Note: If you haven't already, read My Former Coworkers, which is the prequel to this story.
***
Following that afternoon threesome with our mutual former coworker, Cindy and I were seeing each other whenever we could manage it and the sex was pretty much outstanding. A couple of months later, when she was preparing to leave on a vacation with her boys, I think we were both a little bummed that it would be a while before we could get naked together again. She was obviously excited to be taking a trip with her sons, though, and I definitely didn't want to intrude on their time together so I just promised that I'd keep in touch while she was gone. Little did I know that one entirely innocent vacation photo would get us both so stirred up.
She posted a pretty standard vacation photo on social media showing her lower legs and feet with the resort pool in the background, indicating how she was spending that particular afternoon with her boys. Since it left pretty much everything to the imagination, I shot her a message asking if she was wearing a bikini or a one-piece swimsuit. Her reply was that she was wearing a conservative, mom-appropriate one-piece so as not to embarrass her boys. She followed that up by asking if I wanted to see it.
"I'd rather see you taking it off," I replied, "Can you send me photos when you're getting ready to shower and maybe a video of your shower?"
I wasn't entirely serious but I was hopeful. I figured that, even sharing a suite with her sons, she probably had a fair amount of privacy at least when she was changing and showering. The question was whether she'd feel comfortable doing something like that for me with them nearby.
"I'll see what I can do," was her response, which I found to be pretty encouraging. Sure enough, later that afternoon, she uploaded a series of photos to the file-sharing site where we exchanged such things. She apologized for not including a video, especially since she admitted that the photo session had gotten her worked up enough to quickly and quietly satisfy her own needs during her shower. I glanced through the photos when she posted them but, since she'd admitted to taking matters into her own hands, I had an idea of how to let her know not only the effect of her photos on me but also that she wasn't the only one a little pent up.
When I was alone later that evening, I brought the photos up on my laptop and set up a slideshow. She'd taken the photos in the bathroom mirror in their suite using her phone, progressing from fully covered by her swimsuit, to her boobs exposed, to her pussy nearly exposed, to her pussy just exposed (and recently groomed, by the looks of her bush), to the swimsuit at her knees, then at her ankles then completely naked. She also included several shots from behind in the mix, as well. It didn't even take a full cycle through them before I was rigid so, once I was ready to go, I just had to hit the record button on my phone. I'd positioned it so that, as I stroked my stiff cock, she'd not only get to see that in the foreground, but that I was stroking to her photos in the background. Between being a bit pent up and her photos being so hot, it wasn't going to take long before I was spewing, though I didn't necessarily want to end up with too short of a video. As it turned out, I was able to provide her with a couple of minutes of my hand sliding up and down my rigid tool before I started spewing, my copious jizz spilling over my fist. It felt good to release the sexual tension but it was better having done so to her photos.
Later that night, a while after I'd let her know that there was a short video available for her, she messaged me to let me know that she'd enjoyed the video and that, despite her kids being in the next room, she had stroked her pussy under the covers while sitting in bed watching it. She thanked me for recording and sharing the video and apologized that she hadn't been able to reciprocate because it had been both too dark and too risky. The next day, however, when she was taking her shower, she managed to shoot a nice, long video of that as well as of her getting herself off again while showering. It was so ridiculously hot to watch that, when I shot my own video again, my cumshot was monumental. We agreed, however, that we didn't need to keep recording and sending videos since it'd be just a few more days before we'd be able to see each other naked in person.
Once they were back from their trip, her boys immediately spent some time with their dad since he hadn't seen them for as long as I hadn't seen Cindy. She invited me to come by as soon as they were gone and was ready for me when I arrived. She opened the door wearing her one-piece swimsuit and my cock started to stiffen immediately.
"Look who's all conservative," I said as I admired her body, "I never realized that 'mom-appropriate' could look so fucking hot."
I slipped into her arms as she pushed the door closed and, as we made out in the entryway, my hands were caressing and squeezing her swimsuit-clad ass. I'd have been fine if she'd been wearing a caftan or a muumuu, entirely hiding her figure from me, but I was glad that she was showing it off instead. I'd seen her naked on numerous occasions but somehow this conservative, mom-appropriate swimwear was getting me pretty fired up, maybe just because I'd never seen her in it before aside from the photo series she'd provided.
"Let's go upstairs," she said when she finally pulled her mouth from mine, "I'm gonna fuck you in my swimsuit."
I don't think anything could have appealed to me more so, after locking the front door, I followed her up the stairs, staring at her ass the whole way. Once we were in her bedroom, she pulled my shirt up over my head then worked on getting my belt undone. She squatted as she took my shorts down then dropped my underwear, too, my rigid cock springing out. As I stepped out of my shorts and underwear, she briefly engulfed my cock in her mouth before standing. We climbed onto the bed and she had my lie on my back in the middle of it then straddled me. She pulled her bathing suit aside, revealing her well-groomed bush, then guided my cock to her pussy and lowered herself onto it. We both moaned as her hot, wet pussy engulfed my throbbing cock. She commenced moving up and down on my tool, still holding her swimsuit aside. I reached up to fondle her tits but, while they weren't necessarily squashed within the swimsuit, they were definitely constrained. I pulled the shoulder straps down and she managed to free her arms while continuing to ride my cock. I moved the top of her swimsuit down just enough to free her tits as well then went back to fondling them.
It felt as though seeing her still in her swimsuit but with her tits and pussy exposed made my cock even harder but maybe it was my palms brushing over her hard nipples that was making her moan a bit louder and more steadily. Either way, it was nice to have my cock inside her once again, and my hands on her tits, and it sounded as though she was feeling the same way. I suspected that, with all of the anticipation, it wasn't going to take either of us very long to cum. Of course, this was fine since we had the house to ourselves and plenty of time. As she rode me harder and her tits started bouncing, I moved my hands around to caress her ass while I watched them. Before I got too distracted by her bouncing tits, I also noticed that, as she was holding her swimsuit aside, she also had a finger extended and was stroking her clit. Given this, it didn't surprise me when it appeared that she was on the verge of cumming.
I wasn't quite that close to cumming yet myself, which was surprising given how incredibly hot and wet her pussy felt. The closer she got to cumming, the better it was feeling, so I definitely felt my orgasm stirring but, before spewing was imminent, she dropped down onto my cock and just sat there. After the briefest of moments, she let out a cry and her body started shaking. Since her boobs had ceased bouncing, I brought my hands back around from her ass and went back to fondling them as she was cumming. Her orgasm was long and intense as was typical for her so I just waited her out, knowing that she'd take care of me in some way once she'd recovered. She sat there catching her breath once she'd finished cumming, no longer caressing her clit though I continued to fondle her tits.
