"Sure. Why not?" I said and we went upstairs to his parents bedroom.
My best friend and I had watched several YouTube videos about men who dressed up in women's clothing and, after helping ourselves to his parents liquor cabinet, we decided it would be fun to try on his mom's clothes. At first we tried on her wraps and coats and had fun drunkenly strutting around the room, but then I discovered an assortment of wigs in the back of the walk-in closet. My friend explained they were for the lavish parties his parents attended. I put one on and with the wrap I suddenly looked more female than male.
"Wow. That actually looks good on you," he said.
"Yeah?"
"Want to try a dress?" he asked.
"Do you think it will fit? I don't want to mess it up."
"I think so. You're only a couple inches taller than my mom anyway," he reminded me. That was true. Not only that, but his mom had an athletic build and I... did not. I was short and skinny as bullies would often remind me. The straightness and lack of muscle definition in my arms was the envy of many a girl.
We searched the closet and found a black cocktail dress. I took off my shirt and pants and slipped it on. The hem of the dress went about a third down my thigh but the top fit like a glove, with the little black straps crossing over my petite shoulders.
Jeff looked me over. "It's still not quite right."
It was the hair on my legs we decided. Although light and blond, it was still spoiling the look so we found some stockings and rolled one up each leg. Luckily, my hair stopped an inch or two above my knee so we were able to show a bit of my thigh between the hem of the dress and the top of the stocking. Something we both found sexy on girls.
"Better," he said.
"What about makeup?" I asked.
"You want to go that far?"
"Anything worth doing..." I said.
"...is worth doing right," he finished.
So we dove into the makeup drawer and added some blush to my cheeks and lipstick to my lips and even some eyeliner. I looked like a cheap hooker, but not bad for our first time.
"Damn. I can't believe I'm saying this but you look kind of hot," my friend said.
I checked myself out in the full length mirror and he was right. I did look hot. With the dark wig and makeup I could pass for a goth-whore. Not exactly girl next door...
"If I didn't know you I'd probably hit on you," he said.
"Sure. Like you'd have the balls to hit on me," I joked. We were both pathetic where it came to girls. Neither of us had ever had a girlfriend. He claimed a girl at camp gave him a hand job, but I never believed him. The closest I ever came to female contact was when my mom walked in on me jerking off in the bathroom. We had become so desperately horny that we would often watch porn and jerk off under blankets in his basement.
"Would you fuck me? I'd fuck me." I said in my best 'Buffalo Bill' impression.
"Ha. I don't know about fucking you, but maybe I'd let you suck my dick," he said.
"Right," I said but he seemed serious. I noticed his hand was in his pocket. Was he touching himself?
"What are you doing? Are you fucking hard right now?"
"What?" And his hand sprang from his pants. "Sorry. I'm so fucking horny."
That was true. I could see the outline of his cock through his jeans. I was turned on as well. I wasn't sure if it was the dress, the alcohol... but I was hard too.
"Want to go downstairs and jerk off?" I asked.
"Well... I was thinking what if I jerked off to you in this dress?"
"What?"
"Sorry. Is that gay?"
"I don't know. I guess if I look like a girl it's not gay," I said, checking myself out in the mirror and doing my best to make seductive poses. I wasn't sure about this but something was coming over me. The whole night had taken a sexy turn and I didn't want it to end. "I think it's okay."
"Are you sure?"
"Yeah," I agreed.
He sat on his parents bed, grabbed a blanket and covered his lap, but I didn't want him to use a blanket. For some reason, I wanted to see his cock.
"You don't have to use the blanket," I told him. My heart was pounding. We always used blankets. Did I go too far?
"But then you'll see my cock," he said.
"I know, but you might mess up the blanket when you..." I said, scrambling for an excuse.
"Oh yeah," he agreed. "But that's not fair. You'd see my cock but I wouldn't see yours."
"Now you want to see mine? I thought you were worried this was gay? I'll show you mine, too. Okay?" I said and pulled up my dress a little and slid down my underwear, but I kept my cock hidden for now. I kicked the underwear away and now I was completely naked under the dress.
"We should show at the same time," I told him. "I'll pull up my dress and you take off the blanket."
"Deal. On the count of three."
