Silver Cloud

It's Sunday night, about ten. I'm in my bedroom sitting at the computer. I think my parents are asleep. I hope they are because it would be super embarrassing for them to walk in and see me sitting here naked with my cock hard. I'm going to write down what happened this weekend before I forget the details. So here goes.

It started with Dan's call on Thursday evening. Who's Dan? He lives a couple of blocks away. His parents are long-time friends of my folks, and Dan and my sister are the same age. They're close pals and even dated for a while. So I've known Dan for a long time and we're buddies even though he's three years older than me. Anyway, he's now away at college so I was surprised to get a call from him.

"Hi Katie," he said, as he always does. "What are you up to, sweetie?"

I'll explain. My initials are K.T. Hence Katie. Get it? He started calling me that when my stupid sister told him that she used to dress me up as a girl. From that point on I've been Katie to him. It's a joke, but not a funny one.

"Where are you?" I asked.

"Home," he said.

"You flunked out of school already?" I asked. That too was a joke because Dan is super smart.

"I'm home for the weekend for a friend's twenty-first. The party's tomorrow. I'm heading back Sunday."

"So maybe we can get together," I said.

"I thought you might want to come around now," he said. "There's something you've got to see."

"What?"

"Dad's got a cool new car."

Dan's dad collected vintage autos. He spent a fortune on them.

"What is it?" I asked.

"A '65 Rolls."

"Rolls Royce?"

"Yep. A Silver Cloud. It's so cool. Come and see it."

I walked over. Dan's dad kept some of his collection in a big garage next to the house. Dan opened the door to the garage and turned on the light. I'm not much into cars and don't know anything about them, but this one was beautiful. Dan opened the driver's door and got in. "Come on, get in," he said, opening the passenger door.

The interior smelled of old leather and the wood paneling gleamed in the dim light. The interior was huge. You could have thrown a party in it.

"Is he going to let you drive it?"

Dan rolled his eyes at me. "What do you think?" he said. "A pity, because I bet it's an amazing babe magnet." He got out and opened the back door. He got in the back and I followed him. "What girl wouldn't like to make out on these leather seats?" he said.

"I don't know," I said. I didn't have a lot of experience with girls.

"Well, if you were a girl, would you prefer to make out in the back seat of a Rolls or a Ford?"

"A Rolls I suppose."

"You're not sure? Here, we'll try it out. Let's pretend you're my date and I've managed to get you into the back seat." He moved over and sat close to me. "You look so beautiful against that leather, baby," he said in a husky voice. "Can I kiss your delicious lips?"

I laughed. "I can't imagine you have much luck with lines that that."

"But Katie, sweetie," he continued in the same voice, "you're so pretty." He leaned over and kissed my cheek. I pushed him off.

"Get off me you pervert."

"You're the pervert," he said, "not getting turned on by a Rolls."

He tried to kiss me again. I pushed him away, laughing. "Yep, I'm the pervert. Not the guy who's trying to kiss his ex-girlfriend's younger brother."

"That's ok if he's imagining him as his sexy older sister."

By now we were wrestling in the back seat. He pinned me to the seat and sat over me.

"About that kiss, Katie," he said, moving his face towards mine.

"Is this the only way you can get laid?" I asked. "Holding girls down?"

"Just one little kiss," hesaid. "What's wrong with that?"

"No," I said. "I'll scream and your Dad will see what you're doing in his Rolls."

"Ok," he said. "Give me a kiss and I'll take you for a drive in the Rolls Saturday night."

"Your Dad won't let you drive it."

"They're out Saturday night. He won't know."

I was tempted. "Maybe," I said.

"There's one condition though," Dan said.

"What's that?"

"You'll come dressed as Katie."

"No way!" I said.

"But I can't go for a drive in a Rolls with a boy. That would be kinda gay."

"Oh, right. But it's ok if the boy is dressed as a girl?"

"That's quite different. That's just having fun."

"No. I'm not coming as Katie."

"Please sweetie," he pleaded. "It might be your only chance to get a ride in a Rolls."

"I can live without it."

"Ok, then, I have to resort to this," he said, and started tickling my ribs. I was struggling and struggling and as I did he was lifting up my t-shirt, and then, forcing me down on the seat, he kissed my exposed nipple. As I still struggled, he took it between his lips. A jolt of excitement rushed through my body and I felt my cock beginning to grow.

"Stop! Stop! Ok. It's a deal. I'll come as Katie."

He stopped sucking my nipple. "You promise?"

"Yes."

"With makeup and everything?"

"Yes."

He gently kissed my nipple again and sat up, releasing me. I pulled down my t-shirt to cover my nipples and we sat looking at each other for a moment, neither of us really sure what had just happened.

