halloween party

[RifleX]

Bi-curious guy gets invited to masquerade/halloween party, forgets/doesn't have costume, ends up borrowing wife's clothes and going as a woman. Ends up getting his first bi experiences due to how he's dressed.

Outfit/makeup doesn't make him look like he's really a woman - i.e. his "costume" is being dressed as a slutty woman.

Wife encourages both the cross-dressing and the... results, but not in a demeaning way.

I know... picky picky.

 

[Carnevil9]

Sounds a lot like my "His Better Half" story.......Carney

 

[sirhugs]

Halloween is a good setting for a cd/ts story. My Halloween Dress-Up won best CD story in 2005. Not party based though - just a guy trying to please a girl.

Others you might like:

Hallowe'en Party by tgirl_Mary

Halloween Cross-Dressing Bash by BOSTONFICTIONWRITER, An 8 part series (has lower scores, but might float your boat). Part One is at this url

A story search for keyword "Halloween" in the TS& CD category turns up about 90 stories. I tried to link but it failed...