Chapter 1: Keeping A Secret

My first experience with Femboys and crossdressing in any form started with my best friend Daisy.

He's been my best friend since highschool and when we moved on to college, we of course moved in together as roommates.

One this particular day I had let him know I planned to spend the night with my girlfriend. At least that was the plan. What actually happened was Julie getting called into work at the last second as we were heading out for our date. So disappointed and with more than a bit of blue balls, I headed back to my apartment.

When I arrived I quietly entered the house hearing sensual music coming from the living room. Curious I walked over to see what was going on. At first I assumed Daisy had a girl over but instead I found a shock.

On the couch was Daisy. Eyes shut tight as he rubbed his cock over the silk panties he was wearing. On his laptop some kind of feminization video seemed to be playing based on the sound. He wore a sexy pair of lingerie and an eye catching wig. If I didn't know for a fact it was my roommate I could have easily mistaken him for a sexy babe. I could only stare in shock at the view before me.

After a few moments Daisy finally opened his eyes to see i walked in on her and let out a panicked shiek.

"Dude. What are you doing home. I thought you were gonna be with Julie all night" he asked while desperately grabbing his blanket to cover.

It took a second to reply because I was admittedly staring at his ass and the perfect way the panties he was wearing, hugged his hips. "Umm. Julie got called in last second so we had to cancel."

Daisy looked like he wanted to come up with some lie to explain why you caught him like this before letting out a defeated sigh. "Look man, I know this is weird for you. I just- I been into cross dressing for awhile. I do it when I have the place to myself. I'm sorry to catch you off guard. I'll leave for the night and look for a new place if your uncomfortable." He says clearly nervous about your reaction and trying (and failing) to hold back the tears in his eyes.

It broke my heart to see him like this. He's been my best friend since the day I met him. He's always been more feminine in his looks and nature and that never changed how much I cared about him. The fact he thought this was enough to make me turn my back on him is ridiculous.

I walked closer to him and pulled him into a big hug. "Hey man, don't worry about it. If you like this then great you don't have to hide it around me. It's your home too. And your secret is safe with me obviously." I say with a big smile as Daisy hugs you back and crying happily in your arms.

I held him as he composed himself. Doing your best not to focus on how soft his skin is as his body brushes so closely to me or how good of a view of his bubble butt you have. I'm incredibly lucky he was so absorbed in his emotions that he didn't notice how hard I was getting.

"Thanks John. I was so nervous about how'd you relax. I should have known you'd be understanding. You're my best friend man." He said wiping his tears after breaking the hug.

"Of course man but I gotta know, how'd it start?" I asked curiously.

"Hell idk man. Few pornos here. Few J.O.I. videoed there. Joined a few online forum groups. My favorite was one for local femboys who are getting into cross dressing. They gave me the courage to actually give into my impulses and give it a try. Then last year I decided to actually start dressing up and I just got hooked. I just feel More confident and..... Well cute." he claimed, saying the last part in a barely audible whisper.

I can see what he means. Usually he's so quiet and soft spoken. But in his fem persona he stands more confident and lost his usual stutter he gains when he's nervous. I had lots more questions for him but the whirlwind of a day I had left me Exhausted.

"Okay, that's sounds like stories I gotta hear but later. Right now I got a date with my bed." You both laugh at your lame joke and you make your way to your room. Before you fully leave the room you stop and say to Daisy. "By the way Daisy, your right. It does make you look cute." You say giving him a playful wink before heading to bed.

Unbeknownst to you it took Daisy about ten minutes to get over his blushing fit you gave him.