My co-workers would be surprised to know that...

Strapon fantasy

... I fantasise about two of them. And for each of them the fantasy is the same.

We're alone in a room together, working on a project together. We're laughing, talking, joking .... until at some point I feel her hand on my knee.

I lean towards her. We kiss. Her hand works upward. And I start touching her too, stroking her knee, her thighs.

Finally her hand is on my cock. She is masturbating me, pulling open my fly. And I (they both favour trousers over skirts) start doing the same to her.

Only to feel something rock-hard beneath her trousers. I pull away in shock as I discover she is wearing a strap-on.

'Don't act so surprised.' she smiles. 'I know your internet history. I know what you like.'

There is no point denying it. Slowly she pulls down my trousers, my underwear. And then, looking me in the eye the whole time, she fucks me up the ass with her strapon - seeing how much I love it, how right she was about what I wanted.

When she's done with me she lets me cum in her underwear, which she leaves behind. And tells me that if I don't do her sexual bidding whenever I want from now on, she'll tell everyone to take a look at my porn files ....
 
That I blow hubby in his office...actually...that probably wouldn't surprise them, lol
 
That the person they know as a normal/boring married senior manager on the verge of middle age has a wild past as an utter slut, was once the "toilet" at a piss-play party, used to be a sub for a Master, has stripped naked and masturbated in my current office while alone in the building and is currently having an affair with an old friend who likes to cum up my arse on a regular basis.

I don't have any co-workers, but this post was enough to make me join this thread. But it looks like Miss_Scarlett has left the building. . . a pity.
 
I had a similar fantasy which thanks to my wife was able to actually act upon I guy I worked with was a self confessed 38 year old virgin. He was a short stocky guy and rather nerdy looking. I am fairly tall with a generally naturally muscular physique. I however have a very tiny penis. My wife and I had engaged in threesomes before with other guys who had very superior endowment to mine. Long story short we convinced him to engage with us. He was a bit trepidatious at first but when he saw How pathetic my little cock was flaccid 1.5" compared to his - like a large cucumber pickle to a baby gherkin he felt more confident when he saw his erect penis compared to mine was easily twice my size he looked pretty prideful The final coue was when I fucked my wife and came in about 5 seconds and she looked bored then he fucked her for at least 10 minutes and gave her multiple orgasms. After a while and some foreplay he recovered and fucked her again while I just watched and pulled on my far far inferior cock. Seeing this outwardly beta male best me an outwardly alpha guy in pleasuring my wife was fantastically arousing.
That's hot, I'm retired and so is this guy, but I still picture him fucking my wife. I think of him calling her a dirty whore, and me his cum eating faggot cuckold. I think of him really coming out of his shell. His wife doesn't like sex, but he degrades my wife for being a old lose slut for him.
 
My coworkers would be surprised to know that a former coworker of ours would sometimes bone me as I was face forward atop my desk. ("Really?!? Him? And HER?!? Are you serious?)

Ha! I recently had a female coworker bring him up in conversation as someone she found hot. I feigned barely noticing him.
 
When I shower I like to have one of my Aneros's in my ass while doing so and sometimes use the wall to push it in deeper.
 
They'd be surprised to know that the unassuming older woman that comes to my work, the one who looks like a retired school teacher or librarian, the one who looks looks and acts like she's a good girl, the one who stops to visit me and hangs around for quite a while is driving me out of my fucking mind imagining the things I'd like to do to her.

I feel a strong attraction and I'm pretty sure she does too but I'm too chicken to try and cross that line:(
 
They'd be surprised to know that the unassuming older woman that comes to my work, the one who looks like a retired school teacher or librarian, the one who looks looks and acts like she's a good girl, the one who stops to visit me and hangs around for quite a while is driving me out of my fucking mind imagining the things I'd like to do to her.

I feel a strong attraction and I'm pretty sure she does too but I'm too chicken to try and cross that line:(

You have to find a way to try. No risk, no reward.

Good luck. :)
 
I cum late

We have a weekly sales meeting on Wednesday. I work with a lot of non-office based employees so it's standing room only most weeks. I always show up late to the meeting so I can stand in the back and check out the ladies sweet asses.

3 gals in their late 30's and early 40's are fitness freaks. Two of the ladies rock nice C-cup boob jobs. All take pride in their good looks and flaunt it to acceptable levels in the work place. I especially love it they stand in front of me. I can check out the lingerie discreetly. The scents they wear make me weak.

