Playing Dressup

Jeff and I spent the entire week at school without discussing what had happened. How I had dressed up in his mother's clothes, which turned him on so much he asked if he could jerk off to me. How one thing lead to another and, before we knew it, we were jerking off to each other and even tasting each other's pre-cum! I didn't feel wrong about it, I was actually excited. I spent the week watching pornos and suddenly became envious of girls giving blowjobs and swallowing thick loads of cum. Now I wanted to try that. Luckily, even though we didn't discuss it, we did make plans to spend the night at his house again.

"So..." I said, sitting on the floor of his bedroom and flipping through the pages of a graphic novel. "What are we going to do tonight?"

"I don't know. Play video games, watch movies," he replied.

"Okay," I said, somewhat disappointed. I desperately wanted a repeat of the previous weekend, but was too nervous to bring it up.

"Unless there was something else you wanted to do," he added. Was that it? I still wasn't sure.

"Are your parents going out again?" I asked.

"Yeah."

"So... if we wanted to..."

"We could go into my mom's closet again," he said. "But only if you want."

"I can do that again," I said. Yes. That's what I wanted. Well, I really just wanted to jerk off looking at his cock again. I had been thinking about it all week. I never considered myself gay before, but I couldn't get his cock out of my head. All that cum that shot out... tasting his pre-cum... that might have been the best part. And I guess he wanted to see me as a woman again. I didn't mind. It felt sexy in a weird way to dress up like that. And whatever turned him on was alright by me.

"I've been watching videos on how to do makeup and everything. You're going to look really good this time," he told me.

"I didn't look good last time?" I asked, pretending my feelings were hurt.

"No. You looked great. But now you'll look even better."

I smiled and we went back to what we were doing, but the next few hours were excruciating. My cock would get hard constantly while we waited for his parents to leave, and when they finally did we wasted no time. We raced to his mom's closet.

"I think you should wear that same black dress since it fit so well," Jeff said to me.

"Okay," I said and went into his mom's closet. I took off all my clothes including my underwear and slipped the dress over my head. I found the stockings in her top drawer and rolled them up to my thigh. We both liked the way a girls leg looked when it was partially exposed between the hem of a dress and the top of the stockings, so I copied that for my legs. Then I put on one of his mom's costume wigs and Jeff applied makeup to my face based on the tutorial he had watched earlier.

"Perfect," he said when he was finished. "Take a look."

"Wow," I said, looking in the mirror. I looked like a girl. And not just a girl. A hot girl. If I saw myself somewhere I would fantasize about me. How confusing. "So I guess you want to jerk off to me..."

I noticed Jeff already had his cock out and was stroking it.

"Sorry," he said. "I haven't jerked off all day."

"Me either. Look," I said, pointing at the dress. You could clearly see my cock was hard and pointing straight out making a 'tent pole' in the fabric.

He laughed when he saw it. "We better do something about that too."

"Let's go back to your room," I said and we hurried off to his bedroom and closed the door.

"So should we just jerk off again?" he asked.

"I guess so," I said. "But I think..."

"What?" He asked. "Is there something wrong?"

"No," I said. He seemed overly excited and worried that I might not want to do it. But the opposite was true. I wanted more. "I was thinking. I really liked tasting your pre-cum."

"Yeah? Me too. Yours, I mean," he said. I could see a large glob of pre-cum at the tip of his cock. My mouth was watering.

"Well I was thinking that since I look like a girl, maybe I could give you a blowjob?"

"What?" He asked, his eyes wide and his mouth agape.

"Only if you want to," I said, suddenly embarrassed. Fuck. I shouldn't have asked that. I'd gone too far. It was too gay.

"I think that would be amazing," he said. "As long as you don't mind."

"Really?"

"Yeah. I was actually hoping you would do that, I just didn't know how to ask," he said and ask down on the bed.

"Right here?" I asked.

"Yeah. You think somewhere else is better?"

"No. I think this is fine. I've just never done this before."

"Me either," he said, laughing. Neither of us had done anything before.

