My girlfriend's boss

[neeryo]

My girlfriend, Sarah, has been working at a small company for a couple months now. She does secretarial work for the most part, but also a lot of odd jobs since it's a lean operation. I've gotten the feeling that she had a crush on her boss, James, ever since her first week on the job. It was just the way she talked about him.

I've only ever heard good things about James. She says he's always very kind to her. He also played a big part in helping her get started in her role when she was hired. James is 35 years old and my girlfriend and I are both 22. I've only ever met James once at a company party, but I can see why Sarah likes him. He's certainly attractive, standing at I'd guess 6'2'' with a moderately muscular build. Seemed like a genuinely funny guy too based on our singular meeting.

I've been into cuckolding for a while now, and Sarah and James have been my go-to fantasy. I don't have any real-world cuckold experience, but I think I'm ready for it if the chance arises. I have come out to Sarah about my cuckolding fetish, and she's been accepting although hesitant to play into it. I've been able to get Sarah to open up a little bit about how she feels about James. She loves to talk about work stories involving him, but for a long time wouldn't admit to having a crush on him. Eventually, she got the message that I really was okay with it and admitted that she does indeed that a "thing" for James.

That was about 6 weeks ago. In the time since we've started bringing up James while having sex and the results have been amazing. It's been some of the best sex either of us have ever had. She'll openly fantasize about James while riding me, and scream his name while she's cumming. It took more of my encouragement, but she has also started wearing slightly more revealing clothes to work. She won't wear anything too over the top, but more often than not she'll show off some deep cleavage or wear a short dress.

Sarah insists that James hasn't noticed her new office outfits, but I figure that impossible. He's either really good at hiding it, or Sarah is really bad at noticing it. I'm not surprised that he isn't openly ogling Sarah, since he knows she is dating me.

I've given Sarah the green light to tease/seduce him all she wants, as long as she tells me about it after work. Sarah enjoys that fantasy while we're having sex, but so far hasn't done anything with James other than wearing the sexy outfits. At this point, I'm praying every day to hear about some new development that happened between them at work.

[armyguyot1]

You probably don't need to do anything but have some patience.

[ucaneffher]

Sounds like she is more than onboard. Be patient but also know that one day when you least expect it, it can and will happen in the blink of an eye.

You’ve planted the seed in her head and it’s currently growing within. The minute the opportunity arises, her legs are going their separate ways and there’s not stopping that.

[SamWarrens]

Keep us all informed!

[v8cobra99]

neeryo - Any updates ?

[SilverStag]

Yes, James has to be careful when contemplating dipping his pen in the company ink...too many employers have been sued, so if he is wise, he will stay away.

It's a great fantasy, but perhaps another guy, with whom she doesn't work is wisest...

[OOAA]

HOT story!!!!!

Any advance?

[SamWarrens]

Any action yet?
Keep us updated.

[neeryo]

Sarah's been coming onto James pretty hard over the past week. She tells me that she's been doing all the textbook flirting while at work with him. Stuff like unnecessary touching, compliments, and finding excuses to talk to James more often than usual. She thinks it is slowly working, and she's thrilled that James has started being flirty in return. Yesterday he even invited her to have a work lunch with him at a casual restaurant near their office. It wasn't a formal date, but Sarah and I pretended like it was in our roleplay that night

I figure it won't be long until they hook up, but Sarah doesn't share my optimism. She wants it to happen (we both constantly fantasize about with each other), but she isn't sure if the mostly innocent flirting will ever escalate to sex.

For everyone concerned about issues with workplace relationships, I appreciate it but I don't think you need to worry in this case. It's a very small company that barely has HR. Sarah could also easily walk away from the job if she had too as I'm lucky enough to make enough for both of us.

[CuriousUK]

So very exciting, really pleased for you (and rather jealous )

[SamWarrens]

Keep us all informed of any developments!

[SamWarrens]

Duplicate post

[SamWarrens]

Keep us all informed of any developments!

[tractorman2]

This is all kinky stuff, and i dont mean to poor cold water on your fantasy but 35 years as a cuck shows me that this has a good chance of finishing in several ways,

James decides to fuck your girlfriend, all well and good, then as she knows plenty about him, maybe he is married after taking her how many times he dare he finds a reason to sack her to protect himself,

James fucks her and she likes it and so does he so it continues, sex is very emotional to a female and if the opportunity comes up having enjoyed good sex with him her emotions take over and your dumped or end up as a fully fledged cuck.

Liberated with a "pass" she gains the desire and want to carry on fucking other men with the risks above.

