Sissy Weekend Ideas

[Cardinal]

Okay here’s the scenario, if you could reply with ideas, suggestions, or challenges to make an unforgettable weekend I would appreciate it.

Two buddies who are both married, closeted sissies (wives of 30 years+ for both have no idea) have an opportunity to spend an entire weekend together alone in a condo in Colorado for a fishing trip.
All suggestions are appreciated.

Edit; this isn’t for a story, it’s for an actual trip that we are taking and we want suggestions on ideas to make it memorable

 

[jk25]

Hmm fishing naked while sword fighting... don't forget to pack plenty of lube.

 

[bi_musings]

Maybe their guide is college-aged and gay. Perhaps they have questions for him about his lifestyle and he offers to come by the condos to share his trout recipe at the end of that day?

 

[PantyMon]

I’ve got some idea. My thoughts tho are rooted
If your in a different part of an area that you’ll feel
Comfortable going out all dolled up.

If so:
- a friendly competition/wager to see which one of
You can get more free drinks at a bar/club
- of course a mani/pedi could be fun especially if your dressed up for it
- lounge by a pool in your bikinis

Or are you both looking for for a some lesbian sissy love between the two of you and in this more of a Romantic weekend always as your alternate persona? If so, I’ve got other ideas too.

 

[Cardinal]

I’ve got some idea. My thoughts tho are rooted
If your in a different part of an area that you’ll feel
Comfortable going out all dolled up.

If so:
- a friendly competition/wager to see which one of
You can get more free drinks at a bar/club
- of course a mani/pedi could be fun especially if your dressed up for it
- lounge by a pool in your bikinis

Or are you both looking for for a some lesbian sissy love between the two of you and in this more of a Romantic weekend always as your alternate persona? If so, I’ve got other ideas too.

Love the challenges! Also some fun ideas for our alone time in the condo, we’ve been toying with (pun intended) sissy dressing and living the weekend together as a couple when in the condo.

 

[PantyMon]

Love the challenges! Also some fun ideas for our alone time in the condo, we’ve been toying with (pun intended) sissy dressing and living the weekend together as a couple when in the condo.

Then perhaps a trip to a Victoria Secrets would also be in order to get yourselves a little something new and exciting.

Might even be fun to explore going out in full dress? Maybe a dinner or something? Even if neither of you are ‘passable’ still could be exhibiting.

 

[Wag_that_tail86]

Hmm fishing naked while sword fighting... don't forget to pack plenty of lube.

...and sunscreen

 

[Wag_that_tail86]

Love the challenges! Also some fun ideas for our alone time in the condo, we’ve been toying with (pun intended) sissy dressing and living the weekend together as a couple when in the condo.

So much fun. One of you should bring the French maid outfit for doing "chores."

 

[Cardinal]

So much fun. One of you should bring the French maid outfit for doing "chores."

Well we are planning a full sissy weekend when in the condo, full sissy clothing and panties. We routinely gamble on everything we do, golf, hunting, bowling, and of course fishing. The difference this time is that the consequences can be just between us inside our condo for the weekend. I like the idea of the loser of a bet serving the other in a maids uniform!

 

[SissySalina]

Why a maid?
Make a bet of best of 18 and the looser has to dress as a hooker and service the winner.

 

[Lori_Lux]

Why a maid?
Make a bet of best of 18 and the looser has to dress as a hooker and service the winner.

The game might not be fun if the prize is for losing

 

[Cardinal]

Why a maid?
Make a bet of best of 18 and the looser has to dress as a hooker and service the winner.

So no real loser then?

 

[Cardinal]

Any competition we have will be fun for both I’m sure.
If he catches more fish and demands a foot rub or makes me do his nails while we are dressed in our sexy sissy clothes we both win!

 

[Cardinal]

Hmm fishing naked while sword fighting... don't forget to pack plenty of lube.

We’ll take the fishing seriously then it’ll be playtime back at the condo, well I’m sure I’ll be enfem under my clothes and waders but no play time while fishing

 

[Cardinal]

Maybe their guide is college-aged and gay. Perhaps they have questions for him about his lifestyle and he offers to come by the condos to share his trout recipe at the end of that day?

