Roleplay with an escort

[TBC4141]

I've always had the urge to try a roleplay on a visit, but have never gone through with it. I guess I've struggled with the confidence to do it and also the right roleplay. Just wondering really is it something other do actually do, how have you arranged it with the girl, did the girl get into it or was it awkward and what sort of scenarios have you played out. May help me with my quest.

[Mrcambridge69]

I’ve had a few roleplay meets. Usually when looking for a suitable SP I look to see if roleplay is on their likes list. When confirming the booking I state I’m after role play and what I would like to do. To date they’ve always agreed. Role plays I’ve engaged in include; Nurse, yoga instructor, secretary and a Marvel dress up for both of us (Review coming on that shortly). Whatever you ask for they’ve heard it before and most will go with the flow or do as you instruct.

[RedKettle]

There are a few threads on here discussing different role play scenarios that you might find helpful.

I have done quite a few of these.  You can search on AW using the roleplay likes to try and find WGs who do them but from experience you will find that a lot just tick that box and are not really into it.  You really need to find one who mentions it in the narrative on the profile - or of course where a UKP review mentions a role play. 

Most of mine recently have been with regulars, although in the past I have done it on a first meeting which adds some nice tension to it.

I tend to first ask if they would consider a role play and if yes then I outline the basic scenario.  I always stress that I am not expecting them to learn any lines, it is understanding the overall idea and then respond to what each other says.

If with a regular I usually stress that I will not be expecting anything to happen that we have not already done between us.  If there is to be anything else, such as a slap or verbal abuse I make that clear and establish she is ok with it. 

Depending on the scenario I offer the chance to have a safeword but with regulars who know me frankly they are pretty confident it will not get out of hand and if they were uncomfortable they would let me know.

I will be communicating the final detail by email and I always say that if they are uncomfortable we can instead just have a normal meeting.

My aim is to make them feel very comfortable with it and happy to take part.  They are under no pressure and know that we can just have the usual fun if they choose.  I think this has paid off and I have have a number of very enjoyable role plays over the years.

[jimbobted]

Have done a few roleplays, mostly as a way to set the scene as it were for a bondage/BDSM meet. But sort of gone off them latterly and just get stuck straight into the action.
Plenty of girls offer the service.

[signy]

At least 90% of my meets include some degree of roleplay, from short and simple to set the scene, through to relatively long and forming a significant part of the experience. I also enjoy dressing-up and roleplay in non-sexual social activities. (Rightly or wrongly, I consider myself something of an expert!). Here are some basic tips for beginners.

Start with something short and simple, then if it's not working, you can forget it and transition to a normal meeting with little lost.

Choose something that the SP explicitly offers in her profile (schoolgirl, secretary, neighbour, etc. are common), so that it is a role she has played before and knows what is expected. Avoid escorts that include roleplay in their likes list, but give no idea as to what roles thay enjoy.

Include the scenario in an email/text/whatever, but keep it short (3-4 sentences). A complicated plot is not desirable and no-one wants to learn lines.

Get her to wear a costume, even if it is easy like for an office roleplay, and wear one yourself, even if just putting on a tie or similar. This helps get you into playing a different character.

Don't worry if it doesn't work; this happens. We have all been in roleplays where one or both parties have collapsed in fits of giggles due to the silliness of it all. Take a breath and pick it up again, or forget it and move on to sex. As ever, you are there to have a good time. It is not a chore to be endured. If necessary, change tack and do what you prefer instead.

[Adoniron]

It's worth doing if you have the confidence to follow it through and more importantly if the girl is good at it and enjoys it. Look for a girl who advertises the service and find out how into it she is before booking.

