I [43M] worked really well with her [F24] again

Some people at the office started to suspect that my colleague and I were fooling around. Nobody really aproached me because of seniority I guess. But not long after she told me people had been asking her questions and warning her she might lose her job if found out. She liked her job she told me and so we remained friends, without benefits.

One Monday she messaged me saying how the girls in the office went out over the weekend she tagged along and met a very cute nerdy shy guy. They had breakfast together and she totally wanted to see him again. I was genuinely happy for her after the last boyfriend she had.

Over the course of a month they were dating and seeing quite a bit of each other, she would always tell me about it in great detail. We had a couple of double dates going to pubs and I had to agree it was a very nice guy. She looked at me at times when I was talking to her boyfriend and I always answered her look with a smile. I guess she was checking to see if I ‘approved’ of him.

A couple of months later our conversations died down quite a bit, we still had coffee at times and she would tell me how happy she is. However one morning she came in and I could see she was upset. I sent her a message asking if she was okay. She replied that she wasn’t too sure if it was appropriate to talk about what upset her. I told her to meet me at the coffee machine.

When she came in I laughed and told her that I think after what we went through we’re a bit past a certain level or appropriateness. So I asked if it was that bad. It took her a bit of courage to come out with it. She made sure to keep her voice down and started to explain. Now as happy as she is with her very sweet boyfriend, he’s not very experienced and a bit of a prude. No, he’s a big prude.

In all the time they were together they have only had sex in the misionary position. He never went down on her and also didn’t like to talk about it. One of the evenings they were at a pub with some friends they were doing truth or dare and someone asked her if she ever had anal. At home she wanted to bring it up because now she was horny and tipsy. He refused to talk about it and she said he just went to sleep.

The reasons for today’s mood she said was that she brought up that he never went down on her and she would at some point like it for him to lick her asshole. She said she used to exact word to convey her frustration. Apparently he got angry and that women shouldn’t talk like that. So she packed up and left in a huff after that.

She came in for a hug and said she missed me. I asked if she wanted me to go talk to him or take him out to the pub or something. She just nodded. She asked me if I remembered the plug I got her. I told her I couldn’t forget as that was one of the sexiest things to happen to me. She blushed. It’s been in a drawer since she met him she said and started to get this itch to wear it again. That made my dick twitch, she instantly looked up at me.

Back at my desk I sent her boyfriend a text asking if he wanted to go grab a pint tonight after work. He replied asking if his girlfriend put me up to it, I said that it was my idea. He agreed. I messaged my colleague saying he still calls you his girlfriend so don’t worry. She thanked me. During the rest of the day some of the sales girls asked her if she wanted to go for drinks because she looked so upset. They knew it was to do with the boyfriend. She would go since her boyfriend went out with me.

We met up at this Irish bar to make him feel a bit at home. We had a couple of drinks and it took a couple more to start talking about what the problem at home was. He really didn’t want to talk about it. I lied that she didn’t tell me but that she was quite upset and that the girls took her out drinking tonight. After some shots he started to open up and tell me about his uptight parents and his upbringing. He said the thing that got him the angriest was her bringin up anal. Did she think he was a homo. I couldn’t help myself and laughed. He gave me an angry look.

It took a bit of explaining that we don’t live in the dark ages anymore and women are no alien species but just as horny and kinky as us. He wasn’t convinced but he did listen. He said that she was a bit too agressive at times and felt that it should be him the be that aggressive. I let him speak but got a text message and quickly peeked at my phone. It was his girlfriend.

She was having a good time with the girls but she is getting very turned on that I am telling his boyfriend how to handle her. I don’t know what she was thinking or how the conversation was going with him but that was kind of hot. So I decided to change tactic with him and do as she thinks we’re doing. I told him that tonight he at least needs to go down on her to reconcile with her. He told me he never done anything like that and wouldn’t know how to begin.

I went to get some more beers which gave me some time to think about things. Coming back I said after this beer you’re going to text her to meet you at your place. Then when she comes in don’t talk to her, just grab her, take her to your bedroom and push her onto your bed. Start with kissing her and telling her how you missed her, but don’t let her speak. Next up lower yourself of the bed and get on your knees. Now roughly pull her close so her pussy is right up in your face. Pull down her pants.

I guess it was pretty hot for him because he started to sober up a bit and showing some fire in his eyes. He wanted to whine about never having gone down on anybody before but I didn’t let him finish. Having some experience licking her delicious cunt I was convinced I could guide him to her climaxing. I knew that she was more sensitive inside and around her opening than just getting clitoral stimulation. So I told him to not only use his tongue but also his fingers. It was a little akward showing him what I meant, and hopefully she was tipsy enough to get really turned on by his new behaviour.

