So, here’s a story you perhaps don’t hear every day. It’s a true story, but it has a couple of layers, so allow me to explain some of the moving parts. I’ll try not to ramble too much so we can get to the juicy stuff. My name is Max and this happened to me. Sometimes I still can’t believe how it all played out. I work at a small business in the hospitality industry.
I’m 40 years old and do IT work for the company, but I have a lot of free time on my hands. My manager doesn’t micro-manage and I get my work done, so I have a lot of autonomy. Probably too much. That’s how this whole thing started.
Now, before we get too far into this, let me begin to introduce the rest of the involved parties. The first person you’ll need to know about is Kelly. She and I used to work in the same office together. Not only in the same building, but literally the same room. She answered phones and did administrative tasks mainly. I was attracted to her immediately. She is about 42, very sexy, and has a MILF vibe about her. She also has a great body in general, but her ass is amazing. I couldn’t help but stare at it every time she left the room. We used to chat a lot and through talking over time, I slowly discovered that she is actually a very kinky lady. She is married, but was open to flirting.
After we’d established that we both were attracted to each other and shared some similar interests sexually it progressed to the point where she’d listen as I openly fantasized about what I wanted to do to her. She got off on it as much as I did, but she wasn’t terribly vocal about it because we worked in such close proximity to other people. She had a lot more to lose than I did if we got caught being naughty. Eventually I even told her that I would jack off under my desk sometimes as we talked. It was easy because my desk was behind hers and she couldn’t see me doing it. When she learned that I had been doing this it turned her on greatly.
I used to get very worked up during these jack off sessions and soon I even began standing in the corner of the room where no one else could see and I’d get her attention and she’d watch me stroke my cock. She loved it, but would get nervous, so I never did it for long. One time when I was getting close I told her to turn around and look me in the eye as I came under my desk. She really like that one. So did I.
I used to tell her about all the kinky sexual dreams and fantasies I’d had and over time she learned about how much of a pervert I really was. The reason I was comfortable sharing all of this with her is because one of the first more open discussions we had about sex I found out that she loved anal sex and being tied up. So I knew she was a naughty little bitch. I told her that I fantasized about having threesomes with her and another woman or man. I shared dreams that included double penetration and cum play. Others had domination, spanking, and incest. She wouldn’t always open up about everything, but I could tell that it all titillated her.
I turned her on to butt plugs and she grew to love them. She even wore one to work a couple of times and enjoyed it, but she said it made her too horny. I think she was worried that things would go too far between us. As it was, I’d already grabbed her tits a couple of times and her ass a few more times than that. One time I even grabbed her cunt from behind. She moved before I could massage it much though. I could tell she enjoyed it, but she always stopped me pretty quickly. She was married after all and had two kids. She loved her husband, but just enjoyed being a little dirty on the side.
Later she stopped working in the office and moved into being a concierge for our company at a local hotel. So, we didn’t talk as much after this, but we’d occasionally email and she was still a kinky little thing. I’d send her links to pictures, animated gifs, videos, and stories regarding what had been turning me on recently or what I’d fantasized about doing to or with her. She told me eventually that when she worked in the office she had seriously considered wearing a short skirt and coming over to me while I was jacking off and just sliding her pussy down on to my cock, but she was afraid of getting caught. Boy do I wish she had actually gone through with it.
Anyhow, as I mentioned, since she had left the office I’d taken to sending her emails with all kinds of stuff to make her horny. I continued to tell her about dreams or fantasies I’d had. Some with her and some without. I even sent her a couple of stories and videos with incest related themes, and although she didn’t say much, she seemed to like them. She’d always been a little uncomfortable with the subject, as most people are, but she’d said enough to indicate that they were somewhat titillating. I think she was just afraid to admit how much they turned her on.
A couple of times I’d emailed her and played a joke on her. I tried to get her to believe I’d had a sexual encounter with another co-worker. I did this not only to have a little fun, but I also did because it turned me on to openly fantasize about things with her. I knew it turned her on some as well. I’d already told her about flights of fancy I’d had involving people we worked with on a few occasions before. The difference here was that I wanted her to believe these things had actually happened. I wanted her to tell me how horny it had made her to hear about these occurrences.
So this leads me to introduce the next person in the story, Lisa. She had recently started working in the other office that was in the back building on our property. We knew each other already because she had actually worked for our company for a while, but her previous position had her out and about and she only came in at the end of the day. I was the one who counted the money she’d made when she came in. Kelly knew her also because of this. She was around my age and we had also developed a slightly flirty relationship over time. She was a bit of freak too it turned out, but her tastes in sex were a bit more pedestrian than mine. I was only somewhat attracted to her. She did have very large breasts though and she was not shy with showing them to me if I asked to see them.
Lisa and I had talked here and there over time and she came to find out that I was pervert also. She didn’t judge, but didn’t fully enjoy the things I did. One of the things that kind of turned me off was that she wasn’t into anal at all. Also, she was kind of sleeping around with various people and I didn’t feel like she had much quality control on that front. So nothing ever happened between us aside from sharing some sexual gossip here and there. I mention her because she plays a minor, but pivotal role in what we’re leading up to.
The first reason Lisa is important to mention is because the first time I’d tried to fool Kelly, it was with a story involving her. Basically I’d told Kelly that she and I had been flirting and at some point she was in the back office alone because everyone was out doing something for the company or was at lunch. There were only 4 people that worked in the back building, so it wasn’t a stretch. Anyhow, I explained that I’d gone back to Lisa’s computer to fix a problem she’d had and we’d ended up flirting a bit. Before all was said and done, I’d jacked off in front of her, gotten her to pull out her tits and put her hand between her legs and play with herself, and finally, I’d fucked her tits and cum on them.
It was a relatively simple tale and she knew a bit about how Lisa and I had flirted, so it worked like a charm. Kelly believed that it had happened and had even written back to talk about some spontaneous sex events she’d engaged in. I could tell it had made her horny. Later I told her that it was an April Fools’ joke and she playfully chided me for lying to her. Like I said, I have too much time on my hands.
After this happened I had told Lisa about the joke because I knew she’d get a kick out of it. She did and in fact I think I could have probably made that whole story/fantasy happen with her, but I really had just come to the conclusion that I didn’t want to mess around with her. I just didn’t feel the chemistry and she was still playing the field with a couple of different guys. I didn’t want to get involved in all that. I was still far more attracted to my flirtation with Kelly anyhow.
Now, this leads me finally to explain how this is all relevant to the series of events that are at the core of this amazing story. Quite a few months after I’d fooled Kelly with that first story, I had thought of a new one to try out on her. This one, loosely involved Lisa, but mostly focused on the third person in the story (aside from myself) that I will now introduce. This woman is named Patti and she’s a little older than the rest of us. She’s probably about 50 or so, but she’s in decent shape. She’s mostly gray, but there is still a bit of brown in her hair. Honestly, when I first met her I didn’t really think much of her. She also works in the back office building, but she’s had that position longer than Lisa. Like Lisa, she came from working out in the field, so I already knew her from when she came in to cash out her daily sales.