[TBC4141]

Very much appreciate all the responses, thank you

[Dr Talueng]

About 10 years ago I booked an SP down in Berkshire, and she said she had various outfits she could wear for me ... all the 'usual' ones - secretary, nurse, fitness instructor, and so on. I chose the schoolgirl outfit, and she immediately said that she wanted to do some kind of roleplay in that outfit. I was okay with that ... seems she already had the roleplay worked out in her head.
On the drive there I was trying to think about how *I* wanted it to go; what I'd say, what we'd do. I thought about telling her off for not doing her homework, and we'd take it from there. She had other ideas, and pretty much took control as soon as we started. Seems she was about to be expelled for various things; I asked her to show me what she'd been doing, and then to demonstrate some of them. 90 minutes of debauchery followed!

[myothernameis]

I've always had the urge to try a roleplay on a visit, but have never gone through with it.

Ask the escort, is there any type of roleplay she wont do, and if she says, she will do any type of roleplay.   There some types of roleplay, which border on the lines.

Like school girl roleplay, which I have known some escorts in Glasgow to do, and some do it very well, maybe to well.  There used to be an escort on AW, around 10 yrs back, had rape down as role play.  I always considered this to be a bad idea on her part, and in general with your booking she would leave the front door open

[myothernameis]

I chose the schoolgirl outfit,

Many years back, I had asked an escort for roleplay, and a schoolgirl roleplay, her reply, she found me vile and disgusting that I would suggest this.  Dont think she had the real concept of what roleplay is about, and would say my suggestion was pretty tame, and sure she would have got a lot worse reply and suggestions

[oddson1970]

Many years back, I had asked an escort for roleplay, and a schoolgirl roleplay, her reply, she found me vile and disgusting that I would suggest this.  Dont think she had the real concept of what roleplay is about, and would say my suggestion was pretty tame, and sure she would have got a lot worse reply and suggestions

l don't think there is anything wrong with the schoolgirl role play as long as the SP is not very young looking.....the lines can get a bit blurred if she is.lts all about having a bit of fun and l think its fine if both parties are comfortable with it.

[mr.bluesky]

l don't think there is anything wrong with the schoolgirl role play as long as the SP is not very young looking.....the lines can get a bit blurred if she is.lts all about having a bit of fun and l think its fine if both parties are comfortable with it.

Never felt the urge for role playing and having a 30+ something service provider dress up as a school girl doesn't do anything for me. They tend to look a bit ridiculous rather than sexy 🙄. A sexy secretary maybe but as for nurses uniform or police woman's uniform thanks but no thanks. I'd rather them dress in some sexy loungerie ( not that it stays on for long enough  )

[Thephoenix]

I prefer my SP experience to be as natural as possible.
Anything fake including fake boobs, lips, dirty talk, orgasm, role plays, gfe etc, just puts me off.

[petermisc]

Many SPs offer uniforms, but struggle with role-play.  You need an SP who is genuinely into role-play.  And you need to give her an outline of what you are after, don't just expect that if you ask for a nurse roleplay for example that she has the same kind of scenario in mind as you.

[stampjones]

Used to be into roleplay many years ago but kind of went off it after a while. As has been said its important to get a girl who’s into it. Either read reviews or trial and error as it was when I did it. The other thing is you need to commit. With a good WG she’ll reflect back what you put into it so if you’re half arsed about it she will be too. Decide on your scenario and go for it. Stay in character. You can follow her lead or not but stay in the moment. If there are certain things you want to happen, discuss with the WG beforehand.

[Mkhelen]

Please make sure you text or email the lady the request first and get a confirmation  a definite yes

Do not turn up with a piece of paper with it written on as thir eats into your time together and doesn't allow the lady time to prep your scenerio


or say surprise me you know best could be
Sloppy blowjob cock worship or a swift kick to the Nutts?? Many variables we offer we want details

It's very difficult for a lady to know at what degree of intensity you want it at

[pythondan]

https://www.ukpunting.com/index.php?topic=260590.0

Link above is for a review of a roleplay that I did with a girl a few years ago. The role she played was an applicant to be my PA and, being in a hotel, it was believable.