I am not wanting to deter you but if your both 22 she has a lot of life to lead and will she see you in this long term? when she comes to accept there are plenty of opportunites out there with more experienced men.

Its a dangerous game we all lead, the one thing most young men doesnt understand is the longer term emotional impact on you both.

[Swingcurious]

Following this

[Whosbeensleeping]

Thanks. Hope to hear more how things are going!

[Anders86]

Hot so far, would like to know how it’s evolve

[SamWarrens]

No updates in a long time so I guess it fizzled out, too.bad.

[neeryo]

Sorry for not updating for so long, honestly I just forgot. Things have not fizzled out. Instead, they've really heated up! Sarah and James have been regularly fucking for about 2 weeks now.

It all started after weeks of ramping sexual tension between them at the office. James was surprisingly cautious to start anything physical with Sarah, but she kept dropping him hints and I kept encouraging her. Sarah would tell me about what happened every day after work. Usually she saved it for while we're in bed together, but it's not just bedroom talk anymore these days.

Sarah started by touching James more and more, which he slowly started to reciprocate. Initially it was small stuff like a hand on the shoulder, touching hands, ect. Soon enough James had his hands on her inner thigh and butt. I think it was only two days later when James asked her to come into his office and they made out for the first time. James held her by her hips, her back against a wall, and they both leaned into their first kiss together. James broke it off after a couple seconds to ask her if she was sure it was okay. She assured him that she wants it and that I want her to do it too. They made out for 20+ minutes that day and Sarah ended up with her shirt off. He played with her tits and Sarah got her hand down his pants, but didn't go any further that day.

That afternoon Sarah was absolutely giddy. We were sitting on our couch while she told me all about it. I had to start masturbating on the spot. Sarah helped me get off by showing me "the tits that James had his way with". She kept playing with her boobs while continuing the rest story. I came when she described what James's cock felt like in his pants. She didn't see it, but she felt him enough to get a sense of how big he is. She couldn't put an exact number to him, but he felt significantly bigger than me (her words more or less) so I estimate he's at least 8 inches. I'm just over 6 inches with average girth, so James is definitely packing.

I wanted to get an update on here ASAP since I've been afk for so long. As I already said, Sarah and James are fucking nowadays, so there is plenty for me to go over even if they stopped all activity today. I'll write another post continuing the story as soon as I have the time. Let me know if there are any specific details you'd like me to focus on!

[wannabecUKold]

She assured him that she wants it and that I want her to do it too.

Congratulations. Great to be cuckolded.

So, James knows that you know. Was he surprised? Has he asked further about you? Presumably he now knows that you know he is now fucking your girlfriend?

You indicated you have met him once. Any plans to meet him again soon, him as her lover, you as her cuckold? Any talk of you being able to watch them have sex?

Is James married?

Hopefully no office gossip yet?
Now they are fucking, James and your gf should redouble their precautions to keep this secret.

[mundyman]

What does your GF look like?
Where and when are they fucking?
She now wearing overtly sexy clothes to work, or sexy stockings or lingerie under her work clothes?
Thanks for sharing!

[lionbrand]

So hot story! Has James already fucked your GF or touched her pussy?

[Gary_evans77]

Super outcome! - More details would be great. How & when did they 1st fuck? Do they go bareback & does he cum inside her?

[neeryo]

She assured him that she wants it and that I want her to do it too.

Congratulations. Great to be cuckolded.

So, James knows that you know. Was he surprised? Has he asked further about you? Presumably he now knows that you know he is now fucking your girlfriend?

You indicated you have met him once. Any plans to meet him again soon, him as her lover, you as her cuckold? Any talk of you being able to watch them have sex?

Is James married?

Hopefully no office gossip yet?
Now they are fucking, James and your gf should redouble their precautions to keep this secret.

James does know me. He was a little surprised at the "situation" but he's more than happy with it now. I've met him a couple more times since my original post here. We are friendly and open about everything that's happening.

He's never been married and I haven't heard about any office gossip from either James or Sarah.

[neeryo]

What does your GF look like?
Where and when are they fucking?
She now wearing overtly sexy clothes to work, or sexy stockings or lingerie under her work clothes?
Thanks for sharing!

Sarah is 5'8'', slim figure, brunette with straight-ish shoulder length hair. She's a C cup and has the hips for a natural hourglass figure. She hasn't wearing anything too overtly sexy to work since it would draw unneeded attention, but she has worn lingerie under her clothes a couple times (at James's request which I LOVE). I know they've fucked in James's office, his car, and once at his house. It's all been hookup style sex, she hasn't slept overnight with him.