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Halloween

Discussion in 'Crossdressing in all its variations' started by paulie slave, Oct 22, 2017.

  1. paulie slave
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    paulie slave Member

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    Hey sissies! Anyone going to sneak out in full sissy attire under the pretence of fancy dress? I've never done it but I'm thinking about asking my Wife if she fancies a wee trip into Edinburgh on the 31st. I've gone into town before in a latex kilt and bondage top but getting my made to measure maid's uniform and heels out of the dusty closet could be fun...
     
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  2. DonnaSue
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    DonnaSue Well-Known Member

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    It is very fun, indeed. Last year, I was led into a BDSM Halloween party by a leash attached to me cage. I was wearing a red bustier, fishnet hose, heels, wig, and a little mask. The mask really helped my feel less embarrassed and humiliated somehow - even though we didn't know many people there. It made for a fun evening which began when we left home and I had to drive the 90 minutes to the party dressed that way!
     
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  3. paulie slave
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    paulie slave Member

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    Wow, that sounds amazing! And a little bit scary.
     
  4. Sissy_Cassandra
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    It's always wonderful when you can traipse around in your finest sissy wear in public.
     
  5. SissyMaid4U
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    My wife and I make it a point to go out every year. We always go to a gay club in a neighboring town to reduce the chance of someone knowing me and get a hotel so we can both drink and dance the night away. Then usually it ends with hot strapon sex back at the hotel. This year we are going as day of the dead girls.
     
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  6. sissyassslut
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    A local casino is holding a costume contest this weekend and I told my KH it sounded like fun. She said she would take me if I dressed like a slut.
     
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  7. tiemeupalso
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    tiemeupalso Active Member

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    what does a slut dress like?
     
  8. paulie slave
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    paulie slave Member

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    I asked my Wife about the 31st but was told no. She's more interested in a party at the house.
     
  9. Mash2214
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    Mash2214 Her Locked Little Boy

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    Halloween is a great time to go out as a sissy. Even if you meet someone that you do know or work with. It's Halloween so you can still justify it to them if you aren't ready to come out of the closet just yet.

    Halloween can be a great time. A few years ago I went to a night club as a Blind man. I spent the whole evening feeling my way around. I had a lot of fun and my wife almost died laughing. Through out the evening I only got slapped once which i thought wasn't bad far a Blind Man.
     
  10. PouchPantyLover
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    My wife let me go out dressed up last year with a group of her friends, but she controlled the costume. It was more comedic than sexual. The theme of the bar hop was pirates and wenches, so I was a pirate wench. I had a lot of people laugh at me. A few guys hit on me (Mostly mockingly, but not all) and women wanting to take their picture with me. All in all it was a fun evening and a thrill to be out somewhat dressed up. Still I'd love to have done it my way, but probably would have been a clear tell.
     
  11. SissyMaid4U
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    We just got back from our Halloween fun. We actually ended up going as pirate and wench. I was her wench of course. The whole night she ordered me to do things like get her drinks, only use the lady's room (I'm 90% passing especially when everyone is drunk) and flirt with guys. She even ordered me to dance in a cage for her amusement and my humiliation. I loved it. When we got back we had fantastic sex with me being the girl. Of course I was in chastity the whole night but I was granted, and took full advantage of an anal orgasm.
     
  12. SissyMaid4U
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  13. Mash2214
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    Mash2214 Her Locked Little Boy

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    Halloween can be such an exciting time you can live out some of your fantasies, like you did , and still keep you personal life a secret. Your only acting the part or are you? Good to hear that you had a good time you little Wench
     
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  14. Cecilia B
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    Halloween is supposably the crossdresser National Holiday. I know the past 3 years, I've had BF in one of those satin little girl party dresses and petticoats. And yes, I've made him lift up his petticoats to show his ruffled panties, too. Some people have asked why I have him in heels, garterbelt and stockings and a bra instead of flats and little white socks, but I just tell them I like him better with adult shoes and some adult underwear and some little girl underwear.
     
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