I used to work in a small business office doing tedious and mindless work. Most of my coworkers were women of varying ages. As the work was easy and repetitious we all chatted quite a lot here and there.And as we all know, if you work with people long enough, some of your more personal business may eventually come up. The room I was in had two desks and I shared it with a woman who was close to my age named Susan. We got to know each other pretty well and in fact at some point our conversations turned sexual.
She was married with two kids, so we didn’t take it any farther than just chatting, but eventually she learned that I would jack off under the desk while we talked. At some point I even started showing her my cock, which she quite enjoyed.
Eventually she moved on to another job and her desk started being shared by a couple of different women. One woman was a full-time employee and the other only worked the weekends. I’ll deal with the full-time woman in another story but the part-time lady was an older woman named Pam. She was super nice and down to earth and had worked with computers when she was younger, so she was pretty sharp.
As it turns out she was a saucy old broad. She was in her late 60s, but still in relatively decent shape. I really thought nothing sexual about her until we had a conversation one Sunday. Unbeknownst to her, I would play with my cock under the desk sometimes while reading dirty stories on the internet. This particular Sunday I had worked myself up a bit and even happened to notice that she was wearing a shirt that showed a lot of cleavage.
She appeared to have sizable tits and once I noticed this, and being horny, I couldn’t stop trying to get a glimpse as I passed her here and there. Now, I don’t know if it was because she could detect the sexual tension that I was feeling or what, but at some point when we were chatting she brought up Susan. Pam had known her from working at a different position previously. All the people in the office knew Pam because she would sometimes come visit us and she was always fun to chat with.
Apparently she and Susan had chatted more and more over time and I guess at some point Susan had talked about me to her. So, Pam suddenly said to me that she heard that I was a naughty boy. I played dumb at first, but she told me a little bit more about what Susan had shared with her and I could tell by the playful twinkle in her eye that Pam wasn’t trying to make me feel bad or anything.
So I broke down and told her a little bit about my chats with Susan. Pam then told me that Susan had indicated that I was quite a little pervert. I laughed and told her that I was indeed and I asked her if that bothered her. She chuckled and said that it didn’t bother her at all and in fact, she had been rather kinky in her day. She also tried to pry a little bit more about what Susan and I had done together. She explained that Susan wouldn’t tell her the whole story, so she always conjured up images in her mind of us fucking in the office or something.
I told her that I would’ve loved to do that, but that Susan being married, never wanted to go farther than just talking. I did tell her though that I would jack off under the desk and Susan knew about it and encouraged it. Then I told her that I would even show her sometimes and Pam seemed to get a thrill out of that.
She suddenly told me that Susan said that I would read dirty stories while she was in the office with me. I told her that that was true and then she pressed more and asked if I’d ever read stories while we were in the office together. I told her that I had and, in fact, I had been reading some just that day. She was somewhat shocked and said that she had no idea, but she seemed amused by the thought. She then took it even farther and mentioned that since I told her that I would jack off while talking to Susan, she asked me if I ever did that while reading stories or if I had done that while she was in the room.
I smirked and didn’t know what to say for a second, but finally told her that I had indeed jacked off while she was in the room and in fact had done it that morning while reading stories. She gasped and smiled big and said, “I can’t believe you!”
I then blew her mind even further and said, “In fact, once we started talking about this more, I couldn’t help myself and…uh….I’m actually playing with my dick right now.”
Her eyes and mouth opened wide and she said, “No way! You really are a pervert aren’t you?”
I laughed and though I felt a bit embarrassed, I told her that I was a pervert and I couldn’t help it that I got horny while reading stories. She giggled over that and told me that it made sense, but added that it was of course not the most work safe activity. I agreed with her, but mentioned that I think part of the reason I liked to do it was because of the little thrill it gave me from the risk of potentially being caught. She laughed and said, “Yeah I get that. I used to be kind of an exhibitionist myself”.
Then she asked, “So you’re still doing it right now while were talking?”
