Hooking Up with a Coworker

It was reccomended that I post here after posting a bunch on Reddit.

I have been this site for a while but have debated about submitting my own story until today. A bit of information though for background. I am Jack and the woman involved is a coworker I'll call Kat. Kat and I are both teachers at the same high school, I had her oldest kid in class a few years ago. She is about 45, married, average height, blondish red hair, glasses, thin, mid-B cup, hourglass figure; she kind of reminds me of the sexy librarian. As for me I am 32, pretty average "dad bod" type of guy, about 6'2 with a 7.5" cock. Okay, that is the background info that everyone really needs to know.

This story occurred about a year ago, Kat and I had worked together at this point for about 5 years and had always been professional but friendly. I had her son in class and then as my student assistant and got to know him and the family well. Once he graduated, I had him house and dog sit for me a few times when I was out of town and got to the point where he had a key to my house, and I quit getting it back.

Anyway, it was around the holidays and we had our staff Christmas party at one of the local bars/restaurants, Kat showed up without her husband which was odd because they seemingly were very close with a happy marriage. She sat down at my table with our other friends and when asked, started talking about how they had gotten into a fight and he had stormed out of their house and how she was sick of his constant working. After everyone got a few drinks in them, the conversation shifted to happier stuff. As the party began to wind down, people began to leave and from our friend group it was just me and Kat. We spent some more time talking about her husband and the fight. She said she was going to head home and I walked her to her car where she hugged me and thanked me for listening to her.

I told her "Anytime, you want to talk or anything, let me know!"

After she left, I left and went to my "normal" bar to catch up with some other friends; after a few hours I decided to head home. When I got home, I saw a car sitting up the street from my house that looked familiar but didn't think anything about it because my neighbors always have people over. I go into the house and let the dog out and put him in his crate where he prefers to sleep. When I get upstairs, I notice that there was a light left on in my room, so I go into the bedroom and there sits Kat reading a book on my bed.

I honestly looked at her and said: "What the hell are you doing here?!"

She got a very small smile on her face and said, "Sorry, I didn't want to be at home and get into fight with Andy (her husband) so I took Brandon's (her son) key to your house and thought I'd come here and take you up on your offer. I can leave if you want."

I told her, "No you're good, I get not wanting to be there when your angry, just didn't expect anyone being here. You want something to drink?"

I had a few craft beers so I ran down to the kitchen and got some and plopped down on the corner of the bed to just talk about stuff. We got caught up on how her kids were doing in school and what was going on in both of our lives' outside of work. At some point we turned the TV on and started watching some random TV and I had moved to leaning against the headboard with her. After a few minutes, she had begun to dose off and leaned against my shoulder. I have to admit, she had a basic black v-neck t-shirt on and I caught myself staring down at the subtle cleavage that she had.

Well, she caught me too, she shifted, looked up and said "Do you like what you see?"

I kind of stuttered and finally said "Kat, you're a beautiful woman, I'm a dude and it's hard not to stare."

She smiled at me, grabbed my face and kissed me hard. I kissed her back for a few seconds before pulling away and saying, "Wait, you have a husband and I don't want to fuck up your marriage."

She responded, "I was angry at the party because he is talking about divorce. We haven't had sex in at least 6 months and my magic wand isn't doing it anymore. I'm a bit annoyed, and I want you, now." With that, I didn't need anymore convincing and began to kiss her again. Her kisses were almost frantic, I could tell she hadn't had much intimacy or affection lately.

After a few minutes of making out, I pulled her onto my lap and lifted her shirt off; I was greeted by a black simple push-up bra. I reached around and unclipped her bra and threw it to the floor. I kissed down her neck and chest where I took one of her nipples into my mouth and began to suck and nibble on it.

As I did that, she was beginning to moan and groan, saying "God, that feels so good." After switching to the other nipple and cupping her breast, getting more moans and groans, she pushed me away and said, "I feel your cock on my leg, I want to see it!." I wasn't going to complain about that and pulled my shirt off as she moved down and undid my belt and jeans, pulling down my pants and boxers.

Once my cock sprang free, she grinned and said "You have a very nice cock Jack."