______________________

Saturday morning I got a text from Dan. "Have to cancel our date tonight. Sorry."

"It wasn't a date," I replied. "But what's your excuse?"

"I met a girl at the party last night. I asked her out."

"That makes me feel really special," I replied.

"I'll make it up to you, Katie sweetie," he wrote.

"You're a bum," I wrote.

He didn't reply, and after a couple of minutes my annoyance passed. Was I really upset that he had canceled? Was I beginning to think of myself as Katie, spurned because he had a date with a real girl? That would be totally weird, I thought.

But that evening, sitting at home bored, I remembered that Dan's parents were away for the night. When my parents were asleep, I took the key to Dan's house that my parents kept in a drawer in our kitchen, tiptoed out of the house and walked down the street to Dan's house. I let myself in and found the garage key on the hook near the back door. I went to the garage. The door of the Rolls was open and I got in the back seat. I opened the gym bag I had brought with me and took out the clothes I had selected from my sister's room. I undressed and put them on: a pair of white thigh high stockings, white bikini panties, and a white camisole. I lay across the wide leather seat and took some photos with my cell phone. When I had one I liked -- my legs spread and my fingers inserted a couple of inches into my panties -- I sent it to Dan. I added a note: "You were right. Girls do get horny in the back seat of a Rolls! Love, Katie"

I waited to see if he would respond.

He wrote back a few minutes later.

"You look so amazing!"

"I'm glad you think so," I replied. "I hope you're having a nice time with what's-her-name while I'm half naked in your dad's Rolls."

"Ok," he replied. "You win. I made a bad choice."

"You mean that you're not going to get laid?" I asked.

"It's not looking likely," he replied.

I pulled my panties down over my thighs and started stroking my cock. When I was hard I took another photo. I sent it to Dan. "Well at least one of us is having sex tonight," I wrote.

He called a minute later. "Hi Katie," he said, sounding nervous.

"Hi Dan," I answered, my voice betraying my excitement.

"Are you playing with your cock?" he asked.

"Yes," I said. The rest of the call was filled with my moans as I made myself cum.

I hung up and lay back on the leather seat thinking about what I had done, wondering whether I should be regretting it. After a few minutes my cock was hard again. No regrets then, I guess, I thought to myself, and masturbated again, this time imagining Dan arriving home and getting into the back seat with me.

_______________

The next morning about nine I was sitting in the kitchen eating breakfast and talking with my parents. Dan called.

"Hi," he said. "What are you doing?"

"Eating breakfast."

"What are you doing later? Do you want to come over?"

"I told Dad I'd go to the store with him to help him carry some gardening stuff." My Dad gave me a questioning look because I hadn't told him any such thing.

"Can you get out of it?"

"I wouldn't want to," I said. "A promise is a promise, after all."

There was a pause on the line.

"Are you still mad at me?" he asked.

"Of course not," I said. "Did you have a nice time last night?"

"No," he said.

"I'm sorry," I said, my voice lacking all sincerity.

"Please Katie, come over this morning. My parents don't get back 'til midday."

I was enjoying his begging. "Let me check with my dad," I said. "Maybe we can go to the garden store this afternoon."

I was quiet for a minute or so. "He's not happy about it, but he knows that you're driving back to school later today, so he's agreed."

"How soon can you be here?"

"Maybe thirty minutes."

"Come as soon as you can."

"Ok, then. Bye." I hung up.

I finished my breakfast. So this is the power girls have, I thought. Yesterday, I was my sister's little brother, to be teased and laughed at. But when a boy wants sex, suddenly he'll take you seriously.

I showered and then returned to my sister's lingerie drawer. I hesitated: black or white? White again, I decided; it goes so well with my blond hair and contrasts nicely with the dark leather in the Rolls. I chose a pair of white lacy boy shorts and the white thigh high stockings I had worn yesterday. Then, instead of a white camisole, I found a white silk chemise in her closet. I went back to my bedroom and dressed. Very pretty, I thought, looking at my reflection in the mirror. I pulled on some track pants and a sweatshirt. I took my gym bag and gathered some make-up from my sister's room. "I'll be back in a couple of hours," I called out to my parents as I left the house.

Dan let me in before I could ring the bell. He closed the door behind me, and we stood looking at each other. I liked the fact that he was nervous.

"Hi Dan," I said.

"Hi Katie," he replied.

"Here's what we're going to do," I said. "I'm going to the bathroom to transform myself into Katie. You're going to go to the Rolls. Ok?"

"Yes," he said.

"You're going to get in the backseat, and you're going to undress. Completely. Ok?"

He nodded his head.

