In the three years that I have lived in an apartment with my friend Joe, I've never thought of him in a sexual way. Recently, I discovered that he is a crossdresser like me. We both just hide it. I was looking in his room for one of my dvd's he borrowed and found wigs, women's clothes and even a Polaroid of him dressed as a woman. The moment my eyes glanced at the picture, my cock grew. It had never occurred to me that he could make a sexy woman. Joe was quite passable.
I forgot about my dvd and took the picture. It was inspiration for several orgasms. A long black haired wig hung down to his shoulders and a black leather corset was squeezing his body tightly. I only wished that the picture went down further so I could see his cock.
Part of me wanted to tell him that I knew. At least then, we would both have someone to share this interest with. I figured I'd talk to him about sexual interests and fetishes, see where it led.
"So...Joe. What kind of things are you into?"
"What do you mean?"
"Well, sexually. Just making conversation. We seem to have a lot in common with other things so I was just curious."
"I don't know, I'm pretty open minded."
"Yeah me too. I have a really big latex and leather fetish. Something about a girl in tight clothing."
"Yeah, I actually like that too. It's really sexy.
It got silent for a moment as we both just sat there, sipping at our beers.
"I got to admit Joe, and I've never told anyone, but I feel like we are pretty good friends, I like trannies."
"Yeah. I don't have an attraction to guys, so that's always confused me but seeing a chick with a big cock just turns me on. I don't know. Even crossdressers are sexy to me. Passable ones."
"Yeah, I guess I can see that. It's different. Well, to be honest with you, I'm kind of into that too."
"Oh yeah?" I said, pretending to be surprised. "We do have a lot of the same interests. Actually, I'm going to admit something else, I like to dress in women's clothes."
I thought for sure, by admitting this, he would in turn do the same.
It got silent again. He looked kind of nervous.
"Okay, Joe. I was hoping you would just tell me but I got to be honest. I was looking for my dvd the other day and found a Polaroid picture of you dressed up."
"Fuck. At least I know where it's at now. Thought I lost it. Why did you take it?"
"Well, to be honest, it really turned me on. You're very passable. You look just like a girl."
It got quiet again before he turned towards me and said, "Did you masturbate to it?"
"Yes. I used it and it helped get all sorts of images in my head. Have you ever been with a cd?"
"No. I've always wanted to try but I've never even been dressed in front of anyone before."
"Yeah, same here. I don't know if you'd want to, but maybe we could dress up for each other. Be a first for us both and who knows what might happen."
"Sure. We could try that. Bit nervous but we've wanted to try it so maybe we should just do it."
We both went into our rooms to get dressed up. I put some eyeliner on and bright red lipstick. There were several wigs but the long blond hair called to me. I slid on my knee high leather boots and snapped on my elbow length latex gloves. The outfit was the hard decision. Over time I've bought several and wasn't sure what Joe would like best. I ended up just choosing a red latex dress with black trim.
When I walked out of my room, he was sitting on the couch waiting for me.
"Wow, you look hot as hell. What do you think about me? You haven't seen me dressed before."
"You're very passable yourself. Damn, you look sexy. Like my outfit?"
He decided to stick with the black haired wig. We think alike, both going with gloves but his were black latex barely covering his wrist. Rather than a dress, he had decided on a short leather skirt with a bra that matched.
"It's incredibly sexy," I said as I stared in awe.
"Thanks, Actually, I didn't have to ask, I can see you have an erection. It's poking at your dress."
I sat down next to Joe and reached my gloved hand under his skirt, amazed at how big his cock was. Moans escaped his pink painted lips as he reached over and started jerking my dick from under the tight dress. The sight was too much. I got down on my knees and pulled up the skirt, revealing his big dick. He looked down at me and put his fingers around my hair, holding tightly as he pushed the head between my lips. It slid in and out with ease as my saliva coated it. I'd lick the plump head then go down the base until I'd gag. He had to be about 9 inches.
"Mm, you suck very well. Do you like your face fucked?"
"Oh yes. Fuck it hard, please."
Joe is normally so shy, but when he is dressed, he is very assertive. His hands pressed on the back of my head, keeping me from backing away at all, while he drove his dick all the way down my throat.
"Yeah take all of that cock my little she-bitch."
This was turning me on immensely. My hand wandered down to my prick. I couldn't help it, I had to start jerking.
"You are doing great, but why don't you get on the ground. We can 69. I'd like to get some of your cock in my mouth as well."
I did as I was told and laid flat. His cock slowly came down towards my face. I licked at the balls before taking the thick shaft into my mouth. He spit on my dick as he rubbed the smooth latex over me, causing me to shiver.
With his weight on me, he started fucking my face again, making it hard to escape for a breath. His tongue licked wildly at my shaft before diving down, pushing the head to the back of his throat. Without warning, Joe shoved a finger in my ass and started fucking me.
"You like that? Fucking your ass?"
All I could do is try to say yes, but it's hard with your mouth full.
"I know you do. You are sucking so good, I'm going to give you a treat."
I had never tried cum but I wanted it so badly at this point. His cock enlarged and I knew what was to come. Within seconds my mouth was being flooded by his hot seed. I swallowed as much as I could. Joe started stroking me faster and I exploded into his gloved hand.
"Wow, that was...amazing," I said as Joe looked me in the eyes so intensely. Slowly he licked up to the palm of his shiny glove, cleaning up my semen. The sight was arousing and then I knew that this had to be the first of many times. I wanted more.