My Former Coworker: Cindy

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.

When she opened her eyes, she smiled down at me then got up, leaving my rigid cock standing straight up. Standing over me, she pushed her swimsuit the rest of the way down then kicked it away. I gazed upon her naked body until she got down on her stomach between my legs and gripped my cock. She pumped it a couple of times before engulfing it in her mouth and causing me to moan. I was glad it was light so that I could watch her sucking my cock and pulled her pillows over to prop up my head. Her skill by itself would have easily been sufficient to make me cum but seeing her engulfing my tool over and over certainly added to the arousal I was feeling. She always seemed like she was enjoying sucking my cock, too; that she was drawing out the pleasure not just for my enjoyment but for her own, as well.

She didn't draw it out so long that it felt as though I was being denied my orgasm so I was on the verge of cumming pretty soon. My cock swelled even more as I got closer but, by this point, she knew the signs that I was getting close. She changed her focus from drawing out the pleasure to making me cum and I was spewing into her mouth moments later. She swallowed my load and continued sucking me off until I was fully spent, then she let my cock fall from her mouth and crawled up next to me. I put my arm around her and she snuggled against me, her naked body against mine.

"That was a great idea," I said after a bit, "a fun little change of pace."

"I'm not done yet," she replied, "I've got something else to show you."

She got up and I watched her as she crossed naked to her walk-in closet. After a couple of minutes, she came back out wearing a bikini and she looked fantastic. As the blood tried to immediately flow back to my spent cock, I wondered when I started becoming aroused by swimsuits, although I realized it was also the person wearing them.

"I haven't worn this one in a while," she said as she modeled it for me.

"You look great," I told her, "You should be wearing this all the time...to the grocery store...to church..."

"How about if we figure out someplace we can go together where I can wear it," she replied, "but, in the meantime..."

She crawled back onto the bed and we started making out as I fondled her tits through her bikini top. I could feel her hard nipples so, rather than undoing the top or taking it off, I kissed my way down along her neck to her collarbone then down her chest. I pulled each cup aside enough so that I could lick and suck her hard nipples, alternating back and forth between them. She moaned and ran her fingers through my hair but I knew that her pussy was undoubtedly becoming wet again so I only lingered briefly. I continued kissing down over her bare stomach then kissed each of her hips as I lay between her spread legs. I lightly caressed her pussy through her bikini bottom then pulled it aside and ran my tongue along her slit, causing her to moan again.

Again, I made no move to remove her bikini bottom, wanting to keep her in it as we'd done with her one-piece. I slurped up the copious juices that were flowing before focusing my tongue on her clit while slipping a couple of fingers into her. As I slowly pumped them in and out, I licked and sucked her clit while holding her bikini bottom aside. I could feel the blood trying to return to my spent cock but its revival was slow so I wouldn't be fucking her in this bikini any time soon. I was just fine with that, though, since not only did we have plenty of time but I also just really enjoyed eating her pussy. I could tell by the way she was moving and the noises she was making that she was just fine with me eating her pussy, as well.

I think the only thing that could have made eating her pussy while she was wearing her bikini even better would have been doing it on the beach or on a chaise lounge at a pool or on a cruise ship. Since it would take some planning to pull something like that off, I was good with devouring her pussy in her bed for now. She was tensing up a bit the longer I was eating her and her moaning was getting louder and longer. Her pussy was also becoming wetter and more engorged, which was a sure sign that she was on the verge of cumming again. Right before her orgasm hit, she went silent momentarily then let out a cry as her body started shaking. I continued to devour her as she experienced another of her typically long and intensely pleasurable orgasms, raising my head only once I knew she was finished.

I got up on my knees and continued admiring her as she was recovering but, though my cock was also recovering, it wasn't quite ready to go yet. I'd never failed to get an erection with Cindy but, as we were both a bit older, it didn't always pop right back up again and she didn't take it personally. She sat up as I was still sucking her flavor off of my fingers, gently stroked my cock then climbed off of the bed.

"Where do you usually take off your swimsuit and why?" she asked, reaching for my hand.

"In the bathroom so you can take a shower," I replied, catching her drift. We headed into the master bathroom, which had a nice sized shower with plenty of room for two. I turned her to face the big mirror over the sinks and cupped her tits then pulled the shoulder straps down which pulled the cups down, revealing her large areolas and hard nipples. As I cupped her bare tits, caressing her hard nipples, she reached back between us and unhooked her bikini top, letting it fall to the floor. My cock was continuing to recover as I fondled her bare tits and when I dropped my hands down to push her bikini bottom down, exposing her well-groomed bush, which I admired in the mirror. Once gravity carried her bikini bottom to the floor, she turned to me and we kissed as I caressed her bare ass then she got the shower started.

