It's been a while, had the itch, decided it was time to post something. Hope you enjoy it. More to come soon.
-J
I was sitting in the chair facing away from the mirror, my sister, Olivia, had been working on my hair for a little over an hour. She was trimming, and dyeing, and doing all these things and kept insisting “trust me.”
Finally it was the big reveal – she spun me around and what the hell had Olivia done.
“What the hell, Olivia?” I exclaimed, probably a little too loudly.
“It’s fine, Jamie, I always liked playing with your hair, it’ll grow back.”
“I look like a damn girl and you dyed it blonde!” I griped.
“That was kind of the idea,” Olivia responded. “It’s a long bob, or a lob, I wanted to try it out and your hair and face are perfect for it.”
“What am I supposed to do now? I have to go to the store after this.”
“Let me put a little makeup on you.”
“What? No way!”
“Seriously, Jamie, it’s not a big deal. You’ll look super cute and no one would ever think you’re a guy.”
“Thanks.”
“You know what I mean, you’ve always had a long hair and you’re not the biggest guy; and not to sound clichéd or anything, but you can’t grow a beard to save your life.”
I just frowned.
“Alright, just a little bit.”
Olivia grabbed her makeup bag and went to work on my face.
An hour later, I was at Shop-A-Lot, this big store that has everything, standing in the DVD section. I picked up a DVD and set it back down and noticed a guy was looking at me. He walked over and picked up the DVD I was looking at.
“Have you ever seen Monty Python?” he asked.
“Nope,” I responded quickly and started to walk away.
“Well, maybe we can watch it together sometime,” he said.
I stopped dead in my tracks, because this guy was asking me out.
“Ha, maybe,” was all I could muster.
“My name is Pete,” he said.
“Jamie.”
“Nice to meet you,” he said. “So, I- I’m not really sure how to do this, it’s been so long, but I saw you and I thought you were gorgeous. I had to come over and talk to you, plus you were looking at a copy of one of my favorite movies.”
“Well, thanks,” I blushed, I think.
“Do you think you’d like to go out to dinner with me?” he asked.
“Uh, I…” I stammered; then my brain exploded and it went into auto-pilot without my knowledge. “Sure, why not.”
Pete beamed and quickly pulled his phone out of his pocket, “Let me get your number and I text you later.”
I nodded, coolly, and gave him my number, my actual number.
When I got home, Olivia was already home and I already had three text messages from Pete.
“Olivia! I am going to kill you!”
Olivia came out of the kitchen with a microwave dinner and a glass of chardonnay – her usual – and cocked her head.
“What’s the matter?” she asked.
“I got asked out on a date!”
“Ha, who cares, you’ll be back to you after you take a shower, you’ll just have to figure something out with your hair, style it differently, it’s a little girly even without the product.”
“I said yes,” I mumbled.
Olivia laughed and nearly dropped her food.
“Oh my god, why?”
“I don’t know, I felt bad for the guy, he was nice,” I said. “He said I was gorgeous.”
Olivia laughed hard; again. “Well, Jamie, not going to lie, you’re pretty hot and you’re wearing those tight jeans and one of my hoodies, so you’re dressed essentially like a twenty-something girl.”
“Jesus Christ, Livy, what am I going to do?”
“Get dolled up and go on a date with a guy,” she said. “Or you can embarrass him and text him that you’re a guy.”
I gritted my teeth. “I can’t.”
“Then let’s go find you something cute to wear, shall we?”
An hour later, after shaving my legs and underarms, I’m standing in front of a full length mirror wearing a green dress. My hair, my sister had done something – pulled it up in back so that it has pieces framing my face.
I looked so much like a girl it was scary.
“God, you’re prettier than me,” Olivia said.
Pete came to pick me up at eight and we thoroughly avoided my nosy sister, despite her lurking around the corner in the kitchen.
“You look great,” Pete said.
“Thanks. So do you.”