When she would come in to cash out back then I thought she was a bit too bubbly and her scraggly hair had that aging hippie vibe. I wasn’t terribly interested in her at that time. She just seemed a little older and kind of boring. She hadn’t let her body go or anything, but I wasn’t particularly attracted to her. It wasn’t until more recently when she worked in the office that I discovered that I began to find her more appealing. This is what led to me writing my new story to try and fool Kelly with. She knew her also, so I honestly didn’t think that she would believe what I was going to tell her in a million years.
What changed my mind about Patti was one day I was walking towards our break room and she came in the back door. We exchanged niceties and I noticed that she had done something new with her hair. It was now curly and more styled. It made all the difference on her and she looked more attractive and youthful. A couple of days later I had run into her again and she was wearing some tightly fitting capri pants. I couldn’t help but notice that her ass looked very nice in them. Part of her job now was to give short walking tours, so I knew she’d been out hoofing it a lot lately. Her body looked very good to me because of it. I also noticed that her breasts were pressing against the fabric of her shirt and I could just make out a little nipple. These two chance encounters are what got my devious mind thinking of a new story to send to my naughty pen pal.
Again, I truly didn’t believe that Kelly would believe this story. For one thing, I’d already fooled her a few months before, but also, she knew Patti and she just didn’t seem like the type of person that would do what I’m about to describe. So I figured she wouldn’t buy it at all.
Now, to tell the next part of the story, I’m going to include the actual emails that I sent to Kelly (edited slightly to protect identities). As you will see, I even created fake emails to try and get Kelly to believe that Patti was communicating with me. Hopefully it will make sense as you read through them.
Sent: Wednesday, January 3, 2015 3:50 PM
Ok, so something very strange and interesting happened a little while ago. You probably aren’t going to believe me after that April Fool’s joke, but I had a very unexpected encounter earlier. Around 12:45 I got a call from Patti in the back office. She said she was getting a weird printer error. So I said I’d come back and look at it. After about 10 mins. I headed to the back building. When I got there I was walking down the hall towards her office and she came out of Robert’s office. I didn’t hear him and I didn’t see anybody else around so maybe she was using the bathroom, who knows? Anyhow, I followed her into her office and she went around her desk and sat down and was smiling. I was thinking, “What the heck is she smiling about?” Before I could even ask her what was going on she said that the printer was working fine and there was no problem. She told me that she just said that to get me to come back there. I was like, “…Ok?” Then she said she wanted to ask me about something personal which is why she tricked me into coming back there when no one was around.
I had no idea what she was going to ask about. I don’t know her much at all except from when I did cashouts back when she worked out in the field. I’ve barely seen her since she works in the back office. I don’t know if you’ve seen her lately, but she changed her hair and it’s like curly now. It actually looks better than it used to and I was surprised also b/c she was actually wearing a shortish skirt. Nothing sexy, but like a khaki skirt that’s just above the knees. She looked better than I remembered her really. Anyhow, she told me that what she was going to ask me about was weird and if I didn’t want to talk about it she would understand. So I’m still thinking, wth? What could she possibly want to ask me about?
Then she told me that she and Lisa talk sometimes when it’s slow. Apparently through talking over time, they’ve shared gossip and some personal things. I found this kind of weird b/c I thought Lisa didn’t really like her, but who knows? I haven’t really talked to Lisa much in the last 3 weeks, although I did see her on Saturday b/c she stopped in the office to say hi. But so, Patti told me that they had talked about sex stuff a bit. Of course then I’m thinking, where’s this going? It turns out they had shared quite a bit of personal sex related stuff and apparently Lisa told Patti that I’m a “freak.” So, then they gossiped a bit more and Patti had asked more about how freaky I am and Lisa told her about some of the stuff I’m into and some of the pictures I’ve shown her (animated ones like some of the ones I’ve sent you).
So I’m feeling a bit anxious now b/c I have no idea what she’s leading up to. Then she asked me not to tell Lisa that she and I have talked b/c Lisa made her promise not to mention anything about it to anyone. She continues and tells me that Lisa told her specifically that I was “way into anal stuff like butt plugs and more.” I must have looked embarrassed or nervous b/c then she was like don’t worry I’m not trying to blackmail your or make fun of you or anything. So I felt a little relieved and asked her what she was getting at then. Then she totally surprised me and said something like, “Well, I’m asking b/c I’m actually a bit of a freak myself…and I wanted to ask you some things.”
So now I’m like holy shit! What the hell is going on? Last week Kelly actually responds to emails and tells me she’s masturbating about me and this week Patti’s asking me about anal stuff! Anyhow, I’m still a little weirded out, but I ask her what she wants to ask me about. So then she tells me she read the Fifty Shades books and some kinkier stuff online and that it got her more interested in kinky sex. She told me that she’s done a little assplay here and there and even had anal sex a few times, but it’s been a long time since she’s done anything. Then she said that Lisa had led her to believe that I was pretty knowledgeable about it and about BDSM type stuff. She asked if I could give her some advice on “anal training” and kinky sex shit basically. Also, she wanted to know if I could share any links to sites online that have information about these things, any good sex toy sites, or any good porn links.
So, wow right? I couldn’t believe what I was hearing. She didn’t even seem embarrassed or nervous about talking about this shit. In fact I almost got the vibe that she was being a little flirty or suggestive that she might want to do something. Like I have no idea what Lisa told her about me. I don’t know if she told her I showed her my cock and jacked off at work and such.
Well, anyhow, I have to say it was interesting and it made me horny, but I kept it relatively professional. I told her I could give her some information and ideas. I did mention that I was no slave master or anything, but that I’d played with some BDSM sex before and had definitely done a lot of anal stuff. I wasn’t sure how deep she wanted to go (no pun intended) so I asked her basically what she might be into and she said she was pretty open minded. So I told her that I was pretty kinky when it came to all kinds of sex stuff. I asked her if fisting turned her off and she said no. In fact she’s claims that she’s been vaginally fisted a few times and came really hard. I told her that was hot, but then I said, I’m also into anal fisting. She’s like, “I know, Lisa told me.” That’s why she wanted to ask me about this stuff. Like she’s definitely into more extreme stuff.
So I was like, “Well damn, I guess it’s on then.” So I told her about some kinky porn sites for pics, videos, and stories and told her that I’d send her some other links later. As for anal training, I told her to go to a sex store or online and get some different sized butt plugs ranging from small to as large as she’s willing to attempt. Told her to start small and maybe wear them around the house or even to work and just get used to them. She seemed to be into that idea. She basically said, “mmm…that sounds kinda fun. I think I’d like to wear one at work maybe as long as I don’t have to give a tour.” We both laughed at that. I also told her about inflatable plugs, which she also seemed interested in.
As I said, I was pretty horny from all this talk, so at the end I was like, “You should tell me if you try the plugs out. Keep me up on your progress, I’d love to hear about it.” And she was like, “Oh, don’t worry. I will. You’ll be the first to know about it.” That was pretty much it, but she did say she’d like to talk more about kinky stuff some other time soon. I told her that would be cool and basically had to leave b/c I needed to go run some errands on my lunch.
So yeah. That happened today. Can you believe that shit?
Well, unbeknownst to me, Kelly was out of town on vacation, so she either didn’t see or couldn’t respond to my emails for over a week. So I just proceeded to send her emails and perpetuate this false narrative.
2nd email from the next day:
Sent: Thursday, January 4, 2015 10:35 AM
Subject: Fw: Toys!