And with that she took the head into her mouth. I'll be honest, I had been going through a bit of a dry spell so feeling a warm, wet mouth on my cock was wonderful. She began to work deeper, being that she was so small she began to gag a little bit, but that didn't stop her. Within a couple of minutes she had taken my entire cock into her mouth and was working my shaft while cupping my balls in her hand. I began to feel the tingling in my pelvis that I knew meant I was getting close.

I stopped her and told her, "Look, you give wonderful head, but I don't want to cum yet because I'd really like to be inside you."

As she let go of my cock, she just grinned and said, "That's fine, I want to feel you inside me too."

We switched positions with her on her back and I unfastened the jeans that she had on and slipped them down her legs revealing a pair of matching simple black panties. I started at her knees and kissed up her thighs to the edge of her panties. As I got closer to her pussy, she began to breathe heavier and began to moan softly. I reached up and slid her panties off and was greeted by a perfectly shaved pussy.

I looked up and said "I never would have thought that you shaved everything."

Her response still makes me laugh today; "I can't stand the itching of the hair when it grows back, so I get a massage and a wax job once every two weeks. The last one was yesterday."

With that I began to gently lick her outer lips and tasting how wet she was, I quickly separated her lips and began to lick her inner pussy and began to focus on her clit as she began to gyrate her hips to my tongue and she moaned out, "Oh god, right there!"

Following her directions I kept up my pressure and pace and all of a sudden I felt her stiffen as her pussy began to flood my mouth as she came.

After regaining her breath she looked at me, and said, "Thank you so much, I can't tell you the last time I had someone eat me out, especially that good!."

She kissed me and told me lay on my back; as she got up and began to lower herself onto me, I said "Kat, I don't have any condoms."

She responded "That's okay, I had my tubes tied after Grant (Her youngest son) was born, so we don't need one and I'd really like for you to cum inside me!" With that, she lowered herself all the way onto me with a little grunt as she got to the bottom. After taking a minute to get used to each other she began to ride me slowly, but began to speed up after a minute or two. I was just amazed that this beautiful woman was on top of me that I honestly didn't know what to do except enjoy the show at first.

After couple of minutes I put one hand on her ass and my thumb on her clit, she let out a loud moan and began to grind against me, and then stiffened up as she came.

She laid down on me for a moment looked at me and said "Thank you for that, I haven't cum from a dick since college, I always had to fake with Andy."

I told her, "no problem, now flip over." She laid down on her back and I got between her legs and she guided me into her.

We fucked missionary for a few minutes before she said, "Will you fuck me doggy style in your mirror? I want to see you fuck me and I want you deep." We repositioned on the bed facing my dresser mirror and I eased back into her and began to work up to a fast and kind of rough rhythm. The entire time she is moaning how good it feels to have me so deep inside of her. At first, I didn't look up, was more focused on her tight ass and maintaining my rhythm. When I finally looked up after a few minutes, it was honestly the hottest thing I've ever seen.

At that moment I knew I was about to blow, and I warned her, and she said" thank god, I can't wait to feel it! Give it to me!" With those words, I let loose one of the biggest orgasms of my life. As I shot all my cum deep inside of her, I started to feel her body tighten around my cock as she came too. She screamed out in pleasure "OH GOD!!" As I slipped out of her, I could see a little of my cum slide out of her pussy.

As we both came down, we kind of collapsed on the bed in a sweaty heap. We cuddled for a little bit without saying much, and then her phone rang. It was one of her kids calling to see where she was at and when she'd be home. She handled the call and stood up and started to get dressed very quickly.

I told her she could shower first to which she said "No I want to feel your cum inside me until I get home and get into bed. As she left, I walked her out to her car, and she kissed me on the cheek and said, "Thanks for a great night, I really needed that." As I watched her drive off, I was still shocked at what happened.

We talked a few times over break, and then when we got back to school, in January, it was like nothing ever happened. Her and her husband ended up getting divorced and she got to keep the house... and I got to spend some time there.

This is the first of many stories with Kat that ultimately led to a couple of threesomes, another MILF FWB, and me meeting my current girlfriend.