BBWs, MILFs, and BBW MILFs from my youth - Part 3

[thechief117]

You guys voted for the married MILF, so here's the story.

At a company I interned at during college, I was assigned to a team that consisted of 5 other people. This MILF was one of them. Most of the time, it was just me, her, and one other person as the others spent a lot of time in meetings or traveling for business. Her and I would spend hours talking while we were alone. Our friendship grew over time and we eventually got really familiar with each other. She would sometimes aggressively flirt with me, despite being married and me being a little younger than her son. She would sit on my desk while we talked about rather intimate topics. I learned she was dabbling in OnlyFans, but was keeping it a secret from her family. And that she was hoping to eventually get assistance helping her page grow as she'd like to go full-time, but didn't know anyone good with a camera and editing skills. Being that young, most of this (laughably) went over my head and just saw it as trusted conversation between two friends. And yes, I still cringe thinking about how oblivious I was.

I remember the first thing she did that made me realize she was actually into me was, while she was sitting on my desk, she spread her legs and gave me a good look up her skirt. To this day, the leopard print panties she wore are burned into my memory. It took me by surprise and she thought that was hilarious. Over the next couple of weeks she would do tease me in various ways, like bend over in front of me or ask if I liked the way her tits or ass looked in her outfit that day. She also texted me a few photos of her in the work bathroom or at her desk. The most I got was a photo of her in her bikini.

Nothing really major happened for weeks. Towards the end of my internship is when she cranked it up a notch.

 

[thechief117]

One day when it was just me and her, she kept texting me, despite her cubicle being just around the corner. Eventually she texted me asking if I liked the way she looked today - a common things she'd usually ask while posing in front of me. In the several selfies she sent, she had pulled her shirt down and was trying to highlight her cleavage.

 

[thechief117]

Feeling coy, I responded:

Me: "Yeah you look great as always"

Her: "Did you notice I got my nails done?"

Me: "Looks like they match your bra 😉"

Her: "Yep"
And she sent the following photos

 

[thechief117]

I remember thinking that I was so slick to get a photo like that from a woman like her. So I responded:

Me: "Nice but I can't really see it"

Her: "That's too bad"

I blew it. I pushed a little too much and messed up. Feeling embarrassed and ashamed, I got back to work. I remember there was dead silence for a few minutes. Then I got a text from her.

 

[thechief117]

Her: "I just love my new nails"
With the following photo

 

[thechief117]

I don't remember if I gasped or if I shifted in my seat, but she knew when I saw her text because I heard her laugh. I said out loud "well that was mean" and she laughed again. She walked over, sat on my desk, and asked if I got too excited. After I told her I was just the right amount of excited, she said prove it.

I leaned back in my chair and showed her the bulge in my pants. She got a little mad and said she meant she wanted me to show her. So I sheepishly unzipped my pants and I took out my cock. The whole time I was staring at the door and jumped every time I heard a random noise.

She told me I had a nice cock and that she loved that she made me hard. She asked me to stroke it. I remember getting a burst of courage and told her she could do it if she wants. She smiled and immediately got in front of me, gabbed my cock, and began to stroke.

 

[thechief117]

She stroked my cock for a few minutes, telling me she loved how it looked and that she always thought I'd have a nice cock. Then she licked it a few times. I recall that the pleasure mixed with the pure shock was almost enough to make me blow my load. She laughed at my reaction, stood up, and said we should get back to work.

A bit confused, I calmed down and went back to work.

 

[thechief117]

Some time passed and I got another text from her.

Her: "I dropped some stuff under my desk and I bet you'd love the view"

 

[thechief117]

When I walked over to her desk, she looked at me and asked what I wanted. In my mind I was playing along, so I told her I wanted her ass. She laughed loudly and told me that wasn't an invitation. But she stood up, turned around, and bent over.

"If you can undo my pants button, you can pull them down." She said in a sexy voice. So I reached around and realized her pants were tight, especially with her bent over. After stumbling with the button for what felt like an eternity and enduring her laughing, it finally came loose. She did that sexy shimmy women do to pull down tight pants, revealing a blue thong that barely showed before disappearing into her thick ass. She told me to take my cock out again.