I looked at her and smiled a knowing smile. She gave me an OMG face then said, “I almost don’t believe you.”
And before I even really thought about it, I blurted out, “Well, I can show you if you want.”
She looked scandalized again, but smiled big. She looked tempted, but ended up telling me that she wasn’t sure if that was a good idea. She added that if she saw it she might want to do more than just look. This was kind of encouraging even though it was weird to be having this conversation with a woman at least 25 years my senior.
She then got a phone call and had a conversation for about 10 or 15 minutes. Before she got off the phone I had been getting worked up with a little fantasy in my mind, as it turned me on for her to know that I was jacking off in the office. I stood up and got her attention and when she looked over she saw me jacking my fat cock and her jaw dropped. She smiled big and looked shocked but waved her hand in such a way as to say put that thing away. I smiled broadly and then sat back down.
When she finally got off the phone she turned around and said, “I cannot believe you did that! I’m going to have to file that under things I can’t unsee!”
I told her that it was OK and that she could definitely file it away for future use if she wanted. She chuckled and once again scolded me for doing that while she was on the phone. I told her that she knew she loved it and she did not disagree.
I then told her that it was interesting that she brought this up today. I explained that I had always just thought of her more as like a grandmotherly figure until we started working together more. And then I explained that just today I found myself staring at her cleavage repeatedly. She seemed somewhat flattered by this.
Then I shocked her again by telling her that since I’d shown her my cock already, she should flash her titties at me. She laughed again and replied, “Oh, I don’t know about that. I didn’t ask to see yours so why should I show you mine?”
I answered, “Because I know you wanted to see my dick, so I just made the decision for you. That means you should help me out.”
She replied, “Umm, Idon’t know if that’s how this whole thing works. Anyhow you don’t want to see these saggy old titties.”
I told her that I absolutely did want to see them, but the conversation got cut short that day as other people came into the office and work took over. I wasn’t going to work with her until the next weekend, but we were friends on Facebook. Occasionally, she would reach out to me on there and it just so happened that she sent me a message on Tuesday. We chatted a bit back and forth and she again brought up what we had discussed in the office.
She told me again that I was a naughty boy and I didn’t deny it. I asked her if she enjoyed it when I showed her that I was jacking off. She beat around the bush a bit, but eventually said she admitted it. So, I asked her if she wanted me to send a picture. She hemmed and hawed a little, but finally she more or less indicated that she wanted me to.
So, I got hard and took a nice shot of my cock and sent it over. She acted scandalized again, but told me that it was hot. I tried to get her to talk nasty and maybe show me her tits, but I think she felt guilty and would never fully engage. We didn’t talk again after that until we worked together on Saturday.
To my surprise, she wore a blouse that showed even more cleavage than the previous week. I was pretty sure she did it for my benefit. The first two hours were pretty normal, but at some point I asked her if she had been enjoying the picture I sent. She giggled and told me that she couldn’t believe I’d sent it. I had to call her on it though and explained how she clearly wanted me to send it and finally got her to admit it.
While we discussed it, I started playing with my cock. I think she noticed my arm moving because she looked at me with a wicked smile and said, “Are you touching yourself again?”
I smiled and replied, “Would you like it if I was?”
She just tried to play it off and said, “You’re so crazy!”
I then replied, “That may be true, but I’m also horny. And my hand has a mind of its own.”
She smirked and responded, “Uh huh. Sure it does. I’m sure it has nothing to do with you being a pervert.”
We both laughed at that and I said, “Yeah, I guess I am. Sorry you have to work with a total freak, sex perv!”
She chuckled, and to my delight said, “Well, I didn’t say it bothered me. Just wanted you to acknowledge that you did it on purpose.”
We joked a bit more about it and then she got a call. I was super horny after all this talk and of course, was jacking off. I worked myself up more and waited until she got off the phone before standing up, getting her attention, and waiting until she looked at me. She turned and her face went beet red, seeing me jerking myself hard. She whispered, “Oh my god! I can’t believe you’re doing it again. You dirty boy!”