I then decided by the end of this “date” I was going to tell Pete that I’m a guy and that this was wrong of me to do, but I didn’t want to embarrass him. I hoped that he’d understand and not try to kill me.
To be honest, Pete was really great company, aside from him complimenting me all the time and telling me how pretty I was. He told me he was a Silicon Valley guy who made an application about something that made him a lot of money and now he consults for other companies. I tuned out when he started talking about the other companies and the applications. When dinner was done, Pete had paid, and as we walked out he had linked his hand with mine. I felt something then that I didn’t think I’d feel, a tingling maybe. We went out to his car, he opened the door for me, and I climbed inside.
We pulled up in front of the house that my sister and I shared, and he put the car in park.
“Listen Jamie, I’m not used to all this, I haven’t been on a real date in a long time. I think you’re beautiful and funny and I’d like to see you again,” he said.
“Pete, there’s something-“ I unbuckled and turned in my seat to face him, Pete was already there and he had put his hand on my face.
“Can I kiss you?” he asked.
“I…” I didn’t respond, but he did so anyway.
We kissed for a moment, our tongues colliding in a haphazard fashion showing that neither of us had done it in a while. Finally, I put my hands against his chest and pushed him softly away.
“Listen, Pete, I have to tell you something before this gets out of hand,” I said. “I’m a guy.”
Pete smiled. “I’m not an idiot, Jamie. I know you’re a guy, but damned if you’re not the prettiest guy I’ve ever seen.”
“You knew I was a guy and you still kissed me!”
“I wanted to kiss you the day I met you and I knew you were a guy there, though, I’m sure no one else could tell,” he said. “It’s just subtle mannerisms you have.”
“I’m not gay, Pete,” I said.
“Either am I, but I had a really nice night tonight, and I’d like to see you again.”
“I don’t know, is that okay?”
“Sure,” Pete was disappointed; I could see it on his face.
“I should go,” I said.
I started to get out of the car, but something stopped me. I turned back to Pete and kissed him hard on the mouth. It was a kiss that we would both remember if it never happened again.
I quickly got out of the car and walked briskly up the walk to the front door. Once inside, I did that whole cliché thing where I leaned against the door and really thought about things for a minute.
To be continued…
I hope everyone enjoys this chapter, sorry it's taken so long. Hopefully the next chapter won't take as long. -J
I woke up the next morning and went into the bathroom and stared at myself in the mirror, my curly-ish hair was messy, but still very girly. I groaned at the sight of the raccoon eyes I had, because I hadn’t taken my makeup off last night. I wiped my face with a towel as best I could and went downstairs where my sister was making breakfast.
“Hey sis,” Olivia said.
“Shut up, Liv.”
“How was your date?” she asked.
I didn’t say anything.
“What’s the matter with you?”
“Nothing.”
“Well dish, tell me about your date,” she set a plate of eggs and bacon in front of me, and sat down at the table.
“It was fine.”
“Really, Jamie?”
“What do you want to hear?” I spread my arms wide “That we kissed? Like really kissed, and I initiated the second kiss!”
“You kissed twice?”
“Yeah.”
“Wow, I didn’t expect that.”
“Either did I, but it happened, and Pete wants to see me again.”
Olivia sat back in her chair and folded her arms across her chest. “Do you like him?”
“I… I kinda do,” I said. “But I’m a guy, and he’s a guy.”
“Sweetie, you don’t look like a guy right now.”
“But I’m a guy, god damn it.”
Olivia laughed.
“But, you really liked how it felt to be a girl, didn’t you?”
I groaned.
I caved a day later and texted Pete, he called me a few hours later, and we chatted for a few. We made a date to go to the movies that night.
Olivia helped me get my hair ready for the date, but she made me do my own makeup, “If you’re going to be a girl, you’ve got to learn how to be a girl,” she said.
Pete picked me up at eight and we went to see some romantic comedy, but truth be told, we didn’t see much of the movie. Pete’s hand made his way around my shoulder, I lifted the divider and leaned into him. He looked down at me, lifted my chin up, and kissed me. The kissing didn’t stop until I pulled away.
