Halloween Crossing dressing

sirhugs

Riding to the Rescue
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I might know something about how the ghoulish "holiday" and crossdressing fit together. My Halloween Dress-up won "Best transsexuals & crossdressing story" of 2005. Though its the last cd story I wrote (so far).

here's another variation on the theme, if anyone wants to take it & start early:

Somewhat vanilla hubby & wife recently moved to a new town. He lost his job in the meltdown. She traded up to this better job, but they don't really know the co workers, and are very nervous.

They are invited to a Halloween party hosted by one of the company's owners that she barely knows. The invitation was couriered to the house. It specifies "Costume Theme: He dresses as She/She dresses like He. Company provides first Prize - a $1000 bonus PLUS an extra week of vacation PLUS a 4 day Caribbean cruise package".

Hubby reads this and spends the whole day alternating between wondering what sort of pervs wife works for and hoping to win the prize. It's been a tough year.

When wife gets home, hubby has turned femme - dressed in one of her favourite outfits, makeup hiding his whiskers, right to earrings, heels, stockings.

She is shocked how he bought in, only reluctantly agrees to try on the male clothes he put out for her - again, a full outfit, suit, shirt, tie, shoes, shocks, briefs, right to a fedora. she exiles hm from the bedroom while she changes [in longer version, insert switching individual parallel masturbation scenes here]

Finally she calls him in. She makes a gorgeous man - think Kim Basinger in 9 1/2 Weeks*. but she's not comfortable with it. He suggests that since the theme does not require full outfits, she should try wearing just some of the clothes.

To his shock, she starts doing a slow strip tease. As she removes each article of clothing she says "How does this look?" He just replies "are you comfortable?" But soon, he's jerking off watching.

Finally, she's down to just the fedora and asks " How does this look?" he replies "are you comfortable?" Her hands are roaming her body, stroking her nipples, finally her slit, as she sighs "yesssss".

massive sex scene ensues in which she keeps fedora on, he is still wearing his femme clothing, skirt hiked up, panties tucked under his balls.

You could stop there, or have the longest version, where they go to the party, him fully femme, her wearing only the fedora (and heels?) and nothing else (maybe a man's trench coat? - insert a little flashing humour? if so, switch the heels for men's shoes). They win the prize. Orgy scene optional.

*If you haven't seen that movie, and esp that scene, go find it, asap.... perhaps the hottest mainstream sex movie ever.
 
crap, its that time of year again....where did this year go? I did notice costco was clearling out an area...wonder if Costco will be putting up xmass stuff next week?

on this story note, I got 3 emails last week from men who have pantyhose fetishes. two of the men love to wear hose. interesting. I might take a stab at this story, where a couple goes to a party and the couple is mistaken as someone else, and they both .......



I might know something about how the ghoulish "holiday" and crossdressing fit together. My Halloween Dress-up won "Best transsexuals & crossdressing story" of 2005. Though its the last cd story I wrote (so far).

here's another variation on the theme, if anyone wants to take it & start early:

Somewhat vanilla hubby & wife recently moved to a new town. He lost his job in the meltdown. She traded up to this better job, but they don't really know the co workers, and are very nervous.

They are invited to a Halloween party hosted by one of the company's owners that she barely knows. The invitation was couriered to the house. It specifies "Costume Theme: He dresses as She/She dresses like He. Company provides first Prize - a $1000 bonus PLUS an extra week of vacation PLUS a 4 day Caribbean cruise package".

Hubby reads this and spends the whole day alternating between wondering what sort of pervs wife works for and hoping to win the prize. It's been a tough year.

When wife gets home, hubby has turned femme - dressed in one of her favourite outfits, makeup hiding his whiskers, right to earrings, heels, stockings.

She is shocked how he bought in, only reluctantly agrees to try on the male clothes he put out for her - again, a full outfit, suit, shirt, tie, shoes, shocks, briefs, right to a fedora. she exiles hm from the bedroom while she changes [in longer version, insert switching individual parallel masturbation scenes here]

Finally she calls him in. She makes a gorgeous man - think Kim Basinger in 9 1/2 Weeks*. but she's not comfortable with it. He suggests that since the theme does not require full outfits, she should try wearing just some of the clothes.

To his shock, she starts doing a slow strip tease. As she removes each article of clothing she says "How does this look?" He just replies "are you comfortable?" But soon, he's jerking off watching.

