Fantasy Roleplay Pictures

Ladies, post some sexy pictures of you dressed up in roleplaying outfits. School girls, teachers, secretaries, police, military, etc.

Gents, what's your favorite roleplaying outfit on a lady?

Here's mine taken this week Sexy secretary was my goal.

Nice pics Ms. Milani! My roleplay fantasy is similar outfit but I'm partial to the boss-employee fantasy. Mkst of my professional life I have had female bosses and I havefantasized about doing them in their office on top of their desk! They call me in asking why I sent out a wrong report or did something wrong and then act very upset and then tell me I have to fuck them right there on the spot to make up for it! Actually had a convo with one boss at a bar after I had moved to another job and we found out we had the same fantasy! Dammit, I wish I wasn't so hesitant and jumped on opportunities! Lol!

They call me in asking why I sent out a wrong report or did something wrong and then act very upset and then tell me I have to fuck them right there on the spot to make up for it! Actually had a convo with one boss at a bar after I had moved to another job and we found out we had the same fantasy! Dammit, I wish I wasn't so hesitant and jumped on opportunities! Lol! Originally Posted by moebeedick

After giving my two weeks notice at one of my old jobs I was able to check the boss taking advantage of employee fantasy off. I had a worker who although wasn't the hottest man had the most intense pheromones. He literally would stand behind a woman and she couldn't see, hear, or consciously smell him but she would just get horny. Every woman in my department felt the same way.

Before I left he came into my office to grab some paperwork. I didn't say anything except "I want you" and I pushed him up against a wall. I unzipped him and got on my knees....he lasted less than a minute. One of my better memories. Unfortunately I never got him to bend me over the desk before I left. The employee taking over for me started shadowing my every move and I couldn't get enough alone time.

After giving my two weeks notice at one of my old jobs I was able to check the boss taking advantage of employee fantasy off. I had a worker who although wasn't the hottest man had the most intense pheromones. He literally would stand behind a woman and she couldn't see, hear, or consciously smell him but she would just get horny. Every woman in my department felt the same way.

Before I left he came into my office to grab some paperwork. I didn't say anything except "I want you" and I pushed him up against a wall. I unzipped him and got on my knees....he lasted less than a minute. One of my better memories. Unfortunately I never got him to bend me over the desk before I left. The employee taking over for me started shadowing my every move and I couldn't get enough alone time. Originally Posted by SA Angel

Lol...gud one!

I always had a fucking the boss fantasy. I wanted to be his secretary that he could bend over his desk and fuck hard. Still a fantasy....

I enjoy the boss/secretary looks. But, even just a casual look can get me going when done right. As long as I get to undress who i am with I'm a happy man. I enjoy removing her clothes and kissing her body as I work them off.

I've had a few opportunities to mingle with some interns. There was one in particular where we would basically say hi, soon she would swing by my desk and say hello, which eventually evolved to hello/hug; hello/hug/cheek; hello/hug/cheek/peck; soon pecks made their way to corner of lips; to full lips, hands made their way to arms; elbows; back; back of neck; lower back; hips; butt; ribcage; and eventually we were saying HI, kiss, squeeze butt/breast and such. We actually planned to take a few hours off to go romp but she was transferred overseas and the opportunity vanished. However she is in town for holiday vacation... so we may try again.
Aside from that, it was interesting to watch people pair off during office parties, you could see in their eyes who had real feelings for their other co-workers. Naturally you had to also watch out for the office gossips who love to spread rumors.

Naturally you had to also watch out for the office gossips who love to spread rumors. Originally Posted by ugotme10

Consider yourself lucky that it didn't get past the Zipless Fuck stage. It's for good reason that people say "Don't get your meat where you get your bacon."

That is a really sexy outfit Ms. Milani.

That is a really sexy outfit Ms. Milani. Originally Posted by db1988

Thank you!

Still waiting to see some other sexy ladies in outfits.

But as of late, I've been developing a bit of a fetish for vinyl, as well as leather and latex.

SEXY!!! I love it!!!

But as of late, I've been developing a bit of a fetish for vinyl, as well as leather and latex.



Originally Posted by Lena Duvall

... Sexy secretary was my goal. Originally Posted by Ms. Milani

SUCCESS!!!!

Ms. Milani, black stockings and sexy high heels ... always been my weakness. Very nice!!

SUCCESS!!!! Originally Posted by JohnnyYanks

Yay! Thank you!

Ms. Milani, black stockings and sexy high heels ... always been my weakness. Very nice!! Originally Posted by Yoyoma

Thank you!