“Pete,” I gasped, “I can’t breathe.”
We both laughed and watched the rest of the movie.
Later, in the car, in front of my house, we went back to kissing. My hand made it’s way up Pete’s leg where I felt, for the first time, his manhood and how aroused his was. It nearly stopped me, but I left my hand on his penis, rubbing slightly.
“Come home with me,” Pete said through breaths.
“I don’t…”
“No, you’re right. Jeez, I’m sorry,” Pete said wiping my lipgloss off his lips.
“Pete…”
“Jamie, I really like you.”
I laughed, “I could tell.”
Pete turned and kissed me lightly on the lips.
“I have to go into the office tomorrow, but what about Friday, I cook you dinner at my place.”
“That sounds really nice, I’d love to.”
We kissed again, a long, passionate kiss, and I opened the door and slipped outside into the night. I smiled at him, “Text me your address, I’ll see you Friday.”
Inside, I went inside and kicked off my flats and sat on the arm of the couch next to Olivia.
“Good date?” she asked; smirking.
“Really good, actually.”
“I assume this is going to continue.”
“He’s going to cook me dinner at his house on Friday,” I said, smiling.
Olivia clicked off the TV and patted the couch next to her, I sat down, smoothing out my dress.
“Jamie, how far are you willing to go with this?” she asked.
“What do you mean?”
“You’re going to his place. What do you think is going to happen there?” she looked at me inquisitively.
“I hadn’t thought of that, but I really like him,” I said.
“Enough to have sex with him?” Olivia asked. “That’s what you’re in for if you go to his place, Jamie.”
On Friday, I pulled into the driveway of a pretty nice house and got out of the car. On the way, I stopped at a CVS and bought a bottle of Wine. The girl at the counter looked really confused by my ID, but I guess I looked enough like my picture where she didn’t care.
I walked up the steps to the house and rang the bell. Pete answered and ushered me into the house, took the wine from me, and immediately gave me a kiss on the lips.
“I missed you,” he said.
“I missed you too.”
Dinner was an Italian dish that his mother had taught him to make for our date, and it was delicious. After dinner we sat on the couch talking, which ultimately let to kissing, which ultimately led to more fondling. Pete was almost immediately aroused when I touched him down there. I continued to stroke him through his pants. We kissed more, until I pulled away. I began unzipping his pants and pulled his boxers down and his penis sprang out. Other than porn and the occasional accident in the locker room shower, I had never seen a penis up close other than my own.
I put my hand around his penis and began stroking him while kissing him deeply. Our tongues colliding with passion. I pulled away again and dropped to my knees in front of Pete. I pulled his pants down further and rubbed his legs with my hands.
“Jamie…” Pete said. “You don’t have to.”
“I want to,” I said, smiling up at him.
I then proceeded to put my mouth on Pete’s penis, stroking it while I sucked him. Pete put his right hand through my hair to the back of my head and pulled me deeper onto his shaft. I felt myself becoming aroused in my panties. I tasted precum first and Pete let go of my head, leaning back on the couch.
“Babe, babe, I’m going to come,” he said.
And he did and I swallowed his cum. I pulled back off his lap and wiped my mouth.
“Holy shit, Jamie.”
“Must’ve been the wine,” I laughed. “Did you like it?”
“Like it?”
Pete grabbed me and I straddled him on the couch, I flipped my hair to one side and he kissed me passionately. I felt him getting hard again, pushing against my leg.
“Pete, I’m not ready for that,” I said, slipping off of him onto the couch.
“I, wow, I’m sorry, I got carried away,” he said, sheepishly.
“Pete,” I said, “I will be ready, but I’m not sure when, but… the way you moaned when I did that…” I pointed to his still exposed manhood. I put my hand back on it and he shuddered.
“I really liked doing that for you,” I said. “I’m glad you liked it.”
To Be Continued…. In… “The Wedding” (No, not their wedding)