Thinking I was about to get lucky, I whipped it out and began to feel for her pussy. As soon as I felt it, she moaned but told me not to put it in. She just wanted me to stroke myself and if I had to cum, I could cum on her ass. So I stroked myself while she shook her ass and brushed it against my cock. At one point, she let my cock rub between her thighs and against her pussy, but that was as far as it went.

Unfortunately, I didn't get to finish. After several minutes, we heard the office door open around the corner and a few coworkers walked in. We scrambled to put things away and made it look like I was helping her with something on her computer.

Nothing else happened the rest of the day.

 

[thechief117]

A few days later, it was just her and I again in the office. She texted me a photo another selfie.

 

[thechief117]

Her: "I'm wearing your favorite bra again"

Me: "And another thong?"

Her: "LOL no just some regular panties"

Me: "Aw man. I bet your ass still looks good in it."

 

[thechief117]

As soon as I sent the last text, I saw her halfway to the bathroom.

A few moments went by and I got a text.

Her: "You tell me"

 

[thechief117]

Before I could respond, she sent another text.

Her: "Oh wait you like my ass in a thong. Is this good enough?"

 

[thechief117]

Me: "You have an amazing ass!"

Her: "What about my tits? Do you like them?"

 

[thechief117]

I told her everything on her looks perfect. She asked if I was stroking myself to her photos and I told her I'd rather have the actual thing. Then she didn't respond right away.

About five minutes went by and then I got another text.

Her: "Are you coming or not?"

 

[thechief117]

I hurried over to the bathroom, walked in, and saw her standing at the sink still wearing just her bra. I recall I was a little grossed out she was barefoot in the office bathroom, but that thought soon left my mind. She walked over and asked me if I wanted to fuck her. Without hesitating I agreed and she told me to deadbolt the door.

While this is arguably the best part of the story, unfortunately she didn't let me take photos. She only let me keep the one I snapped while she was blowing me. Then she asked me to turn off my phone or she would leave.

After almost making me cum from just a bj, she put her hands on the wall, bent over, and told me to fuck her from behind. I told her I don't have any condoms, but she didn't want to use one anyway. So I spread her ass, felt for her pussy, and guided myself inside her. She moaned and told me it had been a few weeks since she and her husband had had actual sex and she didn't want to wait any longer, especially after seeing how hard she made me.

I remember her pussy was so wet, I slipped out a few times. While we probably could have gone on for hours, we were still in an office bathroom so we had to wrap it up quickly.

Me: "Where do you want me to cum?"

Her: "Inside me"

Me: "Really?"

Her: "Yes! Fill my pussy with that thick, young cum!"

I released a huge load of cum into her pussy before I pulled my cock out. She put her middle finger into her pussy, pulled it out, then licked the cum off of her finger. She told me I tasted great. Then she said maybe we should have pulled out because it's not a safe day for her. I immediately froze and looked at her. She laughed and told me she was kidding. Then, without even cleaning up, she put her clothes back on and left the bathroom.

 

[thechief117]

Later that night, I got a text from her saying she needed to clean extra to get all of me out of her.

 

[thechief117]

While my internship eventually came to an end, we kept in touch for a some time. She told me she had some fun ideas for her OnlyFans, such as I could be her male talent for videos. Nothing ever came of it though. We texted less and less as each week passed and eventually drifted apart.

I heard from her a few years later. She tried to get her OnlyFans up and running by making content on a regular basis. She made some money, but nothing significant. One day, she got caught trying to make some sexy video in her cubicle and was fired. She mostly working part time at stores after that. When she messaged me, we caught up a bit and decided to meet at a park near where she lived.

We jumped right back into flirting like we did when we worked together. She even sent me something for old time's sake. She had gained a little weight and looked a little older, but I thought she still looked good.

 

[Unique6328]

Great story, did it continue on from here?

 

[spaceship]

Fantastic story and a sexy lady! Well written and photographed. I bet these photos and those memories have been replayed many times.