Finally, she's down to just the fedora and asks " How does this look?" he replies "are you comfortable?" Her hands are roaming her body, stroking her nipples, finally her slit, as she sighs "yesssss".

massive sex scene ensues in which she keeps fedora on, he is still wearing his femme clothing, skirt hiked up, panties tucked under his balls.

You could stop there, or have the longest version, where they go to the party, him fully femme, her wearing only the fedora (and heels?) and nothing else (maybe a man's trench coat? - insert a little flashing humour? if so, switch the heels for men's shoes). They win the prize. Orgy scene optional.

*If you haven't seen that movie, and esp that scene, go find it, asap.... perhaps the hottest mainstream sex movie ever.
 
Back in 2006 I submitted a story to the Halloween contest called A Game of Tricks and Treats where the husband dressed as a cheerleader for his company costume party (and his wife dressed as a football player - complete with a strap-on hiding in the pants)...
 
Back in 2006 I submitted a story to the Halloween contest called A Game of Tricks and Treats where the husband dressed as a cheerleader for his company costume party (and his wife dressed as a football player - complete with a strap-on hiding in the pants)...

sounds like quite a game ;)
 
Back in 2006 I submitted a story to the Halloween contest called A Game of Tricks and Treats where the husband dressed as a cheerleader for his company costume party (and his wife dressed as a football player - complete with a strap-on hiding in the pants)...

I've gotten a lot of emails these past 6 weeks from men who love the idea of being in a threesome and giving the other guy a blow job. interesting...
 
What is it about Halloween and Crossdressing? :devil:

I've done a lot of Captioned Images dealing with those topics, and my one actuall TG fiction piece was also about that.

I've had quite a few ideas; here are some of the highlights.

1) Inspired by a TG girl i saw that was 40 but looked much younger, a college guy goes home for Halloween weekend, dresses in a girls costume, and passes for a high school hottie! :eek: At a School party, who does he hook up with? Teacher from old school? Brother's friends? His Brother?:D

2) This one is a little supernatural,and not actually what I like in my stories, but it is kinda hot: A young man finds a maids uniform hidden in his room. As soon as he finds it, he's compelled to wear it, finding it makes him look more feminine (he slowly changes into a woman as it goes). Turns out the costume is haunted by the ghost of an actual Maid, who is using it to control the young man and get revenge on her killer!

3)Halloween at work; I used to always be jealous of people who got to dress up at work (but not sure which gender i was more jealous of...). So, this idea is less rounded out. A guy dresses as a woman/in a woman's costume for work. He might work at a bookstore, or he could be a banker, or even a teacher. (I always liked the idea of a cd teacher, for some reason)

4) A really nasty, wrong one. Going off my incest kink; Dressing in a hot female costume this year, a young man attracts the attention of his dad/brother. Was this all just hormones, or did the young Twink plan it?
 
What is it about Halloween and Crossdressing? :devil:

I've done a lot of Captioned Images dealing with those topics, and my one actuall TG fiction piece was also about that.

I've had quite a few ideas; here are some of the highlights.

1) Inspired by a TG girl i saw that was 40 but looked much younger, a college guy goes home for Halloween weekend, dresses in a girls costume, and passes for a high school hottie! :eek: At a School party, who does he hook up with? Teacher from old school? Brother's friends? His Brother?:D

2) This one is a little supernatural,and not actually what I like in my stories, but it is kinda hot: A young man finds a maids uniform hidden in his room. As soon as he finds it, he's compelled to wear it, finding it makes him look more feminine (he slowly changes into a woman as it goes). Turns out the costume is haunted by the ghost of an actual Maid, who is using it to control the young man and get revenge on her killer!

3)Halloween at work; I used to always be jealous of people who got to dress up at work (but not sure which gender i was more jealous of...). So, this idea is less rounded out. A guy dresses as a woman/in a woman's costume for work. He might work at a bookstore, or he could be a banker, or even a teacher. (I always liked the idea of a cd teacher, for some reason)

4) A really nasty, wrong one. Going off my incest kink; Dressing in a hot female costume this year, a young man attracts the attention of his dad/brother. Was this all just hormones, or did the young Twink plan it?

all nice variations. I too like the cd teacher idea for some reason...
 
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