I laughed and told her, “I definitely am a dirty boy, but you’re a dirty old woman for liking it!”
She giggled again and said, “Maybe so. You better put that thing away! I already told you I might want to do more than just look.”
So I replied, “Hmmm….you think that’s going to discourage me? What if that’s what I want?”
She then said, “Goodness! You know you don’t really want anything to do with an old lady like me. You’re just horny!”
Then I replied, “Um, you’re wrong there. I’m a real perv remember? Older women turn me on, younger women turn me on. I just like women and I like being dirty. Why don’t you show me your tits? I see that you wore a more revealing shirt for me today.”
She was a bit taken aback by all this. I don’t think she expected me to try and take things further. She laughed nervously and just said again that I was a very bad boy and that if I didn’t sit back down, she might have to give me a spanking. To that I couldn’t help myself and replied, “Oooh, but what if I like that too? I told you I was a freak.”
She laughed again and told me again that I was crazy. So, I tried to make her a deal. I said, “If you show me your tits, I’ll let you spank me on my bare bottom.”
She seemed slightly tempted by this, but I think she was kind of afraid of following through on any of this. I don’t think she actually believe that I actually had any real sexual interest in her.
So things kind of winded down that day and I honestly thought that would be the end of it. She seemed to be amused and somewhat titillated by the whole thing, but I got the impression that she wasn’t seriously considering taking things any further. To my surprise, the next day we worked together again and things had changed a bit. The first thing I noticed is that she again wore a blouse that exposed a lot of cleavage, but I noticed that she wasn’t wearing a bra. Her thick nipples clearly stuck out through the thin material of her shirt.
Also, she kicked off the sexual banter again. I wasn’t going to mention it, but she tried to playfully give me shit for showing her my cock the day before. I gathered that she must have been thinking about it more and was possibly getting hornier about the idea. So though I had planned to leave well enough alone, I now decided to try and push things even further today.
We chatted a little bit and things got a kind of spicy, so I finally just said, “Are you feeling frisky today, Pam? I couldn’t help but notice that you wore a nice revealing top for me today and I can see your perky nipples. I’m definitely going to have to play with myself some.”
She laughed and seemed a little self-conscious, but finally replied, “Well, maybe it was for you or maybe it was just subconscious or something.”
I didn’t let her slide that easily and said, “I think you knew exactly what you were doing when you wore that shirt today. I think all this talk and you seeing me jack off has you worked up a bit more than you wanna admit.”
She smiled a big wicked smile and I knew that I had called her on it. I was now jacking my cock pretty hard and while we tiptoed around the subject a bit more I got myself pretty worked up. I stood up and moved to the side of my desk which was closer to her but still couldn’t be seen from outside of our room. Then I got her attention and she turned around and stared unabashedly at me as I stroke my shaft for her.
I said, “You’re not telling me to stop today. I’m pretty sure you like it.”
She replied, “Well I never said I didn’t like it. I just wasn’t sure if this was something we should do at work, but I have to admit it’s kind of exciting for this old gal.”
I told her it was turning me on tremendously to have her watch and I asked her to lean forward a little so I could stare down her blouse. Her face looked a bit flushed now and to my surprise she actually leaned forward a bit and I was able to see more of her sizable tits. I told her they looked amazing and I asked her if she had ever been titty fucked. She looked a bit shocked at the question but to my surprise she answered with, ”Well thank you. And yes, of course. I don’t think any woman with breasts my size could make it through life without that happening at least once.“
I giggled a bit as I continued to jack off and I told her how hot that was. I then said, “Why don’t you undo some of the buttons and let me see them?”
She played hard to get for a bit but eventually said, “I might be willing to do that even though I probably shouldn’t. Does our deal from yesterday still stand?”
She was clearly joking about the last part which was a reference to me letting her spank me in return for seeing her juicy tits. I think I surprised her however when I said, “Of course it does. We can go to the back office because it’s Sunday and nobody’s there.”