Many times after the meeting I head home at lunch and pair them up in my mind.
 
They'd be surprised to know that the unassuming older woman that comes to my work, the one who looks like a retired school teacher or librarian, the one who looks looks and acts like she's a good girl, the one who stops to visit me and hangs around for quite a while is driving me out of my fucking mind imagining the things I'd like to do to her.

I feel a strong attraction and I'm pretty sure she does too but I'm too chicken to try and cross that line:(

I would love to know how this works out
 
I agree, it is very scary taking the first step, and it is hard to be sure we have read the signs correctly

Can you take it out of a work environment? Maybe suggest a coffee, and see if she bites?

Life is short and if you feel attracted but don’t do anything and miss the opportunity how would that feel?

If she is straight, she would probably just be flattered that you found her attractive

:kiss:

They'd be surprised to know that the unassuming older woman that comes to my work, the one who looks like a retired school teacher or librarian, the one who looks looks and acts like she's a good girl, the one who stops to visit me and hangs around for quite a while is driving me out of my fucking mind imagining the things I'd like to do to her.

I feel a strong attraction and I'm pretty sure she does too but I'm too chicken to try and cross that line:(
 
I agree, it is very scary taking the first step, and it is hard to be sure we have read the signs correctly

Thanks for the encouragement

This above is what I'm talking about. My instincts tell me she goes out of her way to be around me but on the other hand she could be just a nice woman who likes me but not in the horny perverted way my mind likes to imagine lol

I would be beyond embarrassed if I made a move and it were the latter
 
But ... for me the fear and ‘shall I, shan’t I’ dilemma used to make me stay inside my shell

A single ‘Go for it’ moment that led to amazing, life changing, great things has made me regret all those wasted opportunities

Fantasies are nice, fear of rejection is scary, but fantasies realised can be the start of something beyond your dreams




Thanks for the encouragement

This above is what I'm talking about. My instincts tell me she goes out of her way to be around me but on the other hand she could be just a nice woman who likes me but not in the horny perverted way my mind likes to imagine lol

I would be beyond embarrassed if I made a move and it were the latter
 
I am reserved at work so, they would be surprised that I am an exhibitionist at heart (not a flasher). I am my wife's "slut". I am hers and I will do absolutely anything she wants, any time anywhere and she can do anything she wants, to me or with me. I am into CFNM.
 
It's the traditional dating dance

They'd be surprised to know that the unassuming older woman that comes to my work, the one who looks like a retired school teacher or librarian, the one who looks looks and acts like she's a good girl, the one who stops to visit me and hangs around for quite a while is driving me out of my fucking mind imagining the things I'd like to do to her.

I feel a strong attraction and I'm pretty sure she does too but I'm too chicken to try and cross that line:(
  • Take her off site (coffee, shopping, trip to the library looking for materials).
  • Talk to her, looking for some activity or way to spend more time with her.
  • Invite her to lunch at your place & share any hobbies, interests, music, nick-knacks, collections, etc.
Put yourself on display.
  • Mirror what she wears. If she wears a blouse with one button open, wear yours with 2 buttons open. Complement clothing that makes her look good.
  • Focus on her, keep making eye contact, smile, lean forward, play with your hair, adopting an open body posture (e.g., arms away from the body).
  • Send the usual signals. Palming (displaying an open wrist and palm), self-touching (such as a breast graze), or exposing the neck, perhaps by leaning back or canting the head. Let her see you looking at her body.
  • Coax her to touch you. Put your hand on the table where she can reach it. Sit beside her, lean toward her. Offer your arms to hug her when you meet or part. See if she will let you into her personal space.
As she responds, step things up in subsequent meetings.
  • Have a drink together. Go someplace where you can ask her to dance. Even if she doesn't, drinks will still loosen things up
  • Say how comfortable you feel with/beside her. Tell her that you are affection starved and welcome all you can get.
  • Put you lips on her neck as you small her hair then back off and complement her scent. Stroke her face, hold her hand a bit.
  • Show your arousal. Wear something that shows headlights and flush. Tell her you would enjoy being with her.
  • Under the table, place her hand on your leg. Move it towards your crotch and then put your hand on her leg.
  • Put her hands on your chest and kiss her.
 