As long as he’s a Dom who knows how to control two sissies I guess it could work

 

[Cardinal]

Thanks for your input so far! Showed my buddy this thread and he’s even more excited about our trip to Colorado!
What started out as a fun guys trip to a favorite trout fishing outfitter and having some sissy fun has turned into a full blown 100% sissy weekend and we might do some fishing!
I think this was the nudge that we both probably needed to make this happen.
He’s been texting me ideas about how we’re only allowed to wear panties, even on the plane. He wants us to each buy each other some new panties and nightgowns that we will model for each other in the condo. This is actually a good idea because I don’t own enough panties to last 4 days without having to do laundry. So I’ve been shopping in Esty to really fem him up!
I think I should buy some new toys to take with us too. Would be cute to watch him struggle with a chastity cage or butt plug while standing in a stream wearing waders trying to fish! We’ve never played with either of those but I think it would be fun.
Although we both panty wearing sissies that no one knows about we can take the other role too so we can each enjoy being submissive to the other occasionally instead of just girly girlfriends cuddling in the couch.
We are only a couple of weeks away from our trip so I’m sure we’ll come up with some more fun ideas.

 

[BizTrav]

Oh my...would love to host this party!

 

[Cardinal]

Oh my...would love to host this party!

Do you live somewhere fun that we could visit next time we get away?

 

[Cabeza]

Sounds like so much fun! I’m having a sissy weekend myself this weekend except it’s just with myself. Alone in a rustic cabin all weekend

 

[Cardinal]

Sounds like so much fun! I’m having a sissy weekend myself this weekend except it’s just with myself. Alone in a rustic cabin all weekend

We know how much fun alone time can be! Enjoy!!

 

[Cabeza]

We know how much fun alone time can

I’m just gonna enjoy dressing how I want this weekend. But if I were you and had a friend I think I’d take advantage of the opportunity and go shopping for some cute/sexy clothes together

 

[SexyInMy60s]

Thanks for your input so far! Showed my buddy this thread and he’s even more excited about our trip to Colorado!
What started out as a fun guys trip to a favorite trout fishing outfitter and having some sissy fun has turned into a full blown 100% sissy weekend and we might do some fishing!
I think this was the nudge that we both probably needed to make this happen.
He’s been texting me ideas about how we’re only allowed to wear panties, even on the plane. He wants us to each buy each other some new panties and nightgowns that we will model for each other in the condo. This is actually a good idea because I don’t own enough panties to last 4 days without having to do laundry. So I’ve been shopping in Esty to really fem him up!
I think I should buy some new toys to take with us too. Would be cute to watch him struggle with a chastity cage or butt plug while standing in a stream wearing waders trying to fish! We’ve never played with either of those but I think it would be fun.
Although we both panty wearing sissies that no one knows about we can take the other role too so we can each enjoy being submissive to the other occasionally instead of just girly girlfriends cuddling in the couch.
We are only a couple of weeks away from our trip so I’m sure we’ll come up with some more fun ideas.

I think I’d be excited about finding a quiet, isolated place in the woods and fucking like bunnies.

Also a couple of sissy ideas: thigh-high stockings (garter belts are a big plus) and some sexy red lipstick for extra cocksucking fun.

 

[Cardinal]

I have a cute sissy skirt with garter straps, not sure of stockings because how would I explain my shaved legs after a weekend away with my friend? Oh yeah we’ve been using red lip stick for a while, we both like that

 

[ToniTot]

Okay here’s the scenario, if you could reply with ideas, suggestions, or challenges to make an unforgettable weekend I would appreciate it.

Two buddies who are both married, closeted sissies (wives of 30 years+ for both have no idea) have an opportunity to spend an entire weekend together alone in a condo in Colorado for a fishing trip.
All suggestions are appreciated.

Edit; this isn’t for a story, it’s for an actual trip that we are taking and we want suggestions on ideas to make it memorable

mmmmmmm good chance of getting your fill of Trouser Trout...

 

[Wag_that_tail86]

Sounds like so much fun! I’m having a sissy weekend myself this weekend except it’s just with myself. Alone in a rustic cabin all weekend

Lovely!