She got a mischievous look in her eye and she said, “Do you really want me to spank you?”
As I jacked my cock even harder I told her, “Absolutely! I would love for an older woman to spank me. That would turn me on quite a bit actually.”
She seemed quite pleased with my answer and added, Well, well. You are a very naughty boy aren’t you?”
I nodded and said, “I sure am. And naughty boys need to get their punishments don’t they?”
I could tell now that she was tremendously turned on and without saying another word she looked out the door to our office to make sure no one was there and then proceeded to unbutton her blouse most of the way and let her large tits come into view. Sure, they were a bit saggy, but honestly they looked really sexy to me. I told her as much and stared at them lustfully as I played with myself.
I’ve then asked her if I could play with them and she thought about it for a second before saying, “Yes, but maybe we should go to that back office like you said. It makes me nervous up here with other people around.”
I couldn’t believe that this was about to go down. Not only was I doing this at work, but with a considerably older woman. So I put my dick back in my pants and told her that I would go first and that she could join me in about five minutes so that it wouldn’t seem too weird.
She agreed and I headed out. Much to my delight, she showed up as expected about eight minutes later. I could tell she was a little bit nervous that we were alone now and that things might go places she didn’t want, but I just decided to keep her turned on and brought her back to the task at hand. I asked her, “So Pam, where do you want your naughty boy to be for his spanking?”
She smirked wickedly and told me that I could just bend over the desk and she would stand behind me. So I walked over to it, dropped my pants and underwear, and bent over the desk before looking back at her. She laughed and said this is so weird I cannot believe we’re doing this.”
I told her that it was definitely a bit strange, but that it turned me on quite a lot to be doing this with her at work. I asked her if it was making her pussy throb a little bit. She looked at me straight and responded, “What do you think?”
I told her that if it was anything like my dick, then it was probably pretty amped up right now. She nodded before saying, “So you want your spanking with my tits out or not?”
I replied, “Well of course! Is there any other way to do it?”
She guffawed before unbuttoning her shirt and gracing my vision once more with the giant boobs she had hidden under there. To my surprise she walked up and became rather dominant. It was hot when she got stern with me and told me that I was a sick pervert and needed to get punished. Then I felt the first smack on my ass and it stung but felt good.
So, she proceeded to spank me faster and harder while listing out all the perverted things that I’d done with her and Susan, and how that was really not work appropriate at all. Soon my cock was rock hard and pressing against the desk and she took note of it.
She said, “My, my. You certainly do seem to enjoy getting spanked by an older woman.”
As she said this, her hand lingered on my ass and rubbed my cheeks. I looked back at her and said, “You have no idea how much this is turning me on. You already know I’m a big pervert, but you don’t know how dirty I actually am.”
I then told her that if she had a strap-on here, I would even let her fuck me up my ass and I think this simultaneously shocked her and gave her pussy a jolt of excitement.
She said, “Wow! You are even dirtier than I thought. I’ve never done anything like that. Are you bisexual?”
I replied, “Well, I’m bi-curious, but I mostly prefer women. If I brought a strap-on in would that be something you’d be interested in trying?”
She thought about it for a second and then responded, “You know, it’s not something I’ve ever really fantasized about, but now that you have brought it up and you seem serious about it…..yeah, I guess it would actually maybe get my motor running to try something like that.”
As she was speaking her hand was now fondling my ass and slid around the bottom curve and I felt her lightly brush her fingers against my balls before absentmindedly moving up between my crack a little bit. This whole situation had taken a little bit of a turn and I found that I liked it quite a bit and it seem that Pam liked it too. Her ministrations on my ass and balls were getting me going even more.
So I told her, “That feels really good. Feel free to keep exploring back there if you want.”
She replied breathlessly, “Ok.”
And I soon felt her other hand wrap around my shaft as she continued to tease up and down my ass crack. I said, “Oh God, Pam! Yeah! Play with my fucking cock while you tease my asshole!”