I knew we were both clean, aside from the residual fluids from our fucking, so I didn't think Cindy really wanted us to shower necessarily. I had a pretty good feeling about what she did want to do, which she preferred to do in the shower where it required less clean up. Once we were both inside with the water running, she squeezed some body wash into my hands and took some for herself. With hers all lathered up, she started spreading it on my cock and balls with both hands, getting it back to being fully rigid. Meanwhile, since I knew the drill, I was spreading mine between her ass cheeks, making sure it was slippery and sudsy back there. When my cock was ready, she released it and turned to brace herself against the wall. Standing behind her, I slipped my cock between her ass cheeks and easily entered her snug asshole.

I had been pleasantly surprised the first time she'd asked me to fuck her ass and once again when I discovered how hard and how easily she came when I did. We hadn't done it a lot, partly because she liked to do it in the shower and we didn't have the opportunity to shower together all that much. When she was especially fired up, though, that was usually when she wanted it in the ass and I was more than happy to oblige. Her tight asshole combined with the lubrication felt amazing to me and, according to her, she'd feel some initial discomfort followed by intense pleasure. This time was no different; once I started to slowly fuck her ass, she went from being slightly tense to suddenly shaking like crazy and crying out. I continued to fuck her as she was cumming and, once that first orgasm had tapered off, she was pushing back against my slow, gentle thrusting. We gradually picked up the pace and it wasn't long before she had another powerful orgasm.

Of the few times I'd fucked her ass, I'd cum inside it even fewer. The pleasure she felt, it turned out, was so intense that she usually had me stop before I got there. She always took care of me, though, and this time was no exception. She had me stop fucking her ass after the third intense orgasm so I slipped out and she turned to face me again then jammed her tongue in my mouth. We made out passionately for a moment before she grabbed the body wash to clean my cock again in anticipation of having me stick it somewhere else.

"That was amazing, as always," she said, "so how would you like to continue?"

"I've actually got an idea to go along with tonight's theme," I replied, "but let's finish up in here and I'll fill you in...in more ways than one."

She laughed then we rinsed off the body wash and turned off the shower. We grabbed a couple of towels and dried off ourselves and each other before stepping out. My cock was still rigid and sticking out in front of me and Cindy was anxious to do something with it.

"Okay, so what's the plan?" she asked.

"When you were at the hotel watching the video of me stroking my cock," I asked, "what were you wearing?"

"A nightshirt," she replied.

"Can you get it and put it on?" I asked.

"Of course," she replied and headed from the bathroom into her walk-in closet while I went back to her bed.

"Now set yourself up like you were that night," I said. She turned the bed down and propped the pillows I'd used earlier up against the headboard then slipped under the covers and sat up against the pillows. I got on the bed and knelt close to her.

"I don't have my phone, though," she said, "It's plugged in downstairs."

"That's okay," I said, "I believe I was doing something like this in the video."

I started stroking my cock as she watched.

"Now show me what you were doing while you were watching it," I said. She positioned the covers so that I could see as she hiked the hem of her nightshirt up to her waist exposing her pussy. She then started stroking her pussy which only made my cock even harder. I didn't want to make myself spew so I stopped stroking it and lay beside her, reaching down to take over caressing her pussy. She moaned while reaching to take over gently stroking my rigid tool as I caressed her clit. I was also alternately probing her pussy with a finger and could feel it becoming even hotter and wetter so I definitely planned on fucking her again but I wanted to make her cum again first. We didn't kiss or anything; she had closed her eyes and was just savoring the building pleasure while I was gazing at her pussy as my fingers explored it.

"Remember you don't have to stay quiet this time," I whispered because she was uncharacteristically quiet and I was wondering if she actually felt like she was back in that hotel room. It turned out that she was actually right on the verge of cumming already and, just moments after I said that, she let out a cry and her body started shaking. I continued to stroke and probe her pussy as she was cumming, feeling it flooded with even more lubrication. Once she'd finished cumming, she opened her eyes and kissed me.

"Here's what I would have done had I been there with you," I told her then pulled the covers down after sucking her flavor off of my fingers. I took her hands and helped her up onto her knees, kissed her as I ran my hands over her ass which was covered by the nightshirt, then I turned her and lay her down in the middle of the bed. I pushed the hem of her nightshirt up just enough to expose her pussy then lowered myself over her as I guided my cock into her. We both moaned as my cock filled her and I supported myself over her on my forearms. I brought my lips to hers and we started making out as I slid my cock slowly in and out of her hot, wet pussy.

Of course, fucking her slowly didn't last long because it felt so damn good sliding my cock in and out of her. As I picked up the pace, she was raising her hips to accept each thrust, guaranteeing maximum penetration. We eventually had to quit making out so I raised up some, supporting myself with a hand planted on either side of her head. She was running her hands along my lats, which were quite prominent in this position, and had pulled her knees up towards her tits. I wasn't necessarily fucking her harder, just faster the closer I got to cumming. She didn't seem to mind judging by how, the longer I was fucking her, the more vocal she was getting. She wasn't just moaning by this point; she was saying things like "oh yeah" and "oh God yes" and "fuck me," which I obviously took as a good sign. I was hoping she'd cum again but I wasn't trying to hold back my own orgasm to make sure that she did.