Ok, so the madness continues. Yesterday before I left I got an email from Patti telling me she was on her way to buy some toys. And a few minutes ago I got this email. Can you believe this shit?
– Forwarded Message –
Sent: Thursday, January 4, 2015 10:15 AM
good morning! got some toys at Dirty Dolls. they have a lot of fun stuff. I wish I could afford it all!! lol!
couldn’t wait to get home with my new things. had soooo much fun playing with the butt plugs and a vibrator last night! didn’t get to the largest plug I bought, but I used all three smaller ones. the smallest one was easy 😉 the more medium sized ones stretched me a bit, but jesus did I cum hard! they felt amazing! in fact, I have the small/medium one in now and it’s awesome! it’s making me so damn horny! I can barely focus on work.
but man, I love these things! playing last night was so great. they only thing that would make it better is if somebody else was doing it to me and it wasn’t me doing it alone 😉
I hope all this isn’t making you feel uncomfortable or whatever…but do you think maybe later when I go to lunch you might wanna come check on my progress? Around 2? I know where we can have some privacy 😉
Sent: Thursday, January 4, 2015 10:35 AM
Subject: Fw: Jeezus
Then I got this email!
– Forwarded Message –
Sent: Thursday, January 4, 2015 10:21 AM
I can’t believe I sent that last email! I don’t know what’s gotten into me! well…actually I do…but I hope you don’t think I’m a weirdo! lol!
Sent: Thursday, January 4, 2015 11:00 AM
Subject: Fw: Re: Toys!
Well, I’m probably going to hell for this. I went back and forth in my head, but this is what I sent her back.
– Forwarded Message –
Sent: Thursday, January 4, 2015 10:56 AM
Subject: Re: Toys!
Well damn! I’m speechless! You’ve been a busy girl haven’t you?
I’m glad you’ve been enjoying the toys. I figured you would. And I have to say, your email made me insanely horny. Not gonna lie, my cock is rock hard. I couldn’t help but pull it out and play with it some. Have you been touching yourself this morning also?
I really, really probably shouldn’t meet you, but my willpower isn’t very strong and you’re hitting me where I’m weakest when you tell me about playing with butt plugs. So, yes, I’m very interested in “checking on your progress.” I’ll do a thorough job 🙂 Where should we meet?
And no, you’re not a weirdo. Well, no more so than I am.
So, I still hadn’t heard back from Kelly at this point. As I mentioned, I didn’t know she was on vacation. I wasn’t sure what it meant that she hadn’t gotten back to me, but I had gone this far with the story and had made myself very horny. I decided to take it to its logical end 😉
Sent: Thursday, January 4, 2015 4:07 PM
Subject: total disbelief!
Holy shit! Holy shit! Holy fucking shit! It went down. Seriously! I know you’re not going to believe me, but I’m really not kidding.
I’m gonna keep this one short b/c I’ve already been interrupted twice while trying to write this and I’m gonna keep getting interrupted since it’s that time of the day and all. I’ll give you the more detailed version later, but…long story short:
I met Patti at the back a little after 2 and she took me into the downstairs office that no one is in.
It was a little awkward at first, but basically she told me to take control and do what I wanted.
Made her sit on the corner of the desk and bounce on the plug in her ass while I fondled her roughly through her clothes. Then I took her shirt and bra off and played with her tits. They’re kinda small, but not too bad.
Took off her skirt and panties and bent her over the desk. Her ass is even nicer than I expected.
Spanked her a bit, but we had to keep it kind of quiet.
Fingered her pussy and played with the butt plug. She shaves thank god.
Licked her pussy and pumped the plug in and out of her ass.
Pulled the plug out and used 3 then 4 fingers to stretch her further as I kept licking her clit. She came like a banshee.
Talked very dirty to her the whole time and treated her like a slut and she loved it.
Wanted to fuck her mouth, but we didn’t have that much time.
Told her to bend over the desk and that I was going to fuck her in the ass. She was down, but made me wear a condom.
I still can’t believe it, but I bent Patti over the desk and totally fucked her in the ass. At work.
I didn’t last long b/c I was so horny. After getting her used to it, which didn’t take long b/c of her playing with plugs and my fingers, I pumped in and out probably only like 15 times before I blew my load while buried all the way in her ass.
Jesus Christ. I still can’t believe it. She wants to do it again soon. She said when she knows me better she might let me cum on her or in her mouth or ass. I had no idea she was such a kinky bitch before yesterday. Was kinda weird and hot doing this shit to an older woman. I mean she’s mostly gray!
This email is still longer than I meant to make it, but wow. My mind is still blown! I absolutely cannot believe that this happened.
So, that was that as far as the story, but I didn’t hear from Kelly for another few days because of her vacation. I had started to get worried when I didn’t hear back. I thought perhaps I’d gone too far and that she was pissed at me. When I finally did hear back, it wasn’t really what I’d expected. She told me why she hadn’t been in touch and apologized. She couldn’t check the email on vacation because she was always with her husband and kids. She’d turned off the email account on her phone because the notifications kept popping up and her husband used it sometimes. She didn’t want him slipping upon our messages.
She went on to explain that she was pretty shocked by the emails I’d sent her. She had believed them, but instead of them titillating her, she was basically a little grossed out. She was still thinking of the Patti that used to come into the office with frazzled hair. Also, though Kelly was bicurious and thoughts of being with women turned her on sometimes, she was mostly straight, so I doubt she was attracted to Patti like I was. I know I hadn’t been at first either. Sometimes it takes time and perspective to appreciate someone’s allure. Probably for me also, I’d begun to sort of fetishize her. I was really turned on by the idea of a slightly older woman that I would never have expected such behavior from, wanting to get assfucked by me at work. Plus just the fact that I’m as ass man. I liked seeing her in tight capri pants. Obviously it made me think of very naughty stuff. The whole thing was probably seen very differently by Kelly.
So, I told her about the joke and apologized for taking it too far. I really did feel bad about it afterwards. I’d already started to doubt the whole thing when I didn’t hear back from her. When I finally did and she wasn’t into it really, I felt even worse. I told her I wouldn’t play any pranks on her again in the future. I also explained that I didn’t think she’d really take it seriously. In reading back over the emails I’d sent her later, I seriously felt like it wouldn’t fool anyone, but I guess it did. She was miffed for a bit, but she understood that I was just having a bit of fun and that it turned me on. So, it didn’t take long before we were back to just occasionally chatting and talking dirty, sending links, etc.
Ok, here’s where things really get interesting. The email stuff described above happened in early January 2015 as you can see. Fast forward to early April (a year after the first joke I’d played) and let’s pick up there. I had gotten over feeling bad about the second joke I’d played. Kelly and I were back to normal. I finally got around to telling Lisa about it. I didn’t go into full detail because I knew she didn’t care about anal sex and might even be a bit put off by that. I just kind of shortened it and led her to believe that I’d told Kelly that I’d flirted with and fucked Patti. I even mentioned that what had made me think about it was that Patti had been looking better recently. She didn’t say much about that, but as with the first one, she thought it was pretty funny. Kind of like Kelly, she wasn’t into it, but then she didn’t really like Patti much. She did find the humor in how I had tricked Kelly though. Lisa’s kind of sadistic that way.