The SP has now disappeared after a brief period in which she offered bareback  - not even hinted at on the occasions that I saw her but I would not return because of it if she were to come out of retirement.

[Stevelondon]

I enjoy the occasional roleplay. As has been said. It’s important you get the right SP to do the job. Bit difficult with someone you have not met before who might just not be into stuff you have in mind.
I would also say it’s probably best not to over complicate things. As MKH. Says. Too many variables are difficult to remember.

Had a great patient/nurse thing once upon a time.
Wish that hospital was still open 😂

[albert56]

Roleplay can be a lot of fun. But as many above have said it needs the right SP. A lot seem to put this down as a service offered without any real ability for it or experience in it....

[Jayj]

Something I’ve enjoyed in the past but don’t really bother now.

More interestingly I had an SP friend who roped me in on a number of these usually as an outcall quite often very elaborate role play scenarios usually cuckold husband coming home, on a couple of occasions they went on for days in advance of the meeting to build the reality, at the other end of the scale she would have me call mid meet put me on speakerphone  pretending to be the SP’s husband, boss, father while her punter was banging away 😂

[nbarnes]

I've done a couple of French maid roleplays - pretty sexy

The 2nd one, my regular just put the costume on unsolicited, and asked if I wanted to play 'spank the maid' - that was a lot of fun.

Roleplay is a weird one, its amazing when it comes off, and makes you both feel ridiculous when it doesn't! (hopefully you should be able to laugh about it!)

I suppose you could call dom\sub roleplay as well - I love both, but dom generally means no sex, and hot subs (that don't cost a queens ransom) are very difficult to find these days.

[signy]

I suppose you could call dom\sub roleplay as well ...

If you are going down that line, then virtually every meeting is a roleplay. Certainly the SP will be playing a role, and often the client will be as well. Punting is not the place to look for truth and honesty, even if it isn't in a bad way, the whole experience is a morass of half-truths and embellishments.

[post impressionist]

I guess I've struggled with the confidence to do it and also the right roleplay.

You have to want to play the part, whatever it is.  If you go into it feeling shy or embarrassed it won't work. Same with the SP; they've got to be really up for it (sometimes taking the lead).

So, 1. find the right SP (not just someone who mentions 'role-play'); 2. work out a role-play that you really want to live.  If you can't get both it's not really going to come off.

BTW I've found pornstars are enthusiastic role-players - could be pricey though.

[Stevelondon]

Roleplay can be a lot of fun. But as many above have said it needs the right SP. A lot seem to put this down as a service offered without any real ability for it or experience in it....

Yep I agree. Roleplay to some might just be a case of wearing a schoolgirl outfit or nurse etc and have nothing to do roleplays whatsoever.

[senordingdongs]

Did a teacher roleplay with a lady 20+ years my senior recently. Glasses, pencil skirt and busty blouse. She just started it. The story was I’d missed a top grade by 1 mark and had to fuck her up the arse to gain it back.

And yes I certainly worked hard to get it back lol

[Home Alone]

Did a teacher roleplay with a lady 20+ years my senior recently. Glasses, pencil skirt and busty blouse. She just started it. The story was I’d missed a top grade by 1 mark and had to fuck her up the arse to gain it back.

And yes I certainly worked hard to get it back lol

And will you be reviewing this paragon? Please?

There are some - well, at least one, to my certain knowledge!  - of us, who might fancy being Headmaster of her school - I guess I may well be old enough - who didn't approve of her way of awarding marks, and wanted to show his displeasure.   

[senordingdongs]

And will you be reviewing this paragon? Please?

There are some - well, at least one, to my certain knowledge!  - of us, who might fancy being Headmaster of her school - I guess I may well be old enough - who didn't approve of her way of awarding marks, and wanted to show his displeasure.   

