My Girlfriend was Flirting at Work!

By: HappyTwoPlease

Hello,

My gf has had a crush on someone we will call "Jim" at work for a while. He's mid 40s, she's late 20s.

Jim is a manager for a different department that often works with hers. Recently they started a new project, this being their first since Jim got divorced. I could tell by the look in her eyes when she told me this development that she was going to pounce.

It's been hot to see her put a little extra into her work outfits for his attention. She keeps it professional, just hotter. I figured out the days she works directly with him by the push up bras, tight skirts and dresses. Surely at least some people at the office know she's trying to get someone's attention, even tho her desk has relationship pics on display. She'd give me updates as she worked in a little flirting with him whenever they were alone and soon enough he started to text her outside of office hours.

Jim complimented her but kept it professional. She was scared to make the first move. Frustrated, she told me she was going to give obvious signs any chance she got with him alone. Intentionally dropping things to bend over, unbuttoning the top of her shirt, sitting closer, etc. As a cuck I love when she gives me the details and turn into her cheerleader lol.

It was working. Jim broke the professionalism and sent compliments about her outfits and appearance, she'd reciprocate. Then he sent a "creep shot" he took of her ass bending over. "Your bf is a lucky guy," Jim wrote with it. She concurred and asked what he was going to do with the pic. The sexting took off.

My gf was showing me their convo in real time as I felt her up slowly. Jim asked if I was home and she told him we were in the living room together, concealing that I was involved. Jim instructed my gf to sneak off to take and send him pics. It visibly scratched an itch she had as she nearly went skipping to the bathroom alone.

Returning in just her panties, I ate her out as they continued to sext. From there she played along with this new "sneaky" dynamic. She wasn't showing me their messages anymore. Even if he started to sext when we were cuddling and I could see her phone, she'd reposition. She updated me when he invited her to his place for dinner.

While most of our cucking has had me there, she has met solo with regulars. I asked if she wanted to go alone and mentioned it would be the first time she went alone for the first hook up.

"Yeah it's fine, I've known him for a while." She replied and told me it was going to happen soon.

With Jim being the closest person in our lives to have my gf I commented on how hot and daring it was to have someone local know. She agreed but mentioned they were still gonna be low key for professional reasons. I told her it sounds perfect and she laughed.

"How did he react? Was he weirded out? Not care?" I asked, referring to exposing me as a cuck. "Wellll he doesn't know anything other than I want to fuck him rn." She told me.

Surprised, I asked why. She explained it just hadn't come up yet. It kinda annoyed me that Jim would get her to cheat on me from his perspective. Everyone else in our years of doing this has known before getting in the bedroom. Considering the last time she showed me their convos was the beginning of her "sneaking" off to send him pics, I should've seen it coming.

Realizing how much she is enjoying the cheating fantasy, I didn't press her to tell him. Simply asked that she just stays communicating with me throughout. Plus I had subconsciously played along too. She wasn't good at hiding when they sexted but I acted oblivious around it for a couple weeks.

As the "dinner" got closer, the horny anticipation grew. I found myself really turned on by a new first experience in this dynamic after years of adventures. She was going to his place straight from work and teased how long I wasn't going to see her for.

The day before she asked me to help her pick something to wear. The tight dress that was just long enough to be professional was decided already because she was wearing it the first time Jim snuck an ass grab in at work. But she was tired of her lingerie. Stumped she asked me to buy her a new set. I get a twisted pleasure buying her lingerie that another man gets to experience her in first, sometimes only for them. So of course I drove her to the store.

Arriving she stopped and told me it was going to be a surprise. I gave her my card and left her to shop alone. When we got home she told me to wait on the couch. "No way!" I thought to myself, growing rock hard. Emerging from the bedroom my gf had put on her comfy clothes, yoga pants and my hoodie, hands behind her back walking over.

"You don't get to see my new lingerie until after Jim fucks me in it." She whispered in my ear.

I nodded and she pulled my chastity cage out from behind her back.

"No playing with yourself tomorrow, you have to wait for me to get home, ok?"

I nodded again, squirming and letting out a defeated moan as I wrapped both arms around her waist and gently rubbed her ass.

"That's a good boy. My good boy, my little cucky." She giggled as she pulled down my pants to the sight of my rock hard 4 inches.

She squeezed me partially into my cage. I was too hard to fit so she delivered a little light ball busting. A trick she had learned to deflate me if I was acting up.

The next morning she reminded me that I am not to see the lingerie I bought her yet. I got to see her fully clothed just before heading out. Hair and makeup done beautifully. A tight dress hugging her curves. We kissed goodbye.

On my way home from work she let me know she was headed to Jim's place and when she got there. I sent her love and asked for pics/vids.

I didn't get any updates for a while. Eventually she called me and made up a story about everyone working late so her boss was buying them all drinks. I played along and told her to enjoy herself, no rush at all!

After hanging up she texted me saying it's hard to send pics/vids since he doesn't know I'm aware. But she quickly got off 2 pics. On her knees blowing him, still fully dressed. They didn't even make it to the bedroom. Second was my first sight of her in the new lingerie. It looked like he had fucked her in missionary, pulled out and came all over her pussy and stomach. His load already marking the panties. She looked so sexy I was pumped.

A couple hours going by now she only sent little winky faces, things of that nature occasionally. I started to fixate on her. My imagination flooding my thoughts with all the possibilities. I was dying to know what they were doing. I had to make myself busy with something to calm down so I did chores. Finally she got off a bunch of pics and short vids.

The first vid was her deepthroating from his pov, the second them in missionary from her pov getting bounced around.

The pics tho, It opened with my gf on all 4s crawling into his bedroom.

Then 2 pics of her head laying over the edge of the bed. First his pov showing her body laid out and a glimpse of her in between his legs, balls in mouth, stroking him. The second a reach around pic of her head hanging upside down with his cock in her mouth eyes wide open staring into the camera.

Next were 2 of her in doggy. First one her holding the camera looking back. Her ass arched up, Jim stood behind. Her face also in the shot, a little blurry, yet making a sexy "orgasm face". The second doggy pic was his pov doing anal(!!!).

Last image a huge facial covered her. I wish I could share those but she insisted they were for us only.

"Enjoy! Cleaning up now." She wrote.

I was stuck scrolling through the pics over and over waiting for her to let me know she was headed home.

It took longer than I thought but finally a "hehe ok now im home."

When she got home we went straight to the bedroom. Jim had surprised her with one last round after she had cleaned up and gotten fully dressed. She told me he lifted her dress and fucked her standing against the wall. He left a gift she teased. Pulling her dress up I could see cum leaking down her legs. I helped her pull the dress off and she laid in bed showing me her creampied pussy.

We made out in bed while I got my clothes off. She uncaged me and told me if I could clean her without cumming I could fuck her.

I made my way down and tried not to cum. She moaned and teased me about other things they had done that weren't captured. On the brink I had licked her clean and we made love briefly before I finished.

They are planning to fuck again already tomorrow.

HappyTwoPlease

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