I watched him walk through the house, then heard him open the garage door. I went to the bathroom and took off my sweatshirt and track pants. I put on some blush, some eyeliner and some lipstick, remembering what my sister had done when she made me up. I took my time, imagining Dan naked in the Rolls waiting for me. Katie, you are so pretty, I thought as I finished making myself up, admiring my reflection in the mirror.

I walked to the garage and got in the back seat. As my eyes got used to the dim light, I made out Dan's naked body. His cock was hard.

"Have you been touching yourself?" I asked.

"No," he said.

"So why are you so hard?"

"I was thinking about you. About the pictures you sent me last night."

"So you liked how I was dressed?"

"It was amazing."

"And what about now? You like me in these panties too?"

"You are incredibly sexy."

I had been intending to not touch him until he begged me to, but now, seeing him naked and hard, my resolve failed me, and I moved closer to him. I leaned forward and kissed him lightly on the lips. "I was thinking about you kissing me when I was here last night," I said. "I imagined you coming back and finding me here." I kissed him again. "I imagined that you were naked, like you are now, with your cock hard." My hand went to his cock and held it gently. He took a sharp intake of breath. I kissed him again. "I imagined holding your hard cock and stroking it, just like I'm doing now."

"That feels so wonderful," he whispered through his soft moans.

"So you'll never break a date with me in the future?"

"Never. I promise."

I held his cock more firmly and stroked it faster. He came quickly, his cum splashing over my hand. I lay down on the seat and pulled him down beside me so his head was on my shoulder. I continued to stroke his cock, gently now, hearing his breathing relax. We lay together like that for a long time.

Then Dan propped himself on his elbow and looked down at me, smiling. His fingers undid the buttons on my chemise and folded it back, exposing my nipples. He leaned over and took one of them in his lips and caressed it gently with his tongue until it was erect. His hand went to my waist, then down over my hips to the outside of my thigh. Then it moved to the inside of my legs and ran back up until it touched my panties. He held my cock through the thin material, then pulled my panties down to release it.

I lay back on the leather seat moaning at the touch of his hand on my cock and the caress of his lips on my nipple. Then his head moved down over my abdomen and stomach until his mouth was on my cock. I moved my hips as he sucked me, pushing into his mouth and pulling out. His hand went between my legs and held my balls. Two fingers slipped further back to caress my opening. I came in his mouth with a long loud yell, my cum shooting out spurt after spurt as his grip tightened and he thrust his fingers deep into me.

Dan kissed me again, deeply.

"Have you ever tasted your own cum before?" he asked.

I nodded. "I used to see if I could shoot it into my mouth. I could only do it if I masturbated upside down. But then it ended up in my hair more often than my mouth."

"I'd like to see you do that," he said.

"And I'd like to watch you masturbate. When you get back to school, send me videos of you playing with yourself. Unless, of course, you have way too many girlfriends to masturbate for me."

He kissed me again. "None like you, sweetie," he said. "And what about you? Is Katie going to have other boyfriends while I'm away?"

I hadn't thought about it. "Would you be jealous?" I asked.

He laughed. "Hugely! But also turned on by the thought."

"We've only just become lovers and you're already thinking of me as a slut!"

"Am I wrong?" he asked.

"Maybe," I said. "But, there again, maybe not. I've got a lot to learn about what Katie wants."

_________________________________

I came out of the bathroom dressed in my sweatshirt and track pants. Dan had a broad smile on his face. "We're not going to see each other for weeks and you're smiling?" I asked.

"I'm smiling because even though you're dressed like that I still see you as Katie." He put his arms around my waist and pulled to me him. I stood on my tiptoes and returned his kisses. His hands slid down over my ass and he pulled my body against his.

"Have a safe drive back to school, baby," I said.

"Maybe I should leave tomorrow instead," he said.

"But you'll miss classes."

"But we'll have some more time together."

"And what would we do with that?"

"Spend more time making love?"

"Sex? What a typical boy! How about just cuddling and talking?"

"We can do that too," he said.

I laughed. "I was kidding! I want you to sneak into my bedroom tonight and make love to me."

I kissed him again and walked home.

_______________________

It's almost eleven and Dan is about to arrive and Katie has yet to get dressed. I've chosen a sheer negligee for her. She tried it on earlier. It's tight, but it fits. She has a pair of skimpy white panties to wear under it. I've been thinking about Katie watching Dan undressing and seeing his beautiful cock again. I've been imagining how Katie will ask him to pull down her panties and make love to her. I've been imagining him putting her on her knees and slipping his big cock into her pussy while she tries to stifle her moans so not to wake her parents. Maybe I'll write some more tomorrow. For now though, Katie has to get ready for her boyfriend's visit.