Oh My God... There would be so many...
So let's do the kinky ones:
  1. I regularly wear women's underwear
  2. I sometimes wear pantyhose under my business suit
  3. I dream about one of my colleagues dominating me
Not too kinky ones:
  1. I have horrible crush on one of my students
  2. I have slept with one of my colleagues
and the rest... As I said, would be too long including that I read Lit at work :D
 
  • Take her off site (coffee, shopping, trip to the library looking for materials).
  • Talk to her, looking for some activity or way to spend more time with her.
  • Invite her to lunch at your place & share any hobbies, interests, music, nick-knacks, collections, etc.
Put yourself on display.
  • Mirror what she wears. If she wears a blouse with one button open, wear yours with 2 buttons open. Complement clothing that makes her look good.
  • Focus on her, keep making eye contact, smile, lean forward, play with your hair, adopting an open body posture (e.g., arms away from the body).
  • Send the usual signals. Palming (displaying an open wrist and palm), self-touching (such as a breast graze), or exposing the neck, perhaps by leaning back or canting the head. Let her see you looking at her body.
  • Coax her to touch you. Put your hand on the table where she can reach it. Sit beside her, lean toward her. Offer your arms to hug her when you meet or part. See if she will let you into her personal space.
As she responds, step things up in subsequent meetings.
  • Have a drink together. Go someplace where you can ask her to dance. Even if she doesn't, drinks will still loosen things up
  • Say how comfortable you feel with/beside her. Tell her that you are affection starved and welcome all you can get.
  • Put you lips on her neck as you small her hair then back off and complement her scent. Stroke her face, hold her hand a bit.
  • Show your arousal. Wear something that shows headlights and flush. Tell her you would enjoy being with her.
  • Under the table, place her hand on your leg. Move it towards your crotch and then put your hand on her leg.
  • Put her hands on your chest and kiss her.

Uummm! HLTW , the OP, is a bloke!

Good advice though for a woman.
 
Wow, where were you whenI was 18, life would have been so much easier :D

Genuinely great advice, and as you say, no different to a heterosexual dating dance

  • Take her off site (coffee, shopping, trip to the library looking for materials).
  • Talk to her, looking for some activity or way to spend more time with her.
  • Invite her to lunch at your place & share any hobbies, interests, music, nick-knacks, collections, etc.
Put yourself on display.
  • Mirror what she wears. If she wears a blouse with one button open, wear yours with 2 buttons open. Complement clothing that makes her look good.
  • Focus on her, keep making eye contact, smile, lean forward, play with your hair, adopting an open body posture (e.g., arms away from the body).
  • Send the usual signals. Palming (displaying an open wrist and palm), self-touching (such as a breast graze), or exposing the neck, perhaps by leaning back or canting the head. Let her see you looking at her body.
  • Coax her to touch you. Put your hand on the table where she can reach it. Sit beside her, lean toward her. Offer your arms to hug her when you meet or part. See if she will let you into her personal space.
As she responds, step things up in subsequent meetings.
  • Have a drink together. Go someplace where you can ask her to dance. Even if she doesn't, drinks will still loosen things up
  • Say how comfortable you feel with/beside her. Tell her that you are affection starved and welcome all you can get.
  • Put you lips on her neck as you small her hair then back off and complement her scent. Stroke her face, hold her hand a bit.
  • Show your arousal. Wear something that shows headlights and flush. Tell her you would enjoy being with her.
  • Under the table, place her hand on your leg. Move it towards your crotch and then put your hand on her leg.
  • Put her hands on your chest and kiss her.
 
As it’s Lit, some of the fun is about being free to talk about stuff we would never do in public forums, so ...

Oh My God... There would be so many...
So let's do the kinky ones:
  1. I regularly wear women's underwear

    Me too
  2. I sometimes wear pantyhose under my business suit

    And again, me too
  3. I dream about one of my colleagues dominating me

    Interesting, who? M or F?
Not too kinky ones:
  1. I have horrible crush on one of my students

    Again, in the modern world know you wouldn’t be able to act on this, but what about them drives you crazy?
  2. I have slept with one of my colleagues

    Only once? How did it happen? What happened afterwards?

    Not looking to pry, or ‘hit on you’, just fun sharing experiences
and the rest... As I said, would be too long including that I read Lit at work :D
 
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