Room Mate To Boyfriend

I was living alone when a old high school friend told me he needed a place to live. I needed help with the rent and it was a big house so I said ok. But I had a secret to hide, I was a crossdresser. I had a lot of clothes and loved to dress. Kevin moved in and things went well, he traveled a lot for his job so I found time to dress.
Kevin told me he was going to Saint Louise for the weekend. He left Friday night and I was going to dress as Amy for the weekend. I dressed in a skirt, blouse, pantyhose heels, did my makeup put on a wig and went down stairs to get something to drink. I was at the fridge when when I heard excuse me I turned around and their was Kevin! I did not know what to say, Kevin looked at me and said Randy? I did not know what to do I was frozen. Kevin said I am sorry I got to go and left. I was terrifed who was he going to tell what can I do? I started to cry.
Kevin came home Sunday night he did not say anything about Friday. Monday night I had to know. I said about the other day, he stopped me and said this is your house you can do what you want. Are you going to tell anyone? He said no, how long have you been dressing? I said all my life. I ask him do you dress? He said he did when he was little but not for a long time. He said you looked good do you have a lot of clothes? I told him I did, he said can I see them? I said ok lets go up stairs. We went to my room it has two closets, I showed him Amy's.
Kevin did not know what to say, I have dresses on one side skirts and blouses on the other. Where did you get all this, out of mail order, how many pairs of shoes are there? About 40 or so that is my passion! He ask me if I would dress as Amy for him? I said ok told him to go down stairs and wait.
I dressed in a blue dress, hose, heels, did my makeup put on a wig and went down stairs. He looked at me and just said wow! I set next to him crossed my legs and showed him pictures of me dressed. He started running his hand over my leg and telling me how good I looked. I leaned over and kissed him. He was shy so I rubbed his rock hard **** and he moned with pleasure. I unzipped his pantspulled out his ****. I dropped to my knees and ran my tougne over the head then up and down the sides around his balls and back up I did it again and again then he came I cleaned up every drop, looked up at him and said you know this changes everything boyfriend!
ammilnet ammilnet
11 Responses Dec 8, 2012

OMGosh, what a sexy story! Do you still get along with Kevin?

Oh my! Oh wow!! Sexy story!!! Hope you two stayed together as a couple!!

Great story girl.
Love you

Baby- Such a great story. Your very lucky. Have fun with your new 'boyfriend'. I know I would.

So tell us about all of the changes in your living arrangements with Kevin.

Such a wonderful story.

You lucky girl. Getting caught a great benefit for you. I am happy for you. Hope you two make each other happy.

Very sexy story. I would love to have a closet stuffed with girly things as well

Incredibly sexy story. Wish it would have happened to me. So nice to hear you enjoy kissing as well. I'd love to meet Randy & Amy both sometime. I just have panties & thigh highs of my own and borrow my wifes lingerie to wear when I am alone at home. I have tried skirts and dresses and love them but my wife has not worn them for years and gave away most. Funny now that I think about it, she is the more masculine one in the home and I am the more feminine one.

How can one be so lucky!!!

He is one lucky bastard. Hot story, please add me