Anyhow, the only reason I’d even mentioned it to her is because I was feeling a bit turned on and sometimes I make dumb decisions when I’m thinking with the little head. I wanted to see how she would respond when I told her. She just chuckled a bit about and we discussed how it was crazy that Kelly believed it. She didn’t take the bait and want to know more about it, so I let it go. After she left, I didn’t even really think much more about it.
About 4 days after I had told Lisa about the joke, I got a call from Patti. She asked if I had time to come show her something on the computer. For half a second it flashed through my mind that she somehow knew about the joke, but I quickly dismissed the notion. As I mentioned, I didn’t think Lisa and Patti were that close and I figured that Lisa wouldn’t do that to me.
When I got to her office, she was nice enough. We both said hi and such and then I asked her to tell me about she wanted me to show her. She asked me to close the door behind me, which I found kind of odd. She didn’t waste much time. She told me that she didn’t really have a computer question. I was pretty nervous all of the sudden. She told me to sit down and she proceeded to tell me she and Lisa had been talking a couple of days before. Apparently, even though Lisa’s not a big fan, they still gossip occasionally and so Patti knows probably more than she should about her sex life. Which made sense because actually that’s how Lisa had been with me.
It dawned on me that maybe Lisa wasn’t the best person to tell this stuff to. I could totally see her being a bit loose with her lips, if you will. So, this is probably why it’s not the best idea to have interoffice affairs and flirtations. Anyhow, Patti basically let me know that while they were gossiping, Lisa basically said, “I know someone who wants to fuck you!”
Patti said she was surprised at this, but asked her to explain. Lisa apparently wasted no time in spilling the beans on how I would talk to her and Kelly about sex stuff. Then she told her about the jokes I’d played and I guess she surmised from my choice of subjects that I wanted to fuck Patti. Which obviously wasn’t far from the truth. So, I turned three shades of red and she noticed it. She took this as me admitting that it was true. I tried to explain to her that it was just a prank and that the reason I’d used her is because it was fairly unbelievable. I told her about how I figured that Kelly would see right through it.
So then she said, “So you don’t want to fuck me?”
Of course I had to be tactful now. I didn’t want to offend her. I still didn’t know where this was headed. I was fully convinced that she was going to tell other people around the office about what had been going on and I might possibly even get fired. So, I basically said, that it wasn’t that. I explained that I did find her attractive, but that’s not why I had made up the story. I must have done a good job of clarifying because she chilled out a bit and seemed to understand where I was coming from. I also told her that obviously I wasn’t ever expecting her to know about this. She agreed with me on that and said that she thought Lisa liked to stir shit up sometimes.
Next she said she was cool with everything and that it was no big deal. She said she even was a little flattered to find out I thought she was attractive. She mentioned that she thought she’d seen me eyeing her ass a couple of times, but she wasn’t sure. I apologized for that, but she told me not to. Apparently, she was single and hadn’t had much action in a while, so she said it was nice to be seen as sexy sometimes. I told her she was definitely an attractive woman and that she shouldn’t feel bad about herself.
I was relieved that things were working out ok and she wasn’t offended or pissed. Just as I thought I was about to be on my way and that the situation to had blown over, she said, “So, can I see the emails you sent to Kelly?”
I was struck dumb for a few seconds with that one. I wasn’t sure what to say. Eventually I told her that I didn’t know about that. I told her that I didn’t want her to read them and feel weird about it and I added that it would make me feel strange to share it with her. She said that she would be cool about it and she said something along the lines of, “It’s kind of fucked up that you can write dirty stories about me, but won’t share them with me when you find out I’m ok with it.”
I sort of had to agree, but I went on to explain that they weren’t quite as simple as I had led Lisa to believe. Immediately I regretted saying that because I could have just written some new emails that were toned down and she would have never known the difference. Instead, I just stoked her curiosity. She jumped on this immediately and basically said that now she really wanted to know what I’d written. So, I kind of just tried to level with her at this point. I explained that the stuff that I talk to Kelly about and that I fantasize about is pretty kinky. I continued by telling her that the story I’d concocted was much dirtier than what I’d shared with Lisa and I didn’t feel like letting her see it would be a good idea.
Of course she persisted in wanting to read the emails. She told me that no matter what the emails said, she wouldn’t get mad at me. She also said that she was no prude and unless they were really gross or morally objectionable, she wouldn’t be upset. Obviously, I could have just refused and I doubt she would have tattled on me, but it dawned on me that I’d kind of like to see what she thought. I mean in a way, it was perfect because it wasn’t me that brought them to her attention. Circumstances beyond my control had caused her to inquire about it, so even if she thought the emails were foul and disgusting, I knew that she knew that I hadn’t planned on her seeing them. That I hadn’t tried to make any inappropriate moves in her direction to bring her into my world of kink.
I’d be lying if I said I wasn’t nervous about taking this next step. Even if she wasn’t totally grossed out by my fantasy, she’d probably think I was a total weirdo and it might not only make things weird between us, but she might spread gossip out about it. Against my better judgement, I decide to take the plunge. I told her I’d forward the emails to her when I got back to my desk. I did ask her for a non-work address to send them to. At the very least I didn’t want this shit sitting on the company server. She gave me one and she could tell that I was hesitant. She reassured me that she would keep it discreet and that this wouldn’t get spread around work. That set my mind at ease a bit.
When I got back to my desk, I went back through the emails and moved them to a folder so I could sort out the order before I sent them on. The only one that was missing was Kelly’s response. I had deleted it after I read it because it made me feel bad. So that’s why it’s not included above. I’d almost deleted them all, but for some reason I kept them. I think because the idea of it still turned me on a bit. I didn’t say anything to Patti about how Kelly responded. I figured she’d ask if she was interested and I’d probably embellish it a bit and get rid of the part about how she thought it was kind of gross.
After I got them together, I took a deep breath and began sending them to her in order. I was positive I’d be soon be receiving an email chiding me for being a depraved asshole or something, but actually I got nothing. For two agonizing days, I got nothing from her. I figured she either hadn’t read them yet or thought I was a perverted piece of shit. Her actual response took me completely by surprise and was nothing short of astonishing:
Sent: Thursday, April 9, 2015 2:37 PM
Hi Max. I read your emails and all I can say is, whoa! You are one sick puppy! I wasn’t sure what to expect, but man…this was definitely a little perverted. Though it wasn’t as freaky as I thought it would be. You sure like asses and anal sex huh? I actually blushed when I thought about you wanting to do that to me. I can’t believe Kelly actually believed that I was like that! Haha! It is kind of funny really.
Well, anyhow, I had to think about this a bit before I wrote you back. I was pretty surprised when I first read it—not grossed out, just wasn’t sure how I felt. If I had seen something like this even a couple of years ago, I would have just told you that you had some problems and I would have left it at that. The thing is, I haven’t been with anyone sexually in about 4 years. I have spent a lot of time alone with my fingers and my toys. I have been on some dates, but nothing has felt right. So, long story short, I have read some stories on the internet and seen a little porn. I’ve never been closed-minded when it came to sex, but the men I dated and my husband of 10 years were never very adventurous. They were ok lovers, but nothing super weird happened. It’s only in the last couple of years that I have started thinking seriously about doing naughtier stuff.
