My first cock was a crossdressers

One friday night back when I was 25 I was in the chat rooms looking for a little action. I had chat with a few ladies that got me nice and hard,but no of them lived in the same city as me and i was looking for more hands on fun. At about midnight a message popped up. “Hi I’m DeeDee whats your name?” “My name is Joe.” I respond. “Hi joe how old are you and where are you from?” She asked me. I tell her my age and where im from. She tells me where she is and its not far from my place. So i ask”How old are your and what are you looking for tonight?” Hoping to get some action.

She responded with”I’m 35 m crossdresser,I’m very passable.” “I even get hit on when i go to the clubs.” I didnt know what to say, I have fantasied about sucking a mans cock,but never had the nerve to do it. I sat there for a few moment not knowing what eles to say. “When he responded with”Did i scare you off sweety?” At this point I became very shy. “No” Was all I replied. “Are you bi honey?” He asked me. “I have been curious.” “What have you been curious to try?” “I what try to suck a dick.” “Well honey I have nice one for you under my skirt.” “would you like to see it?” Nervously I respond. “Yes.” “Then whats your address sweety and I’ll let you see it.”

I’ll said.”I dont know I have never done this before.” “It’s ok to be nervous sweety everbody is ther’re first time.” “I promise I’ll be gental and you dont have to do anything you dont want to do.” Still shy I tell him. “I dont know.” He said. “Well I know your horny so how about I bring over a porn movie we can watch it then you can just sit back and let auntie DeeDee take care of you.” “You wont have to do anything just sit back and let me service your cock.” “I guarantee until I show you my cock,you’ll sware Im a woman.” Being as horny as I am,and the fact that I havent had a blowjob in a while I agreed and gave him my address.

I log out shut off my pc. I turn out all the lightes.I have some Chrismas lights around my livingroom ceiling,it gives off a nice ambient red glow thats perfect for watching movies or getting a bj.I sit down on my couch and Pull out my cock. I start stroking thinking about the bj I’m going to get. But then my mind wonders to his cock, and I sware my cocks gets even harder. I’m thinking I’m going to do it.I’m going to suck my first cock. So here I am sitting on my couch stroking my cock thinking of the dick I’m going suck. How big is it?Will it have any hair?What would it feel like in my mouth?How much will he cum? Where is he going to cum? I have tasted my own cum before and didnt care for it,I dont think Im ready to taste another mans cum.

And at that point I hear a gentle knock on my door. Oh fuck this it it! “I’m thinking to my self. I tuck my now throbbing boner back into my pants,and get up an answer the door. Jaw dropped when I opened the door. There he stood about 5’7” black knee hight socks,short red plaid skirt the stopped right above the knees,White button down blouse. long streight brown hair that went just pasted he’s shoulders. I know the school girl look was a cliche but hell it worked for me. He even had on a pair of pink starter hightops that just made the outfit look cuter. With this sweet little sexy feminine voice he saids. “So are you going to stare at me all night or are you going to let me in?”

As he walks past me I close the door behind him.