Sissy Weekend Ideas

[Wag_that_tail86]

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

This whole plan is just dreamy...and fishing too! We will all be fantasizing about you two alone in the woods...

 

[stargame]

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

I love your style

 

[Cardinal]

Thanks, I’m getting excited about it too, we haven’t had an opportunity like this in a long time.

 

[stargame]

I just did a little shopping for myself. Black lace top stockings and white lace panties are a very fun thing.

 

[LannaLace]

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.

Sounds like fun! You might want to checkout “Ready to Love” brand 6 pack panties on Amazon… I got the thong variety…. They are gorgeous and comforable…but don’t do much for keeping the snake in the cage. Especially when checking how they fit, in the mirror!!!

 

[LannaLace]

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.

You might be interested in my Skipper and the Cabin Gurl stories… they feature some fishing with a lot of spectacular sissy sensational sex!

 

[Cardinal]

You might be interested in my Skipper and the Cabin Gurl stories… they feature some fishing with a lot of spectacular sissy sensational sex!

5 part story! I’ll start it today

 

[BizTrav]

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

Recreation Central!

 

[Cardinal]

Good news! We leave today at 1 pm and we just got an email about being upgraded! The cocktails will begin with wheels up, the weekend is stating out great!

 

[BizTrav]

Happy Travels!
Bring your rain gear...

 

[ncpantyguy4fun]

Good news! We leave today at 1 pm and we just got an email about being upgraded! The cocktails will begin with wheels up, the weekend is stating out great!

We wanna see pictures!!!! My panties are already tight thinking about it.

 

[warner34]

Excited for you both!

 

[pantyboyxxx]

I just did a little shopping for myself. Black lace top stockings and white lace panties are a very fun thing.

we want photos!

 

[Hitchiker69]

A few ideas...
- Do a fem dressed strip show for each other, in turn, to see how aroused you can get the other without touching. Of course it always ends with cocks in mouths, taking turns serving each other, to completion.
- Cook breakfast for one another dressed exclusively in lingerie.
- Share your favorite porn with each other while stroking, dressed in lingerie
- Have a contest: who can make the other cum fastest in a 69 position. Winner tops the first to cum, after sharing a wet sloppy kiss. All while dressed in lingerie.
- Sneak out in the common area after dark, and make out or suck each other where there's a chance of being caught
- Play strip poker XXX style. Loser strips one item each, until nude. Loser of the next hand sexually serves winner however and whatever the winner wants
- Start by booking a cabin at Whispering Oaks, in TN. It's an all male clothing optional resort. Go and have sexy fun, and meet new friends. Tell the wives it's a fishing resort


More to come....

 

[BizTrav]

Good Morning!

 

[Hitchiker69]

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

- Practice, practice, practice kissing, stroking, sucking and fucking

- Both of you bring your favorite toys and vibrators. Or order new ones to be delivered to the resort. Try out new ones together Share with each other, showing exactly how to get yourselves and each other to cum

 

[stargame]

A few ideas...
- Do a fem dressed strip show for each other, in turn, to see how aroused you can get the other without touching. Of course it always ends with cocks in mouths, taking turns serving each other, to completion.
- Cook breakfast for one another dressed exclusively in lingerie.
- Share your favorite porn with each other while stroking, dressed in lingerie
- Have a contest: who can make the other cum fastest in a 69 position. Winner tops the first to cum, after sharing a wet sloppy kiss. All while dressed in lingerie.
- Sneak out in the common area after dark, and make out or suck each other where there's a chance of being caught
- Play strip poker XXX style. Loser strips one item each, until nude. Loser of the next hand sexually serves winner however and whatever the winner wants
- Start by booking a cabin at Whispering Oaks, in TN. It's an all male clothing optional resort. Go and have sexy fun, and meet new friends. Tell the wives it's a fishing resort


More to come....

I will have to bring at least four suitcases of lingerie☆

 

[dodgeboy2]

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

Pick up a deck of gay cards each card had an illustration or explanation of an act either you or he does, they can prove to be awesome.

Play strip poker deciding what the winner gets before starting and just have fun with it.

Make a bet if you catch the biggest fish what does he do for you, if he does what does he want you to do for him.

Have some sort of drinking game betting whatever you feel comfortable with.

Just a few ideas.

 

[Hitchiker69]

The #1 thing you have to do is to invite me to join you. I'll bring my frilliest panties and lingerie, lots of nice smelling & tasting lube, and plenty of wine. I'll play any role you like, with special enthusiasm for cock sucking roles.
I'd love to explore my inner sissy with a pair of like minded men

 

[ncpantyguy4fun]

The #1 thing you have to do is to invite me to join you. I'll bring my frilliest panties and lingerie, lots of nice smelling & tasting lube, and plenty of wine. I'll play any role you like, with special enthusiasm for cock sucking roles.
I'd love to explore my inner sissy with a pair of like minded men

Aint that the truth!!! I love having dress up play dates!

 

[Katecdpt]

My idea of a weekend date night outfit.

 

[stargame]

My idea of a weekend date night outfit.
View attachment 2538882

What panties would you be wearing?

 

[Katecdpt]

I'm thinking black lace thong for this outfit.

 

[BizTrav]

Okay...I vote for Kate's

 

[Ciceri]

Will you be driving? Plan to buy some fish to bring home because I doubt you’ll be spending any time outdoors. Someone mentioned hiring a guide. I think hiring a masseur would be a good idea. Bring at least three changes of clothes per day, makeup, wigs and perfume. Someone mentioned lots of lube and maybe some gay porn while you’re at it. Plan on taking pics/vids to share. Enjoy!