XXX The Mailman Wears Dresses
Postal Service Cross Dressing
Posted on
Add A New Story
The chapter list
Chapter 1
The Next Chapter
 My name is Timmy. I'm a rather frail and feminine kind of male who loves to dress up in girls clothes every chance I get. I was assigned to a Post Office delivery route in a affluent area of midtown. This is where the rich and famous live and work. On my first day, I met my new coworker Faye. Faye had quite a reputation in this Post Office as a loud pushy dominant butch lesbian. I was totally unaware of her reputation.  I didn't know she was gay. I didn't know what gay meant. I was clueless about sex. I didn't even know my love of wearing women's clothes had a name. Eventually she came out and told me "I'm gay". This didn't bother me and I began to realize most people think I'm gay too. Faye and I made quite a team. She always teased me. She told me."You have a pretty face". She also made comments "You walk like a girl" she also noticed, "You are as weak as a girl".  When it came to lifting heavy mail bags, I blushed as she lifted them for me without a problem. She was right, I was like a girl, in stature, strength and interests. We grew quite close almost like girlfriends. She was my protector & confidant. She showed me the ropes of delivering the mail, sorting and dispatching certified, registered and parcel post packages. She ran circles around me. She treated me like a girl. I felt as if she was the man, I was the defenseless girl. We made deliveries together and she would point out, "He's Gay" and "That guy there is a crossdresser". I asked her, "how do you know?" She explained that the combination of the mail they received and meeting them in person left no doubt. "Gay" and "Drag" magazines were a clear clue. She pointed out that certain return addresses were retailers that sold dildos, dresses and shoes for transvestites. Faye knew them all. I got to thinking, "My mailman knows I'm a transvestite." I thought of all the times I bought sissy clothes, dildos, lingerie, dresses & shoes from the same retailers. I finally admitted I was a transvestite. She said, "I already knew. A few times when you bent over I saw your lacy pink underwear poking out of the back of your pants" . It became routine for her to question me, "What are you wearing today honey?" "What's your favorite color?" What dress size are you?" I found myself getting erections more frequently as I fantasized about being dressed and having a man make love to me. She swore, "One of these days I'm going to see you in a dress! I have a hunk that lives in my building that would love to have sex with you!" I thought, "She thinks I'm gay, maybe I am". She gave me copies of gay magazines filled with men having sex with each other. When I returned them, she asked, "What did you think?' I said, "I can't believe anybody could have such a big cock". She asked me, "Did you ever suck cock?" I said "No, a few times men told me they wanted to put their cock in my mouth, I never did. I do fantasize about wearing dresses and having sex with men". She told me "one of these days I'm going to help your dreams come true!" Somehow, I knew it was my destiny to work here, meet Faye and experience having sex for the first time.
The Next Chapter
Gallery Images by nylontoni
Display More Images
Last Post
0 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.