"Here I go," I said and I knelt between his legs and came face to face with his cock, which was bobbing up and down and somehow seemed even bigger than before. I took a deep breath and wrapped my hand around the base of his cock. It was smooth to the touch, and it was so warm. I could feel it throbbing in my hands and there was a huge amount of pre-cum at the tip. I pushed my tongue out and licked it straight from his cock. His whole body shuddered as I brought the pre-cum into my mouth. It wasn't enough to swallow, but I savored the taste. I squeezed my own cock under my dress and could have cum right there on his floor but I held back.

"Come on," he said, impatiently.

I nodded. This was the moment of truth. There was no going back from this. I closed my eyes and took the head of his cock into my mouth and wrapped my lips tightly around his shaft. My tongue pressed against the head and he shuddered again. His cock filled my whole mouth. It felt amazing.

"Holy shit," he moaned.

"Does it feel good?" I asked, pulling away.

"It's the best feeling I've ever had," he said and it sounded like he might pass out. "Keep going."

"Okay," I said and put him back in my mouth. I sucked on his cock like it was a thick milkshake and I jerked up and down his shaft with my hand. I had no idea what I was doing and was relying purely on what I had seen online and what I imagined might feel good if someone was doing this to me. It seemed to be working as I could hear his heavy breathing and moaning. Thank god no one was home.

"Holy shit," he said, panting. "You're so good at this."

The compliment sent a rush of pleasure through me and I realized how much I was enjoying this. Having his cock in my mouth. Causing him such immense pleasure. I was so happy we were doing this. I didn't want it to end.

"I think I'm going to cum," he said. "What do you want me to do?"

"I want to taste it," I said, catching my breath.

"Yeah?"

"Yeah. You can cum in my mouth," I told him and I stroked his cock with both of my hands, opening my mouth as wide as it could go and sticking out my tongue.

"Oh my god this is so fucking hot," he said as he looked me right in the eyes. I must have looked like a porn star, with my hair and makeup, my tongue sticking out waiting to catch the 'money shot'. It was all too much for him to bear...

"Oh shit..." he said and I felt the first blast hit me in the back of the throat. I almost gagged but kept my composure and kept stroking the rest of his thick load onto my outstretched tongue. There was so much of it and it all slid into my mouth. It was surprisingly creamy, with thick and watery parts. It tasted different than the pre-cum. This was saltier. More potent. But I liked it and the mere thought of having all this cum in my mouth was incredible.

When he was finished I swirled the cum inside my mouth, savoring the texture and flavor. Then I swallowed and could literally feel it slide down my throat.

"Oh my god," he said. "That was awesome. What did it taste like? Did you like it?"

"It's hard to describe, but I liked it. A lot. Did it feel good?"

"Dude. It was the best ever. Do you want me to suck yours now?"

I wasn't expecting him to ask that. I figured since I was the one dressed up he only wanted me to do those things and since he had just cum, this was an even bigger surprise.

"Yeah. If you want to. I could just jerk off I guess," I said, giving him an out.

"No. I want to do it too," he said. "Switch places."

I sat on the bed and he kneeled in front of me. He lifted up my dress and my cock sprang out and hit him right in the face. He laughed and grabbed it with his hand. I was so fucking horny I had to hold back. I could have cum right there in his face but I at least wanted to feel what he felt.

"I can't believe we're doing this," he said and then shoved my cock into his mouth. I wasn't prepared for how warm and wet if felt. And I could feel everything; the roof of his mouth, his teeth lightly scraping my cock, his tongue swirling around the head of my cock. He was as into this as I was and that made it feel even better.

And I couldn't hold it any longer.

"I'm going to cum," I warned him.

He sucked me even faster now, clearly an invitation to cum at anytime. So I did. I couldn't see it but I could feel that I shot seven or eight loads into his mouth and he moaned louder with each one until finally he popped off of my cock and opened his mouth. It was all white. Filled to the brim.

"Oh my god," I said, through deep breaths. "Are you going to-"

He closed his mouth and swallowed it all down right in front of me.

"Wow." I said.

"That was a huge load," he said, laughing.

"Are you ok?" I asked, worried that it was too much.

"Yeah. No. I liked it. Like I really liked it."

"Should we do it again?"

To be continued...