I never replied to her message, but the next day she was a lot cheerier when she came into the office. She messaged me asking to meet her for our secret coffee hug. Like a good man slut I obeyed her and met with her and got the biggest hug ever. She thanked me for last night and it was so wonderful to get such a surprise. We chatted some more and I told her a little bit about the pub.

All seemed well for the next two weeks or so untils he messaged me one morning. She said things aren’t that vanilla but she can’t stop thinking about me instructing her boyfriend how to satisfy her. Her ass is dying for a licking and ideally to get fucked by a dick. She said she was even wearing my plug today. Eventhough we had fucked in the past, I never actually had anal with her. I know she has my plug in her ass, it always gnawed in the back of my head that I wish it was my dick instead.

I replied asking if she wanted me to talk to him again. She said if I could please do it. On one condition I told her. She asked me about the condition. I needed to work a bit later tonight because of a deadline and I said I need her help with something. After that I would be more than happy to go and have a drink with the boyfriend again. She asked me what it was I needed help with and I told her she’ll be informed later on.

The day goes by and everybody is leaving the office. The boss is not in because of meetings at another office. She knocks on my door and I tell her to come in. Dressed in a dark blue button up shirt and dark blue tight chinos she comes and takes a seat on one of the chairs in front of my desk. Who told you to sit down I ask her. She looks as if that gave her a fright. She mutters something about she thought blah blah blah. I cut her off and tell her to get up and put her hands on my desk. Her eyes all of a sudden registering what is going on. She stutters that she has a boyfriend. I tell her it’s not her boyfriend. It’s my toy to fuck her. I said I am upset because I don’t get to enjoy any of it. She gulps. I get up and slowly walk over to her.

I place myself behind her and grab her ass. This is mine and I want some of it. She whimpers at that. I put my arms around her and put my now hard dick against her ass. I unbutton her trousers and pull them down. I slap her ass again. As a I pull down her panties I make sure to get on my knees. I tell her to spread her legs and bend over more I want to see my toy. As she does I pull on the toy a little and wiggle it a bit. I can see she is getting wet. What I gave you I can also take away, I say as I slowly pull out the plug. She whimpers not to pull it out. I tell her to be quiet and hold her cheeks apart. She is now on my desk with her upper body and parting her ass cheeks her beautiful wet cunt and asshole right in my face. So you were in need of some licking I hear. She whispers a soft yes. I start with her clit, move my tongue between her lips and get my tip pushing on her opening. She’s so warm. Her lips swollen. My nose now right at her asshole. This is not the kind of licking you were talking about though were you, I ask her. She lets a small no escape her lips and I lick her perineum making my way to her asshole. As I put my tongue flat on her asshole she shivers a little. I start making circles over the rim. Slowly I put my tip every so slightly into her hole, she whimpers. I get up. She cries in dissappointment. I grab my dick out and place the tip at her asshole’s opening. You wanted a dick as well you said. I spit a little that lands just on the tip and her opening. She nods. I press it closer to her opening, she’s spreading her cheeks more. I stop. She whimpers. I ask her what she wants. She tries to look back pleading with her eyes. I ask her again what she wants. Please. Please fuck my asshole. Eventhough she had the plug in the whole day she was pretty tight. I pushed the head in and felt some resistance. Play with your pussy I order her. All too eager she grabbed between her legs. I could feel her knuckled rubbing against my dick as she entered herself. I held on tigher to her hips and pushed myself further in. I rested inside of her until I could start pumping more. I pulled back and pushed in. Her fingers and ass stimulating my dick all together. I started to fasten the pace I could feel my balls aching to release. Her moaning became louder as my hips slammed into her ass. She started to tighten around my dick almost constricting me. I pushed on until I could feel my cum bursting out into her ass. I groaned loudly and slowly pulled out.

As my cum is trying to drip out of her ass I grab the plug and slowly push it back in. I tell her she was a good girl and delivered excellent work today. We got dressed and she kept looking at me. She asks me what had gotten into me and how hot this was. I told her it doesn’t concern her but to be ready when I need further assistance in the future. She nodded happily. As we left the office I slapped her on the ass and told her to go home and suck her boyfriend off for me as a thank you.

Source: reddit.com/r/sexystories/comments/kyj573/i_43m_worked_really_well_with_her_f24_again