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Old 12-02-2021, 09:04 AM   #1
Imgettinghard
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Default 25F & 26M Trip to Boston Looking for Some Dares!

My girlfriend and I are headed to Boston next weekend (from Friday the 10th to Monday the 13th) we are flying there and staying in a hotel. We heard it was pretty cool there close to Christmas! We will mostly be getting around by Uber and public transportation.

She isn’t as daring as me but we think it would be fun to push some limits! Do you have any ideas? Some things I’ve thought about trying: panties with a vibe in them with a remote control that I control while we are out to dinner. Maybe going to get ice from the ice machine wearing only a long shirt for her…. Umm heading to a local sex shop to get new toys… using all the objects(bed, chairs, couch etc) in the room to try new positions…

Yeah as you can tell we need some suggestions! We think it would be fun to get some feedback and we’ll write reports about everything we do!

We don’t want to involve anyone else and like we said she is pretty timid.
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Likes: being nude where I shouldn’t be, and doing something naughty that no one knows about. I like having deadlines of tasks that need to be done or when I do X (some sort of daily thing) I have do to Y. Most anything I haven’t tried, exhibitionism, pictures, videos, predicaments, anal play, light CBT, cross dressing.
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Old 12-02-2021, 09:42 AM   #2
DutchGayDom
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While at the airport swap underwear
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Old 12-02-2021, 10:49 AM   #3
Imgettinghard
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Oh this could be exciting. We’d have to plan accordingly because typically she wears leggings when we travel and she never wears underwear with leggings!
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25/m, straight, athletic and outgoing.

Kik is: imgettinghard

Likes: being nude where I shouldn’t be, and doing something naughty that no one knows about. I like having deadlines of tasks that need to be done or when I do X (some sort of daily thing) I have do to Y. Most anything I haven’t tried, exhibitionism, pictures, videos, predicaments, anal play, light CBT, cross dressing.
Dislikes: cum play/eating, pee... I like to push these!
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Old 12-02-2021, 03:13 PM   #4
tzzzr
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How about working on her timidness a little bit?

Leave the curtains open in the hotel at all times. No covering up for either of you. This is especially fun if it's a highrise with big windows downtown.

Do something to determine which of you has to stand in the window naked either until seen or for five minutes.

Sex in front of the window may max her out but see how far she will go.
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Old 12-03-2021, 04:15 PM   #5
Creamed My Jeans
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Get an uber to the sex shop and tell the driver to wait till you come out of the shop.
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Old 12-04-2021, 04:42 PM   #6
Imgettinghard
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Quote:
Originally Posted by tzzzr View Post
How about working on her timidness a little bit?

Leave the curtains open in the hotel at all times. No covering up for either of you. This is especially fun if it's a highrise with big windows downtown.

Do something to determine which of you has to stand in the window naked either until seen or for five minutes.

Sex in front of the window may max her out but see how far she will go.
Windows open it is. I don’t think that will be too big of a deal. And standing there I can maybe convince her in to! We’ll see about sex in the window.
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25/m, straight, athletic and outgoing.

Kik is: imgettinghard

Likes: being nude where I shouldn’t be, and doing something naughty that no one knows about. I like having deadlines of tasks that need to be done or when I do X (some sort of daily thing) I have do to Y. Most anything I haven’t tried, exhibitionism, pictures, videos, predicaments, anal play, light CBT, cross dressing.
Dislikes: cum play/eating, pee... I like to push these!
Limits: family, friends, permanent.
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Old 12-04-2021, 04:43 PM   #7
Imgettinghard
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Quote:
Originally Posted by Creamed My Jeans View Post
Get an uber to the sex shop and tell the driver to wait till you come out of the shop.
Lol that is hilarious! If we have time to fit it in to the schedule we’ll do this.
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25/m, straight, athletic and outgoing.

Kik is: imgettinghard

Likes: being nude where I shouldn’t be, and doing something naughty that no one knows about. I like having deadlines of tasks that need to be done or when I do X (some sort of daily thing) I have do to Y. Most anything I haven’t tried, exhibitionism, pictures, videos, predicaments, anal play, light CBT, cross dressing.
Dislikes: cum play/eating, pee... I like to push these!
Limits: family, friends, permanent.
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Old 12-04-2021, 10:00 PM   #8
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Have her go naked under a coat and/or barefoot in the sex shop.

Take an Uber there the same way. See how long she will go like that. Maybe find cheap flips in case someone asks to put them on.

Go to a thrift store...each of you has $20.

Buy an outfit for the other. Either before, right after you leave...put on the outfit and destroy, donate, the clothes you wear there. Have a destination and at least an hour that you have to go in the new outfits
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Old 12-04-2021, 10:47 PM   #9
Txalan
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While you are out doing something together, find a place away from the crowds and flash each other and take picture. She shows you her breasts and you unzip and pull out you dick and balls. Maybe with a famous landmark in the background. Pictures you can only share with each other.

Also if you take an Uber, buy a cheap vibrator, make some funny sounds in the back on the drive, pretend you are using it and leave the vibrator in the uber. Let the drivers imagination go wild, when you really didn't do anything.
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