FabSwingers.com forum: Challenge Jane

By (user no longer on site) OP
over a year ago

So I suggested to Jane that it's been some time since I've set her any challenges, I have a good few ideas of challenges I could see her:

Sex with someone she know

Sex with a neighbour

Sex with someone much younger, and much older

Give a stranger a blow job

Invite four guys over

Go with me to a dogging spot and I strip her naked. I have sex with her, other guys watching can cum on her. They don't get to have sex, but she may choose to give them hand or oral relief.

Just some of the things I've been thinking about, I wonder what the collective may consider as good challenges.

For those that may be concerned, Jane doesn't do anything she doesn't want to do, there's no pressure on her to do any of these, but she does like a challenge

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By (user no longer on site)
over a year ago

Weekly shop with no knickers and short skirt to flash as many people as possible?

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By (user no longer on site) OP
over a year ago

"Weekly shop with no knickers and short skirt to flash as many people as possible?"

I think that would challenge her more than meeting a stranger, public is something she really hasn't shown any interest in, but is quite rightly a challenge. This is why a dogging meet would be really hard for her, but I know she'd do it if I challenged her.

I'd like to say why the challenges come about, but I'll be brief. It started when we first met, I challenged her understanding of sexuality from the get go, and sometimes she feels she needs encouragement in the form of a challenge (she's a fitness instructor so is well versed in challenging herself)

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By *ere2help82Man
over a year ago

Bromsgrove

Looking at challenge 2 I feel I might have to look at becoming one of your neighbours!

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By (user no longer on site) OP
over a year ago

"Looking at challenge 2 I feel I might have to look at becoming one of your neighbours!

She would be nervous as hell with someone she knows or a neighbour, she really wouldn't know where to start, so I'll coach her with the kind of signals a guy would pick up on. I know she fancies one of her neighbours, and he's single so it fits with her priority of not having sex with married men unless as a couple.

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By (user no longer on site)
over a year ago

She go to clubs much? Could be nice and dark for a handjob in the shadows

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By *enninemarkMan
over a year ago

huddersfield/manchester

Stocking with the public thing. She could wear a just above knee skirt or dress with seamed sheer stockings underneath. On your instruction (which could be a remote vibe inserted before you went out) she is to start 'accidentily' flashing her stocking tops. The fact she is wearing something not too slutty, makes it look more of an accident to onlookers.

You could continue the flashing bit by setting her tasks like picking something up to show more. Making sure a waiter or barman has seen plenty, getting her to order something whilst to turn up the vibe etc.

Finally, after much teasing, an identified possible target male is the one she is told to go and give a slip of paper to with some contact details. She does this by walking up to him, saying "I have something to give to you." At which point she hitches her skirt and takes the slip of paper from under her stocking top and tells him to be in touch soon!

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By *iveshowcoupleCouple
over a year ago

glasgow

Take her to a swingers club and challenge her to walk through it naked and offer the first guy she fancies a blow job in front of everyone.

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