I considered kinkier sex earlier in life, but just never was with the right person and was kind of afraid to act on it. Anal sex had never been on the agenda…but, like I said, I’ve been lonely the last couple of years and have seen some titillating things on the internet and TV. (It’s funny that you mentioned those 50 Shades of Grey books. I haven’t read them, but I have some friends who did and one of them went on and on about it and told me how it really put a spark back in her marriage.) Anyways, I recently started teasing my ass a little while masturbating and it felt pretty good. I haven’t done much beyond slipping a finger in a little ways, but the results have been quite amazing!
I think I’m interested in experimenting further.
Also, I always enjoyed being spanked and I have been tied up and blindfolded a few times and that was fun. I never went too far with these things. I mean, I actually wanted to go a little more extreme than my husband or boyfriends, but like I said, they were more normal.
So…what I’m trying to say is that after I got over my initial surprise and embarrassment, I got…horny 😉
I’m kind of afraid, and not sure what I can handle, but if you are interested, I want to do it. In real life. At the very least, I’d like to ask you more about kinky sex stuff. Think about it and write me back.
After reading this my mind was totally blown. Never in my wildest dreams did I think my little jokes and perverted fantasies would lead to the possibility of such an interesting opportunity. She wasn’t the naughty vixen like in my emails, but honestly, this was a lot hotter. She was an anal virgin, but was open to playing with me and essentially being taught or trained by me. I went from being nervous and depressed to being intensely horny. Even though I wanted to write her back immediately, I didn’t want to seem overeager and also, I was kind of shaking with anticipation. I couldn’t think of what to write at first. Also, it occurred to me, I wasn’t sure what she meant by “I want to do it. In real life.” What exactly did she want to do? A little experimenting? A finger or two or a toy? Full on anal fucking? It sounded like she was open to all of it.
After calming down a bit and thinking about what I was going to respond with I finally go to work on a response. I was still too excited to write anything long or thought out, but I wanted to keep this ball rolling. So I wrote her back the following:
Sent: Thursday, April 9, 2015 3:20 PM
Subject: Re: OMG!
Your response was…unexpected. To say the least. I thought you were going to think I was a disgusting pervert and just tell me to fuck off. So very glad you didn’t. Your email really caught me off guard and I went from being very worried, to…uh…having an erection. J I’d like to discuss this more in person perhaps, but yes, I’m VERY interested.
That being said, when you wrote you want to “…do it. In real life.” Can you tell me what you’re interested in doing exactly?
Looking forward to talking more soon! You’re awesome!
After I sent this, she responded quickly with the following. Mind further blown!!
Sent: Thursday, April 9, 2015 3:26 PM
Subject: Re:Re: OMG!
I want to do your emails. Know what I mean? I want us to make your emails happen in real life 😉
So, as you can imagine, I was left reeling after reading this. I seriously almost felt like I was in a dream. Things like this don’t normally happen in waking life. At least not to me. I certainly wasn’t complaining. Just feeling a bit dazed perhaps. Needless to say, I wrote her back and told her that I was absolutely into this idea. I asked her when she wanted to start. She told me that she wanted it to be as similar as possible to the way it played out in the emails. So she said that she was going to go buy some toys that evening so she could do some “homework,” but we could maybe do the actual re-enactment the next week. It was a Thursday, so that only left Friday in the work week. Also, it was dependent on conditions in the office really. She said if she was too busy or if there were too many people around, then we’d have to hold off. She explained that usually there was a time of day when she was alone in the office, but not always.
As it turned out, it wasn’t until the following Tuesday that things finally got started. It was really difficult to wait for this to happen. I was horny as shit during the days leading up to the main event. Monday was particularly disappointing. As much as she wanted to get to it, she said there was just too much going on at work. I was about to go out of my mind with anticipation and arousal. I jacked off fantasizing about what we were going to do and I came sitting at my desk. Finally I could think a bit more clearly. By Monday evening, I was already filled with erotic anticipation again. This couldn’t happen soon enough.
Thankfully, around 1:15 on Tuesday, I got a call. It was Patti and she said she was having trouble with her printer. The game had begun. Now that it was actually happening, I was really nervous. I don’t know why, but I felt really jittery. I was excited, but I just felt weird. Once I got back to her office and we started talking, it mostly went away. She had chosen to wear some particularly tight shorts and a blouse that was rather low cut. I think she had on a push up bra as well, because her tits were looking perky and her cleavage was on display. She looked really fucking sexy. After we chatted a bit, she finally broke the ice and said, “I don’t really have a printer problem. I just wanted you to come back here so I could ask you some things.”
So, I played along and we had a conversation similar to the one in the first email. She mentioned that she and Lisa had been talking about sex related stuff and that Lisa had mentioned that I was a freak. As in the email, this led into us discussing anal sex, butt plugs, and BDSM. I gave her my advice and told her about some sites to check out for porn and erotica. All in all, it was very similar to the story I had come up with. I couldn’t help but get very horny during this. I had a major boner in my pants and she certainly noticed it.
We talked about most of the stuff from my fantasy with some minor changes. When I brought up fisting, she said she’d never tried it, but had always wondered would it would feel like in her pussy. She was a little more trepidatious about anal fisting. I told her that it’s definitely not something you just jump into. It requires time and practice. I also threw in that although I had seen men fist women’s and men’s asses before, what turned me on more for some reason was seeing a women’s hand buried in another lady’s formerly tight asshole. Also, I mentioned that I liked seeing women fist their own asses. She seemed to be interested in this and I could see her face getting a bit flushed.
Before the conversation ended we had revisited butt plugs and I gave her some advice on what toys to buy and I explained about wearing them around the house or even at work. She joined in and said that it really turned her on to think about doing it at work. I agreed that it was really hot. As much as I wanted to just bend her over and fuck her on the desk right then and there, I figured I should go along with the story. So I wrapped the conversation up and mentioned that she should let me know if she tried the plugs out. She had apparently memorized the line from the story because she responded by saying, “Oh don’t worry. I will. You’ll be the first to know about it!” This was already turning out to be a lot of fun.
I went back to my desk and couldn’t even focus on my job. The rest of the day was a haze. I was so excited for the next step in this reenactment. Just before I left for the day, I got an email from Patti that said she was heading to the sex toy store right after work. She told me she’d been horny as hell ever since we talked. She couldn’t wait to go get some new toys to play with that night. She also told me she’d fill me in on how things went the following day. I couldn’t have been more amped up. This was completely amazing. Obviously, this was more to go along with the story because I knew she’d already purchased the toys the previous week. I’m sure she’d be doing a lot of practicing though.
That night after work I couldn’t calm down. I couldn’t stop thinking about her putting toys in her ass for the first time. Sometimes when I get turned on by thinking about something kinky happening to someone else, I like to experience it first hand and imagine myself in their shoes. So I pulled out a couple of my own butt plugs and used them on my own ass while I jacked off and thought of pushing them into Patti’s tight asshole. I came very hard with these images in my head and a medium sized plug deep inside my rectum. After I recovered, I had a couple of beers and watched some TV until I fell asleep. The next day couldn’t arrive soon enough.
When I got to work the following day, it was again difficult to concentrate on things I had to do. Thankfully, I didn’t have to wait long to hear from Patti. Around 10:30 AM, I got a message from her. This is what she wrote:
Sent: Wednesday, April 15, 2015 10:29 AM
Well, I got some new toys as promised! I got three different sized plugs (and a new vibrator!). Holy god, you were right! I feel like a whole new world has been opened up for me. Once I was warmed up 😉 I had some of the most intense masturbation sessions I’ve ever had. I came so hard, again and again!