She wasn’t a WG she’s a divorced lady I help out when she needs something doing

[myothernameis]

Anyone tried the housewife role play 

[RedKettle]

Anyone tried the housewife role play 

Most days

[Keema]

Not done them for a long time, but one in particular stands out - asked her to be a sex kitten, a real feline kitten. She had a tail plug, I brought cream, laser pen, cat collar and ears, all communication from her was in purrs and miaows.  All great fun from a very playful girl - she even hissed at me when I pulled out her plug a bit too quickly at the end!

[Bonker]

Better ideas than some you could have had...litter tray, a live mouse

[akauya]

The only time I tried role play was with a lover and I couldn't stop laughing as I felt completely ridiculous. I had to take it seriously for her though as she was well into it.

Based on that experience I don't think I'd pay to role play.

Hats off to you guys who are into it. I just feel too self conscious doing that.

[puntingking]

l don't think there is anything wrong with the schoolgirl role play as long as the SP is not very young looking.....the lines can get a bit blurred if she is.lts all about having a bit of fun and l think its fine if both parties are comfortable with it.

As long as both of participants are both consentual adults over the legal age it doesn't matter what role-playing both participants decides to do.


 

[Home Alone]

She wasn’t a WG she’s a divorced lady I help out when she needs something doing

Oh, bugger!!

Well, please tell her from me that, although I've never met her - and likely never will - I think she's missed her true vocation! 

[Nagilum]

I've always had the urge to try a roleplay on a visit, but have never gone through with it. I guess I've struggled with the confidence to do it and also the right roleplay. Just wondering really is it something other do actually do, how have you arranged it with the girl, did the girl get into it or was it awkward and what sort of scenarios have you played out. May help me with my quest.

You may feel more confident if you have seen her before. Try and see the WG a couple times, see if you feel comfortable with her and then ask for your fantasy to be played out.

[Nagilum]

Did a teacher roleplay with a lady 20+ years my senior recently. Glasses, pencil skirt and busty blouse. She just started it. The story was I’d missed a top grade by 1 mark and had to fuck her up the arse to gain it back.

And yes I certainly worked hard to get it back lol

You've been on Porn Hub again, havent you! 

[Bonker]

I've tried a few but the girls overdid the acting.  So much so that it felt like a pantomime.

Oh no it didn't. It's behind you. Well take it out you bugger.
(That's enough,  Ed)

[Roman77]

I've experienced role play in my younger days on a couple of occasions. The old secretary and teacher scenario. Both times it ended up with us laughing  .
We weren't winning any awards for our acting. In a strange way it helped us relax making the meeting more enjoyable. Think the problem is role play and wearing outfits are two different things. Personally I find nurses, schoolgirl etc. a turn off (yes I know I'm strange). I much prefer classy lingerie on a woman.

[signy]

We weren't winning any awards for our acting. In a strange way it helped us relax making the meeting more enjoyable. Think the problem is role play and wearing outfits are two different things. Personally I find nurses, schoolgirl etc. a turn off (yes I know I'm strange). I much prefer classy lingerie on a woman.

Good point. This can still be a good place to start if you fancy roleplay. You know how you want a woman dressed, so work from there...

The lingerie shop and the pervy assistant. May I measure/help you madam?

The classic travelling salesman. (Do men travelling in women's underwear still exist, or did they ever in reality?).

The helpful neighbour rescuing a woman trapped in her bedroom by a dodgy lock; so, so grateful, especially to a man handy with a tool.

[Home Alone]

I've experienced role play in my younger days on a couple of occasions. The old secretary and teacher scenario. Both times it ended up with us laughing  .
We weren't winning any awards for our acting. In a strange way it helped us relax making the meeting more enjoyable. Think the problem is role play and wearing outfits are two different things. Personally I find nurses, schoolgirl etc. a turn off (yes I know I'm strange). I much prefer classy lingerie on a woman.

Surely, there's nothing to stop her wearing classy lingerie under her nurse's uniform??    For me, that would be a win-win situation.

