still pleasantly surprised that I'd been able to last and enjoy this for so long. I wouldn't have an issue finally blasting my load deep inside her, though, especially since it looked like she'd be cumming again before I did first.

When she pushed back hard and held there, I made sure that my throbbing cock was fully embedded inside her and held there myself. A moment later, she cried out and started shaking so, assuming her hot, wet pussy was getting even hotter and wetter, I couldn't resist slowly sliding in and out of her a few times as she was cumming; the feeling certainly didn't disappoint. I still wasn't quite there yet myself, despite how amazing her pussy felt and how much I was enjoying fucking her, but once again I was not complaining. Her orgasm appeared to be another long and intensely pleasurable one, which I was thinking must be the norm for her, but I was glad to have been able to help her get there. I was still slowly fucking her and assuming I'd be cumming into her before too long when she apparently finished cumming because she moved forward so that my cock slipped out of her.

As she was straightening up on her knees, I moved around and lay on my back so that my upper body was near where she was kneeling. She caught on right away and moved laterally so that she was straddling my head then gently gripped my stiff cock while leaning forward. As she was slowly pumping it, I was gazing up at her trim, brown bush, then she engulfed my cock in her mouth and I let out a moan. I lay there, gazing at her pussy and enjoying the pleasurable feeling of her sucking my cock before raising my head and running my tongue along her slit. I brought my hands up to caress her ass while licking her slit and slurping up the copious juices she was producing. She moaned with my cock filling her mouth but continued to skillfully blow me. I could already feel my orgasm building up again and I was perfectly okay with finishing up in her mouth.

For whatever reason, going back to when we'd first started working together, I'd always had this sense that she was probably a good cocksucker. I had no evidence of any kind, no hearsay, no stories, but I know that I thought on more than one occasion that I'd love to have her suck my cock to find out for sure. Maybe, because I knew nothing about her sexually or her sexual history, I had this vision of her where she was saving herself but was willing to suck cock instead and had honed her skills doing that. No idea why I was thinking like that but, even as we got to know each other better, we never delved into sexual discussions so I had at the very least held onto this belief, whether valid or not. Now that I was experiencing her skills firsthand, I had to think that there was a possibility that I'd been right, but we were also quite a bit older so these skills could have actually been developed while we'd known each other.

Whatever the case, I was enjoying the pleasure she was able to provide with her mouth though I was not doing anything to try to hold back my orgasm to enjoy it for longer. I was focusing on how good it felt while also doing my best to put some focus on making her feel just as good. To that end, I slipped a finger into her hot, wet pussy and was sliding it in and out while licking and sucking her clit. I wasn't necessarily trying to draw the pleasure out for her, especially since she'd already cum several times, but was doing what I could to elevate the pleasure, if that was even possible. I wasn't sure whether she was trying to draw out the pleasure for me or not or maybe even for herself if she was happy having my stiff cock in her mouth. With how amazing it felt to have her lips sliding up and down my shaft, there would have been only so much she could do to draw it out because my orgasm was building pretty quickly as a result.

Once it felt as though I was right on the verge of cumming, I did take a break from licking her clit and let my head drop back to focus on the pleasure. I continued to slide my finger in and out of her pussy as I was gazing up at it while moaning louder and longer the closer I was getting. When I finally started to spew into her mouth, she never even flinched, just continuing to suck me off as she was swallowing my load. The groan I let out was in part due to the intense pleasure but also in part due to relief after a long build up. By the time I was fully spent and starting to soften, I'd gone back to licking and sucking her clit so that, when she released my cock from her mouth, she was immediately moaning loud and long herself.

With her focus now solely on her own pleasure, it wasn't long before she was obviously on the verge of cumming once again. I kept my goal of trying to provide the most pleasure that I could rather than pushing her toward an orgasm but they ultimately were one and the same. She was tensing up just a bit right before briefly going silent then letting out a cry as her entire body was shaking. I continued sliding my finger in and out of her now hotter and wetter pussy while licking and sucking her clit as she was cumming, hoping to prolong or elevate the pleasure even more. Once again it was a long and obviously highly pleasurable orgasm so it was rewarding for me to have been able to help her get there, though doubtfully as rewarding as it was for her.

When she'd obviously finished cumming, I slipped my finger out of her and let my head drop back while still gazing up at her pussy. After taking a moment to recover, she moved off of me and we repositioned ourselves, lying side-by-side with our heads on her pillows.

"That was long overdue," she finally said, "but well worth the wait. Even better than I ever imagined."

"So you've been imagining what it'd be like, too?" I asked.

"For a while now," she replied, "but it never felt like the right time until tonight, though I feel like tonight wasn't completely our decision."

"Right?" I responded, "Like the universe was telling us that the time was finally right."

"Exactly," she replied, "and I feel like we've just scratched the surface but maybe we should fuel up for the night ahead?"

"That's a good plan," I said, "then we can come back here and keep going all night long."

"I would love to think that I have that kind of stamina," she replied, with a laugh, "and that I wouldn't need any sleep before my training tomorrow but, yeah, let's give it a shot."

We got up and gathered our clothes, dressing again though I was mostly watching her until she was covered up then realized I needed to catch up. We headed out of the hotel, going where we'd originally discussed having dinner, ate lightly but each had a cocktail and talked about what had already happened and what we wanted to do once we were back at the hotel. She had one particular fantasy from when we'd worked together that she wanted to make a reality and I was completely onboard with it. As soon as we were back in her room with the door locked behind us, she crawled under the desk where her laptop was set up and where she had some paperwork spread out, then had me sit in the chair and roll up to the desk like I was working. She had such a big smile on her face, which gave a good indication of just how excited she was to be doing this.

I knew what was coming but it was still incredibly hot when she ran her hand up my leg and started to massage my growing cock through my shorts. As it continued to stiffen, she worked on getting my shorts open then extracted my cock, gently pumping it before engulfing it in her mouth. I was moaning as she was once again skillfully sucking my stiff cock while I tried to maintain the illusion that we were at work since that was her fantasy. This time, I was completely focused on the pleasure I was feeling just as she was completely focused on the pleasure she was providing. I had already indicated that I wanted to swap positions before we finished up with this fantasy so I fully intended to give her all of my attention, as well, at that time. For now, though, even given that I'd already fucked her and had blown a load down her throat, I was still feeling like this was the best thing I'd ever experienced.

This time I knew she had to be working some oral magic to draw out the pleasure because, as incredible as it felt, it seemed as though I should have cum very quickly as a result. The only explanation for being able to enjoy her cocksucking for so long is that she knew some tricks to make it feel incredibly good but not immediately make me cum. I would have been more than happy to sit there while she was sucking my cock for, maybe not the entire rest of the night, but let's say a good long time. I did have to lean back though, and stop pretending to work, so that I could watch. It was unbelievably hot to see her under the desk, fully dressed, pumping the base of my cock while it disappeared into her mouth. Even though having her sucking my cock had been a longtime fantasy, watching as it was actually happening was another level entirely.