My SO has holidays for the next couple of weeks but I am self employed working from home with no,option to join her. I'm thinking of getting some role play going, I'm thinking of a boss/secretary scenario. It was one we used to do when we were young and very inexperienced so it was just a dress up session really. I'm thinking of making it a bit more edgy but beyond a few very ordinary ideas I wondered what else a 'Boss' should expect from his 'assistant', any thoughts?
Personally I think as the boss u should have ur assistant wait for u under your desk when u arrive first think in the morning, that's the first thing....
A good secretary should have a perfect telephone manner and the phone should never go unanswered. Can she keep her cool when things start getting hot?
Did this kind of thing for real a few years ago. We were just about to get into a bit of morning sex on a day off when my wife's colleague called to ask a few questions. Whilst she was chatting I slipped it in . Was great fun seeing her struggling to keep a straight face and hold a conversation with me merrily thrusting away!
I'm just assuming you're the boss, a bit of role reversal could be fun too.
The film secretary with Maggie Gyllenhaal should be some great inspiration for you. It's an awesome film. Some note scribing, going from one room to the other on all fours and bending over the desk for a spanking could definitely be fun in the role play!! Of course a BJ under the desk whilst on a conference call is the ultimate dream for me!
We are quite active roleplayers. We made this more fun by starting outside the bedroom . I took my "secretary" to lunch to take down some dictation. She did get some looks from people that know us as she wore spectacles ( the sexy type) and she doesnt normally wear glasses. Dress wise we are quite" neat "dressers normally and therefore smart office looking attire was'nt too different. to what we sometimes normally wear. We did this around a Friday dnner time when a lot of business type people would be frequenting the pub we normally go into and therefore we didnt stand out .The alcohol makes you more relaxed and and more at ease with your character roles .
I can't really suggest anything "edgy" as I dont know your boundaries . We went in the direction of the Secretary film as she made a lot of mistakes in the notes ! Impact play is within our boundaries .
I can only suggest that you keep everything within your defined boundaries and anything new discussed before hand .Just make sure you both know your safewords just in case something doesn't feel right and you have to abort the play . Play Safe ,Enjoy and have a Laugh !
For more material and ideas , just place "secretary" in the search button of some porn sites . This may give you some ideas. In fact its the only good use I get from looking at some porn sites . We always do this together .
First I would look back at what made your previous secretary role play fun and what you enjoyed. Take notes and add these into future play, but as for some pointers and certain things you can do to make it more real, you will need to find your boundaries. What does she like? If she’s into orders and slight degradation then a simple “to do” list left on the kitchen side in the morning would be perfect. Examples of chores/duties could be:
1. Address the boss as “sir” when spoken to
2. Always have a ponytail and dress neat
3. Give panties to sir when requested
4. Ensure office is tidy and papers are filed
5. Lunch to be made for sir at particular time
6. Any chore given by sir no matter how obscene to be completed
7. Toilet breaks to be requested and only allowed under sirs approval.
If you just want to dress up and have a quick and steamy session, then look into dirty talk for when you get down to it. Make sure you both dress the part so the “Boss” should be suited or at least smartly dressed with tie and trousers. The “secretary” should have a black dress with tights and black rimmed glasses with hair up in a bun or ponytail. Make sure during she only refers to you as sir or boss or Mr “last name”.
The roles can be as complex or simple as you like so have fun and see what makes her move in all the right ways ☺️
When we do the boss/secetary thing, we normally do spankings for poor performance, under desk blow jobs (boobs out of course), obsence instructions and requested toilet breaks etc. In this scenario, he's always in total control of my orgasms and I only get them when he's pleased with my performance. In addition, I'm not allowed to touch my intimate areas without him instructing me.
I always have a pony tail and I take out the hair tie during the session. The dark rimmed glasses are a must too.
It is about the only time he is in total control, and it's fun once in a while!
Maybe a bit clichéd in the end but she came into see me in very relaxed casual attire. I still where something smart casual even if working at home. I told her she needed to be better presented in my office.
She understood where I was talking this and gave a sorry look. I told her to remove her trousers which she did standing in front of me as I sat in my chair. Her panties were again not suitable in the eyes of this game. Removal of her shirt led to much the same disappointment.
Nudity was the only solution and she was complimented. The final compliance to office standards at this stage was that I needed to taste her but as we took this away from a husband and wife dynamic I refused to go down on her (she isn't into that anyway). She followed the instruction to place her hands between her legs and let me taste her fingers.
When I was satisfied I pulled her to me and turned her so she was sharing the seat but facing away from me, as if presenting to the rest of the room. I took hold of her breasts and forcefully massaged her between her legs, she cam in seconds and came hard (she does loves this type of position).
She then obliged by facing me and stroking me as I told her oral and penetration are reserved for my wife.
It was good fun and I'm looking to enforce some rules when in my office more routinely now.
Personal favourite is having my OH call me when he knows I’m in public and making really filthy talk whilst I have to maintain that I’m a good secretary and keep my telephone manner appropriate, sending filthy photos as a sex presentation too and having him rate me is a lot of fun!