She started jacking me off and pushing her finger slightly against my anus. It was so hot I couldn’t help myself. I blurted out that she should wet her finger and work it into my ass. To my surprise she did as requested. She stroked me harder and soon had a delightful finger buried up my ass. I asked her if she enjoyed doing this to me and she responded, “It’s definitely a new experience and like I said, this is not something that I have ever really fantasized about, but I’m not gonna lie. This is pretty fucking hot! I kinda wished we did have a strap on here”
I told her that I would definitely bring it in the future and she seemed very pleased about this. Then I asked her if we could we switch things up a little bit and she agreed. So I turned around to face her and before she could say yes or no, I reached out and grabbed her lovely tits and they felt amazing. She moaned out loud at the sudden contact and pressure.
She moaned even louder when I leaned down and took one of her nipples in my mouth and sucked it good. She definitely seem to enjoy it, but when I tried to grab her ass she stopped me and told me that she was the one in control and that I wasn’t allowed to do that without permission. I got the impression that she was a little nervous about showing me her body. So I left it alone for the time being.
I said “Ok, and well here’s what I really had in mind,” before sitting on the edge of the desk. I told her that she kept mentioning in the office before that if I kept exposing myself to her that she would come over and do something about it. So, I told her that now was her chance to do something about it. She took my meaning and rolled a chair in front of me.
First, she jacked me off a little bit before actually taking me in her mouth. It felt fucking divine. I couldn’t believe I was getting my cock sucked at work by a considerably older woman. She took me deeper and deeper until I was bumping the back of her throat. I wasn’t sure how far we should go, so I didn’t try to push it any deeper.
To my surprise she actually stopped for a second and told me, “It’s been a while since I’ve done this, so might take me a time or two to get back into the swing of it, but I used to be able to deep throat.”
That said two things to me. One, she wanted this to happen again and two, that I might have a 66-year-old woman deep throating me and the whole idea was tremendously exciting. She started sucking me again and now she began to play with my balls. I moaned and told her that I felt good and also told her that she should play with my ass again. To my surprise I felt a moistened finger work its way back into my tight anus. It felt amazing and I was already getting close.
She continued to suck me even deeper and finger my asshole while I reached forward and played with her pendulous tits. To my surprise, under her own initiative, she worked another finger into my ass and was soon sucking me quite hard while pumping her digits in and out of me. I grunted with tremendous pleasure and told her that I was going to cum soon. To my delight she only sucked harder and started to work a third finger into my ass.
I groaned in ecstasy as she sucked and finger-fucked me. I think she could tell that I was getting close because she really started going to town on me once she got that third finger buried. I told her that I was literally about to blow and I started moaning continuously. She clearly wanted to swallow my cum because she continued to suck and started to bang my ass even harder.
This pushed me over the edge and I almost yelled out as I began firing a nice thick load of spunk down her throat. I couldn’t help myself and said, “Oh fuck, Pam! Jesus Christ! Yeah, suck me and fuck my asshole with your fingers. You are such a nasty old bitch! You’re making me cum so hard!”
It was one of the best orgasms of my life. And she swallowed my entire load which turned me on tremendously to think about. After I finished coming, she lovingly cleaned me up. I thanked her tremendously for doing that for me and I asked her if she wanted me to return the favor. She replied, “Not this time, but maybe in the future.”
Again, I think she was self-conscious about her body and her age and didn’t want to go any further yet. I told her ok and that if she ever needed my services that I was available. Then I asked her if she enjoyed what we had done and she smiled broadly and said, “Oh my god, yes! Here I was thinking that my sex life was on the decline and then you show up and I have a bunch of new experiences. That was the nastiest, kinkiest sex session I’ve ever experienced. And I think I want more.”
And with that we cleaned ourselves up and headed back to our office. We didn’t fool around anymore the rest of that day but we discussed it at length and I realized that I had awakened a kinky monster in this older woman. She definitely wanted to do some more experimenting and I was 100% game.
Let me know if you liked this and where I should go next. Should I keep it more realistic, or get weird and kinky with it? Ideas? Thanks!