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KassieandHaley Amateur Jackinchatter

109 posts since 2020-05-19
31 year old curious male
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Hi everyone, looking for some hot, detailed roleplay here. I am a 27 year old male, who loves to get dominated and feminizied. I have a bunch of pictures of hot women who i would love to dress like and look like. I am into crossdressing, toying, bondage, feminization, humiliation etc. If you really want to get my blood pulsing, we can include my ex gf Kassie. I cheated on her, and im sure she would love to get her revenge.


We can either dress me up like the sissy version of the women, or we can do an EXCHANGE pill roleplay where i turn into one of them!

My perfect roleplay would go like this:
I have agreed with Kassie in order to keep my apartment and have her move out, i must be her slave for a day. You are her new man, and you two take me to the mall. She puts a dog collar on me and leads me through the mall. You take me into a store and get me set up with a bra, panties and stockings. You then take me to forever 21 and get me a cute mall appropriate outfit to wear around. Then to the wig store, and then i have to sit down with Kassie for a mani-pedi. A quick trip into Sephora where Kassie will do my makeup, giving me a full sissy look. Maybe we then go buy some sluttier outfits for later, maybe the Adults only store for some toys.
When we get back to your place, maybe i am the cuckold in the corner for you guys, maybe I am the entertainment for your guys night. I could be a fashion model for you, whatever your heart desires.


Obviously im open to more roles but i hope that gives you a solid idea of what i like.

Skype is [email protected]
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KassieandHaley Amateur Jackinchatter

109 posts since 2020-05-19
31 year old curious male
KassieandHaley's Avatar
Hi everyone, looking for some hot, detailed roleplay here. I am a 27 year old male, who loves to get dominated and feminizied. I have a bunch of pictures of hot women who i would love to dress like and look like. I am into crossdressing, toying, bondage, feminization, humiliation etc. If you really want to get my blood pulsing, we can include my ex gf Kassie. I cheated on her, and im sure she would love to get her revenge.


We can either dress me up like the sissy version of the women, or we can do an EXCHANGE pill roleplay where i turn into one of them!

My perfect roleplay would go like this:
I have agreed with Kassie in order to keep my apartment and have her move out, i must be her slave for a day. You are her new man, and you two take me to the mall. She puts a dog collar on me and leads me through the mall. You take me into a store and get me set up with a bra, panties and stockings. You then take me to forever 21 and get me a cute mall appropriate outfit to wear around. Then to the wig store, and then i have to sit down with Kassie for a mani-pedi. A quick trip into Sephora where Kassie will do my makeup, giving me a full sissy look. Maybe we then go buy some sluttier outfits for later, maybe the Adults only store for some toys.
When we get back to your place, maybe i am the cuckold in the corner for you guys, maybe I am the entertainment for your guys night. I could be a fashion model for you, whatever your heart desires.


Obviously im open to more roles but i hope that gives you a solid idea of what i like.

Skype is [email protected]
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That sounds fun. I agree, I have had urges to be more feminine when I chat. I love when people are so sweet to me and treat me nice and pamper me, just like a girl. I'd love to find someone that can treat me like that on here.
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KassieandHaley Amateur Jackinchatter

109 posts since 2020-05-19
31 year old curious male
KassieandHaley's Avatar
Hi everyone, looking for some hot, detailed roleplay here. I am a 27 year old male, who loves to get dominated and feminizied. I have a bunch of pictures of hot women who i would love to dress like and look like. I am into crossdressing, toying, bondage, feminization, humiliation etc. If you really want to get my blood pulsing, we can include my ex gf Kassie. I cheated on her, and im sure she would love to get her revenge.


We can either dress me up like the sissy version of the women, or we can do an EXCHANGE pill roleplay where i turn into one of them!

My perfect roleplay would go like this:
I have agreed with Kassie in order to keep my apartment and have her move out, i must be her slave for a day. You are her new man, and you two take me to the mall. She puts a dog collar on me and leads me through the mall. You take me into a store and get me set up with a bra, panties and stockings. You then take me to forever 21 and get me a cute mall appropriate outfit to wear around. Then to the wig store, and then i have to sit down with Kassie for a mani-pedi. A quick trip into Sephora where Kassie will do my makeup, giving me a full sissy look. Maybe we then go buy some sluttier outfits for later, maybe the Adults only store for some toys.
When we get back to your place, maybe i am the cuckold in the corner for you guys, maybe I am the entertainment for your guys night. I could be a fashion model for you, whatever your heart desires.


Obviously im open to more roles but i hope that gives you a solid idea of what i like.

Skype is [email protected]
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jj2101 said:
That sounds fun. I agree, I have had urges to be more feminine when I chat. I love when people are so sweet to me and treat me nice and pamper me, just like a girl. I'd love to find someone that can treat me like that on here.


I also agree with you. I couldn't figure it out cause I have no intention to be this way in real life, but just something about coming here and letting someone be nice to me and treat me sweet and nice and take care of me that I love, even if it means I have to act like a girl. I'd love to find someone who would regularly treat me like that on here. It is just a great escape from reality for a change.
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completeloser Novice Jackinchatter

6 posts since 2007-11-26
48 year old bisexual male from Minnesota
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I think that guys in general are really hungry for affection more than anything. I enjoy the idea of sissy role play because of the female energy that it has, while still have the raw sexual desire that I know as a man, then I know is in my partner.
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completeloser said:
I think that guys in general are really hungry for affection more than anything. I enjoy the idea of sissy role play because of the female energy that it has, while still have the raw sexual desire that I know as a man, then I know is in my partner.


Great point. Guys can't just be emotional and sensitive with each other like girls can. I envy girls that can just gossip and be so close with their girlfriends and hug them and cry with them and share everything with them. It just isn't "acceptable" for guys to do that.
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