[jimbobted]

I've experienced role play in my younger days on a couple of occasions. The old secretary and teacher scenario. Both times it ended up with us laughing  .
We weren't winning any awards for our acting. In a strange way it helped us relax making the meeting more enjoyable. Think the problem is role play and wearing outfits are two different things. Personally I find nurses, schoolgirl etc. a turn off (yes I know I'm strange). I much prefer classy lingerie on a woman.

I have only done roleplay as part of BDSM stuff. For a vanilla punt I think it would feel a bit silly and superfluous. Even with BDSM meets sometimes the roleplay is quickly forgotten.

[Stevelondon]

I have only done roleplay as part of BDSM stuff. For a vanilla punt I think it would feel a bit silly and superfluous. Even with BDSM meets sometimes the roleplay is quickly forgotten.

Had some memorable roleplay punts outside of the BDSM field. It’s the knack of finding the SP who understands what you are wanting and can play the role etc.
As has been said. Sometimes the actual scenario gets problems simply because the punter stops playing his part. 😂

It wasn’t exactly a BDSM scene I was in but it bordered close to it. Strict therapist who was teaching me the ways to pleasure a woman using my tongue and toys.
She had me in a chastity cage to ensure I understood that sex was not on offer.
I got sent away completely frustrated and told to return the following day.
Still didn’t get sex but at least I was unlocked and relieved 😂

Don’t ask. It was twenty years ago and she is definitely not around anymore. 😂

[puntingking]

The best role play for me is where the wg acts as my wife or girlfriend with all the good bits. 

[Watts.E.Dunn]

The best role play for me is where the wg acts as my wife or girlfriend with all the good bits. 

And they, the good bits are;?...

[JimmySW]

A girl I saw some time ago had schoolgirl uniform listed so I asked for that - when I turned up she actually looked like a regular schoolgirl! I was expecting a slutty look, short skirt, shirt buttons mostly undone etc - I won't make that mistake again as it really didn't do anything for me!

[puntingking]

A girl I saw some time ago had schoolgirl uniform listed so I asked for that - when I turned up she actually looked like a regular schoolgirl! I was expecting a slutty look, short skirt, shirt buttons mostly undone etc - I won't make that mistake again as it really didn't do anything for me!

maybe next time be clear - state that you want her to dress up as a "slutty school girl". she obviously thought you wanted a regular schoolgirl look.

i went to a wg house once and she had like 10 different types of school girl outfits (no kidding)     

[Jindybandy]

This would probably cost a pretty penny (I assume), but you’d think some of the ‘porn stars who escort’ lot would be good at “acting” and might offer that service. Anyone ever done that level of role play with a pornstar WG and effectively acted out a porn movie?

[Mr_Shins]

I did "roleplay" in fetish/BDSM kind of meets. Otherwise it has simply been getting the escort to dress in a particular way - it used to frequently be office-wear due to when I was working in offices and seeing lots of women about.

Outfits, not costumes. None of the women in the office wear clothes from a costume shop. Nor do nurses get their outfits there. Maybe some men are attracted to such outfits, and I guess if it's a type of uniform not accessible to the public (e.g. police officer) then they may need to buy parts of it from a costume shop, but that's all really. "Oh but that's not sexy...". But I didn't ask you to dress as a porn-star I asked you to dress as a (nurse / police officer / office worker) because I find that sexy...

To me roleplay is playing out some kind of fantasy that is taboo in real life (thus approaching women in your real office to do these things would be sexual harassment).

[jimbobted]

To me roleplay is playing out some kind of fantasy that is taboo in real life (thus approaching women in your real office to do these things would be sexual harassment).

Exactly this. One of my favourites in a BDSM meet is for the girl to be my boss and play an utter bitch. I tell her I'm quitting and she's then prepared to do anything to make me change my mind.
Another good one is I'm recruiting for an "office slut" and she's turned up for interview and practical assessment. Stuff that could never happen in real life.

[puntingking]

I quite like the first role play idea