Now I understand also why you said that when you get into it, you start to want them bigger and deeper. I could almost see taking a woman’s fist now. Hee hee.
I have a medium plug in now and it feels so so so good! I’m having trouble doing my job. I’m so damn horny!! Do you think maybe you’d like to come check on my progress in a little while? Maybe around noon when I go to lunch? I just want to make sure I’m doing it right J
This was outstanding! I was so excited that she was into this so wholeheartedly. It appeared that she truly did like the butt plugs and was eager to take this thing further. I couldn’t believe that in about two hours I might be fucking Patti in the ass or at least molesting her kinky little body. Before I had even processed this first email, I received a quick follow up:
Sent: Wednesday, April 15, 2015 10:41 AM
I can’t believe I basically just asked you to meet me so you can inspect my naked ass with a butt plug inserted! I’m just…so fucking turned on. I can’t even think straight with this thing inside me. My pussy is drenched. Good thing I brought another pair of panties to change into. I hope you don’t think I’m being too forward.
I felt like if my dick got any harder it would break and fall off. She was pushing my buttons in all the right ways with these emails. I don’t think she was playing either. I really sensed that she was super turned on. I bet her naughty little pussy was drenched. I wrote her back quickly. I decided to be cheeky and literally copied and pasted part of the email response from this stage in my fantasy:
Sent: Wednesday, April 15, 2015 10:55 AM
Well damn! I’m speechless! You’ve been a busy girl haven’t you?
I’m glad you’ve been enjoying the toys. I figured you would. And I have to say, your email made me insanely horny. Not gonna lie, my cock is rock hard. I couldn’t help but pull it out and play with it some. Have you been touching yourself this morning also?
I really, really probably shouldn’t meet you, but my willpower isn’t very strong and you’re hitting me where I’m weakest when you tell me about playing with butt plugs. So, yes, I’m very interested in “checking on your progress.” I’ll do a thorough job 🙂 Where should we meet?
And regarding your second email, don’t be nervous. I mean, I’m a bit keyed up too, but mostly excited. You’re in good hands with me. J You have no idea how horny it makes me to hear about how wet your pussy is from all this! Can’t wait to see you!
So, this thing was really about to happen. She wrote back to my email and told me that my reassurances made her feel a little better. She told me to meet her in the vacant office on the bottom floor of the back building where she was. Just like in my story. This was a good location in the story and in real life because it was separate from all the other offices. You had to go into it from outside the building and you had to use a little code on the lock, which she provided for me. There was an interior entrance, but it just went into a garage and it was always locked. This office hadn’t been used in a couple of years. It was perfect for our needs. She also mentioned that she had tidied it up a bit, which was very practical on her part. I guess it would have been fairly dirty and dusty. It was about get very nasty in there.
I wrote her back a short email and confirmed the meeting time. I was about to jump out of my skin. Again, I felt like I was in a dream. How could this possibly be happening in real life? It wasn’t that this was really that crazy. I mean let’s be honest, it was just a 40 year old guy about to do some naughty stuff with a slightly older woman. I’m sure it happens all over the place every day. It had never happened to me though. Furthermore, as I mentioned before, the fact that through a series of coincidences a joke/fantasy of mine had actually come to life was just nutty. The fact that it was happening at work added another layer of surreality to it. I was just along for the ride at this point.
After sitting at my desk for that last hour, unable to do any work, it was finally time to head back to see Patti. I got up from my chair and somewhat shakily started walking towards the entrance to the building. I was feeling nervous again. Hopefully I would feel better by the time I got to the back office. I was actually glad for the walk I had to make. I did indeed feel a little less shaky when I go there. My hand was slightly wavering when I went to punch in the code on the door however. I was mostly just excited now.
When I walked in, Patti was standing by the desk smiling. She had on a very short, flouncy skirt and she must have taken off her bra because her smallish tits and nipples were on full display in the very tight top she had on. She look positively slutty. Her make up enhanced this fuck me vibe. There wasn’t too much of it, but she’d put on some eye shadow and some lipstick and looked kinda like a bad girl. We greeted each other and I told her hot she looked. She thanked me and said I was looking very sexy as well.
The office looked nicer than the last time I’d been in it. No dust anymore and it smelled decent. She apparently plugged in an air freshener. Also, there were a couple of small pillows on a nearby chair. I assumed she’d brought those also. They would help during the fucking I planned on giving her on or over the desk. There was a bag sitting next to the chair as well. I assumed she’d brought some lube and maybe even some other toys, but I wasn’t sure.
I walked closer to her and I could see that she was shaking a little. She looked a little tense. I asked her if she was nervous and she replied that she was. I told her she had nothing to worry about. She nodded, but I could tell she was scared. So I decided I would just take control and see where this went. I got right in front of her and looked her in the eye and asked, “Are you ready to be a good little slut for me Patti?”
She nodded again and gave a slight smile. Then I asked her if she had the butt plug inserted as requested. She said she did. I moved towards her and grabbed her arms and put them behind her back and held them together as I leaned in for our first kiss. It was surprisingly passionate. After we made out a bit, I moved her down to the corner of the desk and situated her ass over it. I told her to bounce on the plug as we tongue kissed some more. She whimpered a bit as this happened. Then I moved my hands up and groped her tits. They weren’t very large, but her nipples were hard as diamonds. I tweaked them a little while forcing my tongue further into her mouth. She responded by hungrily kissing me back.
I had her stand up and lifted her shirt over her head. Her tits were definitely a bit smallish and slightly saggy, but not bad. She had nice perky pink nipples. I fondled one breast while I took the nipple on the other into my mouth and sucked it. She moaned a bit at this. She was very turned on and sensitive it would seem as she shivered a bit when I first sucked it in. I moved my free hand down her back and onto her skirt covered ass and squeezed one of her plump buttocks. It felt wonderful. I played with it a bit as I moved my mouth over and licked her other nipple for a bit. She shuddered slightly as I sucked it and continued to fondle her ass. It was time to move on to something kinkier now though.
I lifted my head from her breast and told her sternly to turn around. She complied quickly. I leaned my body against hers so she could feel my hard cock against her ass. Then I cupped her breasts in my hands. Tweaked the nipples a bit more before sliding my hands down her stomach and onto her hips. I grinded my crouch against her luscious ass while holding her firmly around the waist. She groaned with pleasure as I did what I wanted to her. I moved one of my hands right between her legs and grabbed her cunt firmly. She kind of gasped and pressed it against my hand more firmly. It wasn’t time to play with that yet though.
I quickly moved my hands back to her hips and slid the dress down her legs and told her to step out of it. She had on a pair of very small, very cute pink panties. I could just make out the base of the plug through the fabric. Her juicy ass looked fantastic in the cute little undies. I grabbed a handful of ass cheek and began fondling the focal point of a lot of fantasies for me recently. After squeezing and kneading each buttock for a bit I swiftly pulled her panties down. She breathed in quickly, clearly taken by surprise. I resumed fondling her ass, but now I was able to feel the smooth texture of her skin. She was clearly enjoying the attention as she was letting out little gasps and sighs as I molested her.
