MichelleSEmass's Blog

Chicago visit

Well I got to go out to Chicago on business for a couple of days. I took advantage of the trip and was able to bring some of my girlie things and I was able to get a makeover at Transformations by Rori each night I went out, Rori selected a new blond wig for me and gave me makeovers that made me look really hot!!

One of the nites I got all made up and dressed in a hot black cocktail dress that was slinky and had a sheer lace top. Beneath I had on a black waist cincher, bra, garters, backseam stockings and red heels. I had left Rori’s all dressed and made up that way so I was looking hot ... Continue»
Posted by MichelleSEmass 1 year ago  |  4

[Story] Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and... Continue»
Posted by MichelleSEmass 2 years ago  |  6

Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and al... Continue»
Posted by MichelleSEmass 2 years ago

The Video Store

I had been itching to go to the local Adult Video Store in Providence. This time I wanted to go dressed. I had been before, dressing in panties and bra under my guy clothes but this time I wanted to go in all dressed up. I chose a black satin party dress with white polka dots. It had a bit of a crinoline underneath and looked hot. Underneath I wore a black corset with garters, stockings, red sissy panties and a red lace bra. I finished it off with my long blond wig and red 5” heels. It was a bit cold out so I wore a white fur coat.

I parked near the bookstore and walked about a block. It... Continue»
Posted by MichelleSEmass 2 years ago  |  4

My fantasy...

I've had a fantasy recently that I meet a guy online who tells me he wants me to dress up in a special dress and go to one of the local video booths with gloryholes with him. I agree and he tells me he will by the dress and send it to me at my post office box. I give him my measurements and wait. The rather large package arrives and I am told NOT to open it until that nite. We set the date and I get a hotel room nearby. I dress in my open bottom girdle with 6 garters, panties, bra, stockings, do my wig and makeup an then open the box.

What I find is a frilly little girls dress in my si... Continue»
Posted by MichelleSEmass 2 years ago  |  1

[Story] Chaz

Chaz

I met Chaz online. It was to be the first time I met and dressed for a guy without my wife’s knowledge. She had stopped being into dressing me or letting me dress around her. She felt we needed to get back to “normal” play.

Chaz told me he wanted me to come over in the afternoon around 3 pm after he got home from his teaching job. From our online conversation I knew that he was single, had an apartment, was a top and was looking to get sucked. He seemed a bit indifferent towards my dressing but that was ok.

I arrived at his place which was on the second floor of a big three st... Continue»
Posted by MichelleSEmass 2 years ago  |  3

[Story] Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 2 years ago  |  7

[Story] Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 2 years ago  |  10

[Story] Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 2 years ago  |  12
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