I told her that she was being a very good little whore for me so far. She smiled a little and seemed somewhat proud of this, but I then told her that she was still a naughty little bitch and needed a spanking for that. She seemed a little surprised that I’d called her the b word and she pouted a little at this. I didn’t react at all and simply told her to bend over the desk. She did as she was told and I stood back to admire the lovely ample buttocks and shaved cunt on display. Her body really was in pretty good shape for her age. I actually quite enjoyed the little bit of extra flesh that being a mature woman provided to her shapely ass.
She jumped when the first spank hit her left ass cheek and again, but less so when I smacked the right one. I wasn’t going too hard on her, but I gave her some rather firm swats. I did this a few times until she had a nice rosy glow to her bottom. I told her she was a very obedient slut and that she had done a great job of accepting her punishment. Now I was ready to fulfill a fantasy I had long had. I told her to stand up straight again, but she was to stay facing away from me. I slid my hand down on to her ass again and rubbed the recently spanked redness a bit before moving into the cleft between her cheeks. I pressed on the base of the plug a little and looked at the side of her face as I put some pressure on it. She seemed to enjoy it being pushed deeper into her ass.
After teasing her like this for a few moments I slowly withdrew the toy. It turned out to be a nicely sized plug. Probably somewhere between a small and medium. Not too bad for walking around at work. No wonder she was so horny. I knew what that size felt like and it was a real turn on to wear in public. After I removed it, I again praised her for being such a skilled whore. Then I did something I’d wanted to do to a woman at work for a long time. I spit on my fingers and teased the rim of her anus before slowly sliding two inside her as far as they would go. She whimpered a little and winced slightly. It felt fucking amazing. Nice and warm and lubed up. I moved them in and out a bit before spitting on them again and then inserting three fingers. Once they were inserted half way I spread them out a little to stretch her sphincter a bit more. She moaned a bit and I asked her if she enjoyed having my fingers deep inside her asshole. She nodded and emphatically said she did. This was making my cock very hard.
I moved the fingers in and out of her ass a few times and then pulled them out and held them in front of her face. Then I told her, “Since this is our first time together, I won’t make you take my fingers into your mouth after they’ve been in your ass, but in the future, when I know you’re clean, this will be expected of you. Now, spit on them for me.”
She looked slightly shocked, but again, she did as she was told. I had her do it a couple of times to get them nice and slippery. Then I pushed them back into her tight asshole. They went in with no resistance. I started pumping them in and out of her faster and put my mouth up to her ear and asked her, “Do like getting your naughty asshole fingered by men you hardly know at work? Do you like being my little anal slut?”
She moaned and said “Yes…yessss…I do.”
I think it was safe to say, she was enjoying it. It was so fucking hot to have my fingers buried in Patti’s ass. It was turning me on so much. I leaned into her as I pumped her increasingly roughly and I whispered more dirty shit into her ear. I’m not even sure what all I said, but she was getting in it. I told her I was going to fuck in her the ass soon, but first she was going to suck my cock. She nodded her assent. I pushed my fingers all the way inside and then guided her slowly to the chair with them inserted. I had picked up the butt plug on the way.
When we got to the chair and I asked if she had brought lube and she pulled it out of the bag next to the chair. I pulled my fingers out of her ass and applied some of the liquid to the toy. Then I placed the tip against her pretty little rosebud pucker hole and pushed it all the way in in one smooth motion. She didn’t even wince. She was nice and loose now. I told her to sit in the chair and I took off my shirt. Then I told her to get take down my pants and underwear and take my cock out. As she did this I explained to her that this time was for my pleasure mostly and that next time we met it would be for her. She told me that she understood as my cock bobbed in front of her face. I spoke harshly to her and said, “Ok…take my cock in your mouth and suck me like the obedient little whore you are.”
Her mouth tentatively took just my head inside. It was warm and wet and felt wonderful. Copious pre-cum had been leaking from my pisshole, so I’m sure she tasted it as she began to suck me. She wasn’t taking me very deep at first, but as she got more into it I began bumping the entrance to her throat. I told her to play with my balls as I grabbed her head and started pumping her mouth harder. It felt great, but I was greedy and wanted more. I told her that if she wanted to really please me she was going to have to take me deeper into her throat. She tried taking me further a few times, but kept gagging. It still felt fucking awesome every time my cock head pushed into the tighter restriction of the entrance to her throat.
There was more saliva now though and she was going slightly deeper each time. One of the times she got me in I held her head for a few seconds and let her choke on me. When I let go she coughed a bit and took some deep breaths. She had an almost defiant look in her eye though. I got the impression that she liked having her boundaries pushed. This had really gotten me going though and I was ready to work another tight orifice on her body. I had her get up and grabbed one of the pillows. We walked back to the desk and I put the pillow down and told her to bend over the desk. She did as instructed. I reached between her legs with my non-ass hand and felt how wet her cunt was. I teased her lips and clit a bit before sliding two fingers into her hot fuck tunnel. She moaned deeply. She was definitely enjoying this. I fingered her a bit before switching gears a little bit. I had gotten ahead of myself.
Since this was her first time and since it was in the emails, I decided to give her a little pleasure before I fully took my own. I bent down behind her and spread her legs further. Then I kissed up the back of her thighs and moved closer to the wonderful smelling cunt that was on display. She whimpered and sighed with pleasure as I teased her. After a bit of this I buried my face in the moist hole and she groaned with enjoyment. I pushed my tongue as far into her honey pot as I could and went to town on her. I then slurped my way down and took her erect pink clit into my mouth and sucked it. She screamed quietly with surprise and gratification. As I worked her little button, I teased the plug in her ass and slid two fingers back into her pussy.
She was now grinding back against my face and fingers. Her nasty cunt was leaking profusely now and she was breathing heavily. I began pumping the plug in and out of her asshole and she started moaning constantly. I told her I was glad that she was enjoying it because I was going to be fucking the well lubricated hole very soon. She seemed to enjoy this thought because she started getting a little jerkier in her bucking and I could tell she was close to cumming. I pushed my fingers in her pussy as far as they would go and held them there as I continued sliding my velvety tongue over her clit. She began fucking back against my hand and saying all kinds of nasty shit like, “Oh god…yeah…fuck me…fuck my dirty…fucking holes…pump it in and out and suck me…oh shit…oh shit…fucking fuck I’m your good slut baby…I’m your nasty whore slut…”
You get the drift. I don’t remember the exact words, but it was something like that. As she was getting so into it, I started holding the plug in in a fixed position and let her continue to fuck back against my hands. The butt plug was literally going completely in and out of her anus with every thrust. It was awesome. Finally she pushed completely back against my hands and impaled her holes fully as she started to cum. It was insanely hot. She was whimpering and moaning constantly as her climax overtook her. She was definitely going to make a good anal bitch for me considering how much she enjoyed this.
After she quit shuddering and her breathing slowed down a bit, I removed the butt plug with no hesitation and it came out with a slight pop. Her pretty little anus gaped slightly and looked ready for my cock. I told her to reach under herself and play with her glistening pussy. I lubed up my throbbing prick and readied it for action. It was incredibly arousing to look down at the enflamed and slightly open cunt lips as she moved her slippery fingers all over her pussy. The sticky, primed asshole above it was even more arousing at this moment. I was finally ready to work my thick rod into her tight back door.
I leaned down slightly and spit the saliva I had built up in my mouth onto her nasty rosebud. Then I moved closer and pressed the tip of my prick against it and slowly worked it inside her. She stiffened up a bit, but didn’t wince or make any noise. It was going in very smoothly. Probably because we had taken our time and properly prepared her ass. She had been playing with plugs for the last few days and we had obviously already worked it open some today. She was ready for a nice buggering.
Her fingers had zeroed in on her clit as I eased in to full penetration. I was now buried deep within her warm, tight rectum and it was like a velvet heaven for me. My balls were pressed against her moist labia. She whimpered a bit as I held it deep inside. Obviously she had already been stretched a bit, but nothing had been this far into her ass before. I then moved slowly back out until the head was just inside the tight ring of her anus. She moaned slightly as it remained there stretching her. Then she said, “Oh fuckkkk…it feels really good right there when it opens me up…so fucking…much.”
This was music to my ears. She was already getting off on this. I pushed back inside to the hilt and gradually worked in and out more and more quickly until she was used to feeling. It didn’t take long as she seemed to be a natural at this. It probably had something to do with all the plugs she been using lately, but also, she seemed to just enjoy anal sex. Not everyone’s into it, but she was a winner! Before I knew it, I was fucking her pretty little asshole nice and deep and hard.
As I was getting more and more into it, it suddenly dawned on me that I was at freaking work and I was pounding a woman in the ass. A woman that I barely knew and that a week ago I assumed would never in a million years allow me to use her like this. Best of all, she was fucking loving it and moaning out loud how good it felt. This was beyond astounding. Her tight asshole felt amazing. This was by far the best anal sex I’d ever had and I wasn’t really sure how long I was going to last. The whole situation was intensely arousing. So between that and the physical sensation of fucking this older woman’s beautiful butthole, I was already getting close.
I wanted to savor this a little though, so I slowed down a bit. Now that she was loose, I wanted to do something hot. I pulled all the way out and then popped the head back in before each thrust. She really seemed to enjoy this and begged me to keep it up. Unbelievably, I think she was getting close again already. It felt so amazing each time my cock slipped out and then pushed back in past the restricting ring of her anus. I did it slowly at first, but before long I pumped it in and out more quickly. Soon, I just wanted to be back inside fully and started going deeper and not pulling out. I was back to properly ass fucking this slut. We were both moaning and groaning in shared pleasure.
Her hand was massaging and occasionally spanking and slapping her clit and pussy as I continued to pound her. At one point she slid two fingers into her pussy and teased her love button with her thumb. I could feel the fingers in her cunt and they only added to the tight pressure for my cock in her bowels. I told her I was getting close and asked her where she wanted me to cum. As my thrusting became increasingly intense with my impending orgasm she could barely get out the words, but she managed to finally say, “Ohh…ohh…fucking…pump…your…creamy…load…into my…tight…fucking…asshole…I’ve never…felt…hot sperm…deep…in my…ass…before!”
Oh god! This was so good and so hot to hear. It drove me over the edge and as I pounded her for all I was worth, I started spurting my jizz in her ass and pushed my cock as far into her as it would go. She could feel the warm oozing and pulsing deep in her bowels and she then began to cum as well. She spasmed and shook on my impaling tool. This was by far the most intense and satisfying cum I had ever had and I suspect she felt the same. Later she actually told me as much.
After we both had come down a bit from our orgasms, I slowly withdrew my deflated cock and watched as her gaping sphincter closed back up some. Not completely obviously. Not after the pounding it had taken. I realized that I needed a picture of this. I told her to stay where she was and grabbed my phone. I snapped a couple of shots of her beautiful and enflamed used holes from behind. I wanted this to remember the day with, but also, Kelly wouldn’t fucking believe this in a million years. Now I had proof!!
When I was done taking the pictures, I sat down on the desk next to her and she flipped over and sat next to me. We hugged and cuddled a bit, tenderly basking in the warm glow of our kinky sex. We kissed some more and as we kind of wrapped it up, she told me she could feel my cum starting to drip from her ass. She said it felt really sexy and hot. She told me that she never fully understood how good it could feel to be used and to act like a slut. She told me she was hooked and asked how soon we could do it again. Internally, all I could say was wow! This was a naughty ass woman after my own heart.
I told her we should do it again very soon. We both agreed that it was insanely arousing, not only because of what we had done, but where we had done it. She told me that she might also be hooked on being kinky at work. She told me she’d never been much of an exhibitionist or a risky public sex person, but she wanted to see what kind of boundaries we could push. I was totally game! She said she might want to do stuff in our offices or even some other places. All I could say was yes, yes, yes!
We finally cleaned up and had to get back to work. We had totally lost track of time and had been at it for over an hour already. Obviously we didn’t want to draw any attention to ourselves. So, she left first and texted me that it was ok for me to head out as well. No one was around. I wasn’t too worried about it, but better safe than sorry.
Since then we have had a few other adventures together and are kind of dating actually. We’re still feeling each other out, but the sex has been fucking outstanding. We’ll see where everything heads. I’ll tell more about some of the kinky fun we’ve had in later stories, but for now I’m going to wrap this one up. I know you probably didn’t believe what I said at the beginning of the story, but this did actually happen. The description of the actual sex in the office was probably slightly embellished because it was from memory and from my perspective mostly, though Patti and I did discuss it at length afterwards. It’s essentially how it all went down and it was great.
As a sort of post-script, I wanted to also tell you about what happened when I told Kelly about this. Of course she didn’t believe me and even acted kind of bitchy about it at first. She reiterated that the whole scenario grossed her out and she didn’t understand why I had brought it back up. I, of course explained that it wasn’t expected and that I hadn’t planned it and told her that it was indeed the truth. I sent her the picture of Patti’s used pussy and ass along with another picture I had taken the week after our first fuck. I used a tripod and a self-timer and it was of Patti, totally naked, sitting on her actual desk at work. I was between her legs eating her out and Patti was smiling at the camera.
Kelly responded to this email with amazement and disbelief. This is what she said:
Sent: Thursday, April 23, 2015 11:46 AM
Subject: Re: Proof!
That is just completely insane!! I really didn’t believe you at all. Holy shit Max! How the hell did this happen? I can’t believe Patti really did all that stuff with you. Is she a total skank?
And…how did you get that picture in her office!! Y’all are crazy! Weren’t you afraid of getting caught!
This is just too much! I’ll call you later so we can talk about it…I have to hear more about this. I have to go now because I have a customer.
You’re a crazy freak! 😉
So, later we did talk on the phone and I explained everything to her. I told her that next time we had a session, I would film some of it. She acted like she didn’t want to see it, but later when I sent her some footage I had gotten she wrote me back and said she had to admit that it was kind of hot. She also agreed that Patti was sexier than she had originally thought. She mentioned that this was making her wish we’d done some stuff when she worked in the office. It was awesome that she was coming around like this.
As it stands right now, Kelly has hinted that she might want to play with me and Patti at some point in the future. I told Patti about it and she said she’d be up for it. Neither of them has been with a woman, but they are both very curious about it. I’m really, really hoping that I can get something to happen between the three of us. We’ll see. In the interim, I’ve been quite enjoying my dirty little work slut. Now that we’re kind of seeing each other, we’ve been having a lot of fun outside of work as well. As I said, I’ll post another piece or two about some of our other kinky adventures later on. I hope you enjoyed this one!